NP-MRD: Showing NP-Card for (4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid (NP0239273)

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Record Information

Version

2.0

Created at

2022-09-06 22:50:17 UTC

Updated at

2022-09-06 22:50:17 UTC

NP-MRD ID

NP0239273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid

Description

Oleuropeic acid, also known as oleuropeate, 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. (4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid is found in Abies chensiensis, Eucalyptus cypellocarpa and Olea europaea. (4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid was first documented in 2017 (PMID: 29122531). Based on a literature review a small amount of articles have been published on Oleuropeic acid (PMID: 35420422) (PMID: 34201471) (PMID: 35496018) (PMID: 31509411).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7534    0.7195   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -0.3367    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -0.5547    1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -1.5365   -0.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854    0.2229    0.1227 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0536    0.7010   -1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5123    0.4834   -1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3213    0.1799   -0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -0.0219   -0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2531    0.0821   -1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6329   -0.3477    0.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658    0.0485    0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4704   -0.7576    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3369    1.7069   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133    0.6287   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7368    0.6227   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270   -0.6800    1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827    0.3414    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -1.4454    1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593   -1.7115   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347    1.0984    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098    1.8076   -1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    0.2207   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104    0.5867   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998    0.0979    1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052    1.0496    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -0.4424    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1096   -1.1588    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -1.6049    0.0851 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
  2  5  1  0
  5 13  1  0
 13 12  1  0
 12  8  1  0
  8  7  2  0
  7  6  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  6  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  1
 13 28  1  0
 13 29  1  0
 12 26  1  0
 12 27  1  0
  7 24  1  0
  6 22  1  0
  6 23  1  0
 11 25  1  0
M  END


  Mrv1652309072200502D          

 13 13  0  0  1  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   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
    0.0000    0.8250    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
  5  2  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1CCC(=CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O3/c1-10(2,13)8-5-3-7(4-6-8)9(11)12/h3,8,13H,4-6H2,1-2H3,(H,11,12)/t8-/m1/s1

> <INCHI_KEY>
BFYWJELXORKNFO-MRVPVSSYSA-N

> <FORMULA>
C10H16O3

> <MOLECULAR_WEIGHT>
184.235

> <EXACT_MASS>
184.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.073727505706746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid

> <JCHEM_LOGP>
1.3659901066666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.402251855488597

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.807589585591339

> <JCHEM_PKA_STRONGEST_BASIC>
-0.873256083467102

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
50.1791

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid

> <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       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12    5                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
Oleuropeate	Generator

Chemical Formula

C₁₀H₁₆O₃

Average Mass

184.2350 Da

Monoisotopic Mass

184.10994 Da

IUPAC Name

(4S)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid

Traditional Name

(4S)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1CCC(=CC1)C(O)=O

InChI Identifier

InChI=1S/C10H16O3/c1-10(2,13)8-5-3-7(4-6-8)9(11)12/h3,8,13H,4-6H2,1-2H3,(H,11,12)/t8-/m1/s1

InChI Key

BFYWJELXORKNFO-MRVPVSSYSA-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
Abies chensiensis	LOTUS Database	35616633
Eucalyptus cypellocarpa	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633

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
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.37	ChemAxon
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.18 m³·mol⁻¹	ChemAxon
Polarizability	20.07 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010848

Chemspider ID

163683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

188320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu W, Li M, Wang G, Ma H, Mu Y, Zheng D, Huang X, Li L: New Monoterpene Acid and Gallic Acid Glucose Esters with Anti-Inflammatory Activity from Blue Gum (Eucalyptus globulus) Leaves. J Agric Food Chem. 2022 Apr 27;70(16):4981-4994. doi: 10.1021/acs.jafc.2c00828. Epub 2022 Apr 14. [PubMed:35420422 ]
Okba MM, El-Shiekh RA, Abu-Elghait M, Sobeh M, Ashour RMS: HPLC-PDA-ESI-MS/MS Profiling and Anti-Biofilm Potential of Eucalyptussideroxylon Flowers. Antibiotics (Basel). 2021 Jun 23;10(7):761. doi: 10.3390/antibiotics10070761. [PubMed:34201471 ]
Mei RF, Shi YX, Duan WH, Ding H, Zhang XR, Cai L, Ding ZT: Biotransformation of alpha-terpineol by Alternaria alternata. RSC Adv. 2020 Feb 11;10(11):6491-6496. doi: 10.1039/c9ra08042b. eCollection 2020 Feb 7. [PubMed:35496018 ]
Li Y, Li D, An Q, Ma H, Mu Y, Qiao W, Zhang Z, Zhang J, Huang X, Li L: New Acylated Phenolic Glycosides with ROS-Scavenging Activity from Psidium guajava Leaves. J Agric Food Chem. 2019 Oct 9;67(40):11089-11098. doi: 10.1021/acs.jafc.9b04318. Epub 2019 Sep 25. [PubMed:31509411 ]
Okba MM, El Gedaily RA, Ashour RM: UPLC-PDA-ESI-qTOF-MS profiling and potent anti-HSV-II activity of Eucalyptus sideroxylon leaves. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Nov 15;1068-1069:335-342. doi: 10.1016/j.jchromb.2017.10.065. Epub 2017 Nov 2. [PubMed:29122531 ]
LOTUS database [Link]

Showing NP-Card for (4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid (NP0239273)

MOL for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

3D MOL for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

3D SDF for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

3D-SDF for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

PDB for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

3D PDB for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

SMILES for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

INCHI for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

Structure for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)

3D Structure for NP0239273 ((4s)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid)