NP-MRD: Showing NP-Card for (3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0165748)

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Record Information

Version

2.0

Created at

2022-09-03 00:57:58 UTC

Updated at

2022-09-03 00:57:58 UTC

NP-MRD ID

NP0165748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

Description

Kigelin belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. (3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one was first documented in 2009 (PMID: 19708666). Based on a literature review very few articles have been published on Kigelin (PMID: 20560113).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.6925    2.5972    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988    1.4652    0.3647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6863    0.6663    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    0.9704    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.1820    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -0.9236   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6631   -1.2324   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8343   -2.3133   -1.8790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843   -0.4294   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.7789   -1.2821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9242   -1.6503   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -1.7065   -0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362   -2.7110   -1.6101 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -1.2590   -0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0852    0.1763   -0.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4504    0.5113    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882    0.5375    0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0704    2.3351    2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696    2.9999    1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364    3.3666    0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3078    1.8264    1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -2.9800   -2.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5653   -1.0280    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5678   -2.1674   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4229   -2.4458   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9015    0.7157   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    1.5009    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1516   -0.2874    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556    0.5753    1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    1.6077    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -0.1210    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  9  3  1  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
 15 26  1  6
 16 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
  8 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
M  END


  Mrv1652309032202572D          

 17 18  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  5 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(=O)O[C@H](C)C2)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O5/c1-6-4-7-5-8(15-2)11(16-3)10(13)9(7)12(14)17-6/h5-6,13H,4H2,1-3H3/t6-/m1/s1

> <INCHI_KEY>
VXWBNPSAWLNEKD-ZCFIWIBFSA-N

> <FORMULA>
C12H14O5

> <MOLECULAR_WEIGHT>
238.239

> <EXACT_MASS>
238.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.04464497042111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
2.2642784579999993

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.190584938354583

> <JCHEM_PKA_STRONGEST_BASIC>
-3.19852641771568

> <JCHEM_POLAR_SURFACE_AREA>
64.99

> <JCHEM_REFRACTIVITY>
60.71900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₅

Average Mass

238.2390 Da

Monoisotopic Mass

238.08412 Da

IUPAC Name

(3R)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(=O)O[C@H](C)C2)C(O)=C1OC

InChI Identifier

InChI=1S/C12H14O5/c1-6-4-7-5-8(15-2)11(16-3)10(13)9(7)12(14)17-6/h5-6,13H,4H2,1-3H3/t6-/m1/s1

InChI Key

VXWBNPSAWLNEKD-ZCFIWIBFSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.8	ALOGPS
logP	2.26	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.72 m³·mol⁻¹	ChemAxon
Polarizability	24.04 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002833

Chemspider ID

20052735

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22295076

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Higgins CA, Bell T, Delbederi Z, Feutren-Burton S, McClean B, O'Dowd C, Watters W, Armstrong P, Waugh D, van den Berg H: Growth inhibitory activity of extracted material and isolated compounds from the fruits of Kigelia pinnata. Planta Med. 2010 Nov;76(16):1840-6. doi: 10.1055/s-0030-1250046. Epub 2010 Jun 17. [PubMed:20560113 ]
Higgins CA, Delbederi Z, McGarel K, Mills T, McGrath O, Feutren-Burton S, Watters W, Armstrong P, Johnston PG, Waugh D, van den Berg H: Synthesis and in vitro and in vivo evaluation of a series of dihydroisocoumarin derivatives conjugated with fatty acids, alcohols, and amines as potential anticancer agents. Bioconjug Chem. 2009 Sep;20(9):1737-51. doi: 10.1021/bc900122g. [PubMed:19708666 ]
LOTUS database [Link]

Showing NP-Card for (3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0165748)

MOL for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D MOL for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D SDF for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D-SDF for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

PDB for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D PDB for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

SMILES for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

INCHI for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

Structure for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D Structure for NP0165748 ((3r)-8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)