26,27-bisnorcholest-5,16-dien-23-yn-3beta,7alpha-diol - Compound Card

26,27-bisnorcholest-5,16-dien-23-yn-3beta,7alpha-diol

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26,27-bisnorcholest-5,16-dien-23-yn-3beta,7alpha-diol

Structure
Zoomed Structure
  • Family: Animalia - Callyspongiidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC#CC[C@H](C1=CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](O)C=C2[C@]1(C)CC[C@@H](C2)O)C
InChI InChI=1S/C25H36O2/c1-5-6-7-16(2)19-8-9-20-23-21(11-13-25(19,20)4)24(3)12-10-18(26)14-17(24)15-22(23)27/h8,15-16,18,20-23,26-27H,7,9-14H2,1-4H3/t16-,18+,20+,21+,22-,23+,24+,25-/m1/s1
InChIKey DQRSKBYIQKZPLS-AHTLGIBHSA-N
Formula C25H36O2
HBA 2
HBD 2
MW 368.56
Rotatable Bonds 2
TPSA 40.46
LogP 4.87
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 368.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Callyspongia aff. implexa Callyspongiidae Animalia 178537

Showing of synonyms

  • Abdelmohsen UR, Cheng C, et al. (2015). Antichlamydial sterol from the Red Sea sponge Callyspongia aff. Implexa.. Planta Medica,2015,81(5),382-387. [View] [PubMed]
Pubchem: 162817410

No compound-protein relationship available.

Structure

SMILES: C1=CCC(C12)C3C(CC2)C4C(=CC3)CCCC4

Level: 0

Mol. Weight: 368.56 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.35
Plasma Protein Binding
69.26
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.87
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.77
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.8
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
Toxic
T. Pyriformis
-9.97
Rat (Acute)
1.98
Rat (Chronic Oral)
1.71
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
403.8
Hydration Free Energy
-2.98
Log(D) at pH=7.4
4.52
Log(P)
5.36
Log S
-5.32
Log(Vapor Pressure)
-7.48
Melting Point
165.39
pKa Acid
11.28
pKa Basic
6.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9496
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9496
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8968
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8968
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8937
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8937
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8906
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8906
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8784
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8784
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8670
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8670
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8455
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8455
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8444
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8444
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8290
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8195
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8195
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.8055
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.8055
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7857
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7857
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7539
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7539
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7484
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7484
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7431
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7382
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7382
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7357
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7357
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7276
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7276
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7250
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7250
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7231
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7231
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7022
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7022

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