Sphaerolabdadiene-3,14-diol - Compound Card

Sphaerolabdadiene-3,14-diol

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Sphaerolabdadiene-3,14-diol

Structure
Zoomed Structure
  • Family: Sphaerococcaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Bromoditerpene
Canonical Smiles C=CC(CCC1C(=CCC(C1(C)CCC(C(=C)C)O)Br)C)(O)C
InChI InChI=1S/C20H33BrO2/c1-7-19(5,23)12-10-16-15(4)8-9-18(21)20(16,6)13-11-17(22)14(2)3/h7-8,16-18,22-23H,1-2,9-13H2,3-6H3
InChIKey UXNHALFPXFVTMG-UHFFFAOYSA-N
Formula C20H33BrO2
HBA 2
HBD 2
MW 385.39
Rotatable Bonds 8
TPSA 40.46
LogP 5.16
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 384.17
Number of Lipinski Rule Violations 1
# 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: 15508165
Nmrshiftdb2: 70059589

No compound-protein relationship available.

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 82.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
8.58
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.57
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.71
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.32
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.2
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.42
Rat (Acute)
2.98
Rat (Chronic Oral)
1.58
Fathead Minnow
4.5
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
346.26
Hydration Free Energy
-4.7
Log(D) at pH=7.4
4.12
Log(P)
5.06
Log S
-4.6
Log(Vapor Pressure)
-5.84
Melting Point
54.37
pKa Acid
10.61
pKa Basic
5.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9177
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9177
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8885
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8885
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8858
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8858
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8661
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8661
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8636
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8636
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8471
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8471
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8412
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8412
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.8399
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.8399
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8209
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8209
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8171
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8171
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8145
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8145
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8133
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8133
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8053
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8053
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7969
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7969
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7926
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7926
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7873
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7873
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7836
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7836
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7786
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7786
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7776
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7776
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7776
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7776
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7755
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7755
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7751
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7751
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7726
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7726
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7709
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7709
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7682
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7682
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7650
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7650
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7628
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7628
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7618
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7618
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7615
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7615
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7558
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7558
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7512
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7512
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7510
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7510
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7471
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7471
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7459
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7459
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7446
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7446
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7445
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7445
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7434
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7434
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7429
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7429
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7417
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7417
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7404
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7404
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7387
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7387
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7361
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7361
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7354
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7354
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7330
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7330
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7324
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7324
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7324
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7324
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7314
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7314
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7304
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7304
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7277
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7277
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7262
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7262
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7234
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7234
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7226
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7226
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7211
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7211
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7201
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7201
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7199
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7199
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7198
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7198
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7138
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7138
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7113
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7113
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7106
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7106
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7100
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7100
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7097
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7097
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 4 0.7091
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 4 0.7091
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7088
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7088
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7081
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7081
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7070
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7070
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7067
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7067
Epoxide hydrolase LasB B6ZK72 LSD19_STRLS Streptomyces lasalocidi 3 0.7063
Epoxide hydrolase LasB B6ZK72 LSD19_STRLS Streptomyces lasalocidi 3 0.7063
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7054
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7054
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7029
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7029
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7025
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7025
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7024
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7024
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7022
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7022
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7017
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7017
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7013
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7013
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7012
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7012

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