(1S,2S,4R,5S,7S,11S,12R,15R,23S)-4,11-dihydroxy-18-methoxy-6-oxa-8,16-diazaoctacyclo[10.10.1.01,15.02,7.04,15.05,12.08,23.017,22]tricosa-17(22),18,20-trien-3-one

Details

• Internal ID: 7a22fe9f-24cd-4a21-bf73-3a539143c8b0
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: (1S,2S,4R,5S,7S,11S,12R,15R,23S)-4,11-dihydroxy-18-methoxy-6-oxa-8,16-diazaoctacyclo[10.10.1.01,15.02,7.04,15.05,12.08,23.017,22]tricosa-17(22),18,20-trien-3-one
• SMILES (Canonical): COC1=CC=CC2=C1NC34C25C6C7N8C5C(CC3)(C(CC8)O)C(C4(C6=O)O)O7
• SMILES (Isomeric): COC1=CC=CC2=C1N[C@@]34[C@@]25[C@H]6[C@H]7N8[C@@H]5[C@](CC3)([C@H](CC8)O)[C@@H]([C@]4(C6=O)O)O7
• InChI: InChI=1S/C21H22N2O5/c1-27-10-4-2-3-9-13(10)22-19-7-6-18-11(24)5-8-23-15-12(20(9,19)16(18)23)14(25)21(19,26)17(18)28-15/h2-4,11-12,15-17,22,24,26H,5-8H2,1H3/t11-,12+,15-,16+,17-,18-,19+,20+,21-/m0/s1
• InChI Key: ILDUBPPRVJNUPW-ZVMUKCEYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂N₂O₅
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.15287181 g/mol
• Topological Polar Surface Area (TPSA): 91.30 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8262	82.62%
Caco-2	-	0.6083	60.83%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6617	66.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9077	90.77%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4740	47.40%
P-glycoprotein inhibitior	-	0.8087	80.87%
P-glycoprotein substrate	+	0.5597	55.97%
CYP3A4 substrate	+	0.6984	69.84%
CYP2C9 substrate	-	0.8118	81.18%
CYP2D6 substrate	+	0.4090	40.90%
CYP3A4 inhibition	-	0.6959	69.59%
CYP2C9 inhibition	-	0.8212	82.12%
CYP2C19 inhibition	-	0.7754	77.54%
CYP2D6 inhibition	-	0.7939	79.39%
CYP1A2 inhibition	-	0.8532	85.32%
CYP2C8 inhibition	-	0.6186	61.86%
CYP inhibitory promiscuity	-	0.9239	92.39%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6055	60.55%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9800	98.00%
Skin irritation	-	0.7871	78.71%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4806	48.06%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.5134	51.34%
skin sensitisation	-	0.8330	83.30%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6703	67.03%
Acute Oral Toxicity (c)	III	0.5937	59.37%
Estrogen receptor binding	+	0.7903	79.03%
Androgen receptor binding	+	0.7407	74.07%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	+	0.5700	57.00%
Aromatase binding	+	0.7143	71.43%
PPAR gamma	+	0.5711	57.11%
Honey bee toxicity	-	0.8580	85.80%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.4324	43.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.79%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	93.59%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.57%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.53%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.16%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.63%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.18%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.99%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.73%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.00%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.59%	97.14%
CHEMBL4208	P20618	Proteasome component C5	85.07%	90.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.79%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.53%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.42%	93.04%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.20%	82.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.55%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.34%	89.62%
CHEMBL1937	Q92769	Histone deacetylase 2	80.27%	94.75%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.00%	90.24%

Plants that contains it

• Kopsia teoi

Cross-Links

• PubChem: 163104444
• LOTUS: LTS0148623
• wikiData: Q105115109