Showing NP-Card for Khellin (NP0002895)

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Record Information
Version2.0
Created at2020-11-23 19:43:02 UTC
Updated at2021-08-19 23:59:30 UTC
NP-MRD IDNP0002895
Secondary Accession NumbersNone
Natural Product Identification
Common NameKhellin
Provided ByBMRBBMRB logo
DescriptionKhellin, 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002895 (Khellin)

     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
Download

3D MOL for NP0002895 (Khellin)

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
Download

3D SDF for NP0002895 (Khellin)

     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
> <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

$$$$
Download

3D-SDF for NP0002895 (Khellin)

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
Download

PDB for NP0002895 (Khellin)

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
Download

3D PDB for NP0002895 (Khellin)

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
Download

SMILES for NP0002895 (Khellin)

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

INCHI for NP0002895 (Khellin)

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
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View in JSmol
Synonyms
ValueSource
4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-oneChEBI
KhellineChEBI
KhellinumChEBI
QuelinaChEBI
KhelloydHMDB
AmmivinHMDB
VisamminHMDB
KhellinMeSH
Chemical FormulaC14H12O5
Average Mass260.2450 Da
Monoisotopic Mass260.06847 Da
IUPAC Name4,9-dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one
Traditional Namekelamin
CAS Registry NumberNot 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 KeyHSMPDPBYAYSOBC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium nutansLOTUS Database
Ammi visnagaKNApSAcK Database
Annona muricataKNApSAcK Database
Dioscorea deltoideaLOTUS Database
Dioscorea parvifloraLOTUS Database
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentFuranochromones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point154.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point482.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1040 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP1.770 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.28ALOGPS
logP1.72ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)14.59ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.87 m³·mol⁻¹ChemAxon
Polarizability26.05 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0253797
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002431
Chemspider ID3696
KEGG Compound IDC09010
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKhellin
METLIN IDNot Available
PubChem Compound3828
PDB IDNot Available
ChEBI ID6133
Good Scents IDrw1253141
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]