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

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

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

Structure
Zoomed Structure
  • 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)O)O[C@@H]1OC[C@H](C([C@@H]1O)O)O)O)O)O
InChI InChI=1S/C50H80O24/c1-18-9-31(56)50(66-16-18)19(2)32-26(74-50)11-24-22-6-5-20-10-21(7-8-48(20,3)23(22)12-30(55)49(24,32)4)67-45-40(64)37(61)41(29(15-53)70-45)71-47-43(73-46-39(63)36(60)34(58)27(13-51)68-46)42(35(59)28(14-52)69-47)72-44-38(62)33(57)25(54)17-65-44/h18-29,31-47,51-54,56-64H,5-17H2,1-4H3/t18-,19+,20?,21+,22?,23?,24?,25-,26?,27?,28?,29?,31+,32?,33?,34-,35-,36?,37?,38+,39+,40+,41+,42?,43+,44+,45-,46+,47+,48+,49-,50?/m1/s1
InChIKey IAVKEJWSSFYUBV-CFKPLKNDSA-N
Formula C50H80O24
HBA 24
HBD 13
MW 1065.17
Rotatable Bonds 11
TPSA 372.36
LogP -4.12
Number Rings 10
Number Aromatic Rings 0
Heavy Atom Count 74
Formal Charge 0
Fraction CSP3 0.98
Exact Mass 1064.5
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: 162817620
Nmrshiftdb2: 70098256

No compound-protein relationship available.

Structure

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

Level: 4

Mol. Weight: 1065.17 g/mol

Structure

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

Level: 3

Mol. Weight: 1065.17 g/mol

Structure

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

Level: 3

Mol. Weight: 1065.17 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)CCOC2OC4CCCOC4

Level: 3

Mol. Weight: 1065.17 g/mol

Structure

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

Level: 2

Mol. Weight: 1065.17 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1065.17 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1065.17 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1065.17 g/mol

Structure

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

Level: 1

Mol. Weight: 1065.17 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1065.17 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1065.17 g/mol

Structure

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

Level: 0

Mol. Weight: 1065.17 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1065.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
381729.39
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
49888437.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
41.5
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
0.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-1160283.76
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.37
Liver Injury II
Safe
hERG Blockers
Safe
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
-90545113567.8
Rat (Acute)
3.9
Rat (Chronic Oral)
193.46
Fathead Minnow
114294034.71
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
10183809226.43
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-5654.55
Log(P)
-1.96
Log S
-1.71
Log(Vapor Pressure)
-335347551.05
Melting Point
185.15
pKa Acid
-2443446.93
pKa Basic
-19643.84
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 3 0.8480
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8480
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8474
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8474
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7731
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7731
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7720
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7720
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7619
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7619
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7489
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7489
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7153
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7153
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7087
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7087
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7018
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7018
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7002
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7002

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