NP-MRD: Showing NP-Card for Khellin (NP0002895)

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Record Information

Version

2.0

Created at

2020-11-23 19:43:02 UTC

Updated at

2021-08-19 23:59:30 UTC

NP-MRD ID

NP0002895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Khellin

Provided By

BMRB

Description

Khellin, also known as quelina or khelloyd, belongs to the class of organic compounds known as furanochromones. These are polycyclic aromatic compounds containing a furan ring fused to a 1-benzopyran-4-one ring system. Thus, khellin is considered to be an aromatic polyketide. Khellin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Khellin is found in Allium nutans, Dioscorea deltoidea and Dioscorea parviflora. Khellin was first documented in 2003 (PMID: 12880095). Based on a literature review a small amount of articles have been published on Khellin (PMID: 19639121) (PMID: 21069311) (PMID: 24069365).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.6226   -4.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -3.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -1.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -2.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3377    0.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8389    0.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    2.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    3.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6624    0.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104    2.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050    3.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638    1.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5693    0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213   -0.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0679   -0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -5.1308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958   -3.0349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706   -5.1560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3027   -1.5017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1696    1.5586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788    4.5914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208    1.6846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032    3.5090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    2.7273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -1.6144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3936    1.2924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761   -0.5320    0.0000 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
  8  4  1  0
 19 12  2  0
  1 20  1  1
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
 11 25  1  6
 11 26  1  0
 11 27  1  0
 15 28  1  0
 17 29  1  6
 17 30  1  0
 17 31  1  0
M  END

NP0002895
     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.8858    3.5433    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5744    2.7667   -0.5257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619    1.5459   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404    1.4718   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078    2.3618   -0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5793    1.7723   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099    0.3862   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    0.2207   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -0.9298   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -2.1534   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -2.8312    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -0.8163   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404   -1.9686   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482   -3.0873   -0.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.8445   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.5874   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -0.5249   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0348    0.4833   -0.3212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278    0.3993   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213    2.9207    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    3.9132    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    4.4190    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429    2.2462   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1695   -0.3832   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -3.9342    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7089   -2.5378    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040   -2.6487    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918   -2.7254   -0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957   -0.4832    0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6062    0.3912   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7567   -1.3855   -0.6455 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
  8  4  1  0
 19 12  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END


     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.6226   -4.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -3.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -1.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -2.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3377    0.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8389    0.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    2.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    3.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6624    0.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104    2.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050    3.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638    1.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5693    0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213   -0.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0679   -0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -5.1308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958   -3.0349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706   -5.1560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3027   -1.5017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1696    1.5586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0208    1.6846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032    3.5090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    2.7273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -1.6144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3936    1.2924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761   -0.5320    0.0000 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
  8  4  1  0
 19 12  2  0
  1 20  1  1
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
 11 25  1  6
 11 26  1  0
 11 27  1  0
 15 28  1  0
 17 29  1  6
 17 30  1  0
 17 31  1  0
M  END
> <DATABASE_ID>
NP0002895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC=CC2=C(OC)C2=C1OC(C)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

> <INCHI_KEY>
HSMPDPBYAYSOBC-UHFFFAOYSA-N

> <FORMULA>
C14H12O5

> <MOLECULAR_WEIGHT>
260.245

> <EXACT_MASS>
260.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.045009190028267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9-dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
1.715334138666667

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.588092988959911

> <JCHEM_PKA_STRONGEST_BASIC>
-2.84951258935728

> <JCHEM_POLAR_SURFACE_AREA>
57.900000000000006

> <JCHEM_REFRACTIVITY>
68.8747

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kelamin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002895
     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.8858    3.5433    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5744    2.7667   -0.5257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619    1.5459   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404    1.4718   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078    2.3618   -0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5793    1.7723   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099    0.3862   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    0.2207   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -0.9298   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -2.1534   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -2.8312    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -0.8163   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404   -1.9686   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482   -3.0873   -0.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.8445   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.5874   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -0.5249   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0348    0.4833   -0.3212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278    0.3993   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213    2.9207    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    3.9132    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    4.4190    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429    2.2462   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1695   -0.3832   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -3.9342    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7089   -2.5378    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040   -2.6487    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918   -2.7254   -0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957   -0.4832    0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6062    0.3912   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7567   -1.3855   -0.6455 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
  8  4  1  0
 19 12  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.467   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.372   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.467  -0.476   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4    5    8                                                       
CONECT    5    4   18                                                       
CONECT    6    7    9                                                       
CONECT    7    1    6   19                                                  
CONECT    8    4   11   12                                                  
CONECT    9    6   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11    8   10   16                                                  
CONECT   12    8   14   18                                                  
CONECT   13   10   14   19                                                  
CONECT   14   12   13   17                                                  
CONECT   15    9                                                            
CONECT   16    2   11                                                       
CONECT   17    3   14                                                       
CONECT   18    5   12                                                       
CONECT   19    7   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    NP0002895
HETATM    1  C1  UNL     1       0.886   3.543   0.596  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.574   2.767  -0.526  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.062   1.546  -0.491  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.440   1.472  -0.559  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.408   2.362  -0.659  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.579   1.772  -0.688  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.410   0.386  -0.601  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.043   0.221  -0.520  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.292  -0.930  -0.416  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.889  -2.153  -0.379  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.312  -2.831   0.780  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.092  -0.816  -0.350  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.840  -1.969  -0.246  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.248  -3.087  -0.215  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.201  -1.845  -0.182  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.784  -0.587  -0.222  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.267  -0.525  -0.148  1.00  0.00           C  
HETATM   18  O5  UNL     1       2.035   0.483  -0.321  1.00  0.00           O  
HETATM   19  C14 UNL     1       0.728   0.399  -0.385  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.921   2.921   1.525  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.938   3.913   0.446  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.241   4.419   0.729  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.543   2.246  -0.765  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.170  -0.383  -0.598  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.245  -3.934   0.598  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.709  -2.538   1.638  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.404  -2.649   0.979  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.792  -2.725  -0.102  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.596  -0.483   0.918  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.606   0.391  -0.666  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.757  -1.386  -0.645  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    8
CONECT    5    6
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9
CONECT    9   10   12
CONECT   10   11
CONECT   11   25   26   27
CONECT   12   13   19   19
CONECT   13   14   14   15
CONECT   15   16   16   28
CONECT   16   17   18
CONECT   17   29   30   31
CONECT   18   19
END

NP0002895
     RDKit          3D

31 33  0  0  0  0  0  0  0  0999 V2000
    0.8858    3.5433    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5744    2.7667   -0.5257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619    1.5459   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404    1.4718   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078    2.3618   -0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5793    1.7723   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099    0.3862   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    0.2207   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -0.9298   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -2.1534   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -2.8312    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -0.8163   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404   -1.9686   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482   -3.0873   -0.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.8445   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.5874   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -0.5249   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0348    0.4833   -0.3212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278    0.3993   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213    2.9207    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    3.9132    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    4.4190    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429    2.2462   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1695   -0.3832   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -3.9342    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7089   -2.5378    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040   -2.6487    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918   -2.7254   -0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957   -0.4832    0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6062    0.3912   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7567   -1.3855   -0.6455 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
  8  4  1  0
 19 12  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one	ChEBI
Khelline	ChEBI
Khellinum	ChEBI
Quelina	ChEBI
Khelloyd	HMDB
Ammivin	HMDB
Visammin	HMDB
Khellin	MeSH

Chemical Formula

C₁₄H₁₂O₅

Average Mass

260.2450 Da

Monoisotopic Mass

260.06847 Da

IUPAC Name

4,9-dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one

Traditional Name

kelamin

CAS Registry Number

Not Available

SMILES

COC1=C2OC=CC2=C(OC)C2=C1OC(C)=CC2=O

InChI Identifier

InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

InChI Key

HSMPDPBYAYSOBC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	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
Allium nutans	LOTUS Database	35616633
Ammi visnaga	KNApSAcK Database	22123792
Annona muricata	KNApSAcK Database	22123792
Dioscorea deltoidea	LOTUS Database	35616633
Dioscorea parviflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanochromones. These are polycyclic aromatic compounds containing a furan ring fused to a 1-benzopyran-4-one ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Furanochromones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	154.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	482.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1040 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	1.770 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.28	ALOGPS
logP	1.72	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.87 m³·mol⁻¹	ChemAxon
Polarizability	26.05 Å³	ChemAxon
Number of Rings	3	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

HMDB0253797

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002431

Chemspider ID

3696

KEGG Compound ID

C09010

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Khellin

METLIN ID

Not Available

PubChem Compound

3828

PDB ID

Not Available

ChEBI ID

6133

Good Scents ID

rw1253141

References

General References

Mawatari K, Mashiko S, Watanabe M, Nakagomi K: Fluorometric determination of khellin in human urine and serum by high-performance liquid chromatography using postcolumn photoirradiation. Anal Sci. 2003 Jul;19(7):1071-3. doi: 10.2116/analsci.19.1071. [PubMed:12880095 ]
Omar S, Eriksson LA: Computational study of khellin excited states and photobinding to DNA. Photochem Photobiol Sci. 2009 Aug;8(8):1179-86. doi: 10.1039/b905147c. Epub 2009 Jul 6. [PubMed:19639121 ]
Vanachayangkul P, Chow N, Khan SR, Butterweck V: Prevention of renal crystal deposition by an extract of Ammi visnaga L. and its constituents khellin and visnagin in hyperoxaluric rats. Urol Res. 2011 Jun;39(3):189-95. doi: 10.1007/s00240-010-0333-y. Epub 2010 Nov 11. [PubMed:21069311 ]
Vrzal R, Frauenstein K, Proksch P, Abel J, Dvorak Z, Haarmann-Stemmann T: Khellin and visnagin differentially modulate AHR signaling and downstream CYP1A activity in human liver cells. PLoS One. 2013 Sep 19;8(9):e74917. doi: 10.1371/journal.pone.0074917. eCollection 2013. [PubMed:24069365 ]

Showing NP-Card for Khellin (NP0002895)

MOL for NP0002895 (Khellin)

3D MOL for NP0002895 (Khellin)

3D SDF for NP0002895 (Khellin)

3D-SDF for NP0002895 (Khellin)

PDB for NP0002895 (Khellin)

3D PDB for NP0002895 (Khellin)

SMILES for NP0002895 (Khellin)

INCHI for NP0002895 (Khellin)

Structure for NP0002895 (Khellin)

3D Structure for NP0002895 (Khellin)