NP-MRD: Showing NP-Card for methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate (NP0290299)

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Record Information

Version

2.0

Created at

2022-09-09 20:54:57 UTC

Updated at

2022-09-09 20:54:57 UTC

NP-MRD ID

NP0290299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate

Description

Methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-decahydronaphthalen-2-yl)prop-2-enoate belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-decahydronaphthalen-2-yl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241501232D          

 21 22  0  0  0  0            999 V2000
   -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 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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    0.7145   -0.4125    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   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
    2.8579   -2.4750    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790   -2.8162    0.0000 O   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
    1.4289   -2.4750    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)C1CCC2(C)CCCC(=C)C2(OO)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O5/c1-10-6-5-8-15(3)9-7-12(11(2)14(18)20-4)13(17)16(10,15)21-19/h12-13,17,19H,1-2,5-9H2,3-4H3

> <INCHI_KEY>
FSMBSUGHWJTUSY-UHFFFAOYSA-N

> <FORMULA>
C16H24O5

> <MOLECULAR_WEIGHT>
296.363

> <EXACT_MASS>
296.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.617004042784266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-decahydronaphthalen-2-yl)prop-2-enoate

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.597156245666666

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.934534816984122

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.676718630933072

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4519964230787137

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.87499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1H-naphthalen-2-yl)prop-2-enoate

> <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      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.627  -5.257   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18   20                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    7   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-decahydronaphthalen-2-yl)prop-2-enoic acid	Generator

Chemical Formula

C₁₆H₂₄O₅

Average Mass

296.3630 Da

Monoisotopic Mass

296.16237 Da

IUPAC Name

methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-decahydronaphthalen-2-yl)prop-2-enoate

Traditional Name

methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1H-naphthalen-2-yl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)C1CCC2(C)CCCC(=C)C2(OO)C1O

InChI Identifier

InChI=1S/C16H24O5/c1-10-6-5-8-15(3)9-7-12(11(2)14(18)20-4)13(17)16(10,15)21-19/h12-13,17,19H,1-2,5-9H2,3-4H3

InChI Key

FSMBSUGHWJTUSY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclic alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Hydroperoxide
Secondary alcohol
Peroxol
Monocarboxylic acid or derivatives
Alkyl hydroperoxide
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	2.08	ALOGPS
logP	2.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	31.62 Å³	ChemAxon
Number of Rings	2	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 methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate (NP0290299)

MOL for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

3D MOL for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

3D SDF for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

3D-SDF for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

PDB for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

3D PDB for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

SMILES for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

INCHI for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

Structure for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)

3D Structure for NP0290299 (methyl 2-(8a-hydroperoxy-1-hydroxy-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-yl)prop-2-enoate)