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

Family: 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)O)O[C@@H]1OC[C@H](C([C@@H]1O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)O)O)O)O
InChI	InChI=1S/C56H90O28/c1-19-10-33(62)56(74-17-19)20(2)34-28(84-56)12-26-24-7-6-22-11-23(8-9-54(22,4)25(24)13-32(61)55(26,34)5)76-51-43(71)40(68)46(31(16-59)79-51)81-53-48(83-52-42(70)39(67)36(64)29(14-57)77-52)47(37(65)30(15-58)78-53)82-49-44(72)45(27(60)18-73-49)80-50-41(69)38(66)35(63)21(3)75-50/h19-31,33-53,57-60,62-72H,6-18H2,1-5H3/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-,56?/m1/s1
InChIKey	RDVFKWXDYPJTQW-KWELZAGVSA-N
Formula	C₅₆H₉₀O₂₈
HBA	28
HBD	15
MW	1211.31
Rotatable Bonds	13
TPSA	431.28
LogP	-5.27
Number Rings	11
Number Aromatic Rings	0
Heavy Atom Count	84
Formal Charge	0
Fraction CSP3	0.98
Exact Mass	1210.56
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: 162950916

Nmrshiftdb2: 70098257

No compound-protein relationship available.

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(C8OC9CCCCO9)OC(OCC1)CC1OC1CCCCO1

Level: 5

Mol. Weight: 859.11 g/mol

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

Level: 4

Mol. Weight: 758.99 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCC8)CC8OC(OCC9)CC9OC1CCCCO1

Level: 4

Mol. Weight: 758.99 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC(C3OC4CCCCO4)CCOC3OC5CCCOC5

Level: 4

Mol. Weight: 486.6 g/mol

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

Level: 3

Mol. Weight: 658.87 g/mol

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

Level: 3

Mol. Weight: 658.87 g/mol

SMILES: O1CCCCC1OC2C(OC3CCCCO3)CCOC2OC4CCCOC4

Level: 3

Mol. Weight: 386.49 g/mol

SMILES: O1CCCCC1OC(COCC2)C2OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 386.49 g/mol

SMILES: C1OCCCC1OC(OCC2)CC2OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 386.49 g/mol

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

Level: 2

Mol. Weight: 558.76 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCOCC3

Level: 2

Mol. Weight: 286.37 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 286.37 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 286.37 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 286.37 g/mol

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

Level: 1

Mol. Weight: 458.64 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 186.25 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 186.25 g/mol

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

Level: 0

Mol. Weight: 358.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.63
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 2796594779.44
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 365482011277.0

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.62
Plasma Protein Binding: 34.85
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: 1.15
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -8500283058.1
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -3471.13
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: -663332143353472.6
Rat (Acute): 4.13
Rat (Chronic Oral): 1422789.11
Fathead Minnow: 837315670200.34
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: 74606492567981.62
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -41473755.28
Log(P): -4829.91
Log S: -1.49
Log(Vapor Pressure): -2456753574700.92
Melting Point: -743476.0
pKa Acid: -17901325891.94
pKa Basic: -144015621.78

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9317
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9317
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9101
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9101
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8866
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8866
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.8816
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.8816
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8777
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8777
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8658
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8658
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8563
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8563
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8386
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8386
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7854
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7854
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7808
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7808
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7745
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7745
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7734
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7734
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7664
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7664
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7516
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7516
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7363
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7363
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7350
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7350
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7328
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7328
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7309
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7309
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7302
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7302
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7294
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7294
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7230
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7230
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	4	0.7224
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	4	0.7224
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7200
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7200
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7114
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7114
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7093
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7093
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7041
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7041

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