Botcineric acid

Details

• Internal ID: b5a1bd16-b1ef-472d-bb14-e7a0f240152e
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohols
• IUPAC Name: (2R,3S)-3-hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-[(E,4S)-4-hydroxydec-2-enoyl]oxy-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid
• SMILES (Canonical): CCCCCCC(C=CC(=O)OC1C(C(C(OC1C)(C)C(C(C)C(=O)O)O)O)C)O
• SMILES (Isomeric): CCCCCC[C@@H](/C=C/C(=O)O[C@@H]1[C@H]([C@@H]([C@@](O[C@H]1C)(C)[C@H]([C@@H](C)C(=O)O)O)O)C)O
• InChI: InChI=1S/C22H38O8/c1-6-7-8-9-10-16(23)11-12-17(24)29-18-13(2)19(25)22(5,30-15(18)4)20(26)14(3)21(27)28/h11-16,18-20,23,25-26H,6-10H2,1-5H3,(H,27,28)/b12-11+/t13-,14-,15+,16+,18-,19+,20+,22+/m1/s1
• InChI Key: CIZAXJJDWVUEEL-AFQFPRFFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₈O₈
• Molecular Weight: 430.50 g/mol
• Exact Mass: 430.25666817 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• Homobotcinolide
• (2R,3S)-3-hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-[(E,4S)-4-hydroxydec-2-enoyl]oxy-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid
• Botcinerate
• (2R,3S)-3-Hydroxy-3-((2S,3S,4S,5R,6S)-3-hydroxy-5-(((4S)-4-hydroxydec-2-enoyl)oxy)-2,4,6-trimethyloxan-2-yl)-2-methylpropanoate
• (2R,3S)-3-hydroxy-3-((2S,3S,4S,5R,6S)-3-hydroxy-5-((E,4S)-4-hydroxydec-2-enoyl)oxy-2,4,6-trimethyloxan-2-yl)-2-methylpropanoic acid
• (2R,3S)-3-Hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoate
• RefChem:121078
• 177182-59-1
• orb2564123
• CHEBI:202432
• HY-N12652
• CS-1010888

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7885	78.85%
Caco-2	-	0.7919	79.19%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7806	78.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	+	0.8600	86.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8546	85.46%
P-glycoprotein inhibitior	-	0.5883	58.83%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6316	63.16%
CYP2C9 substrate	-	0.8047	80.47%
CYP2D6 substrate	-	0.9055	90.55%
CYP3A4 inhibition	+	0.5663	56.63%
CYP2C9 inhibition	-	0.8886	88.86%
CYP2C19 inhibition	-	0.7071	70.71%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.9152	91.52%
CYP2C8 inhibition	-	0.6360	63.60%
CYP inhibitory promiscuity	-	0.9538	95.38%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7430	74.30%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9675	96.75%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9329	93.29%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5992	59.92%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5676	56.76%
skin sensitisation	-	0.8537	85.37%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8876	88.76%
Acute Oral Toxicity (c)	III	0.4013	40.13%
Estrogen receptor binding	+	0.6509	65.09%
Androgen receptor binding	-	0.5491	54.91%
Thyroid receptor binding	-	0.5903	59.03%
Glucocorticoid receptor binding	+	0.7609	76.09%
Aromatase binding	+	0.6104	61.04%
PPAR gamma	-	0.5351	53.51%
Honey bee toxicity	-	0.8627	86.27%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5239	52.39%
Fish aquatic toxicity	+	0.9561	95.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.21%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	96.70%	98.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.69%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.67%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.64%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	96.60%	93.56%
CHEMBL2996	Q05655	Protein kinase C delta	94.09%	97.79%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	94.05%	96.47%
CHEMBL230	P35354	Cyclooxygenase-2	93.17%	89.63%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.01%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.93%	97.29%
CHEMBL340	P08684	Cytochrome P450 3A4	88.46%	91.19%
CHEMBL4040	P28482	MAP kinase ERK2	88.44%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.21%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.78%	94.08%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.24%	92.86%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.95%	100.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.55%	92.08%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	85.25%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.15%	94.73%
CHEMBL3045	P05771	Protein kinase C beta	84.51%	97.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.98%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	82.79%	92.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.33%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.32%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.05%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.91%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.79%	97.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.68%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.08%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11711675
• LOTUS: LTS0181521
• wikiData: Q77371302