NP-MRD: Showing NP-Card for (2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0181360)

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Record Information

Version

2.0

Created at

2022-09-03 19:51:54 UTC

Updated at

2022-09-03 19:51:54 UTC

NP-MRD ID

NP0181360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

Description

SINENSIN belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. (2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one is found in Abies nephrolepis, Cornus mas, Crocus chrysanthus, Helichrysum arenarium and Pseudotsuga menziesii. (2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one was first documented in 2001 (PMID: 11368567). SINENSIN is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 23888242).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006292D          

 32 35  0  0  0  0            999 V2000
10001.0655 9998.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.635710002.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6409 9998.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.214110000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7852 9998.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0707 9997.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.785210001.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.354210000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3542 9999.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.066210000.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0662 9999.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7807 9999.5841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.780710000.4092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.354910000.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.640410000.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925910000.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9258 9999.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6403 9999.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3549 9999.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.922210001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.207810002.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.493210001.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.493210000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.207710000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.922310000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.784510000.8252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.070010000.4127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.0700 9999.5876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.7845 9999.1752    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4990 9999.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.499010000.4127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4951 9999.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
  1 11  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 16  4  1  0  0  0  0
 18  3  1  0  0  0  0
 10 14  1  0  0  0  0
 19 11  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 20  1  0  0  0  0
 13 23  1  6  0  0  0
 20  2  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31  4  1  6  0  0  0
 29  5  1  6  0  0  0
 28  9  1  1  0  0  0
 27  8  1  6  0  0  0
 26  7  1  1  0  0  0
 12 32  1  1  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    2.9898   -2.1311   -2.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8495   -1.8925   -1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -1.3294   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227   -1.5567   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -2.3233   -2.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -0.9920   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751   -0.2186    0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989    0.3690    0.8988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    0.2580    0.4111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6610    1.5116    0.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7958    1.3166   -0.6488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2436    2.6846   -1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3893    2.5929   -1.9390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8681    0.6786    0.2056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0410    0.4999   -0.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3207   -0.6400    0.6970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2345   -1.3395    1.4812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403   -0.3497    1.4518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5085   -1.5215    1.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -0.0002    0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091   -0.5425    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.3675    1.0666 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190   -1.0514    0.7904 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1580   -0.0744    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719    1.0402    1.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2046    2.0218    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0743    1.9375   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0284    2.9463   -0.2608 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793    0.8433   -0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310   -0.1411   -0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9391   -2.1756   -0.1918 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4921   -3.3033    0.5474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -2.7969   -2.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870   -1.1979   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -0.3466   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5288    0.6495   -1.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4535    3.1143   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841    3.3898   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9674    3.4027   -1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0233    1.3497    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7235    1.1064   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182   -1.2686   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8735   -1.7783    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2566    0.4122    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061   -2.2466    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068    0.6129    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483   -1.5029    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6092    1.1653    2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743    2.8887    1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9529    2.8850    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6480    0.7597   -1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9801   -0.9725   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8219   -2.4953   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486   -3.8806    0.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 31  1  0
 31 32  1  0
 31 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
  9 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 11  1  0
 20  7  1  0
 30 24  1  0
 21  3  1  0
 13 39  1  0
 12 37  1  0
 12 38  1  0
 11 36  1  6
  9 35  1  6
  6 34  1  0
  5 33  1  0
 31 53  1  6
 32 54  1  0
 23 47  1  1
 20 46  1  0
 25 48  1  0
 26 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  1  0
 18 44  1  1
 19 45  1  0
 16 42  1  6
 17 43  1  0
 14 40  1  1
 15 41  1  0
M  END


  Mrv1652309272006292D          

 32 35  0  0  0  0            999 V2000
10001.0655 9998.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.635710002.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6409 9998.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.214110000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7852 9998.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0707 9997.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.785210001.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.354210000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3542 9999.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.066210000.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0662 9999.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7807 9999.5841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.780710000.4092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.354910000.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.640410000.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925910000.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9258 9999.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6403 9999.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3549 9999.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.922210001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.207810002.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.493210001.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.493210000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.207710000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.922310000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.784510000.8252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.070010000.4127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.0700 9999.5876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.7845 9999.1752    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4990 9999.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.499010000.4127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4951 9999.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
  1 11  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 16  4  1  0  0  0  0
 18  3  1  0  0  0  0
 10 14  1  0  0  0  0
 19 11  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 20  1  0  0  0  0
 13 23  1  6  0  0  0
 20  2  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31  4  1  6  0  0  0
 29  5  1  6  0  0  0
 28  9  1  1  0  0  0
 27  8  1  6  0  0  0
 26  7  1  1  0  0  0
 12 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0181360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)[C@H](O)[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17-25,27-29H,7H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1

> <INCHI_KEY>
UDIXYHJHYVDNOG-JUIPTLLLSA-N

> <FORMULA>
C21H22O11

> <MOLECULAR_WEIGHT>
450.396

> <EXACT_MASS>
450.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.42636809253155

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
-0.14811850366666623

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.513555505048016

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.468144526125949

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437586574

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
104.77239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8668.6568663.569   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8675.3208670.517   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8665.9968663.569   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.3338668.207   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8660.6668663.589   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8659.3328662.816   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8660.6668669.747   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8657.9958668.207   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8657.9958665.129   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8668.6578668.201   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8668.6578665.121   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.9918665.890   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.9918667.431   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3298667.431   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9958668.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6628667.430   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6618665.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.9958665.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.3298665.891   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8673.9888669.747   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.6558670.516   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.3218669.746   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.3218668.207   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.6548667.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8673.9888668.207   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8660.6648668.207   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8659.3318667.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8659.3318665.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8660.6648665.127   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8661.9988665.897   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8661.9988667.437   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8671.3248665.120   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   20                                                            
CONECT    3   18                                                            
CONECT    4   16   31                                                       
CONECT    5    6   29                                                       
CONECT    6    5                                                            
CONECT    7   26                                                            
CONECT    8   27                                                            
CONECT    9   28                                                            
CONECT   10   13   14                                                       
CONECT   11   12    1   19                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   10   23                                                  
CONECT   14   15   19   10                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    4                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19    3                                                  
CONECT   19   18   14   11                                                  
CONECT   20   21   25    2                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   13                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   27   31    7                                                  
CONECT   27   26   28    8                                                  
CONECT   28   27   29    9                                                  
CONECT   29   28   30    5                                                  
CONECT   30   29   31                                                       
CONECT   31   26   30    4                                                  
CONECT   32   12                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-7-(beta-D-Glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
(2R,3R)-7-(β-D-Glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
Dihydrokaempferol 7-O-beta-D-glucopyranoside	PhytoBank
Dihydrokaempferol 7-O-β-D-glucopyranoside	PhytoBank
Dihydrokaempferol 7-O-beta-D-glucoside	PhytoBank
Dihydrokaempferol 7-O-β-D-glucoside	PhytoBank
Dihydrokaempferol 7-O-glucoside	PhytoBank
Dihydrokaempferol 7-glucoside	PhytoBank
Aromadendrin-7-O-glucoside	PhytoBank
Glucosyl-7-aromadendrin	PhytoBank
Senecin	PhytoBank

Chemical Formula

C₂₁H₂₂O₁₁

Average Mass

450.3960 Da

Monoisotopic Mass

450.11621 Da

IUPAC Name

(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)[C@H](O)[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H22O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17-25,27-29H,7H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1

InChI Key

UDIXYHJHYVDNOG-JUIPTLLLSA-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
Abies nephrolepis	LOTUS Database	35616633
Cornus mas	LOTUS Database	35616633
Crocus chrysanthus	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Flavanonol
Flavan
Phenolic glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
O-glycosyl compound
Chromone
Glycosyl compound
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Vinylogous acid
Ketone
Secondary alcohol
Organoheterocyclic compound
Ether
Acetal
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aldehyde
Alcohol
Primary alcohol
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	-0.38	ALOGPS
logP	-0.15	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.77 m³·mol⁻¹	ChemAxon
Polarizability	43.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

8631810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10456395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Carulli G, Rocco M, Panichi A, Chios CF, Ciurli E, Mannucci C, Sordi E, Caracciolo F, Papineschi F, Benedetti E, Petrini M: Treatment of oral mucositis in hematologic patients undergoing autologous or allogeneic transplantation of peripheral blood stem cells: a prospective, randomized study with a mouthwash containing camelia sinensis leaf extract. Hematol Rep. 2013 Apr 4;5(1):21-5. doi: 10.4081/hr.2013.e6. Print 2013 Jan 25. [PubMed:23888242 ]
Tsai CH, Stern A, Chiou JF, Chern CL, Liu TZ: Rapid and specific detection of hydroxyl radical using an ultraweak chemiluminescence analyzer and a low-level chemiluminescence emitter: application to hydroxyl radical-scavenging ability of aqueous extracts of Food constituents. J Agric Food Chem. 2001 May;49(5):2137-41. doi: 10.1021/jf001071k. [PubMed:11368567 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0181360)

MOL for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0181360 ((2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)