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3 ’,5 ’-dihydroxycinnamoyl-3beta,28,30-dihydroxylup-20(29)-ene
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Pentacyclic Triterpene
| Canonical Smiles | OCC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)OC(=O)/C=C/c1cc(O)cc(c1)O)CO |
|---|---|
| InChI | InChI=1S/C39H56O6/c1-24(22-40)28-11-16-39(23-41)18-17-37(5)29(34(28)39)8-9-31-36(4)14-13-32(35(2,3)30(36)12-15-38(31,37)6)45-33(44)10-7-25-19-26(42)21-27(43)20-25/h7,10,19-21,28-32,34,40-43H,1,8-9,11-18,22-23H2,2-6H3/b10-7+/t28-,29+,30-,31+,32-,34+,36-,37+,38+,39+/m0/s1 |
| InChIKey | BCHMCFWVEJOQSJ-XOXWBHJLSA-N |
| Formula | C39H56O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 620.87 |
| Rotatable Bonds | 6 |
| TPSA | 107.22 |
| LogP | 7.65 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 45 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.72 |
| Exact Mass | 620.41 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Oxystigma mannii | Leguminosae/Fabaceae | Plantae | 162862 |
Showing of synonyms
3 ’,5 ’-dihydroxycinnamoyl-3beta,28,30-dihydroxylup-20(29)-ene
- Peyeino J, Tabekoueng G, et al. (2021). Terpenoids from Cameroonian Oxystigma mannii (Baill.) Harms. Scientific African, 2021, 12, e00751. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OC(C2)CCC3C2CCC4C3CCC5C4CCC(C56)CCC6
Level: 1
Mol. Weight: 620.87 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 620.87 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 620.87 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.19
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.820
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 21.04
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.370
- Plasma Protein Binding
- 96.45
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 9.430
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.830
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.120
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.240
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -41823.050
- Rat (Acute)
- 2.150
- Rat (Chronic Oral)
- 2.730
- Fathead Minnow
- 71.600
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 1529.700
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 7.430
- Log(P)
- 6.65
- Log S
- -6.93
- Log(Vapor Pressure)
- -41.97
- Melting Point
- 268.78
- pKa Acid
- 8.74
- pKa Basic
- 5.22
| 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 | 0.9299 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.9227 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9129 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.9081 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9069 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9067 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9020 |
| NADPH-dependent 7-cyano-7-deazaguanine reductase | Q9KTK0 | QUEF_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8895 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8861 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8791 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8780 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8724 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.8682 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8574 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8573 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8570 |
| tRNA-guanine(15) transglycosylase | O58843 | ATGT_PYRHO | Pyrococcus horikoshii | 3 | 0.8501 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8470 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.8447 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.8411 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8403 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8317 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.8124 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.8088 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8058 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8006 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7964 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7922 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7855 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7767 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7745 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7623 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7589 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 3 | 0.7556 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | P62617 | ISPF_ECOLI | Escherichia coli | 3 | 0.7550 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7466 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7415 |
| Flavin-dependent thymidylate synthase | Q9WYT0 | THYX_THEMA | Thermotoga maritima | 3 | 0.7408 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7395 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7328 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7326 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7317 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7296 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7261 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7261 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7247 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7227 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7223 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7217 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7210 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7199 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7194 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7190 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7187 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7143 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7116 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7110 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7108 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7098 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7089 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7073 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7067 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7031 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7019 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7015 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7005 |