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Russelioside G

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

Canonical Smiles	COC1C[C@H](O[C@H]2CC[C@]3(C(=CCC4[C@@H]3C[C@@H](CC(=O)c3ccccc3)[C@]3([C@]4(O)CC[C@@H]3[C@H](OC(=O)C)C)C)C2)C)OC([C@H]1O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O)C
InChI	InChI=1S/C44H64O13/c1-23(53-25(3)46)30-15-17-44(51)31-13-12-27-18-29(14-16-42(27,4)32(31)19-28(43(30,44)5)20-33(47)26-10-8-7-9-11-26)55-36-21-34(52-6)40(24(2)54-36)57-41-39(50)38(49)37(48)35(22-45)56-41/h7-12,23-24,28-32,34-41,45,48-51H,13-22H2,1-6H3/t23-,24?,28+,29+,30-,31?,32+,34?,35?,36+,37-,38?,39+,40-,41+,42+,43-,44+/m1/s1
InChIKey	XVANCJMSPAVRPC-XDXNUYJKSA-N
Formula	C₄₄H₆₄O₁₃
HBA	13
HBD	5
MW	800.98
Rotatable Bonds	11
TPSA	190.67
LogP	3.85
Number Rings	7
Number Aromatic Rings	1
Heavy Atom Count	57
Formal Charge	0
Fraction CSP3	0.77
Exact Mass	800.43
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Caralluma russeliana	Apocynaceae	Plantae	120809

Showing of synonyms

Abdel-Sattar E, Ahmed AA, et al. (2007). Acylated pregnane glycosides from Caralluma russeliana. Phytochemistry,2007,68(10),1459-1463. [View] [PubMed]

Pubchem: 162817562

Nmrshiftdb2: 70098481

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)CC2CC(C3C(C24)CCC4)C5C(=CC3)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 800.98 g/mol

SMILES: c1ccccc1C(=O)CC2CC(C3C(C24)CCC4)C5C(=CC3)CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 800.98 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 800.98 g/mol

SMILES: c1ccccc1C(=O)CC2CC(C3C(C24)CCC4)C5C(=CC3)CCCC5

Level: 1

Mol. Weight: 800.98 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 800.98 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 800.98 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 800.98 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 800.98 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 800.98 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 67.010
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 9476.03

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.960
Plasma Protein Binding: 104.58
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: 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: Inhibitor

Excretion

Clearance: 3.880
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -223.360
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.470
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.940
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -17200295.900
Rat (Acute): 4.610
Rat (Chronic Oral): 3.670
Fathead Minnow: 21718.520
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: 1931373.690
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 4.320
Log(P): 4.19
Log S: -4.03
Log(Vapor Pressure): -63490.67
Melting Point: 206.05
pKa Acid: -399.0
pKa Basic: 5.38

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8858
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8858
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8183
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8183
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8034
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8034
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7634
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7634
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7592
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7592
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7405
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7405
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7353
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7353
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7324
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7324
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7319
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7319
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7215
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7215
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7215
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7215
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7204
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7204
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7187
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7187
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7159
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7159
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7148
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7148
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7126
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7126
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7120
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7120
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7109
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7109
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7075
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7075
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7032
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7032
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7018
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7018
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7008
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7008

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