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Crispioside B
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OC[C@H]1O[C@@H](OC(=O)[C@]2(C)CCC[C@@]3([C@@H]2CC[C@]24[C@H]3CC[C@H](C2)[C@@](C4)(O)CO)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C26H42O9/c1-23-7-3-8-24(2,22(32)35-21-20(31)19(30)18(29)15(11-27)34-21)16(23)6-9-25-10-14(4-5-17(23)25)26(33,12-25)13-28/h14-21,27-31,33H,3-13H2,1-2H3/t14-,15-,16+,17+,18-,19+,20-,21+,23-,24-,25+,26+/m1/s1 |
| InChIKey | XKXZHTWOHXJEOL-HMQRFDIMSA-N |
| Formula | C26H42O9 |
| HBA | 9 |
| HBD | 6 |
| MW | 498.61 |
| Rotatable Bonds | 4 |
| TPSA | 156.91 |
| LogP | 0.47 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.96 |
| Exact Mass | 498.28 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Francoeuria crispa | Asteraceae | Plantae | 1548540 |
Showing of synonyms
Crispioside B
CHEMBL3357412
- Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OC(=O)C(CCC2)C(CC3)C2C(C345)CCC(C4)CC5
Level: 1
Mol. Weight: 498.61 g/mol
SMILES: C1CC(C2)CCC(C123)C4C(CC3)CCCC4
Level: 0
Mol. Weight: 498.61 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 498.61 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.82
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.03
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.34
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.87
- Plasma Protein Binding
- 87.88
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -0.34
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.32
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.85
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.35
- 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
- -334.85
- Rat (Acute)
- 3.39
- Rat (Chronic Oral)
- 3.52
- Fathead Minnow
- 3.57
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 530.66
- Hydration Free Energy
- -3.02
- Log(D) at pH=7.4
- 2.28
- Log(P)
- 0.84
- Log S
- -2.74
- Log(Vapor Pressure)
- -13.4
- Melting Point
- 211.03
- pKa Acid
- 6.53
- pKa Basic
- 6.89
| 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 | 0.8178 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8178 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7784 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7784 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7436 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7436 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7392 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7392 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7135 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7135 |