Structure

Physi-Chem Properties

Molecular Weight:  707.74
Volume:  527.227
LogP:  8.807
LogD:  3.356
LogS:  -10.202
# Rotatable Bonds:  7
TPSA:  66.38
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.246
Synthetic Accessibility Score:  3.101
Fsp3:  0.143
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.762
MDCK Permeability:  4.605873073160183e-06
Pgp-inhibitor:  0.998
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.375
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  112.12519836425781%
Volume Distribution (VD):  6.53
Pgp-substrate:  1.7457468509674072%

ADMET: Metabolism

CYP1A2-inhibitor:  0.156
CYP1A2-substrate:  0.764
CYP2C19-inhibitor:  0.108
CYP2C19-substrate:  0.373
CYP2C9-inhibitor:  0.861
CYP2C9-substrate:  0.979
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.339
CYP3A4-inhibitor:  0.018
CYP3A4-substrate:  0.892

ADMET: Excretion

Clearance (CL):  7.96
Half-life (T1/2):  0.041

ADMET: Toxicity

hERG Blockers:  0.105
Human Hepatotoxicity (H-HT):  0.028
Drug-inuced Liver Injury (DILI):  0.87
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.999
Maximum Recommended Daily Dose:  0.973
Skin Sensitization:  0.955
Carcinogencity:  0.123
Eye Corrosion:  0.003
Eye Irritation:  0.921
Respiratory Toxicity:  0.796

Download Data

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

  Natural Product: NPC72636

Natural Product ID:  NPC72636
Common Name*:   Chlorophellin B
IUPAC Name:   2,4-dichloro-3-methoxy-5,6-bis(2,3,5,6-tetrachloro-4-methoxyphenoxy)phenol
Synonyms:   Chlorophellin B
Standard InCHIKey:  CPORQNGPHLLMIO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H10Cl10O6/c1-33-15-4(22)8(26)18(9(27)5(15)23)36-20-13(31)17(35-3)12(30)14(32)21(20)37-19-10(28)6(24)16(34-2)7(25)11(19)29/h32H,1-3H3
SMILES:  COc1c(c(c(c(c1Cl)Cl)Oc1c(c(c(c(c1Oc1c(c(c(c(c1Cl)Cl)OC)Cl)Cl)O)Cl)OC)Cl)Cl)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL521730
PubChem CID:   44587462
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004155] Diphenylethers

*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 = 2.0 n.a. PMID[489958]

☑ 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 NPC72636 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
1.0 High Similarity NPC45134
1.0 High Similarity NPC258837
0.7714 Intermediate Similarity NPC235370
0.7557 Intermediate Similarity NPC175931
0.7517 Intermediate Similarity NPC475423
0.7429 Intermediate Similarity NPC205213
0.7266 Intermediate Similarity NPC76915
0.7266 Intermediate Similarity NPC151617
0.7163 Intermediate Similarity NPC214289
0.7063 Intermediate Similarity NPC205850
0.6994 Remote Similarity NPC56379
0.6966 Remote Similarity NPC126216
0.6966 Remote Similarity NPC105147
0.6966 Remote Similarity NPC228875
0.6779 Remote Similarity NPC110677
0.6611 Remote Similarity NPC195675
0.6594 Remote Similarity NPC232654
0.6575 Remote Similarity NPC471811
0.6575 Remote Similarity NPC471809
0.6557 Remote Similarity NPC39409
0.6556 Remote Similarity NPC469622
0.6556 Remote Similarity NPC189589
0.6547 Remote Similarity NPC124712
0.6519 Remote Similarity NPC471814
0.6519 Remote Similarity NPC471808
0.6513 Remote Similarity NPC216836
0.6513 Remote Similarity NPC37074
0.6513 Remote Similarity NPC469621
0.6494 Remote Similarity NPC214860
0.648 Remote Similarity NPC28160
0.6467 Remote Similarity NPC192810
0.6447 Remote Similarity NPC298845
0.6429 Remote Similarity NPC45824
0.6424 Remote Similarity NPC221090
0.6412 Remote Similarity NPC63479
0.641 Remote Similarity NPC161203
0.6403 Remote Similarity NPC307875
0.64 Remote Similarity NPC152722
0.6387 Remote Similarity NPC208769
0.6378 Remote Similarity NPC121100
0.6369 Remote Similarity NPC94236
0.6369 Remote Similarity NPC37196
0.6364 Remote Similarity NPC247146
0.6358 Remote Similarity NPC217854
0.6346 Remote Similarity NPC287780
0.6344 Remote Similarity NPC471806
0.6344 Remote Similarity NPC471810
0.6333 Remote Similarity NPC145780
0.6333 Remote Similarity NPC175804
0.6329 Remote Similarity NPC310854
0.6329 Remote Similarity NPC106215
0.6316 Remote Similarity NPC25817
0.6312 Remote Similarity NPC103976
0.6312 Remote Similarity NPC326797
0.6312 Remote Similarity NPC102904
0.6312 Remote Similarity NPC474282
0.6312 Remote Similarity NPC107551
0.6312 Remote Similarity NPC48956
0.6312 Remote Similarity NPC176051
0.6312 Remote Similarity NPC276490
0.6306 Remote Similarity NPC127624
0.6306 Remote Similarity NPC202762
0.6306 Remote Similarity NPC86655
0.6299 Remote Similarity NPC210355
0.629 Remote Similarity NPC471805
0.629 Remote Similarity NPC471813
0.6289 Remote Similarity NPC261873
0.6289 Remote Similarity NPC281521
0.6289 Remote Similarity NPC134968
0.6289 Remote Similarity NPC201357
0.6289 Remote Similarity NPC472337
0.6289 Remote Similarity NPC283009
0.6289 Remote Similarity NPC255147
0.6282 Remote Similarity NPC60756
0.6282 Remote Similarity NPC229231
0.6273 Remote Similarity NPC25966
0.6273 Remote Similarity NPC22517
0.6273 Remote Similarity NPC245207
0.6273 Remote Similarity NPC319647
0.6273 Remote Similarity NPC127218
0.6267 Remote Similarity NPC276195
0.6266 Remote Similarity NPC60982
0.6266 Remote Similarity NPC229442
0.6266 Remote Similarity NPC168059
0.6258 Remote Similarity NPC266691
0.6257 Remote Similarity NPC188618
0.6257 Remote Similarity NPC471807
0.625 Remote Similarity NPC472336
0.625 Remote Similarity NPC472334
0.6242 Remote Similarity NPC472597
0.6242 Remote Similarity NPC193334
0.6235 Remote Similarity NPC22317
0.6235 Remote Similarity NPC291101
0.6235 Remote Similarity NPC259519
0.6235 Remote Similarity NPC266197
0.6226 Remote Similarity NPC170694
0.6226 Remote Similarity NPC103967
0.6218 Remote Similarity NPC58164
0.6218 Remote Similarity NPC10225
0.6211 Remote Similarity NPC272157
0.6211 Remote Similarity NPC90615
0.6211 Remote Similarity NPC25111
0.6211 Remote Similarity NPC201145
0.6211 Remote Similarity NPC73535
0.6211 Remote Similarity NPC6262
0.6211 Remote Similarity NPC474390
0.6203 Remote Similarity NPC7903
0.6203 Remote Similarity NPC160991
0.6203 Remote Similarity NPC474134
0.6203 Remote Similarity NPC35932
0.6203 Remote Similarity NPC131128
0.6203 Remote Similarity NPC184447
0.6203 Remote Similarity NPC16208
0.6196 Remote Similarity NPC471389
0.6196 Remote Similarity NPC247291
0.6196 Remote Similarity NPC8577
0.6188 Remote Similarity NPC260898
0.6188 Remote Similarity NPC112939
0.6188 Remote Similarity NPC112246
0.6188 Remote Similarity NPC474206
0.6188 Remote Similarity NPC47398
0.6188 Remote Similarity NPC195022
0.6188 Remote Similarity NPC234333
0.6188 Remote Similarity NPC470356
0.6188 Remote Similarity NPC121812
0.6188 Remote Similarity NPC94750
0.6184 Remote Similarity NPC71579
0.6184 Remote Similarity NPC262253
0.6184 Remote Similarity NPC473411
0.6178 Remote Similarity NPC299221
0.6178 Remote Similarity NPC220935
0.6178 Remote Similarity NPC91291
0.6178 Remote Similarity NPC311680
0.6178 Remote Similarity NPC234488
0.6178 Remote Similarity NPC472338
0.6178 Remote Similarity NPC51840
0.6174 Remote Similarity NPC204617
0.6173 Remote Similarity NPC55947
0.6173 Remote Similarity NPC19869
0.6164 Remote Similarity NPC269528
0.6164 Remote Similarity NPC36661
0.6159 Remote Similarity NPC107161
0.6154 Remote Similarity NPC63179
0.615 Remote Similarity NPC471803
0.615 Remote Similarity NPC471804
0.615 Remote Similarity NPC471812
0.6149 Remote Similarity NPC173660
0.6149 Remote Similarity NPC162659
0.6149 Remote Similarity NPC270456
0.6149 Remote Similarity NPC300846
0.6149 Remote Similarity NPC476639
0.6149 Remote Similarity NPC230734
0.6149 Remote Similarity NPC306441
0.6149 Remote Similarity NPC114155
0.6149 Remote Similarity NPC16435
0.6149 Remote Similarity NPC227503
0.6149 Remote Similarity NPC265433
0.6149 Remote Similarity NPC248727
0.6149 Remote Similarity NPC474639
0.6144 Remote Similarity NPC95168
0.6139 Remote Similarity NPC309787
0.6139 Remote Similarity NPC82503
0.6135 Remote Similarity NPC160283
0.6135 Remote Similarity NPC295719
0.6135 Remote Similarity NPC73505
0.6135 Remote Similarity NPC262189
0.6135 Remote Similarity NPC165026
0.6135 Remote Similarity NPC254759
0.6135 Remote Similarity NPC34431
0.6131 Remote Similarity NPC281549
0.6129 Remote Similarity NPC181361
0.6129 Remote Similarity NPC171533
0.6125 Remote Similarity NPC256307
0.6125 Remote Similarity NPC317380
0.6125 Remote Similarity NPC66840
0.6121 Remote Similarity NPC110067
0.6121 Remote Similarity NPC34245
0.6121 Remote Similarity NPC47633
0.6121 Remote Similarity NPC85264
0.6121 Remote Similarity NPC102044
0.6121 Remote Similarity NPC91492
0.6121 Remote Similarity NPC256555
0.6121 Remote Similarity NPC7439
0.6115 Remote Similarity NPC202582
0.6115 Remote Similarity NPC470258
0.6115 Remote Similarity NPC190629
0.6115 Remote Similarity NPC226788
0.6115 Remote Similarity NPC273295
0.6115 Remote Similarity NPC222004
0.6115 Remote Similarity NPC218856
0.6115 Remote Similarity NPC210623
0.6115 Remote Similarity NPC285339
0.6115 Remote Similarity NPC3439
0.6111 Remote Similarity NPC211549
0.6108 Remote Similarity NPC112251
0.6107 Remote Similarity NPC161768
0.6104 Remote Similarity NPC122792
0.6104 Remote Similarity NPC228972
0.6101 Remote Similarity NPC6451
0.6101 Remote Similarity NPC218884

  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 NPC72636 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
0.7429 Intermediate Similarity NPD915 Approved
0.6528 Remote Similarity NPD9685 Approved
0.609 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6084 Remote Similarity NPD9552 Approved
0.6078 Remote Similarity NPD1157 Approved
0.6051 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6013 Remote Similarity NPD3027 Phase 3
0.6 Remote Similarity NPD1613 Approved
0.6 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6 Remote Similarity NPD1338 Clinical (unspecified phase)
0.5986 Remote Similarity NPD9501 Approved
0.5976 Remote Similarity NPD1940 Clinical (unspecified phase)
0.5845 Remote Similarity NPD291 Approved
0.5793 Remote Similarity NPD4538 Approved
0.5793 Remote Similarity NPD4537 Clinical (unspecified phase)
0.5793 Remote Similarity NPD4536 Approved
0.5767 Remote Similarity NPD1184 Approved
0.5762 Remote Similarity NPD191 Approved
0.5755 Remote Similarity NPD9296 Approved
0.575 Remote Similarity NPD4908 Phase 1
0.5739 Remote Similarity NPD2801 Approved
0.5723 Remote Similarity NPD2370 Clinical (unspecified phase)
0.5679 Remote Similarity NPD4907 Clinical (unspecified phase)
0.5677 Remote Similarity NPD1010 Approved
0.5663 Remote Similarity NPD5588 Approved
0.5663 Remote Similarity NPD5960 Phase 3
0.566 Remote Similarity NPD9549 Phase 2
0.5657 Remote Similarity NPD1715 Phase 1
0.5657 Remote Similarity NPD1714 Approved
0.5652 Remote Similarity NPD3537 Clinical (unspecified phase)
0.5649 Remote Similarity NPD1548 Phase 1
0.5614 Remote Similarity NPD5058 Phase 3

  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