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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:40 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002183

Secondary Accession Numbers

HMDB0062579
HMDB02183
HMDB62579

Metabolite Identification

Common Name

Docosahexaenoic acid

Description

true

Structure

MOL SDF PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₂

Average Molecular Weight

328.4883

Monoisotopic Molecular Weight

328.240230268

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

6217-54-5

SMILES

Not Available

InChI Identifier

InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

MBMBGCFOFBJSGT-KUBAVDMBSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Docosahexaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	4132.5	Standard polar	33892256
Docosahexaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2242.9	Standard non polar	33892256
Docosahexaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2521.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Docosahexaenoic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C	2562.9	Semi standard non polar	33892256
Docosahexaenoic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C	2809.9	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Adipose Tissue
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Retina
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	94.2 +/- 31.3 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	4.66 +/- 3.3 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	90.9 +/- 21.6 uM	Adult (>18 years old)	Male	Normal	18633173	details
Blood	Detected and Quantified	98.7 +/- 41.0 uM	Adult (>18 years old)	Female	Normal	18633173	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	2.3 +/- 1.2 uM	Adult (>18 years old)	Both	Normal	2361977	details
Blood	Detected and Quantified	0.9 +/- 0.3 uM	Adult (>18 years old)	Both	Normal	2361977	details
Blood	Detected and Quantified	1.777 +/- 0.796 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.990 +/- 0.009 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	128.5 +/- 46.1 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected and Quantified	103.504 +/- 30.442 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	100.460 +/- 24.354 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	66.973 +/- 21.310 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	0.00347 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	0.00391 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	0.00414 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	0.00461 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	60.885 +/- 12.177 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	154.252 +/- 47.155 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	165.607 +/- 68.496 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	189.352 +/- 70.0177 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	255.260 +/- 75.162 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	420 +/- 110 uM	Adult (>18 years old)	Male	Normal	14608088	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.15 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	12967724	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	5.5 +/- 6.3 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	14643447	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	64.7 +/- 39.2 uM	Adult (>18 years old)	Both	Hypertension	18633173	details
Blood	Detected and Quantified	56.6 +/- 36.7 uM	Adult (>18 years old)	Male	Essential hypertension	18633173	details
Blood	Detected and Quantified	83.0 +/- 39.0 uM	Adult (>18 years old)	Female	Essential hypertension	18633173	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Blood	Detected and Quantified	20.66 uM	Newborn (0-30 days old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	122.36 uM	Infant (0-1 year old)	Male	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	135.43 uM	Newborn (0-30 days old)	Female	Rhizomelic chondrodysplasia punctata	9818927	details
Blood	Detected and Quantified	144.700-160.300 uM	Children (1-13 years old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	64.3 +/- 28.5 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Blood	Detected and Quantified	146.733 +/- 61.798 uM	Adult (>18 years old)	Both	Depression	21185973	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.43 +/- 0.3 uM	Adult (>18 years old)	Both	Stroke	12967724	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	4.4 +/- 9.4 umol/mmol creatinine	Adult (>18 years old)	Both	Thyroid cancer	14643447	details

Associated Disorders and Diseases

Disease References

Hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Essential hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Major depressive disorder
Sublette ME, Segal-Isaacson CJ, Cooper TB, Fekri S, Vanegas N, Galfalvy HC, Oquendo MA, Mann JJ: Validation of a food frequency questionnaire to assess intake of n-3 polyunsaturated fatty acids in subjects with and without major depressive disorder. J Am Diet Assoc. 2011 Jan;111(1):117-123.e1-2. doi: 10.1016/j.jada.2010.10.007. [PubMed:21185973 ]
Rhizomelic chondrodysplasia punctata
Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Stroke
Pilitsis JG, Coplin WM, O'Regan MH, Wellwood JM, Diaz FG, Fairfax MR, Michael DB, Phillis JW: Measurement of free fatty acids in cerebrospinal fluid from patients with hemorrhagic and ischemic stroke. Brain Res. 2003 Sep 26;985(2):198-201. [PubMed:12967724 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Thyroid cancer
Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]

Associated OMIM IDs

145500 (Hypertension)
608516 (Major depressive disorder)
215100 (Rhizomelic chondrodysplasia punctata)
243500 (Isovaleric acidemia)
601367 (Stroke)
114500 (Colorectal cancer)

External Links

Not Available

References

Synthesis Reference

Wright, Stephen W.; Kuo, Elaine Y.; Corey, E. J. An effective process for the isolation of Docosahexaenoic acid in quantity from cod liver oil. Journal of Organic Chemistry (1987), 52(19), 4399-4401.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Woodman RJ, Mori TA, Burke V, Puddey IB, Barden A, Watts GF, Beilin LJ: Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients. Atherosclerosis. 2003 Jan;166(1):85-93. [PubMed:12482554 ]
Watanabe A, Saito S, Tsuchida T, Higuchi K, Okita M: Low plasma levels of docosahexaenoic acid in patients with liver cirrhosis and its correction with a polyunsaturated fatty acid-enriched soft oil capsule. Nutrition. 1999 Apr;15(4):284-8. [PubMed:10319360 ]
Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S. [PubMed:10617968 ]
Gomez de Segura IA, Valderrabano S, Vazquez I, Vallejo-Cremades MT, Gomez-Garcia L, Sanchez M, de Miguel E: Protective effects of dietary enrichment with docosahexaenoic acid plus protein in 5-fluorouracil-induced intestinal injury in the rat. Eur J Gastroenterol Hepatol. 2004 May;16(5):479-85. [PubMed:15097041 ]
Shingu T, Karanian JW, Kim HY, Yergey JA, Salem N Jr: Discovery of novel brain lipoxygenase products formed from docosahexaenoic acid (22:6w3). Adv Alcohol Subst Abuse. 1988;7(3-4):235-40. [PubMed:2975919 ]
Hong S, Tjonahen E, Morgan EL, Lu Y, Serhan CN, Rowley AF: Rainbow trout (Oncorhynchus mykiss) brain cells biosynthesize novel docosahexaenoic acid-derived resolvins and protectins-Mediator lipidomic analysis. Prostaglandins Other Lipid Mediat. 2005 Dec;78(1-4):107-16. Epub 2005 Jun 13. [PubMed:16303609 ]
Hibbeln JR, Bissette G, Umhau JC, George DT: Omega-3 status and cerebrospinal fluid corticotrophin releasing hormone in perpetrators of domestic violence. Biol Psychiatry. 2004 Dec 1;56(11):895-7. [PubMed:15576068 ]
Jorgensen MH, Hernell O, Hughes E, Michaelsen KF: Is there a relation between docosahexaenoic acid concentration in mothers' milk and visual development in term infants? J Pediatr Gastroenterol Nutr. 2001 Mar;32(3):293-6. [PubMed:11345178 ]
Crabtree JT, Gordon MJ, Campbell FM, Dutta-Roy AK: Differential distribution and metabolism of arachidonic acid and docosahexaenoic acid by human placental choriocarcinoma (BeWo) cells. Mol Cell Biochem. 1998 Aug;185(1-2):191-8. [PubMed:9746226 ]
Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70. [PubMed:9134186 ]
Martinez M: Severe deficiency of docosahexaenoic acid in peroxisomal disorders: a defect of delta 4 desaturation? Neurology. 1990 Aug;40(8):1292-8. [PubMed:2143272 ]
Bohles H, Arndt S, Ohlenschlager U, Beeg T, Gebhardt B, Sewell AC: Maternal plasma homocysteine, placenta status and docosahexaenoic acid concentration in erythrocyte phospholipids of the newborn. Eur J Pediatr. 1999 Mar;158(3):243-6. [PubMed:10094448 ]
Crawford MA, Bloom M, Broadhurst CL, Schmidt WF, Cunnane SC, Galli C, Gehbremeskel K, Linseisen F, Lloyd-Smith J, Parkington J: Evidence for the unique function of docosahexaenoic acid during the evolution of the modern hominid brain. Lipids. 1999;34 Suppl:S39-47. [PubMed:10419087 ]
Andersson L, Sternby B, Nilsson A: Hydrolysis of phosphatidylethanolamine by human pancreatic phospholipase A2. Effect of bile salts. Scand J Gastroenterol. 1994 Feb;29(2):182-7. [PubMed:8171289 ]
Brossard N, Croset M, Normand S, Pousin J, Lecerf J, Laville M, Tayot JL, Lagarde M: Human plasma albumin transports [13C]docosahexaenoic acid in two lipid forms to blood cells. J Lipid Res. 1997 Aug;38(8):1571-82. [PubMed:9300779 ]
Berry CB, Hayes D, Murphy A, Wiessner M, Rauen T, McBean GJ: Differential modulation of the glutamate transporters GLT1, GLAST and EAAC1 by docosahexaenoic acid. Brain Res. 2005 Mar 10;1037(1-2):123-33. [PubMed:15777760 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Enzyme Details

2. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Enzyme Details

3. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Enzyme Details

4. Cytochrome P450 2U1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the hydroxylation of arachidonic acid, docosahexaenoic acid and other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes.
Gene Name:: CYP2U1
Uniprot ID:: Q7Z449
Molecular weight:: 61986.525

Enzyme Details

5. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Showing metabocard for Docosahexaenoic acid (HMDB0002183)

MOL for HMDB0002183 (Docosahexaenoic acid)

3D MOL for HMDB0002183 (Docosahexaenoic acid)

3D SDF for HMDB0002183 (Docosahexaenoic acid)

3D-SDF for HMDB0002183 (Docosahexaenoic acid)

PDB for HMDB0002183 (Docosahexaenoic acid)

3D PDB for HMDB0002183 (Docosahexaenoic acid)

SMILES for HMDB0002183 (Docosahexaenoic acid)

INCHI for HMDB0002183 (Docosahexaenoic acid)

Structure for HMDB0002183 (Docosahexaenoic acid)

3D Structure for HMDB0002183 (Docosahexaenoic acid)

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions