NP-MRD: Showing NP-Card for Khellactone (NP0139487)

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Record Information

Version

2.0

Created at

2022-06-29 19:56:37 UTC

Updated at

2022-06-29 19:56:37 UTC

NP-MRD ID

NP0139487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Khellactone

Description

9,10-Dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Khellactone is found in Ammi visnaga, Angelica keiskei, Citrus sinensis, Cyclospermum leptophyllum, Musineon divaricatum and Peucedanum japonicum. 9,10-Dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5283   -0.9167    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443   -0.0467    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    1.3952    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.1479    1.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0537    0.0609    1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    0.5720    2.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725    0.7466    1.9619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426    0.4188    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038    0.6090    0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    0.2605   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6531   -0.2491   -1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.5518   -2.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -0.3934   -1.4278 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354   -0.0913   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839   -0.2670   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -0.8046   -1.0890 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2941   -2.2123   -1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.3713   -1.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9724    0.7067   -1.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4247   -0.3317    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2888   -1.6008    1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -1.5924   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8390    1.4267   -0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9395    1.7703    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833    1.9827   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563    0.8136    3.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7048    1.1451    2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6079    1.0090    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311    0.3866   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907   -0.5438   -2.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -2.5238   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114   -1.2031   -1.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    0.5440   -2.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 15 14  1  0
 14  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8  7  1  0
  7  6  2  0
 18  2  1  0
 13 14  1  0
  6  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 16 30  1  6
 17 31  1  0
 18 32  1  6
 19 33  1  0
  9 28  1  0
 10 29  1  0
  7 27  1  0
  6 26  1  0
M  END


  Mrv1652308231918572D          

 19 21  0  0  0  0            999 V2000
    4.6465   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-14(2)13(17)11(16)10-8(19-14)5-3-7-4-6-9(15)18-12(7)10/h3-6,11,13,16-17H,1-2H3

> <INCHI_KEY>
HKXQUNNSKMWIKJ-UHFFFAOYSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.261

> <EXACT_MASS>
262.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.13669861986301

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.8133974599999996

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.00124267753813

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.556364734556386

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7357969855433533

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
67.54840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,10-dihydroxy-8,8-dimethyl-9H,10H-pyrano[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.414  -6.517   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.494  -6.517   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3    4   12                                                  
CONECT    8    5   10   19                                                  
CONECT    9    6   15   18                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10   13   16                                                  
CONECT   12    7   10   18                                                  
CONECT   13   11   14   17                                                  
CONECT   14    1    2   13   19                                             
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   13                                                            
CONECT   18    9   12                                                       
CONECT   19    8   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Carduben	MeSH, HMDB
Visnadine	MeSH, HMDB
Visnadin	MeSH, HMDB

Chemical Formula

C₁₄H₁₄O₅

Average Mass

262.2610 Da

Monoisotopic Mass

262.08412 Da

IUPAC Name

9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one

Traditional Name

9,10-dihydroxy-8,8-dimethyl-9H,10H-pyrano[2,3-h]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2

InChI Identifier

InChI=1S/C14H14O5/c1-14(2)13(17)11(16)10-8(19-14)5-3-7-4-6-9(15)18-12(7)10/h3-6,11,13,16-17H,1-2H3

InChI Key

HKXQUNNSKMWIKJ-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ammi visnaga	LOTUS Database	35616633
Angelica keiskei	LOTUS Database	35616633
Citrus sinensis	LOTUS Database	35616633
Cyclospermum leptophyllum	LOTUS Database	35616633
Musineon divaricatum	LOTUS Database	35616633
Peucedanum japonicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Secondary alcohol
1,2-diol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.21	ALOGPS
logP	0.81	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.55 m³·mol⁻¹	ChemAxon
Polarizability	26.14 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

HMDB0138052

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093038

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

253856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Khellactone (NP0139487)

MOL for NP0139487 (Khellactone)

3D MOL for NP0139487 (Khellactone)

3D SDF for NP0139487 (Khellactone)

3D-SDF for NP0139487 (Khellactone)

PDB for NP0139487 (Khellactone)

3D PDB for NP0139487 (Khellactone)

SMILES for NP0139487 (Khellactone)

INCHI for NP0139487 (Khellactone)

Structure for NP0139487 (Khellactone)

3D Structure for NP0139487 (Khellactone)