4alpha-hydroxy-guaia-1,12-dien-8beta,11-olide - Compound Card

4alpha-hydroxy-guaia-1,12-dien-8beta,11-olide

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4alpha-hydroxy-guaia-1,12-dien-8beta,11-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@@H](C1=C)C[C@@H]1C(=CC[C@@]1(C)O)[C@H](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+/m0/s1
InChIKey XRMJVTYQUFNCJQ-RPMKOLLGSA-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 Francoeuria crispa Asteraceae Plantae 1548540
2 Pulicaria undulata Asteraceae Plantae 119186

Showing of synonyms

  • Abdel Bar F.M, Elsbaey M, et al. (2020). Phytochemical, antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1b,2a,3b,19a,23-pentahydroxy-urs-12-en-28-oic acid. Natural product research, 2020, 34(6), 804-809. [View] [PubMed]
  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
Pubchem: 14021502
Nmrshiftdb2: 70071716

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
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
43.74
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
11.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
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
3.85
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
0.66
Rat (Acute)
2.81
Rat (Chronic Oral)
1.72
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
320.2
Hydration Free Energy
-5.7
Log(D) at pH=7.4
1.7
Log(P)
1.8
Log S
-2.65
Log(Vapor Pressure)
-4.65
Melting Point
131.46
pKa Acid
8.72
pKa Basic
6.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8417
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8417
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8414
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8414
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8144
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8144
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7971
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7971
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7960
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7960
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7663
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7663
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7477
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7477
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7411
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7411
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7409
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7409
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7390
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7390
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7356
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7356
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7243
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7243
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7215
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7215
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7213
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7213
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7209
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7209
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7200
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7200
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7196
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7196
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7189
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7189
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7173
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7173
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7162
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7162
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7153
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7153
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7152
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7152
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7148
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7148
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7129
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7129
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7096
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7096
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7060
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7030
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7030
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7024
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7024
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7006
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7006

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