MiMeDB: Showing metabocard for Glucaric acid (MMDBc0029503)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:24:56 UTC

Update Date

2024-04-30 19:36:22 UTC

Metabolite ID

MMDBc0029503

Metabolite Identification

Common Name

Glucaric acid

Description

Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221919572D          

 14 13  0  0  0  0            999 V2000
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029503

> <DATABASE_NAME>
MIME

> <SMILES>
OC(C(O)C(O)C(O)=O)C(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)

> <INCHI_KEY>
DSLZVSRJTYRBFB-UHFFFAOYSA-N

> <FORMULA>
C6H10O8

> <MOLECULAR_WEIGHT>
210.1388

> <EXACT_MASS>
210.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.028666329598853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,4,5-tetrahydroxyhexanedioic acid

> <ALOGPS_LOGP>
-1.77

> <JCHEM_LOGP>
-3.089469772666667

> <ALOGPS_LOGS>
-0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.541069050878398

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8286041594909985

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7307040369214137

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
38.1384

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mucic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.875  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.207  -1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.541   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.208   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.875  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.127   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    5    9                                                  
CONECT    4    2    6   10                                                  
CONECT    5    3   11   12                                                  
CONECT    6    4   13   14                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
Galactarate	Generator
D-(+)-Saccharic acid	HMDB
D-2,3,4,5-Tetrahydroxyhexanedioic acid	HMDB
D-Galactarate	HMDB
D-Glucarate	HMDB
D-Glucosaccharic acid	HMDB
D-Mucic acid	HMDB
D-Saccharic acid	HMDB
L-Gularic acid	HMDB
Galactaric acid, sodium salt	MeSH
Galactaric acid	MeSH
Strontium galactarate mono-hydrate	MeSH

Molecular Formula

C₆H₁₀O₈

Average Mass

210.1388

Monoisotopic Mass

210.037567296

IUPAC Name

2,3,4,5-tetrahydroxyhexanedioic acid

Traditional Name

mucic acid

CAS Registry Number

87-73-0

SMILES

OC(C(O)C(O)C(O)=O)C(O)C(O)=O

InChI Identifier

InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)

InChI Key

DSLZVSRJTYRBFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Fatty acyl
Fatty acid
Secondary alcohol
Polyol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	63.1 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.1	ChemAxon
logS	-0.52	ALOGPS
pKa (Strongest Acidic)	2.83	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.14 m³·mol⁻¹	ChemAxon
Polarizability	17.03 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-0933000000-4354d91fb6ad4c55395c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-0933000000-4354d91fb6ad4c55395c	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bf-9400000000-b80ffbca6c943091f16e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive	splash10-00b9-6011394000-83b916b3001ad13cf34d	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9210000000-dfdea7f6942307da5753	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-2940000000-22b8846ff96b55a07794	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-8900000000-38caf68471e622d34534	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9200000000-c906f4dd996e2d278b62	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0adr-8920000000-2a3c57d9a8f8d68f4850	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9600000000-1a400678d7f40d843bb4	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ap0-9400000000-287c531a974e2bd85d70	2015-04-25	View Spectrum
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

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Feces
Liver
Prostate
Urine

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	Data Source	Reference
MMDBr0001309	D-Glucurono-6,3-lactone	Glucaric acid	Not Available	VMH	3779687
MMDBr0001310	D-Glucurono-6,3-lactone	Glucaric acid	aldehyde dehydrogenase 1 family, member B1	VMH	3779687
MMDBr0007828	Glucaric acid	5-Dehydro-4-deoxy-D-glucarate	Not Available	VMH	30371894
MMDBr0007829	Glucaric acid	2-Dehydro-3-deoxy-D-glucarate	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	124	Human ; Human feces; Human sputum; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	34	Pig ; Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Actinobacteria	9	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	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
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	2.8	0.33			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	6526537
Human Urine	Detected and Quantified	2.9	0.2			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	6526537
Human Urine	Detected and Quantified	3.91	5.53			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	8.4		5.8	12.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	44.819	50.56			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	26.533	12.667			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.19	0.64			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.5	0.66			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.56		0.27	4.0	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	2.57	1.18			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected but not Quantified									HMDB
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001205

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00767

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mucic acid

METLIN ID

Not Available

PubChem Compound

607

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Herzberg M, Tenenbaum E, Fishel B, Wiener MH: D-Glucaric acid and gamma-glutamyltransferase as indices of hepatic enzyme induction in pregnancy. Clin Chem. 1977 Mar;23(3):596-8. [PubMed:13946 ]
Matsushiro T, Suzuki N, Sato T, Maki T: Effects of diet on glucaric acid concentration in bile and the formation of calcium bilirubinate gallstones. Gastroenterology. 1977 Apr;72(4 Pt 1):630-3. [PubMed:320083 ]
Roth B, Heimann G, Gladtke E: [Excretion of D-glucaric-acid in newborns with non-hemolytic hyperbilirubinemia after phenobarbital treatment (author's transl)]. Padiatr Padol. 1977;12(4):385-93. [PubMed:904946 ]
Sorrell MF, Burnett DA, Tuma DJ, Barak AJ: Paradoxical urinary excretion of D-glucaric acid in acute viral hepatitis. Clin Pharmacol Ther. 1976 Sep;20(3):365-8. doi: 10.1002/cpt1976203365. [PubMed:954355 ]
Levy G, Khanna NN, Soda DM, Tsuzuki O, Stern L: Pharmacokinetics of acetaminophen in the human neonate: formation of acetaminophen glucuronide and sulfate in relation to plasma bilirubin concentration and D-glucaric acid excretion. Pediatrics. 1975 Jun;55(6):818-25. [PubMed:1134883 ]
Traeger A, Horvath T, Rechenbach C, Javor T: Beta-adrenoceptor blocking drugs and cytochrome P-450: the influence of propranolol treatment on caffeine, antipyrine, D-glucaric acid and indocyanine green elimination in patients with hepatic disorders. Int J Clin Pharmacol Res. 1986;6(3):235-9. [PubMed:3744626 ]
Marsh CA: Biosynthesis of D-glucaric acid in mammals: a free-radical mechanism? Carbohydr Res. 1986 Sep 15;153(1):119-31. doi: 10.1016/s0008-6215(00)90201-5. [PubMed:3779687 ]
Walaszek Z, Szemraj J, Narog M, Adams AK, Kilgore J, Sherman U, Hanausek M: Metabolism, uptake, and excretion of a D-glucaric acid salt and its potential use in cancer prevention. Cancer Detect Prev. 1997;21(2):178-90. [PubMed:9101079 ]
Zoltaszek R, Hanausek M, Kilianska ZM, Walaszek Z: [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy Hig Med Dosw (Online). 2008 Sep 5;62:451-62. [PubMed:18772850 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Glucaric acid (MMDBc0029503)

MOL for #<Metabolite:0x00007fecf0e91ff8>

3D MOL for #<Metabolite:0x00007fecf0e91ff8>

3D SDF for #<Metabolite:0x00007fecf0e91ff8>

3D-SDF for #<Metabolite:0x00007fecf0e91ff8>

PDB for #<Metabolite:0x00007fecf0e91ff8>

3D PDB for #<Metabolite:0x00007fecf0e91ff8>

SMILES for #<Metabolite:0x00007fecf0e91ff8>

INCHI for #<Metabolite:0x00007fecf0e91ff8>

Structure for #<Metabolite:0x00007fecf0e91ff8>

3D Structure for #<Metabolite:0x00007fecf0e91ff8>