NPASS Compound

Structure

CID162973 OpenBabel06191715532D 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 -4.1858 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9948 -0.3538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4781 0.4833 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 -1.6743 1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6173 0.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3022 0.7915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 1.4500 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 0.9337 -0.2502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1129 0.2650 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 -0.0000 -0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3486 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5510 0.1832 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 -1.6743 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8974 -0.7193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 0.4833 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3486 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 -1.5300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1262 0.9584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8628 -0.6687 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 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 21 22 1 6 0 0 0 22 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	4.216
LogD:	3.786
LogS:	-4.489
# 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:	4.598
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:	-4.846
MDCK Permeability:	2.5050730982911773e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.358

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	96.7815170288086%
Volume Distribution (VD):	2.503
Pgp-substrate:	4.547635555267334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.454
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	6.532
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.243
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.315
Carcinogencity:	0.358
Eye Corrosion:	0.013
Eye Irritation:	0.049
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC162973

Natural Product ID:	NPC162973
*Common Name:**	(Rel 5S,6R,8R,9R,10S)-6-Acetoxy-9-Hydroxy-13(14)-Labden-16,15-Olide
IUPAC Name:	[(1R,3R,4R,4aS,8aS)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-4-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	FFOPQHZFBMZAKK-UJHQHGQKSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14-13-17(27-15(2)23)18-20(3,4)9-6-10-21(18,5)22(14,25)11-7-16-8-12-26-19(16)24/h8,14,17-18,25H,6-7,9-13H2,1-5H3/t14-,17-,18+,21+,22-/m1/s1
SMILES:	C[C@@H]1C[C@H]([C@H]2C(C)(C)CCC[C@]2(C)[C@]1(CCC1=CCOC1=O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436598
PubChem CID:	10022565
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]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	whole plant	Cholistan desert near district Bahawalpur (Punjab), Pakistan	2003-Oct	PMID[20542692]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[2082684]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21922656]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
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]
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]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	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]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22188	Piper aequale	Species	Piperaceae	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]
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[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]
NPO21373	Vitex trifolia	Species	Lamiaceae	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]
NPO21298	Leucanthemum maximum	Species	Asteraceae	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]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	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]
NPO21505	Calea megacephala	Species	Asteraceae	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]
NPO22062	Leptothorax acervorum	Species	Formicidae	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]
NPO22582	Smenospongia echina	Species	Thorectidae	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]
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]
NPO22248	Alkanna hirsutissima	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22323	Pinus picea	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22710	Acrocomia sclerocarpa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12225	Amsinckia menziesii	Species	Boraginaceae	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]
NPO14247	Melaleuca uncinata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21113	Coronophora gregaria	Species	Nitschkiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	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]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21998	Corydalis cornuta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7080	Monascus purpureus	Species	Aspergillaceae	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]
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]
NPO21247	Nephroma australe	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	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]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[552629]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	45400.0	nM	PMID[552629]

☑ 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 NPC162973 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	205
0.1-0.2	1209
0.2-0.3	3907
0.3-0.4	6805
0.4-0.5	13662
0.5-0.6	6977
0.6-0.7	6598
0.7-0.8	3021
0.8-0.85	254
0.85-0.9	48
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC471413
0.9684	High Similarity	NPC471412
0.9468	High Similarity	NPC29952
0.9149	High Similarity	NPC7349
0.9053	High Similarity	NPC105490
0.899	High Similarity	NPC476081
0.8922	High Similarity	NPC275539
0.8922	High Similarity	NPC189075
0.8868	High Similarity	NPC471816
0.8866	High Similarity	NPC134072
0.8866	High Similarity	NPC234993
0.8824	High Similarity	NPC110496
0.88	High Similarity	NPC475038
0.88	High Similarity	NPC109195
0.88	High Similarity	NPC476769
0.8788	High Similarity	NPC471041
0.875	High Similarity	NPC139692
0.8725	High Similarity	NPC34768
0.8713	High Similarity	NPC120321
0.8713	High Similarity	NPC254202
0.8687	High Similarity	NPC72647
0.8687	High Similarity	NPC107806
0.8673	High Similarity	NPC209297
0.8673	High Similarity	NPC475380
0.8641	High Similarity	NPC67321
0.8641	High Similarity	NPC302788
0.8641	High Similarity	NPC187435
0.86	High Similarity	NPC476767
0.86	High Similarity	NPC117685
0.86	High Similarity	NPC324841
0.86	High Similarity	NPC47024
0.8586	High Similarity	NPC475446
0.8586	High Similarity	NPC311241
0.8586	High Similarity	NPC84335
0.8586	High Similarity	NPC100912
0.8586	High Similarity	NPC38530
0.8585	High Similarity	NPC90952
0.8585	High Similarity	NPC4573
0.8585	High Similarity	NPC194951
0.8585	High Similarity	NPC12046
0.8585	High Similarity	NPC269530
0.8585	High Similarity	NPC277769
0.8571	High Similarity	NPC90014
0.8571	High Similarity	NPC276110
0.8544	High Similarity	NPC469607
0.8529	High Similarity	NPC180204
0.8529	High Similarity	NPC112009
0.8515	High Similarity	NPC11974
0.8505	High Similarity	NPC157441
0.8505	High Similarity	NPC25909
0.8485	Intermediate Similarity	NPC242848
0.8485	Intermediate Similarity	NPC473964
0.8469	Intermediate Similarity	NPC140277
0.8462	Intermediate Similarity	NPC179380
0.8462	Intermediate Similarity	NPC216636
0.8462	Intermediate Similarity	NPC319438
0.8447	Intermediate Similarity	NPC118911
0.8438	Intermediate Similarity	NPC174342
0.8431	Intermediate Similarity	NPC165250
0.8431	Intermediate Similarity	NPC295791
0.8416	Intermediate Similarity	NPC54705
0.8416	Intermediate Similarity	NPC251680
0.8416	Intermediate Similarity	NPC470074
0.8416	Intermediate Similarity	NPC16601
0.8416	Intermediate Similarity	NPC201406
0.8411	Intermediate Similarity	NPC470063
0.8404	Intermediate Similarity	NPC65661
0.84	Intermediate Similarity	NPC285513
0.84	Intermediate Similarity	NPC473963
0.84	Intermediate Similarity	NPC254496
0.84	Intermediate Similarity	NPC474343
0.8396	Intermediate Similarity	NPC179642
0.8396	Intermediate Similarity	NPC472666
0.8381	Intermediate Similarity	NPC306265
0.8381	Intermediate Similarity	NPC476802
0.8381	Intermediate Similarity	NPC89171
0.8367	Intermediate Similarity	NPC472871
0.8365	Intermediate Similarity	NPC478208
0.835	Intermediate Similarity	NPC478057
0.835	Intermediate Similarity	NPC160583
0.8349	Intermediate Similarity	NPC469794
0.8349	Intermediate Similarity	NPC72772
0.8349	Intermediate Similarity	NPC196931
0.8333	Intermediate Similarity	NPC475958
0.8318	Intermediate Similarity	NPC469655
0.8318	Intermediate Similarity	NPC96739
0.8318	Intermediate Similarity	NPC474871
0.8318	Intermediate Similarity	NPC260786
0.8318	Intermediate Similarity	NPC474846
0.8318	Intermediate Similarity	NPC469656
0.8318	Intermediate Similarity	NPC174471
0.8317	Intermediate Similarity	NPC316598
0.8317	Intermediate Similarity	NPC108368
0.8317	Intermediate Similarity	NPC57079
0.8317	Intermediate Similarity	NPC216478
0.8317	Intermediate Similarity	NPC278673
0.8317	Intermediate Similarity	NPC23364
0.8302	Intermediate Similarity	NPC322912
0.8302	Intermediate Similarity	NPC112457
0.8302	Intermediate Similarity	NPC474243
0.83	Intermediate Similarity	NPC202833
0.83	Intermediate Similarity	NPC93245
0.83	Intermediate Similarity	NPC194132
0.8298	Intermediate Similarity	NPC32223
0.8288	Intermediate Similarity	NPC469380
0.8283	Intermediate Similarity	NPC476415
0.8283	Intermediate Similarity	NPC250075
0.8283	Intermediate Similarity	NPC103527
0.8283	Intermediate Similarity	NPC57117
0.8273	Intermediate Similarity	NPC475809
0.8273	Intermediate Similarity	NPC134430
0.8273	Intermediate Similarity	NPC473968
0.8265	Intermediate Similarity	NPC473944
0.8265	Intermediate Similarity	NPC472975
0.8265	Intermediate Similarity	NPC78594
0.8252	Intermediate Similarity	NPC31058
0.8252	Intermediate Similarity	NPC475320
0.8252	Intermediate Similarity	NPC22388
0.8252	Intermediate Similarity	NPC469606
0.8252	Intermediate Similarity	NPC273005
0.8252	Intermediate Similarity	NPC136289
0.8252	Intermediate Similarity	NPC472552
0.8247	Intermediate Similarity	NPC5509
0.8241	Intermediate Similarity	NPC221511
0.8241	Intermediate Similarity	NPC89227
0.8241	Intermediate Similarity	NPC170212
0.8241	Intermediate Similarity	NPC215643
0.8241	Intermediate Similarity	NPC151216
0.8241	Intermediate Similarity	NPC101825
0.8241	Intermediate Similarity	NPC17138
0.8241	Intermediate Similarity	NPC265499
0.8241	Intermediate Similarity	NPC475391
0.8235	Intermediate Similarity	NPC306856
0.8235	Intermediate Similarity	NPC474718
0.8235	Intermediate Similarity	NPC476299
0.8235	Intermediate Similarity	NPC38855
0.8235	Intermediate Similarity	NPC476274
0.8235	Intermediate Similarity	NPC474012
0.8224	Intermediate Similarity	NPC253906
0.8224	Intermediate Similarity	NPC5103
0.8218	Intermediate Similarity	NPC51499
0.8218	Intermediate Similarity	NPC175351
0.8218	Intermediate Similarity	NPC132753
0.8218	Intermediate Similarity	NPC121402
0.8218	Intermediate Similarity	NPC253826
0.8218	Intermediate Similarity	NPC474921
0.8218	Intermediate Similarity	NPC224356
0.8218	Intermediate Similarity	NPC151681
0.8211	Intermediate Similarity	NPC106416
0.8211	Intermediate Similarity	NPC86316
0.8208	Intermediate Similarity	NPC476479
0.82	Intermediate Similarity	NPC157686
0.82	Intermediate Similarity	NPC259042
0.82	Intermediate Similarity	NPC316215
0.82	Intermediate Similarity	NPC266899
0.82	Intermediate Similarity	NPC134067
0.82	Intermediate Similarity	NPC183012
0.819	Intermediate Similarity	NPC1679
0.819	Intermediate Similarity	NPC127609
0.819	Intermediate Similarity	NPC471206
0.819	Intermediate Similarity	NPC472645
0.819	Intermediate Similarity	NPC51719
0.8182	Intermediate Similarity	NPC234858
0.8182	Intermediate Similarity	NPC154363
0.8182	Intermediate Similarity	NPC472303
0.8182	Intermediate Similarity	NPC475657
0.8182	Intermediate Similarity	NPC190286
0.8182	Intermediate Similarity	NPC176840
0.8182	Intermediate Similarity	NPC147272
0.8182	Intermediate Similarity	NPC471127
0.8173	Intermediate Similarity	NPC120009
0.8173	Intermediate Similarity	NPC471938
0.8173	Intermediate Similarity	NPC36688
0.8173	Intermediate Similarity	NPC471208
0.8173	Intermediate Similarity	NPC95585
0.8173	Intermediate Similarity	NPC95899
0.8173	Intermediate Similarity	NPC282233
0.8165	Intermediate Similarity	NPC469496
0.8165	Intermediate Similarity	NPC962
0.8165	Intermediate Similarity	NPC159333
0.8165	Intermediate Similarity	NPC471204
0.8165	Intermediate Similarity	NPC474937
0.8165	Intermediate Similarity	NPC469454
0.8165	Intermediate Similarity	NPC71889
0.8165	Intermediate Similarity	NPC469463
0.8163	Intermediate Similarity	NPC232202
0.8163	Intermediate Similarity	NPC51486
0.8163	Intermediate Similarity	NPC78973
0.8158	Intermediate Similarity	NPC473979
0.8155	Intermediate Similarity	NPC224720
0.8155	Intermediate Similarity	NPC475099
0.8155	Intermediate Similarity	NPC222875
0.8155	Intermediate Similarity	NPC268829
0.8155	Intermediate Similarity	NPC476240
0.8155	Intermediate Similarity	NPC81530
0.8155	Intermediate Similarity	NPC247701
0.8155	Intermediate Similarity	NPC303559
0.8155	Intermediate Similarity	NPC472554
0.8155	Intermediate Similarity	NPC25177
0.8155	Intermediate Similarity	NPC472643

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 NPC162973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1497
0.2-0.3	3546
0.3-0.4	2402
0.4-0.5	1004
0.5-0.6	258
0.6-0.7	169
0.7-0.8	96
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD7638	Approved
0.8416	Intermediate Similarity	NPD7639	Approved
0.8416	Intermediate Similarity	NPD7640	Approved
0.8131	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6686	Approved
0.787	Intermediate Similarity	NPD6899	Approved
0.787	Intermediate Similarity	NPD6881	Approved
0.7863	Intermediate Similarity	NPD7507	Approved
0.785	Intermediate Similarity	NPD5739	Approved
0.785	Intermediate Similarity	NPD6675	Approved
0.785	Intermediate Similarity	NPD7128	Approved
0.785	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD7748	Approved
0.7736	Intermediate Similarity	NPD7632	Discontinued
0.7727	Intermediate Similarity	NPD7290	Approved
0.7727	Intermediate Similarity	NPD6883	Approved
0.7727	Intermediate Similarity	NPD7102	Approved
0.7706	Intermediate Similarity	NPD6011	Approved
0.7706	Intermediate Similarity	NPD7320	Approved
0.7692	Intermediate Similarity	NPD7902	Approved
0.7685	Intermediate Similarity	NPD6008	Approved
0.7679	Intermediate Similarity	NPD4632	Approved
0.7667	Intermediate Similarity	NPD7319	Approved
0.7658	Intermediate Similarity	NPD8130	Phase 1
0.7658	Intermediate Similarity	NPD6869	Approved
0.7658	Intermediate Similarity	NPD6650	Approved
0.7658	Intermediate Similarity	NPD6847	Approved
0.7658	Intermediate Similarity	NPD6649	Approved
0.7658	Intermediate Similarity	NPD6617	Approved
0.7636	Intermediate Similarity	NPD6373	Approved
0.7636	Intermediate Similarity	NPD6372	Approved
0.7636	Intermediate Similarity	NPD6012	Approved
0.7636	Intermediate Similarity	NPD6014	Approved
0.7636	Intermediate Similarity	NPD6013	Approved
0.7619	Intermediate Similarity	NPD4225	Approved
0.7615	Intermediate Similarity	NPD5701	Approved
0.7589	Intermediate Similarity	NPD8297	Approved
0.7589	Intermediate Similarity	NPD6882	Approved
0.7549	Intermediate Similarity	NPD7515	Phase 2
0.7549	Intermediate Similarity	NPD6079	Approved
0.7545	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3573	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7478	Intermediate Similarity	NPD6009	Approved
0.7476	Intermediate Similarity	NPD6399	Phase 3
0.7475	Intermediate Similarity	NPD1694	Approved
0.7436	Intermediate Similarity	NPD6319	Approved
0.7434	Intermediate Similarity	NPD6053	Discontinued
0.7414	Intermediate Similarity	NPD7328	Approved
0.7414	Intermediate Similarity	NPD7327	Approved
0.7407	Intermediate Similarity	NPD5211	Phase 2
0.7404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7900	Approved
0.7395	Intermediate Similarity	NPD7604	Phase 2
0.7383	Intermediate Similarity	NPD5286	Approved
0.7383	Intermediate Similarity	NPD5285	Approved
0.7383	Intermediate Similarity	NPD4696	Approved
0.7373	Intermediate Similarity	NPD5983	Phase 2
0.7358	Intermediate Similarity	NPD4755	Approved
0.735	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD7492	Approved
0.7315	Intermediate Similarity	NPD5344	Discontinued
0.7315	Intermediate Similarity	NPD5223	Approved
0.7288	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7273	Intermediate Similarity	NPD6616	Approved
0.7273	Intermediate Similarity	NPD5141	Approved
0.7265	Intermediate Similarity	NPD6335	Approved
0.7264	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5222	Approved
0.7264	Intermediate Similarity	NPD5221	Approved
0.7248	Intermediate Similarity	NPD5224	Approved
0.7248	Intermediate Similarity	NPD5226	Approved
0.7248	Intermediate Similarity	NPD5225	Approved
0.7248	Intermediate Similarity	NPD4633	Approved
0.7241	Intermediate Similarity	NPD6274	Approved
0.7228	Intermediate Similarity	NPD3618	Phase 1
0.7228	Intermediate Similarity	NPD5330	Approved
0.7228	Intermediate Similarity	NPD6684	Approved
0.7228	Intermediate Similarity	NPD7334	Approved
0.7228	Intermediate Similarity	NPD7521	Approved
0.7228	Intermediate Similarity	NPD7146	Approved
0.7228	Intermediate Similarity	NPD6409	Approved
0.7222	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD6648	Approved
0.7213	Intermediate Similarity	NPD7078	Approved
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7203	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7100	Approved
0.7196	Intermediate Similarity	NPD6084	Phase 2
0.7196	Intermediate Similarity	NPD5173	Approved
0.7196	Intermediate Similarity	NPD6083	Phase 2
0.7182	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD5175	Approved
0.7179	Intermediate Similarity	NPD6317	Approved
0.7167	Intermediate Similarity	NPD6370	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD8294	Approved
0.7119	Intermediate Similarity	NPD6314	Approved
0.7119	Intermediate Similarity	NPD6313	Approved
0.7115	Intermediate Similarity	NPD6698	Approved
0.7115	Intermediate Similarity	NPD46	Approved
0.7105	Intermediate Similarity	NPD4634	Approved
0.7103	Intermediate Similarity	NPD4697	Phase 3
0.7094	Intermediate Similarity	NPD6868	Approved
0.7087	Intermediate Similarity	NPD5737	Approved
0.7087	Intermediate Similarity	NPD6903	Approved
0.7087	Intermediate Similarity	NPD6672	Approved
0.7087	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8378	Approved
0.7083	Intermediate Similarity	NPD8335	Approved
0.7083	Intermediate Similarity	NPD6016	Approved
0.7083	Intermediate Similarity	NPD8380	Approved
0.7083	Intermediate Similarity	NPD8296	Approved
0.7083	Intermediate Similarity	NPD6015	Approved
0.7083	Intermediate Similarity	NPD8033	Approved
0.7083	Intermediate Similarity	NPD8379	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7048	Intermediate Similarity	NPD5693	Phase 1
0.7027	Intermediate Similarity	NPD4754	Approved
0.7025	Intermediate Similarity	NPD5988	Approved
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6412	Phase 2
0.6972	Remote Similarity	NPD5696	Approved
0.6967	Remote Similarity	NPD8328	Phase 3
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6371	Approved
0.6942	Remote Similarity	NPD6908	Approved
0.6942	Remote Similarity	NPD6909	Approved
0.6942	Remote Similarity	NPD7503	Approved
0.6942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4729	Approved
0.693	Remote Similarity	NPD5128	Approved
0.693	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6903	Remote Similarity	NPD4767	Approved
0.6903	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6411	Approved
0.6863	Remote Similarity	NPD3665	Phase 1
0.6863	Remote Similarity	NPD3133	Approved
0.6863	Remote Similarity	NPD3666	Approved
0.6863	Remote Similarity	NPD4786	Approved
0.6857	Remote Similarity	NPD6051	Approved
0.6857	Remote Similarity	NPD6080	Approved
0.6857	Remote Similarity	NPD6904	Approved
0.6857	Remote Similarity	NPD6673	Approved
0.685	Remote Similarity	NPD7260	Phase 2
0.6842	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3667	Approved
0.681	Remote Similarity	NPD5250	Approved
0.681	Remote Similarity	NPD5135	Approved
0.681	Remote Similarity	NPD5169	Approved
0.681	Remote Similarity	NPD5247	Approved
0.681	Remote Similarity	NPD5248	Approved
0.681	Remote Similarity	NPD5249	Phase 3
0.681	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5251	Approved
0.6803	Remote Similarity	NPD6921	Approved
0.68	Remote Similarity	NPD7525	Registered
0.6792	Remote Similarity	NPD5785	Approved
0.6752	Remote Similarity	NPD5217	Approved
0.6752	Remote Similarity	NPD5216	Approved
0.6752	Remote Similarity	NPD5215	Approved
0.6752	Remote Similarity	NPD5127	Approved
0.6746	Remote Similarity	NPD6033	Approved
0.6731	Remote Similarity	NPD4623	Approved
0.6731	Remote Similarity	NPD4519	Discontinued
0.6729	Remote Similarity	NPD5284	Approved
0.6729	Remote Similarity	NPD5281	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6724	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4753	Phase 2
0.6698	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD7838	Discovery
0.6635	Remote Similarity	NPD5329	Approved
0.6635	Remote Similarity	NPD1733	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data