8alpha,19-dihydroxylabd-13E-en-15-oic acid - Compound Card

8alpha,19-dihydroxylabd-13E-en-15-oic acid

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8alpha,19-dihydroxylabd-13E-en-15-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@]1(C)CCC[C@]2(C1CC[C@@]([C@@H]2CC/C(=C/C(=O)O)/C)(C)O)C
InChI InChI=1S/C20H34O4/c1-14(12-17(22)23)6-7-16-19(3)10-5-9-18(2,13-21)15(19)8-11-20(16,4)24/h12,15-16,21,24H,5-11,13H2,1-4H3,(H,22,23)/b14-12+/t15?,16-,18+,19+,20-/m1/s1
InChIKey IYSBWLRXTOIYFZ-RDAPGVDQSA-N
Formula C20H34O4
HBA 3
HBD 3
MW 338.49
Rotatable Bonds 5
TPSA 77.76
LogP 3.76
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 338.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crassocephalum mannii Asteraceae-Compositae Plantae 189252

Showing of synonyms

  • Hegazy MEF, Ohta S, et al. (2008). Cyclooxygenase (COX)-1 and -2 Inhibitory Labdane Diterpenes from Crassocephalum mannii. Journal of Natural Products,2008,71,1070-1073. [View] [PubMed]
Pubchem: 162909346
Nmrshiftdb2: 70121413

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 338.49 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
70.5
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.17
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
-1.41
Rat (Acute)
2.04
Rat (Chronic Oral)
2.31
Fathead Minnow
3.93
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
402.92
Hydration Free Energy
-7.68
Log(D) at pH=7.4
1.03
Log(P)
3.51
Log S
-3.54
Log(Vapor Pressure)
-7.17
Melting Point
159.5
pKa Acid
4.82
pKa Basic
9.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9187
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9187
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8526
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8526
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8427
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8427
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8380
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8380
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8295
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8295
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8186
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8186
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7980
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7980
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7967
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7967
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7915
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7915
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7861
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7861
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7803
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7803
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7776
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7776
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7720
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7720
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7717
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7717
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7710
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7710
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7615
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7615
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7608
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7608
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7459
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7459
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7409
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7409
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7323
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7323
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7220
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7220
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7211
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7211
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7189
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7189
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7124
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7124
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7076
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7076
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7007
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7007

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