MiMeDB: Showing metabocard for 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid (MMDBc0055337)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:49:33 UTC

Update Date

2025-10-07 16:09:04 UTC

Metabolite ID

MMDBc0055337

Metabolite Identification

Common Name

3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid

Description

3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid is a dioxo compound belonging to the class of fatty acids. There is limited literature available on this metabolite, indicating that further research may be necessary to fully understand its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221492D          

 19 20  0  0  1  0            999 V2000
    2.4782    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  1  0  0  0
  9  3  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13  1  1  6  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  0  0  0  0
  8 18  1  6  0  0  0
  9 19  1  1  0  0  0
M  CHG  1  17  -1
M  END
> <DATABASE_ID>
MMDBc0055337

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CCC(=O)[C@@]2([H])CCC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O4/c1-13-7-6-10(14)8(2-5-12(16)17)9(13)3-4-11(13)15/h8-9H,2-7H2,1H3,(H,16,17)/p-1/t8-,9-,13-/m0/s1

> <INCHI_KEY>
PCCFNLPWOFTZPJ-RVBZMBCESA-M

> <FORMULA>
C13H17O4

> <MOLECULAR_WEIGHT>
237.276

> <EXACT_MASS>
237.113232607

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.583760268001022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate

> <JCHEM_LOGP>
1.7877208216666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.33866395065536

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.393278109476852

> <JCHEM_PKA_STRONGEST_BASIC>
-7.1448963184852

> <JCHEM_POLAR_SURFACE_AREA>
74.27

> <JCHEM_REFRACTIVITY>
71.5907

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-hexahydroinden-4-yl]propanoate

> <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       4.626   3.072   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.788  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O-1
HETATM   18  H   UNK     0       4.787  -1.540   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       6.121   0.770   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2    5    8                                                       
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    2   12                                                       
CONECT    6    7   10                                                       
CONECT    7    6   13                                                       
CONECT    8    2    9   10   18                                             
CONECT    9    3    8   13   19                                             
CONECT   10    6    8   14                                                  
CONECT   11    4   13   15                                                  
CONECT   12    5   16   17                                                  
CONECT   13    1    7    9   11                                             
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

Synonyms

Value	Source
3-[(3AS,4S,7as)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate	ChEBI
3-[(3AS,4S,7as)-7a-methyl-1,5-dioxo-octahydroinden-4-yl]propanoate	ChEBI
9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-Oate(1-)	ChEBI
3-[(3AS,4S,7as)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid	Generator
3-[(3AS,4S,7as)-7a-methyl-1,5-dioxo-octahydroinden-4-yl]propanoic acid	Generator
9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-Oic acid(1-)	Generator
9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-Oic acid	Generator

Molecular Formula

C₁₃H₁₇O₄

Average Mass

237.276

Monoisotopic Mass

237.113232607

IUPAC Name

3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate

Traditional Name

3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-hexahydroinden-4-yl]propanoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CCC(=O)[C@@]2([H])CCC([O-])=O

InChI Identifier

InChI=1S/C13H18O4/c1-13-7-6-10(14)8(2-5-12(16)17)9(13)3-4-11(13)15/h8-9H,2-7H2,1H3,(H,16,17)/p-1/t8-,9-,13-/m0/s1

InChI Key

PCCFNLPWOFTZPJ-RVBZMBCESA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocyclic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Carbocyclic fatty acids

Alternative Parents

Substituents

Carbocyclic fatty acid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

dioxo monocarboxylic acid anion (CHEBI:63692 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.79	ChemAxon
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.27 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.59 m³·mol⁻¹	ChemAxon
Polarizability	24.58 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

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	135.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-24	27.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	367.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	549.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	423.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	321.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2135.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	72.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	455.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	447.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	282.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	183.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	157.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	118.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	349.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	283.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	358.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1207.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1041.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_1	C[C@]12CCC(O[Si](C)(C)C)=C(CCC(=O)[O-])[C@@H]1CCC2=O	standard non polar	2025-10-24	1806.6
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_2	C[C@]12CCC(=O)[C@@H](CCC(=O)[O-])[C@@H]1CC=C2O[Si](C)(C)C	standard non polar	2025-10-24	1711.23
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_3	C[C@]12CC=C(O[Si](C)(C)C)[C@@H](CCC(=O)[O-])[C@@H]1CCC2=O	standard non polar	2025-10-24	1785.05
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_4	C[C@]12CCC(O[Si](C)(C)C)=C(CCC(=O)[O-])[C@@H]1CC=C2O[Si](C)(C)C	standard non polar	2025-10-24	1489.1
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_5	C[C@]12CC=C(O[Si](C)(C)C)[C@@H](CCC(=O)[O-])[C@@H]1CC=C2O[Si](C)(C)C	standard non polar	2025-10-24	2151.15
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_1	C[C@]12CCC(O[Si](C)(C)C)=C(CCC(=O)[O-])[C@@H]1CCC2=O	standard polar	2025-10-24	2140.36
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_2	C[C@]12CCC(=O)[C@@H](CCC(=O)[O-])[C@@H]1CC=C2O[Si](C)(C)C	standard polar	2025-10-24	1657.0
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_3	C[C@]12CC=C(O[Si](C)(C)C)[C@@H](CCC(=O)[O-])[C@@H]1CCC2=O	standard polar	2025-10-24	2031.31
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_4	C[C@]12CCC(O[Si](C)(C)C)=C(CCC(=O)[O-])[C@@H]1CC=C2O[Si](C)(C)C	standard polar	2025-10-24	2253.74
Gas Chromatography	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid_TMS_5	C[C@]12CC=C(O[Si](C)(C)C)[C@@H](CCC(=O)[O-])[C@@H]1CC=C2O[Si](C)(C)C	standard polar	2025-10-24	1957.11

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0038889	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA	3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid	Thioesterase TesA	Hydrolysis	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
Bacteria/Eubacteria	Actinobacteria	3	Human
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human supragingival plaque

Exposure Sources

Other Exposures

Source Type	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

13086844

KEGG Compound ID

Not Available

BioCyc ID

CPD-13711

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15944652

PDB ID

Not Available

ChEBI ID

63692

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoic acid (MMDBc0055337)

MOL for #<Metabolite:0x00007f9ab566f650>

3D MOL for #<Metabolite:0x00007f9ab566f650>

3D SDF for #<Metabolite:0x00007f9ab566f650>

3D-SDF for #<Metabolite:0x00007f9ab566f650>

PDB for #<Metabolite:0x00007f9ab566f650>

3D PDB for #<Metabolite:0x00007f9ab566f650>

SMILES for #<Metabolite:0x00007f9ab566f650>

INCHI for #<Metabolite:0x00007f9ab566f650>

Structure for #<Metabolite:0x00007f9ab566f650>

3D Structure for #<Metabolite:0x00007f9ab566f650>