Structure

Physi-Chem Properties

Molecular Weight:  652.33
Volume:  672.887
LogP:  7.975
LogD:  5.053
LogS:  -2.828
# Rotatable Bonds:  7
TPSA:  121.38
# H-Bond Aceptor:  6
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.166
Synthetic Accessibility Score:  6.163
Fsp3:  0.667
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.024
MDCK Permeability:  2.011295327974949e-05
Pgp-inhibitor:  0.602
Pgp-substrate:  0.979
Human Intestinal Absorption (HIA):  0.263
20% Bioavailability (F20%):  0.797
30% Bioavailability (F30%):  0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.129
Plasma Protein Binding (PPB):  100.3741226196289%
Volume Distribution (VD):  5.002
Pgp-substrate:  0.966772735118866%

ADMET: Metabolism

CYP1A2-inhibitor:  0.151
CYP1A2-substrate:  0.956
CYP2C19-inhibitor:  0.469
CYP2C19-substrate:  0.558
CYP2C9-inhibitor:  0.172
CYP2C9-substrate:  0.993
CYP2D6-inhibitor:  0.488
CYP2D6-substrate:  0.417
CYP3A4-inhibitor:  0.146
CYP3A4-substrate:  0.501

ADMET: Excretion

Clearance (CL):  2.724
Half-life (T1/2):  0.18

ADMET: Toxicity

hERG Blockers:  0.135
Human Hepatotoxicity (H-HT):  0.193
Drug-inuced Liver Injury (DILI):  0.06
AMES Toxicity:  0.444
Rat Oral Acute Toxicity:  0.953
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.965
Carcinogencity:  0.087
Eye Corrosion:  0.003
Eye Irritation:  0.716
Respiratory Toxicity:  0.927

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

  Natural Product: NPC237517

Natural Product ID:  NPC237517
Common Name*:   Cylindrocyclophane A2
IUPAC Name:   n.a.
Synonyms:   Cylindrocyclophane A2
Standard InCHIKey:  LERNCFONJSWYRR-CCNIBDGSSA-N
Standard InCHI:  InChI=1S/C36H54Cl2O6/c1-4-5-13-24-14-8-6-11-22(2)36(44)27-20-30(41)34(31(42)21-27)25(16-10-17-32(37)38)15-9-7-12-23(3)35(43)26-18-28(39)33(24)29(40)19-26/h18-25,32,35-36,39-44H,4-17H2,1-3H3/t22-,23-,24-,25+,35+,36+/m0/s1
SMILES:  CCCC[C@H]1CCCC[C@H](C)[C@H](c2cc(c([C@H](CCCC[C@H](C)[C@H](c3cc(c1c(c3)O)O)O)CCCC(Cl)Cl)c(c2)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1224860
PubChem CID:   46939339
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]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. Database[FooDB]
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]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10879 Lasius meridionalis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4198 Ungernia vvedenskyi Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23436 Cladrastis sikokiana Species Fabaceae 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]
NPO19804 Lycopodium saururus Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5335 0stoc sp Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO834 Peperomia clusiifolia Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8623 Anneissia japonica Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9705 Meyerozyma guilliermondii Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7788 Rana catesbeiana Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4541 Capnella lacertiliensis Species Nephtheidae 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]
NPO1537 Vaccinium arctostaphylos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8426 Tinospora rumphii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7240 Osteospermum oppositifolium Species Asteraceae 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
NPT139 Cell Line HT-29 Homo sapiens EC50 = 1700.0 nM PMID[467826]
NPT2 Others Unspecified IC50 = 2550.0 nM PMID[467826]

☑ 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 NPC237517 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 NPC111723
1.0 High Similarity NPC91204
0.9917 High Similarity NPC32715
0.9917 High Similarity NPC98200
0.9832 High Similarity NPC174729
0.95 High Similarity NPC122175
0.9244 High Similarity NPC9592
0.9244 High Similarity NPC48781
0.8824 High Similarity NPC23804
0.873 High Similarity NPC139774
0.8667 High Similarity NPC261343
0.8667 High Similarity NPC319803
0.8527 High Similarity NPC66331
0.85 High Similarity NPC224527
0.8385 Intermediate Similarity NPC257947
0.8333 Intermediate Similarity NPC186385
0.8333 Intermediate Similarity NPC19808
0.8333 Intermediate Similarity NPC33728
0.8333 Intermediate Similarity NPC299568
0.8306 Intermediate Similarity NPC115808
0.8279 Intermediate Similarity NPC166995
0.825 Intermediate Similarity NPC174981
0.824 Intermediate Similarity NPC470760
0.8235 Intermediate Similarity NPC99836
0.8235 Intermediate Similarity NPC12640
0.8235 Intermediate Similarity NPC201662
0.8226 Intermediate Similarity NPC84999
0.8226 Intermediate Similarity NPC246760
0.8189 Intermediate Similarity NPC223451
0.8167 Intermediate Similarity NPC204901
0.8167 Intermediate Similarity NPC305603
0.8167 Intermediate Similarity NPC54844
0.8167 Intermediate Similarity NPC158253
0.8167 Intermediate Similarity NPC232523
0.8167 Intermediate Similarity NPC61033
0.8151 Intermediate Similarity NPC246056
0.8151 Intermediate Similarity NPC37802
0.814 Intermediate Similarity NPC18128
0.814 Intermediate Similarity NPC77789
0.813 Intermediate Similarity NPC473521
0.8115 Intermediate Similarity NPC475018
0.811 Intermediate Similarity NPC151197
0.8083 Intermediate Similarity NPC470700
0.8083 Intermediate Similarity NPC302681
0.8083 Intermediate Similarity NPC39664
0.8083 Intermediate Similarity NPC118286
0.8083 Intermediate Similarity NPC39097
0.8083 Intermediate Similarity NPC109691
0.8067 Intermediate Similarity NPC218879
0.8067 Intermediate Similarity NPC244513
0.8067 Intermediate Similarity NPC227458
0.8065 Intermediate Similarity NPC117846
0.8031 Intermediate Similarity NPC206
0.8017 Intermediate Similarity NPC66834
0.8 Intermediate Similarity NPC134829
0.7984 Intermediate Similarity NPC43525
0.7967 Intermediate Similarity NPC132720
0.7953 Intermediate Similarity NPC320864
0.7937 Intermediate Similarity NPC232165
0.7923 Intermediate Similarity NPC39029
0.792 Intermediate Similarity NPC263753
0.7917 Intermediate Similarity NPC475225
0.7917 Intermediate Similarity NPC323810
0.7917 Intermediate Similarity NPC102216
0.7917 Intermediate Similarity NPC241891
0.7907 Intermediate Similarity NPC69006
0.7903 Intermediate Similarity NPC225679
0.7903 Intermediate Similarity NPC476632
0.7903 Intermediate Similarity NPC4493
0.7903 Intermediate Similarity NPC165770
0.7899 Intermediate Similarity NPC137415
0.7899 Intermediate Similarity NPC294186
0.7899 Intermediate Similarity NPC24407
0.7899 Intermediate Similarity NPC166313
0.7899 Intermediate Similarity NPC192032
0.7899 Intermediate Similarity NPC11280
0.7899 Intermediate Similarity NPC147310
0.7895 Intermediate Similarity NPC82299
0.7891 Intermediate Similarity NPC190514
0.7891 Intermediate Similarity NPC144343
0.7868 Intermediate Similarity NPC472590
0.7857 Intermediate Similarity NPC107240
0.7852 Intermediate Similarity NPC472797
0.7846 Intermediate Similarity NPC24125
0.784 Intermediate Similarity NPC228452
0.7836 Intermediate Similarity NPC473221
0.7833 Intermediate Similarity NPC71002
0.7833 Intermediate Similarity NPC106396
0.7833 Intermediate Similarity NPC302219
0.7833 Intermediate Similarity NPC24404
0.7833 Intermediate Similarity NPC471228
0.7833 Intermediate Similarity NPC242342
0.7833 Intermediate Similarity NPC53051
0.7833 Intermediate Similarity NPC222522
0.7833 Intermediate Similarity NPC85479
0.7833 Intermediate Similarity NPC249828
0.7833 Intermediate Similarity NPC94351
0.7833 Intermediate Similarity NPC235762
0.7833 Intermediate Similarity NPC146798
0.7833 Intermediate Similarity NPC313030
0.7833 Intermediate Similarity NPC168303
0.7829 Intermediate Similarity NPC469644
0.7829 Intermediate Similarity NPC121866
0.7829 Intermediate Similarity NPC191866
0.7829 Intermediate Similarity NPC184302
0.782 Intermediate Similarity NPC33654
0.7803 Intermediate Similarity NPC261992
0.7787 Intermediate Similarity NPC248904
0.7778 Intermediate Similarity NPC211179
0.7778 Intermediate Similarity NPC38604
0.7769 Intermediate Similarity NPC472071
0.7752 Intermediate Similarity NPC471671
0.775 Intermediate Similarity NPC143659
0.775 Intermediate Similarity NPC284011
0.775 Intermediate Similarity NPC72947
0.775 Intermediate Similarity NPC100340
0.7737 Intermediate Similarity NPC471517
0.7734 Intermediate Similarity NPC114064
0.7727 Intermediate Similarity NPC188997
0.7727 Intermediate Similarity NPC71094
0.7724 Intermediate Similarity NPC474352
0.7721 Intermediate Similarity NPC472796
0.7721 Intermediate Similarity NPC472795
0.7717 Intermediate Similarity NPC473137
0.7717 Intermediate Similarity NPC12656
0.7714 Intermediate Similarity NPC472800
0.7705 Intermediate Similarity NPC292452
0.7705 Intermediate Similarity NPC474839
0.7705 Intermediate Similarity NPC471350
0.7704 Intermediate Similarity NPC26576
0.7698 Intermediate Similarity NPC302371
0.7692 Intermediate Similarity NPC217174
0.7687 Intermediate Similarity NPC476254
0.7687 Intermediate Similarity NPC131397
0.768 Intermediate Similarity NPC224870
0.7674 Intermediate Similarity NPC69261
0.7674 Intermediate Similarity NPC33270
0.7674 Intermediate Similarity NPC470759
0.7674 Intermediate Similarity NPC15860
0.7674 Intermediate Similarity NPC219070
0.7674 Intermediate Similarity NPC172219
0.7674 Intermediate Similarity NPC127894
0.7674 Intermediate Similarity NPC304510
0.7674 Intermediate Similarity NPC277588
0.7667 Intermediate Similarity NPC174911
0.7667 Intermediate Similarity NPC10588
0.7667 Intermediate Similarity NPC294741
0.7667 Intermediate Similarity NPC166761
0.7661 Intermediate Similarity NPC63698
0.7661 Intermediate Similarity NPC61885
0.7656 Intermediate Similarity NPC808
0.7652 Intermediate Similarity NPC237667
0.7647 Intermediate Similarity NPC311293
0.7647 Intermediate Similarity NPC148366
0.7623 Intermediate Similarity NPC119860
0.7623 Intermediate Similarity NPC30506
0.7619 Intermediate Similarity NPC469912
0.7619 Intermediate Similarity NPC54373
0.7619 Intermediate Similarity NPC151537
0.7615 Intermediate Similarity NPC154030
0.7615 Intermediate Similarity NPC469609
0.7612 Intermediate Similarity NPC224342
0.7603 Intermediate Similarity NPC477685
0.76 Intermediate Similarity NPC473524
0.76 Intermediate Similarity NPC202647
0.7597 Intermediate Similarity NPC123559
0.7597 Intermediate Similarity NPC92
0.7597 Intermediate Similarity NPC150624
0.7597 Intermediate Similarity NPC469663
0.7597 Intermediate Similarity NPC38893
0.7597 Intermediate Similarity NPC477137
0.7597 Intermediate Similarity NPC308311
0.7589 Intermediate Similarity NPC327735
0.7578 Intermediate Similarity NPC249270
0.7578 Intermediate Similarity NPC120280
0.7561 Intermediate Similarity NPC117115
0.7559 Intermediate Similarity NPC228425
0.7556 Intermediate Similarity NPC105031
0.7554 Intermediate Similarity NPC472798
0.7538 Intermediate Similarity NPC244816
0.7538 Intermediate Similarity NPC221549
0.7538 Intermediate Similarity NPC477136
0.7538 Intermediate Similarity NPC50521
0.7538 Intermediate Similarity NPC476266
0.7537 Intermediate Similarity NPC474160
0.7537 Intermediate Similarity NPC53567
0.7521 Intermediate Similarity NPC72729
0.752 Intermediate Similarity NPC262365
0.7519 Intermediate Similarity NPC35797
0.7519 Intermediate Similarity NPC192948
0.7519 Intermediate Similarity NPC476633
0.7519 Intermediate Similarity NPC474486
0.7519 Intermediate Similarity NPC53906
0.75 Intermediate Similarity NPC230479
0.75 Intermediate Similarity NPC477037
0.75 Intermediate Similarity NPC26879
0.75 Intermediate Similarity NPC325544
0.75 Intermediate Similarity NPC469610
0.75 Intermediate Similarity NPC291789
0.75 Intermediate Similarity NPC469913

  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 NPC237517 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
0.8333 Intermediate Similarity NPD4750 Phase 3
0.763 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7559 Intermediate Similarity NPD7635 Approved
0.7536 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD846 Approved
0.7459 Intermediate Similarity NPD940 Approved
0.7442 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD288 Approved
0.7407 Intermediate Similarity NPD4749 Approved
0.7377 Intermediate Similarity NPD1242 Phase 1
0.7338 Intermediate Similarity NPD3027 Phase 3
0.7333 Intermediate Similarity NPD844 Approved
0.7295 Intermediate Similarity NPD3020 Approved
0.7266 Intermediate Similarity NPD4908 Phase 1
0.7214 Intermediate Similarity NPD4625 Phase 3
0.7188 Intermediate Similarity NPD3021 Approved
0.7188 Intermediate Similarity NPD3022 Approved
0.7174 Intermediate Similarity NPD3094 Phase 2
0.7163 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1610 Phase 2
0.7097 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD3091 Approved
0.7063 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1613 Approved
0.7049 Intermediate Similarity NPD2859 Approved
0.7049 Intermediate Similarity NPD2860 Approved
0.7031 Intermediate Similarity NPD2342 Discontinued
0.7007 Intermediate Similarity NPD3092 Approved
0.6985 Remote Similarity NPD4589 Approved
0.6967 Remote Similarity NPD2933 Approved
0.6967 Remote Similarity NPD2934 Approved
0.6966 Remote Similarity NPD2568 Approved
0.695 Remote Similarity NPD2861 Phase 2
0.6939 Remote Similarity NPD6099 Approved
0.6939 Remote Similarity NPD6100 Approved
0.6918 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6885 Remote Similarity NPD845 Approved
0.6884 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6884 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6861 Remote Similarity NPD3095 Discontinued
0.6842 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7041 Phase 2
0.6838 Remote Similarity NPD1548 Phase 1
0.6831 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6828 Remote Similarity NPD2238 Phase 2
0.6815 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6783 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6761 Remote Similarity NPD602 Approved
0.6761 Remote Similarity NPD599 Approved
0.6761 Remote Similarity NPD859 Approved
0.6761 Remote Similarity NPD858 Approved
0.6759 Remote Similarity NPD6405 Approved
0.6759 Remote Similarity NPD6407 Approved
0.6757 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6755 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6741 Remote Similarity NPD6671 Approved
0.6739 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7390 Discontinued
0.6719 Remote Similarity NPD9500 Approved
0.6719 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6712 Remote Similarity NPD1555 Discontinued
0.6694 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6692 Remote Similarity NPD6124 Clinical (unspecified phase)
0.6689 Remote Similarity NPD4536 Approved
0.6689 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6689 Remote Similarity NPD4538 Approved
0.6689 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1792 Phase 2
0.6667 Remote Similarity NPD497 Approved
0.6645 Remote Similarity NPD3892 Phase 2
0.664 Remote Similarity NPD1809 Phase 2
0.662 Remote Similarity NPD6696 Suspended
0.6619 Remote Similarity NPD5846 Approved
0.6619 Remote Similarity NPD6516 Phase 2
0.6604 Remote Similarity NPD37 Approved
0.6597 Remote Similarity NPD5736 Approved
0.6594 Remote Similarity NPD7741 Discontinued
0.6593 Remote Similarity NPD496 Approved
0.6593 Remote Similarity NPD498 Approved
0.6593 Remote Similarity NPD495 Approved
0.6581 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6575 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6565 Remote Similarity NPD1445 Approved
0.6565 Remote Similarity NPD1444 Approved
0.6562 Remote Similarity NPD1616 Discontinued
0.6556 Remote Similarity NPD5762 Approved
0.6556 Remote Similarity NPD5763 Approved
0.6549 Remote Similarity NPD4659 Approved
0.6541 Remote Similarity NPD5451 Approved
0.6533 Remote Similarity NPD5588 Approved
0.6533 Remote Similarity NPD5960 Phase 3
0.6525 Remote Similarity NPD1201 Approved
0.6519 Remote Similarity NPD6057 Approved
0.6519 Remote Similarity NPD6056 Approved
0.65 Remote Similarity NPD2932 Approved
0.65 Remote Similarity NPD4059 Approved
0.65 Remote Similarity NPD3019 Approved
0.6486 Remote Similarity NPD4060 Phase 1
0.6486 Remote Similarity NPD943 Approved
0.6483 Remote Similarity NPD3018 Phase 2
0.6481 Remote Similarity NPD4966 Approved
0.6481 Remote Similarity NPD4965 Approved
0.6481 Remote Similarity NPD4967 Phase 2
0.6479 Remote Similarity NPD2233 Approved
0.6479 Remote Similarity NPD2230 Approved
0.6479 Remote Similarity NPD2232 Approved
0.6471 Remote Similarity NPD2229 Approved
0.6471 Remote Similarity NPD2228 Approved
0.6471 Remote Similarity NPD2234 Approved
0.6471 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5283 Phase 1
0.6458 Remote Similarity NPD1470 Approved
0.6458 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4103 Phase 2
0.6458 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7340 Approved
0.6447 Remote Similarity NPD7266 Discontinued
0.6442 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6434 Remote Similarity NPD4359 Approved
0.6429 Remote Similarity NPD4093 Discontinued
0.6424 Remote Similarity NPD7743 Approved
0.6424 Remote Similarity NPD7742 Approved
0.6423 Remote Similarity NPD9614 Approved
0.6423 Remote Similarity NPD9618 Approved
0.642 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6419 Remote Similarity NPD6663 Approved
0.6408 Remote Similarity NPD1091 Approved
0.6402 Remote Similarity NPD6234 Discontinued
0.64 Remote Similarity NPD5314 Approved
0.64 Remote Similarity NPD4097 Suspended
0.64 Remote Similarity NPD1607 Approved
0.6383 Remote Similarity NPD5126 Approved
0.6383 Remote Similarity NPD2286 Discontinued
0.6383 Remote Similarity NPD4626 Approved
0.6383 Remote Similarity NPD5125 Phase 3
0.6382 Remote Similarity NPD5405 Approved
0.6382 Remote Similarity NPD5404 Approved
0.6382 Remote Similarity NPD5406 Approved
0.6382 Remote Similarity NPD5408 Approved
0.6376 Remote Similarity NPD3062 Approved
0.6376 Remote Similarity NPD3620 Phase 2
0.6376 Remote Similarity NPD3061 Approved
0.6376 Remote Similarity NPD3059 Approved
0.6376 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6369 Remote Similarity NPD7447 Phase 1
0.6369 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6364 Remote Similarity NPD2231 Phase 2
0.6364 Remote Similarity NPD6674 Discontinued
0.6364 Remote Similarity NPD2235 Phase 2
0.6364 Remote Similarity NPD5177 Phase 3
0.6364 Remote Similarity NPD2561 Approved
0.6364 Remote Similarity NPD2562 Approved
0.6358 Remote Similarity NPD3555 Approved
0.6358 Remote Similarity NPD3553 Approved
0.6358 Remote Similarity NPD3552 Approved
0.6358 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6358 Remote Similarity NPD3554 Approved
0.6357 Remote Similarity NPD7330 Discontinued
0.6357 Remote Similarity NPD5303 Approved
0.6357 Remote Similarity NPD5304 Approved
0.6357 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6352 Remote Similarity NPD2370 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5058 Phase 3
0.6346 Remote Similarity NPD6815 Approved
0.6345 Remote Similarity NPD1133 Approved
0.6345 Remote Similarity NPD1134 Approved
0.6345 Remote Similarity NPD1135 Approved
0.6345 Remote Similarity NPD1129 Approved
0.6345 Remote Similarity NPD1131 Approved
0.634 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6333 Remote Similarity NPD5124 Phase 1
0.6333 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6333 Remote Similarity NPD5735 Approved
0.6331 Remote Similarity NPD7228 Approved
0.6329 Remote Similarity NPD6090 Discontinued
0.6325 Remote Similarity NPD6959 Discontinued
0.6323 Remote Similarity NPD3400 Discontinued
0.6319 Remote Similarity NPD2983 Phase 2
0.6319 Remote Similarity NPD2982 Phase 2
0.6316 Remote Similarity NPD968 Approved
0.6316 Remote Similarity NPD1510 Phase 2
0.6308 Remote Similarity NPD3028 Approved
0.6306 Remote Similarity NPD7212 Phase 2
0.6306 Remote Similarity NPD7213 Phase 3
0.6303 Remote Similarity NPD9093 Approved
0.6299 Remote Similarity NPD970 Clinical (unspecified phase)
0.6296 Remote Similarity NPD1934 Approved
0.6296 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6294 Remote Similarity NPD422 Phase 1
0.6286 Remote Similarity NPD9613 Approved
0.6286 Remote Similarity NPD9616 Approved
0.6286 Remote Similarity NPD9615 Approved
0.6277 Remote Similarity NPD7843 Approved
0.6276 Remote Similarity NPD8651 Approved
0.6275 Remote Similarity NPD2935 Discontinued
0.6275 Remote Similarity NPD1551 Phase 2
0.6273 Remote Similarity NPD4380 Phase 2
0.6272 Remote Similarity NPD7473 Discontinued

  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