NP-MRD: Showing NP-Card for (+)-Aquaticoside C (NP0074377)

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Record Information

Version

2.0

Created at

2022-04-28 19:32:42 UTC

Updated at

2022-04-28 19:32:42 UTC

NP-MRD ID

NP0074377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Aquaticoside C

Description

(1S,4aS,6S,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (+)-Aquaticoside C is found in Veronica anagallis-aquatica . Based on a literature review very few articles have been published on (1S,4aS,6S,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221322D          

 34 37  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    7.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    8.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  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
 21 26  1  0  0  0  0
  5 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  1  0  0  0
 29 31  1  6  0  0  0
  3 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -4.9182   -2.2182    1.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360   -2.5763    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6740   -3.9700    0.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5679   -4.1356   -0.4537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712   -3.9335    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -2.7214    0.7168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3621   -2.8968    2.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -4.0779    2.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2247   -4.9702    1.8548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3422   -4.2195    3.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7379   -2.0003    3.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4223   -0.8539    2.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -0.4821    1.3510 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4688    0.1361    0.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537    1.4523    0.4597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3957    1.4297   -0.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1483    1.8243   -1.3213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8158    0.7576   -0.9993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444    0.8454   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1861    1.5333   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.2774    0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637    1.4478   -1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5915    2.1642   -0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8863    2.0670   -1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664    1.2279   -2.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1138    0.5145   -2.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    0.6139   -2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2075    3.2078   -0.9681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4740    4.1235   -1.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    3.5697    0.4054 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7831    4.2201    1.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111    2.4305    1.2107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5969    3.0726    2.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356   -1.7469    0.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0157   -1.1910    2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6482   -2.9278    2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941   -4.7325    1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1875   -3.6511   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306   -3.6575   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112   -4.8533    0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838   -2.3490    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0076   -4.5208    4.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984   -2.1689    4.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.1117    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460    1.7278    0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683    1.8213   -2.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6235    0.3675    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -0.1620   -1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3951    2.8241    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7031    2.6223   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1579    1.1357   -2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3271   -0.1483   -3.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0191    0.0502   -2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2630    3.4841   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049    4.9832   -1.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    4.3900    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    5.1237    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155    1.8769    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957    3.2772    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837   -1.5464   -0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  5  6  1  0
  6 34  1  0
 34 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 13 12  1  0
 12 11  1  0
 11  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 34  2  1  0
  2  1  2  3
  2  3  1  0
  7  6  1  0
 32 15  1  0
 27 22  1  0
  4 38  1  0
  3 37  1  1
  5 39  1  0
  5 40  1  0
  6 41  1  6
 34 60  1  6
 13 44  1  1
 15 45  1  6
 17 46  1  6
 18 47  1  0
 18 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  1
 29 55  1  0
 30 56  1  6
 31 57  1  0
 32 58  1  1
 33 59  1  0
 11 43  1  0
 10 42  1  0
  1 35  1  0
  1 36  1  0
M  END


  Mrv1652304282221322D          

 34 37  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    7.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    8.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  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
 21 26  1  0  0  0  0
  5 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  1  0  0  0
 29 31  1  6  0  0  0
  3 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@H]2[C@H]([C@H](O[C@@H]3O[C@H](COC(=O)C4=CC=CC=C4)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(O)=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O11/c1-10-14(24)7-12-13(20(28)29)8-32-22(16(10)12)34-23-19(27)18(26)17(25)15(33-23)9-31-21(30)11-5-3-2-4-6-11/h2-6,8,12,14-19,22-27H,1,7,9H2,(H,28,29)/t12-,14+,15-,16-,17-,18+,19-,22+,23+/m1/s1

> <INCHI_KEY>
YNPRPYLCRQBHMQ-JJOYARITSA-N

> <FORMULA>
C23H26O11

> <MOLECULAR_WEIGHT>
478.45

> <EXACT_MASS>
478.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.68891099903588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,6S,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
0.009234914000000797

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.206833476563093

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.22301266303596

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9757981017183504

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
112.2278

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,6S,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <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  O   UNK     0       6.258   3.613   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.259   9.003   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.925  11.313   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925  12.853   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.591  13.623   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.259  13.623   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.259  15.163   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.592  15.933   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.926  15.163   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.926  13.623   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.592  12.853   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.258  -1.007   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.590  -1.007   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29    4                                                       
CONECT   31   29                                                            
CONECT   32    3   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,6S,7as)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator

Chemical Formula

C₂₃H₂₆O₁₁

Average Mass

478.4500 Da

Monoisotopic Mass

478.14751 Da

IUPAC Name

(1S,4aS,6S,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

Traditional Name

(1S,4aS,6S,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-7-methylidene-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@H]2[C@H]([C@H](O[C@@H]3O[C@H](COC(=O)C4=CC=CC=C4)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(O)=O)C1=C

InChI Identifier

InChI=1S/C23H26O11/c1-10-14(24)7-12-13(20(28)29)8-32-22(16(10)12)34-23-19(27)18(26)17(25)15(33-23)9-31-21(30)11-5-3-2-4-6-11/h2-6,8,12,14-19,22-27H,1,7,9H2,(H,28,29)/t12-,14+,15-,16-,17-,18+,19-,22+,23+/m1/s1

InChI Key

YNPRPYLCRQBHMQ-JJOYARITSA-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
Veronica anagallis-aquatica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Benzenoid
Cyclic alcohol
Vinylogous ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	-0.46	ALOGPS
logP	0.0092	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.23 m³·mol⁻¹	ChemAxon
Polarizability	46.69 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	Yes	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

10191063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21579245

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Aquaticoside C (NP0074377)

MOL for NP0074377 ((+)-Aquaticoside C)

3D MOL for NP0074377 ((+)-Aquaticoside C)

3D SDF for NP0074377 ((+)-Aquaticoside C)

3D-SDF for NP0074377 ((+)-Aquaticoside C)

PDB for NP0074377 ((+)-Aquaticoside C)

3D PDB for NP0074377 ((+)-Aquaticoside C)

SMILES for NP0074377 ((+)-Aquaticoside C)

INCHI for NP0074377 ((+)-Aquaticoside C)

Structure for NP0074377 ((+)-Aquaticoside C)

3D Structure for NP0074377 ((+)-Aquaticoside C)