Synonym
Conocurvone; Conocurvon; NSC650891; NSC-650891; NSC 650891
IUPAC/Chemical Name
(8,8':9',8''-Ter-3H-naphtho(2,1-b)pyran)-7,7',7'',10,10',10''-hexone, 9,9''-dihydroxy-3,3',3''-trimethyl-3,3',3''-tris(4-methyl-3-pentenyl)-, (3R,3'R,3''R)-
InChi Key
IJDNMADFCZSLQD-UPMPAGDASA-N
InChi Code
InChI=1S/C60H56O11/c1-31(2)13-10-25-58(7)28-22-34-40(69-58)19-16-37-43(34)53(64)47(49-52(63)39-18-21-42-36(45(39)55(66)57(49)68)24-30-60(9,71-42)27-12-15-33(5)6)46(50(37)61)48-51(62)38-17-20-41-35(44(38)54(65)56(48)67)23-29-59(8,70-41)26-11-14-32(3)4/h13-24,28-30,67-68H,10-12,25-27H2,1-9H3/t58-,59-,60-/m1/s1
SMILES Code
O=C(C(C(C(C1=CC=C2C(C=C[C@](CC/C=C(C)/C)(C)O2)=C31)=O)=C(C(C(C4=CC=C5C(C=C[C@](CC/C=C(C)/C)(C)O5)=C64)=O)=C(O)C6=O)C3=O)=C7O)C8=CC=C9C(C=C[C@](CC/C=C(C)/C)(C)O9)=C8C7=O
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
>2 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
2934.99.9001
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Soluble in DMSO |
0.0 |
100.00 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
953.09
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.
| 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: Emadi A, Harwood JS, Kohanim S, Stagliano KW. Regiocontrolled synthesis of the trimeric quinone framework of conocurvone. Org Lett. 2002 Feb 21;4(4):521-4. doi: 10.1021/ol010272m. PMID: 11843581.
2: Crosby IT, Bourke DG, Jones ED, de Bruyn PJ, Rhodes D, Vandegraaff N, Cox S, Coates JA, Robertson AD. Antiviral agents 2. Synthesis of trimeric naphthoquinone analogues of conocurvone and their antiviral evaluation against HIV. Bioorg Med Chem. 2010 Sep 1;18(17):6442-50. doi: 10.1016/j.bmc.2010.06.105. Epub 2010 Aug 3. PMID: 20685126.
3: Vlietinck AJ, De Bruyne T, Apers S, Pieters LA. Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med. 1998 Mar;64(2):97-109. doi: 10.1055/s-2006-957384. PMID: 9525100.
4: Crosby IT, Bourke DG, Jones ED, Jeynes TP, Cox S, Coates JA, Robertson AD. Antiviral agents 3. Discovery of a novel small molecule non-nucleoside inhibitor of hepatitis B virus (HBV). Bioorg Med Chem Lett. 2011 Mar 15;21(6):1644-8. doi: 10.1016/j.bmcl.2011.01.109. Epub 2011 Jan 31. PMID: 21333535.
5: Stagliano KW, Emadi A, Lu Z, Malinakova HC, Twenter B, Yu M, Holland LE, Rom AM, Harwood JS, Amin R, Johnson AA, Pommier Y. Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone. Bioorg Med Chem. 2006 Aug 15;14(16):5651-65. doi: 10.1016/j.bmc.2006.04.034. Epub 2006 Jun 5. PMID: 16737818.
6: Dai JR, Decosterd LA, Gustafson KR, Cardellina JH 2nd, Gray GN, Boyd MR. Novel naphthoquinones from Conospermum incurvum. J Nat Prod. 1994 Nov;57(11):1511-6. doi: 10.1021/np50113a006. PMID: 7853001.
