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Ferruginol
- Family: Plantae - Verbenaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | CC(c1cc2CC[C@@H]3[C@](c2cc1O)(C)CCCC3(C)C)C |
|---|---|
| InChI | InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1 |
| InChIKey | QXNWVJOHUAQHLM-AZUAARDMSA-N |
| Formula | C20H30O |
| HBA | 1 |
| HBD | 1 |
| MW | 286.46 |
| Rotatable Bonds | 1 |
| TPSA | 20.23 |
| LogP | 5.55 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 286.23 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Juniperus phoenicea | Cupressaceae | Plantae | 61308 |
| 2 | Tetraclinis articulata | Cupressaceae | Plantae | 13717 |
| 3 | Cupressus arizonica | Cupressaceae | Plantae | 49011 |
| 4 | Fuerstia africana | Lamiaceae | Plantae | 204226 |
| 5 | Clerodendrum eriophyllum | Verbenaceae | Plantae | 54214 |
Showing of synonyms
Ferruginol
514-62-5
(+)-Ferruginol
Trans-Ferruginol
N2CMM6X37M
(4bS,8aS)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
DTXSID20331722
Podocarpa-8,11,13-trien-12-ol, 13-isopropyl-
(4BS,8AS)-4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-3-PHENANTHRENOL
3-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-, (4BS-TRANS)-
DTXCID70282816
(4bs,8as)-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
Qxnwvjohuaqhlm-azuaardmsa-n
3-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bS,8aS)-
CHEBI:78274
Abieta-8,11,13-trien-12-ol
UNII-N2CMM6X37M
CHEMBL197308
MEGxp0_000699
AC1L9C4T
XBG37SPT8G
SureCN155580
SCHEMBL155580
8,11,13-abietatrien-12-ol
ACon1_000701
FERRUGINOL, (+/-)-
HY-N6033
12-hydroxyabieta-8,11,13-triene
BDBM50483056
AKOS032948384
FF29416
FS-7565
DA-68969
CS-0032206
C09092
Abieta-9(11),8(14),12-trien-12-ol #
Q3743828
BRD-K27959543-001-01-3
PODOCARPA-8,11,13-TRIEN-12-OL, 13-ISOPROPYL-, (+/-)-
(4bs,8as)-4b,8,8-trimethyl-2-propane-2-yl-5,6,7,8a,9,10-hexa hydrophenanthren-3-ol
(4BS,8AS)-4B,8,8-TRIMETHYL-2-(PROPAN-2-YL)-4B,5,6,7,8,8A,9,10-OCTAHYDROPHENANTHREN-3-OL
10219-82-6
3-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-, (4BR,8AR)-REL-
3-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-, TRANS-
REL-(4BR,8AR)-4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-3-PHENANTHRENOL
- Koch A, Orjala J, et al. (2006). An antimalarial abietane diterpene from Fuerstia africana T.C.E. Fries. Biochemical Systematics and Ecology,2006,34,270-272. [View] [PubMed]
- Machumi F, Samoylenko V, et al. (2010). Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum. Natural Product Communication,2010,5(6),853-858. [View] [PubMed]
- Cheraif I, Jannet HB, et al. (2007). Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene. Biochemical Systematics and Ecology,2007,35,813 -820. [View]
- Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [View]
- Barrero AF, Quılez del Moral JF, et al. (2003). Diterpenoids from Tetraclinis articulata that inhibit various human leukocyte functions. Journal of Natural Products,2003,66(6),844-850. [View] [PubMed]
Pubchem:
442027
Cas:
514-62-5
Zinc:
ZINC000004097893
Kegg Ligand:
C09092
Chebi:
78274
Nmrshiftdb2:
60019713
Metabolights:
MTBLC78274
Chembl:
CHEMBL197308
Comptox:
DTXSID20331722
Bindingdb:
50483056
CPRiL:
119726
SMILES: c1cccc(c12)CCC3C2CCCC3
Level: 0
Mol. Weight: 286.46 g/mol
Anti-leishmanial
Antibacterial
Antimalarial
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 90.76
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.54
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 3.04
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.11
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.55
- 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
- 3.63
- Rat (Acute)
- 2.01
- Rat (Chronic Oral)
- 2.07
- Fathead Minnow
- 4.15
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 333.9
- Hydration Free Energy
- -2.56
- Log(D) at pH=7.4
- 5.45
- Log(P)
- 5.59
- Log S
- -5.89
- Log(Vapor Pressure)
- -5.76
- Melting Point
- 136.72
- pKa Acid
- 12.1
- pKa Basic
- 7.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 4 | 0.7318 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 4 | 0.7318 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7191 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7191 |