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Integrifoliodiol

Family: Rutaceae
Kingdom: Plantae
Class: Phenylpropanoid

Canonical Smiles	OC/C=C/c1ccc(cc1)OC/C=C(/CO)\C
InChI	InChI=1S/C14H18O3/c1-12(11-16)8-10-17-14-6-4-13(5-7-14)3-2-9-15/h2-8,15-16H,9-11H2,1H3/b3-2+,12-8+
InChIKey	HBYDSAUNWMQLKR-NQPRBDNZSA-N
Formula	C₁₄H₁₈O₃
HBA	3
HBD	2
MW	234.29
Rotatable Bonds	6
TPSA	49.69
LogP	2.01
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	17
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	234.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zanthoxylum tessmannii	Rutaceae	Plantae	1291627

Showing of synonyms

Kenmoe Djeukeu C, Kouam Kenmogne A, et al. (2019). A New Aromatic Amide from the Roots of Zanthoxylum tessmannii (Rutaceae).. Chemistry & biodiversity,2019, 16(4), e1800590. [View] [PubMed]

Pubchem: 132535187

Zinc: ZINC000238750417

Nmrshiftdb2: 60077416

No compound-protein relationship available.

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -4.5
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.68
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.63
Plasma Protein Binding: 38.39
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.73
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.7
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.94
Micronucleos: Safe
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: 1.57
Rat (Acute): 1.96
Rat (Chronic Oral): 2.32
Fathead Minnow: 4.64
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 346.98
Hydration Free Energy: -11.84
Log(D) at pH=7.4: 1.4
Log(P): 1.91
Log S: -2.64
Log(Vapor Pressure): -5.81
Melting Point: 106.47
pKa Acid: 11.35
pKa Basic: 4.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.9730
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9455
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.9336
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.9248
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9186
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9159
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.9144
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.9125
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8951
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8803
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8742
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8721
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8717
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8651
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8645
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8640
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8575
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8422
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8303
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.8230
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8203
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8197
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8177
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7948
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7946
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7941
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7921
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7899
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7816
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7803
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7798
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.7794
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7783
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	3	0.7780
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.7738
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7699
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7691
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7679
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7652
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7626
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7620
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7608
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	3	0.7580
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7570
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7569
Peroxisome proliferator-activated receptor alpha	Q07869	PPARA_HUMAN	Homo sapiens	3	0.7558
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	4	0.7517
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7479
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7468
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7457
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7451
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Q9WY79	MURE_THEMA	Thermotoga maritima	3	0.7424
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7421
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7409
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7397
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7393
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7390
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7385
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7381
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7377
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7372
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7366
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7356
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.7351
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7340
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7335
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7313
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7297
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7286
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7285
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7281
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7275
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7274
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7273
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7273
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7273
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	2	0.7266
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7261
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7257
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7256
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7244
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7238
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7236
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7231
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7230
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7218
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7208
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	2	0.7205
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7199
Metallophosphoesterase	A3DJ38	A3DJ38_HUNT2	Clostridium thermocellum	2	0.7193
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7186
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7184
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	2	0.7183
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7171
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7163
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7158
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7156
Type IV pilus retractation ATPase PilT	P24559	PILT_PSEAE	Pseudomonas aeruginosa	3	0.7155
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7152
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7149
Aminopeptidase N	P15145	AMPN_PIG	Sus scrofa	2	0.7146
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7142
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7139
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7131
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7128
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7126
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7121
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7118
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7115
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7109
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7107
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7101
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7100
Gamma-aminobutyric acid type B receptor subunit 1	Q9UBS5	GABR1_HUMAN	Homo sapiens	2	0.7089
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7081
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7071
Protein claret segregational	P20480	NCD_DROME	Drosophila melanogaster	2	0.7070
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7061
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7050
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7048
Angiotensin-converting enzyme	Q10714	ACE_DROME	Drosophila melanogaster	2	0.7038
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7036
Nucleoside diphosphate kinase	A5J299	A5J299_PENVA	Penaeus vannamei	2	0.7032
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	2	0.7027
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7023
Carboxypeptidase A1	P00730	CBPA1_BOVIN	Bos taurus	2	0.7022
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7022
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7017
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	2	0.7016
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7013
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	2	0.7012
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7002

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