2alpha,16-dihydroxy-4beta-carboxy-O-beta-D-glucopyranosyl-19-nor-totarol - Compound Card

2alpha,16-dihydroxy-4beta-carboxy-O-beta-D-glucopyranosyl-19-nor-totarol

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2alpha,16-dihydroxy-4beta-carboxy-O-beta-D-glucopyranosyl-19-nor-totarol

Structure
Zoomed Structure
  • Family: Plantae - Podocarpaceae
  • Kingdom: Plantae
  • Class: Terpenoid
Canonical Smiles OC[C@H]1O[C@@H](OC(=O)[C@@]2(C)C[C@H](O)C[C@]3(C2CCc2c3ccc(c2C(CO)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C26H38O10/c1-12(10-27)19-14-4-7-18-25(2,15(14)5-6-16(19)30)8-13(29)9-26(18,3)24(34)36-23-22(33)21(32)20(31)17(11-28)35-23/h5-6,12-13,17-18,20-23,27-33H,4,7-11H2,1-3H3/t12?,13-,17-,18?,20-,21+,22-,23+,25-,26+/m1/s1
InChIKey RJYJAKTWROQSLA-NOXHKGLNSA-N
Formula C26H38O10
HBA 10
HBD 7
MW 510.58
Rotatable Bonds 5
TPSA 177.14
LogP -0.19
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 510.25
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Podocarpus gracilior Podocarpaceae Plantae 165205

Showing of synonyms

  • Faiella L, Temraz A, et al. (2012). Terpenoids from the leaves of Podocarpus gracilior. Phytochemistry Letters,2012,5(2),297-300. [View]
Pubchem: 163081939
Nmrshiftdb2: 70058107

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCc(c34)cccc4

Level: 1

Mol. Weight: 510.58 g/mol

Structure

SMILES: c1cccc(c12)CCC3C2CCCC3

Level: 0

Mol. Weight: 510.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 510.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.51
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.26
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
73.72
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
Non-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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.43
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.2
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.75
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-364.5
Rat (Acute)
3.67
Rat (Chronic Oral)
3.62
Fathead Minnow
4.04
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
529.09
Hydration Free Energy
-3.11
Log(D) at pH=7.4
1.09
Log(P)
-0.05
Log S
-2.36
Log(Vapor Pressure)
-12.48
Melting Point
169.14
pKa Acid
5.22
pKa Basic
6.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8098
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8098
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8020
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8020
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7996
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7996
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7756
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7756
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7666
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7666
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7561
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7561
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7464
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7464
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7269
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7269
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7244
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7244
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7178
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7178
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7094
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7094

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