[(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-[(Z)-2-methylbut-2-enoyl]oxy-11-oxo-4,12-dioxapentacyclo[7.7.0.01,6.02,13.010,15]hexadec-2-en-5-yl] (2R,3S)-3-hydroxy-2-methylbutanoate

Details

• Internal ID: 98f3b3ff-eaad-425c-a1c3-1b843b186d4d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-[(Z)-2-methylbut-2-enoyl]oxy-11-oxo-4,12-dioxapentacyclo[7.7.0.01,6.02,13.010,15]hexadec-2-en-5-yl] (2R,3S)-3-hydroxy-2-methylbutanoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2CC34C5CC(C3C2(C(=O)OC1C4=COC5OC(=O)C(C)C(C)O)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H]2C[C@]34[C@@H]5C[C@@H]([C@@H]3[C@]2(C(=O)O[C@H]1C4=CO[C@@H]5OC(=O)[C@H](C)[C@H](C)O)C)O
• InChI: InChI=1S/C25H32O9/c1-6-10(2)20(28)32-17-14-8-25-13-7-16(27)19(25)24(14,5)23(30)33-18(17)15(25)9-31-22(13)34-21(29)11(3)12(4)26/h6,9,11-14,16-19,22,26-27H,7-8H2,1-5H3/b10-6-/t11-,12+,13-,14-,16+,17-,18+,19-,22-,24+,25-/m1/s1
• InChI Key: SMKHURCHQAAFHG-DSFPCPNSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₉
• Molecular Weight: 476.50 g/mol
• Exact Mass: 476.20463259 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 9
• 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	+	0.9646	96.46%
Caco-2	-	0.7400	74.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7277	72.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8209	82.09%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7447	74.47%
P-glycoprotein inhibitior	+	0.5805	58.05%
P-glycoprotein substrate	+	0.5868	58.68%
CYP3A4 substrate	+	0.6921	69.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.7641	76.41%
CYP2C9 inhibition	-	0.9318	93.18%
CYP2C19 inhibition	-	0.9351	93.51%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.8425	84.25%
CYP2C8 inhibition	-	0.6716	67.16%
CYP inhibitory promiscuity	-	0.9462	94.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4499	44.99%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9417	94.17%
Skin irritation	+	0.5481	54.81%
Skin corrosion	-	0.9222	92.22%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4077	40.77%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.6479	64.79%
skin sensitisation	-	0.8213	82.13%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.5084	50.84%
Estrogen receptor binding	+	0.8224	82.24%
Androgen receptor binding	+	0.6680	66.80%
Thyroid receptor binding	+	0.5659	56.59%
Glucocorticoid receptor binding	+	0.6634	66.34%
Aromatase binding	+	0.5831	58.31%
PPAR gamma	+	0.5712	57.12%
Honey bee toxicity	-	0.6548	65.48%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9733	97.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.53%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.39%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.80%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.61%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.31%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.36%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.21%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.20%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.87%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.70%	91.07%
CHEMBL2581	P07339	Cathepsin D	89.56%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.38%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	84.80%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	84.37%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.85%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	81.45%	98.03%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.41%	93.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.85%	83.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.55%	100.00%

Plants that contains it

• Trixis grisebachii

Cross-Links

• PubChem: 162850084
• LOTUS: LTS0025531
• wikiData: Q105255981