Pimaric acid

Details

• Internal ID: af2513c0-c3e4-4cfb-83b4-51405e496751
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• SMILES (Canonical): CC1(CCC2C(=C1)CCC3C2(CCCC3(C)C(=O)O)C)C=C
• SMILES (Isomeric): C[C@]1(CC[C@H]2C(=C1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)C(=O)O)C)C=C
• InChI: InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1
• InChI Key: MHVJRKBZMUDEEV-APQLOABGSA-N
• Popularity: 319 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.50 g/mol
• Exact Mass: 302.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.21
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Dextropimaric acid
• 127-27-5
• d-Pimaric acid
• Usic acid
• PIMARIC ACID, D
• (+)-Pimaric acid
• Pimara-8(14),15-dien-19-oic acid
• .alpha.-Pimaric acid
• NSC2956
• delta8(14)-Pimaric acid
• CHEBI:39
• UNII-88R98Z71NI
• alpha-Pimaric acid
• 88R98Z71NI
• NSC-2956
• (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• NSC 2956
• (1R,4aR,4bS,7S,10aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• .delta.8(14)-Pimaric acid
• alpha-Pimaricacid
• 13a-methyl-13-vinylpodocarp-8(14)-ene-15-oic acid
• ST053518
• PIMARIC ACID [MI]
• 13-alpha-methyl-13-vinylpodocarp-8(14)-ene-15-oic acid
• Podocarp-8(14)-en-15-oic acid, 13.alpha.-methyl-13-vinyl-
• SCHEMBL177983
• CHEMBL1410398
• DTXSID80858728
• 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6, 7,9,10,10a-dodecahydro-1,4a, 7-trimethyl-, (1R-(1.alpha.,4a.beta.,4b.alpha., 7.beta.,10a.alpha.))-
• 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R,4aR,4bS,7S,10aR)-
• 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-, [1R-(1.alpha.,.4a.beta.,4b.alpha.,7.beta.,10a.alpha.)]-
• HY-N3063
• TNP00231
• AKOS024282152
• NCGC00017305-01
• MS-24370
• CS-0023138
• C09159
• Q418035
• Podocarp-8(14)-en-15-oic acid, 13alpha-methyl-13-vinyl-
• (1R,4AR,4BS,7S,10AR)-7-ETHENYL-1,2,3,4,4A,4B,5,6,7,9,10,10A-DODECAHYDRO-1,4A,7-TRIMETHYL-1-PHENANTHRENECARBOXYLIC ACID
• 1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a- dodecahydrophenanthrene-1-carboxylic acid
• 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6, 7,9,10,10a-dodecahydro-1,4a, 7-trimethyl-, (1R-(1alpha,4abeta,4balpha, 7beta,10aalpha))-
• 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R,4aR,7S)-
• 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-, (1theta-(1alpha,4abeta,4balpha,7beta,10aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.8606	86.06%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4127	41.27%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	-	0.4703	47.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.7840	78.40%
P-glycoprotein inhibitior	-	0.8340	83.40%
P-glycoprotein substrate	-	0.8784	87.84%
CYP3A4 substrate	+	0.5658	56.58%
CYP2C9 substrate	-	0.5859	58.59%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.8276	82.76%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.7575	75.75%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.7748	77.48%
CYP2C8 inhibition	-	0.7309	73.09%
CYP inhibitory promiscuity	-	0.8959	89.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5883	58.83%
Eye corrosion	-	0.9683	96.83%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.6521	65.21%
Skin corrosion	-	0.9781	97.81%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4622	46.22%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5348	53.48%
skin sensitisation	+	0.7018	70.18%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6388	63.88%
Acute Oral Toxicity (c)	III	0.7692	76.92%
Estrogen receptor binding	+	0.5627	56.27%
Androgen receptor binding	+	0.5861	58.61%
Thyroid receptor binding	+	0.7158	71.58%
Glucocorticoid receptor binding	+	0.8038	80.38%
Aromatase binding	-	0.4893	48.93%
PPAR gamma	-	0.5488	54.88%
Honey bee toxicity	-	0.9105	91.05%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3622	P33261	Cytochrome P450 2C19	7943.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	6309.6 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.14%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.50%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.46%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.90%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.36%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.60%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.58%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.38%	95.89%

Plants that contains it

• Acacia simplicifolia
• Anisochilus harmandii
• Asparagus racemosus
• Bowdichia virgilioides
• Brucea antidysenterica
• Calamus draco
• Centaurea zuccariniana
• Chamaecyparis pisifera
• Cousinia canescens
• Ferula marmarica
• Firmiana simplex
• Grazielia serrata
• Larix gmelinii var. gmelinii
• Nauclea parva
• Phagnalon bicolor
• Pinus massoniana
• Pinus merkusii
• Pinus nigra
• Pinus palustris
• Pinus pinaster
• Pinus resinosa
• Pinus taeda
• Pinus yunnanensis
• Squamopappus skutchii
• Strychnos tomentosa
• Symplocos glauca
• Teucrium scorodonia
• Tinospora hainanensis
• Titanotrichum oldhamii
• Uvaria littoralis
• Veronica anagallis
• Waitzia acuminata
• Wrightia tinctoria

Cross-Links

• PubChem: 220338
• NPASS: NPC283908
• ChEMBL: CHEMBL1410398
• LOTUS: LTS0206738
• wikiData: Q418035