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Warburganal
- Family: Plantae - Canellaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | O=CC1=CC[C@@H]2[C@]([C@@]1(O)C=O)(C)CCCC2(C)C |
|---|---|
| InChI | InChI=1S/C15H22O3/c1-13(2)7-4-8-14(3)12(13)6-5-11(9-16)15(14,18)10-17/h5,9-10,12,18H,4,6-8H2,1-3H3/t12-,14-,15+/m0/s1 |
| InChIKey | QGMWDUUHVVLHNP-AEGPPILISA-N |
| Formula | C15H22O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 250.34 |
| Rotatable Bonds | 2 |
| TPSA | 54.37 |
| LogP | 2.28 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 250.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 2 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 3 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 4 | Warburgia stuhlmannii | Canellaceae | Plantae | 549618 |
Showing of synonyms
Warburganal
62994-47-2
(1S,4aS,8aS)-1-hydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
UNII-4A48Y1F67H
4A48Y1F67H
WARBURGANAL [MI]
(-)-WARBURGANAL
WARBURGANAL, (-)-
DTXSID20212204
(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-Octahydro-1-hydroxy-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde
1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-, (1alpha,4aalpha,8abeta)-
1,2-naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-, (1S,4aS,8aS)-
1,2-NAPHTHALENEDICARBOXALDEHYDE, 1,4,4A,5,6,7,8,8A-OCTAHYDRO-1-HYDROXY-5,5,8A-TRIMETHYL-, (1S-(1.ALPHA.,4A.ALPHA.,8A.BETA.))-
DTXCID80134695
1,2-NAPHTHALENEDICARBOXALDEHYDE, 1,4,4A,5,6,7,8,8A-OCTAHYDRO-1-HYDROXY-5,5,8A-TRIMETHYL-, (1S-(1ALPHA,4AALPHA,8ABETA))-
CHEBI:10032
AC1L2I6T
AC1Q6A4Q
(1s,4as,8as)-1-hydroxy-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
CHEMBL452492
SCHEMBL4244667
NSC711690
NSC-711690
C09748
Q27108559
1R,4aS,8aS)-1-Hydroxy-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
- Opiyo SA, Manguro LOA, et al. (2011). 7alpha-Acetylugandensolide and antimicrobial properties of Warburgia ugandensis extracts and isolates against sweet potato pathogens. Phytochemistry Letters,2011,4(2),161-165. [View] [PubMed]
- Taniguchi M, Kubo I. (1993). Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.. Journal of Natural Products,1993,56(9),1539-1546. [View] [PubMed]
- Rugutt JK, Ngigi AN, et al. (2006). Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. Phytomedicine,2006,13(8),576-583. [View] [PubMed]
Pubchem:
72502
Cas:
62994-47-2
Kegg Ligand:
C09748
Chebi:
10032
Nmrshiftdb2:
20233990
Chembl:
CHEMBL452492
Comptox:
DTXSID20212204
No compound-protein relationship available.
SMILES: C1C=CCC(C12)CCCC2
Level: 0
Mol. Weight: 250.34 g/mol
Antibacterial
Antifungal
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.48
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.15
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.02
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- -0.04
- Plasma Protein Binding
- 40.12
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.3
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.63
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.5
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.46
- Micronucleos
- Safe
- 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
- 0.57
- Rat (Acute)
- 2.97
- Rat (Chronic Oral)
- 1.09
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 316.21
- Hydration Free Energy
- -7.05
- Log(D) at pH=7.4
- 3.16
- Log(P)
- 3.35
- Log S
- -2.91
- Log(Vapor Pressure)
- -5.35
- Melting Point
- 117.27
- pKa Acid
- 5.56
- pKa Basic
- 5.6
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8247 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8247 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7739 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7739 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7622 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7622 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7300 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7300 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7276 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7276 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7042 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7042 |