NPASS Compound

Structure

NPC159690 OpenBabel06302215212D 35 38 0 0 1 0 0 0 0 0999 V2000 -0.2308 -3.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 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 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7170 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3972 3.2219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3944 3.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8944 4.0132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 2.3209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9326 2.5434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6128 1.8104 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3180 0.8548 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3431 0.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6629 1.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3682 2.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9982 0.1218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5877 2.0329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -0.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -2.6270 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 3 7 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 7 8 1 0 0 0 0 7 35 1 1 0 0 0 8 9 1 0 0 0 0 8 34 1 6 0 0 0 9 10 1 6 0 0 0 11 9 1 1 0 0 0 11 12 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 14 13 1 1 0 0 0 14 15 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 6 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 20 21 1 1 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 25 1 0 0 0 0 25 26 1 1 0 0 0 25 27 1 0 0 0 0 27 28 1 6 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.35
Volume:	523.383
LogP:	3.767
LogD:	4.247
LogS:	-4.442
# Rotatable Bonds:	5
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	5.271
Fsp3:	0.897
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:	-4.83
MDCK Permeability:	4.8088702897075564e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.276
20% Bioavailability (F20%):	0.254
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	92.73603057861328%
Volume Distribution (VD):	0.89
Pgp-substrate:	2.115980625152588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	5.39
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.2
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.598
Carcinogencity:	0.035
Eye Corrosion:	0.014
Eye Irritation:	0.039
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC159690

Natural Product ID:	NPC159690
*Common Name:**	LRRBQWHWKJDDAW-XSTACDCCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LRRBQWHWKJDDAW-XSTACDCCSA-N
Standard InCHI:	InChI=1S/C29H48O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h7,15-16,18-26,30-33H,8-14H2,1-6H3/b17-7+/t16-,18-,19+,20-,21+,22+,23-,24+,25+,26+,28+,29+/m0/s1
SMILES:	C/C=C(C(C)C)/[C@H]([C@@H]([C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@@H]([C@@H](C[C@]4(C)[C@@H]3CC[C@]12C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001774] Brassinolides and derivatives

*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
NPO21105	Madhuca longifolia	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141115]
NPO16139	Garcinia lancilimba	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[17541202]
NPO18438	Samanea saman	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21228101]
NPO7210	Rhizophora mucronata	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19035	Croton cajucara	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18464	Pilocarpus goudotianus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19035	Croton cajucara	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7210	Rhizophora mucronata	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20942	Isoplexis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16139	Garcinia lancilimba	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1856	Tomophagus colossus	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18464	Pilocarpus goudotianus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21240	Pinus elliottii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13111	Aplophyllum dubium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18438	Samanea saman	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16994	Codiaeum variegatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21105	Madhuca longifolia	Species	Sapotaceae	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 NPC159690 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	201
0.1-0.2	1248
0.2-0.3	4035
0.3-0.4	8250
0.4-0.5	13059
0.5-0.6	6184
0.6-0.7	6833
0.7-0.8	2754
0.8-0.85	126
0.85-0.9	7
0.9-0.95	0
0.95-1	0

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 NPC159690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1481
0.2-0.3	3771
0.3-0.4	2439
0.4-0.5	759
0.5-0.6	229
0.6-0.7	236
0.7-0.8	67
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