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Penicilloside B

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

Canonical Smiles	OCC1O[C@@](OCC2O[C@H](O[C@H]3[C@H](O)C[C@@H](OC3C)O)C([C@H]([C@@H]2O)O)O)(O[C@H]2CC[C@]3(C(C2)CC[C@@]2(C3CC[C@]3([C@]2(O)[C@H](O)C[C@@H]3C(OC(=O)c2ccccc2)C)C)O)C)C([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C46H70O20/c1-21(62-40(57)23-8-6-5-7-9-23)26-17-31(49)45(59)43(26,4)14-12-30-42(3)13-11-25(16-24(42)10-15-44(30,45)58)65-46(39(56)36(54)33(51)28(19-47)66-46)60-20-29-34(52)35(53)37(55)41(63-29)64-38-22(2)61-32(50)18-27(38)48/h5-9,21-22,24-39,41,47-56,58-59H,10-20H2,1-4H3/t21?,22?,24?,25-,26+,27+,28?,29?,30?,31+,32+,33+,34+,35-,36-,37?,38+,39?,41+,42-,43+,44-,45+,46-/m0/s1
InChIKey	LFGJCJVUOXLYQA-CTQJHBNESA-N
Formula	C₄₆H₇₀O₂₀
HBA	20
HBD	12
MW	943.05
Rotatable Bonds	11
TPSA	324.44
LogP	-1.7
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	66
Formal Charge	0
Fraction CSP3	0.85
Exact Mass	942.45
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: 162817496

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC(CC2)C(C23)CCC4C3CCC5C4CCC(C5)OC6(CCCCO6)OCC7CCCC(O7)OC8CCCOC8

Level: 4

Mol. Weight: 943.05 g/mol

SMILES: c1ccccc1C(=O)OCC(CC2)C(C23)CCC4C3CCC5C4CCC(C5)OC6(CCCCO6)OCC7CCCCO7

Level: 3

Mol. Weight: 943.05 g/mol

SMILES: C1OCCCC1OC(O2)CCCC2COC3(CCCCO3)OC(C4)CCC5C4CCC6C5CCC(C67)CCC7

Level: 3

Mol. Weight: 943.05 g/mol

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

Level: 2

Mol. Weight: 943.05 g/mol

SMILES: O1CCCCC1COC2(CCCCO2)OC(C3)CCC4C3CCC5C4CCC(C56)CCC6

Level: 2

Mol. Weight: 943.05 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 943.05 g/mol

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

Level: 1

Mol. Weight: 943.05 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 943.05 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 943.05 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 943.05 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 943.05 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 943.05 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 943.05 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.74
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 4209.21
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 550940.87

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.82
Plasma Protein Binding: 71.38
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: 1.09
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -12808.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.21
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -999929192.69
Rat (Acute): 3.81
Rat (Chronic Oral): 3.83
Fathead Minnow: 1262205.67
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 112459293.75
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -46.55
Log(P): 0.81
Log S: -2.16
Log(Vapor Pressure): -3703105.49
Melting Point: 203.81
pKa Acid: -26896.81
pKa Basic: -196.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8856
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8856
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8599
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8599
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7283
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7283
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7215
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7215
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7165
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7165
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7142
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7142
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7126
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7126
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7094
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7094
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7080
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7080
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7034
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7034

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