NP-MRD: Showing NP-Card for Loureiriol (NP0140301)

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Record Information

Version

2.0

Created at

2022-06-29 21:22:11 UTC

Updated at

2022-06-29 21:22:11 UTC

NP-MRD ID

NP0140301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Loureiriol

Description

Loureiriol belongs to the class of organic compounds known as homoisoflavans. These are homoisoflavonoids with a structure based on the chromane system. Chromone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran. Loureiriol was first documented in 2002 (PMID: 12357401). Based on a literature review very few articles have been published on Loureiriol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.2182    1.0267    0.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -0.0023    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950    0.2382    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    1.4449   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4672    2.4906   -0.5143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949    1.6185   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    0.5931   -0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9325    0.7692   -0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110   -0.6174   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7946   -0.8042    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -2.0015    0.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -2.3854    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -1.3437    0.4821 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6623   -1.4777    1.7568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -1.5662   -0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2814   -0.5991   -0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3327   -0.9212    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728   -0.0327    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609    1.1600   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214    2.0389   -0.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    1.4931   -1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708    0.5846   -1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7279    3.3983   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562    2.5714   -1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737    0.6217   -1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8058   -1.4332    0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060   -3.3676    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886   -2.5911   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770   -0.6246    2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -1.5260   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5368   -2.6069   -0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3479   -1.8522    0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2045   -0.2736    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3805    2.7427    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3121    2.4112   -1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480    0.8233   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 13  1  0
 13 14  1  1
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 16 22  1  0
 22 21  2  0
 21 19  1  0
  2 13  1  0
  3 10  1  0
 20 34  1  0
 18 33  1  0
 17 32  1  0
 15 30  1  0
 15 31  1  0
 14 29  1  0
 12 27  1  0
 12 28  1  0
  9 26  1  0
  8 25  1  0
  6 24  1  0
  5 23  1  0
 22 36  1  0
 21 35  1  0
M  END


  Mrv1652306292223222D          

 22 24  0  0  1  0            999 V2000
    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  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  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
    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    0.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    1.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593    2.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
  8 12  1  0  0  0  0
  6 13  1  0  0  0  0
  2 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  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
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
  2 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C[C@@]2(O)COC3=CC(O)=CC(O)=C3C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c17-10-3-1-9(2-4-10)7-16(21)8-22-13-6-11(18)5-12(19)14(13)15(16)20/h1-6,17-19,21H,7-8H2/t16-/m1/s1

> <INCHI_KEY>
CKOAWBPJSODKQL-MRXNPFEDSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.123472839109358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
2.4248016559999996

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.14655304927217

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.74966430564705

> <JCHEM_PKA_STRONGEST_BASIC>
-4.086385403695158

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
77.67750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-2H-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.205  -0.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.928   0.643   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.467   0.697   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.190   2.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.374   3.363   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.835   3.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.112   1.949   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.097   4.723   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.518   0.536   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3   14   22                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    1                                                       
CONECT   12    8                                                            
CONECT   13    6                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2820 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C[C@@]2(O)COC3=CC(O)=CC(O)=C3C2=O)C=C1

InChI Identifier

InChI=1S/C16H14O6/c17-10-3-1-9(2-4-10)7-16(21)8-22-13-6-11(18)5-12(19)14(13)15(16)20/h1-6,17-19,21H,7-8H2/t16-/m1/s1

InChI Key

CKOAWBPJSODKQL-MRXNPFEDSA-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 homoisoflavans. These are homoisoflavonoids with a structure based on the chromane system. Chromone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavans

Direct Parent

Homoisoflavans

Alternative Parents

Substituents

Homoisoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Acyloin
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Tertiary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aldehyde
Organic oxide
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9897141

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11722425

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Likhitwitayawuid K, Sawasdee K, Kirtikara K: Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracaena loureiri. Planta Med. 2002 Sep;68(9):841-3. doi: 10.1055/s-2002-34403. [PubMed:12357401 ]

Showing NP-Card for Loureiriol (NP0140301)

MOL for NP0140301 (Loureiriol)

3D MOL for NP0140301 (Loureiriol)

3D SDF for NP0140301 (Loureiriol)

3D-SDF for NP0140301 (Loureiriol)

PDB for NP0140301 (Loureiriol)

3D PDB for NP0140301 (Loureiriol)

SMILES for NP0140301 (Loureiriol)

INCHI for NP0140301 (Loureiriol)

Structure for NP0140301 (Loureiriol)

3D Structure for NP0140301 (Loureiriol)