NP-MRD: Showing NP-Card for 3b,5a,6b-Cholestanetriol (NP0087116)

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Record Information

Version

2.0

Created at

2022-05-11 16:40:33 UTC

Updated at

2022-05-11 16:40:33 UTC

NP-MRD ID

NP0087116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3b,5a,6b-Cholestanetriol

Description

PE(16:0/18:0), Also known as PE(34:0), Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages. Thus, PE(16:0/18:0) Is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:0/18:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:0/18:0) Exists in all living species, ranging from bacteria to humans. Within humans, PE(16:0/18:0) Participates in a number of enzymatic reactions. In particular, cytidine monophosphate and PE(16:0/18:0) Can be biosynthesized from CDP-ethanolamine and DG(16:0/18:0/0:0); Which is mediated by the enzyme choline/ethanolaminephosphotransferase. In addition, PE(16:0/18:0) Can be biosynthesized from PS(16:0/18:0) Through the action of the enzyme phosphatidylserine decarboxylase. A phosphatidylethanolamine 34:1 Zwitterion obtained by transfer of a proton from the phosphate to the amino group of 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine. 3b,5a,6b-Cholestanetriol is found in Echinogorgia aurantiaca, Eunicea laciniata and Plexaurella grisea. In humans, PE(16:0/18:0) Is involved in phosphatidylcholine biosynthesis.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HMDB03990.mol
  Mrv0541 02231219512D          

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M  END

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M  END

HMDB03990.mol
  Mrv0541 02231219512D          

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  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 12 19  1  1  0  0  0
  9 20  1  1  0  0  0
  5 21  1  1  0  0  0
  7 22  1  1  0  0  0
  2 23  1  1  0  0  0
  4 24  1  6  0  0  0
 10 25  1  6  0  0  0
 18 26  1  6  0  0  0
 11 27  1  6  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087116

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1

> <INCHI_KEY>
YMMFNKXZULYSOQ-RUXQDQFYSA-N

> <FORMULA>
C27H48O3

> <MOLECULAR_WEIGHT>
420.6682

> <EXACT_MASS>
420.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.697384889840905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,7,8-triol

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
5.211471134

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.715005071511072

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.28748790470204

> <JCHEM_PKA_STRONGEST_BASIC>
-2.728020209621212

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
122.61249999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cholestane-3β,5α,6β-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB03990.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.373  -2.530   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.373  -4.070   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.039  -4.840   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.706  -4.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.706  -2.530   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.039  -1.760   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.372  -4.840   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.038  -4.070   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.038  -2.530   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.372  -1.760   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.295  -1.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.295  -0.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.038   0.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.372  -0.220   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.760  -2.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.665  -0.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.760   0.256   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.236   1.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.456   1.312   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.038  -0.990   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -3.706  -0.990   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.372  -6.380   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -7.707  -4.840   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.706  -5.610   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      -2.372  -3.300   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       1.147   2.810   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       0.295  -3.300   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       3.742   2.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.218   3.506   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.725   3.826   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.200   5.291   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.111   6.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.707   5.611   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   24                                             
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9    5   14   25                                             
CONECT   11    9   12   15   27                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   26   28                                                  
CONECT   19   12                                                            
CONECT   20    9                                                            
CONECT   21    5                                                            
CONECT   22    7                                                            
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25   10                                                            
CONECT   26   18                                                            
CONECT   27   11                                                            
CONECT   28   18   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine	ChEBI
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine zwitterion	ChEBI
2-Ammonioethyl (2R)-3-(palmitoyloxy)-2-(stearoyloxy)propyl phosphate	ChEBI
2-Ammonioethyl (2R)-3-(palmitoyloxy)-2-(stearoyloxy)propyl phosphoric acid	Generator
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine	HMDB
PE(34:0)	HMDB
Phophatidylethanolamine(16:0/18:0)	HMDB
GPEtn(34:0)	HMDB
Phophatidylethanolamine(34:0)	HMDB
GPEtn(16:0/18:0)	HMDB
3beta,5alpha,6beta-Cholestanetriol	ChEBI
3beta,5alpha,6beta-Trihydroxycholestane	ChEBI
Cholestane-3-beta,5-alpha,6-beta-triol	ChEBI
Cholestane-3beta-5alpha,6beta-triol	ChEBI
3β,5α,6β-cholestanetriol	Generator
3b,5a,6b-Trihydroxycholestane	Generator
3β,5α,6β-trihydroxycholestane	Generator
Cholestane-3-b,5-a,6-b-triol	Generator
Cholestane-3-β,5-α,6-β-triol	Generator
Cholestane-3b-5a,6b-triol	Generator
Cholestane-3β-5α,6β-triol	Generator
5-alpha,6-beta-Dihydroxycholestanol	HMDB
5alpha,6beta-Dihydroxycholestanol	HMDB
Cholesta-3beta,5alpha,6beta-triol	HMDB
Cholestane-3,5,6-triol	HMDB, MeSH
Cholestane-3beta,5alpha,6beta-triol	HMDB
CT	HMDB
Cholestane-3,5,6-triol, (3beta, 5beta, 6beta)-isomer	MeSH, HMDB
Cholestane-3,5,6-triol, (3beta, 6beta)-isomer	MeSH, HMDB
Cholestane-3 beta,5 alpha,6 beta-triol	MeSH, HMDB
5alpha-Cholestane-3beta,5,6beta-triol	MeSH, HMDB
Cholestane-3,5,6-triol, (3beta, 5alpha, 6alpha)-isomer	MeSH, HMDB
Cholestane-3,5,6-triol, (3beta)-isomer	MeSH, HMDB
Cholestane-3,5,6-triol, (3beta, 5alpha, 6beta)-isomer	MeSH, HMDB
3b,5a,6b-Cholestanetriol	Generator
5a,6b-Dihydroxycholestanol	Generator, HMDB
5Α,6β-dihydroxycholestanol	Generator, HMDB

Chemical Formula

C₂₇H₄₈O₃

Average Mass

420.6682 Da

Monoisotopic Mass

420.36035 Da

IUPAC Name

(1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,7,8-triol

Traditional Name

cholestane-3β,5α,6β-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1

InChI Key

YMMFNKXZULYSOQ-RUXQDQFYSA-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
Echinogorgia aurantiaca	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Eunicea laciniata	LOTUS Database	35616633
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
Plexaurella grisea	LOTUS Database	35616633
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 phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

Alternative Parents

Substituents

Diacylglycero-3-phosphoethanolamine
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Primary amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1,2-diacyl-sn-glycero-3-phosphoethanolamine (CHEBI:73126 )
Diacylglycerophosphoethanolamines (LMGP02011225 )

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	5.11	ALOGPS
logP	5.21	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-2.7	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	122.61 m³·mol⁻¹	ChemAxon
Polarizability	52.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0008925

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB026115

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

5326793

PDB ID

Not Available

ChEBI ID

73006

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3b,5a,6b-Cholestanetriol (NP0087116)

MOL for NP0087116 (3b,5a,6b-Cholestanetriol)

3D MOL for NP0087116 (3b,5a,6b-Cholestanetriol)

3D SDF for NP0087116 (3b,5a,6b-Cholestanetriol)

3D-SDF for NP0087116 (3b,5a,6b-Cholestanetriol)

PDB for NP0087116 (3b,5a,6b-Cholestanetriol)

3D PDB for NP0087116 (3b,5a,6b-Cholestanetriol)

SMILES for NP0087116 (3b,5a,6b-Cholestanetriol)

INCHI for NP0087116 (3b,5a,6b-Cholestanetriol)

Structure for NP0087116 (3b,5a,6b-Cholestanetriol)

3D Structure for NP0087116 (3b,5a,6b-Cholestanetriol)