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Lasidiol-10-anisate

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpenoid

Canonical Smiles	COc1ccc(cc1)C(=O)O[C@H]1C=C(C)CC[C@]2([C@]1(C)CC[C@@H]2C(C)C)O
InChI	InChI=1S/C23H32O4/c1-15(2)19-11-12-22(4)20(14-16(3)10-13-23(19,22)25)27-21(24)17-6-8-18(26-5)9-7-17/h6-9,14-15,19-20,25H,10-13H2,1-5H3/t19-,20+,22-,23+/m1/s1
InChIKey	IYDWZZNRGMWKMG-SKWRMQMOSA-N
Formula	C₂₃H₃₂O₄
HBA	4
HBD	1
MW	372.51
Rotatable Bonds	4
TPSA	55.76
LogP	4.76
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.61
Exact Mass	372.23
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula vesceritensis	Apiaceae	Plantae	1514058

Showing of synonyms

Oughlissi-Dehak K, Lawton P, et al. (2008). Sesquiterpenes from aerial parts of Ferula vesceritensis. Phytochemistry,2008,69(9),1933-1938. [View] [PubMed]

Pubchem: 162891810

Zinc: ZINC000238759845

Nmrshiftdb2: 70003257

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2C=CCCC(C23)CCC3

Level: 1

Mol. Weight: 372.51 g/mol

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 372.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 372.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.62
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.510
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.690
Plasma Protein Binding: 80.05
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: 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: 6.070
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.940
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.600
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.230
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: -3.560
Rat (Acute): 2.490
Rat (Chronic Oral): 2.080
Fathead Minnow: 3.960
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 387.250
Hydration Free Energy: -4.020
Log(D) at pH=7.4: 4.650
Log(P): 5.58
Log S: -5.6
Log(Vapor Pressure): -6.38
Melting Point: 132.91
pKa Acid: 9.41
pKa Basic: 4.95

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9578
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9578
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9182
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9182
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8188
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8188
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8178
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8178
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8147
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8147
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7919
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7919
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.7586
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.7586
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7572
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7572
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7558
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7558
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7551
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7551
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7533
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7533
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7360
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7360
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7359
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7359
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7347
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7347
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7324
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7324
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7304
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7304
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7298
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7298
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7293
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7293
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7270
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7270
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7240
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7240
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7228
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7228
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7217
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7217
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7211
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7211
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7136
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7136
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7132
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7132
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	2	0.7092
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	2	0.7092
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7075
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7075
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7072
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7072
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7064
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7064
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7037
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7037
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7017
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7017

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