7- hydroxy-labda-8(17),13(16),14-trien-19-yl-7’-O-methyl-(E)-coumarate - Compound Card

7- hydroxy-labda-8(17),13(16),14-trien-19-yl-7’-O-methyl-(E)-coumarate

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7- hydroxy-labda-8(17),13(16),14-trien-19-yl-7’-O-methyl-(E)-coumarate

Structure
Zoomed Structure
  • Family: Araucariaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles C=CC(=C)CC[C@H]1C(=C)[C@@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)COC(=O)/C=C/c1ccc(cc1)OC
InChI InChI=1S/C30H40O4/c1-7-21(2)9-15-25-22(3)26(31)19-27-29(4,17-8-18-30(25,27)5)20-34-28(32)16-12-23-10-13-24(33-6)14-11-23/h7,10-14,16,25-27,31H,1-3,8-9,15,17-20H2,4-6H3/b16-12+/t25-,26-,27-,29+,30+/m0/s1
InChIKey SCNSPEWZQZSSIK-ZGFXGWPZSA-N
Formula C30H40O4
HBA 4
HBD 1
MW 464.65
Rotatable Bonds 9
TPSA 55.76
LogP 6.52
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 464.29
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]
Pubchem: 132504630

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 310.44 g/mol

Structure

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

Level: 0

Mol. Weight: 150.26 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
98.65
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.87
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.0
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.17
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
-143.06
Rat (Acute)
3.8
Rat (Chronic Oral)
2.64
Fathead Minnow
4.52
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
476.49
Hydration Free Energy
-2.78
Log(D) at pH=7.4
5.79
Log(P)
6.52
Log S
-6.57
Log(Vapor Pressure)
-8.51
Melting Point
120.36
pKa Acid
10.84
pKa Basic
5.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9223
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8980
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8961
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8948
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8841
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8650
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8589
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8585
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8581
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8494
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8268
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7756
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7743
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7719
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7684
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7665
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7633
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7620
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7595
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7585
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7569
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7569
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7558
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7556
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7537
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7536
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7495
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7482
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7477
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7470
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7462
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7448
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7431
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7422
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7409
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7407
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7407
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7406
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7404
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7389
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7385
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7380
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7378
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7375
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7373
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7373
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7373
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7369
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7361
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7354
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7342
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7341
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7334
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7326
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7321
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7313
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7311
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7308
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7307
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7302
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7290
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7285
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7282
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7273
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7269
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7259
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7242
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7241
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7229
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7225
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7221
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7218
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7217
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7214
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 2 0.7213
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7210
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7210
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7208
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7205
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7195
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7194
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7193
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7193
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7192
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7192
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7185
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7181
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7179
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7175
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 2 0.7170
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7167
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7159
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7156
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7155
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7151
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7148
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7141
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7137
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7134
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7130
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7124
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7123
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7120
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7120
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7116
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7115
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7114
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7109
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7103
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7102
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7092
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7088
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7085
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7070
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7068
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7061
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7060
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7060
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7059
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7057
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7042
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7040
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7039
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7030
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7020
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7020
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7016
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7010
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7010
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7009
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 2 0.7006

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