Hydroxymethylbilane

Hydroxymethylbilane

Identifiers
CAS Number	73023-76-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16645 Y
ChEMBL	ChEMBL273676 Y
ChemSpider	767 Y
MeSH	hydroxymethylbilane
PubChem CID	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(c[nH]c1Cc2c(c(c([nH]2)Cc3[nH]c(c(c3CCC(=O)O)CC(=O)O)Cc4c(c(c([nH]4)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).
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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 either the enzyme uroporphyrinogen III synthase converts it into uroporphyrinogen III, or the compound undergoes spontaneous cyclization and become a uroporphyrinogen I.

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