Paxilline

Details

• Internal ID: 4edaee1e-81d0-40fa-8d9a-bb57f3d7e9a8
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one
• SMILES (Canonical): CC12CCC3C(=CC(=O)C(O3)C(C)(C)O)C1(CCC4C2(C5=C(C4)C6=CC=CC=C6N5)C)O
• SMILES (Isomeric): C[C@]12CC[C@H]3C(=CC(=O)[C@H](O3)C(C)(C)O)[C@@]1(CC[C@@H]4[C@@]2(C5=C(C4)C6=CC=CC=C6N5)C)O
• InChI: InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1
• InChI Key: ACNHBCIZLNNLRS-UBGQALKQSA-N
• Popularity: 355 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₃NO₄
• Molecular Weight: 435.60 g/mol
• Exact Mass: 435.24095853 g/mol
• Topological Polar Surface Area (TPSA): 82.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.96
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 57186-25-1
• NSC 658707
• BRN 5317894
• UNII-3T9U9Z96L7
• MLS000028812
• C27H33NO4
• CHEBI:34907
• 3T9U9Z96L7
• (1s,2r,5s,7r,11s,14s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one
• 1233509-81-3
• SMR000058863
• paxillin
• 2H-1-Benzopyrano(5',6':6,7)indeno(1,2-b)indol-3(4bh)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2-alpha,4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-
• 2H-Pyrano(2'',3'':5',6')benz(1',2':6,7)indeno(1,2-b)indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-
• 2H-Pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-rel-
• PAXILINE
• NSC-658707
• (+)-paxilline
• Spectrum5_001975
• CBiol_001842
• BSPBio_001427
• KBioGR_000147
• KBioSS_000147
• SCHEMBL361232
• CHEMBL410063
• cid_105008
• BDBM50854
• KBio2_000147
• KBio2_002715
• KBio2_005283
• KBio3_000293
• KBio3_000294
• DTXSID10972643
• Bio1_000128
• Bio1_000617
• Bio1_001106
• Bio2_000147
• Bio2_000627
• HMS1361H09
• HMS1791H09
• HMS1989H09
• HMS2232J18
• HMS3268F05
• HMS3402H09
• 2H-1-Benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, [2R-(2.alpha.,4b.beta.,6a.alpha.,12b.beta.,12c.alpha.,14a.beta.)]-
• HY-N6778
• C27-H33-N-O4
• HB1056
• KC-155
• MFCD00083464
• AKOS024456907
• Paxilline, powder, >=98% (HPLC)
• IDI1_033897
• NCGC00025342-05
• NCGC00025342-07
• LS-39378
• CS-0026740
• F82145
• SR-01000597527
• SR-01000597527-1
• BRD-K38251852-001-02-5
• BRD-K38251852-001-06-6
• Q10860377
• EDD20523-48C0-4594-B22A-1FE297F60611
• (2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-[1]benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
• (2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
• (2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a, 7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-h ydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2 '',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
• (2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
• NCGC00025342-07_C27H33NO4_(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	-	0.6489	64.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5652	56.52%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8715	87.15%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	+	0.9513	95.13%
P-glycoprotein inhibitior	-	0.4615	46.15%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7110	71.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8701	87.01%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.6108	61.08%
CYP inhibitory promiscuity	-	0.6863	68.63%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4773	47.73%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9663	96.63%
Skin irritation	-	0.6857	68.57%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6463	64.63%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5358	53.58%
skin sensitisation	-	0.7958	79.58%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5848	58.48%
Acute Oral Toxicity (c)	III	0.5447	54.47%
Estrogen receptor binding	+	0.8685	86.85%
Androgen receptor binding	+	0.7438	74.38%
Thyroid receptor binding	+	0.6704	67.04%
Glucocorticoid receptor binding	+	0.8262	82.62%
Aromatase binding	+	0.7868	78.68%
PPAR gamma	+	0.6900	69.00%
Honey bee toxicity	-	0.8738	87.38%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9786	97.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	39810.7 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.13%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.16%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.57%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.23%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.36%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.27%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.93%	99.23%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	92.49%	94.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.10%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.29%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.10%	97.09%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.49%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.16%	96.09%
CHEMBL1902	P62942	FK506-binding protein 1A	86.19%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.73%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	84.84%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.85%	94.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	83.81%	95.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.57%	95.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.47%	94.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.96%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.96%	97.14%
CHEMBL2535	P11166	Glucose transporter	81.82%	98.75%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.61%	85.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.60%	93.04%
CHEMBL5028	O14672	ADAM10	80.78%	97.50%

Plants that contains it

• Lolium perenne
• Machilus obovatifolia

Cross-Links

• PubChem: 105008
• NPASS: NPC235900
• ChEMBL: CHEMBL410063
• LOTUS: LTS0076337
• wikiData: Q10860377