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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:11:07 UTC

Update Date

2022-03-07 02:57:02 UTC

HMDB ID

HMDB0041495

Secondary Accession Numbers

HMDB41495

Metabolite Identification

Common Name

ent-16a-Hydroxy-17-acetoxy-19-kauranal

Description

ent-16a-Hydroxy-17-acetoxy-19-kauranal, also known as annosquamosin a (terpene) or annosquamosin a?, 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. ent-16a-Hydroxy-17-acetoxy-19-kauranal 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 02241214242D          

 26 29  0  0  0  0            999 V2000
   -2.8853    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1710   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1710    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310    1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    0.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581   -1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839   -1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4097   -1.7987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641    0.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7948    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797    1.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797    0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097   -0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 20  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END

HMDB0041495
     RDKit          3D
ent-16a-Hydroxy-17-acetoxy-19-kauranal
 60 63  0  0  0  0  0  0  0  0999 V2000
    7.0954   -0.1396    0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463   -0.3803    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510   -1.5604    1.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446    0.6236    0.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    0.5055    1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -0.3664    0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257   -1.6839    0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437   -0.3867    0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251   -0.7111   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -1.9888   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.8282   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0765   -0.4288    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -0.2464    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    0.1849    2.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0210   -1.6027    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -2.2968    2.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.6911    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.7892   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2719    1.8613   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    0.4943   -0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468    0.0412   -1.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491    0.4393   -1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    1.6944   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    1.5593   -1.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971    0.2307   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -0.8919   -1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2548    0.9222    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7136   -0.5245    1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -0.7431   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    1.4694    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488   -0.0070    2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909   -2.1701    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -1.2139    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    0.5935    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399   -2.5115   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1348   -2.6523    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -2.1128   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842   -2.5525    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.2421    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599    1.2088    2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -0.5222    3.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616    0.2542    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6157   -1.9955    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633    0.1203   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419    1.2020    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    1.6785   -1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228    2.8168   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589    2.1563    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    2.6170   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413    0.8828   -2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945   -0.6622   -2.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -0.5292   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    0.3640   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504    2.4684   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134    2.1264    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1952    2.0346   -2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954    2.2132   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    0.2255   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -0.6828   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -1.8352   -1.4153 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25  6  1  0
 22  9  1  0
 26  9  1  0
 20 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
M  END


  Mrv0541 02241214242D          

 26 29  0  0  0  0            999 V2000
   -2.8853    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1710   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1710    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310    1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    0.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581   -1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839   -1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4097   -1.7987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641    0.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7948    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797    1.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797    0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097   -0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 20  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041495

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-15(24)26-14-22(25)12-21-10-7-17-19(2,13-23)8-4-9-20(17,3)18(21)6-5-16(22)11-21/h13,16-18,25H,4-12,14H2,1-3H3

> <INCHI_KEY>
FCHGRGOUMXZTFS-UHFFFAOYSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.503

> <EXACT_MASS>
362.245709576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.035696256338056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
3.0758685416666687

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.752230213691345

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3445745045314057

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
99.03799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041495
     RDKit          3D
ent-16a-Hydroxy-17-acetoxy-19-kauranal
 60 63  0  0  0  0  0  0  0  0999 V2000
    7.0954   -0.1396    0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463   -0.3803    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510   -1.5604    1.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446    0.6236    0.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    0.5055    1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -0.3664    0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257   -1.6839    0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437   -0.3867    0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251   -0.7111   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -1.9888   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.8282   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0765   -0.4288    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -0.2464    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    0.1849    2.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0210   -1.6027    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -2.2968    2.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.6911    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.7892   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2719    1.8613   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    0.4943   -0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468    0.0412   -1.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491    0.4393   -1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    1.6944   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    1.5593   -1.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971    0.2307   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -0.8919   -1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2548    0.9222    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7136   -0.5245    1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -0.7431   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    1.4694    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488   -0.0070    2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909   -2.1701    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -1.2139    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    0.5935    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399   -2.5115   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1348   -2.6523    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -2.1128   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842   -2.5525    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.2421    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599    1.2088    2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -0.5222    3.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616    0.2542    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6157   -1.9955    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633    0.1203   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419    1.2020    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    1.6785   -1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228    2.8168   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589    2.1563    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    2.6170   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413    0.8828   -2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945   -0.6622   -2.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -0.5292   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    0.3640   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504    2.4684   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134    2.1264    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1952    2.0346   -2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954    2.2132   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    0.2255   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -0.6828   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -1.8352   -1.4153 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25  6  1  0
 22  9  1  0
 26  9  1  0
 20 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.386   0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.386  -1.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.053  -2.022   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.722  -1.251   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.722   0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.053   1.058   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.388  -2.022   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.058  -1.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.058   0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.388   1.058   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.270   1.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.270   2.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.058   3.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.388   2.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.722   1.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.282  -3.358   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.823  -3.358   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.365  -3.358   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.360   1.503   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.484   0.290   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.695   2.273   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.695   0.732   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.695  -0.809   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.031  -1.580   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.031  -3.121   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.365  -0.809   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16   17                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   15                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15    5                                                            
CONECT   16    3                                                            
CONECT   17    3   18                                                       
CONECT   18   17                                                            
CONECT   19   12   20   21   22                                             
CONECT   20    9   19                                                       
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0041495
HETATM    1  C1  UNL     1       7.095  -0.140   0.676  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.646  -0.380   1.017  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.351  -1.560   1.314  1.00  0.00           O  
HETATM    4  O2  UNL     1       4.745   0.624   0.997  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.402   0.506   1.285  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.650  -0.366   0.364  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.026  -1.684   0.297  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.144  -0.387   0.689  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.425  -0.711  -0.578  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.370  -1.989  -0.519  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.799  -1.828  -0.137  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.077  -0.429   0.366  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.360  -0.246   1.064  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.167   0.185   2.530  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.021  -1.603   1.137  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.897  -2.297   2.130  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.343   0.691   0.465  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.783   1.789  -0.374  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.272   1.861  -0.391  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.781   0.494  -0.785  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.647   0.041  -1.949  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.349   0.439  -1.169  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.427   1.694  -0.858  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.888   1.559  -1.059  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.497   0.231  -1.043  1.00  0.00           C  
HETATM   26  C22 UNL     1       1.590  -0.892  -1.573  1.00  0.00           C  
HETATM   27  H1  UNL     1       7.255   0.922   0.471  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.714  -0.524   1.515  1.00  0.00           H  
HETATM   29  H3  UNL     1       7.389  -0.743  -0.217  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.889   1.469   1.477  1.00  0.00           H  
HETATM   31  H5  UNL     1       3.349  -0.007   2.303  1.00  0.00           H  
HETATM   32  H6  UNL     1       2.591  -2.170   1.042  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.994  -1.214   1.432  1.00  0.00           H  
HETATM   34  H8  UNL     1       0.963   0.594   1.128  1.00  0.00           H  
HETATM   35  H9  UNL     1      -0.240  -2.511  -1.509  1.00  0.00           H  
HETATM   36  H10 UNL     1       0.135  -2.652   0.227  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.425  -2.113  -0.999  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.084  -2.552   0.682  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.272  -0.242   1.126  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.560   1.209   2.695  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.584  -0.522   3.238  1.00  0.00           H  
HETATM   42  H16 UNL     1      -2.062   0.254   2.711  1.00  0.00           H  
HETATM   43  H17 UNL     1      -4.616  -1.995   0.324  1.00  0.00           H  
HETATM   44  H18 UNL     1      -5.163   0.120  -0.070  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.942   1.202   1.283  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.218   1.679  -1.399  1.00  0.00           H  
HETATM   47  H21 UNL     1      -4.123   2.817  -0.051  1.00  0.00           H  
HETATM   48  H22 UNL     1      -1.959   2.156   0.632  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.998   2.617  -1.151  1.00  0.00           H  
HETATM   50  H24 UNL     1      -2.841   0.883  -2.669  1.00  0.00           H  
HETATM   51  H25 UNL     1      -1.994  -0.662  -2.548  1.00  0.00           H  
HETATM   52  H26 UNL     1      -3.518  -0.529  -1.674  1.00  0.00           H  
HETATM   53  H27 UNL     1      -0.309   0.364  -2.299  1.00  0.00           H  
HETATM   54  H28 UNL     1       0.050   2.468  -1.597  1.00  0.00           H  
HETATM   55  H29 UNL     1       0.113   2.126   0.119  1.00  0.00           H  
HETATM   56  H30 UNL     1       2.195   2.035  -2.049  1.00  0.00           H  
HETATM   57  H31 UNL     1       2.395   2.213  -0.316  1.00  0.00           H  
HETATM   58  H32 UNL     1       3.466   0.226  -1.553  1.00  0.00           H  
HETATM   59  H33 UNL     1       1.275  -0.683  -2.598  1.00  0.00           H  
HETATM   60  H34 UNL     1       2.113  -1.835  -1.415  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   30   31
CONECT    6    7    8   25
CONECT    7   32
CONECT    8    9   33   34
CONECT    9   10   22   26
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   20   39
CONECT   13   14   15   17
CONECT   14   40   41   42
CONECT   15   16   16   43
CONECT   17   18   44   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   22
CONECT   21   50   51   52
CONECT   22   23   53
CONECT   23   24   54   55
CONECT   24   25   56   57
CONECT   25   26   58
CONECT   26   59   60
END

HMDB0041495
     RDKit          3D
ent-16a-Hydroxy-17-acetoxy-19-kauranal
 60 63  0  0  0  0  0  0  0  0999 V2000
    7.0954   -0.1396    0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463   -0.3803    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510   -1.5604    1.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446    0.6236    0.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    0.5055    1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -0.3664    0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257   -1.6839    0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437   -0.3867    0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251   -0.7111   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -1.9888   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.8282   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0765   -0.4288    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -0.2464    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    0.1849    2.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0210   -1.6027    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -2.2968    2.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.6911    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.7892   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2719    1.8613   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    0.4943   -0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468    0.0412   -1.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491    0.4393   -1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    1.6944   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    1.5593   -1.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971    0.2307   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -0.8919   -1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2548    0.9222    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7136   -0.5245    1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -0.7431   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    1.4694    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488   -0.0070    2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909   -2.1701    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -1.2139    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    0.5935    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399   -2.5115   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1348   -2.6523    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -2.1128   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842   -2.5525    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.2421    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599    1.2088    2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -0.5222    3.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616    0.2542    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6157   -1.9955    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633    0.1203   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419    1.2020    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    1.6785   -1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228    2.8168   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589    2.1563    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    2.6170   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413    0.8828   -2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945   -0.6622   -2.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -0.5292   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    0.3640   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504    2.4684   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134    2.1264    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1952    2.0346   -2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954    2.2132   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    0.2255   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -0.6828   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -1.8352   -1.4153 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25  6  1  0
 22  9  1  0
 26  9  1  0
 20 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17-(Acetyloxy)-16-hydroxy-(4alpha,16alpha)-kauran-18-al	HMDB
Annosquamosin a (terpene)	HMDB
Annosquamosin a?	HMDB
{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₄

Average Molecular Weight

362.503

Monoisotopic Molecular Weight

362.245709576

IUPAC Name

{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

Traditional Name

{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

CAS Registry Number

177742-55-1

SMILES

CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3

InChI Identifier

InChI=1S/C22H34O4/c1-15(24)26-14-22(25)12-21-10-7-17-19(2,13-23)8-4-9-20(17,3)18(21)6-5-16(22)11-21/h13,16-18,25H,4-12,14H2,1-3H3

InChI Key

FCHGRGOUMXZTFS-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: HMDB0041495)
Cell membrane (HMDB: HMDB0041495)

Cellular substructure

Extracellular (HMDB: HMDB0041495)
Membrane (HMDB: HMDB0041495)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041495)

Source

Endogenous

Endogenous (HMDB: HMDB0041495)

Plant

Plant (HMDB: HMDB0041495)

Animal

Animal (HMDB: HMDB0041495)

Exogenous

Food

Food (HMDB: HMDB0041495)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0041495)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0041495)

Cellular process

Cell signaling (HMDB: HMDB0041495)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0041495)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041495)

Nutrient

Nutrient (HMDB: HMDB0041495)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041495)

Emulsifier (HMDB: HMDB0041495)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162 - 164 °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	0.0039 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.04 m³·mol⁻¹	ChemAxon
Polarizability	41.04 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]+	181.615	31661259
DarkChem	[M-H]-	179.417	31661259
DeepCCS	[M-2H]-	217.125	30932474
DeepCCS	[M+Na]+	192.352	30932474
AllCCS	[M+H]+	190.2	32859911
AllCCS	[M+H-H2O]+	187.8	32859911
AllCCS	[M+NH4]+	192.4	32859911
AllCCS	[M+Na]+	193.0	32859911
AllCCS	[M-H]-	190.9	32859911
AllCCS	[M+Na-2H]-	191.6	32859911
AllCCS	[M+HCOO]-	192.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
ent-16a-Hydroxy-17-acetoxy-19-kauranal	CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3	3059.3	Standard polar	33892256
ent-16a-Hydroxy-17-acetoxy-19-kauranal	CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3	2621.5	Standard non polar	33892256
ent-16a-Hydroxy-17-acetoxy-19-kauranal	CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3	2855.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
ent-16a-Hydroxy-17-acetoxy-19-kauranal,1TMS,isomer #1	CC(=O)OCC1(O[Si](C)(C)C)CC23CCC4C(C)(C=O)CCCC4(C)C2CCC1C3	2853.1	Semi standard non polar	33892256
ent-16a-Hydroxy-17-acetoxy-19-kauranal,1TBDMS,isomer #1	CC(=O)OCC1(O[Si](C)(C)C(C)(C)C)CC23CCC4C(C)(C=O)CCCC4(C)C2CCC1C3	3113.4	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 - ent-16a-Hydroxy-17-acetoxy-19-kauranal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2093000000-f88d4e65f5821a536dde	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal GC-MS (1 TMS) - 70eV, Positive	splash10-05vy-9257600000-c5ce5b4024d192e590f8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 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 - ent-16a-Hydroxy-17-acetoxy-19-kauranal 10V, Positive-QTOF	splash10-0ik9-0009000000-601730cc795d54dcec25	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 20V, Positive-QTOF	splash10-0udj-1249000000-6f7fdeab20f4a0727747	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 40V, Positive-QTOF	splash10-01ox-4592000000-0723b57af8338ac5e737	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 10V, Negative-QTOF	splash10-03di-5009000000-1435685bf3d29f6d2435	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 20V, Negative-QTOF	splash10-0bt9-9007000000-339dabc3914bf7448828	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 40V, Negative-QTOF	splash10-0a4l-9051000000-4ed3107bae59a0e34a78	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 10V, Negative-QTOF	splash10-03di-0009000000-64c7eccecc0e967c403c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 20V, Negative-QTOF	splash10-03di-0029000000-9a68be9e7af1b9aa936e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 40V, Negative-QTOF	splash10-0079-2090000000-8ac52bcc9d493686ae93	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 10V, Positive-QTOF	splash10-01q9-0049000000-15a296bfd2bde7abc4c9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 20V, Positive-QTOF	splash10-02mi-0594000000-8cf01656333229e29aea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-16a-Hydroxy-17-acetoxy-19-kauranal 40V, Positive-QTOF	splash10-01w1-0921000000-36ca0c7950a7b831bfac	2021-09-24	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

FDB021465

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

73753379

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 ent-16a-Hydroxy-17-acetoxy-19-kauranal (HMDB0041495)

MOL for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

3D MOL for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

3D SDF for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

3D-SDF for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

PDB for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

3D PDB for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

SMILES for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

INCHI for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

Structure for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

3D Structure for HMDB0041495 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra