12S-hydroxybromosphaerodiol - Compound Card

12S-hydroxybromosphaerodiol

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12S-hydroxybromosphaerodiol

Structure
Zoomed Structure
  • Family: Plantae - Sphaerococcaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Bromoditerpene
Canonical Smiles BrC[C@@]12CC[C@]3([C@H]([C@@H]2[C@H](C=C[C@H]1C(C)C)O)[C@](C)(O)[C@H](C[C@@H]3Br)O)C
InChI InChI=1S/C20H32Br2O3/c1-11(2)12-5-6-13(23)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(24)19(17,4)25/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15-,16-,17-,18+,19+,20-/m0/s1
InChIKey WQVRLEHPQYWZGE-VHXYLUBJSA-N
Formula C20H32Br2O3
HBA 3
HBD 3
MW 480.28
Rotatable Bonds 2
TPSA 60.69
LogP 3.88
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 478.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sphaerococcus coronopifolius Sphaerococcaceae Plantae 31467

Showing of synonyms

  • Etahiri S, Bultel-Poncé V, et al. (2001). New bromoditerpenes from the red alga Sphaerococcus coronopifolius. Journal of Natural Products,2001,64(8),1024-1027. [View] [PubMed]
Pubchem: 21592263
Nmrshiftdb2: 70059588

No compound-protein relationship available.

Structure

SMILES: C1C=CCC2CCC(C3C12)CCCC3

Level: 0

Mol. Weight: 480.28 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
65.96
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
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.75
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.45
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-0.53
Rat (Acute)
3.17
Rat (Chronic Oral)
1.67
Fathead Minnow
3.89
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
378.47
Hydration Free Energy
-7.32
Log(D) at pH=7.4
4.61
Log(P)
3.8
Log S
-4.45
Log(Vapor Pressure)
-7.69
Melting Point
175.08
pKa Acid
8.57
pKa Basic
4.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9022
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9022
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8974
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8974
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8520
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8520
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8335
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8335
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8286
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8286
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8063
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8063
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7970
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7970
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
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7871
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7871
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7830
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7830
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7770
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7770
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7768
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7768
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7694
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7694
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7582
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7582
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7460
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7460
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7396
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7396
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7392
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7392
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7347
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7347
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7343
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7343
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7343
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7343
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7292
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7292
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7274
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7274
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7232
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7232
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7139
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7139
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7057
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7057

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