NP-MRD: Showing NP-Card for [4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate (NP0059166)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 04:27:10 UTC

Updated at

2022-04-28 04:27:11 UTC

NP-MRD ID

NP0059166

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate

Description

(1'S,2R,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-11'-yl (2Z,6R,7S)-6,7-dihydroxyocta-2,4-dienoate belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. [4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate is found in Myrothecium verrucaria. Based on a literature review very few articles have been published on (1'S,2R,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-11'-yl (2Z,6R,7S)-6,7-dihydroxyocta-2,4-dienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206272D          

 29 32  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -0.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -0.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381   -2.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095   -2.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941   -3.1043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7073   -2.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654   -3.9113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0500   -4.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522   -4.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  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
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 11 26  1  6  0  0  0
 10 27  1  6  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
  2 29  1  1  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -6.3830    1.2009    1.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9335    0.9913    1.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.1568    2.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -0.3655    1.8217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6073   -1.7092    1.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284   -2.4345    0.7707 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1638   -2.7362    0.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137   -1.3776   -0.0887 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1243   -1.5867   -1.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4825   -1.1958   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -0.6894   -0.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886   -1.4339   -2.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5540   -1.1190   -2.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2991   -0.5074   -1.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047   -0.2208   -1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639    0.4137   -0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7026    0.0748   -0.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1958    1.9104   -0.2914 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7741    2.3911    1.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424    2.2519   -0.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9564   -0.6105   -0.4892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8192    0.0754   -1.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2837    0.3354    0.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9931    1.0894    0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2389    1.3685    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0278    2.0679    1.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0170   -1.6743   -0.4658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4604   -2.3529   -1.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2955   -1.4565   -0.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0128    0.7080    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6793    0.7011    2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6236    2.2670    2.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9529   -0.9467    2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718    0.0952    2.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297   -3.3462    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098   -3.4364   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -3.1097    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -0.9056    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503   -1.8998   -3.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324   -1.3264   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -0.2536   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0520   -0.4649   -2.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8826    0.0265    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9714   -0.0322   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7109    2.4251   -1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5912    1.5962    1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946    3.2842    1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8459    2.6296    0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4689    1.9615    0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    1.0876   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739    0.0982   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050   -0.5178   -2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266    0.7372    1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710    1.0586    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2170    2.1826    1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    2.1055   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0036    0.8493   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6832    2.7931    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3804    2.4969    1.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307   -1.9795   -2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7740   -3.4284   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  1
 23 21  1  0
 21 22  1  6
 21 27  1  0
 27 28  1  0
 28 29  1  0
 21  8  1  0
 27 29  1  1
 27  6  1  0
 23  4  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 18 45  1  6
 20 49  1  0
 16 43  1  1
 17 44  1  0
 15 42  1  0
 14 41  1  0
 13 40  1  0
 12 39  1  0
  8 38  1  1
  7 36  1  0
  7 37  1  0
  6 35  1  1
  4 34  1  1
  3 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 26 58  1  0
 26 59  1  0
 25 56  1  0
 25 57  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
 28 60  1  0
 28 61  1  0
M  END


  Mrv1652304282206272D          

 29 32  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -0.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -0.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381   -2.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095   -2.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941   -3.1043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7073   -2.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654   -3.9113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0500   -4.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522   -4.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  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
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 11 26  1  6  0  0  0
 10 27  1  6  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
  2 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0059166

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H](O)\C=C\C=C/C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)CC[C@]3(C)[C@]1(C)[C@@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O6/c1-14-9-10-21(3)17(11-14)28-19-12-18(22(21,4)23(19)13-27-23)29-20(26)8-6-5-7-16(25)15(2)24/h5-8,11,15-19,24-25H,9-10,12-13H2,1-4H3/b7-5+,8-6-/t15-,16+,17+,18+,19+,21-,22+,23+/m0/s1

> <INCHI_KEY>
MUIQEOKJENXWJC-KDFJAXKNSA-N

> <FORMULA>
C23H32O6

> <MOLECULAR_WEIGHT>
404.503

> <EXACT_MASS>
404.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.100996200081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2Z,4E,6R,7S)-6,7-dihydroxyocta-2,4-dienoate

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
2.315885966999998

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.406924140806225

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.743006307701847

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0343806227928694

> <JCHEM_POLAR_SURFACE_AREA>
88.52000000000001

> <JCHEM_REFRACTIVITY>
109.8722

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2Z,4E,6R,7S)-6,7-dihydroxyocta-2,4-dienoate

> <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       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.165   0.707   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.485  -0.799   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.949  -1.275   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.340  -1.830   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.660  -3.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.125  -3.812   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.444  -5.319   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.909  -5.795   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.054  -4.765   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.229  -7.301   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.693  -7.777   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.084  -8.331   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.770   1.580   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.338   3.058   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11   29                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   27   28                                             
CONECT   11   10    2   12   26                                             
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   11                                                            
CONECT   27   10   28                                                       
CONECT   28   27   10                                                       
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1's,2R,2'r,7'r,9'r,11'r)-1',2',5'-Trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-11'-yl (2Z,6R,7S)-6,7-dihydroxyocta-2,4-dienoic acid	Generator

Chemical Formula

C₂₃H₃₂O₆

Average Mass

404.5030 Da

Monoisotopic Mass

404.21989 Da

IUPAC Name

(1'S,2R,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2Z,4E,6R,7S)-6,7-dihydroxyocta-2,4-dienoate

Traditional Name

(1'S,2R,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2Z,4E,6R,7S)-6,7-dihydroxyocta-2,4-dienoate

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H](O)\C=C\C=C/C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)CC[C@]3(C)[C@]1(C)[C@@]21CO1

InChI Identifier

InChI=1S/C23H32O6/c1-14-9-10-21(3)17(11-14)28-19-12-18(22(21,4)23(19)13-27-23)29-20(26)8-6-5-7-16(25)15(2)24/h5-8,11,15-19,24-25H,9-10,12-13H2,1-4H3/b7-5+,8-6-/t15-,16+,17+,18+,19+,21-,22+,23+/m0/s1

InChI Key

MUIQEOKJENXWJC-KDFJAXKNSA-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
Myrothecium verrucaria	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Fatty alcohol
Oxepane
Fatty acid ester
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.69	ALOGPS
logP	2.32	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.87 m³·mol⁻¹	ChemAxon
Polarizability	43.1 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	Yes	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

162913037

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate (NP0059166)

MOL for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

3D MOL for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

3D SDF for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

3D-SDF for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

PDB for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

3D PDB for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

SMILES for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

INCHI for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

Structure for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)

3D Structure for NP0059166 ([4beta(2Z,4E,6S,7S)]-12,13-Epoxy-trichothec-9-en-4-ol 6,7-dihydroxy-2,4-octadienoate)