NP-MRD: Showing NP-Card for (2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid (NP0195787)

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Record Information

Version

2.0

Created at

2022-09-04 13:43:15 UTC

Updated at

2022-09-04 13:43:15 UTC

NP-MRD ID

NP0195787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid

Description

Harzianum A 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. (2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid was first documented in 2020 (PMID: 32067246). Based on a literature review a small amount of articles have been published on Harzianum A (PMID: 35104534) (PMID: 35270115) (PMID: 32613360).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215432D          

 29 32  0  0  0  0            999 V2000
    5.6625    1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900    1.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286    1.9488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    1.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8612    0.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480   -0.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634    0.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -0.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -0.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -0.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -0.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9454   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299   -0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3432   -1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -2.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1277   -1.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6736   -0.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    0.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    0.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409    1.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 21 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.5965   -0.5244   -3.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -0.2452   -1.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -1.2309   -0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8806   -0.9080    0.6665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4086   -1.9915    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658   -2.1453    1.4746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3518   -2.1947    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411   -0.7192   -0.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3622   -0.5264   -0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -0.2012   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -0.0608   -2.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285   -0.0078   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741   -0.1319   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418    0.0555   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7627    0.2224   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6267    0.5290   -1.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9339    0.6773   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8353    0.9864   -1.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4561    1.1252   -3.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1759    1.1334   -1.6902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    0.0667    0.9794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8049    1.3263    1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172   -0.9301    2.1016 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2719   -1.0792    2.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -0.6072    3.4132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0853    0.3417    0.8972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4601    0.7682    2.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4529    1.4689    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846    1.1452   -1.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067   -1.6208   -3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6996   -0.3963   -3.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    0.0866   -3.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1809   -2.2606   -1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8967   -0.7053    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -3.0595    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3692   -2.6801    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8989   -2.6868   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -0.5320   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1455    0.2284   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748   -0.3859    0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324    0.3115    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2450    0.0217    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2885    0.6456   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2464    0.5601    0.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4222    1.5244   -0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3727    1.6089    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793    2.1952    1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765    1.2329    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0263   -2.0538    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4979   -0.2969    3.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3767    1.4246    2.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    1.3616    2.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8013   -0.1055    2.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    1.9284   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    2.3087    0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0471    1.7962   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3555    1.4370   -0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
  8 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29  2  1  0
 26  4  1  0
 23  6  1  0
 23 25  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  1
  6 35  1  1
  7 36  1  0
  7 37  1  0
  8 38  1  6
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
 24 50  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
M  END


  Mrv1652309042215432D          

 29 32  0  0  0  0            999 V2000
    5.6625    1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900    1.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286    1.9488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    1.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8612    0.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480   -0.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634    0.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -0.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -0.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -0.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -0.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9454   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299   -0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3432   -1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -2.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1277   -1.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6736   -0.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    0.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    0.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409    1.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 21 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2OC3CC(OC(=O)\C=C\C=C\C=C\C(O)=O)C(C)(C33CO3)C2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O6/c1-15-10-11-21(2)16(12-15)28-18-13-17(22(21,3)23(18)14-27-23)29-20(26)9-7-5-4-6-8-19(24)25/h4-9,12,16-18H,10-11,13-14H2,1-3H3,(H,24,25)/b5-4+,8-6+,9-7+

> <INCHI_KEY>
FVRDNLIUSWSBCT-WUJFNTSISA-N

> <FORMULA>
C23H28O6

> <MOLECULAR_WEIGHT>
400.471

> <EXACT_MASS>
400.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.571963562737224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid

> <JCHEM_LOGP>
3.3771360956666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.201582219405669

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9213652265911043

> <JCHEM_POLAR_SURFACE_AREA>
85.36

> <JCHEM_REFRACTIVITY>
109.67689999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      10.570   2.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.128   2.056   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.939   3.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.497   2.493   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.467   3.638   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.929   3.546   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.043   2.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.474   0.809   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.330  -0.222   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.865   0.255   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.545   1.761   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.280  -0.776   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.744  -0.299   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.889  -1.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.353  -0.853   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.498  -1.884   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.963  -1.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.107  -2.438   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.787  -3.944   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -9.572  -1.962   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.899   0.224   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.991  -1.313   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.244   0.974   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.106  -0.560   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.434  -0.004   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.875   0.536   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.999   1.764   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.935   0.651   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.503   2.129   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    8   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21    4   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    2                                                       
CONECT   27   21    6   28   29                                             
CONECT   28   27   29                                                       
CONECT   29   28   27                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
Trichodermyl 2',4',6'-octatriendioate	MeSH
Harzianum b	MeSH

Chemical Formula

C₂₃H₂₈O₆

Average Mass

400.4710 Da

Monoisotopic Mass

400.18859 Da

IUPAC Name

(2E,4E,6E)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid

Traditional Name

(2E,4E,6E)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

CC1=CC2OC3CC(OC(=O)\C=C\C=C\C=C\C(O)=O)C(C)(C33CO3)C2(C)CC1

InChI Identifier

InChI=1S/C23H28O6/c1-15-10-11-21(2)16(12-15)28-18-13-17(22(21,3)23(18)14-27-23)29-20(26)9-7-5-4-6-8-19(24)25/h4-9,12,16-18H,10-11,13-14H2,1-3H3,(H,24,25)/b5-4+,8-6+,9-7+

InChI Key

FVRDNLIUSWSBCT-WUJFNTSISA-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

Not Available

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
Medium-chain fatty acid
Fatty acid ester
Heterocyclic fatty acid
Oxepane
Dicarboxylic acid or derivatives
Oxane
Unsaturated fatty acid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
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	3.38	ChemAxon
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.68 m³·mol⁻¹	ChemAxon
Polarizability	43.57 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

4948229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6444304

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hussain R, Yadav R, Ahmed M, Khan TA, Kumar D, Akhter Y: Interplay between two spin states determines the hydroxylation catalyzed by P450 monooxygenase from Trichoderma brevicompactum. J Comput Chem. 2020 May 30;41(14):1330-1336. doi: 10.1002/jcc.26177. Epub 2020 Feb 17. [PubMed:32067246 ]
Mahato DK, Pandhi S, Kamle M, Gupta A, Sharma B, Panda BK, Srivastava S, Kumar M, Selvakumar R, Pandey AK, Suthar P, Arora S, Kumar A, Gamlath S, Bharti A, Kumar P: Trichothecenes in food and feed: Occurrence, impact on human health and their detection and management strategies. Toxicon. 2022 Mar;208:62-77. doi: 10.1016/j.toxicon.2022.01.011. Epub 2022 Jan 31. [PubMed:35104534 ]
Diaz-Diaz M, Bernal-Cabrera A, Trapero A, Medina-Marrero R, Sifontes-Rodriguez S, Cupull-Santana RD, Garcia-Bernal M, Agusti-Brisach C: Characterization of Actinobacterial Strains as Potential Biocontrol Agents against Macrophomina phaseolina and Rhizoctonia solani, the Main Soil-Borne Pathogens of Phaseolus vulgaris in Cuba. Plants (Basel). 2022 Feb 26;11(5):645. doi: 10.3390/plants11050645. [PubMed:35270115 ]
Yin M, Fasoyin OE, Wang C, Yue Q, Zhang Y, Dun B, Xu Y, Zhang L: Herbicidal efficacy of harzianums produced by the biofertilizer fungus, Trichoderma brevicompactum. AMB Express. 2020 Jul 1;10(1):118. doi: 10.1186/s13568-020-01055-x. [PubMed:32613360 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid (NP0195787)

MOL for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

3D MOL for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

3D SDF for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

3D-SDF for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

PDB for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

3D PDB for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

SMILES for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

INCHI for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

Structure for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)

3D Structure for NP0195787 ((2e,4e,6e)-8-oxo-8-{1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yloxy}octa-2,4,6-trienoic acid)