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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:54:18 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036735

Secondary Accession Numbers

HMDB36735

Metabolite Identification

Common Name

Bilobalide A

Description

Bilobalide A belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. Bilobalide A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0036735
     RDKit          3D
Bilobalide A
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.8340   -1.0260   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    0.1223    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    1.3599   -0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770    0.2287    1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -0.2400   -0.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5497   -0.4146   -1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565   -1.6436    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.8083   -0.7876 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9367   -2.8050   -0.3031 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -2.2009    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255   -2.7417    0.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -0.8023    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376   -0.4784   -0.5622 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3894    0.1084   -1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560   -0.5075   -2.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    1.4701   -1.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460    1.6219   -1.1339 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7911    2.8369   -0.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    2.5947    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281    3.4156    1.8382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    1.1264    1.1283 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6757    0.6418    2.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6516    0.5005   -0.1012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8290   -0.6367   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302   -1.7292    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -1.6252   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    1.5367   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.2566   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852    2.2724    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -0.5750    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513    1.2358    1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948    0.1353    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869   -0.1719   -2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168   -2.3934   -0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -1.6190    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -1.9740   -1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229   -0.1981    0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.8838    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    1.5483   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    1.1440    1.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5181    1.3184    3.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23  5  1  1
 13  8  1  0
 23 17  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  6
 12 37  1  0
 12 38  1  0
 17 39  1  6
 21 40  1  1
 22 41  1  0
M  END


  Mrv0541 01101310022D          

 25 28  0  0  0  0            999 V2000
    0.3884   -1.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609   -1.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285   -2.1995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0254   -2.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4747   -1.7212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1709   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1853   -1.3757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7401   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9555   -0.2551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9555   -1.0800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7402   -1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2250   -0.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.8972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390   -0.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9555    0.5699    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -0.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2716   -1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872   -2.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685   -1.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -2.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717   -3.0234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 12  6  1  0  0  0  0
  4  9  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
  2 15  2  0  0  0  0
  8 16  2  0  0  0  0
 11 17  1  1  0  0  0
 14 18  2  0  0  0  0
 13 19  1  1  0  0  0
  6 20  1  6  0  0  0
  6 21  1  1  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
  4 25  1  1  0  0  0
  9  8  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0036735

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1

> <INCHI_KEY>
MOLPUWBMSBJXER-NRSGSQFTSA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.2986

> <EXACT_MASS>
326.100167552

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.39069790074211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-0.5177614286666664

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.776747765035385

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.974249820349915

> <JCHEM_PKA_STRONGEST_BASIC>
-3.37953725747988

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
69.98790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036735
     RDKit          3D
Bilobalide A
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.8340   -1.0260   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    0.1223    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    1.3599   -0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770    0.2287    1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -0.2400   -0.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5497   -0.4146   -1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565   -1.6436    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.8083   -0.7876 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9367   -2.8050   -0.3031 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -2.2009    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255   -2.7417    0.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -0.8023    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376   -0.4784   -0.5622 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3894    0.1084   -1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560   -0.5075   -2.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    1.4701   -1.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460    1.6219   -1.1339 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7911    2.8369   -0.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    2.5947    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281    3.4156    1.8382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    1.1264    1.1283 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6757    0.6418    2.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6516    0.5005   -0.1012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8290   -0.6367   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302   -1.7292    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -1.6252   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    1.5367   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.2566   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852    2.2724    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -0.5750    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513    1.2358    1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948    0.1353    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869   -0.1719   -2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168   -2.3934   -0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -1.6190    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -1.9740   -1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229   -0.1981    0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.8838    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    1.5483   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    1.1440    1.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5181    1.3184    3.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23  5  1  1
 13  8  1  0
 23 17  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  6
 12 37  1  0
 12 38  1  0
 17 39  1  6
 21 40  1  1
 22 41  1  0
M  END

HEADER    PROTEIN                                 10-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JAN-13         0                                  
HETATM    1  C   UNK     0       0.725  -2.169   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.114  -3.461   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.855  -4.658   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.293  -4.106   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.781  -4.504   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.619  -3.213   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.186  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.281  -1.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.213  -2.568   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.115  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.650  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.650  -2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.115  -2.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.020  -1.246   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.651  -3.541   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.259  -1.235   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       3.650   1.064   0.000  0.00  0.00           H+0
HETATM   18  O   UNK     0       7.560  -1.246   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.655  -2.492   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.107  -3.611   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.389  -4.546   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.595  -3.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.595  -4.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.196  -4.700   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       2.374  -5.644   0.000  0.00  0.00           H+0
CONECT    1    2    9                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   25                                             
CONECT    5    4    6                                                       
CONECT    6    5   12   20   21                                             
CONECT    7    8   11                                                       
CONECT    8    7   16    9                                                  
CONECT    9    1    4   12    8                                             
CONECT   10   11   14                                                       
CONECT   11    7   10   12   17                                             
CONECT   12    6    9   13   11                                             
CONECT   13   12   14   19                                                  
CONECT   14   13   10   18                                                  
CONECT   15    2                                                            
CONECT   16    8                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   13                                                            
CONECT   20    6   22   23   24                                             
CONECT   21    6                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   20                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036735
HETATM    1  C1  UNL     1      -2.834  -1.026  -0.418  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.898   0.122   0.025  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.479   1.360  -0.570  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.177   0.229   1.528  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.553  -0.240  -0.354  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.550  -0.415  -1.776  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.157  -1.644   0.133  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.069  -1.808  -0.788  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.937  -2.805  -0.303  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.115  -2.201   0.158  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.225  -2.742   0.214  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.704  -0.802   0.546  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.738  -0.478  -0.562  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.389   0.108  -1.715  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.056  -0.507  -2.580  1.00  0.00           O  
HETATM   16  O5  UNL     1       2.129   1.470  -1.668  1.00  0.00           O  
HETATM   17  C12 UNL     1       0.846   1.622  -1.134  1.00  0.00           C  
HETATM   18  O6  UNL     1       0.791   2.837  -0.430  1.00  0.00           O  
HETATM   19  C13 UNL     1       0.758   2.595   0.926  1.00  0.00           C  
HETATM   20  O7  UNL     1       0.528   3.416   1.838  1.00  0.00           O  
HETATM   21  C14 UNL     1       1.054   1.126   1.128  1.00  0.00           C  
HETATM   22  O8  UNL     1       0.676   0.642   2.336  1.00  0.00           O  
HETATM   23  C15 UNL     1       0.652   0.501  -0.101  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.829  -0.637  -0.712  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.030  -1.729   0.427  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.399  -1.625  -1.217  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.282   1.537  -1.625  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.606   1.257  -0.495  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.285   2.272   0.064  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.748  -0.575   2.113  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.951   1.236   1.930  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.295   0.135   1.709  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.387  -0.172  -2.186  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.917  -2.393  -0.055  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.259  -1.619   1.147  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.744  -1.974  -1.821  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.623  -0.198   0.505  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.254  -0.884   1.533  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.118   1.548  -1.951  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.194   1.144   1.165  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.518   1.318   3.037  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4    5
CONECT    3   27   28   29
CONECT    4   30   31   32
CONECT    5    6    7   23
CONECT    6   33
CONECT    7    8   34   35
CONECT    8    9   13   36
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   37   38
CONECT   13   14   23
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   23   39
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   23   40
CONECT   22   41
END

HMDB0036735
     RDKit          3D
Bilobalide A
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.8340   -1.0260   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    0.1223    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    1.3599   -0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770    0.2287    1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -0.2400   -0.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5497   -0.4146   -1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565   -1.6436    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.8083   -0.7876 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9367   -2.8050   -0.3031 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -2.2009    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255   -2.7417    0.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -0.8023    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376   -0.4784   -0.5622 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3894    0.1084   -1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560   -0.5075   -2.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    1.4701   -1.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460    1.6219   -1.1339 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7911    2.8369   -0.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    2.5947    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281    3.4156    1.8382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    1.1264    1.1283 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6757    0.6418    2.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6516    0.5005   -0.1012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8290   -0.6367   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302   -1.7292    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -1.6252   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    1.5367   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.2566   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852    2.2724    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -0.5750    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513    1.2358    1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948    0.1353    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869   -0.1719   -2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168   -2.3934   -0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -1.6190    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -1.9740   -1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229   -0.1981    0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.8838    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    1.5483   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    1.1440    1.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5181    1.3184    3.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23  5  1  1
 13  8  1  0
 23 17  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  6
 12 37  1  0
 12 38  1  0
 17 39  1  6
 21 40  1  1
 22 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Bilobalide	HMDB
(-)-Bilobalide	MeSH

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.2986

Monoisotopic Molecular Weight

326.100167552

IUPAC Name

(1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione

Traditional Name

(1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione

CAS Registry Number

33570-04-6

SMILES

[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2

InChI Identifier

InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1

InChI Key

MOLPUWBMSBJXER-NRSGSQFTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ginkgolides and bilobalides

Alternative Parents

Substituents

Bilobalide
Diterpenoid
Tricarboxylic acid or derivatives
Furofuran
Acylal
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
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

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °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	10.3 g/L	ALOGPS
logP	0.16	ALOGPS
logP	-0.52	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	11.97	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.99 m³·mol⁻¹	ChemAxon
Polarizability	29.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.31	31661259
DarkChem	[M-H]-	171.773	31661259
DeepCCS	[M-2H]-	209.093	30932474
DeepCCS	[M+Na]+	185.509	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	176.0	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bilobalide A	[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2	3941.5	Standard polar	33892256
Bilobalide A	[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2	2296.2	Standard non polar	33892256
Bilobalide A	[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2	2718.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bilobalide A,1TMS,isomer #1	CC(C)(C)[C@]1(O[Si](C)(C)C)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]2OC(=O)[C@@H](O)[C@@]231	2613.2	Semi standard non polar	33892256
Bilobalide A,1TMS,isomer #2	CC(C)(C)[C@]1(O)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]2OC(=O)[C@@H](O[Si](C)(C)C)[C@@]231	2641.9	Semi standard non polar	33892256
Bilobalide A,2TMS,isomer #1	CC(C)(C)[C@]1(O[Si](C)(C)C)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]2OC(=O)[C@@H](O[Si](C)(C)C)[C@@]231	2682.0	Semi standard non polar	33892256
Bilobalide A,1TBDMS,isomer #1	CC(C)(C)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]2OC(=O)[C@@H](O)[C@@]231	2841.1	Semi standard non polar	33892256
Bilobalide A,1TBDMS,isomer #2	CC(C)(C)[C@]1(O)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]2OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]231	2852.5	Semi standard non polar	33892256
Bilobalide A,2TBDMS,isomer #1	CC(C)(C)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]2OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]231	3108.0	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 - Bilobalide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-7090000000-409b29d29f5d92b036e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilobalide A GC-MS (2 TMS) - 70eV, Positive	splash10-06dr-9025400000-db65ccd917ab30b1e85a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilobalide A 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 - Bilobalide A 10V, Positive-QTOF	splash10-0a6r-0039000000-fd571dbea940514eb044	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 20V, Positive-QTOF	splash10-0a7i-1096000000-473f19a2a3e09916098b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 40V, Positive-QTOF	splash10-014r-3091000000-c7c1e8b2c82cbd9fa2db	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 10V, Negative-QTOF	splash10-0059-0089000000-7e83fcc43328f0da5170	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 20V, Negative-QTOF	splash10-057i-0097000000-41ff44d74a98fc8c733b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 40V, Negative-QTOF	splash10-000l-3190000000-cc31694b1766c38571fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 10V, Negative-QTOF	splash10-004i-0009000000-860df1894ebe815b95f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 20V, Negative-QTOF	splash10-004i-2039000000-09a3e28dac6072fa36c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 40V, Negative-QTOF	splash10-000i-1190000000-ea4455a1fec72fb52745	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 10V, Positive-QTOF	splash10-004i-0009000000-0de6306d29da47cbad7b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 20V, Positive-QTOF	splash10-056r-0039000000-e3b3433b12e8c877e6be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilobalide A 40V, Positive-QTOF	splash10-0a4l-9020000000-72a7050fc022305ce16d	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11875005

PDB ID

Not Available

ChEBI ID

Not Available

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 Bilobalide A (HMDB0036735)

MOL for HMDB0036735 (Bilobalide A)

3D MOL for HMDB0036735 (Bilobalide A)

3D SDF for HMDB0036735 (Bilobalide A)

3D-SDF for HMDB0036735 (Bilobalide A)

PDB for HMDB0036735 (Bilobalide A)

3D PDB for HMDB0036735 (Bilobalide A)

SMILES for HMDB0036735 (Bilobalide A)

INCHI for HMDB0036735 (Bilobalide A)

Structure for HMDB0036735 (Bilobalide A)

3D Structure for HMDB0036735 (Bilobalide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra