[(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl] (3S)-3-hydroxybutanoate

Details

• Internal ID: 8afd034e-b043-4354-ab98-0b49e200ff85
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Lycorine-type amaryllidaceae alkaloids
• IUPAC Name: [(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl] (3S)-3-hydroxybutanoate
• InChI: InChI=1S/C20H23NO6/c1-10(22)4-17(24)27-20-14(23)5-11-2-3-21-8-12-6-15-16(26-9-25-15)7-13(12)18(20)19(11)21/h5-7,10,14,18-20,22-23H,2-4,8-9H2,1H3/t10-,14-,18-,19+,20+/m0/s1
• InChI Key: AMVDLCRDRNPXIY-SGPJTXGESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₆
• Molecular Weight: 373.40 g/mol
• Exact Mass: 373.15253745 g/mol
• Topological Polar Surface Area (TPSA): 88.50 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9687	96.87%
Caco-2	+	0.5417	54.17%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7659	76.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8979	89.79%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7599	75.99%
BSEP inhibitior	+	0.8385	83.85%
P-glycoprotein inhibitior	-	0.6938	69.38%
P-glycoprotein substrate	-	0.5242	52.42%
CYP3A4 substrate	+	0.6119	61.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6950	69.50%
CYP3A4 inhibition	-	0.6641	66.41%
CYP2C9 inhibition	-	0.9245	92.45%
CYP2C19 inhibition	-	0.8277	82.77%
CYP2D6 inhibition	-	0.5397	53.97%
CYP1A2 inhibition	-	0.5613	56.13%
CYP2C8 inhibition	-	0.8103	81.03%
CYP inhibitory promiscuity	-	0.7824	78.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.4061	40.61%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9854	98.54%
Skin irritation	-	0.7640	76.40%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6601	66.01%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8255	82.55%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7095	70.95%
Acute Oral Toxicity (c)	III	0.6344	63.44%
Estrogen receptor binding	+	0.6297	62.97%
Androgen receptor binding	+	0.5615	56.15%
Thyroid receptor binding	-	0.5822	58.22%
Glucocorticoid receptor binding	+	0.6090	60.90%
Aromatase binding	-	0.6171	61.71%
PPAR gamma	+	0.5470	54.70%
Honey bee toxicity	-	0.8017	80.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.9050	90.50%

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	98.89%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.94%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.53%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.14%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.29%	96.77%
CHEMBL4040	P28482	MAP kinase ERK2	93.62%	83.82%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.49%	90.71%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	89.37%	90.24%
CHEMBL4208	P20618	Proteasome component C5	89.11%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.83%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.69%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.05%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.16%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.19%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.18%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.04%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.90%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.54%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.86%	89.50%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.63%	96.25%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.81%	83.57%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.42%	97.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.56%	100.00%

Plants that contains it

• Lycoris traubii

Cross-Links

• PubChem: 44570381
• LOTUS: LTS0171668
• wikiData: Q104914961