Structure

Physi-Chem Properties

Molecular Weight:  575.62
Volume:  297.175
LogP:  6.171
LogD:  2.677
LogS:  -7.443
# Rotatable Bonds:  2
TPSA:  29.46
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.388
Synthetic Accessibility Score:  2.636
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:  -4.783
MDCK Permeability:  1.5620162230334245e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.936
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.541
Plasma Protein Binding (PPB):  103.01492309570312%
Volume Distribution (VD):  3.539
Pgp-substrate:  7.5951828956604%

ADMET: Metabolism

CYP1A2-inhibitor:  0.959
CYP1A2-substrate:  0.157
CYP2C19-inhibitor:  0.766
CYP2C19-substrate:  0.099
CYP2C9-inhibitor:  0.825
CYP2C9-substrate:  0.769
CYP2D6-inhibitor:  0.073
CYP2D6-substrate:  0.746
CYP3A4-inhibitor:  0.074
CYP3A4-substrate:  0.133

ADMET: Excretion

Clearance (CL):  0.665
Half-life (T1/2):  0.128

ADMET: Toxicity

hERG Blockers:  0.084
Human Hepatotoxicity (H-HT):  0.128
Drug-inuced Liver Injury (DILI):  0.794
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.935
Maximum Recommended Daily Dose:  0.908
Skin Sensitization:  0.872
Carcinogencity:  0.107
Eye Corrosion:  0.441
Eye Irritation:  0.973
Respiratory Toxicity:  0.815

Download Data

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

  Natural Product: NPC97157

Natural Product ID:  NPC97157
Common Name*:   3,4,6-Tribromo-2-(2,4-Dibromophenoxy)Phenol
IUPAC Name:   3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
Synonyms:  
Standard InCHIKey:  FAGFPLJEMPQMRV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H5Br5O2/c13-5-1-2-9(6(14)3-5)19-12-10(17)7(15)4-8(16)11(12)18/h1-4,18H
SMILES:  Brc1ccc(c(c1)Br)Oc1c(O)c(Br)cc(c1Br)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL186098
PubChem CID:   11093078
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
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens IC50 = 6000.0 nM PMID[542430]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 8730.0 nM PMID[542431]
NPT35 Others n.a. CLogP = 7.34 n.a. PMID[542430]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens IC50 = 5000.0 nM PMID[542430]
NPT2 Others Unspecified IC50 = 9000.0 nM PMID[542430]
NPT447 Organism Streptomyces Streptomyces IZ = 12.0 mm PMID[542431]
NPT447 Organism Streptomyces Streptomyces IZ = 3.0 mm PMID[542431]
NPT447 Organism Streptomyces Streptomyces IZ = 2.0 mm PMID[542431]
NPT447 Organism Streptomyces Streptomyces IZ = 15.0 mm PMID[542431]
NPT447 Organism Streptomyces Streptomyces IZ = 13.0 mm PMID[542431]

☑ 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 NPC97157 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 NPC64130
1.0 High Similarity NPC159866
1.0 High Similarity NPC295879
1.0 High Similarity NPC175520
1.0 High Similarity NPC25134
0.9913 High Similarity NPC40302
0.9913 High Similarity NPC137922
0.9913 High Similarity NPC474375
0.9826 High Similarity NPC196371
0.9826 High Similarity NPC226737
0.9826 High Similarity NPC299939
0.9826 High Similarity NPC153580
0.9826 High Similarity NPC47769
0.9744 High Similarity NPC230013
0.9744 High Similarity NPC197576
0.9744 High Similarity NPC68350
0.9744 High Similarity NPC81149
0.9744 High Similarity NPC131940
0.9739 High Similarity NPC63317
0.9739 High Similarity NPC41232
0.9652 High Similarity NPC44270
0.9652 High Similarity NPC86007
0.9573 High Similarity NPC173511
0.9573 High Similarity NPC88733
0.9565 High Similarity NPC191194
0.9565 High Similarity NPC104124
0.9322 High Similarity NPC170824
0.9068 High Similarity NPC71186
0.904 High Similarity NPC178301
0.896 High Similarity NPC206183
0.896 High Similarity NPC222684
0.8898 High Similarity NPC264379
0.8814 High Similarity NPC162294
0.8729 High Similarity NPC221301
0.872 High Similarity NPC45728
0.8268 Intermediate Similarity NPC163019
0.8268 Intermediate Similarity NPC1744
0.8261 Intermediate Similarity NPC319933
0.8102 Intermediate Similarity NPC8577
0.8031 Intermediate Similarity NPC235166
0.7652 Intermediate Similarity NPC475466
0.7542 Intermediate Similarity NPC314803
0.75 Intermediate Similarity NPC271942
0.7407 Intermediate Similarity NPC13004
0.7343 Intermediate Similarity NPC286337
0.7313 Intermediate Similarity NPC236265
0.7297 Intermediate Similarity NPC152947
0.7286 Intermediate Similarity NPC245386
0.7203 Intermediate Similarity NPC114325
0.7143 Intermediate Similarity NPC303011
0.7132 Intermediate Similarity NPC220311
0.7043 Intermediate Similarity NPC252149
0.7037 Intermediate Similarity NPC219444
0.7 Intermediate Similarity NPC226493
0.7 Intermediate Similarity NPC160081
0.6985 Remote Similarity NPC84606
0.697 Remote Similarity NPC86947
0.6929 Remote Similarity NPC85049
0.6871 Remote Similarity NPC89341
0.687 Remote Similarity NPC319826
0.6866 Remote Similarity NPC38483
0.6849 Remote Similarity NPC160932
0.6842 Remote Similarity NPC76915
0.6842 Remote Similarity NPC151617
0.6835 Remote Similarity NPC134219
0.6825 Remote Similarity NPC307875
0.6818 Remote Similarity NPC50782
0.6807 Remote Similarity NPC318429
0.6795 Remote Similarity NPC474535
0.6786 Remote Similarity NPC474147
0.6786 Remote Similarity NPC473708
0.6781 Remote Similarity NPC168680
0.6776 Remote Similarity NPC473608
0.6765 Remote Similarity NPC205213
0.6763 Remote Similarity NPC142776
0.6761 Remote Similarity NPC11449
0.6752 Remote Similarity NPC475697
0.6742 Remote Similarity NPC94217
0.6741 Remote Similarity NPC214289
0.6739 Remote Similarity NPC473572
0.6739 Remote Similarity NPC474169
0.6733 Remote Similarity NPC109346
0.6724 Remote Similarity NPC125306
0.6716 Remote Similarity NPC9248
0.6715 Remote Similarity NPC290451
0.6715 Remote Similarity NPC127389
0.6714 Remote Similarity NPC43706
0.6712 Remote Similarity NPC213471
0.6695 Remote Similarity NPC206876
0.6692 Remote Similarity NPC473358
0.6691 Remote Similarity NPC137117
0.6667 Remote Similarity NPC229213
0.6667 Remote Similarity NPC47790
0.6667 Remote Similarity NPC33244
0.6667 Remote Similarity NPC471488
0.6646 Remote Similarity NPC469979
0.6642 Remote Similarity NPC205850
0.6621 Remote Similarity NPC163560
0.6621 Remote Similarity NPC244890
0.6615 Remote Similarity NPC7097
0.6615 Remote Similarity NPC54543
0.6615 Remote Similarity NPC36108
0.6615 Remote Similarity NPC246358
0.6615 Remote Similarity NPC233731
0.6606 Remote Similarity NPC126128
0.6606 Remote Similarity NPC473462
0.6606 Remote Similarity NPC298981
0.6606 Remote Similarity NPC207819
0.6606 Remote Similarity NPC110454
0.6603 Remote Similarity NPC135103
0.6594 Remote Similarity NPC145780
0.6593 Remote Similarity NPC293619
0.6589 Remote Similarity NPC124712
0.6571 Remote Similarity NPC74478
0.6571 Remote Similarity NPC122792
0.6571 Remote Similarity NPC228972
0.6571 Remote Similarity NPC213414
0.6554 Remote Similarity NPC156356
0.6549 Remote Similarity NPC122359
0.6549 Remote Similarity NPC78061
0.6549 Remote Similarity NPC159987
0.6547 Remote Similarity NPC126216
0.6547 Remote Similarity NPC105147
0.6547 Remote Similarity NPC228875
0.6545 Remote Similarity NPC226001
0.6544 Remote Similarity NPC470626
0.6538 Remote Similarity NPC471495
0.6533 Remote Similarity NPC250597
0.6525 Remote Similarity NPC194519
0.6525 Remote Similarity NPC87113
0.6525 Remote Similarity NPC3221
0.6522 Remote Similarity NPC307253
0.6522 Remote Similarity NPC227976
0.6522 Remote Similarity NPC204932
0.6515 Remote Similarity NPC8547
0.6515 Remote Similarity NPC156840
0.6515 Remote Similarity NPC195873
0.6515 Remote Similarity NPC257124
0.6515 Remote Similarity NPC139617
0.6515 Remote Similarity NPC173746
0.6515 Remote Similarity NPC78918
0.6512 Remote Similarity NPC41594
0.6507 Remote Similarity NPC303993
0.6503 Remote Similarity NPC150929
0.65 Remote Similarity NPC105999
0.65 Remote Similarity NPC38980
0.6496 Remote Similarity NPC281298
0.6496 Remote Similarity NPC310338
0.6496 Remote Similarity NPC117759
0.649 Remote Similarity NPC184632
0.6488 Remote Similarity NPC301941
0.6488 Remote Similarity NPC214188
0.6488 Remote Similarity NPC74618
0.6486 Remote Similarity NPC224663
0.6485 Remote Similarity NPC225130
0.6479 Remote Similarity NPC156854
0.6479 Remote Similarity NPC58607
0.6479 Remote Similarity NPC17837
0.6479 Remote Similarity NPC304630
0.6479 Remote Similarity NPC134431
0.6479 Remote Similarity NPC178284
0.6479 Remote Similarity NPC191037
0.6458 Remote Similarity NPC474536
0.6458 Remote Similarity NPC105702
0.6454 Remote Similarity NPC48990
0.6454 Remote Similarity NPC114901
0.6454 Remote Similarity NPC293701
0.6449 Remote Similarity NPC117780
0.6449 Remote Similarity NPC165133
0.6449 Remote Similarity NPC242885
0.6449 Remote Similarity NPC95614
0.6449 Remote Similarity NPC56214
0.6449 Remote Similarity NPC61516
0.6449 Remote Similarity NPC10932
0.6449 Remote Similarity NPC232084
0.6449 Remote Similarity NPC227217
0.6449 Remote Similarity NPC232316
0.6449 Remote Similarity NPC474146
0.6449 Remote Similarity NPC247364
0.6439 Remote Similarity NPC471487
0.6434 Remote Similarity NPC41706
0.6434 Remote Similarity NPC470699
0.6434 Remote Similarity NPC147821
0.6434 Remote Similarity NPC210355
0.6434 Remote Similarity NPC319625
0.6434 Remote Similarity NPC111247
0.6434 Remote Similarity NPC50368
0.6434 Remote Similarity NPC118787
0.6434 Remote Similarity NPC163332
0.6434 Remote Similarity NPC183181
0.6434 Remote Similarity NPC292056
0.6429 Remote Similarity NPC296202
0.6429 Remote Similarity NPC132725
0.6429 Remote Similarity NPC307039
0.6424 Remote Similarity NPC474851
0.6424 Remote Similarity NPC474850
0.6424 Remote Similarity NPC118794
0.6403 Remote Similarity NPC189844
0.6403 Remote Similarity NPC14007
0.6403 Remote Similarity NPC224814

  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 NPC97157 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
0.7203 Intermediate Similarity NPD9296 Approved
0.6992 Remote Similarity NPD291 Approved
0.6807 Remote Similarity NPD9365 Approved
0.6765 Remote Similarity NPD915 Approved
0.6515 Remote Similarity NPD228 Approved
0.6512 Remote Similarity NPD968 Approved
0.6489 Remote Similarity NPD556 Approved
0.6364 Remote Similarity NPD9295 Approved
0.6276 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6268 Remote Similarity NPD4379 Clinical (unspecified phase)
0.625 Remote Similarity NPD9299 Approved
0.6231 Remote Similarity NPD9244 Approved
0.6231 Remote Similarity NPD9501 Approved
0.6216 Remote Similarity NPD1558 Phase 1
0.6212 Remote Similarity NPD290 Approved
0.6212 Remote Similarity NPD9552 Approved
0.6207 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6148 Remote Similarity NPD9094 Approved
0.6107 Remote Similarity NPD1613 Approved
0.6107 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6048 Remote Similarity NPD4010 Discontinued
0.6045 Remote Similarity NPD2684 Approved
0.6028 Remote Similarity NPD1798 Approved
0.6028 Remote Similarity NPD1797 Approved
0.6014 Remote Similarity NPD3027 Phase 3
0.5976 Remote Similarity NPD2296 Approved
0.5957 Remote Similarity NPD1548 Phase 1
0.5942 Remote Similarity NPD5283 Phase 1
0.5913 Remote Similarity NPD9087 Approved
0.5887 Remote Similarity NPD1102 Approved
0.5887 Remote Similarity NPD1103 Approved
0.5887 Remote Similarity NPD1408 Clinical (unspecified phase)
0.5874 Remote Similarity NPD6516 Phase 2
0.5874 Remote Similarity NPD5846 Approved
0.587 Remote Similarity NPD7843 Approved
0.5857 Remote Similarity NPD6671 Approved
0.5847 Remote Similarity NPD9088 Approved
0.5804 Remote Similarity NPD1357 Approved
0.5793 Remote Similarity NPD1535 Discovery
0.5793 Remote Similarity NPD1610 Phase 2
0.5793 Remote Similarity NPD1091 Approved
0.5783 Remote Similarity NPD4288 Approved
0.5775 Remote Similarity NPD5536 Phase 2
0.5772 Remote Similarity NPD9494 Approved
0.5766 Remote Similarity NPD3021 Approved
0.5766 Remote Similarity NPD3022 Approved
0.5753 Remote Similarity NPD1481 Phase 2
0.5745 Remote Similarity NPD7157 Approved
0.5745 Remote Similarity NPD191 Approved
0.5743 Remote Similarity NPD1318 Phase 2
0.5743 Remote Similarity NPD3827 Clinical (unspecified phase)
0.5734 Remote Similarity NPD7533 Approved
0.5734 Remote Similarity NPD7534 Approved
0.5724 Remote Similarity NPD155 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6583 Phase 3
0.5714 Remote Similarity NPD6582 Phase 2
0.5704 Remote Similarity NPD9697 Approved
0.5686 Remote Similarity NPD4060 Phase 1
0.5686 Remote Similarity NPD3620 Phase 2
0.5686 Remote Similarity NPD3619 Clinical (unspecified phase)
0.5667 Remote Similarity NPD2250 Discontinued
0.5658 Remote Similarity NPD3144 Approved
0.5658 Remote Similarity NPD3145 Approved
0.5656 Remote Similarity NPD9089 Approved
0.5643 Remote Similarity NPD5535 Approved
0.5643 Remote Similarity NPD821 Approved
0.5641 Remote Similarity NPD1169 Approved
0.5638 Remote Similarity NPD1203 Approved
0.5629 Remote Similarity NPD3537 Clinical (unspecified phase)
0.5629 Remote Similarity NPD5752 Clinical (unspecified phase)
0.5625 Remote Similarity NPD1894 Discontinued
0.5621 Remote Similarity NPD2674 Phase 3
0.5615 Remote Similarity NPD2934 Approved
0.5615 Remote Similarity NPD2933 Approved
0.5608 Remote Similarity NPD2983 Phase 2
0.5608 Remote Similarity NPD2982 Phase 2
0.56 Remote Similarity NPD6584 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