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Argeloside A

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Steroid
- Subclass: Pregnane Glycoside

Canonical Smiles	CO[C@@H]1C[C@@H](OC([C@H]1O[C@H]1C[C@@H](OC)[C@@H](C(O1)C)O[C@@H]1OC(C)[C@H]([C@@H](C1O)OC)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)C)O[C@H]1[C@H](O)C[C@@H](OC1C)O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@@]43O[C@H]3[C@@H]2[C@](O4)(C)OC3)C)C1)COC(=O)C
InChI	InChI=1S/C56H88O24/c1-24-45(33(59)18-38(69-24)73-30-13-16-55(23-67-28(5)58)29(17-30)11-12-32-31(55)14-15-53(6)50-37-22-68-54(50,7)80-56(32,53)79-37)75-39-19-34(64-8)46(25(2)70-39)76-40-20-35(65-9)47(26(3)71-40)77-52-44(63)49(66-10)48(27(4)72-52)78-51-43(62)42(61)41(60)36(21-57)74-51/h11,24-27,30-52,57,59-63H,12-23H2,1-10H3/t24?,25?,26?,27?,30-,31-,32+,33+,34+,35+,36?,37+,38-,39-,40-,41+,42-,43?,44?,45+,46+,47+,48+,49+,50-,51-,52-,53+,54+,55+,56-/m0/s1
InChIKey	NUHQNAFCQWNZHH-KKUBQSGSSA-N
Formula	C₅₆H₈₈O₂₄
HBA	24
HBD	6
MW	1145.3
Rotatable Bonds	16
TPSA	295.36
LogP	1.21
Number Rings	11
Number Aromatic Rings	0
Heavy Atom Count	80
Formal Charge	0
Fraction CSP3	0.95
Exact Mass	1144.57
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Solenostemma argel	Apocynaceae	Plantae	219273
2	Solenostemma argel	Apocynaceae	Plantae	219273

Showing of synonyms

Plaza A, Bifulco G, et al. (2003). Argeloside A and B, two novel 14,15-secopregnane glycosides from Solenostemma argel. Tetrahedron Letters,2003,44(47),8553-8558. [View]
Plaza A, Perrone A, et al. (2005). New antiproliferative 14,15-secopregnane glycosides from Solenostemma argel. Tetrahedron,2005,61(31),7470-7480. [View]

Pubchem: 163077988

Nmrshiftdb2: 60048181

No compound-protein relationship available.

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC(OC8)CCC8OC(OC9)CCC9OC(OC1)CCC1OC1CCCCO1

Level: 5

Mol. Weight: 1145.3 g/mol

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 4

Mol. Weight: 1145.3 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCC(OC3)OC4CCC(OC4)OC5CCCOC5

Level: 4

Mol. Weight: 1145.3 g/mol

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 3

Mol. Weight: 1145.3 g/mol

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1145.3 g/mol

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC8CCCCO8

Level: 2

Mol. Weight: 1145.3 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1145.3 g/mol

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC7CCCCO7

Level: 1

Mol. Weight: 1145.3 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1145.3 g/mol

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCCC6

Level: 0

Mol. Weight: 1145.3 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1145.3 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp): -5.93
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 31425332.690
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 4106922580.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.560
Plasma Protein Binding: 84.19
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: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 3.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -95517712.140
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -39.820
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -7453866696861.420
Rat (Acute): 4.340
Rat (Chronic Oral): 15989.180
Fathead Minnow: 9408923493.470
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 838353282126.740
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -466021.840
Log(P): -51.78
Log S: -4.0
Log(Vapor Pressure): -27606552148.13
Melting Point: -5813.15
pKa Acid: -201157187.71
pKa Basic: -1618288.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7670
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7670
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7098
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7098

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