(2R,3S)-N-{(2Z,5R,6R,7S)-7-[(3S,5Z,8S,9R)-9,14-dihydroxy-12-methoxy-8-methyl-1-oxo-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclododecin-3-yl]-6-hydroxy-5-methyloct-2-en-1-yl}-3-hydroxy-2-methylhexanamide

Details

• Internal ID: 5ddc5b99-19d5-42c1-b97c-6057009f7f08
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (2R,3S)-N-[(Z,5R,6R,7S)-7-[(4S,6Z,9S,10R)-10,16-dihydroxy-14-methoxy-9-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),6,13,15-tetraen-4-yl]-6-hydroxy-5-methyloct-2-enyl]-3-hydroxy-2-methylhexanamide
• SMILES (Canonical): CCCC(C(C)C(=O)NCC=CCC(C)C(C(C)C1CC=CCC(C(CC2=C(C(=CC(=C2)OC)O)C(=O)O1)O)C)O)O
• SMILES (Isomeric): CCC[C@@H]([C@@H](C)C(=O)NC/C=C\C[C@@H](C)[C@H]([C@H](C)[C@@H]1C/C=C\C[C@@H]([C@@H](CC2=C(C(=CC(=C2)OC)O)C(=O)O1)O)C)O)O
• InChI: InChI=1S/C33H51NO8/c1-7-12-26(35)22(4)32(39)34-16-11-10-14-21(3)31(38)23(5)29-15-9-8-13-20(2)27(36)18-24-17-25(41-6)19-28(37)30(24)33(40)42-29/h8-11,17,19-23,26-27,29,31,35-38H,7,12-16,18H2,1-6H3,(H,34,39)/b9-8-,11-10-/t20-,21+,22+,23+,26-,27+,29-,31+/m0/s1
• InChI Key: UXPPKIOUXFFKDI-QGMVIAOPSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₁NO₈
• Molecular Weight: 589.80 g/mol
• Exact Mass: 589.36146759 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.31
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 12

Synonyms

• (2R,3S)-N-{(2Z,5R,6R,7S)-7-[(3S,5Z,8S,9R)-9,14-dihydroxy-12-methoxy-8-methyl-1-oxo-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclododecin-3-yl]-6-hydroxy-5-methyloct-2-en-1-yl}-3-hydroxy-2-methylhexanamide
• XBC

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9087	90.87%
Caco-2	-	0.8002	80.02%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6077	60.77%
OATP2B1 inhibitior	-	0.7224	72.24%
OATP1B1 inhibitior	+	0.8230	82.30%
OATP1B3 inhibitior	+	0.9089	90.89%
MATE1 inhibitior	-	0.8646	86.46%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7797	77.97%
P-glycoprotein inhibitior	+	0.7392	73.92%
P-glycoprotein substrate	+	0.7106	71.06%
CYP3A4 substrate	+	0.6794	67.94%
CYP2C9 substrate	-	0.8035	80.35%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	+	0.7052	70.52%
CYP2C9 inhibition	-	0.7846	78.46%
CYP2C19 inhibition	-	0.7865	78.65%
CYP2D6 inhibition	-	0.8143	81.43%
CYP1A2 inhibition	-	0.5949	59.49%
CYP2C8 inhibition	+	0.5836	58.36%
CYP inhibitory promiscuity	-	0.8054	80.54%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6615	66.15%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9373	93.73%
Skin irritation	-	0.7913	79.13%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6828	68.28%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8742	87.42%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6500	65.00%
Acute Oral Toxicity (c)	III	0.6170	61.70%
Estrogen receptor binding	+	0.7947	79.47%
Androgen receptor binding	+	0.7029	70.29%
Thyroid receptor binding	+	0.5264	52.64%
Glucocorticoid receptor binding	+	0.7471	74.71%
Aromatase binding	+	0.6275	62.75%
PPAR gamma	+	0.6212	62.12%
Honey bee toxicity	-	0.7135	71.35%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9175	91.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.05%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.33%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.71%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.31%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.97%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.88%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.14%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.10%	91.07%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	91.01%	80.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.99%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	90.76%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.65%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.61%	99.23%
CHEMBL2535	P11166	Glucose transporter	88.97%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	88.33%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	85.78%	95.93%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.60%	85.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.75%	97.09%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	83.52%	96.25%
CHEMBL261	P00915	Carbonic anhydrase I	82.92%	96.76%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.66%	95.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.10%	96.38%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.99%	93.56%
CHEMBL4208	P20618	Proteasome component C5	81.57%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	80.77%	98.59%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 16093996
• LOTUS: LTS0094515
• wikiData: Q105280968