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Integerrimine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C/1\C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 |
|---|---|
| InChI | InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4+/t11-,14-,15-,18-/m1/s1 |
| InChIKey | HKODIGSRFALUTA-IKZAEVNJSA-N |
| Formula | C18H25NO5 |
| HBA | 6 |
| HBD | 1 |
| MW | 335.4 |
| Rotatable Bonds | 0 |
| TPSA | 76.07 |
| LogP | 1.19 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 335.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Senecio halleri | Asteraceae | Plantae | 214899 |
| 2 | Senecio incanus | Asteraceae | Plantae | 189239 |
| 3 | Senecio leucophyllus | Asteraceae | Plantae | 214900 |
| 4 | Senecio delphinifolius | Asteraceae | Plantae | 214896 |
| 5 | Senecio othonnae | Asteraceae | Plantae | 214901 |
| 6 | Senecio paludosus | Asteraceae | Plantae | 189244 |
| 7 | Senecio alpinus | Asteraceae | Plantae | 189227 |
| 8 | Senecio ambiguus | Asteraceae | Plantae | 189228 |
| 9 | Senecio aquaticus | Asteraceae | Plantae | 189230 |
| 10 | Senecio cineraria | Asteraceae | Plantae | 252537 |
| 11 | Senecio erucifolius | Asteraceae | Plantae | 189238 |
| 12 | Senecio giganteus | Asteraceae | Plantae | 214897 |
| 13 | Senecio gnaphalodes | Asteraceae | Plantae | 2868836 |
| 14 | Senecio jacobaea | Asteraceae | Plantae | 98722 |
| 15 | Senecio pancicii | Asteraceae | Plantae | 189245 |
| 16 | Senecio subalpinus | Asteraceae | Plantae | 189250 |
| 17 | Solanecio angulatus | Asteraceae | Plantae | 1670880 |
| 18 | Solanecio mannii | Asteraceae | Plantae | — |
| 19 | Solanecio tuberosus var. tuberosus | Asteraceae | Plantae | 189251 |
| 20 | Crotalaria agatiflora | Leguminosae/Fabaceae | Plantae | 1127378 |
| 21 | Crotalaria albicaulis | Leguminosae/Fabaceae | Plantae | 1132156 |
| 22 | Crotalaria axillaris | Leguminosae/Fabaceae | Plantae | 1132589 |
| 23 | Crotalaria gillettii | Leguminosae/Fabaceae | Plantae | 1132206 |
| 24 | Crotalaria incana | Leguminosae/Fabaceae | Plantae | 46447 |
| 25 | Crotalaria laburnifolia | Leguminosae/Fabaceae | Plantae | 992673 |
| 26 | Crotalaria mildbraedii | Leguminosae/Fabaceae | Plantae | 1977593 |
Showing of synonyms
Integerrimine
Squalidine
Squalidin
Inegerrimine
Intergerrimine
NSC 79540
UNII-3179A6U4PN
(15E)-12-Hydroxysenecionan-11,16-dione
3179A6U4PN
Senecionan-11,16-dione, 12-hydroxy-, (15E)-
DTXSID601016480
NSC-79540
(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE, 3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-5,6-DIMETHYL-, (3E,5R,6R,14AR,14BR)-
DTXCID801474670
SENECIONINE C15-TRANS ISOMER
480-79-5
(-)-Integerrimine
CHEBI:5935
(1R,4E,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
Senecionan-11,16-dione, 12-hydroxy-
Aureine
Senecionin
CHEMBL488203
MSK160719
DA-74500
XI161635
SENECIONINE C15-TRANS ISOMER [MI]
1ST160719
HY-122772
CS-0088878
NS00094202
Q27106934
(5R,6R,9a1R,14aR,E)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
- Pelser PB, De Vos H, et al. (2005). Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae). Phytochemistry,2005,66,1285-1295. [View] [PubMed]
- Asres K, Sporer F, et al. (2008). Occurrence of pyrrolizidine alkaloids in three Ethiopian Solanecio species. Biochemical Systematics and Ecology,2008,36(5-6),399-407. [View] [PubMed]
- Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
CPRiL:
6189
SMILES: C1OC(=O)CCCC(=C)C(=O)OC(C2C1=3)CCN2CC3
Level: 0
Mol. Weight: 335.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.88
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.93
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.02
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.61
- Plasma Protein Binding
- 28.96
- 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
- 5.45
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.69
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.09
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.83
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -3.39
- Rat (Acute)
- 3.71
- Rat (Chronic Oral)
- 1.76
- Fathead Minnow
- 4.07
- 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
- 378.83
- Hydration Free Energy
- -9.95
- Log(D) at pH=7.4
- 1.2
- Log(P)
- 1.31
- Log S
- -2.24
- Log(Vapor Pressure)
- -7.26
- Melting Point
- 179.24
- pKa Acid
- 6.86
- pKa Basic
- 6.7
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8413 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8413 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8038 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8038 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7817 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7817 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7803 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7803 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7707 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7707 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7508 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7508 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7407 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7407 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7403 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7403 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7386 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7386 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7062 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7062 |