4beta-dihydroxy-5alpha(H)-guaia-1(10),11(13)-dien-8alpha,12-olide - Compound Card

4beta-dihydroxy-5alpha(H)-guaia-1(10),11(13)-dien-8alpha,12-olide

Select a section from the left sidebar

4beta-dihydroxy-5alpha(H)-guaia-1(10),11(13)-dien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2C(C1=C)CC1C(=C(C2)C)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/h11-13,17H,2,4-7H2,1,3H3/t11?,12?,13-,15-/m1/s1
InChIKey CLYBLORMANTURF-UJFKTDLFSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.36
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 Pulicaria crispa Asteraceae Plantae 119186

Showing of synonyms

  • Dendougui H, Benayache S, et al. (2000). Sesquiterpene lactones from Pulicaria crispa. Fitoterapia,2000,71,373-378. [View] [PubMed]
Pubchem: 162905673

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC2)C1CC(C=23)CCC3

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
42.81
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
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
11.16
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.03
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
-0.86
Rat (Acute)
2.48
Rat (Chronic Oral)
1.77
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
319.26
Hydration Free Energy
-5.76
Log(D) at pH=7.4
1.65
Log(P)
2.04
Log S
-2.47
Log(Vapor Pressure)
-5.08
Melting Point
118.09
pKa Acid
9.62
pKa Basic
6.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8552
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8552
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7967
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7967
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7856
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7856
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7801
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7801
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7791
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7791
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7763
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7763
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7590
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7590
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7475
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7475
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7409
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7409
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7388
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7388
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7286
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7286
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7263
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7263
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7257
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7257
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7248
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7248
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7241
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7241
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7161
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7161
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7153
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7153
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7136
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7136
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7134
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7134
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7121
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7121
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7109
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7109
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7093
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7093
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7001
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7001

Download SDF