NP-MRD: Showing NP-Card for (+/-)-Liquiritigenin (NP0138429)

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Record Information

Version

1.0

Created at

2022-06-29 17:29:10 UTC

Updated at

2022-06-29 17:29:10 UTC

NP-MRD ID

NP0138429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+/-)-Liquiritigenin

Description

(+/-)-Liquiritigenin is found in Astragalus microcephalus, Brosimum acutifolium, Butea monosperma, Clausena excavata, Crinum bulbispermum, Dalbergia odorifera, Dalbergia parviflora, Dracaena draco, Echinosophora koreensis, Erythrina fusca, Flemingia macrophylla, Glycyrrhiza glabra, Glycyrrhiza inflata, Glycyrrhiza pallidiflora, Glycyrrhiza uralensis, Hedysarum polybotrys, Lespedeza cyrtobotrya, Maackia amurensis, Melilotus messanensis, Oxytropis falcata, Oxytropis trichophysa, Pancratium maritimum, Platymiscium floribundum, Pterocarpus santalinus, Sinofranchetia chinensis and Spatholobus suberectus. It was first documented in 1989 (PMID: 16667124). Based on a literature review a significant number of articles have been published on Speciogynine (PMID: 19352635) (PMID: 20839627) (PMID: 15787450) (PMID: 22976322).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218512D          

 29 32  0  0  1  0            999 V2000
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -4.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 19  9  1  1  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -3.3543   -0.0125   -3.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496   -0.9155   -2.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258   -1.0075   -1.0055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1682   -1.9466   -0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012   -1.3134   -0.9579 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1628   -2.0880   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796   -1.6277   -1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -0.2077   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956    0.5799   -0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298    1.7666   -0.0054 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699    1.7875    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1597    2.7521    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5050    2.4906    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9549    1.2437    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0664    0.2942   -0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320   -0.9596   -0.4360 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9010   -1.3203   -0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    0.5184   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276    0.0847   -0.7959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8397    0.4170    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567    0.2597   -0.2267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2483    0.3100    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9230    0.5324    2.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445    0.7401    2.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3714    1.4931    3.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6736    0.0897    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0345   -0.1263   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6394    0.1269    1.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9838   -0.0847    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.2362   -4.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.9396   -2.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3315   -0.5316   -3.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6648   -1.9704   -2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631   -0.7016   -2.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2387   -1.5987   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173   -2.1649    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710   -2.8342   -1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2863   -1.9283    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9728   -3.1530   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4166   -1.6611   -2.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2782   -2.2723   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3464    2.6168    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8004    3.7317    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2046    3.2700    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956    1.0230    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3790   -0.9737    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4121   -0.8786   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9802   -2.4290   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    0.6327   -1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.3576    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565    1.4544    0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130    1.1221   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696    0.5410    2.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    1.0413    4.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424    2.5011    3.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    1.6175    3.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4052    0.7362    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0297   -1.0175    0.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6097   -0.1675    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
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 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 21  3  1  0
 19  5  1  0
 18  8  1  0
 18 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  1
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
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  7 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  6
 20 50  1  0
 20 51  1  0
 21 52  1  6
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
M  END


  Mrv1652309122218512D          

 29 32  0  0  1  0            999 V2000
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -4.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 19  9  1  1  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3=C(NC4=CC=CC(OC)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16-,19-/m0/s1

> <INCHI_KEY>
LELBFTMXCIIKKX-CYSPOEIOSA-N

> <FORMULA>
C23H30N2O4

> <MOLECULAR_WEIGHT>
398.503

> <EXACT_MASS>
398.220557454

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.34535420030845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_LOGP>
3.299593586666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.67027620485117

> <JCHEM_PKA_STRONGEST_BASIC>
7.042108351851677

> <JCHEM_POLAR_SURFACE_AREA>
63.79

> <JCHEM_REFRACTIVITY>
112.91320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.228  -6.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.921  -5.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.303  -6.305   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.841  -6.217   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.624  -8.006   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.919  -8.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.076  -3.818   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.462  -3.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.153   0.309   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.536  -0.891   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.381  -2.178   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    8   11                                                  
CONECT   19    9    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2570 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

CAS Registry Number

69097-97-8

SMILES

OC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2

InChI Key

FURUXTVZLHCCNA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astragalus microcephalus	LOTUS Database	35616633
Brosimum acutifolium	LOTUS Database	35616633
Butea monosperma	LOTUS Database	35616633
Clausena excavata	LOTUS Database	35616633
Crinum bulbispermum	LOTUS Database	35616633
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Dracaena draco	LOTUS Database	35616633
Echinosophora koreensis	LOTUS Database	35616633
Erythrina fusca	LOTUS Database	35616633
Flemingia macrophylla	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Glycyrrhiza inflata	LOTUS Database	35616633
Glycyrrhiza pallidiflora	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Hedysarum polybotrys	LOTUS Database	35616633
Lespedeza cyrtobotrya	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Melilotus messanensis	LOTUS Database	35616633
Oxytropis falcata	LOTUS Database	35616633
Oxytropis trichophysa	LOTUS Database	35616633
Pancratium maritimum	LOTUS Database	35616633
Platymiscium floribundum	LOTUS Database	35616633
Pterocarpus santalinus	LOTUS Database	35616633
Sinofranchetia chinensis	LOTUS Database	35616633
Spatholobus suberectus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.3	ChemAxon
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.91 m³·mol⁻¹	ChemAxon
Polarizability	45.35 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

C00025211

Chemspider ID

16739323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560577

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Valianou L, Stathopoulou K, Karapanagiotis I, Magiatis P, Pavlidou E, Skaltsounis AL, Chryssoulakis Y: Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles. Anal Bioanal Chem. 2009 Jun;394(3):871-82. doi: 10.1007/s00216-009-2767-z. Epub 2009 Apr 8. [PubMed:19352635 ]
Gaur R, Kumar S, Trivedi P, Bhakuni RS, Bawankule DU, Pal A, Shanker K: Liquiritigenin derivatives and their hepatotoprotective activity. Nat Prod Commun. 2010 Aug;5(8):1243-6. [PubMed:20839627 ]
Falcao MJ, Pouliquem YB, Lima MA, Gramosa NV, Costa-Lotufo LV, Militao GC, Pessoa C, de Moraes MO, Silveira ER: Cytotoxic flavonoids from Platymiscium floribundum. J Nat Prod. 2005 Mar;68(3):423-6. doi: 10.1021/np049854d. [PubMed:15787450 ]
Hartwig UA, Maxwell CA, Joseph CM, Phillips DA: Interactions among Flavonoid nod Gene Inducers Released from Alfalfa Seeds and Roots. Plant Physiol. 1989 Nov;91(3):1138-42. doi: 10.1104/pp.91.3.1138. [PubMed:16667124 ]
Mikell JR, Khan IA: Bioconversion of 7-hydroxyflavanone: isolation, characterization and bioactivity evaluation of twenty-one phase I and phase II microbial metabolites. Chem Pharm Bull (Tokyo). 2012;60(9):1139-45. doi: 10.1248/cpb.c12-00296. [PubMed:22976322 ]

Showing NP-Card for (+/-)-Liquiritigenin (NP0138429)

MOL for NP0138429 ((+/-)-Liquiritigenin)

3D MOL for NP0138429 ((+/-)-Liquiritigenin)

3D SDF for NP0138429 ((+/-)-Liquiritigenin)

3D-SDF for NP0138429 ((+/-)-Liquiritigenin)

PDB for NP0138429 ((+/-)-Liquiritigenin)

3D PDB for NP0138429 ((+/-)-Liquiritigenin)

SMILES for NP0138429 ((+/-)-Liquiritigenin)

INCHI for NP0138429 ((+/-)-Liquiritigenin)

Structure for NP0138429 ((+/-)-Liquiritigenin)

3D Structure for NP0138429 ((+/-)-Liquiritigenin)