Structure

Physi-Chem Properties

Molecular Weight:  342.26
Volume:  399.569
LogP:  4.451
LogD:  4.451
LogS:  -2.797
# Rotatable Bonds:  13
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.304
Synthetic Accessibility Score:  2.756
Fsp3:  0.478
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.035
MDCK Permeability:  6.113865674706176e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.038
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.055
Plasma Protein Binding (PPB):  100.09505462646484%
Volume Distribution (VD):  4.157
Pgp-substrate:  0.6555355787277222%

ADMET: Metabolism

CYP1A2-inhibitor:  0.81
CYP1A2-substrate:  0.721
CYP2C19-inhibitor:  0.87
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.526
CYP2C9-substrate:  0.988
CYP2D6-inhibitor:  0.983
CYP2D6-substrate:  0.939
CYP3A4-inhibitor:  0.775
CYP3A4-substrate:  0.104

ADMET: Excretion

Clearance (CL):  5.262
Half-life (T1/2):  0.962

ADMET: Toxicity

hERG Blockers:  0.237
Human Hepatotoxicity (H-HT):  0.18
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.356
Rat Oral Acute Toxicity:  0.017
Maximum Recommended Daily Dose:  0.843
Skin Sensitization:  0.973
Carcinogencity:  0.206
Eye Corrosion:  0.14
Eye Irritation:  0.933
Respiratory Toxicity:  0.83

Download Data

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

  Natural Product: NPC242342

Natural Product ID:  NPC242342
Common Name*:   5-(Heptadeca-8,11,14-Trienyl)Benzene-1,3-Diol
IUPAC Name:   5-[(8Z,11Z,14Z)-heptadeca-8,11,14-trienyl]benzene-1,3-diol
Synonyms:  
Standard InCHIKey:  YPIUYRIMBUVEFO-PDBXOOCHSA-N
Standard InCHI:  InChI=1S/C23H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h3-4,6-7,9-10,18-20,24-25H,2,5,8,11-17H2,1H3/b4-3-,7-6-,10-9-
SMILES:  CC/C=CC/C=CC/C=CCCCCCCCc1cc(O)cc(c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL401127
PubChem CID:   6440713
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0001286] Benzenediols
          • [CHEMONTID:0000137] Resorcinols

*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
NPO5292 Stylogyne turbacensis Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[17629327]
NPO5292 Stylogyne turbacensis Species Primulaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 8700.0 nM PMID[533912]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 8700.0 nM PMID[533912]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 104000.0 nM PMID[533912]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 25000.0 nM PMID[533912]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 600.0 nM PMID[533912]

☑ 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 NPC242342 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 NPC168303
1.0 High Similarity NPC313030
1.0 High Similarity NPC146798
1.0 High Similarity NPC71002
1.0 High Similarity NPC249828
1.0 High Similarity NPC94351
1.0 High Similarity NPC222522
1.0 High Similarity NPC53051
1.0 High Similarity NPC302219
1.0 High Similarity NPC24404
1.0 High Similarity NPC85479
1.0 High Similarity NPC106396
0.9895 High Similarity NPC284011
0.9895 High Similarity NPC24407
0.9895 High Similarity NPC137415
0.9895 High Similarity NPC11280
0.9895 High Similarity NPC72947
0.9895 High Similarity NPC166313
0.9895 High Similarity NPC294186
0.9895 High Similarity NPC192032
0.9895 High Similarity NPC147310
0.9789 High Similarity NPC10588
0.9789 High Similarity NPC166761
0.9596 High Similarity NPC61033
0.9596 High Similarity NPC232523
0.9596 High Similarity NPC305603
0.9596 High Similarity NPC158253
0.9596 High Similarity NPC204901
0.9592 High Similarity NPC134829
0.9495 High Similarity NPC39664
0.9495 High Similarity NPC39097
0.9495 High Similarity NPC109691
0.9495 High Similarity NPC470700
0.9495 High Similarity NPC302681
0.9495 High Similarity NPC99836
0.9495 High Similarity NPC118286
0.9495 High Similarity NPC12640
0.9495 High Similarity NPC201662
0.949 High Similarity NPC241891
0.94 High Similarity NPC54844
0.9394 High Similarity NPC37802
0.9394 High Similarity NPC246056
0.9293 High Similarity NPC218879
0.9293 High Similarity NPC244513
0.9293 High Similarity NPC227458
0.9286 High Similarity NPC143659
0.9286 High Similarity NPC100340
0.9216 High Similarity NPC33728
0.9216 High Similarity NPC19808
0.9158 High Similarity NPC94139
0.9158 High Similarity NPC162314
0.9158 High Similarity NPC210497
0.9158 High Similarity NPC147284
0.9158 High Similarity NPC295295
0.9158 High Similarity NPC306884
0.9158 High Similarity NPC3358
0.9135 High Similarity NPC166995
0.9118 High Similarity NPC174981
0.91 High Similarity NPC30506
0.91 High Similarity NPC102216
0.9038 High Similarity NPC224527
0.9038 High Similarity NPC4493
0.9038 High Similarity NPC225679
0.9038 High Similarity NPC165770
0.9038 High Similarity NPC476632
0.9029 High Similarity NPC186385
0.9029 High Similarity NPC299568
0.898 High Similarity NPC291789
0.8952 High Similarity NPC43525
0.8947 High Similarity NPC192
0.8889 High Similarity NPC80027
0.8868 High Similarity NPC117846
0.8868 High Similarity NPC263753
0.8868 High Similarity NPC62546
0.8868 High Similarity NPC162113
0.8868 High Similarity NPC23804
0.8824 High Similarity NPC474839
0.8812 High Similarity NPC315022
0.88 High Similarity NPC275053
0.88 High Similarity NPC161571
0.88 High Similarity NPC48730
0.88 High Similarity NPC248573
0.88 High Similarity NPC248396
0.88 High Similarity NPC129373
0.8796 High Similarity NPC123559
0.8785 High Similarity NPC107240
0.8776 High Similarity NPC32714
0.8762 High Similarity NPC168657
0.875 High Similarity NPC63698
0.875 High Similarity NPC61885
0.8737 High Similarity NPC27974
0.8725 High Similarity NPC119860
0.8725 High Similarity NPC315936
0.8716 High Similarity NPC127894
0.8716 High Similarity NPC219070
0.8716 High Similarity NPC15860
0.8716 High Similarity NPC470759
0.8704 High Similarity NPC53906
0.8704 High Similarity NPC246760
0.8704 High Similarity NPC84999
0.87 High Similarity NPC260775
0.8692 High Similarity NPC319803
0.8692 High Similarity NPC261343
0.8673 High Similarity NPC76938
0.8641 High Similarity NPC292452
0.8624 High Similarity NPC114064
0.8614 High Similarity NPC12931
0.8614 High Similarity NPC70677
0.8614 High Similarity NPC130756
0.8611 High Similarity NPC22610
0.8611 High Similarity NPC276737
0.86 High Similarity NPC152097
0.86 High Similarity NPC474073
0.8598 High Similarity NPC473521
0.8585 High Similarity NPC224870
0.8571 High Similarity NPC55903
0.8558 High Similarity NPC248904
0.8558 High Similarity NPC469913
0.8557 High Similarity NPC55561
0.8545 High Similarity NPC474933
0.8545 High Similarity NPC470760
0.8545 High Similarity NPC69261
0.8545 High Similarity NPC33270
0.8532 High Similarity NPC808
0.8529 High Similarity NPC477685
0.8529 High Similarity NPC252105
0.8505 High Similarity NPC268032
0.8491 Intermediate Similarity NPC202647
0.8468 Intermediate Similarity NPC48781
0.8468 Intermediate Similarity NPC9592
0.8468 Intermediate Similarity NPC144343
0.8468 Intermediate Similarity NPC206
0.8468 Intermediate Similarity NPC190514
0.8462 Intermediate Similarity NPC471350
0.8455 Intermediate Similarity NPC150624
0.8455 Intermediate Similarity NPC141090
0.8455 Intermediate Similarity NPC115808
0.8454 Intermediate Similarity NPC280347
0.8454 Intermediate Similarity NPC318325
0.8454 Intermediate Similarity NPC123273
0.8454 Intermediate Similarity NPC177420
0.8454 Intermediate Similarity NPC242240
0.8447 Intermediate Similarity NPC196479
0.8447 Intermediate Similarity NPC108497
0.8431 Intermediate Similarity NPC294741
0.8431 Intermediate Similarity NPC72729
0.8421 Intermediate Similarity NPC150837
0.8416 Intermediate Similarity NPC475078
0.8416 Intermediate Similarity NPC79241
0.8416 Intermediate Similarity NPC6597
0.8411 Intermediate Similarity NPC475018
0.8411 Intermediate Similarity NPC242178
0.8407 Intermediate Similarity NPC24125
0.84 Intermediate Similarity NPC26244
0.84 Intermediate Similarity NPC222146
0.84 Intermediate Similarity NPC274678
0.8393 Intermediate Similarity NPC217174
0.8393 Intermediate Similarity NPC184302
0.8381 Intermediate Similarity NPC164576
0.8381 Intermediate Similarity NPC155072
0.8378 Intermediate Similarity NPC277588
0.8364 Intermediate Similarity NPC167934
0.8351 Intermediate Similarity NPC113460
0.8351 Intermediate Similarity NPC25493
0.8351 Intermediate Similarity NPC19680
0.835 Intermediate Similarity NPC80800
0.8333 Intermediate Similarity NPC299762
0.8333 Intermediate Similarity NPC33675
0.8333 Intermediate Similarity NPC237667
0.8319 Intermediate Similarity NPC223451
0.8317 Intermediate Similarity NPC312132
0.8317 Intermediate Similarity NPC473388
0.8317 Intermediate Similarity NPC259512
0.8302 Intermediate Similarity NPC176527
0.8302 Intermediate Similarity NPC66834
0.83 Intermediate Similarity NPC245187
0.83 Intermediate Similarity NPC151715
0.83 Intermediate Similarity NPC316301
0.83 Intermediate Similarity NPC27323
0.83 Intermediate Similarity NPC152415
0.8286 Intermediate Similarity NPC47284
0.8283 Intermediate Similarity NPC231150
0.8283 Intermediate Similarity NPC304541
0.8273 Intermediate Similarity NPC228287
0.8273 Intermediate Similarity NPC180508
0.8269 Intermediate Similarity NPC168393
0.8269 Intermediate Similarity NPC235762
0.8269 Intermediate Similarity NPC471228
0.8265 Intermediate Similarity NPC258219
0.8252 Intermediate Similarity NPC130103
0.8252 Intermediate Similarity NPC174911
0.8247 Intermediate Similarity NPC407
0.8247 Intermediate Similarity NPC23167
0.8247 Intermediate Similarity NPC307235
0.8246 Intermediate Similarity NPC218753
0.8241 Intermediate Similarity NPC2682
0.8241 Intermediate Similarity NPC94045
0.823 Intermediate Similarity NPC191866
0.8224 Intermediate Similarity NPC58427
0.8224 Intermediate Similarity NPC34864

  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 NPC242342 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
0.9091 High Similarity NPD846 Approved
0.9091 High Similarity NPD940 Approved
0.9029 High Similarity NPD4750 Phase 3
0.88 High Similarity NPD1242 Phase 1
0.8586 High Similarity NPD844 Approved
0.84 Intermediate Similarity NPD2859 Approved
0.84 Intermediate Similarity NPD2860 Approved
0.8333 Intermediate Similarity NPD3020 Approved
0.8317 Intermediate Similarity NPD288 Approved
0.83 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.83 Intermediate Similarity NPD2933 Approved
0.83 Intermediate Similarity NPD2934 Approved
0.8252 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.802 Intermediate Similarity NPD845 Approved
0.8 Intermediate Similarity NPD9089 Approved
0.7982 Intermediate Similarity NPD3021 Approved
0.7982 Intermediate Similarity NPD3022 Approved
0.7938 Intermediate Similarity NPD111 Approved
0.7895 Intermediate Similarity NPD9093 Approved
0.7881 Intermediate Similarity NPD4749 Approved
0.787 Intermediate Similarity NPD1444 Approved
0.787 Intermediate Similarity NPD1445 Approved
0.7768 Intermediate Similarity NPD7635 Approved
0.7719 Intermediate Similarity NPD6671 Approved
0.7692 Intermediate Similarity NPD1809 Phase 2
0.7686 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1792 Phase 2
0.7642 Intermediate Similarity NPD4625 Phase 3
0.7642 Intermediate Similarity NPD3027 Phase 3
0.7581 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD9094 Approved
0.7477 Intermediate Similarity NPD2342 Discontinued
0.7431 Intermediate Similarity NPD9500 Approved
0.7419 Intermediate Similarity NPD4908 Phase 1
0.7417 Intermediate Similarity NPD1610 Phase 2
0.7398 Intermediate Similarity NPD858 Approved
0.7398 Intermediate Similarity NPD602 Approved
0.7398 Intermediate Similarity NPD859 Approved
0.7398 Intermediate Similarity NPD599 Approved
0.7391 Intermediate Similarity NPD2229 Approved
0.7391 Intermediate Similarity NPD2228 Approved
0.7391 Intermediate Similarity NPD2234 Approved
0.7383 Intermediate Similarity NPD9273 Approved
0.7373 Intermediate Similarity NPD1548 Phase 1
0.7373 Intermediate Similarity NPD3091 Approved
0.7368 Intermediate Similarity NPD228 Approved
0.7328 Intermediate Similarity NPD1791 Approved
0.7328 Intermediate Similarity NPD1793 Approved
0.7302 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3092 Approved
0.7273 Intermediate Similarity NPD422 Phase 1
0.725 Intermediate Similarity NPD4059 Approved
0.725 Intermediate Similarity NPD3019 Approved
0.725 Intermediate Similarity NPD2932 Approved
0.7248 Intermediate Similarity NPD3028 Approved
0.7217 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD2568 Approved
0.7207 Intermediate Similarity NPD9610 Approved
0.7207 Intermediate Similarity NPD9608 Approved
0.72 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD9618 Approved
0.7179 Intermediate Similarity NPD9614 Approved
0.7177 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD3094 Phase 2
0.7176 Intermediate Similarity NPD6099 Approved
0.7176 Intermediate Similarity NPD6100 Approved
0.7167 Intermediate Similarity NPD4093 Discontinued
0.7158 Intermediate Similarity NPD9087 Approved
0.7155 Intermediate Similarity NPD9379 Approved
0.7155 Intermediate Similarity NPD9377 Approved
0.713 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD2684 Approved
0.7097 Intermediate Similarity NPD6696 Suspended
0.7094 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD943 Approved
0.7054 Intermediate Similarity NPD1613 Approved
0.7054 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD9088 Approved
0.7034 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD2983 Phase 2
0.7016 Intermediate Similarity NPD2982 Phase 2
0.7009 Intermediate Similarity NPD7843 Approved
0.7 Intermediate Similarity NPD9615 Approved
0.7 Intermediate Similarity NPD9616 Approved
0.7 Intermediate Similarity NPD9613 Approved
0.7 Intermediate Similarity NPD856 Approved
0.7 Intermediate Similarity NPD16 Approved
0.6992 Remote Similarity NPD1201 Approved
0.6975 Remote Similarity NPD7157 Approved
0.6967 Remote Similarity NPD4626 Approved
0.6967 Remote Similarity NPD2286 Discontinued
0.6967 Remote Similarity NPD9384 Approved
0.6967 Remote Similarity NPD3095 Discontinued
0.6967 Remote Similarity NPD9381 Approved
0.6967 Remote Similarity NPD1751 Approved
0.6963 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6949 Remote Similarity NPD5283 Phase 1
0.6942 Remote Similarity NPD316 Approved
0.6939 Remote Similarity NPD9294 Approved
0.6935 Remote Similarity NPD2233 Approved
0.6935 Remote Similarity NPD2981 Phase 2
0.6935 Remote Similarity NPD2232 Approved
0.6935 Remote Similarity NPD2230 Approved
0.6935 Remote Similarity NPD9269 Phase 2
0.693 Remote Similarity NPD968 Approved
0.6929 Remote Similarity NPD2861 Phase 2
0.6929 Remote Similarity NPD5736 Approved
0.6929 Remote Similarity NPD3018 Phase 2
0.6923 Remote Similarity NPD2238 Phase 2
0.6917 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6905 Remote Similarity NPD1133 Approved
0.6905 Remote Similarity NPD1131 Approved
0.6905 Remote Similarity NPD1129 Approved
0.6905 Remote Similarity NPD1135 Approved
0.6905 Remote Similarity NPD1134 Approved
0.6899 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6885 Remote Similarity NPD9268 Approved
0.688 Remote Similarity NPD9622 Approved
0.688 Remote Similarity NPD4659 Approved
0.688 Remote Similarity NPD1755 Approved
0.687 Remote Similarity NPD290 Approved
0.687 Remote Similarity NPD9265 Clinical (unspecified phase)
0.686 Remote Similarity NPD317 Approved
0.686 Remote Similarity NPD318 Approved
0.685 Remote Similarity NPD6584 Phase 3
0.6846 Remote Similarity NPD6407 Approved
0.6846 Remote Similarity NPD6405 Approved
0.6842 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6833 Remote Similarity NPD255 Approved
0.6833 Remote Similarity NPD256 Approved
0.6829 Remote Similarity NPD4589 Approved
0.6825 Remote Similarity NPD5310 Approved
0.6825 Remote Similarity NPD5311 Approved
0.681 Remote Similarity NPD74 Approved
0.681 Remote Similarity NPD9266 Approved
0.6803 Remote Similarity NPD5304 Approved
0.6803 Remote Similarity NPD7330 Discontinued
0.6803 Remote Similarity NPD5303 Approved
0.6803 Remote Similarity NPD1759 Phase 1
0.68 Remote Similarity NPD2561 Approved
0.68 Remote Similarity NPD2562 Approved
0.68 Remote Similarity NPD1608 Approved
0.6794 Remote Similarity NPD1240 Approved
0.6777 Remote Similarity NPD405 Clinical (unspecified phase)
0.6777 Remote Similarity NPD9493 Approved
0.6774 Remote Similarity NPD3496 Discontinued
0.6772 Remote Similarity NPD4103 Phase 2
0.6772 Remote Similarity NPD3055 Approved
0.6772 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6772 Remote Similarity NPD1470 Approved
0.6772 Remote Similarity NPD3053 Approved
0.6752 Remote Similarity NPD5451 Approved
0.675 Remote Similarity NPD475 Phase 2
0.675 Remote Similarity NPD497 Approved
0.6742 Remote Similarity NPD230 Phase 1
0.6726 Remote Similarity NPD4817 Approved
0.6726 Remote Similarity NPD4818 Approved
0.6724 Remote Similarity NPD9267 Approved
0.6724 Remote Similarity NPD9264 Approved
0.6724 Remote Similarity NPD9263 Approved
0.6723 Remote Similarity NPD821 Approved
0.6721 Remote Similarity NPD1758 Phase 1
0.6719 Remote Similarity NPD9621 Approved
0.6719 Remote Similarity NPD9620 Approved
0.6719 Remote Similarity NPD2195 Approved
0.6719 Remote Similarity NPD2194 Approved
0.6719 Remote Similarity NPD9619 Approved
0.6718 Remote Similarity NPD6663 Approved
0.6716 Remote Similarity NPD651 Clinical (unspecified phase)
0.6694 Remote Similarity NPD2668 Approved
0.6694 Remote Similarity NPD709 Approved
0.6694 Remote Similarity NPD2667 Approved
0.6694 Remote Similarity NPD1778 Approved
0.6692 Remote Similarity NPD1607 Approved
0.6691 Remote Similarity NPD7390 Discontinued
0.6667 Remote Similarity NPD3637 Approved
0.6667 Remote Similarity NPD496 Approved
0.6667 Remote Similarity NPD3635 Approved
0.6667 Remote Similarity NPD2231 Phase 2
0.6667 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6346 Approved
0.6667 Remote Similarity NPD7741 Discontinued
0.6667 Remote Similarity NPD2235 Phase 2
0.6667 Remote Similarity NPD3636 Approved
0.6667 Remote Similarity NPD498 Approved
0.6667 Remote Similarity NPD495 Approved
0.6667 Remote Similarity NPD1555 Discontinued
0.6667 Remote Similarity NPD9545 Approved
0.6643 Remote Similarity NPD7447 Phase 1
0.6642 Remote Similarity NPD6111 Discontinued
0.6641 Remote Similarity NPD2797 Approved
0.6641 Remote Similarity NPD598 Approved
0.6641 Remote Similarity NPD597 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