4-[[(4aR,5S,6R,8aR)-5-[2-[(3R,5S)-5-[(2S,4R)-4-[2-[(1S,2R,4aR,8aR)-5-(3-carboxypropanoyloxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]oxolan-2-yl]oxyoxolan-3-yl]ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy]-4-oxobutanoic acid

Details

• Internal ID: 65a9d658-7bac-4d48-828c-459d5b1409bb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 4-[[(4aR,5S,6R,8aR)-5-[2-[(3R,5S)-5-[(2S,4R)-4-[2-[(1S,2R,4aR,8aR)-5-(3-carboxypropanoyloxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]oxolan-2-yl]oxyoxolan-3-yl]ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy]-4-oxobutanoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3CC(OC3)OC4CC(CO4)CCC5(C(CCC6(C5CCC=C6COC(=O)CCC(=O)O)C)C)C)CCC=C2COC(=O)CCC(=O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC[C@@H]3C[C@@H](OC3)O[C@H]4C[C@H](CO4)CC[C@]5([C@@H](CC[C@@]6([C@@H]5CCC=C6COC(=O)CCC(=O)O)C)C)C)CCC=C2COC(=O)CCC(=O)O)C
• InChI: InChI=1S/C48H74O11/c1-31-17-21-47(5)35(29-55-41(53)15-13-39(49)50)9-7-11-37(47)45(31,3)23-19-33-25-43(57-27-33)59-44-26-34(28-58-44)20-24-46(4)32(2)18-22-48(6)36(10-8-12-38(46)48)30-56-42(54)16-14-40(51)52/h9-10,31-34,37-38,43-44H,7-8,11-30H2,1-6H3,(H,49,50)(H,51,52)/t31-,32-,33-,34-,37-,38-,43+,44+,45+,46+,47+,48+/m1/s1
• InChI Key: MMHRWDFWBWUNGX-GIINAREQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₄O₁₁
• Molecular Weight: 827.10 g/mol
• Exact Mass: 826.52311317 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 9.20
• Atomic LogP (AlogP): 9.66
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	-	0.8525	85.25%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8041	80.41%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.8267	82.67%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.9437	94.37%
P-glycoprotein inhibitior	+	0.7646	76.46%
P-glycoprotein substrate	-	0.5624	56.24%
CYP3A4 substrate	+	0.6741	67.41%
CYP2C9 substrate	-	0.6166	61.66%
CYP2D6 substrate	-	0.8883	88.83%
CYP3A4 inhibition	-	0.7282	72.82%
CYP2C9 inhibition	-	0.8534	85.34%
CYP2C19 inhibition	-	0.9316	93.16%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	+	0.7347	73.47%
CYP inhibitory promiscuity	-	0.9436	94.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4710	47.10%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9001	90.01%
Skin irritation	-	0.5493	54.93%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.6308	63.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.4135	41.35%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5524	55.24%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8361	83.61%
Acute Oral Toxicity (c)	I	0.4149	41.49%
Estrogen receptor binding	+	0.7661	76.61%
Androgen receptor binding	+	0.7236	72.36%
Thyroid receptor binding	-	0.5068	50.68%
Glucocorticoid receptor binding	+	0.6863	68.63%
Aromatase binding	+	0.6480	64.80%
PPAR gamma	+	0.6916	69.16%
Honey bee toxicity	-	0.7776	77.76%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9937	99.37%

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	99.08%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.22%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.82%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.30%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	92.60%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	91.94%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.33%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.76%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.60%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	86.25%	97.79%
CHEMBL2581	P07339	Cathepsin D	85.44%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.25%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.51%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.24%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.17%	95.56%

Plants that contains it

• Baccharis heterophylla
• Baccharis patagonica
• Baccharis peruviana

Cross-Links

• PubChem: 162903228
• LOTUS: LTS0212533
• wikiData: Q105167757