NP-MRD: Showing NP-Card for (1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde (NP0156508)

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Record Information

Version

2.0

Created at

2022-09-02 13:43:49 UTC

Updated at

2022-09-02 13:43:49 UTC

NP-MRD ID

NP0156508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde

Description

6-Epi-Ophiobolin A 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. (1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde is found in Bipolaris cookei and Drechslera gigantea. (1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde was first documented in 2006 (PMID: 16962149). Based on a literature review a small amount of articles have been published on 6-epi-Ophiobolin A (PMID: 23668986) (PMID: 33074690) (PMID: 32202757) (PMID: 31693792).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215432D          

 29 32  0  0  1  0            999 V2000
    0.7063   -3.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -3.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8039   -3.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886   -2.2435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6295   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.9096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9146   -0.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9138   -1.1943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9453   -0.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390   -0.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1982   -0.8305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5427   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0173   -0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6658   -1.2426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7637   -2.0618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5730   -2.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9193   -2.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9753   -1.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146   -0.8964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9514   -0.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567   -0.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2537   -2.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6576   -3.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -4.1391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -2.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -2.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881   -1.4790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8824   -2.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
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 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
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 20 22  1  6  0  0  0
 16 23  1  0  0  0  0
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  9 28  1  0  0  0  0
 12 28  1  0  0  0  0
  9 29  1  6  0  0  0
  5 29  1  0  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
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   -0.5409   -0.9755   -2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2528    0.9350    1.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2719    0.2191    1.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151    0.0273   -0.2464 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0886   -1.2534   -0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988    1.1429   -0.9929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8153    1.3518    1.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9734    2.4593    2.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    2.8250    3.5177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5918    0.8732    1.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -0.2248    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304   -0.0744   -0.3331 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0896    0.8391   -0.9505 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7021    3.2490    1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9718   -1.6973    0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1291   -3.1560   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485   -2.6942   -2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5340   -3.5064   -0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192   -0.8513   -3.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060    0.6689   -2.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5185   -2.0204   -2.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -0.4438   -3.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887   -2.9940   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353   -2.3961   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9404    1.1034   -1.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802   -0.1534   -2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0282   -0.9283    0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2963    2.0705    0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5741   -0.7468    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1396    0.9195    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846   -1.3150   -1.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0907   -1.2136    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1940    1.0280   -0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  2  2  3
  2  1  1  0
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  9  7  1  0
 28  9  1  0
 28 12  1  0
 20 15  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  7 40  1  1
  6 38  1  0
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  5 37  1  6
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 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
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 28 65  1  1
  4 36  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
M  END


  Mrv1652309022215432D          

 29 32  0  0  1  0            999 V2000
    0.7063   -3.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -3.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8039   -3.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886   -2.2435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6295   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.9096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9146   -0.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9453   -0.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5730   -2.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4146   -0.8964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.1567   -0.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2537   -2.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6576   -3.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -4.1391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -2.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6881   -1.4790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8824   -2.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
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  5  6  1  0  0  0  0
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  9 29  1  6  0  0  0
  5 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H](O[C@@]11CC[C@]2(C)C[C@H]3[C@@H](C(=O)C[C@@]3(C)O)\C(C=O)=C/C[C@@H]12)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22-,23+,24+,25-/m0/s1

> <INCHI_KEY>
MWYYLZRWWNBROW-RXAKKKFQSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.23616996867605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,3S,3'R,5R,7'R,9'E,11'R,14'R)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecan]-9'-ene-10'-carbaldehyde

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.535256972666666

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.948071183160895

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.615091202879062

> <JCHEM_PKA_STRONGEST_BASIC>
-2.989416208149593

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
115.04379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,3S,3'R,5R,7'R,9'E,11'R,14'R)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecan]-9'-ene-10'-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.318  -7.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.850  -5.896   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.864  -4.713   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.367  -5.633   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.899  -4.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.042  -2.908   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.994  -1.698   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.574  -0.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.439  -2.229   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.498  -0.690   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.980  -0.271   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.837  -1.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.480  -0.151   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.366  -1.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.576  -2.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.759  -3.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.270  -4.147   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.916  -5.545   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.021  -2.803   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.974  -1.673   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.976  -0.504   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.493  -0.210   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.807  -5.059   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.561  -6.402   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.775  -7.726   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.278  -5.242   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.067  -4.290   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.885  -2.761   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.380  -3.768   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28   29                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   28                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    9   12                                                  
CONECT   29    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5590 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H](O[C@@]11CC[C@]2(C)C[C@H]3[C@@H](C(=O)C[C@@]3(C)O)\C(C=O)=C/C[C@@H]12)C=C(C)C

InChI Identifier

InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22-,23+,24+,25-/m0/s1

InChI Key

MWYYLZRWWNBROW-RXAKKKFQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bipolaris cookei	LOTUS Database	35616633
Drechslera gigantea	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Ophiobolane sesterterpenoids

Alternative Parents

Substituents

Ophiobolane sesterterpenoid
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Ketone
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Aldehyde
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.85	ALOGPS
logS	-4.7	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31118877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12303079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R, Motta A: Ophiobolin E and 8-epi-ophiobolin J produced by Drechslera gigantea, a potential mycoherbicide of weedy grasses. Phytochemistry. 2006 Oct;67(20):2281-7. doi: 10.1016/j.phytochem.2006.07.016. Epub 2006 Sep 7. [PubMed:16962149 ]
Wang QX, Yang JL, Qi QY, Bao L, Yang XL, Liu MM, Huang P, Zhang LX, Chen JL, Cai L, Liu HW: 3-Anhydro-6-hydroxy-ophiobolin A, a new sesterterpene inhibiting the growth of methicillin-resistant Staphylococcus aureus and inducing the cell death by apoptosis on K562, from the phytopathogenic fungus Bipolaris oryzae. Bioorg Med Chem Lett. 2013 Jun 15;23(12):3547-50. doi: 10.1016/j.bmcl.2013.04.034. Epub 2013 Apr 22. [PubMed:23668986 ]
Zatout R, Masi M, Sangermano F, Vurro M, Zonno MC, Santoro E, Calabro V, Superchi S, Evidente A: Drophiobiolins A and B, Bioactive Ophiobolan Sestertepenoids Produced by Dreschslera gigantea. J Nat Prod. 2020 Nov 25;83(11):3387-3396. doi: 10.1021/acs.jnatprod.0c00836. Epub 2020 Oct 19. [PubMed:33074690 ]
Harmange Magnani CS, Thach DQ, Haelsig KT, Maimone TJ: Syntheses of Complex Terpenes from Simple Polyprenyl Precursors. Acc Chem Res. 2020 Apr 21;53(4):949-961. doi: 10.1021/acs.accounts.0c00055. Epub 2020 Mar 23. [PubMed:32202757 ]
Thach DQ, Brill ZG, Grover HK, Esguerra KV, Thompson JK, Maimone TJ: Total Synthesis of (+)-6-epi-Ophiobolin A. Angew Chem Int Ed Engl. 2020 Jan 20;59(4):1532-1536. doi: 10.1002/anie.201913150. Epub 2019 Dec 12. [PubMed:31693792 ]
LOTUS database [Link]

Showing NP-Card for (1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde (NP0156508)

MOL for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

3D MOL for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

3D SDF for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

3D-SDF for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

PDB for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

3D PDB for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

SMILES for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

INCHI for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

Structure for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)

3D Structure for NP0156508 ((1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carbaldehyde)