NP-MRD: Showing NP-Card for 3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one (NP0254780)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 19:03:05 UTC

Updated at

2022-09-07 19:03:05 UTC

NP-MRD ID

NP0254780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one

Description

3-(Docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one is found in Pinnigorgia flava. Based on a literature review very few articles have been published on 3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methyl-2,5-dihydrofuran-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072221032D          

 30 30  0  0  0  0            999 V2000
   10.5690   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2834   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9979   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7124   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4269   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1413   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8558   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5703   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2847   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9992   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7137   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4282   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4282   -5.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1426   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1426   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8571   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5716   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2860   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0005   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7150   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4295   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1439   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8584   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6121   -4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1641   -4.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7161   -4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8315   -5.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7516   -5.5380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9446   -5.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3315   -5.9185    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END


  Mrv1652309072221032D          

 30 30  0  0  0  0            999 V2000
   10.5690   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2834   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9979   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7124   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4269   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1413   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8558   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5703   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2847   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9992   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7137   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4282   -6.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4282   -5.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1426   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1426   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8571   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5716   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2860   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0005   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7150   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4295   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1439   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8584   -4.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6121   -4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1641   -4.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7161   -4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8315   -5.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7516   -5.5380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9446   -5.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3315   -5.9185    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0254780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC=CCC=CCC=CCCCCCC1=CC(C)(O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-25-24-27(2,29)30-26(25)28/h11-12,14-15,17-18,24,29H,3-10,13,16,19-23H2,1-2H3

> <INCHI_KEY>
JVTMISSEQVWUHD-UHFFFAOYSA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.646

> <EXACT_MASS>
416.329045277

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.61587666908247

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
9.066181857

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.720036982919414

> <JCHEM_PKA_STRONGEST_BASIC>
-4.233455823671048

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
131.627

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-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      19.729 -13.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.062 -12.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.396 -13.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.730 -12.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.063 -13.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.397 -12.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.731 -13.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.065 -12.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.398 -13.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.732 -12.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.066 -13.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.399 -12.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.399 -10.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.733 -10.026   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.733  -8.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.067  -7.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.400  -8.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.734  -7.716   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.068  -8.486   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      42.401  -7.716   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.735  -8.486   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.069  -7.716   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.402  -8.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      47.809  -7.859   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      48.840  -9.004   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      49.870  -7.859   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      50.086  -9.909   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      48.070 -10.338   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      46.563 -10.017   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      45.419 -11.048   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    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                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₃

Average Mass

416.6460 Da

Monoisotopic Mass

416.32905 Da

IUPAC Name

3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC=CCC=CCC=CCCCCCC1=CC(C)(O)OC1=O

InChI Identifier

InChI=1S/C27H44O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-25-24-27(2,29)30-26(25)28/h11-12,14-15,17-18,24,29H,3-10,13,16,19-23H2,1-2H3

InChI Key

JVTMISSEQVWUHD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pinnigorgia flava	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
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	9.07	ChemAxon
pKa (Strongest Acidic)	11.72	ChemAxon
pKa (Strongest Basic)	-4.2	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	18	ChemAxon
Refractivity	131.63 m³·mol⁻¹	ChemAxon
Polarizability	52.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

74051545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one (NP0254780)

MOL for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

3D MOL for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

3D SDF for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

3D-SDF for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

PDB for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

3D PDB for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

SMILES for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

INCHI for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

Structure for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)

3D Structure for NP0254780 (3-(docosa-6,9,12-trien-1-yl)-5-hydroxy-5-methylfuran-2-one)