NP-MRD: Showing NP-Card for Ipomeamaronolide (NP0049747)

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Record Information

Version

2.0

Created at

2022-03-17 21:17:29 UTC

Updated at

2022-03-17 21:17:30 UTC

NP-MRD ID

NP0049747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ipomeamaronolide

Description

Ipomeamaronolide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Ipomeamaronolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ipomeamaronolide has been detected, but not quantified in, potato and root vegetables. This could make ipomeamaronolide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312142D          

 19 20  0  0  0  0            999 V2000
   -5.3767    2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6623    1.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2893    1.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483    2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4484    0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688    2.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689    0.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478    2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5189    2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6623    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2333    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    1.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768    2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913    2.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8044    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2333    1.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0776    2.9169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6044    1.5444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913    1.6070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  2  0  0  0  0
 13  4  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  2  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)CC1(C)CCC(O1)C1=CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-10(2)8-11(16)9-15(3)6-4-13(19-15)12-5-7-18-14(12)17/h5,10,13H,4,6-9H2,1-3H3

> <INCHI_KEY>
WZUJTFLPWFXBST-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.792619543990142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[5-methyl-5-(4-methyl-2-oxopentyl)oxolan-2-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.5771748756666657

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.06624603530147

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.849742722506171

> <JCHEM_PKA_STRONGEST_BASIC>
-4.221206672787484

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
71.7616

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[5-methyl-5-(4-methyl-2-oxopentyl)oxolan-2-yl]-5H-furan-2-one

> <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     -10.037   4.800   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.703   2.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.273   2.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.210   5.276   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.837   1.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.742   5.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.369   1.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.369   4.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.702   4.800   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.703   4.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.035   4.030   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.517   3.143   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.890   3.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.850   3.913   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.368   4.030   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.035   2.490   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.012   5.445   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.995   2.883   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.224   3.000   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    6   13                                                       
CONECT    5    7   12                                                       
CONECT    6    4   15                                                       
CONECT    7    5   18                                                       
CONECT    8   10   11                                                       
CONECT    9   11   15                                                       
CONECT   10    1    2    8                                                  
CONECT   11    8    9   16                                                  
CONECT   12    5   13   14                                                  
CONECT   13    4   12   19                                                  
CONECT   14   12   17   18                                                  
CONECT   15    3    6    9   19                                             
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    7   14                                                       
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2,3,4,5-Tetrahydro-5-methyl-5-(4-methyl-2-oxopentyl)-[2,3'-bifuran]-2'(5'H)-one, 9ci	HMDB

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3328 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

3-[5-methyl-5-(4-methyl-2-oxopentyl)oxolan-2-yl]-2,5-dihydrofuran-2-one

Traditional Name

3-[5-methyl-5-(4-methyl-2-oxopentyl)oxolan-2-yl]-5H-furan-2-one

CAS Registry Number

92448-61-8

SMILES

CC(C)CC(=O)CC1(C)CCC(O1)C1=CCOC1=O

InChI Identifier

InChI=1S/C15H22O4/c1-10(2)8-11(16)9-15(3)6-4-13(19-15)12-5-7-18-14(12)17/h5,10,13H,4,6-9H2,1-3H3

InChI Key

WZUJTFLPWFXBST-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.03	ALOGPS
logP	2.58	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.76 m³·mol⁻¹	ChemAxon
Polarizability	28.79 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

HMDB0040905

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020741

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ipomeamaronolide (NP0049747)

MOL for NP0049747 (Ipomeamaronolide)

3D MOL for NP0049747 (Ipomeamaronolide)

3D SDF for NP0049747 (Ipomeamaronolide)

3D-SDF for NP0049747 (Ipomeamaronolide)

PDB for NP0049747 (Ipomeamaronolide)

3D PDB for NP0049747 (Ipomeamaronolide)

SMILES for NP0049747 (Ipomeamaronolide)

INCHI for NP0049747 (Ipomeamaronolide)

Structure for NP0049747 (Ipomeamaronolide)

3D Structure for NP0049747 (Ipomeamaronolide)