7-hydroxylabda-8(17),13(16),14-trien-19-yl-(Z)-coumarate - Compound Card

7-hydroxylabda-8(17),13(16),14-trien-19-yl-(Z)-coumarate

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7-hydroxylabda-8(17),13(16),14-trien-19-yl-(Z)-coumarate

Structure
Zoomed Structure
  • Family: Plantae - Araucariaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles C=CC(=C)CC[C@H]1C(=C)[C@@H](O)CC2[C@]1(C)CCC[C@]2(C)COC(=O)/C=C\c1ccc(cc1)O
InChI InChI=1S/C29H38O4/c1-6-20(2)8-14-24-21(3)25(31)18-26-28(4,16-7-17-29(24,26)5)19-33-27(32)15-11-22-9-12-23(30)13-10-22/h6,9-13,15,24-26,30-31H,1-3,7-8,14,16-19H2,4-5H3/b15-11-/t24-,25-,26?,28+,29+/m0/s1
InChIKey QNRUJSRLFGSDSM-BZCLDTFKSA-N
Formula C29H38O4
HBA 4
HBD 2
MW 450.62
Rotatable Bonds 8
TPSA 66.76
LogP 6.22
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 450.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Araucaria bidwillii Araucariaceae Plantae 56993

Showing of synonyms

  • Ebada S, Talaat A, et al. (2017). Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. Tetrahedron, 2017, 73(21), 3048-3055. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(C23)CC(=C)CC3

Level: 1

Mol. Weight: 450.62 g/mol

Structure

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

Level: 0

Mol. Weight: 450.62 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.23
Plasma Protein Binding
94.29
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.51
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.0
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
-83.39
Rat (Acute)
3.28
Rat (Chronic Oral)
2.57
Fathead Minnow
4.35
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
466.75
Hydration Free Energy
-2.74
Log(D) at pH=7.4
5.33
Log(P)
6.1
Log S
-6.43
Log(Vapor Pressure)
-8.98
Melting Point
125.1
pKa Acid
9.86
pKa Basic
4.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9493
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9336
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9029
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8963
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8956
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8943
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8512
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8493
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8422
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8405
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8395
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8340
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8326
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8245
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8208
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8152
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8128
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.8125
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8084
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8029
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8014
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7894
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7881
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7878
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7865
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7842
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7785
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7778
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7748
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7738
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7708
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7663
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7637
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 3 0.7630
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7617
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7598
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7562
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7560
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7549
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.7545
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7525
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7519
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7515
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7504
Genome polyprotein A9LIE0 A9LIE0_9FLAV dengue virus type 3 3 0.7493
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7464
Genome polyprotein Q8QL64 Q8QL64_9FLAV Modoc virus 3 0.7461
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7438
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7426
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7419
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7400
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7391
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7388
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7386
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7383
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7379
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7378
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7377
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7365
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7365
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7358
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7355
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7353
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7350
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7337
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7332
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7315
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7312
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7311
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7309
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7307
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7294
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7294
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7291
Genome polyprotein Q6YMS4 POLG_DEN3S Dengue virus type 3 3 0.7288
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7278
Mevalonate kinase P17256 KIME_RAT Rattus norvegicus 3 0.7272
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 2 0.7271
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7266
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7264
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7259
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7258
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7250
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7245
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7241
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7234
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7234
Argininosuccinate synthase P59846 ASSY_THET8 Thermus thermophilus 3 0.7226
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7222
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7215
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7213
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7209
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7207
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7198
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7197
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7190
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7188
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7185
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7183
Argininosuccinate synthase P59846 ASSY_THET8 Thermus thermophilus 3 0.7160
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7156
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7153
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7152
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7151
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7148
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7146
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7139
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7137
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7135
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7131
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7128
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7128
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 2 0.7124
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7117
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7115
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7115
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7107
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7104
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7104
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7102
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7101
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7096
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7093
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7090
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7089
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2 O95340 PAPS2_HUMAN Homo sapiens 2 0.7083
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 2 0.7083
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7082
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7072
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 4 0.7070
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7068
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7067
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7066
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7065
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7064
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7063
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7060
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7059
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7056
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7051
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7050
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7049
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7043
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7041
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7040
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7037
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 2 0.7034
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7032
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7029
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7024
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7024
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7023
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7022
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7021
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7010
Chromosome partitioning protein ParA B0ZE06 B0ZE06_ECOLX Escherichia coli 3 0.7006
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7001
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7001

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