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Showing NP-Card for 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol (NP0334340)

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Record Information
Version2.0
Created at2024-09-09 23:14:18 UTC
Updated at2024-09-09 23:14:19 UTC
NP-MRD IDNP0334340
Secondary Accession NumbersNone
Natural Product Identification
Common Name4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol
Description4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-ol belongs to ergosterols and derivatives class of compounds. Those are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. 4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-ol can be found in a number of food items such as loganberry, cardamom, pineapple, and sweet cherry, which makes 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol a potential biomarker for the consumption of these food products.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)


  Mrv2104 05242323522D          

 30 33  0  0  0  0            999 V2000
    0.0089    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    3.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    3.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3636    1.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4185    2.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9005    3.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9427    1.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7496    1.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3642    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1712    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0935    3.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5145    3.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2866    3.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7075    3.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8115    2.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3906    1.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0046    2.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5837    1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6456    2.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0665    3.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316    2.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4525    2.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8735    3.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  2  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 20  1  0  0  0  0
 10 11  1  0  0  0  0
 10 22  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  1  0  0  0  0
 13 25  2  0  0  0  0
 14 16  1  0  0  0  0
 14 26  1  0  0  0  0
 15 17  1  0  0  0  0
 15 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 21 27  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
M  END
Download

3D MOL for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)

Download
3D SDF for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)

  Mrv2104 05242323522D          

 30 33  0  0  0  0            999 V2000
    0.0089    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    3.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    3.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3636    1.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4185    2.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9005    3.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9427    1.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7496    1.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3642    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1712    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0935    3.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5145    3.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2866    3.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7075    3.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8115    2.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3906    1.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0046    2.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5837    1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6456    2.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0665    3.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316    2.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4525    2.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8735    3.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  2  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 20  1  0  0  0  0
 10 11  1  0  0  0  0
 10 22  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  1  0  0  0  0
 13 25  2  0  0  0  0
 14 16  1  0  0  0  0
 14 26  1  0  0  0  0
 15 17  1  0  0  0  0
 15 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 21 27  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CCC(C)C1CC=C2C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3

> <INCHI_KEY>
HLAWVOWADPNAGN-UHFFFAOYNA-N

> <FORMULA>
C29H46O

> <MOLECULAR_WEIGHT>
410.686

> <EXACT_MASS>
410.354866101

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.57595130003121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1H,2H,4H,5H,5aH,6H,7H,8H,9H,9aH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

> <JCHEM_LOGP>
6.967997836333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.957245922127218

> <JCHEM_PKA_STRONGEST_BASIC>
-1.067900633661555

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
129.99759999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1H,2H,4H,5H,5aH,6H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthren-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)
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PDB for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0       0.017   3.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.317   6.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.651   2.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.652   6.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -17.479   3.409   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.248   5.447   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.881   6.522   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.984   4.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.318   3.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.960   2.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.466   2.768   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.146   2.259   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.653   1.939   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -11.375   6.201   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -15.894   7.162   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.868   5.881   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.387   6.842   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.317   4.560   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.651   3.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.652   4.560   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -16.448   4.553   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -11.929   3.592   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.986   3.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.942   4.233   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.423   3.272   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.405   5.057   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.924   6.018   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.392   4.417   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.911   5.377   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -18.430   6.338   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   19                                                       
CONECT    9    8   20                                                       
CONECT   10   11   22                                                       
CONECT   11   10   24                                                       
CONECT   12   13   23                                                       
CONECT   13   12   25                                                       
CONECT   14   16   26                                                       
CONECT   15   17   27                                                       
CONECT   16   14   28                                                       
CONECT   17   15   29                                                       
CONECT   18    1    2   19                                                  
CONECT   19    3    8   18                                                  
CONECT   20    4    9   23                                                  
CONECT   21    5   24   27                                                  
CONECT   22   10   25   26                                                  
CONECT   23   12   20   28                                                  
CONECT   24   11   21   29                                                  
CONECT   25   13   22   28                                                  
CONECT   26   14   22   29                                                  
CONECT   27   15   21   30                                                  
CONECT   28    6   16   23   25                                             
CONECT   29    7   17   24   26                                             
CONECT   30   27                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

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3D PDB for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)
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SMILES for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)
CC(C)C(=C)CCC(C)C1CC=C2C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3
Download
INCHI for NP0334340 (4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol)
InChI=1/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3
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View in JSmol
Synonyms
ValueSource
(3b,4a,5a)-4-Methylergosta-8,14,24(28)-trien-3-olGenerator
(3Β,4α,5α)-4-methylergosta-8,14,24(28)-trien-3-olGenerator
Chemical FormulaC29H46O
Average Mass410.6860 Da
Monoisotopic Mass410.35487 Da
IUPAC Name6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1H,2H,4H,5H,5aH,6H,7H,8H,9H,9aH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
Traditional Name6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1H,2H,4H,5H,5aH,6H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthren-7-ol
CAS Registry NumberNot Available
SMILES
CC(C)C(=C)CCC(C)C1CC=C2C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3
InChI Identifier
InChI=1/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3
InChI KeyHLAWVOWADPNAGN-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a  derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassErgostane steroids  
Direct ParentErgosterols and derivatives  
Alternative Parents
Substituents
  • Ergosterol-skeleton
    • 

  • Hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.97ChemAxon
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130 m³·mol⁻¹ChemAxon
Polarizability52.58 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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References
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