NP-MRD: Showing NP-Card for (1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol (NP0205697)

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Record Information

Version

2.0

Created at

2022-09-05 01:39:47 UTC

Updated at

2022-09-05 01:39:47 UTC

NP-MRD ID

NP0205697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol

Description

Stigmastane-3beta,5alpha,6beta-triol, also known as 5alpha,6beta-dihydroxysitosterol or sitostanetriol, 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. Thus, stigmastane-3beta,5alpha,6beta-triol is considered to be a sterol. (1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol is found in Apis mellifera, Breynia fruticosa and Machilus zuihoensis. (1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol was first documented in 2003 (PMID: 12898426). Based on a literature review very few articles have been published on stigmastane-3beta,5alpha,6beta-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309052203392D          

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M  END

     RDKit          3D

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M  END

  Mrv1652309052203392D          

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    5.7001    0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.1499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4675   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  1  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H52O3/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-16-26(31)29(32)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h18-26,30-32H,7-17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,26-,27-,28-,29+/m1/s1

> <INCHI_KEY>
VGSSUFQMXBFFTM-METNKUIYSA-N

> <FORMULA>
C29H52O3

> <MOLECULAR_WEIGHT>
448.732

> <EXACT_MASS>
448.391645534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
56.317618324870956

> <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)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,7,8-triol

> <JCHEM_LOGP>
5.943058895333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <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>
131.76209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7R,8R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,7,8-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      15.479  -0.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.939  -0.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.169  -1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.629  -1.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.859  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.549  -4.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.549  -1.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.018  -1.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.697  -0.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.031   0.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.351   2.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.207   3.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.527   4.794   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.383   5.824   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.992   5.270   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.847   6.300   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.312   6.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.776   7.252   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.097   8.758   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.921   6.222   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.601   4.715   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.136   4.239   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.281   3.209   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.816   2.733   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.960   1.702   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.640   0.196   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.176  -0.280   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.206  -1.424   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.939  -3.020   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.479  -3.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.169  -4.354   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   11    8   29                                             
CONECT   29   28                                                            
CONECT   30    3   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
5alpha,6beta-Dihydroxysitosterol	ChEBI
Sitostanetriol	ChEBI
5a,6b-Dihydroxysitosterol	Generator
5Α,6β-dihydroxysitosterol	Generator
Stigmastane-3b,5a,6b-triol	Generator
Stigmastane-3β,5α,6β-triol	Generator
5 alpha-Stigmastane-3 beta,5,6 beta-triol 3-monobenzoate	MeSH
5 alpha-Stigmastane-3 beta,5,6 beta-triol 3-monobenzoate, (3beta)-isomer	MeSH

Chemical Formula

C₂₉H₅₂O₃

Average Mass

448.7320 Da

Monoisotopic Mass

448.39165 Da

IUPAC Name

(1S,2R,5S,7R,8R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,7,8-triol

Traditional Name

(1S,2R,5S,7R,8R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,7,8-triol

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H52O3/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-16-26(31)29(32)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h18-26,30-32H,7-17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,26-,27-,28-,29+/m1/s1

InChI Key

VGSSUFQMXBFFTM-METNKUIYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis mellifera	LOTUS Database	35616633
Breynia fruticosa	LOTUS Database	35616633
Machilus zuihoensis	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

Substituents

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
3-hydroxysteroid
3-beta-hydroxysteroid
6-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:67593 )
triol (CHEBI:67593 )
5alpha-hydroxy steroid (CHEBI:67593 )
6beta-hydroxy steroid (CHEBI:67593 )

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	5.94	ChemAxon
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	6	ChemAxon
Refractivity	131.76 m³·mol⁻¹	ChemAxon
Polarizability	56.32 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2300310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3036251

PDB ID

Not Available

ChEBI ID

67593

Good Scents ID

Not Available

References

General References

Chang KC, Duh CY, Chen IS, Tsai IL: A cytotoxic butenolide, two new dolabellane diterpenoids, a chroman and a benzoquinol derivative formosan Casearia membranacea. Planta Med. 2003 Jul;69(7):667-72. doi: 10.1055/s-2003-41120. [PubMed:12898426 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol (NP0205697)

MOL for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

3D MOL for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

3D SDF for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

3D-SDF for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

PDB for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

3D PDB for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

SMILES for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

INCHI for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

Structure for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)

3D Structure for NP0205697 ((1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol)