Marmaricin - Compound Card

Marmaricin

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Marmaricin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Sesquiterpenoid Coumarin
Canonical Smiles C=C1CCC2C([C@@H]1COc1ccc3c(c1)oc(=O)cc3)(C)CCC(C2(C)C)O
InChI InChI=1S/C24H30O4/c1-15-5-9-20-23(2,3)21(25)11-12-24(20,4)18(15)14-27-17-8-6-16-7-10-22(26)28-19(16)13-17/h6-8,10,13,18,20-21,25H,1,5,9,11-12,14H2,2-4H3/t18-,20?,21?,24?/m1/s1
InChIKey FCWYNTDTQPCVPG-FLEJBNJMSA-N
Formula C24H30O4
HBA 4
HBD 1
MW 382.5
Rotatable Bonds 3
TPSA 59.67
LogP 4.94
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 382.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula marmarica Apiaceae Plantae 1514035

Showing of synonyms

  • Dawidar AA, Abu-Mustafa E, et al. (1979). Marmaricin, a new sesquiterpenoid coumarin from Ferula marmarica L.. Chemical and Pharmaceutical Bulletin,1979,27(12),3153-3155. [View]
Pubchem: 162922419
Nmrshiftdb2: 70112896

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCC(=C)C2COc(cc3)cc(c34)oc(=O)cc4

Level: 1

Mol. Weight: 382.5 g/mol

Structure

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 382.5 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 382.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.31
Plasma Protein Binding
76.11
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.87
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.23
Micronucleos
Safe
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
Toxic
T. Pyriformis
-6.81
Rat (Acute)
2.97
Rat (Chronic Oral)
1.61
Fathead Minnow
4.59
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
451.11
Hydration Free Energy
-5.14
Log(D) at pH=7.4
4.17
Log(P)
4.89
Log S
-5.68
Log(Vapor Pressure)
-8.1
Melting Point
149.7
pKa Acid
7.68
pKa Basic
7.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9755
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9755
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9567
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9567
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9522
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9522
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9486
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9486
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9409
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9409
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9216
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9216
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8945
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8945
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8813
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8813
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8531
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8417
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8417
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8364
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8364
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8283
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8283
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8138
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8138
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8114
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8114
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7932
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7932
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7916
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7916
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7896
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7896
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7863
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7863
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7806
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7806
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7722
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7722
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7720
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7720
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7719
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7719
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7688
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7688
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7686
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7686
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7664
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7664
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7660
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7660
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7650
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7650
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7642
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7642
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7625
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7625
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7623
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7623
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7608
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7608
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7607
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7607
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7563
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7563
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7555
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7555
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7548
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7548
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7531
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7531
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7526
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7526
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7524
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7524
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7523
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7523
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7496
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7496
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7493
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7493
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7461
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7461
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7458
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7458
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7449
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7449
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7449
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7449
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7444
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7444
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7431
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7431
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7416
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7416
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7415
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7415
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7414
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7414
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7394
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7394
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7390
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7390
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7383
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7383
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7377
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7377
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7369
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7369
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7357
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7357
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7335
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7335
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7329
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7329
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7324
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7324
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7317
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7317
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7270
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7270
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7256
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7256
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7251
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7251
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7222
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7222
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7219
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7219
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7216
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7216
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7211
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7211
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7210
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7210
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7152
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7152
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7150
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7150
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7149
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7149
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7148
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7148
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7148
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7148
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7128
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7128
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7121
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7121
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7119
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7119
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7109
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7109
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7107
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7107
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7091
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7091
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7054
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7054
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7041
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7041
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7007
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7007
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7007
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7007

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