6-O-alpha-l-(3”-O-trans-caffeoyl) rhamnopyranosylcatalpol - Compound Card

6-O-alpha-l-(3”-O-trans-caffeoyl) rhamnopyranosylcatalpol

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6-O-alpha-l-(3”-O-trans-caffeoyl) rhamnopyranosylcatalpol

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](O[C@@H]2OC=CC3C2[C@@]2(CO)O[C@H]2[C@H]3O[C@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)OC(=O)/C=C/c2ccc(c(c2)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C30H38O17/c1-11-19(36)25(44-17(35)5-3-12-2-4-14(33)15(34)8-12)23(40)29(42-11)45-24-13-6-7-41-27(18(13)30(10-32)26(24)47-30)46-28-22(39)21(38)20(37)16(9-31)43-28/h2-8,11,13,16,18-29,31-34,36-40H,9-10H2,1H3/b5-3+/t11-,13?,16-,18?,19-,20-,21+,22-,23+,24+,25+,26+,27+,28+,29-,30-/m1/s1
InChIKey MFIJTASICGGFJA-VAFNCXQRSA-N
Formula C30H38O17
HBA 17
HBD 9
MW 670.62
Rotatable Bonds 9
TPSA 267.05
LogP -3.06
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 670.21
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Premna odorata Lamiaceae Plantae 1037421

Showing of synonyms

  • Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 670.62 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 670.62 g/mol

Structure

SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5

Level: 2

Mol. Weight: 670.62 g/mol

Structure

SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4

Level: 1

Mol. Weight: 670.62 g/mol

Structure

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 670.62 g/mol

Structure

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 670.62 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 670.62 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 670.62 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 670.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.22
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
105.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
42.53
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.970
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.390
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.510
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.480
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
-193740.910
Rat (Acute)
2.770
Rat (Chronic Oral)
4.430
Fathead Minnow
258.830
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
15754.800
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-1.820
Log(P)
-1.99
Log S
-2.22
Log(Vapor Pressure)
-528.25
Melting Point
168.13
pKa Acid
3.3
pKa Basic
2.18
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 0.9343
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9076
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8868
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8844
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8684
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8547
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8457
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8422
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8389
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8346
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8318
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8226
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8219
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8205
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8083
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8015
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7962
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7895
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7865
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7847
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7847
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7796
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7689
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7678
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7572
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7560
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7547
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7536
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7532
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7498
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7496
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7492
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7443
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7421
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7376
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7371
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7351
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7340
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7333
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7307
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7275
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7271
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7258
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7240
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7195
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7195
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7191
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7191
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7165
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7159
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7149
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7148
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7146
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7145
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7122
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7116
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7107
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7099
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7089
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7074
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7072
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7068
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7067
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7054
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7053
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7050
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7041
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7039
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7037
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7028
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7021
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7004

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