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Siccayne

Family: Fungi - Pleosporomycetidae
Kingdom: Fungi
Class: Cyclohexanoid
- Subclass: Oxygenated Cyclohexanoid

Canonical Smiles	CC(=C)C#Cc1cc(O)ccc1O
InChI	InChI=1S/C11H10O2/c1-8(2)3-4-9-7-10(12)5-6-11(9)13/h5-7,12-13H,1H2,2H3
InChIKey	ZUEGEPDZNAILQJ-UHFFFAOYSA-N
Formula	C₁₁H₁₀O₂
HBA	2
HBD	2
MW	174.2
Rotatable Bonds	0
TPSA	40.46
LogP	2.03
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	13
Formal Charge	0
Fraction CSP3	0.09
Exact Mass	174.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Parastagonospora nodorum	Pleosporomycetidae	Fungi	13684

Showing of synonyms

El-Demerdash A, Genta-Jouve G, et al. (2019). Highly oxygenated isoprenylated cyclohexanoids from the fungus Parastagonospora nodorum SN15. Phytochemistry, 2019, 166, 112056. [View] [PubMed]

Pubchem: 189063

Cas: 22944-03-2

Chebi: 156304

Nmrshiftdb2: 70007751

Chembl: CHEMBL455767

No compound-protein relationship available.

SMILES: c1ccccc1

Level: 0

Mol. Weight: 174.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.46
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.3
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.63
Plasma Protein Binding: 46.31
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: 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: 11.32
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.31
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.17
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.45
Micronucleos: Toxic
NR-AhR: Toxic
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: 4.19
Rat (Acute): 2.47
Rat (Chronic Oral): 2.34
Fathead Minnow: 4.05
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 302.77
Hydration Free Energy: -8.8
Log(D) at pH=7.4: 2.86
Log(P): 2.22
Log S: -1.74
Log(Vapor Pressure): -3.92
Melting Point: 94.42
pKa Acid: 9.95
pKa Basic: 5.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.9378
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9288
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.9155
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8985
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8838
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8815
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8791
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8481
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8435
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8433
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.8419
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8389
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8376
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8289
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.8019
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8018
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7999
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7961
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7939
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7875
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7848
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7799
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	3	0.7784
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7738
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7677
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7660
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7629
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7595
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7588
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7582
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7519
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	3	0.7486
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7485
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7483
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7406
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7382
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7363
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7351
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7345
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7312
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7308
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7277
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7275
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7273
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7245
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7210
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7202
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7194
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7193
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7192
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7177
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	3	0.7159
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7137
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7134
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7129
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7128
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7117
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7090
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7088
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7079
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7078
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7055
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7048
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7034
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7025
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7021
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7005

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