3alpha,7beta-dihydroxy-5beta,6beta-epoxyeudesm-4(15)-ene-11-(O-beta-D-fucopyranoside-2',4'-diangelate-3'-acetate) - Compound Card

3alpha,7beta-dihydroxy-5beta,6beta-epoxyeudesm-4(15)-ene-11-(O-beta-D-fucopyranoside-2',4'-diangelate-3'-acetate)

Select a section from the left sidebar

3alpha,7beta-dihydroxy-5beta,6beta-epoxyeudesm-4(15)-ene-11-(O-beta-D-fucopyranoside-2',4'-diangelate-3'-acetate)

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles C/C=C(\C(=O)O[C@H]1C(O[C@@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)/C(=C\C)/C)C)OC([C@@]1(O)CC[C@@]2([C@]3([C@@H]1O3)C(=C)[C@@H](CC2)O)C)(C)C)/C
InChI InChI=1S/C33H48O11/c1-11-17(3)26(36)41-23-20(6)39-28(25(24(23)40-21(7)34)42-27(37)18(4)12-2)43-30(8,9)32(38)16-15-31(10)14-13-22(35)19(5)33(31)29(32)44-33/h11-12,20,22-25,28-29,35,38H,5,13-16H2,1-4,6-10H3/b17-11-,18-12-/t20-,22-,23+,24+,25-,28?,29-,31-,32-,33-/m1/s1
InChIKey AKACNUARSZZVHH-FYJKLWJNSA-N
Formula C33H48O11
HBA 11
HBD 2
MW 620.74
Rotatable Bonds 8
TPSA 150.35
LogP 3.59
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 620.32
Number of Lipinski Rule Violations 2
# 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: 162987380
Nmrshiftdb2: 70014201

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC2CCC(C(C123)O3)COC4CCCCO4

Level: 1

Mol. Weight: 620.74 g/mol

Structure

SMILES: C=C1CCCC2CCCC(C123)O3

Level: 0

Mol. Weight: 620.74 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 620.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
67.01
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.74
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
8.29
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
Toxic
T. Pyriformis
-16197.61
Rat (Acute)
5.18
Rat (Chronic Oral)
2.48
Fathead Minnow
38.03
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
214.17
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.91
Log(P)
4.44
Log S
-4.92
Log(Vapor Pressure)
-7.9
Melting Point
112.18
pKa Acid
5.68
pKa Basic
-1.34
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 2 0.7203
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7203
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7090
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7090

Download SDF