(4→2)-abeo-16-hydroxy-cleroda-2,13(14)-dien-15,16-olide-3-al - Compound Card

(4→2)-abeo-16-hydroxy-cleroda-2,13(14)-dien-15,16-olide-3-al

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(4→2)-abeo-16-hydroxy-cleroda-2,13(14)-dien-15,16-olide-3-al

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles O=C1C=C(C(O1)O)CC[C@@]1(C)[C@H](C)CC[C@@]2(C1CC(=C2C)C(=O)C)C
InChI InChI=1S/C21H30O4/c1-12-6-8-21(5)13(2)16(14(3)22)11-17(21)20(12,4)9-7-15-10-18(23)25-19(15)24/h10,12,17,19,24H,6-9,11H2,1-5H3/t12-,17?,19?,20+,21+/m1/s1
InChIKey RVBHTIFGFJJJCV-IHUWYVHRSA-N
Formula C21H30O4
HBA 4
HBD 1
MW 346.47
Rotatable Bonds 4
TPSA 63.6
LogP 3.94
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 346.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Polyalthia longifolia Annonaceae Plantae 235806

Showing of synonyms

  • Edmond M.P, Mostafa N.M, et al. (2021). Two clerodane diterpenes isolated from Polyalthia longifolia leaves: comparative structural features, antihistaminic and anti-Helicobacter pylori activities. Nat Prod Res, 2021, 35(23), 5282-5286.. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1CCC(CCC2)C(C23)CC=C3

Level: 1

Mol. Weight: 346.47 g/mol

Structure

SMILES: C1=CCC(C12)CCCC2

Level: 0

Mol. Weight: 346.47 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 346.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
72.86
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
7.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.28
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.28
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.27
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
-1.55
Rat (Acute)
2.37
Rat (Chronic Oral)
1.7
Fathead Minnow
3.97
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
393.65
Hydration Free Energy
-5.16
Log(D) at pH=7.4
2.94
Log(P)
2.85
Log S
-4.54
Log(Vapor Pressure)
-6.41
Melting Point
155.65
pKa Acid
7.51
pKa Basic
5.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8951
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8764
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8495
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8101
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8020
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7973
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7959
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7944
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7739
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7665
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7584
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7569
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7532
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7435
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7397
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7287
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7236
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7235
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7219
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7215
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7165
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7147
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7138
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7106
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7100
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7094
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7094
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7083
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7058
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7052
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7039
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7014

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