Select a section from the left sidebar
7-hydroxy-labda-8(17),13(16),14-trien-19-yl-(E)-coumarate
- Family: Plantae - Araucariaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpene
| Canonical Smiles | C=CC(=C)CC[C@H]1C(=C)[C@@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)COC(=O)/C=C/c1ccc(cc1)O |
|---|---|
| InChI | InChI=1S/C29H38O4/c1-6-20(2)8-14-24-21(3)25(31)18-26-28(4,16-7-17-29(24,26)5)19-33-27(32)15-11-22-9-12-23(30)13-10-22/h6,9-13,15,24-26,30-31H,1-3,7-8,14,16-19H2,4-5H3/b15-11+/t24-,25-,26-,28+,29+/m0/s1 |
| InChIKey | QNRUJSRLFGSDSM-SLEPOLRFSA-N |
| Formula | C29H38O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 450.62 |
| Rotatable Bonds | 8 |
| TPSA | 66.76 |
| LogP | 6.22 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.48 |
| Exact Mass | 450.28 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Araucaria bidwillii | Araucariaceae | Plantae | 56993 |
Showing of synonyms
7-hydroxy-labda-8(17),13(16),14-trien-19-yl-(E)-coumarate
- Ebada S, Talaat A, et al. (2017). Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. Tetrahedron, 2017, 73(21), 3048-3055. [View]
Pubchem:
132504632
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OCC2CCCC(C23)CC(=C)CC3
Level: 1
Mol. Weight: 450.62 g/mol
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 450.62 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 450.62 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.62
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.61
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.23
- Plasma Protein Binding
- 96.83
- 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
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.49
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.47
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.03
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.01
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -81.07
- Rat (Acute)
- 3.27
- Rat (Chronic Oral)
- 2.58
- Fathead Minnow
- 4.27
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 469.63
- Hydration Free Energy
- -2.73
- Log(D) at pH=7.4
- 5.42
- Log(P)
- 6.07
- Log S
- -6.45
- Log(Vapor Pressure)
- -9.04
- Melting Point
- 135.95
- pKa Acid
- 9.9
- pKa Basic
- 4.78
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9249 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.9207 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8984 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8911 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8497 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8480 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8399 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8374 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.8284 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8248 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8185 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8165 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8135 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8016 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7983 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7871 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7870 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7867 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7804 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7775 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7734 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7680 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7527 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7518 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7514 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7491 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7470 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.7468 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7439 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7432 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7401 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7391 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7377 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7335 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7331 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7326 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7326 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7314 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7307 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7294 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7289 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7289 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7287 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7285 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7283 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7280 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7278 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7270 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7268 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7258 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7254 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7243 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7239 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7228 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7220 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7210 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7209 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7206 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7193 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7178 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7173 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7160 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7149 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7140 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7131 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7131 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7128 |
| RIO-type serine/threonine-protein kinase Rio1 | O28471 | RIO1_ARCFU | Archaeoglobus fulgidus | 2 | 0.7127 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7101 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7100 |
| Protein kinase C iota type | Q62074 | KPCI_MOUSE | Mus musculus | 2 | 0.7095 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7093 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7091 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 2 | 0.7081 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7078 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7076 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7074 |
| Ethylene receptor 1 | P49333 | ETR1_ARATH | Arabidopsis thaliana | 3 | 0.7072 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7070 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7069 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7061 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7059 |
| Phosphoglycerate kinase 1 | P00558 | PGK1_HUMAN | Homo sapiens | 3 | 0.7056 |
| Ribonuclease TTHA0252 | Q5SLP1 | RNSE_THET8 | Thermus thermophilus | 3 | 0.7054 |
| Succinyl-CoA:acetate CoA-transferase | B3EY95 | SCACT_ACEAC | Acetobacter aceti | 2 | 0.7051 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7050 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7050 |
| Kynurenine--oxoglutarate transaminase 1 | Q16773 | KAT1_HUMAN | Homo sapiens | 2 | 0.7049 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7043 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7041 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7040 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7026 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7022 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 2 | 0.7016 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7016 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7015 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7015 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7014 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7009 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7007 |