1beta,8beta-dihydroxyeudesman-4(15),7(11)-dien-8alpha,l2-olide - Compound Card

1beta,8beta-dihydroxyeudesman-4(15),7(11)-dien-8alpha,l2-olide

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1beta,8beta-dihydroxyeudesman-4(15),7(11)-dien-8alpha,l2-olide

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1CC[C@H]([C@]2([C@H]1CC1=C(C)C(=O)O[C@]1(C2)O)C)O
InChI InChI=1S/C15H20O4/c1-8-4-5-12(16)14(3)7-15(18)11(6-10(8)14)9(2)13(17)19-15/h10,12,16,18H,1,4-7H2,2-3H3/t10-,12+,14+,15-/m0/s1
InChIKey WSGUEAHXLYQKIH-BTQDYEIMSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.68
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
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: 12009778
Nmrshiftdb2: 60032409

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 264.32 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
41.2
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.02
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.57
Micronucleos
Safe
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
-1.31
Rat (Acute)
2.94
Rat (Chronic Oral)
1.74
Fathead Minnow
3.92
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
326.13
Hydration Free Energy
-7.99
Log(D) at pH=7.4
1.39
Log(P)
2.02
Log S
-2.25
Log(Vapor Pressure)
-6.22
Melting Point
160.35
pKa Acid
6.88
pKa Basic
5.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8824
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8824
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8680
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8680
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8346
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8346
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8042
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8042
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8021
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8021
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7957
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7957
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7398
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7398
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7387
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7387
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7352
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7352
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7322
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7322
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7302
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7302
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7220
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7220
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7183
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7183
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7155
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7155
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7134
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7134

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