Select a section from the left sidebar
3-O-[alpha-L-rhamnopyranosyl (1–2)-alpha-L-arabinopyranosyl]-hederagenin
- Family: Plantae - Araliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene Saponin
| Canonical Smiles | OC[C@]1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O |
|---|---|
| InChI | InChI=1S/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)/t21-,23-,24-,25+,26+,27-,28-,29-,30+,31+,32+,33-,34-,37-,38-,39+,40+,41-/m0/s1 |
| InChIKey | KEOITPILCOILGM-LLJOFIFVSA-N |
| Formula | C41H66O12 |
| HBA | 11 |
| HBD | 7 |
| MW | 750.97 |
| Rotatable Bonds | 6 |
| TPSA | 195.6 |
| LogP | 3.52 |
| Number Rings | 7 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 53 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 750.46 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Polyscias fulva | Araliaceae | Plantae | 150522 |
Showing of synonyms
3-O-[alpha-L-rhamnopyranosyl (1–2)-alpha-L-arabinopyranosyl]-hederagenin
Alpha-Hederin
27013-91-8
Helixin
Koronaroside A
Hederoside C
Tauroside E
Prosapogenin CP3b
Glycoside L-E1
Akeboside Stc
Pulsatilla saponin A
Nepalin 2
.alpha.-Hederin
Akebia saponin PD
Kizuta saponin K6
Alpha-Hederine
Helixin (VAN)
Alpha-Hederin hydrate
Alpha-Hederine [French]
Rha-Ara-3beta-hederagenin
EINECS 248-166-5
NSC 106553
BRN 0076156
4H15F0GLV2
ALFA-HEDERINA
.ALPHA.-HEDERIN [MI]
ALFA-HEDERINA [WHO-DD]
(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
DTXSID80909168
4-17-00-02560 (Beilstein Handbook Reference)
NSC-106553
(4alpha)-3beta-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxyolean-12-en-28-oic acid
Olean-12-en-28-oic acid, 3-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxy-, (3-beta,4-alpha)-
(4alpha)-3beta-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid
(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-((2S,3R,4S,5S)-4,5-dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl)oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-((2S,3R,4S,5S)-4,5-dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Alpha-Hederin (8CI)
DTXCID101338235
(4.ALPHA.)-3.BETA.-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.ALPHA.-L-ARABINOPYRANOSYL)OXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID
248-166-5
Kalopanaxsaponin A
Sapindoside A
CHEBI:69370
Hederin
(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-(((2S,3R,4S,5S)-4,5-Dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
UNII-4H15F0GLV2
NSC106553
Akebiasaponin PD
Kizutasaponin K6
Alpha-Hederin (Standard)
CHEMBL447565
SCHEMBL3007691
HY-N0255R
HY-N0255
S3914
AKOS032961986
CCG-270437
CS-5690
FH65830
AC-33961
DA-50355
NS00050007
C08954
Q25105925
3-O-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabinopyranosyl hederagenin
(4.ALPHA.)-3.BETA.-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.ALPHA.- L-ARABINOPYRANOSYL)OXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID
(4ALPHA)-3BETA-((2-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL)-ALPHA- L-ARABINOPYRANOSYL)OXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID
(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylicacid
(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-(((2S,3R,4S,5S)-4,5-Dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10
(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-(((2S,3R,4S,5S)-4,5-Dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylicacid
104748-88-1
3beta-{[2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy}-23-hydroxyolean-12-en-28-oic acid
OLEAN-12-EN-28-OIC ACID, 3-((2-O-(6-DEOXY-ALPHA-L- MANNOPYRANOSYL)-ALPHA-L-ARABINOPYRANOSYL)OXY)-23-HYDROXY-, (3-BETA,4-ALPHA)-
Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.alpha.-L-arabinopyranosyl]oxy]-23-hydroxy-, (3.beta., 4.alpha.)
Pubchem:
73296
Cas:
27013-91-8
Zinc:
ZINC000095098996
Kegg Ligand:
C08954
Chebi:
69370
Nmrshiftdb2:
60026601
Metabolights:
MTBLC69370
Chembl:
CHEMBL447565
CPRiL:
71382
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7
Level: 2
Mol. Weight: 750.97 g/mol
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6
Level: 1
Mol. Weight: 750.97 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 750.97 g/mol
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 750.97 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 750.97 g/mol
Antidermatophytic
Absorption
- Caco-2 (logPapp)
- -5.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 0.1
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 789.02
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.16
- Plasma Protein Binding
- 108.1
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 3.9
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -18.76
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.78
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.47
- Micronucleos
- Safe
- 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
- -1432838.45
- Rat (Acute)
- 2.85
- Rat (Chronic Oral)
- 3.19
- Fathead Minnow
- 1814.45
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 158022.25
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 3.29
- Log(P)
- 3.93
- Log S
- -3.62
- Log(Vapor Pressure)
- -5107.63
- Melting Point
- 243.03
- pKa Acid
- -6.86
- pKa Basic
- 8.12