ANPDB

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Alpinoside B

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

Canonical Smiles	CO[C@@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@]4(C3C[C@@H](OC(=O)/C=C/c3ccccc3)[C@]3([C@]4(O)CC[C@@]3(O)C(=O)C)C)O)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/C57H84O22/c1-28-47(77-42-25-36(69-8)48(29(2)72-42)78-52-46(64)50(70-9)49(30(3)73-52)79-51-45(63)44(62)43(61)37(27-58)75-51)35(68-7)24-41(71-28)74-34-18-19-53(5)33(23-34)17-20-56(66)38(53)26-39(76-40(60)16-15-32-13-11-10-12-14-32)54(6)55(65,31(4)59)21-22-57(54,56)67/h10-17,28-30,34-39,41-52,58,61-67H,18-27H2,1-9H3/b16-15+/t28?,29?,30?,34-,35+,36+,37?,38?,39+,41-,42-,43+,44-,45?,46?,47+,48+,49+,50+,51-,52-,53-,54+,55+,56-,57+/m0/s1
InChIKey	CBAZUPHAXPSNQN-ABANGKNFSA-N
Formula	C₅₇H₈₄O₂₂
HBA	22
HBD	8
MW	1121.28
Rotatable Bonds	16
TPSA	306.74
LogP	1.5
Number Rings	9
Number Aromatic Rings	1
Heavy Atom Count	79
Formal Charge	0
Fraction CSP3	0.79
Exact Mass	1120.55
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Oxystelma esculentum	Apocynaceae	Plantae	126763

Showing of synonyms

Hamed AI, Sheded MG, et al. (2004). Polyhydroxypregnane glycosides from Oxystelma esculentum var. Alpine. Phytochemistry,2004,65(7),975-980. [View] [PubMed]

Pubchem: 163040658

Nmrshiftdb2: 70080323

No compound-protein relationship available.

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

Level: 5

Mol. Weight: 1121.28 g/mol

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

Level: 4

Mol. Weight: 1121.28 g/mol

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

Level: 4

Mol. Weight: 1121.28 g/mol

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

Level: 3

Mol. Weight: 1121.28 g/mol

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

Level: 3

Mol. Weight: 1121.28 g/mol

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1121.28 g/mol

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

Level: 2

Mol. Weight: 1121.28 g/mol

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

Level: 2

Mol. Weight: 1121.28 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1121.28 g/mol

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

Level: 1

Mol. Weight: 1121.28 g/mol

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

Level: 1

Mol. Weight: 1121.28 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1121.28 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 1121.28 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1121.28 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1121.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.15
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 5833635.420
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 762388043.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.730
Plasma Protein Binding: 87.81
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: 3.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -17731416.870
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -8.080
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: Toxic
T. Pyriformis: -1383697685328.620
Rat (Acute): 4.820
Rat (Chronic Oral): 2969.590
Fathead Minnow: 1746624908.470
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: 155627621337.500
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -86495.160
Log(P): -7.11
Log S: -3.51
Log(Vapor Pressure): -5124738604.16
Melting Point: -150.07
pKa Acid: -37341711.15
pKa Basic: -300399.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7179
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7179
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7174
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7174
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7026
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7026

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