Structure

Physi-Chem Properties

Molecular Weight:  453.3
Volume:  490.784
LogP:  3.52
LogD:  2.727
LogS:  -3.898
# Rotatable Bonds:  8
TPSA:  88.59
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.458
Synthetic Accessibility Score:  5.225
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:  -5.066
MDCK Permeability:  1.0093918717757333e-05
Pgp-inhibitor:  0.269
Pgp-substrate:  0.947
Human Intestinal Absorption (HIA):  0.075
20% Bioavailability (F20%):  0.684
30% Bioavailability (F30%):  0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.817
Plasma Protein Binding (PPB):  87.35895538330078%
Volume Distribution (VD):  1.254
Pgp-substrate:  6.452601432800293%

ADMET: Metabolism

CYP1A2-inhibitor:  0.142
CYP1A2-substrate:  0.634
CYP2C19-inhibitor:  0.548
CYP2C19-substrate:  0.545
CYP2C9-inhibitor:  0.584
CYP2C9-substrate:  0.438
CYP2D6-inhibitor:  0.81
CYP2D6-substrate:  0.723
CYP3A4-inhibitor:  0.954
CYP3A4-substrate:  0.616

ADMET: Excretion

Clearance (CL):  4.905
Half-life (T1/2):  0.608

ADMET: Toxicity

hERG Blockers:  0.264
Human Hepatotoxicity (H-HT):  0.81
Drug-inuced Liver Injury (DILI):  0.286
AMES Toxicity:  0.035
Rat Oral Acute Toxicity:  0.774
Maximum Recommended Daily Dose:  0.94
Skin Sensitization:  0.124
Carcinogencity:  0.157
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.848

Download Data

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

  Natural Product: NPC474177

Natural Product ID:  NPC474177
Common Name*:   Lyngbyatoxi B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RLQWNZUFDRUTMZ-LERHOHMLSA-N
Standard InCHI:  InChI=1S/C27H39N3O3/c1-8-27(6,12-11-22(32)16(2)3)20-9-10-21-23-18(14-28-24(20)23)13-19(15-31)29-26(33)25(17(4)5)30(21)7/h8-10,14,17,19,22,25,28,31-32H,1-2,11-13,15H2,3-7H3,(H,29,33)/t19-,22?,25-,27-/m0/s1
SMILES:  OC[C@H]1N=C(O)[C@H](C(C)C)N(c2c3c(C1)c[nH]c3c(cc2)[C@](CCC(C(=C)C)O)(C=C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463245
PubChem CID:   14779552
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 = 2.2 uM PMID[520371]

☑ 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 NPC474177 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 NPC133366
0.9766 High Similarity NPC65215
0.9766 High Similarity NPC173028
0.9708 High Similarity NPC204565
0.9649 High Similarity NPC474707
0.9593 High Similarity NPC317030
0.9302 High Similarity NPC233936
0.9274 High Similarity NPC229332
0.8883 High Similarity NPC314957
0.8506 High Similarity NPC160105
0.8457 Intermediate Similarity NPC201700
0.84 Intermediate Similarity NPC49954
0.84 Intermediate Similarity NPC474561
0.8391 Intermediate Similarity NPC194640
0.8391 Intermediate Similarity NPC311276
0.8372 Intermediate Similarity NPC469762
0.8315 Intermediate Similarity NPC314603
0.8315 Intermediate Similarity NPC34508
0.8314 Intermediate Similarity NPC469785
0.8295 Intermediate Similarity NPC54988
0.8287 Intermediate Similarity NPC300688
0.8286 Intermediate Similarity NPC40779
0.8278 Intermediate Similarity NPC151939
0.8239 Intermediate Similarity NPC470508
0.8229 Intermediate Similarity NPC282231
0.8226 Intermediate Similarity NPC95783
0.8198 Intermediate Similarity NPC469765
0.8198 Intermediate Similarity NPC25008
0.8198 Intermediate Similarity NPC469786
0.8198 Intermediate Similarity NPC259644
0.8198 Intermediate Similarity NPC469760
0.8198 Intermediate Similarity NPC469763
0.8198 Intermediate Similarity NPC73952
0.8171 Intermediate Similarity NPC279918
0.815 Intermediate Similarity NPC75540
0.815 Intermediate Similarity NPC212376
0.815 Intermediate Similarity NPC211572
0.815 Intermediate Similarity NPC80597
0.815 Intermediate Similarity NPC70922
0.8146 Intermediate Similarity NPC63751
0.8132 Intermediate Similarity NPC270009
0.8125 Intermediate Similarity NPC16667
0.8114 Intermediate Similarity NPC67056
0.8043 Intermediate Similarity NPC192270
0.8033 Intermediate Similarity NPC472443
0.8011 Intermediate Similarity NPC230869
0.8 Intermediate Similarity NPC472444
0.8 Intermediate Similarity NPC163055
0.8 Intermediate Similarity NPC280548
0.799 Intermediate Similarity NPC300183
0.799 Intermediate Similarity NPC475506
0.7979 Intermediate Similarity NPC213629
0.7978 Intermediate Similarity NPC68354
0.7977 Intermediate Similarity NPC105818
0.7977 Intermediate Similarity NPC24678
0.7967 Intermediate Similarity NPC329688
0.7967 Intermediate Similarity NPC189812
0.7967 Intermediate Similarity NPC472586
0.7955 Intermediate Similarity NPC129721
0.7949 Intermediate Similarity NPC155143
0.7943 Intermediate Similarity NPC207726
0.7935 Intermediate Similarity NPC215795
0.7935 Intermediate Similarity NPC176199
0.7927 Intermediate Similarity NPC473640
0.7927 Intermediate Similarity NPC265576
0.7903 Intermediate Similarity NPC19679
0.7898 Intermediate Similarity NPC285469
0.7887 Intermediate Similarity NPC100321
0.788 Intermediate Similarity NPC248454
0.788 Intermediate Similarity NPC59269
0.788 Intermediate Similarity NPC293472
0.7877 Intermediate Similarity NPC102423
0.7869 Intermediate Similarity NPC37423
0.7869 Intermediate Similarity NPC275305
0.7861 Intermediate Similarity NPC165495
0.7857 Intermediate Similarity NPC158129
0.7849 Intermediate Similarity NPC314372
0.7841 Intermediate Similarity NPC38736
0.7838 Intermediate Similarity NPC213468
0.7838 Intermediate Similarity NPC248041
0.7838 Intermediate Similarity NPC126709
0.7826 Intermediate Similarity NPC267885
0.7819 Intermediate Similarity NPC188387
0.7819 Intermediate Similarity NPC163421
0.7817 Intermediate Similarity NPC98715
0.7814 Intermediate Similarity NPC313791
0.7789 Intermediate Similarity NPC46413
0.7784 Intermediate Similarity NPC145885
0.7784 Intermediate Similarity NPC84827
0.7784 Intermediate Similarity NPC14113
0.7778 Intermediate Similarity NPC235684
0.7778 Intermediate Similarity NPC94752
0.7772 Intermediate Similarity NPC110500
0.7772 Intermediate Similarity NPC149155
0.7772 Intermediate Similarity NPC203468
0.7765 Intermediate Similarity NPC131718
0.776 Intermediate Similarity NPC470498
0.775 Intermediate Similarity NPC127677
0.775 Intermediate Similarity NPC258062
0.7746 Intermediate Similarity NPC159856
0.7742 Intermediate Similarity NPC283219
0.774 Intermediate Similarity NPC470507
0.7739 Intermediate Similarity NPC475288
0.7733 Intermediate Similarity NPC190296
0.773 Intermediate Similarity NPC288785
0.7714 Intermediate Similarity NPC187951
0.7711 Intermediate Similarity NPC223791
0.7711 Intermediate Similarity NPC107077
0.7711 Intermediate Similarity NPC271862
0.7705 Intermediate Similarity NPC194411
0.77 Intermediate Similarity NPC473362
0.77 Intermediate Similarity NPC225821
0.77 Intermediate Similarity NPC46225
0.77 Intermediate Similarity NPC166492
0.7684 Intermediate Similarity NPC171171
0.7677 Intermediate Similarity NPC476874
0.7653 Intermediate Similarity NPC171317
0.765 Intermediate Similarity NPC78020
0.7647 Intermediate Similarity NPC475602
0.7644 Intermediate Similarity NPC471506
0.7641 Intermediate Similarity NPC11445
0.7635 Intermediate Similarity NPC320968
0.7634 Intermediate Similarity NPC150048
0.7634 Intermediate Similarity NPC203754
0.7632 Intermediate Similarity NPC314002
0.7632 Intermediate Similarity NPC15102
0.7624 Intermediate Similarity NPC162860
0.7622 Intermediate Similarity NPC472123
0.7619 Intermediate Similarity NPC139291
0.7619 Intermediate Similarity NPC469358
0.7619 Intermediate Similarity NPC472108
0.7619 Intermediate Similarity NPC48938
0.7617 Intermediate Similarity NPC243716
0.7616 Intermediate Similarity NPC469779
0.7616 Intermediate Similarity NPC469783
0.7616 Intermediate Similarity NPC469780
0.7616 Intermediate Similarity NPC469761
0.7616 Intermediate Similarity NPC469784
0.7616 Intermediate Similarity NPC469767
0.7616 Intermediate Similarity NPC469768
0.7614 Intermediate Similarity NPC124005
0.7614 Intermediate Similarity NPC293917
0.7614 Intermediate Similarity NPC37548
0.76 Intermediate Similarity NPC129042
0.7598 Intermediate Similarity NPC87856
0.7598 Intermediate Similarity NPC151976
0.7594 Intermediate Similarity NPC326575
0.7592 Intermediate Similarity NPC315555
0.759 Intermediate Similarity NPC195239
0.759 Intermediate Similarity NPC157828
0.7588 Intermediate Similarity NPC193761
0.7586 Intermediate Similarity NPC475422
0.7582 Intermediate Similarity NPC472587
0.7579 Intermediate Similarity NPC228835
0.7579 Intermediate Similarity NPC204717
0.7576 Intermediate Similarity NPC470497
0.7574 Intermediate Similarity NPC87755
0.7573 Intermediate Similarity NPC132211
0.7573 Intermediate Similarity NPC203614
0.7573 Intermediate Similarity NPC204491
0.7572 Intermediate Similarity NPC469766
0.7569 Intermediate Similarity NPC473320
0.7568 Intermediate Similarity NPC6982
0.7566 Intermediate Similarity NPC71037
0.7561 Intermediate Similarity NPC267965
0.7558 Intermediate Similarity NPC73767
0.7558 Intermediate Similarity NPC110126
0.7554 Intermediate Similarity NPC154293
0.7554 Intermediate Similarity NPC317430
0.7553 Intermediate Similarity NPC133261
0.7547 Intermediate Similarity NPC476492
0.754 Intermediate Similarity NPC134586
0.7539 Intermediate Similarity NPC62510
0.7537 Intermediate Similarity NPC478158
0.7526 Intermediate Similarity NPC472110
0.7526 Intermediate Similarity NPC472109
0.7526 Intermediate Similarity NPC220765
0.7525 Intermediate Similarity NPC54420
0.7525 Intermediate Similarity NPC323927
0.7524 Intermediate Similarity NPC250835
0.7514 Intermediate Similarity NPC135141
0.7514 Intermediate Similarity NPC92796
0.7513 Intermediate Similarity NPC198339
0.7513 Intermediate Similarity NPC321708
0.7513 Intermediate Similarity NPC232130
0.75 Intermediate Similarity NPC211997
0.75 Intermediate Similarity NPC64436
0.75 Intermediate Similarity NPC49217
0.75 Intermediate Similarity NPC184476
0.7487 Intermediate Similarity NPC99666
0.7486 Intermediate Similarity NPC469813
0.7486 Intermediate Similarity NPC476446
0.7486 Intermediate Similarity NPC78375
0.7476 Intermediate Similarity NPC54744
0.7476 Intermediate Similarity NPC229348
0.7475 Intermediate Similarity NPC470499
0.7461 Intermediate Similarity NPC46580
0.7461 Intermediate Similarity NPC17059
0.746 Intermediate Similarity NPC248462
0.746 Intermediate Similarity NPC55772

  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 NPC474177 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
0.8305 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD2144 Approved
0.8242 Intermediate Similarity NPD3038 Discontinued
0.8207 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.8087 Intermediate Similarity NPD6595 Phase 3
0.8033 Intermediate Similarity NPD4076 Approved
0.8033 Intermediate Similarity NPD4079 Approved
0.7978 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD3506 Approved
0.7978 Intermediate Similarity NPD3505 Approved
0.7944 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD8431 Approved
0.7869 Intermediate Similarity NPD5065 Approved
0.7802 Intermediate Similarity NPD1326 Approved
0.7802 Intermediate Similarity NPD1325 Approved
0.7789 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD482 Approved
0.7771 Intermediate Similarity NPD2172 Phase 1
0.775 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD8386 Phase 2
0.773 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD3100 Discontinued
0.7713 Intermediate Similarity NPD2095 Phase 2
0.7713 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD2092 Phase 2
0.7713 Intermediate Similarity NPD2094 Phase 2
0.7688 Intermediate Similarity NPD8272 Phase 2
0.7672 Intermediate Similarity NPD2091 Phase 2
0.7672 Intermediate Similarity NPD2096 Phase 2
0.7668 Intermediate Similarity NPD3404 Approved
0.765 Intermediate Similarity NPD7957 Phase 1
0.765 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.765 Intermediate Similarity NPD4638 Approved
0.765 Intermediate Similarity NPD4639 Approved
0.765 Intermediate Similarity NPD4640 Approved
0.7634 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD750 Phase 2
0.7614 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7948 Phase 1
0.7558 Intermediate Similarity NPD786 Approved
0.7512 Intermediate Similarity NPD3330 Phase 1
0.7473 Intermediate Similarity NPD1403 Approved
0.7473 Intermediate Similarity NPD1404 Approved
0.7463 Intermediate Similarity NPD8072 Approved
0.7463 Intermediate Similarity NPD7470 Discontinued
0.7461 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD3961 Discontinued
0.7459 Intermediate Similarity NPD5021 Discontinued
0.7459 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD2640 Approved
0.7459 Intermediate Similarity NPD2641 Approved
0.7449 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD5901 Discontinued
0.7411 Intermediate Similarity NPD7944 Discontinued
0.7407 Intermediate Similarity NPD8122 Approved
0.7407 Intermediate Similarity NPD8123 Approved
0.7405 Intermediate Similarity NPD2639 Approved
0.7405 Intermediate Similarity NPD2642 Approved
0.7389 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD1722 Approved
0.7366 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD1038 Approved
0.736 Intermediate Similarity NPD4703 Approved
0.736 Intermediate Similarity NPD4702 Approved
0.7356 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD2382 Approved
0.7354 Intermediate Similarity NPD2381 Approved
0.7354 Intermediate Similarity NPD4075 Phase 2
0.7354 Intermediate Similarity NPD2380 Approved
0.7353 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD8073 Approved
0.7327 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD4181 Approved
0.7302 Intermediate Similarity NPD4128 Approved
0.7297 Intermediate Similarity NPD3323 Discontinued
0.7287 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD3116 Approved
0.7287 Intermediate Similarity NPD3117 Approved
0.7278 Intermediate Similarity NPD4463 Approved
0.7278 Intermediate Similarity NPD4462 Approved
0.7268 Intermediate Similarity NPD3082 Discontinued
0.7263 Intermediate Similarity NPD5100 Phase 3
0.7254 Intermediate Similarity NPD5596 Phase 2
0.7251 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7618 Phase 3
0.7236 Intermediate Similarity NPD7619 Phase 3
0.7232 Intermediate Similarity NPD3717 Discontinued
0.7228 Intermediate Similarity NPD484 Approved
0.7216 Intermediate Similarity NPD4957 Phase 2
0.7216 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6281 Approved
0.7206 Intermediate Similarity NPD4886 Phase 2
0.7198 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD802 Phase 2
0.7184 Intermediate Similarity NPD1392 Approved
0.7177 Intermediate Similarity NPD8093 Discontinued
0.7177 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD5426 Phase 3
0.7167 Intermediate Similarity NPD4547 Phase 3
0.7165 Intermediate Similarity NPD2391 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD4999 Phase 3
0.715 Intermediate Similarity NPD4998 Phase 3
0.7143 Intermediate Similarity NPD4601 Approved
0.7143 Intermediate Similarity NPD4600 Approved
0.7135 Intermediate Similarity NPD5255 Approved
0.7127 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD4499 Approved
0.7114 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD2383 Phase 1
0.7105 Intermediate Similarity NPD3610 Approved
0.7105 Intermediate Similarity NPD3609 Approved
0.7104 Intermediate Similarity NPD2837 Discontinued
0.7101 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD5862 Discovery
0.709 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD6664 Approved
0.7078 Intermediate Similarity NPD7824 Approved
0.7077 Intermediate Similarity NPD5106 Approved
0.7077 Intermediate Similarity NPD5105 Approved
0.7075 Intermediate Similarity NPD5612 Discontinued
0.7062 Intermediate Similarity NPD8094 Discontinued
0.7056 Intermediate Similarity NPD706 Phase 1
0.7051 Intermediate Similarity NPD7271 Approved
0.705 Intermediate Similarity NPD4615 Phase 2
0.7048 Intermediate Similarity NPD5066 Phase 2
0.7048 Intermediate Similarity NPD5067 Phase 2
0.7042 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6026 Approved
0.7027 Intermediate Similarity NPD2580 Discontinued
0.7024 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD4511 Phase 1
0.7021 Intermediate Similarity NPD5140 Approved
0.7021 Intermediate Similarity NPD5138 Approved
0.702 Intermediate Similarity NPD8020 Approved
0.702 Intermediate Similarity NPD8021 Approved
0.7014 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD5555 Phase 1
0.7 Intermediate Similarity NPD4699 Discontinued
0.7 Intermediate Similarity NPD3014 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3013 Phase 3
0.6986 Remote Similarity NPD7731 Approved
0.6986 Remote Similarity NPD7730 Approved
0.6983 Remote Similarity NPD1592 Phase 3
0.6981 Remote Similarity NPD8488 Clinical (unspecified phase)
0.6979 Remote Similarity NPD4112 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7001 Phase 3
0.6963 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7423 Phase 2
0.695 Remote Similarity NPD8063 Discontinued
0.6943 Remote Similarity NPD2928 Phase 2
0.6939 Remote Similarity NPD8408 Discontinued
0.6938 Remote Similarity NPD8322 Phase 2
0.6935 Remote Similarity NPD6141 Clinical (unspecified phase)
0.6935 Remote Similarity NPD3002 Clinical (unspecified phase)
0.6931 Remote Similarity NPD8129 Discovery
0.6923 Remote Similarity NPD4037 Approved
0.6923 Remote Similarity NPD4122 Approved
0.6923 Remote Similarity NPD31 Approved
0.6923 Remote Similarity NPD4034 Approved
0.6923 Remote Similarity NPD32 Approved
0.6923 Remote Similarity NPD4039 Approved
0.6923 Remote Similarity NPD4036 Approved
0.6923 Remote Similarity NPD4038 Approved
0.6923 Remote Similarity NPD4035 Approved
0.6923 Remote Similarity NPD4033 Approved
0.6923 Remote Similarity NPD1683 Approved
0.6916 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5082 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5913 Phase 3
0.6915 Remote Similarity NPD5081 Phase 1
0.6906 Remote Similarity NPD5254 Discontinued
0.6905 Remote Similarity NPD2509 Approved
0.6905 Remote Similarity NPD2510 Approved
0.69 Remote Similarity NPD7234 Approved
0.69 Remote Similarity NPD7233 Approved
0.6898 Remote Similarity NPD2581 Approved
0.6898 Remote Similarity NPD2582 Approved
0.6898 Remote Similarity NPD3402 Phase 1
0.6895 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6895 Remote Similarity NPD2720 Phase 1
0.689 Remote Similarity NPD3003 Approved
0.6888 Remote Similarity NPD5899 Approved

  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