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Brefeldin A
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Lactone
| Canonical Smiles | O[C@@H]1C[C@@H]2[C@@H](C1)/C=C/CCC[C@@H](OC(=O)/C=C/[C@H]2O)C |
|---|---|
| InChI | InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1 |
| InChIKey | KQNZDYYTLMIZCT-KQPMLPITSA-N |
| Formula | C16H24O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 280.36 |
| Rotatable Bonds | 0 |
| TPSA | 66.76 |
| LogP | 1.96 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.69 |
| Exact Mass | 280.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Penicillium sp. | Trichocomaceae | Fungi | 5081 |
Showing of synonyms
Brefeldin A
Ascotoxin
Decumbin
Cyanein
20350-15-6
Synergisidin
Nectrolide
Cyanaein
(+)-Brefeldin A
Brefeldin A prodrug
NSC-89671
CCRIS 9386
XG0D35F9K6
CHEBI:48080
NSC 56310
NSC 89671
NSC-56310
BREFELDIN A [MI]
NSC-107456
NSC-244390
NSC 107456
NSC 244390
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
NSC89671
(1R,2R,3E,7S,11E,13S,15S)-2,15-dihydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-dien-5-one
(1S,2E,7S,10E,12R,13R,15S)-12,15-dihydroxy-7-methyl-8-oxabicyclo[11.3.0]hexadeca-2,10-dien-9-one
4H-Cyclopent(f)oxacyclotridecin-4-one,1,6,7,8,9,11a-beta,12,13,14,14a-alpha-decahydro-1-beta-13-alpha-dihydroxy-6-beta-methyl-
60132-23-2
4H-Cyclopent(f)oxacyclotridecin-4-one, 1,6,7,8,9,11a-beta,12,13,14,14a-alpha-decahydro-1-beta-13-alpha-dihydroxy-6-beta-methyl-
DTXSID00880041
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta(f)oxacyclotridecin-4-one
(1R,2R,3E,7S,11E,13S,15S)-2,15-dihydroxy-7-methyl-6-oxabicyclo(11.3.0)hexadeca-3,11-dien-5-one
(1S,2E,7S,10E,12R,13R,15S)-12,15-dihydroxy-7-methyl-8-oxabicyclo(11.3.0)hexadeca-2,10-dien-9-one
1,6,7,8,9,11a,12,13,14,14a-Decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent[f]oxacyclotridecin-4-one
DTXCID001022598
1,6,7,8,9,11a,12,13,14,14a-Decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent(f)oxacyclotridecin-4-one
4H-Cyclopent(f)oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-
606-528-3
951-399-1
Brefeldin-A
Bredfeldin A
MLS001074108
SMR000653527
Pfizer B 174987
Antibiotic from Penicillium cyaneum
4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-
SR-01000000180
MLS002701937
MLS002702862
UNII-XG0D35F9K6
NSC107456
NSC244390
Gamma,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid lambda-lactone
4H-CYCLOPENT(F)OXACYCLOTRIDECIN-4-ONE, 1,6,7,8,9,11A,12,13,14,14A-DECAHYDRO-1,13-DIHYDROXY-6-METHYL-, (1R,2E,6S,10E,11AS,13S,14AR)-
B 174987
Probes1_000313
SCHEMBL29267
MLS002153500
CHEMBL19980
PFIZER B174987
BDBM97307
Cid_5287620
KQNZDYYTLMIZCT-KQPMLPITSA-N
HMS2233O20
BFA
EX-A5726
S7046
AKOS030526113
AB15917
CCG-208161
CS-3783
DB07348
NCGC00022909-02
HY-16592
SMR000768725
TOXIC SOLID, N.O.S. (BREFELDIN A)
SW220015-1
C73840
Q168790
SR-01000000180-5
SR-01000000180-7
BRD-K77841042-001-11-7
BRD-K77841042-001-14-1
Brefeldin A, from Penicillium brefeldianum, >=99% (HPLC and TLC)
Brefeldin A, >=99% (HPLC and TLC), BioXtra, for molecular biology
(1S,2E,7S,10E,12R,13R,15S)-7-methyl-12,15-bis(oxidanyl)-8-oxabicyclo[11.3.0]hexadeca-2,10-dien-9-one
11006-23-8
4H-Cyclopent[f]oxacyclotridecin-4-one,6,7,8,9,11a,12,13, 14,14a-decahydro-1,13-dihydroxy-6-methyl-, [1R-(1R*,2E,6S*, 10E,11aS*,13S*,14aR*)]-
4H-Cyclopent[f]oxacyclotridecin-4-one,6,7,8,9,11a.beta.,12,13,14,14a.alpha.-decahydro- 1.beta.,13.alpha.-dihydroxy-6.beta.-methyl-
Pfizer B 174987 4H-Cyclopent[f]oxacyclotridecin-4-one,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-
Pubchem:
5287620
Cas:
20350-15-6
Gnps:
CCMSLIB00000215907
Zinc:
ZINC000012371944
Chebi:
48080
Nmrshiftdb2:
60059372
Metabolights:
MTBLC48080
Chembl:
CHEMBL19980
Comptox:
DTXSID00880041
Drugbank:
DB07348
Pdb Ligand:
AFB
Bindingdb:
97307
CPRiL:
5029
SMILES: C1CCC(C12)CC=CC(=O)OCCCCC=C2
Level: 0
Mol. Weight: 280.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.54
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 40.98
- 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
- 2.16
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.68
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.16
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.99
- 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
- -3.01
- Rat (Acute)
- 2.72
- Rat (Chronic Oral)
- 1.87
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 387.19
- Hydration Free Energy
- -9.71
- Log(D) at pH=7.4
- 1.73
- Log(P)
- 1.53
- Log S
- -3.33
- Log(Vapor Pressure)
- -6.7
- Melting Point
- 148.47
- pKa Acid
- 8.59
- pKa Basic
- 6.48
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8965 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.8490 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8088 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8007 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7191 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7113 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7112 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7022 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7011 |