Roseoside - Compound Card

Roseoside

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Roseoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Megastigmane Glycoside
Canonical Smiles OC[C@H]1O[C@@H](O[C@@H](/C=C/[C@@]2(O)C(=CC(=O)CC2(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C19H30O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-7,11,13-17,20,22-25H,8-9H2,1-4H3/b6-5+/t11-,13-,14-,15+,16-,17-,19-/m1/s1
InChIKey SWYRVCGNMNAFEK-MHXFFUGFSA-N
Formula C19H30O8
HBA 8
HBD 5
MW 386.44
Rotatable Bonds 5
TPSA 136.68
LogP -0.58
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 386.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ruellia tuberosa Acanthaceae Plantae 441035
2 Ruellia patula Acanthaceae Plantae 441006
3 Tribulus parvispinus Zygophyllaceae Plantae 2603131
4 Conyza aegyptiaca Asteraceae Plantae 741633
5 Crepis sancta Asteraceae Plantae —

Showing of synonyms

  • Mahmouda AA, Al-Shihrya SS, et al. (2009). Biological activity of a phloroglucinol glucoside derivative from Conyza aegyptiaca. Zeitschrift fur Naturforschung C,2009,64,513-517. [View] [PubMed]
  • Samy MN, Khalil HE, et al. (2013). Chemical constituents from the leaves of Ruellia tuberosa. Chemistry of Natural Compounds,2013,49(1),175-176. [View]
  • Ebada S, El-Kashef D, et al. (2019). Cytotoxic eudesmane sesquiterpenes from Crepis sancta. Phytochemistry Letters, 2019, 33, 46-48. [View] [PubMed]
  • Perrone A, Plaza A, et al. (2005). Cytotoxic furostanol saponins and a megastigmane glucoside from Tribulus parvispinus. Journal of Natural Products,2005,68(10),1549-1553. [View] [PubMed]
  • Samy MN, Khalil HE, et al. (2011). Three new flavonoid glycosides, byzantionoside B 6’-O-Sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chemical and Pharmaceutical Bulletin,2011,59(6),725-729. [View] [PubMed]
Pubchem: 9930064
Nmrshiftdb2: 60028459
CPRiL: 79655
Structure

SMILES: O=C1C=CC(CC1)C=CCOC2CCCCO2

Level: 1

Mol. Weight: 386.44 g/mol

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 386.44 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 386.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.21
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.650
Plasma Protein Binding
59.48
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.920
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.500
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.980
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.050
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-6.750
Rat (Acute)
2.570
Rat (Chronic Oral)
2.990
Fathead Minnow
3.930
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
452.870
Hydration Free Energy
-16.820
Log(D) at pH=7.4
0.120
Log(P)
-1.03
Log S
-1.39
Log(Vapor Pressure)
-11.75
Melting Point
141.75
pKa Acid
6.48
pKa Basic
5.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8883
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8883
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8092
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8092
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7523
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7523
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7438
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7438
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7426
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7426
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7417
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7417
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7320
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7320
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7227
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7227
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7168
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7168
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7154
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7154
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7086
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7086

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