NPASS Compound

Structure

NPC148858 OpenBabel06302216162D 22 24 0 0 1 0 0 0 0 0999 V2000 3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0491 0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 5 3 1 1 0 0 0 5 6 1 0 0 0 0 5 22 1 0 0 0 0 7 6 1 1 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 1 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 10 11 1 0 0 0 0 12 11 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 1 0 0 0 19 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	343.751
LogP:	4.63
LogD:	4.162
LogS:	-5.046
# Rotatable Bonds:	1
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	4.74
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.675
MDCK Permeability:	2.2753814846510068e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	95.77564239501953%
Volume Distribution (VD):	1.341
Pgp-substrate:	2.678116798400879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.341
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	9.739
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.321
Carcinogencity:	0.025
Eye Corrosion:	0.982
Eye Irritation:	0.692
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC148858

Natural Product ID:	NPC148858
*Common Name:**	JBQIJRIILPMQRP-GBZDAYACSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JBQIJRIILPMQRP-GBZDAYACSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-7-13(2)14-12-16-19(5,22-14)11-8-15-18(3,4)10-9-17(21)20(15,16)6/h7,14-17,21H,8-12H2,1-6H3/b13-7+/t14-,15-,16-,17+,19+,20-/m0/s1
SMILES:	C/C=C(C)/[C@@H]1C[C@H]2[C@@](C)(CC[C@H]3C(C)(C)CC[C@H]([C@]23C)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101321339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(98)00208-8]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[22122667]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22122667]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26575	Scapania undulata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4408	Alstonia rostrata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10837	Matthiola incana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25961	Liatris graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26275	Dactynotus rudbeckiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7055	Lychnophora hakeaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26575	Scapania undulata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO937	Limnodynastes terraereginae	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26818	Euphorbia kaleniczenkii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26178	Guarea glabra	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26390	Triphasia trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26519	Acanthodoris nanaimoensis	Species	Onchidorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25939	Lupinus macounii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26360	Methysticodendron amesianum	n.a.	n.a.	n.a.	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC148858 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	167
0.1-0.2	1343
0.2-0.3	4688
0.3-0.4	12494
0.4-0.5	10243
0.5-0.6	6336
0.6-0.7	5466
0.7-0.8	1739
0.8-0.85	181
0.85-0.9	31
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID

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 NPC148858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1537
0.2-0.3	4064
0.3-0.4	2308
0.4-0.5	634
0.5-0.6	200
0.6-0.7	194
0.7-0.8	52
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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