6-hydroxystigmast-4-en-3-one - Compound Card

6-hydroxystigmast-4-en-3-one

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6-hydroxystigmast-4-en-3-one

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Steroid
Canonical Smiles CC[C@@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(C2=CC(=O)CC[C@]12C)O)C
InChI InChI=1S/C29H48O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h16,18-20,22-25,27,31H,7-15,17H2,1-6H3/t19-,20-,22+,23-,24+,25+,27?,28-,29-/m1/s1
InChIKey IWNCBADONFSAAW-ATPUVMSWSA-N
Formula C29H48O2
HBA 2
HBD 1
MW 428.7
Rotatable Bonds 6
TPSA 37.3
LogP 7.2
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 428.37
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Neoboutonia macrocalyx Euphorbiaceae Plantae 1260343

Showing of synonyms

  • Namukobe J, Kiremire BT, et al. (2014). Cycloartane triterpenes from the leaves of Neoboutonia macrocalyx L.. Phytochemistry,2014,102,189-196. [View] [PubMed]
Pubchem: 71307329
Nmrshiftdb2: 70016570

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 428.7 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.76
Plasma Protein Binding
84.47
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.56
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.76
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.44
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
-46.88
Rat (Acute)
2.27
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
449.15
Hydration Free Energy
-3.12
Log(D) at pH=7.4
6.02
Log(P)
6.92
Log S
-6.23
Log(Vapor Pressure)
-7.88
Melting Point
149.69
pKa Acid
11.91
pKa Basic
7.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9295
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9295
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9091
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9091
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8759
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8759
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8176
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8176
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7712
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7712
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7646
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7646
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7577
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7577
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7543
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7543
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7499
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7499
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7444
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7444
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7290
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7290
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7271
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7271
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7206
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7206
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7196
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7196
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7103
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7103
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7098
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7098
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7061
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7061
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7058
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7058

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