NPASS Compound

Structure

NPC18729 OpenBabel06302216032D 65 72 0 0 1 0 0 0 0 0999 V2000 7.6875 1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8333 0.9863 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.8333 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.9791 -0.4932 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1250 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1250 0.9863 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.9791 1.4795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2708 1.4795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2708 2.4658 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1250 2.9589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1250 3.9452 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2708 4.4384 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2708 5.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 5.9178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 3.9452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 2.9589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5625 2.4658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7083 2.9589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7083 3.9452 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8542 4.4384 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 3.9452 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8542 4.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7083 3.9452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8542 5.4247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8542 2.4658 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8542 1.4795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9863 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8542 1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7083 0.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7083 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5625 0.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8542 -0.4932 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8542 -1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7083 -1.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5625 -1.4795 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5625 -3.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5625 -0.4932 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4166 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2708 -0.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2708 -1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1250 -1.9726 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.9791 -1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8333 -1.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8196 -1.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3264 -1.1184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8333 -2.9589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9791 -3.4521 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1250 -2.9589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1250 -3.9452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2708 -3.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 -2.9589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 -1.9726 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5625 -2.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9791 -4.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9863 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4932 -0.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8542 5.4247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5625 4.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9791 4.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9791 2.4658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2708 -0.4932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9791 -1.4795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6875 -0.4932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 7 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 3 65 1 0 0 0 0 4 5 1 0 0 0 0 4 64 1 0 0 0 0 5 6 1 0 0 0 0 5 63 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 10 62 1 0 0 0 0 11 12 1 0 0 0 0 11 61 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 60 1 0 0 0 0 20 21 1 0 0 0 0 20 59 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 56 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 31 38 1 0 0 0 0 31 32 1 0 0 0 0 31 33 1 0 0 0 0 33 34 1 0 0 0 0 33 56 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 36 53 1 0 0 0 0 36 37 1 0 0 0 0 36 38 1 0 0 0 0 38 39 1 0 0 0 0 39 40 1 0 0 0 0 40 41 2 0 0 0 0 41 53 1 0 0 0 0 41 42 1 0 0 0 0 42 49 1 0 0 0 0 42 43 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 44 46 1 0 0 0 0 44 47 1 0 0 0 0 47 48 1 0 0 0 0 48 49 1 0 0 0 0 48 55 1 0 0 0 0 49 50 1 0 0 0 0 49 51 1 0 0 0 0 51 52 1 0 0 0 0 52 53 1 0 0 0 0 53 54 1 0 0 0 0 56 57 1 0 0 0 0 56 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	926.52
Volume:	914.473
LogP:	3.036
LogD:	2.721
LogS:	-3.377
# Rotatable Bonds:	8
TPSA:	274.75
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	8
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.123
Synthetic Accessibility Score:	6.309
Fsp3:	0.938
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.765
MDCK Permeability:	0.00010695897799450904
Pgp-inhibitor:	0.286
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	84.93621063232422%
Volume Distribution (VD):	0.227
Pgp-substrate:	10.175825119018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.229
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	0.491
Half-life (T1/2):	0.022

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.336
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.001
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC18729

Natural Product ID:	NPC18729
*Common Name:**	ISTWCKNDZOSMPU-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ISTWCKNDZOSMPU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C48H78O17/c1-21-29(51)31(53)35(57)40(60-21)64-37-32(54)30(52)24(20-49)61-41(37)65-38-34(56)33(55)36(39(58)59)63-42(38)62-28-13-14-46(7)25(44(28,4)5)12-15-48(9)26(46)11-10-22-23-18-43(2,3)19-27(50)45(23,6)16-17-47(22,48)8/h10,21,23-38,40-42,49-57H,11-20H2,1-9H3,(H,58,59)
SMILES:	CC1C(C(C(C(O1)OC1C(C(C(CO)OC1OC1C(C(C(C(=O)O)OC1OC1CCC2(C)C(CCC3(C)C2CC=C2C4CC(C)(C)CC(C4(C)CCC32C)O)C1(C)C)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	188384
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[11141122]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25679337]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30892	Pueraria thomsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25628	Abrus pulchellus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30892	Pueraria thomsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25628	Abrus pulchellus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4545	Canavalia gladiata	Species	Fabaceae	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

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 NPC18729 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	282
0.1-0.2	1992
0.2-0.3	5500
0.3-0.4	10948
0.4-0.5	10876
0.5-0.6	6687
0.6-0.7	3662
0.7-0.8	1846
0.8-0.85	332
0.85-0.9	114
0.9-0.95	337
0.95-1	121

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 NPC18729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	2284
0.2-0.3	3889
0.3-0.4	1740
0.4-0.5	564
0.5-0.6	246
0.6-0.7	123
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

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