3beta,16alpha,23,28-tetrahydroxyoleana-11,13(18)-dien-30-oic acid 3-O-beta-D-glucopyranosyl-(1→2)-beta-D-glucopyranosyl-(1→3)-beta-D-fucopyranoside - Compound Card

3beta,16alpha,23,28-tetrahydroxyoleana-11,13(18)-dien-30-oic acid 3-O-beta-D-glucopyranosyl-(1→2)-beta-D-glucopyranosyl-(1→3)-beta-D-fucopyranoside

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3beta,16alpha,23,28-tetrahydroxyoleana-11,13(18)-dien-30-oic acid 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=CC3=C4C[C@](C)(CC[C@@]4([C@@H](C[C@@]23C)O)CO)C(=O)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/C48H76O20/c1-21-30(54)37(67-41-38(34(58)32(56)25(18-50)65-41)68-39-35(59)33(57)31(55)24(17-49)64-39)36(60)40(63-21)66-29-10-11-44(3)26(45(29,4)19-51)9-12-46(5)27(44)8-7-22-23-15-43(2,42(61)62)13-14-48(23,20-52)28(53)16-47(22,46)6/h7-8,21,24-41,49-60H,9-20H2,1-6H3,(H,61,62)/t21-,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	JABXAGIYFFXHDD-AIJDJSTBSA-N
Formula	C₄₈H₇₆O₂₀
HBA	19
HBD	13
MW	973.12
Rotatable Bonds	11
TPSA	335.44
LogP	-1.43
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	68
Formal Charge	0
Fraction CSP3	0.9
Exact Mass	972.49
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: 162874141

Nmrshiftdb2: 60045925

No compound-protein relationship available.

SMILES: C1CCCC(C1=C23)CCC3C4C(C=C2)C5C(CC4)CC(CC5)OC(OCC6)CC6OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 973.12 g/mol

SMILES: C1CCCC(C1=C23)CCC3C4C(C=C2)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 973.12 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCOCC3

Level: 2

Mol. Weight: 973.12 g/mol

SMILES: C1CCCC(C1=C23)CCC3C4C(C=C2)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 973.12 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 973.12 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 973.12 g/mol

SMILES: C1CCCC(C1=C23)CCC3C4C(C=C2)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 973.12 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 973.12 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.42
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 8027.700
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1050044.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.920
Plasma Protein Binding: 76.13
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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 1.080
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 214342414.240
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -107.210
Log(P): -0.01
Log S: -1.82
Log(Vapor Pressure): -7058019.94
Melting Point: 231.94
pKa Acid: -51342.74
pKa Basic: -391.71

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7521
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7521