Campylospermone A - Compound Card

Campylospermone A

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Campylospermone A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Biflavonoid
Canonical Smiles Oc1ccc(cc1)[C@H]1Oc2cc(O)ccc2C(=O)[C@@H]1[C@@H]1[C@H](Oc2c(C1=O)ccc(c2)O)c1ccc(cc1)O
InChI InChI=1S/C30H22O8/c31-17-5-1-15(2-6-17)29-25(27(35)21-11-9-19(33)13-23(21)37-29)26-28(36)22-12-10-20(34)14-24(22)38-30(26)16-3-7-18(32)8-4-16/h1-14,25-26,29-34H/t25-,26-,29+,30+/m0/s1
InChIKey RZCBRIXDECISPR-SRPPIYJJSA-N
Formula C30H22O8
HBA 8
HBD 4
MW 510.5
Rotatable Bonds 3
TPSA 133.52
LogP 5.07
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 510.13
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ormocarpum kirkii Leguminosae/Fabaceae Plantae 77284
2 Campylospermum mannii Ochnaceae Plantae 1321792
3 Ludwigia leptocarpa Ochnaceae Plantae 1401410
4 Ochna holstii Ochnaceae Plantae 1389766

Showing of synonyms

  • Kalenga TM, Ndoile MM, et al. (2021). Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii. Journal of natural products,2021, 84(2), 364-372. [View] [PubMed]
  • Elo Manga S, Tih A, et al. (2009). Biflavonoid constituents of Campylospermum mannii. Biochemical Systematics and Ecology, 2009, 37(4), 402-404. [View]
  • Adem FA, Mbaveng AT, et al. (2019). Cytotoxicity of isoflavones and biflavonoids from Ormocarpum kirkii towards multi-factorial drug resistant cancer. Phytomedicine, 2019, 58, 152853. [View]
Pubchem: 100987456
Nmrshiftdb2: 70039499

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 510.5 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 510.5 g/mol

Structure

SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 510.5 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 510.5 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 510.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 510.5 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-5.61
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.500
Plasma Protein Binding
96.58
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.110
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.760
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.530
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
-2656.530
Rat (Acute)
2.240
Rat (Chronic Oral)
2.980
Fathead Minnow
15.870
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
575.770
Hydration Free Energy
-3.060
Log(D) at pH=7.4
3.690
Log(P)
3.8
Log S
-6.45
Log(Vapor Pressure)
-10.86
Melting Point
364.75
pKa Acid
7.46
pKa Basic
5.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9683
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9025
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.9004
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8908
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8830
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8813
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.8811
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8780
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8668
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8627
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8625
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8554
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8530
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8514
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8505
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8494
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8427
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8391
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8377
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8323
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8298
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8256
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8248
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8209
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8158
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8093
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8078
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8076
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8060
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8049
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8000
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7995
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7975
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7925
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7923
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7884
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7864
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7847
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7812
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7765
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7758
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7755
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7691
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7665
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7664
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7646
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7615
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7610
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7561
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7556
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7556
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7497
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7486
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7477
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7434
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7420
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7409
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7408
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7398
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7398
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7385
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7384
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7349
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7334
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7331
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7331
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7327
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7309
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7296
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7280
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7225
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7210
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7178
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7170
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7140
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7114
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 5 0.7113
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7091
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7090
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7082
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7082
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7076
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7073
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7067
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7060
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7059
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7056
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7052
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7029
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7024
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7021
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7019
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7010
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7002

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