(1S,4R,5E,7S,10Z,20S,21S)-4-ethyl-17-hydroxy-7-[(1S)-1-hydroxy-3-methylbut-2-enyl]-10,21-dimethyl-8,24,26-trioxa-14-azatetracyclo[13.8.2.11,20.019,25]hexacosa-5,10,15,17,19(25)-pentaene-9,13,22-trione

Details

• Internal ID: aef9fbf7-e4c2-4ac9-923c-fdc9babbd9a5
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: (1S,4R,5E,7S,10Z,20S,21S)-4-ethyl-17-hydroxy-7-[(1S)-1-hydroxy-3-methylbut-2-enyl]-10,21-dimethyl-8,24,26-trioxa-14-azatetracyclo[13.8.2.11,20.019,25]hexacosa-5,10,15,17,19(25)-pentaene-9,13,22-trione
• SMILES (Canonical): CCC1CCC23CC(=O)C(C(O2)C4=C(O3)C(=CC(=C4)O)NC(=O)CC=C(C(=O)OC(C=C1)C(C=C(C)C)O)C)C
• SMILES (Isomeric): CC[C@@H]\1CC[C@]23CC(=O)[C@H]([C@H](O2)C4=C(O3)C(=CC(=C4)O)NC(=O)C/C=C(\C(=O)O[C@@H](/C=C1)[C@H](C=C(C)C)O)/C)C
• InChI: InChI=1S/C31H39NO8/c1-6-20-8-9-26(24(34)13-17(2)3)38-30(37)18(4)7-10-27(36)32-23-15-21(33)14-22-28-19(5)25(35)16-31(39-28,12-11-20)40-29(22)23/h7-9,13-15,19-20,24,26,28,33-34H,6,10-12,16H2,1-5H3,(H,32,36)/b9-8+,18-7-/t19-,20+,24+,26+,28+,31+/m1/s1
• InChI Key: NXQKNJIQGBLGMU-XVYITHGISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₉NO₈
• Molecular Weight: 553.60 g/mol
• Exact Mass: 553.26756720 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 5.04
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9287	92.87%
Caco-2	-	0.8240	82.40%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5204	52.04%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.8234	82.34%
OATP1B3 inhibitior	+	0.9155	91.55%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8572	85.72%
BSEP inhibitior	+	0.9843	98.43%
P-glycoprotein inhibitior	+	0.8326	83.26%
P-glycoprotein substrate	+	0.6820	68.20%
CYP3A4 substrate	+	0.7024	70.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	-	0.6769	67.69%
CYP2C9 inhibition	-	0.7943	79.43%
CYP2C19 inhibition	-	0.7423	74.23%
CYP2D6 inhibition	-	0.9218	92.18%
CYP1A2 inhibition	-	0.7727	77.27%
CYP2C8 inhibition	+	0.6751	67.51%
CYP inhibitory promiscuity	-	0.7345	73.45%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5192	51.92%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9533	95.33%
Skin irritation	-	0.7696	76.96%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	-	0.6328	63.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4113	41.13%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.5089	50.89%
skin sensitisation	-	0.8209	82.09%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6936	69.36%
Acute Oral Toxicity (c)	III	0.6697	66.97%
Estrogen receptor binding	+	0.8067	80.67%
Androgen receptor binding	+	0.7380	73.80%
Thyroid receptor binding	+	0.5247	52.47%
Glucocorticoid receptor binding	+	0.8204	82.04%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7360	73.60%
Honey bee toxicity	-	0.7390	73.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9187	91.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.24%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.79%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.01%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.87%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.18%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	94.50%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.87%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.56%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.49%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.93%	97.09%
CHEMBL325	Q13547	Histone deacetylase 1	90.77%	95.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.94%	94.45%
CHEMBL3310	Q96DB2	Histone deacetylase 11	89.07%	88.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.80%	90.08%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.42%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.74%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.35%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.09%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.50%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.75%	100.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.55%	82.38%
CHEMBL4208	P20618	Proteasome component C5	82.24%	90.00%
CHEMBL236	P41143	Delta opioid receptor	80.96%	99.35%
CHEMBL1902	P62942	FK506-binding protein 1A	80.80%	97.05%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.31%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.16%	97.21%

Plants that contains it

• Aegiceras corniculatum
• Ajuga integrifolia
• Allium multibulbosum
• Arbutus menziesii
• Bruguiera gymnorhiza
• Cinnamosma madagascariensis
• Echiochilon pauciflorum
• Helichrysum nudifolium
• Hypoxis nyasica
• Isoberlinia angolensis
• Macaranga sinensis
• Mirabilis jalapa
• Nicoteba betonica
• Otostegia fruticosa
• Paranephelius uniflorus
• Rhododendron aureum
• Seriphidium lessingianum
• Sonneratia alba
• Tephroseris integrifolia
• Terminalia tetraphylla
• Teucrium orientale
• Veltheimia capensis
• Xylopia aethiopica

Cross-Links

• PubChem: 53235715
• NPASS: NPC143008