NP-MRD: Showing NP-Card for 7alpha,25-Dihydroxycholesterol (NP0087481)

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Record Information

Version

2.0

Created at

2022-05-11 16:50:51 UTC

Updated at

2022-05-11 16:50:51 UTC

NP-MRD ID

NP0087481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha,25-Dihydroxycholesterol

Description

4-Oxo-Retinoic acid, also known as 4-oxo-retinoate or 4-oxo-atra, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. 4-Oxo-Retinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Oxo-retinoic acid can be biosynthesized from 4-hydroxyretinoic acid; which is catalyzed by the enzyme cytochrome P450 26A1. In humans, 4-oxo-retinoic acid is involved in retinol metabolism. 7alpha,25-Dihydroxycholesterol was first documented in 1979 (PMID: 435468). A retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring (PMID: 2051220) (PMID: 25492813) (PMID: 2772923) (PMID: 8794203).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220352D          

 33 36  0  0  1  0            999 V2000
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   16.6351   -5.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3425   -6.5268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 26 32  1  0  0  0  0
  6 33  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02231220352D          

 33 36  0  0  1  0            999 V2000
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  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
 13 15  2  0  0  0  0
 21 23  1  0  0  0  0
  1 29  1  6  0  0  0
  2 30  1  1  0  0  0
  5 31  1  6  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
 26 32  1  0  0  0  0
  6 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
BQMSKLCEWBSPPY-IKVTXIKFSA-N

> <FORMULA>
C27H46O3

> <MOLECULAR_WEIGHT>
418.6523

> <EXACT_MASS>
418.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.17246487870763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.488917008666668

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.5307684666132

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204233421519334

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6890459247935982

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
123.89109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7α,25-dihydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      33.713  -9.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.379 -10.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.713  -8.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      36.381  -9.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.052  -9.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.373 -12.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.060  -7.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.379  -7.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.706  -6.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.381  -8.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.705 -10.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.052  -8.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.052 -12.953   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.060  -6.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.705 -12.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.378  -9.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.692  -9.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.421  -5.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.693  -5.236   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.378 -12.953   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.044 -10.644   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.781  -6.032   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.044 -12.183   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.142  -5.242   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      25.697 -12.953   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      40.508  -6.032   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      41.869  -5.248   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.502  -7.605   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.706 -11.447   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      32.366  -9.104   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      31.039 -11.414   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      41.886  -6.827   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      33.768 -12.989   0.000  0.00  0.00           O+0
CONECT    1    4   29    2    3                                             
CONECT    2    5    6   30    1                                             
CONECT    3    7    8    9    1                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   31                                             
CONECT    6    2   13   33                                                  
CONECT    7    3   14   10                                                  
CONECT    8    3   12                                                       
CONECT    9    3                                                            
CONECT   10    4    7                                                       
CONECT   11    5   15   16   17                                             
CONECT   12    5    8                                                       
CONECT   13    6   15                                                       
CONECT   14    7   18   19                                                  
CONECT   15   11   20   13                                                  
CONECT   16   11   21                                                       
CONECT   17   11                                                            
CONECT   18   14   22                                                       
CONECT   19   14                                                            
CONECT   20   15   23                                                       
CONECT   21   16   23                                                       
CONECT   22   18   24                                                       
CONECT   23   20   25   21                                                  
CONECT   24   22   26                                                       
CONECT   25   23                                                            
CONECT   26   24   27   28   32                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    5                                                            
CONECT   32   26                                                            
CONECT   33    6                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-oxo-all-trans-Retinoic acid	ChEBI
4-oxo-AtRA	ChEBI
4-oxo-all-trans-Retinoate	Generator
4-oxo-Retinoate	Generator
4-Keto-retinoate	HMDB
4-Keto-retinoic acid	HMDB
4-Ketoretinoate	HMDB
4-Ketoretinoic acid	HMDB
4-Oxoretinoate	HMDB
4-Oxoretinoic acid	HMDB
4-Oxotretinoin	HMDB
all-trans-4-Oxoretinoate	HMDB
all-trans-4-Oxoretinoic acid	HMDB
Ro 11-4824	HMDB
Ro 12-4824	HMDB
4-oxo-13-cis-Retinoic acid	HMDB
4-oxo-Isotretinoin	HMDB
4-oxo-trans-Retinoic acid	HMDB
4-Oxoretinoic acid, (13-cis)-isomer	HMDB
3beta,7alpha,25-Trihydroxycholest-5-ene	ChEBI
5-Cholesten-3beta,7alpha,25-triol	ChEBI
Cholest-5-ene-3beta,7alpha,25-triol	ChEBI
3b,7a,25-Trihydroxycholest-5-ene	Generator
3β,7α,25-trihydroxycholest-5-ene	Generator
5-Cholesten-3b,7a,25-triol	Generator
5-Cholesten-3β,7α,25-triol	Generator
Cholest-5-ene-3b,7a,25-triol	Generator
Cholest-5-ene-3β,7α,25-triol	Generator
7-alpha,25-Dihydroxycholesterol	HMDB
7alpha,25-Dihydroxycholesterol	HMDB, KEGG
Cholest-5-ene-3-b,7-a,25-triol	HMDB
Cholest-5-ene-3-beta,7-alpha,25-triol	HMDB
7a,25-Dihydroxycholesterol	Generator
7Α,25-dihydroxycholesterol	Generator

Chemical Formula

C₂₇H₄₆O₃

Average Mass

418.6523 Da

Monoisotopic Mass

418.34470 Da

IUPAC Name

(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

Traditional Name

7α,25-dihydroxycholesterol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

InChI Key

BQMSKLCEWBSPPY-IKVTXIKFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Cyclohexenone
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:80656 )
Retinoids (C16678 )
Retinoids (LMPR01090026 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.54	ALOGPS
logP	4.49	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.89 m³·mol⁻¹	ChemAxon
Polarizability	52.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006285

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023877

KNApSAcK ID

Not Available

Chemspider ID

4941652

KEGG Compound ID

C16678

BioCyc ID

Not Available

BiGG ID

2430195

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437063

PDB ID

Not Available

ChEBI ID

80656

Good Scents ID

Not Available

References

General References

Eckhoff C, Collins MD, Nau H: Human plasma all-trans-, 13-cis- and 13-cis-4-oxoretinoic acid profiles during subchronic vitamin A supplementation: comparison to retinol and retinyl ester plasma levels. J Nutr. 1991 Jul;121(7):1016-25. doi: 10.1093/jn/121.7.1016. [PubMed:2051220 ]
Topletz AR, Tripathy S, Foti RS, Shimshoni JA, Nelson WL, Isoherranen N: Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41. doi: 10.1124/mol.114.096784. Epub 2014 Dec 9. [PubMed:25492813 ]
Eckhoff C, Lofberg B, Chahoud I, Bochert G, Nau H: Transplacental pharmacokinetics and teratogenicity of a single dose of retinol (vitamin A) during organogenesis in the mouse. Toxicol Lett. 1989 Aug;48(2):171-84. doi: 10.1016/0378-4274(89)90172-0. [PubMed:2772923 ]
Frolik CA, Roberts AB, Tavela TE, Roller PP, Newton DL, Sporn MB: Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver. Biochemistry. 1979 May 15;18(10):2092-7. doi: 10.1021/bi00577a039. [PubMed:435468 ]
Stahl W, Hanusch M, Sies H: 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells. Adv Exp Med Biol. 1996;387:121-8. doi: 10.1007/978-1-4757-9480-9_17. [PubMed:8794203 ]

Showing NP-Card for 7alpha,25-Dihydroxycholesterol (NP0087481)

MOL for NP0087481 (7alpha,25-Dihydroxycholesterol)

3D MOL for NP0087481 (7alpha,25-Dihydroxycholesterol)

3D SDF for NP0087481 (7alpha,25-Dihydroxycholesterol)

3D-SDF for NP0087481 (7alpha,25-Dihydroxycholesterol)

PDB for NP0087481 (7alpha,25-Dihydroxycholesterol)

3D PDB for NP0087481 (7alpha,25-Dihydroxycholesterol)

SMILES for NP0087481 (7alpha,25-Dihydroxycholesterol)

INCHI for NP0087481 (7alpha,25-Dihydroxycholesterol)

Structure for NP0087481 (7alpha,25-Dihydroxycholesterol)

3D Structure for NP0087481 (7alpha,25-Dihydroxycholesterol)