5-acetyloxy-5-(6-hydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl)-3-methylpent-2-enoic acid

Details

• Internal ID: 00997693-f166-4d03-9bde-1511b4fb950a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 5-acetyloxy-5-(6-hydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl)-3-methylpent-2-enoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)C(CC(=CC(=O)O)C)OC(=O)C)CCC(C2=C)O)C
• SMILES (Isomeric): CC1CCC2(C(C1(C)C(CC(=CC(=O)O)C)OC(=O)C)CCC(C2=C)O)C
• InChI: InChI=1S/C22H34O5/c1-13(12-20(25)26)11-19(27-16(4)23)22(6)14(2)9-10-21(5)15(3)17(24)7-8-18(21)22/h12,14,17-19,24H,3,7-11H2,1-2,4-6H3,(H,25,26)
• InChI Key: VTPJBCUNWKVPKU-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.24062418 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9863	98.63%
Caco-2	+	0.5248	52.48%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8362	83.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8724	87.24%
OATP1B3 inhibitior	-	0.2662	26.62%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.8390	83.90%
P-glycoprotein inhibitior	-	0.6491	64.91%
P-glycoprotein substrate	-	0.7612	76.12%
CYP3A4 substrate	+	0.6464	64.64%
CYP2C9 substrate	-	0.7828	78.28%
CYP2D6 substrate	-	0.9079	90.79%
CYP3A4 inhibition	-	0.5143	51.43%
CYP2C9 inhibition	-	0.9160	91.60%
CYP2C19 inhibition	-	0.9086	90.86%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9077	90.77%
CYP2C8 inhibition	-	0.6720	67.20%
CYP inhibitory promiscuity	-	0.9071	90.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.7195	71.95%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.8828	88.28%
Skin irritation	+	0.6224	62.24%
Skin corrosion	-	0.9623	96.23%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3944	39.44%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.6902	69.02%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6269	62.69%
Acute Oral Toxicity (c)	III	0.7476	74.76%
Estrogen receptor binding	+	0.7320	73.20%
Androgen receptor binding	+	0.5812	58.12%
Thyroid receptor binding	+	0.6067	60.67%
Glucocorticoid receptor binding	+	0.7776	77.76%
Aromatase binding	+	0.7521	75.21%
PPAR gamma	+	0.5918	59.18%
Honey bee toxicity	-	0.7165	71.65%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.15%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.01%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.11%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.89%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	87.31%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.30%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.49%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.25%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.59%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.26%	95.89%

Plants that contains it

• Plectranthus ornatus

Cross-Links

• PubChem: 72777084
• LOTUS: LTS0139828
• wikiData: Q105292916