NP-MRD: Showing NP-Card for lyratol d (NP0243146)

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Record Information

Version

2.0

Created at

2022-09-07 03:37:56 UTC

Updated at

2022-09-07 03:37:56 UTC

NP-MRD ID

NP0243146

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lyratol d

Description

Lyratol D belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively. Lyratol D is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. lyratol d is found in Solanum lyratum. lyratol d was first documented in 2009 (PMID: 19336938). Based on a literature review a small amount of articles have been published on lyratol D (PMID: 26281590) (PMID: 28123569).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    1.1180    2.3144    0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090    1.0388    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851    1.1453    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507    0.0339   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406    0.1455   -0.2873 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074   -1.1654   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -1.2708    0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987   -2.5908   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1447   -0.1615    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821   -0.3339    0.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128   -0.0412   -0.5638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3110    1.3308   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441    1.1303   -1.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718    1.7500   -2.9793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    0.1137   -1.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526   -0.2565   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1607    0.6881    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722   -1.6984    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310    2.9121   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2212    2.1802    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    2.9591    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6969    2.1159    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9939    0.0689    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097   -2.0387   -0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493   -2.9334    0.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0407   -3.3705   -0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.5479   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -1.3773    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5810    0.3137    1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -0.7074   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    2.1145   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4358    1.5659   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8082    0.1102    1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8382    1.4852    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179    1.2016    1.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8981   -2.0484   -0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1837   -2.3321   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -1.8442    1.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9  2  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv1652309072205372D          

 18 19  0  0  1  0            999 V2000
    1.0344   -3.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -3.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1479   -3.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610   -3.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3195   -2.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7064   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -1.7224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -1.7224    0.0000 O   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
    1.7384   -0.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -0.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243146

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(C)=C1C[C@@H]1CC(=O)OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-12(16)6-10(2)13(9)7-11-8-14(17)18-15(11,3)4/h5-6,11,16H,7-8H2,1-4H3/t11-/m1/s1

> <INCHI_KEY>
JEUPLAJVBQWXMD-LLVKDONJSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.525297343530376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(4-hydroxy-2,6-dimethylphenyl)methyl]-5,5-dimethyloxolan-2-one

> <JCHEM_LOGP>
3.513325919666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.74917795413664

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958847282154005

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
70.596

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(4-hydroxy-2,6-dimethylphenyl)methyl]-5,5-dimethyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.931  -5.752   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.466  -5.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.678  -6.307   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.143  -5.831   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.287  -6.861   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.463  -4.324   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.319  -3.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.639  -1.788   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.146  -3.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.291  -2.739   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.755  -3.215   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.231  -4.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.771  -4.680   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.676  -5.926   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.247  -3.215   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.245  -0.968   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.757  -0.968   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
(4R)-4-(4-Hydroxy-2,6-dimethylbenzyl)-5,5-dimethyldihydrofuran-2(3H)-one	ChEBI

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(4R)-4-[(4-hydroxy-2,6-dimethylphenyl)methyl]-5,5-dimethyloxolan-2-one

Traditional Name

(4R)-4-[(4-hydroxy-2,6-dimethylphenyl)methyl]-5,5-dimethyloxolan-2-one

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(C)=C1C[C@@H]1CC(=O)OC1(C)C

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-12(16)6-10(2)13(9)7-11-8-14(17)18-15(11,3)4/h5-6,11,16H,7-8H2,1-4H3/t11-/m1/s1

InChI Key

JEUPLAJVBQWXMD-LLVKDONJSA-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
Solanum lyratum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-xylene
Xylene
M-cresol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:66608 )
butan-4-olide (CHEBI:66608 )
sesquiterpene lactone (CHEBI:66608 )

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	3.51	ChemAxon
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.6 m³·mol⁻¹	ChemAxon
Polarizability	27.53 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

Not Available

Chemspider ID

28286226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42604343

PDB ID

Not Available

ChEBI ID

66608

Good Scents ID

Not Available

References

General References

Ren Y, Shen L, Zhang DW, Dai SJ: Two new sesquiterpenoids from Solanum lyratum with cytotoxic activities. Chem Pharm Bull (Tokyo). 2009 Apr;57(4):408-10. doi: 10.1248/cpb.57.408. [PubMed:19336938 ]
Nie XP, Zhang L, Yao F, Xiao K, Dai SJ: [Studies on sesquiterpenes from Solanum septemlobum]. Zhongguo Zhong Yao Za Zhi. 2015 Apr;40(8):1514-7. [PubMed:26281590 ]
Chen M, Wu J, Zhang XX, Wang Q, Yan SH, Wang HD, Liu SL, Zou X: Anticancer activity of sesquiterpenoids extracted from Solanum lyratum via the induction of mitochondria-mediated apoptosis. Oncol Lett. 2017 Jan;13(1):370-376. doi: 10.3892/ol.2016.5404. Epub 2016 Nov 21. [PubMed:28123569 ]
LOTUS database [Link]

Showing NP-Card for lyratol d (NP0243146)

MOL for NP0243146 (lyratol d)

3D MOL for NP0243146 (lyratol d)

3D SDF for NP0243146 (lyratol d)

3D-SDF for NP0243146 (lyratol d)

PDB for NP0243146 (lyratol d)

3D PDB for NP0243146 (lyratol d)

SMILES for NP0243146 (lyratol d)

INCHI for NP0243146 (lyratol d)

Structure for NP0243146 (lyratol d)

3D Structure for NP0243146 (lyratol d)