(2R,3R,4R)-N-[(3R)-3-[4-[(E)-3-[(2S,3S,5S,7S,8R,9R)-2-[(1R,3R,4R,5S,6S,7E,9E,11E,13E)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl]-3,7-dihydroxy-4,4,8-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]prop-1-enyl]-1,3-oxazol-2-yl]butyl]-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamide

Details

• Internal ID: b4b0052a-921b-42b6-9b3a-2a0b1708d211
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Aromatic monoterpenoids
• IUPAC Name: (2R,3R,4R)-N-[(3R)-3-[4-[(E)-3-[(2S,3S,5S,7S,8R,9R)-2-[(1R,3R,4R,5S,6S,7E,9E,11E,13E)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl]-3,7-dihydroxy-4,4,8-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]prop-1-enyl]-1,3-oxazol-2-yl]butyl]-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamide
• SMILES (Canonical): CC1C(CC2(C(C(C(O2)C(CC(C(C)C(C(C)C=C(C)C(=CC=CC(=CC#N)C)C)O)O)OC)O)(C)C)OC1CC=CC3=COC(=N3)C(C)CCNC(=O)C(C(C(COC)N(C)C)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@]2(C([C@@H]([C@H](O2)[C@@H](C[C@H]([C@@H](C)[C@H]([C@@H](C)/C=C(\C)/C(=C/C=C/C(=C/C#N)/C)/C)O)O)OC)O)(C)C)O[C@@H]1C/C=C/C3=COC(=N3)[C@H](C)CCNC(=O)[C@@H]([C@@H]([C@@H](COC)N(C)C)O)O)O
• InChI: InChI=1S/C50H80N4O12/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(63-13)45-46(60)49(8,9)50(66-45)26-39(56)34(6)40(65-50)19-15-18-36-27-64-48(53-36)31(3)21-23-52-47(61)44(59)43(58)37(28-62-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-60H,19,21,23,25-26,28H2,1-13H3,(H,52,61)/b16-14+,18-15+,29-20+,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45-,46-,50+/m1/s1
• InChI Key: FRXOVDDVHJLWBQ-PFUZMBLPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₀N₄O₁₂
• Molecular Weight: 929.20 g/mol
• Exact Mass: 928.57727400 g/mol
• Topological Polar Surface Area (TPSA): 241.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 24

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6623	66.23%
Caco-2	-	0.8647	86.47%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.5684	56.84%
OATP2B1 inhibitior	-	0.8640	86.40%
OATP1B1 inhibitior	+	0.8111	81.11%
OATP1B3 inhibitior	+	0.9373	93.73%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9866	98.66%
P-glycoprotein inhibitior	+	0.7444	74.44%
P-glycoprotein substrate	+	0.8286	82.86%
CYP3A4 substrate	+	0.7579	75.79%
CYP2C9 substrate	-	0.7900	79.00%
CYP2D6 substrate	-	0.8371	83.71%
CYP3A4 inhibition	-	0.9634	96.34%
CYP2C9 inhibition	-	0.8926	89.26%
CYP2C19 inhibition	-	0.8966	89.66%
CYP2D6 inhibition	-	0.9087	90.87%
CYP1A2 inhibition	-	0.8551	85.51%
CYP2C8 inhibition	+	0.7922	79.22%
CYP inhibitory promiscuity	-	0.9663	96.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5238	52.38%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9179	91.79%
Ames mutagenesis	-	0.5278	52.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7569	75.69%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.6178	61.78%
skin sensitisation	-	0.8433	84.33%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7587	75.87%
Acute Oral Toxicity (c)	III	0.5713	57.13%
Estrogen receptor binding	+	0.8051	80.51%
Androgen receptor binding	+	0.7168	71.68%
Thyroid receptor binding	+	0.6377	63.77%
Glucocorticoid receptor binding	+	0.7582	75.82%
Aromatase binding	+	0.6129	61.29%
PPAR gamma	+	0.8301	83.01%
Honey bee toxicity	-	0.5967	59.67%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.6261	62.61%

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	99.23%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.53%	98.95%
CHEMBL1914	P06276	Butyrylcholinesterase	96.36%	95.00%
CHEMBL221	P23219	Cyclooxygenase-1	95.64%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	95.11%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	94.09%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.45%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.06%	96.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.29%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.12%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.39%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.03%	95.71%
CHEMBL3837	P07711	Cathepsin L	88.76%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.75%	89.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.24%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.05%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.75%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.51%	98.75%
CHEMBL1937	Q92769	Histone deacetylase 2	87.30%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.89%	85.14%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.72%	89.67%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.92%	93.10%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.17%	96.90%
CHEMBL5028	O14672	ADAM10	82.09%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.08%	97.09%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	81.84%	96.25%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.65%	88.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101702401
• LOTUS: LTS0105215
• wikiData: Q105000487