(1S,4R,13S)-cembra-2E,7E,11E-trien-4,13-diol - Compound Card

(1S,4R,13S)-cembra-2E,7E,11E-trien-4,13-diol

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(1S,4R,13S)-cembra-2E,7E,11E-trien-4,13-diol

Structure
Zoomed Structure
  • Family: Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\CC[C@@](C)(O)/C=C/[C@@H](C[C@H](/C(=C/CC1)/C)O)C(C)C
InChI InChI=1S/C20H34O2/c1-15(2)18-11-13-20(5,22)12-7-9-16(3)8-6-10-17(4)19(21)14-18/h9-11,13,15,18-19,21-22H,6-8,12,14H2,1-5H3/b13-11+,16-9+,17-10+/t18-,19+,20+/m0/s1
InChIKey DFSPZTIKYKYOMU-UPMYUHBTSA-N
Formula C20H34O2
HBA 2
HBD 2
MW 306.49
Rotatable Bonds 1
TPSA 40.46
LogP 4.78
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 306.26
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • El-Ezz RFA, Ahmed SA, et al. (2012). Bioactive cembranoids from the Red Sea soft coral Sarcophyton glaucum. Tetrahedron Letters,2012,54,989-992. [View]
Pubchem: 162897639
Nmrshiftdb2: 70081750

No compound-protein relationship available.

Structure

SMILES: C1=CCCCC=CCCCC=CCC1

Level: 0

Mol. Weight: 190.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.15

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.71
Plasma Protein Binding
66.23
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.85
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.17
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.17
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
-2.23
Rat (Acute)
1.93
Rat (Chronic Oral)
1.87
Fathead Minnow
4.58
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
348.14
Hydration Free Energy
-6.32
Log(D) at pH=7.4
3.59
Log(P)
5.52
Log S
-4.32
Log(Vapor Pressure)
-4.98
Melting Point
105.96
pKa Acid
10.92
pKa Basic
7.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9603
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9603
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9050
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9050
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8429
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8429
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8258
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8258
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7937
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7937
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7935
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7935
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7890
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7890
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7784
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7784
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7763
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7763
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7708
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7708
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7678
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7678
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7675
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7675
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7634
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7634
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7566
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7566
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7559
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7525
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7525
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7491
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7491
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7453
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7453
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7427
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7427
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7405
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7405
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7392
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7392
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7358
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7358
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7331
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7331
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7324
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7324
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7287
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7287
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7277
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7277
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7198
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7198
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7197
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7197
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7159
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7159
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7153
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7153
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7136
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7136
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7107
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7107
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7099
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7099
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7087
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7087
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7084
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7084
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7081
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7081
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7073
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7073

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