(1R,2R,4aR,5R,8aS)-2-acetyloxy-5-[2-(furan-3-yl)-2-oxoethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: d6b52ca5-2663-423c-b56d-b81fc259a17a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (1R,2R,4aR,5R,8aS)-2-acetyloxy-5-[2-(furan-3-yl)-2-oxoethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• InChI: InChI=1S/C22H28O6/c1-13-5-6-18-21(3,16(13)11-17(24)15-8-10-27-12-15)9-7-19(28-14(2)23)22(18,4)20(25)26/h8,10,12,16,18-19H,1,5-7,9,11H2,2-4H3,(H,25,26)/t16-,18+,19-,21-,22-/m1/s1
• InChI Key: VZIHDWNPKBLDMB-YICCBXQDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 4.26
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9851	98.51%
Caco-2	-	0.5250	52.50%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6295	62.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7172	71.72%
OATP1B3 inhibitior	-	0.5535	55.35%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.6343	63.43%
P-glycoprotein inhibitior	-	0.4759	47.59%
P-glycoprotein substrate	-	0.7382	73.82%
CYP3A4 substrate	+	0.6666	66.66%
CYP2C9 substrate	+	0.7993	79.93%
CYP2D6 substrate	-	0.8804	88.04%
CYP3A4 inhibition	+	0.7212	72.12%
CYP2C9 inhibition	-	0.7518	75.18%
CYP2C19 inhibition	-	0.6882	68.82%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	+	0.6698	66.98%
CYP2C8 inhibition	+	0.6179	61.79%
CYP inhibitory promiscuity	-	0.6917	69.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5988	59.88%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9290	92.90%
Skin irritation	+	0.5407	54.07%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7209	72.09%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.7068	70.68%
skin sensitisation	-	0.8411	84.11%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.5786	57.86%
Acute Oral Toxicity (c)	I	0.3485	34.85%
Estrogen receptor binding	+	0.7131	71.31%
Androgen receptor binding	+	0.6280	62.80%
Thyroid receptor binding	+	0.5753	57.53%
Glucocorticoid receptor binding	+	0.7674	76.74%
Aromatase binding	+	0.5676	56.76%
PPAR gamma	+	0.5722	57.22%
Honey bee toxicity	-	0.8619	86.19%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	95.98%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	91.98%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.97%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.01%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.76%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	87.86%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.83%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.73%	91.11%
CHEMBL5028	O14672	ADAM10	87.64%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.33%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.63%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.20%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.67%	93.04%

Plants that contains it

• Dodonaea petiolaris

Cross-Links

• PubChem: 162849341
• LOTUS: LTS0052805
• wikiData: Q105299777