Structure

Physi-Chem Properties

Molecular Weight:  243.05
Volume:  229.517
LogP:  3.014
LogD:  3.225
LogS:  -4.558
# Rotatable Bonds:  1
TPSA:  53.72
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.657
Synthetic Accessibility Score:  2.638
Fsp3:  0.154
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.799
MDCK Permeability:  3.288434891146608e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.344
Plasma Protein Binding (PPB):  93.33130645751953%
Volume Distribution (VD):  0.699
Pgp-substrate:  4.2886834144592285%

ADMET: Metabolism

CYP1A2-inhibitor:  0.994
CYP1A2-substrate:  0.572
CYP2C19-inhibitor:  0.945
CYP2C19-substrate:  0.258
CYP2C9-inhibitor:  0.636
CYP2C9-substrate:  0.868
CYP2D6-inhibitor:  0.904
CYP2D6-substrate:  0.894
CYP3A4-inhibitor:  0.884
CYP3A4-substrate:  0.203

ADMET: Excretion

Clearance (CL):  14.991
Half-life (T1/2):  0.281

ADMET: Toxicity

hERG Blockers:  0.05
Human Hepatotoxicity (H-HT):  0.31
Drug-inuced Liver Injury (DILI):  0.925
AMES Toxicity:  0.692
Rat Oral Acute Toxicity:  0.176
Maximum Recommended Daily Dose:  0.553
Skin Sensitization:  0.411
Carcinogencity:  0.934
Eye Corrosion:  0.003
Eye Irritation:  0.076
Respiratory Toxicity:  0.943

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

  Natural Product: NPC168922

Natural Product ID:  NPC168922
Common Name*:   Maculine
IUPAC Name:   n.a.
Synonyms:   Maculine
Standard InCHIKey:  VPNYHHBCMOYPCJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H9NO4/c1-15-12-7-2-3-16-13(7)14-9-5-11-10(4-8(9)12)17-6-18-11/h2-5H,6H2,1H3
SMILES:  COc1c2cc3OCOc3cc2nc2c1cco2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503675
PubChem CID:   68232
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0002374] Furanoquinolines

*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
NPO29436 Vepris punctata Species Rutaceae Eukaryota wood Madagascar rainforest n.a. PMID[12713408]
NPO29436 Vepris punctata Species Rutaceae Eukaryota wood Madagascar Rainforest n.a. PMID[15165160]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[18950230]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15500 Aconitum volubile Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16406 Leptospermum recurvum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16000 Cetorhinus maximus Species Alopiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13941 Aeollanthus buchnerianus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21284 Cynoglossum viridiflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20279 Parmelia damaziana Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29436 Vepris punctata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19166 Helianthus niveus Species Asteraceae 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
NPT179 Cell Line A2780 Homo sapiens IC50 = 4.0 ug.mL-1 PMID[500065]
NPT81 Cell Line A549 Homo sapiens IC50 = 9500.0 nM PMID[500066]

☑ 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 NPC168922 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
0.9724 High Similarity NPC1608
0.9668 High Similarity NPC217176
0.9412 High Similarity NPC173250
0.9406 High Similarity NPC208364
0.9231 High Similarity NPC188400
0.9163 High Similarity NPC120513
0.9104 High Similarity NPC298436
0.9087 High Similarity NPC34770
0.8915 High Similarity NPC16066
0.8894 High Similarity NPC97746
0.8844 High Similarity NPC166712
0.8805 High Similarity NPC160100
0.8777 High Similarity NPC203373
0.8739 High Similarity NPC101312
0.8728 High Similarity NPC58209
0.8726 High Similarity NPC269367
0.8559 High Similarity NPC140296
0.8364 Intermediate Similarity NPC131885
0.8178 Intermediate Similarity NPC205372
0.7719 Intermediate Similarity NPC46561
0.7712 Intermediate Similarity NPC253675
0.7661 Intermediate Similarity NPC89549
0.7571 Intermediate Similarity NPC303374
0.754 Intermediate Similarity NPC315634
0.754 Intermediate Similarity NPC100734
0.754 Intermediate Similarity NPC88923
0.75 Intermediate Similarity NPC308137
0.75 Intermediate Similarity NPC310211
0.7489 Intermediate Similarity NPC219664
0.748 Intermediate Similarity NPC284685
0.7479 Intermediate Similarity NPC119134
0.7468 Intermediate Similarity NPC198503
0.746 Intermediate Similarity NPC230683
0.7446 Intermediate Similarity NPC169402
0.7435 Intermediate Similarity NPC116238
0.7434 Intermediate Similarity NPC249583
0.7427 Intermediate Similarity NPC6786
0.7424 Intermediate Similarity NPC203168
0.7407 Intermediate Similarity NPC204385
0.7389 Intermediate Similarity NPC45190
0.7388 Intermediate Similarity NPC124313
0.7381 Intermediate Similarity NPC191489
0.738 Intermediate Similarity NPC146418
0.7377 Intermediate Similarity NPC207283
0.7377 Intermediate Similarity NPC84164
0.7364 Intermediate Similarity NPC279401
0.7364 Intermediate Similarity NPC79293
0.7354 Intermediate Similarity NPC280714
0.735 Intermediate Similarity NPC174760
0.7339 Intermediate Similarity NPC247803
0.7325 Intermediate Similarity NPC166722
0.7308 Intermediate Similarity NPC208084
0.7302 Intermediate Similarity NPC206201
0.7284 Intermediate Similarity NPC182907
0.7284 Intermediate Similarity NPC189903
0.7281 Intermediate Similarity NPC4687
0.7277 Intermediate Similarity NPC150239
0.7269 Intermediate Similarity NPC134637
0.7265 Intermediate Similarity NPC87560
0.7265 Intermediate Similarity NPC195120
0.7255 Intermediate Similarity NPC209981
0.7243 Intermediate Similarity NPC108342
0.724 Intermediate Similarity NPC183537
0.7237 Intermediate Similarity NPC470042
0.7237 Intermediate Similarity NPC300156
0.7225 Intermediate Similarity NPC41216
0.7203 Intermediate Similarity NPC118154
0.7203 Intermediate Similarity NPC157983
0.7198 Intermediate Similarity NPC472098
0.7195 Intermediate Similarity NPC99891
0.7171 Intermediate Similarity NPC77878
0.716 Intermediate Similarity NPC22481
0.7156 Intermediate Similarity NPC62069
0.7155 Intermediate Similarity NPC179287
0.7155 Intermediate Similarity NPC87413
0.7149 Intermediate Similarity NPC107123
0.7149 Intermediate Similarity NPC207971
0.713 Intermediate Similarity NPC254957
0.713 Intermediate Similarity NPC474595
0.7124 Intermediate Similarity NPC264176
0.7121 Intermediate Similarity NPC471978
0.7118 Intermediate Similarity NPC268077
0.7113 Intermediate Similarity NPC314633
0.7109 Intermediate Similarity NPC185197
0.7106 Intermediate Similarity NPC3207
0.7105 Intermediate Similarity NPC66815
0.7104 Intermediate Similarity NPC471979
0.7103 Intermediate Similarity NPC473188
0.7102 Intermediate Similarity NPC473187
0.7097 Intermediate Similarity NPC124300
0.7094 Intermediate Similarity NPC474594
0.7093 Intermediate Similarity NPC234197
0.7089 Intermediate Similarity NPC148409
0.7072 Intermediate Similarity NPC45389
0.7068 Intermediate Similarity NPC291609
0.7064 Intermediate Similarity NPC146976
0.7061 Intermediate Similarity NPC90875
0.7059 Intermediate Similarity NPC66083
0.7059 Intermediate Similarity NPC469439
0.7056 Intermediate Similarity NPC210296
0.7056 Intermediate Similarity NPC193238
0.7041 Intermediate Similarity NPC196449
0.7041 Intermediate Similarity NPC314222
0.704 Intermediate Similarity NPC78609
0.7037 Intermediate Similarity NPC278525
0.7036 Intermediate Similarity NPC473800
0.7031 Intermediate Similarity NPC199277
0.7031 Intermediate Similarity NPC135887
0.7029 Intermediate Similarity NPC280799
0.7021 Intermediate Similarity NPC236668
0.7014 Intermediate Similarity NPC194040
0.7012 Intermediate Similarity NPC310618
0.7009 Intermediate Similarity NPC187501
0.7004 Intermediate Similarity NPC71124
0.7 Intermediate Similarity NPC148124
0.6991 Remote Similarity NPC312872
0.6983 Remote Similarity NPC321428
0.698 Remote Similarity NPC233334
0.6979 Remote Similarity NPC171409
0.6979 Remote Similarity NPC96405
0.6977 Remote Similarity NPC473833
0.6974 Remote Similarity NPC5374
0.6967 Remote Similarity NPC24019
0.6958 Remote Similarity NPC99724
0.6953 Remote Similarity NPC210828
0.6953 Remote Similarity NPC86834
0.6953 Remote Similarity NPC39679
0.6949 Remote Similarity NPC39500
0.6942 Remote Similarity NPC21638
0.6942 Remote Similarity NPC473449
0.6936 Remote Similarity NPC295479
0.6936 Remote Similarity NPC220241
0.6936 Remote Similarity NPC23294
0.6935 Remote Similarity NPC184680
0.6933 Remote Similarity NPC305984
0.6931 Remote Similarity NPC207620
0.693 Remote Similarity NPC112937
0.6929 Remote Similarity NPC165964
0.6926 Remote Similarity NPC13603
0.6926 Remote Similarity NPC318068
0.6926 Remote Similarity NPC194740
0.6926 Remote Similarity NPC317572
0.6917 Remote Similarity NPC472099
0.6917 Remote Similarity NPC225279
0.691 Remote Similarity NPC135549
0.6908 Remote Similarity NPC470785
0.6908 Remote Similarity NPC227824
0.6907 Remote Similarity NPC296482
0.6907 Remote Similarity NPC53069
0.6907 Remote Similarity NPC202768
0.6906 Remote Similarity NPC169716
0.6905 Remote Similarity NPC471013
0.6905 Remote Similarity NPC148896
0.6905 Remote Similarity NPC180668
0.6902 Remote Similarity NPC67401
0.6902 Remote Similarity NPC302807
0.6894 Remote Similarity NPC303951
0.6894 Remote Similarity NPC470020
0.689 Remote Similarity NPC270515
0.6887 Remote Similarity NPC85879
0.6887 Remote Similarity NPC475301
0.6887 Remote Similarity NPC53255
0.6887 Remote Similarity NPC326930
0.6885 Remote Similarity NPC282346
0.6885 Remote Similarity NPC248903
0.6878 Remote Similarity NPC268223
0.6873 Remote Similarity NPC129897
0.6873 Remote Similarity NPC472436
0.687 Remote Similarity NPC474688
0.687 Remote Similarity NPC477019
0.6865 Remote Similarity NPC15406
0.6863 Remote Similarity NPC10904
0.686 Remote Similarity NPC144452
0.6857 Remote Similarity NPC246381
0.6857 Remote Similarity NPC471762
0.6853 Remote Similarity NPC475844
0.6851 Remote Similarity NPC325297
0.6851 Remote Similarity NPC174758
0.6846 Remote Similarity NPC128115
0.6846 Remote Similarity NPC54066
0.6844 Remote Similarity NPC26928
0.684 Remote Similarity NPC474183
0.684 Remote Similarity NPC470784
0.6838 Remote Similarity NPC313189
0.6833 Remote Similarity NPC184408
0.6822 Remote Similarity NPC472435
0.682 Remote Similarity NPC148183
0.682 Remote Similarity NPC215837
0.682 Remote Similarity NPC152768
0.6818 Remote Similarity NPC60621
0.6816 Remote Similarity NPC157931
0.6815 Remote Similarity NPC172222
0.6809 Remote Similarity NPC82548
0.6805 Remote Similarity NPC46451
0.6802 Remote Similarity NPC476999
0.6798 Remote Similarity NPC131017
0.6794 Remote Similarity NPC328928
0.679 Remote Similarity NPC210434
0.6789 Remote Similarity NPC274640
0.6787 Remote Similarity NPC277351

  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 NPC168922 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
0.7602 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD7803 Approved
0.748 Intermediate Similarity NPD7955 Approved
0.748 Intermediate Similarity NPD7956 Approved
0.7409 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7406 Intermediate Similarity NPD4885 Approved
0.7381 Intermediate Similarity NPD7708 Approved
0.7359 Intermediate Similarity NPD3257 Approved
0.7316 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD4328 Approved
0.7295 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4952 Phase 3
0.7234 Intermediate Similarity NPD3258 Approved
0.7213 Intermediate Similarity NPD5805 Approved
0.7202 Intermediate Similarity NPD6963 Approved
0.7202 Intermediate Similarity NPD6964 Approved
0.7176 Intermediate Similarity NPD6228 Discontinued
0.716 Intermediate Similarity NPD4373 Phase 2
0.7149 Intermediate Similarity NPD1505 Phase 2
0.7143 Intermediate Similarity NPD4846 Phase 2
0.7106 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6974 Phase 3
0.7082 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6962 Phase 2
0.7056 Intermediate Similarity NPD6790 Phase 1
0.7046 Intermediate Similarity NPD5632 Approved
0.7028 Intermediate Similarity NPD6716 Phase 1
0.7028 Intermediate Similarity NPD1483 Discontinued
0.7026 Intermediate Similarity NPD5658 Approved
0.7024 Intermediate Similarity NPD8102 Discontinued
0.7012 Intermediate Similarity NPD3925 Approved
0.7012 Intermediate Similarity NPD5488 Discontinued
0.7008 Intermediate Similarity NPD7859 Phase 2
0.6996 Remote Similarity NPD5482 Discontinued
0.6993 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6988 Remote Similarity NPD7417 Discontinued
0.6974 Remote Similarity NPD2778 Approved
0.6972 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6965 Remote Similarity NPD8091 Phase 3
0.6948 Remote Similarity NPD7885 Phase 2
0.6948 Remote Similarity NPD7886 Phase 2
0.6947 Remote Similarity NPD4418 Discontinued
0.694 Remote Similarity NPD3507 Phase 2
0.6936 Remote Similarity NPD683 Approved
0.692 Remote Similarity NPD5293 Phase 2
0.692 Remote Similarity NPD5417 Clinical (unspecified phase)
0.692 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6907 Remote Similarity NPD3815 Phase 1
0.6907 Remote Similarity NPD3816 Phase 1
0.6898 Remote Similarity NPD4898 Clinical (unspecified phase)
0.6895 Remote Similarity NPD3920 Phase 2
0.6892 Remote Similarity NPD6517 Phase 3
0.6885 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6883 Remote Similarity NPD2779 Approved
0.6883 Remote Similarity NPD956 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6494 Phase 2
0.6875 Remote Similarity NPD5519 Discontinued
0.6846 Remote Similarity NPD5930 Phase 3
0.6842 Remote Similarity NPD5512 Phase 3
0.6835 Remote Similarity NPD6745 Discontinued
0.6835 Remote Similarity NPD5866 Approved
0.6829 Remote Similarity NPD5924 Discontinued
0.6822 Remote Similarity NPD648 Clinical (unspecified phase)
0.6813 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6805 Remote Similarity NPD3763 Approved
0.6803 Remote Similarity NPD6247 Clinical (unspecified phase)
0.6802 Remote Similarity NPD1867 Approved
0.6797 Remote Similarity NPD6244 Phase 3
0.6797 Remote Similarity NPD6243 Phase 3
0.6793 Remote Similarity NPD5416 Discontinued
0.679 Remote Similarity NPD6160 Clinical (unspecified phase)
0.679 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6784 Remote Similarity NPD3328 Phase 2
0.6783 Remote Similarity NPD5532 Phase 2
0.6783 Remote Similarity NPD8463 Approved
0.6777 Remote Similarity NPD7180 Phase 3
0.6769 Remote Similarity NPD6550 Discontinued
0.6763 Remote Similarity NPD7395 Discontinued
0.6761 Remote Similarity NPD7589 Clinical (unspecified phase)
0.676 Remote Similarity NPD7853 Phase 2
0.6751 Remote Similarity NPD1166 Clinical (unspecified phase)
0.6748 Remote Similarity NPD3259 Approved
0.6747 Remote Similarity NPD6625 Approved
0.6708 Remote Similarity NPD7559 Phase 2
0.6707 Remote Similarity NPD3263 Phase 3
0.6695 Remote Similarity NPD5429 Discontinued
0.6694 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5479 Discontinued
0.6681 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6679 Remote Similarity NPD5450 Discontinued
0.6679 Remote Similarity NPD5922 Phase 3
0.6667 Remote Similarity NPD5005 Approved
0.6667 Remote Similarity NPD5006 Approved
0.6667 Remote Similarity NPD1467 Approved
0.6667 Remote Similarity NPD8459 Approved
0.6667 Remote Similarity NPD1466 Phase 3
0.6667 Remote Similarity NPD2899 Discontinued
0.6667 Remote Similarity NPD8460 Approved
0.6642 Remote Similarity NPD3217 Phase 2
0.664 Remote Similarity NPD7797 Approved
0.664 Remote Similarity NPD7796 Approved
0.664 Remote Similarity NPD7729 Clinical (unspecified phase)
0.6639 Remote Similarity NPD4897 Phase 2
0.6639 Remote Similarity NPD6242 Discontinued
0.6639 Remote Similarity NPD8479 Phase 2
0.6639 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6638 Remote Similarity NPD3922 Approved
0.6638 Remote Similarity NPD4420 Approved
0.6638 Remote Similarity NPD3924 Approved
0.6638 Remote Similarity NPD3921 Approved
0.6638 Remote Similarity NPD3923 Approved
0.6628 Remote Similarity NPD4369 Phase 2
0.6627 Remote Similarity NPD4875 Phase 3
0.6627 Remote Similarity NPD4876 Phase 3
0.6625 Remote Similarity NPD7069 Discontinued
0.6624 Remote Similarity NPD7222 Phase 2
0.6621 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6603 Remote Similarity NPD8255 Phase 2
0.66 Remote Similarity NPD7284 Clinical (unspecified phase)
0.6598 Remote Similarity NPD3945 Discontinued
0.6581 Remote Similarity NPD8466 Approved
0.6581 Remote Similarity NPD8467 Approved
0.6581 Remote Similarity NPD8465 Approved
0.658 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6573 Remote Similarity NPD7426 Phase 1
0.6573 Remote Similarity NPD5640 Discontinued
0.657 Remote Similarity NPD5902 Approved
0.657 Remote Similarity NPD5903 Approved
0.6564 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6561 Remote Similarity NPD3006 Discontinued
0.656 Remote Similarity NPD5022 Discontinued
0.655 Remote Similarity NPD8359 Phase 2
0.6549 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6548 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6546 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6542 Remote Similarity NPD5914 Approved
0.6537 Remote Similarity NPD6495 Clinical (unspecified phase)
0.6535 Remote Similarity NPD4368 Phase 2
0.6534 Remote Similarity NPD3442 Approved
0.6534 Remote Similarity NPD3441 Approved
0.6531 Remote Similarity NPD3875 Discontinued
0.6528 Remote Similarity NPD6530 Approved
0.6528 Remote Similarity NPD6531 Approved
0.6522 Remote Similarity NPD2951 Discontinued
0.6519 Remote Similarity NPD5459 Phase 2
0.6518 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6515 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6513 Remote Similarity NPD4305 Clinical (unspecified phase)
0.6511 Remote Similarity NPD7255 Clinical (unspecified phase)
0.6504 Remote Similarity NPD5070 Clinical (unspecified phase)
0.65 Remote Similarity NPD4558 Phase 2
0.65 Remote Similarity NPD4506 Discontinued
0.6498 Remote Similarity NPD5833 Phase 1
0.6494 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5857 Phase 3
0.6486 Remote Similarity NPD8426 Approved
0.6486 Remote Similarity NPD8425 Approved
0.6485 Remote Similarity NPD7452 Approved
0.6485 Remote Similarity NPD7453 Approved
0.6478 Remote Similarity NPD5507 Approved
0.6478 Remote Similarity NPD5506 Approved
0.6475 Remote Similarity NPD7588 Discontinued
0.6468 Remote Similarity NPD4995 Approved
0.6468 Remote Similarity NPD6874 Approved
0.6468 Remote Similarity NPD4996 Approved
0.6464 Remote Similarity NPD6252 Clinical (unspecified phase)
0.646 Remote Similarity NPD4204 Approved
0.646 Remote Similarity NPD4203 Approved
0.646 Remote Similarity NPD8428 Approved
0.646 Remote Similarity NPD8427 Approved
0.646 Remote Similarity NPD8429 Approved
0.6449 Remote Similarity NPD3949 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3003 Approved
0.6443 Remote Similarity NPD7031 Phase 1
0.6438 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4925 Approved
0.6429 Remote Similarity NPD5513 Phase 2
0.6423 Remote Similarity NPD8100 Phase 3
0.6423 Remote Similarity NPD3354 Phase 2
0.6423 Remote Similarity NPD4429 Discontinued
0.6421 Remote Similarity NPD8363 Approved
0.6421 Remote Similarity NPD8364 Approved
0.6417 Remote Similarity NPD7558 Phase 2
0.6405 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6398 Remote Similarity NPD1880 Phase 3
0.6398 Remote Similarity NPD1768 Approved
0.6391 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6389 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6388 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6386 Remote Similarity NPD4049 Phase 2
0.6382 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6375 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6375 Remote Similarity NPD3842 Clinical (unspecified phase)
0.6374 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6367 Remote Similarity NPD1638 Discovery
0.6364 Remote Similarity NPD6608 Clinical (unspecified phase)
0.636 Remote Similarity NPD7064 Clinical (unspecified phase)
0.636 Remote Similarity NPD5817 Discontinued
0.6357 Remote Similarity NPD8016 Phase 3
0.6357 Remote Similarity NPD5905 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