NP-MRD: Showing NP-Card for (6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol (NP0325092)

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Record Information

Version

2.0

Created at

2022-09-12 05:34:54 UTC

Updated at

2022-09-12 05:34:54 UTC

NP-MRD ID

NP0325092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol

Description

Stigmastadienol 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. (6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol is found in Hippophae rhamnoides. (6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol was first documented in 2008 (PMID: 26049228). Based on a literature review a significant number of articles have been published on Stigmastadienol (PMID: 28964371) (PMID: 35327258) (PMID: 32549600) (PMID: 30552561) (PMID: 29494522) (PMID: 26593597).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207342D          

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M  END

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 16 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0325092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC=C(C=CO)C(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-20(2)22(16-19-30)10-9-21(3)25-13-14-26-24-12-11-23-8-6-7-17-28(23,4)27(24)15-18-29(25,26)5/h10,16,19-21,23-27,30H,6-9,11-15,17-18H2,1-5H3/t21-,23?,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
DSOKBBPJHVYCBQ-KZSQEHGRSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.563709677024846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-(propan-2-yl)hepta-1,3-dien-1-ol

> <JCHEM_LOGP>
8.336794861666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.764787092554604

> <JCHEM_PKA_STRONGEST_BASIC>
-5.526082125716617

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.11839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-isopropylhepta-1,3-dien-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.685  -7.663   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.630  -8.878   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   16   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   15   12   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O

Average Mass

412.7020 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-(propan-2-yl)hepta-1,3-dien-1-ol

Traditional Name

(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-isopropylhepta-1,3-dien-1-ol

CAS Registry Number

Not Available

SMILES

C[C@H](CC=C(C=CO)C(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H48O/c1-20(2)22(16-19-30)10-9-21(3)25-13-14-26-24-12-11-23-8-6-7-17-28(23,4)27(24)15-18-29(25,26)5/h10,16,19-21,23-27,30H,6-9,11-15,17-18H2,1-5H3/t21-,23?,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

DSOKBBPJHVYCBQ-KZSQEHGRSA-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
Hippophae rhamnoides	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

Triterpenoid
Stigmastane-skeleton
Enol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	8.34	ChemAxon
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.12 m³·mol⁻¹	ChemAxon
Polarizability	52.56 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00061284

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

129636643

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ammar S, Kelebek H, Zribi A, Abichou M, Selli S, Bouaziz M: LC-DAD/ESI-MS/MS characterization of phenolic constituents in Tunisian extra-virgin olive oils: Effect of olive leaves addition on chemical composition. Food Res Int. 2017 Oct;100(Pt 3):477-485. doi: 10.1016/j.foodres.2016.11.001. Epub 2016 Nov 5. [PubMed:28964371 ]
Balbino S, Vincek D, Trtanj I, Egredija D, Gajdos-Kljusuric J, Kraljic K, Obranovic M, Skevin D: Assessment of Pumpkin Seed Oil Adulteration Supported by Multivariate Analysis: Comparison of GC-MS, Colourimetry and NIR Spectroscopy Data. Foods. 2022 Mar 14;11(6):835. doi: 10.3390/foods11060835. [PubMed:35327258 ]
Duman E, Ozcan MM: The influence of industrial refining stages on the physico-chemical properties, fatty acid composition and sterol contents in hazelnut oil. J Food Sci Technol. 2020 Jul;57(7):2501-2506. doi: 10.1007/s13197-020-04285-w. Epub 2020 Feb 3. [PubMed:32549600 ]
Gornas P, Czubinski J, Rudzinska M, Grygier A, Ying Q, Chakradhari S, Sahu PK, Misina I, Urvaka E, Patel KS: Selected Uncommon Legumes as a Source of Essential Fatty Acids, Tocopherols, Tocotrienols, Sterols, Carotenoids, and Squalene. Plant Foods Hum Nutr. 2019 Mar;74(1):91-98. doi: 10.1007/s11130-018-0706-x. [PubMed:30552561 ]
Montesano D, Blasi F, Simonetti MS, Santini A, Cossignani L: Chemical and Nutritional Characterization of Seed Oil from Cucurbita maxima L. (var. Berrettina) Pumpkin. Foods. 2018 Mar 1;7(3):30. doi: 10.3390/foods7030030. [PubMed:29494522 ]
Soltana H, Tekaya M, Amri Z, El-Gharbi S, Nakbi A, Harzallah A, Mechri B, Hammami M: Characterization of fig achenes' oil of Ficus carica grown in Tunisia. Food Chem. 2016 Apr 1;196:1125-30. doi: 10.1016/j.foodchem.2015.10.053. Epub 2015 Oct 22. [PubMed:26593597 ]
Kim JA, Son JH, Song SB, Yang SY, Kim YH: Sterols isolated from seeds of Panax ginseng and their antiinflammatory activities. Pharmacogn Mag. 2013 Apr;9(34):182-5. doi: 10.4103/0973-1296.111288. [PubMed:23772116 ]
Lukic M, Lukic I, Krapac M, Sladonja B, Pilizota V: Sterols and triterpene diols in olive oil as indicators of variety and degree of ripening. Food Chem. 2013 Jan 1;136(1):251-8. doi: 10.1016/j.foodchem.2012.08.005. Epub 2012 Aug 11. [PubMed:23017420 ]
Shin EC, Pegg RB, Phillips RD, Eitenmiller RR: Commercial peanut (Arachis hypogaea L.) cultivars in the United States: phytosterol composition. J Agric Food Chem. 2010 Aug 25;58(16):9137-46. doi: 10.1021/jf102150n. Epub 2010 Aug 2. [PubMed:20677801 ]
Temime SB, Manai H, Methenni K, Baccouri B, Abaza L, Daoud D, Casas JS, Bueno EO, Zarrouk M: Sterolic composition of Chetoui virgin olive oil: Influence of geographical origin. Food Chem. 2008 Sep 15;110(2):368-74. doi: 10.1016/j.foodchem.2008.02.012. Epub 2008 Feb 14. [PubMed:26049228 ]
LOTUS database [Link]

Showing NP-Card for (6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol (NP0325092)

MOL for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

3D MOL for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

3D SDF for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

3D-SDF for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

PDB for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

3D PDB for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

SMILES for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

INCHI for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

Structure for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)

3D Structure for NP0325092 ((6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol)