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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:24:16 UTC

Update Date

2022-03-07 02:55:38 UTC

HMDB ID

HMDB0038120

Secondary Accession Numbers

HMDB38120

Metabolite Identification

Common Name

Ovalicin

Description

Ovalicin belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Based on a literature review a significant number of articles have been published on Ovalicin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0038120
     RDKit          3D
Ovalicin
 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.4473   -2.7402   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087   -1.7297    0.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987   -0.6393    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.3158    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521   -1.1718    1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2382    0.9880    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.0856   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938    1.5952   -0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    1.3501   -2.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    2.3940   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4011    0.6294    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    1.1614    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0539    0.4560    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051   -0.4659    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    1.7698    0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    0.9569   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.4377   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    0.6150   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9200   -0.4143    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574   -1.8023   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8740   -0.1475    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672   -3.0458   -0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822   -2.2883   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -3.6033    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -0.8496   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8736    1.2204    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    0.8509   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078    2.8437   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    2.6127    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343    1.7410   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317    0.4538   -2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689    0.3664    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -0.7260    2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    0.0207    1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -1.3990    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.3718   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2591   -0.5738   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936    1.0817   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3197    1.6161    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8789   -2.1057   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -1.8588   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2436   -2.5078    0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070    0.5233    2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7730    0.3304    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.0868    2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 11  3  1  0
 16 13  1  0
 10  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END


  Mrv0541 02241220062D          

 21 23  0  0  0  0            999 V2000
   -2.5003   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3595    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3595    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554    0.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991    0.9184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3595   -1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -2.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    2.2686    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 17  2  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038120

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C(=O)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O5/c1-10(2)5-6-12-14(3,21-12)16(18)13(19-4)11(17)7-8-15(16)9-20-15/h5,12-13,18H,6-9H2,1-4H3

> <INCHI_KEY>
NESRXFGQJARQNM-UHFFFAOYSA-N

> <FORMULA>
C16H24O5

> <MOLECULAR_WEIGHT>
296.3588

> <EXACT_MASS>
296.162373878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.525411250548302

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.2611042726666666

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.883374979118631

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.50277529161838

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7462992967283735

> <JCHEM_POLAR_SURFACE_AREA>
71.59

> <JCHEM_REFRACTIVITY>
76.70150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038120
     RDKit          3D
Ovalicin
 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.4473   -2.7402   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087   -1.7297    0.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987   -0.6393    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.3158    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521   -1.1718    1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2382    0.9880    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.0856   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938    1.5952   -0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    1.3501   -2.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    2.3940   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4011    0.6294    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    1.1614    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0539    0.4560    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051   -0.4659    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    1.7698    0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    0.9569   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.4377   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    0.6150   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9200   -0.4143    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574   -1.8023   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8740   -0.1475    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672   -3.0458   -0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822   -2.2883   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -3.6033    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -0.8496   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8736    1.2204    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    0.8509   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078    2.8437   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    2.6127    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343    1.7410   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317    0.4538   -2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689    0.3664    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -0.7260    2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    0.0207    1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -1.3990    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.3718   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2591   -0.5738   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936    1.0817   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3197    1.6161    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8789   -2.1057   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -1.8588   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2436   -2.5078    0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070    0.5233    2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7730    0.3304    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.0868    2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 11  3  1  0
 16 13  1  0
 10  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.667  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.667  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.335  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.006  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.006  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.335   0.382   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.671   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.663  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.671   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.663   2.695   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.663   1.206   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.565   1.714   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.105   1.714   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.006   1.155   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.671  -2.695   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.663  -1.925   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.335  -4.235   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.998   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.333   2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.667   1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.333   4.235   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7   14                                             
CONECT    6    1    5   12   13                                             
CONECT    7    5    8    9   11                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   18                                                       
CONECT   11    7    9                                                       
CONECT   12    6   13                                                       
CONECT   13    6   12                                                       
CONECT   14    5                                                            
CONECT   15    4   16                                                       
CONECT   16   15                                                            
CONECT   17    3                                                            
CONECT   18   10   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0038120
HETATM    1  C1  UNL     1      -1.447  -2.740  -0.108  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.709  -1.730   0.814  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.199  -0.639   0.162  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.601  -0.316   0.559  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.252  -1.172   1.120  1.00  0.00           O  
HETATM    6  C4  UNL     1      -4.238   0.988   0.307  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.299   2.086  -0.018  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.994   1.595  -0.645  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.118   1.350  -2.117  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.361   2.394  -1.533  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.401   0.629   0.297  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.731   1.161   1.600  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.054   0.456   0.247  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.705  -0.466   1.285  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.800   1.770   0.307  1.00  0.00           O  
HETATM   16  C11 UNL     1       0.886   0.957  -0.862  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.281   0.438  -1.151  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.230   0.615  -0.041  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.920  -0.414   0.410  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.857  -1.802  -0.089  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.874  -0.147   1.554  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.367  -3.046  -0.660  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.782  -2.288  -0.890  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.926  -3.603   0.337  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.261  -0.850  -0.951  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.874   1.220   1.210  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.946   0.851  -0.537  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.708   2.844  -0.710  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.012   2.613   0.916  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.034   1.741  -2.648  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.632   0.454  -2.495  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.869   0.366   2.183  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.065  -0.726   2.044  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.524   0.021   1.837  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.025  -1.399   0.805  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.430   1.372  -1.772  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.259  -0.574  -1.595  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.694   1.082  -1.992  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.320   1.616   0.367  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.879  -2.106  -0.474  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.625  -1.859  -0.914  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.244  -2.508   0.691  1.00  0.00           H  
HETATM   43  H22 UNL     1       4.307   0.523   2.243  1.00  0.00           H  
HETATM   44  H23 UNL     1       5.773   0.330   1.140  1.00  0.00           H  
HETATM   45  H24 UNL     1       5.140  -1.087   2.064  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4   11   25
CONECT    4    5    5    6
CONECT    6    7   26   27
CONECT    7    8   28   29
CONECT    8    9   10   11
CONECT    9   10   30   31
CONECT   11   12   13
CONECT   12   32
CONECT   13   14   15   16
CONECT   14   33   34   35
CONECT   15   16
CONECT   16   17   36
CONECT   17   18   37   38
CONECT   18   19   19   39
CONECT   19   20   21
CONECT   20   40   41   42
CONECT   21   43   44   45
END

HMDB0038120
     RDKit          3D
Ovalicin
 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.4473   -2.7402   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087   -1.7297    0.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987   -0.6393    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.3158    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521   -1.1718    1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2382    0.9880    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.0856   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938    1.5952   -0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    1.3501   -2.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    2.3940   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4011    0.6294    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    1.1614    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0539    0.4560    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051   -0.4659    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    1.7698    0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    0.9569   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.4377   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    0.6150   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9200   -0.4143    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574   -1.8023   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8740   -0.1475    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672   -3.0458   -0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822   -2.2883   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -3.6033    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -0.8496   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8736    1.2204    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    0.8509   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078    2.8437   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    2.6127    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343    1.7410   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317    0.4538   -2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689    0.3664    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -0.7260    2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    0.0207    1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -1.3990    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.3718   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2591   -0.5738   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936    1.0817   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3197    1.6161    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8789   -2.1057   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -1.8588   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2436   -2.5078    0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070    0.5233    2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7730    0.3304    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.0868    2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 11  3  1  0
 16 13  1  0
 10  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Ovalicin	HMDB
Antibiotic FR 125756	HMDB
Antibiotic SL 1846	HMDB
FR 125756	HMDB
Graphinone	HMDB
OVA	HMDB
SL 1846	HMDB
Ovalicin	MeSH

Chemical Formula

C₁₆H₂₄O₅

Average Molecular Weight

296.3588

Monoisotopic Molecular Weight

296.162373878

IUPAC Name

4-hydroxy-5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

Traditional Name

4-hydroxy-5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

CAS Registry Number

19683-98-8

SMILES

COC1C(=O)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C

InChI Identifier

InChI=1S/C16H24O5/c1-10(2)5-6-12-14(3,21-12)16(18)13(19-4)11(17)7-8-15(16)9-20-15/h5,12-13,18H,6-9H2,1-4H3

InChI Key

NESRXFGQJARQNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038120)
Cytoplasm (HMDB: HMDB0038120)

Cytoplasm (HMDB: HMDB0038120)
Extracellular (HMDB: HMDB0038120)

Source

Exogenous

Food

Food (HMDB: HMDB0038120)

Process

Not Available

Role

Industrial application

Emulsifier (HMDB: HMDB0038120)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038120)

Biological role

Nutrient

Nutrient (HMDB: HMDB0038120)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	93 - 94 °C	Not Available
Boiling Point	447.51 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	87.11 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.136 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.66 g/L	ALOGPS
logP	1.37	ALOGPS
logP	1.26	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	31.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.054	31661259
DarkChem	[M-H]-	167.4	31661259
DeepCCS	[M+H]+	172.451	30932474
DeepCCS	[M-H]-	170.093	30932474
DeepCCS	[M-2H]-	203.227	30932474
DeepCCS	[M+Na]+	178.544	30932474
AllCCS	[M+H]+	170.3	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	176.9	32859911
AllCCS	[M+Na-2H]-	177.2	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ovalicin	COC1C(=O)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	2980.9	Standard polar	33892256
Ovalicin	COC1C(=O)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	1985.0	Standard non polar	33892256
Ovalicin	COC1C(=O)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	2183.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ovalicin,1TMS,isomer #1	COC1C(=O)CCC2(CO2)C1(O[Si](C)(C)C)C1(C)OC1CC=C(C)C	2088.5	Semi standard non polar	33892256
Ovalicin,1TMS,isomer #2	COC1=C(O[Si](C)(C)C)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	2031.7	Semi standard non polar	33892256
Ovalicin,1TMS,isomer #3	COC1C(O[Si](C)(C)C)=CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	2073.8	Semi standard non polar	33892256
Ovalicin,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)CCC2(CO2)C1(O[Si](C)(C)C)C1(C)OC1CC=C(C)C	2111.3	Semi standard non polar	33892256
Ovalicin,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)CCC2(CO2)C1(O[Si](C)(C)C)C1(C)OC1CC=C(C)C	2203.5	Standard non polar	33892256
Ovalicin,2TMS,isomer #2	COC1C(O[Si](C)(C)C)=CCC2(CO2)C1(O[Si](C)(C)C)C1(C)OC1CC=C(C)C	2139.4	Semi standard non polar	33892256
Ovalicin,2TMS,isomer #2	COC1C(O[Si](C)(C)C)=CCC2(CO2)C1(O[Si](C)(C)C)C1(C)OC1CC=C(C)C	2144.7	Standard non polar	33892256
Ovalicin,1TBDMS,isomer #1	COC1C(=O)CCC2(CO2)C1(O[Si](C)(C)C(C)(C)C)C1(C)OC1CC=C(C)C	2299.3	Semi standard non polar	33892256
Ovalicin,1TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	2268.1	Semi standard non polar	33892256
Ovalicin,1TBDMS,isomer #3	COC1C(O[Si](C)(C)C(C)(C)C)=CCC2(CO2)C1(O)C1(C)OC1CC=C(C)C	2327.2	Semi standard non polar	33892256
Ovalicin,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)CCC2(CO2)C1(O[Si](C)(C)C(C)(C)C)C1(C)OC1CC=C(C)C	2548.4	Semi standard non polar	33892256
Ovalicin,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)CCC2(CO2)C1(O[Si](C)(C)C(C)(C)C)C1(C)OC1CC=C(C)C	2594.6	Standard non polar	33892256
Ovalicin,2TBDMS,isomer #2	COC1C(O[Si](C)(C)C(C)(C)C)=CCC2(CO2)C1(O[Si](C)(C)C(C)(C)C)C1(C)OC1CC=C(C)C	2577.0	Semi standard non polar	33892256
Ovalicin,2TBDMS,isomer #2	COC1C(O[Si](C)(C)C(C)(C)C)=CCC2(CO2)C1(O[Si](C)(C)C(C)(C)C)C1(C)OC1CC=C(C)C	2494.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ovalicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00nb-9210000000-329c323563e1be107af9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ovalicin GC-MS (1 TMS) - 70eV, Positive	splash10-0v4s-9142000000-0bf94d77007d949d08b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ovalicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 10V, Positive-QTOF	splash10-0002-2290000000-f820e427b754915d3899	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 20V, Positive-QTOF	splash10-001i-9250000000-468812ea23e5b64a80e4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 40V, Positive-QTOF	splash10-0159-9100000000-6b3446d243425499d069	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 10V, Negative-QTOF	splash10-006t-1960000000-2c6aac846b953c8e3a07	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 20V, Negative-QTOF	splash10-004i-1910000000-983d9cdd8ed9209acebd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 40V, Negative-QTOF	splash10-0a4i-9300000000-6afdfd2df0ed2c6e227e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 10V, Positive-QTOF	splash10-0002-0090000000-96589f7cc0013639dc55	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 20V, Positive-QTOF	splash10-00mk-4690000000-6f6aa2018867973d0c9a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 40V, Positive-QTOF	splash10-015c-9200000000-6b453a3881c2fb353127	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 10V, Negative-QTOF	splash10-0002-0090000000-b313da874220964052e1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 20V, Negative-QTOF	splash10-0002-2890000000-2788eea3fb502d885823	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ovalicin 40V, Negative-QTOF	splash10-0abc-6910000000-8557b607575f31a959c0	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

284995

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1491431

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Methionine aminopeptidase 1

General function:: Involved in aminopeptidase activity
Specific function:: Removes the amino-terminal methionine from nascent proteins. Required for normal progression through the cell cycle
Gene Name:: METAP1
Uniprot ID:: P53582
Molecular weight:: 43214.9

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Methionine aminopeptidase 2

General function:: Involved in aminopeptidase activity
Specific function:: Removes the amino-terminal methionine from nascent proteins. The catalytic activity of human METAP2 toward Met-Val peptides is consistently two orders of magnitude higher than that of METAP1, suggesting that it is responsible for processing proteins containing N-terminal Met-Val and Met-Thr sequences in vivo
Gene Name:: METAP2
Uniprot ID:: P50579
Molecular weight:: 52891.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for Ovalicin (HMDB0038120)

MOL for HMDB0038120 (Ovalicin)

3D MOL for HMDB0038120 (Ovalicin)

3D SDF for HMDB0038120 (Ovalicin)

3D-SDF for HMDB0038120 (Ovalicin)

PDB for HMDB0038120 (Ovalicin)

3D PDB for HMDB0038120 (Ovalicin)

SMILES for HMDB0038120 (Ovalicin)

INCHI for HMDB0038120 (Ovalicin)

Structure for HMDB0038120 (Ovalicin)

3D Structure for HMDB0038120 (Ovalicin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References