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(3S)-butylphthalide

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Benzolactone
- Subclass: Phthalide

Canonical Smiles	CCCC[C@@H]1OC(=O)c2c1cccc2
InChI	InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3/t11-/m0/s1
InChIKey	HJXMNVQARNZTEE-NSHDSACASA-N
Formula	C₁₂H₁₄O₂
HBA	2
HBD	0
MW	190.24
Rotatable Bonds	3
TPSA	26.3
LogP	3.09
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	14
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	190.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Apium graveolens	Apiaceae	Plantae	4045

Showing of synonyms

Sbai H, Zribi I, et al. (2017). Bioguided fractionation and isolation of phytotoxic compounds from Apium graveolens L. aerial parts (Apiaceae). South African Journal of Botany, 2017, 108, 423–430. [View] [PubMed]

Pubchem: 11116832

Cas: 3413-15-8

Zinc: ZINC000001850826

Nmrshiftdb2: 70093975

Chembl: CHEMBL250205

Comptox: DTXSID80455776

Bindingdb: 50180660

CPRiL: 421313

SMILES: O=C1OCc(c12)cccc2

Level: 0

Mol. Weight: 190.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.52
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.46
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.22

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.67
Plasma Protein Binding: 64.49
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: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: 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: 5.93
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.18
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.11
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.94
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: 1.73
Rat (Acute): 1.91
Rat (Chronic Oral): 2.21
Fathead Minnow: 4.03
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 299.36
Hydration Free Energy: -4.48
Log(D) at pH=7.4: 3.27
Log(P): 3.09
Log S: -2.96
Log(Vapor Pressure): -3.55
Melting Point: 41.25
pKa Acid: 9.8
pKa Basic: 4.97

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.9429
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9386
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.9381
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.9195
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.9169
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.9154
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.9032
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8757
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8595
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8082
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.8069
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8042
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.8034
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7968
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7941
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7923
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7918
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7910
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7888
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7871
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7862
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7844
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7842
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7831
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7821
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7815
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7806
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7744
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7717
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7716
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7713
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7706
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7699
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7693
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7681
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7650
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7640
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7639
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7608
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7600
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7573
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7557
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7540
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7515
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7514
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7495
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7475
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7467
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7432
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7429
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7418
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7392
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7389
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	2	0.7373
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7357
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7351
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7321
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7318
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7296
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7292
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7288
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	2	0.7264
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7251
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7244
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	2	0.7242
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7237
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7234
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7234
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7230
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7228
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7212
Phenylpyruvate C(3)-methyltransferase	Q643C8	MPPJ_STRHY	Streptomyces hygroscopicus	2	0.7207
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	2	0.7191
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7183
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7176
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7167
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7167
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7166
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7159
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7139
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7138
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7133
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	3	0.7118
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7103
Fumarate reductase subunit D	P0A8Q3	FRDD_ECOLI	Escherichia coli	2	0.7090
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7084
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7070
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7060
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7053
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7052
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	2	0.7052
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7050
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	2	0.7022
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7020
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7010

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