Structure

Physi-Chem Properties

Molecular Weight:  403.82
Volume:  272.061
LogP:  3.93
LogD:  2.826
LogS:  -6.019
# Rotatable Bonds:  0
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.575
Synthetic Accessibility Score:  6.072
Fsp3:  0.778
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  3
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.738
MDCK Permeability:  3.922561518265866e-05
Pgp-inhibitor:  0.714
Pgp-substrate:  0.858
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.642
Plasma Protein Binding (PPB):  99.1136245727539%
Volume Distribution (VD):  1.794
Pgp-substrate:  0.8213510513305664%

ADMET: Metabolism

CYP1A2-inhibitor:  0.103
CYP1A2-substrate:  0.972
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.829
CYP2C9-inhibitor:  0.051
CYP2C9-substrate:  0.045
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.103
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.635

ADMET: Excretion

Clearance (CL):  7.751
Half-life (T1/2):  0.025

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.517
Drug-inuced Liver Injury (DILI):  0.937
AMES Toxicity:  0.491
Rat Oral Acute Toxicity:  0.935
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.954
Carcinogencity:  0.31
Eye Corrosion:  0.737
Eye Irritation:  0.974
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC262768

Natural Product ID:  NPC262768
Common Name*:   Endosulfan
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RDYMFSUJUZBWLH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H6Cl6O3S/c10-5-6(11)8(13)4-2-18-19(16)17-1-3(4)7(5,12)9(8,14)15/h3-4H,1-2H2
SMILES:  C1C2C(COS(=O)O1)C1(C(=C(C2(C1(Cl)Cl)Cl)Cl)Cl)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL194399
PubChem CID:   3224
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000463] Organic oxoanionic compounds
        • [CHEMONTID:0004456] Organic sulfites
          • [CHEMONTID:0002074] Sulfite esters

*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
NPO15826 Cortex magnoliae officinalis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT299 Individual Protein Androgen Receptor Rattus norvegicus IC50 = 23442.29 nM PMID[533043]
NPT1587 Individual Protein Estradiol 17-beta-dehydrogenase 1 Homo sapiens Activity = 25.0 % PMID[533044]
NPT1588 Individual Protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens Activity = 51.1 % PMID[533044]
NPT1587 Individual Protein Estradiol 17-beta-dehydrogenase 1 Homo sapiens IC50 = 48250.0 nM PMID[533044]
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 50118.7 nM PMID[533045]
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 79432.8 nM PMID[533045]
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 31622.8 nM PMID[533045]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 39810.7 nM PMID[533045]
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 39810.7 nM PMID[533045]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 19952.6 nM PMID[533045]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 2511.9 nM PMID[533045]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 1412.5 nM PMID[533045]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 39810.7 nM PMID[533045]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 31622.8 nM PMID[533045]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 66824.2 nM PMID[533045]
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency n.a. 66824.2 nM PMID[533045]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 21131.7 nM PMID[533045]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 50118.7 nM PMID[533052]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 38942.8 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 61192.7 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 48942.3 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 68519.9 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 68659.4 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 61068.4 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 55008.2 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 61614.6 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 55008.2 nM PubChem BioAssay data set
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 24529.2 nM PubChem BioAssay data set
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 55008.2 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 54914.1 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 54914.1 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 55008.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency = 31622.8 nM PMID[533045]
NPT2 Others Unspecified Potency = 25118.9 nM PMID[533045]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 14125.4 nM PMID[533045]
NPT98 Individual Protein HERG Homo sapiens Potency n.a. 28183.8 nM PMID[533045]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition > 80.0 % PMID[533046]
NPT866 Individual Protein Peroxisome proliferator-activated receptor alpha Homo sapiens Potency n.a. 44668.4 nM PMID[533045]
NPT2 Others Unspecified Potency n.a. 42163.2 nM PMID[533045]
NPT2 Others Unspecified mortality = 82.8 % PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera TIME = 124.8 hr PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera TIME = 208.8 hr PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera mortality = 92.5 % PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera mortality = 89.5 % PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera mortality = 94.1 % PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera mortality = 91.5 % PMID[533047]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera mortality = 93.3 % PMID[533047]
NPT118 Organism Oryza sativa Oryza sativa Activity = 3.31 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 3.38 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 16.56 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 18.33 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 21.75 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 10.0 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 7.94 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 8.26 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 34.55 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 34.02 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 2.46 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 2.4 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 5.0 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 7.78 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 17.08 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 7.83 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 5.98 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 7.17 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 30.0 mg PMID[533048]
NPT118 Organism Oryza sativa Oryza sativa Activity = 28.12 mg PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera GI = 2.24 % PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera GI = 5.66 % PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera Survival = 32.22 % PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera Survival = 67.5 % PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera TIME = 348.0 hr PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera TIME = 288.0 hr PMID[533048]
NPT5551 Organism Sogatella furcifera Sogatella furcifera Ratio < 1.0 n.a. PMID[533048]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 0.7 n.a. PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera LD50 = 37.6 microgAi/g PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera LD50 = 27.5 microgAi/g PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera LD50 = 37.9 microgAi/g PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera LD50 = 36.2 microgAi/g PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera LD50 = 34.0 microgAi/g PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera LD50 = 25.9 microgAi/g PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 1.0 n.a. PMID[533049]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 0.1 n.a. PMID[533049]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 117.81 % PMID[533051]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 111.64 % PMID[533051]
NPT610 Others Molecular identity unknown Potency n.a. 15848.9 nM PMID[533045]
NPT610 Others Molecular identity unknown Potency n.a. 66824.2 nM PMID[533045]
NPT2 Others Unspecified Potency n.a. 43694.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 55008.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24529.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61614.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68519.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1935.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76880.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61720.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38857.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68659.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54914.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54427.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38876.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24311.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61192.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12209.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 49026.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61068.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38942.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34341.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30669 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27333.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54538.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48508.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48607.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21712 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 38876.2 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 38942.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48942.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19517.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21861.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43321.1 nM PubChem BioAssay data set
NPT27377 ORGANISM Earias Earias mortality = 99.4 % PMID[533047]

☑ 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 NPC262768 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
0.679 Remote Similarity NPC314496

  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 NPC262768 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
NPD

  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