Taxuspinanane A

Details

• Internal ID: ec28950e-4dc3-4533-b313-e0ac1057adcf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-(4-methylhexanoylamino)-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• SMILES (Canonical): CCC(C)CCC(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• SMILES (Isomeric): CCC(C)CCC(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H]([C@H]4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• InChI: InChI=1S/C47H59NO14/c1-9-25(2)20-21-34(52)48-36(29-16-12-10-13-17-29)37(53)43(56)60-31-23-47(57)41(61-42(55)30-18-14-11-15-19-30)39-45(8,32(51)22-33-46(39,24-58-33)62-28(5)50)40(54)38(59-27(4)49)35(26(31)3)44(47,6)7/h10-19,25,31-33,36-39,41,51,53,57H,9,20-24H2,1-8H3,(H,48,52)/t25?,31-,32-,33+,36-,37+,38+,39-,41-,45+,46-,47+/m0/s1
• InChI Key: LNTOLDCVMUNKRU-GVZBEMDZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₅₉NO₁₄
• Molecular Weight: 862.00 g/mol
• Exact Mass: 861.39355556 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 4.25
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 13

Synonyms

• SCHEMBL44478
• CHEMBL449978
• [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-(4-methylhexanoylamino)-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.8809	88.09%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6088	60.88%
OATP2B1 inhibitior	-	0.7400	74.00%
OATP1B1 inhibitior	-	0.5287	52.87%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.8700	87.00%
OCT2 inhibitior	-	0.7776	77.76%
BSEP inhibitior	+	0.9721	97.21%
P-glycoprotein inhibitior	+	0.7821	78.21%
P-glycoprotein substrate	+	0.9327	93.27%
CYP3A4 substrate	+	0.7748	77.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	+	0.5373	53.73%
CYP2C9 inhibition	-	0.8298	82.98%
CYP2C19 inhibition	-	0.8153	81.53%
CYP2D6 inhibition	-	0.9108	91.08%
CYP1A2 inhibition	-	0.8449	84.49%
CYP2C8 inhibition	+	0.9467	94.67%
CYP inhibitory promiscuity	-	0.7164	71.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4907	49.07%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9110	91.10%
Skin irritation	-	0.7477	74.77%
Skin corrosion	-	0.9302	93.02%
Ames mutagenesis	-	0.8337	83.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7189	71.89%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6765	67.65%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.5587	55.87%
Acute Oral Toxicity (c)	III	0.6273	62.73%
Estrogen receptor binding	+	0.8246	82.46%
Androgen receptor binding	+	0.8226	82.26%
Thyroid receptor binding	+	0.7014	70.14%
Glucocorticoid receptor binding	+	0.7887	78.87%
Aromatase binding	+	0.6226	62.26%
PPAR gamma	+	0.8108	81.08%
Honey bee toxicity	-	0.6527	65.27%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9904	99.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.96%	90.17%
CHEMBL2581	P07339	Cathepsin D	99.61%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.65%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.86%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.58%	96.47%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.28%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	94.92%	87.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.09%	86.33%
CHEMBL2535	P11166	Glucose transporter	92.19%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.99%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	91.96%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.81%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.10%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.95%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.63%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.93%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.57%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.47%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.35%	82.69%
CHEMBL5028	O14672	ADAM10	89.13%	97.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.17%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	86.79%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.26%	94.62%
CHEMBL4302	P08183	P-glycoprotein 1	85.98%	92.98%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.31%	89.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.67%	89.34%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.90%	94.08%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.64%	97.14%
CHEMBL4267	P37173	TGF-beta receptor type II	82.62%	88.18%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.46%	81.11%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.54%	89.23%

Plants that contains it

• Taxus baccata
• Taxus cuspidata

Cross-Links

• PubChem: 10700798
• NPASS: NPC275170