NP-MRD: Showing NP-Card for 7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone (NP0060452)

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Record Information

Version

2.0

Created at

2022-04-28 05:30:09 UTC

Updated at

2022-04-28 05:30:09 UTC

NP-MRD ID

NP0060452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone

Description

Kurarinone belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, kurarinone is considered to be a flavonoid lipid molecule. 7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone is found in Gentiana macrophylla and Sophora flavescens . 7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone was first documented in 2000 (PMID: 10843587). Kurarinone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 21831037) (PMID: 22932446) (PMID: 23333426).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006312D          

 32 34  0  0  0  0            999 V2000
 9999.268010001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.553510001.4667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.839010001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.124610001.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.410110001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.695610001.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.410110000.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.553510002.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.839010002.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.268010002.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.841110000.2271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2680 9997.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5494 9997.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6919 9997.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8349 9998.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.264310001.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.834910001.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.120510001.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.120510000.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8349 9999.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.549410000.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.549410001.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.268010000.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5535 9999.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5534 9998.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2679 9998.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.693310000.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9788 9999.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9788 9998.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6933 9998.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4078 9998.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4078 9999.8101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 20 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  1 23  1  0  0  0  0
 26 12  1  0  0  0  0
 24 11  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 32  1  0  0  0  0
 30 14  2  0  0  0  0
 32 19  1  6  0  0  0
 28 23  2  0  0  0  0
 26 29  2  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -2.4250   -1.1389    1.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6437   -1.0483    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6830   -1.9702   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -0.0893   -0.4734 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8055    0.9201   -1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7674    1.5354   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044    2.8348    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467    3.7441   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7855    3.4078    0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -0.7104   -1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -1.6934   -0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300   -3.0356   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994   -3.4448   -1.8443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902   -4.0047   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -3.6280    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5116   -4.5754    0.9206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2639   -5.9363    0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -2.2789    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.3075   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203   -0.0085    0.2927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    0.4348    1.3511 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9530    1.5729    0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095    1.8343    1.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252    2.9380    0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3821    3.7637   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0726    4.8650   -0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    3.5071   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032    2.4296   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1183    2.1307   -0.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7799   -0.5785    2.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9404   -1.8450    1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9870   -2.5100    1.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835   -1.8507    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -0.5219    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4797   -2.9883    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -1.6633    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -1.9708   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711    0.5522    0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121    1.7385   -1.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223    0.4094   -2.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795    0.9056    0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    4.8222   -0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458    3.5614   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604    3.6642   -1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2086    4.3792    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6459    2.7416    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2689    3.6972    1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -1.1520   -2.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    0.0691   -1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4128   -4.4314   -1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -5.0598   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0670   -6.5301    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -6.0575   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2660   -6.1829    1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551    0.9547    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    1.2200    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9047    3.0902    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6820    4.8037   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    4.1666   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068    2.7314   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632   -0.8629    3.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.3499    2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 18  2  0
 18 31  1  0
 31 32  2  0
 31 30  1  0
 30 21  1  0
 21 20  1  0
 20 19  1  0
 19 11  2  0
 11 10  1  0
 10  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 11 12  1  0
 12 13  1  0
 12 14  2  0
 21 22  1  0
 22 28  2  0
 28 29  1  0
 28 27  1  0
 27 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 14 15  1  0
 23 22  1  0
 19 18  1  0
 17 52  1  0
 17 53  1  0
 17 54  1  0
 30 61  1  0
 30 62  1  0
 21 55  1  1
 10 48  1  0
 10 49  1  0
  4 38  1  1
  5 39  1  0
  5 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  1 33  1  0
  1 34  1  0
 13 50  1  0
 14 51  1  0
 29 60  1  0
 27 59  1  0
 26 58  1  0
 24 57  1  0
 23 56  1  0
M  END


  Mrv1652309272006312D          

 32 34  0  0  0  0            999 V2000
 9999.268010001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.553510001.4667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.839010001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.124610001.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.410110001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.695610001.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.410110000.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.553510002.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.839010002.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.268010002.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.841110000.2271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2680 9997.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5494 9997.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6919 9997.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8349 9998.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.264310001.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.834910001.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.120510001.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.120510000.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8349 9999.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.549410000.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.549410001.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.268010000.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5535 9999.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5534 9998.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2679 9998.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.693310000.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9788 9999.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9788 9998.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6933 9998.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4078 9998.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4078 9999.8101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 20 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  1 23  1  0  0  0  0
 26 12  1  0  0  0  0
 24 11  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 32  1  0  0  0  0
 30 14  2  0  0  0  0
 32 19  1  6  0  0  0
 28 23  2  0  0  0  0
 26 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0060452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C[C@H](OC2=C(C[C@@H](CC=C(C)C)C(C)=C)C(O)=C1)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O6/c1-14(2)6-7-16(15(3)4)10-19-21(29)12-24(31-5)25-22(30)13-23(32-26(19)25)18-9-8-17(27)11-20(18)28/h6,8-9,11-12,16,23,27-29H,3,7,10,13H2,1-2,4-5H3/t16-,23+/m1/s1

> <INCHI_KEY>
LTTQKYMNTNISSZ-MWTRTKDXSA-N

> <FORMULA>
C26H30O6

> <MOLECULAR_WEIGHT>
438.52

> <EXACT_MASS>
438.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.1100205714438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
5.316102160666667

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.022860929291335

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.070991132286398

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6155629142739985

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
124.67349999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kurarinone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.3008668.635   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.9678669.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.6338668.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.2998669.405   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8659.9668668.635   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8658.6328669.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9668667.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.9678670.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.6338671.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3008671.715   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8662.6378667.091   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8665.3008662.450   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8663.9598661.675   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8667.9588662.450   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8671.9588664.777   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8674.6278669.397   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8671.9588669.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.6258668.629   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.6258667.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.9588666.319   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8673.2928667.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.2928668.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8665.3008667.082   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8663.9678666.312   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8663.9668664.772   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8665.3008664.002   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8667.9618667.082   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0    8666.6278666.312   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8666.6278664.772   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8667.9618664.002   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8669.2958664.772   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8669.2958666.312   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   24                                                            
CONECT   12   13   26                                                       
CONECT   13   12                                                            
CONECT   14   30                                                            
CONECT   15   20                                                            
CONECT   16   22                                                            
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21   15                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17   16                                                  
CONECT   23   24    1   28                                                  
CONECT   24   23   25   11                                                  
CONECT   25   24   26                                                       
CONECT   26   25   12   29                                                  
CONECT   27   28   32                                                       
CONECT   28   29   27   23                                                  
CONECT   29   28   30   26                                                  
CONECT   30   29   31   14                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27   19                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone	ChEBI
Norkurarinone	MeSH
(-)-Kurarinone	PhytoBank

Chemical Formula

C₂₆H₃₀O₆

Average Mass

438.5200 Da

Monoisotopic Mass

438.20424 Da

IUPAC Name

(2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

kurarinone

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C[C@H](OC2=C(C[C@@H](CC=C(C)C)C(C)=C)C(O)=C1)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C26H30O6/c1-14(2)6-7-16(15(3)4)10-19-21(29)12-24(31-5)25-22(30)13-23(32-26(19)25)18-9-8-17(27)11-20(18)28/h6,8-9,11-12,16,23,27-29H,3,7,10,13H2,1-2,4-5H3/t16-,23+/m1/s1

InChI Key

LTTQKYMNTNISSZ-MWTRTKDXSA-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
Gentiana macrophylla	Plant	KNApSAcK
Sophora flavescens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
5-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Aromatic monoterpenoid
Chromane
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
Aryl alkyl ketone
Anisole
Aryl ketone
Resorcinol
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavanone (CHEBI:66150 )
monomethoxyflavanone (CHEBI:66150 )
flavanones (C17446 )
Flavanones (LMPK12140499 )

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	4.24	ALOGPS
logP	5.32	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.67 m³·mol⁻¹	ChemAxon
Polarizability	47.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00014195

Chemspider ID

10155207

KEGG Compound ID

C17446

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11982640

PDB ID

Not Available

ChEBI ID

66150

Good Scents ID

Not Available

References

General References

Kang TH, Jeong SJ, Ko WG, Kim NY, Lee BH, Inagaki M, Miyamoto T, Higuchi R, Kim YC: Cytotoxic lavandulyl flavanones from Sophora flavescens. J Nat Prod. 2000 May;63(5):680-1. doi: 10.1021/np990567x. [PubMed:10843587 ]
Berghe WV, De Naeyer A, Dijsselbloem N, David JP, De Keukeleire D, Haegeman G: Attenuation of ERK/RSK2-driven NFkappaB gene expression and cancer cell proliferation by kurarinone, a lavandulyl flavanone isolated from Sophora flavescens ait. roots. Endocr Metab Immune Disord Drug Targets. 2011 Sep 1;11(3):247-61. doi: 10.2174/187153011796429790. [PubMed:21831037 ]
Seo OW, Kim JH, Lee KS, Lee KS, Kim JH, Won MH, Ha KS, Kwon YG, Kim YM: Kurarinone promotes TRAIL-induced apoptosis by inhibiting NF-kappaB-dependent cFLIP expression in HeLa cells. Exp Mol Med. 2012 Nov 30;44(11):653-64. doi: 10.3858/emm.2012.44.11.074. [PubMed:22932446 ]
Kim BH, Na KM, Oh I, Song IH, Lee YS, Shin J, Kim TY: Kurarinone regulates immune responses through regulation of the JAK/STAT and TCR-mediated signaling pathways. Biochem Pharmacol. 2013 Apr 15;85(8):1134-44. doi: 10.1016/j.bcp.2013.01.005. Epub 2013 Jan 17. [PubMed:23333426 ]

Showing NP-Card for 7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone (NP0060452)

MOL for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

3D MOL for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

3D SDF for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

3D-SDF for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

PDB for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

3D PDB for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

SMILES for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

INCHI for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

Structure for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)

3D Structure for NP0060452 (7,2',4'-Trihydroxy-8-lavandulyl-5-methoxyflavanone)