MiMeDB: Showing metabocard for Betaenone C (MMDBc0003396)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:27:04 UTC

Update Date

2022-08-31 06:20:51 UTC

Metabolite ID

MMDBc0003396

Metabolite Identification

Common Name

Betaenone C

Description

Betaenone C belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Based on a literature review a significant number of articles have been published on Betaenone C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142123272D          

 33 34  0  0  1  0            999 V2000
    4.2868   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    0.3627    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
    1.6771   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -3.6892    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0198   -3.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -2.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646   -3.2005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -4.4645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  2  0  0  0  0
 12  2  1  1  0  0  0
 12  7  1  0  0  0  0
 13  3  1  6  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  6  0  0  0
 18 14  1  0  0  0  0
 19  4  1  6  0  0  0
 19 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20  5  1  1  0  0  0
 20 15  1  6  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  6  1  6  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 15  2  0  0  0  0
 24 18  2  0  0  0  0
 19 25  1  1  0  0  0
 21 26  1  1  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 12 29  1  6  0  0  0
 13 30  1  1  0  0  0
 14 31  1  1  0  0  0
 16 32  1  6  0  0  0
 17 33  1  1  0  0  0
M  END


  Mrv1652305142123272D          

 33 34  0  0  1  0            999 V2000
    4.2868   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    0.3627    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
    1.6771   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -3.6892    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0198   -3.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -2.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646   -3.2005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -4.4645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  2  0  0  0  0
 12  2  1  1  0  0  0
 12  7  1  0  0  0  0
 13  3  1  6  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  6  0  0  0
 18 14  1  0  0  0  0
 19  4  1  6  0  0  0
 19 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20  5  1  1  0  0  0
 20 15  1  6  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  6  1  6  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 15  2  0  0  0  0
 24 18  2  0  0  0  0
 19 25  1  1  0  0  0
 21 26  1  1  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 12 29  1  6  0  0  0
 13 30  1  1  0  0  0
 14 31  1  1  0  0  0
 16 32  1  6  0  0  0
 17 33  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0003396

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h8-9,12-14,16-17,22,25-26H,7,10-11H2,1-6H3/b9-8-/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1

> <INCHI_KEY>
YRYPVWAJOMXOHH-ITBWMFDCSA-N

> <FORMULA>
C21H34O5

> <MOLECULAR_WEIGHT>
366.498

> <EXACT_MASS>
366.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.26072957131397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,4aS,5R,7R,8aS)-3-[(2R)-butan-2-yl]-2,7-dihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
3.301582396333334

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.012540553495345

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.984156952230563

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7876078507569906

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
100.97169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
betaenone C

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.850  -1.037   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.528   0.677   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.131  -5.707   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.120  -6.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.637  -6.619   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.765  -5.329   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.860   0.677   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.518  -1.037   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       1.614  -5.974   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.594  -8.334   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.668  -3.850   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6   21                                                            
CONECT    7    1   12                                                       
CONECT    8    9   15   27                                                  
CONECT    9    8   22   28                                                  
CONECT   10   13   19                                                       
CONECT   11   14   19                                                       
CONECT   12    2    7   17   29                                             
CONECT   13    3   10   16   30                                             
CONECT   14   11   16   18   31                                             
CONECT   15    8   20   23                                                  
CONECT   16   13   14   20   32                                             
CONECT   17   12   20   21   33                                             
CONECT   18   14   21   24                                                  
CONECT   19    4   10   11   25                                             
CONECT   20    5   15   16   17                                             
CONECT   21    6   17   18   26                                             
CONECT   22    9                                                            
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26   21                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Synonyms

Not Available

Molecular Formula

C₂₁H₃₄O₅

Average Mass

366.498

Monoisotopic Mass

366.240624195

IUPAC Name

(2S,3R,4R,4aS,5R,7R,8aS)-3-[(2R)-butan-2-yl]-2,7-dihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one

Traditional Name

betaenone C

CAS Registry Number

Not Available

SMILES

[H]\C(O)=C(/[H])C(=O)[C@@]1(C)[C@@]([H])([C@]([H])(C)CC)[C@](C)(O)C(=O)[C@@]2([H])C[C@](C)(O)C[C@@]([H])(C)[C@]12[H]

InChI Identifier

InChI=1S/C21H34O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h8-9,12-14,16-17,22,25-26H,7,10-11H2,1-6H3/b9-8-/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1

InChI Key

YRYPVWAJOMXOHH-ITBWMFDCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Vinylogous acid
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Cyclic alcohol
Acryloyl-group
Ketone
Enol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.29	ALOGPS
logP	3.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.97 m³·mol⁻¹	ChemAxon
Polarizability	40.26 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

Spectra

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0017144	dehydroprobetaenone I	Betaenone C	Cytochrome P450 monooxygenase bet2	Oxygenation	RHEA	34755880
MMDBr0017145	dehydroprobetaenone I	Betaenone C	Cytochrome P450 monooxygenase bet2	Oxygenation	RHEA	34755880
MMDBr0017148	Betaenone C	betaenone A	FAD-linked oxidoreductase orf1	Redox reaction	RHEA	34755880
MMDBr0017149	Betaenone C	betaenone A	FAD-linked oxidoreductase orf1	Redox reaction	RHEA	34755880
MMDBr0017269	Betaenone C	Water	Cytochrome P450 monooxygenase sthD	Oxygenation	RHEA	34755880
MMDBr0017270	Betaenone C	Water	Cytochrome P450 monooxygenase sthD	Oxygenation	RHEA	34755880
MMDBr0025764	Betaenone C	betaenone B	Short-chain dehydrogenase/reductase sthC	Dehydrogenation; Reduction	RHEA	34755880
MMDBr0025765	Betaenone C	betaenone B	Short-chain dehydrogenase/reductase sthC	Dehydrogenation; Reduction	RHEA	34755880

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	3		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

C00000530

Chemspider ID

10349243

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Betaenone C

METLIN ID

Not Available

PubChem Compound

23244602

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Betaenone C (MMDBc0003396)

MOL for #<Metabolite:0x00007fd10894b7f0>

3D MOL for #<Metabolite:0x00007fd10894b7f0>

3D SDF for #<Metabolite:0x00007fd10894b7f0>

3D-SDF for #<Metabolite:0x00007fd10894b7f0>

PDB for #<Metabolite:0x00007fd10894b7f0>

3D PDB for #<Metabolite:0x00007fd10894b7f0>

SMILES for #<Metabolite:0x00007fd10894b7f0>

INCHI for #<Metabolite:0x00007fd10894b7f0>

Structure for #<Metabolite:0x00007fd10894b7f0>

3D Structure for #<Metabolite:0x00007fd10894b7f0>