NP-MRD: Showing NP-Card for beta-Cortolone (NP0339221)

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Record Information

Version

2.0

Created at

2024-09-11 20:29:44 UTC

Updated at

2024-09-11 20:29:45 UTC

NP-MRD ID

NP0339221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Cortolone

Description

PC(O-16:0/16:1(9Z)), also known as gpcho(16:0/16:1) Or gpcho(32:1), Belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Thus, PC(O-16:0/16:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. The Palmityl alcohol moiety is derived from animal fats and vegetable oils, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. PC(O-16:0/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, PC(O-16:0/16:1(9Z)) has been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, and cow milks. This could make PC(O-16:0/16:1(9Z)) a potential biomarker for the consumption of these foods. PCs can be synthesized via three different routes. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. Fatty acids containing 16, 18 and 20 carbons are the most common.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208192D          

 26 29  0  0  1  0            999 V2000
   10.8890  -12.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8847  -12.8952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1723  -12.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4563  -12.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4519  -13.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1637  -14.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8804  -13.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5927  -14.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3094  -13.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3137  -12.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6014  -12.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6056  -11.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8933  -11.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3223  -11.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0347  -11.6690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0304  -12.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8136  -12.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3016  -12.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8206  -11.4182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4363  -10.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2196  -11.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8353  -10.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2687  -10.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6530  -10.6104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7753  -10.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7353  -14.1214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 26  1  1  0  0  0
  6  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 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 15 25  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  1  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
M  END


  Mrv0541 02251208192D          

 26 29  0  0  1  0            999 V2000
   10.8890  -12.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8847  -12.8952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1723  -12.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4563  -12.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4519  -13.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1637  -14.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8804  -13.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5927  -14.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3094  -13.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3137  -12.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6014  -12.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6056  -11.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8933  -11.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3223  -11.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0347  -11.6690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0304  -12.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8136  -12.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3016  -12.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8206  -11.4182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4363  -10.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2196  -11.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8353  -10.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2687  -10.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6530  -10.6104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7753  -10.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7353  -14.1214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 26  1  1  0  0  0
  6  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 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 15 25  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  1  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC(=O)C3C(CCC4C[C@@H](O)CC[C@]34C)C1CC[C@@]2(O)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,17-18,22-23,25-26H,3-11H2,1-2H3/t12?,13-,14?,15?,17?,18?,19-,20-,21+/m0/s1

> <INCHI_KEY>
JXCOSKURGJMQSG-YDGYSZIMSA-N

> <FORMULA>
C21H34O5

> <MOLECULAR_WEIGHT>
366.4917

> <EXACT_MASS>
366.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.23913449672382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5S,14S,15S)-14-(1,2-dihydroxyethyl)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
0.8838380473333329

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.311743825717326

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.99017402955257

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569620677009655

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
97.4429

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,14S,15S)-14-(1,2-dihydroxyethyl)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      20.326 -22.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.318 -24.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.988 -23.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.652 -24.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.644 -25.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.972 -26.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.310 -25.611   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.640 -26.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.978 -25.625   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.986 -24.085   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.656 -23.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.664 -21.768   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      20.334 -20.991   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.002 -21.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.331 -21.782   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.323 -23.322   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.785 -23.806   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.696 -22.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.798 -21.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.948 -20.290   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.410 -20.773   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      29.559 -19.749   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      26.635 -18.782   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      25.486 -19.806   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.847 -20.268   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.306 -26.360   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11    2   10   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19   25                                             
CONECT   16   10   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18   20   24                                             
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25   15                                                            
CONECT   26    5                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
1-Palmityl-2-palmitoleoyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(16:0/16:1)	HMDB
Gpcho(16:0/16:1n7)	HMDB
Gpcho(16:0/16:1W7)	HMDB
Gpcho(32:1)	HMDB
Lecithin	HMDB
PC Ae C32:1	HMDB
PC(16:0/16:1)	HMDB
PC(16:0/16:1n7)	HMDB
PC(16:0/16:1W7)	HMDB
PC(32:1)	HMDB
PC(O-32:1)	HMDB
Phosphatidylcholine(16:0/16:1)	HMDB
Phosphatidylcholine(16:0/16:1n7)	HMDB
Phosphatidylcholine(16:0/16:1W7)	HMDB
Phosphatidylcholine(32:1)	HMDB
1-Hexadecanyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine	HMDB
b-Cortolon	HMDB
b-Cortolone	HMDB, Generator
beta-Cortolon	HMDB
Β-cortolone	Generator

Chemical Formula

C₂₁H₃₄O₅

Average Mass

366.4917 Da

Monoisotopic Mass

366.24062 Da

IUPAC Name

(2S,5S,14S,15S)-14-(1,2-dihydroxyethyl)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

Traditional Name

(2S,5S,14S,15S)-14-(1,2-dihydroxyethyl)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

CAS Registry Number

Not Available

SMILES

C[C@]12CC(=O)C3C(CCC4C[C@@H](O)CC[C@]34C)C1CC[C@@]2(O)C(O)CO

InChI Identifier

InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,17-18,22-23,25-26H,3-11H2,1-2H3/t12?,13-,14?,15?,17?,18?,19-,20-,21+/m0/s1

InChI Key

JXCOSKURGJMQSG-YDGYSZIMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-alkyl,2-acylglycero-3-phosphocholines

Alternative Parents

Substituents

1-alkyl,2-acylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Glycerol ether
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-alkyl,2-acylglycerophosphocholines (LMGP01020182 )

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	1.26	ALOGPS
logP	0.88	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.44 m³·mol⁻¹	ChemAxon
Polarizability	41.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013404

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029404

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

52923742

PDB ID

Not Available

ChEBI ID

89906

Good Scents ID

Not Available

References

General References

Showing NP-Card for beta-Cortolone (NP0339221)

MOL for NP0339221 (beta-Cortolone)

3D MOL for NP0339221 (beta-Cortolone)

3D SDF for NP0339221 (beta-Cortolone)

3D-SDF for NP0339221 (beta-Cortolone)

PDB for NP0339221 (beta-Cortolone)

3D PDB for NP0339221 (beta-Cortolone)

SMILES for NP0339221 (beta-Cortolone)

INCHI for NP0339221 (beta-Cortolone)

Structure for NP0339221 (beta-Cortolone)

3D Structure for NP0339221 (beta-Cortolone)