Structure

Physi-Chem Properties

Molecular Weight:  175.96
Volume:  132.164
LogP:  2.131
LogD:  0.763
LogS:  -1.252
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.562
Synthetic Accessibility Score:  2.912
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.319
MDCK Permeability:  0.0006443135789595544
Pgp-inhibitor:  0.001
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.995
Plasma Protein Binding (PPB):  59.54576110839844%
Volume Distribution (VD):  1.314
Pgp-substrate:  41.029685974121094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.449
CYP1A2-substrate:  0.668
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.902
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.249
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.33
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  9.559
Half-life (T1/2):  0.783

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.028
Drug-inuced Liver Injury (DILI):  0.256
AMES Toxicity:  0.499
Rat Oral Acute Toxicity:  0.194
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.122
Carcinogencity:  0.721
Eye Corrosion:  0.236
Eye Irritation:  0.969
Respiratory Toxicity:  0.702

Download Data

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

  Natural Product: NPC69906

Natural Product ID:  NPC69906
Common Name*:   Chlorobutanol
IUPAC Name:   1,1,1-trichloro-2-methylpropan-2-ol
Synonyms:   Chlorbutol; Chloretone; Chlorobutanol; Trichlorisobutylalcohol
Standard InCHIKey:  OSASVXMJTNOKOY-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
SMILES:  CC(C)(C(Cl)(Cl)Cl)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1439973
PubChem CID:   5977
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001670] Tertiary alcohols

*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
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26081757]
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[27169184]
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2494 Xanthium strumarium Species Asteraceae 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
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency = 112201.8 nM PMID[454508]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[454510]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 17782.8 nM PMID[454510]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29855.4 nM PMID[454511]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 33498.3 nM PMID[454511]
NPT2 Others Unspecified Potency n.a. 26832.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29849.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 11882.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2683.2 nM PubChem BioAssay data set
NPT98 Individual Protein HERG Homo sapiens IC50 = 4365158.32 nM PMID[454509]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 1694.4 nM PMID[454510]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2685.5 nM PMID[454510]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[454511]
NPT2 Others Unspecified AC50 n.a. 1258.9 nM PMID[454512]
NPT2 Others Unspecified Ac50 n.a. 1.259 uM PMID[454512]
NPT2 Others Unspecified Ac50 n.a. 39.81 uM PMID[454512]
NPT2 Others Unspecified AC50 n.a. 39810.7 nM PMID[454512]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -5.06 % PMID[454513]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 36.32 % PMID[454514]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.16 % PMID[454515]

☑ 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 NPC69906 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
0.6667 Remote Similarity NPC152773
0.6154 Remote Similarity NPC106054
0.5769 Remote Similarity NPC254757

  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 NPC69906 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
1.0 High Similarity NPD8606 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