NPASS Compound

Structure

NPC275631 OpenBabel06302216022D 26 27 0 0 1 0 0 0 0 0999 V2000 0.9511 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 4.8090 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 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1831 -0.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1831 -0.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 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 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 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 3 5 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 8 7 1 1 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 6 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 12 13 2 0 0 0 0 14 15 1 6 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 22 1 6 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	516.944
LogP:	5.511
LogD:	4.633
LogS:	-4.859
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.905
Fsp3:	0.933
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:	-4.823
MDCK Permeability:	1.3712809959542938e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.421

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	89.83776092529297%
Volume Distribution (VD):	1.1
Pgp-substrate:	3.6133971214294434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.313
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.433
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.729
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	4.601
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.577
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.928
Carcinogencity:	0.04
Eye Corrosion:	0.948
Eye Irritation:	0.645
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC275631

Natural Product ID:	NPC275631
*Common Name:**	LTXDJOCJYDKONK-CMNSMLFUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LTXDJOCJYDKONK-CMNSMLFUSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-7-10(3)18(23)25-13-9-20(6,8-2)15(12(5)17(21)22)16-14(13)11(4)19(24)26-16/h7-8,13-16H,2,4-5,9H2,1,3,6H3,(H,21,22)/b10-7-/t13-,14+,15+,16-,20+/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@H]1C[C@@](C)(C=C)[C@H](C(=C)C(=O)O)[C@@H]2[C@@H]1C(=C)C(=O)O2
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: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
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[14695790]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[16124764]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	flowers	Yuxi Town, Fuqing City, Fujian Province, China	2005-SEP	PMID[17583953]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	bark	Indonesia	n.a.	PMID[1965200]
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277312]
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	diseased bulbs	n.a.	n.a.	PMID[9677274]
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24850	Datura metel	Species	Solanaceae	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 NPC275631 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	179
0.1-0.2	1160
0.2-0.3	3861
0.3-0.4	6568
0.4-0.5	14012
0.5-0.6	7427
0.6-0.7	6726
0.7-0.8	2592
0.8-0.85	138
0.85-0.9	30
0.9-0.95	3
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 NPC275631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1536
0.2-0.3	3552
0.3-0.4	2428
0.4-0.5	944
0.5-0.6	274
0.6-0.7	218
0.7-0.8	43
0.8-0.85	0
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