MiMeDB: Showing metabocard for Ophiobolin F (MMDBc0003546)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:32:48 UTC

Update Date

2022-08-31 06:21:04 UTC

Metabolite ID

MMDBc0003546

Metabolite Identification

Common Name

Ophiobolin F

Description

(1R,3S,4R,7S,11S,12R)-1,4,8-trimethyl-12-[(2S)-6-methylhept-5-en-2-yl]tricyclo[9.3.0.0³,⁷]tetradec-8-en-4-ol belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. Based on a literature review very few articles have been published on (1R,3S,4R,7S,11S,12R)-1,4,8-trimethyl-12-[(2S)-6-methylhept-5-en-2-yl]tricyclo[9.3.0.0³,⁷]tetradec-8-en-4-ol.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652305142123322D          

 31 33  0  0  1  0            999 V2000
   -2.3952    1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    2.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853    1.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917    1.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9130   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372   -1.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    0.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    0.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988    0.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461    0.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4465   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566   -1.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461   -1.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840    1.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    0.4678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3083    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -0.1595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6240   -0.0948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4682   -0.0948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3083   -0.8570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7839   -0.8570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9356   -1.3928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4379   -2.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.0952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    0.6027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7990   -0.0948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.0948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.6718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10 11  1  4  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17  8  2  0  0  0  0
 18  3  1  6  0  0  0
 18  9  1  0  0  0  0
 19  4  1  0  0  0  0
 19 10  2  0  0  0  0
 20 12  1  0  0  0  0
 20 18  1  6  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 22 11  1  0  0  0  0
 22 20  1  0  0  0  0
 23 16  1  0  0  0  0
 23 21  1  0  0  0  0
 24  5  1  6  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25  6  1  6  0  0  0
 25 15  1  0  0  0  0
 25 23  1  0  0  0  0
 25 26  1  1  0  0  0
 18 27  1  1  0  0  0
 20 28  1  1  0  0  0
 21 29  1  6  0  0  0
 22 30  1  1  0  0  0
 23 31  1  6  0  0  0
M  END

  Mrv1652305142123322D          

 31 33  0  0  1  0            999 V2000
   -2.3952    1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    2.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853    1.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917    1.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9130   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372   -1.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    0.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    0.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988    0.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461    0.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4465   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566   -1.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461   -1.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840    1.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    0.4678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3083    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -0.1595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6240   -0.0948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4682   -0.0948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3083   -0.8570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7839   -0.8570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9356   -1.3928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4379   -2.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.0952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    0.6027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7990   -0.0948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.0948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.6718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10 11  1  4  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17  8  2  0  0  0  0
 18  3  1  6  0  0  0
 18  9  1  0  0  0  0
 19  4  1  0  0  0  0
 19 10  2  0  0  0  0
 20 12  1  0  0  0  0
 20 18  1  6  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 22 11  1  0  0  0  0
 22 20  1  0  0  0  0
 23 16  1  0  0  0  0
 23 21  1  0  0  0  0
 24  5  1  6  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25  6  1  6  0  0  0
 25 15  1  0  0  0  0
 25 23  1  0  0  0  0
 25 26  1  1  0  0  0
 18 27  1  1  0  0  0
 20 28  1  1  0  0  0
 21 29  1  6  0  0  0
 22 30  1  1  0  0  0
 23 31  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0003546

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(CCC=C(C)C)[C@@]1([H])CC[C@]2(C)C[C@@]3([H])[C@]([H])(CC[C@@]3(C)O)C(C)=CC[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O/c1-17(2)8-7-9-18(3)20-12-14-24(5)16-23-21(13-15-25(23,6)26)19(4)10-11-22(20)24/h8,10,18,20-23,26H,7,9,11-16H2,1-6H3/t18-,20+,21+,22-,23-,24+,25+/m0/s1

> <INCHI_KEY>
JNYWQVTXIGGOTC-PFZGDJCMSA-N

> <FORMULA>
C25H42O

> <MOLECULAR_WEIGHT>
358.61

> <EXACT_MASS>
358.323565972

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
45.88894026023138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,7S,11S,12R)-1,4,8-trimethyl-12-[(2S)-6-methylhept-5-en-2-yl]tricyclo[9.3.0.0^{3,7}]tetradec-8-en-4-ol

> <ALOGPS_LOGP>
6.70

> <JCHEM_LOGP>
6.4979309690000004

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.717679402228008

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7352870294654695

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
114.20519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.94e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,7S,11S,12R)-1,4,8-trimethyl-12-[(2S)-6-methylhept-5-en-2-yl]tricyclo[9.3.0.0^{3,7}]tetradec-8-en-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      -4.471   2.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.443   4.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.586   2.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.131   2.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.438  -3.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.096  -3.660   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.442   1.764   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.957   1.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.558   0.593   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.619   1.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.197   1.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.713  -1.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.167  -0.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.026  -2.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.526  -1.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.619  -2.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.957   2.654   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.072   0.873   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.042   1.246   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.072  -0.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.632  -0.177   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.607  -0.177   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.042  -1.600   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.197  -1.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.213  -2.600   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.151  -3.822   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       1.072   2.044   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.661   1.125   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       7.092  -0.177   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.147  -0.177   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.801  -3.121   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5   24                                                            
CONECT    6   25                                                            
CONECT    7    8    9                                                       
CONECT    8    7   17                                                       
CONECT    9    7   18                                                       
CONECT   10   11   19                                                       
CONECT   11   10   22                                                       
CONECT   12   14   20                                                       
CONECT   13   15   21                                                       
CONECT   14   12   24                                                       
CONECT   15   13   25                                                       
CONECT   16   23   24                                                       
CONECT   17    1    2    8                                                  
CONECT   18    3    9   20   27                                             
CONECT   19    4   10   21                                                  
CONECT   20   12   18   22   28                                             
CONECT   21   13   19   23   29                                             
CONECT   22   11   20   24   30                                             
CONECT   23   16   21   25   31                                             
CONECT   24    5   14   16   22                                             
CONECT   25    6   15   23   26                                             
CONECT   26   25                                                            
CONECT   27   18                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₄₂O

Average Mass

358.61

Monoisotopic Mass

358.323565972

IUPAC Name

(1R,3S,4R,7S,11S,12R)-1,4,8-trimethyl-12-[(2S)-6-methylhept-5-en-2-yl]tricyclo[9.3.0.0^{3,7}]tetradec-8-en-4-ol

Traditional Name

(1R,3S,4R,7S,11S,12R)-1,4,8-trimethyl-12-[(2S)-6-methylhept-5-en-2-yl]tricyclo[9.3.0.0^{3,7}]tetradec-8-en-4-ol

CAS Registry Number

Not Available

SMILES

[H][C@](C)(CCC=C(C)C)[C@@]1([H])CC[C@]2(C)C[C@@]3([H])[C@]([H])(CC[C@@]3(C)O)C(C)=CC[C@@]12[H]

InChI Identifier

InChI=1S/C25H42O/c1-17(2)8-7-9-18(3)20-12-14-24(5)16-23-21(13-15-25(23,6)26)19(4)10-11-22(20)24/h8,10,18,20-23,26H,7,9,11-16H2,1-6H3/t18-,20+,21+,22-,23-,24+,25+/m0/s1

InChI Key

JNYWQVTXIGGOTC-PFZGDJCMSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Ophiobolin F (MMDBc0003546)

MOL for #<Metabolite:0x00007f833d6ab428>

3D MOL for #<Metabolite:0x00007f833d6ab428>

3D SDF for #<Metabolite:0x00007f833d6ab428>

3D-SDF for #<Metabolite:0x00007f833d6ab428>

PDB for #<Metabolite:0x00007f833d6ab428>

3D PDB for #<Metabolite:0x00007f833d6ab428>

SMILES for #<Metabolite:0x00007f833d6ab428>

INCHI for #<Metabolite:0x00007f833d6ab428>

Structure for #<Metabolite:0x00007f833d6ab428>

3D Structure for #<Metabolite:0x00007f833d6ab428>