NPs Basic Information

Name
Wortmannin
Molecular Formula C23H24O8
IUPAC Name*
[(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate
SMILES
CC(=O)O[C@@H]1C[C@]2([C@@H](CCC2=O)C3=C1[C@]4([C@H](OC(=O)C5=COC(=C54)C3=O)COC)C)C
InChI
InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1
InChIKey
QDLHCMPXEPAAMD-QAIWCSMKSA-N
Synonyms
wortmannin; 19545-26-7; Wartmannin; KY 12420; SL-2052; Antibiotic SL-2052; NSC221019; XVA4O219QW; KY-12420; MLS002703028; CHEMBL428496; CHEBI:52289; NSC-627609; Pi 3-Kinase Inhibitor; (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate; (1alpha,11alpha)-11-(Acetyloxy)-1-(methoxymethyl)-2-oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione; (1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate; (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b-decahydro-1H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate; (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b-decahydro-1H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate.; (1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-[(methyloxy)methyl]-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate; MFCD00133927; UNII-XVA4O219QW; wortmanin; NSC627609; Wortmannin, Wm; 3H-FURO(4,3,2-DE)INDENO(4,5-H)-2-BENZOPYRAN-3,6,9-TRIONE, 11-(ACETYLOXY)-1,6B,7,8,9A,10,11,11B-OCTAHYDRO-1-(METHOXYMETHYL)-9A,11B-DIMETHYL-, (1S,6BR,9AS,11R,11BR)-; 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-; nchembio866-comp1; NSC 627609; BRN 0067676; WORTMANNIN [MI]; (+)-WORTMANNIN; SCHEMBL4531; BSPBio_001232; 4-19-00-03134 (Beilstein Handbook Reference); cid_312145; GTPL6060; MEGxm0_000446; DTXSID8040642; Wortmannin,Penicillium wortmannin; ACon0_000951; BDBM15234; HMS1792N13; HMS1990N13; HMS3403N13; Wortmannin, Penicillium funiculosum; EX-A1930; ZINC1619592; s2758; ST-415; Wortmannin - CAS 19545-26-7; CCG-208290; CS-5073; DB08059; KY12420; NSC-221019; Wortmannin, from Penicillium funiculosum; Wortmannin; SL-2052; KY-12420; NCGC00163485-01; NCGC00163485-02; AC-35862; BS-16306; HY-10197; NCI60_001835; SMR001566836; W0007; CU-00000000011-1; J-012661; BRD-K87343924-001-02-4; 3,2-DE]INDENO[4,5-H][2]BENZOPYRAN-11-YL ACETATE; Wortmannin, from Penicillium funiculosum, >=98% (HPLC and TLC); 3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,; (1R,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b- decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate; (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-ylacetate; (1S,6BR,9AS,11R,11BR)-9A,11B-DIMETHYL-1-[(METHYLOXY)METHYL]-3,6,9-TRIOXO-1,6,6B,7,8,9,9A,10,11,11B-DECAHYDRO-3H-FURO[4,; [(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate; 2-Oxaandrosta-5,5,4-bc]furan-3,7,17-trione, 11-(acetyloxy)-1-(methoxymethyl)-, (1.alpha.,11.alpha.)-; 3H-Furo[4,2-de]indeno[4,5,-h]-2-benzopyran-3,6,9-trione, 11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6br,9aS,11R,11bR); 3H-Furo[4,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6br,9aS,11R,11bR); 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-; 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione,11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-; 6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-; octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, [1S-(1alpha,6baalpha,9abeta,11alpha,11bbeta)]-
CAS 19545-26-7
PubChem CID 312145
ChEMBL ID CHEMBL428496
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Steroids and steroid deri
        • Subclass: Oxasteroids and derivativ
          • Direct Parent: Oxasteroids and derivativ

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Physi-Chem Properties

Molecular Weight: 428.4 ALogp: 1.2
HBD: 0 HBA: 8
Rotatable Bonds: 4 Lipinski's rule of five: Accepted
Polar Surface Area: 109.0 Aromatic Rings: 5
Heavy Atoms: 31 QED Weighted: 0.675

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.889 MDCK Permeability: 0.00005250
Pgp-inhibitor: 0.987 Pgp-substrate: 0.479
Human Intestinal Absorption (HIA): 0.012 20% Bioavailability (F20%): 0.958
30% Bioavailability (F30%): 0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.781 Plasma Protein Binding (PPB): 84.34%
Volume Distribution (VD): 1.185 Fu: 17.86%

ADMET: Metabolism

CYP1A2-inhibitor: 0.086 CYP1A2-substrate: 0.314
CYP2C19-inhibitor: 0.125 CYP2C19-substrate: 0.258
CYP2C9-inhibitor: 0.228 CYP2C9-substrate: 0.056
CYP2D6-inhibitor: 0.015 CYP2D6-substrate: 0.098
CYP3A4-inhibitor: 0.629 CYP3A4-substrate: 0.355

ADMET: Excretion

Clearance (CL): 4.469 Half-life (T1/2): 0.484

ADMET: Toxicity

hERG Blockers: 0.004 Human Hepatotoxicity (H-HT): 0.263
Drug-inuced Liver Injury (DILI): 0.329 AMES Toxicity: 0.136
Rat Oral Acute Toxicity: 0.961 Maximum Recommended Daily Dose: 0.896
Skin Sensitization: 0.222 Carcinogencity: 0.94
Eye Corrosion: 0.003 Eye Irritation: 0.03
Respiratory Toxicity: 0.726
*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.