Chiliadenol C - Compound Card

Chiliadenol C

Select a section from the left sidebar

Chiliadenol C

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Peroxide
Canonical Smiles C=CC(CC[C@H]1OO[C@@H](CC1=C)C=C(C)C)(O)C
InChI InChI=1S/C15H24O3/c1-6-15(5,16)8-7-14-12(4)10-13(17-18-14)9-11(2)3/h6,9,13-14,16H,1,4,7-8,10H2,2-3,5H3/t13-,14-,15?/m1/s1
InChIKey HYZUYRMHHUNOMH-GRKKQISMSA-N
Formula C15H24O3
HBA 3
HBD 1
MW 252.35
Rotatable Bonds 5
TPSA 38.69
LogP 3.32
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chiliadenus montanus Asteraceae Plantae 1458965

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
Pubchem: 102125250
Nmrshiftdb2: 70083414

No compound-protein relationship available.

Structure

SMILES: C=C1CCOOC1

Level: 0

Mol. Weight: 252.35 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.14
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.29
Plasma Protein Binding
44.69
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.02
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.13
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.35
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
0.84
Rat (Acute)
1.83
Rat (Chronic Oral)
1.64
Fathead Minnow
4.15
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
282.82
Hydration Free Energy
-5.05
Log(D) at pH=7.4
2.26
Log(P)
3.94
Log S
-3.07
Log(Vapor Pressure)
-4.06
Melting Point
34.13
pKa Acid
9.32
pKa Basic
4.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9493
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9493
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.9025
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.9025
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9022
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9022
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8769
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8769
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8754
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8754
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8656
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8656
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8647
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8647
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8617
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8617
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8533
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8533
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.8109
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.8109
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8055
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8055
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8042
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8042
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.8035
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.8035
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.8014
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.8014
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8008
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8008
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7949
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7949
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7923
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7923
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7902
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7902
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7899
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7899
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7851
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7851
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7831
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7831
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7819
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7819
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7813
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7813
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7813
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7813
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7744
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7744
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7734
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7734
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7682
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7682
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7673
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7673
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7668
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7668
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7667
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7667
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7665
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7665
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7649
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7649
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7647
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7647
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7640
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7640
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7613
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7613
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7608
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7608
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7608
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7608
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7603
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7603
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7600
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7600
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7574
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7574
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7569
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7569
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7563
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7563
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7560
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7560
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7552
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7552
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7549
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7549
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7548
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7548
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7540
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7540
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 3 0.7493
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 3 0.7493
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7479
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7479
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7464
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7464
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7420
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7420
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7409
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7409
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7375
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7375
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7373
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7373
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7371
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7371
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7369
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7369
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7368
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7368
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7352
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7352
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7303
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7303
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7292
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7292
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7279
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7279
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7259
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7259
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7257
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7257
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7249
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7249
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7246
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7246
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7243
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7243
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7240
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7240
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7210
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7210
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7200
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7200
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7191
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7184
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7184
Retinoic acid receptor RXR-alpha P28700 RXRA_MOUSE Mus musculus 3 0.7180
Retinoic acid receptor RXR-alpha P28700 RXRA_MOUSE Mus musculus 3 0.7180
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7169
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7169
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7168
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7168
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7159
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7159
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7132
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7132
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7129
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7129
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 3 0.7126
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 3 0.7126
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7099
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7099
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7098
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7098
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7081
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7081
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7073
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7073
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7032
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7032
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7027
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7027

Download SDF