NPASS Compound

Structure

CID22832 OpenBabel06191715352D 33 36 0 0 1 0 0 0 0 0999 V2000 -9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -1.7321 0.0000 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 -5.1962 0.0000 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 -6.0622 -1.5000 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 -7.7942 -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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 -0.0000 -1.0000 0.0000 C 0 0 2 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 -8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 14 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 16 2 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 23 1 0 0 0 0 9 15 1 0 0 0 0 10 31 1 0 0 0 0 11 14 2 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 26 2 0 0 0 0 14 30 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 17 8 1 6 0 0 0 17 19 1 0 0 0 0 17 33 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 6 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.12
Volume:	430.443
LogP:	1.305
LogD:	0.785
LogS:	-3.944
# Rotatable Bonds:	5
TPSA:	179.28
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	3.884
Fsp3:	0.318
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.161
MDCK Permeability:	1.7462500181864016e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.702
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	85.75164794921875%
Volume Distribution (VD):	0.788
Pgp-substrate:	11.502311706542969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.369
CYP1A2-substrate:	0.343
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.42
CYP2D6-inhibitor:	0.187
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	4.361
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.732
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.669
Carcinogencity:	0.183
Eye Corrosion:	0.003
Eye Irritation:	0.092
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC22832

Natural Product ID:	NPC22832
*Common Name:**	5-Hydroxy-2-(3-Hydroxy-4-Methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxychromen-4-One
IUPAC Name:	5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	WKUHPOMCLBLCOV-MIUGBVLSSA-N
Standard InCHI:	InChI=1S/C22H22O11/c1-30-14-3-2-9(4-11(14)24)15-7-13(26)18-12(25)5-10(6-16(18)32-15)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-7,17,19-25,27-29H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES:	COc1ccc(cc1O)c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488001
PubChem CID:	11016019
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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350171]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	Green Island, Taiwan	2002-MAY	PMID[16180809]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17268112]
NPO6365	Pachychalina alcaloidifera	Species	Niphatidae	Eukaryota	n.a.	Brazilian	n.a.	PMID[17346073]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	leaves	n.a.	n.a.	PMID[20634065]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24895781]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	flower buds	n.a.	n.a.	PMID[25987378]
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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[6893493]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[6893493]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4702	Trichosanthes rosthornii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4702	Trichosanthes rosthornii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4702	Trichosanthes rosthornii	Species	Cucurbitaceae	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]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4702	Trichosanthes rosthornii	Species	Cucurbitaceae	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]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16845	Euodia bodinieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4877	Euodia officinalis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8314	Euodia ruticarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26501	Palafoxia texana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8710	Licaria brasiliensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1068	Platytaenia lasiocarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21533	Smilax bracteata	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26387	Linum crispum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2352	Tynanthus panurensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6365	Pachychalina alcaloidifera	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25123	Scutellaria sieberi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4702	Trichosanthes rosthornii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1420	Tenebrio obscurus	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1763	Rabdosia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26056	Atroxima liberica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO832	Pseudocinchona pachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25071	Aspergillus albus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25444	Christisonia bicolor	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8830	Crotalaria orixensis	Species	Fabaceae	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	3
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	6
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	28.9	%	PMID[536565]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	27.74	%	PMID[536569]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	23.36	%	PMID[536569]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	29.79	%	PMID[536569]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[536570]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	111.5	%	PMID[536566]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	107.5	%	PMID[536566]
NPT21762	SINGLE PROTEIN	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	21830.0	nM	PMID[536568]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[536569]

☑ 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 NPC22832 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	426
0.1-0.2	1792
0.2-0.3	3996
0.3-0.4	9596
0.4-0.5	8579
0.5-0.6	4089
0.6-0.7	5044
0.7-0.8	5333
0.8-0.85	1813
0.85-0.9	1409
0.9-0.95	452
0.95-1	168

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC311830
0.9935	High Similarity	NPC222936
0.9935	High Similarity	NPC88023
0.9935	High Similarity	NPC309025
0.9935	High Similarity	NPC270335
0.9935	High Similarity	NPC191306
0.9935	High Similarity	NPC19709
0.9935	High Similarity	NPC284960
0.9935	High Similarity	NPC243930
0.9873	High Similarity	NPC229729
0.9871	High Similarity	NPC473043
0.9871	High Similarity	NPC189142
0.9871	High Similarity	NPC77660
0.981	High Similarity	NPC120099
0.981	High Similarity	NPC195257
0.981	High Similarity	NPC186807
0.981	High Similarity	NPC201292
0.981	High Similarity	NPC203050
0.981	High Similarity	NPC93337
0.981	High Similarity	NPC226294
0.981	High Similarity	NPC219904
0.981	High Similarity	NPC209296
0.981	High Similarity	NPC223747
0.981	High Similarity	NPC45638
0.981	High Similarity	NPC105025
0.981	High Similarity	NPC469931
0.981	High Similarity	NPC225434
0.981	High Similarity	NPC58053
0.981	High Similarity	NPC475942
0.9809	High Similarity	NPC236934
0.9809	High Similarity	NPC21100
0.9809	High Similarity	NPC210073
0.9809	High Similarity	NPC197285
0.9809	High Similarity	NPC115674
0.9809	High Similarity	NPC5778
0.9808	High Similarity	NPC168822
0.9806	High Similarity	NPC182045
0.9748	High Similarity	NPC231194
0.9748	High Similarity	NPC51326
0.9748	High Similarity	NPC206123
0.9747	High Similarity	NPC317489
0.9747	High Similarity	NPC146792
0.9747	High Similarity	NPC265530
0.9747	High Similarity	NPC58716
0.9747	High Similarity	NPC52550
0.9747	High Similarity	NPC84362
0.9747	High Similarity	NPC226304
0.9747	High Similarity	NPC325555
0.9747	High Similarity	NPC223424
0.9747	High Similarity	NPC45618
0.9747	High Similarity	NPC173637
0.9747	High Similarity	NPC127546
0.9745	High Similarity	NPC277205
0.9744	High Similarity	NPC300537
0.9744	High Similarity	NPC127782
0.9742	High Similarity	NPC110349
0.9688	High Similarity	NPC117260
0.9688	High Similarity	NPC172807
0.9688	High Similarity	NPC307518
0.9688	High Similarity	NPC48773
0.9688	High Similarity	NPC153755
0.9688	High Similarity	NPC235575
0.9688	High Similarity	NPC205076
0.9688	High Similarity	NPC254540
0.9688	High Similarity	NPC476405
0.9688	High Similarity	NPC211594
0.9688	High Similarity	NPC256760
0.9686	High Similarity	NPC86008
0.9686	High Similarity	NPC229687
0.9684	High Similarity	NPC145038
0.9684	High Similarity	NPC88789
0.9684	High Similarity	NPC274618
0.9684	High Similarity	NPC8856
0.9684	High Similarity	NPC113968
0.9684	High Similarity	NPC135599
0.9684	High Similarity	NPC118284
0.9684	High Similarity	NPC277174
0.9684	High Similarity	NPC179950
0.9684	High Similarity	NPC73855
0.9684	High Similarity	NPC328940
0.9684	High Similarity	NPC56077
0.9684	High Similarity	NPC253662
0.9684	High Similarity	NPC276222
0.9684	High Similarity	NPC281131
0.9684	High Similarity	NPC308404
0.9682	High Similarity	NPC29830
0.9682	High Similarity	NPC88043
0.9627	High Similarity	NPC24043
0.9627	High Similarity	NPC4390
0.9627	High Similarity	NPC101026
0.9627	High Similarity	NPC42773
0.9627	High Similarity	NPC472993
0.9627	High Similarity	NPC21666
0.9627	High Similarity	NPC45522
0.9627	High Similarity	NPC208668
0.9627	High Similarity	NPC204693
0.9627	High Similarity	NPC169977
0.9625	High Similarity	NPC44328
0.9625	High Similarity	NPC84265
0.9625	High Similarity	NPC150767
0.9625	High Similarity	NPC183357
0.9625	High Similarity	NPC21190
0.9625	High Similarity	NPC95866
0.9625	High Similarity	NPC78734
0.9625	High Similarity	NPC224462
0.9625	High Similarity	NPC105511
0.9625	High Similarity	NPC245014
0.9625	High Similarity	NPC177731
0.9625	High Similarity	NPC285197
0.9625	High Similarity	NPC22195
0.9625	High Similarity	NPC79056
0.9625	High Similarity	NPC244776
0.9625	High Similarity	NPC105095
0.9625	High Similarity	NPC282987
0.9625	High Similarity	NPC116864
0.9625	High Similarity	NPC67105
0.9623	High Similarity	NPC477502
0.9623	High Similarity	NPC45400
0.9623	High Similarity	NPC116745
0.962	High Similarity	NPC165720
0.962	High Similarity	NPC475497
0.962	High Similarity	NPC55786
0.962	High Similarity	NPC475366
0.962	High Similarity	NPC240431
0.962	High Similarity	NPC19388
0.962	High Similarity	NPC284277
0.9568	High Similarity	NPC198199
0.9568	High Similarity	NPC476472
0.9568	High Similarity	NPC473327
0.9568	High Similarity	NPC294815
0.9568	High Similarity	NPC19108
0.9568	High Similarity	NPC477848
0.9568	High Similarity	NPC220173
0.9568	High Similarity	NPC16194
0.9565	High Similarity	NPC134532
0.9565	High Similarity	NPC245452
0.9565	High Similarity	NPC203259
0.9565	High Similarity	NPC33054
0.9565	High Similarity	NPC176740
0.9565	High Similarity	NPC471748
0.9565	High Similarity	NPC26230
0.9565	High Similarity	NPC180918
0.9565	High Similarity	NPC155877
0.9565	High Similarity	NPC3583
0.9565	High Similarity	NPC259152
0.9565	High Similarity	NPC60735
0.9565	High Similarity	NPC261254
0.9565	High Similarity	NPC190003
0.9565	High Similarity	NPC175107
0.9565	High Similarity	NPC471725
0.9563	High Similarity	NPC95855
0.9563	High Similarity	NPC293629
0.9563	High Similarity	NPC170675
0.9563	High Similarity	NPC52382
0.9563	High Similarity	NPC43587
0.9563	High Similarity	NPC270578
0.9563	High Similarity	NPC472381
0.9563	High Similarity	NPC210042
0.9563	High Similarity	NPC471457
0.9563	High Similarity	NPC112755
0.9563	High Similarity	NPC472383
0.9563	High Similarity	NPC227508
0.956	High Similarity	NPC181616
0.956	High Similarity	NPC254306
0.956	High Similarity	NPC99957
0.9557	High Similarity	NPC94777
0.9548	High Similarity	NPC261866
0.9509	High Similarity	NPC233994
0.9509	High Similarity	NPC211532
0.9509	High Similarity	NPC472385
0.9509	High Similarity	NPC169733
0.9509	High Similarity	NPC198324
0.9506	High Similarity	NPC88560
0.9506	High Similarity	NPC239549
0.9506	High Similarity	NPC236191
0.9506	High Similarity	NPC172033
0.9506	High Similarity	NPC51774
0.9506	High Similarity	NPC175230
0.9503	High Similarity	NPC255157
0.9503	High Similarity	NPC44558
0.9503	High Similarity	NPC149011
0.9503	High Similarity	NPC235260
0.9503	High Similarity	NPC20505
0.9503	High Similarity	NPC471416
0.9503	High Similarity	NPC155763
0.9503	High Similarity	NPC204937
0.9503	High Similarity	NPC474434
0.9503	High Similarity	NPC34287
0.9503	High Similarity	NPC254855
0.9503	High Similarity	NPC67326
0.9503	High Similarity	NPC29958
0.9503	High Similarity	NPC259896
0.9503	High Similarity	NPC218488
0.9503	High Similarity	NPC156869
0.9503	High Similarity	NPC212748
0.9503	High Similarity	NPC136042
0.95	High Similarity	NPC92565
0.95	High Similarity	NPC160156
0.95	High Similarity	NPC93099
0.95	High Similarity	NPC275454

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 NPC22832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	929
0.2-0.3	1887
0.3-0.4	2692
0.4-0.5	1822
0.5-0.6	919
0.6-0.7	320
0.7-0.8	141
0.8-0.85	20
0.85-0.9	16
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.981	High Similarity	NPD7054	Approved
0.9748	High Similarity	NPD7472	Approved
0.9625	High Similarity	NPD7074	Phase 3
0.9565	High Similarity	NPD6797	Phase 2
0.9506	High Similarity	NPD7251	Discontinued
0.95	High Similarity	NPD3818	Discontinued
0.9448	High Similarity	NPD4338	Clinical (unspecified phase)
0.9448	High Similarity	NPD7808	Phase 3
0.9363	High Similarity	NPD4381	Clinical (unspecified phase)
0.9231	High Similarity	NPD1934	Approved
0.9136	High Similarity	NPD6167	Clinical (unspecified phase)
0.9136	High Similarity	NPD6168	Clinical (unspecified phase)
0.9136	High Similarity	NPD6166	Phase 2
0.9051	High Similarity	NPD2393	Clinical (unspecified phase)
0.9051	High Similarity	NPD2801	Approved
0.897	High Similarity	NPD7804	Clinical (unspecified phase)
0.8875	High Similarity	NPD3817	Phase 2
0.8839	High Similarity	NPD1511	Approved
0.8742	High Similarity	NPD4380	Phase 2
0.8726	High Similarity	NPD1512	Approved
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.8704	High Similarity	NPD3882	Suspended
0.8588	High Similarity	NPD6559	Discontinued
0.8424	Intermediate Similarity	NPD7075	Discontinued
0.8385	Intermediate Similarity	NPD1653	Approved
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5494	Approved
0.8314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD6801	Discontinued
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD5403	Approved
0.8198	Intermediate Similarity	NPD5844	Phase 1
0.8193	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7685	Pre-registration
0.8153	Intermediate Similarity	NPD2796	Approved
0.8137	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8098	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5401	Approved
0.8081	Intermediate Similarity	NPD7473	Discontinued
0.8059	Intermediate Similarity	NPD7199	Phase 2
0.8059	Intermediate Similarity	NPD6959	Discontinued
0.8035	Intermediate Similarity	NPD7228	Approved
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6234	Discontinued
0.7931	Intermediate Similarity	NPD3751	Discontinued
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7875	Intermediate Similarity	NPD7266	Discontinued
0.7865	Intermediate Similarity	NPD8313	Approved
0.7865	Intermediate Similarity	NPD8312	Approved
0.7861	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD37	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6599	Discontinued
0.784	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1240	Approved
0.7826	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4966	Approved
0.7824	Intermediate Similarity	NPD4967	Phase 2
0.7824	Intermediate Similarity	NPD4965	Approved
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7584	Approved
0.7785	Intermediate Similarity	NPD1933	Approved
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD3027	Phase 3
0.7736	Intermediate Similarity	NPD1607	Approved
0.7733	Intermediate Similarity	NPD919	Approved
0.773	Intermediate Similarity	NPD3750	Approved
0.7722	Intermediate Similarity	NPD943	Approved
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD230	Phase 1
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6776	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.7657	Intermediate Similarity	NPD3926	Phase 2
0.7644	Intermediate Similarity	NPD1247	Approved
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7617	Intermediate Similarity	NPD8151	Discontinued
0.7616	Intermediate Similarity	NPD7768	Phase 2
0.7602	Intermediate Similarity	NPD8455	Phase 2
0.7595	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD6190	Approved
0.7572	Intermediate Similarity	NPD3749	Approved
0.7562	Intermediate Similarity	NPD447	Suspended
0.7556	Intermediate Similarity	NPD7240	Approved
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7455	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7783	Phase 2
0.7448	Intermediate Similarity	NPD7696	Phase 3
0.7448	Intermediate Similarity	NPD7697	Approved
0.7448	Intermediate Similarity	NPD7698	Approved
0.744	Intermediate Similarity	NPD2534	Approved
0.744	Intermediate Similarity	NPD2532	Approved
0.744	Intermediate Similarity	NPD2533	Approved
0.7423	Intermediate Similarity	NPD3748	Approved
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7407	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6823	Phase 2
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD6534	Approved
0.7385	Intermediate Similarity	NPD7585	Approved
0.7385	Intermediate Similarity	NPD7701	Phase 2
0.7382	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1091	Approved
0.7353	Intermediate Similarity	NPD920	Approved
0.7349	Intermediate Similarity	NPD2800	Approved
0.7349	Intermediate Similarity	NPD6674	Discontinued
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7583	Approved
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7296	Intermediate Similarity	NPD9494	Approved
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7273	Intermediate Similarity	NPD7801	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD3226	Approved
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4908	Phase 1
0.725	Intermediate Similarity	NPD6832	Phase 2
0.7246	Intermediate Similarity	NPD1243	Approved
0.7246	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD6844	Discontinued
0.724	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7195	Intermediate Similarity	NPD6651	Approved
0.7179	Intermediate Similarity	NPD7680	Approved
0.7176	Intermediate Similarity	NPD7390	Discontinued
0.717	Intermediate Similarity	NPD1203	Approved
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7159	Intermediate Similarity	NPD5353	Approved
0.7158	Intermediate Similarity	NPD6212	Phase 3
0.7158	Intermediate Similarity	NPD6213	Phase 3
0.7158	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD8319	Approved
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2344	Approved
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7108	Intermediate Similarity	NPD2799	Discontinued
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7072	Intermediate Similarity	NPD5242	Approved
0.7069	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD3268	Approved
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD5006	Approved
0.7041	Intermediate Similarity	NPD5005	Approved
0.7037	Intermediate Similarity	NPD6841	Approved
0.7037	Intermediate Similarity	NPD6842	Approved
0.7037	Intermediate Similarity	NPD6843	Phase 3
0.7035	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD422	Phase 1
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.7012	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3225	Approved
0.6995	Remote Similarity	NPD7930	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