Structure

Physi-Chem Properties

Molecular Weight:  249.86
Volume:  143.224
LogP:  2.995
LogD:  2.407
LogS:  -3.112
# Rotatable Bonds:  0
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.752
Synthetic Accessibility Score:  2.04
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.378
MDCK Permeability:  2.028139897447545e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.059
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.961
Plasma Protein Binding (PPB):  97.17951965332031%
Volume Distribution (VD):  3.543
Pgp-substrate:  5.807557106018066%

ADMET: Metabolism

CYP1A2-inhibitor:  0.919
CYP1A2-substrate:  0.447
CYP2C19-inhibitor:  0.473
CYP2C19-substrate:  0.366
CYP2C9-inhibitor:  0.304
CYP2C9-substrate:  0.688
CYP2D6-inhibitor:  0.163
CYP2D6-substrate:  0.718
CYP3A4-inhibitor:  0.033
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  0.983
Half-life (T1/2):  0.746

ADMET: Toxicity

hERG Blockers:  0.077
Human Hepatotoxicity (H-HT):  0.141
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.941
Maximum Recommended Daily Dose:  0.039
Skin Sensitization:  0.727
Carcinogencity:  0.343
Eye Corrosion:  0.926
Eye Irritation:  0.992
Respiratory Toxicity:  0.64

Download Data

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

  Natural Product: NPC252149

Natural Product ID:  NPC252149
Common Name*:   2,6-Dibromophenol
IUPAC Name:   2,6-dibromophenol
Synonyms:   2,6-Dibromo-Phenol
Standard InCHIKey:  SSIZLKDLDKIHEV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H4Br2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H
SMILES:  Brc1cccc(c1O)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL111507
PubChem CID:   11847
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0002320] Halophenols
          • [CHEMONTID:0002764] Bromophenols
            • [CHEMONTID:0002768] O-bromophenols

*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
NPO24264 Pinus luchuensis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[12502340]
NPO23838 Kitasatospora kifunensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17191679]
NPO23565 Kadsura polysperma Species Schisandraceae Eukaryota stems Emei County of Sichuan Province, China 2009-AUG PMID[22329624]
NPO23838 Kitasatospora kifunensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24495 Heteropanax fragrans Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20740 Balanoglossus biminiensis Species Ptychoderidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23565 Kadsura polysperma Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13714 Abuta grandifolia Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23974 Mallotus claoxyloides Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24264 Pinus luchuensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22158 Terminalia oblonga Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23748 Aquilegia olympica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23132 Adenochlaena siamensis Species Euphorbiaceae 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
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens IC50 > 100000.0 nM PMID[506106]
NPT1007 Protein Complex GABA-A receptor; alpha-1/beta-2/gamma-2 Homo sapiens EC50 = 100000000.0 nM PMID[506105]
NPT693 Organism Xenopus laevis Xenopus laevis EC50 = 100000000.0 nM PMID[506105]
NPT35 Others n.a. CLogP = 3.0 n.a. PMID[506105]
NPT35 Others n.a. CLogP = 3.36 n.a. PMID[506106]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens IC50 > 100000.0 nM PMID[506106]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[506106]

☑ 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 NPC252149 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
0.9048 High Similarity NPC319826
0.8171 Intermediate Similarity NPC100980
0.7941 Intermediate Similarity NPC473358
0.7843 Intermediate Similarity NPC54543
0.7791 Intermediate Similarity NPC65517
0.7745 Intermediate Similarity NPC471495
0.7642 Intermediate Similarity NPC94217
0.76 Intermediate Similarity NPC319933
0.7547 Intermediate Similarity NPC33244
0.7547 Intermediate Similarity NPC471488
0.7528 Intermediate Similarity NPC204932
0.7477 Intermediate Similarity NPC115803
0.7444 Intermediate Similarity NPC270094
0.7423 Intermediate Similarity NPC475466
0.7333 Intermediate Similarity NPC4154
0.7297 Intermediate Similarity NPC44270
0.7297 Intermediate Similarity NPC86007
0.7294 Intermediate Similarity NPC215445
0.7264 Intermediate Similarity NPC471487
0.7222 Intermediate Similarity NPC59387
0.7207 Intermediate Similarity NPC104124
0.7204 Intermediate Similarity NPC265146
0.7204 Intermediate Similarity NPC124436
0.7204 Intermediate Similarity NPC38459
0.7204 Intermediate Similarity NPC33756
0.717 Intermediate Similarity NPC473372
0.7168 Intermediate Similarity NPC196371
0.7168 Intermediate Similarity NPC153580
0.7168 Intermediate Similarity NPC47769
0.7168 Intermediate Similarity NPC299939
0.7168 Intermediate Similarity NPC226737
0.7143 Intermediate Similarity NPC100395
0.7128 Intermediate Similarity NPC286904
0.7128 Intermediate Similarity NPC248817
0.7128 Intermediate Similarity NPC150837
0.7128 Intermediate Similarity NPC175313
0.708 Intermediate Similarity NPC63317
0.708 Intermediate Similarity NPC180207
0.708 Intermediate Similarity NPC41232
0.7064 Intermediate Similarity NPC76400
0.7054 Intermediate Similarity NPC191194
0.7053 Intermediate Similarity NPC197783
0.7053 Intermediate Similarity NPC155393
0.7043 Intermediate Similarity NPC64130
0.7043 Intermediate Similarity NPC159866
0.7043 Intermediate Similarity NPC175520
0.7043 Intermediate Similarity NPC295879
0.7043 Intermediate Similarity NPC25134
0.7043 Intermediate Similarity NPC97157
0.7018 Intermediate Similarity NPC471486
0.7018 Intermediate Similarity NPC170824
0.7 Intermediate Similarity NPC322285
0.6979 Remote Similarity NPC184169
0.6979 Remote Similarity NPC407
0.6979 Remote Similarity NPC307235
0.6979 Remote Similarity NPC280254
0.6979 Remote Similarity NPC23167
0.6957 Remote Similarity NPC173511
0.6957 Remote Similarity NPC88733
0.6957 Remote Similarity NPC474375
0.6957 Remote Similarity NPC137922
0.6957 Remote Similarity NPC40302
0.6923 Remote Similarity NPC213414
0.6907 Remote Similarity NPC113460
0.6907 Remote Similarity NPC104216
0.6907 Remote Similarity NPC157213
0.6907 Remote Similarity NPC25493
0.6907 Remote Similarity NPC27974
0.6875 Remote Similarity NPC79844
0.6842 Remote Similarity NPC38483
0.6842 Remote Similarity NPC117759
0.6838 Remote Similarity NPC68350
0.6838 Remote Similarity NPC230013
0.6838 Remote Similarity NPC131940
0.6838 Remote Similarity NPC105999
0.6838 Remote Similarity NPC81149
0.6838 Remote Similarity NPC197576
0.6837 Remote Similarity NPC258219
0.6837 Remote Similarity NPC123273
0.6837 Remote Similarity NPC318325
0.6837 Remote Similarity NPC177420
0.6837 Remote Similarity NPC98772
0.6837 Remote Similarity NPC242240
0.6837 Remote Similarity NPC280347
0.6786 Remote Similarity NPC162294
0.6783 Remote Similarity NPC474146
0.6768 Remote Similarity NPC300017
0.6768 Remote Similarity NPC47950
0.6768 Remote Similarity NPC151764
0.6768 Remote Similarity NPC300478
0.6768 Remote Similarity NPC55561
0.6768 Remote Similarity NPC312304
0.6768 Remote Similarity NPC288923
0.6768 Remote Similarity NPC277758
0.6768 Remote Similarity NPC192
0.6752 Remote Similarity NPC296202
0.6735 Remote Similarity NPC19680
0.67 Remote Similarity NPC45040
0.67 Remote Similarity NPC204210
0.67 Remote Similarity NPC155908
0.67 Remote Similarity NPC306074
0.67 Remote Similarity NPC304541
0.67 Remote Similarity NPC270547
0.67 Remote Similarity NPC231150
0.67 Remote Similarity NPC174048
0.67 Remote Similarity NPC322888
0.6696 Remote Similarity NPC221301
0.6667 Remote Similarity NPC70436
0.6667 Remote Similarity NPC7830
0.6667 Remote Similarity NPC124576
0.6667 Remote Similarity NPC45728
0.6639 Remote Similarity NPC99280
0.6639 Remote Similarity NPC478071
0.6637 Remote Similarity NPC50782
0.6634 Remote Similarity NPC181709
0.6634 Remote Similarity NPC29373
0.6634 Remote Similarity NPC306884
0.6634 Remote Similarity NPC138117
0.6634 Remote Similarity NPC325292
0.6634 Remote Similarity NPC162314
0.6634 Remote Similarity NPC210497
0.6634 Remote Similarity NPC147284
0.6634 Remote Similarity NPC3358
0.6634 Remote Similarity NPC271440
0.6634 Remote Similarity NPC55903
0.6634 Remote Similarity NPC94139
0.6612 Remote Similarity NPC13004
0.661 Remote Similarity NPC116562
0.661 Remote Similarity NPC47790
0.6585 Remote Similarity NPC11449
0.6585 Remote Similarity NPC475735
0.6585 Remote Similarity NPC178301
0.6583 Remote Similarity NPC142776
0.6579 Remote Similarity NPC264379
0.6569 Remote Similarity NPC16649
0.6569 Remote Similarity NPC114325
0.6569 Remote Similarity NPC32977
0.6569 Remote Similarity NPC289769
0.6569 Remote Similarity NPC76938
0.6569 Remote Similarity NPC128062
0.6569 Remote Similarity NPC152415
0.6569 Remote Similarity NPC27323
0.6569 Remote Similarity NPC245187
0.6569 Remote Similarity NPC81010
0.6569 Remote Similarity NPC151715
0.6569 Remote Similarity NPC316301
0.6525 Remote Similarity NPC136543
0.6505 Remote Similarity NPC26244
0.6505 Remote Similarity NPC246679
0.6505 Remote Similarity NPC257182
0.6505 Remote Similarity NPC286006
0.6505 Remote Similarity NPC274678
0.6505 Remote Similarity NPC313650
0.6505 Remote Similarity NPC8392
0.6505 Remote Similarity NPC32714
0.6505 Remote Similarity NPC107522
0.6504 Remote Similarity NPC206183
0.6504 Remote Similarity NPC222684
0.65 Remote Similarity NPC137117
0.6471 Remote Similarity NPC295295
0.6471 Remote Similarity NPC229213
0.6466 Remote Similarity NPC71186
0.6446 Remote Similarity NPC220311
0.6442 Remote Similarity NPC259512
0.6442 Remote Similarity NPC473388
0.6442 Remote Similarity NPC82664
0.6442 Remote Similarity NPC132271
0.6442 Remote Similarity NPC312132
0.6442 Remote Similarity NPC202986
0.6442 Remote Similarity NPC216520
0.6442 Remote Similarity NPC283711
0.6442 Remote Similarity NPC292730
0.642 Remote Similarity NPC56072
0.6417 Remote Similarity NPC474169
0.6417 Remote Similarity NPC473572
0.64 Remote Similarity NPC259017
0.6393 Remote Similarity NPC43706
0.6381 Remote Similarity NPC315921
0.6381 Remote Similarity NPC225464
0.6381 Remote Similarity NPC475078
0.6381 Remote Similarity NPC88420
0.6381 Remote Similarity NPC79241
0.6381 Remote Similarity NPC32674
0.6381 Remote Similarity NPC260000
0.6381 Remote Similarity NPC77492
0.6381 Remote Similarity NPC474073
0.6381 Remote Similarity NPC109955
0.6381 Remote Similarity NPC152097
0.6381 Remote Similarity NPC6597
0.6381 Remote Similarity NPC156313
0.6381 Remote Similarity NPC201967
0.6381 Remote Similarity NPC291789
0.6381 Remote Similarity NPC107619
0.6371 Remote Similarity NPC474091
0.6346 Remote Similarity NPC222146
0.6346 Remote Similarity NPC144682
0.6344 Remote Similarity NPC66655
0.6341 Remote Similarity NPC78061
0.6341 Remote Similarity NPC122359
0.6341 Remote Similarity NPC473708

  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 NPC252149 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
0.8171 Intermediate Similarity NPD9087 Approved
0.8061 Intermediate Similarity NPD9244 Approved
0.7791 Intermediate Similarity NPD9088 Approved
0.7444 Intermediate Similarity NPD9089 Approved
0.7333 Intermediate Similarity NPD9093 Approved
0.7204 Intermediate Similarity NPD9073 Approved
0.7204 Intermediate Similarity NPD111 Approved
0.6979 Remote Similarity NPD9094 Approved
0.6907 Remote Similarity NPD9295 Approved
0.6634 Remote Similarity NPD845 Approved
0.6569 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6569 Remote Similarity NPD2934 Approved
0.6569 Remote Similarity NPD2933 Approved
0.6569 Remote Similarity NPD9296 Approved
0.6505 Remote Similarity NPD844 Approved
0.6505 Remote Similarity NPD2859 Approved
0.6505 Remote Similarity NPD2860 Approved
0.6504 Remote Similarity NPD9718 Approved
0.6442 Remote Similarity NPD288 Approved
0.6381 Remote Similarity NPD9273 Approved
0.6381 Remote Similarity NPD9095 Approved
0.6381 Remote Similarity NPD68 Approved
0.6381 Remote Similarity NPD9096 Approved
0.6381 Remote Similarity NPD9097 Approved
0.6346 Remote Similarity NPD1809 Phase 2
0.6344 Remote Similarity NPD9294 Approved
0.6321 Remote Similarity NPD3020 Approved
0.6279 Remote Similarity NPD1169 Approved
0.6275 Remote Similarity NPD9365 Approved
0.6262 Remote Similarity NPD1242 Phase 1
0.6262 Remote Similarity NPD289 Clinical (unspecified phase)
0.6204 Remote Similarity NPD846 Approved
0.6204 Remote Similarity NPD940 Approved
0.6091 Remote Similarity NPD9608 Approved
0.6091 Remote Similarity NPD9610 Approved
0.6 Remote Similarity NPD9500 Approved
0.5984 Remote Similarity NPD1223 Clinical (unspecified phase)
0.5982 Remote Similarity NPD968 Approved
0.5982 Remote Similarity NPD1444 Approved
0.5982 Remote Similarity NPD1445 Approved
0.5929 Remote Similarity NPD9507 Approved
0.5929 Remote Similarity NPD2342 Discontinued
0.5929 Remote Similarity NPD9265 Clinical (unspecified phase)
0.5909 Remote Similarity NPD291 Approved
0.5877 Remote Similarity NPD9266 Approved
0.5877 Remote Similarity NPD74 Approved
0.5826 Remote Similarity NPD9380 Clinical (unspecified phase)
0.5826 Remote Similarity NPD1792 Phase 2
0.5826 Remote Similarity NPD3021 Approved
0.5826 Remote Similarity NPD3022 Approved
0.5789 Remote Similarity NPD9264 Approved
0.5789 Remote Similarity NPD9263 Approved
0.5789 Remote Similarity NPD9267 Approved
0.5776 Remote Similarity NPD9376 Approved
0.5776 Remote Similarity NPD9280 Clinical (unspecified phase)
0.5726 Remote Similarity NPD228 Approved
0.569 Remote Similarity NPD4750 Phase 3
0.5678 Remote Similarity NPD1105 Clinical (unspecified phase)
0.5678 Remote Similarity NPD9377 Approved
0.5678 Remote Similarity NPD7635 Approved
0.5678 Remote Similarity NPD9379 Approved
0.5676 Remote Similarity NPD3028 Approved
0.5664 Remote Similarity NPD9501 Approved
0.5652 Remote Similarity NPD9552 Approved
0.5652 Remote Similarity NPD290 Approved
0.563 Remote Similarity NPD2228 Approved
0.563 Remote Similarity NPD2229 Approved
0.563 Remote Similarity NPD2234 Approved
0.56 Remote Similarity NPD9250 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