Diosgenin-3-O-beta-D-glucopyranosyl-(1→3)-beta-D-glucopyranosyl-(1→4)-[alpha-L-rhamnopyranosyl-(1→2]-beta-D-glucopyranoside - Compound Card

Diosgenin-3-O-beta-D-glucopyranosyl-(1→3)-beta-D-glucopyranosyl-(1→4)-[alpha-L-rhamnopyranosyl-(1→2]-beta-D-glucopyranoside

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Diosgenin-3-O-beta-D-glucopyranosyl-(1→3)-beta-D-glucopyranosyl-(1→4)-[alpha-L-rhamnopyranosyl-(1→2]-beta-D-glucopyranoside

Family: Plantae - Arecaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Triterpenoid Saponin

Canonical Smiles	C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3C[C@H]2C1[C@@H]([C@@]1(O2)OCC(CC1)C)C)C)OC1[C@H]([C@H]([C@@H](C(O1)CO)OC1[C@H]([C@H]([C@@H](C(O1)CO)O)O)O)O)OC1[C@H]([C@H]([C@H](C(O1)C)O)O)O
InChI	InChI=1S/C45H72O17/c1-19-8-13-45(55-18-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-35(52)33(50)31(48)21(3)56-40)37(54)38(29(17-47)59-42)60-41-36(53)34(51)32(49)28(16-46)58-41/h6,19-21,23-42,46-54H,7-18H2,1-5H3/t19?,20-,21?,23-,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	OLAMGHNQGZIWHZ-OFAQLBCSSA-N
Formula	C₄₅H₇₂O₁₇
HBA	17
HBD	9
MW	885.05
Rotatable Bonds	8
TPSA	255.91
LogP	0.21
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	62
Formal Charge	0
Fraction CSP3	0.96
Exact Mass	884.48
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Raphia farinifera	Arecaceae	Plantae	93338

Showing of synonyms

Tapondjou L, Siems K, et al. (2015). Steroidal saponins from the mesocarp of the fruits of Raphia farinifera (Arecaceae) and their cytotoxic activity. Natural Product Communications, 2015, 10(11), 1941-1944. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC(C7OC8CCCCO8)OCC(C7)OC9CCCCO9

Level: 3

Mol. Weight: 885.05 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 2

Mol. Weight: 885.05 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 2

Mol. Weight: 885.05 g/mol

SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 885.05 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 885.05 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 885.05 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6

Level: 0

Mol. Weight: 885.05 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 885.05 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -6.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1266.0
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 166268.38

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.86
Plasma Protein Binding: 76.07
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: 0.39
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 33937015.88
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -3.85
Log(P): 2.39
Log S: -2.64
Log(Vapor Pressure): -1117378.68
Melting Point: 221.83
pKa Acid: -8063.06
pKa Basic: -35.68

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7057
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7003