NP-MRD: Showing NP-Card for Lonchocarpenin (NP0051473)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:49:35 UTC

Updated at

2022-04-27 22:49:35 UTC

NP-MRD ID

NP0051473

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lonchocarpenin

Description

Lonchocarpenin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, lonchocarpenin is considered to be a flavonoid lipid molecule. Lonchocarpenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lonchocarpenin is found in Apis cerana and Derris scandens . Lonchocarpenin was first documented in 2013 (PMID: 24079177). A hydroxycoumarin that is 2H,8H-benzodipyran-2-one substituted by a hydroxy group at position 4, a methoxy group at position 5, 4-methoxyphenyl group at position 3 and two methyl groups at position 8 respectively (PMID: 24705564).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161523592D          

 33 36  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 24 30  2  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    8.9882   -1.4060    1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2794   -1.0628    0.2610 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8976   -0.9789    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743   -0.6398   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -0.5355   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193   -0.7752    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704   -0.6678    0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    0.5729    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707    1.7394    0.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    0.5885    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.7857    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    2.9881    0.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1160    3.7995   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801    1.8151    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0726    0.6260   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -0.5891   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -1.8851   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340   -1.8272   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3425   -2.4404    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8217   -2.3907    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8185   -3.2210    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0480   -0.5786   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281   -1.6976   -0.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164   -1.8107   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925   -2.9197   -0.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374    0.6513   -0.2427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880    1.8171   -0.1615 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0159    2.0337   -1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2309    1.7000    0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    3.0549    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1149    3.0809    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7229   -1.1179    1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -1.2158    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0695   -1.4784    1.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6472   -2.3806    1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8562   -0.5827    2.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8524   -0.4459   -1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3949   -0.2681   -1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    1.7122    0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0516    4.2962   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794    3.2224   -1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593    4.5536   -1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -2.3856   -1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -2.5451    0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9598   -1.2832   -1.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3547   -2.6513    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0852   -3.1332   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1374   -1.3960   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618   -2.5863    2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112   -3.7495    1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271   -4.0199    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6383    2.9294   -1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2697    2.2229   -2.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6776    1.1808   -1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0069    1.0095    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6623    2.6942    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7553    1.3418    1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    4.0297    0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500    4.0105    0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325   -1.3110    2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6119   -1.4795    2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 32  1  0
 32 33  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 27 30  1  0
 30 31  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 33  3  1  0
 24  7  1  0
 22 10  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
 32 60  1  0
 33 61  1  0
  9 39  1  0
 13 40  1  0
 13 41  1  0
 13 42  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
M  END


  Mrv1533004161523592D          

 33 36  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 24 30  2  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=C(O)C2=C(OC)C3=C(OC(C)(C)C=C3)C(CC=C(C)C)=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O6/c1-15(2)7-12-18-23-19(13-14-27(3,4)33-23)24(31-6)21-22(28)20(26(29)32-25(18)21)16-8-10-17(30-5)11-9-16/h7-11,13-14,28H,12H2,1-6H3

> <INCHI_KEY>
CCYKXDPVYWRNMH-UHFFFAOYSA-N

> <FORMULA>
C27H28O6

> <MOLECULAR_WEIGHT>
448.515

> <EXACT_MASS>
448.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.34593881395169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-5-methoxy-3-(4-methoxyphenyl)-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-2H,8H-pyrano[3,2-g]chromen-2-one

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
5.011748381666667

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.4085402458871314

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4115232556445125

> <JCHEM_POLAR_SURFACE_AREA>
74.22

> <JCHEM_REFRACTIVITY>
129.4556

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lonchocarpenin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.186  -4.353   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.196  -6.067   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   32                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   30                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24   12   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31    9   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₆

Average Mass

448.5150 Da

Monoisotopic Mass

448.18859 Da

IUPAC Name

4-hydroxy-5-methoxy-3-(4-methoxyphenyl)-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-2H,8H-pyrano[3,2-g]chromen-2-one

Traditional Name

lonchocarpenin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=C(O)C2=C(OC)C3=C(OC(C)(C)C=C3)C(CC=C(C)C)=C2OC1=O

InChI Identifier

InChI=1S/C27H28O6/c1-15(2)7-12-18-23-19(13-14-27(3,4)33-23)24(31-6)21-22(28)20(26(29)32-25(18)21)16-8-10-17(30-5)11-9-16/h7-11,13-14,28H,12H2,1-6H3

InChI Key

CCYKXDPVYWRNMH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Apis cerana	LOTUS Database	35616633
Solori scandens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Hydroxyisoflavonoids

Direct Parent

Hydroxyisoflavonoids

Alternative Parents

Substituents

Isoflav-3-enone skeleton
Hydroxyisoflavonoid
Pyranocoumarin
Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Benzopyran
1-benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxybenzene (CHEBI:6521 )
hydroxycoumarin (CHEBI:6521 )
3-Arylcoumarins (C10491 )
Other Flavonoids (LMPK12160024 )

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	4.66	ALOGPS
logP	5.01	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	6.41	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.46 m³·mol⁻¹	ChemAxon
Polarizability	49.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00002543

Chemspider ID

Not Available

KEGG Compound ID

C10491

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54699185

PDB ID

Not Available

ChEBI ID

6521

Good Scents ID

Not Available

References

General References

Rajemiarimiraho M, Banzouzi JT, Rakotonandrasana SR, Chalard P, Benoit-Vical F, Rasoanaivo LH, Raharisololalao A, Randrianjah R: Pyranocoumarin and triterpene from Millettia richardiana. Nat Prod Commun. 2013 Aug;8(8):1099-100. [PubMed:24079177 ]
Rajemiarimiraho M, Banzouzi JT, Nicolau-Travers ML, Ramos S, Cheikh-Ali Z, Bories C, Rakotonandrasana OL, Rakotonandrasana S, Andrianary PA, Benoit-Vical F: Antiprotozoal activities of Millettia richardiana (Fabaceae) from Madagascar. Molecules. 2014 Apr 3;19(4):4200-11. doi: 10.3390/molecules19044200. [PubMed:24705564 ]

Showing NP-Card for Lonchocarpenin (NP0051473)

MOL for NP0051473 (Lonchocarpenin)

3D MOL for NP0051473 (Lonchocarpenin)

3D SDF for NP0051473 (Lonchocarpenin)

3D-SDF for NP0051473 (Lonchocarpenin)

PDB for NP0051473 (Lonchocarpenin)

3D PDB for NP0051473 (Lonchocarpenin)

SMILES for NP0051473 (Lonchocarpenin)

INCHI for NP0051473 (Lonchocarpenin)

Structure for NP0051473 (Lonchocarpenin)

3D Structure for NP0051473 (Lonchocarpenin)