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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (22) Show 22 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:02 UTC

HMDB ID

HMDB0000490

Secondary Accession Numbers

HMDB00490

Metabolite Identification

Common Name

Etiocholanolone

Description

Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness).

Structure

MOL SDF PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

53-42-9

SMILES

Not Available

InChI Identifier

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1

InChI Key

QGXBDMJGAMFCBF-BNSUEQOYSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000490)

Genetic disorder

Inborn errors of metabolism

Familial mediterranean fever (HMDB: HMDB0000490)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 4886315)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000490)

Excreta

Biofluid or Excreta

Urine (PMID: 8187312)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000490)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000490)

Source

Exogenous

Exogenous (HMDB: HMDB0000490)

Food

Food (HMDB: HMDB0000490)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000490)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000490)

Molecular messenger

Hormone (HMDB: HMDB0000490)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000490)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000490)

Biomarker

Familial mediterranean fever (MarkerDB: MDB00000174)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Predicted Molecular Properties

Not Available

Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.74 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9518 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2548.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	411.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	656.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1266.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1493.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	294.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	415.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	23.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C	2294.0	Standard polar	33892256
Etiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C	2445.5	Standard non polar	33892256
Etiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C	2635.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanolone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2=O	2570.6	Semi standard non polar	33892256
Etiocholanolone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2576.5	Semi standard non polar	33892256
Etiocholanolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2600.9	Semi standard non polar	33892256
Etiocholanolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2517.3	Standard non polar	33892256
Etiocholanolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2936.0	Standard polar	33892256
Etiocholanolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)CC[C@H]4[C@@H]3CC[C@@H]2C1	2814.7	Semi standard non polar	33892256
Etiocholanolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2849.6	Semi standard non polar	33892256
Etiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3133.8	Semi standard non polar	33892256
Etiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2774.2	Standard non polar	33892256
Etiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3181.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Androstenedione Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0012 +/- 0.00013 uM	Adult (>18 years old)	Male	Normal	4886315	details
Blood	Detected and Quantified	0.0013 +/- 0.00017 uM	Adult (>18 years old)	Both	Normal	4886315	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Urine	Detected and Quantified	0.36 (0.11-0.67) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8187312	details
Urine	Detected and Quantified	0.27 (0.18-0.34) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11085621	details
Urine	Detected and Quantified	0.21 (0.13-0.28) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11085621	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.004 +/- 0.0009 uM	Adult (>18 years old)	Both	Familial Mediterranean Fever	4886315	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Urine	Detected and Quantified	0.59 +/- 0.05 umol/mmol creatinine	Adult (>18 years old)	Female	Hirsutism	8187312	details

Associated Disorders and Diseases

Disease References

Familial mediterranean fever
George JM, Wolff SM, Diller E, Bartter FC: Recurrent fever of unknown etiology: failure to demonstrate association between fever and plasma unconjugated etiocholanolone. J Clin Invest. 1969 Mar;48(3):558-63. [PubMed:4886315 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Hirsutism
Gilad S, Chayen R, Tordjman K, Kisch E, Stern N: Assessment of 5 alpha-reductase activity in hirsute women: comparison of serum androstanediol glucuronide with urinary androsterone and aetiocholanolone excretion. Clin Endocrinol (Oxf). 1994 Apr;40(4):459-64. [PubMed:8187312 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

Not Available

References

Synthesis Reference

Pelli, Beatrice; Traldi, Pietro; Gargano, Michele; Ravasio, Nicoletta; Rossi, Michele. Easy determination of epimeric androsterones by collision spectroscopy: the molar ratio of 5b-androstan-3a-ol-17-one and 5b-androstan-3b-ol-17-one obtained by hydrogenation of 5b-androstane-3,17-dione on copper/alumina. Organic Mass Spectrometry (1987), 22(3), 183-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27. [PubMed:15946323 ]
Hampl R, Starka L, Jansky L: Steroids and thermogenesis. Physiol Res. 2006;55(2):123-31. Epub 2005 May 24. [PubMed:15910167 ]
Poor V, Juricskay S, Telegdy E: Urinary steroids in men with male-pattern alopecia. J Biochem Biophys Methods. 2002 Oct-Nov;53(1-3):123-30. [PubMed:12406594 ]
George JM, Wolff SM, Diller E, Bartter FC: Recurrent fever of unknown etiology: failure to demonstrate association between fever and plasma unconjugated etiocholanolone. J Clin Invest. 1969 Mar;48(3):558-63. [PubMed:4886315 ]

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

Etiocholanolone + NAD → Etiocholanedione + NADH + Hydrogen Ion	details
Etiocholanolone + NADP → Etiocholanedione + NADPH + Hydrogen Ion	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

3. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Showing metabocard for Etiocholanolone (HMDB0000490)

MOL for HMDB0000490 (Etiocholanolone)

3D MOL for HMDB0000490 (Etiocholanolone)

3D SDF for HMDB0000490 (Etiocholanolone)

3D-SDF for HMDB0000490 (Etiocholanolone)

PDB for HMDB0000490 (Etiocholanolone)

3D PDB for HMDB0000490 (Etiocholanolone)

SMILES for HMDB0000490 (Etiocholanolone)

INCHI for HMDB0000490 (Etiocholanolone)

Structure for HMDB0000490 (Etiocholanolone)

3D Structure for HMDB0000490 (Etiocholanolone)

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

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