Doridosine

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

MedKoo CAT#: 413900

CAS#: 73027-05-1

Description: Doridosine is a new hypotensive N-methylpurine riboside from the nudibranch Anisodoris nobilis

Chemical Structure

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Doridosine
CAS# 73027-05-1
Instruction

Theoretical Analysis

MedKoo Cat#: 413900
Name: Doridosine
CAS#: 73027-05-1
Chemical Formula: C11H15N5O5
Exact Mass: 297.11
Molecular Weight: 297.270
Elemental Analysis: C, 44.44; H, 5.09; N, 23.56; O, 26.91

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Doridosine; 1-Methylisoguanosine

IUPAC/Chemical Name: Adenosine, N,6-didehydro-1,2,3,6-tetrahydro-1-methyl-2-oxo-

InChi Key: WRKSCDGOQXKDME-KQYNXXCUSA-N

InChi Code: InChI=1S/C11H15N5O5/c1-15-8(12)5-9(14-11(15)20)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,12,17-19H,2H2,1H3,(H,14,20)/t4-,6-,7-,10-/m1/s1

SMILES Code: OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC(C(N3C)=N)=C2NC3=O)O1)O)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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 297.27 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Kim YH, Nachman RJ, Pavelka L, Mosher HS, Fuhrman FA, Fuhrman GJ. Doridosine, 1-methylisoguanosine, from Anisodoris nobilis; structure, pharmacological properties and synthesis. J Nat Prod. 1981 Mar-Apr;44(2):206-14. doi: 10.1021/np50014a011. PMID: 7241154.

2: Tao PL, Yen MH, Shyu WS, Chern JW. Doridosine derivatives: binding at adenosine receptors and in vivo effects. Eur J Pharmacol. 1993 Oct 19;243(2):135-9. doi: 10.1016/0014-2999(93)90372-o. PMID: 8276062.

3: Fuhrman FA, Fuhrman GJ, Kim YH, Pavelka LA, Mosher HS. Doridosine: a new hypotensive N-methylpurine riboside from the nudibranch Anisodoris nobilis. Science. 1980 Jan 11;207(4427):193-5. doi: 10.1126/science.7350655. PMID: 7350655.

4: Liaw YC, Chern JW, Lin GS, Wang AH. Unusual conformational flexibility in N1-substituted uncommon purine nucleosides. Crystal structure of 1-allyl- isoguanosine and 1-allyl-xanthosine. FEBS Lett. 1992 Feb 3;297(1-2):4-8. doi: 10.1016/0014-5793(92)80315-8. PMID: 1551434.

5: Goya P, Martínez A. Synthesis and cytostatic screening of an SO2 analogue of doridosine. Arch Pharm (Weinheim). 1988 Feb;321(2):99-101. doi: 10.1002/ardp.19883210213. PMID: 3369933.

6: Davies LP, Baird-Lambert J, Hall JG. 1-Methylisoguanosine: interaction with central adenosine receptors and lack of antagonism of its in vivo effects by a benzodiazepine antagonist. Neuropharmacology. 1987 May;26(5):493-7. doi: 10.1016/0028-3908(87)90033-5. PMID: 3037418.

7: Fuhrman FA, Fuhrman GJ. Effects of some naturally-occurring purine ribosides on purinergic receptors in cardiac and smooth muscle. Comp Biochem Physiol C Comp Pharmacol. 1982;72(2):203-10. doi: 10.1016/0306-4492(82)90085-5. PMID: 6128140.

8: Bartlett RT, Cook AF, Holman MJ, McComas WW, Nowoswait EF, Poonian MS, Baird- Lambert JA, Baldo BA, Marwood JF. Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine. J Med Chem. 1981 Aug;24(8):947-54. doi: 10.1021/jm00140a007. PMID: 7328598.

9: Harden FA, Quinn RJ, Scammells PJ. Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine. J Med Chem. 1991 Sep;34(9):2892-8. doi: 10.1021/jm00113a031. PMID: 1895306.

10: Marwood JF. The cardiovascular actions of 1-methylisoguanosine. Clin Exp Pharmacol Physiol. 1981 Nov-Dec;8(6):575-84. doi: 10.1111/j.1440-1681.1981.tb00769.x. PMID: 7333043.