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(S)-p-hydroxyphenopyrrozin
- Family: Fungi - Bionectriaceae
- Kingdom: Fungi
- Class: Alkaloid
| Canonical Smiles | C1(=C([C@H]2N(C1=O)CCC2)c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C13H13NO3/c15-9-5-3-8(4-6-9)11-10-2-1-7-14(10)13(17)12(11)16/h3-6,10,15-16H,1-2,7H2/t10-/m0/s1 |
| InChIKey | KFPFLSSRTQAZQF-JTQLQIEISA-N |
| Formula | C13H13NO3 |
| HBA | 3 |
| HBD | 2 |
| MW | 231.25 |
| Rotatable Bonds | 1 |
| TPSA | 60.77 |
| LogP | 1.67 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.31 |
| Exact Mass | 231.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bionectria sp. | Bionectriaceae | Fungi | — |
Showing of synonyms
(S)-p-hydroxyphenopyrrozin
(7aS)-p-hydroxyphenopyrrozin
(8S)-2-hydroxy-1-(4-hydroxyphenyl)-5,6,7,8-tetrahydropyrrolizin-3-one
7a(S)-p-hydroxyphenopyrrozin
CHEMBL479677
CHEBI:226663
No compound-protein relationship available.
SMILES: c1ccccc1C2=CC(=O)N(C23)CCC3
Level: 1
Mol. Weight: 231.25 g/mol
SMILES: C1=CC(=O)N(C12)CCC2
Level: 0
Mol. Weight: 231.25 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 231.25 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.02
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.51
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.5
- Plasma Protein Binding
- 42.64
- 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
- Inhibitor
- CYP 2C19 Substrate
- 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
- 7.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.52
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.57
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.45
- Micronucleos
- Toxic
- 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
- 2.07
- Rat (Acute)
- 2.1
- Rat (Chronic Oral)
- 2.56
- Fathead Minnow
- 3.96
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 376.63
- Hydration Free Energy
- -12.49
- Log(D) at pH=7.4
- 0.49
- Log(P)
- 0.24
- Log S
- -2.27
- Log(Vapor Pressure)
- -7.27
- Melting Point
- 232.96
- pKa Acid
- 7.11
- pKa Basic
- 5.51
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.9054 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8996 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8738 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8684 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8135 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7960 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7791 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7709 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7702 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7467 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7308 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7299 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7298 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7284 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7219 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7195 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7176 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7158 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7156 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7139 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7136 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7115 |
| Ethylene receptor 1 | P49333 | ETR1_ARATH | Arabidopsis thaliana | 3 | 0.7108 |
| Acyl-CoA:acyl-CoA alkyltransferase | Q8PDX2 | OLEA_XANCP | Xanthomonas campestris pv. campestris | 3 | 0.7035 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7021 |
| Adenosine monophosphate-protein transferase | Q8ZVF7 | Q8ZVF7_PYRAE | Pyrobaculum aerophilum | 3 | 0.7011 |