NPASS Compound

Structure

CID297987 OpenBabel06191716102D 43 47 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 2 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 0.8660 -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 1 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 5.1962 -2.0000 0.0000 C 0 0 2 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 -0.0000 -3.0000 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 5.1962 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 7.7942 -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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 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 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 13 2 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 9 24 1 0 0 0 0 10 30 1 0 0 0 0 11 39 1 0 0 0 0 12 16 2 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 40 1 0 0 0 0 14 7 1 1 0 0 0 14 17 1 0 0 0 0 14 41 1 0 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 15 42 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 32 1 6 0 0 0 18 21 1 0 0 0 0 18 33 1 6 0 0 0 19 25 1 0 0 0 0 19 34 2 0 0 0 0 20 22 1 0 0 0 0 20 35 1 1 0 0 0 21 23 1 0 0 0 0 21 36 1 1 0 0 0 22 26 1 0 0 0 0 22 37 1 6 0 0 0 23 27 1 0 0 0 0 23 38 1 6 0 0 0 24 25 2 0 0 0 0 24 40 1 0 0 0 0 25 43 1 0 0 0 0 26 39 1 1 0 0 0 26 41 1 0 0 0 0 27 42 1 0 0 0 0 27 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.15
Volume:	552.318
LogP:	-0.566
LogD:	-0.42
LogS:	-3.632
# Rotatable Bonds:	7
TPSA:	269.43
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.13
Synthetic Accessibility Score:	4.663
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.491
MDCK Permeability:	3.717267463798635e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.824
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	77.64995574951172%
Volume Distribution (VD):	0.657
Pgp-substrate:	15.454928398132324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.13
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.368
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.707
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.15
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC297987

Natural Product ID:	NPC297987
*Common Name:**	Kaempferol 3,7-Di-O-Beta-D-Glucopyranoside
IUPAC Name:	5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
Synonyms:
Standard InCHIKey:	XFFQVRFGLSBFON-DEFKTLOSSA-N
Standard InCHI:	InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-11-5-12(31)16-13(6-11)40-24(9-1-3-10(30)4-2-9)25(19(16)34)43-27-23(38)21(36)18(33)15(8-29)42-27/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
SMILES:	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)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:	CHEMBL2206209
PubChem CID:	6325460
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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[10978212]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO16949	Aster oharai	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193011]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO30524	Equisetum debile	Species	Equisetaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666861]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21466157]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524113]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO4394	Pelargonium graveolens	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23027699]
NPO3860.1	Allium victorialis	Under-species	n.a.	n.a.	Leaves	Taeback, GangWon province, Korea	2011-Jan	PMID[23149227]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[26434122]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14125	Corydalis ochotensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17655	Heliotropium amplexicaule	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10437	Periploca calophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO4394	Pelargonium graveolens	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17655	Heliotropium amplexicaule	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14125	Corydalis ochotensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10437	Periploca calophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4394	Pelargonium graveolens	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4394	Pelargonium graveolens	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17655	Heliotropium amplexicaule	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16735	Sophora tometosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16949	Aster oharai	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5425	Polygala nyikensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8527	Holboellia fargesi	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10437	Periploca calophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14880	Ephydatia syriaca	Species	Spongillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4394	Pelargonium graveolens	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10340	Crepis rubra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18109	Thorecta marginalis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8173	Lupinus multiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11568	Dendroctonus ponderosae	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17245	Prumnopitys ferruginoides	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6958	Pseudaegle trifoliata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2383	Mimosa acacioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14125	Corydalis ochotensis	Species	Papaveraceae	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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	106.0	%	PMID[468884]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	28890.0	nM	PMID[468884]

☑ 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 NPC297987 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	463
0.1-0.2	1791
0.2-0.3	4346
0.3-0.4	10009
0.4-0.5	8386
0.5-0.6	4748
0.6-0.7	5902
0.7-0.8	5160
0.8-0.85	1042
0.85-0.9	384
0.9-0.95	379
0.95-1	87

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135846
1.0	High Similarity	NPC64305
1.0	High Similarity	NPC170052
0.9934	High Similarity	NPC471079
0.9934	High Similarity	NPC304741
0.9934	High Similarity	NPC136761
0.9934	High Similarity	NPC470405
0.9869	High Similarity	NPC276377
0.9869	High Similarity	NPC215710
0.9869	High Similarity	NPC473438
0.9869	High Similarity	NPC246943
0.9869	High Similarity	NPC265885
0.9869	High Similarity	NPC249281
0.9869	High Similarity	NPC163242
0.9869	High Similarity	NPC173582
0.9869	High Similarity	NPC476215
0.9869	High Similarity	NPC116458
0.9869	High Similarity	NPC181465
0.9869	High Similarity	NPC139320
0.9869	High Similarity	NPC253788
0.9806	High Similarity	NPC289667
0.9806	High Similarity	NPC76831
0.9806	High Similarity	NPC292929
0.9805	High Similarity	NPC240306
0.9804	High Similarity	NPC187379
0.9803	High Similarity	NPC135391
0.9803	High Similarity	NPC77672
0.9803	High Similarity	NPC133671
0.9803	High Similarity	NPC54802
0.9803	High Similarity	NPC78263
0.9803	High Similarity	NPC197304
0.9744	High Similarity	NPC11432
0.9744	High Similarity	NPC476470
0.9744	High Similarity	NPC64425
0.9744	High Similarity	NPC189564
0.9744	High Similarity	NPC221342
0.9744	High Similarity	NPC256188
0.9744	High Similarity	NPC142142
0.9744	High Similarity	NPC203145
0.9744	High Similarity	NPC477613
0.9744	High Similarity	NPC186816
0.9744	High Similarity	NPC32641
0.9744	High Similarity	NPC12013
0.974	High Similarity	NPC470125
0.9739	High Similarity	NPC320283
0.9739	High Similarity	NPC41121
0.9739	High Similarity	NPC472459
0.9739	High Similarity	NPC111929
0.9737	High Similarity	NPC323593
0.9737	High Similarity	NPC203500
0.9737	High Similarity	NPC307938
0.9679	High Similarity	NPC135358
0.9679	High Similarity	NPC287889
0.9675	High Similarity	NPC153342
0.9673	High Similarity	NPC182634
0.9673	High Similarity	NPC65003
0.9673	High Similarity	NPC473512
0.9673	High Similarity	NPC44931
0.9673	High Similarity	NPC108831
0.9673	High Similarity	NPC129827
0.9613	High Similarity	NPC129217
0.9613	High Similarity	NPC282169
0.9613	High Similarity	NPC224530
0.9613	High Similarity	NPC85707
0.9613	High Similarity	NPC48093
0.9613	High Similarity	NPC259957
0.9613	High Similarity	NPC216496
0.9613	High Similarity	NPC159579
0.961	High Similarity	NPC22062
0.961	High Similarity	NPC138811
0.961	High Similarity	NPC473634
0.9605	High Similarity	NPC143851
0.9605	High Similarity	NPC83283
0.9605	High Similarity	NPC210003
0.9605	High Similarity	NPC39360
0.9605	High Similarity	NPC29763
0.956	High Similarity	NPC209550
0.956	High Similarity	NPC254855
0.956	High Similarity	NPC29958
0.956	High Similarity	NPC156869
0.956	High Similarity	NPC136042
0.956	High Similarity	NPC277532
0.956	High Similarity	NPC255157
0.956	High Similarity	NPC175429
0.956	High Similarity	NPC164704
0.956	High Similarity	NPC138990
0.956	High Similarity	NPC470712
0.956	High Similarity	NPC259896
0.956	High Similarity	NPC67326
0.9554	High Similarity	NPC85751
0.9554	High Similarity	NPC19240
0.9554	High Similarity	NPC129264
0.9554	High Similarity	NPC205824
0.9551	High Similarity	NPC298171
0.9551	High Similarity	NPC244875
0.9551	High Similarity	NPC475382
0.9551	High Similarity	NPC150164
0.9551	High Similarity	NPC27942
0.9548	High Similarity	NPC473623
0.9545	High Similarity	NPC288084
0.9542	High Similarity	NPC39351
0.9542	High Similarity	NPC26195
0.9542	High Similarity	NPC72649
0.9542	High Similarity	NPC95090
0.9542	High Similarity	NPC97052
0.9542	High Similarity	NPC169248
0.9542	High Similarity	NPC27408
0.95	High Similarity	NPC470716
0.95	High Similarity	NPC60735
0.95	High Similarity	NPC470714
0.95	High Similarity	NPC474522
0.95	High Similarity	NPC33054
0.95	High Similarity	NPC176740
0.95	High Similarity	NPC203259
0.95	High Similarity	NPC471748
0.95	High Similarity	NPC134532
0.95	High Similarity	NPC26230
0.95	High Similarity	NPC470715
0.95	High Similarity	NPC471725
0.95	High Similarity	NPC155877
0.9497	High Similarity	NPC5319
0.949	High Similarity	NPC121703
0.949	High Similarity	NPC66087
0.949	High Similarity	NPC311850
0.949	High Similarity	NPC179198
0.949	High Similarity	NPC80068
0.949	High Similarity	NPC473644
0.949	High Similarity	NPC278419
0.9487	High Similarity	NPC303913
0.9487	High Similarity	NPC101636
0.9487	High Similarity	NPC47923
0.9484	High Similarity	NPC104677
0.9481	High Similarity	NPC206378
0.9481	High Similarity	NPC295613
0.9481	High Similarity	NPC170475
0.9481	High Similarity	NPC473657
0.9437	High Similarity	NPC95866
0.9437	High Similarity	NPC285197
0.9437	High Similarity	NPC67105
0.9434	High Similarity	NPC275454
0.943	High Similarity	NPC72016
0.943	High Similarity	NPC139060
0.9427	High Similarity	NPC259834
0.9427	High Similarity	NPC131745
0.9427	High Similarity	NPC44947
0.9423	High Similarity	NPC246469
0.9423	High Similarity	NPC142860
0.9423	High Similarity	NPC97285
0.9423	High Similarity	NPC271270
0.9419	High Similarity	NPC122809
0.9419	High Similarity	NPC60966
0.9419	High Similarity	NPC156457
0.9419	High Similarity	NPC6985
0.9419	High Similarity	NPC161749
0.9419	High Similarity	NPC197896
0.9419	High Similarity	NPC258035
0.9419	High Similarity	NPC313163
0.9412	High Similarity	NPC88484
0.9412	High Similarity	NPC259767
0.9412	High Similarity	NPC121001
0.9412	High Similarity	NPC259182
0.9383	High Similarity	NPC19108
0.9383	High Similarity	NPC476472
0.9383	High Similarity	NPC294815
0.9383	High Similarity	NPC253685
0.9383	High Similarity	NPC473327
0.9383	High Similarity	NPC16194
0.9383	High Similarity	NPC220173
0.9375	High Similarity	NPC227508
0.9371	High Similarity	NPC308404
0.9371	High Similarity	NPC253662
0.9371	High Similarity	NPC145038
0.9371	High Similarity	NPC262222
0.9371	High Similarity	NPC8856
0.9371	High Similarity	NPC179950
0.9371	High Similarity	NPC298666
0.9371	High Similarity	NPC68592
0.9371	High Similarity	NPC276222
0.9371	High Similarity	NPC118284
0.9371	High Similarity	NPC274618
0.9371	High Similarity	NPC88789
0.9371	High Similarity	NPC56077
0.9371	High Similarity	NPC281131
0.9367	High Similarity	NPC124155
0.9367	High Similarity	NPC183672
0.9367	High Similarity	NPC257566
0.9363	High Similarity	NPC210961
0.9363	High Similarity	NPC472994
0.9363	High Similarity	NPC477629
0.9363	High Similarity	NPC477628
0.9363	High Similarity	NPC270675
0.9363	High Similarity	NPC195685
0.9359	High Similarity	NPC73511
0.9359	High Similarity	NPC308265
0.9355	High Similarity	NPC261866
0.9351	High Similarity	NPC106625
0.9325	High Similarity	NPC219043
0.9325	High Similarity	NPC292019
0.9325	High Similarity	NPC14187
0.9325	High Similarity	NPC8573

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 NPC297987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	926
0.2-0.3	1922
0.3-0.4	2801
0.4-0.5	1867
0.5-0.6	853
0.6-0.7	244
0.7-0.8	105
0.8-0.85	15
0.85-0.9	5
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD6797	Phase 2
0.9497	High Similarity	NPD7804	Clinical (unspecified phase)
0.9441	High Similarity	NPD7251	Discontinued
0.9419	High Similarity	NPD4381	Clinical (unspecified phase)
0.9383	High Similarity	NPD7808	Phase 3
0.9198	High Similarity	NPD7472	Approved
0.9136	High Similarity	NPD7054	Approved
0.903	High Similarity	NPD4338	Clinical (unspecified phase)
0.8963	High Similarity	NPD7074	Phase 3
0.879	High Similarity	NPD4380	Phase 2
0.8727	High Similarity	NPD3818	Discontinued
0.872	High Similarity	NPD6168	Clinical (unspecified phase)
0.872	High Similarity	NPD6167	Clinical (unspecified phase)
0.872	High Similarity	NPD6166	Phase 2
0.8718	High Similarity	NPD5403	Approved
0.8696	High Similarity	NPD7075	Discontinued
0.8679	High Similarity	NPD6801	Discontinued
0.859	High Similarity	NPD5401	Approved
0.8526	High Similarity	NPD6799	Approved
0.8509	High Similarity	NPD7096	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD5402	Approved
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1934	Approved
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8302	Intermediate Similarity	NPD1512	Approved
0.8282	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8176	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD2801	Approved
0.816	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2796	Approved
0.8072	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3751	Discontinued
0.8047	Intermediate Similarity	NPD3787	Discontinued
0.8	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7952	Intermediate Similarity	NPD8455	Phase 2
0.7871	Intermediate Similarity	NPD1240	Approved
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD1607	Approved
0.7764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7725	Intermediate Similarity	NPD7584	Approved
0.7719	Intermediate Similarity	NPD5494	Approved
0.7717	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6776	Approved
0.7688	Intermediate Similarity	NPD6782	Approved
0.7688	Intermediate Similarity	NPD6781	Approved
0.7688	Intermediate Similarity	NPD6778	Approved
0.7688	Intermediate Similarity	NPD6777	Approved
0.7688	Intermediate Similarity	NPD6779	Approved
0.7688	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD7435	Discontinued
0.7651	Intermediate Similarity	NPD1653	Approved
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7602	Intermediate Similarity	NPD3749	Approved
0.7566	Intermediate Similarity	NPD7698	Approved
0.7566	Intermediate Similarity	NPD7696	Phase 3
0.7566	Intermediate Similarity	NPD7697	Approved
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD7768	Phase 2
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7701	Phase 2
0.75	Intermediate Similarity	NPD1091	Approved
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7228	Approved
0.7453	Intermediate Similarity	NPD3748	Approved
0.7443	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7429	Intermediate Similarity	NPD6232	Discontinued
0.7423	Intermediate Similarity	NPD7874	Approved
0.7423	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6534	Approved
0.7419	Intermediate Similarity	NPD6535	Approved
0.7405	Intermediate Similarity	NPD6798	Discontinued
0.7401	Intermediate Similarity	NPD7473	Discontinued
0.7394	Intermediate Similarity	NPD7699	Phase 2
0.7394	Intermediate Similarity	NPD7700	Phase 2
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1933	Approved
0.7371	Intermediate Similarity	NPD7199	Phase 2
0.7358	Intermediate Similarity	NPD6233	Phase 2
0.7356	Intermediate Similarity	NPD919	Approved
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7344	Intermediate Similarity	NPD8319	Approved
0.7344	Intermediate Similarity	NPD8320	Phase 1
0.732	Intermediate Similarity	NPD7585	Approved
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1203	Approved
0.7296	Intermediate Similarity	NPD7801	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7278	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD2800	Approved
0.7268	Intermediate Similarity	NPD7583	Approved
0.7262	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.7253	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7228	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7204	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7240	Approved
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7191	Intermediate Similarity	NPD3926	Phase 2
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.717	Intermediate Similarity	NPD4908	Phase 1
0.7169	Intermediate Similarity	NPD1243	Approved
0.7168	Intermediate Similarity	NPD37	Approved
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD2533	Approved
0.716	Intermediate Similarity	NPD2532	Approved
0.716	Intermediate Similarity	NPD2534	Approved
0.7159	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7134	Intermediate Similarity	NPD3225	Approved
0.7101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD943	Approved
0.7097	Intermediate Similarity	NPD8150	Discontinued
0.7081	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4340	Discontinued
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7051	Intermediate Similarity	NPD422	Phase 1
0.7048	Intermediate Similarity	NPD2344	Approved
0.7037	Intermediate Similarity	NPD4062	Phase 3
0.703	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD7390	Discontinued
0.7	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6212	Phase 3
0.7	Intermediate Similarity	NPD6213	Phase 3
0.6994	Remote Similarity	NPD3226	Approved
0.6988	Remote Similarity	NPD6099	Approved
0.6988	Remote Similarity	NPD6100	Approved
0.6982	Remote Similarity	NPD3887	Approved
0.6982	Remote Similarity	NPD2354	Approved
0.6981	Remote Similarity	NPD2797	Approved
0.6971	Remote Similarity	NPD6844	Discontinued
0.697	Remote Similarity	NPD7097	Phase 1
0.6951	Remote Similarity	NPD230	Phase 1
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3027	Phase 3
0.6897	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4288	Approved
0.6882	Remote Similarity	NPD2309	Approved
0.6869	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2403	Approved
0.6864	Remote Similarity	NPD2654	Approved
0.686	Remote Similarity	NPD4662	Approved
0.686	Remote Similarity	NPD4661	Approved
0.6848	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD447	Suspended
0.6845	Remote Similarity	NPD2346	Discontinued
0.6839	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4361	Phase 2
0.6826	Remote Similarity	NPD4308	Phase 3

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