NP-MRD: Showing NP-Card for (2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate (NP0331033)

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Record Information

Version

2.0

Created at

2022-09-12 16:58:22 UTC

Updated at

2022-09-12 16:58:22 UTC

NP-MRD ID

NP0331033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Description

Brevipolide J belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate is found in Hyptis brevipes. (2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate was first documented in 2013 (PMID: 23282042). Based on a literature review very few articles have been published on Brevipolide J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218582D          

 30 32  0  0  1  0            999 V2000
   -6.1283   -6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283   -5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -4.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -4.4270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -6.4895    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 14  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  1  0  0  0
 21 19  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    9.8825    0.2915   -1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0756    0.6218    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036    0.4011    0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0838   -0.1641   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6981   -0.3953   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9106   -0.0747    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768   -0.2976    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574   -0.8373   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965   -1.0584   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7850   -1.5691   -1.7935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7364   -0.6837    0.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6418   -0.8718    0.4255 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8997   -1.8225    1.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7977    1.4667    0.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    0.3452    0.7428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6030    1.4170    1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    1.4780   -0.0089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5499    1.0210   -0.9939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1405    2.1175   -1.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5566   -0.0010   -0.6190 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7634    0.7195    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8673   -0.2543    0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0596   -1.2767   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1070   -1.4813   -1.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2360   -2.4355   -2.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0802   -0.5461   -1.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5720    0.5001    1.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9298    0.7310    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5644    1.2997    2.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6512   -0.7293   -1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7816    1.0288   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9463    0.2798   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6869   -0.4268   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -0.8448   -1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8858   -0.0260    1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3530   -1.1356   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0141   -1.3342   -0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -2.8429    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0317   -1.8253    2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2930   -0.6618    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9828    2.1679    2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642    1.1047    2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8966    2.2950   -0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.5662   -1.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3393    2.7844   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2688   -0.7904    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0378    1.5778   -0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4733    1.0603    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6050   -0.1415    0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8983   -1.9395   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9355    0.7491    2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0239    1.5535    3.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
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  7  8  2  0
  8  9  1  0
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 14 15  2  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
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 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
  6 28  1  0
 28 29  2  0
 29 30  1  0
 29  3  1  0
 18 16  1  0
 27 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  7 36  1  0
  8 37  1  0
 12 38  1  6
 13 39  1  0
 13 40  1  0
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 16 42  1  6
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 20 47  1  0
 21 48  1  1
 22 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 28 53  1  0
 30 54  1  0
M  END


  Mrv1652309122218582D          

 30 32  0  0  1  0            999 V2000
   -6.1283   -6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283   -5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -4.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -4.4270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -6.4895    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 14  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  1  0  0  0
 21 19  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C\C(=O)O[C@@H](C)C(=O)[C@H]2C[C@@H]2[C@H](O)[C@H]2CC=CC(=O)O2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O8/c1-12(29-20(25)9-7-13-6-8-17(28-2)16(23)10-13)21(26)14-11-15(14)22(27)18-4-3-5-19(24)30-18/h3,5-10,12,14-15,18,22-23,27H,4,11H2,1-2H3/b9-7+/t12-,14-,15-,18+,22-/m0/s1

> <INCHI_KEY>
BDIGJZNTLJAZGG-YVGDPVPUSA-N

> <FORMULA>
C22H24O8

> <MOLECULAR_WEIGHT>
416.426

> <EXACT_MASS>
416.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.918853524043215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(1S,2S)-2-[(S)-hydroxy[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
2.9118265580000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.884288422965469

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.822912873674362

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2823129983168586

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
107.57600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(1S,2S)-2-[(S)-hydroxy[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.439 -12.114   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -11.439 -10.574   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -10.106  -9.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.106  -8.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.772  -7.494   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.438  -8.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.105  -7.494   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.771  -8.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.437  -7.494   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.437  -5.954   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.104  -8.264   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.770  -7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.770  -5.954   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -8.264   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.564  -9.804   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.897  -7.494   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.437  -7.494   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.771  -8.264   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.771  -9.804   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.105  -7.494   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.438  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.772  -5.954   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.772  -7.494   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.106  -8.264   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.438  -8.264   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -7.438  -9.804   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.772 -10.574   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.772 -12.114   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   18                                                       
CONECT   18   17   16   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28    6   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₈

Average Mass

416.4260 Da

Monoisotopic Mass

416.14712 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C\C(=O)O[C@@H](C)C(=O)[C@H]2C[C@@H]2[C@H](O)[C@H]2CC=CC(=O)O2)C=C1O

InChI Identifier

InChI=1S/C22H24O8/c1-12(29-20(25)9-7-13-6-8-17(28-2)16(23)10-13)21(26)14-11-15(14)22(27)18-4-3-5-19(24)30-18/h3,5-10,12,14-15,18,22-23,27H,4,11H2,1-2H3/b9-7+/t12-,14-,15-,18+,22-/m0/s1

InChI Key

BDIGJZNTLJAZGG-YVGDPVPUSA-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
Hyptis brevipes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Dihydropyranone
Fatty acid ester
Alpha-acyloxy ketone
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

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

28536083

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71521916

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Suarez-Ortiz GA, Cerda-Garcia-Rojas CM, Hernandez-Rojas A, Pereda-Miranda R: Absolute configuration and conformational analysis of brevipolides, bioactive 5,6-dihydro-alpha-pyrones from Hyptis brevipes. J Nat Prod. 2013 Jan 25;76(1):72-8. doi: 10.1021/np300740h. Epub 2013 Jan 2. [PubMed:23282042 ]
LOTUS database [Link]

Showing NP-Card for (2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate (NP0331033)

MOL for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D MOL for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D SDF for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

PDB for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D PDB for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

SMILES for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

INCHI for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

Structure for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D Structure for NP0331033 ((2s)-1-[(1s,2s)-2-[(s)-hydroxy[(2r)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)