NP-MRD: Showing NP-Card for Lettucenin A (NP0048583)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:45 UTC

Updated at

2022-03-17 20:58:45 UTC

NP-MRD ID

NP0048583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lettucenin A

Description

Lettucenin A belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Lettucenin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lettucenin A has been detected, but not quantified in, lettuces and romaine lettuces. Lettucenin A is found in Taraxacum officinale. This could make lettucenin a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309182D          

 18 20  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    0.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  3  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  2  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O3/c1-8-3-6-11-12(7-16)15(17)18-14(11)13-9(2)4-5-10(8)13/h3,6-7H,2,4-5H2,1H3

> <INCHI_KEY>
PATCUDSVUMFCMB-UHFFFAOYSA-N

> <FORMULA>
C15H12O3

> <MOLECULAR_WEIGHT>
240.254

> <EXACT_MASS>
240.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.478300149308158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-9-methylidene-2-oxo-2H,7H,8H,9H-azuleno[4,5-b]furan-3-carbaldehyde

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
1.205812489666667

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.202021137866186

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
70.71839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-9-methylidene-2-oxo-7H,8H-azuleno[4,5-b]furan-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.239   0.498   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    6    8                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    3   11                                                       
CONECT    7   12   16                                                       
CONECT    8    1    3   10                                                  
CONECT    9    2    4   13                                                  
CONECT   10    5    8   13                                                  
CONECT   11    6   12   14                                                  
CONECT   12    7   11   15                                                  
CONECT   13    9   10   14                                                  
CONECT   14   11   13   18                                                  
CONECT   15   12   17   18                                                  
CONECT   16    7                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₃

Average Mass

240.2540 Da

Monoisotopic Mass

240.07864 Da

IUPAC Name

6-methyl-9-methylidene-2-oxo-2H,7H,8H,9H-azuleno[4,5-b]furan-3-carbaldehyde

Traditional Name

6-methyl-9-methylidene-2-oxo-7H,8H-azuleno[4,5-b]furan-3-carbaldehyde

CAS Registry Number

97915-46-3

SMILES

CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1

InChI Identifier

InChI=1S/C15H12O3/c1-8-3-6-11-12(7-16)15(17)18-14(11)13-9(2)4-5-10(8)13/h3,6-7H,2,4-5H2,1H3

InChI Key

PATCUDSVUMFCMB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lactuca sativa	FooDB	KNAPSACK
Taraxacum officinale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Cycloheptafurans

Sub Class

Not Available

Direct Parent

Cycloheptafurans

Alternative Parents

Substituents

Cycloheptafuran
Aryl-aldehyde
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
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	2.6	ALOGPS
logP	1.21	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.72 m³·mol⁻¹	ChemAxon
Polarizability	25.48 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

HMDB0036738

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015675

KNApSAcK ID

C00020829

Chemspider ID

155799

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

178999

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lettucenin A (NP0048583)

MOL for NP0048583 (Lettucenin A)

3D MOL for NP0048583 (Lettucenin A)

3D SDF for NP0048583 (Lettucenin A)

3D-SDF for NP0048583 (Lettucenin A)

PDB for NP0048583 (Lettucenin A)

3D PDB for NP0048583 (Lettucenin A)

SMILES for NP0048583 (Lettucenin A)

INCHI for NP0048583 (Lettucenin A)

Structure for NP0048583 (Lettucenin A)

3D Structure for NP0048583 (Lettucenin A)