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Gardenifolin G

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COC(=O)/C=C/c1cc(OC)c2c(c1)[C@@H](CO)[C@H](O2)c1ccc(c(c1)OC)O
InChI	InChI=1S/C21H22O7/c1-25-17-10-13(5-6-16(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-/m1/s1
InChIKey	DPDJZJNYBSGDHT-DWDFQXMKSA-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]

Pubchem: 92852583

Zinc: ZINC000028862511

Chembl: CHEMBL4126146

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 386.4 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 386.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.4 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.55
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.700
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.71

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.120
Plasma Protein Binding: 73.73
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: 10.960
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.220
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.700
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.530
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): 2.170
Rat (Chronic Oral): 2.780
Fathead Minnow: 4.950
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 453.090
Hydration Free Energy: -6.490
Log(D) at pH=7.4: 3.210
Log(P): 1.97
Log S: -4.21
Log(Vapor Pressure): -8.4
Melting Point: 152.09
pKa Acid: 8.44
pKa Basic: 2.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9226
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9002
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8998
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8997
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.8868
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8834
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8796
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8702
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8574
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8565
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8525
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8481
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8441
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8229
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8216
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8196
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8160
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8085
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8010
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7981
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7960
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7928
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7915
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7905
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7900
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7855
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7852
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7849
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7842
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7824
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7813
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7675
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7654
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7633
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7608
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7590
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7575
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7573
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7568
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7532
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7526
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7506
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7497
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7472
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7468
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7455
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7449
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7440
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7439
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7439
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7437
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7435
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7391
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7384
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7373
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7369
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7367
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7360
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7357
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7352
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7350
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7346
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7330
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7324
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7317
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7302
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7297
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7276
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7269
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7265
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7254
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7236
BMP-2-inducible protein kinase	Q9NSY1	BMP2K_HUMAN	Homo sapiens	2	0.7234
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7212
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7208
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7202
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7198
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7174
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7173
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7156
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7155
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7151
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7146
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7130
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7127
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7120
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7117
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7104
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7096
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7091
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7090
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7089
Metallophosphoesterase	A3DJ38	A3DJ38_HUNT2	Clostridium thermocellum	2	0.7089
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7064
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7062
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7061
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7059
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7057
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7057
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7057
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7041
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7024
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7021
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7017

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