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Matricolone
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sequiterpene Lactone
| Canonical Smiles | O=C1CCC2=C3C=C[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(C)O)C |
|---|---|
| InChI | InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1 |
| InChIKey | CCCIJQPRIXGQOE-XWSJACJDSA-N |
| Formula | C19H24O2 |
| HBA | 2 |
| HBD | 1 |
| MW | 284.4 |
| Rotatable Bonds | 0 |
| TPSA | 37.3 |
| LogP | 3.72 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.63 |
| Exact Mass | 284.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Matricaria chamomilla | Asteraceae | Plantae | 98504 |
Showing of synonyms
Matricolone
Methyltrienolone
METRIBOLONE
965-93-5
R-1881
Metribolone [INN:DCF]
Metribolonum [INN-Latin]
17beta-Hydroxy-17-methylestra-4,9,11-trien-3-one
Metribolona [INN-Spanish]
NSC-92858
R1881 (synthetic androgen)
CHEBI:379896
2C323EGI97
METRIBOLONE [INN]
NSC 92858
(8S,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
METRIBOLONE [MART.]
METHYLTRIENOLONE [MI]
METRIBOLONE [WHO-DD]
DTXSID8034162
Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)-
17-methyloestra-4,9,11-trien-3-one,17beta-ol
Metribolonum (INN-Latin)
Metribolona (INN-Spanish)
METRIBOLONE (MART.)
Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl-
17.BETA.-HYDROXY-17-METHYLESTRA-4,9,11-TRIEN-3-ONE
(8S,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta(a)phenanthren-3-one
DTXCID6014162
17 beta-Hydroxy-17 alpha-methylestra-4,9,11-trien-3-one
Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl-(8CI)
Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)-(9CI)
663-842-3
Metribolona
R1881
17alpha-Methyltrienolone
Metribolonum
R 1881
RU 1881
17-beta-Hydroxy-17-methylestra-4,9,11-trien-3-one
[3H]methyltrienolone
(17BETA)-17-HYDROXY-17-METHYLESTRA-4,9,11-TRIEN-3-ONE
(8S,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one
Ru-1881
Metribolone (1.0mg/ml in Acetonitrile)
MLS002695156
UNII-2C323EGI97
Methyl trienolone
1xow
1e3g
2ao6
Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17b)-
[3H]R1881
[3H]-R1881
17.alpha.-Methyltrienolone
17-.alpha.-Methyltrienolone
SCHEMBL114862
CHEMBL166444
GTPL2857
GTPL3457
CCCIJQPRIXGQOE-XWSJACJDSA-N
GLXC-02541
(1S,3aS,3bS,11aS)-1-hydroxy-1,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,11aH-cyclopenta[a]phenanthren-7-one
NSC92858
BDBM50367916
AKOS015840270
DB02998
AC-32028
R1881, >=98% (HPLC)
A845615
Q3333717
17-.beta.-Hydroxy-17-methylestra-4,11-trien-3-one
17alpha-Methyl-3-oxo-4,9,11-estratrien-17beta-ol
17alpha-methyl-4,9,11,estratrien-17beta-ol-3-one
3-Oxo-17beta-hydroxy-17-methylestra-4,9,11-triene
17alpha-Methyl-17beta-hydroxyestr-4,9,11-trien-3-one
17alpha-Methyl-17beta-hydroxyestra-4,9,11-trien-3-one
Estra-4,11-trien-3-one, 17.beta.-hydroxy-17-methyl-
17alpha-methyl-17beta-hydroxy-estra-4,9,11-trien-3-one
3-Oxo-17beta-hydroxy-17alpha-methylestra-4,9,11-triene
(17beta)-17-hydroxy-17-methyl-estra-4,9,11-triene-3-one
17-beta-hydroxy-17-methylestra-4,9,11-trien-3-one (9CI)
17alpha-Methyl-17beta-hydroxyestra-4,9(10),11-trien-3-one
Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl- (8CI)
17-beta-hydroxy-17-methyl-19-norandrosta-4,9,11-triene-3-one
Estra-4,11-trien-3-one, 17-hydroxy-17-methyl-, (17.beta.)-
Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl- (7CI,8CI)
Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)- (9CI)
17BETA-HYDROXY-17METHYL-19NORANDROSTA-4,9,11-TRIEN-3-ONE
- Zaiter L, Bouheroum M, et al. (2007). Sesquiterpene lactones and other constituents from Matricaria chamomilla L.. Biochemical Systematics and Ecology,2007,35,533-538. [View]
Pubchem:
261000
Cas:
965-93-5
Zinc:
ZINC000003814420
Kegg Ligand:
C14257
Chebi:
379896
Nmrshiftdb2:
70093581
Chembl:
CHEMBL166444
Comptox:
DTXSID8034162
Drugbank:
DB02998
Pdb Ligand:
R18
Bindingdb:
50367916
CPRiL:
7192
SMILES: C1CCC(C12)C3C(C=C2)=C4C(CC3)=CC(=O)CC4
Level: 0
Mol. Weight: 284.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.270
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.65
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.920
- Plasma Protein Binding
- 66.31
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-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
- 10.080
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.280
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.210
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.480
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Toxic
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- 0.440
- Rat (Acute)
- 2.020
- Rat (Chronic Oral)
- 1.700
- Fathead Minnow
- 3.920
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 389.740
- Hydration Free Energy
- -5.630
- Log(D) at pH=7.4
- 2.490
- Log(P)
- 2.81
- Log S
- -4.09
- Log(Vapor Pressure)
- -5.82
- Melting Point
- 153.52
- pKa Acid
- 11.79
- pKa Basic
- 6.06
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9333 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9333 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9290 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9290 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9204 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9204 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8477 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8477 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8403 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8403 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.8377 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.8377 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8363 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8363 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 4 | 0.8192 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 4 | 0.8192 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8115 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8115 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8073 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8073 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7948 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7948 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7917 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7917 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7869 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7869 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7698 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7698 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7688 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7688 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7658 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7658 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7609 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7609 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7543 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7543 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7512 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7512 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7506 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7506 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7436 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7436 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7425 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7425 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7392 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7392 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7371 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7371 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7299 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7299 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7268 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7268 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7255 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7255 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7242 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7242 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 4 | 0.7223 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 4 | 0.7223 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7210 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7210 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7196 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7196 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7193 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7193 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7187 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7187 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7138 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7138 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7115 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7115 |
| Androgen receptor | P19091 | ANDR_MOUSE | Mus musculus | 4 | 0.7111 |
| Androgen receptor | P19091 | ANDR_MOUSE | Mus musculus | 4 | 0.7111 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7100 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7100 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7087 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7087 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7082 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7082 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7038 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7038 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7021 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7021 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7009 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7009 |