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Pycnanthulignene A

Family: Plantae - Myristicaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc2c(cc1OC)C=C([C@@H]([C@H]2c1ccc(cc1)O)C)C
InChI	InChI=1S/C20H22O3/c1-12-9-15-10-18(22-3)19(23-4)11-17(15)20(13(12)2)14-5-7-16(21)8-6-14/h5-11,13,20-21H,1-4H3/t13-,20-/m0/s1
InChIKey	HCDYEUTVLWYHQC-RBZFPXEDSA-N
Formula	C₂₀H₂₂O₃
HBA	3
HBD	1
MW	310.39
Rotatable Bonds	3
TPSA	38.69
LogP	4.59
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	310.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pycnanthus angolensis	Myristicaceae	Plantae	224864

Showing of synonyms

Kuete V, Nono EC, et al. (2011). Antimicrobial activities of the CH2Cl2-CH3OH (1:1) extracts and compounds from the roots and fruits of Pycnanthus angolensis (Myristicaceae).. Natural product research,2011, 25(4), 432-443. [View] [PubMed]

Pubchem: 46186375

Zinc: ZINC000049050032

Nmrshiftdb2: 70078094

Chembl: CHEMBL1087927

No compound-protein relationship available.

SMILES: c1cccc(c12)C(CC=C2)c3ccccc3

Level: 1

Mol. Weight: 310.39 g/mol

SMILES: C1=CCCc(c12)cccc2

Level: 0

Mol. Weight: 310.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 310.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.94
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.720
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.980
Plasma Protein Binding: 86.74
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.380
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.270
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.970
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.280
Micronucleos: Safe
NR-AhR: Toxic
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: 2.540
Rat (Acute): 2.080
Rat (Chronic Oral): 2.370
Fathead Minnow: 4.850
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 404.230
Hydration Free Energy: -6.880
Log(D) at pH=7.4: 4.030
Log(P): 4.64
Log S: -5.4
Log(Vapor Pressure): -6.6
Melting Point: 150.29
pKa Acid: 10.38
pKa Basic: 4.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.9509
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9494
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9273
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9213
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9111
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8975
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8923
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8857
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8834
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.8798
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8712
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8689
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8688
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8543
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8508
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8469
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8451
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8438
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8389
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8349
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8331
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8236
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8229
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.8159
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8146
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8123
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7993
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7954
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7945
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.7917
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7915
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7863
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7861
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7832
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7830
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7802
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7781
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7779
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7775
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7751
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7715
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7678
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7588
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7546
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7532
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7528
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7510
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7506
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7491
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7466
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7449
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7441
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7438
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7420
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7415
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7405
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7397
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7393
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7372
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7369
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7368
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7357
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7352
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7351
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7331
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7324
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7309
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7307
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	4	0.7298
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7290
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7251
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7247
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7245
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7234
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7225
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7223
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7221
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7220
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7207
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7198
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7192
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7176
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7139
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7135
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7132
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7118
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7110
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7102
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7092
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7084
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7071
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7067
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7066
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7045
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7038
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7032
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7029
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7026
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7019
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7012
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7010
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7005

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