NP-MRD: Showing NP-Card for viscosumic acid (NP0029444)

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Record Information

Version

2.0

Created at

2021-06-19 21:04:08 UTC

Updated at

2021-06-29 23:56:47 UTC

NP-MRD ID

NP0029444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

viscosumic acid

Provided By

JEOL Database JEOL Logo

Description

Viscosumic acid is also known as viscosumate. viscosumic acid is found in Persicaria lapathifolia and Polygonum viscosum. viscosumic acid was first documented in 2004 (PMID: 15074598). Based on a literature review very few articles have been published on Viscosumic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123043D          

 38 39  0  0  0  0            999 V2000
   -1.9918   -0.3167   -2.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262    0.8156   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186    1.4286   -3.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    2.5381   -3.4509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7142    3.6291   -4.5141 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2776    4.7416   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.5538   -2.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    5.4460   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374    5.3122   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    6.4664   -1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725    3.3242   -2.1853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386    2.4086   -0.9548 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6465    1.8806   -0.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7932    1.2607    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5734    2.2824    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    0.6402    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    1.2425   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    0.6340   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -1.2153   -2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.0546   -2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483   -0.5678   -3.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.0958   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    2.0697   -3.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.3210   -5.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2348    3.9250   -4.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153    5.5865   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    6.9689   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.6646   -2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.9777   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.1144   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    2.6911   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.4537    0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    2.6434    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    1.8347    2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    3.1464    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.3972    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.1272    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    0.1637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 17 18  2  0  0  0  0
  4 11  1  0  0  0  0
  2  1  1  0  0  0  0
  4 23  1  1  0  0  0
  2 17  1  0  0  0  0
  7  8  1  0  0  0  0
  2  3  2  0  0  0  0
  8  9  2  0  0  0  0
 17 12  1  0  0  0  0
  8 10  1  0  0  0  0
 12 11  1  0  0  0  0
 11 28  1  6  0  0  0
 11  7  1  0  0  0  0
 12 13  1  0  0  0  0
  7  6  2  0  0  0  0
 13 14  1  0  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
  5  4  1  0  0  0  0
 14 16  1  0  0  0  0
 12 29  1  1  0  0  0
  3 22  1  0  0  0  0
  6 26  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 10 27  1  0  0  0  0
 13 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  1  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
M  END

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.9918   -0.3167   -2.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262    0.8156   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186    1.4286   -3.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    2.5381   -3.4509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7142    3.6291   -4.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    4.7416   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.5538   -2.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    5.4460   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374    5.3122   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    6.4664   -1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725    3.3242   -2.1853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386    2.4086   -0.9548 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6465    1.8806   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932    1.2607    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5734    2.2824    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    0.6402    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    1.2425   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    0.6340   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -1.2153   -2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.0546   -2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483   -0.5678   -3.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.0958   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    2.0697   -3.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.3210   -5.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2348    3.9250   -4.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153    5.5865   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    6.9689   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.6646   -2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.9777   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.1144   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    2.6911   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.4537    0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    2.6434    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    1.8347    2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    3.1464    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.3972    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.1272    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    0.1637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 17 18  2  0
  4 11  1  0
  2  1  1  0
  4 23  1  1
  2 17  1  0
  7  8  1  0
  2  3  2  0
  8  9  2  0
 17 12  1  0
  8 10  1  0
 12 11  1  0
 11 28  1  6
 11  7  1  0
 12 13  1  0
  7  6  2  0
 13 14  1  0
  6  5  1  0
 14 15  1  0
  5  4  1  0
 14 16  1  0
 12 29  1  1
  3 22  1  0
  6 26  1  0
  5 24  1  0
  5 25  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 10 27  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  1
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv1652306192123043D          

 38 39  0  0  0  0            999 V2000
   -1.9918   -0.3167   -2.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262    0.8156   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186    1.4286   -3.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    2.5381   -3.4509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7142    3.6291   -4.5141 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2776    4.7416   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.5538   -2.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    5.4460   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374    5.3122   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    6.4664   -1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725    3.3242   -2.1853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386    2.4086   -0.9548 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6465    1.8806   -0.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7932    1.2607    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5734    2.2824    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    0.6402    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    1.2425   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    0.6340   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -1.2153   -2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.0546   -2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483   -0.5678   -3.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.0958   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    2.0697   -3.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.3210   -5.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2348    3.9250   -4.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153    5.5865   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    6.9689   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.6646   -2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.9777   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.1144   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    2.6911   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.4537    0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    2.6434    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    1.8347    2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    3.1464    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.3972    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.1272    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    0.1637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 17 18  2  0  0  0  0
  4 11  1  0  0  0  0
  2  1  1  0  0  0  0
  4 23  1  1  0  0  0
  2 17  1  0  0  0  0
  7  8  1  0  0  0  0
  2  3  2  0  0  0  0
  8  9  2  0  0  0  0
 17 12  1  0  0  0  0
  8 10  1  0  0  0  0
 12 11  1  0  0  0  0
 11 28  1  6  0  0  0
 11  7  1  0  0  0  0
 12 13  1  0  0  0  0
  7  6  2  0  0  0  0
 13 14  1  0  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
  5  4  1  0  0  0  0
 14 16  1  0  0  0  0
 12 29  1  1  0  0  0
  3 22  1  0  0  0  0
  6 26  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 10 27  1  0  0  0  0
 13 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  1  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])([H])[C@]2([H])C([H])=C(C(=O)[C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8(2)6-12-13-10(7-9(3)14(12)16)4-5-11(13)15(17)18/h5,7-8,10,12-13H,4,6H2,1-3H3,(H,17,18)/t10-,12+,13-/m1/s1

> <INCHI_KEY>
PAAFIIOBYWWYMS-KGYLQXTDSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.650999711363625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,7aR)-6-methyl-4-(2-methylpropyl)-5-oxo-3a,4,5,7a-tetrahydro-1H-indene-3-carboxylic acid

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
3.228724117333334

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7462531588009576

> <JCHEM_PKA_STRONGEST_BASIC>
-4.879199476251773

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
71.0347

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,7S,7aS)-5-methyl-7-(2-methylpropyl)-6-oxo-3,3a,7,7a-tetrahydroindene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.9918   -0.3167   -2.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262    0.8156   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186    1.4286   -3.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    2.5381   -3.4509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7142    3.6291   -4.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    4.7416   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.5538   -2.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    5.4460   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374    5.3122   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    6.4664   -1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725    3.3242   -2.1853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386    2.4086   -0.9548 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6465    1.8806   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932    1.2607    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5734    2.2824    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    0.6402    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    1.2425   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    0.6340   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -1.2153   -2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.0546   -2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483   -0.5678   -3.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.0958   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    2.0697   -3.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.3210   -5.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2348    3.9250   -4.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153    5.5865   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    6.9689   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.6646   -2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.9777   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.1144   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    2.6911   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.4537    0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    2.6434    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    1.8347    2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    3.1464    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.3972    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.1272    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    0.1637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 17 18  2  0
  4 11  1  0
  2  1  1  0
  4 23  1  1
  2 17  1  0
  7  8  1  0
  2  3  2  0
  8  9  2  0
 17 12  1  0
  8 10  1  0
 12 11  1  0
 11 28  1  6
 11  7  1  0
 12 13  1  0
  7  6  2  0
 13 14  1  0
  6  5  1  0
 14 15  1  0
  5  4  1  0
 14 16  1  0
 12 29  1  1
  3 22  1  0
  6 26  1  0
  5 24  1  0
  5 25  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 10 27  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  1
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.992  -0.317  -2.796  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.026   0.816  -2.632  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.419   1.429  -3.667  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.559   2.538  -3.451  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.714   3.629  -4.514  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.278   4.742  -3.674  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.012   4.554  -2.368  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.376   5.446  -1.266  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.037   5.312  -0.106  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.153   6.466  -1.660  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.173   3.324  -2.185  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.239   2.409  -0.955  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.647   1.881  -0.620  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.793   1.261   0.787  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.573   2.282   1.904  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.187   0.640   0.932  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.731   1.242  -1.211  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.256   0.634  -0.278  0.00  0.00           O+0
HETATM   19  H   UNK     0      -1.620  -1.215  -2.293  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.966  -0.055  -2.370  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.148  -0.568  -3.851  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.598   1.096  -4.686  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.549   2.070  -3.341  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.414   3.321  -5.296  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.235   3.925  -4.973  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.815   5.587  -4.084  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.314   6.969  -0.835  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.874   3.665  -2.269  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.170   2.978  -0.113  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.930   1.114  -1.353  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.379   2.691  -0.717  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.062   0.454   0.908  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.541   2.643   1.922  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.773   1.835   2.884  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.236   3.146   1.788  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.972   1.397   0.829  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.353  -0.127   0.168  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.301   0.164   1.911  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1   17    3                                                  
CONECT    3    4    2   22                                                  
CONECT    4    3   11   23    5                                             
CONECT    5    6    4   24   25                                             
CONECT    6    7    5   26                                                  
CONECT    7    8   11    6                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   27                                                       
CONECT   11    4   12   28    7                                             
CONECT   12   17   11   13   29                                             
CONECT   13   12   14   30   31                                             
CONECT   14   13   15   16   32                                             
CONECT   15   14   33   34   35                                             
CONECT   16   14   36   37   38                                             
CONECT   17   18    2   12                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
   -1.9918   -0.3167   -2.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262    0.8156   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186    1.4286   -3.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    2.5381   -3.4509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7142    3.6291   -4.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    4.7416   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.5538   -2.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756    5.4460   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374    5.3122   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    6.4664   -1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725    3.3242   -2.1853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386    2.4086   -0.9548 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6465    1.8806   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932    1.2607    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5734    2.2824    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    0.6402    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    1.2425   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    0.6340   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -1.2153   -2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.0546   -2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483   -0.5678   -3.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.0958   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    2.0697   -3.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.3210   -5.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2348    3.9250   -4.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153    5.5865   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    6.9689   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.6646   -2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.9777   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.1144   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    2.6911   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.4537    0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    2.6434    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    1.8347    2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    3.1464    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.3972    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.1272    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    0.1637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 17 18  2  0
  4 11  1  0
  2  1  1  0
  4 23  1  1
  2 17  1  0
  7  8  1  0
  2  3  2  0
  8  9  2  0
 17 12  1  0
  8 10  1  0
 12 11  1  0
 11 28  1  6
 11  7  1  0
 12 13  1  0
  7  6  2  0
 13 14  1  0
  6  5  1  0
 14 15  1  0
  5  4  1  0
 14 16  1  0
 12 29  1  1
  3 22  1  0
  6 26  1  0
  5 24  1  0
  5 25  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 10 27  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  1
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
Viscosumate	Generator
4-Isobutyl-6-methyl-5-oxo-3a,4,5,7a-teterahydro-1H-inden-13-Oic acid	MeSH

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3aS,4S,7aR)-6-methyl-4-(2-methylpropyl)-5-oxo-3a,4,5,7a-tetrahydro-1H-indene-3-carboxylic acid

Traditional Name

(3aR,7S,7aS)-5-methyl-7-(2-methylpropyl)-6-oxo-3,3a,7,7a-tetrahydroindene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])([H])[C@]2([H])C([H])=C(C(=O)[C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H20O3/c1-8(2)6-12-13-10(7-9(3)14(12)16)4-5-11(13)15(17)18/h5,7-8,10,12-13H,4,6H2,1-3H3,(H,17,18)/t10-,12+,13-/m1/s1

InChI Key

PAAFIIOBYWWYMS-KGYLQXTDSA-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
Persicaria lapathifolia	LOTUS Database	35616633
Persicaria viscosa	JEOL database	Datta, B. K., et al, Phytochemistry 54, 201 (2000)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	2.94	ALOGPS
logP	3.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.03 m³·mol⁻¹	ChemAxon
Polarizability	27.65 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

8620122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10444703

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Datta BK, Datta SK, Chowdhury MM, Khan TH, Kundu JK, Rashid MA, Nahar L, Sarker SD: Analgesic, antiinflammatory and CNS depressant activities of sesquiterpenes and a flavonoid glycoside from Polygonum viscosum. Pharmazie. 2004 Mar;59(3):222-5. doi: 10.1002/chin.200428184. [PubMed:15074598 ]
Datta, B. K., et al. (2000). Datta, B. K., et al, Phytochemistry 54, 201 (2000). Phytochem..

Showing NP-Card for viscosumic acid (NP0029444)

MOL for NP0029444 (viscosumic acid)

3D MOL for NP0029444 (viscosumic acid)

3D SDF for NP0029444 (viscosumic acid)

3D-SDF for NP0029444 (viscosumic acid)

PDB for NP0029444 (viscosumic acid)

3D PDB for NP0029444 (viscosumic acid)

SMILES for NP0029444 (viscosumic acid)

INCHI for NP0029444 (viscosumic acid)

Structure for NP0029444 (viscosumic acid)

3D Structure for NP0029444 (viscosumic acid)