Fibrostatin E

Fibrostatin E

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Fibrostatin E
Category Enzyme inhibitors
Catalog number BBF-01710
CAS 91776-44-2
Molecular Weight 409.41
Molecular Formula C18H19NO8S

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Description

Fibrostatin E is a proline hydroxylase inhibitor produced by Strptomyces catenulae.

Specification

Synonyms L-Cysteine, N-acetyl-S-((5,8-dihydro-1-hydroxy-7-(hydroxymethyl)-3-methoxy-5,8-dioxo-2-naphthalenyl)methyl)-
IUPAC Name (2R)-2-acetamido-3-[[1-hydroxy-7-(hydroxymethyl)-3-methoxy-5,8-dioxonaphthalen-2-yl]methylsulfanyl]propanoic acid
Canonical SMILES CC(=O)NC(CSCC1=C(C=C2C(=O)C=C(C(=O)C2=C1O)CO)OC)C(=O)O
InChI InChI=1S/C18H19NO8S/c1-8(21)19-12(18(25)26)7-28-6-11-14(27-2)4-10-13(22)3-9(5-20)16(23)15(10)17(11)24/h3-4,12,20,24H,5-7H2,1-2H3,(H,19,21)(H,25,26)/t12-/m0/s1
InChI Key XMGJRXDFMZYRQG-LBPRGKRZSA-N

Properties

Melting Point 174°C

Reference Reading

1. Fibrostatins, new inhibitors of prolyl hydroxylase. I. Taxonomy, isolation and characterization
T Ishimaru, T Kanamaru, K Ohta, H Okazaki J Antibiot (Tokyo). 1987 Sep;40(9):1231-8. doi: 10.7164/antibiotics.40.1231.
Fibrostatins, potent inhibitors of prolyl hydroxylase, were isolated as orange crystals from the culture broth of strain No. 23924, which was identified as Streptomyces catenulae subsp. griseospora. In vitro inhibitory activity (ID50 value) of fibrostatins A, B, C, D, E and F against prolyl hydroxylase of chick embryos was 23, 39, 29, 180, 10 and 14 microM, respectively.
2. Structures of fibrostatins, new inhibitors of prolyl hydroxylase
K Ohta, F Kasahara, T Ishimaru, Y Wada, T Kanamaru, H Okazaki J Antibiot (Tokyo). 1987 Sep;40(9):1239-48. doi: 10.7164/antibiotics.40.1239.
The structures of six inhibitors of prolyl hydroxylase, fibrostatins A, B, C, D, E and F produced by a strain of Streptomyces, were deduced to be 1, 2, 3, 4, 5 and 6, respectively, from chemical and spectroscopic evidence, especially from extensive 13C NMR studies including selective decoupling and low power selective decoupling experiments monitored by 13C-1H long-range couplings. These compounds are the first naturally occurring 2,6,7- or 3,6,7-tri-substituted or 2,3,6,7-tetra-substituted 5-hydroxy-1,4-naphthoquinone inhibitors possessing N-acetyl-L-cystein-S-yl moieties in the molecule.

Bio Calculators

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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