NP-MRD: Showing NP-Card for (3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one (NP0049872)

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Record Information

Version

2.0

Created at

2022-03-17 21:19:28 UTC

Updated at

2022-03-17 21:19:28 UTC

NP-MRD ID

NP0049872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one

Description

(3Beta,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one, also known as 28-homoteasterone, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3beta,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3beta,22R,23R,24S)-3,22,23-trihydroxystigmastan-6-one has been detected, but not quantified in, radish and root vegetables. (3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one is found in Raphanus sativus. This could make (3beta,22R,23R,24S)-3,22,23-trihydroxystigmastan-6-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210292D          

 33 36  0  0  0  0            999 V2000
   -2.9133   -2.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2565   -1.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4207   -1.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -0.9023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -1.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506   -1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506   -0.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898   -0.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688   -0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688    0.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    0.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640    0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2565   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    2.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    2.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875    3.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181   -3.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0107   -3.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -3.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875   -3.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431    3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640    3.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    0.9023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    0.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640    1.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431    1.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  2 22  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  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 12  1  0  0  0  0
 10 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 31  1  0  0  0  0
 18 19  1  0  0  0  0
 18 28  1  0  0  0  0
 18 32  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END


  Mrv0541 02241210292D          

 33 36  0  0  0  0            999 V2000
   -2.9133   -2.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2565   -1.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4207   -1.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -0.9023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -1.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506   -1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506   -0.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898   -0.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688   -0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688    0.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    0.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640    0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2565   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    2.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    2.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875    3.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181   -3.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0107   -3.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -3.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875   -3.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431    3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640    3.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    0.9023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    0.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640    1.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431    1.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  2 22  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  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 12  1  0  0  0  0
 10 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 31  1  0  0  0  0
 18 19  1  0  0  0  0
 18 28  1  0  0  0  0
 18 32  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049872

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C(C)C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O4/c1-7-19(16(2)3)27(33)26(32)17(4)21-8-9-22-20-15-25(31)24-14-18(30)10-12-29(24,6)23(20)11-13-28(21,22)5/h16-24,26-27,30,32-33H,7-15H2,1-6H3

> <INCHI_KEY>
DYENWMUXSKPFLC-UHFFFAOYSA-N

> <FORMULA>
C29H50O4

> <MOLECULAR_WEIGHT>
462.7049

> <EXACT_MASS>
462.370910088

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.57230737139258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
5.0210910559999995

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.858403102254705

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.640097745450323

> <JCHEM_PKA_STRONGEST_BASIC>
-2.696313461282922

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
132.4604

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.438  -4.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.212  -3.675   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.519  -2.143   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.051  -1.684   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.447  -1.071   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.914  -1.530   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.762  -3.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.230  -3.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.841  -2.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.841  -0.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.221  -1.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.688  -0.460   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.688   1.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.688   1.532   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.608   0.306   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.293   0.460   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.212  -0.765   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.058   4.442   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.591   4.442   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.510   5.821   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.455  -5.207   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.680  -4.288   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.834  -5.820   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.753  -6.893   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.284  -6.280   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.510  -7.199   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.760   5.973   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.293   5.821   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.058   7.199   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.591   1.684   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.058   1.838   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.293   3.217   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.760   3.523   0.000  0.00  0.00           O+0
CONECT    1    2   25                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   15                                             
CONECT   11   10                                                            
CONECT   12    6   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16   15   17   31                                                  
CONECT   17   16                                                            
CONECT   18   19   28   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22    2    7   21   23                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25    1   24   26                                                  
CONECT   26   25                                                            
CONECT   27   28                                                            
CONECT   28   18   27   29                                                  
CONECT   29   28                                                            
CONECT   30   31                                                            
CONECT   31   16   30   32                                                  
CONECT   32   18   31   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3b,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one	Generator
(3Β,22R,23R,24S)-3,22,23-trihydroxystigmastan-6-one	Generator
28-Homoteasterone	HMDB

Chemical Formula

C₂₉H₅₀O₄

Average Mass

462.7049 Da

Monoisotopic Mass

462.37091 Da

IUPAC Name

14-(5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

Traditional Name

14-(5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

CAS Registry Number

90524-90-6

SMILES

CCC(C(C)C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C29H50O4/c1-7-19(16(2)3)27(33)26(32)17(4)21-8-9-22-20-15-25(31)24-14-18(30)10-12-29(24,6)23(20)11-13-28(21,22)5/h16-24,26-27,30,32-33H,7-15H2,1-6H3

InChI Key

DYENWMUXSKPFLC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Oryza sativa	FooDB	KNAPSACK
Raphanus sativus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	4.14	ALOGPS
logP	5.02	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-2.7	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	132.46 m³·mol⁻¹	ChemAxon
Polarizability	55.57 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0039713

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019349

KNApSAcK ID

C00036259

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

73834440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one (NP0049872)

MOL for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

3D MOL for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

3D SDF for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

3D-SDF for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

PDB for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

3D PDB for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

SMILES for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

INCHI for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

Structure for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)

3D Structure for NP0049872 ((3alpha,22R,23R,24S)-3,22,23-Trihydroxystigmastan-6-one)