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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:11 -0600
Update Date	2015-06-03 15:53:46 -0600
Secondary Accession Numbers	ECMDB01137
Identification
Name:	Hydroxymethylbilane
Description	Hydroxymethylbilane is a molecule involved in the metabolism of porphyrin. In the third step, it is generated by the enzyme porphobilinogen deaminase , and in the next step the enzyme uroporphyrinogen I synthase converts it into uroporphyrinogen I. -- Wikipedia
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x942ccd94> Close
Synonyms:	3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)bilane-2,7,12,17-tetrapropanoate 3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)bilane-2,7,12,17-tetrapropanoic acid 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-Biline-2,7,12,17-tetrapropanoate 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-Biline-2,7,12,17-tetrapropanoic acid 3-[2-[[4-(2-Carboxyethyl)-5-[[4-(2-carboxyethyl)-5-[[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl]propanoate 3-[2-[[4-(2-Carboxyethyl)-5-[[4-(2-carboxyethyl)-5-[[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl]propanoic acid HMB Hydroxymethylbilane Preuroporphyrinogen
Chemical Formula:	C40H46N4O17
Weight:	Average: 854.8098 Monoisotopic: 854.285796066
InChI Key:	WDFJYRZCZIUBPR-UHFFFAOYSA-N
InChI:	InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)
CAS number:	73023-76-4
IUPAC Name:	3-(5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-2-yl]methyl}-2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-1H-pyrrol-3-yl)propanoic acid
Traditional IUPAC Name:	3-(5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-2-yl]methyl}-2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-1H-pyrrol-3-yl)propanoic acid
SMILES:	OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1
Chemical Taxonomy
Description	belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Tetrapyrroles and derivatives
Sub Class	Not Available
Direct Parent	Tetrapyrroles and derivatives
Alternative Parents	Substituted pyrroles Heteroaromatic compounds Carboxylic acids Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Aromatic alcohols
Substituents	Tetrapyrrole skeleton Substituted pyrrole Pyrrole Heteroaromatic compound Azacycle Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Aromatic alcohol Organic oxygen compound Organic nitrogen compound Alcohol Primary alcohol Organooxygen compound Organonitrogen compound Carbonyl group Organic oxide Organopnictogen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	bilanes (CHEBI:16645 )
Physical Properties
State:	Solid
Charge:	-8
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.032 g/L ALOGPS logP 0.53 ALOGPS logP 0.97 ChemAxon logS -4.4 ALOGPS pKa (Strongest Acidic) 3.25 ChemAxon Physiological Charge -8 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 13 ChemAxon Polar Surface Area 381.79 Ų ChemAxon Rotatable Bond Count 27 ChemAxon Refractivity 209.92 m³·mol⁻¹ ChemAxon Polarizability 85.68 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Hydroxymethylbilane <> Water + Uroporphyrinogen III Water + 4 Porphobilinogen > Hydroxymethylbilane +4 Ammonium 4 Porphobilinogen + Water <> Hydroxymethylbilane +4 Ammonia Water + Porphobilinogen <> Hydrogen ion + Ammonia + Hydroxymethylbilane 4 Porphobilinogen + Water > Hydroxymethylbilane +4 Ammonia Hydroxymethylbilane > Uroporphyrinogen III + Water Hydroxymethylbilane <> Water + Uroporphyrinogen III 4 Porphobilinogen + Water <> Hydroxymethylbilane +4 Ammonia 4 Porphobilinogen + Water <> Hydroxymethylbilane +4 Ammonia
SMPDB Pathways:	Porphyrin metabolism PW000936
KEGG Pathways:	Metabolic pathways eco01100 Porphyrin and chlorophyll metabolism ec00860
EcoCyc Pathways:	tetrapyrrole biosynthesis I PWY-5188
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014u-0000000790-0465e102e331b86b0303 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-0000000940-84d7b7307b952e375d11 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-002f-0000000910-4cfaaf03b9bff04a3a7d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-052o-0000000790-1398b69ce01f9c5d047c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-0000000940-b283797ea8328ef028d6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052f-1000001930-9e9b406ad31d6bf35cf0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01ox-0000000900-be1376bf8d447c596ca6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03xu-0000000900-a2d6c191927cc76b8b5b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-01w4-0100020900-38c7a5fb40b79705b420 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000f-0000000960-014b54cbe7492f0da108 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0007-0000000900-ab9d5ede3ef2151c6c9e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-01oy-1110001910-bfe90c78d3e5c8f93825 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16645 HMDB ID HMDB01137 Pubchem Compound ID 788 Kegg ID C01024 ChemSpider ID 767 Wikipedia Hydroxymethylbilane BioCyc ID HYDROXYMETHYLBILANE EcoCyc ID HYDROXYMETHYLBILANE

Enzymes