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(22R,25R)-26-[(beta-D-glucopyranosyl)oxy]-16beta,22-dihydroxycholest-5-en-3beta-yl O-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](C1[C@@H](C(CC[C@H](COC1[C@H]([C@H]([C@@H](C(O1)CO)O)O)O)C)C1[C@H]([C@H]([C@@H](C(O1)CO)O)O)OC1[C@H]([C@H]([C@H](C(O1)C)O)O)O)C)O)C)OO
InChI	InChI=1S/C45H76O18/c1-19(18-58-42-38(55)36(53)33(50)30(17-47)61-42)6-8-24(40-41(37(54)34(51)29(16-46)60-40)62-43-39(56)35(52)32(49)21(3)59-43)20(2)31-28(48)15-27-25-9-7-22-14-23(63-57)10-12-44(22,4)26(25)11-13-45(27,31)5/h7,19-21,23-43,46-57H,6,8-18H2,1-5H3/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+/m1/s1
InChIKey	AUBURRGMJUSMGH-ULHJWARASA-N
Formula	C₄₅H₇₆O₁₈
HBA	18
HBD	12
MW	905.09
Rotatable Bonds	14
TPSA	298.14
LogP	-0.43
Number Rings	7
Number Aromatic Rings	0
Heavy Atom Count	63
Formal Charge	0
Fraction CSP3	0.96
Exact Mass	904.5
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: O1CCCCC1OCCCCC(C2C(CCCO2)OC3CCCCO3)CC(CC4)C(C45)CCC6C5CC=C7C6CCCC7

Level: 3

Mol. Weight: 905.09 g/mol

SMILES: O1CCCCC1OCCCCC(C2CCCCO2)CC(CC3)C(C34)CCC5C4CC=C6C5CCCC6

Level: 2

Mol. Weight: 905.09 g/mol

SMILES: O1CCCCC1OC(CCCO2)C2CCC3CCC(C34)C5C(CC4)C6C(=CC5)CCCC6

Level: 2

Mol. Weight: 905.09 g/mol

SMILES: O1CCCCC1OCCCCCC2C(CCCO2)OC3CCCCO3

Level: 2

Mol. Weight: 905.09 g/mol

SMILES: O1CCCCC1OCCCCCCC2CCC(C23)C4C(CC3)C5C(=CC4)CCCC5

Level: 1

Mol. Weight: 905.09 g/mol

SMILES: O1CCCCC1CCC2CCC(C23)C4C(CC3)C5C(=CC4)CCCC5

Level: 1

Mol. Weight: 905.09 g/mol

SMILES: O1CCCCC1CCCCCOC2CCCCO2

Level: 1

Mol. Weight: 905.09 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 905.09 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 905.09 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 905.09 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -6.6
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1033.93
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 135937.89

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 83.13
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: 1.56
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -3156.67
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.71
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.44
Micronucleos: Toxic
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: -246721265.38
Rat (Acute): 4.03
Rat (Chronic Oral): 4.23
Fathead Minnow: 311441.22
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: 27745727.05
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -1.82
Log(P): 0.36
Log S: -2.43
Log(Vapor Pressure): -913476.26
Melting Point: 234.38
pKa Acid: -6567.86
pKa Basic: -20.59

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8124
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8055
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7796
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7753
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7266
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7068

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