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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:45 UTC

Update Date

2022-03-07 02:52:57 UTC

HMDB ID

HMDB0031380

Secondary Accession Numbers

HMDB31380

Metabolite Identification

Common Name

(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide

Description

(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a significant number of articles have been published on (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide.

Structure

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


  Mrv0541 02241208582D          

 28 32  0  0  0  0            999 V2000
   -2.4192   -0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4192   -1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -1.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917   -1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917   -0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048    0.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -1.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355   -1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355   -0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773    0.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645    0.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178   -2.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -2.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701    1.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -1.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    1.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975    1.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    2.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993    1.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    2.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -0.2822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7 28  1  0  0  0  0
  8  9  1  0  0  0  0
  8 21  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  2  0  0  0  0
 14 15  2  0  0  0  0
 14 27  1  0  0  0  0
 15 16  1  0  0  0  0
 16 26  2  0  0  0  0
 19 20  2  0  0  0  0
 19 28  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

HMDB0031380
     RDKit          3D
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide
 56 60  0  0  0  0  0  0  0  0999 V2000
    1.2194   -3.3861    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -2.1692   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -2.2032   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -0.8964   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850   -0.5296   -2.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560    0.0084   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    0.9426   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083    1.8119   -1.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1656    1.7741    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002    0.7122   -1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559    1.2362   -2.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    0.6477   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642   -0.2475    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -0.4318    2.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686   -1.7797    2.4717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    0.3485    2.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    1.7125    2.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459    2.4130    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    3.6261    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    1.4200    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569    1.9380   -1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678    0.8147   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1377   -0.5299   -1.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594   -0.4439    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188   -0.0466   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -1.8024    0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    0.5962    0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140   -0.8527    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698   -3.5143    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -4.3266   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -3.3849    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -3.0536   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522    0.2977   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    1.5774   -1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    1.7529   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9124    2.8863   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    1.9737    0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    1.3194    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    2.7679    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695   -0.0355    2.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -1.8123    3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722   -0.0360    3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4364    2.6936   -0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8861    2.4828   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.7115   -2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    1.0728   -2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650   -1.1762   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -1.0524   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447   -0.6910   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8636   -0.2171    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2874    1.0221   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -1.6397    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -2.5064    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8424   -2.3248    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708    1.3958    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.8661    1.1362 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 13 28  1  0
 28  2  1  0
 28  6  1  0
 20 12  1  0
 27 16  1  0
 27 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
M  END


  Mrv0541 02241208582D          

 28 32  0  0  0  0            999 V2000
   -2.4192   -0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4192   -1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -1.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917   -1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917   -0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048    0.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -1.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355   -1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355   -0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773    0.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645    0.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178   -2.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -2.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701    1.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -1.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    1.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975    1.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    2.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993    1.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    2.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -0.2822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7 28  1  0  0  0  0
  8  9  1  0  0  0  0
  8 21  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  2  0  0  0  0
 14 15  2  0  0  0  0
 14 27  1  0  0  0  0
 15 16  1  0  0  0  0
 16 26  2  0  0  0  0
 19 20  2  0  0  0  0
 19 28  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031380

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C12C(C(C)=CC1=O)C1=C(C2=O)C23CCCC(C)(C)C2C(OC3=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O5/c1-10(2)23-12(24)9-11(3)14(23)13-15(19(23)26)22-8-6-7-21(4,5)18(22)17(16(13)25)28-20(22)27/h9-10,14,16-18,25H,6-8H2,1-5H3

> <INCHI_KEY>
IEPYKUBVROCHOQ-UHFFFAOYSA-N

> <FORMULA>
C23H28O5

> <MOLECULAR_WEIGHT>
384.4654

> <EXACT_MASS>
384.193674006

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.09718852354684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-7,13,13-trimethyl-4-(propan-2-yl)-18-oxapentacyclo[9.5.2.0¹,¹².0²,⁹.0⁴,⁸]octadeca-2(9),6-diene-3,5,17-trione

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.293089614

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.075437589610083

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.815570360554126

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4575307188895126

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
103.44039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-4-isopropyl-7,13,13-trimethyl-18-oxapentacyclo[9.5.2.0¹,¹².0²,⁹.0⁴,⁸]octadeca-2(9),6-diene-3,5,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031380
     RDKit          3D
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide
 56 60  0  0  0  0  0  0  0  0999 V2000
    1.2194   -3.3861    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -2.1692   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -2.2032   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -0.8964   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850   -0.5296   -2.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560    0.0084   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    0.9426   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083    1.8119   -1.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1656    1.7741    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002    0.7122   -1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559    1.2362   -2.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    0.6477   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642   -0.2475    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -0.4318    2.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686   -1.7797    2.4717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    0.3485    2.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    1.7125    2.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459    2.4130    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    3.6261    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    1.4200    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569    1.9380   -1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678    0.8147   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1377   -0.5299   -1.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594   -0.4439    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188   -0.0466   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -1.8024    0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    0.5962    0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140   -0.8527    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698   -3.5143    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -4.3266   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -3.3849    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -3.0536   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522    0.2977   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    1.5774   -1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    1.7529   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9124    2.8863   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    1.9737    0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    1.3194    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    2.7679    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695   -0.0355    2.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -1.8123    3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722   -0.0360    3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4364    2.6936   -0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8861    2.4828   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.7115   -2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    1.0728   -2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650   -1.1762   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -1.0524   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447   -0.6910   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8636   -0.2171    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2874    1.0221   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -1.6397    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -2.5064    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8424   -2.3248    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708    1.3958    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.8661    1.1362 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 13 28  1  0
 28  2  1  0
 28  6  1  0
 20 12  1  0
 27 16  1  0
 27 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.516  -0.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.516  -2.222   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.182  -2.993   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.851  -2.222   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.851  -0.681   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.182   0.087   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.518  -2.993   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.813  -2.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.813  -0.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.518   0.087   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.954   0.347   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.327   1.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.204   1.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.480   0.511   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.794   2.012   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.460   2.775   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.953  -4.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.411  -4.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.453   0.809   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.438   2.351   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.149  -2.993   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.975   2.922   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.929   3.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.021   4.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.559   3.641   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.460   4.317   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.516  -0.632   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.682  -0.527   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17   18                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   28                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9   13                                                  
CONECT   11    9   12   14                                                  
CONECT   12   11   13   16   23                                             
CONECT   13   10   12   22                                                  
CONECT   14   11   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   12   15   26                                                  
CONECT   17    3                                                            
CONECT   18    3                                                            
CONECT   19    5   20   28                                                  
CONECT   20   19                                                            
CONECT   21    8                                                            
CONECT   22   13                                                            
CONECT   23   12   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   16                                                            
CONECT   27   14                                                            
CONECT   28    7   19                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0031380
HETATM    1  C1  UNL     1       1.219  -3.386   0.386  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.787  -2.169  -0.247  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.253  -2.203  -1.503  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.750  -0.896  -1.882  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.385  -0.530  -2.899  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.356   0.008  -0.792  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.474   0.943  -0.420  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.908   1.812  -1.572  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.166   1.774   0.783  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.100   0.712  -1.154  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.956   1.236  -2.289  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.201   0.648  -0.011  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.664  -0.247   0.877  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.104  -0.432   2.110  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.269  -1.780   2.472  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.360   0.348   2.201  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.968   1.713   2.491  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.846   2.413   1.304  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.621   3.626   1.185  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.038   1.420   0.215  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.657   1.938  -1.013  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.168   0.815  -1.858  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.138  -0.530  -1.195  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.759  -0.444   0.209  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.219  -0.047  -0.118  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.872  -1.802   0.833  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.107   0.596   0.951  1.00  0.00           C  
HETATM   28  C23 UNL     1       1.914  -0.853   0.364  1.00  0.00           C  
HETATM   29  H1  UNL     1       1.570  -3.514   1.432  1.00  0.00           H  
HETATM   30  H2  UNL     1       1.543  -4.327  -0.141  1.00  0.00           H  
HETATM   31  H3  UNL     1       0.116  -3.385   0.284  1.00  0.00           H  
HETATM   32  H4  UNL     1       2.282  -3.054  -2.186  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.352   0.298  -0.165  1.00  0.00           H  
HETATM   34  H6  UNL     1       4.948   1.577  -1.921  1.00  0.00           H  
HETATM   35  H7  UNL     1       3.230   1.753  -2.423  1.00  0.00           H  
HETATM   36  H8  UNL     1       3.912   2.886  -1.231  1.00  0.00           H  
HETATM   37  H9  UNL     1       2.095   1.974   0.838  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.592   1.319   1.695  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.668   2.768   0.665  1.00  0.00           H  
HETATM   40  H12 UNL     1       0.569  -0.036   2.936  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.884  -1.812   3.227  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.972  -0.036   3.018  1.00  0.00           H  
HETATM   43  H15 UNL     1      -2.436   2.694  -0.779  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.886   2.483  -1.612  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.674   0.712  -2.845  1.00  0.00           H  
HETATM   46  H18 UNL     1      -3.238   1.073  -2.118  1.00  0.00           H  
HETATM   47  H19 UNL     1      -2.865  -1.176  -1.773  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.189  -1.052  -1.215  1.00  0.00           H  
HETATM   49  H21 UNL     1      -4.545  -0.691  -0.942  1.00  0.00           H  
HETATM   50  H22 UNL     1      -4.864  -0.217   0.765  1.00  0.00           H  
HETATM   51  H23 UNL     1      -4.287   1.022  -0.368  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.958  -1.640   1.942  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.090  -2.506   0.549  1.00  0.00           H  
HETATM   54  H26 UNL     1      -3.842  -2.325   0.575  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.871   1.396   1.229  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.715  -0.866   1.136  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3   28
CONECT    3    4   32
CONECT    4    5    5    6
CONECT    6    7   10   28
CONECT    7    8    9   33
CONECT    8   34   35   36
CONECT    9   37   38   39
CONECT   10   11   11   12
CONECT   12   13   13   20
CONECT   13   14   28
CONECT   14   15   16   40
CONECT   15   41
CONECT   16   17   27   42
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   27
CONECT   21   22   43   44
CONECT   22   23   45   46
CONECT   23   24   47   48
CONECT   24   25   26   27
CONECT   25   49   50   51
CONECT   26   52   53   54
CONECT   27   55
CONECT   28   56
END

HMDB0031380
     RDKit          3D
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide
 56 60  0  0  0  0  0  0  0  0999 V2000
    1.2194   -3.3861    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -2.1692   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -2.2032   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -0.8964   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850   -0.5296   -2.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560    0.0084   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    0.9426   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083    1.8119   -1.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1656    1.7741    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002    0.7122   -1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559    1.2362   -2.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    0.6477   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642   -0.2475    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -0.4318    2.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686   -1.7797    2.4717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    0.3485    2.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    1.7125    2.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459    2.4130    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    3.6261    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    1.4200    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569    1.9380   -1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678    0.8147   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1377   -0.5299   -1.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594   -0.4439    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188   -0.0466   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -1.8024    0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    0.5962    0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140   -0.8527    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698   -3.5143    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -4.3266   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -3.3849    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -3.0536   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522    0.2977   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    1.5774   -1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    1.7529   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9124    2.8863   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    1.9737    0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    1.3194    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    2.7679    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695   -0.0355    2.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -1.8123    3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722   -0.0360    3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4364    2.6936   -0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8861    2.4828   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.7115   -2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    1.0728   -2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650   -1.1762   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -1.0524   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447   -0.6910   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8636   -0.2171    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2874    1.0221   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -1.6397    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -2.5064    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8424   -2.3248    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708    1.3958    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.8661    1.1362 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 13 28  1  0
 28  2  1  0
 28  6  1  0
 20 12  1  0
 27 16  1  0
 27 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6b,7a,12b,13b)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	Generator
(6Β,7α,12β,13β)-7-hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	Generator

Chemical Formula

C₂₃H₂₈O₅

Average Molecular Weight

384.4654

Monoisotopic Molecular Weight

384.193674006

IUPAC Name

10-hydroxy-7,13,13-trimethyl-4-(propan-2-yl)-18-oxapentacyclo[9.5.2.0¹,¹².0²,⁹.0⁴,⁸]octadeca-2(9),6-diene-3,5,17-trione

Traditional Name

10-hydroxy-4-isopropyl-7,13,13-trimethyl-18-oxapentacyclo[9.5.2.0¹,¹².0²,⁹.0⁴,⁸]octadeca-2(9),6-diene-3,5,17-trione

CAS Registry Number

403613-16-1

SMILES

CC(C)C12C(C(C)=CC1=O)C1=C(C2=O)C23CCCC(C)(C)C2C(OC3=O)C1O

InChI Identifier

InChI=1S/C23H28O5/c1-10(2)23-12(24)9-11(3)14(23)13-15(19(23)26)22-8-6-7-21(4,5)18(22)17(16(13)25)28-20(22)27/h9-10,14,16-18,25H,6-8H2,1-5H3

InChI Key

IEPYKUBVROCHOQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031380)

Source

Exogenous

Food

Food (HMDB: HMDB0031380)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031380)

Endogenous

Plant

Plant (HMDB: HMDB0031380)

Animal

Animal (HMDB: HMDB0031380)

Endogenous (HMDB: HMDB0031380)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031380)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031380)

Lipid metabolism pathway (HMDB: HMDB0031380)

Cellular process

Cell signaling (HMDB: HMDB0031380)

Biochemical process

Lipid transport (HMDB: HMDB0031380)

Role

Biological role

Energy source (HMDB: HMDB0031380)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031380)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	245 °C	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	0.11 g/L	ALOGPS
logP	2.96	ALOGPS
logP	3.29	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.82	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	103.44 m³·mol⁻¹	ChemAxon
Polarizability	40.1 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	187.98	31661259
DarkChem	[M-H]-	187.352	31661259
DeepCCS	[M-2H]-	229.608	30932474
DeepCCS	[M+Na]+	204.836	30932474
AllCCS	[M+H]+	189.0	32859911
AllCCS	[M+H-H2O]+	186.5	32859911
AllCCS	[M+NH4]+	191.3	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	197.7	32859911
AllCCS	[M+Na-2H]-	197.9	32859911
AllCCS	[M+HCOO]-	198.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.45 minutes	32390414
Predicted by Siyang on May 30, 2022	16.049 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2976.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	320.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	140.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	625.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	833.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1244.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	562.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1687.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	208.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	255.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	CC(C)C12C(C(C)=CC1=O)C1=C(C2=O)C23CCCC(C)(C)C2C(OC3=O)C1O	3889.3	Standard polar	33892256
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	CC(C)C12C(C(C)=CC1=O)C1=C(C2=O)C23CCCC(C)(C)C2C(OC3=O)C1O	2927.2	Standard non polar	33892256
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	CC(C)C12C(C(C)=CC1=O)C1=C(C2=O)C23CCCC(C)(C)C2C(OC3=O)C1O	2963.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide,1TMS,isomer #1	CC1=CC(=O)C2(C(C)C)C(=O)C3=C(C(O[Si](C)(C)C)C4OC(=O)C35CCCC(C)(C)C45)C12	2933.7	Semi standard non polar	33892256
(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide,1TBDMS,isomer #1	CC1=CC(=O)C2(C(C)C)C(=O)C3=C(C(O[Si](C)(C)C(C)(C)C)C4OC(=O)C35CCCC(C)(C)C45)C12	3134.6	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 - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-4935000000-e817af62ede7e6781fc4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide GC-MS (1 TMS) - 70eV, Positive	splash10-047u-9412300000-f5f3c91584e40bda4bf5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 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 - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 10V, Positive-QTOF	splash10-000i-0009000000-437cd2eca9d88ad06c5c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 20V, Positive-QTOF	splash10-014r-2129000000-37b6ff4a2e6a02b20514	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 40V, Positive-QTOF	splash10-01b9-9464000000-bd167c35d2dcaabcf8bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 10V, Negative-QTOF	splash10-001i-0009000000-11fc57598cf6c5282e05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 20V, Negative-QTOF	splash10-001i-0009000000-e7e67bc3b31bc597cb59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 40V, Negative-QTOF	splash10-02g9-1923000000-d2e0ff755b2d0e5bc15e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 10V, Negative-QTOF	splash10-001i-0009000000-a1f14e47f80cf18311f3	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 20V, Negative-QTOF	splash10-001r-0009000000-e580a84f708d2c7ebd52	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 40V, Negative-QTOF	splash10-014i-3719000000-44feec1ac79fbf693984	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 10V, Positive-QTOF	splash10-000i-0009000000-feedb729141e890033a0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 20V, Positive-QTOF	splash10-00kr-0009000000-25f6778205961372084e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide 40V, Positive-QTOF	splash10-014r-1319000000-49071520eda573e8c52c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB003447

KNApSAcK ID

Not Available

Chemspider ID

35013356

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73880583

PDB ID

Not Available

ChEBI ID

175053

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 (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide (HMDB0031380)

MOL for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D MOL for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D SDF for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D-SDF for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

PDB for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D PDB for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

SMILES for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

INCHI for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

Structure for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D Structure for HMDB0031380 ((6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra