Structure

Physi-Chem Properties

Molecular Weight:  371.76
Volume:  194.748
LogP:  3.562
LogD:  2.014
LogS:  -3.17
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.451
Synthetic Accessibility Score:  3.214
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.896
MDCK Permeability:  1.545763916510623e-05
Pgp-inhibitor:  0.02
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.812
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.282
Plasma Protein Binding (PPB):  99.42707824707031%
Volume Distribution (VD):  1.772
Pgp-substrate:  2.3990297317504883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.75
CYP1A2-substrate:  0.175
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.087
CYP2C9-inhibitor:  0.532
CYP2C9-substrate:  0.735
CYP2D6-inhibitor:  0.035
CYP2D6-substrate:  0.202
CYP3A4-inhibitor:  0.074
CYP3A4-substrate:  0.085

ADMET: Excretion

Clearance (CL):  0.667
Half-life (T1/2):  0.658

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.208
Drug-inuced Liver Injury (DILI):  0.121
AMES Toxicity:  0.29
Rat Oral Acute Toxicity:  0.274
Maximum Recommended Daily Dose:  0.03
Skin Sensitization:  0.715
Carcinogencity:  0.415
Eye Corrosion:  0.932
Eye Irritation:  0.968
Respiratory Toxicity:  0.887

Download Data

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

  Natural Product: NPC110800

Natural Product ID:  NPC110800
Common Name*:   2,3,6-Tribromo-4,5-Dihydroxybenzaldehyde
IUPAC Name:   2,3,6-tribromo-4,5-dihydroxybenzaldehyde
Synonyms:  
Standard InCHIKey:  KZJVMYOEIYAKSP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H3Br3O3/c8-3-2(1-11)4(9)6(12)7(13)5(3)10/h1,12-13H
SMILES:  C(=O)c1c(c(c(c(c1Br)O)O)Br)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL374606
PubChem CID:   21778116
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000124] Aldehydes
            • [CHEMONTID:0003213] Aryl-aldehydes
              • [CHEMONTID:0001345] Benzaldehydes
                • [CHEMONTID:0003978] Hydroxybenzaldehydes

*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
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[11141124]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15844965]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17602526]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae 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
NPT41 Individual Protein Aldose reductase Homo sapiens IC50 = 0.25 ug.mL-1 PMID[571158]
NPT35 Others n.a. IC50 = 24700.0 nM PMID[571157]

☑ 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 NPC110800 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
0.9091 High Similarity NPC199089
0.9008 High Similarity NPC474135
0.8561 High Similarity NPC214553
0.8358 Intermediate Similarity NPC105702
0.8333 Intermediate Similarity NPC50782
0.8333 Intermediate Similarity NPC473608
0.8231 Intermediate Similarity NPC227976
0.7939 Intermediate Similarity NPC100395
0.7868 Intermediate Similarity NPC134219
0.7847 Intermediate Similarity NPC250597
0.7836 Intermediate Similarity NPC219444
0.7778 Intermediate Similarity NPC84606
0.7664 Intermediate Similarity NPC142776
0.7574 Intermediate Similarity NPC47790
0.7554 Intermediate Similarity NPC13004
0.7535 Intermediate Similarity NPC303011
0.75 Intermediate Similarity NPC55113
0.7481 Intermediate Similarity NPC474146
0.7464 Intermediate Similarity NPC137117
0.7403 Intermediate Similarity NPC135103
0.7368 Intermediate Similarity NPC278102
0.7279 Intermediate Similarity NPC271942
0.7279 Intermediate Similarity NPC168680
0.7254 Intermediate Similarity NPC150929
0.7241 Intermediate Similarity NPC471328
0.7203 Intermediate Similarity NPC85049
0.719 Intermediate Similarity NPC178097
0.7163 Intermediate Similarity NPC220311
0.7153 Intermediate Similarity NPC117759
0.7153 Intermediate Similarity NPC226493
0.7153 Intermediate Similarity NPC160081
0.7113 Intermediate Similarity NPC43706
0.7063 Intermediate Similarity NPC473708
0.7063 Intermediate Similarity NPC474147
0.7059 Intermediate Similarity NPC79844
0.7044 Intermediate Similarity NPC474535
0.7032 Intermediate Similarity NPC226514
0.7025 Intermediate Similarity NPC294870
0.7007 Intermediate Similarity NPC163560
0.7 Intermediate Similarity NPC475697
0.6966 Remote Similarity NPC474536
0.696 Remote Similarity NPC475466
0.6959 Remote Similarity NPC245386
0.6867 Remote Similarity NPC224663
0.6863 Remote Similarity NPC184632
0.6857 Remote Similarity NPC180207
0.6786 Remote Similarity NPC38483
0.6779 Remote Similarity NPC244890
0.6776 Remote Similarity NPC160932
0.6763 Remote Similarity NPC150919
0.6763 Remote Similarity NPC28169
0.6761 Remote Similarity NPC136543
0.6735 Remote Similarity NPC474614
0.6713 Remote Similarity NPC229213
0.6712 Remote Similarity NPC473787
0.6712 Remote Similarity NPC117237
0.6712 Remote Similarity NPC203719
0.6688 Remote Similarity NPC89341
0.6687 Remote Similarity NPC305490
0.6667 Remote Similarity NPC473572
0.6667 Remote Similarity NPC156654
0.6667 Remote Similarity NPC474169
0.6645 Remote Similarity NPC177967
0.6645 Remote Similarity NPC471237
0.6624 Remote Similarity NPC84426
0.6617 Remote Similarity NPC163734
0.6617 Remote Similarity NPC219913
0.6601 Remote Similarity NPC471236
0.6601 Remote Similarity NPC197766
0.6577 Remote Similarity NPC298268
0.6561 Remote Similarity NPC109346
0.6533 Remote Similarity NPC259017
0.6483 Remote Similarity NPC225710
0.6474 Remote Similarity NPC118794
0.6444 Remote Similarity NPC19149
0.6405 Remote Similarity NPC237330
0.6405 Remote Similarity NPC144662
0.64 Remote Similarity NPC226855
0.6387 Remote Similarity NPC156356
0.6382 Remote Similarity NPC300678
0.6376 Remote Similarity NPC16651
0.6376 Remote Similarity NPC158654
0.6376 Remote Similarity NPC32163
0.637 Remote Similarity NPC116562
0.6364 Remote Similarity NPC274613
0.6358 Remote Similarity NPC152947
0.6329 Remote Similarity NPC147137
0.6323 Remote Similarity NPC471690
0.6299 Remote Similarity NPC312155
0.6275 Remote Similarity NPC50763
0.6268 Remote Similarity NPC4665
0.6267 Remote Similarity NPC107672
0.6267 Remote Similarity NPC324209
0.6267 Remote Similarity NPC214620
0.625 Remote Similarity NPC270848
0.625 Remote Similarity NPC122599
0.625 Remote Similarity NPC272868
0.6234 Remote Similarity NPC156124
0.6234 Remote Similarity NPC304929
0.6234 Remote Similarity NPC1321
0.6233 Remote Similarity NPC295317
0.6233 Remote Similarity NPC294361
0.6233 Remote Similarity NPC236520
0.6225 Remote Similarity NPC234175
0.6209 Remote Similarity NPC264145
0.6197 Remote Similarity NPC163154
0.6194 Remote Similarity NPC204582
0.6187 Remote Similarity NPC54543
0.6185 Remote Similarity NPC475688
0.6184 Remote Similarity NPC261759
0.6184 Remote Similarity NPC94810
0.617 Remote Similarity NPC231717
0.6169 Remote Similarity NPC111888
0.6164 Remote Similarity NPC476534
0.6164 Remote Similarity NPC260837
0.6163 Remote Similarity NPC191557
0.6154 Remote Similarity NPC18646
0.6154 Remote Similarity NPC139519
0.6144 Remote Similarity NPC66905
0.6144 Remote Similarity NPC117609
0.6143 Remote Similarity NPC473358
0.6143 Remote Similarity NPC222084
0.6139 Remote Similarity NPC81137
0.6136 Remote Similarity NPC475120
0.6129 Remote Similarity NPC283823
0.6129 Remote Similarity NPC159418
0.6129 Remote Similarity NPC239855
0.6127 Remote Similarity NPC148969
0.6121 Remote Similarity NPC470710
0.6115 Remote Similarity NPC475111
0.6115 Remote Similarity NPC156892
0.6111 Remote Similarity NPC61062
0.6111 Remote Similarity NPC299252
0.6111 Remote Similarity NPC277394
0.6111 Remote Similarity NPC160839
0.6104 Remote Similarity NPC469526
0.6104 Remote Similarity NPC291001
0.6104 Remote Similarity NPC43613
0.6104 Remote Similarity NPC34070
0.6099 Remote Similarity NPC114682
0.6099 Remote Similarity NPC212718
0.6092 Remote Similarity NPC288747
0.6087 Remote Similarity NPC187913
0.6087 Remote Similarity NPC299154
0.6087 Remote Similarity NPC6984
0.6074 Remote Similarity NPC88896
0.6069 Remote Similarity NPC174087
0.6069 Remote Similarity NPC230349
0.6067 Remote Similarity NPC288945
0.6067 Remote Similarity NPC85565
0.6065 Remote Similarity NPC135801
0.6058 Remote Similarity NPC52087
0.6058 Remote Similarity NPC79672
0.6051 Remote Similarity NPC208760
0.6043 Remote Similarity NPC34715
0.6043 Remote Similarity NPC303264
0.6043 Remote Similarity NPC226699
0.6043 Remote Similarity NPC29883
0.604 Remote Similarity NPC86900
0.6039 Remote Similarity NPC26697
0.6039 Remote Similarity NPC233056
0.6038 Remote Similarity NPC141368
0.6038 Remote Similarity NPC239943
0.6038 Remote Similarity NPC325625
0.6038 Remote Similarity NPC206207
0.6034 Remote Similarity NPC203426
0.6027 Remote Similarity NPC63126
0.6027 Remote Similarity NPC283844
0.6026 Remote Similarity NPC474715
0.6026 Remote Similarity NPC473626
0.6026 Remote Similarity NPC4170
0.6026 Remote Similarity NPC120066
0.6026 Remote Similarity NPC111845
0.6026 Remote Similarity NPC294226
0.6026 Remote Similarity NPC138472
0.6014 Remote Similarity NPC471488
0.6014 Remote Similarity NPC33244
0.6014 Remote Similarity NPC216216
0.6014 Remote Similarity NPC11824
0.6013 Remote Similarity NPC247250
0.6013 Remote Similarity NPC324929
0.6013 Remote Similarity NPC767
0.6012 Remote Similarity NPC275278
0.6 Remote Similarity NPC17525
0.6 Remote Similarity NPC4796
0.6 Remote Similarity NPC225036
0.6 Remote Similarity NPC105525
0.6 Remote Similarity NPC68350
0.6 Remote Similarity NPC471495
0.6 Remote Similarity NPC131587
0.6 Remote Similarity NPC105999
0.6 Remote Similarity NPC81149
0.6 Remote Similarity NPC12218
0.6 Remote Similarity NPC197576
0.6 Remote Similarity NPC75763
0.6 Remote Similarity NPC131940
0.6 Remote Similarity NPC230013
0.5976 Remote Similarity NPC287495
0.5976 Remote Similarity NPC9370
0.5975 Remote Similarity NPC112068

  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 NPC110800 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
0.6712 Remote Similarity NPD9494 Approved
0.6667 Remote Similarity NPD9244 Approved
0.6483 Remote Similarity NPD9269 Phase 2
0.6319 Remote Similarity NPD9268 Approved
0.6234 Remote Similarity NPD230 Phase 1
0.6078 Remote Similarity NPD9718 Approved
0.6065 Remote Similarity NPD943 Approved
0.6043 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6036 Remote Similarity NPD2296 Approved
0.5912 Remote Similarity NPD651 Clinical (unspecified phase)
0.5811 Remote Similarity NPD9545 Approved
0.5783 Remote Similarity NPD7422 Clinical (unspecified phase)
0.5676 Remote Similarity NPD405 Clinical (unspecified phase)
0.5602 Remote Similarity NPD6190 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