NP-MRD: Showing NP-Card for (-)-Medicocarpin (NP0044193)

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Record Information

Version

1.0

Created at

2021-11-12 23:56:19 UTC

Updated at

2021-11-26 17:46:27 UTC

NP-MRD ID

NP0044193

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Medicocarpin

Description

(-)-Medicocarpin is found in Glycyrrhiza kansuensis, Glycyrrhiza pallidiflora, Gueldenstaedtia verna, Medicago sativa , Medicago truncatula, Ononis spinosa , Taxus fuana, Taxus yunnanensis, Trifolium repens and Trifolium spp.. It was first documented in 2008 (Tsunoda, et al.).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100562D          

 33 37  0  0  1  0            999 V2000
    5.9909    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672    1.0551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743   -0.4151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2672   -0.1358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198   -0.8255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5435   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9145   -0.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -1.5624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8015   -2.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5252   -1.6095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1542   -2.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725   -0.9198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2489   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
  7 19  1  1  0  0  0
  6 20  1  1  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
  2 22  2  0  0  0  0
 23  1  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    8.2529   -0.9765    2.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4261   -0.8864    1.5395 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3148   -0.7262    0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4293   -0.6332   -0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3385   -0.4743   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -0.4002   -0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9449   -0.4928    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433   -0.6535    1.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -0.3971    0.7276 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.8401   -0.4294 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4603   -0.3763   -0.4339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695   -1.1325    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -0.7373    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248    0.4427   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976    0.9529   -0.4498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6521    0.3764    0.0766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5320    0.1332   -1.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6689   -0.5408   -0.5672 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4473   -0.9559   -1.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8147    0.1515   -2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4807    0.4213    0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6126   -0.2116    0.8073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6173    0.8137    1.4576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2906    1.7134    2.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2880    1.3770    1.0209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4914    1.5359    2.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250    1.2149   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947    0.8167   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907    1.5915   -1.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426    1.2581   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.2296   -1.5120 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2190   -0.9476    3.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6135   -1.8308    3.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6979   -0.0573    3.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4293   -0.6901   -1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4166   -0.3997   -2.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376   -0.7241    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9249   -1.9298   -0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -2.0755    0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299   -1.3383    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5204   -0.5810    0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4092   -1.3911    0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -1.4835   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8596   -1.6301   -2.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6717    0.4829   -2.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7758    1.2851   -0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3994    0.3653    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4288   -0.0979    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893    1.2507    2.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    2.3277    0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3801    2.5176    2.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704    2.1560   -1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802    1.6015   -2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867    1.7917   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720   -0.7368   -2.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 27  2  0
 27 28  1  0
 28 11  2  0
 11 10  1  0
 10 31  1  0
 31  6  1  0
  6  7  2  0
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  8  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
 31 30  1  0
 30 29  1  0
 11 12  1  0
 12 13  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
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 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 13  1  0
 29 28  1  0
  9 10  1  0
  6  5  1  0
 25 16  1  0
 27 52  1  0
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 31 55  1  6
  8 37  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
 30 53  1  0
 30 54  1  0
 12 39  1  0
 13 40  1  0
 16 41  1  1
 18 42  1  1
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 19 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 23 48  1  1
 24 49  1  0
 25 50  1  6
 26 51  1  0
M  END


  Mrv1652311132100562D          

 33 37  0  0  1  0            999 V2000
    5.9909    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672    1.0551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743   -0.4151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2672   -0.1358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198   -0.8255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5435   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9145   -0.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -1.5624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8015   -2.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5252   -1.6095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1542   -2.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725   -0.9198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2489   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
  7 19  1  1  0  0  0
  6 20  1  1  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
  2 22  2  0  0  0  0
 23  1  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044193

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12COC3=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=CC=C3[C@]1([H])OC1=CC(OC)=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O9/c1-27-10-2-4-12-14-9-28-15-7-11(3-5-13(15)21(14)30-16(12)6-10)29-22-20(26)19(25)18(24)17(8-23)31-22/h2-7,14,17-26H,8-9H2,1H3/t14-,17+,18+,19-,20+,21-,22+/m0/s1

> <INCHI_KEY>
PVEMGMOWXQUWRD-NJAOXFEXSA-N

> <FORMULA>
C22H24O9

> <MOLECULAR_WEIGHT>
432.425

> <EXACT_MASS>
432.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.19226881991378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
0.2411553029999996

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196090792974335

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200140018647128

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437225645

> <JCHEM_POLAR_SURFACE_AREA>
127.07000000000002

> <JCHEM_REFRACTIVITY>
105.20550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0      11.183   0.946   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.800   2.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.263   2.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.188   1.881   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.070  -0.607   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.260  -0.768   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.404  -0.641   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.699   0.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.418   3.345   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       5.726   1.969   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.739  -0.775   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       7.415  -0.606   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.028  -0.341   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.565  -0.253   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.410  -1.541   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.948  -1.453   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.640  -0.077   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.718  -2.916   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.563  -4.204   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.180  -3.004   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.488  -4.380   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.335  -1.717   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.798  -1.805   0.000  0.00  0.00           O+0
CONECT    1    2   23                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   10   20                                             
CONECT    7    6    8   17   19                                             
CONECT    8    7    9   16                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    6                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15    8                                                       
CONECT   17    7   18                                                       
CONECT   18   17    4                                                       
CONECT   19    7                                                            
CONECT   20    6                                                            
CONECT   21    5   22                                                       
CONECT   22   21    2                                                       
CONECT   23    1   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Medicarpin 3-O-glucoside	Kegg

Chemical Formula

C₂₂H₂₄O₉

Average Mass

432.4250 Da

Monoisotopic Mass

432.14203 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

[H][C@@]12COC3=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=CC=C3[C@]1([H])OC1=CC(OC)=CC=C21

InChI Identifier

InChI=1S/C22H24O9/c1-27-10-2-4-12-14-9-28-15-7-11(3-5-13(15)21(14)30-16(12)6-10)29-22-20(26)19(25)18(24)17(8-23)31-22/h2-7,14,17-26H,8-9H2,1H3/t14-,17+,18+,19-,20+,21-,22+/m0/s1

InChI Key

PVEMGMOWXQUWRD-NJAOXFEXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, 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
Glycyrrhiza kansuensis	Plant	KNApSAcK
Glycyrrhiza pallidiflora	Plant	KNApSAcK
Gueldenstaedtia verna	LOTUS Database	35616633
Medicago sativa	Plant	KNApSAcK
Medicago truncatula	Plant	KNApSAcK
Ononis spinosa	Plant	KNApSAcK
Taxus fuana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Trifolium spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Polyol
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterocarpans (CHEBI:80390 )
pterocarpans (C16223 )
Pterocarpanes (C16223 )

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	1.26	ALOGPS
logP	0.24	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.21 m³·mol⁻¹	ChemAxon
Polarizability	44.19 Å³	ChemAxon
Number of Rings	5	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

FDB030082

KNApSAcK ID

C00010183

Chemspider ID

Not Available

KEGG Compound ID

C16223

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724664

PDB ID

Not Available

ChEBI ID

80390

Good Scents ID

Not Available

References

General References

Yuki Tsunoda, Masafumi Okawa, Junei Kinjo, Tsuyoshi Ikeda, Toshihiro Nohara (2008). Studies on the Constituents of Gueldenstaedtia multiflora. Chemical and Pharmaceutical Bulletin, 2008 Volume 56 Issue 8 Pages 1138-1142. DOI: 10.1248/cpb.56.1138. Chemical and Pharmaceutical Bulletin.

Showing NP-Card for (-)-Medicocarpin (NP0044193)

MOL for NP0044193 ((-)-Medicocarpin)

3D MOL for NP0044193 ((-)-Medicocarpin)

3D SDF for NP0044193 ((-)-Medicocarpin)

3D-SDF for NP0044193 ((-)-Medicocarpin)

PDB for NP0044193 ((-)-Medicocarpin)

3D PDB for NP0044193 ((-)-Medicocarpin)

SMILES for NP0044193 ((-)-Medicocarpin)

INCHI for NP0044193 ((-)-Medicocarpin)

Structure for NP0044193 ((-)-Medicocarpin)

3D Structure for NP0044193 ((-)-Medicocarpin)