NP-MRD: Showing NP-Card for 6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid (NP0330402)

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Record Information

Version

1.0

Created at

2022-09-12 15:43:25 UTC

Updated at

2022-09-12 15:43:26 UTC

NP-MRD ID

NP0330402

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid

Description

6-Hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. 6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid is found in Acacia concinna. 6-Hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171512502D          

 14 13  0  0  0  0            999 V2000
    1.9520    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    2.5559    0.0000 O   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
    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
   -1.2375   -0.7145    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
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    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
  2  4  1  0  0  0  0
  4  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
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0330402

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O4/c1-3-10(2,14)6-4-5-8(7-11)9(12)13/h3,5,11,14H,1,4,6-7H2,2H3,(H,12,13)

> <INCHI_KEY>
AFIOEQLZPSGSDD-UHFFFAOYSA-N

> <FORMULA>
C10H16O4

> <MOLECULAR_WEIGHT>
200.234

> <EXACT_MASS>
200.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.21668103406831

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.5584138949999997

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.23743072324309

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.636872941116815

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2856675692668298

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
53.69850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.644   3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   4.771   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.080   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   13                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoate	Generator

Chemical Formula

C₁₀H₁₆O₄

Average Mass

200.2340 Da

Monoisotopic Mass

200.10486 Da

IUPAC Name

6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid

Traditional Name

6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid

CAS Registry Number

Not Available

SMILES

CC(O)(CCC=C(CO)C(O)=O)C=C

InChI Identifier

InChI=1S/C10H16O4/c1-3-10(2,14)6-4-5-8(7-11)9(12)13/h3,5,11,14H,1,4,6-7H2,2H3,(H,12,13)

InChI Key

AFIOEQLZPSGSDD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acacia concinna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Hydroxy acid
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary alcohol
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	0.56	ALOGPS
logP	0.56	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	53.7 m³·mol⁻¹	ChemAxon
Polarizability	21.22 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

53639916

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid (NP0330402)

MOL for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

3D MOL for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

3D SDF for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

3D-SDF for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

PDB for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

3D PDB for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

SMILES for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

INCHI for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

Structure for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)

3D Structure for NP0330402 (6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid)