Heitziamide A - Compound Card

Heitziamide A

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Heitziamide A

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Benzodioxole
Canonical Smiles CC(CNC(=O)[C@@H]1CC(=CC[C@H]1c1ccc2c(c1)OCO2)CCC=C(C)C)C
InChI InChI=1S/C24H33NO3/c1-16(2)6-5-7-18-8-10-20(21(12-18)24(26)25-14-17(3)4)19-9-11-22-23(13-19)28-15-27-22/h6,8-9,11,13,17,20-21H,5,7,10,12,14-15H2,1-4H3,(H,25,26)/t20-,21+/m0/s1
InChIKey HCTXZDQPRLPYOB-LEWJYISDSA-N
Formula C24H33NO3
HBA 3
HBD 1
MW 383.53
Rotatable Bonds 7
TPSA 47.56
LogP 5.35
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 383.25
Number of Lipinski Rule Violations 1
# 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: 44513068
Nmrshiftdb2: 60075741

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)C3CC=CCC3

Level: 1

Mol. Weight: 383.53 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 383.53 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 383.53 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.49
Plasma Protein Binding
100.56
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.63
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.04
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.07
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
Safe
T. Pyriformis
-9.4
Rat (Acute)
2.16
Rat (Chronic Oral)
1.93
Fathead Minnow
4.67
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
427.64
Hydration Free Energy
-5.73
Log(D) at pH=7.4
4.09
Log(P)
6.2
Log S
-5.79
Log(Vapor Pressure)
-7.5
Melting Point
97.22
pKa Acid
10.38
pKa Basic
5.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9529
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.9525
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9100
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8898
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8797
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8756
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8719
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8710
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8661
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8629
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8610
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8599
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8592
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8554
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8449
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8403
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8326
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8285
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8192
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8186
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8170
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8164
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8145
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8135
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8113
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.8059
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8035
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8017
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8001
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7997
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7983
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7979
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7943
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7934
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7933
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7897
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7880
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7816
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7813
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7796
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7777
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7774
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7763
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7759
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7737
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7733
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7724
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7700
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7676
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7667
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7667
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7637
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7625
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7616
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7615
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7603
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7603
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7596
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7576
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7574
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7570
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7546
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7542
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7530
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7507
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7481
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7469
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7461
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7461
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7461
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7458
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7433
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7423
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7422
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7421
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7416
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7414
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7410
Virginiamycin A acetyltransferase P26839 VATA_STAAU Staphylococcus aureus 4 0.7392
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7379
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7367
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7360
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7359
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7357
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7350
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7341
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7331
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7323
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7319
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7309
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7309
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7307
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7296
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7275
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7274
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7271
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7269
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7263
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7251
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7250
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7236
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7233
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7203
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7203
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7202
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7190
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 2 0.7183
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7178
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7176
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7176
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7174
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7173
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7164
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7163
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7160
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7152
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7145
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 3 0.7139
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7134
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7125
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7120
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7115
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7110
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7108
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7098
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7090
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7086
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7079
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7073
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7060
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7044
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7036
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7030
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7026
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7026
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7024
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7024
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7022
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7019
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7018
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7017
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7016
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7006
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7005
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7004
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7001

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