NP-MRD: Showing NP-Card for (2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0158227)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 15:46:53 UTC

Updated at

2022-09-02 15:46:54 UTC

NP-MRD ID

NP0158227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

3,4-Dihydroxy-trans-cinnamic acid (2S)-2beta-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3alpha-yl ester belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. (2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Laguncularia racemosa. Based on a literature review very few articles have been published on 3,4-Dihydroxy-trans-cinnamic acid (2S)-2beta-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3alpha-yl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217462D          

 32 35  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    0.6629   -0.1415   -1.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622    0.2102   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184    0.1143    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335   -0.3401   -0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -0.4607    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9536   -0.1169    1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2470   -0.2435    1.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2001   -0.7386    0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5160   -0.8708    1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8537   -1.0867   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8370   -1.5865   -1.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -0.9603   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048    0.6881    0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    0.7730   -0.2279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0117    2.1614   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091    3.1699    0.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    2.3257   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9612    3.5733   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121    4.6725   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3020    3.7081   -1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1621    2.6318   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5090    2.7970   -1.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6214    1.3838   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850    1.2231   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020   -0.0019   -0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5098   -0.0575    0.5242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1283   -1.4530    0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -1.9418    1.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3806   -3.2795    2.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856   -4.1459    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610   -3.6649   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -2.3453   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    0.4143    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185   -0.6390   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    0.2689    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5050    0.0363    2.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2059   -1.2261    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6099   -1.8545   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3049   -1.2449   -1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086    0.4259   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4042    5.6033   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7136    4.6799   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1605    2.9791   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2680    0.5171   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    0.4701    1.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -1.3135    2.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -3.6246    3.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0906   -5.1845    1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7687   -4.3298   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4210   -1.9749   -1.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  2  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 14 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 23 21  1  0
 32 27  1  0
 24 17  1  0
 12  5  1  0
 22 43  1  0
 20 42  1  0
 19 41  1  0
 14 40  1  6
  3 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 26 45  1  1
 23 44  1  0
 28 46  1  0
 29 47  1  0
 30 48  1  0
 31 49  1  0
 32 50  1  0
M  END


  Mrv1652309022217462D          

 32 35  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)[C@@H](OC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@@H](OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H18O8/c25-15-11-18(28)21-19(12-15)31-23(14-4-2-1-3-5-14)24(22(21)30)32-20(29)9-7-13-6-8-16(26)17(27)10-13/h1-12,23-28H/b9-7+/t23-,24+/m0/s1

> <INCHI_KEY>
ONJCIGFCUCTTGU-UWMQVQQRSA-N

> <FORMULA>
C24H18O8

> <MOLECULAR_WEIGHT>
434.4

> <EXACT_MASS>
434.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.97534632508305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-5,7-dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
4.850274986

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.000374910904824

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.739269502938561

> <JCHEM_PKA_STRONGEST_BASIC>
-4.961279787458862

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
114.17660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   14   27                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate (2S)-2b-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3a-yl ester	Generator
3,4-Dihydroxy-trans-cinnamate (2S)-2beta-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3alpha-yl ester	Generator
3,4-Dihydroxy-trans-cinnamate (2S)-2β-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3α-yl ester	Generator
3,4-Dihydroxy-trans-cinnamic acid (2S)-2b-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3a-yl ester	Generator
3,4-Dihydroxy-trans-cinnamic acid (2S)-2β-phenyl-4-oxo-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3α-yl ester	Generator

Chemical Formula

C₂₄H₁₈O₈

Average Mass

434.4000 Da

Monoisotopic Mass

434.10017 Da

IUPAC Name

(2S,3S)-5,7-dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3S)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)[C@@H](OC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@@H](OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C24H18O8/c25-15-11-18(28)21-19(12-15)31-23(14-4-2-1-3-5-14)24(22(21)30)32-20(29)9-7-13-6-8-16(26)17(27)10-13/h1-12,23-28H/b9-7+/t23-,24+/m0/s1

InChI Key

ONJCIGFCUCTTGU-UWMQVQQRSA-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
Laguncularia racemosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanonol
Hydroxyflavonoid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Chromone
Chromane
Benzopyran
1-benzopyran
Catechol
Styrene
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-acyloxy ketone
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Enoate ester
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.12	ALOGPS
logP	4.85	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.18 m³·mol⁻¹	ChemAxon
Polarizability	42.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

27024937

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45378687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0158227)

MOL for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0158227 ((2s,3s)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)