NP-MRD: Showing NP-Card for Isocedrolic acid (NP0064693)

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Record Information

Version

2.0

Created at

2022-04-28 08:53:14 UTC

Updated at

2022-04-28 08:53:14 UTC

NP-MRD ID

NP0064693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isocedrolic acid

Description

(1S,2R,5S,7R,8R)-8-hydroxy-6,6,8-trimethyltricyclo[5.3.1.0¹,⁵]Undecane-2-carboxylic acid belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Isocedrolic acid is found in Juniperus formosana Hayata. and Juniperus squamata . Based on a literature review very few articles have been published on (1S,2R,5S,7R,8R)-8-hydroxy-6,6,8-trimethyltricyclo[5.3.1.0¹,⁵]Undecane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282210532D          

 18 20  0  0  1  0            999 V2000
   -0.2335    0.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -0.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3953   -1.0245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9913   -0.4196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5965    0.3517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2530    0.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0510    0.5657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5777    0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307   -0.1019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3971   -0.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601    0.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -0.3144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    1.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090   -2.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993   -2.3651    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  4  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  1  0  0  0
  9 13  1  6  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  3 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0064693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CC[C@@H](C(O)=O)[C@@]22C[C@H]1[C@](C)(O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-13(2)10-5-4-9(12(16)17)15(10)7-6-14(3,18)11(13)8-15/h9-11,18H,4-8H2,1-3H3,(H,16,17)/t9-,10-,11+,14+,15+/m0/s1

> <INCHI_KEY>
FRJSLEWOWKLZSF-ABNINFQISA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7R,8R)-8-hydroxy-6,6,8-trimethyltricyclo[5.3.1.0^{1,5}]undecane-2-carboxylic acid

> <JCHEM_LOGP>
2.127255859666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.700151061597917

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5155930684417177

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
68.21779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7R,8R)-8-hydroxy-6,6,8-trimethyltricyclo[5.3.1.0^{1,5}]undecane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.436   0.304   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.649  -1.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.738  -1.912   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.850  -0.783   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.114   0.657   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.339   1.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.829   1.056   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.945   0.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.911  -0.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.475  -1.750   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.910  -2.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.086   0.805   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.399  -0.587   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.405   3.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.886   3.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.999  -3.430   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.443  -3.963   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.185  -4.415   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    8   11                                             
CONECT    5    4    1    6                                                  
CONECT    6    5    7   14   15                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10   12   13                                             
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    6                                                            
CONECT   15    6                                                            
CONECT   16    3   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,7R,8R)-8-Hydroxy-6,6,8-trimethyltricyclo[5.3.1.0,]undecane-2-carboxylate	Generator

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3540 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

(1S,2R,5S,7R,8R)-8-hydroxy-6,6,8-trimethyltricyclo[5.3.1.0^{1,5}]undecane-2-carboxylic acid

Traditional Name

(1S,2R,5S,7R,8R)-8-hydroxy-6,6,8-trimethyltricyclo[5.3.1.0^{1,5}]undecane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2CC[C@@H](C(O)=O)[C@@]22C[C@H]1[C@](C)(O)CC2

InChI Identifier

InChI=1S/C15H24O3/c1-13(2)10-5-4-9(12(16)17)15(10)7-6-14(3,18)11(13)8-15/h9-11,18H,4-8H2,1-3H3,(H,16,17)/t9-,10-,11+,14+,15+/m0/s1

InChI Key

FRJSLEWOWKLZSF-ABNINFQISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Juniperus formosana Hayata.	Plant	KNApSAcK
Juniperus squamata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Cedrane and isocedrane sesquiterpenoids

Alternative Parents

Substituents

Cedrane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.13	ChemAxon
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.52	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	1	ChemAxon
Refractivity	68.22 m³·mol⁻¹	ChemAxon
Polarizability	0 Å³	ChemAxon
Number of Rings	3	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

162964540

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isocedrolic acid (NP0064693)

MOL for NP0064693 (Isocedrolic acid)

3D MOL for NP0064693 (Isocedrolic acid)

3D SDF for NP0064693 (Isocedrolic acid)

3D-SDF for NP0064693 (Isocedrolic acid)

PDB for NP0064693 (Isocedrolic acid)

3D PDB for NP0064693 (Isocedrolic acid)

SMILES for NP0064693 (Isocedrolic acid)

INCHI for NP0064693 (Isocedrolic acid)

Structure for NP0064693 (Isocedrolic acid)

3D Structure for NP0064693 (Isocedrolic acid)