NP-MRD: Showing NP-Card for 5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid (NP0155121)

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Record Information

Version

2.0

Created at

2022-09-02 12:07:42 UTC

Updated at

2022-09-02 12:07:42 UTC

NP-MRD ID

NP0155121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid

Description

5-Ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid is found in Senecio angulatus. 5-Ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -1.4122   -1.0920   -1.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -0.1575   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5884    0.0302   -1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -0.2118   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -1.2287   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4329   -1.5392    0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7023    0.6581    0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756    1.6501    1.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    0.4353    1.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145    0.4750   -0.2622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7672    1.9827   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1256    0.2847   -0.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.1130    1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -0.2104    1.9126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346   -0.6004    1.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -1.2899   -1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466   -1.5869   -2.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0027   -0.4587   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    1.1472   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3676   -1.8306   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9616   -1.7859    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434   -0.7761    0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9803   -2.4694    0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0189    1.1502    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6487    2.3261    0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    2.3736   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6941    2.4739   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8147    0.4461   -0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9453   -0.0828    1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 15  1  0
 13 14  2  0
  4  7  1  0
  7  9  1  0
  7  8  2  0
  6 21  1  0
  6 22  1  0
  6 23  1  0
  5 20  1  0
  3 18  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
  9 24  1  0
M  END


  Mrv1533004201503122D          

 15 14  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(CC(=C)C(C)(O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O5/c1-4-7(8(11)12)5-6(2)10(3,15)9(13)14/h4,15H,2,5H2,1,3H3,(H,11,12)(H,13,14)

> <INCHI_KEY>
AKOXKNVOTFFDSM-UHFFFAOYSA-N

> <FORMULA>
C10H14O5

> <MOLECULAR_WEIGHT>
214.217

> <EXACT_MASS>
214.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.48874350572563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
0.9855777173333331

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.598969993871022

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6728175987373968

> <JCHEM_PKA_STRONGEST_BASIC>
-4.08957788442055

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
53.168000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104  -3.231   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.564  -4.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.540  -5.335   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.770  -6.668   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.080  -5.335   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
5-Ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioate	Generator

Chemical Formula

C₁₀H₁₄O₅

Average Mass

214.2170 Da

Monoisotopic Mass

214.08412 Da

IUPAC Name

5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid

Traditional Name

5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid

CAS Registry Number

Not Available

SMILES

CC=C(CC(=C)C(C)(O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H14O5/c1-4-7(8(11)12)5-6(2)10(3,15)9(13)14/h4,15H,2,5H2,1,3H3,(H,11,12)(H,13,14)

InChI Key

AKOXKNVOTFFDSM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Senecio angulatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
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	0.75	ALOGPS
logP	0.99	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.17 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	0	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

73845285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid (NP0155121)

MOL for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

3D MOL for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

3D SDF for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

3D-SDF for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

PDB for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

3D PDB for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

SMILES for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

INCHI for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

Structure for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)

3D Structure for NP0155121 (5-ethylidene-2-hydroxy-2-methyl-3-methylidenehexanedioic acid)