NP-MRD: Showing NP-Card for Sibirioside A (NP0075782)

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Record Information

Version

2.0

Created at

2022-04-28 21:00:56 UTC

Updated at

2022-04-28 21:00:56 UTC

NP-MRD ID

NP0075782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sibirioside A

Description

Sibirioside A belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Sibirioside A is found in Scrophularia ningpoensis and Veronicastrum sibiricum. Sibirioside A was first documented in 2011 (PMID: 21839598). Based on a literature review a small amount of articles have been published on Sibirioside A (PMID: 30347747) (PMID: 28326841).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223002D          

 33 35  0  0  1  0            999 V2000
    2.4282   -3.5987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2352   -3.7702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4901   -4.5548    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -5.1679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1311   -4.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8762   -4.2118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0692   -4.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -3.2556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073   -3.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -3.6972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476   -2.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0546   -2.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165   -1.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714   -0.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    0.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124    0.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -0.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1931   -5.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6410   -6.5657    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9736   -7.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285   -7.8352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0535   -7.8352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3085   -7.0506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0931   -6.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -8.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7436   -8.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231   -8.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890   -5.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820   -6.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971   -4.7264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872   -3.1571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1733   -2.8141    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  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  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  1  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 23 26  1  6  0  0  0
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 27 28  1  0  0  0  0
 20 29  1  6  0  0  0
 29 30  1  0  0  0  0
  3 31  1  1  0  0  0
  2 32  1  6  0  0  0
  1 33  1  1  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    2.9149   -0.1184    2.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954   -0.2607    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5598    0.0878    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633    0.5300    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8241    0.8888    1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2982    0.7927   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6151    1.1466   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4683    1.6033    0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0022    1.7051    1.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6846    1.3448    2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426   -0.7221    0.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260   -1.0658    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -1.5439   -0.6340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1565   -1.8783   -0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290   -1.2106   -1.0288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3916   -1.3771   -0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597   -0.2879   -0.1134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4316    0.7116   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0331    0.0850   -2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4718    0.3513    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4541    0.9342    1.7176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0586    0.7905    3.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    1.4024    3.4643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7334    0.1981    1.4907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7545    1.0505    1.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3926   -0.8141    0.4456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2789   -2.1031    0.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -1.5360   -2.4785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6503   -2.8690   -2.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -0.7668   -2.8969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0034    0.4887   -3.4064 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659   -0.5351   -1.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5815   -0.5936   -2.1936 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8236   -0.0262   -0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1209    0.6196    2.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006    0.4502   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9641    1.0623   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4955    1.8811    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6849    2.0625    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3854    1.4481    3.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749   -0.1339    0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529   -1.8011    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284   -2.4966   -0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752   -0.1130   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486    1.2517   -1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    1.4075   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9953   -0.0183   -2.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6058    2.0065    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8153    1.2879    3.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0516   -0.2687    3.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435    2.2877    3.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920   -0.3243    2.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6513    1.9327    1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1847   -0.8017   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9673   -2.7088    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7269   -1.2134   -3.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -3.1873   -3.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.2880   -3.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977    1.1026   -2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1124    0.4818   -1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102   -1.3297   -2.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
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 17 18  1  0
 18 19  1  0
 17 16  1  6
 16 15  1  0
 15 14  1  0
 14 13  1  0
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 11  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
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 13 32  1  0
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 32 30  1  0
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 28 29  1  0
 17 26  1  0
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 28 15  1  0
 10  5  1  0
 23 51  1  0
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 21 48  1  6
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 12 42  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 32 60  1  1
 33 61  1  0
 30 58  1  6
 31 59  1  0
 28 56  1  6
 29 57  1  0
 26 54  1  6
 27 55  1  0
 24 52  1  1
 25 53  1  0
M  END


  Mrv1652304282223002D          

 33 35  0  0  1  0            999 V2000
    2.4282   -3.5987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2352   -3.7702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4901   -4.5548    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -5.1679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1311   -4.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8762   -4.2118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0692   -4.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -3.2556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073   -3.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -3.6972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9736   -7.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285   -7.8352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0535   -7.8352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3085   -7.0506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0931   -6.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -8.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7436   -8.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231   -8.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890   -5.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820   -6.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971   -4.7264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872   -3.1571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1733   -2.8141    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
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  9 10  2  0  0  0  0
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 12 13  1  0  0  0  0
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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  1  0  0  0
 20 19  1  1  0  0  0
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 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 23 26  1  6  0  0  0
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 20 29  1  6  0  0  0
 29 30  1  0  0  0  0
  3 31  1  1  0  0  0
  2 32  1  6  0  0  0
  1 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0075782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](COC(=O)\C=C\C3=CC=CC=C3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O12/c22-8-12-16(26)19(29)21(10-23,32-12)33-20-18(28)17(27)15(25)13(31-20)9-30-14(24)7-6-11-4-2-1-3-5-11/h1-7,12-13,15-20,22-23,25-29H,8-10H2/b7-6+/t12-,13-,15-,16-,17+,18-,19+,20-,21+/m1/s1

> <INCHI_KEY>
ASHAUBLELZYXKD-ZJKHXSAOSA-N

> <FORMULA>
C21H28O12

> <MOLECULAR_WEIGHT>
472.443

> <EXACT_MASS>
472.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.77842526426758

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
-1.24

> <JCHEM_LOGP>
-1.4949442456666664

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.395584027616426

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.84196414751296

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981433338188096

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
108.34179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.533  -6.718   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.039  -7.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.515  -8.502   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.484  -9.647   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.978  -9.327   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.502  -7.862   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.996  -7.542   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.520  -6.077   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.014  -5.757   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.017  -6.901   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.462  -4.292   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.969  -3.972   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.444  -2.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.951  -2.187   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.427  -0.723   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.396   0.422   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.890   0.102   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.414  -1.363   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.960 -11.111   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.930 -12.256   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.684 -13.161   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.160 -14.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.700 -14.626   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.176 -13.161   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.640 -12.685   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.605 -15.872   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.255 -15.872   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.723 -15.711   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.899 -11.111   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.393 -11.432   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.021  -8.823   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.070  -5.893   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.057  -5.253   0.000  0.00  0.00           O+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    4   20                                                       
CONECT   20   19   21   24   29                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   20   25                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   22   28                                                       
CONECT   28   27                                                            
CONECT   29   20   30                                                       
CONECT   30   29                                                            
CONECT   31    3                                                            
CONECT   32    2                                                            
CONECT   33    1                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₁₂

Average Mass

472.4430 Da

Monoisotopic Mass

472.15808 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](COC(=O)\C=C\C3=CC=CC=C3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H28O12/c22-8-12-16(26)19(29)21(10-23,32-12)33-20-18(28)17(27)15(25)13(31-20)9-30-14(24)7-6-11-4-2-1-3-5-11/h1-7,12-13,15-20,22-23,25-29H,8-10H2/b7-6+/t12-,13-,15-,16-,17+,18-,19+,20-,21+/m1/s1

InChI Key

ASHAUBLELZYXKD-ZJKHXSAOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Scrophularia ningpoensis	Plant	KNApSAcK
Veronicastrum sibiricum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Styrene
Ketal
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Secondary alcohol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Primary alcohol
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
logP	-1.2	ALOGPS
logP	-1.5	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	108.34 m³·mol⁻¹	ChemAxon
Polarizability	45.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037821

Chemspider ID

4885195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6326022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang YF, Liu LJ, Xu F, Shang MY, Liu GX, Cai SQ: Investigation of the In Vivo Metabolism of Sibirioside A and Angoroside C in Rats by HPLC-ESI-IT-TOF-MS(n). Molecules. 2018 Oct 19;23(10):2702. doi: 10.3390/molecules23102702. [PubMed:30347747 ]
Zhang J, Ip FCF, Liang Y, Ip NY, Zhong BL, Lai CW, Xu SH: A new iridoid glycoside and a new cinnamoyl glycoside from Scrophularia ningpoensis Hemsl. Nat Prod Res. 2017 Oct;31(20):2361-2368. doi: 10.1080/14786419.2017.1306704. Epub 2017 Mar 22. [PubMed:28326841 ]
Jing J, Chan CO, Xu L, Jin D, Cao X, Mok DK, Parekh HS, Chen S: Development of an in-line HPLC fingerprint ion-trap mass spectrometric method for identification and quality control of Radix Scrophulariae. J Pharm Biomed Anal. 2011 Dec 5;56(4):830-5. doi: 10.1016/j.jpba.2011.07.032. Epub 2011 Jul 30. [PubMed:21839598 ]

Showing NP-Card for Sibirioside A (NP0075782)

MOL for NP0075782 (Sibirioside A)

3D MOL for NP0075782 (Sibirioside A)

3D SDF for NP0075782 (Sibirioside A)

3D-SDF for NP0075782 (Sibirioside A)

PDB for NP0075782 (Sibirioside A)

3D PDB for NP0075782 (Sibirioside A)

SMILES for NP0075782 (Sibirioside A)

INCHI for NP0075782 (Sibirioside A)

Structure for NP0075782 (Sibirioside A)

3D Structure for NP0075782 (Sibirioside A)