NP-MRD: Showing NP-Card for Ursolic acid (trans-3-O-hydroxycinnamoyl-) (NP0050168)

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Record Information

Version

2.0

Created at

2022-03-17 21:24:23 UTC

Updated at

2022-03-17 21:24:23 UTC

NP-MRD ID

NP0050168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ursolic acid (trans-3-O-hydroxycinnamoyl-)

Description

(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-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 belongs to the class of organic compounds known as triterpenoids. Ursolic acid (trans-3-O-hydroxycinnamoyl-) is found in Monochaetum vulcanicum. These are terpene molecules containing six isoprene units (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-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 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Ursolic acid (trans-3-O-hydroxycinnamoyl-)
  Mrv1652304022019552D          
  Mrv0541 01231311332D          
 44 49  0  0  1  0            999 V2000
    7.0979   -1.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4611    0.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7562   -0.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883   -0.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0919   -3.1756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8328   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1183   -0.2642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3676   -0.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5472   -0.2642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3610   -1.5417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8461   -1.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5472    0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1051   -1.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5892   -1.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2848    1.0019    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1183    0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2848   -0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6029   -0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322    0.5779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3631   -1.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8140   -1.5477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8328    0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3739    0.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8210   -0.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8295   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2641    1.8968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8109    1.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322    2.3562    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1795   -2.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0045   -2.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8109    1.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7499    0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5418    2.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0227    3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3851   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -1.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562   -1.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2402   -1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5273   -1.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2369   -2.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8112   -1.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8080   -2.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  1  0  0  0
  1 36  1  0  0  0  0
  2 33  1  0  0  0  0
  3 33  2  0  0  0  0
  4 36  2  0  0  0  0
  5 44  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 20  1  1  0  0  0
  7  8  1  0  0  0  0
  7 16  1  1  0  0  0
  8 10  1  0  0  0  0
  8 18  1  0  0  0  0
  8 24  1  1  0  0  0
  9 12  1  0  0  0  0
  9 17  1  0  0  0  0
  9 26  1  6  0  0  0
 10 13  1  1  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 15 12  1  6  0  0  0
 12 23  2  0  0  0  0
 14 22  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 19  1  0  0  0  0
 15 27  1  0  0  0  0
 16 23  1  0  0  0  0
 17 21  1  0  0  0  0
 18 25  1  0  0  0  0
 19 21  1  0  0  0  0
 19 28  1  0  0  0  0
 19 33  1  1  0  0  0
 22 25  1  0  0  0  0
 27 29  1  0  0  0  0
 27 34  1  1  0  0  0
 28 32  1  0  0  0  0
 29 32  1  0  0  0  0
 29 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  2  0  0  0  0
 42 44  2  0  0  0  0
 43 44  1  0  0  0  0
M  END

Ursolic acid (trans-3-O-hydroxycinnamoyl-)
  Mrv1652304022019552D          
  Mrv0541 01231311332D          
 44 49  0  0  1  0            999 V2000
    7.0979   -1.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4611    0.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7562   -0.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883   -0.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0919   -3.1756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8328   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1183   -0.2642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3676   -0.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5472   -0.2642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3610   -1.5417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8461   -1.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5472    0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1051   -1.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5892   -1.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2848    1.0019    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1183    0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2848   -0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6029   -0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322    0.5779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3631   -1.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8140   -1.5477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8328    0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3739    0.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8210   -0.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8295   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2641    1.8968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8109    1.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322    2.3562    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1795   -2.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0045   -2.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8109    1.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7499    0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5418    2.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0227    3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3851   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -1.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562   -1.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2402   -1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5273   -1.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2369   -2.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8112   -1.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8080   -2.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  1  0  0  0
  1 36  1  0  0  0  0
  2 33  1  0  0  0  0
  3 33  2  0  0  0  0
  4 36  2  0  0  0  0
  5 44  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 20  1  1  0  0  0
  7  8  1  0  0  0  0
  7 16  1  1  0  0  0
  8 10  1  0  0  0  0
  8 18  1  0  0  0  0
  8 24  1  1  0  0  0
  9 12  1  0  0  0  0
  9 17  1  0  0  0  0
  9 26  1  6  0  0  0
 10 13  1  1  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 15 12  1  6  0  0  0
 12 23  2  0  0  0  0
 14 22  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 19  1  0  0  0  0
 15 27  1  0  0  0  0
 16 23  1  0  0  0  0
 17 21  1  0  0  0  0
 18 25  1  0  0  0  0
 19 21  1  0  0  0  0
 19 28  1  0  0  0  0
 19 33  1  1  0  0  0
 22 25  1  0  0  0  0
 27 29  1  0  0  0  0
 27 34  1  1  0  0  0
 28 32  1  0  0  0  0
 29 32  1  0  0  0  0
 29 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  2  0  0  0  0
 42 44  2  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)\C=C\C6=CC=C(O)C=C6)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C39H54O5/c1-24-16-21-39(34(42)43)23-22-37(6)28(33(39)25(24)2)13-14-30-36(5)19-18-31(35(3,4)29(36)17-20-38(30,37)7)44-32(41)15-10-26-8-11-27(40)12-9-26/h8-13,15,24-25,29-31,33,40H,14,16-23H2,1-7H3,(H,42,43)/b15-10+/t24-,25+,29+,30-,31+,33+,36+,37-,38-,39+/m1/s1

> <INCHI_KEY>
ZOXDAGKKDOEJBW-YVZDRRNJSA-N

> <FORMULA>
C39H54O5

> <MOLECULAR_WEIGHT>
602.856

> <EXACT_MASS>
602.397124839

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
71.67410581029945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-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>
7.92

> <JCHEM_LOGP>
9.312130806

> <ALOGPS_LOGS>
-6.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.398623989120315

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744115799385438

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9547318749588785

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
175.24659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Ursolic acid (trans-3-O-hydroxycinnamoyl-)        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  O   UNK     0      13.249  -3.654   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.994   1.099   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      25.678  -1.221   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.925  -1.339   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.905  -5.928   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.221  -1.263   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.887  -0.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.486  -1.274   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.555  -0.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.474  -2.878   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.246  -2.867   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.555   1.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.863  -3.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.033  -3.725   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.932   1.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.887   1.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.932  -1.317   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.059  -0.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.327   1.079   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.211  -2.443   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.327  -0.525   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.586  -2.889   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.221   1.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.498   0.266   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.599  -1.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.082  -1.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.893   3.541   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.780   1.903   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.327   4.398   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.268  -5.061   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.808  -5.055   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.780   3.574   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.666   0.319   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.545   4.285   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      24.309   5.938   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.919  -2.879   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.582  -3.644   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.252  -2.868   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.915  -3.633   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.584  -2.858   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.909  -5.173   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.248  -3.623   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.572  -5.938   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.242  -5.163   0.000  0.00  0.00           C+0
CONECT    1   22   36                                                       
CONECT    2   33                                                            
CONECT    3   33                                                            
CONECT    4   36                                                            
CONECT    5   44                                                            
CONECT    6    7    9   11   20                                             
CONECT    7    6    8   16                                                  
CONECT    8    7   10   18   24                                             
CONECT    9    6   12   17   26                                             
CONECT   10    8   13   14                                                  
CONECT   11    6   13                                                       
CONECT   12    9   15   23                                                  
CONECT   13   10   11                                                       
CONECT   14   10   22   30   31                                             
CONECT   15   12   19   27                                                  
CONECT   16    7   23                                                       
CONECT   17    9   21                                                       
CONECT   18    8   25                                                       
CONECT   19   15   21   28   33                                             
CONECT   20    6                                                            
CONECT   21   17   19                                                       
CONECT   22    1   14   25                                                  
CONECT   23   12   16                                                       
CONECT   24    8                                                            
CONECT   25   18   22                                                       
CONECT   26    9                                                            
CONECT   27   15   29   34                                                  
CONECT   28   19   32                                                       
CONECT   29   27   32   35                                                  
CONECT   30   14                                                            
CONECT   31   14                                                            
CONECT   32   28   29                                                       
CONECT   33    2    3   19                                                  
CONECT   34   27                                                            
CONECT   35   29                                                            
CONECT   36    1    4   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39   42                                                       
CONECT   41   39   43                                                       
CONECT   42   40   44                                                       
CONECT   43   41   44                                                       
CONECT   44    5   42   43                                                  
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4AS,6as,6BR,8ar,10S,12ar,12BR,14BS)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-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-carboxylate	Generator
3-(p-Coumaroyl)ursolate	Generator

Chemical Formula

C₃₉H₅₄O₅

Average Mass

602.8560 Da

Monoisotopic Mass

602.39712 Da

IUPAC Name

Traditional Name

(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)\C=C\C6=CC=C(O)C=C6)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O

InChI Identifier

InChI=1S/C39H54O5/c1-24-16-21-39(34(42)43)23-22-37(6)28(33(39)25(24)2)13-14-30-36(5)19-18-31(35(3,4)29(36)17-20-38(30,37)7)44-32(41)15-10-26-8-11-27(40)12-9-26/h8-13,15,24-25,29-31,33,40H,14,16-23H2,1-7H3,(H,42,43)/b15-10+/t24-,25+,29+,30-,31+,33+,36+,37-,38-,39+/m1/s1

InChI Key

ZOXDAGKKDOEJBW-YVZDRRNJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Monochaetum vulcanicum	LOTUS Database	35616633
Vaccinium macrocarpon	FooDB	PHYTOHUB

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
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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	7.92	ALOGPS
logP	9.31	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	175.25 m³·mol⁻¹	ChemAxon
Polarizability	71.67 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24203733

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ursolic acid (trans-3-O-hydroxycinnamoyl-) (NP0050168)

MOL for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

3D MOL for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

3D SDF for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

3D-SDF for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

PDB for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

3D PDB for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

SMILES for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

INCHI for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

Structure for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))

3D Structure for NP0050168 (Ursolic acid (trans-3-O-hydroxycinnamoyl-))