NP-MRD: Showing NP-Card for Ophiobolin A (NP0052032)

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Record Information

Version

2.0

Created at

2022-04-27 23:13:09 UTC

Updated at

2022-04-27 23:13:09 UTC

NP-MRD ID

NP0052032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophiobolin A

Description

ZINC16343419 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. Ophiobolin A is found in Bipolaris oryzae, Cochliobolus heterostrophus, Drechslera gigantea, Helminthosporium turcicum, Helminthosporium zizaniae, Ophiobolus heterostrophus and Ophiobolus miyabeanus. Based on a literature review very few articles have been published on ZINC16343419.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201132D          

 29 32  0  0  1  0            999 V2000
    2.9196   -1.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5681   -0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3872   -0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8973   -1.4668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7994   -2.2860    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1509   -2.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3317   -2.6981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8217   -2.0496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0474   -2.3343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0788   -3.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726   -3.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730   -2.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -1.9705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2221   -1.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159   -1.5099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6644   -0.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0614   -2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -1.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -0.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763   -3.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -2.6322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1089   -2.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7066   -1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0528   -0.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2903   -3.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0849   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7912   -0.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  1  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
  9 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  6  0  0  0
 13 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  7 21  1  6  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  1  0  0  0
 24 25  2  0  0  0  0
 22 26  1  1  0  0  0
 22 27  1  6  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    6.7338   -2.3623    0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6198   -1.3835    1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8040   -0.2727    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -1.4619    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4489   -0.4374    0.6215 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6793    0.6589   -0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759    0.8070   -0.9982 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0887    2.2270   -1.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    0.2222    0.0449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2487    1.0133    1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111    1.2052    1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424    0.7771    0.2481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1965    2.0191   -0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641    0.0432    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4534    0.4046    0.0534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4923    0.2011   -1.4358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9361   -0.0928   -1.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315   -0.0241   -2.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5927   -0.4800   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052   -0.5563    0.6165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0264   -0.0034    1.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758   -1.8318    0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938   -0.9241   -1.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5011   -2.0560   -2.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9335   -3.0953   -2.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4006   -1.1699   -2.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237   -0.4094   -1.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.1699   -0.3715 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1684   -0.9342    0.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4923   -3.1673    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6548   -1.8049    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9869   -2.8582    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -0.2014    2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1305   -0.3650    2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6134    0.6884    1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3838   -2.2830   -0.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5612   -0.0674    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220    0.4182   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652    1.5962    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    0.1590   -1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    2.9041   -0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2983    2.4208   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    2.6169   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550    0.4873    2.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037    1.9912    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921    2.2848    1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875    0.6508    2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0912    1.9405   -1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    2.8429   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2045    2.4366   -0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219   -1.0652    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3303    0.1011    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8511    1.4083    0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138    1.1538   -2.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    0.3503   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1505   -1.4366   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7906   -0.6800    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5484    0.9559    1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2256    0.2603    2.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6411   -2.3618    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5845   -2.0706   -2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -2.1656   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987   -1.1193   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191    0.4513   -2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565   -1.1732    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 29  1  0
  9 29  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  1
 16 23  1  0
 23 24  1  0
 24 25  2  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  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  6
  6 38  1  0
  6 39  1  0
  5 37  1  1
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  6
 16 54  1  6
 19 55  1  0
 19 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 24 61  1  0
 26 62  1  0
 27 63  1  0
 27 64  1  0
 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


  Mrv1652304282201132D          

 29 32  0  0  1  0            999 V2000
    2.9196   -1.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5681   -0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3872   -0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8973   -1.4668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7994   -2.2860    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1509   -2.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3317   -2.6981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8217   -2.0496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0474   -2.3343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0788   -3.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726   -3.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730   -2.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -1.9705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2221   -1.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159   -1.5099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6644   -0.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0614   -2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -1.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -0.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763   -3.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -2.6322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1089   -2.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7066   -1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0528   -0.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2903   -3.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0849   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7912   -0.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  1  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
  9 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  6  0  0  0
 13 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  7 21  1  6  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  1  0  0  0
 24 25  2  0  0  0  0
 22 26  1  1  0  0  0
 22 27  1  6  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0052032

> <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)=CC[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/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1

> <INCHI_KEY>
MWYYLZRWWNBROW-ISPAKYAGSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.67941158684009

> <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,11'S,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>
63.6

> <JCHEM_REFRACTIVITY>
115.04379999999996

> <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,11'S,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                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.450  -2.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.660  -1.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.190  -1.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.142  -2.738   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.959  -4.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.748  -5.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.219  -5.036   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.267  -3.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.822  -4.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.880  -5.896   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.362  -6.316   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.376  -4.889   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.424  -3.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.281  -2.399   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.763  -2.818   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.974  -1.866   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.115  -3.737   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.935  -2.434   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.474  -2.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.216  -1.072   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.862  -6.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.357  -4.913   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.403  -3.784   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.652  -2.439   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.299  -1.041   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.875  -6.376   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.359  -6.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.943  -0.185   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.158   1.140   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11   21                                             
CONECT    8    7    1    9                                                  
CONECT    9    8   10   12   15                                             
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    7                                                            
CONECT   22    5   23   26   27                                             
CONECT   23   22   24                                                       
CONECT   24   23    4   25                                                  
CONECT   25   24                                                            
CONECT   26   22                                                            
CONECT   27   22                                                            
CONECT   28    3   29                                                       
CONECT   29   28                                                            
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

(1'S,2S,3S,3'R,5R,7'R,11'S,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

Traditional Name

(1'S,2S,3S,3'R,5R,7'R,11'S,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

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)=CC[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/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1

InChI Key

MWYYLZRWWNBROW-ISPAKYAGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 oryzae	Fungi	KNApSAcK
Cochliobolus heterostrophus	Fungi	KNApSAcK
Drechslera gigantea	LOTUS Database	35616633
Exserohilum turcicum	Fungi	KNApSAcK
Helminthosporium zizaniae	Fungi	KNApSAcK
Ophiobolus heterostrophus	Fungi	KNApSAcK
Ophiobolus miyabeanus	Fungi	KNApSAcK

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
logP	3.54	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.04 m³·mol⁻¹	ChemAxon
Polarizability	45.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ophiobolin A (NP0052032)

MOL for NP0052032 (Ophiobolin A)

3D MOL for NP0052032 (Ophiobolin A)

3D SDF for NP0052032 (Ophiobolin A)

3D-SDF for NP0052032 (Ophiobolin A)

PDB for NP0052032 (Ophiobolin A)

3D PDB for NP0052032 (Ophiobolin A)

SMILES for NP0052032 (Ophiobolin A)

INCHI for NP0052032 (Ophiobolin A)

Structure for NP0052032 (Ophiobolin A)

3D Structure for NP0052032 (Ophiobolin A)