2beta-acetoxy-1-alpha,6-beta,9-beta-tribenzoyloxy-4-beta-hydroxy-dihydro-beta-agarofuran - Compound Card

2beta-acetoxy-1-alpha,6-beta,9-beta-tribenzoyloxy-4-beta-hydroxy-dihydro-beta-agarofuran

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2beta-acetoxy-1-alpha,6-beta,9-beta-tribenzoyloxy-4-beta-hydroxy-dihydro-beta-agarofuran

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(=O)O[C@@H]1C[C@](C)(O)[C@@]23[C@]([C@H]1OCc1ccccc1)(C)[C@@H](OCc1ccccc1)C[C@H]([C@H]3OCc1ccccc1)C(O2)(C)C
InChI InChI=1S/C38H46O7/c1-26(39)44-31-22-36(4,40)38-33(42-24-28-17-11-7-12-18-28)30(35(2,3)45-38)21-32(41-23-27-15-9-6-10-16-27)37(38,5)34(31)43-25-29-19-13-8-14-20-29/h6-20,30-34,40H,21-25H2,1-5H3/t30-,31-,32+,33-,34+,36+,37-,38+/m1/s1
InChIKey PHHBTJLRALJMPR-DPIYMOMGSA-N
Formula C38H46O7
HBA 7
HBD 1
MW 614.78
Rotatable Bonds 10
TPSA 83.45
LogP 6.4
Number Rings 6
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 614.32
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Salacia longipes Celastraceae Plantae 662028

Showing of synonyms

  • Mba'ning BM, Lenta BN, et al. (2013). Antiplasmodial sesquiterpenes from the seeds of Salacia longipes var. camerunensis.. Phytochemistry,2013, 96, 347-352. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1COC2C(CO3)CC(OCc4ccccc4)C(C235)C(CCC5)OCc6ccccc6

Level: 3

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1COC2C(CO3)CCC(C234)C(CCC4)OCc5ccccc5

Level: 2

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1COC2C(CO3)CC(C(C234)CCCC4)OCc5ccccc5

Level: 2

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1COC(CC(C2)CO3)C(C234)C(CCC4)OCc5ccccc5

Level: 2

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1COC2C(CO3)CCC(C234)CCCC4

Level: 1

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1COC(CCC2)C(C234)CCC(C3)CO4

Level: 1

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1COC(CC(C2)CO3)C(C234)CCCC4

Level: 1

Mol. Weight: 614.78 g/mol

Structure

SMILES: C1CCCC(C123)CCC(C2)CO3

Level: 0

Mol. Weight: 614.78 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 614.78 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.25
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
30.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
105.71
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.95
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.22
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.61
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
-59161.63
Rat (Acute)
3.26
Rat (Chronic Oral)
2.17
Fathead Minnow
87.94
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
3493.81
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.17
Log(P)
6.5
Log S
-5.84
Log(Vapor Pressure)
-105.46
Melting Point
118.75
pKa Acid
9.56
pKa Basic
1.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9387
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9314
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9282
Nociceptin receptor P41146 OPRX_HUMAN Homo sapiens 3 0.8934
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8933
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8789
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8566
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8432
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8335
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8331
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8302
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8232
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8153
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.8111
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8073
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8008
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7978
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7965
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7933
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7908
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7839
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7800
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7794
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7740
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7728
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7712
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7704
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7688
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7672
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7667
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7635
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7634
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7620
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7607
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7582
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7578
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7568
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7565
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7550
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7535
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7534
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7525
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7517
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7517
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7494
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7475
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7471
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7463
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7458
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7451
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7428
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 3 0.7423
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7419
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7414
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7366
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7336
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7335
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7329
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7286
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7278
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7246
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7229
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7219
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7212
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7207
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7206
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7161
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7149
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7117
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7106
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7106
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7106
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7095
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7083
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7071
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7055
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7053
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7044
HAP protein Q8IM15 Q8IM15_PLAF7 Plasmodium falciparum 3 0.7043
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7040
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7037
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7031
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7003
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7002

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