methyl (Z)-3-[(1R,2R,4S,7S,8R,9S,10R,11R,12R,13R,17S)-9,10-diacetyloxy-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: 5d893ab0-7d2d-44c2-8f7c-1a98ee828af1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (Z)-3-[(1R,2R,4S,7S,8R,9S,10R,11R,12R,13R,17S)-9,10-diacetyloxy-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)OC1C2C(C3(C(=O)C(OC3(C2(C45C(O4)C(=O)OC(C5(C1OC(=O)C)C)C6=COC=C6)C)O)(C)C)O)(C)C=CC(=O)OC
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]2[C@@]([C@]3(C(=O)C(O[C@]3([C@]2([C@]45[C@H](O4)C(=O)O[C@H]([C@@]5([C@@H]1OC(=O)C)C)C6=COC=C6)C)O)(C)C)O)(C)/C=C\C(=O)OC
• InChI: InChI=1S/C31H36O14/c1-14(32)41-18-19-26(5,11-9-17(34)39-8)29(37)24(36)25(3,4)45-31(29,38)28(19,7)30-22(44-30)23(35)43-20(16-10-12-40-13-16)27(30,6)21(18)42-15(2)33/h9-13,18-22,37-38H,1-8H3/b11-9-/t18-,19-,20+,21-,22-,26-,27-,28-,29+,30-,31+/m1/s1
• InChI Key: HVLGSQRFTUKQIK-DDQFOKMUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₆O₁₄
• Molecular Weight: 632.60 g/mol
• Exact Mass: 632.21050582 g/mol
• Topological Polar Surface Area (TPSA): 198.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9279	92.79%
Caco-2	-	0.7945	79.45%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7299	72.99%
OATP2B1 inhibitior	-	0.7165	71.65%
OATP1B1 inhibitior	+	0.6978	69.78%
OATP1B3 inhibitior	+	0.8546	85.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9697	96.97%
P-glycoprotein inhibitior	+	0.8197	81.97%
P-glycoprotein substrate	+	0.5174	51.74%
CYP3A4 substrate	+	0.7025	70.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8773	87.73%
CYP3A4 inhibition	+	0.6953	69.53%
CYP2C9 inhibition	-	0.8228	82.28%
CYP2C19 inhibition	-	0.6539	65.39%
CYP2D6 inhibition	-	0.8917	89.17%
CYP1A2 inhibition	-	0.9435	94.35%
CYP2C8 inhibition	+	0.6484	64.84%
CYP inhibitory promiscuity	-	0.7544	75.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.5610	56.10%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8757	87.57%
Skin irritation	-	0.7596	75.96%
Skin corrosion	-	0.9296	92.96%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6447	64.47%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8123	81.23%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8675	86.75%
Acute Oral Toxicity (c)	III	0.4863	48.63%
Estrogen receptor binding	+	0.7577	75.77%
Androgen receptor binding	+	0.7715	77.15%
Thyroid receptor binding	+	0.6541	65.41%
Glucocorticoid receptor binding	+	0.7164	71.64%
Aromatase binding	+	0.6518	65.18%
PPAR gamma	+	0.7020	70.20%
Honey bee toxicity	-	0.7314	73.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5053	50.53%
Fish aquatic toxicity	+	0.9635	96.35%

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	99.83%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.69%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.27%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.57%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.99%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.84%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	89.07%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.30%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.14%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.99%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.08%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.77%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.16%	97.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.69%	94.42%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.26%	95.71%

Plants that contains it

• Harrisonia abyssinica
• Harrisonia perforata

Cross-Links

• PubChem: 10532085
• LOTUS: LTS0230046
• wikiData: Q105034326