NP-MRD: Showing NP-Card for myrsinoic acid b (NP0291423)

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Record Information

Version

1.0

Created at

2022-09-09 22:30:47 UTC

Updated at

2022-09-09 22:30:47 UTC

NP-MRD ID

NP0291423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

myrsinoic acid b

Description

Myrsinoic acid B, also known as myrsinoate b, belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. myrsinoic acid b is found in Myrsine seguinii and Myrsine umbellata. It was first documented in 2002 (PMID: 12005065). Myrsinoic acid B is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 18776663) (PMID: 20118542) (PMID: 21383473) (PMID: 21726763) (PMID: 22523418).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171502082D          

 26 27  0  0  0  0            999 V2000
   -3.4712    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  0  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    5.3542    2.0849   -2.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7731    1.1398   -1.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6201    0.0069   -1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5420    1.3248   -1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604    0.4028   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7060   -0.2777   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.1910    0.3334 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3142   -2.1898    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556   -0.4020    1.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0282   -1.9214   -0.0298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5098   -2.6343    1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149   -1.5410    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246   -1.3779    3.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640   -0.2563    3.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053   -0.0660    4.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6312   -0.8795    5.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6511    1.0540    5.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    0.6751    2.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845    0.4956    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7364    1.4920    0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    1.0164   -0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.8590   -1.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5608    1.1701   -2.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669    0.3691   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.6284    0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051   -1.0268   -0.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4200    2.2590   -2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8484    3.0733   -2.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3532    1.6242   -3.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5817    0.0001   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.9234   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7997    0.0447   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611    2.1601   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272    0.9628    0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -0.3617    0.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047   -0.9044   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9412    0.4653   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172   -1.8529    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9409   -3.2207    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -2.2518   -0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6091    0.4599    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -2.6617   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -3.4521    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2996   -2.9339    1.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497   -2.1211    3.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262    1.0536    5.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889    1.5573    2.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    2.4349    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486    1.7266   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7914    0.7664   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325    1.2091   -3.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    2.1107   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8428    0.3481   -2.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6941   -0.6134   -3.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1830    1.0468   -3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8851    0.2959   -2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19 25  2  0
 25 26  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 26 10  1  0
 25 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  6
 11 43  1  0
 11 44  1  0
 13 45  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 17 46  1  0
M  END


  Mrv1533004171502082D          

 26 27  0  0  0  0            999 V2000
   -3.4712    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)(O)C1CC2=CC(=CC(CC=C(C)C)=C2O1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-14(2)7-6-10-22(5,25)19-13-17-12-18(21(23)24)11-16(20(17)26-19)9-8-15(3)4/h7-8,11-12,19,25H,6,9-10,13H2,1-5H3,(H,23,24)

> <INCHI_KEY>
GZLIPAFSJXROEC-UHFFFAOYSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.593125966071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-hydroxy-6-methylhept-5-en-2-yl)-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
5.046097720000001

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.017185843447969

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.311008724891892

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2286831832353196

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
106.07489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-hydroxy-6-methylhept-5-en-2-yl)-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -6.480   1.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.940   1.365   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.170   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.320  -2.843   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.320   0.237   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.170   2.698   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15   11   22                                                  
CONECT   22   21    9                                                       
CONECT   23   13   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
5-Carboxy-2,3-dihydro-2-(1',5'-dimethyl-1'-hydroxy-4'-hexenyl)-7-(3''-methyl-2''-butenyl)benzofuran	ChEBI
Myrsinoate b	Generator

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

2-(2-hydroxy-6-methylhept-5-en-2-yl)-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

Traditional Name

2-(2-hydroxy-6-methylhept-5-en-2-yl)-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)(O)C1CC2=CC(=CC(CC=C(C)C)=C2O1)C(O)=O

InChI Identifier

InChI=1S/C22H30O4/c1-14(2)7-6-10-22(5,25)19-13-17-12-18(21(23)24)11-16(20(17)26-19)9-8-15(3)4/h7-8,11-12,19,25H,6,9-10,13H2,1-5H3,(H,23,24)

InChI Key

GZLIPAFSJXROEC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Myrsine seguinii	LOTUS Database	35616633
Myrsine umbellata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:66427 )
1-benzofurans (CHEBI:66427 )

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	4.22	ALOGPS
logP	5.05	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.31	ChemAxon
pKa (Strongest Basic)	-3.2	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	106.07 m³·mol⁻¹	ChemAxon
Polarizability	41.59 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

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

Not Available

PDB ID

Not Available

ChEBI ID

66427

Good Scents ID

Not Available

References

General References

Hirota M, Miyazaki S, Minakuchi T, Takagi T, Shibata H: Myrsinoic acids B, C and F, anti-inflammatory compounds from Myrsine seguinii. Biosci Biotechnol Biochem. 2002 Mar;66(3):655-9. doi: 10.1271/bbb.66.655. [PubMed:12005065 ]
Ito S, Narise A, Shimura S: Identification of a methioninase inhibitor, myrsinoic acid B, from Myrsine seguinii Lev., and its inhibitory activities. Biosci Biotechnol Biochem. 2008 Sep;72(9):2411-4. doi: 10.1271/bbb.80045. Epub 2008 Sep 7. [PubMed:18776663 ]
Hess S, Padoani C, Scorteganha LC, Holzmann I, Malheiros A, Yunes RA, Delle Monache F, de Souza MM: Assessment of mechanisms involved in antinociception caused by myrsinoic acid B. Biol Pharm Bull. 2010;33(2):209-15. doi: 10.1248/bpb.33.209. [PubMed:20118542 ]
Ito S, Shimura S, Tanaka T, Yaegaki K: Myrsinoic acid B inhibits the production of hydrogen sulfide by periodontal pathogens in vitro. J Breath Res. 2010 Jun;4(2):026005. doi: 10.1088/1752-7155/4/2/026005. Epub 2010 Apr 9. [PubMed:21383473 ]
Baccarin T, Muceneeki RS, Bresolin TM, Yunes RA, Malheiros A, Lucinda-Silva RM: Development and validation of an HPLC-PDA method for the determination of myrsinoic acid B in the extracts of Rapanea ferruginea Mez. Talanta. 2011 Aug 15;85(2):1221-4. doi: 10.1016/j.talanta.2011.05.017. Epub 2011 May 13. [PubMed:21726763 ]
Antonialli Cde S, da Silva GF, Rocha LW, Monteiro ER, de Souza MM, Malheiros A, Yunes RA, Quintao NL: Antihyperalgesic effects of myrsinoic acid B in pain-like behavior induced by inflammatory and neuropathic pain models in mice. Anesth Analg. 2012 Aug;115(2):461-9. doi: 10.1213/ANE.0b013e318253afd1. Epub 2012 Apr 20. [PubMed:22523418 ]
LOTUS database [Link]

Showing NP-Card for myrsinoic acid b (NP0291423)

MOL for NP0291423 (myrsinoic acid b)

3D MOL for NP0291423 (myrsinoic acid b)

3D SDF for NP0291423 (myrsinoic acid b)

3D-SDF for NP0291423 (myrsinoic acid b)

PDB for NP0291423 (myrsinoic acid b)

3D PDB for NP0291423 (myrsinoic acid b)

SMILES for NP0291423 (myrsinoic acid b)

INCHI for NP0291423 (myrsinoic acid b)

Structure for NP0291423 (myrsinoic acid b)

3D Structure for NP0291423 (myrsinoic acid b)