3beta,16beta,23-trihydroxy-13,28-epoxyolean-11-ene 3-O-beta-D-glucopyranosyl-(1→2)-beta-D- glucopyranosyl-(1→3)-beta-D-fucopyranoside - Compound Card

3beta,16beta,23-trihydroxy-13,28-epoxyolean-11-ene 3-O-beta-D-glucopyranosyl-(1→2)-beta-D- glucopyranosyl-(1→3)-beta-D-fucopyranoside

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3beta,16beta,23-trihydroxy-13,28-epoxyolean-11-ene 3-O-beta-D-glucopyranosyl-(1→2)-beta-D- glucopyranosyl-(1→3)-beta-D-fucopyranoside

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Saikosaponin

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O[C@@H]([C@@H]2O)C)O[C@H]2CC[C@]3(C([C@]2(C)CO)CC[C@@]2(C3C=C[C@]34[C@@]2(C)C[C@@H]([C@@]2(C4CC(C)(C)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C48H78O18/c1-22-30(53)37(65-41-38(34(57)32(55)24(19-50)63-41)66-39-35(58)33(56)31(54)23(18-49)62-39)36(59)40(61-22)64-29-10-11-43(4)25(44(29,5)20-51)8-12-45(6)26(43)9-13-48-27-16-42(2,3)14-15-47(27,21-60-48)28(52)17-46(45,48)7/h9,13,22-41,49-59H,8,10-12,14-21H2,1-7H3/t22-,23-,24-,25?,26?,27?,28+,29+,30+,31-,32-,33+,34+,35-,36-,37+,38-,39+,40+,41+,43+,44+,45-,46+,47-,48+/m1/s1
InChIKey	NXWBRHQQKIQDCN-UXKPDXCRSA-N
Formula	C₄₈H₇₈O₁₈
HBA	18
HBD	11
MW	943.13
Rotatable Bonds	9
TPSA	287.14
LogP	-0.4
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	66
Formal Charge	0
Fraction CSP3	0.96
Exact Mass	942.52
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bupleurum spinosum	Apiaceae	Plantae	199135

Showing of synonyms

Barrero AF, Haïdour A, et al. (2000). Saikosaponins from roots of Bupleurum gibraltaricum and Bupleurum spinosum. Phytochemistry,2000,54(8),741-745. [View] [PubMed]

Pubchem: 46905099

Chembl: CHEMBL1159435

No compound-protein relationship available.

SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC(OCC7)CC7OC(OCCC8)C8OC9CCCCO9

Level: 3

Mol. Weight: 943.13 g/mol

SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC(OCC7)CC7OC8CCCCO8

Level: 2

Mol. Weight: 943.13 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCOCC3

Level: 2

Mol. Weight: 943.13 g/mol

SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 943.13 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 943.13 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 943.13 g/mol

SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 943.13 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 943.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 4402.620
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 576240.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.810
Plasma Protein Binding: 81.3
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: 0.550
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 117624938.310
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -48.250
Log(P): 1.71
Log S: -2.5
Log(Vapor Pressure): -3873157.37
Melting Point: 210.43
pKa Acid: -28135.72
pKa Basic: -200.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7508
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7508