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(7R,8S) dihydrodehydrodiconiferyl alcohol
- Family: Plantae - Pinaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Neolignan
| Canonical Smiles | OCCCc1cc2c(c(c1)O)O[C@H]([C@@H]2CO)c1ccc(c(c1)OC)O |
|---|---|
| InChI | InChI=1S/C19H22O6/c1-24-17-9-12(4-5-15(17)22)18-14(10-21)13-7-11(3-2-6-20)8-16(23)19(13)25-18/h4-5,7-9,14,18,20-23H,2-3,6,10H2,1H3/t14-,18+/m1/s1 |
| InChIKey | PKORXOLYTWDULG-KDOFPFPSSA-N |
| Formula | C19H22O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 346.38 |
| Rotatable Bonds | 6 |
| TPSA | 99.38 |
| LogP | 2.24 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.37 |
| Exact Mass | 346.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cedrus atlantica | Pinaceae | Plantae | 123597 |
Showing of synonyms
(7R,8S) dihydrodehydrodiconiferyl alcohol
(-)-Cedrusin
404335-99-5
AKOS040762662
(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-ol
- Maya B, Abedini A, et al. (2017). A new δ-tocotrienolic acid derivative and other constituents from the cones of Cedrus atlantica and their in vitro antimicrobial activity. Phytochemistry Letters, 2017, 20, 252-258. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)OC(C2)c3ccccc3
Level: 1
Mol. Weight: 346.38 g/mol
SMILES: C1COc(c12)cccc2
Level: 0
Mol. Weight: 346.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 346.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.12
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.98
- Plasma Protein Binding
- 77.88
- 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
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.38
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.88
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.72
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.85
- 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
- -0.64
- Rat (Acute)
- 2.11
- Rat (Chronic Oral)
- 3.1
- Fathead Minnow
- 4.11
- 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
- 441.66
- Hydration Free Energy
- -9.51
- Log(D) at pH=7.4
- 2.17
- Log(P)
- 1.08
- Log S
- -3.56
- Log(Vapor Pressure)
- -8.06
- Melting Point
- 150.75
- pKa Acid
- 7.78
- pKa Basic
- 3.16
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9316 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9315 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.9057 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9020 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8950 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8895 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.8857 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8827 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8804 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8741 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8717 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8715 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8688 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8673 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8542 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8490 |
| Adenosine 5'-monophosphoramidase HINT1 | P49773 | HINT1_HUMAN | Homo sapiens | 3 | 0.8436 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8363 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 4 | 0.8350 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8324 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.8316 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8307 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8305 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8302 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8302 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8299 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8284 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8281 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8182 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8141 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.8099 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8093 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8088 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8078 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.8003 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.7970 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7956 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7955 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7883 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7869 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 3 | 0.7800 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7790 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7777 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7763 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7761 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7705 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7696 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7695 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7666 |
| Gag-Pol polyprotein | O12158 | POL_HV192 | Human immunodeficiency virus type 1 group M subtype C | 3 | 0.7666 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7663 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7651 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7630 |
| Adenylate cyclase 2 | A0A2U2H3Y1 | A0A384LKY8_YERPE | Yersinia pestis | 3 | 0.7618 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7613 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7599 |
| GTP 3',8-cyclase | P69848 | MOAA_STAA8 | Staphylococcus aureus | 3 | 0.7576 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7574 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7561 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7524 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7508 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7478 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7474 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7465 |
| Karilysin | D0EM77 | KLY_TANFA | Tannerella forsythia | 3 | 0.7461 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7451 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 3 | 0.7437 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7434 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7408 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7388 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7383 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7382 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7378 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7378 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7373 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7361 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 4 | 0.7359 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7352 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7349 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7331 |
| Phosphodiesterase | Q8WQX9 | Q8WQX9_9TRYP | Trypanosoma brucei | 3 | 0.7323 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7286 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7283 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7272 |
| Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7250 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7247 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7244 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7240 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 4 | 0.7235 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7217 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7213 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7196 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 3 | 0.7196 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7192 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7171 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 5 | 0.7169 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7167 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7164 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7149 |
| FMN-dependent NAD(P)H:quinone oxidoreductase 1 | Q9I5F3 | AZOR1_PSEAE | Pseudomonas aeruginosa | 2 | 0.7148 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7144 |
| Decapping and exoribonuclease protein | O70348 | DXO_MOUSE | Mus musculus | 3 | 0.7140 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7128 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7125 |
| dTDP-fucosamine acetyltransferase | Q8FBQ3 | WECD_ECOL6 | Escherichia coli O6:H1 | 3 | 0.7122 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7119 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7100 |
| Serine hydroxymethyltransferase | Q7SIB6 | Q7SIB6_GEOSE | Geobacillus stearothermophilus | 3 | 0.7077 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7076 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7074 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7073 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7070 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7068 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7066 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7045 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7044 |
| YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein | Q5SHN1 | Q5SHN1_THET8 | Thermus thermophilus | 3 | 0.7037 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7033 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7028 |
| Ephrin type-A receptor 4 | Q03137 | EPHA4_MOUSE | Mus musculus | 4 | 0.7027 |
| Leucine--tRNA ligase | P07813 | SYL_ECOLI | Escherichia coli | 3 | 0.7025 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7010 |