NP-MRD: Showing NP-Card for 3a,7a,12a-Trihydroxy-5b-cholestan-26-al (NP0087061)

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Record Information

Version

2.0

Created at

2022-05-11 16:38:51 UTC

Updated at

2022-05-11 16:38:51 UTC

NP-MRD ID

NP0087061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,7a,12a-Trihydroxy-5b-cholestan-26-al

Description

3A,7a,12a-Trihydroxy-5b-cholestan-26-al belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, 3a,7a,12a-trihydroxy-5b-cholestan-26-al is considered to be a bile acid lipid molecule. 3Alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al is an intermediate in bile acid biosynthesis. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. Bile acids have potent toxic properties (e.G., Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. 3A,7a,12a-Trihydroxy-5b-cholestan-26-al is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3A,7a,12a-Trihydroxy-5b-cholestan-26-al exists in all living organisms, ranging from bacteria to humans. Within humans, 3a,7a,12a-trihydroxy-5b-cholestan-26-al participates in a number of enzymatic reactions. In particular, 3a,7a,12a-trihydroxy-5b-cholestan-26-al can be biosynthesized from 27-deoxy-5b-cyprinol through its interaction with the enzyme sterol 26-hydroxylase, mitochondrial. In addition, 3a,7a,12a-trihydroxy-5b-cholestan-26-al can be converted into 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid through its interaction with the enzyme sterol 26-hydroxylase, mitochondrial. In humans, 3a,7a,12a-trihydroxy-5b-cholestan-26-al is involved in cerebrotendinous xanthomatosis (ctx). The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219452D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02231219452D          

 36 39  0  0  1  0            999 V2000
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   24.9711  -15.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1618  -11.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7133  -13.9608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1179  -16.1255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4684  -14.7418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.0069  -17.0769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.7338  -15.7281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  6  0  0  0
 17  2  1  6  0  0  0
 18  3  1  6  0  0  0
  4 31  2  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  6  0  0  0
  5 19  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 31  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 14 12  1  1  0  0  0
 15 13  1  1  0  0  0
 14 16  1  0  0  0  0
 14 19  1  0  0  0  0
 14 23  1  0  0  0  0
 15 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 27  1  0  0  0  0
 16 24  1  0  0  0  0
 17 20  1  0  0  0  0
 17 25  1  0  0  0  0
 18 26  1  0  0  0  0
 18 28  1  0  0  0  0
 19 29  1  0  0  0  0
 19 32  1  6  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 20 33  1  1  0  0  0
 21 24  1  0  0  0  0
 21 34  1  6  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 22 35  1  1  0  0  0
 23 30  1  0  0  0  0
 23 36  1  6  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087061

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h15-25,29-31H,5-14H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
USFJGINJGUIFSY-XZULNKEGSA-N

> <FORMULA>
C27H46O4

> <MOLECULAR_WEIGHT>
434.6517

> <EXACT_MASS>
434.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
52.41570405546709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.7560018126666685

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.071715106969688

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15943465417462444

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
123.64039999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

> <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  O   UNK     0      43.738 -24.705   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.105 -31.515   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.851 -31.421   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      53.597 -22.054   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      47.091 -24.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      51.062 -21.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.598 -24.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      50.583 -22.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.077 -23.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.810 -23.852   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.034 -20.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.156 -25.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.099 -27.501   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      45.156 -26.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.087 -29.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.822 -25.950   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      43.847 -30.634   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.187 -30.656   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.613 -26.251   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.822 -29.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.489 -28.260   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.075 -30.645   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.156 -28.260   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      42.489 -26.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.464 -31.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.634 -31.491   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      39.660 -28.172   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      38.200 -28.985   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      47.512 -27.490   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      46.613 -28.730   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      52.569 -20.908   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      47.998 -26.060   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      45.020 -30.101   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      43.808 -27.518   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      41.080 -31.877   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      46.170 -29.359   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   31                                                            
CONECT    5    7   10   19                                                  
CONECT    6    8   11   31                                                  
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12   14                                                            
CONECT   13   15                                                            
CONECT   14   12   16   19   23                                             
CONECT   15   13   21   22   27                                             
CONECT   16    1   14   24                                                  
CONECT   17    2   20   25                                                  
CONECT   18    3   26   28                                                  
CONECT   19    5   14   29   32                                             
CONECT   20   17   21   23   33                                             
CONECT   21   15   20   24   34                                             
CONECT   22   15   25   26   35                                             
CONECT   23   14   20   30   36                                             
CONECT   24   16   21                                                       
CONECT   25   17   22                                                       
CONECT   26   18   22                                                       
CONECT   27   15   28                                                       
CONECT   28   18   27                                                       
CONECT   29   19   30                                                       
CONECT   30   23   29                                                       
CONECT   31    4    6                                                       
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   22                                                            
CONECT   36   23                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-al	ChEBI
3,7,12-Trihydroxycholestan-26-al	ChEBI
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-al	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-al	Generator
(6R)-2-Methyl-6-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanal	HMDB
3-alpha-7-alpha-12-alpha-Trihydroxy-5-beta-cholestan-26-al	HMDB
3alpha,7-alpha,12alpha-Trihydroxy-5beta-cholestan-26-al	HMDB
3 alpha,7-alpha,12 alpha-Trihydroxy-5 beta-cholestan-26-al	HMDB

Chemical Formula

C₂₇H₄₆O₄

Average Mass

434.6517 Da

Monoisotopic Mass

434.33961 Da

IUPAC Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

Traditional Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O

InChI Identifier

InChI=1S/C27H46O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h15-25,29-31H,5-14H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

USFJGINJGUIFSY-XZULNKEGSA-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 trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

27-oxosteroid
26-oxosteroid
Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxide
Organic oxygen compound
Organooxygen compound
Aldehyde
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:16466 )
7alpha-hydroxy steroid (CHEBI:16466 )
cholestanoid (CHEBI:16466 )
12alpha-hydroxy steroid (CHEBI:16466 )
26-oxo steroid (CHEBI:16466 )
C27 bile acids, alcohols, and derivatives (C01301 )
C27 bile acids, alcohols, and derivatives (LMST04030164 )

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	3.92	ALOGPS
logP	3.76	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.07	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.64 m³·mol⁻¹	ChemAxon
Polarizability	52.42 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	Yes	ChemAxon