Isosamarcandin - Compound Card

Isosamarcandin

Select a section from the left sidebar

Isosamarcandin

Structure
Zoomed Structure
  • Family: Plantae - 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-RBBNJCGNSA-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
2 Ferula sinaica Apiaceae Plantae 1514050

Showing of synonyms

  • Ahmed AA (1990). New Sesquiterpenes from Ferula sinaica. Journal of Natural Products,1990,53(2),483-486. [View] [PubMed]
  • Ahmed AA (1999). Sesquiterpene coumarins and sesquiterpenes from Ferula sinaica. Phytochemistry,1999,50(1),109-112. [View]
Pubchem: 101313320
Nmrshiftdb2: 70004549

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 400.52 g/mol

Structure

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

Level: 0

Mol. Weight: 400.52 g/mol

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 400.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
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
92.63
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
7.830
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.130
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
Toxic
Daphnia Maga
5.810
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
-14.570
Rat (Acute)
3.060
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
Safe

General Properties

Boiling Point
458.790
Hydration Free Energy
-5.260
Log(D) at pH=7.4
3.530
Log(P)
4.21
Log S
-4.81
Log(Vapor Pressure)
-8.62
Melting Point
192.02
pKa Acid
7.12
pKa Basic
7.85
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 0.9538
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9538
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9501
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9501
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9431
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9431
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9409
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9409
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9386
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9386
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8960
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8960
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8948
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8948
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8538
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8538
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8514
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8514
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8513
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8513
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8397
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8397
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8315
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8315
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8252
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8252
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8241
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8241
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8056
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8056
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8054
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8054
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8037
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8037
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7955
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7955
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7895
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7895
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7873
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7873
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7800
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7800
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7792
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7792
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7783
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7783
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7748
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7748
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7719
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7719
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7713
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7713
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7665
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7665
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7658
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7658
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7635
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7635
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7609
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7609
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7565
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7565
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7551
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7551
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7548
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7548
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7498
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7498
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7490
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7490
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7489
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7489
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7486
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7486
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7440
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7440
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7431
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7431
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7371
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7371
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7368
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7368
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7337
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7337
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7323
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7323
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7308
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7308
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7298
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7298
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7297
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7297
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7289
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7289
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7287
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7287
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7250
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7250
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7241
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7241
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7216
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7216
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7148
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7148
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7137
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7137
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7134
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7134
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7125
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7125
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7125
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7125
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7122
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7122
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7102
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7102
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7090
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7090
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7090
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7090
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7084
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7084
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7081
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7081
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7078
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7078
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7059
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7059
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7050
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7050
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7024
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7024

Download SDF