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Dorycnic acid
- Family: Plantae - Convolvulaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Acid
| Canonical Smiles | CCCCO[C@@H]1[C@H](OC(=O)/C=C/c2ccc(c(c2)O)O)C[C@@]1(O)[C@@H](CC(=O)O)O |
|---|---|
| InChI | InChI=1S/C20H26O9/c1-2-3-8-28-19-15(11-20(19,27)16(23)10-17(24)25)29-18(26)7-5-12-4-6-13(21)14(22)9-12/h4-7,9,15-16,19,21-23,27H,2-3,8,10-11H2,1H3,(H,24,25)/b7-5+/t15-,16-,19-,20-/m1/s1 |
| InChIKey | JLQVVYXIVAEDIW-HBOIHNFSSA-N |
| Formula | C20H26O9 |
| HBA | 8 |
| HBD | 5 |
| MW | 410.42 |
| Rotatable Bonds | 10 |
| TPSA | 153.75 |
| LogP | 1.18 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 410.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Convolvulus dorycnium | Convolvulaceae | Plantae | 267580 |
Showing of synonyms
Dorycnic acid
- Nacef S, Jannet H, et al. (2010). Phenolic constituents of Convolvulus dorycnium L. flowers. Phytochemistry Letters, 2010, 3(2), 66-69. [View]
Pubchem:
162844177
No compound-protein relationship available.
SMILES: C1CCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 410.42 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 410.42 g/mol
SMILES: C1CCC1
Level: 0
Mol. Weight: 410.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.35
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.64
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -3.53
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.52
- Plasma Protein Binding
- 82.75
- 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
- 7.85
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.2
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.16
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.76
- 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
- -0.52
- Rat (Acute)
- 2.09
- Rat (Chronic Oral)
- 2.95
- Fathead Minnow
- 3.78
- 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
- 454.3
- Hydration Free Energy
- -9.18
- Log(D) at pH=7.4
- -0.55
- Log(P)
- 1.16
- Log S
- -2.36
- Log(Vapor Pressure)
- -12.88
- Melting Point
- 170.47
- pKa Acid
- 4.13
- pKa Basic
- 6.31
| 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 | 0.9351 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9123 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9105 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9092 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9035 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8881 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.8781 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8685 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8684 |
| Mexicain | P84346 | MEX1_JACME | Jacaratia mexicana | 3 | 0.8680 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8655 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.8493 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8490 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.8424 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8373 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8366 |
| Aspartate carbamoyltransferase catalytic subunit | P0A786 | PYRB_ECOLI | Escherichia coli | 3 | 0.8345 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8342 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8307 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8265 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8262 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8231 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8213 |
| Bis(5'-adenosyl)-triphosphatase | P49789 | FHIT_HUMAN | Homo sapiens | 3 | 0.8191 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8187 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8132 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8082 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8056 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8050 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.8024 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8003 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7993 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7966 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7940 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7922 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7921 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 4 | 0.7918 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7898 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7789 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7786 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7774 |
| Ectonucleoside triphosphate diphosphohydrolase I | Q5ZUA2 | Q5ZUA2_LEGPH | Legionella pneumophila subsp. pneumophila | 3 | 0.7772 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7769 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7756 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7740 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7725 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7693 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7681 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7610 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7597 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7542 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7497 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7453 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7431 |
| Mitochondrial dynamics protein MIEF1 | Q9NQG6 | MID51_HUMAN | Homo sapiens | 3 | 0.7426 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7409 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7396 |
| Genome polyprotein | A0EKU1 | A0EKU1_9FLAV | Meaban virus | 3 | 0.7377 |
| Bifunctional hemolysin/adenylate cyclase | P0DKX7 | CYAA_BORPE | Bordetella pertussis | 3 | 0.7361 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7361 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7358 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7346 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7342 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7327 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7319 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7294 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7288 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7262 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7232 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7226 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7222 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7214 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7207 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7206 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7205 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7199 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7182 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7176 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7175 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7175 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7162 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7159 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7159 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7158 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7149 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7145 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7142 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7138 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7138 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7120 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7119 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7116 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7115 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7110 |
| Guanylate kinase | P15454 | KGUA_YEAST | Saccharomyces cerevisiae | 3 | 0.7104 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7102 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7100 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 4 | 0.7100 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7099 |
| Eukaryotic translation initiation factor 4E | P06730 | IF4E_HUMAN | Homo sapiens | 5 | 0.7094 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7085 |
| Eukaryotic translation initiation factor 4E type 3 | Q9DBB5 | IF4E3_MOUSE | Mus musculus | 3 | 0.7083 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7082 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7079 |
| [LysW]-aminoadipate kinase | O50147 | LYSZ_THET2 | Thermus thermophilus | 3 | 0.7077 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7071 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7066 |
| histone deacetylase | A5H660 | A5H660_SCHMA | Schistosoma mansoni | 3 | 0.7062 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7060 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7052 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7051 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7051 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7040 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7039 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7038 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7032 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7032 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 4 | 0.7028 |
| Eukaryotic translation initiation factor 4E-1 | P29557 | IF4E1_WHEAT | Triticum aestivum | 4 | 0.7019 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7017 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7013 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7003 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7001 |