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MedKoo Cat#: 461177 | Name: Ravidomycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ravidomycin is an antitumor antibiotic. It exhibits potent anticancer activities against various cancer cell lines in the presence of visible light.

Chemical Structure

Ravidomycin
Ravidomycin
CAS#74622-75-6

Theoretical Analysis

MedKoo Cat#: 461177

Name: Ravidomycin

CAS#: 74622-75-6

Chemical Formula: C31H33NO9

Exact Mass: 563.2155

Molecular Weight: 563.60

Elemental Analysis: C, 66.06; H, 5.90; N, 2.49; O, 25.55

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Ravidomycin; AY 25545; AY-25545; AY25545;
IUPAC/Chemical Name
(2R,3R,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-(1-hydroxy-10,12-dimethoxy-6-oxo-8-vinyl-6H-dibenzo[c,h]chromen-4-yl)-2-methyltetrahydro-2H-pyran-3-yl acetate
InChi Key
GHLIFBNIGXVDHM-LSXWJJIVSA-N
InChi Code
InChI=1S/C31H33NO9/c1-8-16-11-19-23(21(12-16)37-6)18-13-22(38-7)25-20(34)10-9-17(24(25)29(18)41-31(19)36)30-27(35)26(32(4)5)28(14(2)39-30)40-15(3)33/h8-14,26-28,30,34-35H,1H2,2-7H3/t14-,26-,27-,28+,30+/m1/s1
SMILES Code
Oc1ccc([C@@H]2O[C@H](C)[C@H](OC(C)=O)[C@H](N(C)C)[C@H]2O)c(c1c(OC)cc3c4c(OC)cc(C=C)cc54)c3oc5=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 563.60 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kharel MK, Nybo SE, Shepherd MD, Rohr J. Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters. Chembiochem. 2010 Mar 1;11(4):523-32. doi: 10.1002/cbic.200900673. PubMed PMID: 20140934; PubMed Central PMCID: PMC2879346. 2: Sehgal SN, Czerkawski H, Kudelski A, Pandev K, Saucier R, Vézina C. Ravidomycin (AY-25,545), a new antitumor antibiotic. J Antibiot (Tokyo). 1983 Apr;36(4):355-61. PubMed PMID: 6853365. 3: Rakhit S, Eng C, Baker H, Singh K. Chemical modification of ravidomycin and evaluation of biological activities of its derivatives. J Antibiot (Tokyo). 1983 Nov;36(11):1490-4. PubMed PMID: 6654759. 4: Singh K. Studies on the mechanism of action of ravidomycin (AY-25,545). J Antibiot (Tokyo). 1984 Jan;37(1):71-3. PubMed PMID: 6421790. 5: Greenstein M, Monji T, Yeung R, Maiese WM, White RJ. Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin. Antimicrob Agents Chemother. 1986 May;29(5):861-6. PubMed PMID: 3729344; PubMed Central PMCID: PMC284168. 6: Kharel MK, Lian H, Rohr J. Characterization of the TDP-D-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-D-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate. Org Biomol Chem. 2011 Mar 21;9(6):1799-808. doi: 10.1039/c0ob00854k. Epub 2011 Jan 24. PubMed PMID: 21264378; PubMed Central PMCID: PMC4482361. 7: Yamashita N, Shin-ya K, Furihata K, Hayakawa Y, Seto H. New ravidomycin analogues, FE35A and FE35B, apoptosis inducers produced by Streptomyces rochei. J Antibiot (Tokyo). 1998 Dec;51(12):1105-8. PubMed PMID: 10048570. 8: Kharel MK, Pahari P, Lian H, Rohr J. Enzymatic total synthesis of rabelomycin, an angucycline group antibiotic. Org Lett. 2010 Jun 18;12(12):2814-7. doi: 10.1021/ol1009009. PubMed PMID: 20486694; PubMed Central PMCID: PMC2895501. 9: Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Shaaban KA, Rohr J. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat Prod Rep. 2012 Feb;29(2):264-325. doi: 10.1039/c1np00068c. Epub 2011 Dec 21. Review. PubMed PMID: 22186970. 10: Narita T, Matsumoto M, Mogi K, Kukita K, Kawahara R, Nakashima T. Deacetylravidomycin N-oxide, a new antibiotic. Taxonomy and fermentation of the producing organism and isolation, structure and biological properties of the antibiotic. J Antibiot (Tokyo). 1989 Mar;42(3):347-56. PubMed PMID: 2708127. 11: Lorico A, Long BH. Biochemical characterisation of elsamicin and other coumarin-related antitumour agents as potent inhibitors of human topoisomerase II. Eur J Cancer. 1993;29A(14):1985-91. PubMed PMID: 8280493.

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