Hydroxymethylbilane

Hydroxymethylbilane
Identifiers

CAS Number	73023-76-4^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16645^Y
ChEMBL	ChEMBL273676^Y
ChemSpider	767^Y
MeSH	hydroxymethylbilane
PubChem	788
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
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
Properties
Chemical formula	C₄₀H₄₆N₄O₁₇
Molar mass	854.81 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
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.

early mitochondrial:	D-Aminolevulinic acid

cytosolic:	Porphobilinogen Hydroxymethylbilane Uroporphyrinogen III Coproporphyrinogen III

late mitochondrial:	Protoporphyrinogen IX Protoporphyrin IX

Breakdown of heme

Intestine, excretion in feces

Kidney, excretion in urine

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