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Bulgarsenine
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | O=C1/C=C(/C)\C[C@H](C)[C@@](C)(O)C(=O)OC[C@H]2C3[C@@H](O1)CCN3CC2 |
|---|---|
| InChI | InChI=1S/C18H27NO5/c1-11-8-12(2)18(3,22)17(21)23-10-13-4-6-19-7-5-14(16(13)19)24-15(20)9-11/h9,12-14,16,22H,4-8,10H2,1-3H3/b11-9-/t12-,13-,14-,16?,18+/m0/s1 |
| InChIKey | KUYRTCOXLIWTED-FNBYEZSTSA-N |
| Formula | C18H27NO5 |
| HBA | 6 |
| HBD | 1 |
| MW | 337.42 |
| Rotatable Bonds | 0 |
| TPSA | 76.07 |
| LogP | 1.27 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 337.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Solanecio angulatus | Asteraceae | Plantae | 1670880 |
| 2 | Solanecio mannii | Asteraceae | Plantae | — |
| 3 | Solanecio tuberosus var. tuberosus | Asteraceae | Plantae | 189251 |
Showing of synonyms
Bulgarsenine
KUYRTCOXLIWTED-FNBYEZSTSA-N
Pubchem:
6428024
No compound-protein relationship available.
SMILES: C12C3CCN2CCC1OC(=O)C=CCCCC(=O)OC3
Level: 0
Mol. Weight: 337.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.81
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.98
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.04
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.57
- Plasma Protein Binding
- 28.28
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 6.31
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.0
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.18
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.57
- Micronucleos
- Toxic
- 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
- -3.95
- Rat (Acute)
- 2.57
- Rat (Chronic Oral)
- 1.73
- Fathead Minnow
- 3.82
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 373.69
- Hydration Free Energy
- -7.75
- Log(D) at pH=7.4
- 0.83
- Log(P)
- 1.28
- Log S
- -2.42
- Log(Vapor Pressure)
- -7.12
- Melting Point
- 167.75
- pKa Acid
- 6.95
- pKa Basic
- 7.45
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8662 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8662 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8522 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8522 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8205 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8205 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7910 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7910 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7846 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7846 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7670 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7670 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7601 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7601 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7535 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7535 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.7499 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.7499 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7487 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7487 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7386 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7386 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7282 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7282 |