Structure

Physi-Chem Properties

Molecular Weight:  453.3
Volume:  490.784
LogP:  3.558
LogD:  2.585
LogS:  -4.058
# Rotatable Bonds:  7
TPSA:  88.59
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.48
Synthetic Accessibility Score:  5.094
Fsp3:  0.519
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.84
MDCK Permeability:  1.3241327906143852e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.765
Human Intestinal Absorption (HIA):  0.184
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.844
Plasma Protein Binding (PPB):  95.44286346435547%
Volume Distribution (VD):  0.939
Pgp-substrate:  4.002239227294922%

ADMET: Metabolism

CYP1A2-inhibitor:  0.117
CYP1A2-substrate:  0.39
CYP2C19-inhibitor:  0.662
CYP2C19-substrate:  0.464
CYP2C9-inhibitor:  0.806
CYP2C9-substrate:  0.741
CYP2D6-inhibitor:  0.905
CYP2D6-substrate:  0.706
CYP3A4-inhibitor:  0.957
CYP3A4-substrate:  0.64

ADMET: Excretion

Clearance (CL):  3.807
Half-life (T1/2):  0.806

ADMET: Toxicity

hERG Blockers:  0.171
Human Hepatotoxicity (H-HT):  0.742
Drug-inuced Liver Injury (DILI):  0.233
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.744
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.232
Carcinogencity:  0.675
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.337

Download Data

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

  Natural Product: NPC133366

Natural Product ID:  NPC133366
Common Name*:   Lyngbyatoxin C
IUPAC Name:   n.a.
Synonyms:   Lyngbyatoxin C
Standard InCHIKey:  VMLLPMJDAXPWAA-PIKNDIPASA-N
Standard InCHI:  InChI=1S/C27H39N3O3/c1-8-27(6,13-9-12-26(4,5)33)20-10-11-21-22-18(15-28-23(20)22)14-19(16-31)29-25(32)24(17(2)3)30(21)7/h8-12,15,17,19,24,28,31,33H,1,13-14,16H2,2-7H3,(H,29,32)/b12-9+/t19-,24-,27-/m0/s1
SMILES:  OC[C@H]1N=C(O)[C@H](C(C)C)N(c2c3c(C1)c[nH]c3c(cc2)[C@](C/C=C/C(O)(C)C)(C=C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL517150
PubChem CID:   6441239
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives
              • [CHEMONTID:0002309] Alpha amino acid amides

*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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae 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
NPT2 Others Unspecified ED50 = 0.2 uM PMID[458872]

☑ 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 NPC133366 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
0.9827 High Similarity NPC474177
0.9709 High Similarity NPC65215
0.9709 High Similarity NPC173028
0.9651 High Similarity NPC204565
0.9593 High Similarity NPC474707
0.9538 High Similarity NPC317030
0.9249 High Similarity NPC233936
0.9222 High Similarity NPC229332
0.8737 High Similarity NPC314957
0.8457 Intermediate Similarity NPC160105
0.8409 Intermediate Similarity NPC201700
0.8352 Intermediate Similarity NPC49954
0.8352 Intermediate Similarity NPC474561
0.8343 Intermediate Similarity NPC194640
0.8324 Intermediate Similarity NPC469762
0.8268 Intermediate Similarity NPC34508
0.8268 Intermediate Similarity NPC314603
0.8266 Intermediate Similarity NPC469785
0.8249 Intermediate Similarity NPC54988
0.8239 Intermediate Similarity NPC311276
0.8239 Intermediate Similarity NPC40779
0.8192 Intermediate Similarity NPC470508
0.8187 Intermediate Similarity NPC270009
0.8182 Intermediate Similarity NPC282231
0.815 Intermediate Similarity NPC73952
0.815 Intermediate Similarity NPC25008
0.815 Intermediate Similarity NPC469765
0.815 Intermediate Similarity NPC469763
0.815 Intermediate Similarity NPC469760
0.815 Intermediate Similarity NPC259644
0.815 Intermediate Similarity NPC469786
0.8142 Intermediate Similarity NPC300688
0.8132 Intermediate Similarity NPC151939
0.8125 Intermediate Similarity NPC279918
0.8103 Intermediate Similarity NPC75540
0.8103 Intermediate Similarity NPC80597
0.8103 Intermediate Similarity NPC212376
0.8103 Intermediate Similarity NPC70922
0.8103 Intermediate Similarity NPC211572
0.8101 Intermediate Similarity NPC63751
0.8087 Intermediate Similarity NPC472443
0.8085 Intermediate Similarity NPC95783
0.8079 Intermediate Similarity NPC16667
0.8073 Intermediate Similarity NPC265576
0.8068 Intermediate Similarity NPC67056
0.8054 Intermediate Similarity NPC472444
0.8035 Intermediate Similarity NPC105818
0.8035 Intermediate Similarity NPC24678
0.8 Intermediate Similarity NPC192270
0.7989 Intermediate Similarity NPC176199
0.7989 Intermediate Similarity NPC215795
0.7966 Intermediate Similarity NPC230869
0.7957 Intermediate Similarity NPC163055
0.7956 Intermediate Similarity NPC280548
0.7949 Intermediate Similarity NPC300183
0.7937 Intermediate Similarity NPC213629
0.7935 Intermediate Similarity NPC68354
0.7933 Intermediate Similarity NPC102423
0.7923 Intermediate Similarity NPC472586
0.7912 Intermediate Similarity NPC158129
0.791 Intermediate Similarity NPC129721
0.7898 Intermediate Similarity NPC207726
0.7898 Intermediate Similarity NPC38736
0.7887 Intermediate Similarity NPC473640
0.788 Intermediate Similarity NPC288785
0.7879 Intermediate Similarity NPC475288
0.7869 Intermediate Similarity NPC313791
0.7857 Intermediate Similarity NPC475506
0.7853 Intermediate Similarity NPC285469
0.7846 Intermediate Similarity NPC100321
0.7842 Intermediate Similarity NPC46413
0.7839 Intermediate Similarity NPC473362
0.7839 Intermediate Similarity NPC166492
0.7838 Intermediate Similarity NPC248454
0.7838 Intermediate Similarity NPC293472
0.7838 Intermediate Similarity NPC59269
0.7831 Intermediate Similarity NPC235684
0.7826 Intermediate Similarity NPC275305
0.7826 Intermediate Similarity NPC329688
0.7826 Intermediate Similarity NPC37423
0.7826 Intermediate Similarity NPC189812
0.7821 Intermediate Similarity NPC131718
0.7819 Intermediate Similarity NPC165495
0.7817 Intermediate Similarity NPC155143
0.7814 Intermediate Similarity NPC470498
0.7803 Intermediate Similarity NPC314372
0.7803 Intermediate Similarity NPC159856
0.7797 Intermediate Similarity NPC470507
0.7796 Intermediate Similarity NPC248041
0.7796 Intermediate Similarity NPC213468
0.7796 Intermediate Similarity NPC126709
0.7784 Intermediate Similarity NPC267885
0.7778 Intermediate Similarity NPC98715
0.7771 Intermediate Similarity NPC187951
0.7766 Intermediate Similarity NPC19679
0.7761 Intermediate Similarity NPC271862
0.7742 Intermediate Similarity NPC84827
0.7742 Intermediate Similarity NPC145885
0.7742 Intermediate Similarity NPC14113
0.7737 Intermediate Similarity NPC171171
0.7737 Intermediate Similarity NPC94752
0.773 Intermediate Similarity NPC203468
0.773 Intermediate Similarity NPC110500
0.773 Intermediate Similarity NPC149155
0.7711 Intermediate Similarity NPC127677
0.7711 Intermediate Similarity NPC258062
0.7701 Intermediate Similarity NPC283219
0.7692 Intermediate Similarity NPC471506
0.7688 Intermediate Similarity NPC190296
0.7684 Intermediate Similarity NPC163421
0.7684 Intermediate Similarity NPC314002
0.7684 Intermediate Similarity NPC188387
0.7672 Intermediate Similarity NPC48938
0.767 Intermediate Similarity NPC37548
0.767 Intermediate Similarity NPC124005
0.7663 Intermediate Similarity NPC194411
0.7662 Intermediate Similarity NPC225821
0.7662 Intermediate Similarity NPC46225
0.7659 Intermediate Similarity NPC250835
0.7657 Intermediate Similarity NPC129042
0.7653 Intermediate Similarity NPC232130
0.7637 Intermediate Similarity NPC472587
0.7632 Intermediate Similarity NPC204717
0.7624 Intermediate Similarity NPC473320
0.7622 Intermediate Similarity NPC6982
0.7614 Intermediate Similarity NPC171317
0.7609 Intermediate Similarity NPC78020
0.7602 Intermediate Similarity NPC11445
0.7594 Intermediate Similarity NPC476492
0.7594 Intermediate Similarity NPC203754
0.7594 Intermediate Similarity NPC134586
0.7594 Intermediate Similarity NPC150048
0.7592 Intermediate Similarity NPC15102
0.7586 Intermediate Similarity NPC107077
0.7586 Intermediate Similarity NPC223791
0.7581 Intermediate Similarity NPC472123
0.7579 Intermediate Similarity NPC220765
0.7576 Intermediate Similarity NPC293917
0.7572 Intermediate Similarity NPC469768
0.7572 Intermediate Similarity NPC469767
0.7572 Intermediate Similarity NPC469779
0.7572 Intermediate Similarity NPC469784
0.7572 Intermediate Similarity NPC469761
0.7572 Intermediate Similarity NPC469780
0.7572 Intermediate Similarity NPC469783
0.7569 Intermediate Similarity NPC92796
0.7569 Intermediate Similarity NPC135141
0.7566 Intermediate Similarity NPC198339
0.7561 Intermediate Similarity NPC87856
0.7561 Intermediate Similarity NPC151976
0.7556 Intermediate Similarity NPC184476
0.7554 Intermediate Similarity NPC49217
0.7553 Intermediate Similarity NPC211997
0.7551 Intermediate Similarity NPC157828
0.7551 Intermediate Similarity NPC195239
0.755 Intermediate Similarity NPC476874
0.7549 Intermediate Similarity NPC475422
0.7548 Intermediate Similarity NPC473310
0.7539 Intermediate Similarity NPC228835
0.7538 Intermediate Similarity NPC99666
0.7538 Intermediate Similarity NPC470497
0.7536 Intermediate Similarity NPC132211
0.7536 Intermediate Similarity NPC203614
0.7536 Intermediate Similarity NPC204491
0.7529 Intermediate Similarity NPC469766
0.7526 Intermediate Similarity NPC71037
0.7524 Intermediate Similarity NPC475602
0.7524 Intermediate Similarity NPC267965
0.7514 Intermediate Similarity NPC110126
0.7514 Intermediate Similarity NPC73767
0.7514 Intermediate Similarity NPC317430
0.7513 Intermediate Similarity NPC46580
0.7512 Intermediate Similarity NPC320968
0.75 Intermediate Similarity NPC280290
0.75 Intermediate Similarity NPC162860
0.75 Intermediate Similarity NPC62510
0.7488 Intermediate Similarity NPC54420
0.7487 Intermediate Similarity NPC139291
0.7487 Intermediate Similarity NPC469358
0.7487 Intermediate Similarity NPC32200
0.7487 Intermediate Similarity NPC243716
0.7487 Intermediate Similarity NPC472108
0.7474 Intermediate Similarity NPC321708
0.7463 Intermediate Similarity NPC193761
0.7461 Intermediate Similarity NPC315555
0.746 Intermediate Similarity NPC64436
0.746 Intermediate Similarity NPC326575
0.7452 Intermediate Similarity NPC472027
0.7451 Intermediate Similarity NPC87755
0.7443 Intermediate Similarity NPC242556
0.7437 Intermediate Similarity NPC470499
0.7424 Intermediate Similarity NPC251090
0.7423 Intermediate Similarity NPC17059
0.7421 Intermediate Similarity NPC55772
0.7421 Intermediate Similarity NPC133261
0.7421 Intermediate Similarity NPC248462
0.7419 Intermediate Similarity NPC154293
0.7416 Intermediate Similarity NPC471957
0.7415 Intermediate Similarity NPC478158
0.7411 Intermediate Similarity NPC307963

  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 NPC133366 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
0.8258 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD2144 Approved
0.8197 Intermediate Similarity NPD3038 Discontinued
0.8162 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD6595 Phase 3
0.8 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD4076 Approved
0.7989 Intermediate Similarity NPD4079 Approved
0.7935 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD3506 Approved
0.7935 Intermediate Similarity NPD3505 Approved
0.7923 Intermediate Similarity NPD5065 Approved
0.7884 Intermediate Similarity NPD8431 Approved
0.7857 Intermediate Similarity NPD1325 Approved
0.7857 Intermediate Similarity NPD1326 Approved
0.7749 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD482 Approved
0.7727 Intermediate Similarity NPD2172 Phase 1
0.772 Intermediate Similarity NPD3404 Approved
0.7711 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD8386 Phase 2
0.7688 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD2092 Phase 2
0.7672 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD2095 Phase 2
0.7672 Intermediate Similarity NPD2094 Phase 2
0.767 Intermediate Similarity NPD3100 Discontinued
0.7653 Intermediate Similarity NPD7948 Phase 1
0.765 Intermediate Similarity NPD8272 Phase 2
0.7632 Intermediate Similarity NPD2096 Phase 2
0.7632 Intermediate Similarity NPD2091 Phase 2
0.7609 Intermediate Similarity NPD4638 Approved
0.7609 Intermediate Similarity NPD4640 Approved
0.7609 Intermediate Similarity NPD4639 Approved
0.7594 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD750 Phase 2
0.7576 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD3330 Phase 1
0.7525 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7957 Phase 1
0.7514 Intermediate Similarity NPD786 Approved
0.7512 Intermediate Similarity NPD7470 Discontinued
0.75 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD5901 Discontinued
0.7438 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD1403 Approved
0.7432 Intermediate Similarity NPD1404 Approved
0.7426 Intermediate Similarity NPD8072 Approved
0.7423 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD3961 Discontinued
0.7419 Intermediate Similarity NPD2640 Approved
0.7419 Intermediate Similarity NPD5021 Discontinued
0.7419 Intermediate Similarity NPD2641 Approved
0.7419 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD1038 Approved
0.7405 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD8073 Approved
0.7366 Intermediate Similarity NPD2639 Approved
0.7366 Intermediate Similarity NPD2642 Approved
0.7341 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4462 Approved
0.7333 Intermediate Similarity NPD4463 Approved
0.733 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD1722 Approved
0.7318 Intermediate Similarity NPD4702 Approved
0.7318 Intermediate Similarity NPD4703 Approved
0.7317 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD5100 Phase 3
0.7316 Intermediate Similarity NPD2381 Approved
0.7316 Intermediate Similarity NPD4075 Phase 2
0.7316 Intermediate Similarity NPD2382 Approved
0.7316 Intermediate Similarity NPD2380 Approved
0.7299 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD7944 Discontinued
0.7283 Intermediate Similarity NPD5255 Approved
0.7277 Intermediate Similarity NPD8122 Approved
0.7277 Intermediate Similarity NPD484 Approved
0.7277 Intermediate Similarity NPD4181 Approved
0.7277 Intermediate Similarity NPD8123 Approved
0.7263 Intermediate Similarity NPD4128 Approved
0.7259 Intermediate Similarity NPD6281 Approved
0.7258 Intermediate Similarity NPD3323 Discontinued
0.7255 Intermediate Similarity NPD4886 Phase 2
0.7249 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD3116 Approved
0.7249 Intermediate Similarity NPD3117 Approved
0.7238 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD802 Phase 2
0.7231 Intermediate Similarity NPD3082 Discontinued
0.7225 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD8093 Discontinued
0.7216 Intermediate Similarity NPD2391 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5596 Phase 2
0.7212 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7619 Phase 3
0.72 Intermediate Similarity NPD7618 Phase 3
0.72 Intermediate Similarity NPD4999 Phase 3
0.72 Intermediate Similarity NPD4998 Phase 3
0.7191 Intermediate Similarity NPD3717 Discontinued
0.7179 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD1392 Approved
0.715 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD5426 Phase 3
0.7136 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD3013 Phase 3
0.7129 Intermediate Similarity NPD3014 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD4547 Phase 3
0.7123 Intermediate Similarity NPD5612 Discontinued
0.7109 Intermediate Similarity NPD8094 Discontinued
0.7107 Intermediate Similarity NPD706 Phase 1
0.7092 Intermediate Similarity NPD4957 Phase 2
0.7089 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD4499 Approved
0.7079 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5140 Approved
0.7074 Intermediate Similarity NPD5138 Approved
0.7073 Intermediate Similarity NPD4511 Phase 1
0.7071 Intermediate Similarity NPD2383 Phase 1
0.7068 Intermediate Similarity NPD3610 Approved
0.7068 Intermediate Similarity NPD3609 Approved
0.7065 Intermediate Similarity NPD2837 Discontinued
0.7053 Intermediate Similarity NPD5862 Discovery
0.7053 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD5913 Phase 3
0.705 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD7824 Approved
0.7044 Intermediate Similarity NPD6664 Approved
0.7043 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD2582 Approved
0.7043 Intermediate Similarity NPD2581 Approved
0.7043 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5106 Approved
0.7041 Intermediate Similarity NPD5105 Approved
0.7039 Intermediate Similarity NPD1592 Phase 3
0.7024 Intermediate Similarity NPD4600 Approved
0.7024 Intermediate Similarity NPD4601 Approved
0.7018 Intermediate Similarity NPD7271 Approved
0.7015 Intermediate Similarity NPD4615 Phase 2
0.7014 Intermediate Similarity NPD6220 Phase 3
0.7014 Intermediate Similarity NPD5066 Phase 2
0.7014 Intermediate Similarity NPD5067 Phase 2
0.7009 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7423 Phase 2
0.699 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6989 Remote Similarity NPD2580 Discontinued
0.6986 Remote Similarity NPD8410 Clinical (unspecified phase)
0.6985 Remote Similarity NPD6141 Clinical (unspecified phase)
0.6981 Remote Similarity NPD8458 Clinical (unspecified phase)
0.6976 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6974 Remote Similarity NPD8037 Clinical (unspecified phase)
0.6974 Remote Similarity NPD8036 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7712 Clinical (unspecified phase)
0.697 Remote Similarity NPD5555 Phase 1
0.6965 Remote Similarity NPD4699 Discontinued
0.6965 Remote Similarity NPD5082 Clinical (unspecified phase)
0.6965 Remote Similarity NPD5081 Phase 1
0.6963 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6955 Remote Similarity NPD7730 Approved
0.6955 Remote Similarity NPD7731 Approved
0.6948 Remote Similarity NPD8488 Clinical (unspecified phase)
0.6947 Remote Similarity NPD2720 Phase 1
0.6947 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6943 Remote Similarity NPD4112 Clinical (unspecified phase)
0.6938 Remote Similarity NPD7001 Phase 3
0.6923 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6919 Remote Similarity NPD2882 Phase 1
0.6915 Remote Similarity NPD2565 Phase 2
0.6915 Remote Similarity NPD8063 Discontinued
0.6915 Remote Similarity NPD2564 Approved
0.6901 Remote Similarity NPD4852 Phase 2
0.69 Remote Similarity NPD8021 Approved
0.69 Remote Similarity NPD8020 Approved
0.69 Remote Similarity NPD5590 Clinical (unspecified phase)
0.6898 Remote Similarity NPD6026 Approved
0.6897 Remote Similarity NPD5428 Discontinued
0.6895 Remote Similarity NPD8129 Discovery
0.6893 Remote Similarity NPD4118 Clinical (unspecified phase)
0.689 Remote Similarity NPD4037 Approved
0.689 Remote Similarity NPD4038 Approved
0.689 Remote Similarity NPD31 Approved
0.689 Remote Similarity NPD4039 Approved
0.689 Remote Similarity NPD4036 Approved
0.689 Remote Similarity NPD4033 Approved
0.689 Remote Similarity NPD4034 Approved
0.689 Remote Similarity NPD32 Approved
0.689 Remote Similarity NPD4035 Approved
0.689 Remote Similarity NPD4122 Approved
0.6885 Remote Similarity NPD1683 Approved
0.6884 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6878 Remote Similarity NPD5003 Discontinued
0.6875 Remote Similarity NPD2844 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