1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-beta-D-glucopyranosyl-4,6-di-O-alpha-L-rhamnopyranoside - Compound Card

1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-beta-D-glucopyranosyl-4,6-di-O-alpha-L-rhamnopyranoside

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1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-beta-D-glucopyranosyl-4,6-di-O-alpha-L-rhamnopyranoside

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Anthaquinone
- Subclass: Anthraquinone Glycoside

Canonical Smiles	OC[C@@H]1O[C@H](Oc2cc(C)c(c3c2C(=O)c2c(O)cc(cc2C3=O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C33H40O19/c1-8-4-14(50-33-29(46)26(43)22(39)15(7-34)51-33)17-18(30(8)52-32-28(45)25(42)20(37)10(3)48-32)21(38)12-5-11(6-13(35)16(12)23(17)40)49-31-27(44)24(41)19(36)9(2)47-31/h4-6,9-10,15,19-20,22,24-29,31-37,39,41-46H,7H2,1-3H3/t9-,10-,15-,19-,20-,22-,24+,25+,26+,27+,28+,29-,31-,32-,33-/m0/s1
InChIKey	OCPCKNTWRYVABH-QGYCMPFZSA-N
Formula	C₃₃H₄₀O₁₉
HBA	19
HBD	11
MW	740.66
Rotatable Bonds	7
TPSA	312.05
LogP	-3.93
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.58
Exact Mass	740.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhamnus alaternus	Rhamnaceae	Plantae	280017

Showing of synonyms

Ben Ammar R, Miyamoto T, et al. (2019). Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity. Natural product research,2019, 33(2), 280-286. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1Oc2ccc(OC3CCCCO3)c(c24)C(=O)c5c(C4=O)cc(cc5)OC6CCCCO6

Level: 3

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(C2=O)c1C(=O)c(c23)c(OC4CCCCO4)ccc3OC5CCCCO5

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1Oc2cccc(c23)C(=O)c4c(C3=O)ccc(c4)OC5CCCCO5

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1Oc2cccc(c23)C(=O)c4c(C3=O)cc(cc4)OC5CCCCO5

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.53
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -1.880
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 528.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.690
Plasma Protein Binding: 69.75
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.020
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 100873.230
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1.190
Log(P): -0.97
Log S: -3.52
Log(Vapor Pressure): -3306.09
Melting Point: 253.25
pKa Acid: -3.58
pKa Basic: 3.19

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7058