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Santamarin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC1=CC[C@H]([C@]2([C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CC2)C)O |
|---|---|
| InChI | InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1 |
| InChIKey | PLSSEPIRACGCBO-PFFFPCNUSA-N |
| Formula | C15H20O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 248.32 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 2.21 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 248.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea acaulis | Asteraceae | Plantae | 2969722 |
Showing of synonyms
Santamarin
Santamarine
UNII-15D6KW291H
CHEBI:9023
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one
15D6KW291H
(3aS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-Decahydro-6alpha-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one
Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-
Eudesma-3,11(13)-dien-12-oic acid, 1beta,6alpha-dihydroxy-, gamma-lactone
Eudesma-3,11(13)-dien-12-oic acid, 1.beta.,6.alpha.-dihydroxy-, .gamma.-lactone
(3aS,5aR,6R,9aS,9bS)-6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one
NAPHTHO(1,2-B)FURAN-2(3H)-ONE, 3A,4,5,5A,6,7,9A,9B-OCTAHYDRO-6-HYDROXY-5A,9-DIMETHYL-3-METHYLENE-, (3AS-(3A.ALPHA.,5A.BETA.,6.BETA.,9A.ALPHA.,9B.BETA.))-
Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS-(3aalpha,5abeta,6beta,9aalpha,9bbeta))-
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6a-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2-one
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6a-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6alpha-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2-one
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6I+--hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2-one
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6I+--hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one
(3AS,5ar,6R,9as,9BS)-6-hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho(1,2-b)furan-2-one
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho(1,2-b)furan-2(3H)-one
Naphtho[1,2-b]furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-
Naphtho[1,2-b]furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, [3aS-(3a.alpha.,5a.beta.,6.beta.,9a.alpha.,9b.beta.)]-
(3aS,5aR,6R,9aS,9bS)-6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho(1,2-b)furan-2(3H)-one
(3aS,5aR,6R,9aS,9bS)-6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one
Plssepiracgcbo-uhfffaoysa-n
4290-13-5
Balchanin
(+)-santamarine
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
(3aS,5aR,6R,9aS,9bS)-3a,4,5,5a,6,7,9a,9b-Octahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2(3H)-one
CHEMBL89311
SCHEMBL2551388
DTXSID70911513
HY-N1326
AKOS032948408
FS-9890
CS-0016730
NS00094017
C09544
Q27089375
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g]benzofuran-2-one
(3AS,5AR,6R,9AS,9BS)-6-HYDROXY-5A,9-DIMETHYL-3-METHYLIDENE-2H,3H,3AH,4H,5H,5AH,6H,7H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2-ONE
Naphthol]1,2-b]furan-2(3H)-one,3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene
- Bentamène A, Benayache S, et al. (2005). A new guaianolide and other sesquiterpene lactones from Centaurea acaulis L. (Asteraceae). Biochemical Systematics and Ecology,2005,33,1061-1065. [View]
Pubchem:
188297
Cas:
4290-13-5
Zinc:
ZINC000004098178
Kegg Ligand:
C09544
Chebi:
9023
Nmrshiftdb2:
60030983
Chembl:
CHEMBL89311
CPRiL:
233652
SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCC=C3
Level: 0
Mol. Weight: 248.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.4
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.57
- Plasma Protein Binding
- 43.95
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.02
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.17
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.06
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.94
- 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
- 0.82
- Rat (Acute)
- 2.74
- Rat (Chronic Oral)
- 1.68
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 334.48
- Hydration Free Energy
- -6.17
- Log(D) at pH=7.4
- 1.76
- Log(P)
- 1.89
- Log S
- -2.49
- Log(Vapor Pressure)
- -5.43
- Melting Point
- 143.03
- pKa Acid
- 9.52
- pKa Basic
- 6.41
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8058 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8058 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8056 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8056 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7743 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7743 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7332 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7332 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7150 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7150 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7105 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7105 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7042 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7042 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7030 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7030 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7026 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7026 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7016 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7016 |