NPASS Compound

Structure

CID79571 OpenBabel06191715412D 32 36 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 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 3.4641 4.0000 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 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -4.4152 -0.3090 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 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 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 25 1 0 0 0 0 13 26 1 0 0 0 0 14 31 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 1 1 6 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 1 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 32 1 0 0 0 0 24 29 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 26 27 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.24
Volume:	460.898
LogP:	4.906
LogD:	4.618
LogS:	-4.743
# 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:	0.663
Synthetic Accessibility Score:	4.624
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:	-4.748
MDCK Permeability:	2.471942025294993e-05
Pgp-inhibitor:	0.732
Pgp-substrate:	0.137
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	99.4820785522461%
Volume Distribution (VD):	2.52
Pgp-substrate:	4.187498569488525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.164
CYP2C9-inhibitor:	0.742
CYP2C9-substrate:	0.481
CYP2D6-inhibitor:	0.43
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	9.582
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.738
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.727
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.203
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC79571

Natural Product ID:	NPC79571
*Common Name:**	Isovouacapenol C
IUPAC Name:	[(4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-5-yl] benzoate
Synonyms:	Isovouacapenol C
Standard InCHIKey:	YMUSGWGTHSRGHT-WVTZLOSNSA-N
Standard InCHI:	InChI=1S/C27H34O5/c1-16-18-11-14-31-20(18)15-19-21(16)22(28)23(32-24(29)17-9-6-5-7-10-17)27(30)25(2,3)12-8-13-26(19,27)4/h5-7,9-11,14,16,19,21-23,28,30H,8,12-13,15H2,1-4H3/t16-,19-,21-,22+,23+,26+,27+/m0/s1
SMILES:	C[C@H]1c2ccoc2C[C@H]2[C@H]1[C@H]([C@H]([C@]1(C(C)(C)CCC[C@]21C)O)OC(=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522805
PubChem CID:	3009285
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]
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]
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]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	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]
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]
NPO19416	Streptomyces sakaiensis	Species	Streptomycetaceae	Bacteria	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]
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]
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]
NPO13245	Agelas longissima	Species	Agelasidae	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]
NPO16727	Iris sibirica	Species	Iridaceae	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]
NPO12464	Litsea nitida	Species	Lauraceae	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]
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]
NPO7328	Salvia miniata	Species	Lamiaceae	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]
NPO2351	Echinocardium cordatum	Species	Loveniidae	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]

☑ 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	13

Activity Type	# Activity
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	16.0	mm	PMID[543569]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.0	mm	PMID[543569]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	12.0	mm	PMID[543569]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	15.0	mm	PMID[543569]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[543569]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	13.0	mm	PMID[543569]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	0.6	n.a.	PMID[543569]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	0.2	n.a.	PMID[543569]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	0.2	n.a.	PMID[543569]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Activity	=	0.5	n.a.	PMID[543569]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	0.3	n.a.	PMID[543569]
NPT21	Organism	Aspergillus niger	Aspergillus niger	Activity	=	0.0	n.a.	PMID[543569]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	Activity	=	0.3	n.a.	PMID[543569]

☑ 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 NPC79571 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	331
0.1-0.2	1273
0.2-0.3	2552
0.3-0.4	4839
0.4-0.5	9705
0.5-0.6	8718
0.6-0.7	6668
0.7-0.8	7846
0.8-0.85	547
0.85-0.9	175
0.9-0.95	36
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC8389
0.9801	High Similarity	NPC7059
0.9677	High Similarity	NPC277618
0.9671	High Similarity	NPC194499
0.9554	High Similarity	NPC296558
0.9542	High Similarity	NPC88007
0.9536	High Similarity	NPC294511
0.9536	High Similarity	NPC121615
0.9416	High Similarity	NPC195954
0.9404	High Similarity	NPC212257
0.9404	High Similarity	NPC228842
0.9359	High Similarity	NPC68848
0.9359	High Similarity	NPC18986
0.9299	High Similarity	NPC283209
0.9245	High Similarity	NPC310572
0.9236	High Similarity	NPC188649
0.9231	High Similarity	NPC474611
0.9205	High Similarity	NPC71821
0.9182	High Similarity	NPC121995
0.9177	High Similarity	NPC88841
0.9177	High Similarity	NPC288602
0.9177	High Similarity	NPC285567
0.9125	High Similarity	NPC41689
0.9103	High Similarity	NPC41880
0.9085	High Similarity	NPC69647
0.9085	High Similarity	NPC125182
0.9068	High Similarity	NPC255787
0.9051	High Similarity	NPC287559
0.9045	High Similarity	NPC304692
0.9012	High Similarity	NPC118086
0.8981	High Similarity	NPC104736
0.8957	High Similarity	NPC475641
0.8957	High Similarity	NPC475237
0.8954	High Similarity	NPC255414
0.8951	High Similarity	NPC291742
0.8944	High Similarity	NPC308156
0.8938	High Similarity	NPC14499
0.8938	High Similarity	NPC475039
0.8938	High Similarity	NPC476035
0.8909	High Similarity	NPC56953
0.8909	High Similarity	NPC176413
0.8889	High Similarity	NPC270312
0.8882	High Similarity	NPC56358
0.8875	High Similarity	NPC471003
0.8874	High Similarity	NPC263337
0.8868	High Similarity	NPC140952
0.8868	High Similarity	NPC123153
0.8841	High Similarity	NPC294512
0.8824	High Similarity	NPC5676
0.8805	High Similarity	NPC81405
0.8802	High Similarity	NPC11062
0.8765	High Similarity	NPC62692
0.8765	High Similarity	NPC61967
0.8765	High Similarity	NPC27541
0.8765	High Similarity	NPC126984
0.8758	High Similarity	NPC200782
0.875	High Similarity	NPC84349
0.8734	High Similarity	NPC34421
0.8734	High Similarity	NPC237259
0.8734	High Similarity	NPC302054
0.8734	High Similarity	NPC253201
0.8734	High Similarity	NPC98206
0.8718	High Similarity	NPC211625
0.8712	High Similarity	NPC475779
0.8712	High Similarity	NPC86800
0.871	High Similarity	NPC216755
0.871	High Similarity	NPC286038
0.8704	High Similarity	NPC472773
0.8696	High Similarity	NPC472299
0.8679	High Similarity	NPC155939
0.8679	High Similarity	NPC296807
0.8679	High Similarity	NPC141538
0.8675	High Similarity	NPC202260
0.8671	High Similarity	NPC472672
0.8671	High Similarity	NPC48671
0.8671	High Similarity	NPC268905
0.8667	High Similarity	NPC302392
0.8667	High Similarity	NPC88593
0.8654	High Similarity	NPC66991
0.865	High Similarity	NPC276551
0.865	High Similarity	NPC276735
0.8642	High Similarity	NPC470792
0.8642	High Similarity	NPC82851
0.8642	High Similarity	NPC472771
0.8634	High Similarity	NPC475967
0.8627	High Similarity	NPC121158
0.8616	High Similarity	NPC114880
0.8606	High Similarity	NPC271235
0.8606	High Similarity	NPC160651
0.8606	High Similarity	NPC471397
0.8599	High Similarity	NPC234494
0.8598	High Similarity	NPC470875
0.859	High Similarity	NPC471174
0.8589	High Similarity	NPC469338
0.8589	High Similarity	NPC477405
0.8589	High Similarity	NPC134254
0.8589	High Similarity	NPC39986
0.8589	High Similarity	NPC292389
0.8589	High Similarity	NPC302369
0.858	High Similarity	NPC335761
0.8571	High Similarity	NPC472776
0.8571	High Similarity	NPC475122
0.8571	High Similarity	NPC243577
0.8571	High Similarity	NPC241951
0.8571	High Similarity	NPC470152
0.8571	High Similarity	NPC475759
0.8571	High Similarity	NPC472777
0.8571	High Similarity	NPC472778
0.8571	High Similarity	NPC299038
0.8562	High Similarity	NPC92979
0.8554	High Similarity	NPC470995
0.8553	High Similarity	NPC476201
0.8553	High Similarity	NPC33938
0.8553	High Similarity	NPC246164
0.8553	High Similarity	NPC469503
0.8545	High Similarity	NPC173516
0.8545	High Similarity	NPC472282
0.8545	High Similarity	NPC472774
0.8545	High Similarity	NPC472775
0.8544	High Similarity	NPC470997
0.8543	High Similarity	NPC307401
0.8537	High Similarity	NPC469849
0.8537	High Similarity	NPC470940
0.8537	High Similarity	NPC470182
0.8528	High Similarity	NPC69028
0.8528	High Similarity	NPC5079
0.8528	High Similarity	NPC263432
0.8521	High Similarity	NPC472665
0.8519	High Similarity	NPC307383
0.8519	High Similarity	NPC472671
0.8516	High Similarity	NPC96903
0.8516	High Similarity	NPC472572
0.8516	High Similarity	NPC200471
0.8516	High Similarity	NPC476973
0.8516	High Similarity	NPC177940
0.8516	High Similarity	NPC158663
0.8516	High Similarity	NPC184817
0.8516	High Similarity	NPC171525
0.8516	High Similarity	NPC174982
0.8516	High Similarity	NPC29704
0.8516	High Similarity	NPC473088
0.8516	High Similarity	NPC471104
0.8516	High Similarity	NPC472575
0.8516	High Similarity	NPC472568
0.8516	High Similarity	NPC469349
0.8516	High Similarity	NPC472571
0.8516	High Similarity	NPC470157
0.8516	High Similarity	NPC470159
0.8516	High Similarity	NPC70403
0.8512	High Similarity	NPC148185
0.8506	High Similarity	NPC163087
0.85	High Similarity	NPC282445
0.85	High Similarity	NPC178932
0.8497	Intermediate Similarity	NPC67003
0.8485	Intermediate Similarity	NPC93172
0.8485	Intermediate Similarity	NPC97574
0.8476	Intermediate Similarity	NPC51568
0.8476	Intermediate Similarity	NPC234660
0.8471	Intermediate Similarity	NPC473215
0.8462	Intermediate Similarity	NPC41182
0.8457	Intermediate Similarity	NPC214495
0.8457	Intermediate Similarity	NPC249021
0.8457	Intermediate Similarity	NPC475066
0.8457	Intermediate Similarity	NPC472772
0.8457	Intermediate Similarity	NPC470119
0.8452	Intermediate Similarity	NPC57628
0.8452	Intermediate Similarity	NPC472569
0.8452	Intermediate Similarity	NPC472573
0.8452	Intermediate Similarity	NPC11685
0.8452	Intermediate Similarity	NPC70716
0.8452	Intermediate Similarity	NPC163719
0.8452	Intermediate Similarity	NPC125106
0.8452	Intermediate Similarity	NPC95265
0.8452	Intermediate Similarity	NPC472570
0.8452	Intermediate Similarity	NPC95810
0.8452	Intermediate Similarity	NPC188865
0.8452	Intermediate Similarity	NPC25768
0.8452	Intermediate Similarity	NPC476974
0.8447	Intermediate Similarity	NPC35000
0.8447	Intermediate Similarity	NPC264943
0.8447	Intermediate Similarity	NPC75310
0.8447	Intermediate Similarity	NPC476262
0.8447	Intermediate Similarity	NPC25351
0.8447	Intermediate Similarity	NPC469336
0.8439	Intermediate Similarity	NPC472663
0.8439	Intermediate Similarity	NPC472662
0.8434	Intermediate Similarity	NPC473753
0.8434	Intermediate Similarity	NPC473766
0.8431	Intermediate Similarity	NPC275592
0.8431	Intermediate Similarity	NPC100913
0.8428	Intermediate Similarity	NPC477905
0.8428	Intermediate Similarity	NPC196846
0.8424	Intermediate Similarity	NPC271657
0.8418	Intermediate Similarity	NPC471007
0.8418	Intermediate Similarity	NPC470245
0.8418	Intermediate Similarity	NPC473214
0.8418	Intermediate Similarity	NPC19747
0.8415	Intermediate Similarity	NPC329938
0.8415	Intermediate Similarity	NPC207978
0.8415	Intermediate Similarity	NPC18347

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 NPC79571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	798
0.2-0.3	1482
0.3-0.4	2477
0.4-0.5	2206
0.5-0.6	1252
0.6-0.7	486
0.7-0.8	153
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD8434	Phase 2
0.8387	Intermediate Similarity	NPD4628	Phase 3
0.8125	Intermediate Similarity	NPD6273	Approved
0.811	Intermediate Similarity	NPD5760	Phase 2
0.811	Intermediate Similarity	NPD5761	Phase 2
0.8035	Intermediate Similarity	NPD6764	Approved
0.8035	Intermediate Similarity	NPD6765	Approved
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7458	Discontinued
0.7965	Intermediate Similarity	NPD5844	Phase 1
0.795	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD8127	Discontinued
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7892	Intermediate Similarity	NPD7819	Suspended
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7075	Discontinued
0.7853	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6784	Approved
0.7853	Intermediate Similarity	NPD6785	Approved
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7798	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6801	Discontinued
0.7669	Intermediate Similarity	NPD6799	Approved
0.7665	Intermediate Similarity	NPD7411	Suspended
0.7661	Intermediate Similarity	NPD5494	Approved
0.7651	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8312	Approved
0.764	Intermediate Similarity	NPD8313	Approved
0.7637	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.7607	Intermediate Similarity	NPD7236	Approved
0.7605	Intermediate Similarity	NPD4380	Phase 2
0.7602	Intermediate Similarity	NPD919	Approved
0.7602	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7003	Approved
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD8404	Phase 2
0.7588	Intermediate Similarity	NPD7768	Phase 2
0.7574	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7473	Discontinued
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.753	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD5403	Approved
0.753	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD3817	Phase 2
0.7515	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD3882	Suspended
0.7485	Intermediate Similarity	NPD8166	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4966	Approved
0.7471	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2796	Approved
0.7453	Intermediate Similarity	NPD6100	Approved
0.7453	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3226	Approved
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5402	Approved
0.7421	Intermediate Similarity	NPD7497	Discontinued
0.7416	Intermediate Similarity	NPD7074	Phase 3
0.7414	Intermediate Similarity	NPD6959	Discontinued
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7228	Approved
0.7399	Intermediate Similarity	NPD6234	Discontinued
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7391	Intermediate Similarity	NPD2799	Discontinued
0.7389	Intermediate Similarity	NPD7095	Approved
0.7386	Intermediate Similarity	NPD1608	Approved
0.7381	Intermediate Similarity	NPD7239	Suspended
0.7371	Intermediate Similarity	NPD3787	Discontinued
0.7371	Intermediate Similarity	NPD6232	Discontinued
0.7362	Intermediate Similarity	NPD1549	Phase 2
0.736	Intermediate Similarity	NPD7054	Approved
0.736	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1551	Phase 2
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7342	Intermediate Similarity	NPD3764	Approved
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7318	Intermediate Similarity	NPD7472	Approved
0.7317	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7799	Discontinued
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD7177	Discontinued
0.7301	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5763	Approved
0.7301	Intermediate Similarity	NPD1471	Phase 3
0.7301	Intermediate Similarity	NPD5762	Approved
0.7296	Intermediate Similarity	NPD8032	Phase 2
0.7278	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD2801	Approved
0.725	Intermediate Similarity	NPD4140	Approved
0.724	Intermediate Similarity	NPD7435	Discontinued
0.7238	Intermediate Similarity	NPD7240	Approved
0.7238	Intermediate Similarity	NPD7251	Discontinued
0.7233	Intermediate Similarity	NPD3268	Approved
0.7229	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD7097	Phase 1
0.7216	Intermediate Similarity	NPD1247	Approved
0.7207	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2532	Approved
0.7202	Intermediate Similarity	NPD2533	Approved
0.7202	Intermediate Similarity	NPD2534	Approved
0.7198	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7808	Phase 3
0.7195	Intermediate Similarity	NPD2344	Approved
0.719	Intermediate Similarity	NPD17	Approved
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.7182	Intermediate Similarity	NPD6797	Phase 2
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7178	Intermediate Similarity	NPD1510	Phase 2
0.7161	Intermediate Similarity	NPD3972	Approved
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6677	Suspended
0.7143	Intermediate Similarity	NPD1511	Approved
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD2354	Approved
0.7126	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3887	Approved
0.7125	Intermediate Similarity	NPD2313	Discontinued
0.712	Intermediate Similarity	NPD8407	Phase 2
0.7107	Intermediate Similarity	NPD6832	Phase 2
0.7099	Intermediate Similarity	NPD5735	Approved
0.7098	Intermediate Similarity	NPD3057	Approved
0.7095	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7028	Phase 2
0.7091	Intermediate Similarity	NPD6002	Phase 3
0.7091	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6004	Phase 3
0.7091	Intermediate Similarity	NPD6005	Phase 3
0.7091	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6780	Approved
0.7083	Intermediate Similarity	NPD6776	Approved
0.7083	Intermediate Similarity	NPD6777	Approved
0.7083	Intermediate Similarity	NPD6781	Approved
0.7083	Intermediate Similarity	NPD4107	Approved
0.7083	Intermediate Similarity	NPD6778	Approved
0.7083	Intermediate Similarity	NPD6779	Approved
0.7083	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD8435	Approved
0.7059	Intermediate Similarity	NPD8361	Approved
0.7059	Intermediate Similarity	NPD8360	Approved
0.7059	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1512	Approved
0.7055	Intermediate Similarity	NPD1607	Approved
0.7049	Intermediate Similarity	NPD8368	Discontinued
0.7043	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4060	Phase 1
0.7037	Intermediate Similarity	NPD4307	Phase 2
0.7037	Intermediate Similarity	NPD1240	Approved
0.703	Intermediate Similarity	NPD2935	Discontinued
0.703	Intermediate Similarity	NPD2438	Suspended
0.7025	Intermediate Similarity	NPD3267	Approved
0.7025	Intermediate Similarity	NPD3266	Approved
0.7024	Intermediate Similarity	NPD2309	Approved
0.702	Intermediate Similarity	NPD7874	Approved
0.702	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3533	Approved
0.701	Intermediate Similarity	NPD2972	Approved
0.7006	Intermediate Similarity	NPD2800	Approved
0.7	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5124	Phase 1
0.6994	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7057	Phase 3
0.6989	Remote Similarity	NPD7058	Phase 2
0.6981	Remote Similarity	NPD2798	Approved
0.6978	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7697	Approved
0.6974	Remote Similarity	NPD7696	Phase 3
0.6974	Remote Similarity	NPD7698	Approved
0.697	Remote Similarity	NPD8151	Discontinued
0.6968	Remote Similarity	NPD1778	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