Select a section from the left sidebar
Sphaeropsidin C
- Family: Fungi - Cypress
- Kingdom: Fungi
-
Class: Terpenoid
- Subclass: Pimarane Diterpenoid
| Canonical Smiles | C=C[C@@]1(C)CC[C@]2(C(=C1)C(=O)C[C@@H]1[C@@]2(CCCC1(C)C)C(=O)O)O |
|---|---|
| InChI | InChI=1S/C20H28O4/c1-5-18(4)9-10-20(24)13(12-18)14(21)11-15-17(2,3)7-6-8-19(15,20)16(22)23/h5,12,15,24H,1,6-11H2,2-4H3,(H,22,23)/t15-,18-,19-,20+/m0/s1 |
| InChIKey | VIDNIVWPSMVGJV-MVJPYGJCSA-N |
| Formula | C20H28O4 |
| HBA | 3 |
| HBD | 2 |
| MW | 332.44 |
| Rotatable Bonds | 2 |
| TPSA | 74.6 |
| LogP | 3.5 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 332.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Diplodia quercivora | Botryosphaeriaceae | Fungi | 1281306 |
| 2 | Sphaeropsis sapinea | Cypress | Fungi | 66738 |
Showing of synonyms
Sphaeropsidin C
(4aR,4bR,7R,10aS)-7-ethenyl-4b-hydroxy-1,1,7-trimethyl-9-oxo-3,4,5,6,10,10a-hexahydro-2H-phenanthrene-4a-carboxylic acid
(4AR,4BR,7R,10as)-7-ethenyl-4b-hydroxy-1,1,7-trimethyl-9-oxo-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-4a-carboxylate
193220-38-1
CHEBI:69495
MLS003373235
CHEMBL1934132
SMR002047992
Q27137834
- Andolfi A, Maddau L, et al. (2014). Diplopimarane, a 20-nor-ent-pimarane produced by the oak pathogen Diplodia quercivora. Journal of Natural Products,2014,77(6),2352-2360. [View] [PubMed]
- Evidentea A, Sparapano L, et al. (2002). Sphaeropsidins D and E, two other pimarane diterpenes produced in vitro by the plant pathogenic fungus Sphaeropsis sapinea f. sp. cupressi. Phytochemistry,2002,59,817-823. [View] [PubMed]
Pubchem:
10544575
Cas:
193220-38-1
Chebi:
69495
Nmrshiftdb2:
70010211
Metabolights:
MTBLC69495
Chembl:
CHEMBL1934132
No compound-protein relationship available.
SMILES: C1CCCC(C=12)C3C(CC2=O)CCCC3
Level: 0
Mol. Weight: 332.44 g/mol
Antifungal
Antimicrobial
Phytotoxicity
Zootoxic
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.88
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.55
- Plasma Protein Binding
- 77.93
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.93
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.87
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.82
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.7
- 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
- 0.97
- Rat (Acute)
- 2.18
- Rat (Chronic Oral)
- 2.05
- 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
- 371.0
- Hydration Free Energy
- -9.25
- Log(D) at pH=7.4
- 1.12
- Log(P)
- 4.04
- Log S
- -3.52
- Log(Vapor Pressure)
- -8.59
- Melting Point
- 173.49
- pKa Acid
- 4.83
- pKa Basic
- 7.27