Aquayamycin

Aquayamycin^[1]
Names

Preferred IUPAC name (3R,4aR,12bS)-9-[(2R,4R,5S,6R)-4,5-Dihydroxy-6-methyloxan-2-yl]-3,4a,8,12b-tetrahydroxy-3-methyl-3,4,4a,12b-tetrahydrotetraphene-1,7,12(2H)-trione
Identifiers
CAS Number	26055-63-0^Y
3D model (JSmol)	Interactive image
ChemSpider	66147^Y
MeSH	aquayamycin
PubChem CID	73441
CompTox Dashboard (EPA)	DTXSID40948932
InChI InChI=1S/C25H26O10/c1-10-19(28)14(26)7-15(35-10)11-3-4-12-17(20(11)29)21(30)13-5-6-24(33)9-23(2,32)8-16(27)25(24,34)18(13)22(12)31/h3-6,10,14-15,19,26,28-29,32-34H,7-9H2,1-2H3/t10-,14-,15-,19-,23+,24+,25+/m1/s1^Y Key: KCOULPRVOZDQEL-IFNZWHIZSA-N^Y InChI=1/C25H26O10/c1-10-19(28)14(26)7-15(35-10)11-3-4-12-17(20(11)29)21(30)13-5-6-24(33)9-23(2,32)8-16(27)25(24,34)18(13)22(12)31/h3-6,10,14-15,19,26,28-29,32-34H,7-9H2,1-2H3/t10-,14-,15-,19-,23+,24+,25+/m1/s1 Key: KCOULPRVOZDQEL-IFNZWHIZBY
SMILES C[C@@H]1[C@H]([C@@H](C[C@@H](O1)C2=C(C3=C(C=C2)C(=O)C4=C(C3=O)C=C[C@]5([C@@]4(C(=O)C[C@](C5)(C)O)O)O)O)O)O
Properties
Chemical formula	C₂₅H₂₆O₁₀
Molar mass	486.47 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

Chemical compound

Aquayamycin is an anthraquinone derivative.^[2] It is an inhibitor of the enzyme tyrosine hydroxylase.

Saquayamycins (saquayamycins A, B, C and D) are antibiotics of the aquayamycin group found in Streptomyces nodosus cultures broth.^[3]

References

^ Aquayamycin - Compound Summary, PubChem.
^ Sezaki, M.; Kondo, S.; Maeda, K.; Umezawa, H.; Ono, M. (1970). "The structure of aquayamycin". Tetrahedron. 26 (22): 5171–5190. doi:10.1016/S0040-4020(01)98726-5. PMID 5499897.
^ Uchida, T.; Imoto, M.; Watanabe, Y.; Miura, K.; Dobashi, T.; Matsuda, N.; Sawa, T.; Naganawa, H.; Hamada, M.; Takeuchi, T.; Umezawa, H. (1985). "Saquayamycins, new aquayamycin-group antibiotics". The Journal of Antibiotics. 38 (9): 1171–1181. doi:10.7164/antibiotics.38.1171. PMID 3840796.

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine
Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone
Inhibitors: MAO-B selective: Adarigiline Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone
DBHTooltip Dopamine beta-monooxygenase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products: Tryptophan→5-HTP Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products: Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products: L-Histidine→Histamine Inhibitors: Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products: Histamine→N-Methylhistamine Inhibitors: Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products: Histamine→Imidazole acetic acid Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins