Structure

Physi-Chem Properties

Molecular Weight:  251.84
Volume:  134.718
LogP:  2.34
LogD:  1.165
LogS:  -2.093
# Rotatable Bonds:  0
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.618
Synthetic Accessibility Score:  3.988
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:  -4.433
MDCK Permeability:  2.9681381420232356e-05
Pgp-inhibitor:  0.226
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.979
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.876
Plasma Protein Binding (PPB):  93.10395812988281%
Volume Distribution (VD):  0.583
Pgp-substrate:  16.325925827026367%

ADMET: Metabolism

CYP1A2-inhibitor:  0.869
CYP1A2-substrate:  0.407
CYP2C19-inhibitor:  0.598
CYP2C19-substrate:  0.663
CYP2C9-inhibitor:  0.369
CYP2C9-substrate:  0.602
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.344
CYP3A4-inhibitor:  0.158
CYP3A4-substrate:  0.196

ADMET: Excretion

Clearance (CL):  1.197
Half-life (T1/2):  0.763

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.951
Drug-inuced Liver Injury (DILI):  0.212
AMES Toxicity:  0.966
Rat Oral Acute Toxicity:  0.987
Maximum Recommended Daily Dose:  0.12
Skin Sensitization:  0.944
Carcinogencity:  0.872
Eye Corrosion:  0.991
Eye Irritation:  0.982
Respiratory Toxicity:  0.942

Download Data

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

  Natural Product: NPC103560

Natural Product ID:  NPC103560
Common Name*:   4-Bromo-5-(Bromomethylene)Furan-2(5H)-One
IUPAC Name:   (5Z)-4-bromo-5-(bromomethylidene)furan-2-one
Synonyms:  
Standard InCHIKey:  DPGLBHQUHFJRJS-RQOWECAXSA-N
Standard InCHI:  InChI=1S/C5H2Br2O2/c6-2-4-3(7)1-5(8)9-4/h1-2H/b4-2-
SMILES:  C1=C(/C(=C/Br)/OC1=O)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1253219
PubChem CID:   10131246
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. DOI[10.3923/pjbs.2013.1138.1144]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[17262437]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[18326559]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO10434 Rhodospirillum rubrum Species Rhodospirillaceae Bacteria n.a. n.a. n.a. PMID[18826254]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Essential oil n.a. n.a. PMID[23163425]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[23865201]
NPO3186 Loranthus parasiticus Species Loranthaceae Eukaryota n.a. n.a. n.a. PMID[24467533]
NPO3186 Loranthus parasiticus Species Loranthaceae Eukaryota n.a. fruit n.a. PMID[24467533]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[24508058]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[25650289]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota garlic skin n.a. n.a. PMID[25726329]
NPO13017 Nauclea latifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[31429278]
NPO40616 Aspergillus sp. HNMF114 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31823605]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[8350088]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Bulb n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3186 Loranthus parasiticus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2055 Berberis integerrima Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO9952 Isoplexis sceptrum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3186 Loranthus parasiticus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2055 Berberis integerrima Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3186 Loranthus parasiticus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4177 Libocedrus decurrens Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8146 Aniba megaphylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3186 Loranthus parasiticus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13017 Nauclea latifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1625 Ovibos moschatus Species Bovidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11481 Elephantopus angustifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8817 Herbertus sakuraii Species Herbertaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10434 Rhodospirillum rubrum Species Rhodospirillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2055 Berberis integerrima Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9952 Isoplexis sceptrum Species Plantaginaceae 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
NPT4195 Individual Protein Transcriptional activator protein lasR Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Inhibition = 13.0 % PMID[482285]
NPT2086 Cell Line L-428 Homo sapiens IC50 = 5160.0 nM PMID[482287]
NPT2086 Cell Line L-428 Homo sapiens IC50 = 3050.0 nM PMID[482287]
NPT2 Others Unspecified IC50 = 2708.0 nM PMID[482281]
NPT1726 Organism Vibrio harveyi Vibrio harveyi GI50 = 3155.0 nM PMID[482281]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 128.0 ug.mL-1 PMID[482286]
NPT2 Others Unspecified IC50 = 9900.0 nM PMID[482287]
NPT2 Others Unspecified Activity = 0.42 um3/um2 PMID[482288]
NPT2 Others Unspecified Activity = 2.02 um PMID[482288]
NPT2 Others Unspecified Activity = 0.3 um3/um2 PMID[482288]
NPT2 Others Unspecified Activity = 2.05 um PMID[482288]
NPT2 Others Unspecified Activity = 0.77 um3/um2 PMID[482288]
NPT2 Others Unspecified Activity = 2.18 um PMID[482288]
NPT2 Others Unspecified Activity = 82.56 % PMID[482288]
NPT2 Others Unspecified Activity = 69.51 % PMID[482288]
NPT2 Others Unspecified Activity = 68.05 % PMID[482288]
NPT2 Others Unspecified Activity = 55.61 % PMID[482288]
NPT2 Others Unspecified Activity = 106.31 % PMID[482288]
NPT2 Others Unspecified Activity = 106.1 % PMID[482288]
NPT2 Others Unspecified Activity = 83.09 % PMID[482288]
NPT2 Others Unspecified Activity = 39.22 % PMID[482288]
NPT2 Others Unspecified Activity = 62.45 % PMID[482288]
NPT2 Others Unspecified Activity = 59.71 % PMID[482288]
NPT2 Others Unspecified Activity = 58.9 % PMID[482288]
NPT2 Others Unspecified Activity = 47.39 % PMID[482288]
NPT25696 SINGLE PROTEIN Pseudolysin Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Inhibition = 21.43 % PMID[482289]
NPT2 Others Unspecified Inhibition = 24.03 % PMID[482289]
NPT25697 SINGLE PROTEIN Anthranilate--CoA ligase Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 /JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) Inhibition = 20.19 % PMID[482289]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition > 90.0 % PMID[482290]
NPT610 Others Molecular identity unknown Inhibition = 83.1 % PMID[482291]
NPT610 Others Molecular identity unknown Inhibition = 87.5 % PMID[482291]
NPT610 Others Molecular identity unknown Inhibition = 77.0 % PMID[482291]
NPT610 Others Molecular identity unknown Inhibition = 65.9 % PMID[482291]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa GI > 30.0 % PMID[482291]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa GI = 15.0 % PMID[482291]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 87.9 % PMID[482291]
NPT878 Organism Streptococcus mutans Streptococcus mutans Inhibition = 60.0 % PMID[482292]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium IC50 = 10000.0 nM PMID[482293]
NPT610 Others Molecular identity unknown MIC = 1.0 ug PMID[482294]

☑ 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 NPC103560 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
0.7143 Intermediate Similarity NPC122676
0.68 Remote Similarity NPC90490
0.6667 Remote Similarity NPC82446
0.6522 Remote Similarity NPC147824
0.65 Remote Similarity NPC53136
0.65 Remote Similarity NPC173409
0.6222 Remote Similarity NPC9290
0.6167 Remote Similarity NPC217537
0.6154 Remote Similarity NPC128520
0.6038 Remote Similarity NPC234084
0.6038 Remote Similarity NPC126184
0.5821 Remote Similarity NPC162571
0.5821 Remote Similarity NPC112983
0.5714 Remote Similarity NPC281043
0.5714 Remote Similarity NPC191643
0.5667 Remote Similarity NPC189700

  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 NPC103560 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
0.5745 Remote Similarity NPD9115 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