Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H34O3 |
| Molecular Weight | 298.4608 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCC(O)C(O)=O
InChI
InChIKey=JBSOOFITVPOOSY-KTKRTIGZSA-N
InChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/b10-9-
| Molecular Formula | C18H34O3 |
| Molecular Weight | 298.4608 |
| Charge | 0 |
| Count |
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| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Optical Activity | ( + / - ) |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:37:15 UTC 2023
by
admin
on
Sat Dec 16 11:37:15 UTC 2023
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| Record UNII |
OSV3KVO1BT
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
844021
Created by
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EU-Orphan Drug |
EU/3/11/916
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admin on Sat Dec 16 11:37:15 UTC 2023 , Edited by admin on Sat Dec 16 11:37:15 UTC 2023
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NCI_THESAURUS |
C274
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| Code System | Code | Type | Description | ||
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DTXSID00430863
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9796304
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11607
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PRIMARY | INN | ||
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C105401
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PRIMARY | NCIT | ||
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56472-29-8
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100000181927
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SUB195753
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143096
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2-HYDROXYOLEIC ACID
Created by
admin on Sat Dec 16 11:37:15 UTC 2023 , Edited by admin on Sat Dec 16 11:37:15 UTC 2023
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PRIMARY | Biochem/physiol Actions: 2OHOA induces cell cycle arrest and apoptosis in several cancer cell lines, including glioma, leukemia, breast and colon cancer lines. 2OHOA increases sphingomyelin (SM) levels in the membranes of tumor cells, which typically display decreased SM membrane content, and remodeled membranes, compared with normal cells. The compound has no effect on SM levels in non-cancer cells. | ||
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OSV3KVO1BT
Created by
admin on Sat Dec 16 11:37:15 UTC 2023 , Edited by admin on Sat Dec 16 11:37:15 UTC 2023
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TARGET -> ACTIVATOR |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
2-hydroxyoleic acid An orally bioavailable, synthetic analog of the fatty acid oleic acid, with potential antitumor activity. Upon administration, 2-hydroxyoleic acid (2OHOA) activates sphingomyelin synthase (SMS), thereby increasing the concentration of sphingomyelin (SM) and diacylglycerol (DAG) in the tumor cell membrane and decreasing membrane levels of phosphatidylethanolamine (PE) and phosphatidylcholine (PC). This restores the normal, healthy levels and ratios of membrane lipids. By restoring normal membrane lipid structure and composition, this agent inhibits membrane-protein associated signaling and the aberrant activity of signaling pathways in certain tumor cells, including the Ras/MAPK and PI3K/AKt pathways. This inhibits tumor cell proliferation, induces tumor cell differentiation, and eventually can cause cell death. Check for active clinical trials using this agent. (NCI Thesaurus)
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ACTIVE MOIETY |
2OHOA is an orally administered bio-active lipid that specifically activates SMS1, a key enzyme that catalyses the reversible conversion of PC, PE and Cer into SM and DAG at cell-membrane level. Membrane lipid composition and organization is known to be significantly altered in cancer cells and it has been observed that these changes are enabling increased recruitment to the cell membrane of central proliferation signalling proteins, such as K-Ras. Over-activation of Ras signalling is known to play a critical role in key proliferation pathways including Ras/MAPK, Pi3K/AKT/mTOR or PKC/Cyclin CDK. Activation of SMS1 in cancer cells induces marked increases in its main product (SM), accompanied by reductions in the levels of its substrates (PC and PE), causing normalization of membrane levels of PE, PC and SM. By contrast, Minerval does not significantly alter membrane lipid composition in non-tumour cells, because the enzyme product (SM) is found already in high levels and its substrates are limiting.
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