NPASS Compound

Structure

NPC473642 OpenBabel06302216122D 30 33 0 0 1 0 0 0 0 0999 V2000 4.5380 5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 2.9781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5380 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 2.9781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.4041 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0872 2.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6750 3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0872 4.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 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 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 7 12 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 15 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 18 23 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 23 2 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 27 28 2 0 0 0 0 27 29 1 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	406.709
LogP:	3.054
LogD:	3.603
LogS:	-4.89
# Rotatable Bonds:	9
TPSA:	89.52
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	4.173
Fsp3:	0.455
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:	-4.863
MDCK Permeability:	1.98566685867263e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	72.36493682861328%
Volume Distribution (VD):	2.534
Pgp-substrate:	13.796442985534668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.978
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.667
CYP3A4-inhibitor:	0.989
CYP3A4-substrate:	0.788

ADMET: Excretion

Clearance (CL):	12.822
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.677
Human Hepatotoxicity (H-HT):	0.847
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.975
Carcinogencity:	0.547
Eye Corrosion:	0.003
Eye Irritation:	0.07
Respiratory Toxicity:	0.58

Download Data

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

Natural Product: NPC473642

Natural Product ID:	NPC473642
*Common Name:**	QDUBPFJNGXKXDZ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QDUBPFJNGXKXDZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-25-21(23)15(7-13-3-5-17-19(9-13)29-11-27-17)16(22(24)26-2)8-14-4-6-18-20(10-14)30-12-28-18/h3,5-6,9-10,14-16H,4,7-8,11-12H2,1-2H3
SMILES:	COC(=O)C(CC1CC=C2C(=C1)OCO2)C(CC3=CC4=C(C=C3)OCO4)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566344
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425143]
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087610]
NPO16896	Justicia ciliata	Species	Acanthaceae	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 NPC473642 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 NPC473642 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