NPASS Compound

Structure

CID218161 OpenBabel06191716012D 54 59 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 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 4.5000 0.0000 C 0 0 0 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 1.7321 3.0000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 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 0.8660 -1.5000 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 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 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 0.8660 5.5000 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 -3.4641 1.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -2.5981 -0.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 1 20 2 0 0 0 0 2 10 2 0 0 0 0 2 20 1 0 0 0 0 3 11 1 0 0 0 0 3 21 2 0 0 0 0 4 12 2 0 0 0 0 4 21 1 0 0 0 0 5 15 2 0 0 0 0 5 20 1 0 0 0 0 6 16 2 0 0 0 0 6 21 1 0 0 0 0 7 13 1 0 0 0 0 7 22 2 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 23 2 0 0 0 0 10 23 1 0 0 0 0 11 24 2 0 0 0 0 12 24 1 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 26 2 0 0 0 0 17 27 1 0 0 0 0 18 26 1 0 0 0 0 18 28 2 0 0 0 0 19 50 1 0 0 0 0 22 36 1 0 0 0 0 23 40 1 0 0 0 0 24 41 1 0 0 0 0 25 42 1 0 0 0 0 26 43 1 0 0 0 0 27 32 2 0 0 0 0 27 44 1 0 0 0 0 28 32 1 0 0 0 0 28 51 1 0 0 0 0 29 19 1 1 0 0 0 29 33 1 0 0 0 0 29 52 1 0 0 0 0 30 45 2 0 0 0 0 30 50 1 0 0 0 0 31 46 2 0 0 0 0 31 53 1 0 0 0 0 32 34 1 0 0 0 0 33 35 1 0 0 0 0 33 47 1 6 0 0 0 34 37 1 0 0 0 0 34 48 2 0 0 0 0 35 38 1 0 0 0 0 35 49 1 1 0 0 0 36 37 2 0 0 0 0 36 51 1 0 0 0 0 37 54 1 0 0 0 0 38 39 1 0 0 0 0 38 53 1 6 0 0 0 39 52 1 0 0 0 0 39 54 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	740.17
Volume:	716.158
LogP:	4.398
LogD:	2.772
LogS:	-4.155
# Rotatable Bonds:	12
TPSA:	242.88
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.08
Synthetic Accessibility Score:	4.507
Fsp3:	0.154
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:	-5.997
MDCK Permeability:	2.257762389490381e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.22
Human Intestinal Absorption (HIA):	0.157
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	101.37943267822266%
Volume Distribution (VD):	0.549
Pgp-substrate:	1.001007318496704%

ADMET: Metabolism

CYP1A2-inhibitor:	0.593
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.87
CYP2D6-substrate:	0.365
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	5.499
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.679
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.961
Carcinogencity:	0.163
Eye Corrosion:	0.003
Eye Irritation:	0.681
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC218161

Natural Product ID:	NPC218161
*Common Name:**	Kaempferol-3-O-(2'',6''-Di-E-P-Coumaroyl)-Beta-Glucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	YXXQUJGFZPLXJV-AIBWQOBZSA-N
Standard InCHI:	InChI=1S/C39H32O15/c40-23-9-1-20(2-10-23)5-15-30(45)50-19-29-33(47)35(49)38(53-31(46)16-6-21-3-11-24(41)12-4-21)39(52-29)54-37-34(48)32-27(44)17-26(43)18-28(32)51-36(37)22-7-13-25(42)14-8-22/h1-18,29,33,35,38-44,47,49H,19H2/b15-5+,16-6+/t29-,33-,35+,38-,39+/m1/s1
SMILES:	O=C(OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3628129
PubChem CID:	10439991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075766]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17870137]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[18239317]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[18239317]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18462007]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21417376]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	Urup Island (4557,9 N; 15044,9 E; depth 66 m)	2008-AUG	PMID[21848268]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848268]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4955234]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	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
Ki	5

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	8790.2	nM	PMID[469959]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	344.2	nM	PMID[469959]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	10000.0	nM	PMID[469959]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	4.7	nM	PMID[469959]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	408.9	nM	PMID[469959]

☑ 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 NPC218161 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	422
0.1-0.2	1760
0.2-0.3	4244
0.3-0.4	9454
0.4-0.5	8826
0.5-0.6	4714
0.6-0.7	5760
0.7-0.8	5211
0.8-0.85	1329
0.85-0.9	544
0.9-0.95	347
0.95-1	86

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280642
1.0	High Similarity	NPC96605
0.9938	High Similarity	NPC11847
0.9938	High Similarity	NPC101399
0.9938	High Similarity	NPC217822
0.9938	High Similarity	NPC221288
0.9875	High Similarity	NPC469344
0.9875	High Similarity	NPC188815
0.9811	High Similarity	NPC473278
0.9811	High Similarity	NPC89809
0.9811	High Similarity	NPC260504
0.9755	High Similarity	NPC231787
0.9752	High Similarity	NPC92815
0.9752	High Similarity	NPC164704
0.9752	High Similarity	NPC470712
0.9748	High Similarity	NPC129264
0.9748	High Similarity	NPC85751
0.9748	High Similarity	NPC19240
0.9748	High Similarity	NPC205824
0.9691	High Similarity	NPC474522
0.9691	High Similarity	NPC470715
0.9691	High Similarity	NPC470716
0.9691	High Similarity	NPC470714
0.9686	High Similarity	NPC80068
0.9625	High Similarity	NPC139060
0.956	High Similarity	NPC477628
0.956	High Similarity	NPC270675
0.956	High Similarity	NPC477629
0.956	High Similarity	NPC470125
0.956	High Similarity	NPC472994
0.956	High Similarity	NPC195685
0.956	High Similarity	NPC210961
0.9444	High Similarity	NPC64425
0.9437	High Similarity	NPC216496
0.9437	High Similarity	NPC85707
0.9437	High Similarity	NPC159579
0.9437	High Similarity	NPC282169
0.9437	High Similarity	NPC259957
0.9437	High Similarity	NPC224530
0.9437	High Similarity	NPC48093
0.9437	High Similarity	NPC129217
0.9408	High Similarity	NPC474093
0.9408	High Similarity	NPC104910
0.9405	High Similarity	NPC135831
0.9405	High Similarity	NPC297503
0.9405	High Similarity	NPC97119
0.939	High Similarity	NPC138990
0.939	High Similarity	NPC76047
0.939	High Similarity	NPC175429
0.939	High Similarity	NPC209550
0.939	High Similarity	NPC277532
0.9383	High Similarity	NPC289667
0.9383	High Similarity	NPC292929
0.9383	High Similarity	NPC76831
0.9379	High Similarity	NPC240306
0.9379	High Similarity	NPC27942
0.9379	High Similarity	NPC472876
0.9375	High Similarity	NPC470405
0.9375	High Similarity	NPC471079
0.9375	High Similarity	NPC304741
0.9371	High Similarity	NPC135391
0.9371	High Similarity	NPC197304
0.9371	High Similarity	NPC77672
0.9371	High Similarity	NPC78263
0.9371	High Similarity	NPC54802
0.9371	High Similarity	NPC133671
0.9353	High Similarity	NPC475179
0.9353	High Similarity	NPC97817
0.9353	High Similarity	NPC30011
0.9353	High Similarity	NPC72554
0.9349	High Similarity	NPC75574
0.9341	High Similarity	NPC477895
0.9337	High Similarity	NPC214621
0.9337	High Similarity	NPC223426
0.9337	High Similarity	NPC81042
0.9337	High Similarity	NPC34267
0.9325	High Similarity	NPC256188
0.9325	High Similarity	NPC12013
0.9325	High Similarity	NPC11432
0.9325	High Similarity	NPC189564
0.9325	High Similarity	NPC32641
0.9325	High Similarity	NPC203145
0.9325	High Similarity	NPC221342
0.9325	High Similarity	NPC186816
0.9325	High Similarity	NPC142142
0.9325	High Similarity	NPC477613
0.9325	High Similarity	NPC476470
0.9321	High Similarity	NPC121703
0.9317	High Similarity	NPC135846
0.9317	High Similarity	NPC170052
0.9317	High Similarity	NPC249281
0.9317	High Similarity	NPC101636
0.9317	High Similarity	NPC246943
0.9317	High Similarity	NPC476215
0.9317	High Similarity	NPC473438
0.9317	High Similarity	NPC297987
0.9317	High Similarity	NPC139320
0.9317	High Similarity	NPC181465
0.9317	High Similarity	NPC265885
0.9317	High Similarity	NPC253788
0.9317	High Similarity	NPC215710
0.9317	High Similarity	NPC163242
0.9317	High Similarity	NPC64305
0.9317	High Similarity	NPC116458
0.9317	High Similarity	NPC276377
0.9317	High Similarity	NPC173582
0.9313	High Similarity	NPC104677
0.9313	High Similarity	NPC320283
0.9313	High Similarity	NPC472459
0.9313	High Similarity	NPC41121
0.9313	High Similarity	NPC111929
0.9308	High Similarity	NPC323593
0.9308	High Similarity	NPC203500
0.9308	High Similarity	NPC307938
0.929	High Similarity	NPC162394
0.929	High Similarity	NPC156785
0.929	High Similarity	NPC470718
0.929	High Similarity	NPC241781
0.9286	High Similarity	NPC471030
0.9281	High Similarity	NPC144097
0.9281	High Similarity	NPC61904
0.9264	High Similarity	NPC287889
0.9264	High Similarity	NPC72016
0.9264	High Similarity	NPC135358
0.9259	High Similarity	NPC298171
0.9255	High Similarity	NPC187379
0.9255	High Similarity	NPC136761
0.925	High Similarity	NPC182634
0.925	High Similarity	NPC108831
0.9235	High Similarity	NPC460984
0.9235	High Similarity	NPC223860
0.9235	High Similarity	NPC470717
0.9235	High Similarity	NPC25946
0.9235	High Similarity	NPC21359
0.9235	High Similarity	NPC249560
0.9235	High Similarity	NPC470713
0.9235	High Similarity	NPC470720
0.9235	High Similarity	NPC275977
0.9226	High Similarity	NPC35167
0.9226	High Similarity	NPC253521
0.9226	High Similarity	NPC217520
0.9226	High Similarity	NPC113836
0.9226	High Similarity	NPC139571
0.9226	High Similarity	NPC37668
0.9212	High Similarity	NPC5319
0.9207	High Similarity	NPC298666
0.9207	High Similarity	NPC262222
0.9207	High Similarity	NPC68592
0.9193	High Similarity	NPC138811
0.9193	High Similarity	NPC22062
0.9193	High Similarity	NPC473634
0.9182	High Similarity	NPC29763
0.9182	High Similarity	NPC143851
0.9182	High Similarity	NPC83283
0.9182	High Similarity	NPC210003
0.9182	High Similarity	NPC39360
0.9181	High Similarity	NPC470719
0.9181	High Similarity	NPC33083
0.9181	High Similarity	NPC295625
0.9181	High Similarity	NPC473554
0.9172	High Similarity	NPC179862
0.9141	High Similarity	NPC244875
0.9141	High Similarity	NPC475382
0.9141	High Similarity	NPC150164
0.9136	High Similarity	NPC153342
0.9136	High Similarity	NPC473623
0.913	High Similarity	NPC313163
0.913	High Similarity	NPC129827
0.913	High Similarity	NPC156457
0.913	High Similarity	NPC197896
0.913	High Similarity	NPC44931
0.913	High Similarity	NPC161749
0.913	High Similarity	NPC288084
0.913	High Similarity	NPC65003
0.913	High Similarity	NPC473512
0.913	High Similarity	NPC258035
0.913	High Similarity	NPC43638
0.9125	High Similarity	NPC95090
0.9125	High Similarity	NPC27408
0.9123	High Similarity	NPC470416
0.9119	High Similarity	NPC259767
0.9119	High Similarity	NPC88484
0.9112	High Similarity	NPC293626
0.9112	High Similarity	NPC196127
0.9112	High Similarity	NPC217387
0.9112	High Similarity	NPC258044
0.9112	High Similarity	NPC267680
0.9085	High Similarity	NPC179198
0.9085	High Similarity	NPC66087
0.9085	High Similarity	NPC311850
0.9085	High Similarity	NPC278419
0.9085	High Similarity	NPC473644
0.908	High Similarity	NPC303913
0.9074	High Similarity	NPC43761
0.9074	High Similarity	NPC73511
0.9068	High Similarity	NPC127406
0.9068	High Similarity	NPC473657
0.9068	High Similarity	NPC295613
0.9068	High Similarity	NPC170475
0.9064	High Similarity	NPC36138

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 NPC218161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	933
0.2-0.3	1943
0.3-0.4	2699
0.4-0.5	1892
0.5-0.6	887
0.6-0.7	262
0.7-0.8	112
0.8-0.85	25
0.85-0.9	11
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9212	High Similarity	NPD7804	Clinical (unspecified phase)
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.8994	High Similarity	NPD7808	Phase 3
0.8935	High Similarity	NPD7251	Discontinued
0.8882	High Similarity	NPD4338	Clinical (unspecified phase)
0.8876	High Similarity	NPD6797	Phase 2
0.878	High Similarity	NPD7075	Discontinued
0.8757	High Similarity	NPD7054	Approved
0.8706	High Similarity	NPD7472	Approved
0.8688	High Similarity	NPD5403	Approved
0.865	High Similarity	NPD6801	Discontinued
0.8598	High Similarity	NPD7096	Clinical (unspecified phase)
0.8596	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD5401	Approved
0.8547	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD6799	Approved
0.8483	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5402	Approved
0.84	Intermediate Similarity	NPD8313	Approved
0.84	Intermediate Similarity	NPD8312	Approved
0.8364	Intermediate Similarity	NPD7411	Suspended
0.8363	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8286	Intermediate Similarity	NPD6559	Discontinued
0.8274	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8455	Phase 2
0.8214	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8166	Intermediate Similarity	NPD7768	Phase 2
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD1934	Approved
0.7977	Intermediate Similarity	NPD6959	Discontinued
0.7955	Intermediate Similarity	NPD3751	Discontinued
0.7953	Intermediate Similarity	NPD3882	Suspended
0.7952	Intermediate Similarity	NPD1512	Approved
0.7941	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7435	Discontinued
0.7931	Intermediate Similarity	NPD3787	Discontinued
0.7907	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.784	Intermediate Similarity	NPD2796	Approved
0.7836	Intermediate Similarity	NPD2801	Approved
0.7831	Intermediate Similarity	NPD1511	Approved
0.7824	Intermediate Similarity	NPD8151	Discontinued
0.7784	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7874	Approved
0.7772	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD3750	Approved
0.7709	Intermediate Similarity	NPD5844	Phase 1
0.7708	Intermediate Similarity	NPD7870	Phase 2
0.7708	Intermediate Similarity	NPD7871	Phase 2
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6776	Approved
0.7684	Intermediate Similarity	NPD6782	Approved
0.7684	Intermediate Similarity	NPD6781	Approved
0.7684	Intermediate Similarity	NPD6778	Approved
0.7684	Intermediate Similarity	NPD6779	Approved
0.7684	Intermediate Similarity	NPD6777	Approved
0.7684	Intermediate Similarity	NPD6780	Approved
0.7656	Intermediate Similarity	NPD7696	Phase 3
0.7656	Intermediate Similarity	NPD7698	Approved
0.7656	Intermediate Similarity	NPD7697	Approved
0.7647	Intermediate Similarity	NPD1653	Approved
0.764	Intermediate Similarity	NPD1240	Approved
0.764	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7584	Approved
0.7625	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1551	Phase 2
0.7617	Intermediate Similarity	NPD8319	Approved
0.7617	Intermediate Similarity	NPD8320	Phase 1
0.7602	Intermediate Similarity	NPD7458	Discontinued
0.7598	Intermediate Similarity	NPD7473	Discontinued
0.759	Intermediate Similarity	NPD7701	Phase 2
0.7588	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7685	Pre-registration
0.7563	Intermediate Similarity	NPD7783	Phase 2
0.7563	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1607	Approved
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7528	Intermediate Similarity	NPD6232	Discontinued
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7475	Intermediate Similarity	NPD7801	Approved
0.7472	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD6233	Phase 2
0.7459	Intermediate Similarity	NPD7228	Approved
0.7455	Intermediate Similarity	NPD3748	Approved
0.7429	Intermediate Similarity	NPD1465	Phase 2
0.7425	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6534	Approved
0.7421	Intermediate Similarity	NPD6535	Approved
0.7416	Intermediate Similarity	NPD5494	Approved
0.7411	Intermediate Similarity	NPD7585	Approved
0.7396	Intermediate Similarity	NPD6190	Approved
0.7391	Intermediate Similarity	NPD6832	Phase 2
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7378	Intermediate Similarity	NPD1933	Approved
0.736	Intermediate Similarity	NPD919	Approved
0.736	Intermediate Similarity	NPD7583	Approved
0.7333	Intermediate Similarity	NPD6823	Phase 2
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.7312	Intermediate Similarity	NPD1203	Approved
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7283	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7266	Discontinued
0.7251	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7033	Discontinued
0.7243	Intermediate Similarity	NPD5953	Discontinued
0.7209	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2935	Discontinued
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7186	Intermediate Similarity	NPD7097	Phase 1
0.7176	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD1652	Phase 2
0.7175	Intermediate Similarity	NPD37	Approved
0.717	Intermediate Similarity	NPD1091	Approved
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.7167	Intermediate Similarity	NPD6234	Discontinued
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7112	Intermediate Similarity	NPD7240	Approved
0.711	Intermediate Similarity	NPD7390	Discontinued
0.7104	Intermediate Similarity	NPD3926	Phase 2
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3226	Approved
0.7088	Intermediate Similarity	NPD1247	Approved
0.7073	Intermediate Similarity	NPD4908	Phase 1
0.7069	Intermediate Similarity	NPD2532	Approved
0.7069	Intermediate Similarity	NPD2533	Approved
0.7069	Intermediate Similarity	NPD2534	Approved
0.7066	Intermediate Similarity	NPD5124	Phase 1
0.7066	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD3225	Approved
0.7031	Intermediate Similarity	NPD4287	Approved
0.7024	Intermediate Similarity	NPD6651	Approved
0.7022	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD9717	Approved
0.701	Intermediate Similarity	NPD6212	Phase 3
0.701	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6213	Phase 3
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD3887	Approved
0.6994	Remote Similarity	NPD2354	Approved
0.6988	Remote Similarity	NPD3268	Approved
0.6988	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2800	Approved
0.6974	Remote Similarity	NPD4363	Phase 3
0.6974	Remote Similarity	NPD4360	Phase 2
0.6964	Remote Similarity	NPD230	Phase 1
0.6964	Remote Similarity	NPD4340	Discontinued
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD422	Phase 1
0.6954	Remote Similarity	NPD7440	Discontinued
0.6951	Remote Similarity	NPD2798	Approved
0.6946	Remote Similarity	NPD4062	Phase 3
0.6936	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1548	Phase 1
0.6906	Remote Similarity	NPD4288	Approved
0.6905	Remote Similarity	NPD943	Approved
0.6901	Remote Similarity	NPD5404	Approved
0.6901	Remote Similarity	NPD5405	Approved
0.6901	Remote Similarity	NPD5406	Approved
0.6901	Remote Similarity	NPD5408	Approved
0.6898	Remote Similarity	NPD7799	Discontinued
0.689	Remote Similarity	NPD2797	Approved
0.6889	Remote Similarity	NPD6844	Discontinued
0.6881	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7680	Approved
0.6864	Remote Similarity	NPD447	Suspended
0.6864	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7930	Approved
0.686	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD4308	Phase 3
0.6839	Remote Similarity	NPD7003	Approved
0.6836	Remote Similarity	NPD5049	Phase 3
0.6822	Remote Similarity	NPD8059	Phase 3
0.6822	Remote Similarity	NPD8058	Clinical (unspecified phase)

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