Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone
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![Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/67b49c0986cf441080e7c1381413d441.png "Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone")
Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone
structure -
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CAS No:
14513-15-6
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Formula:
C21H16N2O2S
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Chemical Name:
Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone
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Synonyms:
NSC-1125476;Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone;SIRT1/2 Inhibitor IV, Cambinol;SIRT1/2 Inhibitor IV;CAMBINOL;NSC-1125476;Cambinol;NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone;5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
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CAS No:
Description
Cambinol is a beta-naphtol derivative that inhibits NAD-dependant deacetylases to reduce cell survival under stress. This activity is currently being investigated for its use as a cancer treatment.
Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone Basic Attributes
360.43
360.09324893
8S2PHY4FNC
112546
DTXSID40390573
Characteristics
100.97000
4.54910
1.41g/cm3
235 °C(dec.)
667ºC
357.2ºC
1.771
<0.1mg/mL
Room temp
2.12E-18mmHg at 25°C
Safety Information
3
22
Xn
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Cambinol inhibits the NAD-dependant deacetylases SIRT1 and SIRT2, members of a protein family known as sirtuins. Inhibiting SIRT1 and SIRT2 while cells are under stress increases acetylation of p53, Ku70, and Foxo3a. This inhibition sensitizes cells to the action of drugs like [etoposide] and [paclitaxel], not just other drugs that damage DNA. Although the mechanism of this sensitizing is not defined, it is not dependent on p53, Ku70, or Foxo3a. The independent mechanism suggests the existence of more molecular targets. Cambinol is noncompetitive against NAD and competitive against H-4 peptide, substrates of SIRT2. Inhibiting SIRT2 increases the acetylation of tubulin. Cambinol also increases the acetylation of BCL6, a protein necessary for oncogenesis. Cambinol is also a weak inhibitor of SIRT5.
cambinol
Computed Properties
Molecular Weight:360.4
XLogP3:4.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:360.09324893
Monoisotopic Mass:360.09324893
Topological Polar Surface Area:93.4
Heavy Atom Count:26
Complexity:597
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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