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Neohecogenin 3-O-beta-D-glucopyranosyl-(1→3)-[beta-D-xylopyranosyl-(1→3)-beta-D-xylopyranosyl-(1→2)]-beta-D-glucopyranosyl-(1→4)-beta-D-galacto-pyranoside

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

Canonical Smiles	OCC1O[C@@H](O[C@]2(O)C(CO)O[C@H]([C@H](C2O)O)OC2CCC3([C@H](C2)CCC2C3CC(=O)C3(C2CC2C3C(C)C3(O2)CCC(CO3)C)C)C)[C@H](C([C@H]1O)O[C@@H]1OC(CO)[C@@H](C([C@@H]1O)O)O)OC1OC[C@H]([C@@H]([C@H]1O)OC1OC[C@H]([C@@H]([C@H]1O)O)O)O
InChI	InChI=1S/C55H88O28/c1-20-7-10-54(74-17-20)21(2)34-29(82-54)12-26-24-6-5-22-11-23(8-9-52(22,3)25(24)13-32(61)53(26,34)4)75-50-42(69)46(70)55(71,33(16-58)78-50)83-51-45(44(37(64)31(15-57)77-51)80-49-40(67)38(65)36(63)30(14-56)76-49)81-48-41(68)43(28(60)19-73-48)79-47-39(66)35(62)27(59)18-72-47/h20-31,33-51,56-60,62-71H,5-19H2,1-4H3/t20?,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+/m0/s1
InChIKey	GHMRILAKANAPCR-UCJXFYMRSA-N
Formula	C₅₅H₈₈O₂₈
HBA	28
HBD	15
MW	1197.28
Rotatable Bonds	13
TPSA	431.28
LogP	-5.31
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 decipiens	Agavaceae	Plantae	2695036

Showing of synonyms

Abdel-Gawad MM, El-Sayed MM and Abdel-Hameed ES. (1999). Molluscicidal steroidal saponins and lipid content of Agave decipiens. Fitoterapia,1999,70,371-381. [View]

Pubchem: 162913874

Nmrshiftdb2: 60019328

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

Molluscicidal

Absorption

Caco-2 (logPapp): -6.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 186058499.8
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 24315670387.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.64
Plasma Protein Binding: 21.29
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: 0.62
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -565527426.61
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -231.09
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: -44131771792167.08
Rat (Acute): 4.14
Rat (Chronic Oral): 94657.91
Fathead Minnow: 55706961411.87
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: 4963600585848.18
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -2759261.28
Log(P): -322.57
Log S: -1.41
Log(Vapor Pressure): -163448842200.22
Melting Point: -46568.07
pKa Acid: -1190983103.76
pKa Basic: -9581406.32

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8465
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8465
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7952
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7952
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7920
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7920
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7854
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7854
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7752
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7752
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7741
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7741
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7660
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7660
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7648
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7648
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
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7554
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7554
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7486
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7486
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7445
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7445
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7393
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7393
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7393
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7393
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7392
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7392
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7340
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7340
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7162
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7162
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7149
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7149
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7148
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7148
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7126
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7126
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7124
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7124
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7115
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7115
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7083
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7083
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7060
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7060

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