NP-MRD: Showing NP-Card for 1-(3-Methyl-2-butenoyl)-6-apiosylglucose (NP0049533)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-03-17 21:14:02 UTC

Updated at

2022-03-17 21:14:02 UTC

NP-MRD ID

NP0049533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3-Methyl-2-butenoyl)-6-apiosylglucose

Description

1-(3-Methyl-2-butenoyl)-6-apiosylglucose belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 1-(3-Methyl-2-butenoyl)-6-apiosylglucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1-(3-Methyl-2-butenoyl)-6-apiosylglucose has been detected, but not quantified in, coffee and coffee products. 1-(3-Methyl-2-butenoyl)-6-apiosylglucose is found in Coffea arabica. It was first documented in 2000 (PMID: 11413487). This could make 1-(3-methyl-2-butenoyl)-6-apiosylglucose a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311322D          

 27 28  0  0  0  0            999 V2000
   -3.1960   -9.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3521   -8.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -8.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316   -8.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3822   -7.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3889   -5.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -5.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2329   -6.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -7.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395   -3.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2094   -5.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383   -6.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -0.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -5.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -6.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16 13  1  0  0  0  0
 17  5  1  0  0  0  0
 18  9  2  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  1  0  0  0  0
 24  4  1  0  0  0  0
 24 15  1  0  0  0  0
 25  6  1  0  0  0  0
 25 15  1  0  0  0  0
 26  8  1  0  0  0  0
 26 14  1  0  0  0  0
 27  9  1  0  0  0  0
 27 14  1  0  0  0  0
M  END


  Mrv0541 05061311322D          

 27 28  0  0  0  0            999 V2000
   -3.1960   -9.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3521   -8.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -8.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316   -8.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3822   -7.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3889   -5.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -5.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2329   -6.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -7.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395   -3.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2094   -5.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383   -6.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -0.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -5.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -6.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16 13  1  0  0  0  0
 17  5  1  0  0  0  0
 18  9  2  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  1  0  0  0  0
 24  4  1  0  0  0  0
 24 15  1  0  0  0  0
 25  6  1  0  0  0  0
 25 15  1  0  0  0  0
 26  8  1  0  0  0  0
 26 14  1  0  0  0  0
 27  9  1  0  0  0  0
 27 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)OC1OC(COC2OCC(O)(CO)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O11/c1-7(2)3-9(18)27-14-12(21)11(20)10(19)8(26-14)4-24-15-13(22)16(23,5-17)6-25-15/h3,8,10-15,17,19-23H,4-6H2,1-2H3

> <INCHI_KEY>
MVLVZZLLWUAMRM-UHFFFAOYSA-N

> <FORMULA>
C16H26O11

> <MOLECULAR_WEIGHT>
394.371

> <EXACT_MASS>
394.147511674

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
38.137038288695145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
-1.80

> <JCHEM_LOGP>
-2.1482902610000005

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.308986060782718

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.700336546035096

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
86.34830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 3-methylbut-2-enoate

> <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      -5.966 -18.059   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.124 -16.491   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.687 -15.406   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.851  -7.448   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.832  -1.281   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.556  -3.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.592 -16.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.756  -8.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.313 -13.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.287  -8.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.193  -9.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.566 -11.185   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.035 -11.346   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.339  -1.601   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.845 -13.838   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -7.914  -7.126   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -9.724  -9.617   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -8.471 -12.431   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.512  -2.854   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.771  -1.281   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.477  -6.041   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.129 -10.100   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.408 -12.753   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    7    9                                                       
CONECT    4    8   24                                                       
CONECT    5   16   17                                                       
CONECT    6   16   25                                                       
CONECT    7    1    2    3                                                  
CONECT    8    4   10   26                                                  
CONECT    9    3   18   27                                                  
CONECT   10    8   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   14   21                                                  
CONECT   13   15   16   22                                                  
CONECT   14   12   26   27                                                  
CONECT   15   13   24   25                                                  
CONECT   16    5    6   13   23                                             
CONECT   17    5                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   16                                                            
CONECT   24    4   15                                                       
CONECT   25    6   15                                                       
CONECT   26    8   14                                                       
CONECT   27    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₆H₂₆O₁₁

Average Mass

394.3710 Da

Monoisotopic Mass

394.14751 Da

IUPAC Name

6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 3-methylbut-2-enoate

Traditional Name

6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 3-methylbut-2-enoate

CAS Registry Number

467242-32-6

SMILES

CC(C)=CC(=O)OC1OC(COC2OCC(O)(CO)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H26O11/c1-7(2)3-9(18)27-14-12(21)11(20)10(19)8(26-14)4-24-15-13(22)16(23,5-17)6-25-15/h3,8,10-15,17,19-23H,4-6H2,1-2H3

InChI Key

MVLVZZLLWUAMRM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	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 fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Oxane
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organooxygen compound
Alcohol
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	-1.8	ALOGPS
logP	-2.1	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.35 m³·mol⁻¹	ChemAxon
Polarizability	38.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039952

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019615

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

74029762

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]

Showing NP-Card for 1-(3-Methyl-2-butenoyl)-6-apiosylglucose (NP0049533)

MOL for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

3D MOL for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

3D SDF for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

3D-SDF for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

PDB for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

3D PDB for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

SMILES for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

INCHI for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

Structure for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)

3D Structure for NP0049533 (1-(3-Methyl-2-butenoyl)-6-apiosylglucose)