NP-MRD: Showing NP-Card for 4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate (NP0317745)

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Record Information

Version

2.0

Created at

2022-09-11 17:48:02 UTC

Updated at

2022-09-11 17:48:03 UTC

NP-MRD ID

NP0317745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate

Description

4,8-Diacetyl-T2-tetrol, also known as NT 1 or isoneosolaniol, 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. 4,8-Diacetyl-T2-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate is found in Fusarium compactum and Fusarium sporotrichioides. 4,8-Diacetyl-T2-tetrol is a mycotoxin produced by Fusarium sporotrichioides, Fusarium tricinctum and Haemophilus parainfluenzae.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308172D          

 27 30  0  0  0  0            999 V2000
    4.3097   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -3.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    0.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343    0.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9454   -0.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -2.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    0.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346    0.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5082   -1.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  5  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17 15  1  0  0  0  0
 18  6  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  7  1  0  0  0  0
 21 10  2  0  0  0  0
 22 11  2  0  0  0  0
 23 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 19  1  0  0  0  0
 25 10  1  0  0  0  0
 25 12  1  0  0  0  0
 26 11  1  0  0  0  0
 26 15  1  0  0  0  0
 27 13  1  0  0  0  0
 27 16  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    5.6061   -0.9230    1.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596   -0.6928    0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8051   -1.1069   -0.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607   -0.0752    1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833    0.1255    0.0148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1238   -0.6274    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123   -0.0121   -0.3358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0004   -0.0849   -1.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0860   -1.4331   -2.1818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128    1.4018    0.1827 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0190    2.1451   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    1.5610   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    2.3585   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    1.3575    1.5587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2881    0.5877    2.0720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5871    0.9373    1.3290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6482    0.6173    2.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895    0.0094    0.1252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8219    0.6619   -1.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9020    0.3685   -1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    1.0902   -3.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7273   -0.5319   -1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941   -0.7681    0.1776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4551   -2.1478   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057   -0.8348    1.6999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8889   -1.9671    2.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2279   -1.6399    2.2539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2961   -0.6374    2.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9789   -1.9884    1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4924   -0.3142    1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -0.3219   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2531   -1.6946   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627   -0.6515    1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.3121   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8617    0.4773   -2.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -1.5686   -2.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645    1.9550   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682    3.2107   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021    2.9501   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558    1.6906   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6982    2.9899    0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903    0.7800    3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6312    1.9988    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.1172    1.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041   -0.7399    0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858    0.4571   -3.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1710    1.1899   -3.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    2.1114   -3.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035   -2.6901   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -2.6938    0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555   -2.1908   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710   -1.9589    3.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -2.9321    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  2  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  8  9  1  0
  7 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 23 18  1  0
 25 27  1  1
 25 15  1  0
  7 10  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 18 45  1  1
 16 43  1  6
 17 44  1  0
 15 42  1  1
 10 37  1  6
 11 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
  5 31  1  6
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv0541 05061308172D          

 27 30  0  0  0  0            999 V2000
    4.3097   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -3.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    0.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343    0.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9454   -0.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -2.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    0.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346    0.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5082   -1.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  5  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17 15  1  0  0  0  0
 18  6  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  7  1  0  0  0  0
 21 10  2  0  0  0  0
 22 11  2  0  0  0  0
 23 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 19  1  0  0  0  0
 25 10  1  0  0  0  0
 25 12  1  0  0  0  0
 26 11  1  0  0  0  0
 26 15  1  0  0  0  0
 27 13  1  0  0  0  0
 27 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(O)C2OC3C=C(C)C(CC3(CO)C1(C)C21CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-9-5-13-18(7-20,6-12(9)25-10(2)21)17(4)15(26-11(3)22)14(23)16(27-13)19(17)8-24-19/h5,12-16,20,23H,6-8H2,1-4H3

> <INCHI_KEY>
UROCTWOJYLMRHO-UHFFFAOYSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.4049

> <EXACT_MASS>
382.162767808

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
38.35015507804694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
-0.8538114616666654

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.99435561731842

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.067075095591726

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8036445321833874

> <JCHEM_POLAR_SURFACE_AREA>
114.82000000000001

> <JCHEM_REFRACTIVITY>
90.61519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.045  -2.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.161   0.852   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.379  -5.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.989   0.446   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.415  -3.074   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.901  -0.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.184   0.427   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.582   0.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.601  -2.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.975  -0.129   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.227  -4.893   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.345  -0.574   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.715  -1.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.171   1.610   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.231  -1.648   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.766  -5.381   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.911  -4.108   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.542   1.266   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.531   0.408   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.534  -3.384   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.815  -2.039   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   17                                                            
CONECT    5    9   13                                                       
CONECT    6   12   18                                                       
CONECT    7   18   20                                                       
CONECT    8   19   24                                                       
CONECT    9    1    5   12                                                  
CONECT   10    2   21   25                                                  
CONECT   11    3   22   26                                                  
CONECT   12    6    9   25                                                  
CONECT   13    5   18   27                                                  
CONECT   14   15   16   23                                                  
CONECT   15   14   17   26                                                  
CONECT   16   14   19   27                                                  
CONECT   17    4   15   18   19                                             
CONECT   18    6    7   13   17                                             
CONECT   19    8   16   17   24                                             
CONECT   20    7                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23   14                                                            
CONECT   24    8   19                                                       
CONECT   25   10   12                                                       
CONECT   26   11   15                                                       
CONECT   27   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Isoneosolaniol	HMDB
NT 1	HMDB
NT 1 Toxin	HMDB
Toxin NT 1	HMDB
Toxin NT-1	HMDB
Toxin T 1	HMDB
Toxin T1	HMDB
4'-(Acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetic acid	Generator
4 beta, 8 alpha-Diacetoxy-12,13-epoxytrichothec-9-ene-3 alpha,15-diol	MeSH

Chemical Formula

C₁₉H₂₆O₈

Average Mass

382.4049 Da

Monoisotopic Mass

382.16277 Da

IUPAC Name

4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate

Traditional Name

4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(O)C2OC3C=C(C)C(CC3(CO)C1(C)C21CO1)OC(C)=O

InChI Identifier

InChI=1S/C19H26O8/c1-9-5-13-18(7-20,6-12(9)25-10(2)21)17(4)15(26-11(3)22)14(23)16(27-13)19(17)8-24-19/h5,12-16,20,23H,6-8H2,1-4H3

InChI Key

UROCTWOJYLMRHO-UHFFFAOYSA-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
Fusarium compactum	LOTUS Database	35616633
Fusarium sporotrichioides	LOTUS Database	35616633

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
Oxepane
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
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	0.44	ALOGPS
logP	-0.85	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.62 m³·mol⁻¹	ChemAxon
Polarizability	38.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035201

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013847

KNApSAcK ID

C00012639

Chemspider ID

8198344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10022771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate (NP0317745)

MOL for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

3D MOL for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

3D SDF for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

3D-SDF for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

PDB for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

3D PDB for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

SMILES for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

INCHI for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

Structure for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)

3D Structure for NP0317745 (4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate)