Trichadonic acid - Compound Card

Trichadonic acid

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Trichadonic acid

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpenoid
Canonical Smiles O=C1CC[C@@H]2[C@]([C@H]1C)(C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C)C(=O)O
InChI InChI=1S/C30H48O3/c1-19-20(31)8-9-21-27(19,5)11-10-22-28(21,6)15-17-30(24(32)33)23-18-25(2,3)12-13-26(23,4)14-16-29(22,30)7/h19,21-23H,8-18H2,1-7H3,(H,32,33)/t19-,21+,22-,23+,26+,27+,28-,29+,30-/m0/s1
InChIKey DCZGJIUDCAUZMF-ZAYGEOOPSA-N
Formula C30H48O3
HBA 2
HBD 1
MW 456.71
Rotatable Bonds 1
TPSA 54.37
LogP 7.52
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 456.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Hypericaceae Plantae —

Showing of synonyms

  • Damen F, Simo Mpetga JD, et al. (2022). Roeperone A, a new tetraoxygenated xanthone and other compounds from the leaves of Hypericum roeperianum Schimp. (Hypericaceae).. Natural product research,2022, 36(8), 2071-2077. [View] [PubMed]
Pubchem: 15139591
Nmrshiftdb2: 70096638
CPRiL: 84577
Structure

SMILES: C1CC(=O)CC(CC2)C1C3CCC(C4C23)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 456.71 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.32
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.37
Plasma Protein Binding
99.12
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
3.56
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.95
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.81
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
3.24
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-79.92
Rat (Acute)
2.36
Rat (Chronic Oral)
1.98
Fathead Minnow
3.82
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
473.29
Hydration Free Energy
-2.71
Log(D) at pH=7.4
4.88
Log(P)
5.99
Log S
-6.37
Log(Vapor Pressure)
-9.42
Melting Point
285.81
pKa Acid
5.42
pKa Basic
7.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9385
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7884
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7784
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7754
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7353
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7200
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7107
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7057

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