Wortmannin

Details

• Internal ID: b0116840-dfef-4ab1-a7d3-1f3b818cd63e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxasteroids and derivatives
• 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 (Canonical): CC(=O)OC1CC2(C(CCC2=O)C3=C1C4(C(OC(=O)C5=COC(=C54)C3=O)COC)C)C
• SMILES (Isomeric): 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
• InChI Key: QDLHCMPXEPAAMD-QAIWCSMKSA-N
• Popularity: 9,632 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₈
• Molecular Weight: 428.40 g/mol
• Exact Mass: 428.14711772 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 19545-26-7
• Wartmannin
• Antibiotic SL-2052
• SL-2052
• XVA4O219QW
• NSC221019
• DTXSID8040642
• NSC-627609
• CHEBI:52289
• NSC627609
• [(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
• (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
• MS54
• MS-54
• ((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
• (1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo(4,3,2-de)indeno(4,5-h)-2-benzopyran-3,6,9-trione
• (1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione
• (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
• RefChem:389363
• DTXCID6020642
• (1 Alpha,11 alpha)-11-(acetyloxy)-1-(methoxymethyl)-2-oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione
• 2-Oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione, 11-(acetyloxy)-1-(methoxymethyl)-, (1alpha,11alpha)-
• 606-337-5
• KY 12420
• MFCD00133927
• MLS002703028
• CHEMBL428496
• (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
• 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)-
• KY-12420
• (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.
• UNII-XVA4O219QW
• wortmanin
• Wortmannin?
• 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)-
• SL-2052;KY-12420
• nchembio866-comp1
• NSC 627609
• BRN 0067676
• WORTMANNIN [MI]
• (+)-WORTMANNIN
• SCHEMBL4531
• BSPBio_001232
• 4-19-00-03134 (Beilstein Handbook Reference)
• cid_312145
• GTPL6060
• MEGxm0_000446
• Wortmannin,Penicillium wortmannin
• ACon0_000951
• BDBM15234
• GLXC-07906
• HMS1792N13
• HMS1990N13
• HMS3403N13
• Wortmannin, Penicillium funiculosum
• EX-A1930
• MSK001432
• ST-415
• AKOS027327288
• Wortmannin - CAS 19545-26-7
• CCG-208290
• CS-5073
• DB08059
• NSC-221019
• Wortmannin; SL-2052; KY-12420
• NCGC00163485-01
• NCGC00163485-02
• AC-35862
• BS-16306
• HY-10197
• NCI60_001835
• SMR001566836
• W0007
• CU-00000000011-1
• BRD-K87343924-001-02-4
• BRD-K87343924-001-12-3
• 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,
• 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-
• 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)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.5610	56.10%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8395	83.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8742	87.42%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7366	73.66%
P-glycoprotein inhibitior	+	0.7360	73.60%
P-glycoprotein substrate	-	0.5741	57.41%
CYP3A4 substrate	+	0.6793	67.93%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8921	89.21%
CYP3A4 inhibition	-	0.5766	57.66%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5568	55.68%
CYP inhibitory promiscuity	-	0.7681	76.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5396	53.96%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9052	90.52%
Skin irritation	-	0.6963	69.63%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5190	51.90%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5784	57.84%
skin sensitisation	-	0.8479	84.79%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.8154	81.54%
Estrogen receptor binding	+	0.7911	79.11%
Androgen receptor binding	+	0.6795	67.95%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8255	82.55%
Aromatase binding	+	0.6015	60.15%
PPAR gamma	+	0.7423	74.23%
Honey bee toxicity	-	0.7496	74.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9914	99.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	158.5 nM	Potency	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	141.3 nM	Potency	via Super-PRED
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	1 nM	IC50	via Super-PRED
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	1.2 nM	IC50	via Super-PRED
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	7.6 nM	Kd	via Super-PRED
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	4 nM	IC50	via Super-PRED
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	1.6 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	40 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.84%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.62%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.77%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.71%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.85%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.35%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.04%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.65%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.74%	93.04%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.67%	92.62%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.75%	96.39%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.59%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.33%	96.67%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	80.10%	95.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 312145
• LOTUS: LTS0256688
• wikiData: Q73401372