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2alpha-hydroxyheinsiagenin A 3-O-[alpha-L-rhamnopyranosyl-(1→2)-beta-D-glucopyranosyl-(1→2)]-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)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O
InChI	InChI=1S/C54H85NO19/c1-23(11-10-12-24(2)45(66)55-34-25(3)26(4)68-46(34)67)28-15-16-52(9)33-14-13-32-50(6,7)44(29(58)19-54(32)22-53(33,54)18-17-51(28,52)8)74-49-43(40(64)37(61)31(21-57)71-49)73-48-42(39(63)36(60)30(20-56)70-48)72-47-41(65)38(62)35(59)27(5)69-47/h10-12,23,25-44,47-49,56-65H,13-22H2,1-9H3,(H,55,66)/b11-10+,24-12+/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	XMJLHZREWOAWHR-IYRGMYTGSA-N
Formula	C₅₄H₈₅NO₁₉
HBA	19
HBD	11
MW	1052.26
Rotatable Bonds	13
TPSA	313.08
LogP	0.46
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	74
Formal Charge	0
Fraction CSP3	0.89
Exact Mass	1051.57
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: 134693006

No compound-protein relationship available.

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OCCC7)C7OC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1052.26 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: 1052.26 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OCCC6)C6OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1052.26 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: 1052.26 g/mol

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

Level: 2

Mol. Weight: 1052.26 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1052.26 g/mol

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

Level: 1

Mol. Weight: 1052.26 g/mol

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

Level: 1

Mol. Weight: 1052.26 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1052.26 g/mol

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

Level: 0

Mol. Weight: 1052.26 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1052.26 g/mol

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 1052.26 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -6.27
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 186713.680
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 24402138.45

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.850
Plasma Protein Binding: 91.17
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: 1.250
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -567531.860
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.270
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: -44288711672.430
Rat (Acute): 4.060
Rat (Chronic Oral): 95.430
Fathead Minnow: 55905108.460
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: 4981246794.350
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -2754.190
Log(P): 2.63
Log S: -3.07
Log(Vapor Pressure): -164029794.36
Melting Point: 207.55
pKa Acid: -1195124.33
pKa Basic: -9593.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8492
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7752
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7053

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