Rosarin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	1a16da80-8594-4f27-9ac6-ae51ca71571c
Taxonomy	Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
IUPAC Name	(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol
SMILES (Canonical)	C1=CC=C(C=C1)C=CCOC2C(C(C(C(O2)COC3C(C(C(O3)CO)O)O)O)O)O
SMILES (Isomeric)	C1=CC=C(C=C1)/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H](O3)CO)O)O)O)O)O
InChI	InChI=1S/C20H28O10/c21-9-12-14(22)17(25)20(29-12)28-10-13-15(23)16(24)18(26)19(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19+,20+/m0/s1
InChI Key	IEBFEMIXXHIISM-YZOUKVLTSA-N
Popularity	6 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₀H₂₈O₁₀
Molecular Weight	428.40 g/mol
Exact Mass	428.16824709 g/mol
Topological Polar Surface Area (TPSA)	158.00 Å²
XlogP	-1.40
Atomic LogP (AlogP)	-2.02
H-Bond Acceptor	10
H-Bond Donor	6
Rotatable Bonds	8

Synonyms

Top

84954-93-8

Rosarin (glycoside)

Rosarin, (-)-

UNII-PQA54L0KFI

PQA54L0KFI

Rosarin (constituent of rhodiola rosea) [DSC]

beta-D-Glucopyranoside, (2E)-3-phenyl-2-propen-1-yl 6-o-alpha-L-arabinofuranosyl-

(2R,3R,4S,5S,6R)-2-(cinnamyloxy)-6-((((2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Rosarin, >=98% (HPLC)

SCHEMBL14705646

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8760	87.60%
Caco-2	-	0.8527	85.27%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7047	70.47%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8639	86.39%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7093	70.93%
P-glycoprotein inhibitior	-	0.8248	82.48%
P-glycoprotein substrate	-	0.9630	96.30%
CYP3A4 substrate	-	0.5469	54.69%
CYP2C9 substrate	+	0.5790	57.90%
CYP2D6 substrate	-	0.8176	81.76%
CYP3A4 inhibition	-	0.9041	90.41%
CYP2C9 inhibition	-	0.9094	90.94%
CYP2C19 inhibition	-	0.7858	78.58%
CYP2D6 inhibition	-	0.8737	87.37%
CYP1A2 inhibition	-	0.9049	90.49%
CYP2C8 inhibition	-	0.5886	58.86%
CYP inhibitory promiscuity	-	0.5261	52.61%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5512	55.12%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9601	96.01%
Skin irritation	-	0.8586	85.86%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6833	68.33%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.8915	89.15%
skin sensitisation	-	0.8843	88.43%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.6962	69.62%
Acute Oral Toxicity (c)	III	0.5793	57.93%
Estrogen receptor binding	+	0.5301	53.01%
Androgen receptor binding	-	0.6036	60.36%
Thyroid receptor binding	+	0.5211	52.11%
Glucocorticoid receptor binding	-	0.7159	71.59%
Aromatase binding	+	0.7452	74.52%
PPAR gamma	+	0.7833	78.33%
Honey bee toxicity	-	0.8560	85.60%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	-	0.4273	42.73%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	97.80%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.37%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.98%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.79%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	89.40%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	88.84%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.98%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.05%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.46%	91.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.11%	99.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.72%	94.08%
CHEMBL2581	P07339	Cathepsin D	81.18%	98.95%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.52%	88.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.18%	86.92%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.