(3AR,6R,6AS)-6-((S)-((S)-CYCLOHEX-2-ENYL)(HYDROXY)METHYL)-6A-METHYL-4-OXO-HEXAHYDRO-2H-FURO[3,2-C]PYRROLE-6-CARBALDEHYDE

Identification

Name
(3AR,6R,6AS)-6-((S)-((S)-CYCLOHEX-2-ENYL)(HYDROXY)METHYL)-6A-METHYL-4-OXO-HEXAHYDRO-2H-FURO[3,2-C]PYRROLE-6-CARBALDEHYDE
Accession Number
DB08515
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 279.3315
Monoisotopic: 279.147058165
Chemical Formula
C15H21NO4
InChI Key
YVABESCRHMBHJD-FUQNVFFISA-N
InChI
InChI=1S/C15H21NO4/c1-14-11(7-8-20-14)13(19)16-15(14,9-17)12(18)10-5-3-2-4-6-10/h3,5,9-12,18H,2,4,6-8H2,1H3,(H,16,19)/t10-,11+,12+,14+,15-/m1/s1
IUPAC Name
(3aR,6R,6aS)-6-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-6a-methyl-4-oxo-hexahydro-2H-furo[2,3-c]pyrrole-6-carbaldehyde
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProteasome subunit alpha type-1Not AvailableHuman
UProteasome subunit alpha type-2Not AvailableHuman
UProteasome subunit alpha type-3Not AvailableHuman
UProteasome subunit alpha type-4Not AvailableHuman
UProteasome subunit alpha type-5Not AvailableHuman
UProteasome subunit alpha type-6Not AvailableHuman
UProteasome subunit alpha type-7Not AvailableHuman
UProteasome subunit beta type-1Not AvailableHuman
UProteasome subunit beta type-2Not AvailableHuman
UProteasome subunit beta type-3Not AvailableHuman
UProteasome subunit beta type-4Not AvailableHuman
UProteasome subunit beta type-5Not AvailableHuman
UProteasome subunit beta type-6Not AvailableHuman
UProteasome subunit beta type-7Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11840981
PubChem Substance
99444986
ChemSpider
10015482
HET
SA1
PDB Entries
2fak / 3gpw

Clinical Trials

Clinical Trials
Not Available

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 Solubility2.09 mg/mLALOGPS
logP0.67ALOGPS
logP0.22ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.76ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.63 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.39 m3·mol-1ChemAxon
Polarizability28.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9809
Blood Brain Barrier+0.6323
Caco-2 permeable-0.6723
P-glycoprotein substrateSubstrate0.5119
P-glycoprotein inhibitor INon-inhibitor0.9424
P-glycoprotein inhibitor IINon-inhibitor0.9772
Renal organic cation transporterNon-inhibitor0.8823
CYP450 2C9 substrateNon-substrate0.8162
CYP450 2D6 substrateNon-substrate0.7892
CYP450 3A4 substrateSubstrate0.571
CYP450 1A2 substrateNon-inhibitor0.9068
CYP450 2C9 inhibitorNon-inhibitor0.9284
CYP450 2D6 inhibitorNon-inhibitor0.9678
CYP450 2C19 inhibitorNon-inhibitor0.9118
CYP450 3A4 inhibitorNon-inhibitor0.9806
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9797
Ames testNon AMES toxic0.6215
CarcinogenicityNon-carcinogens0.9669
BiodegradationNot ready biodegradable0.9391
Rat acute toxicity2.4693 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9773
hERG inhibition (predictor II)Non-inhibitor0.9409
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as furopyrroles. These are organic polycyclic compounds containing a furan ring fused to a pyrrole ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Furopyrroles
Sub Class
Not Available
Direct Parent
Furopyrroles
Alternative Parents
Pyrrolidine-2-ones / Beta-hydroxy aldehydes / Tetrahydrofurans / Pyrroles / Furans / Secondary carboxylic acid amides / Secondary alcohols / Lactams / Oxacyclic compounds / Dialkyl ethers
show 5 more
Substituents
Furopyrrole / Beta-hydroxy aldehyde / 2-pyrrolidone / Pyrrolidone / Furan / Pyrrole / Pyrrolidine / Tetrahydrofuran / Carboxamide group / Lactam
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA1
Uniprot ID
P25786
Uniprot Name
Proteasome subunit alpha type-1
Molecular Weight
29555.33 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA2
Uniprot ID
P25787
Uniprot Name
Proteasome subunit alpha type-2
Molecular Weight
25898.405 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA3
Uniprot ID
P25788
Uniprot Name
Proteasome subunit alpha type-3
Molecular Weight
28432.97 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA4
Uniprot ID
P25789
Uniprot Name
Proteasome subunit alpha type-4
Molecular Weight
29483.57 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA5
Uniprot ID
P28066
Uniprot Name
Proteasome subunit alpha type-5
Molecular Weight
26410.82 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA6
Uniprot ID
P60900
Uniprot Name
Proteasome subunit alpha type-6
Molecular Weight
27399.235 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMA7
Uniprot ID
O14818
Uniprot Name
Proteasome subunit alpha type-7
Molecular Weight
27886.615 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB1
Uniprot ID
P20618
Uniprot Name
Proteasome subunit beta type-1
Molecular Weight
26489.09 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB2
Uniprot ID
P49721
Uniprot Name
Proteasome subunit beta type-2
Molecular Weight
22836.02 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB3
Uniprot ID
P49720
Uniprot Name
Proteasome subunit beta type-3
Molecular Weight
22948.7 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB4
Uniprot ID
P28070
Uniprot Name
Proteasome subunit beta type-4
Molecular Weight
29203.995 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB5
Uniprot ID
P28074
Uniprot Name
Proteasome subunit beta type-5
Molecular Weight
28480.01 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB6
Uniprot ID
P28072
Uniprot Name
Proteasome subunit beta type-6
Molecular Weight
25357.48 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Threonine-type endopeptidase activity
Specific Function
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
Gene Name
PSMB7
Uniprot ID
Q99436
Uniprot Name
Proteasome subunit beta type-7
Molecular Weight
29965.16 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. [PubMed:10592235]

Drug created on September 15, 2010 15:32 / Updated on December 01, 2017 16:05