NPASS Compound

Structure

NPC490611 OpenBabel06302216212D 23 25 0 0 1 0 0 0 0 0999 V2000 1.8831 -2.9003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6681 -2.3302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5544 -2.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5669 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6807 -0.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6813 1.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5214 1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5212 0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 1.4561 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6810 1.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5213 1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5215 0.4857 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6814 0.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 0.4853 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3614 1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0614 2.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3104 1.7401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6104 0.8175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 2.4561 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 2 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 11 1 0 0 0 0 6 7 2 0 0 0 0 7 18 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 12 17 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 19 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 19 20 2 0 0 0 0 19 21 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.15
Volume:	324.124
LogP:	2.793
LogD:	1.414
LogS:	-3.667
# Rotatable Bonds:	3
TPSA:	63.41
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.861
Synthetic Accessibility Score:	4.872
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.619
MDCK Permeability:	1.6947493350016885e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	83.91106414794922%
Volume Distribution (VD):	1.226
Pgp-substrate:	16.825178146362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.76
CYP1A2-substrate:	0.554
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.239
CYP2D6-inhibitor:	0.977
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.662

ADMET: Excretion

Clearance (CL):	0.816
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.746
Drug-inuced Liver Injury (DILI):	0.311
AMES Toxicity:	0.767
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.445
Carcinogencity:	0.642
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC490611

Natural Product ID:	NPC490611
*Common Name:**	luteoride d
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SZFNCACTPVVVCZ-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C18H20N2O3/c1-11(2)8-9-13-6-5-7-14-16(13)19-17-18(14,21)10-15(20-23-17)12(3)22-4/h5-9,17,19,21H,1,3,10H2,2,4H3/b9-8+
SMILES:	CC(=C)/C=C/C1=C2C(=CC=C1)C3(CC(=NOC3N2)C(=C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	156581585
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001146] Indolines

*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
NPO41356	Aspergillus fumigatus MR2012 + Streptomyces leeuwenhoekii strain C34	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28744271]
NPO41357	Aspergillus fumigatus MR2012 + Streptomyces leeuwenhoekii strain C34/strain C58	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28744271]

☑ 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 NPC490611 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

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 NPC490611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

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