NP-MRD: Showing NP-Card for andrographic acid (NP0032790)

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Record Information

Version

2.0

Created at

2021-06-19 23:29:57 UTC

Updated at

2021-06-30 00:02:11 UTC

NP-MRD ID

NP0032790

Secondary Accession Numbers

None

Natural Product Identification

Common Name

andrographic acid

Provided By

JEOL Database JEOL Logo

Description

Andrographic acid, also known as andrographate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. andrographic acid is found in Andrographis paniculata. andrographic acid was first documented in 2007 (PMID: 17329890). Based on a literature review very few articles have been published on Andrographic acid (PMID: 31902905).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101293D          

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    4.1013   -0.7772   -0.3787 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101293D          

 54 55  0  0  0  0            999 V2000
   -0.8702   -1.6749   -3.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1419   -0.7486   -3.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -0.2017   -3.8367 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3238   -0.3000   -2.8943 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.2848    0.5222   -0.5928 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.5958    0.7060    1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -0.5683    1.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947    0.9485    2.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -0.2062    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0854    1.3392    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.1069    0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -2.4389   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -2.3465   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    0.9414   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114   -1.6393   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    1.3037   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0197    1.7716   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5316   -0.2762    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -2.6947    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0  0  0  0
 16 17  1  0  0  0  0
 12 13  1  0  0  0  0
  6  8  1  1  0  0  0
 10  6  1  0  0  0  0
  2  1  2  3  0  0  0
  6  5  1  0  0  0  0
 17 18  2  0  0  0  0
 14 13  1  0  0  0  0
 18 19  1  0  0  0  0
 14 16  1  0  0  0  0
 19 20  2  0  0  0  0
  5  4  1  0  0  0  0
 19 24  1  0  0  0  0
  4  3  1  0  0  0  0
 20 21  1  0  0  0  0
  3  2  1  0  0  0  0
 21 23  1  0  0  0  0
  2 16  1  0  0  0  0
 21 22  2  0  0  0  0
 14  5  1  0  0  0  0
 24 25  2  0  0  0  0
 14 15  1  1  0  0  0
 24 26  1  0  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 10 40  1  6  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
  5 33  1  6  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
 16 49  1  6  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 11 41  1  0  0  0  0
 17 50  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 18 51  1  0  0  0  0
 20 52  1  0  0  0  0
 23 53  1  0  0  0  0
 26 54  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  9 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032790

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(\C(\[H])=C(/[H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@](C([H])([H])[H])(C([H])([H])O[H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])/C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-12-4-7-15-19(2,9-8-16(22)20(15,3)11-21)14(12)6-5-13(18(25)26)10-17(23)24/h5-6,10,14-16,21-22H,1,4,7-9,11H2,2-3H3,(H,23,24)(H,25,26)/b6-5+,13-10-/t14-,15+,16-,19+,20+/m1/s1

> <INCHI_KEY>
IMDVHFGRDJPERC-YJCGLWNISA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.06160632747711

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethenyl]but-2-enedioic acid

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.7977737030000012

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.027909029451886

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.870210367305157

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785462066151143

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
98.04519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethenyl]but-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
   -0.8702   -1.6749   -3.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1419   -0.7486   -3.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -0.2017   -3.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -0.3000   -2.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    0.3185   -1.5104 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2848    0.5222   -0.5928 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2454    1.5473   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -0.7772   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2580   -0.5256    0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227    1.1696    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8747    1.3223    1.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    0.4209    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    0.3232    0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552   -0.3695   -0.8466 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9320   -1.8898   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621   -0.1442   -1.8414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8072   -0.5824   -1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8414    0.2525   -1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -0.1175   -0.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1548    0.7777   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5154    0.5625   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5022    1.1278   -0.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5764   -0.2403    1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270   -1.4937   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993   -2.2864   -0.5909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7071   -1.7956    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -2.0473   -4.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -2.0903   -3.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -0.7193   -4.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.8504   -4.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585    0.2195   -3.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6300   -1.3469   -2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879    1.3484   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168    1.1336   -2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0558    1.8523   -0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    2.4580   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474   -1.1875   -1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377   -1.5474    0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7755   -1.3518    0.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4673    2.1873    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    0.7060    1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -0.5683    1.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947    0.9485    2.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -0.2062    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0854    1.3392    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.1069    0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -2.4389   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -2.3465   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    0.9414   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114   -1.6393   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    1.3037   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0197    1.7716   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5316   -0.2762    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -2.6947    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 16 17  1  0
 12 13  1  0
  6  8  1  1
 10  6  1  0
  2  1  2  3
  6  5  1  0
 17 18  2  0
 14 13  1  0
 18 19  1  0
 14 16  1  0
 19 20  2  0
  5  4  1  0
 19 24  1  0
  4  3  1  0
 20 21  1  0
  3  2  1  0
 21 23  1  0
  2 16  1  0
 21 22  2  0
 14  5  1  0
 24 25  2  0
 14 15  1  1
 24 26  1  0
  6  7  1  0
 10 11  1  0
  8  9  1  0
 12 42  1  0
 12 43  1  0
 10 40  1  6
 13 44  1  0
 13 45  1  0
  5 33  1  6
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
 16 49  1  6
 15 46  1  0
 15 47  1  0
 15 48  1  0
 11 41  1  0
 17 50  1  0
  8 37  1  0
  8 38  1  0
  1 27  1  0
  1 28  1  0
 18 51  1  0
 20 52  1  0
 23 53  1  0
 26 54  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  9 39  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      -0.870  -1.675  -3.861  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.142  -0.749  -3.211  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.120  -0.202  -3.837  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324  -0.300  -2.894  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.018   0.319  -1.510  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.285   0.522  -0.593  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.245   1.547  -1.268  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.101  -0.777  -0.379  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.258  -0.526   0.423  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.823   1.170   0.751  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.875   1.322   1.701  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.678   0.421   1.424  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.460   0.323   0.510  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.755  -0.370  -0.847  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.932  -1.890  -0.589  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.462  -0.144  -1.841  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.807  -0.582  -1.286  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.841   0.253  -1.082  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.151  -0.118  -0.554  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.155   0.778  -0.528  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.515   0.563  -0.023  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.502   1.128  -0.459  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.576  -0.240   1.047  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.427  -1.494  -0.082  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.199  -2.286  -0.591  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.707  -1.796   1.013  0.00  0.00           O+0
HETATM   27  H   UNK     0      -0.572  -2.047  -4.837  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.787  -2.090  -3.456  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.362  -0.719  -4.773  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.950   0.850  -4.099  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.159   0.220  -3.375  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.630  -1.347  -2.795  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.688   1.348  -1.728  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.717   1.134  -2.166  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.056   1.852  -0.597  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.711   2.458  -1.561  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.447  -1.188  -1.333  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.538  -1.547   0.140  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.776  -1.352   0.439  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.467   2.187   0.541  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.596   0.706   1.450  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.010  -0.568   1.758  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.395   0.949   2.344  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.336  -0.206   1.048  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.085   1.339   0.327  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.654  -2.107   0.196  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.240  -2.439  -1.482  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.000  -2.346  -0.240  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.537   0.941  -2.012  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.911  -1.639  -1.055  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.712   1.304  -1.337  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.020   1.772  -0.942  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.532  -0.276   1.262  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.013  -2.695   1.249  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    1    3   16                                                  
CONECT    3    4    2   29   30                                             
CONECT    4    5    3   31   32                                             
CONECT    5    6    4   14   33                                             
CONECT    6    8   10    5    7                                             
CONECT    7    6   34   35   36                                             
CONECT    8    6    9   37   38                                             
CONECT    9    8   39                                                       
CONECT   10   12    6   11   40                                             
CONECT   11   10   41                                                       
CONECT   12   10   13   42   43                                             
CONECT   13   12   14   44   45                                             
CONECT   14   13   16    5   15                                             
CONECT   15   14   46   47   48                                             
CONECT   16   17   14    2   49                                             
CONECT   17   16   18   50                                                  
CONECT   18   17   19   51                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   52                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   53                                                       
CONECT   24   19   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   54                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   20                                                            
CONECT   53   23                                                            
CONECT   54   26                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  110    0
END

RDKit          3D

54 55  0  0  0  0  0  0  0  0999 V2000
   -0.8702   -1.6749   -3.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1419   -0.7486   -3.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3238   -0.3000   -2.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    0.3185   -1.5104 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2848    0.5222   -0.5928 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2454    1.5473   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -0.7772   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2580   -0.5256    0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227    1.1696    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8747    1.3223    1.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    0.4209    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    0.3232    0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552   -0.3695   -0.8466 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4621   -0.1442   -1.8414 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.1548    0.7777   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5154    0.5625   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5022    1.1278   -0.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5764   -0.2403    1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270   -1.4937   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993   -2.2864   -0.5909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7071   -1.7956    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -2.0473   -4.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -2.0903   -3.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -0.7193   -4.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.8504   -4.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585    0.2195   -3.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6300   -1.3469   -2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879    1.3484   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168    1.1336   -2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0558    1.8523   -0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    2.4580   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474   -1.1875   -1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377   -1.5474    0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7755   -1.3518    0.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4673    2.1873    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    0.7060    1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -0.5683    1.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947    0.9485    2.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -0.2062    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0854    1.3392    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.1069    0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -2.4389   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -2.3465   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    0.9414   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114   -1.6393   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    1.3037   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0197    1.7716   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5316   -0.2762    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -2.6947    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 16 17  1  0
 12 13  1  0
  6  8  1  1
 10  6  1  0
  2  1  2  3
  6  5  1  0
 17 18  2  0
 14 13  1  0
 18 19  1  0
 14 16  1  0
 19 20  2  0
  5  4  1  0
 19 24  1  0
  4  3  1  0
 20 21  1  0
  3  2  1  0
 21 23  1  0
  2 16  1  0
 21 22  2  0
 14  5  1  0
 24 25  2  0
 14 15  1  1
 24 26  1  0
  6  7  1  0
 10 11  1  0
  8  9  1  0
 12 42  1  0
 12 43  1  0
 10 40  1  6
 13 44  1  0
 13 45  1  0
  5 33  1  6
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
 16 49  1  6
 15 46  1  0
 15 47  1  0
 15 48  1  0
 11 41  1  0
 17 50  1  0
  8 37  1  0
  8 38  1  0
  1 27  1  0
  1 28  1  0
 18 51  1  0
 20 52  1  0
 23 53  1  0
 26 54  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  9 39  1  0
M  END

View in JSmol

Synonyms

Value	Source
Andrographate	Generator

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

(2Z)-2-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethenyl]but-2-enedioic acid

Traditional Name

(2Z)-2-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethenyl]but-2-enedioic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(\C(\[H])=C(/[H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@](C([H])([H])[H])(C([H])([H])O[H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])/C(=O)O[H]

InChI Identifier

InChI=1S/C20H28O6/c1-12-4-7-15-19(2,9-8-16(22)20(15,3)11-21)14(12)6-5-13(18(25)26)10-17(23)24/h5-6,10,14-16,21-22H,1,4,7-9,11H2,2-3H3,(H,23,24)(H,25,26)/b6-5+,13-10-/t14-,15+,16-,19+,20+/m1/s1

InChI Key

IMDVHFGRDJPERC-YJCGLWNISA-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
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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Labdane diterpenoid
Diterpenoid
Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Fatty acid
Fatty acyl
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.6	ALOGPS
logP	1.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.05 m³·mol⁻¹	ChemAxon
Polarizability	39.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17342683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16215024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hanh TTH, My NTT, Cham PT, Quang TH, Cuong NX, Huong TT, Nam NH, Minh CV: Diterpenoids and Flavonoids from Andrographis paniculata. Chem Pharm Bull (Tokyo). 2020;68(1):96-99. doi: 10.1248/cpb.c19-00662. [PubMed:31902905 ]
Li W, Xu X, Zhang H, Ma C, Fong H, van Breemen R, Fitzloff J: Secondary metabolites from Andrographis paniculata. Chem Pharm Bull (Tokyo). 2007 Mar;55(3):455-8. doi: 10.1248/cpb.55.455. [PubMed:17329890 ]
Li, W., et al. (2007). Li, W., et al, Chem. Pharm. Bull. 55, 455 (2007) . Chem. Pharm. Bull..

Showing NP-Card for andrographic acid (NP0032790)

MOL for NP0032790 (andrographic acid)

3D MOL for NP0032790 (andrographic acid)

3D SDF for NP0032790 (andrographic acid)

3D-SDF for NP0032790 (andrographic acid)

PDB for NP0032790 (andrographic acid)

3D PDB for NP0032790 (andrographic acid)

SMILES for NP0032790 (andrographic acid)

INCHI for NP0032790 (andrographic acid)

Structure for NP0032790 (andrographic acid)

3D Structure for NP0032790 (andrographic acid)