2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one - Compound Card

2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one

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2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanosesquiterpene
Canonical Smiles CO[C@@H]1C[C@@H](C)CC(=O)c2c(C/C(=C\1)/C)occ2C
InChI InChI=1S/C16H22O3/c1-10-5-13(18-4)6-11(2)8-15-16(14(17)7-10)12(3)9-19-15/h6,9-10,13H,5,7-8H2,1-4H3/b11-6-/t10-,13-/m1/s1
InChIKey JUFDIKOOORFASQ-LIZARLNVSA-N
Formula C16H22O3
HBA 3
HBD 0
MW 262.35
Rotatable Bonds 1
TPSA 39.44
LogP 3.7
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 262.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Commiphora sphaerocarpa Burseraceae Plantae 318987

Showing of synonyms

  • Dekebo A, Dagne E, et al. (2000). Crystal structures of two furanosesquiterpenes from Commiphora sphaerocarpa. Tetrahedron Letters,2000,41(50),9875-9878. [View] [PubMed]
Pubchem: 44576244

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)CC=CCCCCC2=O

Level: 0

Mol. Weight: 262.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.380
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.850
Plasma Protein Binding
57.61
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.080
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.200
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.240
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.110
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
0.540
Rat (Acute)
2.560
Rat (Chronic Oral)
2.110
Fathead Minnow
4.160
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
325.830
Hydration Free Energy
-6.630
Log(D) at pH=7.4
2.560
Log(P)
3.91
Log S
-2.91
Log(Vapor Pressure)
-5.2
Melting Point
69.0
pKa Acid
9.21
pKa Basic
4.93
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 0.9395
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9395
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9358
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9358
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8957
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8957
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8349
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8349
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8328
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8328
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8289
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8289
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8272
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8272
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8265
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8265
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8246
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8246
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8216
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8216
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8157
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8157
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8112
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8112
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.8091
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.8091
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8051
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8051
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8004
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8004
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7903
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7903
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7864
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7864
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7807
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7807
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7788
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7788
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7785
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7785
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7748
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7748
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7743
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7743
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7711
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7711
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7689
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7689
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7682
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7682
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7682
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7682
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7680
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7680
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7675
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7675
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7645
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7645
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7632
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7632
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7627
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7627
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7611
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7611
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7554
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7554
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7546
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7546
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7545
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7545
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7533
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7533
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7502
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7502
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7501
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7501
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7492
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7492
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7480
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7480
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7478
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7478
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7465
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7465
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7461
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7461
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7436
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7436
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7343
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7343
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7341
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7321
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7321
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7314
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7314
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7308
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7308
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7305
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7305
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7281
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7281
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7276
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7276
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7276
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7276
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7255
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7255
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7254
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7254
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7230
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7230
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7220
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7220
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7201
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7201
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7201
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7201
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7195
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7195
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7190
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7190
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7183
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7183
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7159
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7159
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7155
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7155
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7154
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7154
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7145
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7145
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7117
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7117
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7111
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7111
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7104
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7104
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7098
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7098
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7077
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7077
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7063
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7063
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7061
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7061
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7053
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7053
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7042
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7042
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7020
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7020
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7000
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7000

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