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

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

Select a section from the left sidebar

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

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@@H]([C@@H]1C)C[C@@H]1[C@H]([C@@](C2)(C)O)CC[C@@]1(C)O
InChI InChI=1S/C15H24O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h8-12,17-18H,4-7H2,1-3H3/t8-,9+,10+,11+,12+,14+,15-/m0/s1
InChIKey CXGLIVARJHWMMT-HNHGFODNSA-N
Formula C15H24O4
HBA 4
HBD 2
MW 268.35
Rotatable Bonds 0
TPSA 66.76
LogP 1.49
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 268.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Jasonia candicans Asteraceae-Compositae Plantae 557631

Showing of synonyms

  • Ahmed AA, Mahmoud AA, et al. (1993). New sesquiterpene alpha-methylene lactones from the Egyptian plant Jasonia candicans. Journal of Natural Products,1993,56(8),1276-1280. [View] [PubMed]
Pubchem: 162847976
Nmrshiftdb2: 70105179

No compound-protein relationship available.

Structure

SMILES: O=C(O1)CC(C2)C1CCC(C23)CCC3

Level: 0

Mol. Weight: 194.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
46.71
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.4
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
-1.77
Rat (Acute)
2.37
Rat (Chronic Oral)
1.68
Fathead Minnow
3.54
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
346.72
Hydration Free Energy
-7.36
Log(D) at pH=7.4
0.38
Log(P)
0.99
Log S
-1.98
Log(Vapor Pressure)
-5.87
Melting Point
167.08
pKa Acid
8.78
pKa Basic
7.8
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 0.8842
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8842
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8477
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8477
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8408
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8408
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8317
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8317
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8228
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8228
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8198
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8198
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7984
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7984
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7954
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7954
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7932
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7932
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7772
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7772
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7755
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7755
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7725
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7725
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7703
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7703
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7665
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7665
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7647
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7647
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7618
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7618
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7530
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7530
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7506
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7506
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7492
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7492
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7448
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7448
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7313
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7313
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7295
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7295
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7203
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7203
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7179
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7179
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7139
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7139
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7115
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7115
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7096
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7096
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7093
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7093
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7086
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7086
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7067
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7067
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7047
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7047
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7005
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7005

Download SDF