(5S)-5-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,7-bis(4-hydroxyphenyl)heptan-3-one

Details

• Internal ID: 277ce0a8-a21e-4b92-8368-16ad7f4dc9ff
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (5S)-5-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,7-bis(4-hydroxyphenyl)heptan-3-one
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC(CCC3=CC=C(C=C3)O)CC(=O)CCC4=CC=C(C=C4)O)CO)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@H](CCC3=CC=C(C=C3)O)CC(=O)CCC4=CC=C(C=C4)O)CO)O)O)O)(CO)O
• InChI: InChI=1S/C30H40O13/c31-14-23-24(36)25(37)26(43-29-27(38)30(39,15-32)16-40-29)28(42-23)41-22(12-6-18-3-9-20(34)10-4-18)13-21(35)11-5-17-1-7-19(33)8-2-17/h1-4,7-10,22-29,31-34,36-39H,5-6,11-16H2/t22-,23+,24+,25-,26+,27-,28+,29-,30+/m0/s1
• InChI Key: NUACGMYJCUJZFV-BYWUESOHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₁₃
• Molecular Weight: 608.60 g/mol
• Exact Mass: 608.24689133 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.73
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6696	66.96%
Caco-2	-	0.9060	90.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8408	84.08%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.8798	87.98%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9740	97.40%
P-glycoprotein inhibitior	+	0.6631	66.31%
P-glycoprotein substrate	+	0.5118	51.18%
CYP3A4 substrate	+	0.6816	68.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8335	83.35%
CYP3A4 inhibition	-	0.8713	87.13%
CYP2C9 inhibition	-	0.8679	86.79%
CYP2C19 inhibition	-	0.8264	82.64%
CYP2D6 inhibition	-	0.8953	89.53%
CYP1A2 inhibition	-	0.9100	91.00%
CYP2C8 inhibition	+	0.5209	52.09%
CYP inhibitory promiscuity	-	0.9105	91.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5866	58.66%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.8184	81.84%
Skin corrosion	-	0.9577	95.77%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8231	82.31%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8890	88.90%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6339	63.39%
Acute Oral Toxicity (c)	III	0.5835	58.35%
Estrogen receptor binding	+	0.8131	81.31%
Androgen receptor binding	+	0.7014	70.14%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5428	54.28%
Aromatase binding	+	0.6184	61.84%
PPAR gamma	+	0.7388	73.88%
Honey bee toxicity	-	0.6348	63.48%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8176	81.76%

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	99.24%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.11%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.31%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.17%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.97%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.76%	95.93%
CHEMBL3437	Q16853	Amine oxidase, copper containing	91.96%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.35%	99.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.15%	94.62%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	87.82%	85.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.76%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.57%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.22%	89.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.64%	95.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.19%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.08%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.97%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.34%	95.89%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	82.98%	100.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.95%	94.97%
CHEMBL3401	O75469	Pregnane X receptor	82.80%	94.73%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.54%	100.00%
CHEMBL2514	O95665	Neurotensin receptor 2	81.56%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.72%	92.94%

Plants that contains it

• Betula papyrifera
• Betula pendula

Cross-Links

• PubChem: 162985559
• LOTUS: LTS0117310
• wikiData: Q105185784