NP-MRD: Showing NP-Card for 3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate (NP0260605)

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Record Information

Version

2.0

Created at

2022-09-08 02:49:28 UTC

Updated at

2022-09-08 02:49:28 UTC

NP-MRD ID

NP0260605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate

Description

3-Hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate is found in Edgeworthia chrysantha. 3-Hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
   -4.8800    1.5669    0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9732    0.4129    0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3984   -0.7305    0.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106    0.6792    1.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608    0.3724    0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.0611    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -1.2975    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1479   -2.3371   -0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0144   -1.6771    1.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -1.3800   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533   -0.0664   -0.2418 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2261   -0.1290   -0.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319    0.0636    0.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6065   -0.0072    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.2975    1.7123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2397    1.0785   -1.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507    1.1221   -0.8942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8429    0.9799   -2.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105    2.3882   -0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    2.5136    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0184    1.7234   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8564    1.3861    1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    1.0879    2.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807   -1.9799   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -2.5294   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -3.3022    0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -2.2144    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833   -2.2976    1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054   -0.7652    2.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -2.1650   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0968   -1.6132   -1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6770    0.1503    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0757    0.6250    1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8904   -1.0636    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8105    0.3955   -0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7160    2.0110   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560    1.0758   -2.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397    0.5218   -2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9566    1.9723   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352    0.4089   -2.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    2.6615    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  7  1  0
  7  8  1  0
  7  9  1  0
  7  6  1  0
  6  5  2  0
  5  4  2  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 17  1  0
 17 18  1  0
 17 19  1  1
 17 16  1  0
 16 11  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 11 32  1  1
 10 30  1  0
 10 31  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  4 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 16 36  1  0
 16 37  1  0
M  END


  Mrv1533004241508202D          

 19 19  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    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
   -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 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    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    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
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
  5 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(C)(C)C(=C=CC(C)=O)C(C)(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-10(16)6-7-13-14(3,4)8-12(19-11(2)17)9-15(13,5)18/h6,12,18H,8-9H2,1-5H3

> <INCHI_KEY>
OLSFSBZBHVQLQE-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.31605494294398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
1.217915866333333

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.546483576112934

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.040165441836493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2186309927615016

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
73.03529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16    5                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetic acid	Generator

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate

Traditional Name

3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(C)(C)C(=C=CC(C)=O)C(C)(O)C1

InChI Identifier

InChI=1S/C15H22O4/c1-10(16)6-7-13-14(3,4)8-12(19-11(2)17)9-15(13,5)18/h6,12,18H,8-9H2,1-5H3

InChI Key

OLSFSBZBHVQLQE-UHFFFAOYSA-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
Edgeworthia chrysantha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Megastigmane sesquiterpenoid
Sesquiterpenoid
Acryloyl-group
Cyclic alcohol
Enone
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.97	ALOGPS
logP	1.22	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.04 m³·mol⁻¹	ChemAxon
Polarizability	29.32 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

73194627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate (NP0260605)

MOL for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

3D MOL for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

3D SDF for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

3D-SDF for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

PDB for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

3D PDB for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

SMILES for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

INCHI for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

Structure for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)

3D Structure for NP0260605 (3-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-ylidene)cyclohexyl acetate)