2,3-Bis-Benzo[1,3]Dioxol-5-Ylmethyl-Succinic Acid

Identification

Generic Name
2,3-Bis-Benzo[1,3]Dioxol-5-Ylmethyl-Succinic Acid
DrugBank Accession Number
DB02154
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 386.3521
Monoisotopic: 386.100167552
Chemical Formula
C20H18O8
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot AvailablePseudomonas aeruginosa
UBeta-lactamase IMP-1Not AvailableSerratia marcescens
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
Kingdom
Organic compounds
Super Class
Lignans, neolignans and related compounds
Class
Dibenzylbutane lignans
Sub Class
Not Available
Direct Parent
Dibenzylbutane lignans
Alternative Parents
Benzodioxoles / Dicarboxylic acids and derivatives / Benzenoids / Oxacyclic compounds / Carboxylic acids / Acetals / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acetal / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dibenzylbutane lignan skeleton / Dicarboxylic acid or derivatives / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FFYBYVPVYLMLAR-KBPBESRZSA-N
InChI
InChI=1S/C20H18O8/c21-19(22)13(5-11-1-3-15-17(7-11)27-9-25-15)14(20(23)24)6-12-2-4-16-18(8-12)28-10-26-16/h1-4,7-8,13-14H,5-6,9-10H2,(H,21,22)(H,23,24)/t13-,14-/m0/s1
IUPAC Name
(2S,3S)-2,3-bis[(2H-1,3-benzodioxol-5-yl)methyl]butanedioic acid
SMILES
[H][C@@](CC1=CC=C2OCOC2=C1)(C(O)=O)[C@]([H])(CC1=CC=C2OCOC2=C1)C(O)=O

References

General References
Not Available
PubChem Compound
5496628
PubChem Substance
46508008
ChemSpider
4593420
ChEMBL
CHEMBL1231277
ZINC
ZINC000012501665
PDBe Ligand
BDS
PDB Entries
1jjt

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.117 mg/mLALOGPS
logP1.96ALOGPS
logP3.09Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.24Chemaxon
pKa (Strongest Basic)-4.4Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area111.52 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity93.61 m3·mol-1Chemaxon
Polarizability38.21 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.879
Blood Brain Barrier+0.827
Caco-2 permeable-0.6761
P-glycoprotein substrateSubstrate0.5593
P-glycoprotein inhibitor INon-inhibitor0.9226
P-glycoprotein inhibitor IINon-inhibitor0.598
Renal organic cation transporterNon-inhibitor0.8014
CYP450 2C9 substrateNon-substrate0.8445
CYP450 2D6 substrateNon-substrate0.8629
CYP450 3A4 substrateNon-substrate0.6888
CYP450 1A2 substrateInhibitor0.6398
CYP450 2C9 inhibitorInhibitor0.67
CYP450 2D6 inhibitorNon-inhibitor0.8185
CYP450 2C19 inhibitorInhibitor0.6497
CYP450 3A4 inhibitorInhibitor0.5812
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testAMES toxic0.5273
CarcinogenicityNon-carcinogens0.9203
BiodegradationNot ready biodegradable0.7962
Rat acute toxicity2.5157 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9675
hERG inhibition (predictor II)Non-inhibitor0.7862
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ku-0309000000-7051648f8be9a5e2c89b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000g-0069000000-606948bfe99edb237dbf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0429000000-ab5129b3401195360001
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-0069000000-4174b03eeda583340059
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mk-0869000000-280a67d117f21470d70f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0922000000-923b36df645184c48595
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.68611
predicted
DeepCCS 1.0 (2019)
[M+H]+178.08168
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.9942
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
blaIMP-1
Uniprot ID
Q79MP6
Uniprot Name
Beta-lactamase
Molecular Weight
27119.985 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Serratia marcescens
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Confers resistance to imipenem and broad-spectrum beta-lactams. Also hydrolyzes carbapenems.
Gene Name
Not Available
Uniprot ID
P52699
Uniprot Name
Beta-lactamase IMP-1
Molecular Weight
27119.985 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52