NPs Basic Information

Name
Omacetaxine mepesuccinate
Molecular Formula C29H39NO9
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
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
InChIKey
HYFHYPWGAURHIV-JFIAXGOJSA-N
Synonyms
homoharringtonine; Omacetaxine mepesuccinate; 26833-87-4; Ceflatonin; Myelostat; Synribo; CGX-635; Omapro; Homoharringtonin; (-)-homoharringtonine; NSC-141633; C29H39NO9; CHEBI:71019; (2'R,3S,4S,5R)-(-)-homoharringtonine; Omacetaxine (homoharringtonine); Omacetaxine mepesuccinate [USAN]; 6FG8041S5B; NSC 141633; 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; Synribo (TN); Cephalotaxine, 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester); UNII-6FG8041S5B; NSC141633; NCGC00025155-01; Omacetaxine mepesuccinate [USAN:INN]; BRN 5687925; omacetaxini mepesuccinas; ZJ-C; mepesuccinate d'omacetaxine; mepesuccinato de omacetaxina; Cephalotaxine 4-Methyl (2R)-2-Hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (Ester); MLS001424293; CHEMBL46286; HOMOHARRINGTONINE [MI]; CGX-635-14 (formulation); GTPL7454; SCHEMBL12745687; HMS3267H22; HMS3414N05; HMS3678N03; AMY33459; Homoharringtonine, >=98% (HPLC); BDBM50480293; HB4660; MFCD05618221; NSC758253; s9015; ZINC26011099; AKOS024456585; CCG-269981; DB04865; NC00395; NSC-758253; OMACETAXINE MEPESUCCINATE [INN]; NCGC00025155-02; NCGC00025155-03; NCGC00025155-04; NCGC00025155-07; OMACETAXINE MEPESUCCINATE [MART.]; 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]; Cephalotaxine, 4-methyl-, 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester); (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; 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; Homoharringtonine; Cephalotaxine; [3(R)]-4-methyl 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate
CAS 26833-87-4
PubChem CID 285033
ChEMBL ID CHEMBL46286
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Alkaloids and derivatives
      • Class: Cephalotaxus alkaloids
        • Subclass: No Rank at Level Subclass
          • Direct Parent: Cephalotaxus alkaloids

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 545.6 ALogp: 0.8
HBD: 2 HBA: 10
Rotatable Bonds: 11 Lipinski's rule of five: Rejected
Polar Surface Area: 124.0 Aromatic Rings: 5
Heavy Atoms: 39 QED Weighted: 0.447

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.88 MDCK Permeability: 0.00004850
Pgp-inhibitor: 0.988 Pgp-substrate: 0.002
Human Intestinal Absorption (HIA): 0.002 20% Bioavailability (F20%): 0.138
30% Bioavailability (F30%): 0.69

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.872 Plasma Protein Binding (PPB): 52.93%
Volume Distribution (VD): 2.517 Fu: 37.37%

ADMET: Metabolism

CYP1A2-inhibitor: 0.067 CYP1A2-substrate: 0.605
CYP2C19-inhibitor: 0.172 CYP2C19-substrate: 0.876
CYP2C9-inhibitor: 0.379 CYP2C9-substrate: 0.256
CYP2D6-inhibitor: 0.851 CYP2D6-substrate: 0.316
CYP3A4-inhibitor: 0.945 CYP3A4-substrate: 0.914

ADMET: Excretion

Clearance (CL): 8.199 Half-life (T1/2): 0.224

ADMET: Toxicity

hERG Blockers: 0.109 Human Hepatotoxicity (H-HT): 0.863
Drug-inuced Liver Injury (DILI): 0.206 AMES Toxicity: 0.198
Rat Oral Acute Toxicity: 0.086 Maximum Recommended Daily Dose: 0.941
Skin Sensitization: 0.061 Carcinogencity: 0.851
Eye Corrosion: 0.003 Eye Irritation: 0.008
Respiratory Toxicity: 0.165
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC000702 0.278 D0M4XY 1.000
ENC000361 0.252 D0L1JW 0.313
ENC005626 0.244 D02DKD 0.268
ENC002565 0.238 D04TDQ 0.260
ENC002383 0.238 D0D4HN 0.252
ENC001089 0.236 D0W8WB 0.238
ENC005621 0.233 D09PJX 0.236
ENC002846 0.231 D07VBA 0.228
ENC005153 0.229 D0Y5RZ 0.228
ENC003401 0.223 D07UXP 0.227
*Note: the compound similarity was calculated by RDKIT.