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(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione structure

CAS No:
121-40-4
Formula:
C7H6O4
Chemical Name:
(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Synonyms:
7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-,(1R,6S)-;Terreic acid;7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-,stereoisomer;7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-,(1R)-;(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione;(-)-Terreic acid;18715-99-6

Description

Terreic acid is a 2-hydroxy-1,4-benzoquinone that is 5,6-epoxy. It is a natural product of Aspergillus terreus. It has an antibacterial activity explained by its inhibitory effect on bacterial enzymes MurA and GlmU. It is an inhibitor of Bruton's tyrosine kinase, and has an anti-tumoral activity against HeLa and EAC cells. It has a role as a mycotoxin, an antibacterial agent, an EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor, an EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor, an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, an Aspergillus metabolite and an antineoplastic agent. It is an arene epoxide, a tertiary alpha-hydroxy ketone, a member of monohydroxy-1,4-benzoquinones and a diketone. It derives from a 2-hydroxy-1,4-benzoquinone.

(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione Basic Attributes

Molecular Weight：

154.12

Exact Mass：

154.12

UNII：

XM2Y0DRJ7D

NSC Number：

294734

Characteristics

PSA：

66.90000

XLogP3：

-0.2

Appearance：

Pale yellow solid

Density：

1.1993 (rough estimate)

Melting Point：

127 °C

Boiling Point：

242.5°C (estimate)

Flash Point：

147.4ºC

Refractive Index：

1.4300 (estimate)

Water Solubility：

DMSO: soluble 10mg/mL

Storage Conditions：

Store at +4ºC

Vapor Pressure：

9.63E-06mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

36-45

Marks：

Precautionary statement(s)：

P280

Hazard Statements：

H302 + H312

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

terreic acid

(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione Use and Manufacturing

Selective inhibitor of Bruton's tyrosine kinase (BTK). Inhibits the interaction between PKCbII and BTK (IC 50 ~ 30 mM) and the catalytic activity of BTK but does not affect the activity of PKC. Has little effect on the activities of Lyn, Syk, PKA, casein kinase I, ERK1, ERK2 and p38 kinases.

Computed Properties

Molecular Weight:154.12
XLogP3:-0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:154.02660867
Monoisotopic Mass:154.02660867
Topological Polar Surface Area:66.9
Heavy Atom Count:11
Complexity:289
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of (1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties

(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

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