Structure

Physi-Chem Properties

Molecular Weight:  584.41
Volume:  642.465
LogP:  8.53
LogD:  5.108
LogS:  -2.155
# Rotatable Bonds:  6
TPSA:  121.38
# H-Bond Aceptor:  6
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.201
Synthetic Accessibility Score:  5.844
Fsp3:  0.667
Lipinski Rule-of-5:  Rejected
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:  -5.526
MDCK Permeability:  1.503241128375521e-05
Pgp-inhibitor:  0.749
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.438
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.056
Plasma Protein Binding (PPB):  98.34839630126953%
Volume Distribution (VD):  3.96
Pgp-substrate:  1.55703604221344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.137
CYP1A2-substrate:  0.963
CYP2C19-inhibitor:  0.627
CYP2C19-substrate:  0.348
CYP2C9-inhibitor:  0.224
CYP2C9-substrate:  0.994
CYP2D6-inhibitor:  0.381
CYP2D6-substrate:  0.549
CYP3A4-inhibitor:  0.152
CYP3A4-substrate:  0.429

ADMET: Excretion

Clearance (CL):  4.45
Half-life (T1/2):  0.112

ADMET: Toxicity

hERG Blockers:  0.198
Human Hepatotoxicity (H-HT):  0.237
Drug-inuced Liver Injury (DILI):  0.19
AMES Toxicity:  0.408
Rat Oral Acute Toxicity:  0.719
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.972
Carcinogencity:  0.031
Eye Corrosion:  0.003
Eye Irritation:  0.814
Respiratory Toxicity:  0.916

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

  Natural Product: NPC9592

Natural Product ID:  NPC9592
Common Name*:   Cylindrocyclophane A
IUPAC Name:   n.a.
Synonyms:   Cylindrocyclophane A
Standard InCHIKey:  JCKOOZUMKBNWSJ-WDCWCBICSA-N
Standard InCHI:  InChI=1S/C36H56O6/c1-5-7-15-25-17-11-9-13-23(3)36(42)28-21-31(39)34(32(40)22-28)26(16-8-6-2)18-12-10-14-24(4)35(41)27-19-29(37)33(25)30(38)20-27/h19-26,35-42H,5-18H2,1-4H3/t23-,24-,25-,26-,35+,36+/m0/s1
SMILES:  CCCC[C@H]1CCCC[C@H](C)[C@@H](O)c2cc(O)c(c(c2)O)[C@H](CCCC[C@@H]([C@H](c2cc(c1c(O)c2)O)O)C)CCCC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1224866
PubChem CID:   10348304
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1021/jo00416a020]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11473413]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[12608844]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota leaves n.a. n.a. PMID[17243726]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO33563 0stoc sp. 10022A Species 0stocaceae Bacteria n.a. West Melrose Avenue in Chicago, Illinois (N 41 56.46' W 87 38.39') n.a. PMID[20825206]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24476550]
NPO40250 0stoc sp. CAVN2 Strain 0stocaceae Bacteria n.a. n.a. n.a. PMID[26684177]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. Database[FooDB]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10232 Asclepias viridis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4198 Ungernia vvedenskyi Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9543 Cylindrospermum licheniforme Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23436 Cladrastis sikokiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4724 Stevia eupatoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1969 Streptomyces pilosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8811 Cytisus prolifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28833 Eleutherococcus sieboldianus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5335 0stoc sp Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19804 Lycopodium saururus Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8623 Anneissia japonica Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO834 Peperomia clusiifolia Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7788 Rana catesbeiana Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9705 Meyerozyma guilliermondii Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19541 Smilax moranensis Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8426 Tinospora rumphii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1537 Vaccinium arctostaphylos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7240 Osteospermum oppositifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10879 Lasius meridionalis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23216 Tanaecium pyramidatum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT941 Cell Line HaCaT Homo sapiens IC50 = 5000.0 nM PMID[501134]
NPT2 Others Unspecified IC50 = 33900.0 nM PMID[501133]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC = 300.0 nM PMID[501134]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 100.0 nM PMID[501134]
NPT19 Organism Escherichia coli Escherichia coli MIC > 85000.0 nM PMID[501134]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC > 85000.0 nM PMID[501134]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 85000.0 nM PMID[501134]

☑ 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 NPC9592 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 NPC48781
0.9545 High Similarity NPC23804
0.9402 High Similarity NPC139774
0.9402 High Similarity NPC174729
0.9369 High Similarity NPC319803
0.9369 High Similarity NPC261343
0.9244 High Similarity NPC91204
0.9244 High Similarity NPC237517
0.9244 High Similarity NPC111723
0.9189 High Similarity NPC224527
0.9167 High Similarity NPC98200
0.9167 High Similarity NPC66331
0.9167 High Similarity NPC32715
0.9009 High Similarity NPC186385
0.9009 High Similarity NPC33728
0.9009 High Similarity NPC299568
0.9009 High Similarity NPC19808
0.9008 High Similarity NPC257947
0.8957 High Similarity NPC115808
0.8938 High Similarity NPC166995
0.8919 High Similarity NPC174981
0.8909 High Similarity NPC99836
0.8909 High Similarity NPC201662
0.8909 High Similarity NPC12640
0.8879 High Similarity NPC470760
0.887 High Similarity NPC246760
0.887 High Similarity NPC84999
0.8829 High Similarity NPC158253
0.8829 High Similarity NPC61033
0.8829 High Similarity NPC204901
0.8829 High Similarity NPC232523
0.8829 High Similarity NPC54844
0.8829 High Similarity NPC305603
0.8818 High Similarity NPC37802
0.8818 High Similarity NPC246056
0.8814 High Similarity NPC223451
0.8772 High Similarity NPC473521
0.8761 High Similarity NPC475018
0.875 High Similarity NPC122175
0.875 High Similarity NPC18128
0.875 High Similarity NPC77789
0.8739 High Similarity NPC109691
0.8739 High Similarity NPC302681
0.8739 High Similarity NPC470700
0.8739 High Similarity NPC39664
0.8739 High Similarity NPC39097
0.8739 High Similarity NPC118286
0.8729 High Similarity NPC151197
0.8727 High Similarity NPC218879
0.8727 High Similarity NPC244513
0.8727 High Similarity NPC227458
0.8696 High Similarity NPC117846
0.8661 High Similarity NPC66834
0.8649 High Similarity NPC134829
0.8644 High Similarity NPC206
0.8609 High Similarity NPC43525
0.8596 High Similarity NPC132720
0.8559 High Similarity NPC323810
0.8559 High Similarity NPC320864
0.8559 High Similarity NPC241891
0.8559 High Similarity NPC102216
0.8559 High Similarity NPC475225
0.8547 High Similarity NPC232165
0.8545 High Similarity NPC166313
0.8545 High Similarity NPC294186
0.8545 High Similarity NPC147310
0.8545 High Similarity NPC11280
0.8545 High Similarity NPC24407
0.8545 High Similarity NPC192032
0.8545 High Similarity NPC137415
0.8534 High Similarity NPC263753
0.8522 High Similarity NPC4493
0.8522 High Similarity NPC225679
0.8522 High Similarity NPC476632
0.8522 High Similarity NPC165770
0.8512 High Similarity NPC39029
0.85 High Similarity NPC69006
0.8487 Intermediate Similarity NPC190514
0.8487 Intermediate Similarity NPC144343
0.8468 Intermediate Similarity NPC249828
0.8468 Intermediate Similarity NPC302219
0.8468 Intermediate Similarity NPC146798
0.8468 Intermediate Similarity NPC471228
0.8468 Intermediate Similarity NPC168303
0.8468 Intermediate Similarity NPC53051
0.8468 Intermediate Similarity NPC82299
0.8468 Intermediate Similarity NPC94351
0.8468 Intermediate Similarity NPC222522
0.8468 Intermediate Similarity NPC24404
0.8468 Intermediate Similarity NPC235762
0.8468 Intermediate Similarity NPC313030
0.8468 Intermediate Similarity NPC106396
0.8468 Intermediate Similarity NPC71002
0.8468 Intermediate Similarity NPC85479
0.8468 Intermediate Similarity NPC242342
0.8462 Intermediate Similarity NPC107240
0.8448 Intermediate Similarity NPC228452
0.843 Intermediate Similarity NPC24125
0.8425 Intermediate Similarity NPC472590
0.8417 Intermediate Similarity NPC191866
0.8417 Intermediate Similarity NPC469644
0.8417 Intermediate Similarity NPC184302
0.8417 Intermediate Similarity NPC121866
0.8413 Intermediate Similarity NPC472797
0.8407 Intermediate Similarity NPC248904
0.84 Intermediate Similarity NPC473221
0.8387 Intermediate Similarity NPC33654
0.8378 Intermediate Similarity NPC72947
0.8378 Intermediate Similarity NPC100340
0.8378 Intermediate Similarity NPC284011
0.8378 Intermediate Similarity NPC143659
0.8374 Intermediate Similarity NPC261992
0.8347 Intermediate Similarity NPC472071
0.8333 Intermediate Similarity NPC474352
0.8333 Intermediate Similarity NPC38604
0.8333 Intermediate Similarity NPC211179
0.8333 Intermediate Similarity NPC471671
0.8319 Intermediate Similarity NPC292452
0.8319 Intermediate Similarity NPC471350
0.8319 Intermediate Similarity NPC474839
0.8319 Intermediate Similarity NPC114064
0.8305 Intermediate Similarity NPC12656
0.8305 Intermediate Similarity NPC473137
0.8293 Intermediate Similarity NPC71094
0.8293 Intermediate Similarity NPC188997
0.8291 Intermediate Similarity NPC302371
0.8288 Intermediate Similarity NPC10588
0.8288 Intermediate Similarity NPC166761
0.8288 Intermediate Similarity NPC174911
0.8288 Intermediate Similarity NPC294741
0.8281 Intermediate Similarity NPC471517
0.8276 Intermediate Similarity NPC224870
0.8268 Intermediate Similarity NPC472795
0.8268 Intermediate Similarity NPC472796
0.8264 Intermediate Similarity NPC217174
0.8261 Intermediate Similarity NPC61885
0.8261 Intermediate Similarity NPC63698
0.825 Intermediate Similarity NPC127894
0.825 Intermediate Similarity NPC15860
0.825 Intermediate Similarity NPC219070
0.825 Intermediate Similarity NPC69261
0.825 Intermediate Similarity NPC304510
0.825 Intermediate Similarity NPC470759
0.825 Intermediate Similarity NPC33270
0.825 Intermediate Similarity NPC172219
0.825 Intermediate Similarity NPC277588
0.8244 Intermediate Similarity NPC472800
0.824 Intermediate Similarity NPC131397
0.824 Intermediate Similarity NPC476254
0.8235 Intermediate Similarity NPC808
0.823 Intermediate Similarity NPC119860
0.823 Intermediate Similarity NPC30506
0.8214 Intermediate Similarity NPC477685
0.8211 Intermediate Similarity NPC237667
0.8205 Intermediate Similarity NPC54373
0.8205 Intermediate Similarity NPC469912
0.8205 Intermediate Similarity NPC151537
0.819 Intermediate Similarity NPC202647
0.819 Intermediate Similarity NPC473524
0.8189 Intermediate Similarity NPC311293
0.8189 Intermediate Similarity NPC148366
0.8182 Intermediate Similarity NPC469609
0.8182 Intermediate Similarity NPC154030
0.8167 Intermediate Similarity NPC38893
0.8167 Intermediate Similarity NPC123559
0.8167 Intermediate Similarity NPC308311
0.8167 Intermediate Similarity NPC469663
0.8167 Intermediate Similarity NPC92
0.8167 Intermediate Similarity NPC150624
0.8167 Intermediate Similarity NPC477137
0.816 Intermediate Similarity NPC224342
0.8158 Intermediate Similarity NPC117115
0.8151 Intermediate Similarity NPC249270
0.8151 Intermediate Similarity NPC120280
0.8136 Intermediate Similarity NPC228425
0.8125 Intermediate Similarity NPC72729
0.8108 Intermediate Similarity NPC291789
0.8108 Intermediate Similarity NPC474073
0.8108 Intermediate Similarity NPC79241
0.8108 Intermediate Similarity NPC6597
0.8106 Intermediate Similarity NPC327735
0.8103 Intermediate Similarity NPC262365
0.8099 Intermediate Similarity NPC476266
0.8099 Intermediate Similarity NPC50521
0.8099 Intermediate Similarity NPC477136
0.8099 Intermediate Similarity NPC244816
0.8099 Intermediate Similarity NPC221549
0.8095 Intermediate Similarity NPC105031
0.8087 Intermediate Similarity NPC469913
0.8083 Intermediate Similarity NPC53906
0.8083 Intermediate Similarity NPC192948
0.8083 Intermediate Similarity NPC474486
0.8083 Intermediate Similarity NPC35797
0.808 Intermediate Similarity NPC474160
0.808 Intermediate Similarity NPC53567
0.8077 Intermediate Similarity NPC472798
0.8065 Intermediate Similarity NPC476633
0.8053 Intermediate Similarity NPC91461
0.8053 Intermediate Similarity NPC7686
0.8053 Intermediate Similarity NPC252105

  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 NPC9592 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
0.9009 High Similarity NPD4750 Phase 3
0.8175 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD7635 Approved
0.8062 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8053 Intermediate Similarity NPD940 Approved
0.8053 Intermediate Similarity NPD846 Approved
0.8018 Intermediate Similarity NPD288 Approved
0.7965 Intermediate Similarity NPD1242 Phase 1
0.7937 Intermediate Similarity NPD4749 Approved
0.7928 Intermediate Similarity NPD844 Approved
0.7876 Intermediate Similarity NPD3020 Approved
0.7846 Intermediate Similarity NPD3027 Phase 3
0.7769 Intermediate Similarity NPD4908 Phase 1
0.7731 Intermediate Similarity NPD3022 Approved
0.7731 Intermediate Similarity NPD3021 Approved
0.771 Intermediate Similarity NPD4625 Phase 3
0.7674 Intermediate Similarity NPD3094 Phase 2
0.7652 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7652 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7638 Intermediate Similarity NPD1610 Phase 2
0.7611 Intermediate Similarity NPD2859 Approved
0.7611 Intermediate Similarity NPD2860 Approved
0.76 Intermediate Similarity NPD3091 Approved
0.7563 Intermediate Similarity NPD2342 Discontinued
0.7537 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD1613 Approved
0.7522 Intermediate Similarity NPD2933 Approved
0.7522 Intermediate Similarity NPD2934 Approved
0.75 Intermediate Similarity NPD3092 Approved
0.7434 Intermediate Similarity NPD845 Approved
0.7426 Intermediate Similarity NPD2568 Approved
0.7424 Intermediate Similarity NPD2861 Phase 2
0.7391 Intermediate Similarity NPD6100 Approved
0.7391 Intermediate Similarity NPD6099 Approved
0.7364 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD3095 Discontinued
0.7323 Intermediate Similarity NPD1548 Phase 1
0.7302 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD2238 Phase 2
0.7252 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6671 Approved
0.7218 Intermediate Similarity NPD859 Approved
0.7218 Intermediate Similarity NPD602 Approved
0.7218 Intermediate Similarity NPD858 Approved
0.7218 Intermediate Similarity NPD599 Approved
0.7217 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD6407 Approved
0.7206 Intermediate Similarity NPD6405 Approved
0.72 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD1809 Phase 2
0.7154 Intermediate Similarity NPD1792 Phase 2
0.7153 Intermediate Similarity NPD7390 Discontinued
0.7143 Intermediate Similarity NPD497 Approved
0.7113 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD6696 Suspended
0.7063 Intermediate Similarity NPD496 Approved
0.7063 Intermediate Similarity NPD495 Approved
0.7063 Intermediate Similarity NPD3892 Phase 2
0.7063 Intermediate Similarity NPD498 Approved
0.7054 Intermediate Similarity NPD7741 Discontinued
0.7049 Intermediate Similarity NPD1444 Approved
0.7049 Intermediate Similarity NPD1445 Approved
0.7037 Intermediate Similarity NPD5736 Approved
0.7008 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD37 Approved
0.6992 Remote Similarity NPD4659 Approved
0.6986 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5762 Approved
0.6972 Remote Similarity NPD5763 Approved
0.697 Remote Similarity NPD1201 Approved
0.6947 Remote Similarity NPD4059 Approved
0.6947 Remote Similarity NPD3019 Approved
0.6947 Remote Similarity NPD2932 Approved
0.6929 Remote Similarity NPD2228 Approved
0.6929 Remote Similarity NPD2234 Approved
0.6929 Remote Similarity NPD2229 Approved
0.6929 Remote Similarity NPD5283 Phase 1
0.6929 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6917 Remote Similarity NPD2230 Approved
0.6917 Remote Similarity NPD2233 Approved
0.6917 Remote Similarity NPD2232 Approved
0.6912 Remote Similarity NPD3018 Phase 2
0.6906 Remote Similarity NPD4060 Phase 1
0.6906 Remote Similarity NPD943 Approved
0.6899 Remote Similarity NPD7340 Approved
0.6889 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6889 Remote Similarity NPD4103 Phase 2
0.6889 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6889 Remote Similarity NPD1470 Approved
0.6875 Remote Similarity NPD9614 Approved
0.6875 Remote Similarity NPD9618 Approved
0.687 Remote Similarity NPD4093 Discontinued
0.6863 Remote Similarity NPD4966 Approved
0.6863 Remote Similarity NPD4967 Phase 2
0.6863 Remote Similarity NPD4965 Approved
0.6853 Remote Similarity NPD7266 Discontinued
0.6842 Remote Similarity NPD1091 Approved
0.6835 Remote Similarity NPD6663 Approved
0.6831 Remote Similarity NPD7743 Approved
0.6831 Remote Similarity NPD7742 Approved
0.6818 Remote Similarity NPD9093 Approved
0.6818 Remote Similarity NPD5125 Phase 3
0.6818 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5126 Approved
0.6818 Remote Similarity NPD4626 Approved
0.6818 Remote Similarity NPD2286 Discontinued
0.6809 Remote Similarity NPD4097 Suspended
0.6809 Remote Similarity NPD1607 Approved
0.6809 Remote Similarity NPD5314 Approved
0.6797 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6794 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6794 Remote Similarity NPD5304 Approved
0.6794 Remote Similarity NPD5303 Approved
0.6794 Remote Similarity NPD7330 Discontinued
0.6791 Remote Similarity NPD2235 Phase 2
0.6791 Remote Similarity NPD2231 Phase 2
0.6791 Remote Similarity NPD2562 Approved
0.6791 Remote Similarity NPD2561 Approved
0.6786 Remote Similarity NPD3062 Approved
0.6786 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3061 Approved
0.6786 Remote Similarity NPD3059 Approved
0.6786 Remote Similarity NPD3620 Phase 2
0.6783 Remote Similarity NPD5406 Approved
0.6783 Remote Similarity NPD5408 Approved
0.6783 Remote Similarity NPD5404 Approved
0.6783 Remote Similarity NPD5405 Approved
0.6777 Remote Similarity NPD3028 Approved
0.6774 Remote Similarity NPD6234 Discontinued
0.6774 Remote Similarity NPD968 Approved
0.6765 Remote Similarity NPD1134 Approved
0.6765 Remote Similarity NPD1129 Approved
0.6765 Remote Similarity NPD1133 Approved
0.6765 Remote Similarity NPD1135 Approved
0.6765 Remote Similarity NPD1131 Approved
0.6761 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6761 Remote Similarity NPD3553 Approved
0.6761 Remote Similarity NPD3555 Approved
0.6761 Remote Similarity NPD3552 Approved
0.6761 Remote Similarity NPD3554 Approved
0.6759 Remote Similarity NPD6674 Discontinued
0.6759 Remote Similarity NPD5177 Phase 3
0.6757 Remote Similarity NPD7447 Phase 1
0.6757 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6757 Remote Similarity NPD9089 Approved
0.6746 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6741 Remote Similarity NPD2983 Phase 2
0.6741 Remote Similarity NPD2982 Phase 2
0.6738 Remote Similarity NPD5735 Approved
0.6738 Remote Similarity NPD5124 Phase 1
0.6738 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6736 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6732 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6726 Remote Similarity NPD111 Approved
0.672 Remote Similarity NPD290 Approved
0.6719 Remote Similarity NPD7843 Approved
0.6718 Remote Similarity NPD9613 Approved
0.6718 Remote Similarity NPD9616 Approved
0.6718 Remote Similarity NPD9615 Approved
0.6716 Remote Similarity NPD422 Phase 1
0.6713 Remote Similarity NPD1510 Phase 2
0.6712 Remote Similarity NPD3400 Discontinued
0.6711 Remote Similarity NPD6090 Discontinued
0.6692 Remote Similarity NPD7157 Approved
0.6692 Remote Similarity NPD9381 Approved
0.6692 Remote Similarity NPD9384 Approved
0.6692 Remote Similarity NPD4589 Approved
0.6692 Remote Similarity NPD7725 Approved
0.6692 Remote Similarity NPD1751 Approved
0.6691 Remote Similarity NPD8651 Approved
0.669 Remote Similarity NPD970 Clinical (unspecified phase)
0.6689 Remote Similarity NPD7213 Phase 3
0.6689 Remote Similarity NPD7041 Phase 2
0.6689 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6689 Remote Similarity NPD7212 Phase 2
0.6688 Remote Similarity NPD6959 Discontinued
0.6687 Remote Similarity NPD7228 Approved
0.6667 Remote Similarity NPD1934 Approved
0.6667 Remote Similarity NPD2981 Phase 2
0.6667 Remote Similarity NPD2935 Discontinued
0.6667 Remote Similarity NPD316 Approved
0.6667 Remote Similarity NPD1398 Phase 1
0.6667 Remote Similarity NPD1240 Approved
0.6667 Remote Similarity NPD1551 Phase 2
0.6645 Remote Similarity NPD4380 Phase 2
0.6644 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6644 Remote Similarity NPD2534 Approved
0.6644 Remote Similarity NPD2532 Approved
0.6644 Remote Similarity NPD2533 Approved
0.6642 Remote Similarity NPD2797 Approved
0.6642 Remote Similarity NPD1981 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