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Oleandrigenin 3-O-beta-glucopyranosyl-(1→4)-beta-cymaropyranosyl-(1→4)-beta-digitoxopyranoside

Family: Plantae - Asclepiadaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Cardiac Glycoside

Canonical Smiles	CO[C@H]1C[C@H](O[C@H]2[C@@H](O)C[C@@H](O[C@@H]2C)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)C[C@@H]([C@@H]3C2=CC(=O)OC2)OC(=O)C)C)C)O[C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
InChI	InChI=1S/C44H68O17/c1-20-39(60-34-16-29(53-6)40(21(2)56-34)61-41-38(51)37(50)36(49)31(18-45)59-41)28(47)15-33(55-20)58-25-9-11-42(4)24(14-25)7-8-27-26(42)10-12-43(5)35(23-13-32(48)54-19-23)30(57-22(3)46)17-44(27,43)52/h13,20-21,24-31,33-41,45,47,49-52H,7-12,14-19H2,1-6H3/t20-,21-,24-,25+,26+,27-,28+,29+,30+,31-,33+,34+,35+,36-,37+,38-,39-,40-,41+,42+,43-,44+/m1/s1
InChIKey	SGGQTRPBTCNENJ-PQDIYILCSA-N
Formula	C₄₄H₆₈O₁₇
HBA	17
HBD	6
MW	869.01
Rotatable Bonds	10
TPSA	238.59
LogP	1.39
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	61
Formal Charge	0
Fraction CSP3	0.91
Exact Mass	868.45
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cryptostegia grandiflora	Asclepiadaceae	Plantae	63468

Showing of synonyms

El-Mawla AMAA (2010). Cardiac glycosides from shoot cultures of Cryptostegia grandiflora. Pharmacognosy Research,2010,2(1),15-18. [View] [PubMed]

Pubchem: 101158494

Zinc: ZINC000255264428

Nmrshiftdb2: 60054096

No compound-protein relationship available.

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 869.01 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 869.01 g/mol

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 869.01 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 869.01 g/mol

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 869.01 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 869.01 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 869.01 g/mol

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 869.01 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 869.01 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 869.01 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 869.01 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 869.01 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.09
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 543.990
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 71850.22

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.590
Plasma Protein Binding: 88.26
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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 1.260
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1670.950
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.830
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.470
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -130406785.370
Rat (Acute): 4.370
Rat (Chronic Oral): 3.460
Fathead Minnow: 164616.700
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 14663665.750
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 2.640
Log(P): 1.05
Log S: -3.3
Log(Vapor Pressure): -482733.81
Melting Point: 228.41
pKa Acid: -3437.36
pKa Basic: 3.86

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8973
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8973
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7515
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7515

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