3beta-hydroxy-24-methylenecholest-5-en-7-one - Compound Card

3beta-hydroxy-24-methylenecholest-5-en-7-one

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3beta-hydroxy-24-methylenecholest-5-en-7-one

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O[C@H]1CC[C@]2(C(=CC(=O)[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C)C1)C
InChI InChI=1S/C28H44O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h16-17,19,21-24,26,29H,3,7-15H2,1-2,4-6H3/t19-,21+,22-,23+,24+,26+,27+,28-/m1/s1
InChIKey CGPZMGRJXFVBDD-LTOXSCOASA-N
Formula C28H44O2
HBA 2
HBD 1
MW 412.66
Rotatable Bonds 5
TPSA 37.3
LogP 6.73
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 412.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Antrocaryon klaineanum Anacardiaceae Plantae 289695

Showing of synonyms

  • Fouokeng Y, Akak CM, et al. (2017). The structure of antrocarine E, an ergostane isolated from Antrocaryon klaineanum Pierre (Anacardiaceae).. Fitoterapia,2017, 117, 61-64. [View] [PubMed]
Pubchem: 162893735
Nmrshiftdb2: 60147393

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2C(=O)C=C4C3CCCC4

Level: 0

Mol. Weight: 412.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
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
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.8
Plasma Protein Binding
84.33
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
9.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.17
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.29
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-27.4
Rat (Acute)
2.47
Rat (Chronic Oral)
1.79
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
448.89
Hydration Free Energy
-3.82
Log(D) at pH=7.4
5.42
Log(P)
6.62
Log S
-6.02
Log(Vapor Pressure)
-7.96
Melting Point
155.76
pKa Acid
11.18
pKa Basic
6.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9463
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9463
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9329
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9329
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8999
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8999
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8950
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8950
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8943
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8943
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8815
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8815
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8661
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8661
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8597
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8597
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8563
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8563
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8436
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8436
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.8426
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.8426
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8420
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8420
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8349
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8349
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8336
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8336
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8328
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8328
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8226
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8226
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8132
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8132
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8130
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8130
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8099
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8099
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7967
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7967
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7921
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7921
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7912
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7912
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7871
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7871
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7804
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7804
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7791
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7791
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 4 0.7756
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 4 0.7756
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7744
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7744
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7739
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7739
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7659
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7659
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7557
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7557
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7541
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7541
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7503
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7360
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7360
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7326
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7326
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7301
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7301
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7291
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7291
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7221
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7221
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7202
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7202
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7188
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7188
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7167
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7167
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7146
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7146
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7080
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7080

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