MiMeDB: Showing metabocard for 5-Dehydroavenasterol (MMDBc0052114)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 20:46:15 UTC

Update Date

2024-04-30 20:43:13 UTC

Metabolite ID

MMDBc0052114

Metabolite Identification

Common Name

5-Dehydroavenasterol

Description

5-Dehydroavenasterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 5-Dehydroavenasterol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220532D          

 30 33  0  0  1  0            999 V2000
   13.1470   -9.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5963   -6.8673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5963   -7.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3770   -6.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1674   -7.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8819   -6.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3770   -7.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8819   -8.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8585   -7.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4166   -8.1106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1674   -6.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6333   -5.8318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5963   -6.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4099   -8.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6519   -7.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8951   -8.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4230   -7.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4405   -5.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1542   -9.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6382   -9.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8699   -8.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0823   -5.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8631   -8.9758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6969   -4.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5042   -4.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7604   -3.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0551   -5.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5677   -3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2095   -3.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8624   -5.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  1  0  0  0
 12 18  1  0  0  0  0
 12 22  1  6  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 18 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
M  END


  Mrv0541 02231220532D          

 30 33  0  0  1  0            999 V2000
   13.1470   -9.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5963   -6.8673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5963   -7.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3770   -6.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1674   -7.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8819   -6.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3770   -7.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8819   -8.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8585   -7.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4166   -8.1106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1674   -6.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6333   -5.8318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5963   -6.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4099   -8.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6519   -7.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8951   -8.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4230   -7.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4405   -5.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1542   -9.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6382   -9.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8699   -8.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0823   -5.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8631   -8.9758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6969   -4.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5042   -4.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7604   -3.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0551   -5.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5677   -3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2095   -3.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8624   -5.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  1  0  0  0
 12 18  1  0  0  0  0
 12 22  1  6  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 18 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0052114

> <DATABASE_NAME>
MIME

> <SMILES>
C\C=C(/C(C)C)CC[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25?,26?,27?,28+,29-/m1/s1

> <INCHI_KEY>
XPRWWANUPMYKMF-UUHDPGOWSA-N

> <FORMULA>
C29H46O

> <MOLECULAR_WEIGHT>
410.6749

> <EXACT_MASS>
410.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
51.97925643445713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
8.24

> <JCHEM_LOGP>
7.033317829333334

> <ALOGPS_LOGS>
-6.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
131.46609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-dehydroavenasterol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      24.541 -17.520   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      32.846 -12.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.846 -14.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.304 -12.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.179 -14.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.513 -12.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.304 -14.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.513 -15.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.203 -13.589   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.778 -15.140   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.179 -12.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.782 -10.886   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.846 -11.279   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.765 -16.744   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.350 -14.271   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.538 -16.733   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.790 -13.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.289 -10.569   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.155 -17.546   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.325 -17.590   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.890 -15.084   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.754  -9.740   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.878 -16.755   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.768  -9.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.275  -8.787   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.753  -7.323   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      39.303  -9.933   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.260  -7.006   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      37.724  -6.177   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      40.810  -9.616   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2    3    4    6   13                                             
CONECT    3    2    7    8                                                  
CONECT    4    2    9   12                                                  
CONECT    5    8   10   11                                                  
CONECT    6    2   11                                                       
CONECT    7    3    9                                                       
CONECT    8    3    5   16                                                  
CONECT    9    4    7                                                       
CONECT   10    5   14   15   17                                             
CONECT   11    5    6                                                       
CONECT   12    4   18   22                                                  
CONECT   13    2                                                            
CONECT   14   10   19   20                                                  
CONECT   15   10   21                                                       
CONECT   16    8   19                                                       
CONECT   17   10                                                            
CONECT   18   12   24                                                       
CONECT   19   14   16                                                       
CONECT   20   14   23                                                       
CONECT   21   15   23                                                       
CONECT   22   12                                                            
CONECT   23    1   20   21                                                  
CONECT   24   18   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   28   29                                                  
CONECT   27   25   30                                                       
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   27                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₉H₄₆O

Average Mass

410.6749

Monoisotopic Mass

410.354866094

IUPAC Name

(2R,5S,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

Traditional Name

5-dehydroavenasterol

CAS Registry Number

Not Available

SMILES

C\C=C(/C(C)C)CC[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25?,26?,27?,28+,29-/m1/s1

InChI Key

XPRWWANUPMYKMF-UUHDPGOWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-7-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid (CHEBI:80097 )
Stigmasterols and C24-ethyl derivatives (C15783 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00026 g/L	ALOGPS
logP	8.24	ALOGPS
logP	7.03	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.47 m³·mol⁻¹	ChemAxon
Polarizability	51.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-0019000000-e5b743bee404f9004334	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0gb9-2004900000-620c6d47071be9918bc6	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1029500000-4a6fcef2932d4820b7c9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ow-6149100000-0bf3a0dfb15ec2e1f66e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7189000000-38865e37f6db2820fd67	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0002900000-b532cfb3047b11c1073a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0005900000-bfb72a8e5b9e1f9d8af9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-2019000000-fef11bfaf264bb86495d	2017-09-01	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0006852

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024118

KNApSAcK ID

C00007527

Chemspider ID

Not Available

KEGG Compound ID

C15783

BioCyc ID

CPD-4126

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724575

PDB ID

Not Available

ChEBI ID

80097

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 5-Dehydroavenasterol (MMDBc0052114)

MOL for #<Metabolite:0x00007fecef545d60>

3D MOL for #<Metabolite:0x00007fecef545d60>

3D SDF for #<Metabolite:0x00007fecef545d60>

3D-SDF for #<Metabolite:0x00007fecef545d60>

PDB for #<Metabolite:0x00007fecef545d60>

3D PDB for #<Metabolite:0x00007fecef545d60>

SMILES for #<Metabolite:0x00007fecef545d60>

INCHI for #<Metabolite:0x00007fecef545d60>

Structure for #<Metabolite:0x00007fecef545d60>

3D Structure for #<Metabolite:0x00007fecef545d60>