NPs Basic Information

Name
Paclitaxel
Molecular Formula C47H51NO14
IUPAC Name*
[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
SMILES
CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
InChI
InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChIKey
RCINICONZNJXQF-MZXODVADSA-N
Synonyms
33069-62-4; P88XT4IS4D; Paclitaxel; Taxol; Taxol A; Yewtaxan; Abraxane; Plaxicel; Genaxol; Ebetaxel; Genetaxyl; Capxol; Paxene; Onxol; OncoGel; Cyclopax; Genexol; Intaxel; Mitotax; Pacliex; Paxceed; TaxAlbin; EmPAC; ABI-007; Onxal; Zisu; LipoPac; Taxus Liberte; Taxus stent; EndoTAG 1; LEP-ETU; Genexol-PM; Tocosol Paclitaxel; NSC-125973; (-)-Paclitaxel; Taxus; ABI 007; BMS 181339-01; MBT 0206; Paclitaxel (Taxol); NSC 125973; BMS-181339-01; HSDB 6839; DHP 107; DHP-107; DRG-0190; NK 105; NSC125973; QW 8184; Liposome-entrapped paclitaxel easy-to-use; Paclitaxel (taxus canadensis); CHEMBL428647; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate; 5beta,20-Epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine; CHEBI:45863; nab-paclitaxel; MBT-0206; ABI-007 COMPONENT PACLITAXEL; NK-105; (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betaS*),11alpha,12alpha,12balpha))-beta-(Benzoylamino)-alpha-hydroxybenzenepropanoic acid 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester; QW-8184; NCGC00164367-01; Padexol; MFCD00869953; (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate; Cynviloq; Nanoxel; Sindaxel; Xorane; Cypher select; Coroflex Please; Taxus Express; 7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.; (NAB)-Paclitaxel; SMR000857385; EndoTAG-1; SR-01000075350; Abraxane I.V. Suspension; UNII-P88XT4IS4D; Anzatax; Infinnium; Nanotaxel; Paclical; Pacligel; Paxoral; CCRIS 8143; Paclitaxel,(S); Paclitaxel [USAN:USP:INN:BAN]; Abraxane (TN); (2alpha,5beta,7beta,10beta,13alpha)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl benzoate; [diacetoxy-[(2R,3S)-3-benzamido-2-hydroxy-3-phenyl-propanoyl]oxy-dihydroxy-tetramethyl-oxo-[?]yl] benzoate; 5?,20-Epoxy-1,7?-dihydroxy-9-oxotax-11-ene-2?,4,10?,13?-tetrayl 4,10-diacetate 2-benzoate 13-[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate]; CAS-33069-62-4; IG 001; BMS-181339; Paclitaxel-SSMM-VIP; P-SSMM-VIP; PACLITAXEL [MI]; PACLITAXEL [INN]; PACLITAXEL [JAN]; Prestwick3_000155; PACLITAXEL [HSDB]; PACLITAXEL [USAN]; DSSTox_CID_3413; TAXOL (TN); PACLITAXEL [VANDF]; PACLITAXEL [MART.]; SCHEMBL3976; 3PPC5TL76P; DSSTox_RID_77016; Nova-12005; PACLITAXEL [USP-RS]; PACLITAXEL [WHO-DD]; Paclitaxel, Taxus brevifolia; BIDD:PXR0046; DSSTox_GSID_23413; BSPBio_000290; KBioGR_002509; KBioSS_002517; Paclitaxel (JAN/USP/INN); MLS002154218; MLS002695976; OAS-PAC-100; PACLITAXEL [EMA EPAR]; BPBio1_000320; GTPL2770; MEGxp0_001940; Taxol (TN) (Bristol Meyers); PACLITAXEL [GREEN BOOK]; DTXSID9023413; PACLITAXEL [ORANGE BOOK]; ACon1_002231; KBio2_002509; KBio2_005077; KBio2_007645; KBio3_002987; ANX-513; DHP-208; DTS-301; PACLITAXEL [EP MONOGRAPH]; PACLITAXEL [USP IMPURITY]; SDP-013; cMAP_000068; ORAXOL COMPONENT PACLITAXEL; HMS2090D07; HMS2095O12; HMS2231A16; HMS3712O12; PACLITAXEL [USP MONOGRAPH]; Abraxane (albumin-bound suspension); ABRAXANE COMPONENT PACLITAXEL; ACT02709; HY-B0015; MPI-5018; Tox21_112107; BDBM50001839; NSC745099; ZINC96006020; ABI 007 COMPONENT PACLITAXEL; AKOS007930675; AKOS015969673; AKOS025312303; CCG-220155; CS-1145; DB01229; GS-6554; NSC-745099; NCGC00164367-02; NCGC00164367-03; NCGC00164367-04; NCGC00164367-05; NCGC00164367-10; Paclitaxel, From Taxus brevifolia, 95%; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro-4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate, 12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine; NAB-PACLITAXEL COMPONENT PACLITAXEL; NCI60_000601; Paclitaxel, from Taxus yannanensis, powder; PACLITAXEL IMPURITY L [EP IMPURITY]; AB00513812; D00491; EN300-117275; M02242; N88686; AB00513812-02; AB00513812-03; 069P624; Paclitaxel, Antibiotic for Culture Media Use Only; Q423762; 7,4]benz[1,2-b]oxete,benzenepropanoic acid deriv.; Q-201533; SR-01000075350-1; SR-01000075350-3; SR-01000075350-6; SR-01000075350-7; SR-01000075350-9; BRD-K62008436-001-03-1; BRD-K62008436-001-05-6; BRD-K62008436-001-22-1; Paclitaxel, from semisynthetic (from Taxus sp.), >=97%; Paclitaxel, European Pharmacopoeia (EP) Reference Standard; Paclitaxel, from Taxus brevifolia, >=95% (HPLC), powder; Paclitaxel, United States Pharmacopeia (USP) Reference Standard; 12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine; Paclitaxel, Pharmaceutical Secondary Standard; Certified Reference Material; Paclitaxel natural for peak identification, European Pharmacopoeia (EP) Reference Standard; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro 4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano 5Hcyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate,; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-4,6,12b-Tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (alphaR,betaS)-beta-(benzoylamino)-alpha-hydroxybenzenepropanoate; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (aR,bS)-b-(benzoylamino)-a-hydroxybenzenepropanoate; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate; (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betaS*),11alpha,12alpha,12balpha))-beta-(Benzoylamino)-alpha-hydroxybenzenepropanoic acid 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12; (2beta,5beta,7alpha,8alpha,10alpha,13alpha)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl benzoate; [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate; [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl]benzoate; 1203669-79-7; 4,7beta,10beta-tris(acetyloxy)-13alpha-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate; 4alpha,10beta-bis(acetyloxy)-13alpha-[(2S,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy]-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate; BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-6,12B-BIS(ACETYLOXY)-12-(BENZOYLOXY)-2A,3,4,4A,5,6,9,10,11,12,12A,12B-DODECAHYDRO-4,11-DIHYDROXY-4A,8,13,13-TETRAMETHYL-5-OXO-7,11-METHANO-1H-CYCLODECA(3,4)BENZ(1,2-B)OXET-9-YL ESTER, (.ALPHA.R,.BETA.S)-; Benzenepropanoic acid, 6,12b-bis(acetyl oxy)-12-(benzoyloxy)- 2a,3,4,4a,5,6,9,10,11,12,12a,12b,- dodecahydro-4,11- dihydroxy-4a,8,13,13-tetramethyl-5-oxo- 7,11-methano- 1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR- [2a.alpha.,4.beta.,4a.beta.,6.beta.,9.alpha.(alpha. R*,.beta.S*),11.alpha.,12.alpha.,12a.alpha.,12b.alpha.]]-; Benzenepropanoic acid, b-(benzoylamino)-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (aR,bS)-; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-4,6,12b-tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (alphaR,betaS)-; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 4,6,12b-tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR-[2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha]]-; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2a-alpha,4-beta,4a-beta,6-beta,9-alpha(alpha-R*,beta-S*),11-alpha,12-alpha,12a-alpha, 12b-alpha))-; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-; Paclitaxel semi-synthetic for peak identification, European Pharmacopoeia (EP) Reference Standard; Paclitaxel semi-synthetic for system suitability, European Pharmacopoeia (EP) Reference Standard; Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha- hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine; Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxy-, 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine (8CI); Tax-11-en-9-one,20-epoxy-1,2.alpha.,4,7.beta., 10.beta.,13.alpha.- hexahydroxy-, 4,10-diacetate 2- benzoate,13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine
CAS 33069-62-4
PubChem CID 36314
ChEMBL ID CHEMBL428647
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Prenol lipids
        • Subclass: Diterpenoids
          • Direct Parent: Taxanes and derivatives

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Physi-Chem Properties

Molecular Weight: 853.9 ALogp: 2.5
HBD: 4 HBA: 14
Rotatable Bonds: 14 Lipinski's rule of five: Rejected
Polar Surface Area: 221.0 Aromatic Rings: 7
Heavy Atoms: 62 QED Weighted: 0.126

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.461 MDCK Permeability: 0.00005350
Pgp-inhibitor: 1 Pgp-substrate: 0.997
Human Intestinal Absorption (HIA): 0.098 20% Bioavailability (F20%): 0.995
30% Bioavailability (F30%): 0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.137 Plasma Protein Binding (PPB): 94.57%
Volume Distribution (VD): 0.907 Fu: 6.78%

ADMET: Metabolism

CYP1A2-inhibitor: 0.009 CYP1A2-substrate: 0.022
CYP2C19-inhibitor: 0.099 CYP2C19-substrate: 0.066
CYP2C9-inhibitor: 0.71 CYP2C9-substrate: 0.036
CYP2D6-inhibitor: 0.021 CYP2D6-substrate: 0.058
CYP3A4-inhibitor: 0.79 CYP3A4-substrate: 0.693

ADMET: Excretion

Clearance (CL): 3.416 Half-life (T1/2): 0.028

ADMET: Toxicity

hERG Blockers: 0.28 Human Hepatotoxicity (H-HT): 0.924
Drug-inuced Liver Injury (DILI): 0.94 AMES Toxicity: 0.006
Rat Oral Acute Toxicity: 0.491 Maximum Recommended Daily Dose: 0.857
Skin Sensitization: 0.066 Carcinogencity: 0.027
Eye Corrosion: 0.003 Eye Irritation: 0.005
Respiratory Toxicity: 0.955
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.