NPASS Compound

Structure

CID289021 OpenBabel06191716092D 35 38 0 0 1 0 0 0 0 0999 V2000 1.4863 3.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 4.5827 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 2 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 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 1.7321 -1.0000 0.0000 C 0 0 1 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 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 0.7431 3.6691 0.0000 C 0 0 2 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 6.9282 2.0000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 3.9781 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 0.0000 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 32 1 0 0 0 0 10 20 1 0 0 0 0 11 25 1 0 0 0 0 12 6 1 1 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 19 1 0 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 33 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 1 0 0 0 16 17 1 0 0 0 0 16 26 1 6 0 0 0 17 18 1 0 0 0 0 17 27 1 1 0 0 0 18 22 1 0 0 0 0 18 34 1 6 0 0 0 19 28 2 0 0 0 0 19 29 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 32 1 0 0 0 0 21 35 1 6 0 0 0 22 33 1 0 0 0 0 22 35 1 1 0 0 0 23 1 1 1 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.16
Volume:	461.802
LogP:	0.716
LogD:	0.011
LogS:	-2.252
# Rotatable Bonds:	7
TPSA:	192.44
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	4.637
Fsp3:	0.565
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.15
MDCK Permeability:	5.9967107517877594e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.869
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194
Plasma Protein Binding (PPB):	40.98438262939453%
Volume Distribution (VD):	0.294
Pgp-substrate:	34.4333610534668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	1.781
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.125
Carcinogencity:	0.892
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.786

Download Data

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

Natural Product: NPC289021

Natural Product ID:	NPC289021
*Common Name:**	Negundoside
IUPAC Name:	(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
Synonyms:	Negundoside
Standard InCHIKey:	RFCSGMIUBXUYSE-KLZCBZFCSA-N
Standard InCHI:	InChI=1S/C23H28O12/c1-23(31)7-6-12-13(19(28)29)9-32-21(15(12)23)35-22-18(17(27)16(26)14(8-24)33-22)34-20(30)10-2-4-11(25)5-3-10/h2-5,9,12,14-18,21-22,24-27,31H,6-8H2,1H3,(H,28,29)/t12-,14-,15-,16-,17+,18-,21+,22+,23+/m1/s1
SMILES:	C[C@@]1(CC[C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)OC(=O)c1ccc(cc1)O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519878
PubChem CID:	9935561
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid 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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180830]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	leaves	Tam Kim, Cao Bang Province, in North Vietnam	2000-JUN	PMID[16989521]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	whole plant	Cholistan desert near district Bahawalpur (Punjab), Pakistan	2003-Oct	PMID[20542692]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[2082684]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21922656]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO18530	Shigella flexneri	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26918643]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3254039]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3256207]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668556]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22248	Alkanna hirsutissima	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18571	Drypetes roxburghii	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20043	Vallaris solanacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19074	Buddleja variabilis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20360	Mentha pulegiformis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18530	Shigella flexneri	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14247	Melaleuca uncinata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22454	Picris radicata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16146	Osmundaria colensoi	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21798	Dacrydium biforme	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21298	Leucanthemum maximum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7080	Monascus purpureus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7865	Scapania nemorea	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20678	Grindelia nana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20808	Halopitys incurvus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20184	Streptomyces misawanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20536	Salvia nubicola	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21636	Didemnum inarmatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21247	Nephroma australe	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14394	Hakea saligna	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17108	Lecanora lividocinerea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21736	Abies nobilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22323	Pinus picea	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22762	Eremophila serrulata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12225	Amsinckia menziesii	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21505	Calea megacephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23057	Primula hirsuta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22062	Leptothorax acervorum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22994	Cordyline indivisa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5952	Phegopteris bukoensis	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22582	Smenospongia echina	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22710	Acrocomia sclerocarpa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21113	Coronophora gregaria	Species	Nitschkiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21998	Corydalis cornuta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19921	Polyphaga sinensis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22940	Delphinium campylocentrum	Species	Ranunculaceae	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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	159000.0	nM	PMID[458574]
NPT2	Others	Unspecified		Inhibition	=	8.0	%	PMID[458574]

☑ 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 NPC289021 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	318
0.1-0.2	1121
0.2-0.3	2563
0.3-0.4	4908
0.4-0.5	9904
0.5-0.6	9157
0.6-0.7	9488
0.7-0.8	4967
0.8-0.85	188
0.85-0.9	54
0.9-0.95	24
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158546
0.9722	High Similarity	NPC478234
0.9722	High Similarity	NPC478236
0.9524	High Similarity	NPC478235
0.9524	High Similarity	NPC194705
0.9521	High Similarity	NPC240592
0.9521	High Similarity	NPC117346
0.9459	High Similarity	NPC229354
0.9452	High Similarity	NPC96599
0.9375	High Similarity	NPC77922
0.9375	High Similarity	NPC296659
0.9375	High Similarity	NPC202391
0.9375	High Similarity	NPC473281
0.9286	High Similarity	NPC109990
0.9267	High Similarity	NPC478232
0.9241	High Similarity	NPC251062
0.9241	High Similarity	NPC184464
0.9221	High Similarity	NPC145847
0.9195	High Similarity	NPC475379
0.9189	High Similarity	NPC161955
0.9184	High Similarity	NPC473149
0.9172	High Similarity	NPC186296
0.9167	High Similarity	NPC7518
0.9167	High Similarity	NPC159387
0.9167	High Similarity	NPC154262
0.9167	High Similarity	NPC137501
0.9145	High Similarity	NPC475378
0.9097	High Similarity	NPC476011
0.9091	High Similarity	NPC138993
0.9079	High Similarity	NPC475484
0.9067	High Similarity	NPC474620
0.9051	High Similarity	NPC21956
0.9026	High Similarity	NPC179914
0.8986	High Similarity	NPC474268
0.8986	High Similarity	NPC143246
0.8986	High Similarity	NPC119773
0.8986	High Similarity	NPC475539
0.8968	High Similarity	NPC474936
0.8961	High Similarity	NPC187205
0.8924	High Similarity	NPC301910
0.8924	High Similarity	NPC130730
0.8919	High Similarity	NPC475528
0.8912	High Similarity	NPC478250
0.8897	High Similarity	NPC49597
0.8897	High Similarity	NPC31745
0.8897	High Similarity	NPC220936
0.8854	High Similarity	NPC206815
0.8846	High Similarity	NPC130489
0.8846	High Similarity	NPC208676
0.8824	High Similarity	NPC257847
0.8811	High Similarity	NPC322503
0.8811	High Similarity	NPC470143
0.8811	High Similarity	NPC114116
0.8776	High Similarity	NPC46644
0.8759	High Similarity	NPC471345
0.875	High Similarity	NPC35097
0.8742	High Similarity	NPC189631
0.8733	High Similarity	NPC473147
0.8725	High Similarity	NPC194938
0.8725	High Similarity	NPC63304
0.8718	High Similarity	NPC329997
0.8688	High Similarity	NPC282551
0.8658	High Similarity	NPC475213
0.8658	High Similarity	NPC152796
0.8658	High Similarity	NPC237872
0.8658	High Similarity	NPC88754
0.8658	High Similarity	NPC263397
0.8658	High Similarity	NPC116104
0.8658	High Similarity	NPC293154
0.8658	High Similarity	NPC302286
0.8621	High Similarity	NPC169398
0.8618	High Similarity	NPC120728
0.8609	High Similarity	NPC291153
0.8609	High Similarity	NPC473867
0.8609	High Similarity	NPC212808
0.86	High Similarity	NPC478240
0.8571	High Similarity	NPC170718
0.8553	High Similarity	NPC477627
0.8553	High Similarity	NPC293568
0.8553	High Similarity	NPC117943
0.8543	High Similarity	NPC210330
0.8542	High Similarity	NPC254819
0.8537	High Similarity	NPC195972
0.8523	High Similarity	NPC80098
0.8509	High Similarity	NPC180586
0.8506	High Similarity	NPC116292
0.8506	High Similarity	NPC87630
0.8506	High Similarity	NPC179128
0.8506	High Similarity	NPC267469
0.8503	High Similarity	NPC472132
0.8487	Intermediate Similarity	NPC208293
0.8487	Intermediate Similarity	NPC37838
0.8481	Intermediate Similarity	NPC226759
0.8481	Intermediate Similarity	NPC4747
0.8481	Intermediate Similarity	NPC475663
0.8481	Intermediate Similarity	NPC286919
0.8481	Intermediate Similarity	NPC49173
0.8481	Intermediate Similarity	NPC104275
0.8476	Intermediate Similarity	NPC470685
0.8471	Intermediate Similarity	NPC156624
0.8471	Intermediate Similarity	NPC172920
0.8452	Intermediate Similarity	NPC478249
0.8452	Intermediate Similarity	NPC269914
0.8446	Intermediate Similarity	NPC101686
0.8446	Intermediate Similarity	NPC65262
0.8446	Intermediate Similarity	NPC469364
0.8431	Intermediate Similarity	NPC18789
0.8428	Intermediate Similarity	NPC469384
0.84	Intermediate Similarity	NPC79908
0.8397	Intermediate Similarity	NPC203664
0.8395	Intermediate Similarity	NPC265600
0.8395	Intermediate Similarity	NPC294722
0.8387	Intermediate Similarity	NPC104172
0.8387	Intermediate Similarity	NPC182350
0.8387	Intermediate Similarity	NPC35160
0.8387	Intermediate Similarity	NPC147224
0.8387	Intermediate Similarity	NPC162569
0.8387	Intermediate Similarity	NPC69367
0.8387	Intermediate Similarity	NPC88886
0.8377	Intermediate Similarity	NPC308178
0.8366	Intermediate Similarity	NPC474044
0.8354	Intermediate Similarity	NPC10205
0.8344	Intermediate Similarity	NPC469396
0.8344	Intermediate Similarity	NPC469459
0.8344	Intermediate Similarity	NPC157898
0.8344	Intermediate Similarity	NPC284957
0.8344	Intermediate Similarity	NPC296643
0.8344	Intermediate Similarity	NPC469419
0.8344	Intermediate Similarity	NPC149002
0.8344	Intermediate Similarity	NPC469458
0.8344	Intermediate Similarity	NPC478241
0.8344	Intermediate Similarity	NPC89693
0.8344	Intermediate Similarity	NPC88176
0.8344	Intermediate Similarity	NPC229548
0.8333	Intermediate Similarity	NPC140151
0.8333	Intermediate Similarity	NPC120012
0.8322	Intermediate Similarity	NPC475195
0.8302	Intermediate Similarity	NPC478248
0.8302	Intermediate Similarity	NPC471405
0.8299	Intermediate Similarity	NPC136608
0.8299	Intermediate Similarity	NPC38420
0.8291	Intermediate Similarity	NPC194095
0.8291	Intermediate Similarity	NPC472128
0.8291	Intermediate Similarity	NPC327032
0.8291	Intermediate Similarity	NPC191046
0.8291	Intermediate Similarity	NPC472127
0.8289	Intermediate Similarity	NPC242756
0.8282	Intermediate Similarity	NPC475979
0.828	Intermediate Similarity	NPC469456
0.828	Intermediate Similarity	NPC36130
0.828	Intermediate Similarity	NPC134905
0.8278	Intermediate Similarity	NPC51181
0.8278	Intermediate Similarity	NPC469911
0.8272	Intermediate Similarity	NPC41009
0.8255	Intermediate Similarity	NPC27721
0.8255	Intermediate Similarity	NPC294470
0.8253	Intermediate Similarity	NPC148185
0.825	Intermediate Similarity	NPC43638
0.825	Intermediate Similarity	NPC472860
0.8235	Intermediate Similarity	NPC471028
0.8228	Intermediate Similarity	NPC137813
0.8224	Intermediate Similarity	NPC65833
0.8224	Intermediate Similarity	NPC184053
0.8221	Intermediate Similarity	NPC161151
0.8219	Intermediate Similarity	NPC17567
0.8205	Intermediate Similarity	NPC111785
0.8205	Intermediate Similarity	NPC92117
0.8199	Intermediate Similarity	NPC43761
0.8199	Intermediate Similarity	NPC470607
0.8199	Intermediate Similarity	NPC76211
0.8199	Intermediate Similarity	NPC73511
0.8194	Intermediate Similarity	NPC470330
0.8188	Intermediate Similarity	NPC202729
0.8187	Intermediate Similarity	NPC127406
0.8182	Intermediate Similarity	NPC108455
0.8176	Intermediate Similarity	NPC311492
0.8176	Intermediate Similarity	NPC28836
0.8165	Intermediate Similarity	NPC190217
0.8165	Intermediate Similarity	NPC267091
0.8165	Intermediate Similarity	NPC134819
0.8163	Intermediate Similarity	NPC478255
0.8163	Intermediate Similarity	NPC475824
0.8163	Intermediate Similarity	NPC281798
0.8163	Intermediate Similarity	NPC239358
0.8163	Intermediate Similarity	NPC473777
0.8163	Intermediate Similarity	NPC233692
0.8155	Intermediate Similarity	NPC469438
0.8155	Intermediate Similarity	NPC171706
0.8153	Intermediate Similarity	NPC205054
0.8153	Intermediate Similarity	NPC247219
0.8148	Intermediate Similarity	NPC271479
0.8148	Intermediate Similarity	NPC328093
0.8148	Intermediate Similarity	NPC203020
0.8148	Intermediate Similarity	NPC239966
0.8144	Intermediate Similarity	NPC477617
0.8141	Intermediate Similarity	NPC476173
0.8141	Intermediate Similarity	NPC81835
0.8141	Intermediate Similarity	NPC120621
0.8141	Intermediate Similarity	NPC248257
0.814	Intermediate Similarity	NPC299855

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 NPC289021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	731
0.2-0.3	1558
0.3-0.4	2551
0.4-0.5	2294
0.5-0.6	1241
0.6-0.7	433
0.7-0.8	78
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.865	High Similarity	NPD7685	Pre-registration
0.8137	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7792	Intermediate Similarity	NPD7266	Discontinued
0.7764	Intermediate Similarity	NPD4380	Phase 2
0.7751	Intermediate Similarity	NPD3818	Discontinued
0.7706	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9545	Approved
0.7616	Intermediate Similarity	NPD3764	Approved
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7054	Approved
0.7595	Intermediate Similarity	NPD6190	Approved
0.759	Intermediate Similarity	NPD7075	Discontinued
0.7584	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6559	Discontinued
0.756	Intermediate Similarity	NPD7199	Phase 2
0.7558	Intermediate Similarity	NPD7074	Phase 3
0.7558	Intermediate Similarity	NPD7472	Approved
0.7544	Intermediate Similarity	NPD7799	Discontinued
0.753	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8455	Phase 2
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7455	Intermediate Similarity	NPD6801	Discontinued
0.7429	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6273	Approved
0.7403	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6002	Phase 3
0.7342	Intermediate Similarity	NPD6004	Phase 3
0.7342	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6005	Phase 3
0.7341	Intermediate Similarity	NPD7228	Approved
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7329	Intermediate Similarity	NPD7236	Approved
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.7321	Intermediate Similarity	NPD4966	Approved
0.7317	Intermediate Similarity	NPD1653	Approved
0.7312	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6653	Approved
0.7296	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1934	Approved
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5647	Approved
0.7215	Intermediate Similarity	NPD1510	Phase 2
0.7212	Intermediate Similarity	NPD7239	Suspended
0.7205	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7819	Suspended
0.72	Intermediate Similarity	NPD5844	Phase 1
0.7188	Intermediate Similarity	NPD1549	Phase 2
0.7186	Intermediate Similarity	NPD7411	Suspended
0.7178	Intermediate Similarity	NPD6799	Approved
0.716	Intermediate Similarity	NPD3817	Phase 2
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7028	Phase 2
0.7126	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6599	Discontinued
0.7126	Intermediate Similarity	NPD6166	Phase 2
0.7125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6663	Approved
0.7101	Intermediate Similarity	NPD5760	Phase 2
0.7101	Intermediate Similarity	NPD5761	Phase 2
0.7097	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7435	Discontinued
0.7079	Intermediate Similarity	NPD6765	Approved
0.7079	Intermediate Similarity	NPD6764	Approved
0.7078	Intermediate Similarity	NPD5736	Approved
0.7077	Intermediate Similarity	NPD7930	Approved
0.7072	Intermediate Similarity	NPD8434	Phase 2
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7063	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD5402	Approved
0.7053	Intermediate Similarity	NPD8320	Phase 1
0.7053	Intermediate Similarity	NPD8319	Approved
0.7044	Intermediate Similarity	NPD7097	Phase 1
0.7044	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7585	Approved
0.703	Intermediate Similarity	NPD2534	Approved
0.703	Intermediate Similarity	NPD5401	Approved
0.703	Intermediate Similarity	NPD2532	Approved
0.703	Intermediate Similarity	NPD2533	Approved
0.703	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6534	Approved
0.7027	Intermediate Similarity	NPD6535	Approved
0.7021	Intermediate Similarity	NPD6776	Approved
0.7021	Intermediate Similarity	NPD6782	Approved
0.7021	Intermediate Similarity	NPD6781	Approved
0.7021	Intermediate Similarity	NPD6780	Approved
0.7021	Intermediate Similarity	NPD6778	Approved
0.7021	Intermediate Similarity	NPD6779	Approved
0.7021	Intermediate Similarity	NPD6777	Approved
0.702	Intermediate Similarity	NPD1091	Approved
0.7019	Intermediate Similarity	NPD5762	Approved
0.7019	Intermediate Similarity	NPD5763	Approved
0.7016	Intermediate Similarity	NPD7999	Approved
0.7013	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD6232	Discontinued
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD7497	Discontinued
0.7	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD2801	Approved
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1876	Approved
0.6989	Remote Similarity	NPD7473	Discontinued
0.6983	Remote Similarity	NPD7240	Approved
0.6979	Remote Similarity	NPD7583	Approved
0.6977	Remote Similarity	NPD3749	Approved
0.6974	Remote Similarity	NPD1608	Approved
0.6962	Remote Similarity	NPD1240	Approved
0.6948	Remote Similarity	NPD6362	Approved
0.6948	Remote Similarity	NPD2797	Approved
0.6943	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6785	Approved
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6784	Approved
0.6919	Remote Similarity	NPD7768	Phase 2
0.6919	Remote Similarity	NPD7058	Phase 2
0.6919	Remote Similarity	NPD3882	Suspended
0.6919	Remote Similarity	NPD7057	Phase 3
0.6918	Remote Similarity	NPD5124	Phase 1
0.6918	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7700	Phase 2
0.6915	Remote Similarity	NPD7699	Phase 2
0.691	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5494	Approved
0.6894	Remote Similarity	NPD4308	Phase 3
0.6894	Remote Similarity	NPD2799	Discontinued
0.6894	Remote Similarity	NPD3748	Approved
0.6891	Remote Similarity	NPD7584	Approved
0.689	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD1607	Approved
0.6872	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7874	Approved
0.6867	Remote Similarity	NPD1511	Approved
0.6864	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2861	Phase 2
0.6859	Remote Similarity	NPD9494	Approved
0.6855	Remote Similarity	NPD4140	Approved
0.6854	Remote Similarity	NPD3751	Discontinued
0.6848	Remote Similarity	NPD3887	Approved
0.6848	Remote Similarity	NPD2354	Approved
0.6846	Remote Similarity	NPD9493	Approved
0.6839	Remote Similarity	NPD3094	Phase 2
0.6837	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7783	Phase 2
0.6829	Remote Similarity	NPD1652	Phase 2
0.6824	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7698	Approved
0.6823	Remote Similarity	NPD7697	Approved
0.6823	Remote Similarity	NPD7696	Phase 3
0.6821	Remote Similarity	NPD8151	Discontinued
0.6813	Remote Similarity	NPD1933	Approved
0.6807	Remote Similarity	NPD5058	Phase 3
0.6791	Remote Similarity	NPD6212	Phase 3
0.6791	Remote Similarity	NPD6213	Phase 3
0.6791	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7871	Phase 2
0.6788	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7003	Approved
0.6788	Remote Similarity	NPD7870	Phase 2
0.6788	Remote Similarity	NPD4110	Phase 3
0.6786	Remote Similarity	NPD1512	Approved
0.6776	Remote Similarity	NPD5126	Approved
0.6776	Remote Similarity	NPD17	Approved
0.6776	Remote Similarity	NPD5125	Phase 3
0.6771	Remote Similarity	NPD6823	Phase 2
0.6769	Remote Similarity	NPD7701	Phase 2
0.6768	Remote Similarity	NPD2424	Discontinued
0.6768	Remote Similarity	NPD5958	Discontinued
0.6765	Remote Similarity	NPD3455	Phase 2
0.6765	Remote Similarity	NPD3226	Approved
0.6763	Remote Similarity	NPD5353	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