Natural Product: ENC000623

NPs Basic Information

Download MOL File
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

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: 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:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC006040 0.279 D0C4RB 1.000
ENC003487 0.277 D0O5WP 0.726
ENC004541 0.268 D02HSB 0.678
ENC001481 0.260 D0U4YG 0.286
ENC002627 0.258 D0K3WO 0.269
ENC002198 0.254 D0OG8A 0.262
ENC004463 0.253 D06CWH 0.262
ENC003331 0.252 D07NVU 0.261
ENC002763 0.250 D0P6ZH 0.260
ENC003335 0.250 D0I5WB 0.259
*Note: the compound similarity was calculated by RDKIT.