Structure

Physi-Chem Properties

Molecular Weight:  552.42
Volume:  624.885
LogP:  10.989
LogD:  6.35
LogS:  -3.058
# Rotatable Bonds:  6
TPSA:  80.92
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.287
Synthetic Accessibility Score:  5.617
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:  -5.17
MDCK Permeability:  1.2134677490394097e-05
Pgp-inhibitor:  0.423
Pgp-substrate:  0.739
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  98.47049713134766%
Volume Distribution (VD):  3.283
Pgp-substrate:  1.2824883460998535%

ADMET: Metabolism

CYP1A2-inhibitor:  0.167
CYP1A2-substrate:  0.405
CYP2C19-inhibitor:  0.803
CYP2C19-substrate:  0.372
CYP2C9-inhibitor:  0.14
CYP2C9-substrate:  0.995
CYP2D6-inhibitor:  0.174
CYP2D6-substrate:  0.665
CYP3A4-inhibitor:  0.142
CYP3A4-substrate:  0.095

ADMET: Excretion

Clearance (CL):  7.86
Half-life (T1/2):  0.089

ADMET: Toxicity

hERG Blockers:  0.174
Human Hepatotoxicity (H-HT):  0.236
Drug-inuced Liver Injury (DILI):  0.336
AMES Toxicity:  0.306
Rat Oral Acute Toxicity:  0.582
Maximum Recommended Daily Dose:  0.99
Skin Sensitization:  0.975
Carcinogencity:  0.042
Eye Corrosion:  0.004
Eye Irritation:  0.891
Respiratory Toxicity:  0.87

Download Data

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

  Natural Product: NPC23804

Natural Product ID:  NPC23804
Common Name*:   Cylindrocyclophane F
IUPAC Name:   n.a.
Synonyms:   Cylindrocyclophane F
Standard InCHIKey:  AAGAYZNADYXWIQ-ATACATFBSA-N
Standard InCHI:  InChI=1S/C36H56O4/c1-5-7-15-29-17-11-9-13-25(3)20-28-23-33(39)36(34(40)24-28)30(16-8-6-2)18-12-10-14-26(4)19-27-21-31(37)35(29)32(38)22-27/h21-26,29-30,37-40H,5-20H2,1-4H3/t25-,26-,29-,30-/m0/s1
SMILES:  CCCC[C@H]1CCCC[C@H](C)Cc2cc(O)c(c(c2)O)[C@H](CCCC[C@@H](Cc2cc(c1c(O)c2)O)C)CCCC
Synthetic Gene Cluster:   BGC0001064;
ChEMBL Identifier:   CHEMBL1224868
PubChem CID:   11757351
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]
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 Latex Exudate n.a. n.a. Database[FooDB]
NPO2776 Lactuca sativa Species Asteraceae Eukaryota Leaf 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]
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]
NPO1969 Streptomyces pilosus Species Streptomycetaceae Bacteria 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]
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]
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]
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]
NPO23216 Tanaecium pyramidatum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10879 Lasius meridionalis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]

☑ 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
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[543178]

☑ 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 NPC23804 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
0.9623 High Similarity NPC224527
0.9545 High Similarity NPC9592
0.9545 High Similarity NPC48781
0.9434 High Similarity NPC186385
0.9434 High Similarity NPC19808
0.9434 High Similarity NPC33728
0.9434 High Similarity NPC299568
0.9352 High Similarity NPC166995
0.934 High Similarity NPC174981
0.9333 High Similarity NPC99836
0.9333 High Similarity NPC12640
0.9333 High Similarity NPC201662
0.9273 High Similarity NPC84999
0.9273 High Similarity NPC246760
0.9245 High Similarity NPC204901
0.9245 High Similarity NPC232523
0.9245 High Similarity NPC54844
0.9245 High Similarity NPC158253
0.9238 High Similarity NPC37802
0.9238 High Similarity NPC246056
0.9189 High Similarity NPC115808
0.9151 High Similarity NPC470700
0.9151 High Similarity NPC39097
0.9151 High Similarity NPC118286
0.9151 High Similarity NPC109691
0.9151 High Similarity NPC39664
0.9151 High Similarity NPC302681
0.9143 High Similarity NPC218879
0.9143 High Similarity NPC227458
0.9143 High Similarity NPC244513
0.913 High Similarity NPC122175
0.9107 High Similarity NPC470760
0.9091 High Similarity NPC261343
0.9091 High Similarity NPC117846
0.9091 High Similarity NPC319803
0.9057 High Similarity NPC134829
0.9027 High Similarity NPC206
0.9 High Similarity NPC43525
0.8974 High Similarity NPC139774
0.8974 High Similarity NPC174729
0.8962 High Similarity NPC241891
0.8962 High Similarity NPC102216
0.8952 High Similarity NPC192032
0.8952 High Similarity NPC11280
0.8952 High Similarity NPC294186
0.8952 High Similarity NPC166313
0.8952 High Similarity NPC147310
0.8952 High Similarity NPC24407
0.8952 High Similarity NPC137415
0.8919 High Similarity NPC263753
0.8909 High Similarity NPC4493
0.8909 High Similarity NPC476632
0.8909 High Similarity NPC165770
0.8909 High Similarity NPC225679
0.8879 High Similarity NPC39029
0.887 High Similarity NPC69006
0.8868 High Similarity NPC24404
0.8868 High Similarity NPC53051
0.8868 High Similarity NPC249828
0.8868 High Similarity NPC313030
0.8868 High Similarity NPC146798
0.8868 High Similarity NPC168303
0.8868 High Similarity NPC106396
0.8868 High Similarity NPC302219
0.8868 High Similarity NPC222522
0.8868 High Similarity NPC71002
0.8868 High Similarity NPC85479
0.8868 High Similarity NPC242342
0.8868 High Similarity NPC94351
0.886 High Similarity NPC144343
0.8839 High Similarity NPC107240
0.8824 High Similarity NPC91204
0.8824 High Similarity NPC237517
0.8824 High Similarity NPC111723
0.8796 High Similarity NPC248904
0.8793 High Similarity NPC24125
0.8783 High Similarity NPC191866
0.8774 High Similarity NPC143659
0.8774 High Similarity NPC72947
0.8774 High Similarity NPC100340
0.8774 High Similarity NPC284011
0.875 High Similarity NPC66331
0.875 High Similarity NPC257947
0.875 High Similarity NPC98200
0.875 High Similarity NPC32715
0.8704 High Similarity NPC292452
0.8704 High Similarity NPC474839
0.8696 High Similarity NPC190514
0.8679 High Similarity NPC10588
0.8679 High Similarity NPC166761
0.8649 High Similarity NPC224870
0.8636 High Similarity NPC63698
0.8636 High Similarity NPC61885
0.8621 High Similarity NPC217174
0.8621 High Similarity NPC184302
0.8611 High Similarity NPC119860
0.8611 High Similarity NPC30506
0.8609 High Similarity NPC277588
0.8571 High Similarity NPC151537
0.8559 High Similarity NPC237667
0.8559 High Similarity NPC202647
0.8545 High Similarity NPC305603
0.8545 High Similarity NPC61033
0.8532 High Similarity NPC117115
0.8522 High Similarity NPC114064
0.8512 High Similarity NPC82299
0.8509 High Similarity NPC249270
0.8505 High Similarity NPC72729
0.85 High Similarity NPC224342
0.8496 Intermediate Similarity NPC473521
0.8491 Intermediate Similarity NPC291789
0.8491 Intermediate Similarity NPC79241
0.8491 Intermediate Similarity NPC6597
0.8487 Intermediate Similarity NPC77789
0.8487 Intermediate Similarity NPC18128
0.8482 Intermediate Similarity NPC475018
0.8468 Intermediate Similarity NPC471517
0.8462 Intermediate Similarity NPC151197
0.8448 Intermediate Similarity NPC470759
0.8448 Intermediate Similarity NPC69261
0.8448 Intermediate Similarity NPC33270
0.8448 Intermediate Similarity NPC15860
0.8448 Intermediate Similarity NPC127894
0.8448 Intermediate Similarity NPC219070
0.8443 Intermediate Similarity NPC473221
0.8435 Intermediate Similarity NPC808
0.8435 Intermediate Similarity NPC232165
0.8426 Intermediate Similarity NPC252105
0.8426 Intermediate Similarity NPC477685
0.8417 Intermediate Similarity NPC53567
0.8407 Intermediate Similarity NPC469912
0.8396 Intermediate Similarity NPC312132
0.8396 Intermediate Similarity NPC259512
0.839 Intermediate Similarity NPC223451
0.8378 Intermediate Similarity NPC66834
0.8378 Intermediate Similarity NPC151477
0.8362 Intermediate Similarity NPC150624
0.8349 Intermediate Similarity NPC168393
0.8333 Intermediate Similarity NPC161571
0.8333 Intermediate Similarity NPC120172
0.8333 Intermediate Similarity NPC248573
0.8333 Intermediate Similarity NPC275053
0.832 Intermediate Similarity NPC472590
0.832 Intermediate Similarity NPC8899
0.8319 Intermediate Similarity NPC132720
0.8305 Intermediate Similarity NPC121866
0.8302 Intermediate Similarity NPC32714
0.8291 Intermediate Similarity NPC244816
0.8291 Intermediate Similarity NPC50521
0.8291 Intermediate Similarity NPC221549
0.8288 Intermediate Similarity NPC469913
0.8286 Intermediate Similarity NPC295295
0.8279 Intermediate Similarity NPC105031
0.8276 Intermediate Similarity NPC472893
0.8276 Intermediate Similarity NPC53906
0.8273 Intermediate Similarity NPC315936
0.8273 Intermediate Similarity NPC323810
0.8273 Intermediate Similarity NPC475225
0.8264 Intermediate Similarity NPC96940
0.8257 Intermediate Similarity NPC12221
0.8254 Intermediate Similarity NPC469611
0.825 Intermediate Similarity NPC476633
0.8246 Intermediate Similarity NPC268032
0.8246 Intermediate Similarity NPC54373
0.8241 Intermediate Similarity NPC80027
0.8241 Intermediate Similarity NPC33675
0.8241 Intermediate Similarity NPC299762
0.823 Intermediate Similarity NPC58865
0.8214 Intermediate Similarity NPC320439
0.8211 Intermediate Similarity NPC145659
0.8211 Intermediate Similarity NPC9292
0.8208 Intermediate Similarity NPC76938
0.8205 Intermediate Similarity NPC141001
0.8198 Intermediate Similarity NPC47284
0.8198 Intermediate Similarity NPC99557
0.8198 Intermediate Similarity NPC219286
0.8197 Intermediate Similarity NPC97578
0.819 Intermediate Similarity NPC276737
0.819 Intermediate Similarity NPC22610
0.8189 Intermediate Similarity NPC469610
0.8182 Intermediate Similarity NPC315022
0.8182 Intermediate Similarity NPC471228
0.8182 Intermediate Similarity NPC235762
0.8175 Intermediate Similarity NPC473309
0.8174 Intermediate Similarity NPC62867
0.8174 Intermediate Similarity NPC228452
0.8174 Intermediate Similarity NPC46940
0.8174 Intermediate Similarity NPC177962
0.8167 Intermediate Similarity NPC218753
0.8167 Intermediate Similarity NPC102639
0.8165 Intermediate Similarity NPC129373
0.8165 Intermediate Similarity NPC130756
0.8165 Intermediate Similarity NPC12931
0.8165 Intermediate Similarity NPC48730
0.8165 Intermediate Similarity NPC248396
0.8165 Intermediate Similarity NPC70677
0.816 Intermediate Similarity NPC96719
0.816 Intermediate Similarity NPC109123
0.816 Intermediate Similarity NPC222108
0.8158 Intermediate Similarity NPC296683

  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 NPC23804 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
0.9434 High Similarity NPD4750 Phase 3
0.8426 Intermediate Similarity NPD940 Approved
0.8426 Intermediate Similarity NPD846 Approved
0.8396 Intermediate Similarity NPD288 Approved
0.8333 Intermediate Similarity NPD7635 Approved
0.8333 Intermediate Similarity NPD1242 Phase 1
0.8302 Intermediate Similarity NPD844 Approved
0.8264 Intermediate Similarity NPD4749 Approved
0.8241 Intermediate Similarity NPD3020 Approved
0.807 Intermediate Similarity NPD3022 Approved
0.807 Intermediate Similarity NPD3021 Approved
0.8065 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8016 Intermediate Similarity NPD4625 Phase 3
0.7963 Intermediate Similarity NPD2860 Approved
0.7963 Intermediate Similarity NPD2859 Approved
0.7953 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD2342 Discontinued
0.787 Intermediate Similarity NPD2934 Approved
0.787 Intermediate Similarity NPD2933 Approved
0.7838 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD4908 Phase 1
0.7778 Intermediate Similarity NPD845 Approved
0.7674 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD6100 Approved
0.7669 Intermediate Similarity NPD6099 Approved
0.7661 Intermediate Similarity NPD1610 Phase 2
0.7603 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD1809 Phase 2
0.7463 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD3027 Phase 3
0.7458 Intermediate Similarity NPD1792 Phase 2
0.7445 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD6671 Approved
0.735 Intermediate Similarity NPD1444 Approved
0.735 Intermediate Similarity NPD1445 Approved
0.7339 Intermediate Similarity NPD1548 Phase 1
0.7339 Intermediate Similarity NPD3091 Approved
0.7295 Intermediate Similarity NPD497 Approved
0.7295 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD3094 Phase 2
0.7286 Intermediate Similarity NPD7390 Discontinued
0.7244 Intermediate Similarity NPD1201 Approved
0.7244 Intermediate Similarity NPD3092 Approved
0.7222 Intermediate Similarity NPD3019 Approved
0.7222 Intermediate Similarity NPD2932 Approved
0.7222 Intermediate Similarity NPD4059 Approved
0.7213 Intermediate Similarity NPD498 Approved
0.7213 Intermediate Similarity NPD2234 Approved
0.7213 Intermediate Similarity NPD2229 Approved
0.7213 Intermediate Similarity NPD2228 Approved
0.7213 Intermediate Similarity NPD495 Approved
0.7213 Intermediate Similarity NPD496 Approved
0.7209 Intermediate Similarity NPD6696 Suspended
0.719 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2861 Phase 2
0.7164 Intermediate Similarity NPD1613 Approved
0.7164 Intermediate Similarity NPD943 Approved
0.7164 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD1470 Approved
0.7143 Intermediate Similarity NPD4093 Discontinued
0.7143 Intermediate Similarity NPD9093 Approved
0.7109 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD2286 Discontinued
0.7087 Intermediate Similarity NPD3095 Discontinued
0.7075 Intermediate Similarity NPD9089 Approved
0.7073 Intermediate Similarity NPD5283 Phase 1
0.7073 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD3028 Approved
0.7063 Intermediate Similarity NPD5304 Approved
0.7063 Intermediate Similarity NPD5303 Approved
0.7063 Intermediate Similarity NPD7330 Discontinued
0.7063 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2568 Approved
0.7045 Intermediate Similarity NPD3018 Phase 2
0.704 Intermediate Similarity NPD7340 Approved
0.7037 Intermediate Similarity NPD111 Approved
0.7029 Intermediate Similarity NPD5406 Approved
0.7029 Intermediate Similarity NPD5405 Approved
0.7029 Intermediate Similarity NPD5408 Approved
0.7029 Intermediate Similarity NPD5404 Approved
0.7015 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.6977 Remote Similarity NPD422 Phase 1
0.6963 Remote Similarity NPD6405 Approved
0.6963 Remote Similarity NPD6407 Approved
0.6953 Remote Similarity NPD1751 Approved
0.6953 Remote Similarity NPD4589 Approved
0.6953 Remote Similarity NPD4626 Approved
0.6953 Remote Similarity NPD5238 Clinical (unspecified phase)
0.695 Remote Similarity NPD3892 Phase 2
0.6949 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6934 Remote Similarity NPD4097 Suspended
0.6934 Remote Similarity NPD1607 Approved
0.6923 Remote Similarity NPD2233 Approved
0.6923 Remote Similarity NPD2232 Approved
0.6923 Remote Similarity NPD2230 Approved
0.6917 Remote Similarity NPD5736 Approved
0.6912 Remote Similarity NPD2238 Phase 2
0.6912 Remote Similarity NPD4060 Phase 1
0.6899 Remote Similarity NPD1981 Approved
0.6899 Remote Similarity NPD1980 Approved
0.6899 Remote Similarity NPD1983 Approved
0.6897 Remote Similarity NPD9273 Approved
0.6894 Remote Similarity NPD2797 Approved
0.687 Remote Similarity NPD2982 Phase 2
0.687 Remote Similarity NPD2983 Phase 2
0.6842 Remote Similarity NPD858 Approved
0.6842 Remote Similarity NPD599 Approved
0.6842 Remote Similarity NPD602 Approved
0.6842 Remote Similarity NPD859 Approved
0.6835 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6825 Remote Similarity NPD709 Approved
0.6825 Remote Similarity NPD6387 Discontinued
0.6809 Remote Similarity NPD970 Clinical (unspecified phase)
0.6807 Remote Similarity NPD9500 Approved
0.68 Remote Similarity NPD1398 Phase 1
0.6797 Remote Similarity NPD7741 Discontinued
0.6794 Remote Similarity NPD1608 Approved
0.6794 Remote Similarity NPD2981 Phase 2
0.6788 Remote Similarity NPD6346 Approved
0.6788 Remote Similarity NPD1555 Discontinued
0.6788 Remote Similarity NPD1240 Approved
0.6769 Remote Similarity NPD3023 Approved
0.6769 Remote Similarity NPD3026 Approved
0.6765 Remote Similarity NPD3268 Approved
0.6763 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6761 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7447 Phase 1
0.6759 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6746 Remote Similarity NPD1791 Approved
0.6746 Remote Similarity NPD1793 Approved
0.6744 Remote Similarity NPD3025 Approved
0.6744 Remote Similarity NPD3024 Approved
0.6742 Remote Similarity NPD4659 Approved
0.6738 Remote Similarity NPD5763 Approved
0.6738 Remote Similarity NPD5762 Approved
0.6718 Remote Similarity NPD1611 Approved
0.6716 Remote Similarity NPD2195 Approved
0.6716 Remote Similarity NPD2194 Approved
0.6715 Remote Similarity NPD6663 Approved
0.6714 Remote Similarity NPD1510 Phase 2
0.6713 Remote Similarity NPD3750 Approved
0.6696 Remote Similarity NPD9094 Approved
0.6692 Remote Similarity NPD1283 Approved
0.6691 Remote Similarity NPD5155 Approved
0.6691 Remote Similarity NPD5156 Approved
0.669 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6689 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3635 Approved
0.6667 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1551 Phase 2
0.6667 Remote Similarity NPD2935 Discontinued
0.6667 Remote Similarity NPD37 Approved
0.6667 Remote Similarity NPD3637 Approved
0.6667 Remote Similarity NPD3636 Approved
0.6644 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6644 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6643 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6642 Remote Similarity NPD4103 Phase 2
0.6642 Remote Similarity NPD1164 Approved
0.6642 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6641 Remote Similarity NPD7636 Approved
0.6641 Remote Similarity NPD405 Clinical (unspecified phase)
0.664 Remote Similarity NPD228 Approved
0.6639 Remote Similarity NPD1616 Discontinued
0.6639 Remote Similarity NPD968 Approved
0.6624 Remote Similarity NPD7473 Discontinued
0.6623 Remote Similarity NPD7819 Suspended
0.6618 Remote Similarity NPD2605 Approved
0.6618 Remote Similarity NPD2606 Approved
0.6615 Remote Similarity NPD1651 Approved
0.6615 Remote Similarity NPD5691 Approved
0.6599 Remote Similarity NPD6090 Discontinued
0.6596 Remote Similarity NPD7743 Approved
0.6596 Remote Similarity NPD7742 Approved
0.6596 Remote Similarity NPD651 Clinical (unspecified phase)
0.6593 Remote Similarity NPD6584 Phase 3
0.6593 Remote Similarity NPD4624 Approved
0.6587 Remote Similarity NPD7843 Approved
0.6583 Remote Similarity NPD4818 Approved
0.6583 Remote Similarity NPD4817 Approved
0.6575 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6575 Remote Similarity NPD7041 Phase 2
0.6575 Remote Similarity NPD7212 Phase 2
0.6575 Remote Similarity NPD7213 Phase 3
0.6573 Remote Similarity NPD4256 Phase 2
0.6573 Remote Similarity NPD4257 Approved
0.6569 Remote Similarity NPD7095 Approved
0.6567 Remote Similarity NPD8651 Approved
0.6567 Remote Similarity NPD5310 Approved
0.6567 Remote Similarity NPD5311 Approved
0.6565 Remote Similarity NPD1778 Approved
0.6565 Remote Similarity NPD2668 Approved
0.6565 Remote Similarity NPD17 Approved
0.6565 Remote Similarity NPD2667 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