NPASS Compound

Structure

CID214138 OpenBabel06191716002D 24 26 0 0 0 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 2.5981 -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 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1.7321 -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 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 -1.7321 -2.0000 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 23 1 0 0 0 0 2 3 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 2 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.05
Volume:	308.853
LogP:	1.957
LogD:	1.249
LogS:	-3.541
# Rotatable Bonds:	2
TPSA:	140.59
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	2.632
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.236
MDCK Permeability:	8.455388524453156e-06
Pgp-inhibitor:	0.065
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	94.14209747314453%
Volume Distribution (VD):	0.606
Pgp-substrate:	13.812210083007812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.486
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.575
CYP2C9-substrate:	0.365
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	7.841
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.684
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.156
Skin Sensitization:	0.93
Carcinogencity:	0.056
Eye Corrosion:	0.004
Eye Irritation:	0.931
Respiratory Toxicity:	0.071

Download Data

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

Natural Product: NPC214138

Natural Product ID:	NPC214138
*Common Name:**	2-(3,4-Dihydroxyphenyl)-5,6,7-Trihydroxy-3-Methoxychromen-4-One
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-3-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	QZAXKZRZMAXPSF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O8/c1-23-16-14(22)11-10(5-9(19)12(20)13(11)21)24-15(16)6-2-3-7(17)8(18)4-6/h2-5,17-21H,1H3
SMILES:	COc1c(oc2c(c1=O)c(O)c(c(c2)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478439
PubChem CID:	5320475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002588] 3-O-methylated flavonoids

*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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO24630	Sophora exigua	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(92)80056-K]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO24630	Sophora exigua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10839220]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO25324	Phorbas amaranthus	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104518]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19327990]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20942442]
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	flower	n.a.	PMID[20942442]
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	stem	n.a.	PMID[20942442]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22372931]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO26819	Xanthium pungens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2380717]
NPO26819	Xanthium pungens	Species	Asteraceae	Eukaryota	burrs	n.a.	n.a.	PMID[2380717]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24798144]
NPO24324	Halobacterium salinarum	Species	Halobacteriaceae	Archaea	n.a.	n.a.	n.a.	PMID[24823651]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26523463]
NPO25474	Ocotea pulchella	Species	Lauraceae	Eukaryota	n.a.	stem	n.a.	PMID[27482860]
NPO25474	Ocotea pulchella	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[27482860]
NPO25474	Ocotea pulchella	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[27482860]
NPO8912	Daphne giraldii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27627130]
NPO8912	Daphne giraldii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28371676]
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29131616]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33118348]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655803]
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[436014]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26049	Salvia digitaloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25520	Uncaria laevigata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26744	Heliotropium eichwaldii	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26916	Thermopsis alpina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21594	Sporobolus cynosuroides	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26677	Garcinia pseudoguttifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25520	Uncaria laevigata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26744	Heliotropium eichwaldii	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26916	Thermopsis alpina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26457	Alpinia allughas	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26049	Salvia digitaloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26001	Carlina acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26916	Thermopsis alpina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26457	Alpinia allughas	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25093	Ericameria diffusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26312	Cirsium tanakae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25402	Kuehneromyces mutabilis	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26083	Eumorphia sericea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26049	Salvia digitaloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24653	Calonectria cylindrospora	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10241	Afrocarpus falcatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21702	Decachaeta thieleana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26483	Chrysosplenium echinus	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26744	Heliotropium eichwaldii	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20052	Flemingia chappar	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24510	Turricula parryi	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26975	Aloe vulgaris	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18359	Canella winterana	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25324	Phorbas amaranthus	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24834	Cystoseira jabukae	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26853	Baccharis magellanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8912	Daphne giraldii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23684	Narcissus obesus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26210	Eupatorium birmanicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26645	Beilschmiedia volckii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24324	Halobacterium salinarum	Species	Halobacteriaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO21594	Sporobolus cynosuroides	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26677	Garcinia pseudoguttifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22785	Nicotiana debneyi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25520	Uncaria laevigata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26115	Asterogyne martiana	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24736	Acacia pycnantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26525	Eriostemon thryptomenoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25910	Trichoderma polysporum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25474	Ocotea pulchella	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26001	Carlina acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26786	Berkheya zeyheri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26945	Crangon vulgaris	Species	Crangonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26848	Ligularia lamarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25643	Streptomyces chattanoogensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26709	Phyllanthus discoideus	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26916	Thermopsis alpina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24630	Sophora exigua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26819	Xanthium pungens	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

☑ 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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	57.54	nM	PMID[574190]

☑ 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 NPC214138 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	526
0.1-0.2	2169
0.2-0.3	5584
0.3-0.4	11476
0.4-0.5	5249
0.5-0.6	4195
0.6-0.7	5187
0.7-0.8	4710
0.8-0.85	1815
0.85-0.9	992
0.9-0.95	538
0.95-1	256

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC163524
0.9866	High Similarity	NPC287979
0.9866	High Similarity	NPC305663
0.9866	High Similarity	NPC176665
0.98	High Similarity	NPC261004
0.98	High Similarity	NPC22472
0.98	High Similarity	NPC176300
0.98	High Similarity	NPC105242
0.98	High Similarity	NPC288669
0.98	High Similarity	NPC7846
0.98	High Similarity	NPC18607
0.98	High Similarity	NPC25495
0.98	High Similarity	NPC19687
0.98	High Similarity	NPC9609
0.98	High Similarity	NPC115798
0.98	High Similarity	NPC18772
0.98	High Similarity	NPC143828
0.98	High Similarity	NPC191459
0.98	High Similarity	NPC4481
0.98	High Similarity	NPC152166
0.98	High Similarity	NPC204854
0.98	High Similarity	NPC130894
0.98	High Similarity	NPC253634
0.98	High Similarity	NPC300943
0.9799	High Similarity	NPC266960
0.9799	High Similarity	NPC43243
0.9799	High Similarity	NPC98661
0.9799	High Similarity	NPC247017
0.9799	High Similarity	NPC245546
0.9733	High Similarity	NPC472438
0.9733	High Similarity	NPC235215
0.9733	High Similarity	NPC78302
0.9733	High Similarity	NPC75215
0.9733	High Similarity	NPC203891
0.9733	High Similarity	NPC227192
0.9733	High Similarity	NPC189179
0.9733	High Similarity	NPC7973
0.9733	High Similarity	NPC29841
0.9733	High Similarity	NPC224137
0.9733	High Similarity	NPC101830
0.9733	High Similarity	NPC93376
0.9733	High Similarity	NPC110070
0.9732	High Similarity	NPC201451
0.9732	High Similarity	NPC26227
0.9732	High Similarity	NPC44079
0.9728	High Similarity	NPC77858
0.9728	High Similarity	NPC188871
0.9728	High Similarity	NPC286342
0.9728	High Similarity	NPC149127
0.9728	High Similarity	NPC184136
0.9669	High Similarity	NPC193842
0.9667	High Similarity	NPC55619
0.9667	High Similarity	NPC178854
0.9667	High Similarity	NPC100916
0.9667	High Similarity	NPC49824
0.9667	High Similarity	NPC200388
0.9667	High Similarity	NPC474520
0.9667	High Similarity	NPC268161
0.9667	High Similarity	NPC292107
0.9662	High Similarity	NPC260895
0.966	High Similarity	NPC87125
0.966	High Similarity	NPC270465
0.966	High Similarity	NPC195351
0.96	High Similarity	NPC196439
0.96	High Similarity	NPC138360
0.96	High Similarity	NPC50715
0.96	High Similarity	NPC189960
0.96	High Similarity	NPC92659
0.96	High Similarity	NPC4455
0.96	High Similarity	NPC2476
0.96	High Similarity	NPC280339
0.96	High Similarity	NPC167815
0.96	High Similarity	NPC201136
0.96	High Similarity	NPC163780
0.96	High Similarity	NPC128863
0.96	High Similarity	NPC183597
0.96	High Similarity	NPC32557
0.96	High Similarity	NPC227325
0.96	High Similarity	NPC146165
0.9597	High Similarity	NPC198826
0.9597	High Similarity	NPC301323
0.9597	High Similarity	NPC100887
0.9597	High Similarity	NPC57030
0.9597	High Similarity	NPC212678
0.9597	High Similarity	NPC188203
0.9597	High Similarity	NPC239128
0.9597	High Similarity	NPC131624
0.9597	High Similarity	NPC293183
0.9597	High Similarity	NPC25270
0.9597	High Similarity	NPC279989
0.9597	High Similarity	NPC187498
0.9597	High Similarity	NPC27208
0.9597	High Similarity	NPC256283
0.9597	High Similarity	NPC83508
0.9597	High Similarity	NPC162313
0.9597	High Similarity	NPC241498
0.9597	High Similarity	NPC222830
0.9597	High Similarity	NPC123886
0.9597	High Similarity	NPC71334
0.9597	High Similarity	NPC156222
0.9597	High Similarity	NPC301123
0.9597	High Similarity	NPC275836
0.9597	High Similarity	NPC142540
0.9597	High Similarity	NPC275722
0.9597	High Similarity	NPC82325
0.9597	High Similarity	NPC120163
0.9536	High Similarity	NPC265511
0.9533	High Similarity	NPC86485
0.9533	High Similarity	NPC246204
0.9533	High Similarity	NPC274327
0.9533	High Similarity	NPC255350
0.9533	High Similarity	NPC236223
0.9533	High Similarity	NPC47781
0.9533	High Similarity	NPC250822
0.9533	High Similarity	NPC58382
0.9533	High Similarity	NPC176775
0.9533	High Similarity	NPC270620
0.9533	High Similarity	NPC78326
0.9533	High Similarity	NPC162351
0.9533	High Similarity	NPC179126
0.9533	High Similarity	NPC183878
0.9533	High Similarity	NPC145379
0.9533	High Similarity	NPC276409
0.9533	High Similarity	NPC69394
0.9533	High Similarity	NPC22519
0.9533	High Similarity	NPC231018
0.9533	High Similarity	NPC75279
0.9533	High Similarity	NPC160951
0.953	High Similarity	NPC252933
0.953	High Similarity	NPC125062
0.953	High Similarity	NPC133953
0.953	High Similarity	NPC50403
0.953	High Similarity	NPC200740
0.953	High Similarity	NPC54394
0.953	High Similarity	NPC225731
0.953	High Similarity	NPC28274
0.9524	High Similarity	NPC108406
0.9524	High Similarity	NPC275772
0.9524	High Similarity	NPC239312
0.9524	High Similarity	NPC130230
0.9477	High Similarity	NPC246478
0.947	High Similarity	NPC80534
0.947	High Similarity	NPC20830
0.947	High Similarity	NPC56786
0.947	High Similarity	NPC208197
0.947	High Similarity	NPC133392
0.947	High Similarity	NPC256612
0.947	High Similarity	NPC213622
0.9467	High Similarity	NPC134677
0.9467	High Similarity	NPC55205
0.9463	High Similarity	NPC306821
0.9463	High Similarity	NPC62042
0.9459	High Similarity	NPC12367
0.9459	High Similarity	NPC118726
0.9456	High Similarity	NPC169749
0.9456	High Similarity	NPC20791
0.9456	High Similarity	NPC179271
0.9419	High Similarity	NPC470459
0.9412	High Similarity	NPC195832
0.94	High Similarity	NPC76376
0.94	High Similarity	NPC208043
0.94	High Similarity	NPC236769
0.94	High Similarity	NPC226973
0.9396	High Similarity	NPC159103
0.9396	High Similarity	NPC137062
0.9396	High Similarity	NPC183950
0.9396	High Similarity	NPC296197
0.9396	High Similarity	NPC216318
0.9396	High Similarity	NPC52005
0.9396	High Similarity	NPC287101
0.9396	High Similarity	NPC259713
0.9396	High Similarity	NPC223579
0.9396	High Similarity	NPC17286
0.9392	High Similarity	NPC51443
0.9392	High Similarity	NPC74881
0.9363	High Similarity	NPC76482
0.9359	High Similarity	NPC470457
0.9351	High Similarity	NPC263449
0.9346	High Similarity	NPC470402
0.9346	High Similarity	NPC174908
0.9342	High Similarity	NPC2928
0.9338	High Similarity	NPC199100
0.9338	High Similarity	NPC60972
0.9338	High Similarity	NPC63187
0.9338	High Similarity	NPC180234
0.9338	High Similarity	NPC120537
0.9338	High Similarity	NPC39732
0.9338	High Similarity	NPC37684
0.9338	High Similarity	NPC157784
0.9333	High Similarity	NPC201547
0.9333	High Similarity	NPC219330
0.9333	High Similarity	NPC50728
0.9333	High Similarity	NPC10467
0.9333	High Similarity	NPC45873
0.9333	High Similarity	NPC259058
0.9333	High Similarity	NPC166753
0.9329	High Similarity	NPC276930
0.9329	High Similarity	NPC120464
0.9329	High Similarity	NPC119059
0.932	High Similarity	NPC279121

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 NPC214138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	479
0.1-0.2	1044
0.2-0.3	1952
0.3-0.4	2685
0.4-0.5	1607
0.5-0.6	935
0.6-0.7	301
0.7-0.8	96
0.8-0.85	32
0.85-0.9	11
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9533	High Similarity	NPD2801	Approved
0.9456	High Similarity	NPD1512	Approved
0.932	High Similarity	NPD1511	Approved
0.9156	High Similarity	NPD3882	Suspended
0.9091	High Similarity	NPD3817	Phase 2
0.9085	High Similarity	NPD1934	Approved
0.9026	High Similarity	NPD2393	Clinical (unspecified phase)
0.8957	High Similarity	NPD4338	Clinical (unspecified phase)
0.8875	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD6168	Clinical (unspecified phase)
0.8875	High Similarity	NPD6167	Clinical (unspecified phase)
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8834	High Similarity	NPD6797	Phase 2
0.878	High Similarity	NPD7251	Discontinued
0.865	High Similarity	NPD3818	Discontinued
0.8614	High Similarity	NPD7808	Phase 3
0.8608	High Similarity	NPD5402	Approved
0.8598	High Similarity	NPD7054	Approved
0.8545	High Similarity	NPD7472	Approved
0.85	High Similarity	NPD7075	Discontinued
0.8442	Intermediate Similarity	NPD6799	Approved
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD1247	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5494	Approved
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD943	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8166	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5403	Approved
0.8153	Intermediate Similarity	NPD5401	Approved
0.8146	Intermediate Similarity	NPD1607	Approved
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1465	Phase 2
0.8086	Intermediate Similarity	NPD7819	Suspended
0.8039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD919	Approved
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD3750	Approved
0.7871	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6190	Approved
0.7836	Intermediate Similarity	NPD5844	Phase 1
0.7834	Intermediate Similarity	NPD2800	Approved
0.78	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7727	Intermediate Similarity	NPD447	Suspended
0.7725	Intermediate Similarity	NPD3749	Approved
0.7701	Intermediate Similarity	NPD6559	Discontinued
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7622	Intermediate Similarity	NPD3226	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD920	Approved
0.7602	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2344	Approved
0.7593	Intermediate Similarity	NPD2534	Approved
0.7593	Intermediate Similarity	NPD2532	Approved
0.7593	Intermediate Similarity	NPD2533	Approved
0.758	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD1653	Approved
0.756	Intermediate Similarity	NPD7768	Phase 2
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7452	Intermediate Similarity	NPD6651	Approved
0.7451	Intermediate Similarity	NPD9494	Approved
0.7443	Intermediate Similarity	NPD5953	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6100	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD2309	Approved
0.7389	Intermediate Similarity	NPD1933	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7372	Intermediate Similarity	NPD6233	Phase 2
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD9269	Phase 2
0.7346	Intermediate Similarity	NPD4628	Phase 3
0.733	Intermediate Similarity	NPD7286	Phase 2
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2403	Approved
0.7237	Intermediate Similarity	NPD9717	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD4908	Phase 1
0.7176	Intermediate Similarity	NPD37	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7159	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1608	Approved
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7097	Intermediate Similarity	NPD2797	Approved
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9268	Approved
0.7079	Intermediate Similarity	NPD7228	Approved
0.7073	Intermediate Similarity	NPD2654	Approved
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD4363	Phase 3
0.7045	Intermediate Similarity	NPD5710	Approved
0.7045	Intermediate Similarity	NPD5711	Approved
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7697	Approved
0.7031	Intermediate Similarity	NPD7698	Approved
0.7013	Intermediate Similarity	NPD1481	Phase 2
0.7006	Intermediate Similarity	NPD2861	Phase 2
0.7006	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD3018	Phase 2
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6994	Remote Similarity	NPD4288	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1470	Approved
0.6987	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD3267	Approved
0.6974	Remote Similarity	NPD7701	Phase 2
0.6968	Remote Similarity	NPD6534	Approved
0.6968	Remote Similarity	NPD6535	Approved
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7229	Phase 3
0.6948	Remote Similarity	NPD1201	Approved
0.6948	Remote Similarity	NPD1535	Discovery
0.6931	Remote Similarity	NPD4361	Phase 2
0.6931	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD7584	Approved
0.6919	Remote Similarity	NPD6386	Approved
0.6919	Remote Similarity	NPD6385	Approved
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4625	Phase 3
0.6918	Remote Similarity	NPD7095	Approved
0.6908	Remote Similarity	NPD9545	Approved
0.6905	Remote Similarity	NPD4357	Discontinued

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