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(R)-(+)-byakangelicol

Family: Apiaceae
Kingdom: Plantae
Class: Coumarin

Canonical Smiles	COc1c2ccoc2c(c2c1ccc(=O)o2)OCC1OC1(C)C
InChI	InChI=1S/C17H16O6/c1-17(2)11(23-17)8-21-16-14-10(6-7-20-14)13(19-3)9-4-5-12(18)22-15(9)16/h4-7,11H,8H2,1-3H3
InChIKey	ORBITTMJKIGFNH-UHFFFAOYSA-N
Formula	C₁₇H₁₆O₆
HBA	6
HBD	0
MW	316.31
Rotatable Bonds	4
TPSA	74.34
LogP	3.1
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	316.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Deverra battandieri	Apiaceae	Plantae	1589787

Showing of synonyms

Esseid C, León F, et al. (2021). Coumarins and other constituents from Deverra battandieri. Phytochemistry Letters, 2021, 42, 129-133.. [View]

Pubchem: 616062

Nmrshiftdb2: 60046851

CPRiL: 243932

SMILES: O1CC1COc(c(c23)occ2)c4c(c3)ccc(=O)o4

Level: 1

Mol. Weight: 258.23 g/mol

SMILES: c1coc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 186.17 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 44.05 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.73
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.3
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.11
Plasma Protein Binding: 69.36
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 15.33
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.11
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.55
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.86
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: 2.65
Rat (Acute): 2.78
Rat (Chronic Oral): 1.78
Fathead Minnow: 4.97
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 435.6
Hydration Free Energy: -8.55
Log(D) at pH=7.4: 1.99
Log(P): 2.66
Log S: -4.94
Log(Vapor Pressure): -6.48
Melting Point: 72.06
pKa Acid: 5.67
pKa Basic: 3.97

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9465
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9062
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8979
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8941
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8834
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8772
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8764
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8743
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8705
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8665
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8624
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8593
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8568
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8550
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8549
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8393
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8348
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8293
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8241
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8141
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8138
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.8132
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8123
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.8097
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8025
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7998
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7992
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7967
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7960
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7950
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7875
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7870
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7864
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7860
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7838
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7836
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7827
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7819
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7817
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7806
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7778
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7775
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7743
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7736
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7733
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7731
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7723
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7705
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7667
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7651
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7639
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7626
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7615
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7611
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7598
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7590
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7590
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7585
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7572
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7571
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7549
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7544
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7543
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7518
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7516
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7498
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7492
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7480
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7473
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7455
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7454
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7454
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7453
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7453
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7447
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7445
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7445
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7442
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7439
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7419
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7418
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7414
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7412
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7406
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7398
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7388
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7383
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7375
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7372
Interleukin-2	P60568	IL2_HUMAN	Homo sapiens	2	0.7354
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7353
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	2	0.7350
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7342
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7340
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7339
Acetyl-CoA carboxylase	Q00955	ACAC_YEAST	Saccharomyces cerevisiae	3	0.7332
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7299
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7283
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7283
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7262
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7228
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7226
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7206
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7205
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR0	INHA_MYCTO	Mycobacterium tuberculosis	3	0.7203
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7201
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7200
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7194
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7189
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7188
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7184
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7183
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7177
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7176
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7165
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7157
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7153
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7152
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7133
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7133
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7131
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7125
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7119
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7116
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7109
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7106
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7104
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7094
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7087
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	2	0.7085
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7082
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7079
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7079
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7061
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7060
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7060
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7054
Alpha/beta hydrolase fold	A5VAT9	A5VAT9_SPHWW	Sphingomonas wittichii	2	0.7054
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7054
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7049
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7035
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	4	0.7033
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7028
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7023
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7022
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7020
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7018
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7015
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7014
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7006
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7003

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