Nuciferol A - Compound Card

Nuciferol A

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Nuciferol A

Structure
Zoomed Structure
  • Family: Plantae - Arecaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Sesquinelignan
Canonical Smiles Oc1cc(O)c2c(c1)[C@H]1C[C@](C)(/C=C/c3ccc(c(c3)O)O)c3c([C@H]1CC2=O)cc(c(c3)O)O
InChI InChI=1S/C27H24O7/c1-27(5-4-13-2-3-20(29)21(30)6-13)12-18-15(16-10-22(31)23(32)11-19(16)27)9-25(34)26-17(18)7-14(28)8-24(26)33/h2-8,10-11,15,18,28-33H,9,12H2,1H3/b5-4+/t15-,18+,27+/m1/s1
InChIKey UCLFONLMHVSGEZ-XLOIKJLQSA-N
Formula C27H24O7
HBA 7
HBD 6
MW 460.48
Rotatable Bonds 2
TPSA 138.45
LogP 4.75
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 460.15
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cocos nucifera Arecaceae Plantae 13894

Showing of synonyms

  • Elsbaey M, Jie B, et al. (2019). Nuciferols A and B: Novel sesquineolignans from Cocos nucifera. Tetrahedron Letters, 2019, 60(33), 150948. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(C2)c(cccc3)c3C(CC4=O)C2c(c45)cccc5

Level: 1

Mol. Weight: 460.48 g/mol

Structure

SMILES: c1cccc(c12)C3C(CC2=O)c4c(CC3)cccc4

Level: 0

Mol. Weight: 460.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 460.48 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.09
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.16
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.06
Plasma Protein Binding
96.77
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.17
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.61
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-202.96
Rat (Acute)
2.39
Rat (Chronic Oral)
3.69
Fathead Minnow
5.32
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
608.71
Hydration Free Energy
-3.78
Log(D) at pH=7.4
2.71
Log(P)
4.27
Log S
-4.61
Log(Vapor Pressure)
-11.07
Melting Point
328.21
pKa Acid
6.25
pKa Basic
8.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9289
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9282
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.9166
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.9075
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9030
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8996
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8847
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8775
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8757
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8735
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8720
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8690
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8686
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8685
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8666
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8635
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8581
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8568
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8524
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8506
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8384
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8375
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8353
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8265
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8230
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8200
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8165
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8133
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7891
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7883
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7878
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7862
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7825
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7825
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7798
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7790
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7771
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7745
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7728
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7717
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7681
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7672
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7668
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7654
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7632
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7621
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7552
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7492
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7484
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7449
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7447
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7437
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7417
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7345
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7313
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7285
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7274
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7264
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7258
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7243
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7238
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7225
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7221
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7209
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7204
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7201
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7183
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7172
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7168
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7164
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7145
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7129
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7117
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7103
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7101
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7084
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7083
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7073
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7066
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7062
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7061
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7036
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7035
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7028
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7004
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7003

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