Structure

Physi-Chem Properties

Molecular Weight:  499.13
Volume:  488.55
LogP:  4.483
LogD:  3.42
LogS:  -6.117
# Rotatable Bonds:  4
TPSA:  123.0
# H-Bond Aceptor:  9
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.284
Synthetic Accessibility Score:  2.896
Fsp3:  0.107
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.409
MDCK Permeability:  2.3368425900116563e-05
Pgp-inhibitor:  0.2
Pgp-substrate:  0.138
Human Intestinal Absorption (HIA):  0.151
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  89.41852569580078%
Volume Distribution (VD):  0.324
Pgp-substrate:  12.325382232666016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.707
CYP1A2-substrate:  0.938
CYP2C19-inhibitor:  0.762
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.756
CYP2C9-substrate:  0.94
CYP2D6-inhibitor:  0.094
CYP2D6-substrate:  0.922
CYP3A4-inhibitor:  0.271
CYP3A4-substrate:  0.192

ADMET: Excretion

Clearance (CL):  9.087
Half-life (T1/2):  0.563

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.721
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.458
Rat Oral Acute Toxicity:  0.053
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.435
Carcinogencity:  0.738
Eye Corrosion:  0.003
Eye Irritation:  0.748
Respiratory Toxicity:  0.279

Download Data

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

  Natural Product: NPC129897

Natural Product ID:  NPC129897
Common Name*:   Lamellarin D
IUPAC Name:   n.a.
Synonyms:   Lamellarin D; Lamellarin-D
Standard InCHIKey:  ATHLLZUXVPNPAW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C28H21NO8/c1-34-21-9-14(4-5-17(21)30)24-25-16-11-23(36-3)19(32)12-20(16)37-28(33)27(25)29-7-6-13-8-18(31)22(35-2)10-15(13)26(24)29/h4-12,30-32H,1-3H3
SMILES:  COc1cc(ccc1O)c1c2c3cc(OC)c(cc3oc(=O)c2n2c1c1cc(OC)c(cc1cc2)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL373114
PubChem CID:   9892144
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002257] Substituted pyrroles
          • [CHEMONTID:0002334] Phenylpyrroles

*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
NPO33151 lamellaria sp. Species Lamellariidae Eukaryota n.a. n.a. n.a. PMID[16722644]

☑ 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
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 = 5.0 nM PMID[514917]
NPT404 Cell Line CCRF-CEM Homo sapiens RRI = 144.0 n.a. PMID[514917]
NPT81 Cell Line A549 Homo sapiens GI50 = 200.0 nM PMID[514918]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 5100.0 nM PMID[514918]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 250.0 nM PMID[514918]
NPT165 Cell Line HeLa Homo sapiens IC50 = 10.5 nM PMID[514919]
NPT4598 Cell Line XC Rattus norvegicus IC50 = 12.4 nM PMID[514919]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 10.5 nM PMID[514919]
NPT616 Cell Line MDCK Canis lupus familiaris IC50 = 22.5 nM PMID[514919]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 66.0 nM PMID[514920]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 3.0 nM PMID[514920]
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 = 15000.0 nM PMID[514921]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens Inhibition = 21.0 % PMID[514921]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens Inhibition = 22.0 % PMID[514921]
NPT396 Cell Line T47D Homo sapiens IC50 = 0.08 nM PMID[514923]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 20.0 nM PMID[514923]
NPT91 Cell Line KB Homo sapiens IC50 = 40.0 nM PMID[514923]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 40.0 nM PMID[514923]
NPT81 Cell Line A549 Homo sapiens IC50 = 60.0 nM PMID[514923]
NPT165 Cell Line HeLa Homo sapiens IC50 = 60.0 nM PMID[514923]
NPT168 Cell Line P388 Mus musculus IC50 = 100.0 nM PMID[514923]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 400.0 nM PMID[514923]
NPT171 Cell Line MRC5 Homo sapiens IC50 = 9200.0 nM PMID[514923]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 4470.0 nM PMID[514924]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 320.0 nM PMID[514924]
NPT111 Cell Line K562 Homo sapiens GI50 = 80.0 nM PMID[514924]
NPT65 Cell Line HepG2 Homo sapiens GI50 = 90.0 nM PMID[514924]
NPT83 Cell Line MCF7 Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT380 Cell Line U-251 Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT393 Cell Line HCT-116 Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 = 38.0 nM PMID[514925]
NPT369 Cell Line ACHN Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT1179 Cell Line MKN-28 Homo sapiens GI50 = 50.0 nM PMID[514925]
NPT90 Cell Line DU-145 Homo sapiens GI50 < 10.0 nM PMID[514925]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 31.0 nM PMID[514926]
NPT2511 Cell Line HGC-27 Homo sapiens IC50 = 236.0 nM PMID[514926]
NPT81 Cell Line A549 Homo sapiens IC50 = 4.0 nM PMID[514926]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 25.0 nM PMID[514926]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 88.0 nM PMID[514926]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 720.0 nM PMID[514917]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 49.0 nM PMID[514923]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 80.0 nM PMID[514923]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 400.0 nM PMID[514923]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3200.0 nM PMID[514923]
NPT35 Others n.a. Solubility = 0.56 nM PMID[514926]

☑ 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 NPC129897 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
0.9565 High Similarity NPC318068
0.8831 High Similarity NPC476995
0.8652 High Similarity NPC476996
0.8652 High Similarity NPC476998
0.8609 High Similarity NPC476997
0.8609 High Similarity NPC476994
0.8534 High Similarity NPC476999
0.8481 Intermediate Similarity NPC49672
0.8107 Intermediate Similarity NPC15406
0.8057 Intermediate Similarity NPC77878
0.8057 Intermediate Similarity NPC183537
0.7991 Intermediate Similarity NPC54066
0.7951 Intermediate Similarity NPC119134
0.7895 Intermediate Similarity NPC107123
0.7854 Intermediate Similarity NPC124313
0.7835 Intermediate Similarity NPC191489
0.7819 Intermediate Similarity NPC90875
0.781 Intermediate Similarity NPC233334
0.7805 Intermediate Similarity NPC210296
0.78 Intermediate Similarity NPC134637
0.7787 Intermediate Similarity NPC472589
0.7773 Intermediate Similarity NPC207283
0.7773 Intermediate Similarity NPC84164
0.7769 Intermediate Similarity NPC302807
0.7734 Intermediate Similarity NPC215837
0.7731 Intermediate Similarity NPC473639
0.7713 Intermediate Similarity NPC100734
0.7713 Intermediate Similarity NPC88923
0.7713 Intermediate Similarity NPC315634
0.7712 Intermediate Similarity NPC246658
0.7708 Intermediate Similarity NPC472588
0.7695 Intermediate Similarity NPC201508
0.7654 Intermediate Similarity NPC24019
0.7642 Intermediate Similarity NPC108342
0.7633 Intermediate Similarity NPC255800
0.7633 Intermediate Similarity NPC96584
0.7628 Intermediate Similarity NPC67401
0.7615 Intermediate Similarity NPC469439
0.7611 Intermediate Similarity NPC182907
0.7611 Intermediate Similarity NPC189903
0.7605 Intermediate Similarity NPC473822
0.7585 Intermediate Similarity NPC236668
0.7583 Intermediate Similarity NPC121069
0.7581 Intermediate Similarity NPC166722
0.7568 Intermediate Similarity NPC209981
0.7553 Intermediate Similarity NPC146976
0.7548 Intermediate Similarity NPC470042
0.7519 Intermediate Similarity NPC284685
0.749 Intermediate Similarity NPC22481
0.7479 Intermediate Similarity NPC122463
0.7479 Intermediate Similarity NPC210434
0.7469 Intermediate Similarity NPC174049
0.7462 Intermediate Similarity NPC101312
0.7462 Intermediate Similarity NPC282346
0.7451 Intermediate Similarity NPC203373
0.7439 Intermediate Similarity NPC278525
0.7427 Intermediate Similarity NPC148409
0.7425 Intermediate Similarity NPC172355
0.741 Intermediate Similarity NPC41501
0.7403 Intermediate Similarity NPC478045
0.7398 Intermediate Similarity NPC315914
0.7395 Intermediate Similarity NPC112206
0.7395 Intermediate Similarity NPC202605
0.7391 Intermediate Similarity NPC160100
0.7384 Intermediate Similarity NPC124086
0.7381 Intermediate Similarity NPC475844
0.7381 Intermediate Similarity NPC217554
0.7362 Intermediate Similarity NPC284141
0.7362 Intermediate Similarity NPC472287
0.7362 Intermediate Similarity NPC472286
0.7347 Intermediate Similarity NPC473449
0.7338 Intermediate Similarity NPC116701
0.732 Intermediate Similarity NPC253675
0.7306 Intermediate Similarity NPC94842
0.7302 Intermediate Similarity NPC11408
0.7298 Intermediate Similarity NPC469792
0.729 Intermediate Similarity NPC89549
0.7287 Intermediate Similarity NPC473800
0.728 Intermediate Similarity NPC329631
0.7273 Intermediate Similarity NPC132385
0.7266 Intermediate Similarity NPC58209
0.7261 Intermediate Similarity NPC239763
0.7261 Intermediate Similarity NPC190401
0.7258 Intermediate Similarity NPC246381
0.7244 Intermediate Similarity NPC9482
0.7241 Intermediate Similarity NPC120513
0.7241 Intermediate Similarity NPC13603
0.7211 Intermediate Similarity NPC316292
0.7203 Intermediate Similarity NPC85879
0.7203 Intermediate Similarity NPC53255
0.7202 Intermediate Similarity NPC303384
0.7202 Intermediate Similarity NPC13599
0.7202 Intermediate Similarity NPC191088
0.7202 Intermediate Similarity NPC298840
0.7202 Intermediate Similarity NPC268393
0.7202 Intermediate Similarity NPC3214
0.7195 Intermediate Similarity NPC118121
0.7188 Intermediate Similarity NPC188400
0.7183 Intermediate Similarity NPC208898
0.7177 Intermediate Similarity NPC200888
0.7173 Intermediate Similarity NPC210256
0.7173 Intermediate Similarity NPC164374
0.7173 Intermediate Similarity NPC137929
0.7172 Intermediate Similarity NPC204446
0.7149 Intermediate Similarity NPC474594
0.7149 Intermediate Similarity NPC232225
0.7137 Intermediate Similarity NPC326930
0.7137 Intermediate Similarity NPC475301
0.7131 Intermediate Similarity NPC316841
0.7131 Intermediate Similarity NPC474688
0.7131 Intermediate Similarity NPC469440
0.7126 Intermediate Similarity NPC15801
0.712 Intermediate Similarity NPC274640
0.7119 Intermediate Similarity NPC31930
0.7115 Intermediate Similarity NPC475406
0.7115 Intermediate Similarity NPC34770
0.7107 Intermediate Similarity NPC53069
0.7107 Intermediate Similarity NPC202768
0.7107 Intermediate Similarity NPC203168
0.7107 Intermediate Similarity NPC296482
0.7105 Intermediate Similarity NPC328928
0.7105 Intermediate Similarity NPC471978
0.7105 Intermediate Similarity NPC230683
0.7104 Intermediate Similarity NPC1608
0.7102 Intermediate Similarity NPC207620
0.7101 Intermediate Similarity NPC16452
0.7101 Intermediate Similarity NPC476581
0.7101 Intermediate Similarity NPC36229
0.7095 Intermediate Similarity NPC290689
0.7095 Intermediate Similarity NPC219664
0.7094 Intermediate Similarity NPC473833
0.709 Intermediate Similarity NPC471979
0.7088 Intermediate Similarity NPC473188
0.7087 Intermediate Similarity NPC327904
0.7087 Intermediate Similarity NPC38959
0.7085 Intermediate Similarity NPC280799
0.7082 Intermediate Similarity NPC166712
0.708 Intermediate Similarity NPC328186
0.708 Intermediate Similarity NPC122968
0.708 Intermediate Similarity NPC477787
0.708 Intermediate Similarity NPC228377
0.7077 Intermediate Similarity NPC270515
0.7077 Intermediate Similarity NPC169716
0.7066 Intermediate Similarity NPC146418
0.7064 Intermediate Similarity NPC472284
0.7063 Intermediate Similarity NPC473689
0.7063 Intermediate Similarity NPC475596
0.7063 Intermediate Similarity NPC292416
0.7063 Intermediate Similarity NPC475303
0.7063 Intermediate Similarity NPC474701
0.7059 Intermediate Similarity NPC473183
0.7054 Intermediate Similarity NPC475648
0.7047 Intermediate Similarity NPC277351
0.7042 Intermediate Similarity NPC193238
0.7042 Intermediate Similarity NPC313189
0.7042 Intermediate Similarity NPC321428
0.704 Intermediate Similarity NPC473506
0.7036 Intermediate Similarity NPC319880
0.7036 Intermediate Similarity NPC320324
0.7036 Intermediate Similarity NPC244839
0.7036 Intermediate Similarity NPC30456
0.7034 Intermediate Similarity NPC476578
0.7034 Intermediate Similarity NPC4071
0.7034 Intermediate Similarity NPC476582
0.7033 Intermediate Similarity NPC23614
0.7033 Intermediate Similarity NPC82056
0.7033 Intermediate Similarity NPC100079
0.7033 Intermediate Similarity NPC134702
0.7017 Intermediate Similarity NPC66815
0.7016 Intermediate Similarity NPC76478
0.7016 Intermediate Similarity NPC118189
0.7012 Intermediate Similarity NPC87152
0.7012 Intermediate Similarity NPC475631
0.7012 Intermediate Similarity NPC476110
0.7012 Intermediate Similarity NPC13249
0.7012 Intermediate Similarity NPC475600
0.7011 Intermediate Similarity NPC173250
0.7009 Intermediate Similarity NPC85381
0.7008 Intermediate Similarity NPC237702
0.7008 Intermediate Similarity NPC472435
0.7008 Intermediate Similarity NPC271215
0.7008 Intermediate Similarity NPC149471
0.7004 Intermediate Similarity NPC253482
0.7 Intermediate Similarity NPC304183
0.6996 Remote Similarity NPC41122
0.6996 Remote Similarity NPC217176
0.6996 Remote Similarity NPC318805
0.6988 Remote Similarity NPC148124
0.6988 Remote Similarity NPC144452
0.6988 Remote Similarity NPC208364
0.6985 Remote Similarity NPC165964
0.6984 Remote Similarity NPC475644
0.6984 Remote Similarity NPC470486
0.6984 Remote Similarity NPC471977
0.6984 Remote Similarity NPC471190
0.698 Remote Similarity NPC473184
0.698 Remote Similarity NPC327769
0.6977 Remote Similarity NPC148889
0.6973 Remote Similarity NPC161801
0.6973 Remote Similarity NPC475315

  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 NPC129897 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
0.7951 Intermediate Similarity NPD7417 Discontinued
0.7835 Intermediate Similarity NPD7708 Approved
0.7804 Intermediate Similarity NPD7862 Clinical (unspecified phase)
0.7773 Intermediate Similarity NPD1483 Discontinued
0.7713 Intermediate Similarity NPD7803 Approved
0.7702 Intermediate Similarity NPD6716 Phase 1
0.7692 Intermediate Similarity NPD5866 Approved
0.7659 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD7395 Discontinued
0.7519 Intermediate Similarity NPD7956 Approved
0.7519 Intermediate Similarity NPD7955 Approved
0.7397 Intermediate Similarity NPD7180 Phase 3
0.7383 Intermediate Similarity NPD5482 Discontinued
0.7354 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD4373 Phase 2
0.7341 Intermediate Similarity NPD7885 Phase 2
0.7341 Intermediate Similarity NPD7886 Phase 2
0.7331 Intermediate Similarity NPD7222 Phase 2
0.7317 Intermediate Similarity NPD3263 Phase 3
0.7294 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD6974 Phase 3
0.728 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD5429 Discontinued
0.7231 Intermediate Similarity NPD8463 Approved
0.7229 Intermediate Similarity NPD4952 Phase 3
0.7218 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1505 Phase 2
0.72 Intermediate Similarity NPD6962 Phase 2
0.719 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD7453 Approved
0.7185 Intermediate Similarity NPD7452 Approved
0.7178 Intermediate Similarity NPD7069 Discontinued
0.7163 Intermediate Similarity NPD7690 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD4418 Discontinued
0.7149 Intermediate Similarity NPD7994 Phase 2
0.7149 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6494 Phase 2
0.7128 Intermediate Similarity NPD6745 Discontinued
0.7126 Intermediate Similarity NPD5805 Approved
0.7107 Intermediate Similarity NPD3815 Phase 1
0.7107 Intermediate Similarity NPD3816 Phase 1
0.7097 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD8091 Phase 3
0.7083 Intermediate Similarity NPD7169 Suspended
0.7077 Intermediate Similarity NPD8310 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD5488 Discontinued
0.7052 Intermediate Similarity NPD5450 Discontinued
0.7051 Intermediate Similarity NPD5512 Phase 3
0.7038 Intermediate Similarity NPD3328 Phase 2
0.7026 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7853 Phase 2
0.7019 Intermediate Similarity NPD8461 Discontinued
0.7016 Intermediate Similarity NPD7022 Phase 2
0.7012 Intermediate Similarity NPD3259 Approved
0.7004 Intermediate Similarity NPD2899 Discontinued
0.698 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6969 Remote Similarity NPD4885 Approved
0.6964 Remote Similarity NPD5632 Approved
0.6947 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6947 Remote Similarity NPD8102 Discontinued
0.6944 Remote Similarity NPD4328 Approved
0.6935 Remote Similarity NPD3258 Approved
0.6935 Remote Similarity NPD3763 Approved
0.6932 Remote Similarity NPD3925 Approved
0.6929 Remote Similarity NPD1867 Approved
0.6926 Remote Similarity NPD5416 Discontinued
0.6923 Remote Similarity NPD3923 Approved
0.6923 Remote Similarity NPD3921 Approved
0.6923 Remote Similarity NPD3924 Approved
0.6923 Remote Similarity NPD3922 Approved
0.6917 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6911 Remote Similarity NPD5903 Approved
0.6911 Remote Similarity NPD5902 Approved
0.6907 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4926 Clinical (unspecified phase)
0.689 Remote Similarity NPD7589 Clinical (unspecified phase)
0.689 Remote Similarity NPD5022 Discontinued
0.6885 Remote Similarity NPD6517 Phase 3
0.6884 Remote Similarity NPD8467 Approved
0.6884 Remote Similarity NPD8466 Approved
0.6884 Remote Similarity NPD8465 Approved
0.6878 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2779 Approved
0.6868 Remote Similarity NPD7859 Phase 2
0.6865 Remote Similarity NPD6247 Clinical (unspecified phase)
0.686 Remote Similarity NPD4846 Phase 2
0.6856 Remote Similarity NPD8101 Phase 3
0.6853 Remote Similarity NPD6824 Clinical (unspecified phase)
0.685 Remote Similarity NPD8363 Approved
0.685 Remote Similarity NPD7654 Discontinued
0.685 Remote Similarity NPD8364 Approved
0.6842 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6838 Remote Similarity NPD7673 Phase 3
0.6838 Remote Similarity NPD7426 Phase 1
0.6835 Remote Similarity NPD6550 Discontinued
0.6827 Remote Similarity NPD6456 Discontinued
0.6823 Remote Similarity NPD8427 Approved
0.6823 Remote Similarity NPD8429 Approved
0.6823 Remote Similarity NPD8428 Approved
0.6822 Remote Similarity NPD3006 Discontinued
0.6818 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6138 Clinical (unspecified phase)
0.6815 Remote Similarity NPD8149 Discontinued
0.6813 Remote Similarity NPD5506 Approved
0.6813 Remote Similarity NPD5507 Approved
0.6812 Remote Similarity NPD3920 Phase 2
0.6811 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7558 Phase 2
0.6809 Remote Similarity NPD6625 Approved
0.6806 Remote Similarity NPD6460 Clinical (unspecified phase)
0.6805 Remote Similarity NPD5005 Approved
0.6805 Remote Similarity NPD5006 Approved
0.68 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6789 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6787 Remote Similarity NPD4989 Phase 2
0.6786 Remote Similarity NPD8426 Approved
0.6786 Remote Similarity NPD8459 Approved
0.6786 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8425 Approved
0.6786 Remote Similarity NPD8460 Approved
0.678 Remote Similarity NPD7868 Clinical (unspecified phase)
0.6778 Remote Similarity NPD6530 Approved
0.6778 Remote Similarity NPD6228 Discontinued
0.6778 Remote Similarity NPD6531 Approved
0.6774 Remote Similarity NPD3257 Approved
0.6771 Remote Similarity NPD7403 Phase 1
0.677 Remote Similarity NPD7031 Phase 1
0.676 Remote Similarity NPD6568 Discontinued
0.6758 Remote Similarity NPD5479 Discontinued
0.6758 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7924 Phase 2
0.6752 Remote Similarity NPD7925 Phase 2
0.675 Remote Similarity NPD2778 Approved
0.6747 Remote Similarity NPD5612 Discontinued
0.6746 Remote Similarity NPD8357 Approved
0.6746 Remote Similarity NPD4923 Phase 1
0.6742 Remote Similarity NPD8100 Phase 3
0.6729 Remote Similarity NPD7588 Discontinued
0.6723 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6719 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6718 Remote Similarity NPD6964 Approved
0.6718 Remote Similarity NPD6790 Phase 1
0.6718 Remote Similarity NPD6963 Approved
0.6708 Remote Similarity NPD4420 Approved
0.6707 Remote Similarity NPD4897 Phase 2
0.6706 Remote Similarity NPD6242 Discontinued
0.6706 Remote Similarity NPD5640 Discontinued
0.6705 Remote Similarity NPD7797 Approved
0.6705 Remote Similarity NPD7796 Approved
0.6705 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6703 Remote Similarity NPD5459 Phase 2
0.6693 Remote Similarity NPD5924 Discontinued
0.6693 Remote Similarity NPD7278 Phase 2
0.6693 Remote Similarity NPD7279 Phase 2
0.6693 Remote Similarity NPD3354 Phase 2
0.6693 Remote Similarity NPD4898 Clinical (unspecified phase)
0.6693 Remote Similarity NPD6198 Phase 1
0.668 Remote Similarity NPD7556 Discontinued
0.6679 Remote Similarity NPD8016 Phase 3
0.6679 Remote Similarity NPD5922 Phase 3
0.6679 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8152 Approved
0.6667 Remote Similarity NPD1467 Approved
0.6667 Remote Similarity NPD1466 Phase 3
0.6667 Remote Similarity NPD7585 Approved
0.6667 Remote Similarity NPD8153 Approved
0.6667 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6655 Remote Similarity NPD7684 Approved
0.6655 Remote Similarity NPD7682 Approved
0.6654 Remote Similarity NPD2951 Discontinued
0.6642 Remote Similarity NPD5050 Approved
0.664 Remote Similarity NPD5850 Phase 3
0.6639 Remote Similarity NPD53 Approved
0.6639 Remote Similarity NPD7778 Approved
0.6639 Remote Similarity NPD7777 Approved
0.6627 Remote Similarity NPD4429 Discontinued
0.6626 Remote Similarity NPD7583 Approved
0.6626 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6624 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6615 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6613 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6613 Remote Similarity NPD5914 Approved
0.6611 Remote Similarity NPD6361 Phase 2
0.6604 Remote Similarity NPD6475 Phase 2
0.66 Remote Similarity NPD3945 Discontinued
0.6599 Remote Similarity NPD5658 Approved
0.6598 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6988 Phase 1
0.6596 Remote Similarity NPD8054 Approved
0.6596 Remote Similarity NPD4889 Approved
0.6596 Remote Similarity NPD8053 Approved
0.659 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6588 Remote Similarity NPD8356 Approved
0.6588 Remote Similarity NPD6997 Phase 2
0.6586 Remote Similarity NPD4502 Phase 2
0.6585 Remote Similarity NPD5530 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