MiMeDB: Showing metabocard for 7,8-Didehydrodesmosterol (MMDBc0033507)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:51:28 UTC

Update Date

2024-04-30 20:10:58 UTC

Metabolite ID

MMDBc0033507

Metabolite Identification

Common Name

7,8-Didehydrodesmosterol

Description

7,8-Didehydrodesmosterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 7,8-Didehydrodesmosterol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920232D          

 28 31  0  0  0  0            999 V2000
   -2.4048    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    3.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  7  2  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  2  0  0  0  0
 23 11  1  0  0  0  0
 23 19  1  0  0  0  0
 24 12  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 21  1  0  0  0  0
M  END


  Mrv1652305221920232D          

 28 31  0  0  0  0            999 V2000
   -2.4048    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    3.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  7  2  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  2  0  0  0  0
 23 11  1  0  0  0  0
 23 19  1  0  0  0  0
 24 12  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033507

> <DATABASE_NAME>
MIME

> <SMILES>
CC(CCC=C(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3

> <INCHI_KEY>
RUSSPKPUXDSHNC-UHFFFAOYSA-N

> <FORMULA>
C27H42O

> <MOLECULAR_WEIGHT>
382.6218

> <EXACT_MASS>
382.323565966

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.70776796247964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
7.46

> <JCHEM_LOGP>
6.301730068000001

> <ALOGPS_LOGS>
-5.78

> <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>
122.31649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.489   4.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.383   6.457   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.558   4.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.493   4.025   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.018   3.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.452   2.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.963   5.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.986   0.406   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7    8                                                       
CONECT    7    6   18                                                       
CONECT    8    6   19                                                       
CONECT    9   10   20                                                       
CONECT   10    9   22                                                       
CONECT   11   12   23                                                       
CONECT   12   11   24                                                       
CONECT   13   15   21                                                       
CONECT   14   16   25                                                       
CONECT   15   13   26                                                       
CONECT   16   14   27                                                       
CONECT   17   20   21                                                       
CONECT   18    1    2    7                                                  
CONECT   19    3    8   23                                                  
CONECT   20    9   17   26                                                  
CONECT   21   13   17   28                                                  
CONECT   22   10   24   25                                                  
CONECT   23   11   19   27                                                  
CONECT   24   12   22   27                                                  
CONECT   25   14   22   26                                                  
CONECT   26    4   15   20   25                                             
CONECT   27    5   16   23   24                                             
CONECT   28   21                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

Synonyms

Not Available

Molecular Formula

C₂₇H₄₂O

Average Mass

382.6218

Monoisotopic Mass

382.323565966

IUPAC Name

2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

Traditional Name

2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

CAS Registry Number

1715-86-2

SMILES

CC(CCC=C(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3

InChI Key

RUSSPKPUXDSHNC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a 3-β-hydroxysterol (CPD-8646 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00064 g/L	ALOGPS
logP	7.46	ALOGPS
logP	6.3	ChemAxon
logS	-5.8	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	4	ChemAxon
Refractivity	122.32 m³·mol⁻¹	ChemAxon
Polarizability	47.71 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 (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0019000000-640d2c043114704aa68e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-2159000000-f92f7b9f8ba169d0ff2b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-4459000000-86521888f6a07655c251	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-f27b309e4c0ec709176d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-860c67ddd6590acc68d2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014j-1019000000-9205d494e9dce5c57c99	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Ascomycota	1	Human feces; Human saliva	Unknown

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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012781

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5117446

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Yu H, Wessels A, Tint GS, Patel SB: Partial rescue of neonatal lethality of Dhcr7 null mice by a nestin promoter-driven DHCR7 transgene expression. Brain Res Dev Brain Res. 2005 Apr 21;156(1):46-60. doi: 10.1016/j.devbrainres.2005.01.012. [PubMed:15862627 ]
Solca C, Pandit B, Yu H, Tint GS, Patel SB: Loss of apolipoprotein E exacerbates the neonatal lethality of the Smith-Lemli-Opitz syndrome mouse. Mol Genet Metab. 2007 May;91(1):7-14. doi: 10.1016/j.ymgme.2006.11.009. Epub 2007 Jan 2. [PubMed:17197219 ]

Showing metabocard for 7,8-Didehydrodesmosterol (MMDBc0033507)

MOL for #<Metabolite:0x00007fece82ac8d0>

3D MOL for #<Metabolite:0x00007fece82ac8d0>

3D SDF for #<Metabolite:0x00007fece82ac8d0>

3D-SDF for #<Metabolite:0x00007fece82ac8d0>

PDB for #<Metabolite:0x00007fece82ac8d0>

3D PDB for #<Metabolite:0x00007fece82ac8d0>

SMILES for #<Metabolite:0x00007fece82ac8d0>

INCHI for #<Metabolite:0x00007fece82ac8d0>

Structure for #<Metabolite:0x00007fece82ac8d0>

3D Structure for #<Metabolite:0x00007fece82ac8d0>