NP-MRD: Showing NP-Card for 5b-Cholestane-3a,7a,12a,23S,25-pentol (NP0086593)

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Record Information

Version

2.0

Created at

2022-05-11 16:25:27 UTC

Updated at

2022-05-11 16:25:27 UTC

NP-MRD ID

NP0086593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5b-Cholestane-3a,7a,12a,23S,25-pentol

Description

5B-Cholestane-3a,7a,12a,23S,25-pentol belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. 5B-Cholestane-3a,7a,12a,23S,25-pentol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218332D          

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M  END

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M  END


  Mrv0541 02231218332D          

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  6 29  1  0  0  0  0
  7 29  1  0  0  0  0
 30  8  1  1  0  0  0
 31  9  1  1  0  0  0
 23 10  1  0  0  0  0
 10 11  1  0  0  0  0
 24 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 21  1  0  0  0  0
 13 30  1  0  0  0  0
 14 19  1  0  0  0  0
 14 22  1  0  0  0  0
 15 21  1  0  0  0  0
 20 15  1  0  0  0  0
 16 20  1  0  0  0  0
 16 26  1  0  0  0  0
 25 17  1  0  0  0  0
 17 27  1  0  0  0  0
 18 22  1  0  0  0  0
 18 29  1  0  0  0  0
 19 23  1  0  0  0  0
 20 30  1  0  0  0  0
 21 32  1  6  0  0  0
 22 33  1  1  0  0  0
 23 31  1  0  0  0  0
 24 28  1  0  0  0  0
 24 31  1  0  0  0  0
 25 28  1  0  0  0  0
 25 30  1  0  0  0  0
 28 26  1  0  0  0  0
 26 34  1  6  0  0  0
 27 35  1  6  0  0  0
 27 31  1  0  0  0  0
 29 36  1  0  0  0  0
 20  4  1  1  0  0  0
 28  3  1  1  0  0  0
 25  2  1  6  0  0  0
 11  1  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19?,20?,21-,22+,23-,24-,26-,27+/m0/s1

> <INCHI_KEY>
OXSBBBPDYVCAKC-CTSLUMRNSA-N

> <FORMULA>
C27H48O5

> <MOLECULAR_WEIGHT>
452.667

> <EXACT_MASS>
452.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
53.40520639004772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.048265429999999

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.645063029834372

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.929131741707618

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15943482452902014

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
126.33649999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

> <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  H   UNK     0      26.242 -19.645   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      21.956 -19.181   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      23.347 -17.400   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0      20.434 -21.686   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      28.205 -14.380   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.221  -9.918   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.330  -8.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.426 -17.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.003 -15.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.015 -17.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.064 -18.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.926 -18.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.287 -17.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.701 -13.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.172 -20.926   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.837 -21.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.011 -16.410   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.245 -10.834   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.688 -14.644   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.533 -20.207   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.868 -20.107   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.232 -12.016   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.158 -16.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.618 -18.049   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.953 -17.949   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.199 -20.307   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.372 -15.690   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.257 -18.768   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.776  -9.388   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.591 -18.668   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.676 -16.510   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.506 -20.826   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      27.749 -11.753   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      24.503 -21.127   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      23.430 -14.152   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      26.306  -7.942   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   25                                                            
CONECT    3   28                                                            
CONECT    4   20                                                            
CONECT    5   19                                                            
CONECT    6   29                                                            
CONECT    7   29                                                            
CONECT    8   30                                                            
CONECT    9   31                                                            
CONECT   10   23   11                                                       
CONECT   11   10   24    1                                                  
CONECT   12   13   21                                                       
CONECT   13   12   30                                                       
CONECT   14   19   22                                                       
CONECT   15   21   20                                                       
CONECT   16   20   26                                                       
CONECT   17   25   27                                                       
CONECT   18   22   29                                                       
CONECT   19    5   14   23                                                  
CONECT   20   15   16   30    4                                             
CONECT   21   12   15   32                                                  
CONECT   22   14   18   33                                                  
CONECT   23   10   19   31                                                  
CONECT   24   11   28   31                                                  
CONECT   25   17   28   30    2                                             
CONECT   26   16   28   34                                                  
CONECT   27   17   35   31                                                  
CONECT   28   24   25   26    3                                             
CONECT   29    6    7   18   36                                             
CONECT   30    8   13   20   25                                             
CONECT   31    9   23   24   27                                             
CONECT   32   21                                                            
CONECT   33   22                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   29                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(23S)-5b-Cholestane-3a,7a,12a,23,25-pentol	HMDB
(3alpha,5beta,7alpha,12alpha,23S)-Cholestane-3,7,12,23,25-pentol	HMDB

Chemical Formula

C₂₇H₄₈O₅

Average Mass

452.6670 Da

Monoisotopic Mass

452.35017 Da

IUPAC Name

(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

CAS Registry Number

Not Available

SMILES

[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O

InChI Identifier

InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19?,20?,21-,22+,23-,24-,26-,27+/m0/s1

InChI Key

OXSBBBPDYVCAKC-CTSLUMRNSA-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 pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five 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

Pentahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
Pentahydroxy bile acid, alcohol, or derivatives
Cholestane-skeleton
25-hydroxysteroid
23-hydroxysteroid
3-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	2.33	ALOGPS
logP	2.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	14.93	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.34 m³·mol⁻¹	ChemAxon
Polarizability	53.41 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

HMDB0000483

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022068

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

5470

PubChem Compound

53477695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5b-Cholestane-3a,7a,12a,23S,25-pentol (NP0086593)

MOL for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

3D MOL for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

3D SDF for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

3D-SDF for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

PDB for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

3D PDB for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

SMILES for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

INCHI for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

Structure for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)

3D Structure for NP0086593 (5b-Cholestane-3a,7a,12a,23S,25-pentol)