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3beta-hydroxygermacra-1(10),4-dien-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C/C/1=C\C[C@H](O)/C(=C/[C@@H]2[C@@H](CC1)[C@H](C)C(=O)O2)/C |
|---|---|
| InChI | InChI=1S/C15H22O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,8,11-14,16H,4,6-7H2,1-3H3/b9-5+,10-8+/t11-,12-,13-,14+/m0/s1 |
| InChIKey | RLHPCSSGTQNSJN-FOMNRLOISA-N |
| Formula | C15H22O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 250.34 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 2.6 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 250.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia arborescens | Asteraceae | Plantae | 72386 |
Showing of synonyms
3beta-hydroxygermacra-1(10),4-dien-6alpha,12-olide
MEGxp0_001083
CHEMBL4440983
ACon1_001165
RLHPCSSGTQNSJN-FOMNRLOISA-
InChI=1/C15H22O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,8,11-14,16H,4,6-7H2,1-3H3/b9-5+,10-8+/t11-,12-,13-,14+/m0/s1
- Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
No compound-protein relationship available.
SMILES: C1C(=O)OC(C12)C=CCCC=CCC2
Level: 0
Mol. Weight: 250.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.85
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.24
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.42
- Plasma Protein Binding
- 43.47
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 7.49
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.13
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.2
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.2
- 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
- -0.59
- Rat (Acute)
- 2.24
- Rat (Chronic Oral)
- 1.82
- Fathead Minnow
- 4.29
- 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
- 331.93
- Hydration Free Energy
- -7.09
- Log(D) at pH=7.4
- 1.58
- Log(P)
- 2.41
- Log S
- -2.57
- Log(Vapor Pressure)
- -4.97
- Melting Point
- 122.37
- pKa Acid
- 10.69
- pKa Basic
- 5.74
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9385 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9385 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8751 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8751 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7951 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7951 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7884 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7884 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7664 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7664 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7615 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7615 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7588 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7588 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7576 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7576 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7459 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7459 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7431 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7431 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7334 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7334 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7309 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7309 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 2 | 0.7302 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 2 | 0.7302 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7287 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7287 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7281 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7281 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7266 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7266 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7242 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7242 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 2 | 0.7185 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 2 | 0.7185 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7117 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7117 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7097 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7097 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7089 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7089 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7060 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7060 |