MiMeDB: Showing metabocard for betaenone A (MMDBc0055776)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:06:00 UTC

Update Date

2022-08-12 20:09:27 UTC

Metabolite ID

MMDBc0055776

Metabolite Identification

Common Name

betaenone A

Description

85269-22-3 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on 85269-22-3.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222062D          

 32 34  0  0  1  0            999 V2000
    0.0022   -1.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -1.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482   -1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0374    1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890   -1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5209    1.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9350    1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.5210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5351   -0.3986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8100    0.8327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2343    0.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353   -0.0754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3882   -0.0045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2390    0.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389    0.8450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1062   -0.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3811    0.8205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0921    1.2391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4656    0.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376   -0.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6907    1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5280    0.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9379    2.1178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642    0.2811    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921   -0.8975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1723    0.0915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512   -0.7192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222   -0.8288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
 11  2  1  1  0  0  0
 11  7  1  0  0  0  0
 12  3  1  1  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  1  0  0  0
 18  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19  5  1  1  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  6  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 23 17  2  0  0  0  0
 18 24  1  6  0  0  0
 20 25  1  6  0  0  0
 21 26  1  1  0  0  0
 27 10  1  0  0  0  0
 11 28  1  6  0  0  0
 12 29  1  6  0  0  0
 13 30  1  6  0  0  0
 15 31  1  1  0  0  0
 16 32  1  6  0  0  0
M  END


  Mrv1652306172222062D          

 32 34  0  0  1  0            999 V2000
    0.0022   -1.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -1.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482   -1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0374    1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890   -1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5209    1.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9350    1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.5210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5351   -0.3986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8100    0.8327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2343    0.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353   -0.0754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3882   -0.0045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2390    0.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389    0.8450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1062   -0.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3811    0.8205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0921    1.2391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4656    0.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376   -0.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6907    1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5280    0.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9379    2.1178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642    0.2811    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921   -0.8975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1723    0.0915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512   -0.7192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222   -0.8288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
 11  2  1  1  0  0  0
 11  7  1  0  0  0  0
 12  3  1  1  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  1  0  0  0
 18  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19  5  1  1  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  6  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 23 17  2  0  0  0  0
 18 24  1  6  0  0  0
 20 25  1  6  0  0  0
 21 26  1  1  0  0  0
 27 10  1  0  0  0  0
 11 28  1  6  0  0  0
 12 29  1  6  0  0  0
 13 30  1  6  0  0  0
 15 31  1  1  0  0  0
 16 32  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0055776

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(O)=C1\C(=O)[C@@]2(C)[C@@]([H])([C@]([H])(C)CC)[C@](C)(O)[C@]1(O)[C@@]1([H])C[C@](C)(O)C[C@@]([H])(C)[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O5/c1-7-11(2)16-19(5)15-12(3)8-18(4,24)9-13(15)21(26,20(16,6)25)14(10-22)17(19)23/h10-13,15-16,22,24-26H,7-9H2,1-6H3/b14-10+/t11-,12-,13+,15+,16-,18-,19-,20+,21+/m1/s1

> <INCHI_KEY>
FHJXKTOXQHRDTL-PSWVRJCXSA-N

> <FORMULA>
C21H34O5

> <MOLECULAR_WEIGHT>
366.498

> <EXACT_MASS>
366.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.385491930994775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-12-[(2R)-butan-2-yl]-1,4,11-trihydroxy-10-(hydroxymethylidene)-4,6,8,11-tetramethyltricyclo[6.2.2.0^{2,7}]dodecan-9-one

> <JCHEM_LOGP>
2.1171663536666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.003851863745254

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.743342340812054

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7827863454787947

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
99.45119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-12-[(2R)-butan-2-yl]-1,4,11-trihydroxy-10-(hydroxymethylidene)-4,6,8,11-tetramethyltricyclo[6.2.2.0^{2,7}]dodecan-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       0.004  -3.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.339  -0.766   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.252  -2.545   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.742   1.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.770  -2.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.070   2.987   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.099  -2.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.059   0.037   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.706   2.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.612   2.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.692  -0.973   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.732  -0.744   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.379   1.554   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.304   1.289   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.239  -0.141   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.725  -0.008   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.313   0.262   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.046   1.577   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.065  -0.767   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.711   1.532   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.039   2.313   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.602   0.754   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.430  -1.292   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.889   3.002   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.986   1.574   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.752   3.956   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       3.617   3.953   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.053   0.525   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.959  -1.675   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.055   0.171   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.202  -1.343   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.788  -1.547   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6   20                                                            
CONECT    7    1   11                                                       
CONECT    8   12   18                                                       
CONECT    9   13   18                                                       
CONECT   10   14   22   27                                                  
CONECT   11    2    7   16   28                                             
CONECT   12    3    8   15   29                                             
CONECT   13    9   15   21   30                                             
CONECT   14   10   17   21                                                  
CONECT   15   12   13   19   31                                             
CONECT   16   11   19   20   32                                             
CONECT   17   14   19   23                                                  
CONECT   18    4    8    9   24                                             
CONECT   19    5   15   16   17                                             
CONECT   20    6   16   21   25                                             
CONECT   21   13   14   20   26                                             
CONECT   22   10                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   20                                                            
CONECT   26   21                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

Synonyms

Not Available

Molecular Formula

C₂₁H₃₄O₅

Average Mass

366.498

Monoisotopic Mass

366.240624195

IUPAC Name

(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-12-[(2R)-butan-2-yl]-1,4,11-trihydroxy-10-(hydroxymethylidene)-4,6,8,11-tetramethyltricyclo[6.2.2.0^{2,7}]dodecan-9-one

Traditional Name

(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-12-[(2R)-butan-2-yl]-1,4,11-trihydroxy-10-(hydroxymethylidene)-4,6,8,11-tetramethyltricyclo[6.2.2.0^{2,7}]dodecan-9-one

CAS Registry Number

Not Available

SMILES

[H]\C(O)=C1\C(=O)[C@@]2(C)[C@@]([H])([C@]([H])(C)CC)[C@](C)(O)[C@]1(O)[C@@]1([H])C[C@](C)(O)C[C@@]([H])(C)[C@]21[H]

InChI Identifier

InChI=1S/C21H34O5/c1-7-11(2)16-19(5)15-12(3)8-18(4,24)9-13(15)21(26,20(16,6)25)14(10-22)17(19)23/h10-13,15-16,22,24-26H,7-9H2,1-6H3/b14-10+/t11-,12-,13+,15+,16-,18-,19-,20+,21+/m1/s1

InChI Key

FHJXKTOXQHRDTL-PSWVRJCXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Ketone
Polyol
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	2.12	ChemAxon
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.45 m³·mol⁻¹	ChemAxon
Polarizability	40.39 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	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
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

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	2

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

C00000528

Chemspider ID

62934098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Betaenone_A

METLIN ID

Not Available

PubChem Compound

102093872

PDB ID

Not Available

ChEBI ID

145055

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 A (MMDBc0055776)

MOL for #<Metabolite:0x00007fecb4f815d0>

3D MOL for #<Metabolite:0x00007fecb4f815d0>

3D SDF for #<Metabolite:0x00007fecb4f815d0>

3D-SDF for #<Metabolite:0x00007fecb4f815d0>

PDB for #<Metabolite:0x00007fecb4f815d0>

3D PDB for #<Metabolite:0x00007fecb4f815d0>

SMILES for #<Metabolite:0x00007fecb4f815d0>

INCHI for #<Metabolite:0x00007fecb4f815d0>

Structure for #<Metabolite:0x00007fecb4f815d0>

3D Structure for #<Metabolite:0x00007fecb4f815d0>