2alpha-acetyloxy-4beta-hydroxy-6alpha-angeloyloxy-10beta-benzoyloxydauc-8-ene - Compound Card

2alpha-acetyloxy-4beta-hydroxy-6alpha-angeloyloxy-10beta-benzoyloxydauc-8-ene

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2alpha-acetyloxy-4beta-hydroxy-6alpha-angeloyloxy-10beta-benzoyloxydauc-8-ene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpenes Daucane Ester
Canonical Smiles C/C=C(\C(=O)O[C@H]1CC(=C[C@@H]([C@@]2([C@@H]1[C@@](O)(C[C@@H]2OC(=O)C)C(C)C)C)OC(=O)c1ccccc1)C)/C
InChI InChI=1S/C29H38O7/c1-8-19(5)26(31)35-22-14-18(4)15-23(36-27(32)21-12-10-9-11-13-21)28(7)24(34-20(6)30)16-29(33,17(2)3)25(22)28/h8-13,15,17,22-25,33H,14,16H2,1-7H3/b19-8-/t22-,23-,24-,25+,28-,29+/m0/s1
InChIKey FEVCNFNUZYJNNU-FQIPTQIUSA-N
Formula C29H38O7
HBA 7
HBD 1
MW 498.62
Rotatable Bonds 6
TPSA 99.13
LogP 4.79
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 498.26
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Daucus carota subsp. carota Apiaceae Plantae —

Showing of synonyms

  • Ahmed AA, Bishr MM, et al. (2005). Rare trisubstituted sesquiterpenes daucanes from the wild Daucus carota. Phytochemistry,2005,66(14),1680-1684. [View] [PubMed]
Pubchem: 11518931

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2C=CCCC(C23)CCC3

Level: 1

Mol. Weight: 498.62 g/mol

Structure

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 498.62 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 498.62 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
95.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
10.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.14
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
-281.82
Rat (Acute)
3.41
Rat (Chronic Oral)
2.47
Fathead Minnow
4.31
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
425.36
Hydration Free Energy
-2.62
Log(D) at pH=7.4
4.03
Log(P)
5.65
Log S
-5.45
Log(Vapor Pressure)
-8.23
Melting Point
134.71
pKa Acid
9.4
pKa Basic
3.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8379
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8379
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7061
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7061

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