5beta,11-dihydroxy-iphionan-4one-11-O-(alpha-xylopyranoside-triacetate) - Compound Card

5beta,11-dihydroxy-iphionan-4one-11-O-(alpha-xylopyranoside-triacetate)

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5beta,11-dihydroxy-iphionan-4one-11-O-(alpha-xylopyranoside-triacetate)

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles CC(=O)O[C@H]1[C@@H](OC[C@H]([C@@H]1OC(=O)C)OC(=O)C)OC([C@@H]1CC[C@@]2([C@@](C1)(O)[C@H](CC2)C(=O)C)C)(C)C
InChI InChI=1S/C26H40O10/c1-14(27)19-9-11-25(7)10-8-18(12-26(19,25)31)24(5,6)36-23-22(35-17(4)30)21(34-16(3)29)20(13-32-23)33-15(2)28/h18-23,31H,8-13H2,1-7H3/t18-,19-,20-,21+,22-,23+,25+,26+/m1/s1
InChIKey DUOPFVPGSBUGGE-AIUFNOAXSA-N
Formula C26H40O10
HBA 10
HBD 1
MW 512.6
Rotatable Bonds 7
TPSA 134.66
LogP 2.47
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 512.26
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Iphiona scabra Asteraceae Plantae 211591

Showing of synonyms

  • El-Ghazouly MG, El-Seeakhy NA, et al. (1987). Sesquiterpene xylosides from Iphiona scabra. Phytochemistry,1987,26,439-443. [View]
Pubchem: 162816906
Nmrshiftdb2: 70060816

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC(C2)CCC(C23)CCC3

Level: 1

Mol. Weight: 512.6 g/mol

Structure

SMILES: C1CCC(C12)CCCC2

Level: 0

Mol. Weight: 512.6 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 512.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
71.71
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
10.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.57
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.02
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-208.93
Rat (Acute)
3.26
Rat (Chronic Oral)
2.05
Fathead Minnow
3.94
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
416.16
Hydration Free Energy
-2.74
Log(D) at pH=7.4
1.53
Log(P)
2.53
Log S
-4.27
Log(Vapor Pressure)
-8.35
Melting Point
140.76
pKa Acid
7.21
pKa Basic
3.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9031
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9031
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7553
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7553
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7360
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7360

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