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Solamargine
- 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@]3(O4)CC[C@H](CN3)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/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/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-/m1/s1 |
| InChIKey | MBWUSSKCCUMJHO-ZGXDEBHDSA-N |
| Formula | C45H73NO15 |
| HBA | 16 |
| HBD | 9 |
| MW | 868.07 |
| Rotatable Bonds | 7 |
| TPSA | 238.48 |
| LogP | 0.81 |
| Number Rings | 9 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 61 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.96 |
| Exact Mass | 867.5 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Solanum nigrum | Solanaceae | Plantae | 4112 |
| 2 | Solanum wrightii | Solanaceae | Plantae | 374009 |
Showing of synonyms
Solamargine
20311-51-7
UNII-8KG991E7BN
8KG991E7BN
NSC 407810
DELTA-SOLANIGRINE
(-)-SOLAMARGINE
NSC-407810
(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-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, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-
(1R)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxycyclopent-2-ene-1-carbonitrile
(1R)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxycyclopent-2-ene-1-carbonitrile
(2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-((1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-piperidine)-16-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
.DELTA.-SOLANIGRINE
SOLAMARGINE, (-)-
BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-
BETA.-D-GLUCOPYRANOSIDE, (3BETA,22ALPHA,25R)-SPIROSOL-5-EN-3-YL O-6-DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->4))-
Solamargin
CHEBI:9185
|A-Solanigrine
A-Solamargine
AC1L2K61
(3ss,22a,25R)-Spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1?2)-O-[6-deoxy-a-L-mannopyranosyl-(1?4)]-ss-D-glucopyranoside
D-Solanigrine
MFCD30207844
Solanigrine, (-)-
CHEMBL443114
DTXSID00942456
HY-N0069
MSK163965
S9145
AKOS030526705
CCG-270542
DB12700
OS65545
AS-75093
DA-57990
1ST163965
NS00073646
Q3489126
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0(2),?.0?,?.0(1)(3),(1)?]icosane-6,2'-piperidin]-18-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
(3beta,22alpha,25R)-Spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside
Beta-D-Glucopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-
Solasodine-L-rhamnosido-D-glucoside
(3b,22a,25R)-Spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1?2)-O-[6-deoxy-a-L-mannopyranosyl -(1?4)]-b-D-glucopyranoside
Pubchem:
73611
Cas:
20311-51-7
Gnps:
CCMSLIB00006434719
Zinc:
ZINC000252474776
Kegg Ligand:
C10819
Chebi:
9185
Chembl:
CHEMBL443114
Drugbank:
DB12700
CPRiL:
102700
SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC(C7OC8CCCCO8)OCC(C7)OC9CCCCO9
Level: 3
Mol. Weight: 868.07 g/mol
SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8
Level: 2
Mol. Weight: 868.07 g/mol
SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8
Level: 2
Mol. Weight: 868.07 g/mol
SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3
Level: 2
Mol. Weight: 868.07 g/mol
SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC7CCCCO7
Level: 1
Mol. Weight: 868.07 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 868.07 g/mol
SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6
Level: 0
Mol. Weight: 868.07 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 868.07 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.42
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 746.760
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 98391.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.860
- Plasma Protein Binding
- 87.42
- 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
- 0.360
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -2282.920
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.150
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.500
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -178574742.190
- Rat (Acute)
- 3.650
- Rat (Chronic Oral)
- 4.150
- Fathead Minnow
- 225417.660
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 20081536.510
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 1.990
- Log(P)
- 2.73
- Log S
- -2.94
- Log(Vapor Pressure)
- -661108.48
- Melting Point
- 239.38
- pKa Acid
- -4739.51
- pKa Basic
- -3.77
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7885 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7750 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7296 |