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Alpha-chaconine
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Glycoalkaloid
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@H](C)[C@@H]3N4C[C@H](CC3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-/m0/s1 |
| InChIKey | TYNQWWGVEGFKRU-AJDPQWBVSA-N |
| Formula | C45H73NO14 |
| HBA | 15 |
| HBD | 8 |
| MW | 852.07 |
| Rotatable Bonds | 7 |
| TPSA | 220.46 |
| LogP | 1.18 |
| Number Rings | 9 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 60 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.96 |
| Exact Mass | 851.5 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Solanum tuberosum | Solanaceae | Plantae | 4113 |
Showing of synonyms
Alpha-chaconine
20562-03-2
.alpha.-Chaconine
UNII-5QOL0LIM81
5QOL0LIM81
A-Chaconine
CCRIS 6509
BRN 0077396
.ALPHA.-CHACONINE [MI]
DTXSID501016601
4-21-00-01401 (Beilstein Handbook Reference)
(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.)-SOLANID-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-
Beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-
(2S,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
(2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
2-((4-hydroxy-2-(hydroxymethyl)-6-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-3-yl)oxy)-6-methyloxane-3,4,5-triol
2-{[4-hydroxy-2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl}oxy)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
Alpha-rhamnosyl-(1->2)-(alpha-rhamnosyl-(1->4)-)-beta-D-glucosyl-solanidine
Alpha-rhamnosyl-(1->2)-[alpha-rhamnosyl-(1->4)-]-beta-D-glucosyl-solanidine
DTXCID301474794
633-788-5
BETA-D-GLUCOPYRANOSIDE, (3BETA)-SOLANID-5-EN-3-YL O-6-DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->4))-
Conine
Chaconine
Alpha-?Chaconine
Alpha -Chaconine
(3b)-Solanid-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1-2)-O-(6-deoxy-a-L-mannopyranosyl-(1-4))-b-D-glucopyranoside
??-?Chaconine
|A-?Chaconine (Standard)
CHEBI:10219
TYNQWWGVEGFKRU-AJDPQWBVSA-N
AKOS040760264
HY-129113R
OC29325
DA-50353
MS-31576
HY-129113
CS-0103657
NS00094322
G13546
Q2947331
Pubchem:
442971
Cas:
20562-03-2
Zinc:
ZINC000255270402
Kegg Ligand:
C10796
Chebi:
10219
Metabolights:
MTBLC10219
CPRiL:
138982
SMILES: C1CCCC(C2)N1C3CC(C4C23)C5C(CC4)C6C(=CC5)CC(CC6)OC(C7OC8CCCCO8)OCC(C7)OC9CCCCO9
Level: 3
Mol. Weight: 852.07 g/mol
SMILES: C1CCCC(C2)N1C3CC(C4C23)C5C(CC4)C6C(=CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8
Level: 2
Mol. Weight: 852.07 g/mol
SMILES: C1CCCC(C2)N1C3CC(C4C23)C5C(CC4)C6C(=CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8
Level: 2
Mol. Weight: 852.07 g/mol
SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3
Level: 2
Mol. Weight: 852.07 g/mol
SMILES: C1CCCC(C2)N1C3CC(C4C23)C5C(CC4)C6C(=CC5)CC(CC6)OC7CCCCO7
Level: 1
Mol. Weight: 852.07 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 852.07 g/mol
SMILES: C1CCCC(C2)N1C3CC(C4C23)C5C(CC4)C6C(=CC5)CCCC6
Level: 0
Mol. Weight: 852.07 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 852.07 g/mol
Antiviral
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -6.42
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 491.120
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 64979.58
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.790
- Plasma Protein Binding
- 88.67
- 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
- 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
- 0.590
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -1506.120
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.080
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.010
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -117934041.930
- Rat (Acute)
- 3.440
- Rat (Chronic Oral)
- 4.040
- Fathead Minnow
- 148870.840
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 13261211.530
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.030
- Log(P)
- 3.39
- Log S
- -2.84
- Log(Vapor Pressure)
- -436513.62
- Melting Point
- 224.3
- pKa Acid
- -3103.47
- pKa Basic
- 6.11
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8354 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8354 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7737 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7737 |