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2alpha-hydroxyheinsiagenin A 3-O-[beta-D-glucopyranosyl-(1→2)]-[beta-D-glucopyranosyl-(1→4)]-beta-D-glucopyranoside

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Triterpenoid Saponin

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2[C@H](O)C[C@]34[C@H](C2(C)C)CC[C@@H]2[C@@]4(C3)CC[C@]3([C@@]2(C)CC[C@@H]3[C@@H](/C=C/C=C(/C(=O)N[C@@H]2C(=O)O[C@@H]([C@@H]2C)C)\C)C)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C54H85NO20/c1-23(10-9-11-24(2)45(67)55-34-25(3)26(4)69-46(34)68)27-14-15-52(8)33-13-12-32-50(5,6)44(28(59)18-54(32)22-53(33,54)17-16-51(27,52)7)75-49-43(74-48-40(65)38(63)36(61)30(20-57)71-48)41(66)42(31(21-58)72-49)73-47-39(64)37(62)35(60)29(19-56)70-47/h9-11,23,25-44,47-49,56-66H,12-22H2,1-8H3,(H,55,67)/b10-9+,24-11+/t23-,25+,26-,27-,28-,29-,30-,31-,32+,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44+,47+,48+,49+,51-,52+,53+,54-/m1/s1
InChIKey	YJKGYFLFQBFYCU-YXUCCVFCSA-N
Formula	C₅₄H₈₅NO₂₀
HBA	20
HBD	12
MW	1068.26
Rotatable Bonds	14
TPSA	333.31
LogP	-0.57
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	75
Formal Charge	0
Fraction CSP3	0.89
Exact Mass	1067.57
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Mussaenda luteola	Rubiaceae	Plantae	43523

Showing of synonyms

Mohamed S.M, Bachkeet E.Y, et al. (2015). Potent antitrypanosomal triterpenoid saponins from Mussaenda luteola. Fitoterapia, 2015, 107, 114-121. [View] [PubMed]

Pubchem: 134693007

No compound-protein relationship available.

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(C7OC8CCCCO8)OCC(C7)OC9CCCCO9

Level: 4

Mol. Weight: 1068.26 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1068.26 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 1068.26 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(C6OC7CCCCO7)OCC(C6)OC8CCCCO8

Level: 3

Mol. Weight: 1068.26 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC7CCCCO7

Level: 2

Mol. Weight: 1068.26 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 1068.26 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OC6)CCC6OC7CCCCO7

Level: 2

Mol. Weight: 1068.26 g/mol

SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 1068.26 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CCCC5

Level: 1

Mol. Weight: 1068.26 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC6CCCCO6

Level: 1

Mol. Weight: 1068.26 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1068.26 g/mol

SMILES: C1CCCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 1068.26 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1068.26 g/mol

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 1068.26 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -6.39
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 316381.590
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 41348260.49

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.840
Plasma Protein Binding: 87.77
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: Inhibitor

Excretion

Clearance: 0.920
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -961658.980
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.310
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -75045093277.910
Rat (Acute): 3.910
Rat (Chronic Oral): 161.230
Fathead Minnow: 94728423.070
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 8440486713.570
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -4678.910
Log(P): 1.71
Log S: -2.82
Log(Vapor Pressure): -277940778.92
Melting Point: 213.45
pKa Acid: -2025143.29
pKa Basic: -16274.59

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.9054
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8476
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7947
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	3	0.7418
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7134
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7099
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7073

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