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Holstiinone B
- Family: Plantae - Ochnaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Biflavanone
| Canonical Smiles | COc1ccc(cc1)[C@@H]1Oc2cc(OC)cc(c2C(=O)[C@H]1[C@H]1[C@@H](Oc2c(C1=O)ccc(c2)OC)c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C33H28O9/c1-38-20-10-6-18(7-11-20)33-29(31(37)27-24(35)14-22(40-3)16-26(27)42-33)28-30(36)23-13-12-21(39-2)15-25(23)41-32(28)17-4-8-19(34)9-5-17/h4-16,28-29,32-35H,1-3H3/t28-,29-,32+,33+/m1/s1 |
| InChIKey | PLJRTDCLFWPPEK-KMYPOQQFSA-N |
| Formula | C33H28O9 |
| HBA | 9 |
| HBD | 2 |
| MW | 568.58 |
| Rotatable Bonds | 6 |
| TPSA | 120.75 |
| LogP | 5.69 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.21 |
| Exact Mass | 568.17 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ochna holstii | Ochnaceae | Plantae | 1389766 |
Showing of synonyms
Holstiinone B
No compound-protein relationship available.
SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6
Level: 3
Mol. Weight: 568.58 g/mol
SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5
Level: 2
Mol. Weight: 568.58 g/mol
SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4
Level: 1
Mol. Weight: 568.58 g/mol
SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3
Level: 1
Mol. Weight: 568.58 g/mol
SMILES: c1cccc(c12)OCCC2=O
Level: 0
Mol. Weight: 568.58 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 568.58 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.16
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.500
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 9.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.830
- Plasma Protein Binding
- 89.25
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.510
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.000
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.210
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.230
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- Toxic
- T. Pyriformis
- -19712.120
- Rat (Acute)
- 2.960
- Rat (Chronic Oral)
- 2.920
- Fathead Minnow
- 46.380
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 420.560
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 5.240
- Log(P)
- 5.87
- Log S
- -8.26
- Log(Vapor Pressure)
- -12.74
- Melting Point
- 225.32
- pKa Acid
- 7.73
- pKa Basic
- -1.39
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9546 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.9421 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9354 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.9338 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.9260 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.9198 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.9184 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.9183 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9037 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.9028 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.8972 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8950 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8921 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8860 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8833 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8809 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.8783 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8753 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.8705 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 3 | 0.8663 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8658 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8628 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8484 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8430 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.8397 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8350 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.8233 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8232 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8228 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8134 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.8122 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8122 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8017 |
| Carnitine O-palmitoyltransferase 2, mitochondrial | P18886 | CPT2_RAT | Rattus norvegicus | 3 | 0.7907 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7899 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7895 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7881 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7846 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7845 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7830 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.7830 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7812 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7798 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7737 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7737 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7734 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7721 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7695 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7686 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 4 | 0.7675 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7669 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7654 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7640 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7630 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7619 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7598 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7597 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 3 | 0.7593 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7556 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7529 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7518 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7510 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.7504 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7501 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 3 | 0.7500 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7462 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7459 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7439 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7432 |
| Phosphodiesterase | Q8WQX9 | Q8WQX9_9TRYP | Trypanosoma brucei | 3 | 0.7420 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7418 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7417 |
| Prostaglandin reductase 3 | Q8N4Q0 | PTGR3_HUMAN | Homo sapiens | 4 | 0.7410 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7405 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7398 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7390 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7387 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7371 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7362 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7354 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 3 | 0.7351 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7346 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7337 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | P49354 | FNTA_HUMAN | Homo sapiens | 3 | 0.7335 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7321 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7320 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7312 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7305 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7296 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7290 |
| Glycerol kinase | P0A6F3 | GLPK_ECOLI | Escherichia coli | 4 | 0.7286 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7272 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7257 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7256 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7250 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7247 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7237 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7228 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7200 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7193 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7193 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7188 |
| O-methyltransferase family 2 | D5STZ7 | D5STZ7_PLAL2 | Planctopirus limnophila | 4 | 0.7186 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7181 |
| Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7177 |
| Cytochrome P450 2C5 | P00179 | CP2C5_RABIT | Oryctolagus cuniculus | 3 | 0.7171 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7170 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7168 |
| Cyclic GMP-AMP synthase | Q8C6L5 | CGAS_MOUSE | Mus musculus | 3 | 0.7156 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7153 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7144 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7126 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7122 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7108 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7094 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7094 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7091 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.7088 |
| Uncharacterized protein | Q55S71 | Q55S71_CRYNB | Cryptococcus neoformans var. neoformans serotype D | 4 | 0.7087 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7070 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7065 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7061 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7027 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7024 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 4 | 0.7018 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7007 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7002 |