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Caratuberside G

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

Canonical Smiles	CO[C@@H]1C[C@H](O[C@H]2CC[C@]3(C(=CCC4C3C[C@@H](OC(=O)c3ccccc3)[C@]3([C@]4(O)CC[C@@H]3C(OC(=O)c3ccccc3)C)C)C2)C)OC([C@H]1O[C@H]1C[C@@H](OC)[C@@H](C(O1)C)O[C@@H]1OC(C)[C@H]([C@@H](C1O)OC)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)C
InChI	InChI=1S/C62H88O21/c1-31(76-56(68)35-16-12-10-13-17-35)39-23-25-62(70)40-21-20-37-26-38(22-24-60(37,5)41(40)27-45(61(39,62)6)80-57(69)36-18-14-11-15-19-36)78-46-28-42(71-7)52(32(2)74-46)81-47-29-43(72-8)53(33(3)75-47)82-59-51(67)55(73-9)54(34(4)77-59)83-58-50(66)49(65)48(64)44(30-63)79-58/h10-20,31-34,38-55,58-59,63-67,70H,21-30H2,1-9H3/t31?,32?,33?,34?,38-,39+,40?,41?,42+,43+,44?,45+,46-,47-,48+,49-,50?,51?,52+,53+,54+,55+,58-,59-,60-,61-,62-/m0/s1
InChIKey	SXTZIDNXMZXWCP-DNHKMJRRSA-N
Formula	C₆₂H₈₈O₂₁
HBA	21
HBD	6
MW	1169.37
Rotatable Bonds	17
TPSA	275.51
LogP	4.52
Number Rings	10
Number Aromatic Rings	2
Heavy Atom Count	83
Formal Charge	0
Fraction CSP3	0.74
Exact Mass	1168.58
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Caralluma species	Apocynaceae	Plantae	197242

Showing of synonyms

Abdel-Sattara E, Shehab NG, et al. (2009). Antitrypanosomal activity of some pregnane glycosides isolated from Caralluma species. Phytomedicine,2009,16(6),659-664. [View] [PubMed]

Pubchem: 162868854

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(CC3OC(=O)c5ccccc5)C6C(=CC4)CC(CC6)OC(OC7)CCC7OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 6

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(CC3OC(=O)c5ccccc5)C6C(=CC4)CC(CC6)OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 5

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC(CC2)C(C23)CCC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 5

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 5

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(CC3OC(=O)c5ccccc5)C6C(=CC4)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC(CC2)C(C23)CCC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 1169.37 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(C5C(=CC4)CC(CC5)OC6CCCCO6)CC3OC(=O)c7ccccc7

Level: 3

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(CC3)C5C(=CC4)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 1169.37 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 1169.37 g/mol

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(C5C(=CC4)CCCC5)CC3OC(=O)c6ccccc6

Level: 2

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(CC3)C5C(=CC4)CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC6CCCCO6

Level: 2

Mol. Weight: 1169.37 g/mol

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

Level: 2

Mol. Weight: 1169.37 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(C23)C4C(CC3)C5C(=CC4)CCCC5

Level: 1

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCCC5

Level: 1

Mol. Weight: 1169.37 g/mol

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

Level: 1

Mol. Weight: 1169.37 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1169.37 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 1169.37 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1169.37 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1169.37 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -5.77
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 189961855.810
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 24825776520.37

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.730
Plasma Protein Binding: 94.47
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: Inhibitor

Excretion

Clearance: 3.720
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -577391345.680
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -236.530
Liver Injury II: Toxic
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: Safe
T. Pyriformis: -45057586489832.742
Rat (Acute): 4.760
Rat (Chronic Oral): 96646.340
Fathead Minnow: 56875647319.380
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: 5067729454543.940
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -2817129.870
Log(P): -321.35
Log S: -4.79
Log(Vapor Pressure): -166877768044.02
Melting Point: -47869.04
pKa Acid: -1215967722.75
pKa Basic: -9782409.69

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9062
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9062
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8861
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8861
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8854
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8854
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8803
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8803
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8468
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8468
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8434
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8434
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8058
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8058
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7980
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7980
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.7960
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.7960
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7817
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7817
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	2	0.7803
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	2	0.7803
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7546
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7546
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7475
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7475
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7458
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7458
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7398
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7398
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7357
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7357
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7207
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7207
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7206
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7206
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7191
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7191
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	2	0.7154
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	2	0.7154
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7150
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7150
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7111
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7111
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7092
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7092
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7090
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7090
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7069
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7069
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7045
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7045

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