Sargassaceae meroditerpenoid 9a - Compound Card

Sargassaceae meroditerpenoid 9a

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Sargassaceae meroditerpenoid 9a

Structure
Zoomed Structure
  • Family: Chromista - Sargassaceae-Fucaceae
  • Kingdom: Chromista
  • Class: Terpenoid
    • Subclass: Meroditerpenoid Derivative
Canonical Smiles COc1cc(C)c2c(c1)CC[C@](O2)(C)CC1=C(CC(O)(C)C)C(=O)[C@]2([C@](C1)(C)CCC2)C
InChI InChI=1S/C28H40O4/c1-18-13-21(31-7)14-19-9-12-27(5,32-23(18)19)16-20-15-26(4)10-8-11-28(26,6)24(29)22(20)17-25(2,3)30/h13-14,30H,8-12,15-17H2,1-7H3/t26-,27-,28+/m1/s1
InChIKey HISWTECQBAVTJH-FCEKVYKBSA-N
Formula C28H40O4
HBA 4
HBD 1
MW 440.62
Rotatable Bonds 5
TPSA 55.76
LogP 6.1
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 440.29
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cystoseira baccata Sargassaceae-Fucaceae Chromista 2823494

Showing of synonyms

  • Mokrini R, Mesaoud MB, et al. (2008). Meroditerpenoids and derivatives from the brown alga Cystoseira baccata and their antifouling properties. Journal of Natural Products,2008,71(11),1806-1181. [View] [PubMed]
Pubchem: 162953346
Nmrshiftdb2: 60043630

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=CC2=O)CC(CC3)Oc(c34)cccc4

Level: 1

Mol. Weight: 440.62 g/mol

Structure

SMILES: C1CCC(C12)CC=CC2=O

Level: 0

Mol. Weight: 440.62 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 440.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.470
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.440
Plasma Protein Binding
101.45
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.320
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.310
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
-48.720
Rat (Acute)
2.610
Rat (Chronic Oral)
1.950
Fathead Minnow
4.540
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
461.710
Hydration Free Energy
-3.520
Log(D) at pH=7.4
4.820
Log(P)
6.45
Log S
-5.42
Log(Vapor Pressure)
-7.41
Melting Point
149.63
pKa Acid
10.53
pKa Basic
6.43
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 0.9009
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9009
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8974
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8974
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8967
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8967
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8933
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8933
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8845
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8845
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.8636
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.8636
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8626
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8626
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8252
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8252
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8124
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8124
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8059
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8059
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8041
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8041
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.8036
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.8036
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7990
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7990
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7940
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7940
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7925
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7925
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7903
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7903
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7799
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7799
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7767
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7767
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7718
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7718
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7708
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7708
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7664
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7664
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7650
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7650
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7623
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7623
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7552
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7552
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7534
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7534
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7512
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7512
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7500
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7500
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7466
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7466
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7461
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7461
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7445
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7445
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7422
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7422
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7418
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7418
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7413
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7413
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7386
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7386
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 3 0.7381
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 3 0.7381
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7359
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7359
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7356
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7356
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7345
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7345
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7334
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7334
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7320
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7320
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7293
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7293
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7291
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7274
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7274
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7273
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7273
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7269
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7269
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7244
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7244
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7236
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7236
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7200
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7200
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7193
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7193
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7183
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7183
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7160
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7160
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7148
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7148
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7138
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7138
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7121
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7121
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7121
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7121
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7110
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7110
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7095
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7095
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7088
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7088
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7075
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7075
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7073
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7073
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7042
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7042
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7031
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7031
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7030
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7030
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7028
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7028
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7013
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7013
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7000
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7000

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