Structure

Physi-Chem Properties

Molecular Weight:  101.03
Volume:  101.973
LogP:  2.474
LogD:  1.259
LogS:  -1.222
# Rotatable Bonds:  1
TPSA:  12.36
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.36
Synthetic Accessibility Score:  3.824
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.382
MDCK Permeability:  3.394240775378421e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.223
Plasma Protein Binding (PPB):  14.768240928649902%
Volume Distribution (VD):  1.312
Pgp-substrate:  81.32716369628906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.488
CYP1A2-substrate:  0.255
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.806
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.24
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.535
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.292

ADMET: Excretion

Clearance (CL):  7.598
Half-life (T1/2):  0.676

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.028
Drug-inuced Liver Injury (DILI):  0.092
AMES Toxicity:  0.1
Rat Oral Acute Toxicity:  0.968
Maximum Recommended Daily Dose:  0.132
Skin Sensitization:  0.519
Carcinogencity:  0.71
Eye Corrosion:  0.983
Eye Irritation:  0.99
Respiratory Toxicity:  0.982

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

  Natural Product: NPC266347

Natural Product ID:  NPC266347
Common Name*:   Isopropyl Isothiocyanate
IUPAC Name:   2-isothiocyanatopropane
Synonyms:   Isopropyl Isothiocyanate
Standard InCHIKey:  VHBFEIBMZHEWSX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C4H7NS/c1-4(2)5-3-6/h4H,1-2H3
SMILES:  CC(N=C=S)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2208211
PubChem CID:   75263
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000004] Organosulfur compounds
      • [CHEMONTID:0001234] Isothiocyanates

*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
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[25700090]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23241 Sigesbeckia orientalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23241 Sigesbeckia orientalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29007 Brassica juncea Species Brassicaceae 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
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens EC50 = 530.0 nM PMID[490079]
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens max activation = 82.0 % PMID[490079]
NPT472 Individual Protein Vanilloid receptor Homo sapiens EC50 = 100000.0 nM PMID[490079]
NPT472 Individual Protein Vanilloid receptor Homo sapiens max activation = 50.0 % PMID[490079]
NPT19 Organism Escherichia coli Escherichia coli Activity = 93.0 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Activity = 77.0 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 57.9 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 18.6 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 81.9 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Activity = 80.0 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Activity = 82.0 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 32.9 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 45.7 % PMID[490077]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 9.7 % PMID[490077]
NPT449 Organism Meloidogyne javanica Meloidogyne javanica mortality = 42.86 % PMID[490078]
NPT449 Organism Meloidogyne javanica Meloidogyne javanica mortality = 22.65 % PMID[490078]

☑ 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 NPC266347 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
0.9048 High Similarity NPC51917
0.8261 Intermediate Similarity NPC245814
0.7917 Intermediate Similarity NPC133836
0.76 Intermediate Similarity NPC106203
0.6667 Remote Similarity NPC329501
0.6552 Remote Similarity NPC172064
0.6429 Remote Similarity NPC144939
0.6207 Remote Similarity NPC27723
0.6 Remote Similarity NPC285308
0.5714 Remote Similarity NPC30691
0.5625 Remote Similarity NPC138865

  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 NPC266347 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
0.6429 Remote Similarity NPD8580 Approved

  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