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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 21:44:16 UTC

Update Date

2021-09-23 21:44:16 UTC

HMDB ID

HMDB0302915

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Hardwickiic acid

Description

(+)-hardwickiic acid is a member of the class of compounds known as colensane and clerodane diterpenoids. Colensane and clerodane diterpenoids are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations (+)-hardwickiic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (+)-hardwickiic acid can be found in blackcurrant, which makes (+)-hardwickiic acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302915
     RDKit          3D
(+)-Hardwickiic acid
 51 53  0  0  0  0  0  0  0  0999 V2000
    0.4558   -2.9201    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -1.8172    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -2.0639    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -0.8808    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189    0.3630   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    0.2552   -1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.5724   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159    1.5650    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    0.5036    0.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8826    2.7568    0.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    2.7261   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    2.9395   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    1.6492   -0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.6825    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926   -0.4589    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408   -0.6825    2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610   -0.3376    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014   -0.4376   -0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -0.2728   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327   -1.2460   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587   -0.6273   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    0.6394   -0.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4835    0.9070   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348   -2.8603    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073   -3.9073    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5185   -3.0029    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -1.9311   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0126   -2.7394   -0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342   -2.6978    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818   -0.6739    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261   -1.1182   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873   -0.2730   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.3447   -2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    1.2623   -2.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5696    3.4575    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    3.6248   -0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169    3.4483   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    3.6888   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525    1.9342   -0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1266    1.3417   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.3414    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.0390    2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -1.3034    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    0.3258    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.1473    1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720    0.6037    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.4976   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373    0.1849   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4816   -2.2964   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8996   -1.1072   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131    1.9110   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 15  2  1  0
 23 19  2  0
 14  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
M  END

  Mrv0541 02241223322D          

 23 25  0  0  0  0            999 V2000
    2.6328    0.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    0.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481   -0.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614   -0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    0.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354   -1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374    0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481   -0.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    0.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720    1.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2587    0.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453    0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 19  1  0  0  0  0
 10 11  1  0  0  0  0
 10 22  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302915

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2(C)C(CCC=C2C(O)=O)C1(C)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)

> <INCHI_KEY>
HHWOKJDCJVESIF-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.25763062609803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
5.077313079666666

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4560168800551585

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4717746532202276

> <JCHEM_POLAR_SURFACE_AREA>
50.440000000000005

> <JCHEM_REFRACTIVITY>
91.0766

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302915
     RDKit          3D
(+)-Hardwickiic acid
 51 53  0  0  0  0  0  0  0  0999 V2000
    0.4558   -2.9201    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -1.8172    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -2.0639    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -0.8808    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189    0.3630   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    0.2552   -1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.5724   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159    1.5650    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    0.5036    0.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8826    2.7568    0.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    2.7261   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    2.9395   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    1.6492   -0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.6825    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926   -0.4589    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408   -0.6825    2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610   -0.3376    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014   -0.4376   -0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -0.2728   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327   -1.2460   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587   -0.6273   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    0.6394   -0.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4835    0.9070   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348   -2.8603    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073   -3.9073    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5185   -3.0029    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -1.9311   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0126   -2.7394   -0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342   -2.6978    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818   -0.6739    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261   -1.1182   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873   -0.2730   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.3447   -2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    1.2623   -2.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5696    3.4575    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    3.6248   -0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169    3.4483   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    3.6888   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525    1.9342   -0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1266    1.3417   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.3414    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.0390    2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -1.3034    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    0.3258    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.1473    1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720    0.6037    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.4976   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373    0.1849   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4816   -2.2964   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8996   -1.1072   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131    1.9110   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 15  2  1  0
 23 19  2  0
 14  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  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       4.915   1.067   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.481   0.925   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.623  -0.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.341  -1.495   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.344  -0.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.778  -0.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.779   0.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.213   0.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.641  -1.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.210  -0.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.210  -1.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.493  -2.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.916  -1.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.916  -0.498   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.483   0.071   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.623  -0.925   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.053   1.495   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.495   2.777   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.213   1.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.068   2.634   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.350   1.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.635   0.355   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.631   1.495   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   19                                                            
CONECT   19    8   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   10   14   21   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0302915
HETATM    1  C1  UNL     1       0.456  -2.920   0.815  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.262  -1.817   0.048  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.713  -2.064   0.180  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.596  -0.881   0.249  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.019   0.363  -0.310  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.034   0.255  -1.829  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.857   1.572  -0.032  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.216   1.565   0.410  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.834   0.504   0.607  1.00  0.00           O  
HETATM   10  O2  UNL     1      -4.883   2.757   0.631  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.232   2.726  -0.234  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.868   2.939  -0.681  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.053   1.649  -0.775  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.647   0.682   0.220  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.193  -0.459   0.601  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.041  -0.683   2.122  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.661  -0.338   0.489  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.301  -0.438  -0.835  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.772  -0.273  -0.634  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.733  -1.246  -0.387  1.00  0.00           C  
HETATM   21  C19 UNL     1       5.959  -0.627  -0.271  1.00  0.00           C  
HETATM   22  O3  UNL     1       5.772   0.639  -0.435  1.00  0.00           O  
HETATM   23  C20 UNL     1       4.484   0.907  -0.656  1.00  0.00           C  
HETATM   24  H1  UNL     1       0.335  -2.860   1.892  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.007  -3.907   0.515  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.519  -3.003   0.554  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.118  -1.931  -1.011  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.013  -2.739  -0.675  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.934  -2.698   1.091  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.982  -0.674   1.288  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.526  -1.118  -0.347  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.987  -0.273  -2.080  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.223  -0.345  -2.226  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.129   1.262  -2.310  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.570   3.458   1.293  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.815   3.625  -0.040  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.917   3.448  -1.689  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.393   3.689  -0.014  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.952   1.934  -0.417  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.127   1.342  -1.819  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.792   1.341   1.134  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.851  -1.039   2.630  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.913  -1.303   2.315  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.266   0.326   2.571  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.118  -1.147   1.134  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.972   0.604   1.017  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.221  -1.498  -1.244  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.937   0.185  -1.644  1.00  0.00           H  
HETATM   49  H26 UNL     1       4.482  -2.296  -0.311  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.900  -1.107  -0.079  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.113   1.911  -0.819  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   15   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6    7   14
CONECT    6   32   33   34
CONECT    7    8   11   11
CONECT    8    9    9   10
CONECT   10   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41
CONECT   15   16   17
CONECT   16   42   43   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   23   23
CONECT   20   21   21   49
CONECT   21   22   50
CONECT   22   23
CONECT   23   51
END

HMDB0302915
     RDKit          3D
(+)-Hardwickiic acid
 51 53  0  0  0  0  0  0  0  0999 V2000
    0.4558   -2.9201    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -1.8172    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -2.0639    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -0.8808    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189    0.3630   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    0.2552   -1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.5724   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159    1.5650    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    0.5036    0.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8826    2.7568    0.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    2.7261   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    2.9395   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    1.6492   -0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.6825    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926   -0.4589    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408   -0.6825    2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610   -0.3376    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014   -0.4376   -0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -0.2728   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327   -1.2460   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587   -0.6273   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    0.6394   -0.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4835    0.9070   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348   -2.8603    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073   -3.9073    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5185   -3.0029    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -1.9311   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0126   -2.7394   -0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342   -2.6978    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818   -0.6739    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261   -1.1182   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873   -0.2730   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.3447   -2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    1.2623   -2.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5696    3.4575    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    3.6248   -0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169    3.4483   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    3.6888   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525    1.9342   -0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1266    1.3417   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.3414    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.0390    2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -1.3034    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    0.3258    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.1473    1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720    0.6037    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.4976   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373    0.1849   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4816   -2.2964   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8996   -1.1072   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131    1.9110   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 15  2  1  0
 23 19  2  0
 14  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-[2-(Furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate	Generator
(+)-Hardwickiate	Generator
Hardwickic acid, (-)-isomer	MeSH
Hardwickic acid	MeSH

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(CCC=C2C(O)=O)C1(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)

InChI Key

HHWOKJDCJVESIF-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
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302915)

Food

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Process

Not Available

Role

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	5.33	ALOGPS
logP	5.08	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.08 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	178.634	32859911
AllCCS	[M+H-H2O]+	175.467	32859911
AllCCS	[M+Na]+	182.411	32859911
AllCCS	[M+NH4]+	181.568	32859911
AllCCS	[M-H]-	185.005	32859911
AllCCS	[M+Na-2H]-	185.228	32859911
AllCCS	[M+HCOO]-	185.614	32859911
DeepCCS	[M+H]+	179.105	30932474
DeepCCS	[M-H]-	176.747	30932474
DeepCCS	[M-2H]-	209.633	30932474
DeepCCS	[M+Na]+	185.198	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 - (+)-Hardwickiic acid 10V, Positive-QTOF	splash10-014i-0097000000-fed39af9417d4a080f43	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 20V, Positive-QTOF	splash10-00rj-0391000000-5e076b8451e26c71ba14	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 40V, Positive-QTOF	splash10-00kr-2980000000-7f9587534f8731d22563	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 10V, Negative-QTOF	splash10-014i-0049000000-26269078d2d5b32a37da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 20V, Negative-QTOF	splash10-00xr-0093000000-094c9e1bfbdeae11ab01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 40V, Negative-QTOF	splash10-00ll-1090000000-edf67d81c1d3829d273c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 10V, Positive-QTOF	splash10-014i-0094000000-c8b34837a6610be3fcbb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 20V, Positive-QTOF	splash10-0fz9-0490000000-914b8f387fe0cd72b097	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 40V, Positive-QTOF	splash10-0fxt-5930000000-35dd4033a8477f12cd44	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 10V, Negative-QTOF	splash10-00xr-0098000000-5616871189dc97fa5f81	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 20V, Negative-QTOF	splash10-014i-0095000000-eba827a65da349366bb4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Hardwickiic acid 40V, Negative-QTOF	splash10-0600-3190000000-bf82fbc21d16e353611f	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

FDB006884

KNApSAcK ID

Not Available

Chemspider ID

26503523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559627

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 (+)-Hardwickiic acid (HMDB0302915)

MOL for HMDB0302915 ((+)-Hardwickiic acid)

3D MOL for HMDB0302915 ((+)-Hardwickiic acid)

3D SDF for HMDB0302915 ((+)-Hardwickiic acid)

3D-SDF for HMDB0302915 ((+)-Hardwickiic acid)

PDB for HMDB0302915 ((+)-Hardwickiic acid)

3D PDB for HMDB0302915 ((+)-Hardwickiic acid)

SMILES for HMDB0302915 ((+)-Hardwickiic acid)

INCHI for HMDB0302915 ((+)-Hardwickiic acid)

Structure for HMDB0302915 ((+)-Hardwickiic acid)

3D Structure for HMDB0302915 ((+)-Hardwickiic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra