1alpha,6alpha,8alpha-trihydroxy-5alpha,7betaH-guaia-3,10(14),11(13)-trien-12-oic acid - Compound Card

1alpha,6alpha,8alpha-trihydroxy-5alpha,7betaH-guaia-3,10(14),11(13)-trien-12-oic acid

Select a section from the left sidebar

1alpha,6alpha,8alpha-trihydroxy-5alpha,7betaH-guaia-3,10(14),11(13)-trien-12-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@H]1CC(=C)[C@]2([C@@H]([C@H]([C@@H]1C(=C)C(=O)O)O)C(=CC2)C)O
InChI InChI=1S/C15H20O5/c1-7-4-5-15(20)8(2)6-10(16)11(9(3)14(18)19)13(17)12(7)15/h4,10-13,16-17,20H,2-3,5-6H2,1H3,(H,18,19)/t10-,11+,12+,13-,15+/m0/s1
InChIKey KKQHLFPBXNSIAB-IHWVXMPCSA-N
Formula C15H20O5
HBA 4
HBD 4
MW 280.32
Rotatable Bonds 2
TPSA 97.99
LogP 0.62
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 280.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea coarctata Asteraceae Plantae 282729

Showing of synonyms

  • Hegazy MEF, Abdel-Lateff A, et al. (2008). Anti-inflammatory activity of new guaiane acid derivatives from Achillea coarctata.. Natural Product Communications,2008,3(6),851-856. [View]
Pubchem: 162956201
Nmrshiftdb2: 70043120

No compound-protein relationship available.

Structure

SMILES: C1CCCC(=C)C(C12)CC=C2

Level: 0

Mol. Weight: 280.32 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-5.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
52.11
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
1.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.81
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.12
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
-1.57
Rat (Acute)
2.29
Rat (Chronic Oral)
2.98
Fathead Minnow
4.04
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
363.88
Hydration Free Energy
-14.03
Log(D) at pH=7.4
-1.86
Log(P)
0.8
Log S
-1.48
Log(Vapor Pressure)
-8.97
Melting Point
154.62
pKa Acid
3.74
pKa Basic
6.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8601
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8601
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8082
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8082
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7944
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7944
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7944
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7944
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.7884
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.7884
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7722
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7722
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7713
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7713
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7589
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7589
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7433
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7433
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7337
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7337
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7315
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7315
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7254
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7244
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7244
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7234
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7234
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7231
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7231
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7207
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7207
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7159
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7159
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7096
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7096
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7033
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7033

Download SDF