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2alpha,3beta,14beta-trihydroxy-3-O-(4-deoxy-3-O-(methyl-alpha-L-erythro-pentopyranosyl)-card-4,20(22)-dienolide
- Family: Plantae - Celastraceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Cardenolide
| Canonical Smiles | CO[C@H]1CCO[C@H]([C@H]1O)O[C@@H]1C=C2CC[C@@H]3[C@@H]([C@]2(C[C@H]1O)C)CC[C@]1([C@]3(O)CC[C@@H]1C1=CC(=O)OC1)C |
|---|---|
| InChI | InChI=1S/C29H42O8/c1-27-14-21(30)23(37-26-25(32)22(34-3)8-11-35-26)13-17(27)4-5-20-19(27)6-9-28(2)18(7-10-29(20,28)33)16-12-24(31)36-15-16/h12-13,18-23,25-26,30,32-33H,4-11,14-15H2,1-3H3/t18-,19+,20-,21-,22+,23-,25+,26+,27+,28-,29+/m1/s1 |
| InChIKey | KGHVKLKIEZEJMZ-QPASPVMUSA-N |
| Formula | C29H42O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 518.65 |
| Rotatable Bonds | 4 |
| TPSA | 114.68 |
| LogP | 2.64 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.83 |
| Exact Mass | 518.29 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Salacia staudtiana | Celastraceae | Plantae | 662028 |
Showing of synonyms
2alpha,3beta,14beta-trihydroxy-3-O-(4-deoxy-3-O-(methyl-alpha-L-erythro-pentopyranosyl)-card-4,20(22)-dienolide
CHEMBL229421
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)=CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 518.65 g/mol
SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 518.65 g/mol
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)=CCCC5
Level: 1
Mol. Weight: 518.65 g/mol
SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4
Level: 0
Mol. Weight: 518.65 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 518.65 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 518.65 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.18
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.870
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.24
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.810
- Plasma Protein Binding
- 63.28
- 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
- 5.290
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.920
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -2.500
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.040
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Toxic
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -1572.930
- Rat (Acute)
- 3.810
- Rat (Chronic Oral)
- 2.100
- Fathead Minnow
- 5.230
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 485.490
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.720
- Log(P)
- 1.74
- Log S
- -4.12
- Log(Vapor Pressure)
- -9.82
- Melting Point
- 229.37
- pKa Acid
- 8.26
- pKa Basic
- 6.29
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7936 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7351 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7341 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7006 |