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

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

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7beta-hydroxy-3beta-acetoxy-5beta,6beta-epoxyeudesm-5(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)OC(=O)C)C)(C)C)/C
InChI InChI=1S/C35H50O12/c1-12-18(3)28(38)44-25-21(6)41-30(27(26(25)43-23(8)37)45-29(39)19(4)13-2)46-32(9,10)34(40)17-16-33(11)15-14-24(42-22(7)36)20(5)35(33)31(34)47-35/h12-13,21,24-27,30-31,40H,5,14-17H2,1-4,6-11H3/b18-12-,19-13-/t21-,24-,25+,26+,27-,30?,31-,33-,34-,35-/m1/s1
InChIKey IUDVKUNVWZIINQ-COYPLYOCSA-N
Formula C35H50O12
HBA 12
HBD 1
MW 662.77
Rotatable Bonds 9
TPSA 156.42
LogP 4.16
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 662.33
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: 162934470
Nmrshiftdb2: 70014200

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 662.77 g/mol

Structure

SMILES: C=C1CCCC2CCCC(C123)O3

Level: 0

Mol. Weight: 662.77 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 662.77 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
29.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.34
Plasma Protein Binding
71.1
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
11.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
8.15
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
-59996.34
Rat (Acute)
5.21
Rat (Chronic Oral)
2.27
Fathead Minnow
92.62
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
2686.66
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.27
Log(P)
5.38
Log S
-5.39
Log(Vapor Pressure)
-110.8
Melting Point
99.04
pKa Acid
5.82
pKa Basic
-1.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7654
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7654
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7350
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7350
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7123
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7123

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