7-oxodehydroabietic acid profile

7-oxodehydroabietic acid, also known as 7-oxoabietic acid, is a naturally occurring diterpenoid compound found in various plant species. It is a derivative of abietic acid, a major component of rosin. Research on 7-oxodehydroabietic acid has focused on its diverse biological activities and potential applications.

The compound has been shown to exhibit antioxidant, anti-inflammatory, and antimicrobial properties. Studies have investigated its potential for treating conditions such as cancer, Alzheimer's disease, and bacterial infections.

Its synthesis is achieved through chemical oxidation of abietic acid, and its effects are attributed to its interactions with cellular signaling pathways and its ability to scavenge free radicals.

7-oxodehydroabietic acid is a subject of ongoing research due to its potential as a therapeutic agent and its ability to modulate key biological processes. Its unique structure and biological activities make it a promising candidate for drug development.'
```

7-oxodehydroabietic acid: RN refers to (1R-(1alpha,4beta,10aalpha))-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	29212
CHEMBL ID	597919
SCHEMBL ID	3212768
MeSH ID	M0251172

Synonym
7-oxodehydroabietic acid
podocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-7-oxo-
7-ketodehydroabietic acid
13-isopropyl-7-oxopodocarpa-8,11,13-trien-15-oic acid
brn 3216723
CHEMBL597919
7-oxocallitrisic acid
(1r,4as,10ar)-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2h-phenanthrene-1-carboxylic acid
4-10-00-02942 (beilstein handbook reference)
18684-55-4
unii-i8pnl8flid
1-phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-9-oxo-, (1r,4as,10ar)-
i8pnl8flid ,
SCHEMBL3212768
DTXSID5075074
AKOS027324385
FS-8481
Q27280582
HY-133620
CS-0128446
(1r,4as,10ar)-1,4a-dimethyl-9-oxo-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
EN300-6733727

Bioassays (29)

Assay ID	Title	Year	Journal	Article
AID1295877	Cytotoxicity in human HCT116 cells by SRB assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1295875	Cytotoxicity in human SKOV3 cells by SRB assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1831627	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells with Si-RNA-induced FADS3 knockdown	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1295874	Cytotoxicity in human A549 cells by SRB assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1234145	Stimulation of neurite outgrowth in rat PC12 cells incubated for 96 hrs in absence of 20 ng/ml NGF by phase contrast microscopy	2015	Journal of natural products, Jul-24, Volume: 78, Issue:7	Bioactive Diterpenoids from the Leaves of Callicarpa macrophylla.
AID1831628	Cytotoxicity against mouse AML12 cells assessed as cell viability at 20 uM measured after 24 hrs by MTT assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID539818	Activation of human BK alpha channel expressed in CHO-K1 cells assessed as ionic current at 30 uM by patch clamp electrophysiological assay relative to control	2010	Bioorganic & medicinal chemistry, Dec-15, Volume: 18, Issue:24	Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives.
AID1234144	Stimulation of nerve growth factor-mediated neurite outgrowth in rat PC12 cells incubated for 96 hrs in presence of 20 ng/ml NGF by phase contrast microscopy	2015	Journal of natural products, Jul-24, Volume: 78, Issue:7	Bioactive Diterpenoids from the Leaves of Callicarpa macrophylla.
AID1295870	Neuroprotective activity in rat C6 cells assessed as induction of NGF release at 20 uM after 24 hrs by ELISA	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1831621	Activation of CPT1A in mouse AML12 cells assessed as inhibition of oleic acid-induced lipid accumulation using L-carnitine and palmitoyl CoA as substrates at 20 uM measured after 48 hrs by DNTB reagent based assay relative to control	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1295871	Cytotoxicity in rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1831619	Activation of CPT1A in mouse AML12 cells assessed as inhibition of oleic acid-induced lipid accumulation using L-carnitine and palmitoyl CoA as substrates pretreated with ETO for 6 hrs followed by addition of compound at 20 uM measured after 48 hrs by DNT	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831624	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells assessed as increased expression of CPT1A preincubated with ETO at 40 uM measured after 24 hrs by Oil red O staining based microscopic assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID457057	Inhibition of TNF-alpha-induced NF-kappaB activity in human pNF-kappaB-luc-293 cells	2010	Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2	Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.
AID1831629	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells at 20 uM preincubated with oleic acid for 24 hrs followed by addition of compounds and measured after 24 hrs by Oil red O staining based microscopic assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831626	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells with Si-RNA-induced ECHS1 knockdown	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831616	Cytotoxicity against mouse AML12 cells assessed as cell viability at 5 uM measured after 24 hrs by MTT assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831620	Activation of CPT1A in mouse AML12 cells assessed as inhibition of oleic acid-induced lipid accumulation using L-carnitine and palmitoyl CoA as substrates at 40 uM measured after 48 hrs by DNTB reagent based enzymatic assay relative to control	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831617	Cytotoxicity against mouse AML12 cells assessed as cell viability at 10 uM measured after 24 hrs by MTT assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831623	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells with siRNA-induced CPT1A knockdown at 40 uM measured after 24 hrs by Oil red O staining based microscopic assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID457056	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO release	2010	Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2	Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.
AID1295876	Cytotoxicity in human SK-MEL-2 cells by SRB assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID457055	Antiproliferative activity against human QGY7703 cells	2010	Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2	Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.
AID1831618	Activation of CPT1A in mouse AML12 cells assessed as inhibition of oleic acid-induced lipid accumulation using L-carnitine and palmitoyl CoA as substrates pretreated with ETO for 6 hrs followed by addition of compound at 40 uM measured after 48 hrs by DNT	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID457058	Antiproliferative activity against human LoVo cells	2010	Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2	Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.
AID1295872	Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1831625	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells with Si-RNA-induced ACSL1 knockdown	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831630	Inhibition of oleic acid-induced lipid accumulation in mouse AML12 cells at 40 uM preincubated with oleic acid for 24 hrs followed by addition of compounds and measured after 24 hrs by Oil red O staining based microscopic assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
AID1831622	Cytotoxicity against mouse AML12 cells assessed as cell viability at 40 uM measured after 24 hrs by MTT assay	2021	ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12	Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	4 (22.22)	18.2507
2000's	5 (27.78)	29.6817
2010's	7 (38.89)	24.3611
2020's	2 (11.11)	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	0 (0.00%)	6.00%
Case Studies	1 (5.26%)	4.05%
Observational	0 (0.00%)	0.25%
Other	18 (94.74%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.05	1	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	7	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	2.06	1	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
diethanolamine diethanolamine: RN given refers to parent cpd. diethanolamine : A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.	2.04	1	ethanolamines	human xenobiotic metabolite
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	3.41	7	abietane diterpenoid; monocarboxylic acid	plant metabolite
etoposide [no description available]	2.13	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
dehydroabietic acid dehydroabietic acid: major aquatic toxicant in effluent of pulp and paper mills. dehydroabietic acid : An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group.. dehydroabietate : A monocarboxylic acid anion that is the conjugate base of dehydroabietic acid, obtained by deprotonation of the carboxy group.	3.53	8	abietane diterpenoid; carbotricyclic compound; monocarboxylic acid	allergen; metabolite
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.13	1	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
pimaric acid pimaric acid: RN given refers to (D)-isomer; structure	2.04	1	diterpenoid
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.31	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	2.91	4
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	2.13	1	enone; monomethoxybenzene; phenols
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.04	1	2-trans-abscisic acid
13-epi-sclareol 13-epi-sclareol: an unusual labdane diterpene from the roots of Coleus forskohlii with cell growth inhibitory action in breast and uterine cancers in vitro; structure in first source	2.05	1
dehydroabietinol dehydroabietinol: Isolated from Hyptis suaveolens; structure in first source	2.05	1	abietane diterpenoid; carbotricyclic compound
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	3.51	8

Condition	Relationship Strength	Studies
Allergic Contact Dermatitis [description not available]	2.92	4
Foot Dermatoses Skin diseases of the foot, general or unspecified.	2.11	1
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.92	4
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.44	2
Dermatitis, Irritant A non-allergic contact dermatitis caused by prolonged exposure to irritants and not explained by delayed hypersensitivity mechanisms.	1.98	1
Dermatitis, Eczematous [description not available]	1.98	1
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	1.98	1
Hand Dermatosis [description not available]	1.98	1
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	1.98	1
Hand Dermatoses Skin diseases involving the HANDS.	1.98	1
Contact Dermatitis [description not available]	1.99	1
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	1.99	1
Asthma, Bronchial [description not available]	2	1
Diseases, Occupational [description not available]	2	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2	1

7-oxodehydroabietic acid

Description

Cross-References

Synonyms (22)

Bioassays (29)

Research

Studies (18)

Market Indicators

Research Demand Index: 20.93

Study Types

7-oxodehydroabietic acid

Description

Cross-References

Synonyms (22)

Bioassays (29)

Research

Studies (18)

Market Indicators

Research Demand Index: 20.93

Study Types

Related Drugs (16)

Related Conditions (15)