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Heinsiagenin 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]2CC[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/C54H85NO18/c1-24(11-10-12-25(2)45(65)55-35-26(3)27(4)67-46(35)66)29-15-17-52(9)33-14-13-32-50(6,7)34(16-18-53(32)23-54(33,53)20-19-51(29,52)8)71-48-43(40(62)37(59)30(21-56)69-48)73-49-44(41(63)38(60)31(22-57)70-49)72-47-42(64)39(61)36(58)28(5)68-47/h10-12,24,26-44,47-49,56-64H,13-23H2,1-9H3,(H,55,65)/b11-10+,25-12+/t24-,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	ZTOQAAOUYNVPBT-WEKRTRDKSA-N
Formula	C₅₄H₈₅NO₁₈
HBA	18
HBD	10
MW	1036.26
Rotatable Bonds	13
TPSA	292.85
LogP	1.49
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	73
Formal Charge	0
Fraction CSP3	0.89
Exact Mass	1035.58
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: 134693004

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: 1036.26 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: 1036.26 g/mol

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

Level: 3

Mol. Weight: 1036.26 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: 1036.26 g/mol

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

Level: 2

Mol. Weight: 1036.26 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1036.26 g/mol

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

Level: 1

Mol. Weight: 1036.26 g/mol

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

Level: 1

Mol. Weight: 1036.26 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1036.26 g/mol

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

Level: 0

Mol. Weight: 1036.26 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1036.26 g/mol

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 1036.26 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -6.21
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 130962.290
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 17116121.14

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.950
Plasma Protein Binding: 96.61
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: 1.260
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -398076.680
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.360
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: -31064933671.370
Rat (Acute): 3.910
Rat (Chronic Oral): 67.320
Fathead Minnow: 39212917.970
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 3493938760.850
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1926.090
Log(P): 3.42
Log S: -3.34
Log(Vapor Pressure): -115053499.01
Melting Point: 219.21
pKa Acid: -838254.49
pKa Basic: -6720.28

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7757
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7453
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7069
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7006

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