Structure

Physi-Chem Properties

Molecular Weight:  896.05
Volume:  719.6
LogP:  7.752
LogD:  4.738
LogS:  -3.885
# Rotatable Bonds:  8
TPSA:  121.38
# H-Bond Aceptor:  6
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.147
Synthetic Accessibility Score:  6.363
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:  -5.452
MDCK Permeability:  1.4717863450641744e-05
Pgp-inhibitor:  0.937
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.178
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.044
Plasma Protein Binding (PPB):  100.77840423583984%
Volume Distribution (VD):  4.16
Pgp-substrate:  1.1078733205795288%

ADMET: Metabolism

CYP1A2-inhibitor:  0.243
CYP1A2-substrate:  0.614
CYP2C19-inhibitor:  0.935
CYP2C19-substrate:  0.119
CYP2C9-inhibitor:  0.973
CYP2C9-substrate:  0.994
CYP2D6-inhibitor:  0.085
CYP2D6-substrate:  0.451
CYP3A4-inhibitor:  0.713
CYP3A4-substrate:  0.868

ADMET: Excretion

Clearance (CL):  0.134
Half-life (T1/2):  0.093

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.804
Drug-inuced Liver Injury (DILI):  0.923
AMES Toxicity:  0.386
Rat Oral Acute Toxicity:  0.901
Maximum Recommended Daily Dose:  0.988
Skin Sensitization:  0.963
Carcinogencity:  0.281
Eye Corrosion:  0.003
Eye Irritation:  0.849
Respiratory Toxicity:  0.763

Download Data

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

  Natural Product: NPC139774

Natural Product ID:  NPC139774
Common Name*:   Cylindrocyclophane Ab4
IUPAC Name:   n.a.
Synonyms:   Cylindrocyclophane Ab4
Standard InCHIKey:  OAOGUBBGJGDGQT-PLKRWIMUSA-N
Standard InCHI:  InChI=1S/C36H52Br4O6/c1-21-9-3-5-11-23(13-7-15-31(37)38)34-29(43)19-26(20-30(34)44)36(46)22(2)10-4-6-12-24(14-8-16-32(39)40)33-27(41)17-25(35(21)45)18-28(33)42/h17-24,31-32,35-36,41-46H,3-16H2,1-2H3/t21-,22-,23+,24+,35+,36+/m0/s1
SMILES:  C[C@H]1CCCC[C@H](CCCC(Br)Br)c2c(cc(cc2O)[C@@H]([C@@H](C)CCCC[C@H](CCCC(Br)Br)c2c(cc(cc2O)[C@@H]1O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1224865
PubChem CID:   46939504
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]
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]
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]
NPO1969 Streptomyces pilosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28833 Eleutherococcus sieboldianus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8811 Cytisus prolifer Species Fabaceae 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]
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]

☑ 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 = 500.0 nM PMID[501281]
NPT2 Others Unspecified IC50 = 2230.0 nM PMID[501281]

☑ 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 NPC139774 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9402 High Similarity NPC9592
0.9402 High Similarity NPC48781
0.8974 High Similarity NPC23804
0.8871 High Similarity NPC174729
0.8814 High Similarity NPC261343
0.8814 High Similarity NPC319803
0.873 High Similarity NPC237517
0.873 High Similarity NPC91204
0.873 High Similarity NPC111723
0.8661 High Similarity NPC66331
0.8661 High Similarity NPC98200
0.8661 High Similarity NPC32715
0.8644 High Similarity NPC224527
0.8516 High Similarity NPC257947
0.8475 Intermediate Similarity NPC33728
0.8475 Intermediate Similarity NPC19808
0.8475 Intermediate Similarity NPC186385
0.8475 Intermediate Similarity NPC299568
0.8443 Intermediate Similarity NPC115808
0.8417 Intermediate Similarity NPC166995
0.839 Intermediate Similarity NPC174981
0.8376 Intermediate Similarity NPC201662
0.8376 Intermediate Similarity NPC99836
0.8376 Intermediate Similarity NPC12640
0.8374 Intermediate Similarity NPC470760
0.8361 Intermediate Similarity NPC84999
0.8361 Intermediate Similarity NPC246760
0.832 Intermediate Similarity NPC223451
0.8305 Intermediate Similarity NPC305603
0.8305 Intermediate Similarity NPC204901
0.8305 Intermediate Similarity NPC158253
0.8305 Intermediate Similarity NPC54844
0.8305 Intermediate Similarity NPC61033
0.8305 Intermediate Similarity NPC232523
0.8291 Intermediate Similarity NPC37802
0.8291 Intermediate Similarity NPC246056
0.8268 Intermediate Similarity NPC18128
0.8268 Intermediate Similarity NPC77789
0.8268 Intermediate Similarity NPC122175
0.8264 Intermediate Similarity NPC473521
0.825 Intermediate Similarity NPC475018
0.824 Intermediate Similarity NPC151197
0.822 Intermediate Similarity NPC470700
0.822 Intermediate Similarity NPC118286
0.822 Intermediate Similarity NPC109691
0.822 Intermediate Similarity NPC39097
0.822 Intermediate Similarity NPC39664
0.822 Intermediate Similarity NPC302681
0.8205 Intermediate Similarity NPC244513
0.8205 Intermediate Similarity NPC227458
0.8205 Intermediate Similarity NPC218879
0.8197 Intermediate Similarity NPC117846
0.816 Intermediate Similarity NPC206
0.8151 Intermediate Similarity NPC66834
0.8136 Intermediate Similarity NPC134829
0.8115 Intermediate Similarity NPC43525
0.8099 Intermediate Similarity NPC132720
0.808 Intermediate Similarity NPC320864
0.8065 Intermediate Similarity NPC232165
0.8051 Intermediate Similarity NPC241891
0.8051 Intermediate Similarity NPC102216
0.8051 Intermediate Similarity NPC475225
0.8051 Intermediate Similarity NPC323810
0.8049 Intermediate Similarity NPC263753
0.8047 Intermediate Similarity NPC39029
0.8034 Intermediate Similarity NPC192032
0.8034 Intermediate Similarity NPC24407
0.8034 Intermediate Similarity NPC11280
0.8034 Intermediate Similarity NPC137415
0.8034 Intermediate Similarity NPC147310
0.8034 Intermediate Similarity NPC294186
0.8034 Intermediate Similarity NPC166313
0.8033 Intermediate Similarity NPC4493
0.8033 Intermediate Similarity NPC225679
0.8033 Intermediate Similarity NPC165770
0.8033 Intermediate Similarity NPC476632
0.8031 Intermediate Similarity NPC69006
0.8016 Intermediate Similarity NPC190514
0.8016 Intermediate Similarity NPC144343
0.8015 Intermediate Similarity NPC82299
0.7985 Intermediate Similarity NPC472590
0.7984 Intermediate Similarity NPC107240
0.797 Intermediate Similarity NPC472797
0.7969 Intermediate Similarity NPC24125
0.7967 Intermediate Similarity NPC228452
0.7966 Intermediate Similarity NPC85479
0.7966 Intermediate Similarity NPC249828
0.7966 Intermediate Similarity NPC235762
0.7966 Intermediate Similarity NPC471228
0.7966 Intermediate Similarity NPC168303
0.7966 Intermediate Similarity NPC53051
0.7966 Intermediate Similarity NPC94351
0.7966 Intermediate Similarity NPC24404
0.7966 Intermediate Similarity NPC313030
0.7966 Intermediate Similarity NPC242342
0.7966 Intermediate Similarity NPC106396
0.7966 Intermediate Similarity NPC146798
0.7966 Intermediate Similarity NPC302219
0.7966 Intermediate Similarity NPC222522
0.7966 Intermediate Similarity NPC71002
0.7955 Intermediate Similarity NPC473221
0.7953 Intermediate Similarity NPC469644
0.7953 Intermediate Similarity NPC184302
0.7953 Intermediate Similarity NPC191866
0.7953 Intermediate Similarity NPC121866
0.7939 Intermediate Similarity NPC33654
0.7923 Intermediate Similarity NPC261992
0.7917 Intermediate Similarity NPC248904
0.7895 Intermediate Similarity NPC38604
0.7895 Intermediate Similarity NPC211179
0.7891 Intermediate Similarity NPC472071
0.7881 Intermediate Similarity NPC100340
0.7881 Intermediate Similarity NPC143659
0.7881 Intermediate Similarity NPC72947
0.7881 Intermediate Similarity NPC284011
0.7874 Intermediate Similarity NPC471671
0.7857 Intermediate Similarity NPC114064
0.7852 Intermediate Similarity NPC471517
0.7851 Intermediate Similarity NPC474352
0.7846 Intermediate Similarity NPC188997
0.7846 Intermediate Similarity NPC71094
0.784 Intermediate Similarity NPC473137
0.784 Intermediate Similarity NPC12656
0.7836 Intermediate Similarity NPC472795
0.7836 Intermediate Similarity NPC472796
0.7833 Intermediate Similarity NPC292452
0.7833 Intermediate Similarity NPC474839
0.7833 Intermediate Similarity NPC471350
0.7826 Intermediate Similarity NPC472800
0.7823 Intermediate Similarity NPC302371
0.7812 Intermediate Similarity NPC217174
0.7805 Intermediate Similarity NPC224870
0.7803 Intermediate Similarity NPC131397
0.7803 Intermediate Similarity NPC476254
0.7797 Intermediate Similarity NPC294741
0.7797 Intermediate Similarity NPC166761
0.7797 Intermediate Similarity NPC174911
0.7797 Intermediate Similarity NPC10588
0.7795 Intermediate Similarity NPC33270
0.7795 Intermediate Similarity NPC470759
0.7795 Intermediate Similarity NPC69261
0.7795 Intermediate Similarity NPC127894
0.7795 Intermediate Similarity NPC219070
0.7795 Intermediate Similarity NPC15860
0.7795 Intermediate Similarity NPC277588
0.7795 Intermediate Similarity NPC172219
0.7795 Intermediate Similarity NPC304510
0.7787 Intermediate Similarity NPC63698
0.7787 Intermediate Similarity NPC61885
0.7778 Intermediate Similarity NPC808
0.7769 Intermediate Similarity NPC237667
0.7761 Intermediate Similarity NPC148366
0.7761 Intermediate Similarity NPC311293
0.775 Intermediate Similarity NPC30506
0.775 Intermediate Similarity NPC119860
0.7742 Intermediate Similarity NPC151537
0.7742 Intermediate Similarity NPC469912
0.7742 Intermediate Similarity NPC54373
0.7734 Intermediate Similarity NPC469609
0.7734 Intermediate Similarity NPC154030
0.7731 Intermediate Similarity NPC477685
0.7727 Intermediate Similarity NPC224342
0.7724 Intermediate Similarity NPC473524
0.7724 Intermediate Similarity NPC202647
0.7717 Intermediate Similarity NPC38893
0.7717 Intermediate Similarity NPC123559
0.7717 Intermediate Similarity NPC469663
0.7717 Intermediate Similarity NPC477137
0.7717 Intermediate Similarity NPC150624
0.7717 Intermediate Similarity NPC308311
0.7717 Intermediate Similarity NPC92
0.7698 Intermediate Similarity NPC327735
0.7698 Intermediate Similarity NPC120280
0.7698 Intermediate Similarity NPC249270
0.7686 Intermediate Similarity NPC117115
0.768 Intermediate Similarity NPC228425
0.7669 Intermediate Similarity NPC105031
0.7664 Intermediate Similarity NPC472798
0.7656 Intermediate Similarity NPC50521
0.7656 Intermediate Similarity NPC244816
0.7656 Intermediate Similarity NPC476266
0.7656 Intermediate Similarity NPC221549
0.7656 Intermediate Similarity NPC477136
0.7652 Intermediate Similarity NPC474160
0.7652 Intermediate Similarity NPC53567
0.7647 Intermediate Similarity NPC72729
0.7642 Intermediate Similarity NPC262365
0.7638 Intermediate Similarity NPC474486
0.7638 Intermediate Similarity NPC35797
0.7638 Intermediate Similarity NPC192948
0.7638 Intermediate Similarity NPC53906
0.7634 Intermediate Similarity NPC476633
0.7627 Intermediate Similarity NPC291789
0.7627 Intermediate Similarity NPC6597
0.7627 Intermediate Similarity NPC474073
0.7627 Intermediate Similarity NPC79241
0.7623 Intermediate Similarity NPC469913
0.7615 Intermediate Similarity NPC318581
0.7615 Intermediate Similarity NPC282255
0.7615 Intermediate Similarity NPC3239

  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 NPC139774 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
0.8475 Intermediate Similarity NPD4750 Phase 3
0.7744 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD7635 Approved
0.7647 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7583 Intermediate Similarity NPD846 Approved
0.7583 Intermediate Similarity NPD940 Approved
0.7542 Intermediate Similarity NPD288 Approved
0.7519 Intermediate Similarity NPD4749 Approved
0.75 Intermediate Similarity NPD1242 Phase 1
0.7458 Intermediate Similarity NPD844 Approved
0.7445 Intermediate Similarity NPD3027 Phase 3
0.7417 Intermediate Similarity NPD3020 Approved
0.7372 Intermediate Similarity NPD4908 Phase 1
0.7319 Intermediate Similarity NPD4625 Phase 3
0.7302 Intermediate Similarity NPD3021 Approved
0.7302 Intermediate Similarity NPD3022 Approved
0.7279 Intermediate Similarity NPD3094 Phase 2
0.7266 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1610 Phase 2
0.7213 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3091 Approved
0.7167 Intermediate Similarity NPD2860 Approved
0.7167 Intermediate Similarity NPD2859 Approved
0.7163 Intermediate Similarity NPD1613 Approved
0.7163 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2342 Discontinued
0.7111 Intermediate Similarity NPD3092 Approved
0.7083 Intermediate Similarity NPD2934 Approved
0.7083 Intermediate Similarity NPD2933 Approved
0.7063 Intermediate Similarity NPD2568 Approved
0.705 Intermediate Similarity NPD2861 Phase 2
0.7034 Intermediate Similarity NPD6099 Approved
0.7034 Intermediate Similarity NPD6100 Approved
0.7 Intermediate Similarity NPD845 Approved
0.6985 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6985 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6963 Remote Similarity NPD3095 Discontinued
0.694 Remote Similarity NPD1548 Phase 1
0.6929 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2238 Phase 2
0.6917 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6884 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6857 Remote Similarity NPD602 Approved
0.6857 Remote Similarity NPD859 Approved
0.6857 Remote Similarity NPD858 Approved
0.6857 Remote Similarity NPD599 Approved
0.6853 Remote Similarity NPD6405 Approved
0.6853 Remote Similarity NPD6407 Approved
0.6849 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6671 Approved
0.6838 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6825 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7390 Discontinued
0.6818 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6803 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6794 Remote Similarity NPD6124 Clinical (unspecified phase)
0.6779 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6769 Remote Similarity NPD1792 Phase 2
0.6767 Remote Similarity NPD497 Approved
0.6748 Remote Similarity NPD1809 Phase 2
0.6733 Remote Similarity NPD3892 Phase 2
0.6714 Remote Similarity NPD6696 Suspended
0.6692 Remote Similarity NPD498 Approved
0.6692 Remote Similarity NPD496 Approved
0.6692 Remote Similarity NPD495 Approved
0.6691 Remote Similarity NPD7741 Discontinued
0.669 Remote Similarity NPD5736 Approved
0.6688 Remote Similarity NPD37 Approved
0.6667 Remote Similarity NPD1445 Approved
0.6667 Remote Similarity NPD1444 Approved
0.6667 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6644 Remote Similarity NPD5762 Approved
0.6644 Remote Similarity NPD5763 Approved
0.6643 Remote Similarity NPD4659 Approved
0.6642 Remote Similarity NPD1476 Clinical (unspecified phase)
0.6619 Remote Similarity NPD1201 Approved
0.6594 Remote Similarity NPD2932 Approved
0.6594 Remote Similarity NPD3019 Approved
0.6594 Remote Similarity NPD4059 Approved
0.6575 Remote Similarity NPD4060 Phase 1
0.6575 Remote Similarity NPD943 Approved
0.6573 Remote Similarity NPD3018 Phase 2
0.6571 Remote Similarity NPD2233 Approved
0.6571 Remote Similarity NPD2232 Approved
0.6571 Remote Similarity NPD2230 Approved
0.6567 Remote Similarity NPD2228 Approved
0.6567 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6567 Remote Similarity NPD2229 Approved
0.6567 Remote Similarity NPD5283 Phase 1
0.6567 Remote Similarity NPD2234 Approved
0.6562 Remote Similarity NPD4967 Phase 2
0.6562 Remote Similarity NPD4965 Approved
0.6562 Remote Similarity NPD4966 Approved
0.6549 Remote Similarity NPD1470 Approved
0.6549 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6549 Remote Similarity NPD4103 Phase 2
0.6549 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6544 Remote Similarity NPD7340 Approved
0.6533 Remote Similarity NPD7266 Discontinued
0.6522 Remote Similarity NPD4093 Discontinued
0.6522 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6519 Remote Similarity NPD9614 Approved
0.6519 Remote Similarity NPD9618 Approved
0.651 Remote Similarity NPD7743 Approved
0.651 Remote Similarity NPD7742 Approved
0.6507 Remote Similarity NPD6663 Approved
0.65 Remote Similarity NPD1091 Approved
0.65 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6486 Remote Similarity NPD5314 Approved
0.6486 Remote Similarity NPD1607 Approved
0.6486 Remote Similarity NPD4097 Suspended
0.6481 Remote Similarity NPD6234 Discontinued
0.6475 Remote Similarity NPD5126 Approved
0.6475 Remote Similarity NPD4626 Approved
0.6475 Remote Similarity NPD2286 Discontinued
0.6475 Remote Similarity NPD5125 Phase 3
0.6467 Remote Similarity NPD5405 Approved
0.6467 Remote Similarity NPD5408 Approved
0.6467 Remote Similarity NPD5404 Approved
0.6467 Remote Similarity NPD5406 Approved
0.6463 Remote Similarity NPD3061 Approved
0.6463 Remote Similarity NPD3062 Approved
0.6463 Remote Similarity NPD3620 Phase 2
0.6463 Remote Similarity NPD3059 Approved
0.6463 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6454 Remote Similarity NPD2231 Phase 2
0.6454 Remote Similarity NPD2235 Phase 2
0.6454 Remote Similarity NPD2561 Approved
0.6454 Remote Similarity NPD2562 Approved
0.6452 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7447 Phase 1
0.6449 Remote Similarity NPD5303 Approved
0.6449 Remote Similarity NPD7330 Discontinued
0.6449 Remote Similarity NPD5304 Approved
0.6449 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6447 Remote Similarity NPD6674 Discontinued
0.6447 Remote Similarity NPD5177 Phase 3
0.6443 Remote Similarity NPD3552 Approved
0.6443 Remote Similarity NPD3555 Approved
0.6443 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6443 Remote Similarity NPD3553 Approved
0.6443 Remote Similarity NPD3554 Approved
0.6438 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6434 Remote Similarity NPD1134 Approved
0.6434 Remote Similarity NPD1133 Approved
0.6434 Remote Similarity NPD1129 Approved
0.6434 Remote Similarity NPD1135 Approved
0.6434 Remote Similarity NPD1131 Approved
0.6424 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6419 Remote Similarity NPD5735 Approved
0.6419 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6419 Remote Similarity NPD5124 Phase 1
0.6412 Remote Similarity NPD968 Approved
0.641 Remote Similarity NPD6090 Discontinued
0.641 Remote Similarity NPD9093 Approved
0.6408 Remote Similarity NPD2982 Phase 2
0.6408 Remote Similarity NPD2983 Phase 2
0.6407 Remote Similarity NPD7228 Approved
0.6406 Remote Similarity NPD3028 Approved
0.6405 Remote Similarity NPD3400 Discontinued
0.6402 Remote Similarity NPD6959 Discontinued
0.64 Remote Similarity NPD1510 Phase 2
0.6391 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6387 Remote Similarity NPD7041 Phase 2
0.6387 Remote Similarity NPD7212 Phase 2
0.6387 Remote Similarity NPD7213 Phase 3
0.6387 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6383 Remote Similarity NPD422 Phase 1
0.6382 Remote Similarity NPD970 Clinical (unspecified phase)
0.6377 Remote Similarity NPD9613 Approved
0.6377 Remote Similarity NPD9615 Approved
0.6377 Remote Similarity NPD9616 Approved
0.6375 Remote Similarity NPD1934 Approved
0.637 Remote Similarity NPD7843 Approved
0.6364 Remote Similarity NPD290 Approved
0.6364 Remote Similarity NPD8651 Approved
0.6358 Remote Similarity NPD1551 Phase 2
0.6358 Remote Similarity NPD2935 Discontinued
0.6357 Remote Similarity NPD7725 Approved
0.6357 Remote Similarity NPD4589 Approved
0.6357 Remote Similarity NPD1751 Approved
0.6357 Remote Similarity NPD9384 Approved
0.6357 Remote Similarity NPD9381 Approved
0.6356 Remote Similarity NPD9089 Approved
0.6352 Remote Similarity NPD4380 Phase 2
0.6351 Remote Similarity NPD1240 Approved
0.635 Remote Similarity NPD7157 Approved
0.6347 Remote Similarity NPD7473 Discontinued
0.6346 Remote Similarity NPD2534 Approved
0.6346 Remote Similarity NPD2533 Approved
0.6346 Remote Similarity NPD2532 Approved
0.6346 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6341 Remote Similarity NPD6746 Phase 2
0.6338 Remote Similarity NPD2981 Phase 2
0.6335 Remote Similarity NPD7819 Suspended
0.6333 Remote Similarity NPD111 Approved
0.6331 Remote Similarity NPD316 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