Structure

Physi-Chem Properties

Molecular Weight:  221.05
Volume:  215.603
LogP:  2.944
LogD:  3.039
LogS:  -4.171
# Rotatable Bonds:  3
TPSA:  42.09
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.64
Synthetic Accessibility Score:  2.613
Fsp3:  0.182
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.911
MDCK Permeability:  9.039190445037093e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.871
Plasma Protein Binding (PPB):  93.83911895751953%
Volume Distribution (VD):  1.172
Pgp-substrate:  2.4940240383148193%

ADMET: Metabolism

CYP1A2-inhibitor:  0.991
CYP1A2-substrate:  0.943
CYP2C19-inhibitor:  0.827
CYP2C19-substrate:  0.559
CYP2C9-inhibitor:  0.274
CYP2C9-substrate:  0.918
CYP2D6-inhibitor:  0.422
CYP2D6-substrate:  0.883
CYP3A4-inhibitor:  0.468
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  7.087
Half-life (T1/2):  0.423

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.522
Drug-inuced Liver Injury (DILI):  0.935
AMES Toxicity:  0.868
Rat Oral Acute Toxicity:  0.146
Maximum Recommended Daily Dose:  0.856
Skin Sensitization:  0.925
Carcinogencity:  0.644
Eye Corrosion:  0.741
Eye Irritation:  0.991
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC57446

Natural Product ID:  NPC57446
Common Name*:   QTGIHGJBFQOXDY-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QTGIHGJBFQOXDY-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H11NO2S/c1-14-7-3-4-8-9(6-13)11(15-2)12-10(8)5-7/h3-6,12H,1-2H3
SMILES:  COc1ccc2c(C=O)c([nH]c2c1)SC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   24813533
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles

*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
NPO14915 Uvaria acuminata Species Annonaceae Eukaryota n.a. root n.a. PMID[14709883]
NPO20111 Anthemis auriculata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[16643047]
NPO20111 Anthemis auriculata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO19198 Kalmia latifolia Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[521818]
NPO19198 Kalmia latifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19498 Caesalpinia tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14915 Uvaria acuminata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22077 Dioscorea tokoro Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19498 Caesalpinia tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22077 Dioscorea tokoro Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14915 Uvaria acuminata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19198 Kalmia latifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22077 Dioscorea tokoro Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19198 Kalmia latifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO22720 Kopsia hainanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14915 Uvaria acuminata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23145 Andropogon jwarancusa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24254 Euphorbia sapinii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19498 Caesalpinia tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22522 Senecio speciosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19198 Kalmia latifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21928 Clathrotropis brachypetala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23030 Dalbergia nigra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20111 Anthemis auriculata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1020 Petrosimonia monandra Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22077 Dioscorea tokoro Species Dioscoreaceae 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 NPC57446 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 NPC57446 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