Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:11:50 UTC

Update Date

2022-03-07 02:56:40 UTC

HMDB ID

HMDB0040634

Secondary Accession Numbers

HMDB40634

Metabolite Identification

Common Name

Piperochromanoic acid

Description

Piperochromanoic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a small amount of articles have been published on Piperochromanoic acid.

Structure

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


  Mrv0541 05061312002D          

 26 27  0  0  0  0            999 V2000
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  4  2  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 21 19  2  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 22  2  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
M  END

HMDB0040634
     RDKit          3D
Piperochromanoic acid
 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.1158   -2.8264    1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.8165    1.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763   -2.1530    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.9735   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -1.1703   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7831   -0.1154   -1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0461   -0.3861   -2.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7113    0.5340   -2.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -1.6759   -2.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468    1.1470   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484    1.3436   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729    2.6487   -0.6305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564    0.3037   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748    0.4827    0.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -0.4539    1.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520   -0.1399    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -0.2142    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.1403    1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.1587    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394    1.3637    1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    2.1228    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622    2.1135   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.7418   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6906    0.0330   -1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966    0.4852   -0.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6809   -1.3340   -2.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424   -3.8156    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -2.6018    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -2.9760   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9730   -2.5377    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505   -2.1457   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2345   -1.9136   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7905    1.9502   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    2.7988   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -0.2320    2.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698    0.8491    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.8635    2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    0.4333    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8123   -1.2178    0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577   -0.5111    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4832    2.3018    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    1.5549    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766    0.4807    1.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3481    3.1242    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384    1.9450   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023    2.3918   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    2.8156   -1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949    0.2699   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547    1.5592   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    0.0277    0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8481    0.0314   -1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -1.6924   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3173   -2.0226   -1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202   -1.3637   -2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 15  2  1  0
 13  4  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END


  Mrv0541 05061312002D          

 26 27  0  0  0  0            999 V2000
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  4  2  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 21 19  2  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 22  2  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040634

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C/CCC1OC2=C(O)C=C(C=C2CC1=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O4/c1-14(2)7-5-8-15(3)9-6-10-20-16(4)11-17-12-18(22(24)25)13-19(23)21(17)26-20/h7,9,12-13,20,23H,4-6,8,10-11H2,1-3H3,(H,24,25)/b15-9-

> <INCHI_KEY>
XBOKPWYVDNVFMX-DHDCSXOGSA-N

> <FORMULA>
C22H28O4

> <MOLECULAR_WEIGHT>
356.4553

> <EXACT_MASS>
356.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.84481463600904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3Z)-4,8-dimethylnona-3,7-dien-1-yl]-8-hydroxy-3-methylidene-3,4-dihydro-2H-1-benzopyran-6-carboxylic acid

> <ALOGPS_LOGP>
4.85

> <JCHEM_LOGP>
5.563287358000001

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.836934526043931

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.101747884543857

> <JCHEM_PKA_STRONGEST_BASIC>
-4.974097153392699

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
105.78799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3Z)-4,8-dimethylnona-3,7-dien-1-yl]-8-hydroxy-3-methylidene-2,4-dihydro-1-benzopyran-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040634
     RDKit          3D
Piperochromanoic acid
 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.1158   -2.8264    1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.8165    1.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763   -2.1530    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.9735   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -1.1703   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7831   -0.1154   -1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0461   -0.3861   -2.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7113    0.5340   -2.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -1.6759   -2.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468    1.1470   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484    1.3436   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729    2.6487   -0.6305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564    0.3037   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748    0.4827    0.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -0.4539    1.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520   -0.1399    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -0.2142    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.1403    1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.1587    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394    1.3637    1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    2.1228    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622    2.1135   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.7418   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6906    0.0330   -1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966    0.4852   -0.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6809   -1.3340   -2.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424   -3.8156    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -2.6018    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -2.9760   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9730   -2.5377    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505   -2.1457   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2345   -1.9136   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7905    1.9502   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    2.7988   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -0.2320    2.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698    0.8491    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.8635    2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    0.4333    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8123   -1.2178    0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577   -0.5111    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4832    2.3018    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    1.5549    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766    0.4807    1.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3481    3.1242    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384    1.9450   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023    2.3918   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    2.8156   -1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949    0.2699   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547    1.5592   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    0.0277    0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8481    0.0314   -1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -1.6924   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3173   -2.0226   -1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202   -1.3637   -2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 15  2  1  0
 13  4  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5    7    8                                                       
CONECT    6    9   10                                                       
CONECT    7    5   14                                                       
CONECT    8    5   15                                                       
CONECT    9    6   15                                                       
CONECT   10    6   20                                                       
CONECT   11   16   17                                                       
CONECT   12   17   18                                                       
CONECT   13   18   19                                                       
CONECT   14    1    2    7                                                  
CONECT   15    3    8    9                                                  
CONECT   16    4   11   20                                                  
CONECT   17   11   12   21                                                  
CONECT   18   12   13   22                                                  
CONECT   19   13   21   23                                                  
CONECT   20   10   16   26                                                  
CONECT   21   17   19   26                                                  
CONECT   22   18   24   25                                                  
CONECT   23   19                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0040634
HETATM    1  C1  UNL     1      -1.116  -2.826   1.308  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.011  -1.816   1.087  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.276  -2.153   0.372  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.923  -0.973  -0.209  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.117  -1.170  -0.885  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.783  -0.115  -1.464  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.046  -0.386  -2.166  1.00  0.00           C  
HETATM    8  O1  UNL     1      -7.711   0.534  -2.720  1.00  0.00           O  
HETATM    9  O2  UNL     1      -7.569  -1.676  -2.248  1.00  0.00           O  
HETATM   10  C8  UNL     1      -5.247   1.147  -1.364  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.048   1.344  -0.685  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.573   2.649  -0.631  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.356   0.304  -0.094  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.175   0.483   0.577  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.777  -0.454   1.568  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.352  -0.140   1.973  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.662  -0.214   0.878  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.973   0.140   1.520  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.741   1.159   1.222  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.039   1.364   1.982  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.376   2.123   0.166  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.462   2.114  -0.894  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.583   0.742  -1.455  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.691   0.033  -1.452  1.00  0.00           C  
HETATM   25  C21 UNL     1       5.997   0.485  -0.891  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.681  -1.334  -2.042  1.00  0.00           C  
HETATM   27  H1  UNL     1      -1.342  -3.816   0.963  1.00  0.00           H  
HETATM   28  H2  UNL     1      -0.227  -2.602   1.845  1.00  0.00           H  
HETATM   29  H3  UNL     1      -3.145  -2.976  -0.382  1.00  0.00           H  
HETATM   30  H4  UNL     1      -3.973  -2.538   1.194  1.00  0.00           H  
HETATM   31  H5  UNL     1      -5.550  -2.146  -0.971  1.00  0.00           H  
HETATM   32  H6  UNL     1      -8.235  -1.914  -2.957  1.00  0.00           H  
HETATM   33  H7  UNL     1      -5.791   1.950  -1.832  1.00  0.00           H  
HETATM   34  H8  UNL     1      -2.697   2.799  -0.137  1.00  0.00           H  
HETATM   35  H9  UNL     1      -2.406  -0.232   2.471  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.370   0.849   2.468  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.081  -0.864   2.772  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.406   0.433   0.021  1.00  0.00           H  
HETATM   39  H13 UNL     1       0.812  -1.218   0.444  1.00  0.00           H  
HETATM   40  H14 UNL     1       2.358  -0.511   2.335  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.483   2.302   1.622  1.00  0.00           H  
HETATM   42  H16 UNL     1       3.778   1.555   3.050  1.00  0.00           H  
HETATM   43  H17 UNL     1       4.677   0.481   1.962  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.348   3.124   0.671  1.00  0.00           H  
HETATM   45  H19 UNL     1       1.438   1.945  -0.345  1.00  0.00           H  
HETATM   46  H20 UNL     1       4.402   2.392  -0.388  1.00  0.00           H  
HETATM   47  H21 UNL     1       3.196   2.816  -1.721  1.00  0.00           H  
HETATM   48  H22 UNL     1       2.695   0.270  -1.909  1.00  0.00           H  
HETATM   49  H23 UNL     1       6.155   1.559  -0.911  1.00  0.00           H  
HETATM   50  H24 UNL     1       6.093   0.028   0.114  1.00  0.00           H  
HETATM   51  H25 UNL     1       6.848   0.031  -1.472  1.00  0.00           H  
HETATM   52  H26 UNL     1       5.667  -1.692  -2.357  1.00  0.00           H  
HETATM   53  H27 UNL     1       4.317  -2.023  -1.274  1.00  0.00           H  
HETATM   54  H28 UNL     1       4.020  -1.364  -2.957  1.00  0.00           H  
CONECT    1    2    2   27   28
CONECT    2    3   15
CONECT    3    4   29   30
CONECT    4    5    5   13
CONECT    5    6   31
CONECT    6    7   10   10
CONECT    7    8    8    9
CONECT    9   32
CONECT   10   11   33
CONECT   11   12   13   13
CONECT   12   34
CONECT   13   14
CONECT   14   15
CONECT   15   16   35
CONECT   16   17   36   37
CONECT   17   18   38   39
CONECT   18   19   19   40
CONECT   19   20   21
CONECT   20   41   42   43
CONECT   21   22   44   45
CONECT   22   23   46   47
CONECT   23   24   24   48
CONECT   24   25   26
CONECT   25   49   50   51
CONECT   26   52   53   54
END

HMDB0040634
     RDKit          3D
Piperochromanoic acid
 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.1158   -2.8264    1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.8165    1.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763   -2.1530    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.9735   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -1.1703   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7831   -0.1154   -1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0461   -0.3861   -2.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7113    0.5340   -2.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -1.6759   -2.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468    1.1470   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484    1.3436   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729    2.6487   -0.6305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564    0.3037   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748    0.4827    0.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -0.4539    1.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520   -0.1399    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -0.2142    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.1403    1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.1587    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394    1.3637    1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    2.1228    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622    2.1135   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.7418   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6906    0.0330   -1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966    0.4852   -0.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6809   -1.3340   -2.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424   -3.8156    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -2.6018    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -2.9760   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9730   -2.5377    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505   -2.1457   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2345   -1.9136   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7905    1.9502   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    2.7988   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -0.2320    2.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698    0.8491    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.8635    2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    0.4333    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8123   -1.2178    0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577   -0.5111    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4832    2.3018    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    1.5549    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766    0.4807    1.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3481    3.1242    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384    1.9450   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023    2.3918   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    2.8156   -1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949    0.2699   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547    1.5592   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    0.0277    0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8481    0.0314   -1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -1.6924   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3173   -2.0226   -1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202   -1.3637   -2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 15  2  1  0
 13  4  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4,8-Dimethyl-3,7-nonadienyl)-3,4-dihydro-8-hydroxy-3-methylene-2H-1-benzopyran-6-carboxylic acid, 9ci	HMDB
2-(4,8-Dimethylnona-3,7-dien-1-yl)-8-hydroxy-3-methylidene-3,4-dihydro-2H-1-benzopyran-6-carboxylate	Generator

Chemical Formula

C₂₂H₂₈O₄

Average Molecular Weight

356.4553

Monoisotopic Molecular Weight

356.198759384

IUPAC Name

2-[(3Z)-4,8-dimethylnona-3,7-dien-1-yl]-8-hydroxy-3-methylidene-3,4-dihydro-2H-1-benzopyran-6-carboxylic acid

Traditional Name

2-[(3Z)-4,8-dimethylnona-3,7-dien-1-yl]-8-hydroxy-3-methylidene-2,4-dihydro-1-benzopyran-6-carboxylic acid

CAS Registry Number

110979-03-8

SMILES

CC(C)=CCC\C(C)=C/CCC1OC2=C(O)C=C(C=C2CC1=C)C(O)=O

InChI Identifier

InChI=1S/C22H28O4/c1-14(2)7-5-8-15(3)9-6-10-20-16(4)11-17-12-18(22(24)25)13-19(23)21(17)26-20/h7,9,12-13,20,23H,4-6,8,10-11H2,1-3H3,(H,24,25)/b15-9-

InChI Key

XBOKPWYVDNVFMX-DHDCSXOGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Chromane
Benzopyran
Bicyclic monoterpenoid
1-benzopyran
Hydroxybenzoic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040634)

Source

Endogenous

Endogenous (HMDB: HMDB0040634)

Plant

Plant (HMDB: HMDB0040634)

Animal

Animal (HMDB: HMDB0040634)

Exogenous

Food

Food (HMDB: HMDB0040634)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0040634)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040634)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040634)

Lipid metabolism pathway (HMDB: HMDB0040634)

Cellular process

Cell signaling (HMDB: HMDB0040634)

Biochemical process

Lipid transport (HMDB: HMDB0040634)

Role

Biological role

Energy source (HMDB: HMDB0040634)

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	0.0012 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0099 g/L	ALOGPS
logP	4.85	ALOGPS
logP	5.56	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.79 m³·mol⁻¹	ChemAxon
Polarizability	40.84 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	189.757	31661259
DarkChem	[M-H]-	187.15	31661259
DeepCCS	[M+H]+	187.4	30932474
DeepCCS	[M-H]-	185.042	30932474
DeepCCS	[M-2H]-	218.538	30932474
DeepCCS	[M+Na]+	194.16	30932474
AllCCS	[M+H]+	193.3	32859911
AllCCS	[M+H-H2O]+	190.4	32859911
AllCCS	[M+NH4]+	196.0	32859911
AllCCS	[M+Na]+	196.8	32859911
AllCCS	[M-H]-	190.4	32859911
AllCCS	[M+Na-2H]-	190.9	32859911
AllCCS	[M+HCOO]-	191.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.05 minutes	32390414
Predicted by Siyang on May 30, 2022	19.8484 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.82 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3177.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	501.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	237.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	239.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	882.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	940.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1772.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	702.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1565.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	603.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	520.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	447.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperochromanoic acid	CC(C)=CCC\C(C)=C/CCC1OC2=C(O)C=C(C=C2CC1=C)C(O)=O	4363.4	Standard polar	33892256
Piperochromanoic acid	CC(C)=CCC\C(C)=C/CCC1OC2=C(O)C=C(C=C2CC1=C)C(O)=O	2761.0	Standard non polar	33892256
Piperochromanoic acid	CC(C)=CCC\C(C)=C/CCC1OC2=C(O)C=C(C=C2CC1=C)C(O)=O	2905.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperochromanoic acid,1TMS,isomer #1	C=C1CC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2OC1CC/C=C(/C)CCC=C(C)C	2910.7	Semi standard non polar	33892256
Piperochromanoic acid,1TMS,isomer #2	C=C1CC2=CC(C(=O)O[Si](C)(C)C)=CC(O)=C2OC1CC/C=C(/C)CCC=C(C)C	2821.3	Semi standard non polar	33892256
Piperochromanoic acid,2TMS,isomer #1	C=C1CC2=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2OC1CC/C=C(/C)CCC=C(C)C	2794.1	Semi standard non polar	33892256
Piperochromanoic acid,1TBDMS,isomer #1	C=C1CC2=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2OC1CC/C=C(/C)CCC=C(C)C	3127.8	Semi standard non polar	33892256
Piperochromanoic acid,1TBDMS,isomer #2	C=C1CC2=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C2OC1CC/C=C(/C)CCC=C(C)C	3044.7	Semi standard non polar	33892256
Piperochromanoic acid,2TBDMS,isomer #1	C=C1CC2=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2OC1CC/C=C(/C)CCC=C(C)C	3195.5	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 - Piperochromanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-5695000000-675cd1073a6f17671164	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperochromanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-014r-6920700000-68baededabf430a45104	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperochromanoic acid 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 - Piperochromanoic acid 10V, Positive-QTOF	splash10-0cdr-0319000000-0b884a131889c6bf1838	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 20V, Positive-QTOF	splash10-014i-1911000000-dd13f144965f71f15c72	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 40V, Positive-QTOF	splash10-0aor-8930000000-652f6e899c7c67b93aca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 10V, Negative-QTOF	splash10-0a4i-0009000000-f0c10b219ae7dbed409d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 20V, Negative-QTOF	splash10-08fr-0309000000-61056d6fc3d4c7d3d566	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 40V, Negative-QTOF	splash10-0ue9-1920000000-a576ae7aedeaaacce726	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 10V, Positive-QTOF	splash10-0a4i-3079000000-8570c2d7184360aa2185	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 20V, Positive-QTOF	splash10-0uyl-7494000000-df29f3a47f62646dfaf7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 40V, Positive-QTOF	splash10-0006-5920000000-5c6c0e2b3cff3db659b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 10V, Negative-QTOF	splash10-0a4i-0009000000-a3dd451f5dc822798759	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 20V, Negative-QTOF	splash10-0a4i-0319000000-8f76881f8e9b57c0f47d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperochromanoic acid 40V, Negative-QTOF	splash10-00mo-0690000000-d8fcba27a4bc3785a3ae	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB020425

KNApSAcK ID

C00056455

Chemspider ID

35014986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13845940

PDB ID

Not Available

ChEBI ID

175587

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1884931

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 Piperochromanoic acid (HMDB0040634)

MOL for HMDB0040634 (Piperochromanoic acid)

3D MOL for HMDB0040634 (Piperochromanoic acid)

3D SDF for HMDB0040634 (Piperochromanoic acid)

3D-SDF for HMDB0040634 (Piperochromanoic acid)

PDB for HMDB0040634 (Piperochromanoic acid)

3D PDB for HMDB0040634 (Piperochromanoic acid)

SMILES for HMDB0040634 (Piperochromanoic acid)

INCHI for HMDB0040634 (Piperochromanoic acid)

Structure for HMDB0040634 (Piperochromanoic acid)

3D Structure for HMDB0040634 (Piperochromanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra