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Showing NP-Card for 24-ethylidenelophenol (NP0336510)

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Record Information
Version2.0
Created at2024-09-11 06:36:27 UTC
Updated at2024-09-11 06:36:27 UTC
NP-MRD IDNP0336510
Secondary Accession NumbersNone
Natural Product Identification
Common Name24-ethylidenelophenol
Description24-Ethylidenelophenol 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. 24-ethylidenelophenol was first documented in 1993 (PMID: 8505296). Based on a literature review very few articles have been published on 24-ethylidenelophenol (PMID: 14653780).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336510 (24-ethylidenelophenol)


  Mrv2104 05262309082D          

 31 34  0  0  0  0            999 V2000
   -2.0761   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906   -1.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906   -2.2380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0761   -2.6505    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3617   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617   -1.4130    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6472   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -2.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673   -1.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -0.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -0.1755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7817   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -0.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051   -2.6505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617   -0.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817    0.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2107    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    1.0620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9251    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    2.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3540    2.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  2  0  0  0  0
 29 30  1  0  0  0  0
  4 31  1  6  0  0  0
M  END
Download

3D MOL for NP0336510 (24-ethylidenelophenol)

Download
3D SDF for NP0336510 (24-ethylidenelophenol)

  Mrv2104 05262309082D          

 31 34  0  0  0  0            999 V2000
   -2.0761   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906   -1.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906   -2.2380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0761   -2.6505    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3617   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617   -1.4130    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6472   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -2.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673   -1.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -0.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -0.1755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7817   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -0.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051   -2.6505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617   -0.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817    0.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2107    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    1.0620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9251    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817    1.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    2.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3540    2.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  2  0  0  0  0
 29 30  1  0  0  0  0
  4 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0336510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\CC[C@@H](C)C1CCC2C3=CCC4[C@H](C)[C@@H](O)CC[C@]4(C)C3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8-/t20-,21+,24?,25?,26?,27?,28+,29-,30+/s2

> <INCHI_KEY>
LPZCCMIISIBREI-QCRCFHAJNA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.60235841017136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,7S,9aS,11aR)-6,9a,11a-trimethyl-1-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

> <JCHEM_LOGP>
7.803870137000004

> <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>
135.0877

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S,7S,9aS,11aR)-1-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-6,9a,11a-trimethyl-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0336510 (24-ethylidenelophenol)
Download
PDB for NP0336510 (24-ethylidenelophenol)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.875  -1.868   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.209  -2.638   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.209  -4.178   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.875  -4.948   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.542  -4.178   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.542  -2.638   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.208  -1.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.208  -4.948   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.126  -4.178   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.126  -2.638   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.126   0.442   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.208  -0.328   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.793   0.442   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.459  -0.328   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.459  -1.868   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.126  -1.868   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.126  -0.328   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.543  -4.948   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.542  -1.098   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.459   1.212   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.127   2.752   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.793   1.982   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.460   1.982   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.794   2.752   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.128   1.982   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.461   2.752   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.128   0.442   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.459   2.752   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.794   4.292   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.127   5.062   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.875  -6.488   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   13   21   28                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
CONECT   31    4                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0336510 (24-ethylidenelophenol)
Download
SMILES for NP0336510 (24-ethylidenelophenol)
C\C=C(\CC[C@@H](C)C1CCC2C3=CCC4[C@H](C)[C@@H](O)CC[C@]4(C)C3CC[C@]12C)C(C)C
Download
INCHI for NP0336510 (24-ethylidenelophenol)
InChI=1/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8-/t20-,21+,24?,25?,26?,27?,28+,29-,30+/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC30H50O
Average Mass426.7290 Da
Monoisotopic Mass426.38617 Da
IUPAC Name(6S,7S,9aS,11aR)-6,9a,11a-trimethyl-1-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
Traditional Name(6S,7S,9aS,11aR)-1-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-6,9a,11a-trimethyl-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-7-ol
CAS Registry NumberNot Available
SMILES
C\C=C(\CC[C@@H](C)C1CCC2C3=CCC4[C@H](C)[C@@H](O)CC[C@]4(C)C3CC[C@]12C)C(C)C
InChI Identifier
InChI=1/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8-/t20-,21+,24?,25?,26?,27?,28+,29-,30+/s2
InChI KeyLPZCCMIISIBREI-QCRCFHAJNA-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 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassStigmastanes and derivatives  
Direct ParentStigmastanes and derivatives  
Alternative Parents
Substituents
  • Triterpenoid
    • 

  • Stigmastane-skeleton
    • 

  • 3-beta-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • 3-hydroxy-delta-7-steroid
    • 

  • Delta-7-steroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP7.8ChemAxon
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
Refractivity135.09 m³·mol⁻¹ChemAxon
Polarizability54.6 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 IDC00007321  
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
Good Scents IDNot Available
References
General References
  1. Pascal S, Taton M, Rahier A: Plant sterol biosynthesis. Identification and characterization of two distinct microsomal oxidative enzymatic systems involved in sterol C4-demethylation. J Biol Chem. 1993 Jun 5;268(16):11639-54. [PubMed:8505296  ] 
  2. Darnet S, Rahier A: Plant sterol biosynthesis: identification of two distinct families of sterol 4alpha-methyl oxidases. Biochem J. 2004 Mar 15;378(Pt 3):889-98. doi: 10.1042/BJ20031572. [PubMed:14653780  ]