7-Hydroxystaurosporine

Details

• Internal ID: 5e2dfb6c-e37b-4621-9f0d-e55b8c2c1004
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Carbazoles > Pyrrolocarbazoles > Indolocarbazoles
• IUPAC Name: (2S,3R,4R,6R,18R)-18-hydroxy-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one
• SMILES (Canonical): CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)C(NC6=O)O)NC)OC
• SMILES (Isomeric): C[C@@]12[C@@H]([C@@H](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)[C@H](NC6=O)O)NC)OC
• InChI: InChI=1S/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18-,25-,27-,28+/m1/s1
• InChI Key: PBCZSGKMGDDXIJ-HQCWYSJUSA-N
• Popularity: 826 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₆N₄O₄
• Molecular Weight: 482.50 g/mol
• Exact Mass: 482.19540532 g/mol
• Topological Polar Surface Area (TPSA): 89.70 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• UCN-01
• Ucn 01
• 112953-11-4
• KRX-0601
• UCN01
• UCN-02
• (5s,6r,7r,9r,16r)-16-hydroxy-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-5h,14h-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-14-one
• NSC-638850
• 7BU5H4V94A
• NSC638850
• (2S,3R,4R,6R,18R)-18-hydroxy-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one
• (5S,6R,7R,9R,16R)-16-hydroxy-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14(5H)-one
• UCN
• 1okz
• KW-2401
• (5S,6R,7R,9R,16R)-16-Hydroxy-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[
• 9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-3-hydroxy-10-methoxy-9-methyl-11-(methylamino)-, (3R,9S,10R,11R,13R)-
• NSC 638850
• UNII-7BU5H4V94A
• 9,13-EPOXY-1H,9H-DIINDOLO(1,2,3-GH:3',2',1'-LM)PYRROLO(3,4-J)(1,7)BENZODIAZONIN-1-ONE, 2,3,10,11,12,13-HEXAHYDRO-3-HYDROXY-10-METHOXY-9-METHYL-11-(METHYLAMINO)-, (3R,9S,10R,11R,13R)-
• 8,12-Epoxy-1H,8H-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)triinden-1-one, 2,3,9,10,11,12-hexahydro-3-hydroxy-9-methoxy-8-methyl-10-(methylamino)-
• GTPL7907
• SCHEMBL1551632
• CHEMBL1236539
• BDBM17054
• DTXSID20150238
• KRX0601
• 7-Hydroxystaurosporine [WHO-DD]
• AKOS030230764
• (+)-UCN-01
• DB01933
• 9,13-Epoxy-1H,9H-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-3-hydroxy-10-methoxy-9-methyl-11-(methylamino)-, (3-alpha,9-beta,10-alpha,11-alpha,13-beta)-(+)-
• NCI60_012974
• hydroxy-methoxy-methyl-(methylamino)[?]one
• J-002880
• Q27074035
• 2,10,11,12,13-Hexahydro-3-hydroxy-10-methoxy-9-methyl- 11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]-benzodiazonin-1-one
• 9,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo [3,4-j][1,7]-benzodiazonin-1-one, 2,3,10,11,12,13- hexahydro-3-hydroxy-10-methoxy-9-methyl- 11-(methylamino)-, [3R-(3.alpha., 9.beta., 10.alpha.,11.alpha., 13.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8044	80.44%
Caco-2	-	0.6293	62.93%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Nucleus	0.4033	40.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8722	87.22%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7359	73.59%
BSEP inhibitior	+	0.9503	95.03%
P-glycoprotein inhibitior	+	0.7349	73.49%
P-glycoprotein substrate	+	0.8012	80.12%
CYP3A4 substrate	+	0.7145	71.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8300	83.00%
CYP3A4 inhibition	-	0.7542	75.42%
CYP2C9 inhibition	-	0.8677	86.77%
CYP2C19 inhibition	-	0.8250	82.50%
CYP2D6 inhibition	-	0.8983	89.83%
CYP1A2 inhibition	-	0.7904	79.04%
CYP2C8 inhibition	+	0.7444	74.44%
CYP inhibitory promiscuity	-	0.7792	77.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5980	59.80%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9715	97.15%
Skin irritation	-	0.7925	79.25%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	+	0.6746	67.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6721	67.21%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5251	52.51%
skin sensitisation	-	0.8786	87.86%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5195	51.95%
Acute Oral Toxicity (c)	III	0.5827	58.27%
Estrogen receptor binding	+	0.8190	81.90%
Androgen receptor binding	+	0.6879	68.79%
Thyroid receptor binding	+	0.6317	63.17%
Glucocorticoid receptor binding	+	0.8668	86.68%
Aromatase binding	+	0.7696	76.96%
PPAR gamma	+	0.8115	81.15%
Honey bee toxicity	-	0.6983	69.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.6027	60.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	623 nM	Kd	via Super-PRED
CHEMBL2801	Q13557	CaM kinase II delta	520 nM	Kd	via Super-PRED
CHEMBL3829	Q13555	CaM kinase II gamma	823 nM	Kd	via Super-PRED
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	30 nM	Kd	via Super-PRED
CHEMBL2695	Q05397	Focal adhesion kinase 1	436 nM	Kd	via Super-PRED
CHEMBL3717	P08581	Hepatocyte growth factor receptor	937 nM	Kd	via Super-PRED
CHEMBL3529	Q14164	Inhibitor of nuclear factor kappa B kinase epsilon subunit	528 nM	Kd	via Super-PRED
CHEMBL3778	Q9NWZ3	Interleukin-1 receptor-associated kinase 4	895 nM	Kd	via Super-PRED
CHEMBL5754	Q96L34	MAP/microtubule affinity-regulating kinase 4	8 nM	Kd	via Super-PRED
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	303 nM	Kd	via Super-PRED
CHEMBL5330	Q12851	Mitogen-activated protein kinase kinase kinase kinase 2	631 nM	Kd	via Super-PRED
CHEMBL6166	O95819	Mitogen-activated protein kinase kinase kinase kinase 4	832 nM	Kd	via Super-PRED
CHEMBL4852	Q9Y4K4	Mitogen-activated protein kinase kinase kinase kinase 5	836 nM	Kd	via Super-PRED
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	737 nM	Kd	via Super-PRED
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	436 nM	Kd	via Super-PRED
CHEMBL299	P17252	Protein kinase C alpha	35 nM	Kd	via Super-PRED
CHEMBL3045	P05771	Protein kinase C beta	19 nM	Kd	via Super-PRED
CHEMBL2996	Q05655	Protein kinase C delta	38 nM	Kd	via Super-PRED
CHEMBL3384	Q16512	Protein kinase N1	8 nM	Kd	via Super-PRED
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	191 nM	Kd	via Super-PRED
CHEMBL3231	Q13464	Rho-associated protein kinase 1	955 nM	Kd	via Super-PRED
CHEMBL4924	Q9UK32	Ribosomal protein S6 kinase alpha 6	141 nM	Kd	via Super-PRED
CHEMBL3981	O94804	Serine/threonine-protein kinase 10	3 nM	Kd	via Super-PRED
CHEMBL4202	Q9H2G2	Serine/threonine-protein kinase 2	89 nM	Kd	via Super-PRED
CHEMBL2185	Q96GD4	Serine/threonine-protein kinase Aurora-B	670 nM	Kd	via Super-PRED
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	16 nM	Kd	via Super-PRED
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	9.88 nM; 5.6 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL4598	Q13043	Serine/threonine-protein kinase MST1	114 nM	Kd	via Super-PRED
CHEMBL4708	Q13188	Serine/threonine-protein kinase MST2	45 nM	Kd	via Super-PRED
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	25 nM	Kd	via Super-PRED
CHEMBL5699	Q9H0K1	Serine/threonine-protein kinase SIK2	11 nM	Kd	via Super-PRED
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	393 nM	Kd	via Super-PRED
CHEMBL4599	Q07912	Tyrosine kinase non-receptor protein 2	162 nM	Kd	via Super-PRED
CHEMBL5251	Q06187	Tyrosine-protein kinase BTK	386 nM	Kd	via Super-PRED
CHEMBL3982	P16591	Tyrosine-protein kinase FER	430 nM	Kd	via Super-PRED
CHEMBL3234	P08631	Tyrosine-protein kinase HCK	621 nM	Kd	via Super-PRED
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	67 nM	Kd	via Super-PRED
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	521 nM	Kd	via Super-PRED
CHEMBL2599	P43405	Tyrosine-protein kinase SYK	217 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.97%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.82%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.05%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.70%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.43%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	96.30%	93.03%
CHEMBL2581	P07339	Cathepsin D	95.81%	98.95%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	95.35%	85.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.89%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.19%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	92.95%	95.83%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.37%	91.07%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.02%	93.99%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.85%	92.88%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	90.67%	82.50%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	90.48%	95.52%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.27%	94.00%
CHEMBL4237	O75582	Ribosomal protein S6 kinase alpha 5	89.88%	91.00%
CHEMBL1936	P10721	Stem cell growth factor receptor	89.17%	84.17%
CHEMBL3820	P35557	Hexokinase type IV	88.92%	91.96%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	88.62%	90.95%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	88.55%	80.00%
CHEMBL5314	Q06418	Tyrosine-protein kinase receptor TYRO3	88.31%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.18%	97.09%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	87.70%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.63%	97.14%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	87.16%	88.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.55%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	86.32%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.23%	86.33%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.44%	96.00%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	85.28%	82.86%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.01%	91.38%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	83.14%	81.29%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.94%	95.36%
CHEMBL2527	O96017	Serine/threonine-protein kinase Chk2	81.18%	97.50%
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	80.96%	97.15%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.40%	91.24%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 72271
• LOTUS: LTS0230106
• wikiData: Q27074035