(+)-[1R*,10R*]-cembra-2E,4E,7E,11Z-tetraen-20,10-olide - Compound Card

(+)-[1R*,10R*]-cembra-2E,4E,7E,11Z-tetraen-20,10-olide

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(+)-[1R*,10R*]-cembra-2E,4E,7E,11Z-tetraen-20,10-olide

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Cembranolide Diterpene
Canonical Smiles C/C/1=C\C/C=C(\C)/C=C/[C@H](CCC2=C[C@@H](C1)OC2=O)C(C)C
InChI InChI=1S/C20H28O2/c1-14(2)17-9-8-15(3)6-5-7-16(4)12-19-13-18(11-10-17)20(21)22-19/h6-9,13-14,17,19H,5,10-12H2,1-4H3/b9-8+,15-6+,16-7+/t17-,19-/m1/s1
InChIKey GFSIRKGSRCAQRP-BSTDZIDZSA-N
Formula C20H28O2
HBA 2
HBD 0
MW 300.44
Rotatable Bonds 1
TPSA 26.3
LogP 5.13
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 300.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Croton gratissimus Euphorbiaceae Plantae 316784

Showing of synonyms

  • Mulholland DA, Langat MK, et al. (2010). Cembranolides from the stem bark of the southern African medicinal plant, Croton gratissimus (Euphorbiaceae). Phytochemistry, 2010, 71(11-12), 1381–1386. [View]
Pubchem: 70698096
Chebi: 68875
Metabolights: MTBLC68875

No compound-protein relationship available.

Structure

SMILES: O=C1OC(C=C12)CC=CCC=CC=CCCC2

Level: 0

Mol. Weight: 300.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.95
Plasma Protein Binding
80.46
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
4.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.88
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.46
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.02
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
1.03
Rat (Acute)
1.77
Rat (Chronic Oral)
1.91
Fathead Minnow
4.93
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
358.2
Hydration Free Energy
-3.77
Log(D) at pH=7.4
4.54
Log(P)
5.64
Log S
-5.72
Log(Vapor Pressure)
-4.68
Melting Point
72.71
pKa Acid
9.12
pKa Basic
5.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8753
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8545
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8256
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8119
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8108
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8004
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7961
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7875
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7738
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7730
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7723
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7709
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7708
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7676
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7658
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7602
Retinoic acid receptor RXR-alpha P28700 RXRA_MOUSE Mus musculus 3 0.7585
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7466
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7462
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7441
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7405
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7405
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7392
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7346
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7314
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7285
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7271
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7249
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7241
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7231
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7209
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7150
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7142
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7133
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7130
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7117
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7098
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7090
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7064
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7049
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7043
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7043
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7007

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