Swertiamacroside

Details

• Internal ID: 7c7e40d9-70cc-4e0e-b795-b6d449953893
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Hydroxycinnamic acid glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H28O13/c1-8-14(25)16(27)18(29)20(32-8)31-7-12-15(26)17(28)19(30)21(33-12)34-13(24)5-3-9-2-4-10(22)11(23)6-9/h2-6,8,12,14-23,25-30H,7H2,1H3/b5-3+/t8-,12+,14-,15+,16+,17-,18+,19+,20+,21-/m0/s1
• InChI Key: VMCOATNLXZKVSB-JRQIJAMCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₁₃
• Molecular Weight: 488.40 g/mol
• Exact Mass: 488.15299094 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 128585-97-7
• 1-O-Caffeoyl-O-rutinose ester
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 1-O-Caffeoyl-6-O-alpha-rhamnopyranosyl-beta-glycopyranoside
• beta-D-Glucopyranose, 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, 1-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6180	61.80%
Caco-2	-	0.8873	88.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7170	71.70%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.9072	90.72%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5898	58.98%
P-glycoprotein inhibitior	-	0.8449	84.49%
P-glycoprotein substrate	-	0.8428	84.28%
CYP3A4 substrate	+	0.5493	54.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.8714	87.14%
CYP2C9 inhibition	-	0.8512	85.12%
CYP2C19 inhibition	-	0.8754	87.54%
CYP2D6 inhibition	-	0.9146	91.46%
CYP1A2 inhibition	-	0.8824	88.24%
CYP2C8 inhibition	+	0.5338	53.38%
CYP inhibitory promiscuity	-	0.5828	58.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6818	68.18%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.7980	79.80%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4365	43.65%
Micronuclear	+	0.5566	55.66%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.7805	78.05%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.9513	95.13%
Acute Oral Toxicity (c)	III	0.7757	77.57%
Estrogen receptor binding	+	0.6320	63.20%
Androgen receptor binding	-	0.6810	68.10%
Thyroid receptor binding	+	0.6108	61.08%
Glucocorticoid receptor binding	-	0.4918	49.18%
Aromatase binding	+	0.5474	54.74%
PPAR gamma	+	0.7099	70.99%
Honey bee toxicity	-	0.8463	84.63%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.8733	87.33%

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	99.75%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.75%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.95%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.34%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.33%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.89%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	93.57%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.28%	97.36%
CHEMBL3194	P02766	Transthyretin	89.95%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.70%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.71%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.86%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.09%	80.78%
CHEMBL4208	P20618	Proteasome component C5	85.07%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.24%	99.15%

Plants that contains it

• Achillea leptophylla
• Forsythia suspensa
• Forsythia viridissima
• Iris sanguinea
• Swertia japonica

Cross-Links

• PubChem: 6443992
• NPASS: NPC51400
• LOTUS: LTS0160257
• wikiData: Q105288902