(2R,5S,10R)-2-(10,20-dihydroxy-10-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one - Compound Card

(2R,5S,10R)-2-(10,20-dihydroxy-10-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one

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(2R,5S,10R)-2-(10,20-dihydroxy-10-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC[C@](C1CC[C@]2(C1)[C@H](C)CC(=O)C=C2C)(O)C
InChI InChI=1S/C15H24O3/c1-10-6-13(17)7-11(2)15(10)5-4-12(8-15)14(3,18)9-16/h6,11-12,16,18H,4-5,7-9H2,1-3H3/t11-,12?,14-,15-/m1/s1
InChIKey FWLWCLDHPUPCHO-FMCMVYLNSA-N
Formula C15H24O3
HBA 3
HBD 2
MW 252.35
Rotatable Bonds 2
TPSA 57.53
LogP 2.07
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lycium europaeum Solanaceae Plantae 112873

Showing of synonyms

  • Bendjedou H, Barboni L, et al. (2021). Alkaloids and sesquiterpenes from roots and leaves of Lycium europaeum L. (Solanaceae) with antioxidant and anti-acetylcholinesterase activities. Natural product research, 2021, 35(16), 2784-2788. [View] [PubMed]
Pubchem: 171319597

No compound-protein relationship available.

Structure

SMILES: C1CCCC12C=CC(=O)CC2

Level: 0

Mol. Weight: 252.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.23
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
46.53
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.08
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.44
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
-0.11
Rat (Acute)
2.12
Rat (Chronic Oral)
1.85
Fathead Minnow
3.76
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
339.8
Hydration Free Energy
-9.34
Log(D) at pH=7.4
1.02
Log(P)
1.45
Log S
-2.04
Log(Vapor Pressure)
-5.42
Melting Point
147.48
pKa Acid
10.24
pKa Basic
6.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8991
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8554
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8547
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8510
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8500
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8472
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8436
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8331
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8301
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8239
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8172
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8160
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8001
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7918
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7805
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7718
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7706
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7664
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7601
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7596
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7541
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7480
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7368
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7353
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7324
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7323
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7304
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7285
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7222
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7218
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7203
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7179
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7148
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7103
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7091
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7054
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7047
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7018
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7014

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