(2S,5R)-5-(2-hydroxypropan-2-yl)-2-[(2R)-5-oxohexan-2-yl]cyclohexan-1-one (2-xylopyranoside 2-acetate) - Compound Card

(2S,5R)-5-(2-hydroxypropan-2-yl)-2-[(2R)-5-oxohexan-2-yl]cyclohexan-1-one (2-xylopyranoside 2-acetate)

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(2S,5R)-5-(2-hydroxypropan-2-yl)-2-[(2R)-5-oxohexan-2-yl]cyclohexan-1-one (2-xylopyranoside 2-acetate)

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles CC(=O)CCC[C@]1(C)CC[C@H](CC1=O)C(O[C@@H]1OC[C@H]([C@@H]([C@H]1OC(=O)C)O)O)(C)C
InChI InChI=1S/C22H36O8/c1-13(23)7-6-9-22(5)10-8-15(11-17(22)26)21(3,4)30-20-19(29-14(2)24)18(27)16(25)12-28-20/h15-16,18-20,25,27H,6-12H2,1-5H3/t15-,16-,18+,19-,20+,22-/m1/s1
InChIKey PSZRHBIWRDBKCP-JCDBWPDUSA-N
Formula C22H36O8
HBA 8
HBD 2
MW 428.52
Rotatable Bonds 8
TPSA 119.36
LogP 1.93
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Iphiona mucronata Asteraceae Plantae 2072397

Showing of synonyms

  • Ahmed AA (1990). Sesquiterpene xylosides from Iphiona mucronata. Journal of Natural Products,1990,53(4),1031-1033. [View]
Pubchem: 163048924
Nmrshiftdb2: 70060809

No compound-protein relationship available.

Structure

SMILES: C1CCC(CC1=O)COC2CCCCO2

Level: 1

Mol. Weight: 428.52 g/mol

Structure

SMILES: O=C1CCCCC1

Level: 0

Mol. Weight: 428.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 428.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.4
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
68.54
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
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
8.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.3
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.87
Micronucleos
Toxic
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
-13.61
Rat (Acute)
3.17
Rat (Chronic Oral)
2.32
Fathead Minnow
3.87
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
425.32
Hydration Free Energy
-7.6
Log(D) at pH=7.4
1.6
Log(P)
0.96
Log S
-2.36
Log(Vapor Pressure)
-8.42
Melting Point
133.0
pKa Acid
7.1
pKa Basic
2.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9216
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9216
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9147
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9147
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8912
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8912
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7893
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7893
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7860
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7860
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7768
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7768
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7766
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7766
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7758
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7758
Chitinase Q54276 Q54276_SERMA Serratia marcescens 4 0.7634
Chitinase Q54276 Q54276_SERMA Serratia marcescens 4 0.7634
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7471
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7471
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7346
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7346
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7264
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7264
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7065
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7065
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7032
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7032
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7003
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7003

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