ANPDB

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Argeloside B

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](O)[C@@H](C(O1)C)O[C@H]1C[C@@H](O)[C@@H](C(O1)C)O[C@H]1C[C@@H](OC)[C@@H](C(O1)C)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)C)O[C@H]1[C@H](OC)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/C62H98O26/c1-27-52(82-44-19-37(65)53(28(2)75-44)83-47-23-41(72-11)56(31(5)79-47)86-58-51(69)50(68)49(67)42(24-63)81-58)38(66)20-45(76-27)84-54-30(4)78-48(22-40(54)71-10)85-55-29(3)77-46(21-39(55)70-9)80-34-14-17-61(26-73-32(6)64)33(18-34)12-13-36-35(61)15-16-59(7)57-43-25-74-60(57,8)88-62(36,59)87-43/h12,27-31,34-58,63,65-69H,13-26H2,1-11H3/t27?,28?,29?,30?,31?,34-,35-,36+,37+,38+,39+,40+,41+,42?,43+,44-,45-,46-,47-,48-,49+,50-,51?,52+,53+,54+,55+,56+,57-,58-,59+,60+,61+,62-/m0/s1
InChIKey	FNHGVUUMWYKAFF-LNAHLQCFSA-N
Formula	C₆₂H₉₈O₂₆
HBA	26
HBD	6
MW	1259.44
Rotatable Bonds	18
TPSA	313.82
LogP	2.12
Number Rings	12
Number Aromatic Rings	0
Heavy Atom Count	88
Formal Charge	0
Fraction CSP3	0.95
Exact Mass	1258.63
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: 162955994

Nmrshiftdb2: 60048176

No compound-protein relationship available.

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC(OC8)CCC8OC(OC9)CCC9OC(OC1)CCC1OC(OC1)CCC1OC1CCCCO1

Level: 6

Mol. Weight: 1259.44 g/mol

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

Level: 5

Mol. Weight: 1259.44 g/mol

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC(OC4)CCC4OC(OC5)CCC5OC6CCCCO6

Level: 5

Mol. Weight: 1259.44 g/mol

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

Level: 4

Mol. Weight: 1259.44 g/mol

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

Level: 4

Mol. Weight: 1259.44 g/mol

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

Level: 3

Mol. Weight: 1259.44 g/mol

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1259.44 g/mol

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

Level: 2

Mol. Weight: 1259.44 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1259.44 g/mol

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

Level: 1

Mol. Weight: 1259.44 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1259.44 g/mol

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

Level: 0

Mol. Weight: 1259.44 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1259.44 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp): -6.38
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 4678275208265.360
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 611395281524601.4

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.470
Plasma Protein Binding: 86.05
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: 2.970
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -14219670970646.369
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -5806060.770
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: Toxic
T. Pyriformis: -1109652917034877952.000
Rat (Acute): 826.240
Rat (Chronic Oral): 2380108496.110
Fathead Minnow: 1400699776705282.250
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: 124805202651881792.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -69379234290.860
Log(P): -8076558.69
Log S: -4.94
Log(Vapor Pressure): -4109771660856916.5
Melting Point: -1248809502.22
pKa Acid: -29946165497288.6
pKa Basic: -240916042845.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7942
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7942

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