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Terreic Acid

CAT: 0024-sc-200655ASize: 5 mgDry Ice: NoHazardous: No
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CAS Number
121-40-4

Chemical Information

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

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 antineoplastic agent, an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, an EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor, an Aspergillus metabolite and an EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor. It is a tertiary alpha-hydroxy ketone, an arene epoxide, a diketone and a member of monohydroxy-1,4-benzoquinones. It is functionally related to a 2-hydroxy-1,4-benzoquinone. It is a conjugate acid of a terreate.

CAS Number121-40-4
PubChem CID91437
IUPAC Name(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Molecular FormulaC7H6O4
Molecular Weight154.12
XLogP-0.2
Topological Polar Surface Area66.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Heavy Atom Count11
Formal Charge0
Complexity289
SMILES
CC1=C(C(=O)[C@H]2[C@@H](C1=O)O2)O
InChI
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
InChIKey
ATFNSNUJZOYXFC-RQJHMYQMSA-N
Chemical Structure
2D Structure
2D structure of (1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
CAS: 121-40-4
CID: 91437
Formula: C7H6O4
MW: 154.12
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight154.12
XLogP3-0.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass154.02660867
Monoisotopic Mass154.02660867
Topological Polar Surface Area66.9 Ų
Heavy Atom Count11
Formal Charge0
Complexity289
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
256905(-) -Terreic acid
M33758-01(+/-) -Terreic acid
GW0390-5mgTerreic acid
B6724-10(-)-Terreic acid
MBS5796683(+/-)-Terreic acid
HY-110013A-01(Rac) -Terreic acid
OR1071368-01Acid-apeg6-acid
MBS6083807-01Medronic Acid (Methylenebiphosphonic Acid, Methylenediphosphonic Acid, Methanebisphosphonic Acid, Methanediphosphonic Acid, MDP)
L2500-01Lipoic Acid (Thioctic Acid, (±) -α-Lipoic Acid)
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