Structure

Physi-Chem Properties

Molecular Weight:  704.26
Volume:  694.519
LogP:  8.532
LogD:  5.868
LogS:  -3.154
# Rotatable Bonds:  8
TPSA:  101.15
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.176
Synthetic Accessibility Score:  6.254
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:  -4.833
MDCK Permeability:  1.96141772903502e-05
Pgp-inhibitor:  0.042
Pgp-substrate:  0.414
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.186
Plasma Protein Binding (PPB):  101.0007553100586%
Volume Distribution (VD):  5.33
Pgp-substrate:  0.8948471546173096%

ADMET: Metabolism

CYP1A2-inhibitor:  0.159
CYP1A2-substrate:  0.74
CYP2C19-inhibitor:  0.665
CYP2C19-substrate:  0.778
CYP2C9-inhibitor:  0.124
CYP2C9-substrate:  0.994
CYP2D6-inhibitor:  0.635
CYP2D6-substrate:  0.535
CYP3A4-inhibitor:  0.133
CYP3A4-substrate:  0.287

ADMET: Excretion

Clearance (CL):  2.862
Half-life (T1/2):  0.213

ADMET: Toxicity

hERG Blockers:  0.068
Human Hepatotoxicity (H-HT):  0.139
Drug-inuced Liver Injury (DILI):  0.041
AMES Toxicity:  0.248
Rat Oral Acute Toxicity:  0.982
Maximum Recommended Daily Dose:  0.987
Skin Sensitization:  0.96
Carcinogencity:  0.145
Eye Corrosion:  0.003
Eye Irritation:  0.763
Respiratory Toxicity:  0.929

Download Data

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

  Natural Product: NPC98200

Natural Product ID:  NPC98200
Common Name*:   Cylindrocyclophane C4
IUPAC Name:   n.a.
Synonyms:   Cylindrocyclophane C4
Standard InCHIKey:  WKPXZZKUCLAECJ-KFCUGCEISA-N
Standard InCHI:  InChI=1S/C36H52Cl4O5/c1-22-9-3-5-11-26(14-8-16-33(39)40)35-30(43)20-27(21-31(35)44)36(45)23(2)10-4-6-12-25(13-7-15-32(37)38)34-28(41)18-24(17-22)19-29(34)42/h18-23,25-26,32-33,36,41-45H,3-17H2,1-2H3/t22-,23-,25+,26+,36+/m0/s1
SMILES:  ClC(CCC[C@H]1CCCC[C@H](C)[C@@H](O)c2cc(O)c(c(c2)O)[C@H](CCCC[C@@H](Cc2cc(c1c(O)c2)O)C)CCCC(Cl)Cl)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1224862
PubChem CID:   46939424
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 = 2800.0 nM PMID[507740]
NPT2 Others Unspecified IC50 = 11200.0 nM PMID[507740]

☑ 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 NPC98200 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 NPC32715
0.9917 High Similarity NPC237517
0.9917 High Similarity NPC111723
0.9917 High Similarity NPC91204
0.975 High Similarity NPC174729
0.9583 High Similarity NPC122175
0.9167 High Similarity NPC9592
0.9167 High Similarity NPC48781
0.875 High Similarity NPC23804
0.8661 High Similarity NPC139774
0.8595 High Similarity NPC261343
0.8595 High Similarity NPC319803
0.8462 Intermediate Similarity NPC66331
0.843 Intermediate Similarity NPC224527
0.8321 Intermediate Similarity NPC257947
0.8264 Intermediate Similarity NPC299568
0.8264 Intermediate Similarity NPC186385
0.8264 Intermediate Similarity NPC19808
0.8264 Intermediate Similarity NPC33728
0.824 Intermediate Similarity NPC115808
0.8211 Intermediate Similarity NPC166995
0.8182 Intermediate Similarity NPC174981
0.8175 Intermediate Similarity NPC470760
0.8167 Intermediate Similarity NPC201662
0.8167 Intermediate Similarity NPC12640
0.8167 Intermediate Similarity NPC99836
0.816 Intermediate Similarity NPC84999
0.816 Intermediate Similarity NPC246760
0.8125 Intermediate Similarity NPC223451
0.8099 Intermediate Similarity NPC204901
0.8099 Intermediate Similarity NPC61033
0.8099 Intermediate Similarity NPC158253
0.8099 Intermediate Similarity NPC232523
0.8099 Intermediate Similarity NPC54844
0.8099 Intermediate Similarity NPC305603
0.8083 Intermediate Similarity NPC246056
0.8083 Intermediate Similarity NPC37802
0.8077 Intermediate Similarity NPC77789
0.8077 Intermediate Similarity NPC18128
0.8065 Intermediate Similarity NPC473521
0.8049 Intermediate Similarity NPC475018
0.8047 Intermediate Similarity NPC151197
0.8017 Intermediate Similarity NPC109691
0.8017 Intermediate Similarity NPC302681
0.8017 Intermediate Similarity NPC39664
0.8017 Intermediate Similarity NPC118286
0.8017 Intermediate Similarity NPC470700
0.8017 Intermediate Similarity NPC39097
0.8 Intermediate Similarity NPC218879
0.8 Intermediate Similarity NPC117846
0.8 Intermediate Similarity NPC244513
0.8 Intermediate Similarity NPC227458
0.7969 Intermediate Similarity NPC206
0.7951 Intermediate Similarity NPC66834
0.7934 Intermediate Similarity NPC134829
0.792 Intermediate Similarity NPC43525
0.7903 Intermediate Similarity NPC132720
0.7891 Intermediate Similarity NPC320864
0.7874 Intermediate Similarity NPC232165
0.7863 Intermediate Similarity NPC39029
0.7857 Intermediate Similarity NPC263753
0.7851 Intermediate Similarity NPC241891
0.7851 Intermediate Similarity NPC475225
0.7851 Intermediate Similarity NPC102216
0.7851 Intermediate Similarity NPC323810
0.7846 Intermediate Similarity NPC69006
0.784 Intermediate Similarity NPC225679
0.784 Intermediate Similarity NPC476632
0.784 Intermediate Similarity NPC4493
0.784 Intermediate Similarity NPC165770
0.7836 Intermediate Similarity NPC82299
0.7833 Intermediate Similarity NPC11280
0.7833 Intermediate Similarity NPC294186
0.7833 Intermediate Similarity NPC137415
0.7833 Intermediate Similarity NPC166313
0.7833 Intermediate Similarity NPC147310
0.7833 Intermediate Similarity NPC192032
0.7833 Intermediate Similarity NPC24407
0.7829 Intermediate Similarity NPC190514
0.7829 Intermediate Similarity NPC144343
0.781 Intermediate Similarity NPC472590
0.7795 Intermediate Similarity NPC107240
0.7794 Intermediate Similarity NPC472797
0.7786 Intermediate Similarity NPC24125
0.7778 Intermediate Similarity NPC228452
0.7778 Intermediate Similarity NPC473221
0.7769 Intermediate Similarity NPC24404
0.7769 Intermediate Similarity NPC302219
0.7769 Intermediate Similarity NPC242342
0.7769 Intermediate Similarity NPC471228
0.7769 Intermediate Similarity NPC184302
0.7769 Intermediate Similarity NPC71002
0.7769 Intermediate Similarity NPC249828
0.7769 Intermediate Similarity NPC168303
0.7769 Intermediate Similarity NPC146798
0.7769 Intermediate Similarity NPC53051
0.7769 Intermediate Similarity NPC313030
0.7769 Intermediate Similarity NPC469644
0.7769 Intermediate Similarity NPC222522
0.7769 Intermediate Similarity NPC106396
0.7769 Intermediate Similarity NPC121866
0.7769 Intermediate Similarity NPC85479
0.7769 Intermediate Similarity NPC235762
0.7769 Intermediate Similarity NPC191866
0.7769 Intermediate Similarity NPC94351
0.7761 Intermediate Similarity NPC33654
0.7744 Intermediate Similarity NPC261992
0.7724 Intermediate Similarity NPC248904
0.7721 Intermediate Similarity NPC211179
0.7721 Intermediate Similarity NPC38604
0.771 Intermediate Similarity NPC472071
0.7692 Intermediate Similarity NPC471671
0.7686 Intermediate Similarity NPC100340
0.7686 Intermediate Similarity NPC72947
0.7686 Intermediate Similarity NPC143659
0.7686 Intermediate Similarity NPC284011
0.7681 Intermediate Similarity NPC471517
0.7674 Intermediate Similarity NPC114064
0.7669 Intermediate Similarity NPC188997
0.7669 Intermediate Similarity NPC71094
0.7664 Intermediate Similarity NPC472795
0.7664 Intermediate Similarity NPC472796
0.7661 Intermediate Similarity NPC474352
0.766 Intermediate Similarity NPC472800
0.7656 Intermediate Similarity NPC12656
0.7656 Intermediate Similarity NPC473137
0.7647 Intermediate Similarity NPC26576
0.7642 Intermediate Similarity NPC292452
0.7642 Intermediate Similarity NPC471350
0.7642 Intermediate Similarity NPC474839
0.7638 Intermediate Similarity NPC302371
0.7634 Intermediate Similarity NPC217174
0.763 Intermediate Similarity NPC131397
0.763 Intermediate Similarity NPC476254
0.7619 Intermediate Similarity NPC224870
0.7615 Intermediate Similarity NPC69261
0.7615 Intermediate Similarity NPC277588
0.7615 Intermediate Similarity NPC33270
0.7615 Intermediate Similarity NPC470759
0.7615 Intermediate Similarity NPC127894
0.7615 Intermediate Similarity NPC15860
0.7615 Intermediate Similarity NPC172219
0.7615 Intermediate Similarity NPC219070
0.7615 Intermediate Similarity NPC304510
0.7603 Intermediate Similarity NPC174911
0.7603 Intermediate Similarity NPC166761
0.7603 Intermediate Similarity NPC294741
0.7603 Intermediate Similarity NPC10588
0.76 Intermediate Similarity NPC61885
0.76 Intermediate Similarity NPC63698
0.7597 Intermediate Similarity NPC808
0.7594 Intermediate Similarity NPC237667
0.7591 Intermediate Similarity NPC148366
0.7591 Intermediate Similarity NPC311293
0.7561 Intermediate Similarity NPC119860
0.7561 Intermediate Similarity NPC30506
0.7559 Intermediate Similarity NPC54373
0.7559 Intermediate Similarity NPC469912
0.7559 Intermediate Similarity NPC151537
0.7557 Intermediate Similarity NPC154030
0.7557 Intermediate Similarity NPC469609
0.7556 Intermediate Similarity NPC224342
0.7541 Intermediate Similarity NPC477685
0.754 Intermediate Similarity NPC473524
0.754 Intermediate Similarity NPC202647
0.7538 Intermediate Similarity NPC123559
0.7538 Intermediate Similarity NPC150624
0.7538 Intermediate Similarity NPC38893
0.7538 Intermediate Similarity NPC92
0.7538 Intermediate Similarity NPC308311
0.7538 Intermediate Similarity NPC469663
0.7538 Intermediate Similarity NPC477137
0.7535 Intermediate Similarity NPC327735
0.7519 Intermediate Similarity NPC249270
0.7519 Intermediate Similarity NPC120280
0.75 Intermediate Similarity NPC228425
0.75 Intermediate Similarity NPC117115
0.75 Intermediate Similarity NPC472798
0.75 Intermediate Similarity NPC105031
0.7481 Intermediate Similarity NPC50521
0.7481 Intermediate Similarity NPC474160
0.7481 Intermediate Similarity NPC476266
0.7481 Intermediate Similarity NPC477136
0.7481 Intermediate Similarity NPC244816
0.7481 Intermediate Similarity NPC53567
0.7481 Intermediate Similarity NPC221549
0.7463 Intermediate Similarity NPC476633
0.7462 Intermediate Similarity NPC474486
0.7462 Intermediate Similarity NPC35797
0.7462 Intermediate Similarity NPC53906
0.7462 Intermediate Similarity NPC192948
0.746 Intermediate Similarity NPC262365
0.7459 Intermediate Similarity NPC72729
0.7447 Intermediate Similarity NPC469610
0.7447 Intermediate Similarity NPC474453
0.7445 Intermediate Similarity NPC283049
0.7445 Intermediate Similarity NPC50315
0.7445 Intermediate Similarity NPC26879
0.7445 Intermediate Similarity NPC230479
0.7444 Intermediate Similarity NPC477037

  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 NPC98200 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
0.8264 Intermediate Similarity NPD4750 Phase 3
0.7574 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7635 Approved
0.7482 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD846 Approved
0.7398 Intermediate Similarity NPD940 Approved
0.7355 Intermediate Similarity NPD288 Approved
0.7353 Intermediate Similarity NPD4749 Approved
0.7317 Intermediate Similarity NPD1242 Phase 1
0.7286 Intermediate Similarity NPD3027 Phase 3
0.7273 Intermediate Similarity NPD844 Approved
0.7236 Intermediate Similarity NPD3020 Approved
0.7214 Intermediate Similarity NPD4908 Phase 1
0.7163 Intermediate Similarity NPD4625 Phase 3
0.7132 Intermediate Similarity NPD3021 Approved
0.7132 Intermediate Similarity NPD3022 Approved
0.7122 Intermediate Similarity NPD3094 Phase 2
0.7113 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD1610 Phase 2
0.704 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3091 Approved
0.7014 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD1613 Approved
0.6992 Remote Similarity NPD2860 Approved
0.6992 Remote Similarity NPD2859 Approved
0.6977 Remote Similarity NPD2342 Discontinued
0.6957 Remote Similarity NPD3092 Approved
0.6934 Remote Similarity NPD4589 Approved
0.6918 Remote Similarity NPD2568 Approved
0.6911 Remote Similarity NPD2934 Approved
0.6911 Remote Similarity NPD2933 Approved
0.6901 Remote Similarity NPD2861 Phase 2
0.6892 Remote Similarity NPD6099 Approved
0.6892 Remote Similarity NPD6100 Approved
0.6871 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6835 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6835 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6829 Remote Similarity NPD845 Approved
0.6812 Remote Similarity NPD3095 Discontinued
0.6797 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6797 Remote Similarity NPD7041 Phase 2
0.6788 Remote Similarity NPD1548 Phase 1
0.6783 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6781 Remote Similarity NPD2238 Phase 2
0.6765 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6738 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6736 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6713 Remote Similarity NPD858 Approved
0.6713 Remote Similarity NPD602 Approved
0.6713 Remote Similarity NPD859 Approved
0.6713 Remote Similarity NPD599 Approved
0.6712 Remote Similarity NPD6407 Approved
0.6712 Remote Similarity NPD6405 Approved
0.6711 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6711 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6691 Remote Similarity NPD6671 Approved
0.6691 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7390 Discontinued
0.6667 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9500 Approved
0.6667 Remote Similarity NPD1555 Discontinued
0.6645 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6644 Remote Similarity NPD4538 Approved
0.6644 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6644 Remote Similarity NPD4536 Approved
0.6642 Remote Similarity NPD6124 Clinical (unspecified phase)
0.664 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6618 Remote Similarity NPD497 Approved
0.6617 Remote Similarity NPD1792 Phase 2
0.6601 Remote Similarity NPD3892 Phase 2
0.6587 Remote Similarity NPD1809 Phase 2
0.6573 Remote Similarity NPD6696 Suspended
0.6571 Remote Similarity NPD5846 Approved
0.6571 Remote Similarity NPD6516 Phase 2
0.6562 Remote Similarity NPD37 Approved
0.6552 Remote Similarity NPD5736 Approved
0.6547 Remote Similarity NPD7741 Discontinued
0.6544 Remote Similarity NPD496 Approved
0.6544 Remote Similarity NPD495 Approved
0.6544 Remote Similarity NPD498 Approved
0.6538 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6531 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6515 Remote Similarity NPD1445 Approved
0.6515 Remote Similarity NPD1444 Approved
0.6513 Remote Similarity NPD5762 Approved
0.6513 Remote Similarity NPD5763 Approved
0.6512 Remote Similarity NPD1616 Discontinued
0.6503 Remote Similarity NPD4659 Approved
0.6493 Remote Similarity NPD5451 Approved
0.649 Remote Similarity NPD5960 Phase 3
0.649 Remote Similarity NPD5588 Approved
0.6479 Remote Similarity NPD1201 Approved
0.6478 Remote Similarity NPD6056 Approved
0.6478 Remote Similarity NPD6057 Approved
0.6454 Remote Similarity NPD2932 Approved
0.6454 Remote Similarity NPD3019 Approved
0.6454 Remote Similarity NPD4059 Approved
0.6443 Remote Similarity NPD4060 Phase 1
0.6443 Remote Similarity NPD943 Approved
0.6442 Remote Similarity NPD4967 Phase 2
0.6442 Remote Similarity NPD4966 Approved
0.6442 Remote Similarity NPD4965 Approved
0.6438 Remote Similarity NPD3018 Phase 2
0.6434 Remote Similarity NPD2232 Approved
0.6434 Remote Similarity NPD2230 Approved
0.6434 Remote Similarity NPD2233 Approved
0.6423 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6423 Remote Similarity NPD2234 Approved
0.6423 Remote Similarity NPD5283 Phase 1
0.6423 Remote Similarity NPD2229 Approved
0.6423 Remote Similarity NPD2228 Approved
0.6414 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6414 Remote Similarity NPD4103 Phase 2
0.6414 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6414 Remote Similarity NPD1470 Approved
0.6405 Remote Similarity NPD7266 Discontinued
0.6403 Remote Similarity NPD7340 Approved
0.6402 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6389 Remote Similarity NPD4359 Approved
0.6383 Remote Similarity NPD4093 Discontinued
0.6382 Remote Similarity NPD7742 Approved
0.6382 Remote Similarity NPD7743 Approved
0.638 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6377 Remote Similarity NPD9618 Approved
0.6377 Remote Similarity NPD9614 Approved
0.6376 Remote Similarity NPD6663 Approved
0.6364 Remote Similarity NPD6234 Discontinued
0.6364 Remote Similarity NPD1091 Approved
0.6358 Remote Similarity NPD1607 Approved
0.6358 Remote Similarity NPD5314 Approved
0.6358 Remote Similarity NPD4097 Suspended
0.634 Remote Similarity NPD5405 Approved
0.634 Remote Similarity NPD5404 Approved
0.634 Remote Similarity NPD5408 Approved
0.634 Remote Similarity NPD5406 Approved
0.6338 Remote Similarity NPD5126 Approved
0.6338 Remote Similarity NPD2286 Discontinued
0.6338 Remote Similarity NPD4626 Approved
0.6338 Remote Similarity NPD5125 Phase 3
0.6333 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6333 Remote Similarity NPD3062 Approved
0.6333 Remote Similarity NPD3061 Approved
0.6333 Remote Similarity NPD3059 Approved
0.6333 Remote Similarity NPD3620 Phase 2
0.6329 Remote Similarity NPD7447 Phase 1
0.6329 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6323 Remote Similarity NPD6674 Discontinued
0.6323 Remote Similarity NPD5177 Phase 3
0.6319 Remote Similarity NPD2231 Phase 2
0.6319 Remote Similarity NPD2562 Approved
0.6319 Remote Similarity NPD2561 Approved
0.6319 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6319 Remote Similarity NPD1157 Approved
0.6319 Remote Similarity NPD2235 Phase 2
0.6316 Remote Similarity NPD3555 Approved
0.6316 Remote Similarity NPD3552 Approved
0.6316 Remote Similarity NPD3553 Approved
0.6316 Remote Similarity NPD3554 Approved
0.6312 Remote Similarity NPD5303 Approved
0.6312 Remote Similarity NPD2370 Clinical (unspecified phase)
0.6312 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6312 Remote Similarity NPD5304 Approved
0.6312 Remote Similarity NPD7330 Discontinued
0.6306 Remote Similarity NPD6815 Approved
0.6306 Remote Similarity NPD5058 Phase 3
0.6301 Remote Similarity NPD1129 Approved
0.6301 Remote Similarity NPD1133 Approved
0.6301 Remote Similarity NPD1131 Approved
0.6301 Remote Similarity NPD1135 Approved
0.6301 Remote Similarity NPD1134 Approved
0.6299 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6294 Remote Similarity NPD7228 Approved
0.6291 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6291 Remote Similarity NPD5735 Approved
0.6291 Remote Similarity NPD5124 Phase 1
0.6289 Remote Similarity NPD6090 Discontinued
0.6287 Remote Similarity NPD6959 Discontinued
0.6282 Remote Similarity NPD3400 Discontinued
0.6276 Remote Similarity NPD2983 Phase 2
0.6276 Remote Similarity NPD2982 Phase 2
0.6275 Remote Similarity NPD1510 Phase 2
0.6269 Remote Similarity NPD968 Approved
0.6266 Remote Similarity NPD7213 Phase 3
0.6266 Remote Similarity NPD7212 Phase 2
0.626 Remote Similarity NPD3028 Approved
0.6258 Remote Similarity NPD970 Clinical (unspecified phase)
0.6258 Remote Similarity NPD1934 Approved
0.625 Remote Similarity NPD422 Phase 1
0.625 Remote Similarity NPD9380 Clinical (unspecified phase)
0.625 Remote Similarity NPD9093 Approved
0.6241 Remote Similarity NPD9616 Approved
0.6241 Remote Similarity NPD9615 Approved
0.6241 Remote Similarity NPD9613 Approved
0.6235 Remote Similarity NPD7473 Discontinued
0.6235 Remote Similarity NPD4380 Phase 2
0.6234 Remote Similarity NPD1551 Phase 2
0.6234 Remote Similarity NPD2935 Discontinued
0.6233 Remote Similarity NPD8651 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