15-acetoxy-ent-3,13E-clerodadiene - Compound Card

15-acetoxy-ent-3,13E-clerodadiene

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15-acetoxy-ent-3,13E-clerodadiene

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C/COC(=O)C)/C)CCC=C2C)C
InChI InChI=1S/C22H36O3/c1-16(11-14-25-18(3)24)9-12-22(5)19(15-23)10-13-21(4)17(2)7-6-8-20(21)22/h7,11,19-20,23H,6,8-10,12-15H2,1-5H3/b16-11+/t19-,20-,21-,22-/m0/s1
InChIKey ZHCMWKVQEQTDSC-BGKAJLSSSA-N
Formula C22H36O3
HBA 3
HBD 1
MW 348.53
Rotatable Bonds 6
TPSA 46.53
LogP 5.05
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 348.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Croton sylvaticus Euphorbiaceae Plantae 992677

Showing of synonyms

  • Ndunda B, Langat MK, et al. (2015). Diterpenoid derivatives of Kenyan Croton sylvaticus.. Natural Product Communications,2015,10(4),557-558. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 348.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.500
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
71.16
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.350
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
-0.630
Rat (Acute)
1.840
Rat (Chronic Oral)
1.730
Fathead Minnow
4.200
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
385.980
Hydration Free Energy
-3.970
Log(D) at pH=7.4
4.030
Log(P)
4.99
Log S
-5.45
Log(Vapor Pressure)
-6.05
Melting Point
84.35
pKa Acid
11.93
pKa Basic
6.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9561
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9561
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9444
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9444
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8850
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8850
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8641
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8641
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8571
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8571
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8513
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8513
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8495
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8495
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8476
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8476
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8470
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8470
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8394
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8394
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8354
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8354
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8271
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8271
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8200
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8154
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8154
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8117
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8117
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8093
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8093
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8025
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8025
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8018
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8018
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7997
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7997
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7976
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7976
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7911
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7911
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7899
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7899
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7754
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7754
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7722
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7722
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7714
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7714
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7648
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7648
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7579
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7579
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7574
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7574
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7510
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7510
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7502
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7502
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7423
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7423
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7409
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7409
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7401
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7401
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7357
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7357
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7351
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7351
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7327
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7327
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7308
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7308
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7302
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7302
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7286
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7286
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7223
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7223
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7219
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7219
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7209
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7209
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7185
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7185
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7087
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7087
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7085
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7085
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7078
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7078
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7071
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7071
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7048
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7048
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7013
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7013
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7003
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7003

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