Structure

Physi-Chem Properties

Molecular Weight:  115.05
Volume:  119.269
LogP:  2.908
LogD:  1.591
LogS:  -2.316
# Rotatable Bonds:  3
TPSA:  12.36
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.311
Synthetic Accessibility Score:  3.146
Fsp3:  0.8
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:  -4.38
MDCK Permeability:  3.121318150078878e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.284
Plasma Protein Binding (PPB):  13.468871116638184%
Volume Distribution (VD):  1.516
Pgp-substrate:  85.3573226928711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.435
CYP1A2-substrate:  0.621
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.672
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.081
CYP2D6-inhibitor:  0.069
CYP2D6-substrate:  0.626
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.251

ADMET: Excretion

Clearance (CL):  7.288
Half-life (T1/2):  0.587

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.055
Drug-inuced Liver Injury (DILI):  0.264
AMES Toxicity:  0.303
Rat Oral Acute Toxicity:  0.959
Maximum Recommended Daily Dose:  0.169
Skin Sensitization:  0.899
Carcinogencity:  0.276
Eye Corrosion:  0.991
Eye Irritation:  0.988
Respiratory Toxicity:  0.97

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC245814

Natural Product ID:  NPC245814
Common Name*:   Butyl Isothiocyanate
IUPAC Name:   1-isothiocyanatobutane
Synonyms:   Butyl Isothiocyanate
Standard InCHIKey:  LIMQQADUEULBSO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3
SMILES:  CCCCN=C=S
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1814588
PubChem CID:   11613
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
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[22779710]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. root n.a. PMID[22779710]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[25700090]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[31625742]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota Root 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]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO13645 Armoracia rusticana Species Brassicaceae 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]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13645 Armoracia rusticana 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
NPO13645 NPC245814 Other Plant 152.75 18.8 286.7 mg/100g Database [DUKE]

☑ 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
NPT81 Cell Line A549 Homo sapiens IC50 = 413800.0 nM PMID[486225]
NPT396 Cell Line T47D Homo sapiens IC50 = 305800.0 nM PMID[486225]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 389800.0 nM PMID[486225]
NPT114 Cell Line LoVo Homo sapiens IC50 = 324200.0 nM PMID[486225]
NPT114 Cell Line LoVo Homo sapiens IC50 = 231400.0 nM PMID[486225]
NPT114 Cell Line LoVo Homo sapiens IC50 = 296000.0 nM PMID[486229]
NPT114 Cell Line LoVo Homo sapiens IC50 = 296000.0 nM PMID[486230]
NPT114 Cell Line LoVo Homo sapiens IC50 = 296000.0 nM PMID[486231]
NPT449 Organism Meloidogyne javanica Meloidogyne javanica mortality = 58.59 % PMID[486226]
NPT449 Organism Meloidogyne javanica Meloidogyne javanica mortality = 28.15 % PMID[486226]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 63.3 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 31.7 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 92.5 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 82.5 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 80.0 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 77.5 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum EC50 = 403000.0 nM PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum EC50 = 932000.0 nM PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum EC50 = 87300.0 nM PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 100.0 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 100.0 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 46.7 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 13.3 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition = 0.0 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 29.2 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 11.7 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 5.0 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 72.3 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 70.3 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 48.7 % PMID[486227]
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum GI = 22.8 % PMID[486227]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum GI = 31.66 % PMID[486228]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum GI = 10.74 % PMID[486228]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum GI = 6.38 % PMID[486228]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum GI = 84.36 % PMID[486228]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum GI = 43.87 % PMID[486228]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani GI = 91.6 % PMID[486228]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani GI = 3.72 % PMID[486228]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani GI = 68.24 % PMID[486228]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani GI = 57.74 % PMID[486228]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani GI = 15.49 % PMID[486228]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani EC50 = 42.83 ug.mL-1 PMID[486228]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum EC50 = 26.15 ug.mL-1 PMID[486228]
NPT35 Others n.a. LogP = 2.66 n.a. PMID[486228]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 265000.0 nM PMID[486229]
NPT2 Others Unspecified IC50 = 265000.0 nM PMID[486230]
NPT2 Others Unspecified IC50 = 265000.0 nM PMID[486231]

☑ 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 NPC245814 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
0.913 High Similarity NPC106203
0.9048 High Similarity NPC51917
0.8696 High Similarity NPC133836
0.8261 Intermediate Similarity NPC266347
0.7143 Intermediate Similarity NPC172064
0.6667 Remote Similarity NPC138865
0.6562 Remote Similarity NPC292366
0.6562 Remote Similarity NPC171713
0.6562 Remote Similarity NPC266113
0.6562 Remote Similarity NPC105023
0.6429 Remote Similarity NPC322649
0.6429 Remote Similarity NPC144939
0.6207 Remote Similarity NPC27723
0.6176 Remote Similarity NPC235767
0.6176 Remote Similarity NPC140734
0.6176 Remote Similarity NPC180872
0.6 Remote Similarity NPC329501
0.6 Remote Similarity NPC27869
0.5833 Remote Similarity NPC149602
0.5714 Remote Similarity NPC30691

  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 NPC245814 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
0.6087 Remote Similarity NPD8816 Approved
0.5667 Remote Similarity NPD382 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