Structure Database (LMSD)

Common Name
Dehydroabietic acid
Systematic Name
Synonyms
LM ID
LMPR0104050005
Formula
Exact Mass
Calculate m/z
300.20893
Status
Curated



Classification

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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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