Fissinolide - Compound Card

Fissinolide

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Fissinolide

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C)[C@H]2C(=O)[C@]1(C)[C@H]1CC[C@@]3(C(=C1C2)CC(=O)O[C@H]3c1ccoc1)C
InChI InChI=1S/C29H36O8/c1-15(30)36-26-18-11-17-19(29(5,24(18)33)21(27(26,2)3)13-22(31)34-6)7-9-28(4)20(17)12-23(32)37-25(28)16-8-10-35-14-16/h8,10,14,18-19,21,25-26H,7,9,11-13H2,1-6H3/t18-,19+,21+,25+,26-,28-,29-/m1/s1
InChIKey YOTCKRFNSMJTGD-VRYGVUSESA-N
Formula C29H36O8
HBA 8
HBD 0
MW 512.6
Rotatable Bonds 4
TPSA 109.11
LogP 4.73
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 512.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Khaya senegalensis Meliaceae Plantae 587579

Showing of synonyms

  • Khalid SA, Friedrichsen GM, et al. (1998). Limonoids from Khaya senegalensis. Phytochemistry,1998,49(6),1769-1772. [View] [PubMed]
Pubchem: 101286288
Nmrshiftdb2: 60049522

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C2)C3CCC(C4=C23)C5C(=O)C(C4)CCC5

Level: 1

Mol. Weight: 512.6 g/mol

Structure

SMILES: C1C(=O)OCC(C1=C23)CCC2C4C(=O)C(C3)CCC4

Level: 0

Mol. Weight: 512.6 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 512.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
79.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.990
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.050
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.170
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.960
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-892.260
Rat (Acute)
3.780
Rat (Chronic Oral)
2.500
Fathead Minnow
5.900
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
479.140
Hydration Free Energy
-2.810
Log(D) at pH=7.4
3.530
Log(P)
2.94
Log S
-5.63
Log(Vapor Pressure)
-8.99
Melting Point
232.22
pKa Acid
7.87
pKa Basic
3.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9011
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9011
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8957
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8957
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8928
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8928
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8891
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8891
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8772
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8772
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8750
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8750
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8702
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8702
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8686
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8686
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8633
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8633
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8310
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8310
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8211
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8211
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8204
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8204
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7943
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7943
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7939
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7939
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7855
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7855
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7781
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7781
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7775
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7775
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7724
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7724
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7697
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7697
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7696
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7696
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7675
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7675
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7573
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7573
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7465
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7465
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7446
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7446
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7442
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7442
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7441
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7441
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7414
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7414
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7408
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7408
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7395
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7395
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7384
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7384
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7344
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7344
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7335
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7335
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7278
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7278
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7275
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7275
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7263
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7263
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7244
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7244
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7239
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7239
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7209
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7209
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7198
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7198
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7162
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7162
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7153
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7153
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7150
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7150
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7129
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7129
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7129
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7129
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7127
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7127
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7094
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7094
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7085
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7085
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 2 0.7077
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 2 0.7077
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7077
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7077
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7075
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7075
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7060
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7060
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7044
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7044
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7040
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7040
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7010
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7010
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7009
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7009

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