NP-MRD: Showing NP-Card for 3beta,6beta-stigmast-4-en-3,6-diol (NP0085712)

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Record Information

Version

2.0

Created at

2022-04-29 06:11:29 UTC

Updated at

2022-04-29 06:11:29 UTC

NP-MRD ID

NP0085712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta,6beta-stigmast-4-en-3,6-diol

Description

Stigmast-4-ene-3,6-diol 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,6beta-stigmast-4-en-3,6-diol is found in Erythrophleum fordii, Larix kaempferi and Pileostegia viburnoides var. glabrescens. 3beta,6beta-stigmast-4-en-3,6-diol was first documented in 2021 (PMID: 34834844). Based on a literature review very few articles have been published on Stigmast-4-ene-3,6-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208112D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292208112D          

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   -1.7314    0.8511    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  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  1  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  3 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])C[C@@H](O)C4=C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h16,18-25,27,30-31H,7-15,17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,27-,28-,29-/m1/s1

> <INCHI_KEY>
OOUCIUZOGLWLAN-NDDUEHJASA-N

> <FORMULA>
C29H50O2

> <MOLECULAR_WEIGHT>
430.717

> <EXACT_MASS>
430.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.95038818354929

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,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}]heptadec-6-ene-5,8-diol

> <ALOGPS_LOGP>
6.23

> <JCHEM_LOGP>
6.769573185000002

> <ALOGPS_LOGS>
-6.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.067620151441787

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.40200027230874

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8544933827064227

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
131.12759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,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}]heptadec-6-ene-5,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.767   2.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.088   0.558   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.408  -0.948   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.263  -1.979   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.583  -3.485   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.201  -1.503   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.521   0.004   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       0.842   1.510   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      -0.623   1.034   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -0.943  -0.472   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -0.303   2.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.162   3.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.306   1.986   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.782   3.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.986   0.480   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       1.825  -1.052   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       3.320  -0.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.464   0.740   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.838   2.147   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       5.376   2.066   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.838   4.814   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.148   3.481   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.918   4.814   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.458   4.814   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.228   6.148   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.768   6.148   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.228   3.481   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.768   3.481   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.458   2.147   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.872  -1.424   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.017  -0.394   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.481  -0.869   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.697   1.113   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.232   1.589   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   35                                             
CONECT    3    2    4   31                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    3   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₅₀O₂

Average Mass

430.7170 Da

Monoisotopic Mass

430.38108 Da

IUPAC Name

(1S,2R,5S,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}]heptadec-6-ene-5,8-diol

Traditional Name

(1S,2R,5S,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}]heptadec-6-ene-5,8-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])C[C@@H](O)C4=C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

InChI Identifier

InChI=1S/C29H50O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h16,18-25,27,30-31H,7-15,17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,27-,28-,29-/m1/s1

InChI Key

OOUCIUZOGLWLAN-NDDUEHJASA-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
Erythrophleum fordii	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Pileostegia viburnoides var. glabrescens	Plant	KNApSAcK

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
Stigmastane-skeleton
Triterpenoid
3-hydroxysteroid
Hydroxysteroid
6-hydroxysteroid
3-hydroxy-delta-4-steroid
3-beta-hydroxysteroid
Delta-4-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

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	6.23	ALOGPS
logP	6.77	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	14.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.13 m³·mol⁻¹	ChemAxon
Polarizability	54.95 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

C00055678

Chemspider ID

8726001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10550610

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee D, Lee SR, Park BJ, Song JH, Kim JK, Ko Y, Kang KS, Kim KH: Identification of Renoprotective Phytosterols from Mulberry (Morus alba) Fruit against Cisplatin-Induced Cytotoxicity in LLC-PK1 Kidney Cells. Plants (Basel). 2021 Nov 17;10(11). pii: plants10112481. doi: 10.3390/plants10112481. [PubMed:34834844 ]

Showing NP-Card for 3beta,6beta-stigmast-4-en-3,6-diol (NP0085712)

MOL for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

3D MOL for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

3D SDF for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

3D-SDF for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

PDB for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

3D PDB for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

SMILES for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

INCHI for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

Structure for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)

3D Structure for NP0085712 (3beta,6beta-stigmast-4-en-3,6-diol)