NP-MRD: Showing NP-Card for Odoratol (NP0050594)

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Record Information

Version

2.0

Created at

2022-04-27 21:58:25 UTC

Updated at

2022-04-27 21:58:25 UTC

NP-MRD ID

NP0050594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Odoratol

Description

Odoratol belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, odoratol is considered to be a flavonoid. Odoratol is found in Cedrela fissilis, Cedrela graziovii, Cedrela mexicana , Cedrela odorata , Lathyrus odoratus , Myristica malabarica, Pterocarpus angolensis and Virola surinamensis. Odoratol was first documented in 2008 (PMID: 18991203). Based on a literature review very few articles have been published on Odoratol (PMID: 21269253).

Structure

MOL SDF PDB SMILES InChI

  Mrv1652304272223582D          

 22 23  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
  1  2  2  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
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 19  1  1  0  0  0
  3 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050594

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@@H](O)C(=O)C2=C(O)C=C(OC)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-21-12-5-3-11(4-6-12)9-16(19)17(20)14-8-7-13(22-2)10-15(14)18/h3-8,10,16,18-19H,9H2,1-2H3/t16-/m1/s1

> <INCHI_KEY>
PPOABILDHKLUET-MRXNPFEDSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.326

> <EXACT_MASS>
302.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.840656541522215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.9698280456666666

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.321990336282763

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.922488332838672

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5717109431700997

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
82.1832

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
odoratol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19    9                                                            
CONECT   20    3                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3260 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

(2R)-2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one

Traditional Name

odoratol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@@H](O)C(=O)C2=C(O)C=C(OC)C=C2)C=C1

InChI Identifier

InChI=1S/C17H18O5/c1-21-12-5-3-11(4-6-12)9-16(19)17(20)14-8-7-13(22-2)10-15(14)18/h3-8,10,16,18-19H,9H2,1-2H3/t16-/m1/s1

InChI Key

PPOABILDHKLUET-MRXNPFEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cedrela fissilis	LOTUS Database	35616633
Cedrela graziovii	Plant	KNApSAcK
Cedrela mexicana	Plant	KNApSAcK
Cedrela odorata	Plant	KNApSAcK
Lathyrus odoratus	Plant	KNApSAcK
Myristica malabarica	LOTUS Database	35616633
Pterocarpus angolensis	Plant	KNApSAcK
Virola surinamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
Phenylketone
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Acyloin
Benzenoid
Alpha-hydroxy ketone
Vinylogous acid
Secondary alcohol
Ketone
Ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120574 )

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	2.66	ALOGPS
logP	2.97	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.18 m³·mol⁻¹	ChemAxon
Polarizability	31.84 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

C00000981

Chemspider ID

24846125

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607724

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cazal CM, Choosang K, Severino VG, Soares MS, Sarria AL, Fernandes JB, Silva MF, Vieira PC, Pakkong P, Almeida GM, Vasconcelos MH, Nascimento MS, Pinto MM: Evaluation of effect of triterpenes and limonoids on cell growth, cell cycle and apoptosis in human tumor cell line. Anticancer Agents Med Chem. 2010 Dec;10(10):769-76. doi: 10.2174/187152010794728620. [PubMed:21269253 ]
Leite AC, Ambrozin AR, Fernandes JB, Vieira PC, da Silva MF, de Albuquerque S: Trypanocidal activity of limonoids and triterpenes from Cedrela fissilis. Planta Med. 2008 Dec;74(15):1795-9. doi: 10.1055/s-0028-1088323. Epub 2008 Nov 7. [PubMed:18991203 ]

Showing NP-Card for Odoratol (NP0050594)

MOL for NP0050594 (Odoratol)

3D MOL for NP0050594 (Odoratol)

3D SDF for NP0050594 (Odoratol)

3D-SDF for NP0050594 (Odoratol)

PDB for NP0050594 (Odoratol)

3D PDB for NP0050594 (Odoratol)

SMILES for NP0050594 (Odoratol)

INCHI for NP0050594 (Odoratol)

Structure for NP0050594 (Odoratol)

3D Structure for NP0050594 (Odoratol)