Cholesta-5,22-dien-3beta-ol - Compound Card

Cholesta-5,22-dien-3beta-ol

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Cholesta-5,22-dien-3beta-ol

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC(C/C=C/[C@@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)C
InChI InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6,8-9,18-19,21-25,28H,7,10-17H2,1-5H3/b8-6+/t19-,21-,22-,23+,24-,25-,26-,27+/m0/s1
InChIKey UPGTYLFCVNHBTN-NNLHDAIHSA-N
Formula C27H44O
HBA 1
HBD 1
MW 384.65
Rotatable Bonds 4
TPSA 20.23
LogP 7.16
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 384.34
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea hirsuta Thymelaeaceae Plantae 69845

Showing of synonyms

  • Badawy A, Hassanean H, et al. (2011). Isolates From Thymelaea Hirsuta Inhibit Progression Of Hepatocellular Carcinoma In Vitro And In Vivo. Natural Product Research, 2011,35(11),1799–1798. [View] [PubMed]
Pubchem: 13845851

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 384.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
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
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.74
Plasma Protein Binding
79.49
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
10.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.23
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.01
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-12.82
Rat (Acute)
2.24
Rat (Chronic Oral)
1.88
Fathead Minnow
3.94
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
393.87
Hydration Free Energy
-3.34
Log(D) at pH=7.4
6.36
Log(P)
8.03
Log S
-6.81
Log(Vapor Pressure)
-6.61
Melting Point
142.54
pKa Acid
13.14
pKa Basic
8.28
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 0.9345
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9245
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9203
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9130
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9051
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8947
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8913
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8881
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8856
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8843
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8706
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8657
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.8627
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8610
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8536
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8462
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8427
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8242
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.8201
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8172
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8134
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8087
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7984
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7961
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7857
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7694
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7545
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7538
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7510
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7439
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7372
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7355
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7344
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7328
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7284
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7207
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7199
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7182
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7173
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 4 0.7168
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7138
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7016

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