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22-O-methyl capsicoside D

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Saponin

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2C[C@H]2[C@@H]3[C@H](C)C(O2)(OC)CC[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)C)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)O)O)O
InChI	InChI=1S/C63H106O33/c1-23(21-84-55-47(79)43(75)39(71)32(16-64)87-55)8-13-63(83-5)24(2)37-31(96-63)15-29-27-7-6-25-14-26(9-11-61(25,3)28(27)10-12-62(29,37)4)86-57-49(81)45(77)51(36(20-68)91-57)92-60-54(53(42(74)35(19-67)90-60)94-56-46(78)38(70)30(69)22-85-56)95-59-50(82)52(41(73)34(18-66)89-59)93-58-48(80)44(76)40(72)33(17-65)88-58/h23-60,64-82H,6-22H2,1-5H3/t23-,24+,25+,26+,27-,28+,29+,30-,31+,32-,33-,34-,35-,36-,37+,38+,39-,40-,41-,42-,43+,44+,45-,46-,47-,48-,49-,50-,51+,52+,53+,54-,55-,56+,57-,58+,59+,60+,61+,62+,63?/m1/s1
InChIKey	BOGJTFPGODXYAG-UPIICVHQSA-N
Formula	C₆₃H₁₀₆O₃₃
HBA	33
HBD	19
MW	1391.51
Rotatable Bonds	22
TPSA	513.59
LogP	-7.01
Number Rings	11
Number Aromatic Rings	0
Heavy Atom Count	96
Formal Charge	0
Fraction CSP3	1.0
Exact Mass	1390.66
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cestrum parqui	Solanaceae	Plantae	142762

Showing of synonyms

Mosad R, Ali M, et al. (2017). New cytotoxic steroidal saponins from Cestrum parqui. Phytochemistry Letters, 2017, 22, 167-173. [View]

Pubchem: 76316014

Nmrshiftdb2: 70051095

Chembl: CHEMBL2271375

No compound-protein relationship available.

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(OC9CCCCO9)C8OC(OCC1)CC1OC1CCCCO1

Level: 6

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(OC9CCCCO9)C8OC1CCCCO1

Level: 5

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7OCCC(OC8CCCCO8)C7OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCC8)CC8OC9CCCCO9

Level: 4

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7OCCC(OC8CCCCO8)C7OC9CCCCO9

Level: 4

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC(OCCC7)C7OC(OCC8)CC8OC9CCCCO9

Level: 4

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3C(OC4CCCCO4)CCOC3OC5CCCOC5

Level: 4

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC(OCC7)CC7OC8CCCCO8

Level: 3

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OC2C(OC3CCCCO3)CCOC2OC4CCCOC4

Level: 3

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1391.51 g/mol

SMILES: C1OCCCC1OC(OCCC2)C2OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 2

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1391.51 g/mol

SMILES: O1CCCCC1OCCCCC(C2)OC3CC(C4C23)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 1391.51 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1391.51 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1391.51 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 1391.51 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1391.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 9011867043391078.000
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1177745874669782500

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.550
Plasma Protein Binding: 46.89
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: 1.710
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -27391706962155704.000
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -11184356667.590
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2137551930065624760320.000
Rat (Acute): 1723768.960
Rat (Chronic Oral): 4584862355133.090
Fathead Minnow: 2698205090986915840.000
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 240415368271026192384.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -133646960133305.000
Log(P): -15558081236.35
Log S: -1.46
Log(Vapor Pressure): -7916755795726611000
Melting Point: -2405618095932.17
pKa Acid: -57686048447317900
pKa Basic: -464082473216469.75

No predicted protein targets found for this compound.

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