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Diosgenin
- Family: Plantae - Zygophyllaceae
- Kingdom: Plantae
-
Class: Saponin
- Subclass: Steroidal Saponin
| Canonical Smiles | C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C |
|---|---|
| InChI | InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1 |
| InChIKey | WQLVFSAGQJTQCK-VKROHFNGSA-N |
| Formula | C27H42O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 414.63 |
| Rotatable Bonds | 0 |
| TPSA | 38.69 |
| LogP | 5.71 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 414.31 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Balanites aegyptiaca | Zygophyllaceae | Plantae | 886265 |
| 2 | Raphia vinifera | Arecaceae | Plantae | 1966430 |
| 3 | Senecio angulatus | Asteraceae | Plantae | 189229 |
Showing of synonyms
Diosgenin
512-04-9
Nitogenin
(3beta,25R)-spirost-5-en-3-ol
CHEBI:4629
UNII-K49P2K8WLX
K49P2K8WLX
(20R,25R)-Spirost-5-en-3beta-ol
CCRIS 6803
22alpha-Spirost-5-en-3beta-ol
SP 37
EINECS 208-134-3
NSC 33396
BRN 0094582
Spirost-5-en-3-ol, (3beta,25R)-
(25R)-Spirost-5-en-3beta-ol
DTXSID00895074
5-19-03-00030 (Beilstein Handbook Reference)
Spirost-5-en-3beta-ol, (25R)-
NSC-33396
Spirost-5-en-3-beta-ol, (25R)-
DTXCID301324626
DIOSGENIN (CONSTITUENT OF FENUGREEK SEED)
208-134-3
Diosgenine
3beta-Hydroxy-5-spirostene
DISOGENIN
MFCD00016887
(25R)-5-Spirosten-3beta-ol
(25R)-spirost-5-en-3beta-diol
(25R)-14beta,17beta-spirost-5-en-3beta-ol
(2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-Tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol
Spirost-5-en-3-ol, (3b,25R)-
Nitrogen in
YUV
Diosgenin (Standard)
Diosgenin, >=93%
DIOSGENIN [MI]
3A-Hydroxy-5-spirostene
DIOSGENIN [WHO-DD]
SCHEMBL83359
(25R)-5-Spirosten-3A-ol
CHEMBL412437
HY-N0177R
HY-N0177
BDBM50617158
LMST01080037
MSK159048
(3|A,25R)-Spirost-5-en-3-ol
AKOS015961083
CS-5303
NCGC00386027-01
Spirost-5-en-3-ol, (3-beta,25R)-
AS-13640
NS00014256
S2291
(3.BETA.,25R)-SPIROST-5-EN-3-OL
C08898
M03858
EN300-7388351
Q1107734
BRD-K28690501-001-02-1
DIOSGENIN (CONSTITUENT OF FENUGREEK SEED) [DSC]
Z1741961122
Diosgenin, European Pharmacopoeia (EP) Reference Standard
(25R)-5-Spirosten-3b-ol
3?-Hydroxy-5-spirostene
(2R,5'R)-5'-tetramethylspiro[[?]-2,2'-tetrahydropyran]ol
(25R)-5-Spirosten-3(1/4)?-ol
3(1/4)?-Hydroxy-5-spirostene
(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol
(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'-oxane]-16-ol
- Bousetla A, Keskinkaya H.B, et al. (2023). LC-ESI/MS-phytochemical profiling with antioxidant and antiacetylcholinesterase activities of Algerian Senecio angulatus L.f. extracts. Natural product research, 2023, 37(1), 123-129. [View] [PubMed]
- Dawidar A, Fayez M. (1969). Steroid sapogenins-xiii. The constituents of balanites aegyptiaca. Phytochemistry,1969,8(1),261-265. [View]
- Chi GF, Sop RVT, et al. (2020). Steroidal saponins from Raphia vinifera and their cytotoxic activity. Steroids,2020, 163, 108724. [View] [PubMed]
Pubchem:
99474
Cas:
512-04-9
Gnps:
CCMSLIB00006363650
Zinc:
ZINC000006857614
Kegg Ligand:
C08898
Chebi:
4629
Metabolights:
MTBLC4629
Chembl:
CHEMBL412437
Comptox:
DTXSID00895074
Pdb Ligand:
YUV
Selleck:
Diosgenin
CPRiL:
870
SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6
Level: 0
Mol. Weight: 414.63 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.45
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.08
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.46
- Plasma Protein Binding
- 69.38
- 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
- 19.0
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.28
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.41
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.96
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -59.55
- Rat (Acute)
- 1.95
- Rat (Chronic Oral)
- 1.35
- Fathead Minnow
- 3.82
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 424.91
- Hydration Free Energy
- -3.03
- Log(D) at pH=7.4
- 5.58
- Log(P)
- 6.06
- Log S
- -6.97
- Log(Vapor Pressure)
- -7.72
- Melting Point
- 192.19
- pKa Acid
- 12.84
- pKa Basic
- 8.21
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9202 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9069 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8984 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8758 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8035 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.8023 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7673 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7565 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7435 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7391 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.7035 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7020 |