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Oleandrigenin-beta-D-glucosyl (1→4)-beta-D-digitalose

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Triterpene Glycoside

Canonical Smiles	COC1[C@H](O)[C@H](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)OC([C@@H]1O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O)C
InChI	InChI=1S/C38H58O15/c1-17-32(53-34-30(44)29(43)28(42)25(15-39)52-34)33(47-5)31(45)35(49-17)51-21-8-10-36(3)20(13-21)6-7-23-22(36)9-11-37(4)27(19-12-26(41)48-16-19)24(50-18(2)40)14-38(23,37)46/h12,17,20-25,27-35,39,42-46H,6-11,13-16H2,1-5H3/t17?,20-,21+,22+,23-,24+,25?,27+,28-,29?,30+,31+,32+,33?,34+,35+,36+,37-,38+/m1/s1
InChIKey	DZDCBMUKBVGLRI-LWCXXLNYSA-N
Formula	C₃₈H₅₈O₁₅
HBA	15
HBD	6
MW	754.87
Rotatable Bonds	8
TPSA	220.13
LogP	0.48
Number Rings	7
Number Aromatic Rings	0
Heavy Atom Count	53
Formal Charge	0
Fraction CSP3	0.89
Exact Mass	754.38
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Adenium obesum	Apocynaceae	Plantae	69375

Showing of synonyms

Kiyohara H, Ichino C, et al. (2012). In vitro anti-influenza virus activity of a cardiotonic glycoside from Adenium obesum (Forssk.). Phytomedicine,2012,19(2),111-114. [View] [PubMed]

Pubchem: 162960747

Nmrshiftdb2: 60056846

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 754.87 g/mol

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

Level: 2

Mol. Weight: 754.87 g/mol

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

Level: 2

Mol. Weight: 754.87 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 754.87 g/mol

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

Level: 1

Mol. Weight: 754.87 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 754.87 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 754.87 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 754.87 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 754.87 g/mol

Antiviral

Absorption

Caco-2 (logPapp): -6.36
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 4.930
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1392.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.700
Plasma Protein Binding: 80.67
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: Non-Inhibitor

Excretion

Clearance: 0.780
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -35.260
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.420
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 7.820
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2529543.910
Rat (Acute): 3.960
Rat (Chronic Oral): 3.740
Fathead Minnow: 3199.410
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 281084.960
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 2.420
Log(P): 0.33
Log S: -2.51
Log(Vapor Pressure): -9160.4
Melting Point: 234.38
pKa Acid: -30.76
pKa Basic: 5.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7505
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7505
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7295
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7295
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7015
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7015

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