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7-O-(E-p-coumaroyl)-sylvestroside I

Family: Plantae - Caprifoliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Bisiridoid

Canonical Smiles	C=C[C@H]1[C@@H](OC=C([C@H]1CCOC(=O)/C=C/c1ccc(cc1)O)C(=O)O[C@H]1CC2C([C@H]1C)[C@@H](OC=C2C(=O)OC)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
InChI	InChI=1S/C42H54O21/c1-4-21-22(11-12-56-29(46)10-7-19-5-8-20(45)9-6-19)24(16-57-39(21)62-41-35(51)33(49)31(47)27(14-43)60-41)38(54)59-26-13-23-25(37(53)55-3)17-58-40(30(23)18(26)2)63-42-36(52)34(50)32(48)28(15-44)61-42/h4-10,16-18,21-23,26-28,30-36,39-45,47-52H,1,11-15H2,2-3H3/b10-7+/t18-,21+,22-,23?,26-,27?,28?,30?,31+,32+,33-,34-,35?,36?,39-,40-,41-,42-/m0/s1
InChIKey	QVALXQYGODNJSU-XVSCINMWSA-N
Formula	C₄₂H₅₄O₂₁
HBA	21
HBD	9
MW	894.87
Rotatable Bonds	15
TPSA	316.35
LogP	-1.77
Number Rings	6
Number Aromatic Rings	1
Heavy Atom Count	63
Formal Charge	0
Fraction CSP3	0.6
Exact Mass	894.32
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Scabiosa stellata	Caprifoliaceae	Plantae	596806

Showing of synonyms

Lehbili M, Alabdul Magid A, et al. (2018). Two new bis-iridoids isolated from Scabiosa stellata and their antibacterial, antioxidant, anti-tyrosinase and cytotoxic activities. Fitoterapia, 2018, 125, 41-48. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCCC2CC(OC3CCCCO3)OC=C2C(=O)OC(C4)CC(C45)C(OC=C5)OC6CCCCO6

Level: 4

Mol. Weight: 894.87 g/mol

SMILES: c1ccccc1C=CC(=O)OCCC2CCOC=C2C(=O)OC(C3)CC(C34)C(OC=C4)OC5CCCCO5

Level: 3

Mol. Weight: 894.87 g/mol

SMILES: c1ccccc1C=CC(=O)OCCC2CC(OC3CCCCO3)OC=C2C(=O)OC(C4)CC(C45)COC=C5

Level: 3

Mol. Weight: 894.87 g/mol

SMILES: O1CCCCC1OC(CC2)OC=C2C(=O)OC(C3)CC(C34)C(OC=C4)OC5CCCCO5

Level: 3

Mol. Weight: 894.87 g/mol

SMILES: c1ccccc1C=CC(=O)OCCC2CCOC=C2C(=O)OC(C3)CC(C34)COC=C4

Level: 2

Mol. Weight: 894.87 g/mol

SMILES: c1ccccc1C=CC(=O)OCCC2C=COC(C2)OC3CCCCO3

Level: 2

Mol. Weight: 894.87 g/mol

SMILES: C1CCOC=C1C(=O)OC(C2)CC(C23)C(OC=C3)OC4CCCCO4

Level: 2

Mol. Weight: 894.87 g/mol

SMILES: C1=COCC(C12)CC(C2)OC(=O)C3=COC(CC3)OC4CCCCO4

Level: 2

Mol. Weight: 894.87 g/mol

SMILES: c1ccccc1C=CC(=O)OCCC2C=COCC2

Level: 1

Mol. Weight: 894.87 g/mol

SMILES: C1CCOC=C1C(=O)OC(C2)CC(C23)COC=C3

Level: 1

Mol. Weight: 894.87 g/mol

SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3

Level: 1

Mol. Weight: 894.87 g/mol

SMILES: O1C=CCCC1OC2CCCCO2

Level: 1

Mol. Weight: 894.87 g/mol

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 894.87 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 894.87 g/mol

SMILES: C1=COCCC1

Level: 0

Mol. Weight: 894.87 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 894.87 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.37
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1198.6
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 157420.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.69
Plasma Protein Binding: 58.78
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 5.56
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -3659.7
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.59
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.06
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -285711842.53
Rat (Acute): 3.38
Rat (Chronic Oral): 6.05
Fathead Minnow: 360658.84
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 32128761.65
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -4.23
Log(P): 0.57
Log S: -2.96
Log(Vapor Pressure): -1057880.88
Melting Point: 213.8
pKa Acid: -7629.85
pKa Basic: -38.61

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	0.9026
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8607
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8517
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8360
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8165
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8116
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7987
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7826
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7613
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7509
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7401
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.7386
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7372
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7334
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7303
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7282
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7257
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7245
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7231
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7210
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7205
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7189
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7186
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7184
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7155
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7150
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7123
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7093
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7090
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7070
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7067
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7058
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7050
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7049
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7048
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7043
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7043
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7027
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	2	0.7025
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7018
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7015
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7014
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7013
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7011
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7010
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7006
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7004

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