Structure

Physi-Chem Properties

Molecular Weight:  259.9
Volume:  191.587
LogP:  4.24
LogD:  2.449
LogS:  -4.075
# Rotatable Bonds:  1
TPSA:  29.46
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.774
Synthetic Accessibility Score:  2.542
Fsp3:  0.143
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.591
MDCK Permeability:  2.0023582692374475e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.334
Plasma Protein Binding (PPB):  100.48344421386719%
Volume Distribution (VD):  4.989
Pgp-substrate:  1.5783535242080688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.967
CYP1A2-substrate:  0.929
CYP2C19-inhibitor:  0.157
CYP2C19-substrate:  0.573
CYP2C9-inhibitor:  0.894
CYP2C9-substrate:  0.93
CYP2D6-inhibitor:  0.059
CYP2D6-substrate:  0.477
CYP3A4-inhibitor:  0.144
CYP3A4-substrate:  0.325

ADMET: Excretion

Clearance (CL):  10.808
Half-life (T1/2):  0.318

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.084
Drug-inuced Liver Injury (DILI):  0.734
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.577
Maximum Recommended Daily Dose:  0.78
Skin Sensitization:  0.85
Carcinogencity:  0.332
Eye Corrosion:  0.028
Eye Irritation:  0.942
Respiratory Toxicity:  0.953

Download Data

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

  Natural Product: NPC175931

Natural Product ID:  NPC175931
Common Name*:   Drosophilin A
IUPAC Name:   2,3,5,6-tetrachloro-4-methoxyphenol
Synonyms:  
Standard InCHIKey:  XIWJLPHQDBDOAN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H4Cl4O2/c1-13-7-4(10)2(8)6(12)3(9)5(7)11/h12H,1H3
SMILES:  COc1c(c(c(c(c1Cl)Cl)O)Cl)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL485806
PubChem CID:   68088
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO26288 Phellinus ribis Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[18667308]
NPO26288 Phellinus ribis Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[23215538]
NPO26288 Phellinus ribis Species Hymenochaetaceae 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
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 8.4 n.a. PMID[471305]

☑ 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 NPC175931 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
0.8119 Intermediate Similarity NPC63479
0.7557 Intermediate Similarity NPC72636
0.7557 Intermediate Similarity NPC45134
0.7557 Intermediate Similarity NPC258837
0.713 Intermediate Similarity NPC174048
0.696 Remote Similarity NPC205213
0.6852 Remote Similarity NPC157213
0.6818 Remote Similarity NPC322888
0.6715 Remote Similarity NPC475423
0.6615 Remote Similarity NPC235370
0.6614 Remote Similarity NPC67791
0.6587 Remote Similarity NPC204617
0.6515 Remote Similarity NPC8058
0.6508 Remote Similarity NPC161768
0.6493 Remote Similarity NPC246991
0.6481 Remote Similarity NPC33756
0.6471 Remote Similarity NPC139335
0.6397 Remote Similarity NPC193334
0.633 Remote Similarity NPC23837
0.6241 Remote Similarity NPC33402
0.6186 Remote Similarity NPC307039
0.6182 Remote Similarity NPC38459
0.6121 Remote Similarity NPC114325
0.6121 Remote Similarity NPC16649
0.6042 Remote Similarity NPC252901
0.6019 Remote Similarity NPC124576
0.6016 Remote Similarity NPC232654
0.5981 Remote Similarity NPC65517
0.5968 Remote Similarity NPC233320
0.5968 Remote Similarity NPC124712
0.592 Remote Similarity NPC187958
0.5878 Remote Similarity NPC200207
0.5852 Remote Similarity NPC90577
0.5833 Remote Similarity NPC15350
0.5827 Remote Similarity NPC43411
0.5814 Remote Similarity NPC91452
0.5794 Remote Similarity NPC241549
0.5785 Remote Similarity NPC314803
0.5781 Remote Similarity NPC275627
0.5743 Remote Similarity NPC182475
0.5739 Remote Similarity NPC206876
0.5736 Remote Similarity NPC98372
0.5726 Remote Similarity NPC12987
0.5726 Remote Similarity NPC318429
0.5726 Remote Similarity NPC474603
0.5725 Remote Similarity NPC244403
0.5705 Remote Similarity NPC56379
0.5703 Remote Similarity NPC247871
0.569 Remote Similarity NPC47422
0.568 Remote Similarity NPC17537
0.568 Remote Similarity NPC307875
0.5677 Remote Similarity NPC282294
0.5669 Remote Similarity NPC146096
0.5664 Remote Similarity NPC76453
0.5662 Remote Similarity NPC42644
0.5659 Remote Similarity NPC266932
0.5656 Remote Similarity NPC100870
0.5645 Remote Similarity NPC305205
0.5643 Remote Similarity NPC26576
0.5641 Remote Similarity NPC302546
0.5635 Remote Similarity NPC113457
0.5635 Remote Similarity NPC164576
0.5635 Remote Similarity NPC473653
0.5615 Remote Similarity NPC474920
0.5607 Remote Similarity NPC100980
0.56 Remote Similarity NPC130817

  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 NPC175931 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
0.7458 Intermediate Similarity NPD9685 Approved
0.696 Remote Similarity NPD915 Approved
0.6852 Remote Similarity NPD9295 Approved
0.6589 Remote Similarity NPD1157 Approved
0.6338 Remote Similarity NPD1338 Clinical (unspecified phase)
0.625 Remote Similarity NPD9501 Approved
0.6231 Remote Similarity NPD1010 Approved
0.623 Remote Similarity NPD9552 Approved
0.6182 Remote Similarity NPD9073 Approved
0.6121 Remote Similarity NPD9296 Approved
0.6016 Remote Similarity NPD911 Approved
0.5981 Remote Similarity NPD9088 Approved
0.5957 Remote Similarity NPD1184 Approved
0.5894 Remote Similarity NPD2370 Clinical (unspecified phase)
0.5887 Remote Similarity NPD968 Approved
0.587 Remote Similarity NPD454 Approved
0.5736 Remote Similarity NPD769 Approved
0.5726 Remote Similarity NPD9365 Approved
0.5725 Remote Similarity NPD191 Approved
0.5677 Remote Similarity NPD958 Approved
0.5625 Remote Similarity NPD910 Approved
0.5613 Remote Similarity NPD1714 Approved
0.5613 Remote Similarity NPD1715 Phase 1
0.5607 Remote Similarity NPD9087 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