Structure

Physi-Chem Properties

Molecular Weight:  497.71
Volume:  277.892
LogP:  5.755
LogD:  2.909
LogS:  -6.606
# Rotatable Bonds:  2
TPSA:  29.46
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.528
Synthetic Accessibility Score:  2.367
Fsp3:  0.0
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:  -4.771
MDCK Permeability:  1.743512439134065e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.852
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.553
Plasma Protein Binding (PPB):  100.61129760742188%
Volume Distribution (VD):  2.107
Pgp-substrate:  5.478254795074463%

ADMET: Metabolism

CYP1A2-inhibitor:  0.976
CYP1A2-substrate:  0.176
CYP2C19-inhibitor:  0.826
CYP2C19-substrate:  0.108
CYP2C9-inhibitor:  0.844
CYP2C9-substrate:  0.846
CYP2D6-inhibitor:  0.28
CYP2D6-substrate:  0.852
CYP3A4-inhibitor:  0.098
CYP3A4-substrate:  0.186

ADMET: Excretion

Clearance (CL):  0.855
Half-life (T1/2):  0.151

ADMET: Toxicity

hERG Blockers:  0.072
Human Hepatotoxicity (H-HT):  0.08
Drug-inuced Liver Injury (DILI):  0.773
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.773
Maximum Recommended Daily Dose:  0.165
Skin Sensitization:  0.88
Carcinogencity:  0.145
Eye Corrosion:  0.338
Eye Irritation:  0.98
Respiratory Toxicity:  0.768

Download Data

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

  Natural Product: NPC226737

Natural Product ID:  NPC226737
Common Name*:   2,3-Dibromo-6-(2,4-Dibromophenoxy)Phenol
IUPAC Name:   2,3-dibromo-6-(2,4-dibromophenoxy)phenol
Synonyms:  
Standard InCHIKey:  IANYKPWPWMDJDH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H6Br4O2/c13-6-1-3-9(8(15)5-6)18-10-4-2-7(14)11(16)12(10)17/h1-5,17H
SMILES:  Brc1ccc(c(c1)Br)Oc1ccc(c(c1O)Br)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL256782
PubChem CID:   10839158
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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 7230.0 nM PMID[549493]
NPT447 Organism Streptomyces Streptomyces IZ = 13.0 mm PMID[549493]
NPT447 Organism Streptomyces Streptomyces IZ = 14.0 mm PMID[549493]
NPT447 Organism Streptomyces Streptomyces IZ = 10.0 mm PMID[549493]

☑ 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 NPC226737 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 NPC299939
1.0 High Similarity NPC153580
0.9912 High Similarity NPC41232
0.9912 High Similarity NPC63317
0.9826 High Similarity NPC25134
0.9826 High Similarity NPC64130
0.9826 High Similarity NPC97157
0.9826 High Similarity NPC175520
0.9826 High Similarity NPC295879
0.9826 High Similarity NPC159866
0.9823 High Similarity NPC86007
0.9823 High Similarity NPC44270
0.9739 High Similarity NPC40302
0.9739 High Similarity NPC474375
0.9739 High Similarity NPC88733
0.9739 High Similarity NPC137922
0.9739 High Similarity NPC173511
0.9735 High Similarity NPC191194
0.9735 High Similarity NPC104124
0.9652 High Similarity NPC196371
0.9652 High Similarity NPC47769
0.9573 High Similarity NPC197576
0.9573 High Similarity NPC68350
0.9573 High Similarity NPC81149
0.9573 High Similarity NPC131940
0.9573 High Similarity NPC230013
0.9483 High Similarity NPC170824
0.9187 High Similarity NPC178301
0.9106 High Similarity NPC206183
0.9106 High Similarity NPC222684
0.9052 High Similarity NPC264379
0.8966 High Similarity NPC162294
0.8898 High Similarity NPC71186
0.8879 High Similarity NPC221301
0.8862 High Similarity NPC45728
0.8407 Intermediate Similarity NPC319933
0.84 Intermediate Similarity NPC163019
0.84 Intermediate Similarity NPC1744
0.8222 Intermediate Similarity NPC8577
0.816 Intermediate Similarity NPC235166
0.7672 Intermediate Similarity NPC314803
0.7478 Intermediate Similarity NPC475466
0.7447 Intermediate Similarity NPC286337
0.7391 Intermediate Similarity NPC245386
0.7357 Intermediate Similarity NPC271942
0.7328 Intermediate Similarity NPC114325
0.7259 Intermediate Similarity NPC13004
0.7239 Intermediate Similarity NPC220311
0.7168 Intermediate Similarity NPC252149
0.7164 Intermediate Similarity NPC236265
0.7162 Intermediate Similarity NPC152947
0.7101 Intermediate Similarity NPC160081
0.7101 Intermediate Similarity NPC226493
0.7077 Intermediate Similarity NPC86947
0.7029 Intermediate Similarity NPC85049
0.7 Intermediate Similarity NPC303011
0.6991 Remote Similarity NPC319826
0.697 Remote Similarity NPC38483
0.6966 Remote Similarity NPC89341
0.6947 Remote Similarity NPC151617
0.6947 Remote Similarity NPC76915
0.6944 Remote Similarity NPC160932
0.6935 Remote Similarity NPC307875
0.6923 Remote Similarity NPC318429
0.6889 Remote Similarity NPC219444
0.6883 Remote Similarity NPC474535
0.6867 Remote Similarity NPC473608
0.6866 Remote Similarity NPC205213
0.6861 Remote Similarity NPC142776
0.6857 Remote Similarity NPC11449
0.6846 Remote Similarity NPC94217
0.6842 Remote Similarity NPC125306
0.6842 Remote Similarity NPC214289
0.6839 Remote Similarity NPC475697
0.6838 Remote Similarity NPC84606
0.6838 Remote Similarity NPC473572
0.6838 Remote Similarity NPC474169
0.6824 Remote Similarity NPC109346
0.6818 Remote Similarity NPC9248
0.6815 Remote Similarity NPC127389
0.6815 Remote Similarity NPC290451
0.681 Remote Similarity NPC206876
0.6806 Remote Similarity NPC213471
0.6797 Remote Similarity NPC473358
0.6788 Remote Similarity NPC137117
0.6769 Remote Similarity NPC33244
0.6769 Remote Similarity NPC471488
0.6765 Remote Similarity NPC47790
0.6765 Remote Similarity NPC229213
0.6741 Remote Similarity NPC205850
0.6728 Remote Similarity NPC469979
0.6719 Remote Similarity NPC7097
0.6719 Remote Similarity NPC36108
0.6719 Remote Similarity NPC54543
0.6719 Remote Similarity NPC233731
0.6719 Remote Similarity NPC246358
0.6713 Remote Similarity NPC244890
0.6713 Remote Similarity NPC163560
0.6693 Remote Similarity NPC124712
0.6692 Remote Similarity NPC293619
0.6691 Remote Similarity NPC145780
0.6691 Remote Similarity NPC134219
0.6687 Remote Similarity NPC110454
0.6687 Remote Similarity NPC126128
0.6687 Remote Similarity NPC298981
0.6687 Remote Similarity NPC473462
0.6687 Remote Similarity NPC207819
0.6667 Remote Similarity NPC228972
0.6667 Remote Similarity NPC213414
0.6667 Remote Similarity NPC74478
0.6667 Remote Similarity NPC122792
0.6667 Remote Similarity NPC50782
0.6644 Remote Similarity NPC156356
0.6644 Remote Similarity NPC168680
0.6643 Remote Similarity NPC122359
0.6643 Remote Similarity NPC474147
0.6643 Remote Similarity NPC78061
0.6643 Remote Similarity NPC159987
0.6643 Remote Similarity NPC473708
0.6642 Remote Similarity NPC105147
0.6642 Remote Similarity NPC228875
0.6642 Remote Similarity NPC470626
0.6642 Remote Similarity NPC126216
0.6641 Remote Similarity NPC471495
0.6637 Remote Similarity NPC204932
0.6626 Remote Similarity NPC226001
0.6622 Remote Similarity NPC250597
0.6619 Remote Similarity NPC194519
0.6619 Remote Similarity NPC3221
0.6619 Remote Similarity NPC87113
0.6618 Remote Similarity NPC307253
0.6615 Remote Similarity NPC8547
0.6615 Remote Similarity NPC156840
0.6615 Remote Similarity NPC173746
0.6615 Remote Similarity NPC139617
0.6615 Remote Similarity NPC195873
0.6615 Remote Similarity NPC257124
0.6615 Remote Similarity NPC78918
0.6614 Remote Similarity NPC41594
0.6597 Remote Similarity NPC303993
0.6596 Remote Similarity NPC150929
0.6594 Remote Similarity NPC105999
0.6593 Remote Similarity NPC117759
0.6593 Remote Similarity NPC281298
0.6593 Remote Similarity NPC310338
0.6582 Remote Similarity NPC38980
0.6577 Remote Similarity NPC184632
0.6575 Remote Similarity NPC224663
0.6571 Remote Similarity NPC134431
0.6571 Remote Similarity NPC304630
0.6571 Remote Similarity NPC178284
0.6571 Remote Similarity NPC43706
0.6571 Remote Similarity NPC156854
0.6571 Remote Similarity NPC58607
0.6571 Remote Similarity NPC191037
0.6571 Remote Similarity NPC17837
0.6566 Remote Similarity NPC214188
0.6566 Remote Similarity NPC74618
0.6566 Remote Similarity NPC301941
0.6564 Remote Similarity NPC225130
0.6549 Remote Similarity NPC474536
0.6547 Remote Similarity NPC48990
0.6547 Remote Similarity NPC114901
0.6547 Remote Similarity NPC293701
0.6544 Remote Similarity NPC247364
0.6544 Remote Similarity NPC227217
0.6544 Remote Similarity NPC61516
0.6544 Remote Similarity NPC117780
0.6544 Remote Similarity NPC56214
0.6544 Remote Similarity NPC95614
0.6544 Remote Similarity NPC10932
0.6544 Remote Similarity NPC232084
0.6544 Remote Similarity NPC232316
0.6544 Remote Similarity NPC165133
0.6544 Remote Similarity NPC242885
0.6538 Remote Similarity NPC471487
0.6532 Remote Similarity NPC307039
0.6532 Remote Similarity NPC132725
0.6525 Remote Similarity NPC111247
0.6525 Remote Similarity NPC50368
0.6525 Remote Similarity NPC183181
0.6525 Remote Similarity NPC470699
0.6525 Remote Similarity NPC41706
0.6525 Remote Similarity NPC319625
0.6525 Remote Similarity NPC210355
0.6525 Remote Similarity NPC147821
0.6525 Remote Similarity NPC292056
0.6525 Remote Similarity NPC163332
0.6525 Remote Similarity NPC118787
0.6522 Remote Similarity NPC296202
0.651 Remote Similarity NPC474851
0.651 Remote Similarity NPC474850
0.651 Remote Similarity NPC118794
0.6496 Remote Similarity NPC207613
0.6496 Remote Similarity NPC109083
0.6496 Remote Similarity NPC189844
0.6496 Remote Similarity NPC14007
0.6496 Remote Similarity NPC224814
0.6496 Remote Similarity NPC60962
0.6496 Remote Similarity NPC269843

  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 NPC226737 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
0.7328 Intermediate Similarity NPD9296 Approved
0.7107 Intermediate Similarity NPD291 Approved
0.6923 Remote Similarity NPD9365 Approved
0.6866 Remote Similarity NPD915 Approved
0.6615 Remote Similarity NPD228 Approved
0.6614 Remote Similarity NPD968 Approved
0.6589 Remote Similarity NPD556 Approved
0.6471 Remote Similarity NPD9295 Approved
0.6364 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6357 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6343 Remote Similarity NPD9299 Approved
0.6328 Remote Similarity NPD9501 Approved
0.6328 Remote Similarity NPD9244 Approved
0.6308 Remote Similarity NPD9552 Approved
0.6308 Remote Similarity NPD290 Approved
0.6301 Remote Similarity NPD1558 Phase 1
0.6294 Remote Similarity NPD1530 Clinical (unspecified phase)
0.625 Remote Similarity NPD9094 Approved
0.619 Remote Similarity NPD1612 Clinical (unspecified phase)
0.619 Remote Similarity NPD1613 Approved
0.6136 Remote Similarity NPD2684 Approved
0.6121 Remote Similarity NPD4010 Discontinued
0.6115 Remote Similarity NPD1798 Approved
0.6115 Remote Similarity NPD1797 Approved
0.6096 Remote Similarity NPD3027 Phase 3
0.6049 Remote Similarity NPD2296 Approved
0.6043 Remote Similarity NPD1548 Phase 1
0.6029 Remote Similarity NPD5283 Phase 1
0.6018 Remote Similarity NPD9087 Approved
0.5971 Remote Similarity NPD1103 Approved
0.5971 Remote Similarity NPD1102 Approved
0.5971 Remote Similarity NPD1408 Clinical (unspecified phase)
0.5957 Remote Similarity NPD5846 Approved
0.5957 Remote Similarity NPD6516 Phase 2
0.5956 Remote Similarity NPD7843 Approved
0.5948 Remote Similarity NPD9088 Approved
0.5942 Remote Similarity NPD6671 Approved
0.5887 Remote Similarity NPD1357 Approved
0.5874 Remote Similarity NPD1610 Phase 2
0.5874 Remote Similarity NPD1091 Approved
0.5874 Remote Similarity NPD1535 Discovery
0.5857 Remote Similarity NPD5536 Phase 2
0.5854 Remote Similarity NPD4288 Approved
0.5852 Remote Similarity NPD3022 Approved
0.5852 Remote Similarity NPD3021 Approved
0.585 Remote Similarity NPD9494 Approved
0.5833 Remote Similarity NPD1481 Phase 2
0.5827 Remote Similarity NPD191 Approved
0.5827 Remote Similarity NPD7157 Approved
0.5822 Remote Similarity NPD3827 Clinical (unspecified phase)
0.5822 Remote Similarity NPD1318 Phase 2
0.5816 Remote Similarity NPD7534 Approved
0.5816 Remote Similarity NPD7533 Approved
0.5804 Remote Similarity NPD155 Clinical (unspecified phase)
0.5793 Remote Similarity NPD6583 Phase 3
0.5793 Remote Similarity NPD6582 Phase 2
0.5789 Remote Similarity NPD9697 Approved
0.5762 Remote Similarity NPD3619 Clinical (unspecified phase)
0.5762 Remote Similarity NPD4060 Phase 1
0.5762 Remote Similarity NPD3620 Phase 2
0.575 Remote Similarity NPD9089 Approved
0.5743 Remote Similarity NPD2250 Discontinued
0.5733 Remote Similarity NPD3144 Approved
0.5733 Remote Similarity NPD3145 Approved
0.5725 Remote Similarity NPD821 Approved
0.5725 Remote Similarity NPD5535 Approved
0.5714 Remote Similarity NPD1169 Approved
0.5714 Remote Similarity NPD1203 Approved
0.5705 Remote Similarity NPD3537 Clinical (unspecified phase)
0.5705 Remote Similarity NPD5752 Clinical (unspecified phase)
0.5704 Remote Similarity NPD1894 Discontinued
0.5703 Remote Similarity NPD2933 Approved
0.5703 Remote Similarity NPD2934 Approved
0.5695 Remote Similarity NPD2674 Phase 3
0.5685 Remote Similarity NPD2983 Phase 2
0.5685 Remote Similarity NPD2982 Phase 2
0.5676 Remote Similarity NPD6584 Phase 3
0.5667 Remote Similarity NPD9093 Approved
0.5667 Remote Similarity NPD7095 Approved
0.5659 Remote Similarity NPD2860 Approved
0.5659 Remote Similarity NPD2859 Approved
0.5655 Remote Similarity NPD422 Phase 1
0.5646 Remote Similarity NPD3225 Approved
0.5638 Remote Similarity NPD2861 Phase 2
0.5638 Remote Similarity NPD5266 Clinical (unspecified phase)
0.5629 Remote Similarity NPD6798 Discontinued
0.5625 Remote Similarity NPD1511 Approved
0.5621 Remote Similarity NPD447 Suspended
0.5616 Remote Similarity NPD2235 Phase 2
0.5616 Remote Similarity NPD2981 Phase 2
0.5616 Remote Similarity NPD1608 Approved
0.5616 Remote Similarity NPD2231 Phase 2
0.5612 Remote Similarity NPD769 Approved
0.5608 Remote Similarity NPD2797 Approved
0.5608 Remote Similarity NPD9549 Phase 2
0.56 Remote Similarity NPD4908 Phase 1

  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