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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:53:11 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038562

Secondary Accession Numbers

HMDB38562

Metabolite Identification

Common Name

8-Propanoylneosolaniol

Description

8-Propanoylneosolaniol, also known as 3'-hydroxypapaverine, 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. Based on a literature review a small amount of articles have been published on 8-Propanoylneosolaniol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 01251307582D          

 31 34  0  0  0  0            999 V2000
    0.6689   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6689   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -4.9450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3834   -4.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0978   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -5.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8123   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8123   -4.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7600   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -5.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -5.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -6.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -4.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248   -5.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -6.6873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8232   -5.2789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6239   -5.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -7.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -7.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -7.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -6.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -7.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -8.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -8.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8103   -8.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  6  0  0  0
  2 11  1  0  0  0  0
  3 12  1  6  0  0  0
  5 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 16  1  1  0  0  0
 16 15  1  0  0  0  0
  8 17  1  0  0  0  0
 10 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 13 27  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 20  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  9 15  1  6  0  0  0
M  END

HMDB0038562
     RDKit          3D
8-Propanoylneosolaniol
 61 64  0  0  0  0  0  0  0  0999 V2000
    6.0137    0.4491    2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468    0.1180    0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484   -0.7607    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413   -1.9702    0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.1728   -0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.8625   -0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1994   -0.3074    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997   -0.0429   -0.3012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0805    1.4238   -0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1647    1.9282   -1.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489    3.2691   -1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    3.8063   -2.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    4.0043   -1.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408   -0.8182   -1.5611 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9696   -0.8509   -2.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467   -0.8715   -1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9120   -2.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -2.1237   -1.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -2.2804   -0.5026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8839   -1.3679   -0.7338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1799   -1.1403   -2.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148   -0.1287    0.0859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5106   -0.2109    1.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4164    0.8017    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461    0.7049    2.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229    1.8158    0.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491   -0.3103    0.6456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0961    0.4391    1.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678   -1.8200    0.8767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8653   -2.5459    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2487   -2.2204    1.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113    0.5511    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    1.4153    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6028   -0.3574    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7531   -0.3988    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451    1.0708    0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.9309   -0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    0.6237    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841   -1.0024    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049    2.0425    0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.6603   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    2.9992   -2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    4.6255   -3.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968    4.1737   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271   -0.3327   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -0.8593   -3.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2181   -0.7817   -3.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.9440   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -0.2337   -2.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -3.3445   -0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -1.9486   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097   -1.9538   -2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494    0.7934   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5734   -0.3839    2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576    1.1199    3.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2937    1.2133    2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.0005    2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414    1.1563    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -0.2406    2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -3.6431    1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -2.1322    2.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 16  6  1  0
 29 19  1  0
 27  8  1  0
 29 31  1  1
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  0
  9 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  6
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  1
 20 51  1  1
 21 52  1  0
 22 53  1  6
 25 54  1  0
 25 55  1  0
 25 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
M  END


  Mrv0541 01251307582D          

 31 34  0  0  0  0            999 V2000
    0.6689   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6689   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -4.9450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3834   -4.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0978   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -5.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8123   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8123   -4.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7600   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -5.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -5.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -6.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -4.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248   -5.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -6.6873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8232   -5.2789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6239   -5.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -7.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -7.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -7.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -6.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -7.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -8.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -8.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8103   -8.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  6  0  0  0
  2 11  1  0  0  0  0
  3 12  1  6  0  0  0
  5 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 16  1  1  0  0  0
 16 15  1  0  0  0  0
  8 17  1  0  0  0  0
 10 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 13 27  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 20  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  9 15  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0038562

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O9/c1-6-16(25)30-14-8-21(9-27-12(3)23)15(7-11(14)2)31-19-17(26)18(29-13(4)24)20(21,5)22(19)10-28-22/h7,14-15,17-19,26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22-/m0/s1

> <INCHI_KEY>
ZSGWJLBSFZRJAT-MLXHEQMXSA-N

> <FORMULA>
C22H30O9

> <MOLECULAR_WEIGHT>
438.4682

> <EXACT_MASS>
438.188982558

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
44.423680094631806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl propanoate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.28784979566666713

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.072305054496205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64197376916336

> <JCHEM_POLAR_SURFACE_AREA>
120.89000000000001

> <JCHEM_REFRACTIVITY>
104.39359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038562
     RDKit          3D
8-Propanoylneosolaniol
 61 64  0  0  0  0  0  0  0  0999 V2000
    6.0137    0.4491    2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468    0.1180    0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484   -0.7607    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413   -1.9702    0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.1728   -0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.8625   -0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1994   -0.3074    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997   -0.0429   -0.3012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0805    1.4238   -0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1647    1.9282   -1.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489    3.2691   -1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    3.8063   -2.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    4.0043   -1.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408   -0.8182   -1.5611 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9696   -0.8509   -2.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467   -0.8715   -1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9120   -2.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -2.1237   -1.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -2.2804   -0.5026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8839   -1.3679   -0.7338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1799   -1.1403   -2.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148   -0.1287    0.0859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5106   -0.2109    1.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4164    0.8017    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461    0.7049    2.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229    1.8158    0.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491   -0.3103    0.6456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0961    0.4391    1.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678   -1.8200    0.8767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8653   -2.5459    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2487   -2.2204    1.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113    0.5511    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    1.4153    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6028   -0.3574    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7531   -0.3988    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451    1.0708    0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.9309   -0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    0.6237    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841   -1.0024    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049    2.0425    0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.6603   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    2.9992   -2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    4.6255   -3.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968    4.1737   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271   -0.3327   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -0.8593   -3.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2181   -0.7817   -3.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.9440   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -0.2337   -2.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -3.3445   -0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -1.9486   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097   -1.9538   -2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494    0.7934   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5734   -0.3839    2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576    1.1199    3.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2937    1.2133    2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.0005    2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414    1.1563    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -0.2406    2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -3.6431    1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -2.1322    2.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 16  6  1  0
 29 19  1  0
 27  8  1  0
 29 31  1  1
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  0
  9 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  6
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  1
 20 51  1  1
 21 52  1  0
 22 53  1  6
 25 54  1  0
 25 55  1  0
 25 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
M  END

HEADER    PROTEIN                                 25-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-13         0                                  
HETATM    1  C   UNK     0       1.249  -6.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.085  -7.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.085  -9.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.249 -10.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.582  -9.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.582  -7.691   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.916  -6.921   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.916 -10.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.250  -9.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.250  -7.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.419  -6.921   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.419 -10.001   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.582 -10.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.916 -11.541   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.790  -9.231   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.020 -10.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.351 -12.483   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.003  -9.854   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.498  -9.483   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.645 -13.995   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.752  -9.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.086 -10.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.420  -9.231   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.752  -7.691   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.249 -13.081   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.085 -13.851   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.249 -11.541   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.582 -13.851   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.645 -15.535   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.312 -16.305   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.979 -16.305   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   13                                             
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   14   17                                             
CONECT    9    8   10   16   15                                             
CONECT   10    9    7   18                                                  
CONECT   11    2                                                            
CONECT   12    3   21                                                       
CONECT   13    5   27                                                       
CONECT   14    8                                                            
CONECT   15   16    9                                                       
CONECT   16    9   15                                                       
CONECT   17    8   18   20                                                  
CONECT   18   10   17   19                                                  
CONECT   19   18                                                            
CONECT   20   17   29                                                       
CONECT   21   12   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   26   27   28                                                  
CONECT   26   25                                                            
CONECT   27   13   25                                                       
CONECT   28   25                                                            
CONECT   29   20   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0038562
HETATM    1  C1  UNL     1       6.014   0.449   2.089  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.847   0.118   0.628  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.648  -0.761   0.405  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.641  -1.970   0.656  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.526  -0.173  -0.099  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.293  -0.863  -0.373  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.199  -0.307   0.435  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.100  -0.043  -0.301  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.080   1.424  -0.615  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.165   1.928  -1.312  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.249   3.269  -1.653  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.425   3.806  -2.406  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.290   4.004  -1.297  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.241  -0.818  -1.561  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.970  -0.851  -2.393  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.147  -0.872  -1.822  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.423  -0.912  -2.645  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.666  -2.124  -1.367  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.694  -2.280  -0.503  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.884  -1.368  -0.734  1.00  0.00           C  
HETATM   21  O6  UNL     1      -3.180  -1.140  -2.050  1.00  0.00           O  
HETATM   22  C16 UNL     1      -2.615  -0.129   0.086  1.00  0.00           C  
HETATM   23  O7  UNL     1      -3.511  -0.211   1.213  1.00  0.00           O  
HETATM   24  C17 UNL     1      -4.416   0.802   1.422  1.00  0.00           C  
HETATM   25  C18 UNL     1      -5.346   0.705   2.600  1.00  0.00           C  
HETATM   26  O8  UNL     1      -4.523   1.816   0.688  1.00  0.00           O  
HETATM   27  C19 UNL     1      -1.249  -0.310   0.646  1.00  0.00           C  
HETATM   28  C20 UNL     1      -1.096   0.439   1.941  1.00  0.00           C  
HETATM   29  C21 UNL     1      -1.268  -1.820   0.877  1.00  0.00           C  
HETATM   30  C22 UNL     1      -0.865  -2.546   1.969  1.00  0.00           C  
HETATM   31  O9  UNL     1      -2.249  -2.220   1.840  1.00  0.00           O  
HETATM   32  H1  UNL     1       5.011   0.551   2.545  1.00  0.00           H  
HETATM   33  H2  UNL     1       6.529   1.415   2.245  1.00  0.00           H  
HETATM   34  H3  UNL     1       6.603  -0.357   2.595  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.753  -0.399   0.268  1.00  0.00           H  
HETATM   36  H5  UNL     1       5.745   1.071   0.082  1.00  0.00           H  
HETATM   37  H6  UNL     1       2.518  -1.931  -0.072  1.00  0.00           H  
HETATM   38  H7  UNL     1       1.571   0.624   0.948  1.00  0.00           H  
HETATM   39  H8  UNL     1       0.984  -1.002   1.271  1.00  0.00           H  
HETATM   40  H9  UNL     1       0.105   2.042   0.307  1.00  0.00           H  
HETATM   41  H10 UNL     1       0.831   1.660  -1.250  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.909   2.999  -2.991  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.057   4.625  -3.064  1.00  0.00           H  
HETATM   44  H13 UNL     1      -3.197   4.174  -1.697  1.00  0.00           H  
HETATM   45  H14 UNL     1      -1.027  -0.333  -2.215  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.909  -0.859  -3.500  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.218  -0.782  -3.711  1.00  0.00           H  
HETATM   48  H17 UNL     1       3.813  -1.944  -2.504  1.00  0.00           H  
HETATM   49  H18 UNL     1       4.183  -0.234  -2.229  1.00  0.00           H  
HETATM   50  H19 UNL     1      -2.001  -3.345  -0.506  1.00  0.00           H  
HETATM   51  H20 UNL     1      -3.761  -1.949  -0.322  1.00  0.00           H  
HETATM   52  H21 UNL     1      -3.610  -1.954  -2.412  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.849   0.793  -0.418  1.00  0.00           H  
HETATM   54  H23 UNL     1      -5.573  -0.384   2.721  1.00  0.00           H  
HETATM   55  H24 UNL     1      -4.858   1.120   3.513  1.00  0.00           H  
HETATM   56  H25 UNL     1      -6.294   1.213   2.431  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.168   1.001   2.037  1.00  0.00           H  
HETATM   58  H27 UNL     1      -1.941   1.156   2.052  1.00  0.00           H  
HETATM   59  H28 UNL     1      -1.160  -0.241   2.818  1.00  0.00           H  
HETATM   60  H29 UNL     1      -0.616  -3.643   1.850  1.00  0.00           H  
HETATM   61  H30 UNL     1      -0.351  -2.132   2.841  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   16   37
CONECT    7    8   38   39
CONECT    8    9   14   27
CONECT    9   10   40   41
CONECT   10   11
CONECT   11   12   13   13
CONECT   12   42   43   44
CONECT   14   15   18   45
CONECT   15   16   16   46
CONECT   16   17
CONECT   17   47   48   49
CONECT   18   19
CONECT   19   20   29   50
CONECT   20   21   22   51
CONECT   21   52
CONECT   22   23   27   53
CONECT   23   24
CONECT   24   25   26   26
CONECT   25   54   55   56
CONECT   27   28   29
CONECT   28   57   58   59
CONECT   29   30   31
CONECT   30   31   60   61
END

HMDB0038562
     RDKit          3D
8-Propanoylneosolaniol
 61 64  0  0  0  0  0  0  0  0999 V2000
    6.0137    0.4491    2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468    0.1180    0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484   -0.7607    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413   -1.9702    0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.1728   -0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.8625   -0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1994   -0.3074    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997   -0.0429   -0.3012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0805    1.4238   -0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1647    1.9282   -1.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489    3.2691   -1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    3.8063   -2.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    4.0043   -1.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408   -0.8182   -1.5611 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9696   -0.8509   -2.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467   -0.8715   -1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9120   -2.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -2.1237   -1.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -2.2804   -0.5026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8839   -1.3679   -0.7338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1799   -1.1403   -2.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148   -0.1287    0.0859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5106   -0.2109    1.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4164    0.8017    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461    0.7049    2.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229    1.8158    0.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491   -0.3103    0.6456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0961    0.4391    1.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678   -1.8200    0.8767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8653   -2.5459    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2487   -2.2204    1.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113    0.5511    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    1.4153    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6028   -0.3574    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7531   -0.3988    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451    1.0708    0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.9309   -0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    0.6237    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841   -1.0024    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049    2.0425    0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.6603   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    2.9992   -2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    4.6255   -3.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968    4.1737   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271   -0.3327   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -0.8593   -3.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2181   -0.7817   -3.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.9440   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -0.2337   -2.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -3.3445   -0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -1.9486   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097   -1.9538   -2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494    0.7934   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5734   -0.3839    2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576    1.1199    3.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2937    1.2133    2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.0005    2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414    1.1563    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -0.2406    2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -3.6431    1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -2.1322    2.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 16  6  1  0
 29 19  1  0
 27  8  1  0
 29 31  1  1
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  0
  9 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  6
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  1
 20 51  1  1
 21 52  1  0
 22 53  1  6
 25 54  1  0
 25 55  1  0
 25 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3-Hydroxy-4-methoxybenzyl)-6,7-dimethoxyisoquinoline	HMDB
3'-Hydroxypapaverine	HMDB
(1's,2S,2'r,4's,7'r,9'r,10'r,11's)-11'-(Acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl propanoic acid	HMDB

Chemical Formula

C₂₂H₃₀O₉

Average Molecular Weight

438.4682

Monoisotopic Molecular Weight

438.188982558

IUPAC Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl propanoate

Traditional Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl propanoate

CAS Registry Number

111112-47-1

SMILES

CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C

InChI Identifier

InChI=1S/C22H30O9/c1-6-16(25)30-14-8-21(9-27-12(3)23)15(7-11(14)2)31-19-17(26)18(29-13(4)24)20(21,5)22(19)10-28-22/h7,14-15,17-19,26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22-/m0/s1

InChI Key

ZSGWJLBSFZRJAT-MLXHEQMXSA-N

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
Tricarboxylic acid or derivatives
Oxepane
Oxane
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038562)

Cellular substructure

Extracellular (HMDB: HMDB0038562)
Cytoplasm (HMDB: HMDB0038562)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038562)

Source

Endogenous

Endogenous (HMDB: HMDB0038562)

Animal

Animal (HMDB: HMDB0038562)

Exogenous

Food

Food (HMDB: HMDB0038562)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038562)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038562)

Cellular process

Cell signaling (HMDB: HMDB0038562)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038562)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038562)

Nutrient

Nutrient (HMDB: HMDB0038562)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.03 g/L	ALOGPS
logP	1.4	ALOGPS
logP	0.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.39 m³·mol⁻¹	ChemAxon
Polarizability	44.42 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	202.636	31661259
DarkChem	[M-H]-	197.165	31661259
DeepCCS	[M-2H]-	234.407	30932474
DeepCCS	[M+Na]+	208.602	30932474
AllCCS	[M+H]+	201.2	32859911
AllCCS	[M+H-H2O]+	199.1	32859911
AllCCS	[M+NH4]+	203.0	32859911
AllCCS	[M+Na]+	203.6	32859911
AllCCS	[M-H]-	202.7	32859911
AllCCS	[M+Na-2H]-	203.5	32859911
AllCCS	[M+HCOO]-	204.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Propanoylneosolaniol	CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C	3774.0	Standard polar	33892256
8-Propanoylneosolaniol	CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C	2625.6	Standard non polar	33892256
8-Propanoylneosolaniol	CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C	2748.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Propanoylneosolaniol,1TMS,isomer #1	CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@@H](C=C1C)O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](OC(C)=O)[C@@]2(C)[C@]12CO2	2694.4	Semi standard non polar	33892256
8-Propanoylneosolaniol,1TBDMS,isomer #1	CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@@H](C=C1C)O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](OC(C)=O)[C@@]2(C)[C@]12CO2	2926.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Propanoylneosolaniol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0403-4049000000-d115b39630aeece1635e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Propanoylneosolaniol GC-MS (1 TMS) - 70eV, Positive	splash10-000i-8059800000-54f93b86e5df08994ae5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Propanoylneosolaniol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Propanoylneosolaniol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 10V, Positive-QTOF	splash10-05ds-4009400000-cb9858b3587b7109f82c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 20V, Positive-QTOF	splash10-0ab9-4209100000-00b78b6544f99f24dfbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 40V, Positive-QTOF	splash10-0ab9-9108000000-30c90badecf716957733	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 10V, Negative-QTOF	splash10-000j-5009600000-6be102a2992ef60f2bf8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 20V, Negative-QTOF	splash10-0a4i-8209200000-bb8761e416df51d65d44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 40V, Negative-QTOF	splash10-0a4j-6900000000-0dd057b43862d711226e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 10V, Positive-QTOF	splash10-0ab9-0009000000-45d686b7a96ff33c2190	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 20V, Positive-QTOF	splash10-0a4i-1009000000-ef8eb403238bd216a269	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 40V, Positive-QTOF	splash10-05mx-9012000000-646eaa3cabdea128de0b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 10V, Negative-QTOF	splash10-00di-6019200000-9d24468b96c21b6d10bd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 20V, Negative-QTOF	splash10-0abi-9003000000-b423fec64f40bb621b97	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Propanoylneosolaniol 40V, Negative-QTOF	splash10-008c-9033000000-0220a8fed4c232238bee	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017949

KNApSAcK ID

C00056850

Chemspider ID

159277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

167736

PDB ID

Not Available

ChEBI ID

180728

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 8-Propanoylneosolaniol (HMDB0038562)

MOL for HMDB0038562 (8-Propanoylneosolaniol)

3D MOL for HMDB0038562 (8-Propanoylneosolaniol)

3D SDF for HMDB0038562 (8-Propanoylneosolaniol)

3D-SDF for HMDB0038562 (8-Propanoylneosolaniol)

PDB for HMDB0038562 (8-Propanoylneosolaniol)

3D PDB for HMDB0038562 (8-Propanoylneosolaniol)

SMILES for HMDB0038562 (8-Propanoylneosolaniol)

INCHI for HMDB0038562 (8-Propanoylneosolaniol)

Structure for HMDB0038562 (8-Propanoylneosolaniol)

3D Structure for HMDB0038562 (8-Propanoylneosolaniol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra