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Dihydroauroglaucin

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Benzenoid

Canonical Smiles	CCC/C=C/C=C/c1c(O)cc(c(c1C=O)O)CC=C(C)C
InChI	InChI=1S/C19H24O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h6-10,12-13,21-22H,4-5,11H2,1-3H3/b7-6+,9-8+
InChIKey	JXIPKNRBDKQMAN-BLHCBFLLSA-N
Formula	C₁₉H₂₄O₃
HBA	3
HBD	2
MW	300.4
Rotatable Bonds	7
TPSA	57.53
LogP	4.79
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	300.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ammi majus	Umbelliferae	Plantae	48026

Showing of synonyms

Fathallah N, Raafat M.M, et al. (2019). Bio-Guided Fractionation of Prenylated Benzaldehyde Derivatives as Potent Antimicrobial and Antibiofilm from Ammi majus L. Fruits-Associated Aspergillus amstelodami. Molecules, 2019,24(22),4114. [View] [PubMed]

Pubchem: 51340292

Cas: 77102-91-1

Gnps: CCMSLIB00004679374

Zinc: ZINC000072110340

Chebi: 68190

Nmrshiftdb2: 70006730

Metabolights: MTBLC68190

Chembl: CHEMBL1813665

No compound-protein relationship available.

SMILES: c1ccccc1

Level: 0

Mol. Weight: 300.4 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp): -4.67
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.38
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.55
Plasma Protein Binding: 36.13
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 4.14
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.39
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.16
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.47
Micronucleos: Safe
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: 5.19
Rat (Acute): 2.0
Rat (Chronic Oral): 2.42
Fathead Minnow: 4.88
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: 374.99
Hydration Free Energy: -8.98
Log(D) at pH=7.4: 3.64
Log(P): 5.89
Log S: -4.6
Log(Vapor Pressure): -6.63
Melting Point: 106.85
pKa Acid: 9.17
pKa Basic: 5.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.9441
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9345
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9084
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9063
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8948
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8910
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8883
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8873
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8488
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8487
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8475
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8443
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8338
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.8335
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8310
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8309
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8278
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8210
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8195
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8115
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8108
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8101
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8093
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8069
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8044
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8042
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8035
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.8020
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7982
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7980
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7945
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7935
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7927
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7926
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7920
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7919
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7910
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7905
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7892
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	3	0.7888
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7847
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7847
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7793
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.7790
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7788
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7778
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7735
Histone deacetylase-like amidohydrolase	Q70I53	HDAH_ALCSD	Alcaligenes sp.)	2	0.7726
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7719
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7707
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7703
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7663
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7651
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7638
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7636
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7611
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7608
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7601
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7597
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	4	0.7593
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7588
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7586
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7571
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7555
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7544
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7543
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7543
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7535
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7534
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7531
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7530
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7518
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7499
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7497
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7494
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7490
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7482
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7481
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7478
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7478
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7457
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7442
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7435
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7423
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7410
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7374
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7346
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7341
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7338
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7337
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	2	0.7321
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7319
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7313
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7303
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7299
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7298
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7297
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7296
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7282
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7282
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7273
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7272
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7264
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7257
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7254
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7249
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7247
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7242
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7232
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7230
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	3	0.7229
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	2	0.7199
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7187
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7180
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7177
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7175
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7167
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7162
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7161
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7159
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7150
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7145
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7144
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7131
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7129
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7127
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7121
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7112
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7109
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7109
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7106
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7102
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7094
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7083
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7074
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	3	0.7074
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7055
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7044
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7035
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7030
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7029
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7026
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7025
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7024
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7023
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7022
Alpha/beta hydrolase fold	A5VAT9	A5VAT9_SPHWW	Sphingomonas wittichii	2	0.7020
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7018
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	2	0.7017
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7007
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7007

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