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158233-67-1 molecular structure
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1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(octadecylamino)-1,2-dihydropyrimidin-2-one

ChemBase ID: 133370
Molecular Formular: C27H49N3O5
Molecular Mass: 495.69506
Monoisotopic Mass: 495.36722168
SMILES and InChIs

SMILES:
CCCCCCCCCCCCCCCCCCNc1ccn(c(=O)n1)[C@H]1[C@H]([C@@H]([C@H](O1)CO)O)O
Canonical SMILES:
CCCCCCCCCCCCCCCCCCNc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@@H]1O)O)CO
InChI:
InChI=1S/C27H49N3O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-28-23-18-20-30(27(34)29-23)26-25(33)24(32)22(21-31)35-26/h18,20,22,24-26,31-33H,2-17,19,21H2,1H3,(H,28,29,34)/t22-,24-,25+,26-/m1/s1
InChIKey:
HQHQCEKUGWOYPS-URBBEOKESA-N

Cite this record

CBID:133370 http://www.chembase.cn/molecule-133370.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(octadecylamino)-1,2-dihydropyrimidin-2-one
IUPAC Traditional name
1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(octadecylamino)pyrimidin-2-one
Synonyms
N(4)-octadecyl-ara-C
N4-Stearyl-Ara C
NOAC
N4-Octadecylcytosine β-D-arabinofuranoside
CAS Number
158233-67-1
MDL Number
MFCD00467196
PubChem SID
24898023
162227647
PubChem CID
133043

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
O5508 external link Add to cart Please log in.
Data Source Data ID
PubChem 133043 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.553241  H Acceptors
H Donor LogD (pH = 5.5) 5.027951 
LogD (pH = 7.4) 5.0279493  Log P 5.0279527 
Molar Refractivity 137.607 cm3 Polarizability 54.394547 Å3
Polar Surface Area 114.62 Å2 Rotatable Bonds 20 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Bioassay(PubChem)
RTECS
UW7370900 expand Show data source
German water hazard class
3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - O5508 external link
Other Notes
Lipophilic, cytotoxic derivative of cytosine arabinoside
Application
N4-Stearyl-Ara C (N(4)-octadecyl-ara-C, NOAC) is a lipophilic derivative of Ara-C used to improve the incorporation of Ara-C, an anti-cancer agent, into lipid bilayers of liposomes and/or target cells.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

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