NP-MRD: Showing NP-Card for roccellic acid (NP0198767)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 17:16:32 UTC

Updated at

2022-09-04 17:16:32 UTC

NP-MRD ID

NP0198767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

roccellic acid

Description

Roccellic acid, also known as roccellate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. roccellic acid is found in Roccella phycopsis and Roccellina hypomecha. roccellic acid was first documented in 2003 (PMID: 14613171). Based on a literature review a small amount of articles have been published on Roccellic acid (PMID: 25130294) (PMID: 22936837).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 52  0  0  0  0  0  0  0  0999 V2000
    5.1635   -1.7912   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6226   -0.6303   -1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5934    0.4816   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    1.0316   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    2.1353   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886    1.6622   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3397    0.5559   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975    1.0393    1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -0.0069    2.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572   -0.4873    1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459    0.5951    1.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441    0.1787    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.4154   -0.5975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5223   -1.6729   -0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6950   -1.7964   -1.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6891   -2.7532    0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -0.7569   -0.9764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7717   -1.3735   -2.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6693    0.3320   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1898    0.7821   -1.9654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1022    0.9677    0.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767   -1.8823   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5129   -2.7501   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5950   -1.7733    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5639   -0.2171   -0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901   -0.9748   -2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9637    1.2601   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6904    0.0184   -1.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096    0.2582    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827    1.4493    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.6005    0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807    2.9892   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    2.5004   -0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    1.3029   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251    0.1862   -0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256   -0.2984   -0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    1.3423    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    1.9461    1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    0.2622    3.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -0.9161    2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804   -0.9601    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.1992    2.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351    1.4606    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751    1.0866    2.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838    1.1061    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7667   -0.4722    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572    0.3660   -1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1391   -2.5858    0.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0289   -1.5473   -0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6713   -1.0271   -2.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984   -1.1010   -2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741   -2.4851   -2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1719    1.9775    0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 21  1  0
 19 20  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  6
 17 49  1  1
 18 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
 16 48  1  0
M  END


  Mrv1652309042219162D          

 21 20  0  0  1  0            999 V2000
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.5697    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2842    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC[C@H]([C@H](C)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-15(17(20)21)14(2)16(18)19/h14-15H,3-13H2,1-2H3,(H,18,19)(H,20,21)/t14-,15+/m0/s1

> <INCHI_KEY>
CADNMISJDLVPCK-LSDHHAIUSA-N

> <FORMULA>
C17H32O4

> <MOLECULAR_WEIGHT>
300.439

> <EXACT_MASS>
300.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.67692932102014

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-2-dodecyl-3-methylbutanedioic acid

> <JCHEM_LOGP>
5.577744904333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.956922846149493

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.442310942096954

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
83.29699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-2-dodecyl-3-methylbutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      11.193   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.197   6.462   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      28.530   5.692   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      25.863   5.692   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      28.530   8.772   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.530  10.312   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.198   8.772   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      29.864   6.462   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   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
Roccellate	Generator

Chemical Formula

C₁₇H₃₂O₄

Average Mass

300.4390 Da

Monoisotopic Mass

300.23006 Da

IUPAC Name

(2R,3S)-2-dodecyl-3-methylbutanedioic acid

Traditional Name

(2R,3S)-2-dodecyl-3-methylbutanedioic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC[C@H]([C@H](C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C17H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-15(17(20)21)14(2)16(18)19/h14-15H,3-13H2,1-2H3,(H,18,19)(H,20,21)/t14-,15+/m0/s1

InChI Key

CADNMISJDLVPCK-LSDHHAIUSA-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
Roccella phycopsis	LOTUS Database	35616633
Roccellina hypomecha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.58	ChemAxon
pKa (Strongest Acidic)	4.44	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	83.3 m³·mol⁻¹	ChemAxon
Polarizability	36.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

9624298

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11449446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Parrot D, Peresse T, Hitti E, Carrie D, Grube M, Tomasi S: Qualitative and spatial metabolite profiling of lichens by a LC-MS approach combined with optimised extraction. Phytochem Anal. 2015 Jan-Feb;26(1):23-33. doi: 10.1002/pca.2532. Epub 2014 Aug 6. [PubMed:25130294 ]
Spribille T, Goffinet B, Klug B, Muggia L, Obermayer W, Mayrhofer H: Molecular support for the recognition of the Mycoblastus fucatus group as the new genus Violella (Tephromelataceae, Lecanorales). Lichenologist (Lond). 2011 Sep;43(5):445-466. doi: 10.1017/S0024282911000478. [PubMed:22936837 ]
Brebion F, Delouvrie B, Najera F, Fensterbank L, Malacria M, Vaissermann J: Highly diastereoselective conjugate addition to alkylidene bis(sulfoxides): asymmetric synthesis of (+)-erythro-roccellic acid. Angew Chem Int Ed Engl. 2003 Nov 10;42(43):5342-5. doi: 10.1002/anie.200352356. [PubMed:14613171 ]
LOTUS database [Link]

Showing NP-Card for roccellic acid (NP0198767)

MOL for NP0198767 (roccellic acid)

3D MOL for NP0198767 (roccellic acid)

3D SDF for NP0198767 (roccellic acid)

3D-SDF for NP0198767 (roccellic acid)

PDB for NP0198767 (roccellic acid)

3D PDB for NP0198767 (roccellic acid)

SMILES for NP0198767 (roccellic acid)

INCHI for NP0198767 (roccellic acid)

Structure for NP0198767 (roccellic acid)

3D Structure for NP0198767 (roccellic acid)