MiMeDB: Showing metabocard for Fujenal (MMDBc0010951)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:58:04 UTC

Update Date

2022-08-31 06:32:31 UTC

Metabolite ID

MMDBc0010951

Metabolite Identification

Common Name

Fujenal

Description

(1R,2S)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-octahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carbaldehyde belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review very few articles have been published on (1R,2S)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-octahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carbaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104582D          

 27 30  0  0  1  0            999 V2000
    1.4413   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238   -3.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0069   -4.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029   -2.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -1.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9919   -1.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -2.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656   -3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -2.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -1.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461   -3.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -2.5762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4111   -4.0033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0058   -4.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -4.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1484   -3.2212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2197   -4.1668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8297   -2.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8577   -3.8073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -4.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -5.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461   -0.1017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -2.4839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -3.9252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 12  1  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 16 15  1  0  0  0  0
 18  2  1  1  0  0  0
 18  7  1  1  0  0  0
 14 18  1  1  0  0  0
 18 15  1  0  0  0  0
 19  3  1  6  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  1  0  0  0
 20 14  1  0  0  0  0
 21 11  2  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 13  1  0  0  0  0
 14 26  1  6  0  0  0
 15 27  1  6  0  0  0
M  END


  Mrv1652305152104582D          

 27 30  0  0  1  0            999 V2000
    1.4413   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238   -3.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0069   -4.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029   -2.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -1.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9919   -1.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -2.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656   -3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -2.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -1.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461   -3.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -2.5762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4111   -4.0033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0058   -4.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -4.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1484   -3.2212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2197   -4.1668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8297   -2.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8577   -3.8073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -4.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -5.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461   -0.1017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -2.4839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -3.9252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 12  1  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 16 15  1  0  0  0  0
 18  2  1  1  0  0  0
 18  7  1  1  0  0  0
 14 18  1  1  0  0  0
 18 15  1  0  0  0  0
 19  3  1  6  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  1  0  0  0
 20 14  1  0  0  0  0
 21 11  2  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 13  1  0  0  0  0
 14 26  1  6  0  0  0
 15 27  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0010951

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C12C[C@](CC1=C)(C=O)[C@@]([H])(CC2)[C@]1(C)CCC[C@@]2(C)C(=O)OC(=O)[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-12-9-20(11-21)10-13(12)5-6-14(20)18(2)7-4-8-19(3)15(18)16(22)24-17(19)23/h11,13-15H,1,4-10H2,2-3H3/t13?,14-,15-,18-,19+,20+/m0/s1

> <INCHI_KEY>
YHGCNVZMSCSGOF-FVGLYSEPSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.19600559503598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-octahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carbaldehyde

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.374530441000001

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.781354629492333

> <JCHEM_POLAR_SURFACE_AREA>
60.44

> <JCHEM_REFRACTIVITY>
88.44349999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-tetrahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       2.691  -1.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.391  -6.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.213  -8.239   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.272  -5.163   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.783  -2.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.452  -3.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.763  -4.858   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.763  -6.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.078  -4.191   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.849  -3.421   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.939  -6.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.078  -2.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.282  -1.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.783  -4.809   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.234  -7.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.477  -8.814   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.920  -9.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.744  -6.013   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.744  -7.778   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.282  -5.152   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.468  -7.107   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.948  -8.990   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.261 -10.064   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.519  -9.948   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.939  -0.190   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       8.314  -4.637   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.701  -7.327   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    7    8                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7    4   18                                                       
CONECT    8    4   19                                                       
CONECT    9   12   20                                                       
CONECT   10   13   20                                                       
CONECT   11   20   21                                                       
CONECT   12    1    9   13                                                  
CONECT   13    5   10   12   25                                             
CONECT   14    6   18   20   26                                             
CONECT   15   16   18   19   27                                             
CONECT   16   15   22   24                                                  
CONECT   17   19   23   24                                                  
CONECT   18    2    7   14   15                                             
CONECT   19    3    8   15   17                                             
CONECT   20    9   10   11   14                                             
CONECT   21   11                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   16   17                                                       
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₂₆O₄

Average Mass

330.424

Monoisotopic Mass

330.183109317

IUPAC Name

(1R,2S)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-octahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carbaldehyde

Traditional Name

(1R,2S)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-tetrahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H]C12C[C@](CC1=C)(C=O)[C@@]([H])(CC2)[C@]1(C)CCC[C@@]2(C)C(=O)OC(=O)[C@@]12[H]

InChI Identifier

InChI=1S/C20H26O4/c1-12-9-20(11-21)10-13(12)5-6-14(20)18(2)7-4-8-19(3)15(18)16(22)24-17(19)23/h11,13-15H,1,4-10H2,2-3H3/t13?,14-,15-,18-,19+,20+/m0/s1

InChI Key

YHGCNVZMSCSGOF-FVGLYSEPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Isobenzofuran
Dicarboxylic acid or derivatives
Carboxylic acid anhydride
Tetrahydrofuran
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.37	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.44 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442414

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586009

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Fujenal (MMDBc0010951)

MOL for #<Metabolite:0x00007f46e464ff00>

3D MOL for #<Metabolite:0x00007f46e464ff00>

3D SDF for #<Metabolite:0x00007f46e464ff00>

3D-SDF for #<Metabolite:0x00007f46e464ff00>

PDB for #<Metabolite:0x00007f46e464ff00>

3D PDB for #<Metabolite:0x00007f46e464ff00>

SMILES for #<Metabolite:0x00007f46e464ff00>

INCHI for #<Metabolite:0x00007f46e464ff00>

Structure for #<Metabolite:0x00007f46e464ff00>

3D Structure for #<Metabolite:0x00007f46e464ff00>