Hydroxymethylbilane

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Hydroxymethylbilane

Identifiers
CAS number	73023-76-4
PubChem	788
ChemSpider	767^Y
MeSH	hydroxymethylbilane
ChEBI	CHEBI:16645^Y
ChEMBL	CHEMBL273676^Y
Jmol-3D images	Image 1
SMILES O=C(O)Cc1c(cnc1Cc2c(c(c(n2)Cc3nc(c(c3CCC(=O)O)CC(=O)O)Cc4c(c(c(n4)CO)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O)CCC(=O)O
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)^Y Key: WDFJYRZCZIUBPR-UHFFFAOYSA-N^Y InChI=1/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) Key: WDFJYRZCZIUBPR-UHFFFAOYAI
Properties
Molecular formula	C₄₀H₄₆N₄O₁₇
Molar mass	854.81 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Hydroxymethylbilane (HMB), also known as preuroporphyrinogen, 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 III synthase converts it into uroporphyrinogen III.

In general, defects of heme synthesis after formation of HMB lead to photosensitivity.

Porphyrin biosynthesis

early mitochondrial:	D-Aminolevulinic acid

cytosolic:	Porphobilinogen Hydroxymethylbilane Uroporphyrinogen III Coproporphyrinogen III

late mitochondrial:	Protoporphyrinogen IX Protoporphyrin IX

Heme degradation
and excretion

Breakdown of heme

Intestine, excretion in feces

Kidney, excretion in urine

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

cell/phys (coag, heme, immu, gran), csfs

rbmg/mogr/tumr/hist, sysi/epon, btst

drug (B1/2/3+5+6), btst, trns

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