NP-MRD: Showing NP-Card for andrographidin A (NP0032789)

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Record Information

Version

2.0

Created at

2021-06-19 23:29:54 UTC

Updated at

2021-06-30 00:02:11 UTC

NP-MRD ID

NP0032789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

andrographidin A

Provided By

JEOL Database JEOL Logo

Description

Andrographidin A belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. andrographidin A is found in Andrographis paniculata. andrographidin A was first documented in 2007 (Li, W., et al.). Based on a literature review very few articles have been published on Andrographidin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306202101293D          

 59 62  0  0  0  0            999 V2000
    2.4215    3.6206   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.3109    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    2.4273    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0930    2.0385   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    1.1115    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    0.7850   -0.9215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345    0.0158   -1.9149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5441    0.8988   -2.9327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.1967   -3.9793 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7101    1.2470   -4.9462 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4954    2.1941   -4.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -0.7758   -4.6935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0994   -1.5217   -5.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -1.7412   -3.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3589   -2.5746   -4.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412   -0.9903   -2.5115 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2163    0.5925    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4232    0.9743    2.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6072    1.9073    2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    2.2370    3.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    3.4347    4.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2436   -0.8028    3.8311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2769   -1.9187    3.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582   -1.8519    3.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768   -2.8517    3.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754   -3.9443    2.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -4.0379    2.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -3.0374    2.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3300   -0.3531    1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.7975    0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6781    2.7136   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1291   -1.6657    3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  2  0  0  0  0
 19 18  2  0  0  0  0
  8  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 19 23  1  0  0  0  0
 18 32  1  0  0  0  0
 32 31  1  0  0  0  0
 31 24  1  0  0  0  0
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  9  8  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5  6  1  0  0  0  0
 10 11  1  0  0  0  0
 32 33  2  0  0  0  0
  7 16  1  0  0  0  0
 24 25  1  0  0  0  0
 16 14  1  0  0  0  0
 25 26  2  0  0  0  0
  3  4  1  0  0  0  0
 26 27  1  0  0  0  0
 14 12  1  0  0  0  0
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  4  5  2  0  0  0  0
 28 29  1  0  0  0  0
  5 18  1  0  0  0  0
 29 30  2  0  0  0  0
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 12  9  1  0  0  0  0
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  1 34  1  0  0  0  0
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M  END

     RDKit          3D

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    0.7101    1.2470   -4.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652306202101293D          

 59 62  0  0  0  0            999 V2000
    2.4215    3.6206   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.3109    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5754   -3.9443    2.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -4.0379    2.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -3.0374    2.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -0.7207    3.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3300   -0.3531    1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.7975    0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998    4.2324   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359    4.2099   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    2.7136   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    2.4597   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -0.5316   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -0.3328   -3.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0969    1.8045   -5.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426    0.7948   -5.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    2.4975   -3.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.2284   -5.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8181   -1.4815   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    3.3168    4.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    4.2889    3.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651    3.6425    4.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3970   -1.0045    4.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0056   -2.7739    3.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -4.7235    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -4.8942    1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -3.1612    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107    0.0659    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291   -1.6657    3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  2  0  0  0  0
 19 18  2  0  0  0  0
  8  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 19 23  1  0  0  0  0
 18 32  1  0  0  0  0
 32 31  1  0  0  0  0
 31 24  1  0  0  0  0
 24 23  1  0  0  0  0
  9  8  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5  6  1  0  0  0  0
 10 11  1  0  0  0  0
 32 33  2  0  0  0  0
  7 16  1  0  0  0  0
 24 25  1  0  0  0  0
 16 14  1  0  0  0  0
 25 26  2  0  0  0  0
  3  4  1  0  0  0  0
 26 27  1  0  0  0  0
 14 12  1  0  0  0  0
 27 28  2  0  0  0  0
  4  5  2  0  0  0  0
 28 29  1  0  0  0  0
  5 18  1  0  0  0  0
 29 30  2  0  0  0  0
 30 25  1  0  0  0  0
 12  9  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
  7 38  1  1  0  0  0
 12 43  1  6  0  0  0
 13 44  1  0  0  0  0
 14 45  1  1  0  0  0
 15 46  1  0  0  0  0
 16 47  1  6  0  0  0
 17 48  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  9 39  1  1  0  0  0
 11 42  1  0  0  0  0
  4 37  1  0  0  0  0
 31 58  1  0  0  0  0
 31 59  1  0  0  0  0
 24 52  1  1  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 26 53  1  0  0  0  0
 27 54  1  0  0  0  0
 28 55  1  0  0  0  0
 29 56  1  0  0  0  0
 30 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>
NP0032789

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C3=C2C(=O)C([H])([H])[C@]([H])(O3)C2=C([H])C([H])=C([H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O10/c1-29-15-9-14(32-23-20(28)19(27)18(26)16(10-24)33-23)17-12(25)8-13(11-6-4-3-5-7-11)31-22(17)21(15)30-2/h3-7,9,13,16,18-20,23-24,26-28H,8,10H2,1-2H3/t13-,16+,18+,19-,20+,23+/m0/s1

> <INCHI_KEY>
HTJQSWAVTHDBPX-PHKHNSMASA-N

> <FORMULA>
C23H26O10

> <MOLECULAR_WEIGHT>
462.451

> <EXACT_MASS>
462.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.87246554338671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7,8-dimethoxy-2-phenyl-5-{[(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>
0.59

> <JCHEM_LOGP>
0.20882806900000087

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.131978227175587

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.19221767849804

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463049432

> <JCHEM_POLAR_SURFACE_AREA>
144.14000000000001

> <JCHEM_REFRACTIVITY>
112.3988

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7,8-dimethoxy-2-phenyl-5-{[(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

$$$$

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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    0.1532    0.1967   -3.9793 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7101    1.2470   -4.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    2.1941   -4.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -0.7758   -4.6935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0994   -1.5217   -5.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3589   -2.5746   -4.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4706   -1.9747   -1.5583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163    0.5925    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4232    0.9743    2.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6072    1.9073    2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    2.2370    3.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    3.4347    4.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070    0.4881    3.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436   -0.8028    3.8311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2769   -1.9187    3.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582   -1.8519    3.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768   -2.8517    3.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754   -3.9443    2.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -4.0379    2.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -3.0374    2.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -0.7207    3.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -0.3531    1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.7975    0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998    4.2324   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359    4.2099   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    2.7136   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    2.4597   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -0.5316   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -0.3328   -3.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0969    1.8045   -5.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426    0.7948   -5.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    2.4975   -3.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.2284   -5.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199   -2.2322   -5.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -2.4276   -3.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -3.0366   -3.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -0.4730   -2.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181   -1.4815   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    3.3168    4.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    4.2889    3.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651    3.6425    4.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.9742    4.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970   -1.0045    4.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0056   -2.7739    3.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -4.7235    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -4.8942    1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -3.1612    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107    0.0659    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291   -1.6657    3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  2  0
 19 18  2  0
  8  7  1  0
 12 13  1  0
 14 15  1  0
 16 17  1  0
 19 23  1  0
 18 32  1  0
 32 31  1  0
 31 24  1  0
 24 23  1  0
  9  8  1  0
 20 21  1  0
 21 22  1  0
  5  6  1  0
 10 11  1  0
 32 33  2  0
  7 16  1  0
 24 25  1  0
 16 14  1  0
 25 26  2  0
  3  4  1  0
 26 27  1  0
 14 12  1  0
 27 28  2  0
  4  5  2  0
 28 29  1  0
  5 18  1  0
 29 30  2  0
 30 25  1  0
 12  9  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
  9 10  1  0
  7  6  1  0
  7 38  1  1
 12 43  1  6
 13 44  1  0
 14 45  1  1
 15 46  1  0
 16 47  1  6
 17 48  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  1
 11 42  1  0
  4 37  1  0
 31 58  1  0
 31 59  1  0
 24 52  1  1
 22 49  1  0
 22 50  1  0
 22 51  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
 30 57  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.422   3.621  -0.339  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.934   3.311   0.961  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.890   2.427   1.044  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.093   2.038  -0.034  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.943   1.111   0.147  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.737   0.785  -0.922  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.034   0.016  -1.915  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.544   0.899  -2.933  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.153   0.197  -3.979  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.710   1.247  -4.946  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.495   2.194  -4.215  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.790  -0.776  -4.694  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.099  -1.522  -5.696  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.391  -1.741  -3.673  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.359  -2.575  -4.332  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.041  -0.990  -2.511  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.471  -1.975  -1.558  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.216   0.593   1.418  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.423   0.974   2.503  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.607   1.907   2.317  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.406   2.237   3.388  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.930   3.435   4.001  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.607   0.488   3.776  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.244  -0.803   3.831  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.277  -1.919   3.438  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.058  -1.852   3.878  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.977  -2.852   3.554  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.575  -3.944   2.792  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.256  -4.038   2.360  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.666  -3.037   2.684  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.580  -0.721   3.107  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.330  -0.353   1.671  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.033  -0.798   0.767  0.00  0.00           O+0
HETATM   34  H   UNK     0       1.700   4.232  -0.890  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.336   4.210  -0.222  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.678   2.714  -0.897  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.243   2.460  -1.021  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.198  -0.532  -1.456  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.004  -0.333  -3.530  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.097   1.805  -5.433  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.343   0.795  -5.715  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.913   2.498  -3.494  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.599  -0.228  -5.194  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.720  -2.232  -5.961  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.619  -2.428  -3.301  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.827  -3.037  -3.606  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.945  -0.473  -2.857  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.818  -1.482  -0.776  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.100   3.317   4.358  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.999   4.289   3.319  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.565   3.643   4.867  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.469  -0.974   4.892  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.397  -1.004   4.474  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.006  -2.774   3.896  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.289  -4.723   2.538  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.061  -4.894   1.769  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.686  -3.161   2.328  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.211   0.066   3.538  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.129  -1.666   3.158  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3   20    4    2                                                  
CONECT    4    3    5   37                                                  
CONECT    5    6    4   18                                                  
CONECT    6    5    7                                                       
CONECT    7    8   16    6   38                                             
CONECT    8    7    9                                                       
CONECT    9    8   12   10   39                                             
CONECT   10   11    9   40   41                                             
CONECT   11   10   42                                                       
CONECT   12   13   14    9   43                                             
CONECT   13   12   44                                                       
CONECT   14   15   16   12   45                                             
CONECT   15   14   46                                                       
CONECT   16   17    7   14   47                                             
CONECT   17   16   48                                                       
CONECT   18   19   32    5                                                  
CONECT   19   18   23   20                                                  
CONECT   20    3   21   19                                                  
CONECT   21   20   22                                                       
CONECT   22   21   49   50   51                                             
CONECT   23   19   24                                                       
CONECT   24   31   23   25   52                                             
CONECT   25   24   26   30                                                  
CONECT   26   25   27   53                                                  
CONECT   27   26   28   54                                                  
CONECT   28   27   29   55                                                  
CONECT   29   28   30   56                                                  
CONECT   30   29   25   57                                                  
CONECT   31   32   24   58   59                                             
CONECT   32   18   31   33                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   24                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   31                                                            
CONECT   59   31                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

RDKit          3D

59 62  0  0  0  0  0  0  0  0999 V2000
    2.4215    3.6206   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.3109    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    2.4273    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0930    2.0385   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    1.1115    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    0.7850   -0.9215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345    0.0158   -1.9149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5441    0.8988   -2.9327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.1967   -3.9793 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7101    1.2470   -4.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    2.1941   -4.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -0.7758   -4.6935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0994   -1.5217   -5.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -1.7412   -3.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3589   -2.5746   -4.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412   -0.9903   -2.5115 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4706   -1.9747   -1.5583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163    0.5925    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4232    0.9743    2.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6072    1.9073    2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    2.2370    3.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    3.4347    4.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070    0.4881    3.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436   -0.8028    3.8311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2769   -1.9187    3.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582   -1.8519    3.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768   -2.8517    3.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754   -3.9443    2.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -4.0379    2.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -3.0374    2.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -0.7207    3.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -0.3531    1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.7975    0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998    4.2324   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359    4.2099   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    2.7136   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    2.4597   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -0.5316   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -0.3328   -3.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0969    1.8045   -5.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426    0.7948   -5.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    2.4975   -3.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.2284   -5.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199   -2.2322   -5.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -2.4276   -3.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -3.0366   -3.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -0.4730   -2.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181   -1.4815   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    3.3168    4.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    4.2889    3.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651    3.6425    4.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.9742    4.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970   -1.0045    4.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0056   -2.7739    3.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -4.7235    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -4.8942    1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -3.1612    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107    0.0659    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291   -1.6657    3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  2  0
 19 18  2  0
  8  7  1  0
 12 13  1  0
 14 15  1  0
 16 17  1  0
 19 23  1  0
 18 32  1  0
 32 31  1  0
 31 24  1  0
 24 23  1  0
  9  8  1  0
 20 21  1  0
 21 22  1  0
  5  6  1  0
 10 11  1  0
 32 33  2  0
  7 16  1  0
 24 25  1  0
 16 14  1  0
 25 26  2  0
  3  4  1  0
 26 27  1  0
 14 12  1  0
 27 28  2  0
  4  5  2  0
 28 29  1  0
  5 18  1  0
 29 30  2  0
 30 25  1  0
 12  9  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
  9 10  1  0
  7  6  1  0
  7 38  1  1
 12 43  1  6
 13 44  1  0
 14 45  1  1
 15 46  1  0
 16 47  1  6
 17 48  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  1
 11 42  1  0
  4 37  1  0
 31 58  1  0
 31 59  1  0
 24 52  1  1
 22 49  1  0
 22 50  1  0
 22 51  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
 30 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

C₂₃H₂₆O₁₀

Average Mass

462.4510 Da

Monoisotopic Mass

462.15260 Da

IUPAC Name

(2S)-7,8-dimethoxy-2-phenyl-5-{[(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

(2S)-7,8-dimethoxy-2-phenyl-5-{[(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

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C3=C2C(=O)C([H])([H])[C@]([H])(O3)C2=C([H])C([H])=C([H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C23H26O10/c1-29-15-9-14(32-23-20(28)19(27)18(26)16(10-24)33-23)17-12(25)8-13(11-6-4-3-5-7-11)31-22(17)21(15)30-2/h3-7,9,13,16,18-20,23-24,26-28H,8,10H2,1-2H3/t13-,16+,18+,19-,20+,23+/m0/s1

InChI Key

HTJQSWAVTHDBPX-PHKHNSMASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Andrographis paniculata	JEOL database	Li, W., et al, Chem. Pharm. Bull. 55, 455 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-5-o-glycoside
Flavonoid o-glycoside
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavanone
Flavan
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Monocyclic benzene moiety
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aldehyde
Alcohol
Organic oxygen compound
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	0.59	ALOGPS
logP	0.21	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.4 m³·mol⁻¹	ChemAxon
Polarizability	45.87 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

32700075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13963762

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, W., et al. (2007). Li, W., et al, Chem. Pharm. Bull. 55, 455 (2007) . Chem. Pharm. Bull..

Showing NP-Card for andrographidin A (NP0032789)

MOL for NP0032789 (andrographidin A)

3D MOL for NP0032789 (andrographidin A)

3D SDF for NP0032789 (andrographidin A)

3D-SDF for NP0032789 (andrographidin A)

PDB for NP0032789 (andrographidin A)

3D PDB for NP0032789 (andrographidin A)

SMILES for NP0032789 (andrographidin A)

INCHI for NP0032789 (andrographidin A)

Structure for NP0032789 (andrographidin A)

3D Structure for NP0032789 (andrographidin A)