Alpha-bisabolone-beta-D-fucopyranoside - Compound Card

Alpha-bisabolone-beta-D-fucopyranoside

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Alpha-bisabolone-beta-D-fucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles CC1=CC(=O)[C@@H](CC1)[C@H](CC[C@H](C(C)C)O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)O)O)C
InChI InChI=1S/C21H36O6/c1-11(2)17(27-21-20(25)19(24)18(23)14(5)26-21)9-7-13(4)15-8-6-12(3)10-16(15)22/h10-11,13-15,17-21,23-25H,6-9H2,1-5H3/t13-,14+,15-,17+,18-,19-,20+,21-/m0/s1
InChIKey MAMURXKKLQVDLN-GZJNYRSUSA-N
Formula C21H36O6
HBA 6
HBD 3
MW 384.51
Rotatable Bonds 7
TPSA 96.22
LogP 2.2
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 384.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Calendula arvensis Asteraceae Plantae 99035

Showing of synonyms

  • Ahmed AA, Jakupovic J, et al. (1993). Sesquiterpene glycosides from Calendula arvensis. Journal of Natural Products,1993,56(10),1821-1829. [View] [PubMed]
Pubchem: 162816955
Nmrshiftdb2: 70014199

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC1CCCCOC2CCCCO2

Level: 1

Mol. Weight: 384.51 g/mol

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 384.51 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 384.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
79.5
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
4.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.73
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.35
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.78
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
-6.35
Rat (Acute)
2.83
Rat (Chronic Oral)
2.71
Fathead Minnow
3.78
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
413.34
Hydration Free Energy
-11.08
Log(D) at pH=7.4
2.35
Log(P)
2.33
Log S
-3.06
Log(Vapor Pressure)
-8.81
Melting Point
135.72
pKa Acid
7.5
pKa Basic
5.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8458
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8458
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7808
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7808
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7755
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7755
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7701
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7701
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7436
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7436
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7376
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7376
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7344
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7344
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7337
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7337
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7258
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7258
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7083
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7083
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7034
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7034

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