Structure

Physi-Chem Properties

Molecular Weight:  240.03
Volume:  217.395
LogP:  2.158
LogD:  2.067
LogS:  -3.122
# Rotatable Bonds:  7
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.388
Synthetic Accessibility Score:  5.107
Fsp3:  0.75
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:  -4.365
MDCK Permeability:  1.8762146282824688e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.058
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.707
Plasma Protein Binding (PPB):  64.68437957763672%
Volume Distribution (VD):  0.779
Pgp-substrate:  27.063583374023438%

ADMET: Metabolism

CYP1A2-inhibitor:  0.87
CYP1A2-substrate:  0.917
CYP2C19-inhibitor:  0.495
CYP2C19-substrate:  0.892
CYP2C9-inhibitor:  0.156
CYP2C9-substrate:  0.765
CYP2D6-inhibitor:  0.211
CYP2D6-substrate:  0.673
CYP3A4-inhibitor:  0.147
CYP3A4-substrate:  0.74

ADMET: Excretion

Clearance (CL):  10.365
Half-life (T1/2):  0.735

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.931
Drug-inuced Liver Injury (DILI):  0.968
AMES Toxicity:  0.901
Rat Oral Acute Toxicity:  0.082
Maximum Recommended Daily Dose:  0.453
Skin Sensitization:  0.932
Carcinogencity:  0.972
Eye Corrosion:  0.116
Eye Irritation:  0.797
Respiratory Toxicity:  0.677

Download Data

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

  Natural Product: NPC277288

Natural Product ID:  NPC277288
Common Name*:   Foetisulfide C
IUPAC Name:   [(E)-3-(butan-2-yldisulfanyl)prop-1-enyl] methanesulfinate
Synonyms:   Foetisulfide C
Standard InCHIKey:  OQCBJFYTNWYVQJ-AATRIKPKSA-N
Standard InCHI:  InChI=1S/C8H16O2S3/c1-4-8(2)12-11-7-5-6-10-13(3)9/h5-6,8H,4,7H2,1-3H3/b6-5+
SMILES:  CCC(C)SSC/C=C/OS(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077966
PubChem CID:   11042864
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000004] Organosulfur compounds
      • [CHEMONTID:0002800] Organic disulfides
        • [CHEMONTID:0004089] Dialkyldisulfides

*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
NPO23631 Ferula foetida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23631 Ferula foetida Species Apiaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[453277]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[453277]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[453277]
NPT1031 Cell Line Ca9-22 Homo sapiens IC50 = 16.48 ug.mL-1 PMID[453277]
NPT81 Cell Line A549 Homo sapiens IC50 = 9.14 ug.mL-1 PMID[453277]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 19.21 ug.mL-1 PMID[453277]

☑ 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 NPC277288 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
0.7059 Intermediate Similarity NPC46648
0.6765 Remote Similarity NPC2088
0.6486 Remote Similarity NPC204251
0.6486 Remote Similarity NPC168614
0.6364 Remote Similarity NPC142438
0.6061 Remote Similarity NPC184203
0.6061 Remote Similarity NPC220140
0.5882 Remote Similarity NPC476550
0.5682 Remote Similarity NPC171978
0.5682 Remote Similarity NPC277382

  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 NPC277288 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
0.5946 Remote Similarity NPD9054 Approved
0.5833 Remote Similarity NPD8548 Clinical (unspecified phase)

  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