Ambrosin - Compound Card

Ambrosin

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Ambrosin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@H]1CC[C@@H]2[C@H]([C@]3([C@H]1C=CC3=O)C)OC(=O)C2=C
InChI InChI=1S/C15H18O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h6-8,10-11,13H,2,4-5H2,1,3H3/t8-,10-,11-,13+,15-/m0/s1
InChIKey IFXGCKRDLITNAU-JHSUYXJUSA-N
Formula C15H18O3
HBA 3
HBD 0
MW 246.31
Rotatable Bonds 0
TPSA 43.37
LogP 2.28
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 246.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ambrosia maritima Asteraceae Plantae 1028380
2 Ambrosia maritima Asteraceae Plantae 1028380

Showing of synonyms

  • Saad MMG, Abdelgaleil SAM, et al. (2012). Herbicidal potential of pseudoguaninolide sesquiterpenes on wild oat, Avena fatua L.. Biochemical Systematics and Ecology,2012,44,333-337. [View]
  • Picman AK, Arnason JT, et al. (1986). Hymenin, another sesquiterpene lactone in Ambrosia maritima.. Journal of Natural Products,1986,49(3),556-556. [View]
Pubchem: 92119
Kegg Ligand: C09292
Chebi: 2629
Nmrshiftdb2: 60072065
CPRiL: 86601
Structure

SMILES: C=C1C(=O)OC2C1CCCC(C23)C=CC3=O

Level: 0

Mol. Weight: 246.31 g/mol

Phytotoxicity

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
53.61
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.87
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.48
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.24
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.35
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.54
Rat (Acute)
2.44
Rat (Chronic Oral)
1.7
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
328.46
Hydration Free Energy
-5.34
Log(D) at pH=7.4
2.02
Log(P)
1.43
Log S
-3.22
Log(Vapor Pressure)
-4.69
Melting Point
144.97
pKa Acid
8.94
pKa Basic
5.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8974
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8974
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7977
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7977

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