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Showing NP-Card for 25-Dehydrofungisterol (NP0049184)

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Record Information
Version2.0
Created at2022-03-17 21:08:26 UTC
Updated at2022-03-17 21:08:26 UTC
NP-MRD IDNP0049184
Secondary Accession NumbersNone
Natural Product Identification
Common Name25-Dehydrofungisterol
Description25-Dehydrofungisterol 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. 25-Dehydrofungisterol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 25-dehydrofungisterol has been detected, but not quantified in, several different foods, such as cucumbers, fruits, japanese pumpkins, muskmelons, and watermelons. 25-Dehydrofungisterol is found in Cucurbita maxima and Lagenaria siceraria. This could make 25-dehydrofungisterol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049184 (25-Dehydrofungisterol)


  Mrv0541 05061310342D          

 29 32  0  0  0  0            999 V2000
    6.0409   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -2.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -0.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107    0.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678    0.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8608    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825   -2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616   -1.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755   -2.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7454   -1.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -1.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586   -0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4483   -0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136   -1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206   -1.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -1.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  2  0  0  0  0
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 19 18  1  0  0  0  0
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 21 17  1  0  0  0  0
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 23 10  2  0  0  0  0
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 28  6  1  0  0  0  0
 28 16  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  1  0  0  0  0
 29 22  1  0  0  0  0
M  END
Download

3D MOL for NP0049184 (25-Dehydrofungisterol)

Download
3D SDF for NP0049184 (25-Dehydrofungisterol)

  Mrv0541 05061310342D          

 29 32  0  0  0  0            999 V2000
    6.0409   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -2.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -0.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107    0.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678    0.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8608    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825   -2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616   -1.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755   -2.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7454   -1.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -1.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586   -0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4483   -0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136   -1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206   -1.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -1.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  2  0  0  0  0
 18  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  7  1  0  0  0  0
 19 18  1  0  0  0  0
 20  4  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  1  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  2  0  0  0  0
 24 11  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 25 23  1  0  0  0  0
 26 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  1  0  0  0  0
 28  6  1  0  0  0  0
 28 16  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  1  0  0  0  0
 29 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049184

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(C)C(C)=C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h10,19-22,24-26,29H,1,7-9,11-17H2,2-6H3

> <INCHI_KEY>
ALAYAXMTAIVXMW-UHFFFAOYSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.26364600865401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5,6-dimethylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.01

> <JCHEM_LOGP>
7.052262316

> <ALOGPS_LOGS>
-6.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.361777845540015

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3283583703607977

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
124.94259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(5,6-dimethylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0049184 (25-Dehydrofungisterol)
Download
PDB for NP0049184 (25-Dehydrofungisterol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.276  -1.171   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.943  -3.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.609   0.369   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.608  -3.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.621  -3.902   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.012  -2.827   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.942  -1.171   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.206  -0.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.700   0.172   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.113   0.361   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.607   0.681   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.634  -4.542   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.115  -3.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.128  -4.222   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.391  -3.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.189  -1.933   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.943  -1.941   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.609  -1.171   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.608  -1.941   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.682  -1.613   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.664  -3.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.669  -0.973   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.274  -1.171   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.837  -0.652   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.145  -2.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.652  -2.757   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.867  -1.797   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.171  -3.718   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7    8   19                                                       
CONECT    8    7   20                                                       
CONECT    9   10   21                                                       
CONECT   10    9   23                                                       
CONECT   11   12   24                                                       
CONECT   12   11   25                                                       
CONECT   13   15   22                                                       
CONECT   14   16   26                                                       
CONECT   15   13   27                                                       
CONECT   16   14   28                                                       
CONECT   17   21   22                                                       
CONECT   18    1    2   19                                                  
CONECT   19    3    7   18                                                  
CONECT   20    4    8   24                                                  
CONECT   21    9   17   27                                                  
CONECT   22   13   17   29                                                  
CONECT   23   10   25   26                                                  
CONECT   24   11   20   28                                                  
CONECT   25   12   23   28                                                  
CONECT   26   14   23   27                                                  
CONECT   27    5   15   21   26                                             
CONECT   28    6   16   24   25                                             
CONECT   29   22                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

Download
3D PDB for NP0049184 (25-Dehydrofungisterol)
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SMILES for NP0049184 (25-Dehydrofungisterol)
CC(CCC(C)C(C)=C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C
Download
INCHI for NP0049184 (25-Dehydrofungisterol)
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h10,19-22,24-26,29H,1,7-9,11-17H2,2-6H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC28H46O
Average Mass398.6642 Da
Monoisotopic Mass398.35487 Da
IUPAC Name14-(5,6-dimethylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Name14-(5,6-dimethylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
CAS Registry Number95043-18-8
SMILES
CC(CCC(C)C(C)=C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h10,19-22,24-26,29H,1,7-9,11-17H2,2-6H3
InChI KeyALAYAXMTAIVXMW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrullus lanatusFooDB
Cucumis meloFooDB
Cucumis sativus L.FooDB
Cucurbita maximaPlant
Lagenaria sicerariaLOTUS Database
Chemical Taxonomy
Description 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 ParentsNot Available
SubstituentsNot Available
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
logP7.01ALOGPS
logP7.05ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.94 m³·mol⁻¹ChemAxon
Polarizability50.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038655  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018051  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74051264  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References