3alpha-acetoxy-beta-eudesmol-(alpha-xylopyranoside-triacetate) - Compound Card

3alpha-acetoxy-beta-eudesmol-(alpha-xylopyranoside-triacetate)

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3alpha-acetoxy-beta-eudesmol-(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@@H](C1)C(=C)[C@@H](CC2)O)C)(C)C
InChI InChI=1S/C26H40O9/c1-14-19-12-18(8-10-26(19,7)11-9-20(14)30)25(5,6)35-24-23(34-17(4)29)22(33-16(3)28)21(13-31-24)32-15(2)27/h18-24,30H,1,8-13H2,2-7H3/t18-,19+,20-,21-,22+,23-,24+,26+/m1/s1
InChIKey RXZTXJNLNMJMHG-FAKSQXSBSA-N
Formula C26H40O9
HBA 9
HBD 1
MW 496.6
Rotatable Bonds 6
TPSA 117.59
LogP 3.07
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 496.27
Number of Lipinski Rule Violations 0
# 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: 162816917
Nmrshiftdb2: 70060819

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(C12)CCC(C2)COC3CCCCO3

Level: 1

Mol. Weight: 496.6 g/mol

Structure

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 496.6 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 496.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
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
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
68.52
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
10.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.64
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
-139.68
Rat (Acute)
3.73
Rat (Chronic Oral)
2.32
Fathead Minnow
3.92
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
408.87
Hydration Free Energy
-2.51
Log(D) at pH=7.4
2.23
Log(P)
3.49
Log S
-4.92
Log(Vapor Pressure)
-8.15
Melting Point
124.25
pKa Acid
7.49
pKa Basic
3.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8712
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8712
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7891
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7891
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7819
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7819
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7648
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7530
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7530
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7458
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7406
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7406
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7329
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7329
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7268
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7268
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7223
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7223
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7103
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7103
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7085
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7085
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7060
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7060
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7026
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7026
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7011
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7011

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