NP-MRD: Showing NP-Card for boerhaavic acid (NP0042440)

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Record Information

Version

2.0

Created at

2021-06-21 00:06:13 UTC

Updated at

2021-06-30 00:17:31 UTC

NP-MRD ID

NP0042440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

boerhaavic acid

Provided By

JEOL Database JEOL Logo

Description

boerhaavic acid is found in Boerhaavia diffusa L. (Nyctaginaceae). boerhaavic acid was first documented in 2013 (Do, T. M. L., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102063D          

 57 60  0  0  0  0            999 V2000
    2.2393   -4.2214    2.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103   -3.3266    2.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7426   -2.2488    1.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344   -1.4087    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -0.2592    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811    0.0375    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -0.7871    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4899    0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.0878    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5554   -0.9237    2.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -0.3989    3.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626   -1.5576    4.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3684   -1.1355    5.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.6251    2.9550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9657    1.1828    4.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.7431    2.1553 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.1263    2.2519    0.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.9341    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    1.1210   -0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.3796   -1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3988    1.3809   -3.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2970    2.0222   -4.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    2.0355   -3.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601    1.7184   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4166    1.7383   -0.7183 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.2414    4.4700   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704    5.1374    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.4362   -0.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6448   -4.6771    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7795   -1.6544    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    0.5553    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.0857    4.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -2.3431    4.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4946    1.8436   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5997   -2.5552    1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3211    1.6892   -5.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1504    2.3042   -3.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4452    1.9446   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928    2.7879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6092    2.6117    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018    5.9759    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 11 10  1  0  0  0  0
  3  2  1  0  0  0  0
  7  8  1  0  0  0  0
 10  9  1  0  0  0  0
  6  5  2  0  0  0  0
 14 15  1  0  0  0  0
  5 33  1  0  0  0  0
 16 17  1  0  0  0  0
  6 21  1  0  0  0  0
 18 19  1  0  0  0  0
 33 28  1  0  0  0  0
 21 22  1  0  0  0  0
 28 27  1  0  0  0  0
 27 22  2  0  0  0  0
 12 13  1  0  0  0  0
 22 23  1  0  0  0  0
  9 18  1  0  0  0  0
 23 24  2  0  0  0  0
  5  4  1  0  0  0  0
 24 25  1  0  0  0  0
 18 16  1  0  0  0  0
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  4  3  2  0  0  0  0
 28 29  1  0  0  0  0
 16 14  1  0  0  0  0
 29 30  1  0  0  0  0
  3 20  1  0  0  0  0
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 14 11  1  0  0  0  0
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 20  7  2  0  0  0  0
  2  1  1  0  0  0  0
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  9 38  1  1  0  0  0
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  4 37  1  0  0  0  0
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  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    2.2393   -4.2214    2.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103   -3.3266    2.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4214   -0.2592    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811    0.0375    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2321   -0.4899    0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.0878    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5554   -0.9237    2.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8626   -1.5576    4.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684   -1.1355    5.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.6251    2.9550 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.1204   -2.3431    4.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7  6  1  0
 11 10  1  0
  3  2  1  0
  7  8  1  0
 10  9  1  0
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M  END


  Mrv1652306212102063D          

 57 60  0  0  0  0            999 V2000
    2.2393   -4.2214    2.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103   -3.3266    2.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7426   -2.2488    1.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344   -1.4087    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -0.2592    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811    0.0375    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -0.7871    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4899    0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.0878    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.2284   -0.3989    3.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626   -1.5576    4.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3684   -1.1355    5.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.6251    2.9550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9657    1.1828    4.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.7431    2.1553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6341    2.6404    1.6724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    1.1687    0.9908 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.4076   -1.9341    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    1.1210   -0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.3796   -1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9462    1.6957   -4.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970    2.0222   -4.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    2.0355   -3.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601    1.7184   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4166    1.7383   -0.7183 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0585    2.8005    0.3270 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4263    4.1746   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2414    4.4700   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704    5.1374    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.4362   -0.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -3.7193    3.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7725   -5.0244    3.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -4.6771    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7795   -1.6544    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    0.5553    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.0857    4.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -2.3431    4.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766   -2.0176    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479   -0.2924    5.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553    0.1426    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588    1.9534    3.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    2.3473    2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    3.2285    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.7464    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    1.8436   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5997   -2.5552    1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    1.1301   -2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    1.6892   -5.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7274    2.2710   -5.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    2.3042   -3.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4452    1.9446   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928    2.7879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6092    2.6117    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018    5.9759    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 11 10  1  0  0  0  0
  3  2  1  0  0  0  0
  7  8  1  0  0  0  0
 10  9  1  0  0  0  0
  6  5  2  0  0  0  0
 14 15  1  0  0  0  0
  5 33  1  0  0  0  0
 16 17  1  0  0  0  0
  6 21  1  0  0  0  0
 18 19  1  0  0  0  0
 33 28  1  0  0  0  0
 21 22  1  0  0  0  0
 28 27  1  0  0  0  0
 27 22  2  0  0  0  0
 12 13  1  0  0  0  0
 22 23  1  0  0  0  0
  9 18  1  0  0  0  0
 23 24  2  0  0  0  0
  5  4  1  0  0  0  0
 24 25  1  0  0  0  0
 18 16  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
  4  3  2  0  0  0  0
 28 29  1  0  0  0  0
 16 14  1  0  0  0  0
 29 30  1  0  0  0  0
  3 20  1  0  0  0  0
 30 32  1  0  0  0  0
 14 11  1  0  0  0  0
 30 31  2  0  0  0  0
 20  7  2  0  0  0  0
  2  1  1  0  0  0  0
 11 12  1  0  0  0  0
  9  8  1  0  0  0  0
  9 38  1  1  0  0  0
 14 43  1  6  0  0  0
 15 44  1  0  0  0  0
 16 45  1  1  0  0  0
 17 46  1  0  0  0  0
 18 47  1  6  0  0  0
 19 48  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 11 39  1  1  0  0  0
 13 42  1  0  0  0  0
  4 37  1  0  0  0  0
 20 49  1  0  0  0  0
 28 54  1  6  0  0  0
 23 50  1  0  0  0  0
 24 51  1  0  0  0  0
 25 52  1  0  0  0  0
 26 53  1  0  0  0  0
 29 55  1  0  0  0  0
 29 56  1  0  0  0  0
 32 57  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])OC2=C(OC3=C1C([H])=C([H])C([H])=C3[H])C(O[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])=C([H])C(OC([H])([H])[H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O11/c1-29-10-6-14-21(31-12-5-3-2-4-11(12)13(30-14)8-17(24)25)15(7-10)32-22-20(28)19(27)18(26)16(9-23)33-22/h2-7,13,16,18-20,22-23,26-28H,8-9H2,1H3,(H,24,25)/t13-,16-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
WGMYIKWUVFQALS-FJDBYKCNSA-N

> <FORMULA>
C22H24O11

> <MOLECULAR_WEIGHT>
464.423

> <EXACT_MASS>
464.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.541193789743076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(10R)-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-yl]acetic acid

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
0.11254746866666629

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.140386663376834

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.311281690238983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354988836

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
108.35929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(10R)-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    2.2393   -4.2214    2.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103   -3.3266    2.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7426   -2.2488    1.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344   -1.4087    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -0.2592    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811    0.0375    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -0.7871    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4899    0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.0878    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5554   -0.9237    2.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -0.3989    3.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626   -1.5576    4.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684   -1.1355    5.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.6251    2.9550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9657    1.1828    4.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.7431    2.1553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6341    2.6404    1.6724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    1.1687    0.9908 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1263    2.2519    0.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.9341    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    1.1210   -0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.3796   -1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3988    1.3809   -3.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9462    1.6957   -4.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970    2.0222   -4.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    2.0355   -3.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601    1.7184   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4166    1.7383   -0.7183 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0585    2.8005    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    4.1746   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2414    4.4700   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704    5.1374    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.4362   -0.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -3.7193    3.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7725   -5.0244    3.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -4.6771    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7795   -1.6544    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    0.5553    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.0857    4.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -2.3431    4.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766   -2.0176    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479   -0.2924    5.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553    0.1426    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588    1.9534    3.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    2.3473    2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    3.2285    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.7464    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    1.8436   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5997   -2.5552    1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    1.1301   -2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    1.6892   -5.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7274    2.2710   -5.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    2.3042   -3.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4452    1.9446   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928    2.7879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6092    2.6117    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018    5.9759    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 11 10  1  0
  3  2  1  0
  7  8  1  0
 10  9  1  0
  6  5  2  0
 14 15  1  0
  5 33  1  0
 16 17  1  0
  6 21  1  0
 18 19  1  0
 33 28  1  0
 21 22  1  0
 28 27  1  0
 27 22  2  0
 12 13  1  0
 22 23  1  0
  9 18  1  0
 23 24  2  0
  5  4  1  0
 24 25  1  0
 18 16  1  0
 25 26  2  0
 26 27  1  0
  4  3  2  0
 28 29  1  0
 16 14  1  0
 29 30  1  0
  3 20  1  0
 30 32  1  0
 14 11  1  0
 30 31  2  0
 20  7  2  0
  2  1  1  0
 11 12  1  0
  9  8  1  0
  9 38  1  1
 14 43  1  6
 15 44  1  0
 16 45  1  1
 17 46  1  0
 18 47  1  6
 19 48  1  0
 12 40  1  0
 12 41  1  0
 11 39  1  1
 13 42  1  0
  4 37  1  0
 20 49  1  0
 28 54  1  6
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 29 55  1  0
 29 56  1  0
 32 57  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.239  -4.221   2.758  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.210  -3.327   2.228  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.743  -2.249   1.529  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.734  -1.409   1.012  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.421  -0.259   0.269  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.081   0.038   0.024  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.088  -0.787   0.579  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.232  -0.490   0.343  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.848   0.088   1.509  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.555  -0.924   2.234  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.228  -0.399   3.385  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.863  -1.558   4.167  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.368  -1.135   5.429  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.291   0.625   2.955  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.966   1.183   4.088  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.622   1.743   2.155  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.634   2.640   1.672  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.818   1.169   0.991  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.126   2.252   0.348  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.408  -1.934   1.308  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.609   1.121  -0.679  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.210   1.380  -1.882  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.399   1.381  -3.018  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.946   1.696  -4.260  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.297   2.022  -4.359  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.100   2.035  -3.216  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.560   1.718  -1.960  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.417   1.738  -0.718  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.059   2.801   0.327  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.426   4.175  -0.149  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.241   4.470  -1.006  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.770   5.137   0.529  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.528   0.436  -0.123  0.00  0.00           O+0
HETATM   34  H   UNK     0       1.599  -3.719   3.491  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.773  -5.024   3.276  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.645  -4.677   1.959  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.779  -1.654   1.195  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.093   0.555   2.158  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.497   0.086   4.047  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.120  -2.343   4.345  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.677  -2.018   3.596  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.848  -0.292   5.277  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.055   0.143   2.332  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.459   1.953   3.734  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.980   2.347   2.808  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.173   3.228   1.040  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.498   0.746   0.240  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.495   1.844  -0.279  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.600  -2.555   1.680  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.345   1.130  -2.938  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.321   1.689  -5.149  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.727   2.271  -5.326  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.150   2.304  -3.312  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.445   1.945  -1.043  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.993   2.788   0.574  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.609   2.612   1.256  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.102   5.976   0.143  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    2    4   20                                                  
CONECT    4    5    3   37                                                  
CONECT    5    6   33    4                                                  
CONECT    6    7    5   21                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9   10   18    8   38                                             
CONECT   10   11    9                                                       
CONECT   11   10   14   12   39                                             
CONECT   12   13   11   40   41                                             
CONECT   13   12   42                                                       
CONECT   14   15   16   11   43                                             
CONECT   15   14   44                                                       
CONECT   16   17   18   14   45                                             
CONECT   17   16   46                                                       
CONECT   18   19    9   16   47                                             
CONECT   19   18   48                                                       
CONECT   20    3    7   49                                                  
CONECT   21    6   22                                                       
CONECT   22   21   27   23                                                  
CONECT   23   22   24   50                                                  
CONECT   24   23   25   51                                                  
CONECT   25   24   26   52                                                  
CONECT   26   25   27   53                                                  
CONECT   27   28   22   26                                                  
CONECT   28   33   27   29   54                                             
CONECT   29   28   30   55   56                                             
CONECT   30   29   32   31                                                  
CONECT   31   30                                                            
CONECT   32   30   57                                                       
CONECT   33    5   28                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
CONECT   57   32                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
    2.2393   -4.2214    2.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103   -3.3266    2.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7426   -2.2488    1.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344   -1.4087    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -0.2592    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811    0.0375    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -0.7871    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4899    0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.0878    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5554   -0.9237    2.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -0.3989    3.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626   -1.5576    4.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684   -1.1355    5.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.6251    2.9550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9657    1.1828    4.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.7431    2.1553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6341    2.6404    1.6724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    1.1687    0.9908 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1263    2.2519    0.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.9341    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    1.1210   -0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.3796   -1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3988    1.3809   -3.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9462    1.6957   -4.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970    2.0222   -4.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    2.0355   -3.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601    1.7184   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4166    1.7383   -0.7183 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0585    2.8005    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    4.1746   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2414    4.4700   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704    5.1374    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.4362   -0.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -3.7193    3.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7725   -5.0244    3.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -4.6771    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7795   -1.6544    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    0.5553    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.0857    4.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -2.3431    4.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766   -2.0176    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479   -0.2924    5.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553    0.1426    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588    1.9534    3.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    2.3473    2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    3.2285    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.7464    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    1.8436   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5997   -2.5552    1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    1.1301   -2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    1.6892   -5.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7274    2.2710   -5.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    2.3042   -3.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4452    1.9446   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928    2.7879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6092    2.6117    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018    5.9759    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 11 10  1  0
  3  2  1  0
  7  8  1  0
 10  9  1  0
  6  5  2  0
 14 15  1  0
  5 33  1  0
 16 17  1  0
  6 21  1  0
 18 19  1  0
 33 28  1  0
 21 22  1  0
 28 27  1  0
 27 22  2  0
 12 13  1  0
 22 23  1  0
  9 18  1  0
 23 24  2  0
  5  4  1  0
 24 25  1  0
 18 16  1  0
 25 26  2  0
 26 27  1  0
  4  3  2  0
 28 29  1  0
 16 14  1  0
 29 30  1  0
  3 20  1  0
 30 32  1  0
 14 11  1  0
 30 31  2  0
 20  7  2  0
  2  1  1  0
 11 12  1  0
  9  8  1  0
  9 38  1  1
 14 43  1  6
 15 44  1  0
 16 45  1  1
 17 46  1  0
 18 47  1  6
 19 48  1  0
 12 40  1  0
 12 41  1  0
 11 39  1  1
 13 42  1  0
  4 37  1  0
 20 49  1  0
 28 54  1  6
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 29 55  1  0
 29 56  1  0
 32 57  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₁₁

Average Mass

464.4230 Da

Monoisotopic Mass

464.13186 Da

IUPAC Name

2-[(10R)-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-yl]acetic acid

Traditional Name

[(10R)-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@@]1([H])OC2=C(OC3=C1C([H])=C([H])C([H])=C3[H])C(O[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])=C([H])C(OC([H])([H])[H])=C2[H]

InChI Identifier

InChI=1S/C22H24O11/c1-29-10-6-14-21(31-12-5-3-2-4-11(12)13(30-14)8-17(24)25)15(7-10)32-22-20(28)19(27)18(26)16(9-23)33-22/h2-7,13,16,18-20,22-23,26-28H,8-9H2,1H3,(H,24,25)/t13-,16-,18-,19+,20-,22-/m1/s1

InChI Key

WGMYIKWUVFQALS-FJDBYKCNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boerhavia diffusa	JEOL database	Do, T. M. L., et al, Phytochem. Lett. 6, 544 (2013)

Chemical Taxonomy

Classification

Not classified

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	0.54	ALOGPS
logP	0.11	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.36 m³·mol⁻¹	ChemAxon
Polarizability	45.54 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

Not Available

References

General References

Do, T. M. L., et al. (2013). Do, T. M. L., et al, Phytochem. Lett. 6, 544 (2013). Phytochem..

Showing NP-Card for boerhaavic acid (NP0042440)

MOL for NP0042440 (boerhaavic acid)

3D MOL for NP0042440 (boerhaavic acid)

3D SDF for NP0042440 (boerhaavic acid)

3D-SDF for NP0042440 (boerhaavic acid)

PDB for NP0042440 (boerhaavic acid)

3D PDB for NP0042440 (boerhaavic acid)

SMILES for NP0042440 (boerhaavic acid)

INCHI for NP0042440 (boerhaavic acid)

Structure for NP0042440 (boerhaavic acid)

3D Structure for NP0042440 (boerhaavic acid)