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Lucidin primeveroside
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
- Class: Anthraquinone
| Canonical Smiles | OCc1c(O[C@@H]2O[C@H](CO[C@@H]3OC[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)cc2c(c1O)C(=O)c1c(C2=O)cccc1 |
|---|---|
| InChI | InChI=1S/C26H28O14/c27-6-12-14(5-11-16(19(12)31)18(30)10-4-2-1-3-9(10)17(11)29)39-26-24(36)22(34)21(33)15(40-26)8-38-25-23(35)20(32)13(28)7-37-25/h1-5,13,15,20-28,31-36H,6-8H2/t13-,15-,20+,21-,22+,23-,24-,25+,26-/m1/s1 |
| InChIKey | NVKNRXOMCYTFJF-WFLOGZPDSA-N |
| Formula | C26H28O14 |
| HBA | 14 |
| HBD | 8 |
| MW | 564.5 |
| Rotatable Bonds | 6 |
| TPSA | 232.9 |
| LogP | -2.7 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.46 |
| Exact Mass | 564.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rubia tinctorum | Rubiaceae | Plantae | 29802 |
Showing of synonyms
Lucidin primeveroside
1-hydroxy-2-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-9,10-dione
1-Hydroxy-2-(hydroxymethyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxymethyl)oxan-2-yl)oxyanthracene-9,10-dione
111-833-5
29706-59-0
Lucidinprimeveroside
Lucidin 3-O-beta-primveroside
Lucidin 3-O-primeveroside
9,10-Anthracenedione, 1-hydroxy-2-(hydroxymethyl)-3-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-
1-Hydroxy-2-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
CCRIS 4532
Lucidin 3-O-primveroside
Lucidin primevoroside
Lucidin-primeveroside
Lucidin-3-beta-primeveroside
9,10-anthracenedione, 1-hydroxy-2-(hydroxymethyl)-3-[(6-o-|A-d-xylopyranosyl-|A-d-glucopyranosyl)oxy]-
CHEMBL521217
SCHEMBL23522435
DTXSID40952155
HY-N8022
AKOS040760529
DA-55059
FS-10655
Glucopyranoside, 4-hydroxy-3-(hydroxymethyl)-2-anthraquinonyl 6-O-beta-D- xylopyranosyl-, beta-D-
CS-0138995
NS00094501
E88947
1-hydroxy-2-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-anthracene-9,10-dione
1-HYDROXY-2-(HYDROXYMETHYL)-3-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-({[(2S,3R,4S,5R)-3,4,5-TRIHYDROXYOXAN-2-YL]OXY}METHYL)OXAN-2-YL]OXY}ANTHRACENE-9,10-DIONE
4-Hydroxy-3-(hydroxymethyl)-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-O-pentopyranosylhexopyranoside
- Herzberg G, Druel T, et al. (1998). Three hydroxymethylanthraquinone glycosides from rubia tinctorum. Phytochemistry,1998,49(1),277–279. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3)ccc(c34)C(=O)c5c(C4=O)cccc5
Level: 2
Mol. Weight: 564.5 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4
Level: 1
Mol. Weight: 564.5 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 564.5 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 564.5 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 564.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.65
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.26
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.84
- Plasma Protein Binding
- 78.8
- 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
- 5.63
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.15
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.68
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.88
- 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
- -4288.4
- Rat (Acute)
- 2.68
- Rat (Chronic Oral)
- 4.41
- Fathead Minnow
- 8.8
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 585.21
- Hydration Free Energy
- -2.93
- Log(D) at pH=7.4
- -0.45
- Log(P)
- -0.31
- Log S
- -2.88
- Log(Vapor Pressure)
- -12.93
- Melting Point
- 204.48
- pKa Acid
- 2.41
- pKa Basic
- 7.59
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9190 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.9158 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9048 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8962 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8837 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8749 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.8728 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8240 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8221 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8140 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7998 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7974 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7970 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7929 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7914 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7879 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 4 | 0.7778 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7767 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7751 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7722 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7709 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7664 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7639 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7609 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7608 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7564 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7545 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7532 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7500 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7492 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7486 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7480 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7480 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 2 | 0.7442 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7441 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7435 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 4 | 0.7415 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7413 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7404 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7357 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7339 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7339 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7283 |
| Aurora kinase B-A | Q6DE08 | AUKBA_XENLA | Xenopus laevis | 3 | 0.7270 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7268 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7239 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7238 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7235 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7217 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7217 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7213 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7203 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7142 |
| Interleukin-2 | P60568 | IL2_HUMAN | Homo sapiens | 3 | 0.7141 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7140 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7120 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7103 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7094 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7082 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.7074 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7070 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7066 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7060 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7056 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7054 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 2 | 0.7030 |
| cGMP-dependent protein kinase, putative | A5K0N4 | A5K0N4_PLAVS | Plasmodium vivax | 3 | 0.7024 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7010 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7006 |