NPASS Compound

Structure

CID7349 OpenBabel06191715332D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3486 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8038 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3205 -3.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1839 1.1839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2502 0.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7162 -0.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8222 0.6516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5115 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8675 0.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 -0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5775 -0.8932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 -1.4500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8372 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9667 0.0000 C 0 0 2 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 -1.6743 -2.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7288 -1.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5338 -1.1769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2611 -0.2097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 -1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 22 1 1 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 6 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 6 0 0 0 21 22 1 1 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	4.338
LogD:	4.015
LogS:	-4.474
# Rotatable Bonds:	5
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	4.683
Fsp3:	0.773
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:	-4.774
MDCK Permeability:	2.391977068327833e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.49
30% Bioavailability (F30%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	96.4679946899414%
Volume Distribution (VD):	1.879
Pgp-substrate:	5.334282875061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.374
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.446
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	7.961
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.2
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.584
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.4
Carcinogencity:	0.229
Eye Corrosion:	0.019
Eye Irritation:	0.066
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC7349

Natural Product ID:	NPC7349
*Common Name:**	Vitexilactone
IUPAC Name:	[(1R,3R,4R,4aS,8aS)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
Synonyms:	Vitexilactone
Standard InCHIKey:	FBWWXAGANVJTLU-HEXLTJKYSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14-11-17(27-15(2)23)19-20(3,4)8-6-9-21(19,5)22(14,25)10-7-16-12-18(24)26-13-16/h12,14,17,19,25H,6-11,13H2,1-5H3/t14-,17-,19+,21+,22-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H](C)[C@]([C@@]2([C@@H]1C(C)(C)CCC2)C)(O)CCC1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517619
PubChem CID:	21636178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
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]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	leaves	Tam Kim, Cao Bang Province, in North Vietnam	2000-JUN	PMID[16989521]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17262892]
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]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21163339]
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]
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]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	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]
NPO21373	Vitex trifolia	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]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15454	Vitex rotundifolia	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]
NPO23218	Viscum coloratum	Species	Viscaceae	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]
NPO21298	Leucanthemum maximum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19074	Buddleja variabilis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21373	Vitex trifolia	Species	Lamiaceae	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]
NPO16146	Osmundaria colensoi	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20678	Grindelia nana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20536	Salvia nubicola	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21798	Dacrydium biforme	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20184	Streptomyces misawanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21505	Calea megacephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7865	Scapania nemorea	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21636	Didemnum inarmatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21736	Abies nobilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22062	Leptothorax acervorum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17108	Lecanora lividocinerea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22582	Smenospongia echina	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22762	Eremophila serrulata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14394	Hakea saligna	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22994	Cordyline indivisa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5952	Phegopteris bukoensis	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22323	Pinus picea	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22248	Alkanna hirsutissima	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12225	Amsinckia menziesii	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22710	Acrocomia sclerocarpa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23057	Primula hirsuta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19921	Polyphaga sinensis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21113	Coronophora gregaria	Species	Nitschkiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14247	Melaleuca uncinata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21998	Corydalis cornuta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22940	Delphinium campylocentrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7080	Monascus purpureus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20043	Vallaris solanacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18530	Shigella flexneri	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20360	Mentha pulegiformis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18571	Drypetes roxburghii	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22454	Picris radicata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21247	Nephroma australe	Species	Nephromataceae	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
GI50	2
IC50	5
Others	1

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	GI50	>	5.0	ug.mL-1	PMID[533382]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	>	5.0	ug.mL-1	PMID[533382]
NPT994	Cell Line	ZR-75-30	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[533383]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[533383]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[533383]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[533383]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[533384]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	42500.0	nM	PMID[533384]

☑ 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 NPC7349 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	184
0.1-0.2	1258
0.2-0.3	4274
0.3-0.4	8510
0.4-0.5	13281
0.5-0.6	6755
0.6-0.7	6286
0.7-0.8	1890
0.8-0.85	174
0.85-0.9	71
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC105490
0.9348	High Similarity	NPC324841
0.9333	High Similarity	NPC276110
0.9247	High Similarity	NPC11974
0.9222	High Similarity	NPC140277
0.9149	High Similarity	NPC162973
0.9149	High Similarity	NPC109195
0.9149	High Similarity	NPC475038
0.9053	High Similarity	NPC160583
0.9032	High Similarity	NPC278673
0.9022	High Similarity	NPC475380
0.9022	High Similarity	NPC194132
0.9022	High Similarity	NPC209297
0.8936	High Similarity	NPC38855
0.8936	High Similarity	NPC471413
0.8936	High Similarity	NPC16601
0.8925	High Similarity	NPC51499
0.8925	High Similarity	NPC311241
0.8925	High Similarity	NPC100912
0.8925	High Similarity	NPC475446
0.8889	High Similarity	NPC78973
0.8876	High Similarity	NPC93411
0.8876	High Similarity	NPC106332
0.8866	High Similarity	NPC471206
0.8866	High Similarity	NPC51719
0.8864	High Similarity	NPC471219
0.8864	High Similarity	NPC131813
0.8854	High Similarity	NPC120009
0.8851	High Similarity	NPC32223
0.8842	High Similarity	NPC472554
0.8842	High Similarity	NPC268829
0.8842	High Similarity	NPC471412
0.8842	High Similarity	NPC295110
0.8842	High Similarity	NPC247701
0.8842	High Similarity	NPC222875
0.8842	High Similarity	NPC25177
0.883	High Similarity	NPC72647
0.883	High Similarity	NPC107806
0.883	High Similarity	NPC325229
0.883	High Similarity	NPC275086
0.8791	High Similarity	NPC329842
0.8791	High Similarity	NPC78594
0.8778	High Similarity	NPC170633
0.8776	High Similarity	NPC471205
0.8776	High Similarity	NPC319438
0.8776	High Similarity	NPC216636
0.875	High Similarity	NPC472552
0.875	High Similarity	NPC476081
0.875	High Similarity	NPC474013
0.8736	High Similarity	NPC476927
0.8696	High Similarity	NPC53555
0.8673	High Similarity	NPC220217
0.8673	High Similarity	NPC119855
0.866	High Similarity	NPC97487
0.866	High Similarity	NPC281378
0.866	High Similarity	NPC196471
0.866	High Similarity	NPC45897
0.866	High Similarity	NPC189588
0.866	High Similarity	NPC10232
0.866	High Similarity	NPC472821
0.866	High Similarity	NPC187302
0.8636	High Similarity	NPC102048
0.8617	High Similarity	NPC29952
0.8605	High Similarity	NPC469802
0.8602	High Similarity	NPC161998
0.86	High Similarity	NPC322912
0.8586	High Similarity	NPC122816
0.8586	High Similarity	NPC475074
0.8557	High Similarity	NPC11956
0.8556	High Similarity	NPC471796
0.8556	High Similarity	NPC166857
0.8542	High Similarity	NPC251680
0.8511	High Similarity	NPC472441
0.8506	High Similarity	NPC170303
0.85	High Similarity	NPC38948
0.8495	Intermediate Similarity	NPC472641
0.8495	Intermediate Similarity	NPC110022
0.8495	Intermediate Similarity	NPC472640
0.8485	Intermediate Similarity	NPC34768
0.8485	Intermediate Similarity	NPC186668
0.8469	Intermediate Similarity	NPC471938
0.8469	Intermediate Similarity	NPC23584
0.8469	Intermediate Similarity	NPC120321
0.8462	Intermediate Similarity	NPC291665
0.8438	Intermediate Similarity	NPC218107
0.8427	Intermediate Similarity	NPC96055
0.8427	Intermediate Similarity	NPC306951
0.8421	Intermediate Similarity	NPC134072
0.8421	Intermediate Similarity	NPC234993
0.8421	Intermediate Similarity	NPC165632
0.8416	Intermediate Similarity	NPC206618
0.8409	Intermediate Similarity	NPC471218
0.8409	Intermediate Similarity	NPC256112
0.8409	Intermediate Similarity	NPC2524
0.8404	Intermediate Similarity	NPC57117
0.84	Intermediate Similarity	NPC302788
0.84	Intermediate Similarity	NPC187435
0.84	Intermediate Similarity	NPC67321
0.8387	Intermediate Similarity	NPC473675
0.8387	Intermediate Similarity	NPC234335
0.8387	Intermediate Similarity	NPC472811
0.8384	Intermediate Similarity	NPC471937
0.837	Intermediate Similarity	NPC82876
0.837	Intermediate Similarity	NPC246028
0.837	Intermediate Similarity	NPC261320
0.8367	Intermediate Similarity	NPC472815
0.8367	Intermediate Similarity	NPC471914
0.8351	Intermediate Similarity	NPC477968
0.8351	Intermediate Similarity	NPC20113
0.8351	Intermediate Similarity	NPC477971
0.8351	Intermediate Similarity	NPC228251
0.8351	Intermediate Similarity	NPC161527
0.8351	Intermediate Similarity	NPC219285
0.8351	Intermediate Similarity	NPC477972
0.8333	Intermediate Similarity	NPC30984
0.8333	Intermediate Similarity	NPC253604
0.8333	Intermediate Similarity	NPC177047
0.8317	Intermediate Similarity	NPC181994
0.8317	Intermediate Similarity	NPC50124
0.8316	Intermediate Similarity	NPC111273
0.8316	Intermediate Similarity	NPC471915
0.8315	Intermediate Similarity	NPC311070
0.83	Intermediate Similarity	NPC218158
0.8298	Intermediate Similarity	NPC139692
0.8298	Intermediate Similarity	NPC152778
0.8298	Intermediate Similarity	NPC205034
0.8298	Intermediate Similarity	NPC162615
0.8298	Intermediate Similarity	NPC472812
0.8283	Intermediate Similarity	NPC474822
0.8283	Intermediate Similarity	NPC473523
0.828	Intermediate Similarity	NPC472642
0.828	Intermediate Similarity	NPC280149
0.828	Intermediate Similarity	NPC221111
0.828	Intermediate Similarity	NPC310479
0.828	Intermediate Similarity	NPC220216
0.8265	Intermediate Similarity	NPC475617
0.8242	Intermediate Similarity	NPC475069
0.8242	Intermediate Similarity	NPC175145
0.8235	Intermediate Similarity	NPC475030
0.8229	Intermediate Similarity	NPC16967
0.8218	Intermediate Similarity	NPC179380
0.8211	Intermediate Similarity	NPC279410
0.8211	Intermediate Similarity	NPC119562
0.8211	Intermediate Similarity	NPC472360
0.8211	Intermediate Similarity	NPC472416
0.8211	Intermediate Similarity	NPC201725
0.82	Intermediate Similarity	NPC473543
0.8191	Intermediate Similarity	NPC72845
0.8191	Intermediate Similarity	NPC124374
0.8191	Intermediate Similarity	NPC477574
0.8182	Intermediate Similarity	NPC165250
0.8182	Intermediate Similarity	NPC281880
0.8182	Intermediate Similarity	NPC475344
0.8182	Intermediate Similarity	NPC476769
0.8182	Intermediate Similarity	NPC476471
0.8172	Intermediate Similarity	NPC16265
0.8163	Intermediate Similarity	NPC477721
0.8163	Intermediate Similarity	NPC477716
0.8163	Intermediate Similarity	NPC47024
0.8163	Intermediate Similarity	NPC476767
0.8163	Intermediate Similarity	NPC54705
0.8152	Intermediate Similarity	NPC264546
0.8152	Intermediate Similarity	NPC471779
0.8144	Intermediate Similarity	NPC477718
0.8144	Intermediate Similarity	NPC210337
0.8144	Intermediate Similarity	NPC473244
0.8144	Intermediate Similarity	NPC477719
0.8144	Intermediate Similarity	NPC231751
0.8144	Intermediate Similarity	NPC199099
0.8137	Intermediate Similarity	NPC189075
0.8137	Intermediate Similarity	NPC275539
0.8137	Intermediate Similarity	NPC306265
0.8137	Intermediate Similarity	NPC88701
0.8132	Intermediate Similarity	NPC471795
0.8132	Intermediate Similarity	NPC164424
0.8125	Intermediate Similarity	NPC476720
0.8119	Intermediate Similarity	NPC172867
0.8113	Intermediate Similarity	NPC471816
0.8111	Intermediate Similarity	NPC42476
0.8105	Intermediate Similarity	NPC38232
0.8105	Intermediate Similarity	NPC99653
0.81	Intermediate Similarity	NPC180204
0.81	Intermediate Similarity	NPC112009
0.81	Intermediate Similarity	NPC474124
0.809	Intermediate Similarity	NPC159148
0.8085	Intermediate Similarity	NPC302280
0.8085	Intermediate Similarity	NPC209816
0.8085	Intermediate Similarity	NPC182136
0.8081	Intermediate Similarity	NPC477717
0.8077	Intermediate Similarity	NPC470076
0.8065	Intermediate Similarity	NPC472809
0.8065	Intermediate Similarity	NPC472810
0.8065	Intermediate Similarity	NPC242448
0.8061	Intermediate Similarity	NPC473154
0.8058	Intermediate Similarity	NPC475586
0.8046	Intermediate Similarity	NPC189206
0.8046	Intermediate Similarity	NPC132542
0.8043	Intermediate Similarity	NPC102996
0.8041	Intermediate Similarity	NPC473964
0.8041	Intermediate Similarity	NPC473153

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 NPC7349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1492
0.2-0.3	3824
0.3-0.4	2392
0.4-0.5	827
0.5-0.6	207
0.6-0.7	210
0.7-0.8	34
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD7638	Approved
0.8542	High Similarity	NPD7640	Approved
0.8542	High Similarity	NPD7639	Approved
0.7963	Intermediate Similarity	NPD7328	Approved
0.7963	Intermediate Similarity	NPD7327	Approved
0.789	Intermediate Similarity	NPD7516	Approved
0.7885	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7632	Discontinued
0.781	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD5344	Discontinued
0.77	Intermediate Similarity	NPD4225	Approved
0.7658	Intermediate Similarity	NPD8294	Approved
0.7658	Intermediate Similarity	NPD8377	Approved
0.7624	Intermediate Similarity	NPD6648	Approved
0.7619	Intermediate Similarity	NPD6686	Approved
0.7609	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8033	Approved
0.7589	Intermediate Similarity	NPD8335	Approved
0.7589	Intermediate Similarity	NPD8378	Approved
0.7589	Intermediate Similarity	NPD8380	Approved
0.7589	Intermediate Similarity	NPD8296	Approved
0.7589	Intermediate Similarity	NPD8379	Approved
0.7524	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7748	Approved
0.7426	Intermediate Similarity	NPD7902	Approved
0.7423	Intermediate Similarity	NPD6051	Approved
0.7391	Intermediate Similarity	NPD7525	Registered
0.7328	Intermediate Similarity	NPD7507	Approved
0.7281	Intermediate Similarity	NPD7503	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7264	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD7128	Approved
0.7264	Intermediate Similarity	NPD6675	Approved
0.7264	Intermediate Similarity	NPD5739	Approved
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7129	Intermediate Similarity	NPD7900	Approved
0.7129	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6008	Approved
0.7083	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7115	Discovery
0.7064	Intermediate Similarity	NPD6373	Approved
0.7064	Intermediate Similarity	NPD6372	Approved
0.7037	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD5701	Approved
0.701	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6979	Remote Similarity	NPD6695	Phase 3
0.6972	Remote Similarity	NPD6011	Approved
0.6972	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4632	Approved
0.6939	Remote Similarity	NPD7521	Approved
0.6939	Remote Similarity	NPD3618	Phase 1
0.6939	Remote Similarity	NPD7334	Approved
0.6939	Remote Similarity	NPD6684	Approved
0.6939	Remote Similarity	NPD6409	Approved
0.6939	Remote Similarity	NPD7146	Approved
0.6939	Remote Similarity	NPD5330	Approved
0.6937	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6869	Approved
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6649	Approved
0.6937	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD6650	Approved
0.6937	Remote Similarity	NPD8130	Phase 1
0.6931	Remote Similarity	NPD8035	Phase 2
0.6931	Remote Similarity	NPD7637	Suspended
0.6931	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6915	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD6013	Approved
0.6909	Remote Similarity	NPD6014	Approved
0.69	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD8297	Approved
0.6875	Remote Similarity	NPD6882	Approved
0.6863	Remote Similarity	NPD4202	Approved
0.6832	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD6698	Approved
0.6832	Remote Similarity	NPD7838	Discovery
0.68	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6903	Approved
0.68	Remote Similarity	NPD5737	Approved
0.68	Remote Similarity	NPD6672	Approved
0.6783	Remote Similarity	NPD6009	Approved
0.6765	Remote Similarity	NPD6079	Approved
0.6765	Remote Similarity	NPD5693	Phase 1
0.6762	Remote Similarity	NPD4755	Approved
0.6752	Remote Similarity	NPD6319	Approved
0.6731	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5695	Phase 3
0.6727	Remote Similarity	NPD6412	Phase 2
0.6723	Remote Similarity	NPD7604	Phase 2
0.67	Remote Similarity	NPD7750	Discontinued
0.67	Remote Similarity	NPD7524	Approved
0.67	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3573	Approved
0.6698	Remote Similarity	NPD5696	Approved
0.6698	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6612	Remote Similarity	NPD6336	Discontinued
0.6612	Remote Similarity	NPD6616	Approved
0.661	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD6054	Approved
0.6596	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6335	Approved
0.6574	Remote Similarity	NPD5223	Approved
0.6569	Remote Similarity	NPD6080	Approved
0.6569	Remote Similarity	NPD6904	Approved
0.6569	Remote Similarity	NPD6673	Approved
0.6566	Remote Similarity	NPD3133	Approved
0.6566	Remote Similarity	NPD4786	Approved
0.6566	Remote Similarity	NPD3666	Approved
0.6566	Remote Similarity	NPD3665	Phase 1
0.6562	Remote Similarity	NPD6929	Approved
0.6562	Remote Similarity	NPD4195	Approved
0.6559	Remote Similarity	NPD6926	Approved
0.6559	Remote Similarity	NPD6924	Approved
0.6557	Remote Similarity	NPD7078	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6552	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD6371	Approved
0.6545	Remote Similarity	NPD5141	Approved
0.6538	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD5779	Approved
0.6531	Remote Similarity	NPD3667	Approved
0.6525	Remote Similarity	NPD7101	Approved
0.6525	Remote Similarity	NPD7100	Approved
0.6514	Remote Similarity	NPD5224	Approved
0.6514	Remote Similarity	NPD5225	Approved
0.6514	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD4633	Approved
0.6509	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5222	Approved
0.6509	Remote Similarity	NPD5221	Approved
0.6509	Remote Similarity	NPD4697	Phase 3
0.6504	Remote Similarity	NPD7736	Approved
0.65	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6370	Approved
0.6496	Remote Similarity	NPD6317	Approved
0.6495	Remote Similarity	NPD7509	Discontinued
0.6495	Remote Similarity	NPD7514	Phase 3
0.6495	Remote Similarity	NPD7332	Phase 2
0.646	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5175	Approved
0.6455	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD4754	Approved
0.6449	Remote Similarity	NPD5173	Approved
0.6446	Remote Similarity	NPD8328	Phase 3
0.6442	Remote Similarity	NPD5284	Approved
0.6442	Remote Similarity	NPD7087	Discontinued
0.6442	Remote Similarity	NPD5281	Approved
0.6441	Remote Similarity	NPD6314	Approved
0.6441	Remote Similarity	NPD6313	Approved
0.6436	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4519	Discontinued
0.6436	Remote Similarity	NPD4623	Approved
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6933	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6909	Approved
0.6417	Remote Similarity	NPD6908	Approved
0.641	Remote Similarity	NPD6868	Approved
0.6408	Remote Similarity	NPD4753	Phase 2
0.6404	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD4223	Phase 3
0.6364	Remote Similarity	NPD4221	Approved
0.6354	Remote Similarity	NPD6932	Approved
0.6354	Remote Similarity	NPD5776	Phase 2
0.6354	Remote Similarity	NPD6925	Approved
0.6346	Remote Similarity	NPD5785	Approved
0.6346	Remote Similarity	NPD3168	Discontinued
0.6344	Remote Similarity	NPD4243	Approved
0.6339	Remote Similarity	NPD4768	Approved
0.6339	Remote Similarity	NPD4767	Approved
0.6337	Remote Similarity	NPD5329	Approved
0.6337	Remote Similarity	NPD6893	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