NP-MRD: Showing NP-Card for Epilaccishellolic acid (NP0064700)

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Record Information

Version

2.0

Created at

2022-04-28 08:53:35 UTC

Updated at

2022-04-28 08:53:35 UTC

NP-MRD ID

NP0064700

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epilaccishellolic acid

Description

(1R,2R,5S,7R,10S)-10-hydroxy-6,6-dimethyltricyclo[5.3.1.0¹,⁵]Undec-8-ene-2,8-dicarboxylic 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. Epilaccishellolic acid is found in Laccifer lacca . Based on a literature review very few articles have been published on (1R,2R,5S,7R,10S)-10-hydroxy-6,6-dimethyltricyclo[5.3.1.0¹,⁵]Undec-8-ene-2,8-dicarboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282210532D          

 20 22  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  0  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  2  0  0  0  0  0  0  0  0  0
    1.2790   -1.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356    0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9949   -0.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813    0.8667    0.0000 O   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
    0.7528    1.6157    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
   -0.0993   -2.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -2.3484    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  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  3 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0064700

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@@]3([C@@H](CC[C@@H]13)C(O)=O)[C@@H](O)C=C2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-14(2)9-6-15(11(16)5-7(9)12(17)18)8(13(19)20)3-4-10(14)15/h5,8-11,16H,3-4,6H2,1-2H3,(H,17,18)(H,19,20)/t8-,9-,10-,11-,15-/m0/s1

> <INCHI_KEY>
WMYAHEAQRDFQCZ-DMZJWBPISA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.812837176253517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,7R,10S)-10-hydroxy-6,6-dimethyltricyclo[5.3.1.0^{1,5}]undec-8-ene-2,8-dicarboxylic acid

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.1536725953333338

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.72197773367986

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.026037296936541

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1439584776367813

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
70.4644

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7R,10S)-10-hydroxy-6,6-dimethyltricyclo[5.3.1.0^{1,5}]undec-8-ene-2,8-dicarboxylic 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  O   UNK     0       2.387  -3.466   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.413   0.148   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.457  -0.984   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.872   1.618   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.886   3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.405   3.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.999  -3.430   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.185  -4.415   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.208  -4.384   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5    8   11                                             
CONECT    5    4    1    6                                                  
CONECT    6    5    7   16   17                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6                                                            
CONECT   17    6                                                            
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S,7R,10S)-10-Hydroxy-6,6-dimethyltricyclo[5.3.1.0,]undec-8-ene-2,8-dicarboxylate	Generator

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

(1R,2R,5S,7R,10S)-10-hydroxy-6,6-dimethyltricyclo[5.3.1.0^{1,5}]undec-8-ene-2,8-dicarboxylic acid

Traditional Name

(1R,2R,5S,7R,10S)-10-hydroxy-6,6-dimethyltricyclo[5.3.1.0^{1,5}]undec-8-ene-2,8-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@@]3([C@@H](CC[C@@H]13)C(O)=O)[C@@H](O)C=C2C(O)=O

InChI Identifier

InChI=1S/C15H20O5/c1-14(2)9-6-15(11(16)5-7(9)12(17)18)8(13(19)20)3-4-10(14)15/h5,8-11,16H,3-4,6H2,1-2H3,(H,17,18)(H,19,20)/t8-,9-,10-,11-,15-/m0/s1

InChI Key

WMYAHEAQRDFQCZ-DMZJWBPISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laccifer lacca	-	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
Dicarboxylic acid or derivatives
Secondary alcohol
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	1.41	ALOGPS
logP	1.15	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.46 m³·mol⁻¹	ChemAxon
Polarizability	26.81 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

162858593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epilaccishellolic acid (NP0064700)

MOL for NP0064700 (Epilaccishellolic acid)

3D MOL for NP0064700 (Epilaccishellolic acid)

3D SDF for NP0064700 (Epilaccishellolic acid)

3D-SDF for NP0064700 (Epilaccishellolic acid)

PDB for NP0064700 (Epilaccishellolic acid)

3D PDB for NP0064700 (Epilaccishellolic acid)

SMILES for NP0064700 (Epilaccishellolic acid)

INCHI for NP0064700 (Epilaccishellolic acid)

Structure for NP0064700 (Epilaccishellolic acid)

3D Structure for NP0064700 (Epilaccishellolic acid)