4alpha-hydroxy-1betaH-guaia-9(14),12-dien-8beta,11-olide - Compound Card

4alpha-hydroxy-1betaH-guaia-9(14),12-dien-8beta,11-olide

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4alpha-hydroxy-1betaH-guaia-9(14),12-dien-8beta,11-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1C(=O)O[C@@H]2C1C[C@@H]1[C@@H](C(=C)C2)CC[C@@]1(C)O
InChI InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h10-13,17H,1-2,4-7H2,3H3/t10-,11?,12-,13+,15-/m1/s1
InChIKey GTYUWNQOOLJZBM-ZWOWXGAWSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.21
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Francoeuria crispa Asteraceae Plantae 1548540

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
Pubchem: 44715822

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC(=C)C3C(C2)CCC3

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
42.25
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.75
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
-0.14
Rat (Acute)
2.34
Rat (Chronic Oral)
1.72
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
321.91
Hydration Free Energy
-5.54
Log(D) at pH=7.4
1.48
Log(P)
1.98
Log S
-2.7
Log(Vapor Pressure)
-4.95
Melting Point
123.55
pKa Acid
9.19
pKa Basic
6.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8802
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8802
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8008
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8008
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7933
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7933
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7726
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7726
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7602
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7602
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7577
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7577
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7556
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7556
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7551
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7551
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7512
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7512
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7497
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7497
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7490
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7490
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7482
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7482
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7475
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7475
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7460
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7460
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7454
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7454
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7425
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7425
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7396
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7396
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7358
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7358
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7317
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7317
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7296
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7296
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7271
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7271
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7224
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7224
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7218
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7218
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7205
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7205
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7192
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102

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