16(R/S)-hydroxycleroda-3,13-dien-16,15-olide-2-one - Compound Card

16(R/S)-hydroxycleroda-3,13-dien-16,15-olide-2-one

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16(R/S)-hydroxycleroda-3,13-dien-16,15-olide-2-one

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles O=C1OC(C(=C1)CC[C@]1(C)[C@@H](C)CC[C@]2([C@H]1CC(=O)C=C2C)C)O
InChI InChI=1S/C20H28O4/c1-12-5-7-20(4)13(2)9-15(21)11-16(20)19(12,3)8-6-14-10-17(22)24-18(14)23/h9-10,12,16,18,23H,5-8,11H2,1-4H3/t12-,16-,18?,19+,20+/m0/s1
InChIKey UVNWQSVZIUIVBI-DCVKKMEZSA-N
Formula C20H28O4
HBA 4
HBD 1
MW 332.44
Rotatable Bonds 3
TPSA 63.6
LogP 3.55
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 332.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Polyalthia longifolia Annonaceae Plantae 235806

Showing of synonyms

  • Mostafa N.M, Edmond M.P, et al. (2022). Phytoconstituents and renoprotective effect of Polyalthia longifolia leaves extract on radiationinduced nephritis in rats via TGF-β/smad pathway. Nat Prod Res, 2022, 36(16), 4187-4192.. [View] [PubMed]
Pubchem: 133561910

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1CCC2CCCC(C23)C=CC(=O)C3

Level: 1

Mol. Weight: 332.44 g/mol

Structure

SMILES: C1=CC(=O)CC(C12)CCCC2

Level: 0

Mol. Weight: 332.44 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 332.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.03
Plasma Protein Binding
64.44
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
8.3
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.07
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.52
Micronucleos
Safe
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
-0.51
Rat (Acute)
2.37
Rat (Chronic Oral)
1.62
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
394.93
Hydration Free Energy
-5.9
Log(D) at pH=7.4
2.55
Log(P)
2.34
Log S
-4.34
Log(Vapor Pressure)
-6.71
Melting Point
185.28
pKa Acid
7.48
pKa Basic
5.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7825
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7578
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7550
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7448
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7406
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7383
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7373
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7357
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7329
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7246
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7184
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7104
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7070
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7006

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