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Petiolin J

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	CC(=CCC[C@]1(C)Oc2c(C[C@H]1O)c(O)c(c(c2C(=O)C(C)C)O)C)C
InChI	InChI=1S/C21H30O5/c1-11(2)8-7-9-21(6)15(22)10-14-18(24)13(5)19(25)16(20(14)26-21)17(23)12(3)4/h8,12,15,22,24-25H,7,9-10H2,1-6H3/t15-,21+/m1/s1
InChIKey	QYKLLVVSXTWHIV-VFNWGFHPSA-N
Formula	C₂₁H₃₀O₅
HBA	5
HBD	3
MW	362.47
Rotatable Bonds	5
TPSA	86.99
LogP	4.05
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.57
Exact Mass	362.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum peplidifolium	Hypericaceae	Plantae	1321341

Showing of synonyms

Fobofou SA, Harmon CR, et al. (2016). Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.. Phytochemistry,2016, 124, 108-113. [View] [PubMed]

Pubchem: 46911680

Zinc: ZINC000058592888

Nmrshiftdb2: 70091719

Chembl: CHEMBL1209688

No compound-protein relationship available.

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 362.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.6
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.78
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.86
Plasma Protein Binding: 80.43
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.2
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.35
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.04
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.07
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 0.89
Rat (Acute): 2.25
Rat (Chronic Oral): 2.51
Fathead Minnow: 4.29
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 396.11
Hydration Free Energy: -10.18
Log(D) at pH=7.4: 3.1
Log(P): 5.65
Log S: -4.98
Log(Vapor Pressure): -7.09
Melting Point: 134.83
pKa Acid: 7.17
pKa Basic: 5.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9283
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9237
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9154
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9144
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9060
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9039
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9031
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8879
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8748
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8511
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8391
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.8367
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8367
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8301
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8292
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8286
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.8268
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.8186
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8140
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8131
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8116
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8047
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7998
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7971
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7965
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7943
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7933
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7929
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7920
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7903
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7885
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7884
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7882
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7880
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7868
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7860
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7859
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7833
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7827
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7759
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7728
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7725
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7721
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7719
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7697
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7679
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7657
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7643
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7639
Acyl-homoserine-lactone synthase	Q4VSJ8	Q4VSJ8_BURGL	Burkholderia glumae	5	0.7630
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7600
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7533
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7529
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7520
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7518
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7494
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7492
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7472
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7455
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7450
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7448
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7423
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7411
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7409
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7402
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7348
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7344
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7337
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7335
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7335
DNA double-strand break repair protein Mre11	Q9X1X0	Q9X1X0_THEMA	Thermotoga maritima MSB8	4	0.7329
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7327
Dihydrofolate reductase	P9WNX1	DYR_MYCTU	Mycobacterium tuberculosis	3	0.7288
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7284
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7282
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7273
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7271
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7270
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7258
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7258
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.7256
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7254
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7224
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7213
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7209
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7202
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7189
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7186
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7177
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7152
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7140
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7138
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7120
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7109
orotidine-5'-phosphate decarboxylase	Q8T6J6	Q8T6J6_PLAFA	Plasmodium falciparum	4	0.7082
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7073
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7054
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7042
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7028
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7008

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