1beta,4beta-dihydroxy-5alpha(H)-guaia-1(2),11(13)-dien-8alpha,12-olide - Compound Card

1beta,4beta-dihydroxy-5alpha(H)-guaia-1(2),11(13)-dien-8alpha,12-olide

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1beta,4beta-dihydroxy-5alpha(H)-guaia-1(2),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(=CC[C@]1(C)O)[C@@](C2)(C)O
InChI InChI=1S/C15H20O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h4,9,11-12,17-18H,1,5-7H2,2-3H3/t9?,11?,12-,14+,15+/m1/s1
InChIKey SKXYOUKPVUIPFP-BLSFUNNGSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.33
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 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: 162966531
Nmrshiftdb2: 70132176

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC2)C1CC(C2=3)CCC3

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
33.91
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
7.83
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.0
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.73
Micronucleos
Toxic
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
-2.09
Rat (Acute)
3.27
Rat (Chronic Oral)
1.63
Fathead Minnow
3.88
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
326.29
Hydration Free Energy
-7.94
Log(D) at pH=7.4
0.67
Log(P)
0.44
Log S
-1.78
Log(Vapor Pressure)
-5.82
Melting Point
153.11
pKa Acid
7.52
pKa Basic
6.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8581
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8581
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8503
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8503
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8447
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8447
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8374
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8374
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8307
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8307
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8196
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8196
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7880
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7880
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7857
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7857
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7847
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7847
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7715
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7715
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7710
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7710
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7696
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7696
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7576
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7576
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7408
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7408
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7260
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7260
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7250
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7250
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7214
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7214
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7194
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7194
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7166
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7166
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7142
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7142
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7140
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7140
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7138
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7138
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7040
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7040

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