Structure

Physi-Chem Properties

Molecular Weight:  570.25
Volume:  618.06
LogP:  8.139
LogD:  4.966
LogS:  -2.417
# Rotatable Bonds:  10
TPSA:  86.71
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.146
Synthetic Accessibility Score:  2.955
Fsp3:  0.162
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.85
MDCK Permeability:  1.3269606824906077e-05
Pgp-inhibitor:  0.984
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.565

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  103.51563262939453%
Volume Distribution (VD):  0.309
Pgp-substrate:  0.2665448486804962%

ADMET: Metabolism

CYP1A2-inhibitor:  0.43
CYP1A2-substrate:  0.099
CYP2C19-inhibitor:  0.638
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.517
CYP2C9-substrate:  0.176
CYP2D6-inhibitor:  0.227
CYP2D6-substrate:  0.048
CYP3A4-inhibitor:  0.127
CYP3A4-substrate:  0.121

ADMET: Excretion

Clearance (CL):  1.009
Half-life (T1/2):  0.267

ADMET: Toxicity

hERG Blockers:  0.571
Human Hepatotoxicity (H-HT):  0.923
Drug-inuced Liver Injury (DILI):  0.99
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.098
Maximum Recommended Daily Dose:  0.624
Skin Sensitization:  0.314
Carcinogencity:  0.111
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.568

Download Data

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

  Natural Product: NPC313293

Natural Product ID:  NPC313293
Common Name*:   Benthophoenin
IUPAC Name:   3,7-dibenzoyl-5-[(2E)-3,7-dimethylocta-2,6-dienyl]-10H-phenazine-1-carboxylic acid
Synonyms:   Benthophoenin
Standard InCHIKey:  ZXEFSITWOFAFSF-NCELDCMTSA-N
Standard InCHI:  InChI=1S/C37H34N2O4/c1-24(2)11-10-12-25(3)19-20-39-32-22-28(35(40)26-13-6-4-7-14-26)17-18-31(32)38-34-30(37(42)43)21-29(23-33(34)39)36(41)27-15-8-5-9-16-27/h4-9,11,13-19,21-23,38H,10,12,20H2,1-3H3,(H,42,43)/b25-19+
SMILES:  C/C(=CCn1c2cc(ccc2[nH]c2c1cc(cc2C(=O)O)C(=O)c1ccccc1)C(=O)c1ccccc1)/CCC=C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL499008
PubChem CID:   44584441
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
NPO15351 Streptomyces prunicolor Species Streptomycetaceae Bacteria n.a. mycelium n.a. DOI[10.1021/np50098a008]
NPO15351 Streptomyces prunicolor Species Streptomycetaceae Bacteria 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.15 ug.mL-1 PMID[542966]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.8 ug.mL-1 PMID[542966]

☑ 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 NPC313293 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
0.9643 High Similarity NPC470317
0.8701 High Similarity NPC471742
0.8362 Intermediate Similarity NPC471743
0.7921 Intermediate Similarity NPC182131
0.785 Intermediate Similarity NPC471741
0.7797 Intermediate Similarity NPC27904
0.7405 Intermediate Similarity NPC318183
0.7368 Intermediate Similarity NPC243058
0.7337 Intermediate Similarity NPC253476
0.733 Intermediate Similarity NPC203635
0.7283 Intermediate Similarity NPC43477
0.7268 Intermediate Similarity NPC477998
0.7254 Intermediate Similarity NPC90415
0.7228 Intermediate Similarity NPC189116
0.7211 Intermediate Similarity NPC256268
0.7158 Intermediate Similarity NPC219848
0.7128 Intermediate Similarity NPC292265
0.7108 Intermediate Similarity NPC314648
0.7081 Intermediate Similarity NPC199737
0.7079 Intermediate Similarity NPC478039
0.7045 Intermediate Similarity NPC472241
0.7029 Intermediate Similarity NPC472243
0.7022 Intermediate Similarity NPC472242
0.699 Remote Similarity NPC313796
0.699 Remote Similarity NPC313345
0.699 Remote Similarity NPC314855
0.699 Remote Similarity NPC315638
0.6963 Remote Similarity NPC470548
0.6959 Remote Similarity NPC314098
0.6957 Remote Similarity NPC314297
0.6957 Remote Similarity NPC315545
0.6952 Remote Similarity NPC204867
0.6906 Remote Similarity NPC237649
0.6906 Remote Similarity NPC300596
0.6897 Remote Similarity NPC173295
0.6895 Remote Similarity NPC472118
0.6882 Remote Similarity NPC36495
0.6868 Remote Similarity NPC144691
0.6864 Remote Similarity NPC472244
0.6864 Remote Similarity NPC470343
0.6859 Remote Similarity NPC126676
0.6859 Remote Similarity NPC112336
0.6859 Remote Similarity NPC469671
0.6859 Remote Similarity NPC474814
0.6857 Remote Similarity NPC314834
0.6856 Remote Similarity NPC474041
0.6842 Remote Similarity NPC473484
0.6842 Remote Similarity NPC224970
0.6842 Remote Similarity NPC167724
0.6842 Remote Similarity NPC223595
0.6836 Remote Similarity NPC242933
0.6835 Remote Similarity NPC115588
0.6834 Remote Similarity NPC316405
0.68 Remote Similarity NPC151171
0.6798 Remote Similarity NPC470787
0.6798 Remote Similarity NPC472540
0.6798 Remote Similarity NPC472539
0.6796 Remote Similarity NPC471944
0.6789 Remote Similarity NPC472114
0.6789 Remote Similarity NPC472115
0.6786 Remote Similarity NPC268534
0.6769 Remote Similarity NPC474815
0.6768 Remote Similarity NPC49184
0.6765 Remote Similarity NPC472542
0.6765 Remote Similarity NPC472541
0.6753 Remote Similarity NPC475607
0.6735 Remote Similarity NPC475685
0.6732 Remote Similarity NPC474916
0.6719 Remote Similarity NPC471778
0.6718 Remote Similarity NPC474081
0.6717 Remote Similarity NPC97584
0.6714 Remote Similarity NPC477999
0.6705 Remote Similarity NPC472245
0.6701 Remote Similarity NPC475594
0.67 Remote Similarity NPC473815
0.6667 Remote Similarity NPC130931
0.6651 Remote Similarity NPC274842
0.665 Remote Similarity NPC298320
0.6649 Remote Similarity NPC471130
0.6649 Remote Similarity NPC61013
0.6636 Remote Similarity NPC244856
0.6633 Remote Similarity NPC14849
0.6632 Remote Similarity NPC99632
0.6632 Remote Similarity NPC282339
0.6632 Remote Similarity NPC88970
0.6632 Remote Similarity NPC293458
0.6629 Remote Similarity NPC159722
0.6619 Remote Similarity NPC301292
0.6619 Remote Similarity NPC133156
0.6619 Remote Similarity NPC313112
0.6615 Remote Similarity NPC469726
0.6615 Remote Similarity NPC329338
0.6609 Remote Similarity NPC194562
0.6607 Remote Similarity NPC226143
0.6605 Remote Similarity NPC236424
0.6605 Remote Similarity NPC306644
0.6603 Remote Similarity NPC475223
0.6599 Remote Similarity NPC475761
0.6599 Remote Similarity NPC99043
0.6599 Remote Similarity NPC218594
0.6579 Remote Similarity NPC248117
0.6574 Remote Similarity NPC298449
0.6571 Remote Similarity NPC246983
0.6571 Remote Similarity NPC475448
0.657 Remote Similarity NPC138615
0.657 Remote Similarity NPC311054
0.657 Remote Similarity NPC132874
0.657 Remote Similarity NPC112752
0.657 Remote Similarity NPC218733
0.657 Remote Similarity NPC265642
0.6561 Remote Similarity NPC229893
0.6559 Remote Similarity NPC314223
0.6557 Remote Similarity NPC478075
0.6553 Remote Similarity NPC303214
0.6552 Remote Similarity NPC150863
0.6552 Remote Similarity NPC5630
0.6552 Remote Similarity NPC122235
0.6548 Remote Similarity NPC229353
0.6545 Remote Similarity NPC476231
0.6544 Remote Similarity NPC322064
0.6535 Remote Similarity NPC14994
0.6531 Remote Similarity NPC328611
0.653 Remote Similarity NPC223590
0.6529 Remote Similarity NPC103292
0.6529 Remote Similarity NPC257490
0.6528 Remote Similarity NPC278887
0.6528 Remote Similarity NPC31700
0.6526 Remote Similarity NPC193410
0.6524 Remote Similarity NPC218388
0.6522 Remote Similarity NPC259678
0.6522 Remote Similarity NPC90967
0.652 Remote Similarity NPC203628
0.6515 Remote Similarity NPC475094
0.6515 Remote Similarity NPC147298
0.6515 Remote Similarity NPC182057
0.6515 Remote Similarity NPC131450
0.6514 Remote Similarity NPC473837
0.6514 Remote Similarity NPC314431
0.6514 Remote Similarity NPC280807
0.6509 Remote Similarity NPC225400
0.6505 Remote Similarity NPC21483
0.6505 Remote Similarity NPC198205
0.6503 Remote Similarity NPC314186
0.65 Remote Similarity NPC319645
0.65 Remote Similarity NPC181527
0.6497 Remote Similarity NPC203202
0.6497 Remote Similarity NPC264482
0.6495 Remote Similarity NPC470971
0.6492 Remote Similarity NPC474058
0.6486 Remote Similarity NPC254798
0.648 Remote Similarity NPC177261
0.6479 Remote Similarity NPC472538
0.6479 Remote Similarity NPC222561
0.6479 Remote Similarity NPC471155
0.6479 Remote Similarity NPC470786
0.6476 Remote Similarity NPC176371
0.6476 Remote Similarity NPC232600
0.6476 Remote Similarity NPC136573
0.6474 Remote Similarity NPC123241
0.6473 Remote Similarity NPC170333
0.6471 Remote Similarity NPC150323
0.6471 Remote Similarity NPC473298
0.6471 Remote Similarity NPC161956
0.6471 Remote Similarity NPC471195
0.6471 Remote Similarity NPC471196
0.6471 Remote Similarity NPC258531
0.6471 Remote Similarity NPC279385
0.6471 Remote Similarity NPC112373
0.6471 Remote Similarity NPC179605
0.6465 Remote Similarity NPC186669
0.6465 Remote Similarity NPC25961
0.6459 Remote Similarity NPC90358
0.6459 Remote Similarity NPC107828
0.6458 Remote Similarity NPC469741
0.6453 Remote Similarity NPC107836
0.6453 Remote Similarity NPC181928
0.6453 Remote Similarity NPC21425
0.6452 Remote Similarity NPC250448
0.6449 Remote Similarity NPC270241
0.6445 Remote Similarity NPC15987
0.6445 Remote Similarity NPC288759
0.6442 Remote Similarity NPC198390
0.644 Remote Similarity NPC471122
0.6438 Remote Similarity NPC208522
0.6432 Remote Similarity NPC6974
0.6429 Remote Similarity NPC316202
0.6429 Remote Similarity NPC471164
0.6418 Remote Similarity NPC159963
0.6416 Remote Similarity NPC226794
0.6416 Remote Similarity NPC285394
0.6412 Remote Similarity NPC177684
0.6412 Remote Similarity NPC291962
0.6406 Remote Similarity NPC93653
0.6406 Remote Similarity NPC201424
0.6406 Remote Similarity NPC225319
0.6402 Remote Similarity NPC308943
0.64 Remote Similarity NPC58827
0.64 Remote Similarity NPC307437
0.64 Remote Similarity NPC72473
0.6392 Remote Similarity NPC470069

  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 NPC313293 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
0.7895 Intermediate Similarity NPD4888 Discontinued
0.7831 Intermediate Similarity NPD5504 Discontinued
0.7632 Intermediate Similarity NPD7855 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD1625 Approved
0.754 Intermediate Similarity NPD4330 Approved
0.754 Intermediate Similarity NPD4329 Approved
0.7527 Intermediate Similarity NPD3792 Approved
0.7513 Intermediate Similarity NPD7569 Approved
0.7513 Intermediate Similarity NPD7570 Approved
0.7442 Intermediate Similarity NPD1189 Approved
0.7368 Intermediate Similarity NPD1626 Approved
0.7368 Intermediate Similarity NPD8281 Discontinued
0.7356 Intermediate Similarity NPD5918 Discontinued
0.7345 Intermediate Similarity NPD2737 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD5466 Approved
0.7326 Intermediate Similarity NPD7449 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD5086 Approved
0.7312 Intermediate Similarity NPD3776 Discontinued
0.7297 Intermediate Similarity NPD2037 Approved
0.7273 Intermediate Similarity NPD3377 Discontinued
0.7249 Intermediate Similarity NPD5498 Phase 2
0.7219 Intermediate Similarity NPD5727 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3782 Discontinued
0.7181 Intermediate Similarity NPD5997 Discontinued
0.7158 Intermediate Similarity NPD3755 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5919 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5928 Phase 1
0.7135 Intermediate Similarity NPD3471 Approved
0.7135 Intermediate Similarity NPD3470 Approved
0.7128 Intermediate Similarity NPD2431 Approved
0.7128 Intermediate Similarity NPD6483 Approved
0.7128 Intermediate Similarity NPD6484 Approved
0.7128 Intermediate Similarity NPD2432 Approved
0.712 Intermediate Similarity NPD2506 Approved
0.7112 Intermediate Similarity NPD2454 Approved
0.7112 Intermediate Similarity NPD2455 Approved
0.7104 Intermediate Similarity NPD212 Discontinued
0.7083 Intermediate Similarity NPD5445 Approved
0.7065 Intermediate Similarity NPD5856 Discontinued
0.7049 Intermediate Similarity NPD2836 Approved
0.7042 Intermediate Similarity NPD7858 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD6163 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD1230 Approved
0.7 Intermediate Similarity NPD4161 Discontinued
0.7 Intermediate Similarity NPD7854 Phase 2
0.6984 Remote Similarity NPD7795 Phase 2
0.6977 Remote Similarity NPD1527 Phase 2
0.6973 Remote Similarity NPD2427 Approved
0.6963 Remote Similarity NPD3422 Phase 3
0.6963 Remote Similarity NPD2359 Approved
0.6963 Remote Similarity NPD3423 Phase 2
0.6961 Remote Similarity NPD5748 Phase 2
0.6927 Remote Similarity NPD2083 Clinical (unspecified phase)
0.6927 Remote Similarity NPD2361 Approved
0.6915 Remote Similarity NPD5430 Discontinued
0.6914 Remote Similarity NPD6342 Discontinued
0.6907 Remote Similarity NPD7014 Clinical (unspecified phase)
0.69 Remote Similarity NPD8146 Phase 2
0.6898 Remote Similarity NPD1210 Approved
0.6893 Remote Similarity NPD2010 Phase 3
0.6888 Remote Similarity NPD5923 Phase 1
0.6864 Remote Similarity NPD1574 Approved
0.6859 Remote Similarity NPD7663 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3468 Approved
0.6833 Remote Similarity NPD5933 Phase 3
0.6833 Remote Similarity NPD5932 Phase 3
0.6833 Remote Similarity NPD5931 Phase 3
0.6816 Remote Similarity NPD5937 Approved
0.6816 Remote Similarity NPD2820 Phase 3
0.6813 Remote Similarity NPD7528 Approved
0.6811 Remote Similarity NPD4045 Phase 2
0.6811 Remote Similarity NPD4042 Phase 2
0.6789 Remote Similarity NPD8002 Clinical (unspecified phase)
0.6789 Remote Similarity NPD8003 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7940 Phase 3
0.6786 Remote Similarity NPD7867 Phase 1
0.678 Remote Similarity NPD3170 Approved
0.6776 Remote Similarity NPD8149 Discontinued
0.6771 Remote Similarity NPD1913 Phase 1
0.6771 Remote Similarity NPD1165 Clinical (unspecified phase)
0.6766 Remote Similarity NPD5042 Phase 1
0.676 Remote Similarity NPD2365 Approved
0.6758 Remote Similarity NPD1802 Approved
0.6758 Remote Similarity NPD1801 Approved
0.6748 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6743 Remote Similarity NPD5185 Approved
0.6743 Remote Similarity NPD5184 Approved
0.6743 Remote Similarity NPD5182 Approved
0.674 Remote Similarity NPD6017 Discontinued
0.6738 Remote Similarity NPD7735 Clinical (unspecified phase)
0.6735 Remote Similarity NPD6833 Clinical (unspecified phase)
0.6732 Remote Similarity NPD5194 Approved
0.6732 Remote Similarity NPD5197 Approved
0.6732 Remote Similarity NPD5196 Approved
0.6731 Remote Similarity NPD6480 Clinical (unspecified phase)
0.6722 Remote Similarity NPD4430 Phase 2
0.6719 Remote Similarity NPD2369 Discontinued
0.6718 Remote Similarity NPD8006 Clinical (unspecified phase)
0.6717 Remote Similarity NPD4412 Phase 2
0.6716 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6714 Remote Similarity NPD7301 Phase 3
0.6713 Remote Similarity NPD7878 Phase 2
0.6702 Remote Similarity NPD33 Approved
0.6702 Remote Similarity NPD4393 Approved
0.6702 Remote Similarity NPD4645 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5637 Discontinued
0.67 Remote Similarity NPD4948 Discontinued
0.6698 Remote Similarity NPD5860 Discontinued
0.6696 Remote Similarity NPD7922 Phase 1
0.6685 Remote Similarity NPD6506 Clinical (unspecified phase)
0.6684 Remote Similarity NPD1208 Approved
0.6684 Remote Similarity NPD1211 Clinical (unspecified phase)
0.6683 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6683 Remote Similarity NPD3828 Approved
0.6682 Remote Similarity NPD4082 Approved
0.6667 Remote Similarity NPD2790 Discontinued
0.6667 Remote Similarity NPD7088 Discontinued
0.6667 Remote Similarity NPD2404 Discontinued
0.6667 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4311 Approved
0.6667 Remote Similarity NPD6768 Approved
0.6651 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6635 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5143 Clinical (unspecified phase)
0.6633 Remote Similarity NPD4092 Approved
0.6632 Remote Similarity NPD5183 Approved
0.6632 Remote Similarity NPD3376 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5186 Approved
0.6623 Remote Similarity NPD5488 Discontinued
0.6619 Remote Similarity NPD5901 Discontinued
0.6619 Remote Similarity NPD6987 Phase 1
0.6615 Remote Similarity NPD3587 Clinical (unspecified phase)
0.661 Remote Similarity NPD2791 Discontinued
0.6608 Remote Similarity NPD1640 Clinical (unspecified phase)
0.6603 Remote Similarity NPD7071 Clinical (unspecified phase)
0.6602 Remote Similarity NPD7572 Phase 2
0.6602 Remote Similarity NPD5195 Discontinued
0.6602 Remote Similarity NPD7238 Clinical (unspecified phase)
0.66 Remote Similarity NPD6021 Clinical (unspecified phase)
0.66 Remote Similarity NPD8167 Discontinued
0.6599 Remote Similarity NPD2869 Clinical (unspecified phase)
0.6599 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6597 Remote Similarity NPD8007 Approved
0.6597 Remote Similarity NPD8008 Approved
0.6592 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6592 Remote Similarity NPD7254 Discontinued
0.6591 Remote Similarity NPD2950 Approved
0.6591 Remote Similarity NPD2949 Approved
0.6582 Remote Similarity NPD3978 Clinical (unspecified phase)
0.6582 Remote Similarity NPD4091 Approved
0.6576 Remote Similarity NPD7794 Clinical (unspecified phase)
0.6576 Remote Similarity NPD1553 Approved
0.6575 Remote Similarity NPD6566 Discontinued
0.6575 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6571 Remote Similarity NPD1619 Phase 3
0.657 Remote Similarity NPD4987 Clinical (unspecified phase)
0.657 Remote Similarity NPD5071 Phase 2
0.6566 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7036 Phase 3
0.6562 Remote Similarity NPD7035 Approved
0.6546 Remote Similarity NPD1839 Phase 1
0.6538 Remote Similarity NPD5024 Approved
0.6537 Remote Similarity NPD7429 Clinical (unspecified phase)
0.6537 Remote Similarity NPD5610 Approved
0.6536 Remote Similarity NPD2670 Approved
0.6532 Remote Similarity NPD1593 Approved
0.6531 Remote Similarity NPD3522 Approved
0.6531 Remote Similarity NPD7662 Clinical (unspecified phase)
0.653 Remote Similarity NPD7404 Approved
0.6528 Remote Similarity NPD3795 Approved
0.6528 Remote Similarity NPD3794 Approved
0.6526 Remote Similarity NPD7300 Phase 3
0.6526 Remote Similarity NPD4022 Approved
0.6526 Remote Similarity NPD3472 Approved
0.6526 Remote Similarity NPD7302 Phase 3
0.6526 Remote Similarity NPD7114 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6416 Phase 2
0.6522 Remote Similarity NPD6162 Approved
0.6522 Remote Similarity NPD6161 Approved
0.652 Remote Similarity NPD2336 Approved
0.652 Remote Similarity NPD5871 Discontinued
0.6519 Remote Similarity NPD3434 Clinical (unspecified phase)
0.6519 Remote Similarity NPD3625 Discontinued
0.6519 Remote Similarity NPD4461 Discontinued
0.6519 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6518 Remote Similarity NPD7767 Approved
0.6515 Remote Similarity NPD3998 Approved
0.6515 Remote Similarity NPD3997 Approved
0.6515 Remote Similarity NPD7881 Approved
0.6515 Remote Similarity NPD3999 Approved
0.6513 Remote Similarity NPD4150 Clinical (unspecified phase)
0.6513 Remote Similarity NPD3824 Phase 1
0.6505 Remote Similarity NPD5975 Clinical (unspecified phase)
0.65 Remote Similarity NPD1110 Approved
0.65 Remote Similarity NPD3783 Clinical (unspecified phase)
0.65 Remote Similarity NPD1109 Approved
0.6497 Remote Similarity NPD1541 Approved
0.6497 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6497 Remote Similarity NPD6740 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6657 Clinical (unspecified phase)

  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