NP-MRD: Showing NP-Card for (4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde (NP0226476)

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Record Information

Version

2.0

Created at

2022-09-06 05:31:31 UTC

Updated at

2022-09-06 05:31:31 UTC

NP-MRD ID

NP0226476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde

Description

Mioganal belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. (4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde is found in Zingiber mioga. (4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde was first documented in 2008 (PMID: 18838802). Based on a literature review very few articles have been published on Mioganal.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207312D          

 22 24  0  0  1  0            999 V2000
   -1.0559   -3.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -2.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522   -3.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660   -2.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -1.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   -1.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9834   -2.1136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4152   -1.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8080   -2.1362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1303   -1.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -1.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -1.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192   -1.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418   -0.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6329   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923   -2.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4929   -3.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130   -3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -2.8617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7690   -3.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443   -3.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5515   -2.8166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
  2 22  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@H]3CC=C(C=O)C(C=O)=C[C@@H]3CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-19(2)9-4-10-20(3)17-7-5-15(12-21)16(13-22)11-14(17)6-8-18(19)20/h5,11-14,17-18H,4,6-10H2,1-3H3/t14-,17-,18-,20+/m0/s1

> <INCHI_KEY>
KONNXEJVCJUNNK-PRIDNEQBSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.147865374468225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,6aS,11aS,11bR)-4,4,11b-trimethyl-1H,2H,3H,4H,4aH,5H,6H,6aH,11H,11aH,11bH-cyclohepta[a]naphthalene-8,9-dicarbaldehyde

> <JCHEM_LOGP>
3.827025154666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.960260645109208

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
91.08059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aS,11aS,11bR)-4,4,11b-trimethyl-1H,2H,3H,4aH,5H,6H,6aH,11H,11aH-cyclohepta[a]naphthalene-8,9-dicarbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.971  -5.702   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.510  -5.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.284  -6.739   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.243  -3.861   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.437  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.102  -2.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.836  -3.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.642  -2.633   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.375  -3.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.977  -2.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.460  -2.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.708  -3.058   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.063  -2.325   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.105  -0.786   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.781  -4.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.199  -5.198   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.387  -6.727   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.624  -5.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.108  -5.342   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.302  -6.654   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.763  -6.612   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.029  -5.258   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
14,17-Cyclolabda-12,14(17)-diene-15,16-dial	MeSH

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

(4aS,6aS,11aS,11bR)-4,4,11b-trimethyl-1H,2H,3H,4H,4aH,5H,6H,6aH,11H,11aH,11bH-cyclohepta[a]naphthalene-8,9-dicarbaldehyde

Traditional Name

(4aS,6aS,11aS,11bR)-4,4,11b-trimethyl-1H,2H,3H,4aH,5H,6H,6aH,11H,11aH-cyclohepta[a]naphthalene-8,9-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@H]3CC=C(C=O)C(C=O)=C[C@@H]3CC[C@@H]12

InChI Identifier

InChI=1S/C20H28O2/c1-19(2)9-4-10-20(3)17-7-5-15(12-21)16(13-22)11-14(17)6-8-18(19)20/h5,11-14,17-18H,4,6-10H2,1-3H3/t14-,17-,18-,20+/m0/s1

InChI Key

KONNXEJVCJUNNK-PRIDNEQBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zingiber mioga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxides

Sub Class

Not Available

Direct Parent

Organic oxides

Alternative Parents

Substituents

Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	3.83	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.08 m³·mol⁻¹	ChemAxon
Polarizability	35.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00056888

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

102479664

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abe M, Ozawa Y, Morimitsu Y, Kubota K: Mioganal, a novel pungent principle in myoga (Zingiber mioga Roscoe) and a quantitative evaluation of its pungency. Biosci Biotechnol Biochem. 2008 Oct;72(10):2681-6. doi: 10.1271/bbb.80347. Epub 2008 Oct 7. [PubMed:18838802 ]
LOTUS database [Link]

Showing NP-Card for (4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde (NP0226476)

MOL for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

3D MOL for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

3D SDF for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

3D-SDF for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

PDB for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

3D PDB for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

SMILES for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

INCHI for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

Structure for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)

3D Structure for NP0226476 ((4as,6as,11as,11br)-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,11h,11ah-cyclohepta[a]naphthalene-8,9-dicarbaldehyde)