1beta,4beta-dihydroxy-5alpha(H)-guaia-10(14),11(13)-dien-8alpha,12-olide - Compound Card

1beta,4beta-dihydroxy-5alpha(H)-guaia-10(14),11(13)-dien-8alpha,12-olide

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1beta,4beta-dihydroxy-5alpha(H)-guaia-10(14),11(13)-dien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1C(=O)O[C@H]2C1CC1[C@](C)(O)CC[C@@]1(C(=C)C2)O
InChI InChI=1S/C15H20O4/c1-8-6-11-10(9(2)13(16)19-11)7-12-14(3,17)4-5-15(8,12)18/h10-12,17-18H,1-2,4-7H2,3H3/t10?,11-,12?,14-,15+/m1/s1
InChIKey TUXMPYMXQNASGF-JBDFUULCSA-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: 162853376
Nmrshiftdb2: 70058123

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
35.75
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
7.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.53
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
-2.18
Rat (Acute)
3.16
Rat (Chronic Oral)
1.65
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
327.3
Hydration Free Energy
-7.92
Log(D) at pH=7.4
0.76
Log(P)
0.6
Log S
-1.9
Log(Vapor Pressure)
-6.4
Melting Point
147.92
pKa Acid
7.26
pKa Basic
6.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9099
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9099
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9073
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9073
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8840
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8840
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8750
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8750
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8736
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8736
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8719
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8719
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8676
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8676
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8637
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8637
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8598
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8598
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8573
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8573
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8563
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8563
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8537
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8537
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8278
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8278
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8170
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8170
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8154
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8154
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8152
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8152
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8128
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8128
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8100
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8100
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8049
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8049
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8035
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8035
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8022
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8022
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7999
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7999
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7775
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7775
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7734
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7734
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7733
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7733
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7720
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7720
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7642
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7642
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7559
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7533
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7533
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7531
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7531
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7527
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7527
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7525
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7525
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7521
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7521
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7517
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7517
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7478
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7478
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7407
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7407
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7387
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7387
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7370
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7370
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7295
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7295
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7253
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7253
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7194
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7194
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7148
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7148
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7139
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7130
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7130
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7113
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7113
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7058
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7058
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7057
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7057
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7043
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7043
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7031
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7031
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7019
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7019

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