18-hydroxy-cis-clerodan-3-ene-15-oic acid - Compound Card

18-hydroxy-cis-clerodan-3-ene-15-oic acid

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18-hydroxy-cis-clerodan-3-ene-15-oic acid

Structure
Zoomed Structure
  • Family: Animalia - Apidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OCC1=CCC[C@H]2[C@]1(C)CC[C@H]([C@]2(C)CCC(CC(=O)O)C)C
InChI InChI=1S/C20H34O3/c1-14(12-18(22)23)8-10-19(3)15(2)9-11-20(4)16(13-21)6-5-7-17(19)20/h6,14-15,17,21H,5,7-13H2,1-4H3,(H,22,23)/t14?,15-,17-,19+,20-/m1/s1
InChIKey FVXAJZRADGVLQM-GBQBBRBDSA-N
Formula C20H34O3
HBA 2
HBD 2
MW 322.49
Rotatable Bonds 6
TPSA 57.53
LogP 4.65
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 322.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Apis species Apidae Animalia 7459

Showing of synonyms

  • Piccinelli AL, Mencherini T, et al. (2013). Chemical composition and antioxidant activity of Algerian propolis. Journal of Agricultural and Food Chemistry,2013,61(21),5080-5088. [View] [PubMed]
Pubchem: 163002428
Nmrshiftdb2: 80004900

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 322.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
78.16
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
2.48
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.0
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.4
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.08
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
0.29
Rat (Acute)
2.0
Rat (Chronic Oral)
1.85
Fathead Minnow
3.92
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
387.78
Hydration Free Energy
-6.95
Log(D) at pH=7.4
1.66
Log(P)
4.25
Log S
-4.21
Log(Vapor Pressure)
-7.21
Melting Point
126.69
pKa Acid
5.57
pKa Basic
8.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9472
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9472
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.9009
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.9009
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8643
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8643
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8514
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8514
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8414
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8414
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8197
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8197
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8140
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8140
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8082
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8082
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7901
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7901
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7873
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7873
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7816
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7816
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7558
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7524
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7524
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7463
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7463
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7463
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7463
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7418
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7418
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7416
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7416
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7384
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7384
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7359
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7359
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7299
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7299
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 4 0.7286
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 4 0.7286
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7283
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7283
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7226
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7226
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7125
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7125
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7099
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7099
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7074
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7074

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