3S,4S,5R,7S,9R,14R-3,7-dihydroxy-4,14-dimethyl-7[8→9]-abeo-cholestan-8-one - Compound Card

3S,4S,5R,7S,9R,14R-3,7-dihydroxy-4,14-dimethyl-7[8→9]-abeo-cholestan-8-one

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3S,4S,5R,7S,9R,14R-3,7-dihydroxy-4,14-dimethyl-7[8→9]-abeo-cholestan-8-one

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ingol Diterpene
Canonical Smiles CC(CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@]1(C2=O)[C@@H](O)C[C@@H]2[C@]1(C)CC[C@@H]([C@H]2C)O)C)C)C
InChI InChI=1S/C29H50O3/c1-18(2)9-8-10-19(3)21-11-13-28(7)25(32)29(16-15-26(21,28)5)24(31)17-22-20(4)23(30)12-14-27(22,29)6/h18-24,30-31H,8-17H2,1-7H3/t19-,20+,21-,22+,23+,24+,26-,27+,28+,29-/m1/s1
InChIKey IMRAICJHRXRWPL-ZDVOQKQISA-N
Formula C29H50O3
HBA 3
HBD 2
MW 446.72
Rotatable Bonds 5
TPSA 57.53
LogP 6.4
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.97
Exact Mass 446.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia officinarum Euphorbiaceae Plantae 1130835

Showing of synonyms

  • Daoubi M, Marquez N, et al. (2007). Isolation of new phenylacetylingol derivatives that reactivate HIV-1 latency and a novel spirotriterpenoid from Euphorbia officinarum latex. Bioorganic and Medicinal Chemistry,2007,15,4577-4584. [View] [PubMed]
Pubchem: 44429427
Nmrshiftdb2: 70111154

No compound-protein relationship available.

Structure

SMILES: C1CCCC(CC2)C1C23C(=O)C4C(CC3)CCC4

Level: 0

Mol. Weight: 446.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.45
Plasma Protein Binding
92.09
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
Substrate
CYP 2C9 Inhibitor
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
11.57
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.63
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.81
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.05
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-59.34
Rat (Acute)
2.38
Rat (Chronic Oral)
1.84
Fathead Minnow
3.84
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
452.87
Hydration Free Energy
-3.1
Log(D) at pH=7.4
5.79
Log(P)
7.19
Log S
-5.71
Log(Vapor Pressure)
-8.13
Melting Point
165.12
pKa Acid
9.7
pKa Basic
7.17
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 0.9014
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9014
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8630
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8630
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8421
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8421
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8317
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8317
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8316
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8316
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7952
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7952
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7891
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7891
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7528
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7528
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7457
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7457
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7447
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7447
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7447
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7447
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7446
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7446
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7323
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7323
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7307
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7307
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7231
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7231
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7139
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7139
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7037
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7037

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