NP-MRD: Showing NP-Card for (2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate (NP0243037)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 03:30:06 UTC

Updated at

2022-09-07 03:30:07 UTC

NP-MRD ID

NP0243037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

Description

3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoic acid (S)-2-hydroxy-3-acetoxypropyl ester belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. (2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate is found in Doris verrucosa. Based on a literature review very few articles have been published on 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoic acid (S)-2-hydroxy-3-acetoxypropyl ester.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072205302D          

 30 29  0  0  1  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4296    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1440    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1440    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8585    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5730    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2874    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0019    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7164    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0019    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END


  Mrv1652309072205302D          

 30 29  0  0  1  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4296    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1440    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1440    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8585    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5730    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2874    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0019    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7164    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0019    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C(=O)OC[C@@H](O)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O5/c1-19(2)10-7-11-20(3)12-8-13-21(4)14-9-15-22(5)16-25(28)30-18-24(27)17-29-23(6)26/h10,12,14,16,24,27H,7-9,11,13,15,17-18H2,1-6H3/b20-12+,21-14+,22-16+/t24-/m0/s1

> <INCHI_KEY>
YRLGSSSUMSWYFS-GEZSXCAASA-N

> <FORMULA>
C25H40O5

> <MOLECULAR_WEIGHT>
420.59

> <EXACT_MASS>
420.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.85709861181084

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(acetyloxy)-2-hydroxypropyl (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

> <JCHEM_LOGP>
5.642002229666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.630621113220439

> <JCHEM_PKA_STRONGEST_BASIC>
-3.397766325077379

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
124.83009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(acetyloxy)-2-hydroxypropyl (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

> <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       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.264   4.771   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.598   4.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.599   2.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.267   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.600   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.934   4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.934   2.461   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.268   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.602   4.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.935   4.771   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.269   4.001   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.269   2.461   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.603   4.771   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.936   4.001   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.270   4.771   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      33.604   4.001   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      34.937   4.771   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.604   2.461   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

View in JSmol

Synonyms

Value	Source
3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoate (S)-2-hydroxy-3-acetoxypropyl ester	Generator

Chemical Formula

C₂₅H₄₀O₅

Average Mass

420.5900 Da

Monoisotopic Mass

420.28757 Da

IUPAC Name

(2S)-3-(acetyloxy)-2-hydroxypropyl (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

Traditional Name

(2S)-3-(acetyloxy)-2-hydroxypropyl (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C(=O)OC[C@@H](O)COC(C)=O

InChI Identifier

InChI=1S/C25H40O5/c1-19(2)10-7-11-20(3)12-8-13-21(4)14-9-15-22(5)16-25(28)30-18-24(27)17-29-23(6)26/h10,12,14,16,24,27H,7-9,11,13,15,17-18H2,1-6H3/b20-12+,21-14+,22-16+/t24-/m0/s1

InChI Key

YRLGSSSUMSWYFS-GEZSXCAASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Doris verrucosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
1,3-acyl-sn-glycerol
Diradylglycerol
Diacylglycerol
Glycerolipid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	5.64	ChemAxon
pKa (Strongest Acidic)	13.63	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	124.83 m³·mol⁻¹	ChemAxon
Polarizability	50.86 Å³	ChemAxon
Number of Rings	0	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

10207178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21588864

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate (NP0243037)

MOL for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

3D MOL for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

3D SDF for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

3D-SDF for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

PDB for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

3D PDB for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

SMILES for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

INCHI for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

Structure for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)

3D Structure for NP0243037 ((2s)-3-(acetyloxy)-2-hydroxypropyl (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate)