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Hautriwaic acid
- Family: Plantae - Sapindaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpene
| Canonical Smiles | OC[C@]12CC[C@H]([C@]([C@H]2CCC=C1C(=O)O)(C)CCc1ccoc1)C |
|---|---|
| InChI | InChI=1S/C20H28O4/c1-14-6-10-20(13-21)16(18(22)23)4-3-5-17(20)19(14,2)9-7-15-8-11-24-12-15/h4,8,11-12,14,17,21H,3,5-7,9-10,13H2,1-2H3,(H,22,23)/t14-,17-,19+,20-/m1/s1 |
| InChIKey | PHKSUFCCGLWIMC-SIKIZQCASA-N |
| Formula | C20H28O4 |
| HBA | 3 |
| HBD | 2 |
| MW | 332.44 |
| Rotatable Bonds | 5 |
| TPSA | 70.67 |
| LogP | 4.05 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 332.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dodonaea angustifolia | Sapindaceae | Plantae | 379228 |
| 2 | Dodonaea angustifolia | Sapindaceae | Plantae | 379228 |
| 3 | Dodonaea angustifolia | Sapindaceae | Plantae | 379228 |
Showing of synonyms
Hautriwaic acid
18411-75-1
(4aR,5S,6R,8aS)-5-[2-(furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
DTXSID20904213
AKOS040761817
FS-9347
CS-0024582
- Omosa LK, Amugune B, et al. (2014). Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia. South African Journal of Botany,2014,91,58-62. [View] [PubMed]
- Omosa LK, Midiwo JO, et al. (2010). neo-Clerodane diterpenoids from the leaf exudate of Dodonaea angustifolia. Phytochemistry Letters,2010,3(4),217-220. [View] [PubMed]
- Bekele D, Gebreyesus T. (2009). Phytochemical investigation on the leaves of Dodonaea viscosa var. angustifolia. M.Sc. Thesis-3, Addis Ababa University, Ethiopia,2009. [View] [PubMed]
CPRiL:
188048
SMILES: c1occc1CCC(CCC2)C(C23)CCC=C3
Level: 1
Mol. Weight: 332.44 g/mol
SMILES: C1=CCCC(C12)CCCC2
Level: 0
Mol. Weight: 332.44 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 332.44 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -5.19
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.71
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.2
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.91
- Plasma Protein Binding
- 80.54
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.57
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.16
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.01
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.61
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -0.59
- Rat (Acute)
- 2.24
- Rat (Chronic Oral)
- 2.3
- Fathead Minnow
- 4.02
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 374.54
- Hydration Free Energy
- -8.09
- Log(D) at pH=7.4
- 1.32
- Log(P)
- 3.55
- Log S
- -4.27
- Log(Vapor Pressure)
- -8.85
- Melting Point
- 162.49
- pKa Acid
- 3.31
- pKa Basic
- 7.73
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7967 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7967 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7957 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7957 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7892 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7892 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7817 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7817 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7748 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7748 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7697 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7697 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7627 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7627 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7546 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7546 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7475 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7475 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7475 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7475 |
| Amino-acid acetyltransferase | Q5FAK7 | Q5FAK7_NEIG1 | Neisseria gonorrhoeae | 3 | 0.7433 |
| Amino-acid acetyltransferase | Q5FAK7 | Q5FAK7_NEIG1 | Neisseria gonorrhoeae | 3 | 0.7433 |
| Ornithine transcarbamylase, mitochondrial | P00480 | OTC_HUMAN | Homo sapiens | 3 | 0.7337 |
| Ornithine transcarbamylase, mitochondrial | P00480 | OTC_HUMAN | Homo sapiens | 3 | 0.7337 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7260 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7260 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 2 | 0.7208 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 2 | 0.7208 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7200 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7200 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7187 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7187 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 2 | 0.7144 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 2 | 0.7144 |