Structure Database (LMSD)
Common Name
Dehydroabietic acid
Systematic Name
Synonyms
3D model of Dehydroabietic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Dehydroabietic acid is a diterpene acid that has been found in P. elliottii resin and has diverse biological activities.1,2,3 It is active against L. amazonensis promastigotes (IC50 = 40 µg/ml).1 Dehydroabietic acid (2.5, 5, and 10 µM) increases the number of mitochondrial ridges, decreases mitochondrial outer membrane rupture, and increases the expression of FSP1 and COQ10 in an HL7720 cell model of ferroptosis induced by oleic acid .2 In vivo, dehydroabietic acid (10 and 20 mg/kg) reduces hepatic total cholesterol and triglyceride levels, ferroptosis, and lipid peroxidation in a mouse model of high-fat diet-induced non-alcoholic fatty liver disease (NAFLD). Dehydroabietic acid is also found in wood industry effluents and is considered a pollutant.3 It increases oxygen consumption and cellular heat production and reduces cellular ATP content in isolated rainbow trout (O. mykiss) hepatocytes.
This information has been provided by Cayman Chemical
References
3. Gao, G., Xie, Z., Li, E.-W., et al. Dehydroabietic acid improves nonalcoholic fatty liver disease through activating the Keap1/Nrf2-ARE signaling pathway to reduce ferroptosis. J. Nat. Med. (2021).
String Representations
InChiKey (Click to copy)
NFWKVWVWBFBAOV-MISYRCLQSA-N
InChi (Click to copy)
InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1
SMILES (Click to copy)
[C@@]1([C@@]2([H])[C@@](CCC1)(C)C1=CC=C(C=C1CC2)C(C)C)(C)C(O)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
3
Aromatic Rings
1
Rotatable Bonds
2
Van der Waals Molecular Volume
313.60
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
4.90
Molar Refractivity
89.29
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Updated at
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