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12beta-benzoyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[beta-D-oleandropyranosyl-(1→4)-beta-D-cymaropyranoside]

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

Canonical Smiles	COC1C(O)C(O[C@H]2CC[C@]3([C@H](C2)CC[C@@]2(C3C[C@@H](OC(=O)c3ccccc3)[C@]3([C@]2(O)CC[C@@H]3C(OC(=O)CC(C)C)C)C)O)C)OC(C1OC1OC(COC2OC(CO)C(C(C2O)O)O)C(C(C1O)O)O)C
InChI	InChI=1S/C52H80O21/c1-24(2)19-35(54)67-25(3)30-15-18-52(64)50(30,6)34(72-45(62)27-11-9-8-10-12-27)21-33-49(5)16-14-29(20-28(49)13-17-51(33,52)63)69-48-42(61)44(65-7)43(26(4)68-48)73-47-41(60)39(58)37(56)32(71-47)23-66-46-40(59)38(57)36(55)31(22-53)70-46/h8-12,24-26,28-34,36-44,46-48,53,55-61,63-64H,13-23H2,1-7H3/t25?,26?,28-,29-,30+,31?,32?,33?,34+,36?,37?,38?,39?,40?,41?,42?,43?,44?,46?,47?,48?,49-,50-,51-,52+/m0/s1
InChIKey	HOYNHIJMZRIZCF-SQCCAUONSA-N
Formula	C₅₂H₈₀O₂₁
HBA	21
HBD	10
MW	1041.19
Rotatable Bonds	15
TPSA	319.51
LogP	0.2
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	73
Formal Charge	0
Fraction CSP3	0.85
Exact Mass	1040.52
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Caralluma retrospiciens	Apocynaceae	Plantae	197251

Showing of synonyms

Halim AF and Khalil AT. (1996). Pregnane glycosides from Caralluma retrospiciens. Phytochemistry,1996,42(4),1135-1139. [View] [PubMed]

Pubchem: 162845870

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCC(C5)OC(OC6)CCC6OC(O7)CCCC7COC8CCCCO8

Level: 4

Mol. Weight: 1041.19 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCC(C5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 1041.19 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCC(OC3)OC(C4)CCC5C4CCC6C5CCC(C67)CCC7

Level: 3

Mol. Weight: 1041.19 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCC(C5)OC6CCCCO6

Level: 2

Mol. Weight: 1041.19 g/mol

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

Level: 2

Mol. Weight: 1041.19 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 1041.19 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCCC5

Level: 1

Mol. Weight: 1041.19 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 1041.19 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1041.19 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1041.19 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 1041.19 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1041.19 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1041.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 113230.040
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 14798671.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 48.41
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: 1.980
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -344179.770
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.270
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: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -26858868982.270
Rat (Acute): 4.220
Rat (Chronic Oral): 58.120
Fathead Minnow: 33903590.300
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: 3020873117.520
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1666.470
Log(P): 2.97
Log S: -2.76
Log(Vapor Pressure): -99475733.53
Melting Point: 194.29
pKa Acid: -724748.2
pKa Basic: -5815.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8697
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8697
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8568
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8568
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8464
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8464
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7867
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7867
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7627
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7627
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7383
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7383
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7246
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7246
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7025
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7025

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