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

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

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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
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/h4,8,11-13,17H,2,5-7H2,1,3H3/t8?,11?,12?,13-,15-/m1/s1
InChIKey XRMJVTYQUFNCJQ-OIJBMMOISA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.21
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: 163081225
Nmrshiftdb2: 70058124

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
45.1
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
11.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.46
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.92
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
-0.23
Rat (Acute)
2.73
Rat (Chronic Oral)
1.73
Fathead Minnow
3.93
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
313.79
Hydration Free Energy
-5.75
Log(D) at pH=7.4
1.74
Log(P)
1.93
Log S
-2.61
Log(Vapor Pressure)
-4.6
Melting Point
106.77
pKa Acid
8.83
pKa Basic
6.62
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 0.9274
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9274
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8125
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8125
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8085
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8085
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7874
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7874
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7578
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7578
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7577
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7577
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7484
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7484
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7467
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7467
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7424
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7424
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7354
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7354
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7349
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7349
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7305
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7305
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7294
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7294
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7198
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7198
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7188
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7188
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7043
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7043
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7013
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7013

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