NP-MRD: Showing NP-Card for medicarpin (NP0141354)

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Record Information

Version

1.0

Created at

2022-08-21 21:41:03 UTC

Updated at

2022-08-21 22:07:41 UTC

NP-MRD ID

NP0141354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

medicarpin

Description

(-)-Medicarpin 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. Thus, (-)-medicarpin is considered to be a flavonoid (-)-medicarpin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. medicarpin is found in Arachis hypogaea, Baphia nitida, Bobgunnia madagascariensis, Butea monosperma, Caragana pygmaea, Caragana tibetica, Centrolobium sclerophyllum, Cicer arietinum, Cicer rechingeri, Cladrastis platycarpa, Dalbergia odorifera, Dalbergia stevensonii, Echinosophora koreensis, Erythroxylum barbatum, Galega officinalis, Gliricidia sepium, Glycyrrhiza echinata, Glycyrrhiza glabra, Glycyrrhiza pallidiflora, Glycyrrhiza uralensis, Hedysarum polybotrys, Hedysarum theinum, Lathyrus tuberosus, Lonchocarpus heptaphyllus, Maackia amurensis, Maackia floribunda, Medicago rugosa, Medicago sativa, Medicago truncatula, Melilotus messanensis, Melilotus wolgicus, Millettia leucantha, Mundulea sericea, Myroxylon balsamum, Myroxylon peruiferum, Neorautanenia amboensis, Ononis alopecuroides, Ononis natrix, Ononis vaginalis, Ononis viscosa, Pericopsis angolensis, Platymiscium floribundum, Platymiscium trinitatis, Platymiscium yucatanum, Pueraria montana, Sophora secundiflora, Taverniera abyssinica, Tephrosia purpurea, Tephrosia villosa, Trifolium canescens, Trifolium dichroanthum, Trifolium pratense, Vigna unguiculata and Wisteria brachybotrys. It was first documented in 2021 (PMID: 35649147). Based on a literature review a significant number of articles have been published on (-)-medicarpin (PMID: 35974307) (PMID: 35959633) (PMID: 35874019) (PMID: 35381781).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308212223412D          

 34 37  0  0  1  0            999 V2000
    6.3618   -0.4187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855   -1.0613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016    1.8863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    1.7920    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.5068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0672   -0.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -1.2356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -0.4795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    1.4167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1402    0.2767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001    0.0286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    2.0606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7213   -0.8216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645   -1.6669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -1.7146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382   -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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 21 27  2  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
  6 34  1  0  0  0  0
M  END

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
    5.9498    0.2341    1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339    0.3819    1.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250    0.1844    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -0.1781   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4894   -0.3674   -1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366   -0.1978   -0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011    0.1635    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557    0.3446    1.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2673    0.2744    1.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119   -0.6294    0.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3487   -0.3994    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -1.0922    0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5558   -0.9063    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0571    0.0028   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4350    0.1680   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2112    0.7066   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    0.4970   -0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    1.1945   -1.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625    1.0544   -1.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.3180   -1.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3244    1.1121    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231   -0.6776    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6230    0.0173    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6260   -0.3080   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170   -0.6565   -2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1597    0.6341    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -1.6541    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8385   -1.8210    1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504   -1.4531    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8172    0.8871    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6213    1.4163   -1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663    1.3099   -2.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218    1.7776   -0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -1.0893   -1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  2  0
 16 17  1  0
 17 11  2  0
 11 12  1  0
 12 13  2  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3  8  2  0
  6 20  1  0
 20 19  1  0
 19 18  1  0
 13 14  1  0
 20 10  1  0
 18 17  1  0
  8  7  1  0
 15 30  1  0
 16 31  1  0
 12 28  1  0
 13 29  1  0
 10 27  1  1
  5 25  1  0
  4 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  8 26  1  0
 20 34  1  6
 19 32  1  0
 19 33  1  0
M  END


  Mrv1652308212223412D          

 34 37  0  0  1  0            999 V2000
    6.3618   -0.4187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855   -1.0613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016    1.8863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    1.7920    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.5068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0672   -0.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -1.2356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -0.4795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    1.4167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1402    0.2767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001    0.0286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    2.0606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7213   -0.8216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645   -1.6669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -1.7146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382   -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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 21 27  2  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1[H])[C@]1([H])OC3=C(C([H])=C([H])C(OC([H])([H])[H])=C3[H])[C@]1([H])C([H])([H])O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m0/s1

> <INCHI_KEY>
NSRJSISNDPOJOP-BBRMVZONSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.632256138286664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.509223396333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.420754148461814

> <JCHEM_PKA_STRONGEST_BASIC>
-4.392070210867522

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
73.06110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-22         0                                  
HETATM    1  H   UNK     0      11.875  -0.782   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      11.183   0.594   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.645   0.682   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       9.493  -1.981   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       7.263  -0.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       6.723   3.521   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       9.798   3.345   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       5.726  -0.429   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0       4.070   2.147   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       1.480  -2.307   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.257  -0.895   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.404   2.181   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.699   1.349   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      -3.532   2.645   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.995   0.516   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.867   0.053   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       1.187   3.847   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       3.213  -1.534   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       4.227  -3.111   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.294  -3.201   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0       6.418  -1.805   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   34                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13   14   29                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   21   15   28                                                  
CONECT   28   27                                                            
CONECT   29   16   12   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31    6                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Medicarpin	ChEBI
Medicarpin, (cis-(+-))-isomer	MeSH
6a,11a-Dihydro-9-methoxy-6H-benzofuro(3,2-c)(1)benzopyran-3-ol	MeSH
Medicarpin, (6as-cis)-isomer	MeSH

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2840 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

Traditional Name

(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1[H])[C@]1([H])OC3=C(C([H])=C([H])C(OC([H])([H])[H])=C3[H])[C@]1([H])C([H])([H])O2

InChI Identifier

InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m0/s1

InChI Key

NSRJSISNDPOJOP-BBRMVZONSA-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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl₃, simulated)	john.cort@pnnl.gov	Not Available	Not Available	2022-08-21	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Arachis hypogaea	LOTUS Database	35616633
Baphia nitida	LOTUS Database	35616633
Bobgunnia madagascariensis	LOTUS Database	35616633
Butea monosperma	LOTUS Database	35616633
Caragana pygmaea	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Centrolobium sclerophyllum	LOTUS Database	35616633
Cicer arietinum	LOTUS Database	35616633
Cicer rechingeri	LOTUS Database	35616633
Cladrastis platycarpa	LOTUS Database	35616633
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia stevensonii	LOTUS Database	35616633
Echinosophora koreensis	LOTUS Database	35616633
Erythroxylum barbatum	LOTUS Database	35616633
Galega officinalis	LOTUS Database	35616633
Gliricidia sepium	LOTUS Database	35616633
Glycyrrhiza echinata	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Glycyrrhiza pallidiflora	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Hedysarum polybotrys	LOTUS Database	35616633
Hedysarum theinum	LOTUS Database	35616633
Lathyrus tuberosus	LOTUS Database	35616633
Lonchocarpus latifolius	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maackia fauriei	LOTUS Database	35616633
Medicago rugosa	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Medicago truncatula	LOTUS Database	35616633
Melilotus messanensis	LOTUS Database	35616633
Melilotus wolgicus	LOTUS Database	35616633
Millettia leucantha	LOTUS Database	35616633
Mundulea sericea	LOTUS Database	35616633
Myroxylon balsamum	LOTUS Database	35616633
Myroxylon peruiferum	LOTUS Database	35616633
Neorautanenia amboensis	LOTUS Database	35616633
Ononis alopecuroides	LOTUS Database	35616633
Ononis natrix	LOTUS Database	35616633
Ononis vaginalis	LOTUS Database	35616633
Ononis viscosa	LOTUS Database	35616633
Pericopsis angolensis	LOTUS Database	35616633
Platymiscium floribundum	LOTUS Database	35616633
Platymiscium trinitatis	LOTUS Database	35616633
Platymiscium yucatanum	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633
Sophora secundiflora	LOTUS Database	35616633
Taverniera abyssinica	LOTUS Database	35616633
Tephrosia purpurea	LOTUS Database	35616633
Tephrosia villosa	LOTUS Database	35616633
Trifolium canescens	LOTUS Database	35616633
Trifolium dichroanthum	LOTUS Database	35616633
Trifolium pratense	LOTUS Database	35616633
Vigna unguiculata	LOTUS Database	35616633
Wisteria brachybotrys	LOTUS Database	35616633

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
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

medicarpin (CHEBI:100 )
pterocarpans (C10503 )
Pterocarpanes (C10503 )
Pterocarpans (LMPK12070028 )

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	3.07	ALOGPS
logP	2.51	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.06 m³·mol⁻¹	ChemAxon
Polarizability	28.63 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002547

Chemspider ID

298082

KEGG Compound ID

C10503

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

336327

PDB ID

Not Available

ChEBI ID

100

Good Scents ID

Not Available

References

General References

Xia X, Gong R, Zhang C: Integrative analysis of transcriptome and metabolome reveals flavonoid biosynthesis regulation in Rhododendron pulchrum petals. BMC Plant Biol. 2022 Aug 16;22(1):401. doi: 10.1186/s12870-022-03762-y. [PubMed:35974307 ]
Sharma K, Awasthi P, Prakash R, Khanka S, Bajpai R, Sahasrabuddhe AA, Goel A, Singh D: Maintenance of increased bone mass after PTH withdrawal by sequential medicarpin treatment via augmentation of cAMP-PKA pathway. J Cell Biochem. 2022 Aug 12. doi: 10.1002/jcb.30313. [PubMed:35959633 ]
Alvarez-Rivera G, Sanz A, Cifuentes A, Ibanez E, Paape T, Lucas MM, Pueyo JJ: Flavonoid Accumulation Varies in Medicago truncatula in Response to Mercury Stress. Front Plant Sci. 2022 Jul 7;13:933209. doi: 10.3389/fpls.2022.933209. eCollection 2022. [PubMed:35874019 ]
Chern CM, Lu CK, Liou KT, Wang YH, Tsai KC, Chang CL, Chang CC, Shen YC: Medicarpin isolated from Radix Hedysari ameliorates brain injury in a murine model of cerebral ischemia. J Food Drug Anal. 2021 Dec 15;29(4):581-605. doi: 10.38212/2224-6614.3377. [PubMed:35649147 ]
Yigin AK, Donmez H, Hitit M, Seven S, Eser N, Kurar E, Seven M: The effect of medicarpin on PTEN/AKT signal pathway in head and neck squamous cell carcinoma. J Cancer Res Ther. 2022 Jan-Mar;18(1):180-184. doi: 10.4103/jcrt.jcrt_641_21. [PubMed:35381781 ]

Showing NP-Card for medicarpin (NP0141354)

MOL for NP0141354 (medicarpin)

3D MOL for NP0141354 (medicarpin)

3D SDF for NP0141354 (medicarpin)

3D-SDF for NP0141354 (medicarpin)

PDB for NP0141354 (medicarpin)

3D PDB for NP0141354 (medicarpin)

SMILES for NP0141354 (medicarpin)

INCHI for NP0141354 (medicarpin)

Structure for NP0141354 (medicarpin)

3D Structure for NP0141354 (medicarpin)