NP-MRD: Showing NP-Card for (3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0294129)

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Record Information

Version

2.0

Created at

2022-09-10 02:31:04 UTC

Updated at

2022-09-10 02:31:05 UTC

NP-MRD ID

NP0294129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

4-Alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol , also known as 4-methylcholest-7-en-3-ol or methostenol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. In this pathway, 4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol is enzymatically converted to 4-alpha-methyl-5-alpha-cholest-7-en-3-one via the enzyme 3-keto-steroid reductase (EC: 1.1.1.270) And the cofactor NADP(+). 4-Alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol is involved in the steroid biosynthesis pathway. This pathway is carried out in different ways in animals than in many other organisms, making the pathway a common target for antibiotics and other anti-infective drugs. 4-Alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). This enzyme is responsible for the reduction of the keto group on the C-3 of sterols. 4-Alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol exists in all eukaryotes, ranging from yeast to humans. Steroid biosynthesis is an anabolic metabolic pathway that produces steroids from simple precursors. In addition, steroid metabolism in humans is the target of cholesterol-lowering drugs such as statins. Outside of the human body, 4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol has been detected, but not quantified in, several different foods, such as garden tomato (var.), Potato, oats, pepper (c. Annuum), and alcoholic beverages. (3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Gymnodinium catenatum. This could make 4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304202021192D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304202021192D          

 32 35  0  0  1  0            999 V2000
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   11.1093   -5.3765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5252   -5.4655    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3766   -6.7131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6554   -7.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  1  1  0  0  0  0
 13  1  1  0  0  0  0
  1 22  1  1  0  0  0
 10  2  1  0  0  0  0
  7  2  1  0  0  0  0
  2 23  1  1  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
 14  3  1  0  0  0  0
  6  4  1  0  0  0  0
 15  4  1  0  0  0  0
 11  5  1  0  0  0  0
 16  5  1  0  0  0  0
 17  6  2  0  0  0  0
 12  7  1  0  0  0  0
 18  7  1  0  0  0  0
 12  8  1  0  0  0  0
  9  8  1  0  0  0  0
 19  9  1  0  0  0  0
 14 10  1  0  0  0  0
 20 11  1  0  0  0  0
 12 26  1  6  0  0  0
 21 13  1  0  0  0  0
 18 15  1  0  0  0  0
 17 16  1  0  0  0  0
 24 19  1  0  0  0  0
 21 20  1  0  0  0  0
 20 25  1  1  0  0  0
 27 24  1  0  0  0  0
 24 28  1  0  0  0  0
  3 29  1  6  0  0  0
  4 30  1  6  0  0  0
  5 31  1  6  0  0  0
 11 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0294129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-26,29H,7-9,11-17H2,1-6H3/t19-,20+,22?,23+,24+,25+,26+,27-,28+/m1/s1

> <INCHI_KEY>
LMYZQUNLYGJIHI-DOQVYVCQSA-N

> <FORMULA>
C28H48O

> <MOLECULAR_WEIGHT>
400.6801

> <EXACT_MASS>
400.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
51.94485402734399

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6S,7S,11R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.34

> <JCHEM_LOGP>
7.477861857000003

> <ALOGPS_LOGS>
-7.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.957638198850066

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0677290518229814

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
125.08809999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6S,7S,11R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      19.346  -9.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.341  -7.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.672  -8.593   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.341  -8.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.346 -10.894   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.998  -9.360   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.667  -6.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.994  -3.959   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.320  -4.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.998  -6.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.019 -11.661   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.667  -4.742   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.019  -8.593   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.672  -7.043   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.994  -8.593   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.672 -11.661   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.998 -10.894   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.994  -7.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.646  -3.959   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.677 -10.894   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.677  -9.360   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.346  -7.810   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.341  -5.509   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.071  -4.764   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.335 -11.677   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      23.341  -3.959   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.481  -3.932   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.087  -6.400   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      20.737 -10.036   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      23.380 -10.202   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      19.370 -12.531   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      18.023 -13.306   0.000  0.00  0.00           C+0
CONECT    1    3    5   13   22                                             
CONECT    2   10    7   23    4                                             
CONECT    3    1    6   14   29                                             
CONECT    4    2    6   15   30                                             
CONECT    5    1   11   16   31                                             
CONECT    6    3    4   17                                                  
CONECT    7    2   12   18                                                  
CONECT    8   12    9                                                       
CONECT    9    8   19                                                       
CONECT   10    2   14                                                       
CONECT   11    5   20   32                                                  
CONECT   12    7    8   26                                                  
CONECT   13    1   21                                                       
CONECT   14    3   10                                                       
CONECT   15    4   18                                                       
CONECT   16    5   17                                                       
CONECT   17    6   16                                                       
CONECT   18    7   15                                                       
CONECT   19    9   24                                                       
CONECT   20   11   21   25                                                  
CONECT   21   13   20                                                       
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24   19   27   28                                                  
CONECT   25   20                                                            
CONECT   26   12                                                            
CONECT   27   24                                                            
CONECT   28   24                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32   11                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
4-a-Methyl-5-a-cholest-7-en-3-b-ol	Generator
4-Α-methyl-5-α-cholest-7-en-3-β-ol	Generator
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol	HMDB
4-Methylcholest-7-en-3-ol	HMDB
4alpha-Methyl-5alpha-cholest-7-en-3beta-ol	HMDB
Lophenol	HMDB
Methostenol	HMDB
4-Methylcholest-7-en-3-ol, (3beta,4alpha)-isomer	HMDB

Chemical Formula

C₂₈H₄₈O

Average Mass

400.6801 Da

Monoisotopic Mass

400.37052 Da

IUPAC Name

(1R,2S,5S,6S,7S,11R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

Traditional Name

(1R,2S,5S,6S,7S,11R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-26,29H,7-9,11-17H2,1-6H3/t19-,20+,22?,23+,24+,25+,26+,27-,28+/m1/s1

InChI Key

LMYZQUNLYGJIHI-DOQVYVCQSA-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
Gymnodinium catenatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols 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	7.34	ALOGPS
logP	7.48	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-1.1	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	125.09 m³·mol⁻¹	ChemAxon
Polarizability	51.94 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

HMDB0011605

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50990062

PDB ID

Not Available

ChEBI ID

18378

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0294129)

MOL for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0294129 ((3ar,5as,6s,7s,9as,9br,11ar)-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)