Natural Product: ENC001044

NPs Basic Information

Download MOL File
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

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: 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:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC005378 0.295 D0X4RS 0.242
ENC005151 0.295 D09WYX 0.236
ENC002386 0.288 D01XWG 0.229
ENC003925 0.288 D0D2VS 0.227
ENC003846 0.285 D0Q4SD 0.225
ENC005031 0.277 D0B9EJ 0.224
ENC003138 0.277 D02CJX 0.221
ENC005318 0.273 D0Y0GH 0.220
ENC005188 0.273 D08BDT 0.219
ENC001980 0.269 D07VLY 0.217
*Note: the compound similarity was calculated by RDKIT.