NAV

(1S)-1-C-{(2R)-6-[(2R)-2-Butanyl]-5,10-dihydroxy-4-oxo-1,2,3,4-tetrahydro-2-anthracenyl}-5-deoxy-1-O-methyl-D-xylulose

Identification

Generic Name
(1S)-1-C-{(2R)-6-[(2R)-2-Butanyl]-5,10-dihydroxy-4-oxo-1,2,3,4-tetrahydro-2-anthracenyl}-5-deoxy-1-O-methyl-D-xylulose
DrugBank Accession Number
DB04240
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 430.4908
Monoisotopic: 430.199153314
Chemical Formula
C24H30O7
Synonyms
  • 1,2-HYDRO-1-OXY-3,4-HYDRO-3-(1-METHOXY-2-OXY-3,4-DIHYDROXYPENTYL)-8,9-DIHYDROXY-7-(SEC-BUTYL)-ANTHRACENE
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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 anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Anthracenes
Sub Class
Not Available
Direct Parent
Anthracenes
Alternative Parents
Naphthols and derivatives / Tetralins / Aryl alkyl ketones / 1-hydroxy-4-unsubstituted benzenoids / Monosaccharides / Beta-hydroxy ketones / Acyloins / Vinylogous acids / Alpha-hydroxy ketones / Secondary alcohols
show 4 more
Substituents
1,2-diol / 1-hydroxy-4-unsubstituted benzenoid / 1-naphthol / Acyloin / Alcohol / Alpha-hydroxy ketone / Anthracene / Aromatic homopolycyclic compound / Aryl alkyl ketone / Aryl ketone
show 13 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XGORHSPGULYMCV-HHYQQTLHSA-N
InChI
InChI=1S/C24H30O7/c1-5-11(2)16-7-6-13-8-14-9-15(24(31-4)23(30)20(27)12(3)25)10-17(26)18(14)22(29)19(13)21(16)28/h6-8,11-12,15,20,24-25,27-29H,5,9-10H2,1-4H3/t11-,12-,15-,20+,24+/m1/s1
IUPAC Name
(3R)-7-[(2R)-butan-2-yl]-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-8,9-dihydroxy-1,2,3,4-tetrahydroanthracen-1-one
SMILES
CC[C@@H](C)C1=C(O)C2=C(O)C3=C(C[C@H](CC3=O)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)C=C2C=C1

References

General References
Not Available
PubChem Compound
5288133
PubChem Substance
46504902
ChemSpider
4450362
ZINC
ZINC000012504239
PDBe Ligand
DXA
PDB Entries
1cp8

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 Solubility0.127 mg/mLALOGPS
logP3.01ALOGPS
logP3.72Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.9Chemaxon
pKa (Strongest Basic)-3.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area124.29 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity116.22 m3·mol-1Chemaxon
Polarizability46.15 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8894
Blood Brain Barrier-0.7206
Caco-2 permeable+0.5201
P-glycoprotein substrateSubstrate0.7084
P-glycoprotein inhibitor INon-inhibitor0.7175
P-glycoprotein inhibitor IIInhibitor0.6555
Renal organic cation transporterNon-inhibitor0.9175
CYP450 2C9 substrateNon-substrate0.8073
CYP450 2D6 substrateNon-substrate0.8346
CYP450 3A4 substrateSubstrate0.6193
CYP450 1A2 substrateInhibitor0.7572
CYP450 2C9 inhibitorNon-inhibitor0.8277
CYP450 2D6 inhibitorNon-inhibitor0.7792
CYP450 2C19 inhibitorNon-inhibitor0.7548
CYP450 3A4 inhibitorNon-inhibitor0.6918
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7438
Ames testAMES toxic0.5139
CarcinogenicityNon-carcinogens0.8964
BiodegradationNot ready biodegradable0.9782
Rat acute toxicity2.8088 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.944
hERG inhibition (predictor II)Non-inhibitor0.6012
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/MSsplash10-01qa-0069400000-e59547d5aaff4c0f1449
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1009200000-5ad003984f7338ef6e34
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-3039100000-614849c0a0a2e3f90325
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aba-9005000000-535b99841be6fae24c86
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-2039000000-883e083f45a7395b1bdd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6s-6092200000-a258889ef64cc2946bc8
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]-205.25336
predicted
DeepCCS 1.0 (2019)
[M+H]+207.14877
predicted
DeepCCS 1.0 (2019)
[M+Na]+212.79172
predicted
DeepCCS 1.0 (2019)

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