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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:19:31 UTC

Update Date

2022-03-07 02:54:50 UTC

HMDB ID

HMDB0036263

Secondary Accession Numbers

HMDB36263

Metabolite Identification

Common Name

Annoglabasin C

Description

Annoglabasin C belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Annoglabasin C is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 05061308582D          

 29 32  0  0  0  0            999 V2000
   -0.0795   -0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    3.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -0.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    2.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    1.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290    2.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    1.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 14  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  7  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  3  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  0  0  0  0
 23 15  1  0  0  0  0
 23 19  1  0  0  0  0
 24 14  2  0  0  0  0
 25 18  2  0  0  0  0
 26 18  1  0  0  0  0
 27 19  2  0  0  0  0
 28  4  1  0  0  0  0
 28 19  1  0  0  0  0
 29 14  1  0  0  0  0
 29 23  1  0  0  0  0
M  END

HMDB0036263
     RDKit          3D
Annoglabasin C
 63 66  0  0  0  0  0  0  0  0999 V2000
    4.5536    3.4756    1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    2.5672    0.9406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8150    1.2145    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9653    0.8174    1.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    0.2193    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275   -1.0907    0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -1.3790   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -2.7302   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793   -0.5051   -1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5580    0.2634    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    0.7277    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4107    1.6876    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116    1.0262    1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    0.3618    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034    0.1409    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4805    1.4397   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2895    0.0710    1.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6231    0.1645    2.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6715   -0.1252    1.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3824   -1.0083   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535   -1.5929   -1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001   -1.4987   -1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -0.8226   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -1.8371    0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -0.2598   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -1.3046   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246   -0.5934   -1.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4459    0.5907   -1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    1.5894   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3079    3.7805    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    4.4171    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5857    3.1295    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461   -3.2697    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3205   -2.6456   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757   -3.2823   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154   -0.7146    1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    0.9959    1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664    2.0705    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    2.5663    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4608    0.2708    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611    1.8137    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802    1.0956   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4988    1.2397   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9076    1.8426   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    2.2258    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9203   -1.0381    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3768   -0.6905   -0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -1.8136    0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8441   -2.6837   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875   -1.1618   -2.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   -2.5214   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673   -1.0214   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -1.9864    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -2.8428    0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946   -1.6128    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    0.2739   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873   -1.9194   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327   -1.9823   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673   -0.2094   -2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7423   -1.2882   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    1.0726   -1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    1.8046   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    2.4756   -0.3205 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
  7  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28  5  1  0
 25 11  1  0
 29 11  1  0
 23 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 29 62  1  0
 29 63  1  0
M  END


  Mrv0541 05061308582D          

 29 32  0  0  0  0            999 V2000
   -0.0795   -0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    3.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -0.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    2.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    1.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290    2.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    1.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 14  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  7  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  3  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  0  0  0  0
 23 15  1  0  0  0  0
 23 19  1  0  0  0  0
 24 14  2  0  0  0  0
 25 18  2  0  0  0  0
 26 18  1  0  0  0  0
 27 19  2  0  0  0  0
 28  4  1  0  0  0  0
 28 19  1  0  0  0  0
 29 14  1  0  0  0  0
 29 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036263

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O6/c1-14(24)29-23(19(27)28-4)13-22-11-8-16-20(2,17(22)7-6-15(23)12-22)9-5-10-21(16,3)18(25)26/h15-17H,5-13H2,1-4H3,(H,25,26)

> <INCHI_KEY>
USYOOQFISINJLZ-UHFFFAOYSA-N

> <FORMULA>
C23H34O6

> <MOLECULAR_WEIGHT>
406.5125

> <EXACT_MASS>
406.23553882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.878565763868394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-(acetyloxy)-14-(methoxycarbonyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.852842605666668

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.318411762274317

> <JCHEM_PKA_STRONGEST_BASIC>
-6.891702284780695

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
104.67499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(acetyloxy)-14-(methoxycarbonyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036263
     RDKit          3D
Annoglabasin C
 63 66  0  0  0  0  0  0  0  0999 V2000
    4.5536    3.4756    1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    2.5672    0.9406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8150    1.2145    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9653    0.8174    1.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    0.2193    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275   -1.0907    0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -1.3790   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -2.7302   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793   -0.5051   -1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5580    0.2634    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    0.7277    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4107    1.6876    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116    1.0262    1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    0.3618    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034    0.1409    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4805    1.4397   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2895    0.0710    1.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6231    0.1645    2.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6715   -0.1252    1.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3824   -1.0083   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535   -1.5929   -1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001   -1.4987   -1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -0.8226   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -1.8371    0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -0.2598   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -1.3046   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246   -0.5934   -1.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4459    0.5907   -1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    1.5894   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3079    3.7805    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    4.4171    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5857    3.1295    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461   -3.2697    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3205   -2.6456   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757   -3.2823   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154   -0.7146    1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    0.9959    1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664    2.0705    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    2.5663    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4608    0.2708    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611    1.8137    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802    1.0956   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4988    1.2397   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9076    1.8426   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    2.2258    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9203   -1.0381    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3768   -0.6905   -0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -1.8136    0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8441   -2.6837   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875   -1.1618   -2.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   -2.5214   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673   -1.0214   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -1.9864    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -2.8428    0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946   -1.6128    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    0.2739   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873   -1.9194   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327   -1.9823   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673   -0.2094   -2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7423   -1.2882   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    1.0726   -1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    1.8046   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    2.4756   -0.3205 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
  7  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28  5  1  0
 25 11  1  0
 29 11  1  0
 23 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 29 62  1  0
 29 63  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.148  -0.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.108   0.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.061   5.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.611   5.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.367   0.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.934   4.833   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.975   3.522   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.616   4.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.933   3.166   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.263   2.606   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.792  -0.089   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.905   6.373   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.282   4.089   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.387   2.908   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.801   5.052   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.161   2.021   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   28                                                            
CONECT    5    9   10                                                       
CONECT    6    7   15                                                       
CONECT    7    6   17                                                       
CONECT    8   11   16                                                       
CONECT    9    5   20                                                       
CONECT   10    5   21                                                       
CONECT   11    8   22                                                       
CONECT   12   15   22                                                       
CONECT   13   22   23                                                       
CONECT   14    1   24   29                                                  
CONECT   15    6   12   23                                                  
CONECT   16    8   20   21                                                  
CONECT   17    7   20   22                                                  
CONECT   18   21   25   26                                                  
CONECT   19   23   27   28                                                  
CONECT   20    2    9   16   17                                             
CONECT   21    3   10   16   18                                             
CONECT   22   11   12   13   17                                             
CONECT   23   13   15   19   29                                             
CONECT   24   14                                                            
CONECT   25   18                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28    4   19                                                       
CONECT   29   14   23                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0036263
HETATM    1  C1  UNL     1       4.554   3.476   1.456  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.597   2.567   0.941  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.815   1.214   0.825  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.965   0.817   1.223  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.857   0.219   0.297  1.00  0.00           C  
HETATM    6  O3  UNL     1       3.427  -1.091   0.341  1.00  0.00           O  
HETATM    7  C4  UNL     1       4.586  -1.379  -0.349  1.00  0.00           C  
HETATM    8  C5  UNL     1       5.217  -2.730  -0.331  1.00  0.00           C  
HETATM    9  O4  UNL     1       5.179  -0.505  -1.038  1.00  0.00           O  
HETATM   10  C6  UNL     1       1.558   0.263   1.067  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.489   0.728   0.142  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.411   1.688   0.869  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.712   1.026   1.289  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.365   0.362   0.097  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.803   0.141   0.285  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.481   1.440  -0.237  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.289   0.071   1.682  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.623   0.165   2.725  1.00  0.00           O  
HETATM   19  O6  UNL     1      -5.672  -0.125   1.882  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.382  -1.008  -0.498  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.554  -1.593  -1.542  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.100  -1.499  -1.471  1.00  0.00           C  
HETATM   23  C17 UNL     1      -1.507  -0.823  -0.244  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.418  -1.837   0.826  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.184  -0.260  -0.703  1.00  0.00           C  
HETATM   26  C20 UNL     1       0.796  -1.305  -1.154  1.00  0.00           C  
HETATM   27  C21 UNL     1       1.925  -0.593  -1.873  1.00  0.00           C  
HETATM   28  C22 UNL     1       2.446   0.591  -1.086  1.00  0.00           C  
HETATM   29  C23 UNL     1       1.347   1.589  -0.813  1.00  0.00           C  
HETATM   30  H1  UNL     1       4.308   3.780   2.495  1.00  0.00           H  
HETATM   31  H2  UNL     1       4.437   4.417   0.846  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.586   3.130   1.331  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.946  -3.270   0.613  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.320  -2.646  -0.410  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.876  -3.282  -1.231  1.00  0.00           H  
HETATM   36  H7  UNL     1       1.415  -0.715   1.513  1.00  0.00           H  
HETATM   37  H8  UNL     1       1.682   0.996   1.910  1.00  0.00           H  
HETATM   38  H9  UNL     1       0.066   2.070   1.791  1.00  0.00           H  
HETATM   39  H10 UNL     1      -0.674   2.566   0.250  1.00  0.00           H  
HETATM   40  H11 UNL     1      -1.461   0.271   2.090  1.00  0.00           H  
HETATM   41  H12 UNL     1      -2.361   1.814   1.702  1.00  0.00           H  
HETATM   42  H13 UNL     1      -2.180   1.096  -0.757  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.499   1.240  -0.573  1.00  0.00           H  
HETATM   44  H15 UNL     1      -3.908   1.843  -1.096  1.00  0.00           H  
HETATM   45  H16 UNL     1      -4.422   2.226   0.564  1.00  0.00           H  
HETATM   46  H17 UNL     1      -5.920  -1.038   2.280  1.00  0.00           H  
HETATM   47  H18 UNL     1      -5.377  -0.691  -0.878  1.00  0.00           H  
HETATM   48  H19 UNL     1      -4.639  -1.814   0.256  1.00  0.00           H  
HETATM   49  H20 UNL     1      -3.844  -2.684  -1.660  1.00  0.00           H  
HETATM   50  H21 UNL     1      -3.887  -1.162  -2.537  1.00  0.00           H  
HETATM   51  H22 UNL     1      -1.611  -2.521  -1.484  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.667  -1.021  -2.401  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.460  -1.986   1.237  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.135  -2.843   0.436  1.00  0.00           H  
HETATM   55  H26 UNL     1      -0.795  -1.613   1.680  1.00  0.00           H  
HETATM   56  H27 UNL     1      -0.479   0.274  -1.666  1.00  0.00           H  
HETATM   57  H28 UNL     1       0.287  -1.919  -1.930  1.00  0.00           H  
HETATM   58  H29 UNL     1       1.133  -1.982  -0.370  1.00  0.00           H  
HETATM   59  H30 UNL     1       1.567  -0.209  -2.838  1.00  0.00           H  
HETATM   60  H31 UNL     1       2.742  -1.288  -2.030  1.00  0.00           H  
HETATM   61  H32 UNL     1       3.223   1.073  -1.688  1.00  0.00           H  
HETATM   62  H33 UNL     1       0.754   1.805  -1.733  1.00  0.00           H  
HETATM   63  H34 UNL     1       1.719   2.476  -0.321  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   10   28
CONECT    6    7
CONECT    7    8    9    9
CONECT    8   33   34   35
CONECT   10   11   36   37
CONECT   11   12   25   29
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   23   42
CONECT   15   16   17   20
CONECT   16   43   44   45
CONECT   17   18   18   19
CONECT   19   46
CONECT   20   21   47   48
CONECT   21   22   49   50
CONECT   22   23   51   52
CONECT   23   24   25
CONECT   24   53   54   55
CONECT   25   26   56
CONECT   26   27   57   58
CONECT   27   28   59   60
CONECT   28   29   61
CONECT   29   62   63
END

HMDB0036263
     RDKit          3D
Annoglabasin C
 63 66  0  0  0  0  0  0  0  0999 V2000
    4.5536    3.4756    1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    2.5672    0.9406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8150    1.2145    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9653    0.8174    1.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    0.2193    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275   -1.0907    0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -1.3790   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -2.7302   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793   -0.5051   -1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5580    0.2634    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    0.7277    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4107    1.6876    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116    1.0262    1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    0.3618    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034    0.1409    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4805    1.4397   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2895    0.0710    1.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6231    0.1645    2.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6715   -0.1252    1.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4459    0.5907   -1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    1.5894   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3079    3.7805    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    4.4171    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5857    3.1295    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461   -3.2697    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3205   -2.6456   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757   -3.2823   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154   -0.7146    1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    0.9959    1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664    2.0705    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    2.5663    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4608    0.2708    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611    1.8137    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802    1.0956   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4988    1.2397   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9076    1.8426   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    2.2258    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9203   -1.0381    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3768   -0.6905   -0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -1.8136    0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8441   -2.6837   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875   -1.1618   -2.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   -2.5214   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673   -1.0214   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -1.9864    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -2.8428    0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946   -1.6128    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    0.2739   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873   -1.9194   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327   -1.9823   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673   -0.2094   -2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7423   -1.2882   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    1.0726   -1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    1.8046   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    2.4756   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
14-(Acetyloxy)-14-(methoxycarbonyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₃H₃₄O₆

Average Molecular Weight

406.5125

Monoisotopic Molecular Weight

406.23553882

IUPAC Name

14-(acetyloxy)-14-(methoxycarbonyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

14-(acetyloxy)-14-(methoxycarbonyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

288627-09-8

SMILES

COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O)OC(C)=O

InChI Identifier

InChI=1S/C23H34O6/c1-14(24)29-23(19(27)28-4)13-22-11-8-16-20(2,17(22)7-6-15(23)12-22)9-5-10-21(16,3)18(25)26/h15-17H,5-13H2,1-4H3,(H,25,26)

InChI Key

USYOOQFISINJLZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036263)
Cell membrane (HMDB: HMDB0036263)

Cellular substructure

Extracellular (HMDB: HMDB0036263)
Membrane (HMDB: HMDB0036263)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036263)

Source

Endogenous

Endogenous (HMDB: HMDB0036263)

Plant

Plant (HMDB: HMDB0036263)

Animal

Animal (HMDB: HMDB0036263)

Exogenous

Food

Food (HMDB: HMDB0036263)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036263)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036263)

Cellular process

Cell signaling (HMDB: HMDB0036263)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036263)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036263)

Nutrient

Nutrient (HMDB: HMDB0036263)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036263)

Emulsifier (HMDB: HMDB0036263)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 - 217 °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	0.0018 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.85	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.68 m³·mol⁻¹	ChemAxon
Polarizability	43.88 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.192	31661259
DarkChem	[M-H]-	188.555	31661259
DeepCCS	[M-2H]-	225.921	30932474
DeepCCS	[M+Na]+	201.533	30932474
AllCCS	[M+H]+	196.6	32859911
AllCCS	[M+H-H2O]+	194.4	32859911
AllCCS	[M+NH4]+	198.6	32859911
AllCCS	[M+Na]+	199.1	32859911
AllCCS	[M-H]-	198.6	32859911
AllCCS	[M+Na-2H]-	199.5	32859911
AllCCS	[M+HCOO]-	200.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annoglabasin C	COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O)OC(C)=O	3662.1	Standard polar	33892256
Annoglabasin C	COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O)OC(C)=O	2770.0	Standard non polar	33892256
Annoglabasin C	COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O)OC(C)=O	2939.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annoglabasin C,1TMS,isomer #1	COC(=O)C1(OC(C)=O)CC23CCC4C(C)(C(=O)O[Si](C)(C)C)CCCC4(C)C2CCC1C3	2789.9	Semi standard non polar	33892256
Annoglabasin C,1TBDMS,isomer #1	COC(=O)C1(OC(C)=O)CC23CCC4C(C)(C(=O)O[Si](C)(C)C(C)(C)C)CCCC4(C)C2CCC1C3	3048.0	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 - Annoglabasin C GC-MS (Non-derivatized) - 70eV, Positive	splash10-01oy-2159000000-6169d1b5abb9bbbaf0c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annoglabasin C GC-MS (1 TMS) - 70eV, Positive	splash10-014i-6028900000-2562f1517737b33cfa78	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annoglabasin C 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 - Annoglabasin C 10V, Positive-QTOF	splash10-0a4r-0009300000-b7f28180364ce26eb47b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 20V, Positive-QTOF	splash10-029j-0039000000-eec003bc9b4c3c85bedc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 40V, Positive-QTOF	splash10-0udr-2498000000-627f6465e22688ec5fc0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 10V, Negative-QTOF	splash10-0bt9-2009600000-1c4a3291f0afef12a95f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 20V, Negative-QTOF	splash10-0bt9-3009100000-ae037653df254c006840	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 40V, Negative-QTOF	splash10-0a4i-9005000000-4b7dc605f8e64cd763cf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 10V, Negative-QTOF	splash10-0a4i-0001900000-a63cc413b9db4d874235	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 20V, Negative-QTOF	splash10-052k-5059000000-60b426cc411b072753b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 40V, Negative-QTOF	splash10-0a4i-9012000000-979dd8c196beddf4411f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 10V, Positive-QTOF	splash10-0bt9-0009400000-a0b7db1f1d767f9330d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 20V, Positive-QTOF	splash10-0zfr-1967100000-73da2a0fcf995dcad93d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annoglabasin C 40V, Positive-QTOF	splash10-001l-4952000000-51bf137ce24f6b172e50	2021-09-23	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

FDB015127

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85217363

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 Annoglabasin C (HMDB0036263)

MOL for HMDB0036263 (Annoglabasin C)

3D MOL for HMDB0036263 (Annoglabasin C)

3D SDF for HMDB0036263 (Annoglabasin C)

3D-SDF for HMDB0036263 (Annoglabasin C)

PDB for HMDB0036263 (Annoglabasin C)

3D PDB for HMDB0036263 (Annoglabasin C)

SMILES for HMDB0036263 (Annoglabasin C)

INCHI for HMDB0036263 (Annoglabasin C)

Structure for HMDB0036263 (Annoglabasin C)

3D Structure for HMDB0036263 (Annoglabasin C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra