2-((2S,4aS,7R)-1,2,4a,5,6,7,8,8a-octahydro-2-hydroxy-4a-methyl-1-methylenenaphthalen-7-yl)acrylic acid - Compound Card

2-((2S,4aS,7R)-1,2,4a,5,6,7,8,8a-octahydro-2-hydroxy-4a-methyl-1-methylenenaphthalen-7-yl)acrylic acid

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2-((2S,4aS,7R)-1,2,4a,5,6,7,8,8a-octahydro-2-hydroxy-4a-methyl-1-methylenenaphthalen-7-yl)acrylic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1[C@@H](O)C=C[C@]2(C1C[C@@H](CC2)C(=C)C(=O)O)C
InChI InChI=1S/C15H20O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h5,7,11-13,16H,1-2,4,6,8H2,3H3,(H,17,18)/t11-,12?,13+,15+/m1/s1
InChIKey OLROVKXKIOIJDQ-YKURLNKLSA-N
Formula C15H20O3
HBA 2
HBD 2
MW 248.32
Rotatable Bonds 2
TPSA 57.53
LogP 2.54
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus sempervirens Asteraceae Plantae 65000

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 162873903
Nmrshiftdb2: 60072564

No compound-protein relationship available.

Structure

SMILES: C=C1CC=CC(C12)CCCC2

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
51.27
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.17
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.53
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.21
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
-0.7
Rat (Acute)
2.99
Rat (Chronic Oral)
2.59
Fathead Minnow
3.95
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
323.05
Hydration Free Energy
-8.03
Log(D) at pH=7.4
-0.11
Log(P)
2.46
Log S
-2.77
Log(Vapor Pressure)
-5.98
Melting Point
136.98
pKa Acid
3.87
pKa Basic
6.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8935
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8935
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8478
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8478
Suppressor of disruption of TFIIS P53078 SDT1_YEAST Saccharomyces cerevisiae 3 0.8339
Suppressor of disruption of TFIIS P53078 SDT1_YEAST Saccharomyces cerevisiae 3 0.8339
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8194
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8194
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7941
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7941
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7870
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7870
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7815
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7815
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7702
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7702
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7695
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7695
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7662
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7662
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7551
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7551
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7549
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7549
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7545
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7545
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7507
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7507
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7416
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7416
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7415
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7415
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7332
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7332
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7259
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7259
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7247
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7247
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7117
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7117
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7112
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7112
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7106
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7106
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7086
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7086
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7055
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7055

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