1beta-acetoxyeudesman-4(15),7(11)-dien-8alpha,12-olide - Compound Card

1beta-acetoxyeudesman-4(15),7(11)-dien-8alpha,12-olide

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1beta-acetoxyeudesman-4(15),7(11)-dien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(=O)O[C@@H]1CCC(=C)[C@H]2[C@@]1(C)C[C@@H]1OC(=O)C(=C1C2)C
InChI InChI=1S/C17H22O4/c1-9-5-6-15(20-11(3)18)17(4)8-14-12(7-13(9)17)10(2)16(19)21-14/h13-15H,1,5-8H2,2-4H3/t13-,14-,15+,17+/m0/s1
InChIKey PQZAVXWUUFLUKB-LJIGWXMPSA-N
Formula C17H22O4
HBA 4
HBD 0
MW 290.36
Rotatable Bonds 1
TPSA 52.6
LogP 2.93
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 290.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Smyrnium olusatrum Apiaceae Plantae 40962

Showing of synonyms

  • El-Gamal AA (2001). Sesquiterpene lactones from Smyrnium olusatrum. Phytochemistry,2001,57(8),1197-1200. [View]
Pubchem: 97045423
Nmrshiftdb2: 60047354

No compound-protein relationship available.

Structure

SMILES: C1CCC(=C)C(C2)C1CC(C2=3)OC(=O)C3

Level: 0

Mol. Weight: 290.36 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
50.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.33
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.8
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
-0.38
Rat (Acute)
2.43
Rat (Chronic Oral)
1.89
Fathead Minnow
3.92
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
336.36
Hydration Free Energy
-3.9
Log(D) at pH=7.4
2.49
Log(P)
2.9
Log S
-3.79
Log(Vapor Pressure)
-5.32
Melting Point
103.51
pKa Acid
10.73
pKa Basic
6.1
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 3 0.8821
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8821
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8196
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8196
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8120
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8120
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8033
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8033
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8026
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8026
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7993
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7993
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7905
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7905
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7903
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7903
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7670
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7670
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7648
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7605
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7605
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7567
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7567
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7556
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7556
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7340
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7340
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7122
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7122

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