Omacetaxine Mepesuccinate

Details

• Internal ID: c68be6f8-6fbc-48e1-bc16-08debdda888c
• Taxonomy: Alkaloids and derivatives > Cephalotaxus alkaloids
• IUPAC Name: 1-O-[(2S,3S,6R)-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 (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate
• SMILES (Canonical): CC(C)(CCCC(CC(=O)OC)(C(=O)OC1C2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O)O
• SMILES (Isomeric): CC(C)(CCC[C@@](CC(=O)OC)(C(=O)O[C@H]1[C@H]2C3=CC4=C(C=C3CCN5[C@@]2(CCC5)C=C1OC)OCO4)O)O
• InChI: InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1
• InChI Key: HYFHYPWGAURHIV-JFIAXGOJSA-N
• Popularity: 1,112 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₉NO₉
• Molecular Weight: 545.60 g/mol
• Exact Mass: 545.26248182 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• Omacetaxine mepesuccinate
• 26833-87-4
• Myelostat
• Ceflatonin
• Synribo
• Omapro
• CGX-635
• Homoharringtonin
• (-)-homoharringtonine
• NSC-141633
• NSC 141633
• CHEBI:71019
• UNII-6FG8041S5B
• (2'R,3S,4S,5R)-(-)-homoharringtonine
• omacetaxini mepesuccinas
• 6FG8041S5B
• HHT
• mepesuccinate d'omacetaxine
• mepesuccinato de omacetaxina
• BRN 5687925
• Omacetaxine (homoharringtonine)
• Omacetaxine mepesuccinate [USAN]
• Cephalotaxine 4-Methyl (2R)-2-Hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (Ester)
• Cephalotaxine, 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)
• 1-O-[(2S,3S,6R)-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 (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate
• Cephalotaxine 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate
• Omacetaxine mepesuccinate (USAN)
• Tekinex
• C29H39NO9
• Cephalotaxine, 4-methyl-, 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)
• OMACETAXINE MEPESUCCINATE (MART.)
• OMACETAXINE MEPESUCCINATE [MART.]
• Synribo (TN)
• Omacetaxine mepesuccinate;HHT
• DTXCID8025678
• NSC141633
• NCGC00025155-01
• 1-((1S,3AR,14BS)-2-METHOXY-1,5,6,8,9,14B-HEXAHYDRO-4H-CYCLOPENTA(A)(1,3)DIOXOLO(4,5-H)PYRROLO(2,1-B)(3)BENZAZEPIN-1-YL) 4-METHYL (2R)-2-HYDROXY-2-(4-HYDROXY-4-METHYLPENTYL)BUTANEDIOATE
• 1-[(1S,3aR,14bS)-2-Methoxy-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-H]pyrrolo[2,1-b][3]benzazepin-1-yl] 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate
• Omacetaxine mepesuccinate [USAN:INN]
• ZJ-C
• MLS001424293
• CHEMBL46286
• HOMOHARRINGTONINE [MI]
• CGX-635-14 (formulation)
• GTPL7454
• SCHEMBL12745687
• L01XX40
• HYFHYPWGAURHIV-JFIAXGOJSA-N
• HMS3267H22
• HMS3414N05
• HMS3678N03
• AMY33459
• Homoharringtonine, >=98% (HPLC)
• BDBM50480293
• HB4660
• MFCD05618221
• NSC758253
• s9015
• AKOS024456585
• CCG-269981
• DB04865
• NC00395
• NSC-758253
• OMACETAXINE MEPESUCCINATE [INN]
• Cephalotaxine, O3-((2R)-2,6-dihydroxy-2-(2-methoxy-2-oxoethyl)-6-methyl-1-oxoheptyl)-
• NCGC00025155-02
• NCGC00025155-03
• NCGC00025155-04
• NCGC00025155-07
• OMACETAXINE MEPESUCCINATE [VANDF]
• HY-14944
• NCI60_000917
• OMACETAXINE MEPESUCCINATE [WHO-DD]
• SMR000469230
• H1775
• D08956
• OMACETAXINE MEPESUCCINATE [ORANGE BOOK]
• AB00642561-02
• EN300-22161068
• SR-01000597562
• Q7089373
• SR-01000597562-1
• BRD-K76674262-001-01-7
• BRD-K76674262-001-02-5
• Cephalotaxine, 3-[4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate]
• (2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(13),4,14,19-tetraen-3-yl 1-methyl (3R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)butanedioate
• (S)-1-((11bS,12S,14aR)-13-methoxy-2,3,5,6,11b,12-hexahydro-1H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-12-yl) 4-methyl 2-hydroxy-2-(4-hydroxy-4-methylpentyl)succinate
• 1-((1S,3aR,14bS)-2-Methoxy-1,5,6,8,9,14b-hexahydro-4H- cyclopenta(a)(1,3)dioxolo(4,5-h)pyrrolo(2,1-b)(3)benzazepin-1-yl) 4-methyl (2R)-2- hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9535	95.35%
Caco-2	-	0.6425	64.25%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5237	52.37%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.8643	86.43%
OATP1B3 inhibitior	+	0.9242	92.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9723	97.23%
P-glycoprotein inhibitior	+	0.8185	81.85%
P-glycoprotein substrate	+	0.9327	93.27%
CYP3A4 substrate	+	0.6903	69.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7342	73.42%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5618	56.18%
CYP inhibitory promiscuity	-	0.9428	94.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Danger	0.4609	46.09%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9461	94.61%
Skin irritation	-	0.7768	77.68%
Skin corrosion	-	0.9353	93.53%
Ames mutagenesis	-	0.6260	62.60%
Human Ether-a-go-go-Related Gene inhibition	-	0.5151	51.51%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8405	84.05%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7780	77.80%
Acute Oral Toxicity (c)	III	0.5745	57.45%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.6275	62.75%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.7314	73.14%
PPAR gamma	+	0.5730	57.30%
Honey bee toxicity	-	0.7905	79.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5556	55.56%
Fish aquatic toxicity	+	0.9549	95.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	158.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.31%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.88%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.35%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.80%	96.77%
CHEMBL2581	P07339	Cathepsin D	93.88%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.12%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.84%	92.62%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	90.53%	95.55%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.06%	91.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.23%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.38%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.93%	97.09%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	86.66%	96.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.58%	85.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.58%	95.50%
CHEMBL5028	O14672	ADAM10	86.10%	97.50%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.80%	90.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.64%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.35%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.18%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	83.45%	93.18%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.28%	90.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.44%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.38%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.82%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.85%	100.00%

Plants that contains it

• Cephalotaxus fortunei

Cross-Links

• PubChem: 285033
• LOTUS: LTS0019538
• wikiData: Q7089373