NAV

2-hydroxy-7-methoxy-5-methyl-naphthalene-1-carboxylic acid meso-2,5-dihydroxy-cyclopent-3-enyl ester

Identification

Generic Name
2-hydroxy-7-methoxy-5-methyl-naphthalene-1-carboxylic acid meso-2,5-dihydroxy-cyclopent-3-enyl ester
DrugBank Accession Number
DB08261
Background

2-hydroxy-7-methoxy-5-methyl-naphthalene-1-carboxylic acid meso-2,5-dihydroxy-cyclopent-3-enyl ester is a solid. This compound belongs to the naphthalenecarboxylic acids and derivatives. These are compounds containing a napthalene moiety with a ring carbon which bears a carboxylic acid group or a derivative. This drug targets the protein neocarzinostatin.

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 330.3319
Monoisotopic: 330.110338308
Chemical Formula
C18H18O6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeocarzinostatinNot AvailableStreptomyces carzinostaticus
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 naphthalenecarboxylic acids and derivatives. These are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthalenecarboxylic acids and derivatives
Direct Parent
Naphthalenecarboxylic acids and derivatives
Alternative Parents
Naphthols and derivatives / Salicylic acid and derivatives / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Secondary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-naphthalenecarboxylic acid or derivatives / 2-naphthol / Alcohol / Alkyl aryl ether / Anisole / Aromatic homopolycyclic compound / Carboxylic acid derivative / Carboxylic acid ester / Ether
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Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XILHLKXLRFUQFI-QLPKVWCKSA-N
InChI
InChI=1S/C18H18O6/c1-9-7-10(23-2)8-12-11(9)3-4-13(19)16(12)18(22)24-17-14(20)5-6-15(17)21/h3-8,14-15,17,19-21H,1-2H3/t14-,15+,17+
IUPAC Name
(1R,2R,5S)-2,5-dihydroxycyclopent-3-en-1-yl 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylate
SMILES
[H][C@]1(O)C=C[C@@]([H])(O)[C@]1([H])OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12

References

General References
Not Available
PubChem Compound
446415
PubChem Substance
99444732
ChEMBL
CHEMBL291386
ZINC
ZINC000100036551
PDBe Ligand
NCZ
PDB Entries
1j5i

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 Solubility0.337 mg/mLALOGPS
logP2ALOGPS
logP2.82Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)9.5Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area96.22 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity87.96 m3·mol-1Chemaxon
Polarizability33.73 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9801
Blood Brain Barrier-0.5354
Caco-2 permeable+0.772
P-glycoprotein substrateSubstrate0.539
P-glycoprotein inhibitor INon-inhibitor0.8007
P-glycoprotein inhibitor IINon-inhibitor0.8088
Renal organic cation transporterNon-inhibitor0.8974
CYP450 2C9 substrateNon-substrate0.7515
CYP450 2D6 substrateNon-substrate0.8957
CYP450 3A4 substrateNon-substrate0.5107
CYP450 1A2 substrateInhibitor0.6806
CYP450 2C9 inhibitorInhibitor0.594
CYP450 2D6 inhibitorNon-inhibitor0.8061
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorInhibitor0.6056
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7421
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.9299
BiodegradationNot ready biodegradable0.896
Rat acute toxicity2.6533 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9838
hERG inhibition (predictor II)Non-inhibitor0.8961
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pbc-9021000000-36b749027f2c2902362a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0049000000-20fa2da7b907994c5331
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-0970000000-2e8499ca4287b7d3a1e5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-2192000000-7a31d85504736f5f9988
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001s-4982000000-bb895c0357357db47830
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-1961000000-5727d3e5e5bdba415d67
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053s-9811000000-b9ab235d41c2ef748f02
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]-172.24492
predicted
DeepCCS 1.0 (2019)
[M+H]+174.64049
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.55302
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neocarzinostatin
Kind
Protein
Organism
Streptomyces carzinostaticus
Pharmacological action
Unknown
General Function
NCS has antibiotic activity (for Gram-positive bacteria) and antitumor activity (for certain mouse tumors). NCS binds non-covalently to a chromophore which is the cytotoxic and mutagenic component of the antibiotic. The chromophore binds to DNA as a weak intercalator and causes single- and double-strand breaks.
Specific Function
Dna binding
Gene Name
ncsA
Uniprot ID
P0A3R9
Uniprot Name
Neocarzinostatin
Molecular Weight
14455.08 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]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52