H4B

5,6,7,8-TETRAHYDROBIOPTERIN

Created:	1999-07-08
Last modified:	2011-06-04

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640 entries where H4B is found as a standalone ligand2 entries where H4B is covalently linked to polymer or other heterogen groups

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Chemical Details
Formal Charge	0
Atom Count	32
Chiral Atom Count	3
Bond Count	33
Aromatic Bond Count	6

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Chemical Component Summary
Name	5,6,7,8-TETRAHYDROBIOPTERIN
Systematic Name (OpenEye OEToolkits)	(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one
Formula	C₉ H₁₅ N₅ O₃
Molecular Weight	241.247
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C1C=2NC(CNC=2N=C(N1)N)C(O)C(O)C
SMILES	CACTVS	3.341	C[CH](O)[CH](O)[CH]1CNC2=C(N1)C(=O)NC(=N2)N
SMILES	OpenEye OEToolkits	1.5.0	CC(C(C1CNC2=C(N1)C(=O)NC(=N2)N)O)O
Canonical SMILES	CACTVS	3.341	C[C@H](O)[C@H](O)[C@H]1CNC2=C(N1)C(=O)NC(=N2)N
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[C@@H]([C@@H]([C@H]1CNC2=C(N1)C(=O)NC(=N2)N)O)O
InChI	InChI	1.03	InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
InChIKey	InChI	1.03	FNKQXYHWGSIFBK-RPDRRWSUSA-N

Drug Info: DrugBank

DrugBank ID	DB00360
Name	Sapropterin
Groups	approved investigational
Description	Sapropterin (tetrahydrobiopterin or BH4) is a cofactor in the synthesis of nitric oxide. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase.
Synonyms	Sapropterin dihydrochloride (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin Sapropterin 6R-5,6,7,8-tetrahydrobiopterin 6R-L-5,6,7,8-tetrahydrobiopterin Sapropterina sapropterinum 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone 5,6,7,8-Tetrahydrobiopterin (−)-(6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone 6R-BH4 (6R)-L-erythro-tetrahydrobiopterin R-THBP Tetrahydrobiopterin
Brand Names	Reddy-sapropterin Kuvan Sapropterin Dipharma Sapropterin Dihydrochloride Javygtor Sapropterin dihydrochloride
Indication	For the treatment of tetrahydrobiopterin (BH4) deficiency.
Categories	Alimentary Tract and Metabolism Amines BCRP/ABCG2 Inhibitors Coenzymes Dietary Supplements Enzymes and Coenzymes Ethylamines Heterocyclic Compounds, Fused-Ring Nitric Oxide Synthase Other Miscellaneous Therapeutic Agents P-glycoprotein inhibitors Phenethylamines Phenylalanine Hydroxylase Activator Phenylalanine Hydroxylase Activators Pteridines Pterins Supplements Various Alimentary Tract and Metabolism Products
ATC-Code	A16AX07
CAS number	62989-33-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Phenylalanine-4-hydroxylase	MSTAVLENPGLGRKLSDFGQETSYIEDNCNQNGAISLIFSLKEEVGALAK...	unknown	cofactor
Nitric oxide synthase, endothelial	MGNLKSVAQEPGPPCGLGLGLGLGLCGKQGPATPAPEPSRAPASLLPPAP...	unknown	cofactor
Tyrosine 3-monooxygenase	MPTPDATTPQAKGFRRAVSELDAKQAEAIMVRGQGAPGPSLTGSPWPGTA...	unknown	cofactor
Tryptophan 5-hydroxylase 1	MIEDNKENKDHSLERGRASLIFSLKNEVGGLIKALKIFQEKHVNLLHIES...	unknown	cofactor
Prostaglandin G/H synthase 2	MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...	unknown	inducer
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682