methyl (Z)-3-[(1R,2R,4S,7S,8S,9R,11R,12S,13R,17S)-9-acetyloxy-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.02,4.02,8.013,17]heptadecan-12-yl]prop-2-enoate

Details

• Internal ID: fa63bea9-0b98-4259-b63a-37f429babe0b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (Z)-3-[(1R,2R,4S,7S,8S,9R,11R,12S,13R,17S)-9-acetyloxy-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.02,4.02,8.013,17]heptadecan-12-yl]prop-2-enoate
• SMILES (Canonical): CC(=O)OC1CC2C(C3(C(=O)C(OC3(C2(C45C1(C(OC(=O)C4O5)C6=COC=C6)C)C)O)(C)C)O)(C)C=CC(=O)OC
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@]([C@]3(C(=O)C(O[C@]3([C@]2([C@]45[C@@]1([C@@H](OC(=O)[C@H]4O5)C6=COC=C6)C)C)O)(C)C)O)(C)/C=C\C(=O)OC
• InChI: InChI=1S/C29H34O12/c1-14(30)38-17-12-16-24(4,10-8-18(31)36-7)27(34)22(33)23(2,3)41-29(27,35)26(16,6)28-20(40-28)21(32)39-19(25(17,28)5)15-9-11-37-13-15/h8-11,13,16-17,19-20,34-35H,12H2,1-7H3/b10-8-/t16-,17-,19+,20-,24+,25+,26-,27+,28-,29+/m1/s1
• InChI Key: HOHMQEBYHJKCEM-UTOFRLHLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₂
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.20502652 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9157	91.57%
Caco-2	-	0.7660	76.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	0.7141	71.41%
OATP1B1 inhibitior	-	0.3205	32.05%
OATP1B3 inhibitior	+	0.8363	83.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9593	95.93%
P-glycoprotein inhibitior	+	0.7789	77.89%
P-glycoprotein substrate	+	0.5548	55.48%
CYP3A4 substrate	+	0.7190	71.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8761	87.61%
CYP3A4 inhibition	+	0.6998	69.98%
CYP2C9 inhibition	-	0.8114	81.14%
CYP2C19 inhibition	-	0.7328	73.28%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	-	0.9063	90.63%
CYP2C8 inhibition	+	0.6736	67.36%
CYP inhibitory promiscuity	-	0.8305	83.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.4657	46.57%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8869	88.69%
Skin irritation	-	0.7360	73.60%
Skin corrosion	-	0.9058	90.58%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7053	70.53%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.5321	53.21%
skin sensitisation	-	0.8186	81.86%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8166	81.66%
Acute Oral Toxicity (c)	III	0.3793	37.93%
Estrogen receptor binding	+	0.7659	76.59%
Androgen receptor binding	+	0.7704	77.04%
Thyroid receptor binding	+	0.6584	65.84%
Glucocorticoid receptor binding	+	0.7630	76.30%
Aromatase binding	+	0.7081	70.81%
PPAR gamma	+	0.6651	66.51%
Honey bee toxicity	-	0.7006	70.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9633	96.33%

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	99.89%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.80%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.93%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.08%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	92.00%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.88%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.70%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	86.29%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.13%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	83.57%	90.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.87%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.22%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.35%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.32%	94.00%
CHEMBL5028	O14672	ADAM10	80.90%	97.50%

Plants that contains it

• Harrisonia abyssinica
• Peltodon longipes

Cross-Links

• PubChem: 163014999
• LOTUS: LTS0086847
• wikiData: Q105308232