NP-MRD: Showing NP-Card for 3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one (NP0253789)

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Record Information

Version

2.0

Created at

2022-09-07 17:45:52 UTC

Updated at

2022-09-07 17:45:52 UTC

NP-MRD ID

NP0253789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one

Description

3,4-Dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one is found in Anthemis maritima. 3,4-Dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161516122D          

 19 19  0  0  0  0            999 V2000
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  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
    2.1434   -0.4125    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    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
  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
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253789

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)(O)C1CC(=O)C(=C)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-9(2)6-5-7-15(4,19)11-8-12(16)10(3)13(17)14(11)18/h6,11,13-14,17-19H,3,5,7-8H2,1-2,4H3

> <INCHI_KEY>
CBBNBHQRNCDHQF-UHFFFAOYSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.353

> <EXACT_MASS>
268.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.938838326367392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
1.0384578746666668

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.396939747559859

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.219779483546663

> <JCHEM_PKA_STRONGEST_BASIC>
-2.940147904465282

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
74.5864

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9   18                                                  
CONECT   18   17                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₄

Average Mass

268.3530 Da

Monoisotopic Mass

268.16746 Da

IUPAC Name

3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one

Traditional Name

3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)(O)C1CC(=O)C(=C)C(O)C1O

InChI Identifier

InChI=1S/C15H24O4/c1-9(2)6-5-7-15(4,19)11-8-12(16)10(3)13(17)14(11)18/h6,11,13-14,17-19H,3,5,7-8H2,1-2,4H3

InChI Key

CBBNBHQRNCDHQF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthemis maritima	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

Bisabolane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
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	0.83	ALOGPS
logP	1.04	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.59 m³·mol⁻¹	ChemAxon
Polarizability	29.94 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one (NP0253789)

MOL for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

3D MOL for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

3D SDF for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

3D-SDF for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

PDB for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

3D PDB for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

SMILES for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

INCHI for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

Structure for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)

3D Structure for NP0253789 (3,4-dihydroxy-5-(2-hydroxy-6-methylhept-5-en-2-yl)-2-methylidenecyclohexan-1-one)