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3beta-hydroxyspirosta-5,25(27)-dien-1beta-yl-O-alpha-L-rhamnopyranosyl-(1→2)-O-[beta-D-xylopy ranosyl-(1→3)]-alpha-L-arabinopyranoside

Family: Plantae - Dracaenaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Steroidal Saponin

Canonical Smiles	C=C1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)[C@@H](C[C@@H](C3)O)O[C@@H]1OC[C@@H](C([C@@H]1O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O)O[C@@H]1OC[C@H](C([C@@H]1O)O)O)O)C
InChI	InChI=1S/C43H66O16/c1-18-8-11-43(54-15-18)19(2)30-28(59-43)14-25-23-7-6-21-12-22(44)13-29(42(21,5)24(23)9-10-41(25,30)4)56-40-37(58-39-35(51)33(49)31(47)20(3)55-39)36(27(46)17-53-40)57-38-34(50)32(48)26(45)16-52-38/h6,19-20,22-40,44-51H,1,7-17H2,2-5H3/t19-,20?,22+,23+,24-,25-,26+,27-,28-,29+,30-,31-,32?,33-,34-,35?,36?,37-,38-,39-,40-,41-,42-,43+/m0/s1
InChIKey	KRNSPGCTUAIFKQ-MOAFUGRNSA-N
Formula	C₄₃H₆₆O₁₆
HBA	16
HBD	8
MW	838.99
Rotatable Bonds	6
TPSA	235.68
LogP	0.38
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	59
Formal Charge	0
Fraction CSP3	0.91
Exact Mass	838.44
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.

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

Level: 3

Mol. Weight: 838.99 g/mol

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

Level: 2

Mol. Weight: 838.99 g/mol

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

Level: 2

Mol. Weight: 838.99 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 838.99 g/mol

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

Level: 1

Mol. Weight: 838.99 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 838.99 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 838.99 g/mol

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

Level: 0

Mol. Weight: 838.99 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 838.99 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.38
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 294.92
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 39315.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.8
Plasma Protein Binding: 80.47
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: 1.39
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -910.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.23
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.92
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -71355151.7
Rat (Acute): 3.95
Rat (Chronic Oral): 4.5
Fathead Minnow: 90076.47
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 8022448.09
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.89
Log(P): 2.17
Log S: -2.99
Log(Vapor Pressure): -264015.1
Melting Point: 228.24
pKa Acid: -1852.04
pKa Basic: 4.88

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7091
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7090

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