3-O-beta-D-galactopyranosyl-(1→2)-beta-D-glucurunopyranosyl machaerinic acid 28-O-beta-D-glucopyranosyl ester - Compound Card

3-O-beta-D-galactopyranosyl-(1→2)-beta-D-glucurunopyranosyl machaerinic acid 28-O-beta-D-glucopyranosyl ester

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3-O-beta-D-galactopyranosyl-(1→2)-beta-D-glucurunopyranosyl machaerinic acid 28-O-beta-D-glucopyranosyl ester

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Triterpenoid Saponin

Canonical Smiles	OCC1O[C@@H](O[C@@H]2[C@@H](OC([C@H](C2O)O)C(=O)O)O[C@H]2CC[C@]3(C(C2(C)C)CC[C@@]2(C3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)[C@H](C2)O)C(=O)O[C@@H]2OC(CO)[C@H](C([C@@H]2O)O)O)C)C)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C48H76O20/c1-43(2)16-21-20-8-9-25-45(5)12-11-27(65-41-37(33(57)32(56)36(66-41)38(60)61)67-39-34(58)30(54)28(52)22(18-49)63-39)44(3,4)24(45)10-13-47(25,7)46(20,6)14-15-48(21,17-26(43)51)42(62)68-40-35(59)31(55)29(53)23(19-50)64-40/h8,21-37,39-41,49-59H,9-19H2,1-7H3,(H,60,61)/t21-,22?,23?,24?,25?,26-,27-,28+,29+,30?,31?,32-,33?,34-,35-,36?,37-,39-,40-,41+,45-,46+,47+,48+/m0/s1
InChIKey	ZSSXPARXBNPCIS-WJDHKHCDSA-N
Formula	C₄₈H₇₆O₂₀
HBA	19
HBD	12
MW	973.12
Rotatable Bonds	9
TPSA	332.28
LogP	-0.8
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	68
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	972.49
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Calendula stellata	Asteraceae	Plantae	1565984

Showing of synonyms

Lehbili M, Alabdul Magid A, et al. (2017). Oleanane-type triterpene saponins from Calendula stellata. Phytochemistry, 2017, 144, 33-42. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 973.12 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 973.12 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 973.12 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 973.12 g/mol

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

Level: 1

Mol. Weight: 973.12 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 973.12 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)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): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 6239.01
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 816266.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 81.66
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: 0.55
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 166620601.03
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -78.38
Log(P): 1.0
Log S: -2.07
Log(Vapor Pressure): -5486585.58
Melting Point: 281.83
pKa Acid: -39892.62
pKa Basic: -295.62

No predicted protein targets found for this compound.