3-O-[alpha-L-rhamnopyranosyl (1→4)-beta-D-glucopyranosyl]echinocystic acid 28-O-beta-D-glucopyranosyl ester - Compound Card

3-O-[alpha-L-rhamnopyranosyl (1→4)-beta-D-glucopyranosyl]echinocystic acid 28-O-beta-D-glucopyranosyl ester

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3-O-[alpha-L-rhamnopyranosyl (1→4)-beta-D-glucopyranosyl]echinocystic acid 28-O-beta-D-glucopyranosyl ester

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Saponin
- Subclass: Triterpenoid Saponin

Canonical Smiles	OCC1OC(O[C@H]2CC[C@]3(C(C2(C)C)CC[C@@]2(C3CC=C3[C@]2(C)C[C@H](C2C3CC(C)(C)C[C@H]2C(=O)OC2OC(CO)C(C(C2O)O)O)O)C)C)C(C(C1OC1OC(C)C(C(C1O)O)O)O)O
InChI	InChI=1S/C48H78O18/c1-20-31(52)33(54)36(57)41(61-20)65-39-26(19-50)63-42(38(59)35(39)56)64-29-12-13-46(6)27(45(29,4)5)11-14-47(7)28(46)10-9-23-21-15-44(2,3)16-22(30(21)24(51)17-48(23,47)8)40(60)66-43-37(58)34(55)32(53)25(18-49)62-43/h9,20-22,24-39,41-43,49-59H,10-19H2,1-8H3/t20?,21?,22-,24-,25?,26?,27?,28?,29+,30?,31?,32?,33?,34?,35?,36?,37?,38?,39?,41?,42?,43?,46+,47-,48+/m1/s1
InChIKey	RDVKOHQLZFWWSQ-GFKZTCJOSA-N
Formula	C₄₈H₇₈O₁₈
HBA	18
HBD	11
MW	943.13
Rotatable Bonds	8
TPSA	294.98
LogP	-0.01
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	66
Formal Charge	0
Fraction CSP3	0.94
Exact Mass	942.52
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bupleurum lancifolium	Umbelliferae	Plantae	198842

Showing of synonyms

Achouri A, Derbré S, et al. (2017). Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae). Natural Product Research, 2017,31(19),2286–2292. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC(C3=4)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 943.13 g/mol

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC(C3=4)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 943.13 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 2

Mol. Weight: 943.13 g/mol

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC(C3=4)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 943.13 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 943.13 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 943.13 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

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): -6.56
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 2568.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 336525.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.84
Plasma Protein Binding: 38.15
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: 1.24
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 68691363.92
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -22.7
Log(P): 1.95
Log S: -2.61
Log(Vapor Pressure): -2261848.36
Melting Point: 272.6
pKa Acid: -16392.01
pKa Basic: -105.57

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8796
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.8102