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Costunolide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C/C/1=C\[C@H]2OC(=O)C(=C)[C@@H]2CC/C(=C/CC1)/C |
|---|---|
| InChI | InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1 |
| InChIKey | HRYLQFBHBWLLLL-AHNJNIBGSA-N |
| Formula | C15H20O2 |
| HBA | 2 |
| HBD | 0 |
| MW | 232.32 |
| Rotatable Bonds | 0 |
| TPSA | 26.3 |
| LogP | 3.55 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 232.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Magnolia grandiflora | Magnoliaceae | Plantae | 3406 |
| 2 | Centaurea acaulis | Asteraceae | Plantae | 2969722 |
| 3 | Saussurea lappa | Asteraceae | Plantae | 324593 |
Showing of synonyms
Costunolide
553-21-9
(+)-costunolide
Costunlide
Costus lactone
Costunolid
CHEBI:3900
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
(E,E)-6-alpha-Hydroxygermacra-1(10),4,11(13)-trien-12-oic acid gamma-lactone
CCRIS 6754
(10S,1R)-3,7-dimethyl-11-methylene-13-oxabicyclo[8.3.0]trideca-2,6-dien-12-one
(E,E)-germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha-hydroxy-gamma-lactone
(3aS,6E,10E)-3-Methylene-6,10-dimethyl-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-2-one
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
Isocostunolide
NSC 106404
DTXSID001029520
NSC-106404
(10S,1R)-3,7-dimethyl-11-methylene-13-oxabicyclo(8.3.0)trideca-2,6-dien-12-one
(3aS,6E,10E)-3-methylene-6,10-dimethyl-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca(b)furan-2-one
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2(3H)-one
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2(3H)-one
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2-one
Germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha-hydroxy-, gamma-lactone, (E,E)-
DTXCID301514754
(3AS,6E,10E,11AR)-6,10-DIMETHYL-3-METHYLENE-3,3A,4,5,8,9-HEXAHYDROCYCLODECA(B)FURAN-2(11AH)-ONE
Cyclodeca(b)furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS-(3aR*,6E,10E,11aS*))-
683-148-4
Cyclodeca(b)furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS-(3aR*,6E,10E,11aS*))-(9CI)
(3as,11ar)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2-one
(3as,11ar)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
CHEMBL86416
C15H20O2
Melampolide
NSC106404
MFCD00210262
Costunolide (Standard)
SCHEMBL92714
(+)-costunolide\, Costunolid
Costunolide, >=97% (HPLC)
HY-N0036R
HMS3269I17
HMS3413B19
HMS3677B19
EX-A5462
HY-N0036
BDBM50411242
AKOS015840065
AKOS015969714
CS-1487
FC65612
NCGC00381718-02
(3aS,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-6,10-dimethyl-3-methylene-cyclodeca[b]furan-2(3H)-one
AC-28334
AS-17708
C2921
NS00066990
C09382
Q5175227
BRD-K26833429-001-01-0
BRD-K26833429-001-02-8
BRD-K26833429-001-03-6
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS,6E,10E,11aR)-
- 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]
- Abdelgaleil SAM, Hashinaga F (2007). Allelopathic potential of two sesquiterpene lactones from Magnolia grandiflora L.. Biochemical Systematics and Ecology,2007,35(11),737-742. [View]
- Barrero AF, Oltra JE, et al. (2000). New sources and antifungal activity of sesquiterpene lactones. Fitoterapia,2000,71,60-64. [View] [PubMed]
Pubchem:
5281437
Cas:
553-21-9
Gnps:
CCMSLIB00006519838
Zinc:
ZINC000030726859
Kegg Ligand:
C09382
Chebi:
3900
Nmrshiftdb2:
60024312
Metabolights:
MTBLC3900
Chembl:
CHEMBL86416
Bindingdb:
50411242
Selleck:
Costunolide
CPRiL:
58686
SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2
Level: 0
Mol. Weight: 232.32 g/mol
Allelopathic
Antifungal
Absorption
- Caco-2 (logPapp)
- -4.83
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.23
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.55
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.66
- Plasma Protein Binding
- 56.66
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 7.95
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.55
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.35
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.04
- 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
- 3.09
- Rat (Acute)
- 1.77
- Rat (Chronic Oral)
- 1.97
- Fathead Minnow
- 4.59
- 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
- 309.48
- Hydration Free Energy
- -3.73
- Log(D) at pH=7.4
- 2.99
- Log(P)
- 3.71
- Log S
- -4.39
- Log(Vapor Pressure)
- -3.61
- Melting Point
- 58.29
- pKa Acid
- 9.6
- pKa Basic
- 5.97
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8851 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8851 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.8234 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.8234 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.8233 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.8233 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7968 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7968 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7898 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7898 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7871 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7871 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7848 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7848 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7765 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7765 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7742 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7742 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7738 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7738 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7713 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7713 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7708 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7708 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7700 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7700 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7631 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7631 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7610 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7610 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7597 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7597 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7590 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7590 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7566 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7566 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7547 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7547 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7538 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7538 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7518 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7518 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7486 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7486 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7479 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7479 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 2 | 0.7475 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 2 | 0.7475 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7465 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7465 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7426 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7426 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7386 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7386 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7383 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7383 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7331 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7331 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7330 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7330 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7322 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7322 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7319 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7319 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7318 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7318 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7299 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7299 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7279 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7279 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7278 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7278 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7272 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7272 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7257 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7257 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7256 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7256 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7244 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7244 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7229 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7229 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7214 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7214 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7173 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7173 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7172 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7172 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7169 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7169 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7168 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7168 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7154 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7154 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7154 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7154 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7138 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7138 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7126 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7126 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7093 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7093 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7084 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7084 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7071 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7071 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7017 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7017 |