(23S,24S)-3-beta-23-dihydroxy-1-beta-[O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1→2)-O-[beta-D-xylopyranosyl-(1→3)]-alpha-L-arabinopyranosyl) oxy]spirosta-5,25(27)-dien-24-yl-beta-D-fucopyranoside - Compound Card

(23S,24S)-3-beta-23-dihydroxy-1-beta-[O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1→2)-O-[beta-D-xylopyranosyl-(1→3)]-alpha-L-arabinopyranosyl) oxy]spirosta-5,25(27)-dien-24-yl-beta-D-fucopyranoside

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(23S,24S)-3-beta-23-dihydroxy-1-beta-[O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1→2)-O-[beta-D-xylopyranosyl-(1→3)]-alpha-L-arabinopyranosyl) oxy]spirosta-5,25(27)-dien-24-yl-beta-D-fucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Dracaenaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Saponin
Canonical Smiles CC(=O)OC1[C@H](O[C@@H]2[C@@H](OC[C@@H](C2O[C@@H]2OC[C@H](C([C@@H]2O)O)O)O)O[C@@H]2C[C@H](O)CC3=CC[C@@H]4[C@@H]([C@@]23C)CC[C@]2([C@H]4C[C@H]3[C@@H]2[C@H](C)[C@@]2(O3)OCC(=C)C(C2O)O[C@@H]2O[C@H](C)[C@@H]([C@@H]([C@H]2O)O)O)C)OC([C@@H]([C@@H]1OC(=O)C)OC(=O)C)C
InChI InChI=1S/C55H82O25/c1-20-17-70-55(48(67)42(20)77-50-41(66)39(64)37(62)22(3)71-50)21(2)36-34(80-55)16-31-29-11-10-27-14-28(59)15-35(54(27,9)30(29)12-13-53(31,36)8)76-51-46(44(33(61)19-69-51)78-49-40(65)38(63)32(60)18-68-49)79-52-47(75-26(7)58)45(74-25(6)57)43(23(4)72-52)73-24(5)56/h10,21-23,28-52,59-67H,1,11-19H2,2-9H3/t21-,22+,23?,28+,29+,30-,31-,32+,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 HZKLFYZYQUFAMX-MKXKKFPMSA-N
Formula C55H82O25
HBA 25
HBD 9
MW 1143.24
Rotatable Bonds 11
TPSA 353.27
LogP -1.11
Number Rings 10
Number Aromatic Rings 0
Heavy Atom Count 80
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 1142.51
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Sansevieria trifasciata Dracaenaceae Plantae 39534

Showing of synonyms

  • Teponno RB, Tanaka C, et al. (2016). Trifasciatosides A-J, Steroidal Saponins from Sansevieria trifasciata.. Chemical & pharmaceutical bulletin,2016, 64(9), 1347-1355. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(C(=C)CO2)CC23CC4C5C(CC4O3)C6C(CC5)C7C(=CC6)CCCC7OC8OCCC(OC9CCCCO9)C8OC1CCCCO1

Level: 4

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CCCCC1OC(C(=C)CO2)CC23CC4C5C(CC4O3)C6C(CC5)C7C(=CC6)CCCC7OC(OCCC8)C8OC9CCCCO9

Level: 3

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CCCCC1OC(C(=C)CO2)CC23CC4C5C(CC4O3)C6C(CC5)C7C(=CC6)CCCC7OC(OCC8)CC8OC9CCCCO9

Level: 3

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CC(=C)CCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6OC7OCCC(OC8CCCCO8)C7OC9CCCCO9

Level: 3

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CCCCC1OC(C(=C)CO2)CC23CC4C5C(CC4O3)C6C(CC5)C7C(=CC6)CCCC7OC8CCCCO8

Level: 2

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CC(=C)CCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6OC(OCCC7)C7OC8CCCCO8

Level: 2

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CC(=C)CCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6OC(OCC7)CC7OC8CCCCO8

Level: 2

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CCCCC1OC(C(=C)CO2)CC23CC4C5C(CC4O3)C6C(CC5)C7C(=CC6)CCCC7

Level: 1

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CC(=C)CCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6OC7CCCCO7

Level: 1

Mol. Weight: 1143.24 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1143.24 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1143.24 g/mol

Structure

SMILES: O1CC(=C)CCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6

Level: 0

Mol. Weight: 1143.24 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1143.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.13
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
5269488.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
688661453.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
74.71
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-16016703.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-7.54
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
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1249887336663.33
Rat (Acute)
4.46
Rat (Chronic Oral)
2682.88
Fathead Minnow
1577715707.91
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
140577663217.93
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-78131.15
Log(P)
-7.88
Log S
-3.02
Log(Vapor Pressure)
-4629152350.07
Melting Point
-35.55
pKa Acid
-33730576.86
pKa Basic
-271352.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7707

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