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Calendulagycoside B 6′-O-n-butyl ester

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Saponin

Canonical Smiles	CCCCOC(=O)[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@H]1O[C@@H](CO)[C@H]([C@H]([C@@H]1O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C52H84O19/c1-9-10-21-65-42(62)40-38(61)39(69-43-36(59)34(57)32(55)27(23-53)66-43)41(71-44-37(60)35(58)33(56)28(24-54)67-44)45(70-40)68-31-14-15-49(6)29(48(31,4)5)13-16-51(8)30(49)12-11-25-26-22-47(2,3)17-19-52(26,46(63)64)20-18-50(25,51)7/h11,26-41,43-45,53-61H,9-10,12-24H2,1-8H3,(H,63,64)/t26-,27-,28+,29-,30+,31-,32+,33+,34+,35-,36-,37+,38-,39-,40-,41+,43+,44-,45+,49-,50+,51+,52-/m0/s1
InChIKey	ZVBYEOQPQROTOB-GSBQBKAVSA-N
Formula	C₅₂H₈₄O₁₉
HBA	18
HBD	10
MW	1013.23
Rotatable Bonds	13
TPSA	301.05
LogP	2.06
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	71
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	1012.56
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Calendula officinalis	Asteraceae	Plantae	41496

Showing of synonyms

Ukiya M, Akihisa T, et al. (2006). Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of Marigold (Calendula officinalis) flowers. Journal of Natural Products,2006,69,1692-1696. [View] [PubMed]

Pubchem: 163102910

Nmrshiftdb2: 70067426

No compound-protein relationship available.

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6OCCC(OC7CCCCO7)C6OC8CCCCO8

Level: 3

Mol. Weight: 1013.23 g/mol

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

Level: 2

Mol. Weight: 1013.23 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 1013.23 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1013.23 g/mol

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

Level: 1

Mol. Weight: 1013.23 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1013.23 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1013.23 g/mol

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

Level: 0

Mol. Weight: 1013.23 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1013.23 g/mol

Anti-inflammatory

Antitumor promoting

Absorption

Caco-2 (logPapp): -6.17
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 29886.27
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 3906675.71

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.0
Plasma Protein Binding: 90.38
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: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 1.5
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -90853.35
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.51
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -7090425614.23
Rat (Acute): 3.13
Rat (Chronic Oral): 15.83
Fathead Minnow: 8950161.07
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 797471344.6
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -427.83
Log(P): 4.34
Log S: -2.61
Log(Vapor Pressure): -26260181.56
Melting Point: 203.6
pKa Acid: -191265.83
pKa Basic: -1516.04

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8872
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8872

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