NPASS Compound

Structure

NPC225997 OpenBabel06302215212D 43 44 0 0 1 0 0 0 0 0999 V2000 0.6145 -1.0092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2430 -0.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2059 -0.4299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2059 -1.4077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -2.3265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -2.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1688 -3.0755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0156 -3.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9785 -3.7342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9415 -3.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7883 -3.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4168 -2.3265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2635 -2.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7512 -1.4077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7141 -1.5775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7512 -0.4299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4168 0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2635 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1103 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7883 1.2379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9415 1.7268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9785 1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9785 2.8744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0156 1.7268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1688 1.2379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 1.9869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8468 1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 1.4667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6936 0.9778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6936 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3579 -1.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3357 -1.3357 0.0000 C 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 -2.5403 -0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -1.9556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -3.8246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 2 1 6 0 0 0 3 4 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 1 0 0 0 0 7 43 1 6 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 1 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 24 25 2 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 28 1 1 0 0 0 29 28 1 1 0 0 0 29 30 1 0 0 0 0 29 36 1 0 0 0 0 30 31 1 0 0 0 0 30 42 1 6 0 0 0 31 32 1 0 0 0 0 31 41 1 1 0 0 0 32 33 1 0 0 0 0 32 37 1 6 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 33 36 1 0 0 0 0 37 38 1 0 0 0 0 38 39 2 0 0 0 0 38 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.36
Volume:	640.164
LogP:	3.839
LogD:	3.492
LogS:	-4.514
# Rotatable Bonds:	6
TPSA:	131.75
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	5.888
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818
MDCK Permeability:	5.0632806960493326e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.8
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.829

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.63201141357422%
Volume Distribution (VD):	1.974
Pgp-substrate:	3.451906204223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.486
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.611
CYP3A4-substrate:	0.522

ADMET: Excretion

Clearance (CL):	3.866
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.598
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.614
AMES Toxicity:	0.282
Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.633
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC225997

Natural Product ID:	NPC225997
*Common Name:**	XUIZTHTZQXQZGN-LGLVFHHGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUIZTHTZQXQZGN-LGLVFHHGSA-N
Standard InCHI:	InChI=1S/C34H52O9/c1-10-25-19-22(5)27(36)15-13-12-14-21(4)32(39)41-26(11-2)17-16-20(3)18-23(6)30(25)42-33-29(38)28(37)31(40-24(7)35)34(8,9)43-33/h12-14,16,18-19,25-31,33,36-38H,10-11,15,17H2,1-9H3/b13-12+,20-16+,21-14+,22-19+,23-18+/t25-,26+,27-,28-,29-,30-,31+,33-/m0/s1
SMILES:	CC[C@H]1/C=C(C)/[C@H](C/C=C/C=C(C)/C(=O)O[C@H](CC)C/C=C(C)/C=C(C)/[C@@H]1O[C@@H]1[C@H]([C@@H]([C@H](C(C)(C)O1)OC(=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO18155	Salvia argentea	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[25880372]
NPO16797	Polyangium fumosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14709	Senecio brevilorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15307	Entandrophragma delevoyi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18155	Salvia argentea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9176	Peridinium balticum	Species	Peridiniaceae	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 NPC225997 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	194
0.1-0.2	1324
0.2-0.3	4726
0.3-0.4	9800
0.4-0.5	14452
0.5-0.6	8073
0.6-0.7	3524
0.7-0.8	525
0.8-0.85	56
0.85-0.9	18
0.9-0.95	5
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 NPC225997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1510
0.2-0.3	3930
0.3-0.4	2392
0.4-0.5	865
0.5-0.6	234
0.6-0.7	50
0.7-0.8	6
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