Structure

Physi-Chem Properties

Molecular Weight:  242.14
Volume:  265.848
LogP:  2.053
LogD:  2.539
LogS:  -2.212
# Rotatable Bonds:  5
TPSA:  47.28
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.792
Synthetic Accessibility Score:  1.856
Fsp3:  0.2
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:  -4.609
MDCK Permeability:  9.089688683161512e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.14
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.03
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.371
Plasma Protein Binding (PPB):  89.24939727783203%
Volume Distribution (VD):  2.198
Pgp-substrate:  12.725006103515625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.702
CYP1A2-substrate:  0.767
CYP2C19-inhibitor:  0.826
CYP2C19-substrate:  0.531
CYP2C9-inhibitor:  0.31
CYP2C9-substrate:  0.086
CYP2D6-inhibitor:  0.655
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.602
CYP3A4-substrate:  0.207

ADMET: Excretion

Clearance (CL):  6.393
Half-life (T1/2):  0.636

ADMET: Toxicity

hERG Blockers:  0.068
Human Hepatotoxicity (H-HT):  0.212
Drug-inuced Liver Injury (DILI):  0.074
AMES Toxicity:  0.849
Rat Oral Acute Toxicity:  0.381
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.921
Carcinogencity:  0.543
Eye Corrosion:  0.005
Eye Irritation:  0.648
Respiratory Toxicity:  0.588

Download Data

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

  Natural Product: NPC50686

Natural Product ID:  NPC50686
Common Name*:   NQTMQERLPBHIAG-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  NQTMQERLPBHIAG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H18N2O/c1-18-11-13-7-3-5-9-15(13)17-10-12-6-2-4-8-14(12)16/h2-9,17H,10-11,16H2,1H3
SMILES:  COCc1ccccc1NCc1ccccc1N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   66385053
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000185] Phenylmethylamines
          • [CHEMONTID:0004204] Phenylbenzamines

*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
NPO12570 Salacia macrosperma Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1039/P19790000349]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota rhizomes n.a. n.a. PMID[11000020]
NPO2082 Chromobacterium violaceum Species Chromobacteriaceae Bacteria n.a. n.a. n.a. PMID[17176066]
NPO2082 Chromobacterium violaceum Species Chromobacteriaceae Bacteria n.a. n.a. n.a. PMID[20490411]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. rhizome n.a. PMID[21401114]
NPO2082 Chromobacterium violaceum Species Chromobacteriaceae Bacteria n.a. n.a. n.a. PMID[21779844]
NPO503 Trigonostemon lii Species Euphorbiaceae Eukaryota leaves n.a. n.a. PMID[22342628]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. PMID[27439360]
NPO5865 Justicia gendarussa Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[28613071]
NPO14489 Hyoscyamus albus Species Solanaceae Eukaryota Hairy roots n.a. n.a. PMID[9868154]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16014 Angelica porphyrocaulis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO503 Trigonostemon lii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27100 Evernia olivetorina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14489 Hyoscyamus albus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5616 Cissampelos ovalifolia Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5414 Microsorium brachylepis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2640 Bignonia suberosa Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22035 Kielmeyera elata Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2082 Chromobacterium violaceum Species Chromobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14091 Lecidea confluens Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12570 Salacia macrosperma Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8637 Brassica elongata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6311 0vodinia antillensis Species 0vodiniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1263 Marine bacillus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7880 Greyia flanaganii Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13935 Dendrobium ochreatum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5865 Justicia gendarussa Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27364 Gallus gallus Species Phasianidae 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 NPC50686 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 NPC50686 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