Acetyldrimartol B - Compound Card

Acetyldrimartol B

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Acetyldrimartol B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Sesquiterpene-Coumarin Ether
Canonical Smiles COc1cc2ccc(=O)oc2c(c1OC[C@H]1C(=CC[C@@H]2[C@@]1(C)CCC(C2(C)C)OC(=O)C)C)OC
InChI InChI=1S/C28H36O7/c1-16-8-10-21-27(3,4)22(34-17(2)29)12-13-28(21,5)19(16)15-33-25-20(31-6)14-18-9-11-23(30)35-24(18)26(25)32-7/h8-9,11,14,19,21-22H,10,12-13,15H2,1-7H3/t19-,21-,22?,28-/m0/s1
InChIKey YMIXTMQQHRBULF-QHENICFISA-N
Formula C28H36O7
HBA 7
HBD 0
MW 484.59
Rotatable Bonds 6
TPSA 84.2
LogP 5.53
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 484.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Brocchia cinerea Asteraceae Plantae 282208

Showing of synonyms

  • Greger H, Hofer O (1985). Sesquiterpene-coumarin ethers and polyacetylenes from Brocchia cinerea.. Phytochemistry,1985,24(1),85-88. [View]
Pubchem: 163010842

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)cc(cc2)OCC3C=CCC(C34)CCCC4

Level: 1

Mol. Weight: 484.59 g/mol

Structure

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

Level: 0

Mol. Weight: 484.59 g/mol

Structure

SMILES: C1C=CCC(C12)CCCC2

Level: 0

Mol. Weight: 484.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.480
Plasma Protein Binding
94.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.290
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.140
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
-244.640
Rat (Acute)
2.350
Rat (Chronic Oral)
1.530
Fathead Minnow
5.270
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
487.490
Hydration Free Energy
-2.850
Log(D) at pH=7.4
4.090
Log(P)
5.5
Log S
-6.02
Log(Vapor Pressure)
-7.96
Melting Point
123.78
pKa Acid
8.16
pKa Basic
5.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9198
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9198
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9117
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9117
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8706
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8706
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8686
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8686
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8666
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8666
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8563
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8563
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8489
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8489
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8459
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8459
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8411
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8411
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8247
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8247
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8244
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8244
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8190
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8190
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8178
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8178
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8093
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8093
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8091
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8091
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8079
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8011
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7966
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7966
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7891
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7891
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7881
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7881
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7825
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7825
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7646
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7646
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7645
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7645
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7636
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7636
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7626
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7626
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7581
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7581
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7568
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7568
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7537
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7537
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7505
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7505
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7488
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7488
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7466
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7466
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7456
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7456
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7451
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7451
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7426
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7426
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7425
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7425
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7408
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7408
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7403
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7403
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7393
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7393
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7393
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7393
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7392
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7392
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7387
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7387
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7379
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7379
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7339
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7339
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7314
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7314
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7305
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7305
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7302
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7302
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7295
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7295
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7289
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7289
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7287
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7287
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7259
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7259
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7229
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7229
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7218
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7218
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7210
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7210
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7204
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7204
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7185
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7185
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7175
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7175
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7164
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7164
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7137
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7137
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7107
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7107
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7106
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7106
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7090
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7090
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7084
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7084
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7076
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7076
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7069
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7069
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7045
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7045
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7044
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7044
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7044
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7044
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7024
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7024
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7023
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7023
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7020
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7020
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7019
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7019
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7003
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7003

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