Imbricatolic Acid

Details

• Internal ID: 150fe6c7-7ba0-472e-ad25-4995c81cf905
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aR,5S,8aR)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C)CCO
• SMILES (Isomeric): C[C@@H](CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C)CCO
• InChI: InChI=1S/C20H34O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h14,16-17,21H,2,5-13H2,1,3-4H3,(H,22,23)/t14-,16-,17+,19+,20-/m0/s1
• InChI Key: NSRKLZRKJJQJLD-BEUFEYIVSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.65
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 6832-60-6
• (1S,4aR,5S,8aR)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CHEMBL2048004
• BDBM50155758
• AKOS032948632

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.7544	75.44%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6614	66.14%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8237	82.37%
OATP1B3 inhibitior	+	0.8791	87.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5991	59.91%
BSEP inhibitior	+	0.5996	59.96%
P-glycoprotein inhibitior	-	0.7689	76.89%
P-glycoprotein substrate	-	0.6951	69.51%
CYP3A4 substrate	+	0.5901	59.01%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	+	0.5212	52.12%
CYP2C9 inhibition	-	0.7877	78.77%
CYP2C19 inhibition	-	0.8777	87.77%
CYP2D6 inhibition	-	0.9260	92.60%
CYP1A2 inhibition	-	0.8601	86.01%
CYP2C8 inhibition	-	0.8498	84.98%
CYP inhibitory promiscuity	-	0.8227	82.27%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6589	65.89%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.8029	80.29%
Skin irritation	-	0.6598	65.98%
Skin corrosion	-	0.9722	97.22%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5426	54.26%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6981	69.81%
skin sensitisation	-	0.6258	62.58%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6309	63.09%
Acute Oral Toxicity (c)	III	0.7406	74.06%
Estrogen receptor binding	+	0.7075	70.75%
Androgen receptor binding	+	0.5389	53.89%
Thyroid receptor binding	+	0.7019	70.19%
Glucocorticoid receptor binding	+	0.7055	70.55%
Aromatase binding	-	0.5304	53.04%
PPAR gamma	-	0.5389	53.89%
Honey bee toxicity	-	0.9219	92.19%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	8800 nM	IC50	PMID: 26965864

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.90%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.12%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.62%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.87%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.49%	91.11%
CHEMBL2581	P07339	Cathepsin D	84.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.95%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.30%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.62%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.57%	90.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.36%	96.47%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.31%	96.38%
CHEMBL237	P41145	Kappa opioid receptor	82.25%	98.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.08%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.01%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.30%	100.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	80.01%	95.71%

Plants that contains it

• Actinidia chinensis var. deliciosa
• Araucaria angustifolia
• Asparagus officinalis
• Astragalus dissectus
• Breonia chinensis
• Campylotropis hirtella
• Ceropegia dichotoma
• Crinum moorei
• Crotalaria candicans
• Cryptomeria japonica
• Cupressus arizonica var. nevadensis
• Cupressus sempervirens
• Dendrobium loddigesii
• Dicranopteris linearis
• Distephanus angulifolius
• Eucalyptus apodophylla
• Glycosmis macrophylla
• Gypsophila perfoliata
• Hypericum polyanthemum
• Juniperus chinensis
• Juniperus communis
• Juniperus drupacea
• Juniperus formosana
• Lepidium apetalum
• Lophostemon confertus
• Mentha × gentilis
• Ocotea minarum
• Ononis spinosa
• Orbivestus karaguensis
• Pentaclethra macrophylla
• Periploca sepium
• Pinalia japonica
• Plectranthus hereroensis
• Pterocaulon virgatum
• Rhodiola semenovii
• Salvia sessei
• Sonneratia caseolaris
• Stephania zippeliana
• Veronica polita

Cross-Links

• PubChem: 70688370
• NPASS: NPC91369
• ChEMBL: CHEMBL2048004
• LOTUS: LTS0198731
• wikiData: Q105185214