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Penicilloside F

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(C2)CC[C@@]2(C3C[C@@H](CC(=O)c3ccccc3)[C@]3([C@]2(O)CC[C@@H]3C(=O)C)C)O)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
InChI	InChI=1S/C50H76O15/c1-26(51)34-17-20-50(56)48(34,6)32(22-35(52)30-13-11-10-12-14-30)23-38-47(5)18-16-33(21-31(47)15-19-49(38,50)55)63-39-24-36(57-7)43(28(3)60-39)64-40-25-37(58-8)44(29(4)61-40)65-46-42(54)45(59-9)41(53)27(2)62-46/h10-14,27-29,31-34,36-46,53-56H,15-25H2,1-9H3/t27?,28?,29?,31?,32-,33+,34-,36-,37-,38?,39+,40+,41-,42?,43-,44-,45+,46+,47+,48-,49+,50-/m1/s1
InChIKey	WCGKCTASIYEIPO-MEAPLUFBSA-N
Formula	C₅₀H₇₆O₁₅
HBA	15
HBD	4
MW	917.14
Rotatable Bonds	13
TPSA	198.13
LogP	4.9
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	65
Formal Charge	0
Fraction CSP3	0.84
Exact Mass	916.52
Number of Lipinski Rule Violations	2

#	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: 162817494

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)CC2CC(C3C(C24)CCC4)C5C(CC3)CC(CC5)OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 917.14 g/mol

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

Level: 3

Mol. Weight: 917.14 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 917.14 g/mol

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

Level: 2

Mol. Weight: 917.14 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 917.14 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 917.14 g/mol

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

Level: 1

Mol. Weight: 917.14 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 917.14 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 917.14 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 917.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 917.14 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 917.14 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -5.2
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 3510.770
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 459546.14

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.680
Plasma Protein Binding: 97.86
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: 3.310
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -10688.940
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.860
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.060
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -834056482.380
Rat (Acute): 5.530
Rat (Chronic Oral): 4.000
Fathead Minnow: 1052823.760
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: 93805452.120
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -31.560
Log(P): 4.35
Log S: -5.02
Log(Vapor Pressure): -3088835.69
Melting Point: 195.24
pKa Acid: -22426.14
pKa Basic: -153.52

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.9271
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.9271
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7715
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7715
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7451
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7451
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7450
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7450
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7323
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7323
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7297
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7297
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7282
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7282
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7258
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7258
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7246
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7246
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7246
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7246
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7223
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7223
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7206
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7206
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7195
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7195
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7181
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7181
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7175
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7175
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7152
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7152
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7151
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7151
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7141
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7141
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7132
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7132
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7131
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7131
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7123
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7123
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7091
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7091
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7059
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7059
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7047
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7047
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7000
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7000

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