NPASS Compound

Structure

CID296558 OpenBabel06191716102D 32 36 0 0 1 0 0 0 0 0999 V2000 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 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 0.5000 -3.8660 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 -3.0000 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 -1.7321 1.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -4.4781 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.0000 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 -2.4752 -3.6691 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 31 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 1 0 0 0 21 31 1 0 0 0 0 22 27 1 6 0 0 0 22 32 1 0 0 0 0 23 28 2 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 25 27 1 6 0 0 0 26 4 1 1 0 0 0 26 29 1 0 0 0 0 27 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.24
Volume:	460.898
LogP:	4.824
LogD:	4.36
LogS:	-5.135
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	4.55
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
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:	-4.76
MDCK Permeability:	2.1559239030466415e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	98.31739044189453%
Volume Distribution (VD):	2.214
Pgp-substrate:	6.630395412445068%

ADMET: Metabolism

CYP1A2-inhibitor:	0.213
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.813
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.591
CYP2D6-inhibitor:	0.326
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.499

ADMET: Excretion

Clearance (CL):	10.2
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.486
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.696
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.132
Carcinogencity:	0.175
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC296558

Natural Product ID:	NPC296558
*Common Name:**	Isovouacapenol B
IUPAC Name:	[(4aR,5R,6aR,7S,11aS,11bR)-4a,7-dihydroxy-4,4,7,11b-tetramethyl-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-5-yl] benzoate
Synonyms:	Isovouacapenol B
Standard InCHIKey:	AJGZFQDMKBTWTH-GGUBNDNLSA-N
Standard InCHI:	InChI=1S/C27H34O5/c1-24(2)12-8-13-25(3)19-15-21-18(11-14-31-21)26(4,29)20(19)16-22(27(24,25)30)32-23(28)17-9-6-5-7-10-17/h5-7,9-11,14,19-20,22,29-30H,8,12-13,15-16H2,1-4H3/t19-,20+,22+,25+,26+,27+/m0/s1
SMILES:	O=C(c1ccccc1)O[C@@H]1C[C@@H]2[C@@H]([C@@]3([C@]1(O)C(C)(C)CCC3)C)Cc1c([C@@]2(C)O)cco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491584
PubChem CID:	11812203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np0201523]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193012]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19252323]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2380715]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[2380715]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106289]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783154]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176403]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19683	Pycnothymus rigidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17050	Haemanthus albiflos	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17876	Magnolia henryi	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20618	Penicilliopsis clavariiformis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16034	Lecanora sulphurata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19350	Ephedra altissima	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18899	Keyserlingia koreensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17433	Peltophorum dubium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10957	Cladosiphon okamuranus	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16256	Helleborus viridis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18824	Alpinia pulcherrima	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19495	Bignonia unguiscati	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4171	Isolona pilosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19285	Chromodoris cavae	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17565	Hordeum bulbosum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19554	Coronilla hyrcana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13245	Agelas longissima	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25549	Rhizophagus intraradices	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18576	Vernonia aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6642	Mocis latipes	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16727	Iris sibirica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18326	Eria siamensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1457	Phoma asparagi	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12464	Litsea nitida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18653	Cyathus intermedius	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6570	Cinnamomum philippinense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9142	Aeschynanthus parvifolius	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19222	Mycale tenuis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18986	Betula papyrifera	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15370	Tamarix dioica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19069	Thelepus setosus	Species	Terebellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7328	Salvia miniata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17987	Mycosphaerella nawae	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18747	Bufo bankorensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2351	Echinocardium cordatum	Species	Loveniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11763	Cyperus capitatus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19416	Streptomyces sakaiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15709	Lobelia langeana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1560	Boronia alata	Species	Rutaceae	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
Others	14

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.0	mm	PMID[447965]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.0	mm	PMID[447965]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	14.0	mm	PMID[447965]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	14.0	mm	PMID[447965]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	14.0	mm	PMID[447965]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	12.0	mm	PMID[447965]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	13.0	mm	PMID[447965]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	0.4	n.a.	PMID[447965]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	0.2	n.a.	PMID[447965]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	0.4	n.a.	PMID[447965]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Activity	=	0.4	n.a.	PMID[447965]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	0.4	n.a.	PMID[447965]
NPT21	Organism	Aspergillus niger	Aspergillus niger	Activity	=	0.2	n.a.	PMID[447965]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	Activity	=	0.3	n.a.	PMID[447965]

☑ 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 NPC296558 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	358
0.1-0.2	1318
0.2-0.3	2682
0.3-0.4	5082
0.4-0.5	9776
0.5-0.6	8279
0.6-0.7	5910
0.7-0.8	8211
0.8-0.85	809
0.85-0.9	235
0.9-0.95	30
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC88841
0.9618	High Similarity	NPC288602
0.9615	High Similarity	NPC8389
0.9554	High Similarity	NPC188649
0.9554	High Similarity	NPC79571
0.9487	High Similarity	NPC7059
0.9427	High Similarity	NPC474611
0.9375	High Similarity	NPC277618
0.9363	High Similarity	NPC88007
0.9363	High Similarity	NPC194499
0.9308	High Similarity	NPC68848
0.9308	High Similarity	NPC18986
0.9255	High Similarity	NPC121995
0.9245	High Similarity	NPC287559
0.9241	High Similarity	NPC195954
0.9212	High Similarity	NPC176413
0.9212	High Similarity	NPC56953
0.9146	High Similarity	NPC294512
0.913	High Similarity	NPC283209
0.913	High Similarity	NPC285567
0.9108	High Similarity	NPC121615
0.9108	High Similarity	NPC294511
0.9103	High Similarity	NPC228842
0.9103	High Similarity	NPC212257
0.908	High Similarity	NPC270312
0.9074	High Similarity	NPC56358
0.9068	High Similarity	NPC200782
0.9068	High Similarity	NPC82851
0.9057	High Similarity	NPC41880
0.9038	High Similarity	NPC211625
0.903	High Similarity	NPC475237
0.903	High Similarity	NPC475641
0.9018	High Similarity	NPC86800
0.897	High Similarity	NPC302392
0.8963	High Similarity	NPC310572
0.8957	High Similarity	NPC276735
0.8957	High Similarity	NPC470182
0.8957	High Similarity	NPC470940
0.8938	High Similarity	NPC104736
0.8931	High Similarity	NPC114880
0.8931	High Similarity	NPC282445
0.891	High Similarity	NPC71821
0.8909	High Similarity	NPC255787
0.8909	High Similarity	NPC160651
0.8896	High Similarity	NPC292389
0.8896	High Similarity	NPC472773
0.8896	High Similarity	NPC469338
0.8882	High Similarity	NPC81405
0.8882	High Similarity	NPC249021
0.8882	High Similarity	NPC304692
0.8882	High Similarity	NPC299038
0.8868	High Similarity	NPC476201
0.8848	High Similarity	NPC173516
0.8848	High Similarity	NPC41689
0.8841	High Similarity	NPC469849
0.8841	High Similarity	NPC276551
0.8834	High Similarity	NPC329938
0.8834	High Similarity	NPC472771
0.8827	High Similarity	NPC475967
0.8827	High Similarity	NPC140952
0.8817	High Similarity	NPC472665
0.8812	High Similarity	NPC30222
0.8797	High Similarity	NPC125182
0.8797	High Similarity	NPC69647
0.8795	High Similarity	NPC471397
0.8795	High Similarity	NPC291742
0.8795	High Similarity	NPC271235
0.879	High Similarity	NPC255414
0.8788	High Similarity	NPC475779
0.8788	High Similarity	NPC470875
0.8788	High Similarity	NPC308156
0.878	High Similarity	NPC14499
0.878	High Similarity	NPC475039
0.878	High Similarity	NPC476035
0.878	High Similarity	NPC477405
0.878	High Similarity	NPC39986
0.878	High Similarity	NPC302369
0.878	High Similarity	NPC134254
0.8773	High Similarity	NPC335761
0.8765	High Similarity	NPC472777
0.8765	High Similarity	NPC472776
0.8765	High Similarity	NPC261597
0.8765	High Similarity	NPC472778
0.8758	High Similarity	NPC264943
0.8758	High Similarity	NPC476262
0.8758	High Similarity	NPC35000
0.875	High Similarity	NPC469503
0.8743	High Similarity	NPC118086
0.8735	High Similarity	NPC473753
0.8735	High Similarity	NPC472775
0.8735	High Similarity	NPC472282
0.8735	High Similarity	NPC473766
0.8735	High Similarity	NPC472774
0.8734	High Similarity	NPC19747
0.8726	High Similarity	NPC62799
0.872	High Similarity	NPC149896
0.872	High Similarity	NPC18347
0.872	High Similarity	NPC263432
0.872	High Similarity	NPC69028
0.872	High Similarity	NPC471003
0.872	High Similarity	NPC5079
0.8712	High Similarity	NPC307383
0.8704	High Similarity	NPC107646
0.8696	High Similarity	NPC178932
0.8675	High Similarity	NPC93172
0.8675	High Similarity	NPC97574
0.8675	High Similarity	NPC472141
0.8667	High Similarity	NPC234660
0.8667	High Similarity	NPC476197
0.8667	High Similarity	NPC51568
0.8662	High Similarity	NPC41182
0.8659	High Similarity	NPC477402
0.8659	High Similarity	NPC472653
0.8655	High Similarity	NPC478050
0.865	High Similarity	NPC36655
0.865	High Similarity	NPC167142
0.865	High Similarity	NPC472772
0.8642	High Similarity	NPC214541
0.8642	High Similarity	NPC469336
0.8642	High Similarity	NPC75310
0.8642	High Similarity	NPC44675
0.8634	High Similarity	NPC268905
0.8631	High Similarity	NPC470995
0.8625	High Similarity	NPC476122
0.8625	High Similarity	NPC477404
0.8625	High Similarity	NPC196864
0.8621	High Similarity	NPC472663
0.8621	High Similarity	NPC472662
0.8614	High Similarity	NPC61967
0.8614	High Similarity	NPC261184
0.8614	High Similarity	NPC27541
0.8614	High Similarity	NPC126984
0.8614	High Similarity	NPC62692
0.8614	High Similarity	NPC271657
0.8606	High Similarity	NPC193798
0.8606	High Similarity	NPC470939
0.8606	High Similarity	NPC470792
0.8606	High Similarity	NPC207978
0.8598	High Similarity	NPC123153
0.8598	High Similarity	NPC477403
0.859	High Similarity	NPC263337
0.8589	High Similarity	NPC209364
0.8589	High Similarity	NPC469485
0.8571	High Similarity	NPC18135
0.8554	High Similarity	NPC472139
0.8554	High Similarity	NPC92589
0.8554	High Similarity	NPC198047
0.8554	High Similarity	NPC469846
0.8547	High Similarity	NPC11062
0.8545	High Similarity	NPC475381
0.8545	High Similarity	NPC472299
0.8545	High Similarity	NPC25255
0.8544	High Similarity	NPC5676
0.8537	High Similarity	NPC45101
0.8537	High Similarity	NPC173544
0.8537	High Similarity	NPC286722
0.8537	High Similarity	NPC187149
0.8535	High Similarity	NPC64568
0.8535	High Similarity	NPC476946
0.8521	High Similarity	NPC88593
0.8521	High Similarity	NPC82602
0.8521	High Similarity	NPC472660
0.8519	High Similarity	NPC282239
0.8519	High Similarity	NPC33938
0.8519	High Similarity	NPC44577
0.8519	High Similarity	NPC475777
0.8512	High Similarity	NPC472784
0.8512	High Similarity	NPC472651
0.8509	High Similarity	NPC477905
0.8509	High Similarity	NPC159927
0.8509	High Similarity	NPC469335
0.8503	High Similarity	NPC472664
0.8503	High Similarity	NPC476858
0.8503	High Similarity	NPC476857
0.8503	High Similarity	NPC476856
0.8494	Intermediate Similarity	NPC211777
0.8491	Intermediate Similarity	NPC97904
0.8488	Intermediate Similarity	NPC294149
0.8485	Intermediate Similarity	NPC475226
0.8485	Intermediate Similarity	NPC84349
0.8485	Intermediate Similarity	NPC473368
0.8485	Intermediate Similarity	NPC473473
0.8485	Intermediate Similarity	NPC475295
0.8481	Intermediate Similarity	NPC84479
0.8481	Intermediate Similarity	NPC476944
0.848	Intermediate Similarity	NPC118128
0.848	Intermediate Similarity	NPC472620
0.8471	Intermediate Similarity	NPC20578
0.8471	Intermediate Similarity	NPC121158
0.8471	Intermediate Similarity	NPC102810
0.8471	Intermediate Similarity	NPC62103
0.8466	Intermediate Similarity	NPC302054
0.8466	Intermediate Similarity	NPC217091
0.8466	Intermediate Similarity	NPC106895
0.8466	Intermediate Similarity	NPC253201
0.8466	Intermediate Similarity	NPC34421
0.8466	Intermediate Similarity	NPC237259
0.8466	Intermediate Similarity	NPC98206
0.8462	Intermediate Similarity	NPC125465
0.8462	Intermediate Similarity	NPC469419

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 NPC296558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	809
0.2-0.3	1587
0.3-0.4	2471
0.4-0.5	2183
0.5-0.6	1187
0.6-0.7	419
0.7-0.8	180
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8941	High Similarity	NPD8434	Phase 2
0.8415	Intermediate Similarity	NPD5761	Phase 2
0.8415	Intermediate Similarity	NPD5760	Phase 2
0.8125	Intermediate Similarity	NPD4628	Phase 3
0.8084	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7075	Discontinued
0.8047	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8011	Intermediate Similarity	NPD6559	Discontinued
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7819	Suspended
0.7953	Intermediate Similarity	NPD5494	Approved
0.7943	Intermediate Similarity	NPD5844	Phase 1
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7411	Suspended
0.7844	Intermediate Similarity	NPD7458	Discontinued
0.7831	Intermediate Similarity	NPD920	Approved
0.7824	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8312	Approved
0.7821	Intermediate Similarity	NPD8313	Approved
0.7818	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1934	Approved
0.7811	Intermediate Similarity	NPD6801	Discontinued
0.7809	Intermediate Similarity	NPD6764	Approved
0.7809	Intermediate Similarity	NPD6765	Approved
0.7798	Intermediate Similarity	NPD4380	Phase 2
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7771	Intermediate Similarity	NPD6273	Approved
0.7759	Intermediate Similarity	NPD6232	Discontinued
0.7758	Intermediate Similarity	NPD6799	Approved
0.7755	Intermediate Similarity	NPD8404	Phase 2
0.7738	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3817	Phase 2
0.7719	Intermediate Similarity	NPD5402	Approved
0.7716	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8127	Discontinued
0.7701	Intermediate Similarity	NPD6959	Discontinued
0.7688	Intermediate Similarity	NPD919	Approved
0.767	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6166	Phase 2
0.767	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2801	Approved
0.7654	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD6784	Approved
0.7637	Intermediate Similarity	NPD6785	Approved
0.7619	Intermediate Similarity	NPD5403	Approved
0.7609	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2532	Approved
0.7605	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2534	Approved
0.7605	Intermediate Similarity	NPD2533	Approved
0.7602	Intermediate Similarity	NPD37	Approved
0.7598	Intermediate Similarity	NPD7074	Phase 3
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.759	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7576	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3750	Approved
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7561	Intermediate Similarity	NPD1549	Phase 2
0.7557	Intermediate Similarity	NPD3787	Discontinued
0.7546	Intermediate Similarity	NPD2796	Approved
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7542	Intermediate Similarity	NPD7054	Approved
0.7542	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD7472	Approved
0.7486	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7473	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7003	Approved
0.7457	Intermediate Similarity	NPD1465	Phase 2
0.744	Intermediate Similarity	NPD1511	Approved
0.7439	Intermediate Similarity	NPD6100	Approved
0.7439	Intermediate Similarity	NPD6099	Approved
0.7418	Intermediate Similarity	NPD7251	Discontinued
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1243	Approved
0.741	Intermediate Similarity	NPD2800	Approved
0.7401	Intermediate Similarity	NPD7199	Phase 2
0.7394	Intermediate Similarity	NPD1471	Phase 3
0.7394	Intermediate Similarity	NPD2344	Approved
0.7381	Intermediate Similarity	NPD7236	Approved
0.7378	Intermediate Similarity	NPD1510	Phase 2
0.7378	Intermediate Similarity	NPD3748	Approved
0.7378	Intermediate Similarity	NPD7033	Discontinued
0.7377	Intermediate Similarity	NPD7808	Phase 3
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7363	Intermediate Similarity	NPD6797	Phase 2
0.736	Intermediate Similarity	NPD7229	Phase 3
0.7353	Intermediate Similarity	NPD1512	Approved
0.7349	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6781	Approved
0.7344	Intermediate Similarity	NPD6779	Approved
0.7344	Intermediate Similarity	NPD6776	Approved
0.7344	Intermediate Similarity	NPD6777	Approved
0.7344	Intermediate Similarity	NPD6780	Approved
0.7344	Intermediate Similarity	NPD6778	Approved
0.7344	Intermediate Similarity	NPD6782	Approved
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3764	Approved
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7322	Intermediate Similarity	NPD7685	Pre-registration
0.732	Intermediate Similarity	NPD7497	Discontinued
0.7318	Intermediate Similarity	NPD3926	Phase 2
0.7318	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6355	Discontinued
0.7293	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7799	Discontinued
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8455	Phase 2
0.7256	Intermediate Similarity	NPD1607	Approved
0.7239	Intermediate Similarity	NPD1240	Approved
0.7234	Intermediate Similarity	NPD8360	Approved
0.7234	Intermediate Similarity	NPD8361	Approved
0.7231	Intermediate Similarity	NPD7697	Approved
0.7231	Intermediate Similarity	NPD7698	Approved
0.7231	Intermediate Similarity	NPD7696	Phase 3
0.7228	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD3268	Approved
0.7222	Intermediate Similarity	NPD8151	Discontinued
0.7219	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD6190	Approved
0.7212	Intermediate Similarity	NPD7097	Phase 1
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7204	Intermediate Similarity	NPD8407	Phase 2
0.7198	Intermediate Similarity	NPD7177	Discontinued
0.7195	Intermediate Similarity	NPD447	Suspended
0.7194	Intermediate Similarity	NPD8319	Approved
0.7194	Intermediate Similarity	NPD8320	Phase 1
0.7194	Intermediate Similarity	NPD7871	Phase 2
0.7194	Intermediate Similarity	NPD7870	Phase 2
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7172	Intermediate Similarity	NPD7701	Phase 2
0.7169	Intermediate Similarity	NPD4308	Phase 3
0.7168	Intermediate Similarity	NPD7239	Suspended
0.716	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7095	Approved
0.7158	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD1608	Approved
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD8435	Approved
0.7135	Intermediate Similarity	NPD8368	Discontinued
0.7125	Intermediate Similarity	NPD2797	Approved
0.7117	Intermediate Similarity	NPD6798	Discontinued
0.7098	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD8485	Approved
0.7093	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD230	Phase 1
0.7087	Intermediate Similarity	NPD7907	Approved
0.7083	Intermediate Similarity	NPD6535	Approved
0.7083	Intermediate Similarity	NPD6534	Approved
0.7081	Intermediate Similarity	NPD5953	Discontinued
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD6233	Phase 2
0.7073	Intermediate Similarity	NPD4665	Approved
0.7073	Intermediate Similarity	NPD8032	Phase 2
0.7072	Intermediate Similarity	NPD5711	Approved
0.7072	Intermediate Similarity	NPD5710	Approved
0.7065	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7783	Phase 2
0.7062	Intermediate Similarity	NPD7699	Phase 2
0.7062	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8285	Discontinued
0.7024	Intermediate Similarity	NPD5406	Approved
0.7024	Intermediate Similarity	NPD5405	Approved
0.7024	Intermediate Similarity	NPD5408	Approved
0.7024	Intermediate Similarity	NPD5404	Approved
0.7019	Intermediate Similarity	NPD1203	Approved
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1933	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