Select a section from the left sidebar
7-acetyllycopsamine
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | CC(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](O)C)(C(C)C)O |
|---|---|
| InChI | InChI=1S/C17H27NO6/c1-10(2)17(22,11(3)19)16(21)23-9-13-5-7-18-8-6-14(15(13)18)24-12(4)20/h5,10-11,14-15,19,22H,6-9H2,1-4H3/t11-,14-,15-,17+/m1/s1 |
| InChIKey | RKDOFSJTBIDAHX-CYHLAULCSA-N |
| Formula | C17H27NO6 |
| HBA | 7 |
| HBD | 2 |
| MW | 341.4 |
| Rotatable Bonds | 6 |
| TPSA | 96.3 |
| LogP | 0.24 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.76 |
| Exact Mass | 341.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Echium humile | Boraginaceae | Plantae | 161689 |
| 2 | Anchusa hispida | Boraginaceae | Plantae | 170551 |
| 3 | Lappula spinocarpos | Boraginaceae | Plantae | 1245804 |
| 4 | Ageratum conyzoides | Asteraceae | Plantae | 68299 |
Showing of synonyms
7-acetyllycopsamine
7-Acetylintermedine
74243-01-9
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester, (1R-(1alpha,7(2S*,3R*),7abeta))-
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7aR)-1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester, (2S,3R)-
DTXSID201019870
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl ester, [1R-[1alpha,7(2S*,3R*),7abeta]]-
DTXCID701477738
Acetylintermedine
[(7R,8R)-7-acetyloxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate
O-Acetylintermedine
Intermedine 1-acetate
RW5M8C9CEX
CHEBI:80702
7-O-Acetylintermedine , HPLC Grade
MFCD31631254
MSK167134
AKOS040758324
DA-60553
1ST167134
HY-127011
CS-0091352
NS00094176
Q27149735
((1R,7aR)-1-acetoxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2,3-dihydroxy-2-isopropylbutanoate
(2S,3R)-(1R,7ar)-1-Acetoxy-2,3,5,7a-tetrahydro-1H pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-isopropylbutanoate
- Belete Y, Wondu K, et al. (2020). Natural Toxins of Ageratum conyzoides from Hepatic Vein Occlusive Disease Affected Community in Ethiopia. Nat Prod Chem Res, 2020, 8(1) ,370. [View]
- El-Shazly A, El-Domiaty M, et al. (1998). Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt). Biochemical Systematics and Ecology,1998,26(6),619-636. [View]
- El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile. Phytochemistry,1996,42(1),225-230. [View]
No compound-protein relationship available.
SMILES: C1=CCN(C12)CCC2
Level: 0
Mol. Weight: 341.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.91
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.84
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.95
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.29
- Plasma Protein Binding
- 35.64
- 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
- 7.08
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.66
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.17
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.9
- 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
- -1.63
- Rat (Acute)
- 3.32
- Rat (Chronic Oral)
- 2.02
- Fathead Minnow
- 3.99
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 344.73
- Hydration Free Energy
- -11.25
- Log(D) at pH=7.4
- 0.31
- Log(P)
- 0.75
- Log S
- -1.36
- Log(Vapor Pressure)
- -7.17
- Melting Point
- 138.87
- pKa Acid
- 6.96
- pKa Basic
- 7.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.9160 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.9160 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7923 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7923 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7913 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7913 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7804 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7804 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7781 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7781 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7725 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7725 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7722 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7722 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7715 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7715 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7584 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7584 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7537 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7537 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7455 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7455 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7246 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7246 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7212 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7212 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7208 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7208 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7206 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7206 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7197 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7197 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7196 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7196 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7152 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7152 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7120 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7120 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7106 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7106 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7101 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7101 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7084 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7084 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7066 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7066 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7045 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7045 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7039 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7039 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7018 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7018 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7014 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7014 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7014 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7014 |