Heitziamide B - Compound Card

Heitziamide B

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Heitziamide B

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Benzodioxole
Canonical Smiles CC(CNC(=O)/C=C/c1cc(O)c2c(c1)OCO2)C
InChI InChI=1S/C14H17NO4/c1-9(2)7-15-13(17)4-3-10-5-11(16)14-12(6-10)18-8-19-14/h3-6,9,16H,7-8H2,1-2H3,(H,15,17)/b4-3+
InChIKey DHMCGPVUHSTCIP-ONEGZZNKSA-N
Formula C14H17NO4
HBA 4
HBD 2
MW 263.29
Rotatable Bonds 4
TPSA 67.79
LogP 1.91
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 263.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fagara heitzii Rutaceae Plantae —

Showing of synonyms

  • Mbaze LM, Lado JA, et al. (2009). Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae).. Phytochemistry,2009, 70(11-12), 1442-1447. [View] [PubMed]
Pubchem: 44513069
Nmrshiftdb2: 60075740

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 263.29 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
38.14
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
11.04
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.58
Micronucleos
Toxic
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
4.05
Rat (Acute)
2.07
Rat (Chronic Oral)
1.8
Fathead Minnow
4.2
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
367.15
Hydration Free Energy
-11.41
Log(D) at pH=7.4
2.19
Log(P)
2.9
Log S
-3.27
Log(Vapor Pressure)
-6.31
Melting Point
155.26
pKa Acid
8.16
pKa Basic
4.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.9561
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9474
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9277
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9268
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9267
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9243
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9231
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9229
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9091
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9050
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8982
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8953
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8880
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8811
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8789
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8717
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8679
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8652
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8597
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8595
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8587
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8549
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8549
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8530
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8518
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8507
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8477
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8449
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8448
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8420
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.8410
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8384
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8336
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8304
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8256
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8255
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8247
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8245
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8240
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8206
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8204
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8203
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8190
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8174
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.8167
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8085
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8073
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8070
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8037
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8009
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7898
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7887
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7855
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7825
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7812
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7776
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7760
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7746
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7673
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7669
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7627
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7625
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7610
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7594
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7593
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7579
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7561
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7559
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7544
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7519
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7507
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7494
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7423
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7416
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7357
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7321
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7294
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7260
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7227
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7225
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7219
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7216
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7215
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7196
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7195
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7186
CDP-alcohol phosphatidyltransferase AF-2299-like N-terminal domain-containing protein O27985 O27985_ARCFU Archaeoglobus fulgidus 4 0.7178
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7167
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7166
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7163
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7157
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7150
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7145
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7143
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7139
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7133
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7125
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7125
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7118
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7116
Type II methyltransferase M.HhaI P05102 MTH1_HAEPH Haemophilus parahaemolyticus 3 0.7111
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7098
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7074
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7064
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7063
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7057
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7051
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7047
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7042
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7038
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7038
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7033
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7032
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7023
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7023
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7022
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7010
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7003
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7003

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