2-hydroxy-9-cis-octadecenoic acid profile

2-hydroxy-9-cis-octadecenoic acid: designed to modify the lipid organization of the membrane [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-hydroxyoleic acid : A 2-hydroxy fatty acid that is oleic acid which carries a hydroxy group at position 2. It is an orally bioavailable synthetic hydroxylated fatty acid which modulates the lipid content of cancer cell membranes and induces cell cycle arrest and apoptosis in several cancer cell lines. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	9796304
CHEBI ID	143096
SCHEMBL ID	378126
MeSH ID	M0481525

Synonym
minerval
2-hydroxy-9-cis-octadecenoic acid
(z)-2-hydroxyoctadec-9-enoic acid
2-hydroxy oleic acid
2-hydroxyoleic acid
(9z)-2-hydroxyoctadec-9-enoic acid
2-hydroxy-9z-octadecenoic acid
cis-2-hydroxy-9-octadecenoic acid
2-ohoa
2ohoa
56472-29-8
CHEBI:143096
alpha-hydroxyoleic acid
JBSOOFITVPOOSY-KTKRTIGZSA-N
SCHEMBL378126
2-hydroxyoleicacid
DTXSID00430863
2ohoa, >=98% (hplc)
oxyolsaure
nfx88
nfx-88
sml-0256
idroxioleic acid [inn]
rac-(2r,9z)-2-hydroxyoctadec-9-enoic acid
sml0256
2-hydroxyoleic acid [who-dd]
9-octadecenoic acid, 2-hydroxy-, (z)-
LMFA01050540
9-octadecenoic acid, 2-hydroxy-, (9z)-
2-hydroxy-9z-hexadecenoic acid
Q28816084
HY-129467
CS-0105697
(rac)-idroxioleic acid
unii-osv3kvo1bt
osv3kvo1bt ,
cis-2-hydroxy9-octadecenoic acid
2-hydroxy-9(z)-octadecenoic acid
9-octadecenoicacid,2-hydroxy-,(9z)-
Z2312477358
BP-29870
AKOS040742138

Role	Description
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
apoptosis inducer	Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antihypertensive agent	Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
2-hydroxy fatty acid	Any fatty acid with a hydroxy functional group in the alpha- or 2-position.
long-chain fatty acid	A fatty acid with a chain length ranging from C13 to C22.
hydroxy monounsaturated fatty acid	Any monounsaturated fatty acid carrying one or more hydroxy substituents.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	8 (22.22)	29.6817
2010's	26 (72.22)	24.3611
2020's	2 (5.56)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	3 (7.89%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	35 (92.11%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
4-aminopyridine [no description available]	2.04	1	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.11	1
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.04	1	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
temozolomide [no description available]	2.07	1	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.06	1
thiazoles [no description available]	2.07	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.07	1	organic bromide salt	colorimetric reagent; dye
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.15	1	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
methotrexate [no description available]	2.05	1	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	3.85	3	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
elaidic acid [no description available]	2.04	1	octadec-9-enoic acid	food component
d 609 [no description available]	2.06	1
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.04	1	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
1-palmitoyl-2-oleoylphosphatidylethanolamine 1-palmitoyl-2-oleoylphosphatidylethanolamine: RN given refers to (Z)-isomer; RN for cpd without isomeric designation not available 12/88. 1-palmitoyl-2-oleoyl phosphatidylethanolamine : A phosphatidylethanolamine in which the phosphatidyl acyl groups at C-1 and C-2 are palmitoyl and oleoyl respectively.	2.07	1	(18R,21S)-24-amino-21-hydroxy-21-oxido-15-oxo-16,20,22-trioxa-21lambdalambda(5)-phosphatetracosan-18-yl icosanoate; phosphatidylethanolamine
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.07	1	phosphatidylcholine(1+)
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.5	2	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
thermozymocidin thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog	2.11	1	alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid	antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent
gw 4869 GW 4869: inhibits neutral sphingomyelinase; structure in first source	2.11	1
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.2	5	1,2-diacyl-sn-glycero-3-phosphocholine
glycolipids [no description available]	3.35	6
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	2.05	1	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	2.07	1	dacarbazine
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.04	1

Condition	Relationship Strength	Studies
Cancer of Lung [description not available]	2.54	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.54	2
Experimental Leukemia [description not available]	2.05	1
Benign Neoplasms [description not available]	3.19	5
Leukemia, Lymphocytic, T Cell [description not available]	2.05	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.19	5
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2.05	1
Peripheral Nerve Injury [description not available]	4.37	2
Nerve Pain [description not available]	4.37	2
Injuries, Spinal Cord [description not available]	4.39	2
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	4.37	2
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	4.39	2
Peripheral Nerve Injuries Injuries to the PERIPHERAL NERVES.	4.37	2
Ache [description not available]	3.06	1
Palsy [description not available]	3.06	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	3.06	1
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	3.06	1
Glial Cell Tumors [description not available]	4.38	7
Sphingolipid Storage Diseases [description not available]	2.08	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	4.38	7
Carcinoma, Non-Small Cell Lung [description not available]	2.1	1
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.1	1
Allodynia [description not available]	3.03	1
Abnormal Deep Tendon Reflex [description not available]	3.03	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	3.03	1
Reflex, Abnormal An abnormal response to a stimulus applied to the sensory components of the nervous system. This may take the form of increased, decreased, or absent reflexes.	3.03	1
Experimental Neoplasms [description not available]	2.13	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.48	2
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.57	2
Diseases of Immune System [description not available]	2.17	1
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	2.17	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.06	1
Benign Neoplasms, Brain [description not available]	2.07	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.07	1

2-hydroxy-9-cis-octadecenoic acid

Description

Cross-References

Synonyms (42)

Roles (3)

Drug Classes (3)

Research

Studies (36)

Market Indicators

Research Demand Index: 11.25

Study Types