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β-Rubromycin

CAT: 0931-T35428-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T35428-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
27267-70-5
Target
Antibiotic, Others, Reverse Transcriptase, HIV Protease
Related Pathways
Microbiology/Virology, Proteases/Proteasome, Others
Bioactivity
β-Rubromycin is a bacterial metabolite originally isolated from Streptomyces that has diverse biological activities.1 It inhibits the growth of HMO2, KATO-III, and MCF-7 cells with GI50 values of 0.5, 0.84, and <0.1 μM, respectively. β-rubromycin inhibits HIV-1 reverse transcriptase activity by 39.7% when used at a concentration of 10 μM. It also has antibacterial activity against Gram-positive bacteria. The structure of β-rubromycin was originally described as containing an ortho-quinone group, but it was revised to a para-quinone group in 2000 using organic and biosynthetic methods, as well as spectroscopic analysis.1,2,3
Smiles
COC(=O)c1cc2cc3CC[C@]4(CC5=C(O4)C(=O)c4c(O)c(OC)cc(OC)c4C5=O)Oc3c(O)c2c(=O)o1 |c:13|
Molecular Formula
C27H20O12
Molecular Weight
536.445
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

beta-Rubromycin

Beta-Rubromycin is a member of chromenes.

CAS Number27267-70-5
PubChem CID5464074
IUPAC Namemethyl (2S)-8',10-dihydroxy-5',7'-dimethoxy-4',9,9'-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
Molecular FormulaC27H20O12
Molecular Weight536.4
XLogP4.1
Topological Polar Surface Area164
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Heavy Atom Count39
Formal Charge0
Complexity1170
SMILES
COC1=CC(=C(C2=C1C(=O)C3=C(C2=O)O[C@]4(C3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O)OC
InChI
InChI=1S/C27H20O12/c1-34-13-8-14(35-2)20(29)18-17(13)19(28)12-9-27(39-24(12)22(18)31)5-4-10-6-11-7-15(25(32)36-3)37-26(33)16(11)21(30)23(10)38-27/h6-8,29-30H,4-5,9H2,1-3H3/t27-/m0/s1
InChIKey
FXCBZGHGMRSWJD-MHZLTWQESA-N
Chemical Structure
2D Structure
2D structure of beta-Rubromycin
CAS: 27267-70-5
CID: 5464074
Formula: C27H20O12
MW: 536.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight536.4
XLogP34.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Exact Mass536.09547607
Monoisotopic Mass536.09547607
Topological Polar Surface Area164 Ų
Heavy Atom Count39
Formal Charge0
Complexity1170
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Related Products

CatalogName
T26160-01Rubomycin H

Alternative Products

CatalogName
HY-122482β-Rubromycin
HY-122777γ-Rubromycin
sc-364111AGamma-Rubromycin
207197-01Rubromycin Gamma
GA9971-5mgBeta-Rubromycin
442620-01Beta-Rubromycin discontinued. See 207089
207089-01Rubromycin Beta (Methyl-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[4,3-g]chromene]-7'-carboxylate)

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