NP-MRD: Showing NP-Card for Euscaphic acid (NP0048563)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:26 UTC

Updated at

2022-03-17 20:58:26 UTC

NP-MRD ID

NP0048563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euscaphic acid

Description

Euscaphic acid, also known as jacarandic acid or tormentic acid, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Euscaphic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Euscaphic acid has been detected, but not quantified in, herbs and spices and loquats. This could make euscaphic acid a potential biomarker for the consumption of these foods. Euscaphic acid is found in Acaena pinnatifida, Acanthochlamys bracteata, Agrimonia pilosa, Alchemilla alpina, Alchemilla vulgaris, Anchusa strigosa, Arnebia euchroma, Callicarpa americana, Campsis grandiflora, Cecropia pachystachya, Centella asiatica, Chaenomeles sinensis, Chaenomeles speciosa, Cornus kousa, Cotoneaster symondsii, Drymonia macrophylla, Dysoxylum densiflorum, Elsholtzia bodinieri, Elsholtzia ciliata, Euscaphis japonica, Fragaria ananassa, Geum japonicum, Hedyotis lawsoniae, Hoslundia opposita, Hyptis capitata, Incarvillea arguta, Isodon effusus, Isodon loxothyrsus, Isodon sculponeatus, Laggera pterodonta, Lecanthus peduncularis, Lepechinia caulescens, Leucosceptrum stellipilum, Licania pyrifolia, Margyricarpus setosus, Markhamia tomentosa, Marsypianthes chamaedrys, Licania tomentosa, Mosla scabra, Musanga cecropioides, Myrianthus arboreus, Myrianthus libericus, Myrianthus serratus, Ocimum basilicum, Olea europaea, Paliurus hemsleyanus, Perilla frutescens, Photinia serratifolia, Pimpinella saxifraga, Polylepis incana, Dasiphora fruticosa, Prunus zippeliana, Pygeum topengii, Pyracantha coccinea, Eriobotrya deflexa, Rosa bella, Rosa davidii, Rosa davurica, Rosa laevigata, Rosa multiflora, Rosa roxburghii, Rosa rugosa, Rosa sericea, Rosa sterilis, Rosa taiwanensis, Rosa transmorrisonensis, Rosa woodsii, Rubus allegheniensis, Rubus cochinchinensis, Rubus ellipticus, Rubus irenaeus, Rubus parkeri, Rubus pungens, Rubus ulmifolius, Rubus xanthocarpus, Rumex japonicus, Sanguisorba ancistroides, Sanguisorba officinalis, Sarcopoterium spinosum, Tecoma stans, Ternstroemia gymnanthera, Tiarella polyphylla, Triumfetta cordifolia, Trogopterus xanthipes, Turpinia arguta, Vismia guianensis, Vitex altissima and Vitex negundo. It was first documented in 2000 (PMID: 11413487). A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567) (PMID: 21384845).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 01101308242D          

 38 42  0  0  0  0            999 V2000
   -3.1616    0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761    0.3398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8761   -0.4852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1616   -0.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -0.4852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4471    0.3398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7327    0.7523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7327   -0.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182   -0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.3398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0182    1.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037    0.7523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3037    1.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.9899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4107    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252    0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252    1.5774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1252    3.2274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4107    2.8149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8397    1.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5905   -0.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616   -1.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761   -1.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471    1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037   -0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541    1.5774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    0.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252    4.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906    0.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -1.3102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327   -0.0727    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.1649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    3.2274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 16  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 15 18  1  0  0  0  0
 20 15  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  1  0  0  0
 10 27  1  1  0  0  0
 13 28  1  6  0  0  0
 18 29  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 19 32  1  6  0  0  0
  2 33  1  6  0  0  0
  5 34  1  6  0  0  0
  7 35  1  6  0  0  0
 15 36  1  1  0  0  0
 20 37  1  6  0  0  0
 20 38  1  1  0  0  0
M  END


  Mrv0541 01101308242D          

 38 42  0  0  0  0            999 V2000
   -3.1616    0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761    0.3398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8761   -0.4852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1616   -0.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -0.4852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4471    0.3398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7327    0.7523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7327   -0.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182   -0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.3398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0182    1.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037    0.7523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3037    1.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.9899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4107    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252    0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252    1.5774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1252    3.2274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4107    2.8149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8397    1.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5905   -0.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616   -1.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761   -1.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471    1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037   -0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541    1.5774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    0.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252    4.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906    0.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -1.3102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327   -0.0727    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.1649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    3.2274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 16  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 15 18  1  0  0  0  0
 20 15  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  1  0  0  0
 10 27  1  1  0  0  0
 13 28  1  6  0  0  0
 18 29  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 19 32  1  6  0  0  0
  2 33  1  6  0  0  0
  5 34  1  6  0  0  0
  7 35  1  6  0  0  0
 15 36  1  1  0  0  0
 20 37  1  6  0  0  0
 20 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0048563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@@H](O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
OXVUXGFZHDKYLS-QUFHAEKXSA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.6991

> <EXACT_MASS>
488.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
56.474774216062855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
4.269648307666667

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.570942438093166

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.643417376538086

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0362746208615112

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
136.6646

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JAN-13         0                                  
HETATM    1  C   UNK     0      -5.902   1.404   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.235   0.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.235  -0.906   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.902  -1.676   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.568  -0.906   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.568   0.634   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.234   1.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.234  -1.676   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.901  -0.906   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.901   0.634   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.901   3.714   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.234   2.944   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.567   1.404   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.567   2.944   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.767   3.714   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.767   0.634   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.100   1.404   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.100   2.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.100   6.024   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.767   5.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.434   3.714   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.434   5.254   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.569  -1.676   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.902  -3.216   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.235  -2.446   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.568   2.174   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.901   2.174   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.567  -0.136   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.434   2.174   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.768   2.944   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.434   0.634   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.100   7.564   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.569   1.404   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -4.568  -2.446   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.234  -0.136   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.767   2.174   0.000  0.00  0.00           H+0
HETATM   37  O   UNK     0      -0.567   6.024   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.767   6.794   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   24   25                                             
CONECT    5    4    6    8   34                                             
CONECT    6    1    7    5   26                                             
CONECT    7    6   12   10   35                                             
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    7   13   27                                             
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   10   16   14   28                                             
CONECT   14   11   13   15                                                  
CONECT   15   14   18   20   36                                             
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   21   15   29                                             
CONECT   19   20   22   32                                                  
CONECT   20   15   19   37   38                                             
CONECT   21   18   22                                                       
CONECT   22   21   19                                                       
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   13                                                            
CONECT   29   18   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   19                                                            
CONECT   33    2                                                            
CONECT   34    5                                                            
CONECT   35    7                                                            
CONECT   36   15                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Jacarandic acid	ChEBI
Tormentic acid	ChEBI
Jacarandate	Generator
Tormentate	Generator
Euscaphate	Generator
Acuminatic acid	HMDB
2alpha-Acetyl tormentic acid	HMDB
(2alpha,3beta)-Isomer OF euscaphic acid	HMDB

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.6991 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

(1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

53155-25-2

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@@H](O)C2(C)C

InChI Identifier

InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1

InChI Key

OXVUXGFZHDKYLS-QUFHAEKXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acaena pinnatifida	LOTUS Database	35616633
Acanthochlamys bracteata	LOTUS Database	35616633
Agrimonia pilosa	LOTUS Database	35616633
Alchemilla alpina	LOTUS Database	35616633
Alchemilla vulgaris	LOTUS Database	35616633
Anchusa strigosa	LOTUS Database	35616633
Arnebia euchroma	LOTUS Database	35616633
Callicarpa americana	LOTUS Database	35616633
Campsis grandiflora	LOTUS Database	35616633
Cecropia pachystachya	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Chaenomeles speciosa	LOTUS Database	35616633
Cornus kousa	LOTUS Database	35616633
Cotoneaster symondsii	LOTUS Database	35616633
Drymonia macrophylla	LOTUS Database	35616633
Dysoxylum densiflorum	LOTUS Database	35616633
Elsholtzia bodinieri	LOTUS Database	35616633
Elsholtzia ciliata	LOTUS Database	35616633
Eriobotrya japonica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Euscaphis japonica	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633
Geum japonicum	LOTUS Database	35616633
Hedyotis lawsoniae	LOTUS Database	35616633
Hoslundia opposita	LOTUS Database	35616633
Hyptis capitata	LOTUS Database	35616633
Incarvillea arguta	LOTUS Database	35616633
Isodon effusus	LOTUS Database	35616633
Isodon loxothyrsus	LOTUS Database	35616633
Isodon sculponeatus	LOTUS Database	35616633
Laggera pterodonta	LOTUS Database	35616633
Lecanthus peduncularis	LOTUS Database	35616633
Lepechinia caulescens	LOTUS Database	35616633
Leucosceptrum stellipilum	LOTUS Database	35616633
Licania pyrifolia	LOTUS Database	35616633
Margyricarpus setosus	LOTUS Database	35616633
Markhamia tomentosa	LOTUS Database	35616633
Marsypianthes chamaedrys	LOTUS Database	35616633
Moquilea tomentosa	LOTUS Database	35616633
Mosla scabra	LOTUS Database	35616633
Musanga cecropioides	LOTUS Database	35616633
Myrianthus arboreus	LOTUS Database	35616633
Myrianthus libericus	LOTUS Database	35616633
Myrianthus serratus	LOTUS Database	35616633
Ocimum basilicum	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Paliurus hemsleyanus	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Photinia serratifolia	LOTUS Database	35616633
Pimpinella saxifraga	LOTUS Database	35616633
Polylepis incana	LOTUS Database	35616633
Potentilla fruticosa	LOTUS Database	35616633
Prunus zippeliana	LOTUS Database	35616633
Pygeum topengii	LOTUS Database	35616633
Pyracantha coccinea	LOTUS Database	35616633
Rhaphiolepis deflexa	LOTUS Database	35616633
Rosa bella	LOTUS Database	35616633
Rosa davidii	LOTUS Database	35616633
Rosa davurica	LOTUS Database	35616633
Rosa laevigata	LOTUS Database	35616633
Rosa multiflora	LOTUS Database	35616633
Rosa roxburghii	LOTUS Database	35616633
Rosa rugosa	LOTUS Database	35616633
Rosa sericea	LOTUS Database	35616633
Rosa sterilis (nom. nud.)	LOTUS Database	35616633
Rosa taiwanensis	LOTUS Database	35616633
Rosa transmorrisonensis	LOTUS Database	35616633
Rosa woodsii	LOTUS Database	35616633
Rubus allegheniensis	LOTUS Database	35616633
Rubus cochinchinensis	LOTUS Database	35616633
Rubus ellipticus	LOTUS Database	35616633
Rubus irenaeus	LOTUS Database	35616633
Rubus parkeri	LOTUS Database	35616633
Rubus pungens	LOTUS Database	35616633
Rubus ulmifolius	LOTUS Database	35616633
Rubus xanthocarpus	LOTUS Database	35616633
Rumex japonicus	LOTUS Database	35616633
Sanguisorba ancistroides	LOTUS Database	35616633
Sanguisorba officinalis	LOTUS Database	35616633
Sarcopoterium spinosum	LOTUS Database	35616633
Tecoma stans	LOTUS Database	35616633
Ternstroemia gymnanthera	LOTUS Database	35616633
Tiarella polyphylla	LOTUS Database	35616633
Triumfetta cordifolia	LOTUS Database	35616633
Trogopterus xanthipes	LOTUS Database	35616633
Turpinia arguta	LOTUS Database	35616633
Vismia guianensis	LOTUS Database	35616633
Vitex altissima	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triol (CHEBI:67914 )
hydroxy monocarboxylic acid (CHEBI:67914 )
pentacyclic triterpenoid (CHEBI:67914 )
Ursanes (C17890 )
Dammarenes (C17890 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	4.87	ALOGPS
logP	4.27	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	136.66 m³·mol⁻¹	ChemAxon
Polarizability	56.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036651

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13653335

PDB ID

Not Available

ChEBI ID

67914

Good Scents ID

Not Available

References

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 ]
Zeng N, Shen Y, Li LZ, Jiao WH, Gao PY, Song SJ, Chen WS, Lin HW: Anti-inflammatory triterpenes from the leaves of Rosa laevigata. J Nat Prod. 2011 Apr 25;74(4):732-8. doi: 10.1021/np1007922. Epub 2011 Mar 8. [PubMed:21384845 ]

Showing NP-Card for Euscaphic acid (NP0048563)

MOL for NP0048563 (Euscaphic acid)

3D MOL for NP0048563 (Euscaphic acid)

3D SDF for NP0048563 (Euscaphic acid)

3D-SDF for NP0048563 (Euscaphic acid)

PDB for NP0048563 (Euscaphic acid)

3D PDB for NP0048563 (Euscaphic acid)

SMILES for NP0048563 (Euscaphic acid)

INCHI for NP0048563 (Euscaphic acid)

Structure for NP0048563 (Euscaphic acid)

3D Structure for NP0048563 (Euscaphic acid)