[(2S,3R,4S,5S)-2-[[(1S,4S,4aR,8R,8aR)-8-formyl-4-[(3R)-3-hydroxy-3-methylpent-4-enyl]-3,4a,8-trimethyl-1,4,5,6,7,8a-hexahydronaphthalen-1-yl]oxy]-3,5-dihydroxyoxan-4-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 8d5ed127-fd4f-45e7-b133-1ffff3f9ebd0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3R,4S,5S)-2-[[(1S,4S,4aR,8R,8aR)-8-formyl-4-[(3R)-3-hydroxy-3-methylpent-4-enyl]-3,4a,8-trimethyl-1,4,5,6,7,8a-hexahydronaphthalen-1-yl]oxy]-3,5-dihydroxyoxan-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(COC(C1O)OC2C=C(C(C3(C2C(CCC3)(C)C=O)C)CCC(C)(C=C)O)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@H](CO[C@H]([C@@H]1O)O[C@H]2C=C([C@@H]([C@@]3([C@@H]2[C@](CCC3)(C)C=O)C)CC[C@](C)(C=C)O)C)O
• InChI: InChI=1S/C30H46O8/c1-8-18(3)26(34)38-24-21(32)16-36-27(23(24)33)37-22-15-19(4)20(11-14-29(6,35)9-2)30(7)13-10-12-28(5,17-31)25(22)30/h8-9,15,17,20-25,27,32-33,35H,2,10-14,16H2,1,3-7H3/b18-8+/t20-,21-,22-,23+,24-,25-,27-,28-,29-,30+/m0/s1
• InChI Key: DQMQGSXRKNZKFJ-PFQFNOKLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₈
• Molecular Weight: 534.70 g/mol
• Exact Mass: 534.31926842 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8749	87.49%
Caco-2	-	0.7696	76.96%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7846	78.46%
OATP2B1 inhibitior	-	0.8640	86.40%
OATP1B1 inhibitior	+	0.7803	78.03%
OATP1B3 inhibitior	+	0.9178	91.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5704	57.04%
BSEP inhibitior	+	0.9586	95.86%
P-glycoprotein inhibitior	+	0.6741	67.41%
P-glycoprotein substrate	+	0.5602	56.02%
CYP3A4 substrate	+	0.7132	71.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8854	88.54%
CYP3A4 inhibition	-	0.6627	66.27%
CYP2C9 inhibition	-	0.8542	85.42%
CYP2C19 inhibition	-	0.8420	84.20%
CYP2D6 inhibition	-	0.9504	95.04%
CYP1A2 inhibition	-	0.8105	81.05%
CYP2C8 inhibition	+	0.5961	59.61%
CYP inhibitory promiscuity	-	0.9280	92.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7363	73.63%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9407	94.07%
Skin irritation	+	0.5522	55.22%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4492	44.92%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5652	56.52%
skin sensitisation	-	0.9002	90.02%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8225	82.25%
Acute Oral Toxicity (c)	III	0.5901	59.01%
Estrogen receptor binding	+	0.7454	74.54%
Androgen receptor binding	+	0.6179	61.79%
Thyroid receptor binding	+	0.5564	55.64%
Glucocorticoid receptor binding	+	0.7682	76.82%
Aromatase binding	+	0.6795	67.95%
PPAR gamma	+	0.6227	62.27%
Honey bee toxicity	-	0.7457	74.57%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9869	98.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.14%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.77%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.93%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.39%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.29%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.31%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.23%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.39%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.10%	90.93%
CHEMBL5028	O14672	ADAM10	85.66%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.33%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.79%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.79%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.10%	93.00%
CHEMBL3401	O75469	Pregnane X receptor	83.08%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.82%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.56%	97.28%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.02%	95.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.90%	92.88%
CHEMBL1977	P11473	Vitamin D receptor	81.49%	99.43%
CHEMBL5255	O00206	Toll-like receptor 4	80.53%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.47%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.36%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.07%	97.14%

Plants that contains it

• Gutierrezia sphaerocephala

Cross-Links

• PubChem: 163035075
• LOTUS: LTS0041411
• wikiData: Q104987034