NPASS Compound

Structure

NPC278593 OpenBabel06302215122D 21 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5873 0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5436 0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2346 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 -0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5218 0.6625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 N 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 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 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 4 20 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 2 0 0 0 0 7 21 1 0 0 0 0 9 8 1 1 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 6 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	279.1
Volume:	280.545
LogP:	2.288
LogD:	2.298
LogS:	-3.604
# Rotatable Bonds:	1
TPSA:	64.93
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.839
Synthetic Accessibility Score:	3.498
Fsp3:	0.125
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:	-4.902
MDCK Permeability:	1.4676617865916342e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	56.837825775146484%
Volume Distribution (VD):	2.004
Pgp-substrate:	38.740596771240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.34
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.341
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	3.226
Half-life (T1/2):	0.614

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.759
AMES Toxicity:	0.477
Rat Oral Acute Toxicity:	0.707
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.188
Carcinogencity:	0.204
Eye Corrosion:	0.003
Eye Irritation:	0.091
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC278593

Natural Product ID:	NPC278593
*Common Name:**	SCCCIBBXTCKOTC-LSDHHAIUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SCCCIBBXTCKOTC-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C16H13N3O2/c20-11-7-5-10(6-8-11)14-15-18-16(21)12-3-1-2-4-13(12)19(15)9-17-14/h1-9,14-15,20H,(H,18,21)/t14-,15+/m0/s1
SMILES:	c1ccc2c(c1)C(=N[C@H]1[C@H](c3ccc(cc3)O)N=CN21)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53356217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO27983	Penicillium paneum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21495659]
NPO33640	Penicillium paneum SD-44	Species	Aspergillaceae	Eukaryota	isolated from a marine sediment sample	South China Sea at a depth of 201 m, China	2008-AUG	PMID[21495659]
NPO3185	Isodon walkeri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28116	Carnegia gigantea	Species	Saturniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3185	Isodon walkeri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7701	Myxococcus virescens	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27296	Datura leichhardtii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27940	Betula middendorffi	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27344	Krameria triandra	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27983	Penicillium paneum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27676	Sinularia conferta	Species	Alcyoniidae	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 NPC278593 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 NPC278593 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