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8alpha-hydroxy-11alpha,13-dihydrozaluzanin C
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
Canonical Smiles | O[C@H]1C[C@@H]2[C@H](C1=C)[C@H]1OC(=O)C(C1[C@H](CC2=C)O)C |
---|---|
InChI | InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h8-14,16-17H,1-2,4-5H2,3H3/t8?,9-,10-,11-,12-,13?,14+/m0/s1 |
InChIKey | AEWOONBLAKEKSC-BBPNPORVSA-N |
Formula | C15H20O4 |
HBA | 4 |
HBD | 2 |
MW | 264.32 |
Rotatable Bonds | 0 |
TPSA | 66.76 |
LogP | 1.04 |
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 | Centaurea scoparia | Asteraceae | Plantae | 2072395 |
2 | Volutaria lippii | Asteraceae | Plantae | 41663 |
Showing of synonyms
8alpha-hydroxy-11alpha,13-dihydrozaluzanin C
- Helal AM, Nakamura N, et al. (1997). Guaianolides from Centaurea scoparia. Phytochemistry,1997,45(3),551-554. [View]
- Rafrafi M, Ben Salah H, et al. (2021). Sesquiterpene lactones and flavonoids with chemotaxonomic significance from Volutaria lippii (L.) Cass. Biochemical Systematics and Ecology, 2021, 96, 104249. [View]
Pubchem:
101705725
No compound-protein relationship available.
SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3
Level: 0
Mol. Weight: 264.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.34
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.57
- Plasma Protein Binding
- 38.66
- 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
- 9.86
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.31
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.07
- 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
- -1.37
- Rat (Acute)
- 3.82
- Rat (Chronic Oral)
- 1.73
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 357.38
- Hydration Free Energy
- -8.6
- Log(D) at pH=7.4
- 0.2
- Log(P)
- 0.6
- Log S
- -1.65
- Log(Vapor Pressure)
- -6.62
- Melting Point
- 165.73
- pKa Acid
- 7.81
- pKa Basic
- 5.26
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9005 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9005 |
Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8820 |
Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8820 |
11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8685 |
11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8685 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8638 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8638 |
Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8504 |
Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8504 |
Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 3 | 0.8301 |
Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 3 | 0.8301 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8164 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8164 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.8145 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.8145 |
Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8118 |
Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8118 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7798 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7798 |
Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7720 |
Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7720 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7715 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7715 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7684 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7684 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7664 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7664 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7554 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7554 |
Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7545 |
Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7545 |
Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 4 | 0.7500 |
Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 4 | 0.7500 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7402 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7402 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7387 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7387 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7360 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7360 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7345 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7345 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7342 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7342 |
Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7328 |
Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7328 |
Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7314 |
Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7314 |
Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7298 |
Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7298 |
Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7166 |
Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7166 |
Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7162 |
Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7162 |
Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7141 |
Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7141 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7097 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7097 |
Predicted acetyltransferase | Q97ML2 | Q97ML2_CLOAB | Clostridium acetobutylicum | 3 | 0.7089 |
Predicted acetyltransferase | Q97ML2 | Q97ML2_CLOAB | Clostridium acetobutylicum | 3 | 0.7089 |
Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7049 |
Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7049 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7042 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7042 |
Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7029 |
Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7029 |