Structure

Physi-Chem Properties

Molecular Weight:  591.62
Volume:  305.965
LogP:  6.12
LogD:  2.961
LogS:  -7.193
# Rotatable Bonds:  2
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.38
Synthetic Accessibility Score:  2.956
Fsp3:  0.0
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.874
MDCK Permeability:  1.5071264897414949e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.977
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.194
Plasma Protein Binding (PPB):  101.87525177001953%
Volume Distribution (VD):  3.473
Pgp-substrate:  6.113318920135498%

ADMET: Metabolism

CYP1A2-inhibitor:  0.956
CYP1A2-substrate:  0.141
CYP2C19-inhibitor:  0.736
CYP2C19-substrate:  0.081
CYP2C9-inhibitor:  0.865
CYP2C9-substrate:  0.749
CYP2D6-inhibitor:  0.28
CYP2D6-substrate:  0.529
CYP3A4-inhibitor:  0.125
CYP3A4-substrate:  0.114

ADMET: Excretion

Clearance (CL):  0.733
Half-life (T1/2):  0.28

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.259
Drug-inuced Liver Injury (DILI):  0.561
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.955
Maximum Recommended Daily Dose:  0.951
Skin Sensitization:  0.936
Carcinogencity:  0.112
Eye Corrosion:  0.648
Eye Irritation:  0.963
Respiratory Toxicity:  0.922

Download Data

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

  Natural Product: NPC41232

Natural Product ID:  NPC41232
Common Name*:   3,4,5-Tribromo-2-(2,4-Dibromo-6-Hydroxyphenoxy)Phenol
IUPAC Name:   3,4,5-tribromo-2-(2,4-dibromo-6-hydroxyphenoxy)phenol
Synonyms:  
Standard InCHIKey:  CMVKVDYOAXWOGA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H5Br5O3/c13-4-1-6(15)11(7(18)2-4)20-12-8(19)3-5(14)9(16)10(12)17/h1-3,18-19H
SMILES:  Brc1cc(O)c(c(c1)Br)Oc1c(O)cc(c(c1Br)Br)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464369
PubChem CID:   10077251
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004155] Diphenylethers
          • [CHEMONTID:0001845] Bromodiphenyl ethers

*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
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[11374954]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[15921404]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[1593283]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[18198840]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. at 1020 m depth from Chuuk Atoll, Federated States of Micronesia n.a. PMID[18824352]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[20230038]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[26551342]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[26863083]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[27336796]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[32243140]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. Indo-Pacific n.a. PMID[7494145]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[9748373]

☑ 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
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Inhibition = 100.0 % PMID[490477]

☑ 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 NPC41232 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 NPC63317
0.9912 High Similarity NPC226737
0.9912 High Similarity NPC153580
0.9912 High Similarity NPC299939
0.9825 High Similarity NPC88733
0.9825 High Similarity NPC137922
0.9825 High Similarity NPC40302
0.9825 High Similarity NPC173511
0.9821 High Similarity NPC104124
0.9739 High Similarity NPC64130
0.9739 High Similarity NPC97157
0.9739 High Similarity NPC25134
0.9739 High Similarity NPC295879
0.9739 High Similarity NPC175520
0.9739 High Similarity NPC159866
0.9735 High Similarity NPC86007
0.9735 High Similarity NPC44270
0.9655 High Similarity NPC68350
0.9655 High Similarity NPC230013
0.9655 High Similarity NPC131940
0.9655 High Similarity NPC81149
0.9655 High Similarity NPC197576
0.9652 High Similarity NPC474375
0.9646 High Similarity NPC191194
0.9565 High Similarity NPC170824
0.9565 High Similarity NPC47769
0.9565 High Similarity NPC196371
0.918 High Similarity NPC222684
0.918 High Similarity NPC206183
0.913 High Similarity NPC264379
0.9106 High Similarity NPC178301
0.8974 High Similarity NPC71186
0.8957 High Similarity NPC221301
0.8934 High Similarity NPC45728
0.8879 High Similarity NPC162294
0.8468 Intermediate Similarity NPC163019
0.8468 Intermediate Similarity NPC1744
0.8319 Intermediate Similarity NPC319933
0.8226 Intermediate Similarity NPC235166
0.8148 Intermediate Similarity NPC8577
0.7586 Intermediate Similarity NPC314803
0.7544 Intermediate Similarity NPC475466
0.7445 Intermediate Similarity NPC245386
0.741 Intermediate Similarity NPC271942
0.7376 Intermediate Similarity NPC286337
0.7313 Intermediate Similarity NPC13004
0.7293 Intermediate Similarity NPC220311
0.7241 Intermediate Similarity NPC114325
0.7218 Intermediate Similarity NPC236265
0.7211 Intermediate Similarity NPC152947
0.7153 Intermediate Similarity NPC226493
0.7153 Intermediate Similarity NPC160081
0.708 Intermediate Similarity NPC85049
0.708 Intermediate Similarity NPC252149
0.705 Intermediate Similarity NPC303011
0.7023 Intermediate Similarity NPC38483
0.7014 Intermediate Similarity NPC89341
0.7 Intermediate Similarity NPC86947
0.7 Intermediate Similarity NPC151617
0.7 Intermediate Similarity NPC76915
0.6993 Remote Similarity NPC160932
0.694 Remote Similarity NPC219444
0.6928 Remote Similarity NPC474535
0.6913 Remote Similarity NPC473608
0.6903 Remote Similarity NPC319826
0.6894 Remote Similarity NPC214289
0.6889 Remote Similarity NPC474169
0.6889 Remote Similarity NPC84606
0.6889 Remote Similarity NPC473572
0.6883 Remote Similarity NPC475697
0.6871 Remote Similarity NPC109346
0.6855 Remote Similarity NPC307875
0.6838 Remote Similarity NPC318429
0.6838 Remote Similarity NPC137117
0.6822 Remote Similarity NPC33244
0.6822 Remote Similarity NPC471488
0.6815 Remote Similarity NPC47790
0.6815 Remote Similarity NPC229213
0.6791 Remote Similarity NPC205850
0.6791 Remote Similarity NPC205213
0.6788 Remote Similarity NPC142776
0.6786 Remote Similarity NPC11449
0.6772 Remote Similarity NPC54543
0.6769 Remote Similarity NPC94217
0.6761 Remote Similarity NPC163560
0.6761 Remote Similarity NPC244890
0.6754 Remote Similarity NPC125306
0.6742 Remote Similarity NPC9248
0.6741 Remote Similarity NPC290451
0.6741 Remote Similarity NPC127389
0.6741 Remote Similarity NPC145780
0.6739 Remote Similarity NPC134219
0.6736 Remote Similarity NPC213471
0.6724 Remote Similarity NPC206876
0.6719 Remote Similarity NPC473358
0.6718 Remote Similarity NPC50782
0.6691 Remote Similarity NPC228875
0.6691 Remote Similarity NPC105147
0.6691 Remote Similarity NPC126216
0.6691 Remote Similarity NPC474147
0.6691 Remote Similarity NPC473708
0.669 Remote Similarity NPC156356
0.669 Remote Similarity NPC168680
0.6667 Remote Similarity NPC469979
0.6667 Remote Similarity NPC226001
0.6667 Remote Similarity NPC250597
0.6643 Remote Similarity NPC150929
0.6642 Remote Similarity NPC105999
0.6641 Remote Similarity NPC7097
0.6641 Remote Similarity NPC233731
0.6641 Remote Similarity NPC246358
0.6641 Remote Similarity NPC36108
0.6626 Remote Similarity NPC298981
0.6626 Remote Similarity NPC110454
0.6626 Remote Similarity NPC473462
0.6626 Remote Similarity NPC207819
0.6626 Remote Similarity NPC126128
0.6624 Remote Similarity NPC38980
0.6622 Remote Similarity NPC184632
0.6621 Remote Similarity NPC224663
0.6619 Remote Similarity NPC43706
0.6617 Remote Similarity NPC293619
0.6614 Remote Similarity NPC124712
0.6596 Remote Similarity NPC474536
0.6594 Remote Similarity NPC213414
0.6594 Remote Similarity NPC228972
0.6594 Remote Similarity NPC74478
0.6594 Remote Similarity NPC122792
0.6571 Remote Similarity NPC122359
0.6571 Remote Similarity NPC78061
0.6571 Remote Similarity NPC159987
0.6567 Remote Similarity NPC470626
0.6562 Remote Similarity NPC471495
0.6554 Remote Similarity NPC474850
0.6554 Remote Similarity NPC474851
0.6554 Remote Similarity NPC118794
0.6549 Remote Similarity NPC204932
0.6547 Remote Similarity NPC3221
0.6547 Remote Similarity NPC87113
0.6547 Remote Similarity NPC194519
0.6544 Remote Similarity NPC307253
0.6541 Remote Similarity NPC79844
0.6538 Remote Similarity NPC8547
0.6538 Remote Similarity NPC156840
0.6538 Remote Similarity NPC195873
0.6538 Remote Similarity NPC173746
0.6538 Remote Similarity NPC139617
0.6538 Remote Similarity NPC257124
0.6538 Remote Similarity NPC78918
0.6535 Remote Similarity NPC232654
0.6535 Remote Similarity NPC41594
0.6528 Remote Similarity NPC303993
0.6528 Remote Similarity NPC471328
0.6519 Remote Similarity NPC281298
0.6519 Remote Similarity NPC310338
0.6519 Remote Similarity NPC117759
0.6516 Remote Similarity NPC135103
0.6506 Remote Similarity NPC214188
0.6506 Remote Similarity NPC74618
0.6506 Remote Similarity NPC301941
0.6503 Remote Similarity NPC225130
0.65 Remote Similarity NPC58607
0.65 Remote Similarity NPC156854
0.65 Remote Similarity NPC134431
0.65 Remote Similarity NPC17837
0.65 Remote Similarity NPC178284
0.65 Remote Similarity NPC181361
0.65 Remote Similarity NPC304630
0.65 Remote Similarity NPC191037
0.65 Remote Similarity NPC110677
0.6479 Remote Similarity NPC474614
0.6475 Remote Similarity NPC293701
0.6475 Remote Similarity NPC48990
0.6475 Remote Similarity NPC114901
0.6471 Remote Similarity NPC95614
0.6471 Remote Similarity NPC56214
0.6471 Remote Similarity NPC10932
0.6471 Remote Similarity NPC165133
0.6471 Remote Similarity NPC242885
0.6471 Remote Similarity NPC232084
0.6471 Remote Similarity NPC227217
0.6471 Remote Similarity NPC61516
0.6471 Remote Similarity NPC247364
0.6471 Remote Similarity NPC117780
0.6471 Remote Similarity NPC232316
0.6462 Remote Similarity NPC471487
0.6454 Remote Similarity NPC183181
0.6454 Remote Similarity NPC292056
0.6454 Remote Similarity NPC41706
0.6454 Remote Similarity NPC470699
0.6454 Remote Similarity NPC210355
0.6454 Remote Similarity NPC118787
0.6454 Remote Similarity NPC147821
0.6454 Remote Similarity NPC111247
0.6454 Remote Similarity NPC50368
0.6454 Remote Similarity NPC216836
0.6454 Remote Similarity NPC163332
0.6454 Remote Similarity NPC319625
0.6452 Remote Similarity NPC132725
0.6452 Remote Similarity NPC307039

  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 NPC41232 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
0.7241 Intermediate Similarity NPD9296 Approved
0.7025 Intermediate Similarity NPD291 Approved
0.6838 Remote Similarity NPD9365 Approved
0.6791 Remote Similarity NPD915 Approved
0.6538 Remote Similarity NPD228 Approved
0.6535 Remote Similarity NPD968 Approved
0.6512 Remote Similarity NPD556 Approved
0.6387 Remote Similarity NPD9295 Approved
0.6378 Remote Similarity NPD9244 Approved
0.6338 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6294 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6286 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6269 Remote Similarity NPD9299 Approved
0.625 Remote Similarity NPD9501 Approved
0.6233 Remote Similarity NPD1558 Phase 1
0.6231 Remote Similarity NPD9552 Approved
0.6231 Remote Similarity NPD290 Approved
0.6167 Remote Similarity NPD9094 Approved
0.6159 Remote Similarity NPD4010 Discontinued
0.6122 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6122 Remote Similarity NPD1613 Approved
0.6061 Remote Similarity NPD2684 Approved
0.6043 Remote Similarity NPD1798 Approved
0.6043 Remote Similarity NPD1797 Approved
0.6027 Remote Similarity NPD3027 Phase 3
0.5988 Remote Similarity NPD2296 Approved
0.5971 Remote Similarity NPD1548 Phase 1
0.5956 Remote Similarity NPD5283 Phase 1
0.5929 Remote Similarity NPD9087 Approved
0.5899 Remote Similarity NPD1103 Approved
0.5899 Remote Similarity NPD1408 Clinical (unspecified phase)
0.5899 Remote Similarity NPD1102 Approved
0.5887 Remote Similarity NPD6516 Phase 2
0.5887 Remote Similarity NPD5846 Approved
0.5882 Remote Similarity NPD7843 Approved
0.587 Remote Similarity NPD6671 Approved
0.5862 Remote Similarity NPD9088 Approved
0.5816 Remote Similarity NPD1357 Approved
0.5804 Remote Similarity NPD1091 Approved
0.5804 Remote Similarity NPD1610 Phase 2
0.5804 Remote Similarity NPD1535 Discovery
0.58 Remote Similarity NPD3620 Phase 2
0.58 Remote Similarity NPD3619 Clinical (unspecified phase)
0.5793 Remote Similarity NPD4288 Approved
0.5786 Remote Similarity NPD5536 Phase 2
0.5782 Remote Similarity NPD9494 Approved
0.5778 Remote Similarity NPD3021 Approved
0.5778 Remote Similarity NPD3022 Approved
0.5764 Remote Similarity NPD1481 Phase 2
0.5755 Remote Similarity NPD191 Approved
0.5755 Remote Similarity NPD7157 Approved
0.5753 Remote Similarity NPD1318 Phase 2
0.5753 Remote Similarity NPD3827 Clinical (unspecified phase)
0.5745 Remote Similarity NPD7534 Approved
0.5745 Remote Similarity NPD7533 Approved
0.5734 Remote Similarity NPD155 Clinical (unspecified phase)
0.5724 Remote Similarity NPD6582 Phase 2
0.5724 Remote Similarity NPD6583 Phase 3
0.5714 Remote Similarity NPD9697 Approved
0.5714 Remote Similarity NPD9093 Approved
0.5695 Remote Similarity NPD4060 Phase 1
0.5676 Remote Similarity NPD2250 Discontinued
0.5667 Remote Similarity NPD9089 Approved
0.5667 Remote Similarity NPD3144 Approved
0.5667 Remote Similarity NPD3145 Approved
0.5652 Remote Similarity NPD5535 Approved
0.5652 Remote Similarity NPD821 Approved
0.5649 Remote Similarity NPD1169 Approved
0.5646 Remote Similarity NPD1203 Approved
0.5638 Remote Similarity NPD3537 Clinical (unspecified phase)
0.5638 Remote Similarity NPD5752 Clinical (unspecified phase)
0.5634 Remote Similarity NPD1894 Discontinued
0.5629 Remote Similarity NPD2674 Phase 3
0.5625 Remote Similarity NPD2933 Approved
0.5625 Remote Similarity NPD2934 Approved
0.5616 Remote Similarity NPD2982 Phase 2
0.5616 Remote Similarity NPD2983 Phase 2
0.5608 Remote Similarity NPD6584 Phase 3
0.56 Remote Similarity NPD7095 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