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Penicilloside C

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](C[C@@H]3C(OC(=O)CC(C)C)C)OC(=O)c2ccccc2)C)O)C)C([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C51H78O21/c1-24(2)18-36(54)66-25(3)30-20-35(69-45(62)27-10-8-7-9-11-27)50(64)48(30,6)16-14-34-47(5)15-13-29(19-28(47)12-17-49(34,50)63)71-51(44(61)41(59)38(56)32(22-52)72-51)65-23-33-39(57)40(58)42(60)46(68-33)70-43-26(4)67-37(55)21-31(43)53/h7-11,24-26,28-35,37-44,46,52-53,55-61,63-64H,12-23H2,1-6H3/t25?,26?,28?,29-,30+,31+,32?,33?,34?,35+,37+,38+,39+,40-,41-,42?,43+,44?,46+,47-,48+,49-,50+,51-/m0/s1
InChIKey	FYFGTKMAFSJXSY-UBLXXGHNSA-N
Formula	C₅₁H₇₈O₂₁
HBA	21
HBD	11
MW	1027.16
Rotatable Bonds	14
TPSA	330.51
LogP	-0.1
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	72
Formal Charge	0
Fraction CSP3	0.84
Exact Mass	1026.5
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: 162902917

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC4C3CCC5C4CCC(C5)OC6(CCCCO6)OCC7CCCC(O7)OC8CCCOC8

Level: 4

Mol. Weight: 1027.16 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC4C3CCC5C4CCC(C5)OC6(CCCCO6)OCC7CCCCO7

Level: 3

Mol. Weight: 1027.16 g/mol

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

Level: 3

Mol. Weight: 1027.16 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC4C3CCC5C4CCC(C5)OC6CCCCO6

Level: 2

Mol. Weight: 1027.16 g/mol

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

Level: 2

Mol. Weight: 1027.16 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 1027.16 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC4C3CCC5C4CCCC5

Level: 1

Mol. Weight: 1027.16 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 1027.16 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1027.16 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1027.16 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 1027.16 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1027.16 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1027.16 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -6.49
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 58763.83
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7680599.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.74
Plasma Protein Binding: 74.27
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: 2.01
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -178627.97
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.14
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: -13939917373.24
Rat (Acute): 4.03
Rat (Chronic Oral): 30.45
Fathead Minnow: 17596194.33
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 1567848368.72
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -857.19
Log(P): 2.52
Log S: -2.66
Log(Vapor Pressure): -51628350.61
Melting Point: 189.81
pKa Acid: -376105.85
pKa Basic: -3013.45

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8134
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8134
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7570
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7570
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7017
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7017

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