NP-MRD: Showing NP-Card for Cholesteryl acetate (NP0087082)

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Record Information

Version

1.0

Created at

2022-05-11 16:39:31 UTC

Updated at

2022-05-11 16:39:31 UTC

NP-MRD ID

NP0087082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cholesteryl acetate

Description

2-Methylacetoacetic acid, also known as 2-methyl-3-oxo-butyric acid or 2-acetylpropionic acid, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Methylacetoacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesteryl acetate is found in Baccharoides anthelmintica, Cajanus cajan, Digitalis purpurea, Dioscorea polystachya, Dolichousnea longissima, Heteroxenia ghardaqensis, Pyrosoma atlanticum, Wrightia tinctoria and Zea mays. It was first documented in 1996 (PMID: 9001814). 2-Methylacetoacetic acid, with regard to humans, has been linked to the inborn metabolic disorder beta-ketothiolase deficiency (PMID: 14518824) (PMID: 17371050) (PMID: 9744475).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219472D          

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M  END

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 26 27  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)C1CCC2C3CC=C4C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24?,25?,26?,27?,28+,29-/m1/s1

> <INCHI_KEY>
XUGISPSHIFXEHZ-JUTJDYIZSA-N

> <FORMULA>
C29H48O2

> <MOLECULAR_WEIGHT>
428.6902

> <EXACT_MASS>
428.36543078

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.696553706104574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate

> <ALOGPS_LOGP>
7.40

> <JCHEM_LOGP>
7.554014441

> <ALOGPS_LOGS>
-7.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003272146910708

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
129.76799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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      17.083 -15.989   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      15.759 -13.674   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      25.389 -11.288   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.389 -12.828   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.055 -13.598   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.721 -12.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.845 -10.819   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.055 -10.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.320 -13.609   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.845 -13.298   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.721 -11.288   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.744 -12.058   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.080 -15.202   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.324  -9.356   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.389  -9.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.307 -15.213   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.893 -12.740   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.696 -16.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.332 -12.069   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.867 -16.059   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.433 -13.553   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.831  -9.038   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.420 -15.224   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.296  -8.209   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.309  -7.574   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.816  -7.256   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.294  -5.793   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.753 -15.214   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.266  -4.647   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      32.801  -5.475   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.416 -15.979   0.000  0.00  0.00           C+0
CONECT    1   23   28                                                       
CONECT    2   28                                                            
CONECT    3    4    7    8   15                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    9   11                                                  
CONECT    7    3   12   14                                                  
CONECT    8    3   11                                                       
CONECT    9    6   16   17   19                                             
CONECT   10    4   12                                                       
CONECT   11    6    8                                                       
CONECT   12    7   10                                                       
CONECT   13    5   18                                                       
CONECT   14    7   22   24                                                  
CONECT   15    3                                                            
CONECT   16    9   18   20                                                  
CONECT   17    9   21                                                       
CONECT   18   13   16                                                       
CONECT   19    9                                                            
CONECT   20   16   23                                                       
CONECT   21   17   23                                                       
CONECT   22   14   25                                                       
CONECT   23    1   20   21                                                  
CONECT   24   14                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   29   30                                                  
CONECT   28    1    2   31                                                  
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
2-Methylacetoacetate	Generator
2-Methyl-3-oxo-butyric acid	HMDB
2-Methyl-3-oxo-butyrate	HMDB
2Methyl-3-ketovalerate	HMDB
(+/-)-2-methyl-3-oxobutanoate	HMDB
(+/-)-2-methyl-3-oxobutanoic acid	HMDB
2-Acetylpropionic acid	HMDB
2-Methyl-3-ketobutyric acid	HMDB
2-Methyl-3-oxo-butanoate	HMDB
2-Methyl-3-oxo-butanoic acid	HMDB
2-Methyl-3-oxobutanoate	HMDB
2-Methyl-3-oxobutanoic acid	HMDB
2-Methyl-3-oxobutyric acid	HMDB
2-Methyl-acetoacetic acid	HMDB
3-oxo-2-Methylbutyric acid	HMDB
a-Methylacetoacetic acid	HMDB
alpha-Methylacetoacetate	HMDB
alpha-Methylacetoacetic acid	HMDB
(-)-2-Methyl-3-oxobutanoic acid	HMDB
(2S)-2-Methyl-3-oxobutanoic acid	HMDB
(S)-2-Acetylpropionic acid	HMDB
(S)-2-Methyl-3-oxobutyric acid	HMDB
(±)-2-methyl-3-oxobutanoic acid	HMDB
3-Keto-2-methylbutyrate	HMDB
3-Keto-2-methylbutyric acid	HMDB
Α-methylacetoacetic acid	HMDB
(-)-Cholesteryl acetate	HMDB
(3b)-Cholest-5-en-3-ol acetate	HMDB
3-Cholesteryl acetate	HMDB
3b-Acetoxycholest-5-ene	HMDB
Cholest-5-en-3b-ol acetate	HMDB
Cholest-5-en-3b-yl acetate	HMDB
Cholesterin acetate	HMDB
Cholesterol 3-acetate	HMDB
Cholesterol 3b-acetate	HMDB
Cholesterol acetate	HMDB
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetic acid	Generator, HMDB
Cholesteryl acetate	MeSH
Cholesteryl acetic acid	Generator

Chemical Formula

C₂₉H₄₈O₂

Average Mass

428.6902 Da

Monoisotopic Mass

428.36543 Da

IUPAC Name

(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate

Traditional Name

(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)C1CCC2C3CC=C4C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(C)=O

InChI Identifier

InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24?,25?,26?,27?,28+,29-/m1/s1

InChI Key

XUGISPSHIFXEHZ-JUTJDYIZSA-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
Baccharoides anthelmintica	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cajanus cajan	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Digitalis purpurea	LOTUS Database	35616633
Dioscorea polystachya	LOTUS Database	35616633
Dolichousnea longissima	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Heteroxenia ghardaqensis	LOTUS Database	35616633
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
Pyrosoma atlanticum	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Wrightia tinctoria	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Beta-keto acid
Branched fatty acid
Methyl-branched fatty acid
Short-chain keto acid
Beta-hydroxy ketone
Fatty acyl
1,3-dicarbonyl compound
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	7.4	ALOGPS
logP	7.55	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.77 m³·mol⁻¹	ChemAxon
Polarizability	54.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0003771

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023226

KNApSAcK ID

Not Available

Chemspider ID

24191898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

150996

PDB ID

Not Available

ChEBI ID

37079

Good Scents ID

Not Available

References

General References

Fukao T, Zhang GX, Sakura N, Kubo T, Yamaga H, Hazama A, Kohno Y, Matsuo N, Kondo M, Yamaguchi S, Shigematsu Y, Kondo N: The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. J Inherit Metab Dis. 2003;26(5):423-31. [PubMed:14518824 ]
Fukao T, Kodama A, Aoyanagi N, Tsukino R, Uemura S, Song XQ, Watanebe H, Kuhara T, Matsumoto I, Orii T, Kondo N: Mild form of beta-ketothiolase deficiency (mitochondrial acetoacetyl-CoA thiolase deficiency) in two Japanese siblings: identification of detectable residual activity and cross-reactive material in EB-transformed lymphocytes. Clin Genet. 1996 Oct;50(4):263-6. [PubMed:9001814 ]
Haapalainen AM, Merilainen G, Pirila PL, Kondo N, Fukao T, Wierenga RK: Crystallographic and kinetic studies of human mitochondrial acetoacetyl-CoA thiolase: the importance of potassium and chloride ions for its structure and function. Biochemistry. 2007 Apr 10;46(14):4305-21. doi: 10.1021/bi6026192. Epub 2007 Mar 20. [PubMed:17371050 ]
Fukao T, Nakamura H, Song XQ, Nakamura K, Orii KE, Kohno Y, Kano M, Yamaguchi S, Hashimoto T, Orii T, Kondo N: Characterization of N93S, I312T, and A333P missense mutations in two Japanese families with mitochondrial acetoacetyl-CoA thiolase deficiency. Hum Mutat. 1998;12(4):245-54. doi: 10.1002/(SICI)1098-1004(1998)12:4<245::AID-HUMU5>3.0.CO;2-E. [PubMed:9744475 ]

Showing NP-Card for Cholesteryl acetate (NP0087082)

MOL for NP0087082 (Cholesteryl acetate)

3D MOL for NP0087082 (Cholesteryl acetate)

3D SDF for NP0087082 (Cholesteryl acetate)

3D-SDF for NP0087082 (Cholesteryl acetate)

PDB for NP0087082 (Cholesteryl acetate)

3D PDB for NP0087082 (Cholesteryl acetate)

SMILES for NP0087082 (Cholesteryl acetate)

INCHI for NP0087082 (Cholesteryl acetate)

Structure for NP0087082 (Cholesteryl acetate)

3D Structure for NP0087082 (Cholesteryl acetate)