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19-acetylglucocoroglaucigenin

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Cardenolide Glycoside

Canonical Smiles	OCC1O[C@@](O)(O[C@H]2C(O)O[C@H]([C@H](C2O)O)O[C@H]2CC[C@]3([C@H](C2)CC=C2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)COC(=O)C)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C36H52O17/c1-16(38)49-15-34-9-5-19(50-32-28(43)26(41)29(31(45)51-32)53-36(47)30(44)27(42)25(40)23(13-37)52-36)12-18(34)3-4-22-21(34)6-8-33(2)20(7-10-35(22,33)46)17-11-24(39)48-14-17/h4,11,18-21,23,25-32,37,40-47H,3,5-10,12-15H2,1-2H3/t18-,19-,20+,21-,23?,25+,26?,27?,28-,29+,30-,31?,32+,33+,34+,35-,36+/m0/s1
InChIKey	RCUHGCBEZZBPLV-ILDNDBGNSA-N
Formula	C₃₆H₅₂O₁₇
HBA	17
HBD	9
MW	756.8
Rotatable Bonds	8
TPSA	271.59
LogP	-2.01
Number Rings	7
Number Aromatic Rings	0
Heavy Atom Count	53
Formal Charge	0
Fraction CSP3	0.83
Exact Mass	756.32
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Gomphocarpus sinaicus	Apocynaceae	Plantae	2291033

Showing of synonyms

Abdel-Azim NS, Hammouda FM, et al. (1996). Re-investigation of the cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1996,42(2),523-529. [View]

Pubchem: 162848904

Nmrshiftdb2: 70013532

No compound-protein relationship available.

SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 756.8 g/mol

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 756.8 g/mol

SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 756.8 g/mol

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 756.8 g/mol

SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 756.8 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 756.8 g/mol

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCCC4

Level: 0

Mol. Weight: 756.8 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 756.8 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 756.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.82
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 4.06
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1369.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.88
Plasma Protein Binding: 69.03
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: 1.12
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -34.45
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.26
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.42
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2482876.66
Rat (Acute): 3.35
Rat (Chronic Oral): 3.6
Fathead Minnow: 3141.81
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 274635.41
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.8
Log(P): -2.05
Log S: -1.67
Log(Vapor Pressure): -8967.34
Melting Point: 224.26
pKa Acid: -28.77
pKa Basic: 8.03

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8912
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8912
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8388
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8388
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8205
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8205
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7719
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7719
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7275
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7275
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7003
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7003

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