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Samarcandin

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

Canonical Smiles	O=c1ccc2c(o1)cc(cc2)OC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O
InChI	InChI=1S/C24H32O5/c1-22(2)18-9-12-24(4,27)19(23(18,3)11-10-20(22)25)14-28-16-7-5-15-6-8-21(26)29-17(15)13-16/h5-8,13,18-20,25,27H,9-12,14H2,1-4H3/t18-,19+,20+,23-,24+/m0/s1
InChIKey	WNANPKYNOALKIV-XARGLDOUSA-N
Formula	C₂₄H₃₂O₅
HBA	5
HBD	2
MW	400.52
Rotatable Bonds	3
TPSA	79.9
LogP	4.14
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	400.22
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula sinaica	Apiaceae	Plantae	1514050

Showing of synonyms

Ahmed AA (1999). Sesquiterpene coumarins and sesquiterpenes from Ferula sinaica. Phytochemistry,1999,50(1),109-112. [View]

Pubchem: 71587098

Cas: 28699-16-3

Nmrshiftdb2: 60079921

Comptox: DTXSID20182857

CPRiL: 182686

SMILES: c1cc(=O)oc(c12)cc(cc2)OCC3CCCC(C34)CCCC4

Level: 1

Mol. Weight: 312.41 g/mol

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

Level: 0

Mol. Weight: 146.15 g/mol

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 138.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.62
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.450
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.12

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.890
Plasma Protein Binding: 92.92
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: 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: 7.850
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.160
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.010
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.820
Micronucleos: Toxic
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: Toxic
T. Pyriformis: -14.520
Rat (Acute): 3.080
Rat (Chronic Oral): 1.600
Fathead Minnow: 3.950
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 458.540
Hydration Free Energy: -5.230
Log(D) at pH=7.4: 3.590
Log(P): 3.89
Log S: -4.77
Log(Vapor Pressure): -8.63
Melting Point: 192.32
pKa Acid: 7.11
pKa Basic: 7.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.9476
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.9476
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9453
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9453
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9425
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9425
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9405
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9405
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9395
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9395
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.9350
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.9350
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.9199
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.9199
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9023
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9023
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8822
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8822
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8686
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8686
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8643
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8643
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8631
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8631
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8568
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8568
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8519
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8519
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8496
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8496
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8481
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8481
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8443
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8443
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8424
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8424
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8378
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8378
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8361
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8361
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8331
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8331
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8101
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8101
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8096
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8096
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.8016
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.8016
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7942
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7942
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7890
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7890
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7882
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7882
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7852
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7852
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7818
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7818
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7772
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7772
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7706
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7706
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7693
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7693
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7682
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7682
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7670
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7670
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7646
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7646
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7643
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7643
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7617
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7617
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7580
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7580
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7564
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7564
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7561
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7561
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7547
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7547
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7544
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7544
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7530
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7530
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7510
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7510
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7459
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7459
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7427
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7427
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7422
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7422
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7422
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7422
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7373
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7373
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7367
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7367
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7345
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7345
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7321
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7321
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7321
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7321
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7290
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7290
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7282
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7282
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7279
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7279
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7221
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7221
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7197
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7197
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7192
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7192
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7188
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7188
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7185
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7185
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7184
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7184
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7170
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7170
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7153
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7153
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7149
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7149
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7147
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7147
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7143
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7143
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7143
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7143
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7110
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7110
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7107
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7107
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7101
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7101
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7095
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7095
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7093
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7093
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7090
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7090
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7080
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7080
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7080
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7080
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7064
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7064
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7033
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7033
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7008
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7008

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