Tessmannic acid - Compound Card

Tessmannic acid

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Tessmannic acid

Structure
Zoomed Structure
  • Family: Caesalpiniaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Nor-Halimane Diterpenoid
Canonical Smiles OC(=O)CC[C@@H]1C(=C(C)C)CC[C@H]([C@]1(C)CCc1cocc1)C
InChI InChI=1S/C20H30O3/c1-14(2)17-6-5-15(3)20(4,18(17)7-8-19(21)22)11-9-16-10-12-23-13-16/h10,12-13,15,18H,5-9,11H2,1-4H3,(H,21,22)/t15-,18-,20+/m1/s1
InChIKey OMCFKAYBHWTBQV-ZTNFWEORSA-N
Formula C20H30O3
HBA 2
HBD 1
MW 318.46
Rotatable Bonds 6
TPSA 50.44
LogP 5.47
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 318.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Tessmannia densiflora Caesalpiniaceae Plantae 1911674

Showing of synonyms

  • Kihampa C, Nkunya MH, et al. (2009). Anti-mosquito and antimicrobial nor-halimanoids, isocoumarins and an anilinoid from Tessmannia densiflora. Phytochemistry,2009,70(10),1233-1238. [View] [PubMed]
Pubchem: 44472192
Nmrshiftdb2: 70038069

No compound-protein relationship available.

Structure

SMILES: C=C1CC(CCC1)CCc2ccoc2

Level: 1

Mol. Weight: 190.29 g/mol

Structure

SMILES: C=C1CCCCC1

Level: 0

Mol. Weight: 96.17 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 68.07 g/mol

Antibacterial
Antifungal
Larvicidal

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
89.56
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.82
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.04
Micronucleos
Safe
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
-0.88
Rat (Acute)
2.27
Rat (Chronic Oral)
1.94
Fathead Minnow
3.95
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
359.14
Hydration Free Energy
-6.05
Log(D) at pH=7.4
2.48
Log(P)
5.52
Log S
-4.65
Log(Vapor Pressure)
-7.5
Melting Point
105.85
pKa Acid
6.07
pKa Basic
7.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8151
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8151
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7942
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7942
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7906
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7906
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7877
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7877
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7749
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7749
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7729
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7729
Aspartate-semialdehyde dehydrogenase Q51344 DHAS_PSEAE Pseudomonas aeruginosa 3 0.7687
Aspartate-semialdehyde dehydrogenase Q51344 DHAS_PSEAE Pseudomonas aeruginosa 3 0.7687
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7600
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7600
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7525
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7525
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7374
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7374
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7354
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7354
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7318
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7318
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7303
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7303
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7270
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7270
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7267
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7267
2'-5'-oligoadenylate synthase 1 P00973 OAS1_HUMAN Homo sapiens 2 0.7219
2'-5'-oligoadenylate synthase 1 P00973 OAS1_HUMAN Homo sapiens 2 0.7219
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7219
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7219
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7215
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7215
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7168
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7168
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7126
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7105
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7105
C-C chemokine receptor type 5 P51681 CCR5_HUMAN Homo sapiens 3 0.7093
C-C chemokine receptor type 5 P51681 CCR5_HUMAN Homo sapiens 3 0.7093
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7078
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7078
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7071
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7071
Alpha-aminoadipic semialdehyde dehydrogenase P49419 AL7A1_HUMAN Homo sapiens 2 0.7051
Alpha-aminoadipic semialdehyde dehydrogenase P49419 AL7A1_HUMAN Homo sapiens 2 0.7051
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 2 0.7017
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 2 0.7017
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7001
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7001

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