dimethyl (2R,4S,9R,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.11,6.02,4.09,17.010,15.09,22]docosa-10(15),11,13-triene-16,18-dicarboxylate

Details

• Internal ID: e0eb6018-721a-4e19-aa2f-689442e18474
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: dimethyl (2R,4S,9R,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.11,6.02,4.09,17.010,15.09,22]docosa-10(15),11,13-triene-16,18-dicarboxylate
• SMILES (Canonical): COC1=C(C2=C(C=C1)C34CCN5C3C6(CCC4(N2C(=O)OC)C(C6O)(C(=O)OC)O)C7C(C5)O7)O
• SMILES (Isomeric): COC1=C(C2=C(C=C1)[C@]34CCN5[C@H]3C6(CCC4(N2C(=O)OC)[C@@]([C@@H]6O)(C(=O)OC)O)[C@@H]7[C@H](C5)O7)O
• InChI: InChI=1S/C24H28N2O9/c1-32-12-5-4-11-14(15(12)27)26(20(30)34-3)23-7-6-21(18(28)24(23,31)19(29)33-2)16-13(35-16)10-25-9-8-22(11,23)17(21)25/h4-5,13,16-18,27-28,31H,6-10H2,1-3H3/t13-,16-,17-,18+,21?,22+,23?,24+/m0/s1
• InChI Key: GXDHEFQHGXMJAL-RUSVUQAZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈N₂O₉
• Molecular Weight: 488.50 g/mol
• Exact Mass: 488.17948047 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.12
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6697	66.97%
Caco-2	-	0.5959	59.59%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5351	53.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8973	89.73%
OATP1B3 inhibitior	+	0.9284	92.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7570	75.70%
P-glycoprotein inhibitior	-	0.4560	45.60%
P-glycoprotein substrate	+	0.7318	73.18%
CYP3A4 substrate	+	0.6929	69.29%
CYP2C9 substrate	-	0.8081	80.81%
CYP2D6 substrate	-	0.6642	66.42%
CYP3A4 inhibition	-	0.7422	74.22%
CYP2C9 inhibition	-	0.8037	80.37%
CYP2C19 inhibition	-	0.7715	77.15%
CYP2D6 inhibition	-	0.8342	83.42%
CYP1A2 inhibition	-	0.8312	83.12%
CYP2C8 inhibition	+	0.5252	52.52%
CYP inhibitory promiscuity	-	0.9544	95.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5322	53.22%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9333	93.33%
Skin irritation	-	0.7860	78.60%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5129	51.29%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5378	53.78%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5239	52.39%
Acute Oral Toxicity (c)	III	0.5581	55.81%
Estrogen receptor binding	+	0.7462	74.62%
Androgen receptor binding	+	0.7657	76.57%
Thyroid receptor binding	-	0.5252	52.52%
Glucocorticoid receptor binding	+	0.6224	62.24%
Aromatase binding	+	0.7177	71.77%
PPAR gamma	+	0.6385	63.85%
Honey bee toxicity	-	0.8270	82.70%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9207	92.07%

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	99.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.67%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.08%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.26%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.98%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.61%	95.89%
CHEMBL4208	P20618	Proteasome component C5	90.41%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.95%	86.33%
CHEMBL5028	O14672	ADAM10	86.86%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.94%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.78%	89.62%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.81%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.66%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.46%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.23%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.57%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.11%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.99%	97.14%
CHEMBL2581	P07339	Cathepsin D	81.61%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.12%	89.00%

Plants that contains it

• Kopsia singapurensis

Cross-Links

• PubChem: 101864232
• LOTUS: LTS0113574
• wikiData: Q105023014