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Galbanic acid

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Sesquiterpene Coumarin

Canonical Smiles	OC(=O)CC[C@H]1C(=C(C)C)CC[C@@H]([C@]1(C)COc1ccc2c(c1)oc(=O)cc2)C
InChI	InChI=1S/C24H30O5/c1-15(2)19-9-5-16(3)24(4,20(19)10-11-22(25)26)14-28-18-8-6-17-7-12-23(27)29-21(17)13-18/h6-8,12-13,16,20H,5,9-11,14H2,1-4H3,(H,25,26)/t16-,20-,24-/m0/s1
InChIKey	CVWWNYPTZYQCSE-YFBXQHAESA-N
Formula	C₂₄H₃₀O₅
HBA	4
HBD	1
MW	398.5
Rotatable Bonds	6
TPSA	76.74
LogP	5.43
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	398.21
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula assa-foetida	Apiaceae	Plantae	52471

Showing of synonyms

El-Razek MHA, Ohta S, et al. (2001). Sesquiterpene coumarins from the roots of Ferula assa-foetida. Phytochemistry,2001,58(8),1289-1295. [View]

Pubchem: 7082474

Cas: 3566-55-0

Zinc: ZINC000004042371

Chebi: 175181

Nmrshiftdb2: 60079886

Chembl: CHEMBL1078509

CPRiL: 55872

SMILES: C=C1CC(CCC1)COc(cc2)cc(c23)oc(=O)cc3

Level: 1

Mol. Weight: 398.5 g/mol

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 398.5 g/mol

SMILES: C=C1CCCCC1

Level: 0

Mol. Weight: 398.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.97
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.97
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 2.14
Plasma Protein Binding: 105.55
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 2.65
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.13
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.39
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.14
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -11.48
Rat (Acute): 2.48
Rat (Chronic Oral): 1.99
Fathead Minnow: 4.04
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: 453.89
Hydration Free Energy: -3.96
Log(D) at pH=7.4: 2.14
Log(P): 5.38
Log S: -5.47
Log(Vapor Pressure): -8.92
Melting Point: 167.88
pKa Acid: 5.96
pKa Basic: 6.15

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9544
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9544
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9478
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9478
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.9067
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.9067
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8930
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8930
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8806
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8806
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8779
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8779
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8759
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8759
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8544
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8544
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8341
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8341
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8225
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8225
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8127
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8127
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7985
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7985
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7959
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7959
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7760
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7760
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7736
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7736
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7724
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7724
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7707
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7707
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7701
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7701
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7697
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7697
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7691
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7691
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7668
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7668
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7664
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7664
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7596
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7596
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7510
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7510
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7510
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7510
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7495
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7495
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7486
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7486
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7461
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7461
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7454
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7454
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7452
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7452
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7427
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7427
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7422
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7422
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7396
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7396
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7387
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7387
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7376
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7376
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7310
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7310
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7310
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7310
MutT/nudix family protein	Q5SJY9	Q5SJY9_THET8	Thermus thermophilus	2	0.7308
MutT/nudix family protein	Q5SJY9	Q5SJY9_THET8	Thermus thermophilus	2	0.7308
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7268
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7268
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7227
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7227
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7204
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7204
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7176
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7176
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7167
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7167
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7151
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7151
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7151
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7151
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7148
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7148
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7118
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7118
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7089
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7089
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7046
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7046
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7018
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7018
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7004
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7004

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