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Hecogenin-3-O-beta-D- xylopyranosyl-(1→3)-beta-D-glucopyranosyl-(1→2) [beta-D-xylopyranosyl (1→3)]-beta-D-glucopyranosyl (1→4)-beta-D-galactopyranoside

Family: Plantae - Agavaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Monodesmosidic Spirostanol Saponin

Canonical Smiles	OCC1O[C@@H](O[C@H]2CC[C@]3(C(C2)CCC2C3CC(=O)[C@]3(C2CC2C3[C@H](C)C3(O2)OC[C@@H](C[C@@H]3O)C)C)C)[C@H](C([C@H]1O[C@@H]1OC(CO)[C@H](C([C@@H]1O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O[C@@H]1OC[C@H](C([C@@H]1O)O)O)O)O[C@@H]1OC[C@H](C([C@@H]1O)O)O)O)O)O
InChI	InChI=1S/C55H88O28/c1-19-9-33(62)55(74-16-19)20(2)34-28(83-55)11-25-23-6-5-21-10-22(7-8-53(21,3)24(23)12-32(61)54(25,34)4)75-50-42(70)39(67)44(31(15-58)78-50)79-52-47(46(38(66)30(14-57)77-52)81-49-41(69)36(64)27(60)18-73-49)82-51-43(71)45(37(65)29(13-56)76-51)80-48-40(68)35(63)26(59)17-72-48/h19-31,33-52,56-60,62-71H,5-18H2,1-4H3/t19-,20+,21?,22+,23?,24?,25?,26-,27-,28?,29?,30?,31?,33+,34?,35?,36?,37-,38-,39?,40+,41+,42+,43+,44+,45?,46?,47+,48+,49+,50-,51+,52+,53+,54-,55?/m1/s1
InChIKey	KRXTVTCLGLJGNO-AGLLIFOXSA-N
Formula	C₅₅H₈₈O₂₈
HBA	28
HBD	15
MW	1197.28
Rotatable Bonds	13
TPSA	431.28
LogP	-5.66
Number Rings	11
Number Aromatic Rings	0
Heavy Atom Count	83
Formal Charge	0
Fraction CSP3	0.98
Exact Mass	1196.55
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Agave macroacantha	Agavaceae	Plantae	382123

Showing of synonyms

Eskander J, Lavaud C and Harakat D. (2010). Steroidal saponins from the leaves of Agave macroacantha. Fitoterapia,2010,81,371-374. [View] [PubMed]

Pubchem: 162817617

Nmrshiftdb2: 70098258

No compound-protein relationship available.

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(OC9CCCCO9)C8OC(OCC1)CC1OC1CCCCO1

Level: 5

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(OC9CCCCO9)C8OC1CCCCO1

Level: 4

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC(OCC9)CC9OC1CCCCO1

Level: 4

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3C(OC4CCCCO4)CCOC3OC5CCCOC5

Level: 4

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC9CCCCO9

Level: 3

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCC8)CC8OC9CCCCO9

Level: 3

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC1OC2C(OC3CCCCO3)CCOC2OC4CCCOC4

Level: 3

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1197.28 g/mol

SMILES: C1OCCCC1OC(OCCC2)C2OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 2

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 1197.28 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1197.28 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1197.28 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 1197.28 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1197.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1085485039.66
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 141860076695.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.62
Plasma Protein Binding: 33.21
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: 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: 1.23
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -3299344585.27
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1347.54
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Toxic
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -257469204722651.2
Rat (Acute): 4.07
Rat (Chronic Oral): 552247.97
Fathead Minnow: 325000265058.91
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 28958145139710.64
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -16097836.91
Log(P): -1876.27
Log S: -1.44
Log(Vapor Pressure): -953577019096.71
Melting Point: -286703.62
pKa Acid: -6948311510.76
pKa Basic: -55898959.99

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7578
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7578
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7289
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7289
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7254
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7254
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.7138
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.7138

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