Orbiculin E

Details

• Internal ID: 6acf519c-256c-4b07-b222-806352206f90
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Agarofurans
• IUPAC Name: [(1S,2R,4S,5R,6R,7S,9R,12R)-4,5-diacetyloxy-7-benzoyloxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-12-yl] furan-3-carboxylate
• SMILES (Canonical): CC1CC(C(C2(C13C(C(CC2OC(=O)C4=CC=CC=C4)C(O3)(C)C)OC(=O)C5=COC=C5)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@H]([C@@]2([C@]13[C@@H]([C@@H](C[C@@H]2OC(=O)C4=CC=CC=C4)C(O3)(C)C)OC(=O)C5=COC=C5)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C31H36O10/c1-17-14-23(37-18(2)32)26(38-19(3)33)30(6)24(39-27(34)20-10-8-7-9-11-20)15-22-25(31(17,30)41-29(22,4)5)40-28(35)21-12-13-36-16-21/h7-13,16-17,22-26H,14-15H2,1-6H3/t17-,22-,23+,24+,25-,26+,30-,31-/m1/s1
• InChI Key: GAOKKLOHOKIMQT-KBAKPPLISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₆O₁₀
• Molecular Weight: 568.60 g/mol
• Exact Mass: 568.23084734 g/mol
• Topological Polar Surface Area (TPSA): 128.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.51
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• CHEBI:66826
• 1beta,2beta-diacetoxy-9alpha-benzoyloxy-6alpha-(3-furoyloxy)-dihydro-beta-agarofuran
• (1S,2R,4S,5R,6R,7S,9R,12R)-4,5-diacetoxy-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0(1,6)]dodec-12-yl 3-furoate
• (3R,5S,5aR,6R,7S,9R,9aS,10R)-6,7-bis(acetyloxy)-5-(benzoyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepin-10-yl furan-3-carboxylate
• [(1S,2R,4S,5R,6R,7S,9R,12R)-4,5-diacetyloxy-7-benzoyloxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-12-yl] furan-3-carboxylate
• ((1S,2R,4S,5R,6R,7S,9R,12R)-4,5-diacetyloxy-7-benzoyloxy-2,6,10,10-tetramethyl-11-oxatricyclo(7.2.1.01,6)dodecan-12-yl) furan-3-carboxylate
• (1S,2R,4S,5R,6R,7S,9R,12R)-4,5-Diacetoxy-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo(7.2.1.0(1,6))dodec-12-yl 3-furoate
• (1S,2R,4S,5R,6R,7S,9R,12R)-4,5-Diacetoxy-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo(7.2.1.0(1,6))dodec-12-yl 3-furoic acid
• (1S,2R,4S,5R,6R,7S,9R,12R)-4,5-Diacetoxy-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0(1,6)]dodec-12-yl 3-furoic acid
• RefChem:168422
• 1b,2b-Diacetoxy-9a-benzoyloxy-6a-(3-furoyloxy)-dihydro-b-agarofuran
• 227450-69-3
• Q27135459

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9871	98.71%
Caco-2	-	0.6634	66.34%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5791	57.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8202	82.02%
OATP1B3 inhibitior	+	0.8686	86.86%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9282	92.82%
P-glycoprotein inhibitior	+	0.9118	91.18%
P-glycoprotein substrate	-	0.5768	57.68%
CYP3A4 substrate	+	0.6777	67.77%
CYP2C9 substrate	+	0.5931	59.31%
CYP2D6 substrate	-	0.8574	85.74%
CYP3A4 inhibition	-	0.5476	54.76%
CYP2C9 inhibition	-	0.8377	83.77%
CYP2C19 inhibition	-	0.7795	77.95%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.8284	82.84%
CYP2C8 inhibition	+	0.7676	76.76%
CYP inhibitory promiscuity	-	0.8507	85.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4318	43.18%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8781	87.81%
Skin irritation	-	0.7673	76.73%
Skin corrosion	-	0.8888	88.88%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8952	89.52%
Micronuclear	-	0.6726	67.26%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7414	74.14%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6107	61.07%
Acute Oral Toxicity (c)	III	0.5503	55.03%
Estrogen receptor binding	+	0.8468	84.68%
Androgen receptor binding	+	0.6519	65.19%
Thyroid receptor binding	+	0.6745	67.45%
Glucocorticoid receptor binding	+	0.7704	77.04%
Aromatase binding	+	0.6583	65.83%
PPAR gamma	+	0.7456	74.56%
Honey bee toxicity	-	0.7966	79.66%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5045	50.45%
Fish aquatic toxicity	+	0.9931	99.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.29%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.07%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.69%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.33%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.22%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.09%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.77%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.75%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	88.82%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.49%	97.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.46%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.06%	91.19%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.25%	81.11%
CHEMBL5028	O14672	ADAM10	85.09%	97.50%
CHEMBL1951	P21397	Monoamine oxidase A	84.99%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.36%	83.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.65%	95.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.59%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.78%	89.00%

Plants that contains it

• Celastrus orbiculatus

Cross-Links

• PubChem: 10437950
• NPASS: NPC243302
• LOTUS: LTS0059606
• wikiData: Q27135459