Methyl Dehydroabietate

Details

• Internal ID: ddcd47f8-d46d-43f6-b961-7a7c98943c5d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• InChI: InChI=1S/C21H30O2/c1-14(2)15-7-9-17-16(13-15)8-10-18-20(17,3)11-6-12-21(18,4)19(22)23-5/h7,9,13-14,18H,6,8,10-12H2,1-5H3/t18-,20-,21-/m1/s1
• InChI Key: PGZCJOPTDHWYES-HMXCVIKNSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.50 g/mol
• Exact Mass: 314.224580195 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.99
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 1235-74-1
• Methyl dehydroabietyate
• UNII-4P47O55S2W
• 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, (1R,4aS,10aR)-
• methyl (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• 4P47O55S2W
• NSC-81596
• NSC-146198
• 1-Phenanthrenecarboxylic acid,1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, (1R,4aS,10aR)-
• (1R,4AS,10AR)-1,2,3,4,4A,9,10,10A-OCTAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-1-PHENANTHRENECARBOXYLIC ACID METHYL ESTER
• 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-,methyl ester, (1R-(1alpha,4abeta,10aalpha))-
• DTXSID10880714
• RefChem:157839
• DTXCID90951052
• METHYL DEHYDROABIETATE [INCI]
• 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, (1R-(1alpha,4abeta,10aalpha))-
• 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-,methyl ester, (1R-(1alpha,4abeta,10aalpha))-(9CI)
• Phenanthrene-1-carboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethyl-, methyl ester,, (1R-(1alpha,4abeta,10aalpha))-
• Phenanthrene-1-carboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethyl-, methyl ester,, [1R-(1.alpha.,4a.beta.,10a.alpha.)]-
• 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, [1R-(1.alpha.,4a.beta.,10a.alpha.)]-
• PGZCJOPTDHWYES-UHFFFAOYSA-N
• (1R,4aS,10aR)-methyl 7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate
• MFCD30478690
• Methyl 8,13-abietatrien-18-oate
• NSC 81596
• NSC 146198
• Methyl 8,11,13-abietatrien-18-oate
• Podocarpa-8,13-trien-15-oic acid, 13-isopropyl-, methyl ester
• 1,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid, methyl ester
• 1-Phenanthrenecarboxylic acid,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, [1R-(1.alpha.,4a.beta.,10a.alpha.)]-
• Dehydroabietinsauremethylester
• CHEMBL12798
• orb2813898
• SCHEMBL15526779
• CHEBI:228313
• PGZCJOPTDHWYES-HMXCVIKNSA-N
• NSC81596
• BDBM50483053
• MFCD27976778
• MSK165809
• NSC146198
• AKOS030241375
• Methyl 8,11,13-Abietadien-18-oate
• DA-55395
• DS-19363
• SY269551
• CS-0163127
• NS00076591
• Q27260314
• (1R,4aS,10aR)-methyl7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate
• METHYL (1R,4AS,10AR)-7-ISOPROPYL-1,4A-DIMETHYL-2,3,4,9,10,10A-HEXAHYDROPHENANTHRENE-1-CARBOXYLATE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8815	88.15%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5573	55.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9485	94.85%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7249	72.49%
P-glycoprotein inhibitior	-	0.6356	63.56%
P-glycoprotein substrate	-	0.5379	53.79%
CYP3A4 substrate	+	0.6227	62.27%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.7495	74.95%
CYP3A4 inhibition	-	0.9158	91.58%
CYP2C9 inhibition	-	0.7352	73.52%
CYP2C19 inhibition	+	0.5998	59.98%
CYP2D6 inhibition	-	0.8810	88.10%
CYP1A2 inhibition	-	0.7642	76.42%
CYP2C8 inhibition	-	0.7706	77.06%
CYP inhibitory promiscuity	-	0.8775	87.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7332	73.32%
Carcinogenicity (trinary)	Non-required	0.5791	57.91%
Eye corrosion	-	0.9466	94.66%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.7855	78.55%
Skin corrosion	-	0.9883	98.83%
Ames mutagenesis	-	0.8644	86.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.6938	69.38%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6823	68.23%
skin sensitisation	-	0.8088	80.88%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.9550	95.50%
Acute Oral Toxicity (c)	III	0.7117	71.17%
Estrogen receptor binding	+	0.7893	78.93%
Androgen receptor binding	+	0.6091	60.91%
Thyroid receptor binding	+	0.7252	72.52%
Glucocorticoid receptor binding	+	0.6379	63.79%
Aromatase binding	-	0.4890	48.90%
PPAR gamma	+	0.6351	63.51%
Honey bee toxicity	-	0.8012	80.12%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9975	99.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.30%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.18%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.16%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	93.21%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.97%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.04%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.61%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.24%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.58%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.50%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.15%	91.07%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.42%	91.03%
CHEMBL4208	P20618	Proteasome component C5	84.17%	90.00%
CHEMBL2535	P11166	Glucose transporter	83.91%	98.75%
CHEMBL205	P00918	Carbonic anhydrase II	83.25%	98.44%
CHEMBL268	P43235	Cathepsin K	82.53%	96.85%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.82%	82.69%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.75%	93.56%
CHEMBL5028	O14672	ADAM10	80.16%	97.50%

Plants that contains it

• Aquilaria sinensis
• Cleonia lusitanica
• Ixora chinensis
• Pinus brutia var. pityusa
• Pinus densiflora
• Pinus luchuensis
• Pinus sylvestris var. hamata
• Torreya nucifera

Cross-Links

• PubChem: 14697
• NPASS: NPC221825
• LOTUS: LTS0080951
• wikiData: Q27260314