7-O-(E-caffeoyl)-sylvestroside I - Compound Card

7-O-(E-caffeoyl)-sylvestroside I

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7-O-(E-caffeoyl)-sylvestroside I

Structure
Zoomed Structure
  • Family: Plantae - Caprifoliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Bisiridoid
Canonical Smiles C=C[C@H]1[C@@H](OC=C(C1CCOC(=O)/C=C/c1ccc(c(c1)O)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/C42H54O22/c1-4-19-20(9-10-57-29(47)8-6-18-5-7-24(45)25(46)11-18)22(15-58-39(19)63-41-35(52)33(50)31(48)27(13-43)61-41)38(55)60-26-12-21-23(37(54)56-3)16-59-40(30(21)17(26)2)64-42-36(53)34(51)32(49)28(14-44)62-42/h4-8,11,15-17,19-21,26-28,30-36,39-46,48-53H,1,9-10,12-14H2,2-3H3/b8-6+/t17-,19+,20?,21?,26-,27?,28?,30?,31+,32+,33-,34-,35?,36?,39-,40-,41-,42-/m0/s1
InChIKey GBJKWGZKAQIMJY-BMVVEPAVSA-N
Formula C42H54O22
HBA 22
HBD 10
MW 910.87
Rotatable Bonds 15
TPSA 336.58
LogP -2.07
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 64
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 910.31
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.

Structure

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

Level: 4

Mol. Weight: 910.87 g/mol

Structure

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

Level: 3

Mol. Weight: 910.87 g/mol

Structure

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

Level: 3

Mol. Weight: 910.87 g/mol

Structure

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

Level: 3

Mol. Weight: 910.87 g/mol

Structure

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

Level: 2

Mol. Weight: 910.87 g/mol

Structure

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

Level: 2

Mol. Weight: 910.87 g/mol

Structure

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

Level: 2

Mol. Weight: 910.87 g/mol

Structure

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

Level: 2

Mol. Weight: 910.87 g/mol

Structure

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

Level: 1

Mol. Weight: 910.87 g/mol

Structure

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

Level: 1

Mol. Weight: 910.87 g/mol

Structure

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

Level: 1

Mol. Weight: 910.87 g/mol

Structure

SMILES: O1C=CCCC1OC2CCCCO2

Level: 1

Mol. Weight: 910.87 g/mol

Structure

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 910.87 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 910.87 g/mol

Structure

SMILES: C1=COCCC1

Level: 0

Mol. Weight: 910.87 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 910.87 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
1748.97
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
229371.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
49.45
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
5.56
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-5331.88
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
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
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-416298769.79
Rat (Acute)
3.06
Rat (Chronic Oral)
5.61
Fathead Minnow
525497.07
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
46815681.5
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-12.19
Log(P)
0.41
Log S
-3.02
Log(Vapor Pressure)
-1541528.41
Melting Point
205.61
pKa Acid
-11153.57
pKa Basic
-66.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9359
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9064
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9060
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8934
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8875
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8684
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8563
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8497
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8485
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8453
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8346
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8258
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8219
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8164
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8101
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8073
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8054
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7999
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7927
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7862
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7818
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7808
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7800
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7766
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7721
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7694
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7694
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7634
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7605
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7597
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7520
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7493
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7471
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7414
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7345
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7325
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7307
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7288
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7284
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7278
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7217
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7216
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7212
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7205
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7198
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7193
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7184
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7181
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7179
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7168
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7167
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7165
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7157
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7156
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7135
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7130
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7122
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7120
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7117
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7113
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7112
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7098
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7084
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7068
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7066
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7057
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7051
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7046
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7045
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7041
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7022
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7020
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7019
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7016
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7009
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7001

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