Gardenifolin H - Compound Card

Gardenifolin H

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Gardenifolin H

Structure
Zoomed Structure
  • Family: Rubiaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles COC(=O)/C=C/c1cc(OC)c2c(c1)[C@H](CO)[C@@H](O2)c1ccc(c(c1)O)OC
InChI InChI=1S/C21H22O7/c1-25-17-6-5-13(10-16(17)23)20-15(11-22)14-8-12(4-7-19(24)27-3)9-18(26-2)21(14)28-20/h4-10,15,20,22-23H,11H2,1-3H3/b7-4+/t15-,20-/m0/s1
InChIKey FULHECCATAOIBE-NLYDTBBBSA-N
Formula C21H22O7
HBA 7
HBD 2
MW 386.4
Rotatable Bonds 6
TPSA 94.45
LogP 2.81
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 386.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gardenia ternifolia Rubiaceae Plantae 1237590

Showing of synonyms

  • Tshitenge DT, Feineis D, et al. (2017). Gardenifolins A-H, Scalemic Neolignans from Gardenia ternifolia: Chiral Resolution, Configurational Assignment, and Cytotoxic Activities against the HeLa Cancer Cell Line.. Journal of natural products,2017, 80(5), 1604-1614. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 196.25 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 120.15 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
78.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
10.010
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.740
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.500
Micronucleos
Toxic
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
-10.190
Rat (Acute)
2.190
Rat (Chronic Oral)
2.730
Fathead Minnow
4.960
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
451.940
Hydration Free Energy
-6.720
Log(D) at pH=7.4
3.420
Log(P)
2.18
Log S
-4.26
Log(Vapor Pressure)
-8.26
Melting Point
156.27
pKa Acid
8.55
pKa Basic
2.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9333
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9176
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9130
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9106
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9033
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8971
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8907
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8905
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8889
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8882
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8876
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8831
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8697
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8636
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8579
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8571
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.8533
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8527
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8526
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8444
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8438
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8388
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8366
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8240
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8236
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8135
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8114
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8110
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8060
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8027
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8026
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8026
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8014
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7921
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7916
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7881
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7820
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7769
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7768
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7695
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7659
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7651
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7648
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7640
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7639
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7635
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7632
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7621
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7612
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7606
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7603
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7593
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7577
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7542
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7541
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7495
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7484
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7471
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7468
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7456
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7448
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7441
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7437
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7423
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7421
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7416
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7393
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7375
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7367
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7360
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7360
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7346
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7343
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7340
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7334
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7332
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7309
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7304
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7295
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7294
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7292
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7285
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7264
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7248
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7236
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7228
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7222
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7220
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7215
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7214
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7210
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7185
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7178
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7155
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7143
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7133
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7131
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7120
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7111
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7103
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7097
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7087
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7081
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7080
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7066
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7065
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7060
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7050
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7050
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7047
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7033
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7030
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7029
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7028
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7022
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7010
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7007
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7004

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