(1S)-16-hydroxy-19-methyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,18,20-heptaen-14-one

Details

• Internal ID: f607daae-1122-4089-b690-c34c9b5e3f54
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: (1S)-16-hydroxy-19-methyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,18,20-heptaen-14-one
• SMILES (Canonical): CC1=C(OC(=C2C1=CC3C4=C(CCN3C2=O)C5=CC=CC=C5N4)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): CC1=C(OC(=C2C1=C[C@H]3C4=C(CCN3C2=O)C5=CC=CC=C5N4)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C25H26N2O9/c1-10-13-8-15-18-12(11-4-2-3-5-14(11)26-18)6-7-27(15)22(32)17(13)23(33)35-24(10)36-25-21(31)20(30)19(29)16(9-28)34-25/h2-5,8,15-16,19-21,25-26,28-31,33H,6-7,9H2,1H3/t15-,16+,19+,20-,21+,25-/m0/s1
• InChI Key: RFCSEFDMNDMFCO-OUCBCNBBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆N₂O₉
• Molecular Weight: 498.50 g/mol
• Exact Mass: 498.16383041 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7738	77.38%
Caco-2	-	0.8330	83.30%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6714	67.14%
OATP2B1 inhibitior	-	0.8417	84.17%
OATP1B1 inhibitior	+	0.8296	82.96%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8510	85.10%
P-glycoprotein inhibitior	-	0.4510	45.10%
P-glycoprotein substrate	-	0.5355	53.55%
CYP3A4 substrate	+	0.7043	70.43%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8697	86.97%
CYP3A4 inhibition	-	0.8426	84.26%
CYP2C9 inhibition	-	0.7477	74.77%
CYP2C19 inhibition	-	0.8109	81.09%
CYP2D6 inhibition	-	0.8462	84.62%
CYP1A2 inhibition	-	0.6549	65.49%
CYP2C8 inhibition	+	0.5837	58.37%
CYP inhibitory promiscuity	-	0.5055	50.55%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5565	55.65%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9478	94.78%
Skin irritation	-	0.7708	77.08%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5716	57.16%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8689	86.89%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8295	82.95%
Acute Oral Toxicity (c)	III	0.5644	56.44%
Estrogen receptor binding	+	0.8056	80.56%
Androgen receptor binding	+	0.6508	65.08%
Thyroid receptor binding	+	0.5562	55.62%
Glucocorticoid receptor binding	+	0.6106	61.06%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6280	62.80%
Honey bee toxicity	-	0.7221	72.21%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	-	0.4366	43.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.11%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.18%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.25%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	90.01%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.84%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.79%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.65%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	87.38%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.32%	95.89%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	85.65%	95.48%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.13%	91.71%
CHEMBL2535	P11166	Glucose transporter	83.92%	98.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.22%	95.83%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.13%	90.08%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.79%	93.65%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.52%	88.56%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.38%	85.00%

Plants that contains it

• Nauclea officinalis

Cross-Links

• PubChem: 5487217
• NPASS: NPC190421