Structure

Physi-Chem Properties

Molecular Weight:  592.32
Volume:  602.522
LogP:  4.358
LogD:  3.756
LogS:  -4.823
# Rotatable Bonds:  7
TPSA:  140.98
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.391
Synthetic Accessibility Score:  7.092
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.119
MDCK Permeability:  6.567109085153788e-05
Pgp-inhibitor:  0.991
Pgp-substrate:  0.971
Human Intestinal Absorption (HIA):  0.034
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.074
Plasma Protein Binding (PPB):  78.67701721191406%
Volume Distribution (VD):  0.836
Pgp-substrate:  11.507177352905273%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.1
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.741
CYP2C9-inhibitor:  0.155
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.112
CYP3A4-inhibitor:  0.801
CYP3A4-substrate:  0.746

ADMET: Excretion

Clearance (CL):  14.326
Half-life (T1/2):  0.253

ADMET: Toxicity

hERG Blockers:  0.128
Human Hepatotoxicity (H-HT):  0.429
Drug-inuced Liver Injury (DILI):  0.863
AMES Toxicity:  0.159
Rat Oral Acute Toxicity:  0.83
Maximum Recommended Daily Dose:  0.621
Skin Sensitization:  0.366
Carcinogencity:  0.432
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.275

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

  Natural Product: NPC62800

Natural Product ID:  NPC62800
Common Name*:   Debromoaplysiatoxin
IUPAC Name:   n.a.
Synonyms:   Debromoaplysiatoxin
Standard InCHIKey:  REAZZDPREXHWNV-HJUJCDCNSA-N
Standard InCHI:  InChI=1S/C32H48O10/c1-18(11-12-24(38-7)22-9-8-10-23(34)13-22)29-20(3)26-16-32(41-29)30(5,6)15-19(2)31(37,42-32)17-28(36)39-25(21(4)33)14-27(35)40-26/h8-10,13,18-21,24-26,29,33-34,37H,11-12,14-17H2,1-7H3/t18-,19+,20-,21+,24-,25+,26-,29+,31-,32-/m0/s1
SMILES:  C[C@@H](CC[C@@H](c1cccc(c1)O)OC)[C@@H]1[C@@H](C)[C@@H]2C[C@]3(C(C)(C)C[C@@H](C)[C@@](CC(=O)O[C@H](CC(=O)O2)[C@@H](C)O)(O)O3)O1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2148106
PubChem CID:   5352033
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25612070]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. stem n.a. Database[Article]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16525 Luvunga eleutherandra Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15408 Ophryosporus heptanthus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13880 Iris clarkei Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14059 Dickeya zeae Species Pectobacteriaceae 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
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 933.25 nM PMID[485794]
NPT578 Cell Line SNB-78 Homo sapiens GI50 = 15848.93 nM PMID[485794]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 = 812.83 nM PMID[485794]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 346.74 nM PMID[485794]
NPT81 Cell Line A549 Homo sapiens GI50 = 1148.15 nM PMID[485794]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 = 2041.74 nM PMID[485794]
NPT2722 Cell Line St-4 Homo sapiens GI50 = 363.08 nM PMID[485794]
NPT182 Individual Protein Protein kinase C alpha Homo sapiens Ki = 0.26 nM PMID[485794]
NPT3124 Individual Protein Protein kinase C eta Homo sapiens Ki = 0.11 nM PMID[485794]
NPT80 Cell Line Raji Homo sapiens Activity = 50.0 % PMID[485796]
NPT80 Cell Line Raji Homo sapiens Activity = 60.0 % PMID[485796]
NPT80 Cell Line Raji Homo sapiens Activity = 24.4 % PMID[485796]
NPT80 Cell Line Raji Homo sapiens Activity = 22.9 % PMID[485796]
NPT80 Cell Line Raji Homo sapiens Activity = 21.1 % PMID[485796]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 338.84 nM PMID[485794]
NPT760 Individual Protein Protein kinase C beta Homo sapiens Ki = 0.17 nM PMID[485794]
NPT880 Individual Protein Protein kinase C gamma Homo sapiens Ki = 0.38 nM PMID[485794]
NPT881 Individual Protein Protein kinase C delta Homo sapiens Ki = 0.2 nM PMID[485794]
NPT761 Individual Protein Protein kinase C epsilon Homo sapiens Ki = 0.63 nM PMID[485794]
NPT887 Individual Protein Protein kinase C theta Homo sapiens Ki = 0.11 nM PMID[485794]
NPT35 Others n.a. LogP = 4.4 n.a. PMID[485794]
NPT881 Individual Protein Protein kinase C delta Homo sapiens Ki = 9.7 nM PMID[485795]
NPT35 Others n.a. LogP = 4.4 n.a. PMID[485795]
NPT32 Organism Mus musculus Mus musculus Activity = 80.0 % PMID[485796]
NPT32 Organism Mus musculus Mus musculus Activity = 90.0 % PMID[485796]

☑ 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 NPC62800 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
1.0 High Similarity NPC324262
0.9097 High Similarity NPC51198
0.8571 High Similarity NPC138798
0.8478 Intermediate Similarity NPC476407
0.8446 Intermediate Similarity NPC12006
0.8425 Intermediate Similarity NPC212808
0.8406 Intermediate Similarity NPC470122
0.8406 Intermediate Similarity NPC469705
0.8406 Intermediate Similarity NPC17968
0.84 Intermediate Similarity NPC87403
0.8333 Intermediate Similarity NPC106818
0.8333 Intermediate Similarity NPC469549
0.8323 Intermediate Similarity NPC471873
0.8311 Intermediate Similarity NPC28776
0.8311 Intermediate Similarity NPC473138
0.8298 Intermediate Similarity NPC169398
0.8288 Intermediate Similarity NPC296659
0.8288 Intermediate Similarity NPC202391
0.8286 Intermediate Similarity NPC471066
0.8286 Intermediate Similarity NPC471095
0.8278 Intermediate Similarity NPC299706
0.8278 Intermediate Similarity NPC115466
0.8278 Intermediate Similarity NPC61604
0.8278 Intermediate Similarity NPC245615
0.8276 Intermediate Similarity NPC296643
0.8261 Intermediate Similarity NPC158673
0.8258 Intermediate Similarity NPC471869
0.8252 Intermediate Similarity NPC101686
0.8252 Intermediate Similarity NPC469364
0.8252 Intermediate Similarity NPC65262
0.8239 Intermediate Similarity NPC103398
0.8239 Intermediate Similarity NPC123988
0.8239 Intermediate Similarity NPC180171
0.8239 Intermediate Similarity NPC158325
0.8235 Intermediate Similarity NPC478055
0.8227 Intermediate Similarity NPC164172
0.8224 Intermediate Similarity NPC472128
0.8224 Intermediate Similarity NPC472127
0.8224 Intermediate Similarity NPC160882
0.8214 Intermediate Similarity NPC281798
0.82 Intermediate Similarity NPC158635
0.82 Intermediate Similarity NPC35097
0.82 Intermediate Similarity NPC229882
0.8194 Intermediate Similarity NPC220942
0.8188 Intermediate Similarity NPC23677
0.8188 Intermediate Similarity NPC120728
0.8182 Intermediate Similarity NPC471345
0.8176 Intermediate Similarity NPC473147
0.8176 Intermediate Similarity NPC474268
0.8176 Intermediate Similarity NPC475539
0.8176 Intermediate Similarity NPC320734
0.8176 Intermediate Similarity NPC143246
0.8176 Intermediate Similarity NPC119773
0.8175 Intermediate Similarity NPC123704
0.817 Intermediate Similarity NPC38699
0.817 Intermediate Similarity NPC131532
0.8169 Intermediate Similarity NPC106406
0.8163 Intermediate Similarity NPC194938
0.8163 Intermediate Similarity NPC183824
0.8158 Intermediate Similarity NPC471874
0.8151 Intermediate Similarity NPC164599
0.8146 Intermediate Similarity NPC475407
0.8141 Intermediate Similarity NPC477627
0.8133 Intermediate Similarity NPC478242
0.8133 Intermediate Similarity NPC96599
0.8129 Intermediate Similarity NPC314795
0.8129 Intermediate Similarity NPC469654
0.8125 Intermediate Similarity NPC84789
0.8125 Intermediate Similarity NPC310252
0.8125 Intermediate Similarity NPC302583
0.8125 Intermediate Similarity NPC469696
0.8125 Intermediate Similarity NPC308976
0.8125 Intermediate Similarity NPC100558
0.8117 Intermediate Similarity NPC10945
0.8117 Intermediate Similarity NPC163635
0.8112 Intermediate Similarity NPC470990
0.8108 Intermediate Similarity NPC475528
0.8102 Intermediate Similarity NPC57607
0.8095 Intermediate Similarity NPC204644
0.8095 Intermediate Similarity NPC285550
0.8089 Intermediate Similarity NPC471850
0.8088 Intermediate Similarity NPC469927
0.8085 Intermediate Similarity NPC46137
0.8085 Intermediate Similarity NPC138777
0.8085 Intermediate Similarity NPC235294
0.8085 Intermediate Similarity NPC246869
0.8085 Intermediate Similarity NPC225384
0.8082 Intermediate Similarity NPC476385
0.8082 Intermediate Similarity NPC3218
0.8082 Intermediate Similarity NPC47471
0.8082 Intermediate Similarity NPC476377
0.8082 Intermediate Similarity NPC134405
0.8079 Intermediate Similarity NPC240592
0.8079 Intermediate Similarity NPC117346
0.8075 Intermediate Similarity NPC13989
0.8069 Intermediate Similarity NPC476383
0.8069 Intermediate Similarity NPC68092
0.8069 Intermediate Similarity NPC81515
0.8069 Intermediate Similarity NPC89105
0.8069 Intermediate Similarity NPC64141
0.8069 Intermediate Similarity NPC126739
0.8069 Intermediate Similarity NPC197666
0.8069 Intermediate Similarity NPC197316
0.8069 Intermediate Similarity NPC472350
0.8067 Intermediate Similarity NPC116229
0.8065 Intermediate Similarity NPC223335
0.8065 Intermediate Similarity NPC40920
0.8063 Intermediate Similarity NPC471870
0.8058 Intermediate Similarity NPC106677
0.8058 Intermediate Similarity NPC103533
0.8056 Intermediate Similarity NPC470572
0.8056 Intermediate Similarity NPC472132
0.8052 Intermediate Similarity NPC186316
0.8052 Intermediate Similarity NPC475484
0.805 Intermediate Similarity NPC469419
0.8042 Intermediate Similarity NPC34456
0.8041 Intermediate Similarity NPC63304
0.8038 Intermediate Similarity NPC471861
0.8029 Intermediate Similarity NPC236981
0.8028 Intermediate Similarity NPC473285
0.8028 Intermediate Similarity NPC254275
0.8027 Intermediate Similarity NPC469623
0.8027 Intermediate Similarity NPC148080
0.8027 Intermediate Similarity NPC222433
0.8027 Intermediate Similarity NPC265648
0.8026 Intermediate Similarity NPC473966
0.8026 Intermediate Similarity NPC77310
0.8025 Intermediate Similarity NPC471858
0.8014 Intermediate Similarity NPC473799
0.8014 Intermediate Similarity NPC475530
0.8013 Intermediate Similarity NPC469384
0.8013 Intermediate Similarity NPC53139
0.8 Intermediate Similarity NPC283480
0.8 Intermediate Similarity NPC470330
0.8 Intermediate Similarity NPC476376
0.8 Intermediate Similarity NPC474422
0.8 Intermediate Similarity NPC148323
0.8 Intermediate Similarity NPC260425
0.8 Intermediate Similarity NPC78363
0.7987 Intermediate Similarity NPC136757
0.7987 Intermediate Similarity NPC103910
0.7987 Intermediate Similarity NPC223185
0.7986 Intermediate Similarity NPC263829
0.7986 Intermediate Similarity NPC61181
0.7975 Intermediate Similarity NPC326278
0.7974 Intermediate Similarity NPC56184
0.7973 Intermediate Similarity NPC96795
0.7973 Intermediate Similarity NPC476384
0.7973 Intermediate Similarity NPC76406
0.7973 Intermediate Similarity NPC112
0.7973 Intermediate Similarity NPC293154
0.7973 Intermediate Similarity NPC247032
0.7973 Intermediate Similarity NPC476381
0.7973 Intermediate Similarity NPC119537
0.7973 Intermediate Similarity NPC175214
0.7973 Intermediate Similarity NPC264632
0.7973 Intermediate Similarity NPC205864
0.7973 Intermediate Similarity NPC478250
0.7973 Intermediate Similarity NPC476378
0.7973 Intermediate Similarity NPC476380
0.7973 Intermediate Similarity NPC298257
0.7973 Intermediate Similarity NPC269141
0.7973 Intermediate Similarity NPC242756
0.7973 Intermediate Similarity NPC476375
0.7973 Intermediate Similarity NPC476397
0.7972 Intermediate Similarity NPC114116
0.7962 Intermediate Similarity NPC208676
0.7962 Intermediate Similarity NPC44507
0.7962 Intermediate Similarity NPC130489
0.7961 Intermediate Similarity NPC116292
0.7961 Intermediate Similarity NPC179128
0.7961 Intermediate Similarity NPC267469
0.7961 Intermediate Similarity NPC35160
0.7961 Intermediate Similarity NPC87630
0.7961 Intermediate Similarity NPC69367
0.7961 Intermediate Similarity NPC162569
0.7959 Intermediate Similarity NPC9218
0.7959 Intermediate Similarity NPC100675
0.7959 Intermediate Similarity NPC470991
0.795 Intermediate Similarity NPC476017
0.7949 Intermediate Similarity NPC286919
0.7949 Intermediate Similarity NPC208651
0.7949 Intermediate Similarity NPC475663
0.7949 Intermediate Similarity NPC257309
0.7949 Intermediate Similarity NPC206641
0.7949 Intermediate Similarity NPC471878
0.7949 Intermediate Similarity NPC29552
0.7947 Intermediate Similarity NPC1580
0.7947 Intermediate Similarity NPC471076
0.7947 Intermediate Similarity NPC83975
0.7947 Intermediate Similarity NPC127046
0.7947 Intermediate Similarity NPC192568
0.7945 Intermediate Similarity NPC31745
0.7945 Intermediate Similarity NPC205195
0.7945 Intermediate Similarity NPC220936
0.7943 Intermediate Similarity NPC214246
0.7935 Intermediate Similarity NPC156624
0.7935 Intermediate Similarity NPC82190
0.7935 Intermediate Similarity NPC172920
0.7935 Intermediate Similarity NPC192219

  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 NPC62800 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
0.8069 Intermediate Similarity NPD7266 Discontinued
0.7711 Intermediate Similarity NPD8312 Approved
0.7711 Intermediate Similarity NPD8313 Approved
0.7697 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD7228 Approved
0.7655 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD8455 Phase 2
0.7616 Intermediate Similarity NPD6190 Approved
0.758 Intermediate Similarity NPD37 Approved
0.7562 Intermediate Similarity NPD6234 Discontinued
0.7547 Intermediate Similarity NPD4965 Approved
0.7547 Intermediate Similarity NPD4966 Approved
0.7547 Intermediate Similarity NPD4967 Phase 2
0.747 Intermediate Similarity NPD7074 Phase 3
0.7468 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD8166 Discontinued
0.7434 Intermediate Similarity NPD4628 Phase 3
0.7432 Intermediate Similarity NPD6653 Approved
0.7426 Intermediate Similarity NPD2629 Approved
0.741 Intermediate Similarity NPD7054 Approved
0.741 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD7097 Phase 1
0.7381 Intermediate Similarity NPD7685 Pre-registration
0.7365 Intermediate Similarity NPD7472 Approved
0.7361 Intermediate Similarity NPD5647 Approved
0.7347 Intermediate Similarity NPD6663 Approved
0.7337 Intermediate Similarity NPD7808 Phase 3
0.7333 Intermediate Similarity NPD7033 Discontinued
0.732 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD5736 Approved
0.731 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD7075 Discontinued
0.7278 Intermediate Similarity NPD6559 Discontinued
0.7278 Intermediate Similarity NPD7251 Discontinued
0.7278 Intermediate Similarity NPD7240 Approved
0.7267 Intermediate Similarity NPD8150 Discontinued
0.7267 Intermediate Similarity NPD5402 Approved
0.7254 Intermediate Similarity NPD1091 Approved
0.7248 Intermediate Similarity NPD6355 Discontinued
0.7248 Intermediate Similarity NPD230 Phase 1
0.7246 Intermediate Similarity NPD3818 Discontinued
0.7235 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD4380 Phase 2
0.723 Intermediate Similarity NPD6233 Phase 2
0.7222 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6797 Phase 2
0.7211 Intermediate Similarity NPD7095 Approved
0.7203 Intermediate Similarity NPD1608 Approved
0.7171 Intermediate Similarity NPD6100 Approved
0.7171 Intermediate Similarity NPD6099 Approved
0.7162 Intermediate Similarity NPD6798 Discontinued
0.7152 Intermediate Similarity NPD7199 Phase 2
0.7152 Intermediate Similarity NPD8127 Discontinued
0.7143 Intermediate Similarity NPD1934 Approved
0.7126 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6166 Phase 2
0.7126 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6004 Phase 3
0.7124 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6005 Phase 3
0.7124 Intermediate Similarity NPD6002 Phase 3
0.7124 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5125 Phase 3
0.7113 Intermediate Similarity NPD1778 Approved
0.7113 Intermediate Similarity NPD5126 Approved
0.7108 Intermediate Similarity NPD3787 Discontinued
0.7107 Intermediate Similarity NPD1653 Approved
0.7099 Intermediate Similarity NPD7819 Suspended
0.7099 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4110 Phase 3
0.7095 Intermediate Similarity NPD3027 Phase 3
0.7092 Intermediate Similarity NPD9545 Approved
0.7086 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD8434 Phase 2
0.7059 Intermediate Similarity NPD2935 Discontinued
0.7049 Intermediate Similarity NPD8319 Approved
0.7049 Intermediate Similarity NPD8320 Phase 1
0.7047 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD3764 Approved
0.7047 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD5403 Approved
0.7042 Intermediate Similarity NPD5585 Approved
0.7018 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD5762 Approved
0.7013 Intermediate Similarity NPD5763 Approved
0.7 Intermediate Similarity NPD7157 Approved
0.6993 Remote Similarity NPD17 Approved
0.6982 Remote Similarity NPD7473 Discontinued
0.698 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6975 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6968 Remote Similarity NPD970 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7458 Discontinued
0.6954 Remote Similarity NPD1613 Approved
0.6954 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6954 Remote Similarity NPD4060 Phase 1
0.6951 Remote Similarity NPD3817 Phase 2
0.6951 Remote Similarity NPD8443 Clinical (unspecified phase)
0.695 Remote Similarity NPD9493 Approved
0.6948 Remote Similarity NPD2438 Suspended
0.6941 Remote Similarity NPD3751 Discontinued
0.6939 Remote Similarity NPD3094 Phase 2
0.6939 Remote Similarity NPD2797 Approved
0.6933 Remote Similarity NPD6801 Discontinued
0.6918 Remote Similarity NPD5401 Approved
0.6908 Remote Similarity NPD447 Suspended
0.6906 Remote Similarity NPD7843 Approved
0.6906 Remote Similarity NPD7700 Phase 2
0.6906 Remote Similarity NPD7699 Phase 2
0.6905 Remote Similarity NPD6232 Discontinued
0.6902 Remote Similarity NPD7680 Approved
0.689 Remote Similarity NPD2801 Approved
0.6889 Remote Similarity NPD5048 Discontinued
0.6887 Remote Similarity NPD4062 Phase 3
0.6887 Remote Similarity NPD8032 Phase 2
0.6879 Remote Similarity NPD8368 Discontinued
0.6879 Remote Similarity NPD4198 Discontinued
0.6875 Remote Similarity NPD3019 Approved
0.6875 Remote Similarity NPD2932 Approved
0.6871 Remote Similarity NPD8651 Approved
0.6868 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6859 Remote Similarity NPD4534 Discontinued
0.6853 Remote Similarity NPD7741 Discontinued
0.6852 Remote Similarity NPD3226 Approved
0.6846 Remote Similarity NPD2861 Phase 2
0.6842 Remote Similarity NPD7799 Discontinued
0.6842 Remote Similarity NPD4140 Approved
0.6839 Remote Similarity NPD9570 Approved
0.6839 Remote Similarity NPD6032 Approved
0.6832 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6828 Remote Similarity NPD3496 Discontinued
0.6824 Remote Similarity NPD6362 Approved
0.6821 Remote Similarity NPD7985 Registered
0.6821 Remote Similarity NPD3268 Approved
0.6821 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6674 Discontinued
0.6813 Remote Similarity NPD2533 Approved
0.6813 Remote Similarity NPD2532 Approved
0.6813 Remote Similarity NPD2534 Approved
0.6811 Remote Similarity NPD7435 Discontinued
0.681 Remote Similarity NPD6599 Discontinued
0.6807 Remote Similarity NPD7768 Phase 2
0.6806 Remote Similarity NPD1357 Approved
0.6805 Remote Similarity NPD7315 Approved
0.6803 Remote Similarity NPD4359 Approved
0.6802 Remote Similarity NPD8470 Clinical (unspecified phase)
0.68 Remote Similarity NPD6832 Phase 2
0.6797 Remote Similarity NPD1933 Approved
0.6795 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6795 Remote Similarity NPD2346 Discontinued
0.6795 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6792 Remote Similarity NPD5058 Phase 3
0.6781 Remote Similarity NPD3092 Approved
0.6779 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6779 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6779 Remote Similarity NPD2798 Approved
0.6779 Remote Similarity NPD6085 Phase 2
0.6772 Remote Similarity NPD3400 Discontinued
0.677 Remote Similarity NPD6273 Approved
0.6768 Remote Similarity NPD7411 Suspended
0.6768 Remote Similarity NPD6677 Suspended
0.6761 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6761 Remote Similarity NPD6671 Approved
0.6761 Remote Similarity NPD8407 Phase 2
0.6757 Remote Similarity NPD1283 Approved
0.6752 Remote Similarity NPD1549 Phase 2
0.675 Remote Similarity NPD6799 Approved
0.6748 Remote Similarity NPD5808 Clinical (unspecified phase)
0.674 Remote Similarity NPD6534 Approved
0.674 Remote Similarity NPD6535 Approved
0.6738 Remote Similarity NPD6010 Discontinued
0.6737 Remote Similarity NPD7783 Phase 2
0.6737 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6732 Remote Similarity NPD825 Approved
0.6732 Remote Similarity NPD2979 Phase 3
0.6732 Remote Similarity NPD826 Approved
0.6731 Remote Similarity NPD1551 Phase 2
0.672 Remote Similarity NPD7696 Phase 3
0.672 Remote Similarity NPD7697 Approved
0.672 Remote Similarity NPD8151 Discontinued
0.672 Remote Similarity NPD7698 Approved
0.6711 Remote Similarity NPD2313 Discontinued
0.6709 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6709 Remote Similarity NPD1652 Phase 2
0.6708 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3882 Suspended
0.6705 Remote Similarity NPD5844 Phase 1
0.6691 Remote Similarity NPD2067 Discontinued
0.6689 Remote Similarity NPD4908 Phase 1
0.6689 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6689 Remote Similarity NPD4749 Approved
0.6688 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6688 Remote Similarity NPD5124 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