2alpha,3beta,17,19-tetracetoxyspongia-13-(16),14-diene - Compound Card

2alpha,3beta,17,19-tetracetoxyspongia-13-(16),14-diene

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2alpha,3beta,17,19-tetracetoxyspongia-13-(16),14-diene

Structure
Zoomed Structure
  • Family: Animalia - Chromodorididae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)OC[C@@]1(C)[C@@H](OC(=O)C)[C@@H](OC(=O)C)C[C@]2(C1CC[C@@]1(C2CCc2c1coc2)COC(=O)C)C
InChI InChI=1S/C28H38O9/c1-16(29)34-14-27(6)23-9-10-28(15-35-17(2)30)21-13-33-12-20(21)7-8-24(28)26(23,5)11-22(36-18(3)31)25(27)37-19(4)32/h12-13,22-25H,7-11,14-15H2,1-6H3/t22-,23?,24?,25-,26-,27+,28+/m0/s1
InChIKey UZMPPMSWUGSOSN-VIHXTIAUSA-N
Formula C28H38O9
HBA 9
HBD 0
MW 518.6
Rotatable Bonds 6
TPSA 118.34
LogP 3.9
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 518.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Glossodoris atromarginata Chromodorididae Animalia 154629

Showing of synonyms

  • Fontana A, Mollo E, et al. (1997). Chemical studies of Egyptian Opisthobranchs: spongian diterpenoids from Glossodoris atromarginata. Journal of Natural Products,1997,60(5),444-448. [View]
Pubchem: 10577827
Nmrshiftdb2: 70047098

No compound-protein relationship available.

Structure

SMILES: c1occ(c12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 518.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
78.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.15
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.97
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
Safe
T. Pyriformis
-622.02
Rat (Acute)
2.94
Rat (Chronic Oral)
2.48
Fathead Minnow
5.41
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
445.88
Hydration Free Energy
-2.9
Log(D) at pH=7.4
2.98
Log(P)
2.8
Log S
-5.4
Log(Vapor Pressure)
-8.41
Melting Point
155.18
pKa Acid
11.16
pKa Basic
4.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8643
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8643
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8467
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8467
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8409
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8409
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8310
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8310
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8288
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8288
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7949
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7949
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7795
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7795
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7772
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7772
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7728
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7728
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7667
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7667
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7651
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7651
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7610
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7610
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7588
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7588
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7555
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7555
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7548
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7548
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7535
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7535
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7521
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7521
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7494
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7494
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7480
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7480
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7462
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7462
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7429
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7429
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7417
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7417
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7392
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7392
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7351
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7351
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7329
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7329
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7309
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7309
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7288
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7288
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7287
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7287
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7242
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7242
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7233
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7233
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7227
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7227
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7226
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7226
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7204
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7204
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7197
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7197
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7175
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7175
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7167
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7167
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7156
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7156
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7137
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7137
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7136
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7136
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7131
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7131
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7123
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7123
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7121
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7121
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7116
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7116
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7114
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7114
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7111
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7111
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7109
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7109
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7107
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7107
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7106
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7106
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7095
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7095
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 3 0.7072
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 3 0.7072
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7067
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7067
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7066
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7066
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7060
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7060
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7056
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7056
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7051
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7051
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7044
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7044
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7039
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7039
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7038
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7038
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7009
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7009

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