(9R,10E,12S,15Z,17S,24R)-9-ethyl-4,24-dihydroxy-12-[(1S)-1-hydroxy-3-methylbut-2-enyl]-3,15-dimethyl-13-oxa-19-azatetracyclo[15.6.1.05,23.020,24]tetracosa-1(23),2,4,10,15,20-hexaene-6,14,18,22-tetrone

Details

• Internal ID: 40c44c96-3519-457e-8149-869a9ea65cc4
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: (9R,10E,12S,15Z,17S,24R)-9-ethyl-4,24-dihydroxy-12-[(1S)-1-hydroxy-3-methylbut-2-enyl]-3,15-dimethyl-13-oxa-19-azatetracyclo[15.6.1.05,23.020,24]tetracosa-1(23),2,4,10,15,20-hexaene-6,14,18,22-tetrone
• SMILES (Canonical): CCC1CCC(=O)C2=C(C(=CC3=C2C(=O)C=C4C3(C(C=C(C(=O)OC(C=C1)C(C=C(C)C)O)C)C(=O)N4)O)C)O
• SMILES (Isomeric): CC[C@@H]\1CCC(=O)C2=C(C(=CC3=C2C(=O)C=C4[C@]3([C@H](/C=C(\C(=O)O[C@@H](/C=C1)[C@H](C=C(C)C)O)/C)C(=O)N4)O)C)O
• InChI: InChI=1S/C31H35NO8/c1-6-18-7-9-21(33)27-26-19(12-16(4)28(27)36)31(39)20(29(37)32-25(31)14-23(26)35)13-17(5)30(38)40-24(10-8-18)22(34)11-15(2)3/h8,10-14,18,20,22,24,34,36,39H,6-7,9H2,1-5H3,(H,32,37)/b10-8+,17-13-/t18-,20-,22+,24+,31+/m1/s1
• InChI Key: WLFOUQMJTBECIJ-BLKUEGHMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₅NO₈
• Molecular Weight: 549.60 g/mol
• Exact Mass: 549.23626707 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9260	92.60%
Caco-2	-	0.8329	83.29%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7161	71.61%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.7912	79.12%
OATP1B3 inhibitior	+	0.9243	92.43%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7572	75.72%
BSEP inhibitior	+	0.9077	90.77%
P-glycoprotein inhibitior	+	0.7575	75.75%
P-glycoprotein substrate	+	0.6651	66.51%
CYP3A4 substrate	+	0.6853	68.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.6588	65.88%
CYP2C9 inhibition	-	0.7105	71.05%
CYP2C19 inhibition	-	0.6995	69.95%
CYP2D6 inhibition	-	0.8778	87.78%
CYP1A2 inhibition	-	0.6552	65.52%
CYP2C8 inhibition	+	0.7142	71.42%
CYP inhibitory promiscuity	+	0.5837	58.37%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Danger	0.4330	43.30%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9401	94.01%
Skin irritation	-	0.7436	74.36%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7029	70.29%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	-	0.8081	80.81%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8587	85.87%
Acute Oral Toxicity (c)	III	0.5961	59.61%
Estrogen receptor binding	+	0.8178	81.78%
Androgen receptor binding	+	0.6935	69.35%
Thyroid receptor binding	-	0.4909	49.09%
Glucocorticoid receptor binding	+	0.8188	81.88%
Aromatase binding	+	0.6692	66.92%
PPAR gamma	+	0.7413	74.13%
Honey bee toxicity	-	0.7787	77.87%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9824	98.24%

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	99.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.38%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.56%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.39%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.88%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.50%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.00%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.65%	85.11%
CHEMBL230	P35354	Cyclooxygenase-2	89.43%	89.63%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.98%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.66%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.92%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.29%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.09%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.01%	100.00%
CHEMBL4530	P00488	Coagulation factor XIII	84.50%	96.00%
CHEMBL4208	P20618	Proteasome component C5	84.29%	90.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.92%	90.08%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.27%	90.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.18%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.60%	93.99%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.77%	88.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.69%	93.04%
CHEMBL217	P14416	Dopamine D2 receptor	80.59%	95.62%

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: 72715428
• NPASS: NPC3016