NP-MRD: Showing NP-Card for methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate (NP0230480)

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Record Information

Version

2.0

Created at

2022-09-06 10:56:24 UTC

Updated at

2022-09-06 10:56:24 UTC

NP-MRD ID

NP0230480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate

Description

Methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate 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. methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate is found in Helianthus tuberosus. Methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261501122D          

 27 27  0  0  0  0            999 V2000
   -2.1434   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    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
   -0.7145    7.0125    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END


  Mrv1533004261501122D          

 27 27  0  0  0  0            999 V2000
   -2.1434   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    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
   -0.7145    7.0125    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0230480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC=CCC#CC#CC(OC1OC(CO)C(O)C(O)C1O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O8/c1-3-13(10-8-6-4-5-7-9-11-15(21)25-2)26-19-18(24)17(23)16(22)14(12-20)27-19/h3,7,9,13-14,16-20,22-24H,1,5,11-12H2,2H3

> <INCHI_KEY>
MBJLYSAPIVPYNP-UHFFFAOYSA-N

> <FORMULA>
C19H24O8

> <MOLECULAR_WEIGHT>
380.393

> <EXACT_MASS>
380.147117733

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.76873555592008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.2819666073333328

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.1992706633098

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20844866836316

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810842538717566

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
97.10700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  19.250   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  17.710   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  16.940   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  17.710   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
Methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoic acid	Generator

Chemical Formula

C₁₉H₂₄O₈

Average Mass

380.3930 Da

Monoisotopic Mass

380.14712 Da

IUPAC Name

methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate

Traditional Name

methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC=CCC#CC#CC(OC1OC(CO)C(O)C(O)C1O)C=C

InChI Identifier

InChI=1S/C19H24O8/c1-3-13(10-8-6-4-5-7-9-11-15(21)25-2)26-19-18(24)17(23)16(22)14(12-20)27-19/h3,7,9,13-14,16-20,22-24H,1,5,11-12H2,2H3

InChI Key

MBJLYSAPIVPYNP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus tuberosus	LOTUS Database	35616633

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
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Sugar acid
Fatty acid methyl ester
Oxane
Monosaccharide
Methyl ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen 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	0.97	ALOGPS
logP	0.28	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	97.11 m³·mol⁻¹	ChemAxon
Polarizability	39.77 Å³	ChemAxon
Number of Rings	1	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate (NP0230480)

MOL for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

3D MOL for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

3D SDF for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

3D-SDF for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

PDB for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

3D PDB for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

SMILES for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

INCHI for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

Structure for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)

3D Structure for NP0230480 (methyl 10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}dodeca-3,11-dien-6,8-diynoate)