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(-)-semiglabrinol
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone
| Canonical Smiles | O[C@@H]1[C@@H]2[C@H](OC1(C)C)Oc1c2c2oc(cc(=O)c2cc1)c1ccccc1 |
|---|---|
| InChI | InChI=1S/C21H18O5/c1-21(2)19(23)17-16-14(25-20(17)26-21)9-8-12-13(22)10-15(24-18(12)16)11-6-4-3-5-7-11/h3-10,17,19-20,23H,1-2H3/t17-,19-,20+/m1/s1 |
| InChIKey | XBKLVCYSINXGAW-RLLQIKCJSA-N |
| Formula | C21H18O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 350.37 |
| Rotatable Bonds | 1 |
| TPSA | 68.9 |
| LogP | 3.43 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 350.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tephrosia apollinea | Leguminosae/Fabaceae | Plantae | 1390541 |
Showing of synonyms
(-)-semiglabrinol
Semiglabrinol
(12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.02,7.012,16]hexadeca-1(10),2(7),4,8-tetraen-6-one
(12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo(8.6.0.02,7.012,16)hexadeca-1(10),2(7),4,8-tetraen-6-one
51787-33-8
CHEBI:188973
LMPK12110015
- Khalafallah A, Suleiman S, et al. (2009). Prenylated flavonoids from Tephrosia apollinea. Chinese Chemical Letters, 2009, 20(12), 1465-1468. [View]
No compound-protein relationship available.
SMILES: O1CCC2C1Oc(c23)ccc4c3oc(cc4=O)-c5ccccc5
Level: 1
Mol. Weight: 350.37 g/mol
SMILES: O1CCC2C1Oc(c23)ccc4c3occc4=O
Level: 0
Mol. Weight: 350.37 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 350.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.29
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.35
- Plasma Protein Binding
- 97.06
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.58
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.78
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.47
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.57
- 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
- Safe
- T. Pyriformis
- -4.8
- Rat (Acute)
- 3.32
- Rat (Chronic Oral)
- 1.78
- Fathead Minnow
- 4.85
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 462.65
- Hydration Free Energy
- -7.66
- Log(D) at pH=7.4
- 3.38
- Log(P)
- 3.57
- Log S
- -4.72
- Log(Vapor Pressure)
- -9.15
- Melting Point
- 204.54
- pKa Acid
- 8.63
- pKa Basic
- 3.32
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.9673 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.9198 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9033 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9001 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 4 | 0.8804 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.8634 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8556 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8543 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8270 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8075 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7999 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7937 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 3 | 0.7841 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.7820 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7787 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7704 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7641 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 4 | 0.7632 |
| Interstitial collagenase | P03956 | MMP1_HUMAN | Homo sapiens | 3 | 0.7543 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 3 | 0.7515 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7498 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7469 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7468 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7394 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7368 |
| Angiopoietin-1 receptor | Q02763 | TIE2_HUMAN | Homo sapiens | 3 | 0.7362 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7360 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7350 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7316 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7276 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7266 |
| Sterol 14alpha-demethylase | P9WPP9 | CP51_MYCTU | Mycobacterium tuberculosis | 3 | 0.7219 |
| Actin nucleation-promoting factor WAS | P42768 | WASP_HUMAN | Homo sapiens | 3 | 0.7193 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7188 |
| Flavonoid 3-O-glucosyltransferase | A6XNC6 | UGFGT_MEDTR | Medicago truncatula | 2 | 0.7162 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 3 | 0.7154 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7119 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7058 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7028 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 3 | 0.7012 |