NPASS Compound

Structure

CID277205 OpenBabel06191716082D 33 36 0 0 1 0 0 0 0 0999 V2000 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 22 1 0 0 0 0 7 20 1 0 0 0 0 8 31 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 32 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 33 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 1 0 0 0 16 18 1 0 0 0 0 16 27 2 0 0 0 0 17 19 1 0 0 0 0 17 28 1 6 0 0 0 18 20 2 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 30 1 1 0 0 0 20 32 1 0 0 0 0 21 31 1 6 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.1
Volume:	421.937
LogP:	0.379
LogD:	-0.068
LogS:	-3.848
# Rotatable Bonds:	4
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	4.017
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.372
MDCK Permeability:	7.648081918887328e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.323
Human Intestinal Absorption (HIA):	0.617
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	91.9722671508789%
Volume Distribution (VD):	0.775
Pgp-substrate:	11.057316780090332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	3.776
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.854
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.833
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.616
Respiratory Toxicity:	0.029

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC277205

Natural Product ID:	NPC277205
*Common Name:**	Quercimeritrin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	NSC-115917
Standard InCHIKey:	BBFYUPYFXSSMNV-HMGRVEAOSA-N
Standard InCHI:	InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL248726
PubChem CID:	5282160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843586]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO11304	Vitis thunbergii	Species	Vitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15730246]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[16038562]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO8311	Lespedeza virgata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17890083]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO8311	Lespedeza virgata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484774]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19252323]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[2380715]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2380715]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106289]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	Subaerial Parts	n.a.	n.a.	PMID[30207720]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176403]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23516	Potentilla discolor	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2961	Lomelosia caucasica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23516	Potentilla discolor	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8261	Gleditsia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16256	Helleborus viridis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16596	Dysoxylum schiffneri	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4980	Lycopodium erythraeum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6570	Cinnamomum philippinense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12464	Litsea nitida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10086	Scrophularia scorodonia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO382	Zanthoxylum scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17987	Mycosphaerella nawae	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4171	Isolona pilosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12049	Lecania gerlachei	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18824	Alpinia pulcherrima	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8519	Garcinia andamanica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19416	Streptomyces sakaiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1560	Boronia alata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18576	Vernonia aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7328	Salvia miniata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18653	Cyathus intermedius	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11763	Cyperus capitatus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8261	Gleditsia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9038	Aconitum burnatii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17876	Magnolia henryi	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20597	Phascolion strombus	Species	Phascolionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2351	Echinocardium cordatum	Species	Loveniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17565	Hordeum bulbosum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5899	Ainsliaea uniflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11941	Helleborus serbicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19554	Coronilla hyrcana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15709	Lobelia langeana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10313	Plantago arborescens	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9142	Aeschynanthus parvifolius	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11304	Vitis thunbergii	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14192	Climacoptera transoxana	Species	Tettigoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25549	Rhizophagus intraradices	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6642	Mocis latipes	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19350	Ephedra altissima	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18326	Eria siamensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO931	Malus baccata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2961	Lomelosia caucasica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1457	Phoma asparagi	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19683	Pycnothymus rigidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO222	Phebalium drummondii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19069	Thelepus setosus	Species	Terebellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19285	Chromodoris cavae	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17050	Haemanthus albiflos	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10957	Cladosiphon okamuranus	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19222	Mycale tenuis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8673	Actinopyga echinites	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9041	Libocedrus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18747	Bufo bankorensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13245	Agelas longissima	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16034	Lecanora sulphurata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19495	Bignonia unguiscati	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20618	Penicilliopsis clavariiformis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18986	Betula papyrifera	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18899	Keyserlingia koreensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16727	Iris sibirica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17433	Peltophorum dubium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15370	Tamarix dioica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6028	Laurencia pinnatifida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
NPO454	NPC277205	Other	Pollen Or Spore	2.2	2.2	2.2	mg/100g	Database [DUKE]

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
Others	4

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[468001]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	28.0	ug ml-1	PMID[468002]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	36.55	%	PMID[468003]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	13.02	%	PMID[468003]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	71.65	%	PMID[468000]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC277205 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	459
0.1-0.2	1878
0.2-0.3	4343
0.3-0.4	9952
0.4-0.5	8053
0.5-0.6	4126
0.6-0.7	5204
0.7-0.8	5256
0.8-0.85	1627
0.85-0.9	1172
0.9-0.95	441
0.95-1	186

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC281131
0.9936	High Similarity	NPC88789
0.9936	High Similarity	NPC145038
0.9936	High Similarity	NPC197285
0.9936	High Similarity	NPC276222
0.9936	High Similarity	NPC253662
0.9936	High Similarity	NPC21100
0.9936	High Similarity	NPC308404
0.9936	High Similarity	NPC179950
0.9936	High Similarity	NPC118284
0.9936	High Similarity	NPC274618
0.9936	High Similarity	NPC56077
0.9873	High Similarity	NPC317489
0.9873	High Similarity	NPC52550
0.9873	High Similarity	NPC127546
0.9873	High Similarity	NPC223424
0.9873	High Similarity	NPC173637
0.9873	High Similarity	NPC84362
0.9872	High Similarity	NPC19388
0.9872	High Similarity	NPC240431
0.9872	High Similarity	NPC55786
0.9871	High Similarity	NPC189142
0.9871	High Similarity	NPC77660
0.981	High Similarity	NPC120099
0.981	High Similarity	NPC203050
0.981	High Similarity	NPC219904
0.981	High Similarity	NPC223747
0.981	High Similarity	NPC225434
0.9809	High Similarity	NPC135599
0.9809	High Similarity	NPC113968
0.9809	High Similarity	NPC328940
0.9809	High Similarity	NPC277174
0.9809	High Similarity	NPC73855
0.9808	High Similarity	NPC168822
0.9808	High Similarity	NPC191306
0.9808	High Similarity	NPC270335
0.9808	High Similarity	NPC19709
0.9748	High Similarity	NPC136042
0.9748	High Similarity	NPC282987
0.9748	High Similarity	NPC116864
0.9748	High Similarity	NPC244776
0.9748	High Similarity	NPC259896
0.9748	High Similarity	NPC67326
0.9748	High Similarity	NPC155763
0.9748	High Similarity	NPC245014
0.9748	High Similarity	NPC156869
0.9748	High Similarity	NPC254855
0.9748	High Similarity	NPC255157
0.9748	High Similarity	NPC235260
0.9748	High Similarity	NPC29958
0.9748	High Similarity	NPC67105
0.9748	High Similarity	NPC20505
0.9748	High Similarity	NPC84265
0.9748	High Similarity	NPC206123
0.9748	High Similarity	NPC95866
0.9748	High Similarity	NPC285197
0.9747	High Similarity	NPC265530
0.9747	High Similarity	NPC226304
0.9747	High Similarity	NPC325555
0.9747	High Similarity	NPC92565
0.9747	High Similarity	NPC160156
0.9747	High Similarity	NPC275454
0.9745	High Similarity	NPC311830
0.9745	High Similarity	NPC22832
0.9744	High Similarity	NPC473043
0.9688	High Similarity	NPC117260
0.9688	High Similarity	NPC471748
0.9688	High Similarity	NPC153755
0.9688	High Similarity	NPC175107
0.9688	High Similarity	NPC26230
0.9688	High Similarity	NPC476405
0.9688	High Similarity	NPC190003
0.9688	High Similarity	NPC155877
0.9688	High Similarity	NPC134532
0.9688	High Similarity	NPC60735
0.9688	High Similarity	NPC176740
0.9688	High Similarity	NPC33054
0.9688	High Similarity	NPC471725
0.9688	High Similarity	NPC245452
0.9688	High Similarity	NPC203259
0.9686	High Similarity	NPC52382
0.9686	High Similarity	NPC138927
0.9686	High Similarity	NPC227508
0.9686	High Similarity	NPC270578
0.9684	High Similarity	NPC254306
0.9684	High Similarity	NPC210073
0.9684	High Similarity	NPC8856
0.9684	High Similarity	NPC115674
0.9684	High Similarity	NPC255615
0.9684	High Similarity	NPC67037
0.9682	High Similarity	NPC284960
0.9682	High Similarity	NPC29830
0.9682	High Similarity	NPC309025
0.9682	High Similarity	NPC222936
0.9682	High Similarity	NPC88023
0.9682	High Similarity	NPC243930
0.9627	High Similarity	NPC4390
0.9627	High Similarity	NPC42773
0.9627	High Similarity	NPC101026
0.9627	High Similarity	NPC21666
0.9627	High Similarity	NPC45522
0.9627	High Similarity	NPC24043
0.9627	High Similarity	NPC169977
0.9623	High Similarity	NPC48640
0.9623	High Similarity	NPC229729
0.9623	High Similarity	NPC146792
0.9623	High Similarity	NPC58716
0.9623	High Similarity	NPC149244
0.9623	High Similarity	NPC45618
0.962	High Similarity	NPC34531
0.9618	High Similarity	NPC300537
0.9618	High Similarity	NPC127782
0.9568	High Similarity	NPC473327
0.9568	High Similarity	NPC135277
0.9568	High Similarity	NPC476472
0.9568	High Similarity	NPC210094
0.9568	High Similarity	NPC101191
0.9568	High Similarity	NPC214621
0.9568	High Similarity	NPC34267
0.9568	High Similarity	NPC294815
0.9568	High Similarity	NPC19108
0.9568	High Similarity	NPC477848
0.9568	High Similarity	NPC253685
0.9568	High Similarity	NPC115760
0.9568	High Similarity	NPC294629
0.9568	High Similarity	NPC220173
0.9568	High Similarity	NPC237435
0.9568	High Similarity	NPC43211
0.9568	High Similarity	NPC223426
0.9568	High Similarity	NPC81042
0.9568	High Similarity	NPC16194
0.9568	High Similarity	NPC49344
0.9563	High Similarity	NPC86008
0.9563	High Similarity	NPC105025
0.9563	High Similarity	NPC201292
0.9563	High Similarity	NPC209296
0.9563	High Similarity	NPC58053
0.9563	High Similarity	NPC475942
0.9563	High Similarity	NPC226294
0.9563	High Similarity	NPC186807
0.9563	High Similarity	NPC195257
0.9563	High Similarity	NPC93337
0.9563	High Similarity	NPC469931
0.9563	High Similarity	NPC45638
0.956	High Similarity	NPC5778
0.956	High Similarity	NPC236934
0.9557	High Similarity	NPC88043
0.9554	High Similarity	NPC182045
0.9548	High Similarity	NPC307938
0.9548	High Similarity	NPC323593
0.9548	High Similarity	NPC261866
0.9548	High Similarity	NPC203500
0.9509	High Similarity	NPC144097
0.9509	High Similarity	NPC211532
0.9509	High Similarity	NPC470949
0.9509	High Similarity	NPC8573
0.9509	High Similarity	NPC219043
0.9509	High Similarity	NPC89127
0.9509	High Similarity	NPC14187
0.9509	High Similarity	NPC472385
0.9509	High Similarity	NPC233994
0.9509	High Similarity	NPC202908
0.9509	High Similarity	NPC292019
0.9509	High Similarity	NPC61904
0.9509	High Similarity	NPC169733
0.9509	High Similarity	NPC198324
0.9509	High Similarity	NPC65563
0.9509	High Similarity	NPC122467
0.9509	High Similarity	NPC471669
0.9503	High Similarity	NPC150767
0.9503	High Similarity	NPC218488
0.9503	High Similarity	NPC231194
0.9503	High Similarity	NPC78734
0.9503	High Similarity	NPC51326
0.9503	High Similarity	NPC72249
0.95	High Similarity	NPC45400
0.9497	High Similarity	NPC165720
0.949	High Similarity	NPC110349
0.9487	High Similarity	NPC54802
0.9487	High Similarity	NPC108831
0.9487	High Similarity	NPC78263
0.9487	High Similarity	NPC197304
0.9487	High Similarity	NPC182634
0.9487	High Similarity	NPC77672
0.9487	High Similarity	NPC133671
0.9487	High Similarity	NPC135391
0.9451	High Similarity	NPC89052
0.9451	High Similarity	NPC173837
0.9451	High Similarity	NPC139571
0.9451	High Similarity	NPC217520
0.9451	High Similarity	NPC113836
0.9451	High Similarity	NPC253521
0.9451	High Similarity	NPC168584
0.9451	High Similarity	NPC251417
0.9451	High Similarity	NPC35167
0.9451	High Similarity	NPC37668
0.9448	High Similarity	NPC264735
0.9444	High Similarity	NPC48773
0.9444	High Similarity	NPC254540
0.9444	High Similarity	NPC205076

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC277205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	952
0.2-0.3	1986
0.3-0.4	2681
0.4-0.5	1746
0.5-0.6	907
0.6-0.7	296
0.7-0.8	124
0.8-0.85	13
0.85-0.9	14
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9688	High Similarity	NPD6797	Phase 2
0.9627	High Similarity	NPD7251	Discontinued
0.9568	High Similarity	NPD4338	Clinical (unspecified phase)
0.9563	High Similarity	NPD7054	Approved
0.9503	High Similarity	NPD7472	Approved
0.9448	High Similarity	NPD7808	Phase 3
0.9383	High Similarity	NPD7074	Phase 3
0.9379	High Similarity	NPD3818	Discontinued
0.9363	High Similarity	NPD4381	Clinical (unspecified phase)
0.9136	High Similarity	NPD6167	Clinical (unspecified phase)
0.9136	High Similarity	NPD6168	Clinical (unspecified phase)
0.9136	High Similarity	NPD6166	Phase 2
0.9085	High Similarity	NPD7804	Clinical (unspecified phase)
0.8987	High Similarity	NPD1934	Approved
0.8968	High Similarity	NPD1512	Approved
0.8931	High Similarity	NPD2393	Clinical (unspecified phase)
0.8875	High Similarity	NPD3817	Phase 2
0.8839	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD2801	Approved
0.8742	High Similarity	NPD4380	Phase 2
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.8704	High Similarity	NPD3882	Suspended
0.8537	High Similarity	NPD7075	Discontinued
0.8529	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD5402	Approved
0.848	Intermediate Similarity	NPD6559	Discontinued
0.8438	Intermediate Similarity	NPD5403	Approved
0.8428	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5401	Approved
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8272	Intermediate Similarity	NPD1653	Approved
0.825	Intermediate Similarity	NPD6799	Approved
0.814	Intermediate Similarity	NPD3751	Discontinued
0.8118	Intermediate Similarity	NPD3787	Discontinued
0.8107	Intermediate Similarity	NPD5494	Approved
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8084	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2796	Approved
0.8024	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7989	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7685	Pre-registration
0.7953	Intermediate Similarity	NPD6959	Discontinued
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6232	Discontinued
0.7879	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7473	Discontinued
0.7865	Intermediate Similarity	NPD8312	Approved
0.7865	Intermediate Similarity	NPD8313	Approved
0.7861	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7199	Phase 2
0.7829	Intermediate Similarity	NPD7228	Approved
0.7791	Intermediate Similarity	NPD6190	Approved
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7266	Discontinued
0.7754	Intermediate Similarity	NPD6776	Approved
0.7754	Intermediate Similarity	NPD6778	Approved
0.7754	Intermediate Similarity	NPD6781	Approved
0.7754	Intermediate Similarity	NPD6780	Approved
0.7754	Intermediate Similarity	NPD6782	Approved
0.7754	Intermediate Similarity	NPD6779	Approved
0.7754	Intermediate Similarity	NPD6777	Approved
0.7733	Intermediate Similarity	NPD919	Approved
0.7733	Intermediate Similarity	NPD6234	Discontinued
0.773	Intermediate Similarity	NPD3750	Approved
0.773	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1240	Approved
0.7722	Intermediate Similarity	NPD943	Approved
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7584	Approved
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD3926	Phase 2
0.765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD37	Approved
0.7644	Intermediate Similarity	NPD1247	Approved
0.7632	Intermediate Similarity	NPD7435	Discontinued
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1607	Approved
0.7616	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD4965	Approved
0.7616	Intermediate Similarity	NPD4966	Approved
0.7602	Intermediate Similarity	NPD8455	Phase 2
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3749	Approved
0.7562	Intermediate Similarity	NPD1933	Approved
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7698	Approved
0.7539	Intermediate Similarity	NPD7697	Approved
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7871	Phase 2
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD3748	Approved
0.7398	Intermediate Similarity	NPD7874	Approved
0.7398	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.7363	Intermediate Similarity	NPD7240	Approved
0.736	Intermediate Similarity	NPD7801	Approved
0.736	Intermediate Similarity	NPD7783	Phase 2
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1091	Approved
0.7349	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD2532	Approved
0.7337	Intermediate Similarity	NPD2534	Approved
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2533	Approved
0.7306	Intermediate Similarity	NPD6823	Phase 2
0.7296	Intermediate Similarity	NPD7585	Approved
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7258	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD920	Approved
0.7246	Intermediate Similarity	NPD2800	Approved
0.7245	Intermediate Similarity	NPD7583	Approved
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8319	Approved
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5953	Discontinued
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7211	Intermediate Similarity	NPD4360	Phase 2
0.7211	Intermediate Similarity	NPD4363	Phase 3
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1203	Approved
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7168	Intermediate Similarity	NPD3226	Approved
0.716	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2798	Approved
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.7104	Intermediate Similarity	NPD7286	Phase 2
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7091	Intermediate Similarity	NPD6651	Approved
0.7081	Intermediate Similarity	NPD9494	Approved
0.7076	Intermediate Similarity	NPD7390	Discontinued
0.7069	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6212	Phase 3
0.7068	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6213	Phase 3
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6355	Discontinued
0.703	Intermediate Similarity	NPD5124	Phase 1
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7024	Intermediate Similarity	NPD2346	Discontinued
0.7024	Intermediate Similarity	NPD2344	Approved
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7005	Intermediate Similarity	NPD7680	Approved
0.7	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD9269	Phase 2
0.6971	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD3268	Approved
0.6936	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5711	Approved
0.6923	Remote Similarity	NPD5710	Approved
0.6918	Remote Similarity	NPD422	Phase 1
0.6912	Remote Similarity	NPD7930	Approved
0.6905	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5242	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data