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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:00:53 UTC

Update Date

2022-03-07 02:55:05 UTC

HMDB ID

HMDB0036836

Secondary Accession Numbers

HMDB36836

Metabolite Identification

Common Name

Cascarillin

Description

Cascarillin belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Based on a literature review a significant number of articles have been published on Cascarillin.

Structure

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


  Mrv0541 05061309222D          

 29 31  0  0  0  0            999 V2000
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    5.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074    5.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    3.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    4.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8102    3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    4.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629    3.7938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486    4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    5.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20  3  1  0  0  0  0
 20 10  1  0  0  0  0
 20 18  1  0  0  0  0
 21  4  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22  9  1  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23 12  2  0  0  0  0
 24 14  2  0  0  0  0
 25 16  1  0  0  0  0
 26 19  1  0  0  0  0
 27 21  1  0  0  0  0
 28  8  1  0  0  0  0
 28 11  1  0  0  0  0
 29 14  1  0  0  0  0
 29 17  1  0  0  0  0
M  END

HMDB0036836
     RDKit          3D
Cascarillin
 61 63  0  0  0  0  0  0  0  0999 V2000
   -2.0009    5.1856    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    4.0121   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    4.1616   -2.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    2.8082   -0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404    1.6770   -1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581    0.6054   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -0.2648    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036    0.6192    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -0.9331    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3015   -2.3291   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -3.1887    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883   -2.5065    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -3.3139    1.1721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -1.2292    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -0.6377    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -1.4839   -0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -0.1798   -0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -0.7519   -2.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -0.6237   -3.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1043   -0.1328    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -1.3509    0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951   -2.1726   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1248   -0.9771    0.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556    0.2940    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7355    0.2449    1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1366   -0.9764    1.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -1.7493    1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    1.2777   -0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2233    1.7446   -2.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    5.9479    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577    4.8809    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    5.6526   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424    2.0687   -2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134    1.1218   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920    0.0905   -1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    0.0240    2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    1.2754    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    1.2607    1.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819   -1.0397    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -2.3605   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -2.8821   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602   -3.5975   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -4.1125    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171   -2.4127    2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161   -3.5490    2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.3340    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271   -0.4492    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -1.3008    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268   -1.8370   -1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983   -1.3073   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    0.4786    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465    0.5266   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.0018    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9566   -1.7583   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8675    1.2049    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2993    1.0668    2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726   -2.7931    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081    1.9188   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.2172   -2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190    2.8308   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    1.6727   -3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 17 28  1  0
 28 29  1  0
 28  5  1  0
 14  7  1  0
 27 23  2  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
M  END


  Mrv0541 05061309222D          

 29 31  0  0  0  0            999 V2000
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    5.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074    5.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    3.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    4.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8102    3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    4.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629    3.7938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486    4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    5.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20  3  1  0  0  0  0
 20 10  1  0  0  0  0
 20 18  1  0  0  0  0
 21  4  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22  9  1  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23 12  2  0  0  0  0
 24 14  2  0  0  0  0
 25 16  1  0  0  0  0
 26 19  1  0  0  0  0
 27 21  1  0  0  0  0
 28  8  1  0  0  0  0
 28 11  1  0  0  0  0
 29 14  1  0  0  0  0
 29 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036836

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O7/c1-13-17(29-14(2)24)10-20(3)18(5-6-19(26)21(20,4)27)22(13,12-23)9-16(25)15-7-8-28-11-15/h7-8,11-13,16-19,25-27H,5-6,9-10H2,1-4H3

> <INCHI_KEY>
ZOWKQQIGQBVKSV-UHFFFAOYSA-N

> <FORMULA>
C22H32O7

> <MOLECULAR_WEIGHT>
408.4853

> <EXACT_MASS>
408.214803378

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.870963966274374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetate

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
0.913668752999999

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.063346636264654

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.370705835774963

> <JCHEM_PKA_STRONGEST_BASIC>
-3.188090152769273

> <JCHEM_POLAR_SURFACE_AREA>
117.20000000000002

> <JCHEM_REFRACTIVITY>
104.52729999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-hexahydro-1H-naphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036836
     RDKit          3D
Cascarillin
 61 63  0  0  0  0  0  0  0  0999 V2000
   -2.0009    5.1856    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    4.0121   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    4.1616   -2.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    2.8082   -0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404    1.6770   -1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581    0.6054   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -0.2648    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036    0.6192    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -0.9331    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3015   -2.3291   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -3.1887    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883   -2.5065    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -3.3139    1.1721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -1.2292    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -0.6377    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -1.4839   -0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -0.1798   -0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -0.7519   -2.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -0.6237   -3.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1043   -0.1328    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -1.3509    0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951   -2.1726   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1248   -0.9771    0.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556    0.2940    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7355    0.2449    1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1366   -0.9764    1.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -1.7493    1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    1.2777   -0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2233    1.7446   -2.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    5.9479    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577    4.8809    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    5.6526   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424    2.0687   -2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134    1.1218   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920    0.0905   -1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    0.0240    2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    1.2754    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    1.2607    1.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819   -1.0397    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -2.3605   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -2.8821   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602   -3.5975   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -4.1125    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171   -2.4127    2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161   -3.5490    2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.3340    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271   -0.4492    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -1.3008    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268   -1.8370   -1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983   -1.3073   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    0.4786    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465    0.5266   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.0018    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9566   -1.7583   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8675    1.2049    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2993    1.0668    2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726   -2.7931    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081    1.9188   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.2172   -2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190    2.8308   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    1.6727   -3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 17 28  1  0
 28 29  1  0
 28  5  1  0
 14  7  1  0
 27 23  2  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 29 60  1  0
 29 61  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       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.660   0.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.748   9.921   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.054  10.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.657   5.800   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.657   8.319   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.512   5.745   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.120   8.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.131   7.247   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.984   7.082   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.771   7.970   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.990   0.360   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.234   9.747   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6   18                                                       
CONECT    6    5   19                                                       
CONECT    7    8   15                                                       
CONECT    8    7   28                                                       
CONECT    9   16   22                                                       
CONECT   10   17   20                                                       
CONECT   11   15   28                                                       
CONECT   12   22   23                                                       
CONECT   13    1   17   22                                                  
CONECT   14    2   24   29                                                  
CONECT   15    7   11   16                                                  
CONECT   16    9   15   25                                                  
CONECT   17   10   13   29                                                  
CONECT   18    5   20   22                                                  
CONECT   19    6   21   26                                                  
CONECT   20    3   10   18   21                                             
CONECT   21    4   19   20   27                                             
CONECT   22    9   12   13   18                                             
CONECT   23   12                                                            
CONECT   24   14                                                            
CONECT   25   16                                                            
CONECT   26   19                                                            
CONECT   27   21                                                            
CONECT   28    8   11                                                       
CONECT   29   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0036836
HETATM    1  C1  UNL     1      -2.001   5.186   0.072  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.678   4.012  -0.772  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.816   4.162  -2.033  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.250   2.808  -0.281  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.940   1.677  -1.115  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.958   0.605  -0.923  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.559  -0.265   0.231  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.604   0.619   1.467  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.239  -0.933   0.070  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.302  -2.329  -0.493  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.402  -3.189   0.044  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.288  -2.506   1.033  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.442  -3.314   1.172  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.727  -1.229   0.413  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.802  -0.638   1.284  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.315  -1.484  -0.819  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.785  -0.180  -0.725  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.020  -0.752  -2.079  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.198  -0.624  -3.002  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.104  -0.133   0.009  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.811  -1.351   0.362  1.00  0.00           C  
HETATM   22  O6  UNL     1       3.195  -2.173  -0.706  1.00  0.00           O  
HETATM   23  C17 UNL     1       4.125  -0.977   0.979  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.456   0.294   1.384  1.00  0.00           C  
HETATM   25  C19 UNL     1       5.736   0.245   1.896  1.00  0.00           C  
HETATM   26  O7  UNL     1       6.137  -0.976   1.801  1.00  0.00           O  
HETATM   27  C20 UNL     1       5.220  -1.749   1.262  1.00  0.00           C  
HETATM   28  C21 UNL     1       0.455   1.278  -0.961  1.00  0.00           C  
HETATM   29  C22 UNL     1       1.223   1.745  -2.213  1.00  0.00           C  
HETATM   30  H1  UNL     1      -1.197   5.948   0.034  1.00  0.00           H  
HETATM   31  H2  UNL     1      -2.258   4.881   1.107  1.00  0.00           H  
HETATM   32  H3  UNL     1      -2.923   5.653  -0.366  1.00  0.00           H  
HETATM   33  H4  UNL     1      -1.142   2.069  -2.162  1.00  0.00           H  
HETATM   34  H5  UNL     1      -2.913   1.122  -0.605  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.192   0.090  -1.847  1.00  0.00           H  
HETATM   36  H7  UNL     1      -1.552   0.024   2.400  1.00  0.00           H  
HETATM   37  H8  UNL     1      -0.717   1.275   1.470  1.00  0.00           H  
HETATM   38  H9  UNL     1      -2.487   1.261   1.504  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.182  -1.040   1.096  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.395  -2.360  -1.600  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.637  -2.882  -0.282  1.00  0.00           H  
HETATM   42  H13 UNL     1      -2.060  -3.597  -0.751  1.00  0.00           H  
HETATM   43  H14 UNL     1      -1.011  -4.112   0.567  1.00  0.00           H  
HETATM   44  H15 UNL     1      -1.817  -2.413   2.015  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.616  -3.549   2.101  1.00  0.00           H  
HETATM   46  H17 UNL     1      -4.178   0.334   0.855  1.00  0.00           H  
HETATM   47  H18 UNL     1      -3.527  -0.449   2.314  1.00  0.00           H  
HETATM   48  H19 UNL     1      -4.692  -1.301   1.287  1.00  0.00           H  
HETATM   49  H20 UNL     1      -2.727  -1.837  -1.505  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.898  -1.307  -2.358  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.917   0.479   0.948  1.00  0.00           H  
HETATM   52  H23 UNL     1       2.846   0.527  -0.541  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.329  -2.002   1.124  1.00  0.00           H  
HETATM   54  H25 UNL     1       3.957  -1.758  -1.174  1.00  0.00           H  
HETATM   55  H26 UNL     1       3.868   1.205   1.338  1.00  0.00           H  
HETATM   56  H27 UNL     1       6.299   1.067   2.302  1.00  0.00           H  
HETATM   57  H28 UNL     1       5.273  -2.793   1.061  1.00  0.00           H  
HETATM   58  H29 UNL     1       0.908   1.919  -0.143  1.00  0.00           H  
HETATM   59  H30 UNL     1       2.168   1.217  -2.331  1.00  0.00           H  
HETATM   60  H31 UNL     1       1.419   2.831  -2.100  1.00  0.00           H  
HETATM   61  H32 UNL     1       0.563   1.673  -3.111  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   28   33
CONECT    6    7   34   35
CONECT    7    8    9   14
CONECT    8   36   37   38
CONECT    9   10   17   39
CONECT   10   11   40   41
CONECT   11   12   42   43
CONECT   12   13   14   44
CONECT   13   45
CONECT   14   15   16
CONECT   15   46   47   48
CONECT   16   49
CONECT   17   18   20   28
CONECT   18   19   19   50
CONECT   20   21   51   52
CONECT   21   22   23   53
CONECT   22   54
CONECT   23   24   27   27
CONECT   24   25   25   55
CONECT   25   26   56
CONECT   26   27
CONECT   27   57
CONECT   28   29   58
CONECT   29   59   60   61
END

HMDB0036836
     RDKit          3D
Cascarillin
 61 63  0  0  0  0  0  0  0  0999 V2000
   -2.0009    5.1856    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    4.0121   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    4.1616   -2.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    2.8082   -0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404    1.6770   -1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581    0.6054   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -0.2648    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036    0.6192    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -0.9331    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3015   -2.3291   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -3.1887    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883   -2.5065    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -3.3139    1.1721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -1.2292    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -0.6377    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -1.4839   -0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -0.1798   -0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -0.7519   -2.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -0.6237   -3.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1043   -0.1328    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -1.3509    0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951   -2.1726   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1248   -0.9771    0.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556    0.2940    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7355    0.2449    1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1366   -0.9764    1.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -1.7493    1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    1.2777   -0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2233    1.7446   -2.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    5.9479    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577    4.8809    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    5.6526   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424    2.0687   -2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134    1.1218   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920    0.0905   -1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    0.0240    2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    1.2754    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    1.2607    1.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819   -1.0397    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -2.3605   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -2.8821   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602   -3.5975   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -4.1125    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171   -2.4127    2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161   -3.5490    2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.3340    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271   -0.4492    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -1.3008    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268   -1.8370   -1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983   -1.3073   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    0.4786    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465    0.5266   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.0018    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9566   -1.7583   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8675    1.2049    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2993    1.0668    2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726   -2.7931    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081    1.9188   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.2172   -2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190    2.8308   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    1.6727   -3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 17 28  1  0
 28 29  1  0
 28  5  1  0
 14  7  1  0
 27 23  2  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetic acid	HMDB

Chemical Formula

C₂₂H₃₂O₇

Average Molecular Weight

408.4853

Monoisotopic Molecular Weight

408.214803378

IUPAC Name

4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetate

Traditional Name

4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-hexahydro-1H-naphthalen-2-yl acetate

CAS Registry Number

10118-56-6

SMILES

CC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O

InChI Identifier

InChI=1S/C22H32O7/c1-13-17(29-14(2)24)10-20(3)18(5-6-19(26)21(20,4)27)22(13,12-23)9-16(25)15-7-8-28-11-15/h7-8,11-13,16-19,25-27H,5-6,9-10H2,1-4H3

InChI Key

ZOWKQQIGQBVKSV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Cyclic alcohol
Furan
Tertiary alcohol
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Aromatic alcohol
Hydrocarbon derivative
Aldehyde
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Disposition

Biological location

Cell membrane (HMDB: HMDB0036836)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036836)

Source

Endogenous

Endogenous (HMDB: HMDB0036836)

Animal

Animal (HMDB: HMDB0036836)

Exogenous

Food

Food (HMDB: HMDB0036836)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036836)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036836)

Cellular process

Cell signaling (HMDB: HMDB0036836)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036836)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036836)

Nutrient

Nutrient (HMDB: HMDB0036836)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036836)

Emulsifier (HMDB: HMDB0036836)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	96.99 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	1.31	ALOGPS
logP	0.91	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.53 m³·mol⁻¹	ChemAxon
Polarizability	42.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	191.66	31661259
DarkChem	[M-H]-	185.163	31661259
DeepCCS	[M+H]+	196.393	30932474
DeepCCS	[M-H]-	194.035	30932474
DeepCCS	[M-2H]-	228.229	30932474
DeepCCS	[M+Na]+	204.107	30932474
AllCCS	[M+H]+	197.6	32859911
AllCCS	[M+H-H2O]+	195.2	32859911
AllCCS	[M+NH4]+	199.9	32859911
AllCCS	[M+Na]+	200.5	32859911
AllCCS	[M-H]-	199.8	32859911
AllCCS	[M+Na-2H]-	200.7	32859911
AllCCS	[M+HCOO]-	201.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cascarillin	CC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O	3807.8	Standard polar	33892256
Cascarillin	CC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O	2660.5	Standard non polar	33892256
Cascarillin	CC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O	3083.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cascarillin,1TMS,isomer #1	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O)C(C=O)(CC(O)C2=COC=C2)C1C	3025.8	Semi standard non polar	33892256
Cascarillin,1TMS,isomer #2	CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C	3024.7	Semi standard non polar	33892256
Cascarillin,1TMS,isomer #3	CC(=O)OC1CC2(C)C(CCC(O)C2(C)O)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C	3080.9	Semi standard non polar	33892256
Cascarillin,2TMS,isomer #1	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O[Si](C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C	2998.8	Semi standard non polar	33892256
Cascarillin,2TMS,isomer #2	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C	2971.4	Semi standard non polar	33892256
Cascarillin,2TMS,isomer #3	CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C	2985.3	Semi standard non polar	33892256
Cascarillin,3TMS,isomer #1	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O[Si](C)(C)C)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C	2961.0	Semi standard non polar	33892256
Cascarillin,1TBDMS,isomer #1	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O)C(C=O)(CC(O)C2=COC=C2)C1C	3270.2	Semi standard non polar	33892256
Cascarillin,1TBDMS,isomer #2	CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C	3269.5	Semi standard non polar	33892256
Cascarillin,1TBDMS,isomer #3	CC(=O)OC1CC2(C)C(CCC(O)C2(C)O)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C	3317.7	Semi standard non polar	33892256
Cascarillin,2TBDMS,isomer #1	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C	3475.5	Semi standard non polar	33892256
Cascarillin,2TBDMS,isomer #2	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C	3453.1	Semi standard non polar	33892256
Cascarillin,2TBDMS,isomer #3	CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C	3453.1	Semi standard non polar	33892256
Cascarillin,3TBDMS,isomer #1	CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C	3669.8	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 - Cascarillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1009000000-86634464ced29d7ac651	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cascarillin GC-MS (3 TMS) - 70eV, Positive	splash10-0cdi-5320198000-26e269a772d7d764854f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cascarillin 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 - Cascarillin 10V, Positive-QTOF	splash10-052g-0009200000-be2a1bd9ad5ea310e8bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 20V, Positive-QTOF	splash10-0002-3019000000-7d538a6af9f4798fb3e3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 40V, Positive-QTOF	splash10-0002-9045000000-dae0120e98244640a0a9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 10V, Negative-QTOF	splash10-0a4i-2009600000-fe11de18189371daa65d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 20V, Negative-QTOF	splash10-014i-8019100000-72e5d67a776c02f33e64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 40V, Negative-QTOF	splash10-066u-9026000000-dd273a6bb27cabeeffc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 10V, Positive-QTOF	splash10-0089-1019100000-fc4aafaaa0804dbffa4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 20V, Positive-QTOF	splash10-02mr-2019000000-56a2e86b7ba802777738	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 40V, Positive-QTOF	splash10-0ku6-9504000000-f374e0b86aae15576755	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 10V, Negative-QTOF	splash10-0a4i-2003900000-f69f2d45ab1c6ec32c01	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 20V, Negative-QTOF	splash10-066u-9024000000-27fd02f480488c05f9e2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cascarillin 40V, Negative-QTOF	splash10-014i-4093000000-06ed3cc4320904ca4074	2021-09-23	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

5088211

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1857441

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 Cascarillin (HMDB0036836)

MOL for HMDB0036836 (Cascarillin)

3D MOL for HMDB0036836 (Cascarillin)

3D SDF for HMDB0036836 (Cascarillin)

3D-SDF for HMDB0036836 (Cascarillin)

PDB for HMDB0036836 (Cascarillin)

3D PDB for HMDB0036836 (Cascarillin)

SMILES for HMDB0036836 (Cascarillin)

INCHI for HMDB0036836 (Cascarillin)

Structure for HMDB0036836 (Cascarillin)

3D Structure for HMDB0036836 (Cascarillin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra