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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:41:31 UTC

Update Date

2021-09-23 19:41:31 UTC

HMDB ID

HMDB0302679

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ciliaric acid

Description

Ciliaric acid, also known as ciliarate, is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids 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. Ciliaric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ciliaric acid can be found in sunflower, which makes ciliaric acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302679
     RDKit          3D
Ciliaric acid
 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.3112   -1.5896    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694   -0.1888    0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514    0.6685    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253    1.6105    1.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8792    0.4653    2.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    0.1553   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    1.0481   -1.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1546    0.9389   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5761    0.8352   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504    2.1467    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2709   -0.3152    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652   -1.5881   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720   -1.8141   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -2.1084   -1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -0.7437   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599   -1.0670    1.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.3525    1.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.9965    0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    1.4658    0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    0.6473   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5973    0.0234   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.0181   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -0.8080   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -2.2081   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7724   -2.0499    1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3936   -1.3954    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078    1.2665    3.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096   -0.7730   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892    0.6460   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0197    2.1040   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    0.7896   -2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262    1.9030   -2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814    0.1571   -2.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8758    2.5924    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1043    2.0198    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871    2.9507    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496   -0.4111    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -2.4463    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5438   -1.5695   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -2.7595   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224   -2.1496   -2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424   -0.8085    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -2.1542    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -0.7511    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735    1.7424    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349    1.4349    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.5411    0.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2155    1.0729   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3794    1.0451   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7098   -0.4046    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.6213   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.3540   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.8534   -1.1633 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
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 11  2  1  0
 20 15  1  0
 20  9  1  0
 23 15  1  0
 21 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
M  END


  Mrv0541 02241223402D          

 23 27  0  0  0  0            999 V2000
    0.6643   -0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4235   -0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1832   -0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7272    0.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    0.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430    0.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277   -0.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643    0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314    1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    1.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -0.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -1.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277   -1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4240   -1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8039    0.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -0.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101   -0.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265   -1.5186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302679

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC34CC1C2CC3C1(C)CCCC(C)(C1CC4O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-17-5-4-6-18(2,16(22)23)13(17)8-15(21)20-9-12-11(7-14(17)20)19(12,3)10-20/h11-15,21H,4-10H2,1-3H3,(H,22,23)

> <INCHI_KEY>
REFPIPGRFRVTDA-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.2313538021033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
3.1588684920000007

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.635589846513509

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4031043639739539

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
87.12109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302679
     RDKit          3D
Ciliaric acid
 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.3112   -1.5896    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694   -0.1888    0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514    0.6685    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253    1.6105    1.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8792    0.4653    2.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    0.1553   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    1.0481   -1.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1546    0.9389   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5761    0.8352   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504    2.1467    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2709   -0.3152    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652   -1.5881   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720   -1.8141   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -2.1084   -1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -0.7437   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599   -1.0670    1.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.3525    1.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.9965    0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    1.4658    0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    0.6473   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5973    0.0234   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.0181   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -0.8080   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -2.2081   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7724   -2.0499    1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3936   -1.3954    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078    1.2665    3.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096   -0.7730   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892    0.6460   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0197    2.1040   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    0.7896   -2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262    1.9030   -2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814    0.1571   -2.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8758    2.5924    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1043    2.0198    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871    2.9507    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496   -0.4111    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -2.4463    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5438   -1.5695   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -2.7595   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224   -2.1496   -2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424   -0.8085    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -2.1542    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -0.7511    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735    1.7424    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349    1.4349    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.5411    0.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2155    1.0729   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3794    1.0451   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7098   -0.4046    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.6213   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.3540   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.8534   -1.1633 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
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 11  2  1  0
 20 15  1  0
 20  9  1  0
 23 15  1  0
 21 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
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 20 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  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       1.240  -0.236   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.657  -1.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.075  -0.236   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.957   1.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.540   2.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.357   1.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.422   0.472   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.429   0.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.494   0.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.358  -0.472   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.240   1.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.059   1.890   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.177   3.426   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.122  -2.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.059  -1.181   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.059  -2.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.358  -3.426   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.658  -2.599   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.777  -1.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.367   0.354   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.494  -0.353   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.312  -1.418   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.903  -2.835   0.000  0.00  0.00           O+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7   12                                             
CONECT    7    6    8                                                       
CONECT    8    3    4    7    9                                             
CONECT    9    8                                                            
CONECT   10   11   15   19                                                  
CONECT   11   10   12                                                       
CONECT   12    6   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1   10   14   16                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   10   18   20   22                                             
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   19   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0302679
HETATM    1  C1  UNL     1      -3.311  -1.590   0.887  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.769  -0.189   0.528  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.251   0.668   1.633  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.025   1.611   1.364  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.879   0.465   2.944  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.407   0.155  -0.779  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.626   1.048  -1.672  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.155   0.939  -1.605  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.576   0.835  -0.198  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.950   2.147   0.477  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.271  -0.315   0.467  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.965  -1.588  -0.303  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.472  -1.814  -0.599  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.728  -2.108  -1.957  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.388  -0.744  -0.151  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.960  -1.067   1.210  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.269  -0.352   1.241  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.138   0.997   0.724  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.719   1.466   0.686  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.889   0.647  -0.304  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.597   0.023  -0.214  1.00  0.00           C  
HETATM   22  C19 UNL     1       5.047   0.018  -0.631  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.677  -0.808  -0.985  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.369  -2.208  -0.026  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.772  -2.050   1.712  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.394  -1.395   1.157  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.708   1.266   3.518  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.710  -0.773  -1.347  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.389   0.646  -0.539  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.020   2.104  -1.584  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.909   0.790  -2.739  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.726   1.903  -2.012  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.781   0.157  -2.281  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.876   2.592   0.016  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.104   2.020   1.554  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.187   2.951   0.284  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.950  -0.411   1.538  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.391  -2.446   0.296  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.544  -1.569  -1.242  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.793  -2.759  -0.066  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.122  -2.150  -2.460  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.342  -0.809   2.058  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.159  -2.154   1.237  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.136  -0.751   1.778  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.873   1.742   1.094  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.235   1.435   1.680  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.773   2.541   0.371  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.216   1.073  -1.303  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.379   1.045  -0.939  1.00  0.00           H  
HETATM   50  H27 UNL     1       5.710  -0.405   0.154  1.00  0.00           H  
HETATM   51  H28 UNL     1       5.193  -0.621  -1.535  1.00  0.00           H  
HETATM   52  H29 UNL     1       2.464  -0.354  -1.976  1.00  0.00           H  
HETATM   53  H30 UNL     1       2.981  -1.853  -1.163  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    6   11
CONECT    3    4    4    5
CONECT    5   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   11   20
CONECT   10   34   35   36
CONECT   11   12   37
CONECT   12   13   38   39
CONECT   13   14   15   40
CONECT   14   41
CONECT   15   16   20   23
CONECT   16   17   42   43
CONECT   17   18   21   44
CONECT   18   19   21   45
CONECT   19   20   46   47
CONECT   20   48
CONECT   21   22   23
CONECT   22   49   50   51
CONECT   23   52   53
END

HMDB0302679
     RDKit          3D
Ciliaric acid
 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.3112   -1.5896    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694   -0.1888    0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514    0.6685    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253    1.6105    1.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8792    0.4653    2.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    0.1553   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    1.0481   -1.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1546    0.9389   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5761    0.8352   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504    2.1467    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2709   -0.3152    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652   -1.5881   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720   -1.8141   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -2.1084   -1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -0.7437   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599   -1.0670    1.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.3525    1.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.9965    0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    1.4658    0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    0.6473   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5973    0.0234   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.0181   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -0.8080   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -2.2081   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7724   -2.0499    1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3936   -1.3954    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078    1.2665    3.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096   -0.7730   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892    0.6460   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0197    2.1040   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    0.7896   -2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262    1.9030   -2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814    0.1571   -2.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8758    2.5924    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1043    2.0198    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871    2.9507    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496   -0.4111    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -2.4463    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5438   -1.5695   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -2.7595   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224   -2.1496   -2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424   -0.8085    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -2.1542    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -0.7511    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735    1.7424    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349    1.4349    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.5411    0.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2155    1.0729   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3794    1.0451   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7098   -0.4046    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.6213   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.3540   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.8534   -1.1633 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
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 11  2  1  0
 20 15  1  0
 20  9  1  0
 23 15  1  0
 21 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ciliarate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

2-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

Traditional Name

2-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CC34CC1C2CC3C1(C)CCCC(C)(C1CC4O)C(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-17-5-4-6-18(2,16(22)23)13(17)8-15(21)20-9-12-11(7-14(17)20)19(12,3)10-20/h11-15,21H,4-10H2,1-3H3,(H,22,23)

InChI Key

REFPIPGRFRVTDA-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

Substituents

Atisane diterpenoid
Kaurane diterpenoid
Villanovane, atisane, trachylobane or helvifulvane diterpenoid
Alkaloid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.28	ALOGPS
logP	3.16	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-0.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.12 m³·mol⁻¹	ChemAxon
Polarizability	36.23 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	178.994	32859911
AllCCS	[M+H-H2O]+	176.202	32859911
AllCCS	[M+Na]+	182.313	32859911
AllCCS	[M+NH4]+	181.573	32859911
AllCCS	[M-H]-	184.947	32859911
AllCCS	[M+Na-2H]-	184.998	32859911
AllCCS	[M+HCOO]-	185.195	32859911
DeepCCS	[M-2H]-	211.101	30932474
DeepCCS	[M+Na]+	186.666	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 10V, Positive-QTOF	splash10-0uxr-0049000000-520df8d942fa56e09a73	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 20V, Positive-QTOF	splash10-106r-0294000000-3b3d68e9475e3eed0db5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 40V, Positive-QTOF	splash10-014i-3960000000-88553521233561dbea4c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 10V, Negative-QTOF	splash10-014i-0069000000-08ed6130104893d75b4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 20V, Negative-QTOF	splash10-06di-0093000000-5a1e50fdb6cb8164720a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 40V, Negative-QTOF	splash10-0a4i-1091000000-1036c3395ebd7219baa7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 10V, Positive-QTOF	splash10-01b9-0049000000-c70b4ec8b8c1449834b8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 20V, Positive-QTOF	splash10-00xr-0983000000-4c3f1f37632debbcc6e6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 40V, Positive-QTOF	splash10-0avi-3920000000-3251aecab449020e43a1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 10V, Negative-QTOF	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 20V, Negative-QTOF	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciliaric acid 40V, Negative-QTOF	splash10-014i-1009000000-7e11fc3c22d4c3fa8f87	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB005712

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

73028428

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

Not Available

Showing metabocard for Ciliaric acid (HMDB0302679)

MOL for HMDB0302679 (Ciliaric acid)

3D MOL for HMDB0302679 (Ciliaric acid)

3D SDF for HMDB0302679 (Ciliaric acid)

3D-SDF for HMDB0302679 (Ciliaric acid)

PDB for HMDB0302679 (Ciliaric acid)

3D PDB for HMDB0302679 (Ciliaric acid)

SMILES for HMDB0302679 (Ciliaric acid)

INCHI for HMDB0302679 (Ciliaric acid)

Structure for HMDB0302679 (Ciliaric acid)

3D Structure for HMDB0302679 (Ciliaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra