Structure

Physi-Chem Properties

Molecular Weight:  290.08
Volume:  279.249
LogP:  2.37
LogD:  1.966
LogS:  -3.144
# Rotatable Bonds:  1
TPSA:  96.22
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.742
Synthetic Accessibility Score:  3.42
Fsp3:  0.267
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.881
MDCK Permeability:  1.1869264199049212e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.083
20% Bioavailability (F20%):  0.023
30% Bioavailability (F30%):  0.148

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.075
Plasma Protein Binding (PPB):  90.73925018310547%
Volume Distribution (VD):  1.132
Pgp-substrate:  8.321371078491211%

ADMET: Metabolism

CYP1A2-inhibitor:  0.913
CYP1A2-substrate:  0.89
CYP2C19-inhibitor:  0.055
CYP2C19-substrate:  0.162
CYP2C9-inhibitor:  0.222
CYP2C9-substrate:  0.835
CYP2D6-inhibitor:  0.359
CYP2D6-substrate:  0.332
CYP3A4-inhibitor:  0.408
CYP3A4-substrate:  0.16

ADMET: Excretion

Clearance (CL):  14.633
Half-life (T1/2):  0.788

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.05
Drug-inuced Liver Injury (DILI):  0.832
AMES Toxicity:  0.121
Rat Oral Acute Toxicity:  0.057
Maximum Recommended Daily Dose:  0.349
Skin Sensitization:  0.498
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.162
Respiratory Toxicity:  0.376

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC325983

Natural Product ID:  NPC325983
Common Name*:   Fonsecin
IUPAC Name:   2,5,8-trihydroxy-6-methoxy-2-methyl-3H-benzo[g]chromen-4-one
Synonyms:  
Standard InCHIKey:  FKCYENFBFZUSDP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H14O6/c1-15(19)6-9(17)13-11(21-15)4-7-3-8(16)5-10(20-2)12(7)14(13)18/h3-5,16,18-19H,6H2,1-2H3
SMILES:  COc1cc(O)cc2c1c(O)c1c(c2)OC(CC1=O)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1391235
PubChem CID:   216328
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans
        • [CHEMONTID:0001641] Naphthopyranones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)88611-1]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np058103o]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/JR9620000040]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1966.10858561]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1972.10860562]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1985.10867263]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[10695672]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12458767]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12542363]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. sponge-derived n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15556711]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15620260]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17653510]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17827758]
NPO26158 Aspergillus carbonarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18205129]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20014861]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20028011]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21176790]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21543515]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21774474]
NPO26158 Aspergillus carbonarius Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO26158 Aspergillus carbonarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO27902 Alternaria alternata Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[22377027]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22921072]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24684908]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25044953]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25062661]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25293978]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26040782]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26132344]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26414728]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[27245874]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32159958]
NPO26158 Aspergillus carbonarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[4837062]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[6073032]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. Database[Article]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO27902 Alternaria alternata Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26158 Aspergillus carbonarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PMID[514892]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 3162.3 nM PMID[514892]
NPT1038 Individual Protein Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 35481.3 nM PMID[514892]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency = 14125.4 nM PMID[514892]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 31622.8 nM PMID[514892]
NPT4033 Individual Protein Protein Rev Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1) IC50 = 16241.0 nM PMID[514892]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 25118.9 nM PMID[514892]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 1255.9 nM PMID[514892]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 2511.9 nM PMID[514892]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 50118.7 nM PMID[514892]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 79432.8 nM PMID[514892]
NPT4035 Individual Protein Female germline-specific tumor suppressor gld-1 Caenorhabditis elegans IC50 = 2957.0 nM PMID[514892]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 89125.1 nM PMID[514892]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 10318.3 nM PMID[514892]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 35481.3 nM PMID[514892]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 56234.1 nM PMID[514892]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 15848.9 nM PMID[514892]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 37933.0 nM PMID[514892]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 > 40000.0 nM PMID[514892]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 18356.4 nM PMID[514892]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 31622.8 nM PMID[514892]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 8199.5 nM PMID[514892]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 9200.0 nM PMID[514892]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 6309.6 nM PMID[514892]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 35481.3 nM PMID[514892]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 14125.4 nM PMID[514892]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 28183.8 nM PMID[514892]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 28183.8 nM PMID[514892]
NPT2 Others Unspecified Potency = 6309.6 nM PMID[514892]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[514892]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 89125.1 nM PMID[514892]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[514892]
NPT20798 PROTEIN COMPLEX GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 35481.3 nM PMID[514892]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 89125.1 nM PMID[514892]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 11220.2 nM PMID[514892]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 15848.9 nM PMID[514892]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 44668.4 nM PMID[514892]
NPT84 Individual Protein Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus AC50 = 2920.0 nM PMID[514892]
NPT917 Individual Protein Dengue virus type 2 NS3 protein Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2) IC50 n.a. 38140.0 nM PMID[514892]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[514892]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 56234.1 nM PMID[514892]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 84921.4 nM PMID[514892]
NPT2 Others Unspecified Potency n.a. 8912.5 nM PMID[514892]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Potency n.a. 23778.1 nM PMID[514892]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC325983 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9653 High Similarity NPC22005
0.9653 High Similarity NPC123202
0.9653 High Similarity NPC7943
0.9586 High Similarity NPC256672
0.9586 High Similarity NPC7025
0.9586 High Similarity NPC27221
0.9524 High Similarity NPC72958
0.9524 High Similarity NPC232645
0.9521 High Similarity NPC97028
0.9521 High Similarity NPC97029
0.9521 High Similarity NPC288036
0.9521 High Similarity NPC65589
0.9521 High Similarity NPC158338
0.9521 High Similarity NPC100985
0.9459 High Similarity NPC87708
0.9456 High Similarity NPC202595
0.9441 High Similarity NPC94076
0.9441 High Similarity NPC182255
0.9392 High Similarity NPC474417
0.9392 High Similarity NPC149526
0.9375 High Similarity NPC84266
0.9375 High Similarity NPC310340
0.9371 High Similarity NPC275734
0.9329 High Similarity NPC217447
0.9315 High Similarity NPC267509
0.9267 High Similarity NPC329844
0.9267 High Similarity NPC210942
0.9267 High Similarity NPC169990
0.9262 High Similarity NPC478148
0.9262 High Similarity NPC258249
0.9257 High Similarity NPC291049
0.9257 High Similarity NPC233267
0.9252 High Similarity NPC34802
0.9247 High Similarity NPC32470
0.92 High Similarity NPC40356
0.92 High Similarity NPC154683
0.9189 High Similarity NPC105415
0.9178 High Similarity NPC189650
0.9167 High Similarity NPC178851
0.9133 High Similarity NPC133856
0.9128 High Similarity NPC329933
0.9122 High Similarity NPC245584
0.9122 High Similarity NPC289042
0.9122 High Similarity NPC56433
0.9122 High Similarity NPC118027
0.9122 High Similarity NPC71055
0.9122 High Similarity NPC312929
0.9122 High Similarity NPC126767
0.9122 High Similarity NPC190648
0.911 High Similarity NPC266725
0.9073 High Similarity NPC273483
0.9073 High Similarity NPC175978
0.9067 High Similarity NPC119929
0.9067 High Similarity NPC150928
0.9067 High Similarity NPC227122
0.9067 High Similarity NPC470107
0.9054 High Similarity NPC24136
0.9054 High Similarity NPC196114
0.9054 High Similarity NPC225173
0.9054 High Similarity NPC187282
0.9054 High Similarity NPC163846
0.9054 High Similarity NPC290133
0.9054 High Similarity NPC473927
0.9051 High Similarity NPC259905
0.9048 High Similarity NPC19896
0.9034 High Similarity NPC165172
0.9026 High Similarity NPC85121
0.9026 High Similarity NPC474373
0.902 High Similarity NPC146211
0.902 High Similarity NPC4547
0.902 High Similarity NPC180924
0.9013 High Similarity NPC214632
0.9013 High Similarity NPC135522
0.9013 High Similarity NPC472799
0.9007 High Similarity NPC227166
0.9 High Similarity NPC65775
0.9 High Similarity NPC70764
0.9 High Similarity NPC10027
0.8993 High Similarity NPC125801
0.8986 High Similarity NPC134621
0.8986 High Similarity NPC271288
0.898 High Similarity NPC73028
0.8973 High Similarity NPC220106
0.8973 High Similarity NPC182421
0.8968 High Similarity NPC186325
0.8961 High Similarity NPC201127
0.8961 High Similarity NPC212967
0.8961 High Similarity NPC246647
0.8961 High Similarity NPC272196
0.8961 High Similarity NPC96342
0.8961 High Similarity NPC164110
0.8954 High Similarity NPC149618
0.8954 High Similarity NPC89625
0.8947 High Similarity NPC473967
0.894 High Similarity NPC255641
0.894 High Similarity NPC194379
0.894 High Similarity NPC158866
0.894 High Similarity NPC290954
0.894 High Similarity NPC470568
0.894 High Similarity NPC147735
0.894 High Similarity NPC294646
0.8933 High Similarity NPC37139
0.8931 High Similarity NPC470206
0.8931 High Similarity NPC470207
0.8926 High Similarity NPC237208
0.8926 High Similarity NPC473135
0.8926 High Similarity NPC473132
0.8926 High Similarity NPC470676
0.8926 High Similarity NPC477955
0.8919 High Similarity NPC95123
0.8919 High Similarity NPC166138
0.8919 High Similarity NPC18585
0.8919 High Similarity NPC106985
0.8919 High Similarity NPC66404
0.8917 High Similarity NPC197168
0.8912 High Similarity NPC213322
0.8912 High Similarity NPC17170
0.8912 High Similarity NPC96408
0.8912 High Similarity NPC279650
0.8912 High Similarity NPC166689
0.8912 High Similarity NPC3188
0.8912 High Similarity NPC105648
0.8912 High Similarity NPC156190
0.8912 High Similarity NPC324386
0.8912 High Similarity NPC4743
0.8912 High Similarity NPC312391
0.8912 High Similarity NPC258630
0.891 High Similarity NPC189552
0.891 High Similarity NPC273467
0.891 High Similarity NPC66288
0.891 High Similarity NPC18380
0.8904 High Similarity NPC78913
0.8904 High Similarity NPC18260
0.8904 High Similarity NPC316480
0.8903 High Similarity NPC195167
0.8903 High Similarity NPC177650
0.8889 High Similarity NPC95842
0.8889 High Similarity NPC178964
0.8889 High Similarity NPC242712
0.8889 High Similarity NPC280530
0.8882 High Similarity NPC213052
0.8882 High Similarity NPC470569
0.8875 High Similarity NPC477571
0.8875 High Similarity NPC298778
0.8875 High Similarity NPC477572
0.8875 High Similarity NPC477573
0.8874 High Similarity NPC269420
0.8874 High Similarity NPC473978
0.8874 High Similarity NPC266499
0.8867 High Similarity NPC308200
0.8867 High Similarity NPC10990
0.8867 High Similarity NPC259632
0.8867 High Similarity NPC300988
0.8861 High Similarity NPC25361
0.8859 High Similarity NPC473692
0.8859 High Similarity NPC470673
0.8859 High Similarity NPC470890
0.8859 High Similarity NPC470674
0.8859 High Similarity NPC29577
0.8859 High Similarity NPC469764
0.8859 High Similarity NPC117716
0.8854 High Similarity NPC294965
0.8854 High Similarity NPC15374
0.8854 High Similarity NPC216752
0.8851 High Similarity NPC125855
0.8851 High Similarity NPC228504
0.8851 High Similarity NPC107572
0.8851 High Similarity NPC227579
0.8851 High Similarity NPC220998
0.8851 High Similarity NPC324436
0.8851 High Similarity NPC223500
0.8851 High Similarity NPC166934
0.8851 High Similarity NPC1089
0.8851 High Similarity NPC161506
0.8851 High Similarity NPC265040
0.8851 High Similarity NPC37496
0.8851 High Similarity NPC32739
0.8851 High Similarity NPC324134
0.8851 High Similarity NPC167624
0.8851 High Similarity NPC10937
0.8851 High Similarity NPC76338
0.8851 High Similarity NPC144499
0.8851 High Similarity NPC202981
0.8851 High Similarity NPC182852
0.8851 High Similarity NPC328164
0.8851 High Similarity NPC148757
0.8851 High Similarity NPC78
0.8851 High Similarity NPC296917
0.8851 High Similarity NPC166482
0.8851 High Similarity NPC40833
0.8851 High Similarity NPC194432
0.8851 High Similarity NPC76372
0.8851 High Similarity NPC306829
0.8851 High Similarity NPC64915
0.8851 High Similarity NPC177354
0.8851 High Similarity NPC66515
0.8846 High Similarity NPC119224
0.8846 High Similarity NPC184326
0.8846 High Similarity NPC470810
0.8846 High Similarity NPC292863

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC325983 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.891 High Similarity NPD6959 Discontinued
0.8889 High Similarity NPD7819 Suspended
0.8767 High Similarity NPD1552 Clinical (unspecified phase)
0.8767 High Similarity NPD1550 Clinical (unspecified phase)
0.8733 High Similarity NPD4378 Clinical (unspecified phase)
0.8707 High Similarity NPD970 Clinical (unspecified phase)
0.8707 High Similarity NPD1549 Phase 2
0.8645 High Similarity NPD2393 Clinical (unspecified phase)
0.8621 High Similarity NPD1607 Approved
0.8503 High Similarity NPD1509 Clinical (unspecified phase)
0.8503 High Similarity NPD1510 Phase 2
0.85 High Similarity NPD6232 Discontinued
0.8487 Intermediate Similarity NPD2534 Approved
0.8487 Intermediate Similarity NPD2532 Approved
0.8487 Intermediate Similarity NPD2533 Approved
0.8483 Intermediate Similarity NPD1240 Approved
0.8471 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD1934 Approved
0.8457 Intermediate Similarity NPD7473 Discontinued
0.8421 Intermediate Similarity NPD1511 Approved
0.8397 Intermediate Similarity NPD7411 Suspended
0.8366 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8365 Intermediate Similarity NPD3749 Approved
0.8365 Intermediate Similarity NPD7075 Discontinued
0.8344 Intermediate Similarity NPD3750 Approved
0.8313 Intermediate Similarity NPD6559 Discontinued
0.8312 Intermediate Similarity NPD1512 Approved
0.8291 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8269 Intermediate Similarity NPD3226 Approved
0.8267 Intermediate Similarity NPD2346 Discontinued
0.825 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD5844 Phase 1
0.8217 Intermediate Similarity NPD4380 Phase 2
0.82 Intermediate Similarity NPD6100 Approved
0.82 Intermediate Similarity NPD2796 Approved
0.82 Intermediate Similarity NPD6099 Approved
0.82 Intermediate Similarity NPD1551 Phase 2
0.8187 Intermediate Similarity NPD7768 Phase 2
0.8182 Intermediate Similarity NPD7390 Discontinued
0.8176 Intermediate Similarity NPD2801 Approved
0.8158 Intermediate Similarity NPD2800 Approved
0.8158 Intermediate Similarity NPD1243 Approved
0.8133 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD6599 Discontinued
0.8084 Intermediate Similarity NPD7074 Phase 3
0.8063 Intermediate Similarity NPD1465 Phase 2
0.8027 Intermediate Similarity NPD4625 Phase 3
0.8024 Intermediate Similarity NPD7054 Approved
0.8013 Intermediate Similarity NPD3748 Approved
0.8 Intermediate Similarity NPD6801 Discontinued
0.7987 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD7472 Approved
0.7964 Intermediate Similarity NPD3818 Discontinued
0.7963 Intermediate Similarity NPD3882 Suspended
0.7961 Intermediate Similarity NPD2935 Discontinued
0.7952 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD6166 Phase 2
0.7949 Intermediate Similarity NPD6799 Approved
0.7939 Intermediate Similarity NPD5710 Approved
0.7939 Intermediate Similarity NPD5711 Approved
0.7929 Intermediate Similarity NPD6797 Phase 2
0.7927 Intermediate Similarity NPD5494 Approved
0.7922 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD920 Approved
0.7901 Intermediate Similarity NPD3817 Phase 2
0.7885 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD7251 Discontinued
0.7853 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD7808 Phase 3
0.7812 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD2344 Approved
0.7785 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2799 Discontinued
0.7763 Intermediate Similarity NPD6651 Approved
0.7758 Intermediate Similarity NPD919 Approved
0.7756 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD5406 Approved
0.7727 Intermediate Similarity NPD5408 Approved
0.7727 Intermediate Similarity NPD5404 Approved
0.7727 Intermediate Similarity NPD5405 Approved
0.7724 Intermediate Similarity NPD1201 Approved
0.7688 Intermediate Similarity NPD8313 Approved
0.7688 Intermediate Similarity NPD8312 Approved
0.7687 Intermediate Similarity NPD1283 Approved
0.7673 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3751 Discontinued
0.7643 Intermediate Similarity NPD4628 Phase 3
0.7635 Intermediate Similarity NPD1470 Approved
0.7635 Intermediate Similarity NPD1203 Approved
0.7632 Intermediate Similarity NPD943 Approved
0.763 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD5953 Discontinued
0.7616 Intermediate Similarity NPD2313 Discontinued
0.7603 Intermediate Similarity NPD1610 Phase 2
0.7595 Intermediate Similarity NPD2309 Approved
0.7584 Intermediate Similarity NPD2798 Approved
0.7571 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD1247 Approved
0.7551 Intermediate Similarity NPD1608 Approved
0.754 Intermediate Similarity NPD8151 Discontinued
0.7532 Intermediate Similarity NPD7003 Approved
0.7517 Intermediate Similarity NPD1651 Approved
0.7515 Intermediate Similarity NPD3787 Discontinued
0.7515 Intermediate Similarity NPD7229 Phase 3
0.75 Intermediate Similarity NPD4749 Approved
0.75 Intermediate Similarity NPD411 Approved
0.75 Intermediate Similarity NPD7286 Phase 2
0.7486 Intermediate Similarity NPD6779 Approved
0.7486 Intermediate Similarity NPD6782 Approved
0.7486 Intermediate Similarity NPD6778 Approved
0.7486 Intermediate Similarity NPD6777 Approved
0.7486 Intermediate Similarity NPD6780 Approved
0.7486 Intermediate Similarity NPD6781 Approved
0.7486 Intermediate Similarity NPD6776 Approved
0.7485 Intermediate Similarity NPD7458 Discontinued
0.7483 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1281 Approved
0.7483 Intermediate Similarity NPD4908 Phase 1
0.7471 Intermediate Similarity NPD3926 Phase 2
0.747 Intermediate Similarity NPD5402 Approved
0.7469 Intermediate Similarity NPD5403 Approved
0.7469 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD7199 Phase 2
0.7455 Intermediate Similarity NPD37 Approved
0.7453 Intermediate Similarity NPD5401 Approved
0.7452 Intermediate Similarity NPD1471 Phase 3
0.7442 Intermediate Similarity NPD7177 Discontinued
0.744 Intermediate Similarity NPD6234 Discontinued
0.7436 Intermediate Similarity NPD4308 Phase 3
0.7432 Intermediate Similarity NPD9717 Approved
0.7425 Intermediate Similarity NPD4965 Approved
0.7425 Intermediate Similarity NPD4967 Phase 2
0.7425 Intermediate Similarity NPD4966 Approved
0.7417 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3268 Approved
0.7374 Intermediate Similarity NPD4287 Approved
0.7368 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7783 Phase 2
0.7368 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD7698 Approved
0.7366 Intermediate Similarity NPD7696 Phase 3
0.7366 Intermediate Similarity NPD7435 Discontinued
0.7366 Intermediate Similarity NPD7697 Approved
0.7365 Intermediate Similarity NPD422 Phase 1
0.7365 Intermediate Similarity NPD4288 Approved
0.7355 Intermediate Similarity NPD230 Phase 1
0.7355 Intermediate Similarity NPD1933 Approved
0.7347 Intermediate Similarity NPD17 Approved
0.7329 Intermediate Similarity NPD1548 Phase 1
0.7326 Intermediate Similarity NPD7870 Phase 2
0.7326 Intermediate Similarity NPD7871 Phase 2
0.7325 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4363 Phase 3
0.7308 Intermediate Similarity NPD4360 Phase 2
0.729 Intermediate Similarity NPD1613 Approved
0.729 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD1164 Approved
0.7285 Intermediate Similarity NPD2797 Approved
0.7284 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3764 Approved
0.7273 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD6832 Phase 2
0.7244 Intermediate Similarity NPD447 Suspended
0.7244 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7228 Approved
0.7239 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD4626 Approved
0.7219 Intermediate Similarity NPD6823 Phase 2
0.7215 Intermediate Similarity NPD7033 Discontinued
0.7213 Intermediate Similarity NPD6535 Approved
0.7213 Intermediate Similarity NPD6534 Approved
0.7211 Intermediate Similarity NPD7701 Phase 2
0.72 Intermediate Similarity NPD3972 Approved
0.7195 Intermediate Similarity NPD6273 Approved
0.7186 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD2979 Phase 3
0.7179 Intermediate Similarity NPD4060 Phase 1
0.7179 Intermediate Similarity NPD4307 Phase 2
0.7174 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD4361 Phase 2
0.7171 Intermediate Similarity NPD3266 Approved
0.7171 Intermediate Similarity NPD3267 Approved
0.7167 Intermediate Similarity NPD8150 Discontinued
0.7143 Intermediate Similarity NPD2654 Approved
0.7143 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7874 Approved
0.7134 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5124 Phase 1

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data