NP-MRD: Showing NP-Card for Acoric acid (NP0064582)

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Record Information

Version

2.0

Created at

2022-04-28 08:47:01 UTC

Updated at

2022-04-28 08:47:01 UTC

NP-MRD ID

NP0064582

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acoric acid

Description

Acoric acid, also known as felypressin or acate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Acoric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Acoric acid has been detected, but not quantified in, herbs and spices and root vegetables. Acoric acid is found in Acorus calamus . Acoric acid was first documented in 2006 (PMID: 17177590). This could make acoric acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -1.7102   -2.0249    1.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.4627    0.2606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7753   -2.6567   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426   -0.9517   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189   -1.5585   -1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939    0.1688   -0.3917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7665    1.5288   -0.3896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7820    1.6396    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702    2.6835   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6257    3.9381   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8417    3.9278   -0.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0431    5.1907   -0.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -0.1222    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    0.1134    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919   -0.8162   -0.3720 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3718   -2.0621    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434   -1.0389   -1.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -2.0682   -2.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356    0.1503   -1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -2.8732    1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3641   -1.3420    2.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6695   -2.4702    2.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591   -0.7750    0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -3.0091    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1228   -2.3161   -1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108   -3.4486   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2871    1.6928   -1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868    1.5887    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526    0.8339    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226    2.6452    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    2.7971   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6437    2.6965    0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647    5.4784   -0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4071    0.4532    1.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318   -1.2119    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189    1.1717    0.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -0.1388    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232   -0.2518   -0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7549   -2.5872    0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662   -2.7570   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916   -1.8056    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557    0.0412   -2.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4919    1.0088   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  6  4  1  6
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  3 26  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  0
 16 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
M  END


  Mrv0541 01251306482D          

 19 19  0  0  0  0            999 V2000
   -2.6714   -6.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -6.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -7.5232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6714   -7.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -7.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -6.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -7.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -6.2857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5280   -6.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865   -6.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -6.6982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865   -5.4607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -5.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3736   -7.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -7.0680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871   -8.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037   -8.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840   -8.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -6.6982    0.0000 C   0  0  1  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 19  1  0  0  0  0
  1 19  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  1  0  0  0
 19  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
 10 12  2  0  0  0  0
  8 13  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 14  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064582

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)[C@]1(CC[C@@H](C)C(=O)C1)[C@@H](C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-9(2)14(19)15(11(4)7-13(17)18)6-5-10(3)12(16)8-15/h9-11H,5-8H2,1-4H3,(H,17,18)/t10-,11+,15+/m1/s1

> <INCHI_KEY>
ZIOCYJNRYIRTQD-ZETOZRRWSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.3487

> <EXACT_MASS>
268.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.33041952794271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-[(1S,4R)-4-methyl-1-(2-methylpropanoyl)-3-oxocyclohexyl]butanoic acid

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
3.239001667666666

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.116071562842123

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.638611545875713

> <JCHEM_PKA_STRONGEST_BASIC>
-7.178499440082867

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
71.7313

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-[(1S,4R)-4-methyl-1-(2-methylpropanoyl)-3-oxocyclohexyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-13         0                                  
HETATM    1  C   UNK     0      -4.987 -11.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.320 -12.503   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.320 -14.043   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.987 -14.813   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.653 -14.043   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.654 -11.733   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.654 -14.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.319 -11.733   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.986 -12.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.348 -11.733   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.682 -12.503   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.348 -10.193   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.319 -10.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.564 -13.592   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.077 -13.194   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.963 -15.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.874 -16.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.450 -15.478   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.653 -12.503   0.000  0.00  0.00           C+0
CONECT    1    2   19                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4   19                                                       
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8   19    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8                                                            
CONECT   14   15   16   19                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5    1    8   14                                             
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Acate	Generator
Acic acid	Generator
2-(L-Phenylalanine)-8-L-lysinevasopressin	HMDB
2-L-Phenylalanine-8-L-lysine-vasopressin	HMDB
Felipresina	HMDB
Felipressina	HMDB
Felypressin	HMDB
Felypressine	HMDB
Felypressinum	HMDB
Octapressin	HMDB
Octopressin	HMDB
Phelypressin	HMDB
Phenylalanine lysine vasopressin	HMDB
PLV-2	HMDB
Vasopressin, phenylalanyl-lysyl	HMDB
(3S)-3-[(1S,4R)-4-Methyl-1-(2-methylpropanoyl)-3-oxocyclohexyl]butanoate	Generator
Acoric acid	MeSH

Chemical Formula

C₁₅H₂₄O₄

Average Mass

268.3487 Da

Monoisotopic Mass

268.16746 Da

IUPAC Name

(3S)-3-[(1S,4R)-4-methyl-1-(2-methylpropanoyl)-3-oxocyclohexyl]butanoic acid

Traditional Name

(3S)-3-[(1S,4R)-4-methyl-1-(2-methylpropanoyl)-3-oxocyclohexyl]butanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)[C@]1(CC[C@@H](C)C(=O)C1)[C@@H](C)CC(O)=O

InChI Identifier

InChI=1S/C15H24O4/c1-9(2)14(19)15(11(4)7-13(17)18)6-5-10(3)12(16)8-15/h9-11H,5-8H2,1-4H3,(H,17,18)/t10-,11+,15+/m1/s1

InChI Key

ZIOCYJNRYIRTQD-ZETOZRRWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acorus calamus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Carbocyclic fatty acid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Ketone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.5	ALOGPS
logP	3.24	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.73 m³·mol⁻¹	ChemAxon
Polarizability	29.33 Å³	ChemAxon
Number of Rings	1	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

HMDB0038165

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017395

KNApSAcK ID

C00021588

Chemspider ID

22370263

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15558301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cecanho R, De Luca LA Jr, Ranali J: Cardiovascular effects of felypressin. Anesth Prog. 2006 Winter;53(4):119-25. doi: 10.2344/0003-3006(2006)53[119:CEOF]2.0.CO;2. [PubMed:17177590 ]

Showing NP-Card for Acoric acid (NP0064582)

MOL for NP0064582 (Acoric acid)

3D MOL for NP0064582 (Acoric acid)

3D SDF for NP0064582 (Acoric acid)

3D-SDF for NP0064582 (Acoric acid)

PDB for NP0064582 (Acoric acid)

3D PDB for NP0064582 (Acoric acid)

SMILES for NP0064582 (Acoric acid)

INCHI for NP0064582 (Acoric acid)

Structure for NP0064582 (Acoric acid)

3D Structure for NP0064582 (Acoric acid)