Structure

Physi-Chem Properties

Molecular Weight:  468.11
Volume:  443.515
LogP:  5.42
LogD:  2.422
LogS:  -4.822
# Rotatable Bonds:  1
TPSA:  174.29
# H-Bond Aceptor:  10
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.149
Synthetic Accessibility Score:  3.426
Fsp3:  0.0
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.281
MDCK Permeability:  4.8897450142249e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.964
20% Bioavailability (F20%):  0.051
30% Bioavailability (F30%):  0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  90.20738220214844%
Volume Distribution (VD):  0.44
Pgp-substrate:  17.58315658569336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.969
CYP1A2-substrate:  0.196
CYP2C19-inhibitor:  0.492
CYP2C19-substrate:  0.035
CYP2C9-inhibitor:  0.711
CYP2C9-substrate:  0.107
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.123
CYP3A4-inhibitor:  0.063
CYP3A4-substrate:  0.045

ADMET: Excretion

Clearance (CL):  2.371
Half-life (T1/2):  0.813

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.958
Drug-inuced Liver Injury (DILI):  0.998
AMES Toxicity:  0.179
Rat Oral Acute Toxicity:  0.941
Maximum Recommended Daily Dose:  0.322
Skin Sensitization:  0.617
Carcinogencity:  0.036
Eye Corrosion:  0.003
Eye Irritation:  0.204
Respiratory Toxicity:  0.977

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC227824

Natural Product ID:  NPC227824
Common Name*:   Izumiphenazine A
IUPAC Name:   n.a.
Synonyms:   Izumiphenazine A
Standard InCHIKey:  LUHDREMZHBQHFC-MLIBEQFHSA-N
Standard InCHI:  InChI=1S/C25H16N4O6/c30-14-5-1-3-11-19(14)28-21-13(26-11)7-9-17-16(35-24(9)23(21)32)8-10(25(33)34)18-22(17)29-20-12(27-18)4-2-6-15(20)31/h1-6,8-9,23-24,30-32H,7H2,(H,33,34)/t9-,23+,24+/m0/s1
SMILES:  OC(=O)c1cc2O[C@@H]3[C@H](c2c2c1nc1cccc(c1n2)O)Cc1c([C@H]3O)nc2c(n1)cccc2O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1651325
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004788] Diazanaphthalenes
        • [CHEMONTID:0004789] Benzodiazines
          • [CHEMONTID:0000486] Quinoxalines
            • [CHEMONTID:0000416] Phenazines and derivatives

*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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]

☑ 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
NPT196 Cell Line AGS Homo sapiens Activity = 78.0 % PMID[529756]
NPT196 Cell Line AGS Homo sapiens Activity = 19.0 % PMID[529757]

☑ 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 NPC227824 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
0.8708 High Similarity NPC218388
0.8506 High Similarity NPC291609
0.8465 Intermediate Similarity NPC124300
0.8436 Intermediate Similarity NPC310618
0.7686 Intermediate Similarity NPC165964
0.7588 Intermediate Similarity NPC473800
0.7567 Intermediate Similarity NPC132385
0.752 Intermediate Similarity NPC329631
0.7519 Intermediate Similarity NPC473188
0.7491 Intermediate Similarity NPC101312
0.749 Intermediate Similarity NPC314834
0.7437 Intermediate Similarity NPC314297
0.7437 Intermediate Similarity NPC315545
0.7427 Intermediate Similarity NPC244856
0.7412 Intermediate Similarity NPC475844
0.7397 Intermediate Similarity NPC236424
0.7397 Intermediate Similarity NPC306644
0.7395 Intermediate Similarity NPC313345
0.7395 Intermediate Similarity NPC314855
0.7395 Intermediate Similarity NPC315638
0.7395 Intermediate Similarity NPC313796
0.739 Intermediate Similarity NPC279589
0.7386 Intermediate Similarity NPC89549
0.7366 Intermediate Similarity NPC274842
0.7364 Intermediate Similarity NPC58209
0.7363 Intermediate Similarity NPC45048
0.7358 Intermediate Similarity NPC215837
0.7354 Intermediate Similarity NPC188400
0.7353 Intermediate Similarity NPC314648
0.7338 Intermediate Similarity NPC478083
0.7326 Intermediate Similarity NPC208522
0.7308 Intermediate Similarity NPC270515
0.73 Intermediate Similarity NPC470586
0.7287 Intermediate Similarity NPC160100
0.7255 Intermediate Similarity NPC473187
0.7254 Intermediate Similarity NPC250448
0.725 Intermediate Similarity NPC471736
0.7245 Intermediate Similarity NPC258048
0.7239 Intermediate Similarity NPC152620
0.7233 Intermediate Similarity NPC474701
0.7212 Intermediate Similarity NPC88923
0.7212 Intermediate Similarity NPC100734
0.7212 Intermediate Similarity NPC315634
0.7208 Intermediate Similarity NPC53534
0.7203 Intermediate Similarity NPC161801
0.7203 Intermediate Similarity NPC474188
0.7201 Intermediate Similarity NPC209981
0.72 Intermediate Similarity NPC205372
0.7191 Intermediate Similarity NPC185197
0.7171 Intermediate Similarity NPC179287
0.717 Intermediate Similarity NPC478080
0.7169 Intermediate Similarity NPC473639
0.7165 Intermediate Similarity NPC474688
0.7154 Intermediate Similarity NPC274640
0.7154 Intermediate Similarity NPC284685
0.7148 Intermediate Similarity NPC203373
0.7143 Intermediate Similarity NPC200888
0.7143 Intermediate Similarity NPC148889
0.7143 Intermediate Similarity NPC280714
0.7137 Intermediate Similarity NPC184408
0.7131 Intermediate Similarity NPC51388
0.7126 Intermediate Similarity NPC160898
0.7121 Intermediate Similarity NPC57453
0.7119 Intermediate Similarity NPC308392
0.7115 Intermediate Similarity NPC166712
0.7105 Intermediate Similarity NPC472435
0.7104 Intermediate Similarity NPC41501
0.7097 Intermediate Similarity NPC312645
0.7093 Intermediate Similarity NPC6786
0.7085 Intermediate Similarity NPC118228
0.7082 Intermediate Similarity NPC34770
0.7077 Intermediate Similarity NPC99891
0.7077 Intermediate Similarity NPC477066
0.7075 Intermediate Similarity NPC202503
0.7074 Intermediate Similarity NPC328928
0.7073 Intermediate Similarity NPC472098
0.7073 Intermediate Similarity NPC203168
0.7063 Intermediate Similarity NPC314633
0.7063 Intermediate Similarity NPC191489
0.7057 Intermediate Similarity NPC67401
0.7052 Intermediate Similarity NPC280799
0.7051 Intermediate Similarity NPC110741
0.705 Intermediate Similarity NPC478081
0.7047 Intermediate Similarity NPC140296
0.7043 Intermediate Similarity NPC473182
0.7041 Intermediate Similarity NPC478045
0.7039 Intermediate Similarity NPC90415
0.7036 Intermediate Similarity NPC97746
0.7031 Intermediate Similarity NPC217176
0.7026 Intermediate Similarity NPC472436
0.7024 Intermediate Similarity NPC144452
0.702 Intermediate Similarity NPC252251
0.7016 Intermediate Similarity NPC327769
0.7012 Intermediate Similarity NPC472099
0.7008 Intermediate Similarity NPC17437
0.7008 Intermediate Similarity NPC107836
0.7004 Intermediate Similarity NPC49547
0.6996 Remote Similarity NPC470042
0.6996 Remote Similarity NPC94842
0.6996 Remote Similarity NPC472434
0.6992 Remote Similarity NPC219664
0.6988 Remote Similarity NPC152768
0.6988 Remote Similarity NPC148183
0.6985 Remote Similarity NPC477067
0.6985 Remote Similarity NPC478082
0.6981 Remote Similarity NPC173250
0.698 Remote Similarity NPC74575
0.698 Remote Similarity NPC470931
0.6978 Remote Similarity NPC237901
0.6978 Remote Similarity NPC195788
0.6976 Remote Similarity NPC89508
0.6976 Remote Similarity NPC39500
0.6974 Remote Similarity NPC282346
0.6972 Remote Similarity NPC473179
0.6965 Remote Similarity NPC477531
0.6963 Remote Similarity NPC129897
0.696 Remote Similarity NPC314552
0.6958 Remote Similarity NPC208364
0.6955 Remote Similarity NPC317572
0.6955 Remote Similarity NPC207620
0.6952 Remote Similarity NPC472589
0.6952 Remote Similarity NPC120513
0.695 Remote Similarity NPC182222
0.695 Remote Similarity NPC39370
0.695 Remote Similarity NPC277351
0.6949 Remote Similarity NPC144381
0.6944 Remote Similarity NPC128115
0.694 Remote Similarity NPC472588
0.694 Remote Similarity NPC314222
0.694 Remote Similarity NPC196449
0.6938 Remote Similarity NPC474192
0.6938 Remote Similarity NPC475720
0.6938 Remote Similarity NPC30456
0.6938 Remote Similarity NPC132329
0.6933 Remote Similarity NPC230403
0.6932 Remote Similarity NPC131885
0.6931 Remote Similarity NPC169716
0.6926 Remote Similarity NPC209174
0.6914 Remote Similarity NPC326930
0.6914 Remote Similarity NPC475301
0.691 Remote Similarity NPC243058
0.6908 Remote Similarity NPC168922
0.6906 Remote Similarity NPC471303
0.6905 Remote Similarity NPC148409
0.6905 Remote Similarity NPC208084
0.6902 Remote Similarity NPC21638
0.6902 Remote Similarity NPC473449
0.6899 Remote Similarity NPC475303
0.6899 Remote Similarity NPC260434
0.6899 Remote Similarity NPC475596
0.6898 Remote Similarity NPC472111
0.6897 Remote Similarity NPC476995
0.6897 Remote Similarity NPC473183
0.6895 Remote Similarity NPC220337
0.6895 Remote Similarity NPC294375
0.6894 Remote Similarity NPC314573
0.6894 Remote Similarity NPC194040
0.6889 Remote Similarity NPC13603
0.6886 Remote Similarity NPC471978
0.6885 Remote Similarity NPC223427
0.6882 Remote Similarity NPC210296
0.688 Remote Similarity NPC203635
0.688 Remote Similarity NPC1608
0.688 Remote Similarity NPC16066
0.6879 Remote Similarity NPC260909
0.6877 Remote Similarity NPC329982
0.6875 Remote Similarity NPC473833
0.6875 Remote Similarity NPC473506
0.6873 Remote Similarity NPC473186
0.6873 Remote Similarity NPC469554
0.687 Remote Similarity NPC244741
0.6863 Remote Similarity NPC322482
0.6854 Remote Similarity NPC91868
0.6854 Remote Similarity NPC63971
0.6853 Remote Similarity NPC256268
0.6852 Remote Similarity NPC53255
0.6852 Remote Similarity NPC85879
0.6848 Remote Similarity NPC473185
0.6846 Remote Similarity NPC473105
0.6842 Remote Similarity NPC178858
0.684 Remote Similarity NPC232225
0.6838 Remote Similarity NPC298436
0.6834 Remote Similarity NPC477112
0.6834 Remote Similarity NPC316841
0.6832 Remote Similarity NPC470022
0.6829 Remote Similarity NPC304183
0.6827 Remote Similarity NPC87413
0.6822 Remote Similarity NPC470486
0.6822 Remote Similarity NPC471977
0.6822 Remote Similarity NPC471190
0.6822 Remote Similarity NPC476997
0.6822 Remote Similarity NPC475644
0.682 Remote Similarity NPC473184
0.682 Remote Similarity NPC475406
0.6815 Remote Similarity NPC244543
0.6815 Remote Similarity NPC469589
0.6815 Remote Similarity NPC209769
0.6812 Remote Similarity NPC471979
0.6811 Remote Similarity NPC174760
0.6811 Remote Similarity NPC150239

  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 NPC227824 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
0.792 Intermediate Similarity NPD5488 Discontinued
0.7731 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7417 Discontinued
0.7605 Intermediate Similarity NPD5416 Discontinued
0.7562 Intermediate Similarity NPD7395 Discontinued
0.753 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.751 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6456 Discontinued
0.7451 Intermediate Similarity NPD6716 Phase 1
0.744 Intermediate Similarity NPD6962 Phase 2
0.7419 Intermediate Similarity NPD7426 Phase 1
0.7413 Intermediate Similarity NPD5482 Discontinued
0.7326 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD2951 Discontinued
0.728 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD8091 Phase 3
0.7244 Intermediate Similarity NPD4373 Phase 2
0.722 Intermediate Similarity NPD5429 Discontinued
0.7212 Intermediate Similarity NPD7803 Approved
0.7171 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD7956 Approved
0.7154 Intermediate Similarity NPD7955 Approved
0.7148 Intermediate Similarity NPD5450 Discontinued
0.7137 Intermediate Similarity NPD3746 Discontinued
0.7137 Intermediate Similarity NPD5632 Approved
0.7132 Intermediate Similarity NPD8364 Approved
0.7132 Intermediate Similarity NPD8463 Approved
0.7132 Intermediate Similarity NPD8363 Approved
0.7126 Intermediate Similarity NPD4952 Phase 3
0.7107 Intermediate Similarity NPD5530 Phase 1
0.7103 Intermediate Similarity NPD3925 Approved
0.7098 Intermediate Similarity NPD1505 Phase 2
0.7098 Intermediate Similarity NPD7284 Clinical (unspecified phase)
0.7096 Intermediate Similarity NPD7924 Phase 2
0.7096 Intermediate Similarity NPD7925 Phase 2
0.7089 Intermediate Similarity NPD5512 Phase 3
0.708 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7708 Approved
0.7063 Intermediate Similarity NPD6228 Discontinued
0.7059 Intermediate Similarity NPD5022 Discontinued
0.7054 Intermediate Similarity NPD7853 Phase 2
0.705 Intermediate Similarity NPD7181 Phase 3
0.7024 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD3986 Discontinued
0.7015 Intermediate Similarity NPD8244 Phase 2
0.7012 Intermediate Similarity NPD5930 Phase 3
0.7008 Intermediate Similarity NPD8358 Approved
0.7 Intermediate Similarity NPD6531 Approved
0.7 Intermediate Similarity NPD6530 Approved
0.6992 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2433 Clinical (unspecified phase)
0.6978 Remote Similarity NPD8466 Approved
0.6978 Remote Similarity NPD8465 Approved
0.6978 Remote Similarity NPD8467 Approved
0.6972 Remote Similarity NPD7194 Discontinued
0.696 Remote Similarity NPD5164 Discontinued
0.6955 Remote Similarity NPD8101 Phase 3
0.6943 Remote Similarity NPD3328 Phase 2
0.6939 Remote Similarity NPD7222 Phase 2
0.6932 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7921 Approved
0.6926 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6926 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6917 Remote Similarity NPD8102 Discontinued
0.6914 Remote Similarity NPD4328 Approved
0.6911 Remote Similarity NPD7558 Phase 2
0.6897 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6895 Remote Similarity NPD4502 Phase 2
0.688 Remote Similarity NPD5902 Approved
0.688 Remote Similarity NPD5903 Approved
0.6879 Remote Similarity NPD8459 Approved
0.6879 Remote Similarity NPD8426 Approved
0.6879 Remote Similarity NPD8460 Approved
0.6879 Remote Similarity NPD8425 Approved
0.6875 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5640 Discontinued
0.6875 Remote Similarity NPD7674 Phase 3
0.6875 Remote Similarity NPD7675 Phase 3
0.6875 Remote Similarity NPD3263 Phase 3
0.6875 Remote Similarity NPD6550 Discontinued
0.6873 Remote Similarity NPD7797 Approved
0.6873 Remote Similarity NPD7796 Approved
0.6858 Remote Similarity NPD3006 Discontinued
0.6857 Remote Similarity NPD8428 Approved
0.6857 Remote Similarity NPD6138 Clinical (unspecified phase)
0.6857 Remote Similarity NPD8429 Approved
0.6857 Remote Similarity NPD8427 Approved
0.685 Remote Similarity NPD5506 Approved
0.685 Remote Similarity NPD5507 Approved
0.6848 Remote Similarity NPD7994 Phase 2
0.6848 Remote Similarity NPD3259 Approved
0.6842 Remote Similarity NPD8100 Phase 3
0.6838 Remote Similarity NPD3258 Approved
0.6835 Remote Similarity NPD8357 Approved
0.6827 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6827 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4989 Phase 2
0.6824 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6812 Remote Similarity NPD6773 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6802 Remote Similarity NPD6296 Discontinued
0.6795 Remote Similarity NPD5479 Discontinued
0.6792 Remote Similarity NPD7022 Phase 2
0.6784 Remote Similarity NPD7556 Discontinued
0.6782 Remote Similarity NPD6494 Phase 2
0.6778 Remote Similarity NPD7859 Phase 2
0.6774 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6768 Remote Similarity NPD4368 Phase 2
0.6761 Remote Similarity NPD3003 Approved
0.6757 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6746 Remote Similarity NPD4897 Phase 2
0.674 Remote Similarity NPD8461 Discontinued
0.6734 Remote Similarity NPD7452 Approved
0.6734 Remote Similarity NPD7453 Approved
0.6733 Remote Similarity NPD5866 Approved
0.6732 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2779 Approved
0.6706 Remote Similarity NPD3945 Discontinued
0.6706 Remote Similarity NPD3875 Discontinued
0.6706 Remote Similarity NPD6974 Phase 3
0.6705 Remote Similarity NPD1867 Approved
0.6691 Remote Similarity NPD6276 Discontinued
0.6691 Remote Similarity NPD8370 Discontinued
0.6691 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6691 Remote Similarity NPD7868 Clinical (unspecified phase)
0.668 Remote Similarity NPD4667 Clinical (unspecified phase)
0.668 Remote Similarity NPD3257 Approved
0.668 Remote Similarity NPD7180 Phase 3
0.6679 Remote Similarity NPD7169 Suspended
0.6679 Remote Similarity NPD4894 Discontinued
0.6667 Remote Similarity NPD7548 Discontinued
0.6667 Remote Similarity NPD7069 Discontinued
0.6667 Remote Similarity NPD8324 Phase 2
0.6667 Remote Similarity NPD5891 Approved
0.6667 Remote Similarity NPD1483 Discontinued
0.6667 Remote Similarity NPD8247 Approved
0.6667 Remote Similarity NPD4429 Discontinued
0.6667 Remote Similarity NPD8246 Approved
0.6654 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6654 Remote Similarity NPD6460 Clinical (unspecified phase)
0.6654 Remote Similarity NPD7726 Phase 1
0.6654 Remote Similarity NPD8016 Phase 3
0.6654 Remote Similarity NPD8359 Phase 2
0.6654 Remote Similarity NPD4561 Discontinued
0.6653 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6644 Remote Similarity NPD8310 Clinical (unspecified phase)
0.6643 Remote Similarity NPD7766 Phase 2
0.6642 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6642 Remote Similarity NPD5805 Approved
0.6641 Remote Similarity NPD6247 Clinical (unspecified phase)
0.664 Remote Similarity NPD7571 Clinical (unspecified phase)
0.663 Remote Similarity NPD7996 Phase 2
0.6629 Remote Similarity NPD6790 Phase 1
0.6626 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6621 Remote Similarity NPD8489 Phase 1
0.6616 Remote Similarity NPD5151 Clinical (unspecified phase)
0.6604 Remote Similarity NPD8117 Approved
0.6604 Remote Similarity NPD8116 Phase 3
0.6602 Remote Similarity NPD3912 Discontinued
0.6602 Remote Similarity NPD6985 Discontinued
0.66 Remote Similarity NPD6290 Phase 2
0.6597 Remote Similarity NPD7546 Discontinued
0.6591 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5612 Discontinued
0.6586 Remote Similarity NPD31 Approved
0.6586 Remote Similarity NPD4038 Approved
0.6586 Remote Similarity NPD32 Approved
0.6586 Remote Similarity NPD4036 Approved
0.6586 Remote Similarity NPD4039 Approved
0.6586 Remote Similarity NPD4035 Approved
0.6586 Remote Similarity NPD4033 Approved
0.6586 Remote Similarity NPD4122 Approved
0.6586 Remote Similarity NPD4034 Approved
0.6586 Remote Similarity NPD4037 Approved
0.6585 Remote Similarity NPD2778 Approved
0.6585 Remote Similarity NPD6874 Approved
0.6578 Remote Similarity NPD1466 Phase 3
0.6578 Remote Similarity NPD1467 Approved
0.6576 Remote Similarity NPD2899 Discontinued
0.6576 Remote Similarity NPD5519 Discontinued
0.6576 Remote Similarity NPD7404 Approved
0.6574 Remote Similarity NPD2916 Discontinued
0.6574 Remote Similarity NPD5658 Approved
0.6571 Remote Similarity NPD7673 Phase 3
0.6571 Remote Similarity NPD6988 Phase 1
0.6566 Remote Similarity NPD6964 Approved
0.6566 Remote Similarity NPD6963 Approved
0.6566 Remote Similarity NPD3074 Discontinued
0.6564 Remote Similarity NPD4049 Phase 2
0.6561 Remote Similarity NPD5939 Approved
0.6561 Remote Similarity NPD5936 Approved
0.656 Remote Similarity NPD6245 Phase 2
0.656 Remote Similarity NPD5459 Phase 2
0.6557 Remote Similarity NPD4418 Discontinued
0.6553 Remote Similarity NPD7031 Phase 1
0.6552 Remote Similarity NPD1955 Discontinued
0.655 Remote Similarity NPD5850 Phase 3

  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