NP-MRD: Showing NP-Card for (Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid (NP0331999)

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Record Information

Version

1.0

Created at

2023-10-17 16:25:38 UTC

Updated at

2024-05-14 21:46:44 UTC

NP-MRD ID

NP0331999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid

Description

Based on a literature review very few articles have been published on 2-[(1Z,2R,4R)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]acetic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10172316252D          

 15 15  0  0  1  0            999 V2000
    1.2448    1.8695    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
    0.1842    1.8695    0.0000 C   0  0  0  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
    2.2414    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.7752    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
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
  4 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@@H](O)C[C@](C)(O)\C1=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O4/c1-10(2)5-7(12)6-11(3,15)8(10)4-9(13)14/h4,7,12,15H,5-6H2,1-3H3,(H,13,14)/b8-4-/t7-,11+/m1/s1

> <INCHI_KEY>
ANZXXHVFAVKPRW-RBZOFNCISA-N

> <FORMULA>
C11H18O4

> <MOLECULAR_WEIGHT>
214.261

> <EXACT_MASS>
214.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.224414341885712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1Z,2S,4R)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]acetic acid

> <JCHEM_LOGP>
0.2102429360000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.286769162597489

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.525567434781104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7421612762953673

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
56.051

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1Z,2S,4R)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-23         0                                  
HETATM    1  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.184   0.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.194  -1.447   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   11                                             
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
2-[(1Z,2R,4R)-2,4-Dihydroxy-2,6,6-trimethylcyclohexylidene]acetate	Generator

Chemical Formula

C₁₁H₁₈O₄

Average Mass

214.2610 Da

Monoisotopic Mass

214.12051 Da

IUPAC Name

2-[(1Z,2S,4R)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]acetic acid

Traditional Name

[(1Z,2S,4R)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]acetic acid

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@@H](O)C[C@](C)(O)\C1=C/C(O)=O

InChI Identifier

InChI=1S/C11H18O4/c1-10(2)5-7(12)6-11(3,15)8(10)4-9(13)14/h4,7,12,15H,5-6H2,1-3H3,(H,13,14)/b8-4-/t7-,11+/m1/s1

InChI Key

ANZXXHVFAVKPRW-RBZOFNCISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, C3D6O, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, C3D6O, simulated)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
erecta		Not Available

Chemical Taxonomy

Classification

Not classified

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	0.21	ChemAxon
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-2.7	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	1	ChemAxon
Refractivity	56.05 m³·mol⁻¹	ChemAxon
Polarizability	22.22 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

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

164621376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang X, Liu X, Wang X, Wang H, Zhang LH, Yu H, Yang W, Wu HH: Carotenoid-derived norsesquiterpenoids and sesquiterpenoids from Tagetes erecta L. Phytochemistry. 2023 Nov;215:113860. doi: 10.1016/j.phytochem.2023.113860. Epub 2023 Sep 14. [PubMed:37714249 ]

Showing NP-Card for (Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid (NP0331999)

MOL for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

3D MOL for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

3D SDF for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

3D-SDF for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

PDB for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

3D PDB for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

SMILES for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

INCHI for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

Structure for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)

3D Structure for NP0331999 ((Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene) acetic acid)