1-O-[(2S)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-O-methyl (2S)-2-hydroxy-2-(3-methylbutyl)butanedioate

Details

• Internal ID: f4ca4935-9216-4006-8091-30200271a196
• Taxonomy: Alkaloids and derivatives > Cephalotaxus alkaloids
• IUPAC Name: 1-O-[(2S)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-O-methyl (2S)-2-hydroxy-2-(3-methylbutyl)butanedioate
• SMILES (Canonical): CC(C)CCC(CC(=O)OC)(C(=O)OC1C2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O
• SMILES (Isomeric): CC(C)CC[C@](CC(=O)OC)(C(=O)OC1[C@H]2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O
• InChI: InChI=1S/C28H37NO8/c1-17(2)6-9-28(32,15-23(30)34-4)26(31)37-25-22(33-3)14-27-8-5-10-29(27)11-7-18-12-20-21(36-16-35-20)13-19(18)24(25)27/h12-14,17,24-25,32H,5-11,15-16H2,1-4H3/t24-,25?,27?,28+/m1/s1
• InChI Key: WRCBXHDQHPUVHW-KBXBIZAPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₇NO₈
• Molecular Weight: 515.60 g/mol
• Exact Mass: 515.25191714 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• Cephalotaxine, 4-methyl-, 2-hydroxy-2-(3-methylbutyl)butanedioate (ester), (3(R))-
• Cephalotaxine, 4-methyl-2-hydroxy-2-(3-methylbutyl)butanedioate (ester), (3(R))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	-	0.5524	55.24%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5476	54.76%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8680	86.80%
OATP1B3 inhibitior	+	0.9240	92.40%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8809	88.09%
P-glycoprotein inhibitior	+	0.8159	81.59%
P-glycoprotein substrate	+	0.8638	86.38%
CYP3A4 substrate	+	0.6915	69.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7342	73.42%
CYP3A4 inhibition	+	0.7417	74.17%
CYP2C9 inhibition	-	0.9057	90.57%
CYP2C19 inhibition	-	0.8648	86.48%
CYP2D6 inhibition	-	0.8724	87.24%
CYP1A2 inhibition	-	0.8941	89.41%
CYP2C8 inhibition	+	0.4850	48.50%
CYP inhibitory promiscuity	-	0.9561	95.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Danger	0.4176	41.76%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9430	94.30%
Skin irritation	-	0.7798	77.98%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6714	67.14%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8241	82.41%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8326	83.26%
Acute Oral Toxicity (c)	III	0.6473	64.73%
Estrogen receptor binding	+	0.7495	74.95%
Androgen receptor binding	+	0.8327	83.27%
Thyroid receptor binding	+	0.5695	56.95%
Glucocorticoid receptor binding	+	0.8236	82.36%
Aromatase binding	+	0.6104	61.04%
PPAR gamma	+	0.5396	53.96%
Honey bee toxicity	-	0.7788	77.88%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6056	60.56%
Fish aquatic toxicity	+	0.9435	94.35%

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	99.52%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.34%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.84%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.92%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.90%	92.62%
CHEMBL2581	P07339	Cathepsin D	95.77%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.26%	96.77%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	92.47%	95.55%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.88%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.91%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.21%	97.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.79%	90.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.72%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.45%	95.89%
CHEMBL5028	O14672	ADAM10	86.07%	97.50%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	85.79%	96.25%
CHEMBL340	P08684	Cytochrome P450 3A4	85.61%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.59%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.08%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.03%	89.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.89%	98.75%
CHEMBL237	P41145	Kappa opioid receptor	83.53%	98.10%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.36%	91.03%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	83.10%	87.16%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.87%	97.14%
CHEMBL4581	P52732	Kinesin-like protein 1	82.61%	93.18%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.79%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.94%	96.47%

Plants that contains it

• Cephalotaxus fortunei
• Cephalotaxus hainanensis
• Panax ginseng
• Schisandra chinensis

Cross-Links

• PubChem: 56840949
• NPASS: NPC47452
• LOTUS: LTS0095424
• wikiData: Q105311157