NP-MRD: Showing NP-Card for (1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate (NP0330807)

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Record Information

Version

2.0

Created at

2022-09-12 16:31:46 UTC

Updated at

2022-09-12 16:31:46 UTC

NP-MRD ID

NP0330807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate

Description

Clavigerin C belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate is found in Lepidolaena clavigera. Based on a literature review very few articles have been published on clavigerin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122218312D          

 21 23  0  0  1  0            999 V2000
   -2.1252   -0.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834    0.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252    0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0420   -0.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1620    0.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    0.9603    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8267    1.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0881    0.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7335   -0.2209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3143   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042    0.1305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7830   -0.4645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6713   -1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445   -1.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -2.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -2.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798   -3.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -2.2176    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C[C@]12[C@H]3C[C@@H]1C(C)=C[C@H]3O[C@@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-9(2)5-12(19)8-17-13-7-14(17)15(6-10(13)3)21-16(17)20-11(4)18/h6,9,13-16H,5,7-8H2,1-4H3/t13-,14+,15-,16+,17-/m1/s1

> <INCHI_KEY>
GXJSMKHKQRATHF-BPKGMFCQSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.375

> <EXACT_MASS>
292.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
59.73271253436102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,6R,8R,9R)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0^{3,9}]non-4-en-8-yl acetate

> <JCHEM_LOGP>
2.4927140246666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.044684132854833

> <JCHEM_PKA_STRONGEST_BASIC>
-4.375266294979144

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
78.2008

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,6R,8R,9R)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0^{3,9}]non-4-en-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.967  -0.556   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.582   0.118   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.474   1.654   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.306  -0.744   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.078  -0.070   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.302   1.496   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.867   1.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.410   2.190   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.227   0.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.764   0.742   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.236  -0.412   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.453  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.248   0.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.462  -0.867   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.253  -2.393   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.173  -2.975   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.390  -2.032   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.381  -4.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.807  -5.083   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.016  -6.609   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.024  -4.140   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   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    5   11   15                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₄

Average Mass

292.3750 Da

Monoisotopic Mass

292.16746 Da

IUPAC Name

(1R,3R,6R,8R,9R)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0^{3,9}]non-4-en-8-yl acetate

Traditional Name

(1R,3R,6R,8R,9R)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0^{3,9}]non-4-en-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C[C@]12[C@H]3C[C@@H]1C(C)=C[C@H]3O[C@@H]2OC(C)=O

InChI Identifier

InChI=1S/C17H24O4/c1-9(2)5-12(19)8-17-13-7-14(17)15(6-10(13)3)21-16(17)20-11(4)18/h6,9,13-16H,5,7-8H2,1-4H3/t13-,14+,15-,16+,17-/m1/s1

InChI Key

GXJSMKHKQRATHF-BPKGMFCQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lepidolaena clavigera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Oxepane
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.49	ChemAxon
pKa (Strongest Acidic)	17.04	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.2 m³·mol⁻¹	ChemAxon
Polarizability	59.73 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	Yes	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

101230815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate (NP0330807)

MOL for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

3D MOL for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

3D SDF for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

3D-SDF for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

PDB for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

3D PDB for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

SMILES for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

INCHI for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

Structure for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)

3D Structure for NP0330807 ((1r,3r,6r,8r,9r)-4-methyl-9-(4-methyl-2-oxopentyl)-7-oxatricyclo[4.3.0.0³,⁹]non-4-en-8-yl acetate)