Structure

Physi-Chem Properties

Molecular Weight:  432.4
Volume:  511.255
LogP:  11.238
LogD:  5.041
LogS:  -4.675
# Rotatable Bonds:  22
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.179
Synthetic Accessibility Score:  1.995
Fsp3:  0.793
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.471
MDCK Permeability:  5.527696430362994e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  100.1280288696289%
Volume Distribution (VD):  5.286
Pgp-substrate:  0.4065040051937103%

ADMET: Metabolism

CYP1A2-inhibitor:  0.09
CYP1A2-substrate:  0.149
CYP2C19-inhibitor:  0.345
CYP2C19-substrate:  0.047
CYP2C9-inhibitor:  0.049
CYP2C9-substrate:  0.994
CYP2D6-inhibitor:  0.829
CYP2D6-substrate:  0.085
CYP3A4-inhibitor:  0.37
CYP3A4-substrate:  0.021

ADMET: Excretion

Clearance (CL):  5.469
Half-life (T1/2):  0.143

ADMET: Toxicity

hERG Blockers:  0.721
Human Hepatotoxicity (H-HT):  0.013
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.014
Maximum Recommended Daily Dose:  0.591
Skin Sensitization:  0.979
Carcinogencity:  0.013
Eye Corrosion:  0.984
Eye Irritation:  0.929
Respiratory Toxicity:  0.69

Download Data

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

  Natural Product: NPC166313

Natural Product ID:  NPC166313
Common Name*:   5-N-Tricosylresorcinol
IUPAC Name:   5-tricosylbenzene-1,3-diol
Synonyms:   5-N-Tricosylresorcinol
Standard InCHIKey:  OHTBGMREZYLZQD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C29H52O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-24-28(30)26-29(31)25-27/h24-26,30-31H,2-23H2,1H3
SMILES:  CCCCCCCCCCCCCCCCCCCCCCCc1cc(O)cc(c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1795557
PubChem CID:   155462
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
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[10993146]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. Tsukuba, Japan 1998-JUN PMID[12381108]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO33268 wheat n.a. n.a. n.a. wheat germ n.a. n.a. PMID[19284743]
NPO659 Secale cereale Species Poaceae Eukaryota n.a. n.a. n.a. PMID[21381697]
NPO33268 wheat n.a. n.a. n.a. wheat bran n.a. n.a. PMID[21658963]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. leaf n.a. PMID[24197199]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[24254087]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. PMID[31861466]
NPO659 Secale cereale Species Poaceae Eukaryota n.a. n.a. n.a. PMID[9134744]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO659 Secale cereale Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO659 Secale cereale Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO659 Secale cereale Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO709.1 Triticum durum Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO659 Secale cereale Species Poaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO659 Secale cereale Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19085 Azotobacter vinelandii Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22132 Hordeum vulgare Species Poaceae 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
NPO22132 NPC166313 Dried Or Powder n.a. 0.770615385 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO709.1 NPC166313 Dried Or Powder n.a. 8.695100438 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO659 NPC166313 Dried Or Powder n.a. 0.801900069 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO659 NPC166313 Dried Or Powder n.a. 7.015540803 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO8589 NPC166313 Dried Or Powder n.a. 3.059206793 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO659 NPC166313 n.a. n.a. 0.8 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO659 NPC166313 n.a. n.a. 7.00986 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO8589 NPC166313 n.a. n.a. 3.05419 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO8589 NPC166313 n.a. n.a. 8.69091 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO9299 NPC166313 n.a. n.a. 0.76692 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]

☑ 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
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 50.0 ug.mL-1 PMID[531279]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 50.0 ug.mL-1 PMID[531279]

☑ 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 NPC166313 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 NPC137415
1.0 High Similarity NPC192032
1.0 High Similarity NPC294186
1.0 High Similarity NPC147310
1.0 High Similarity NPC11280
1.0 High Similarity NPC24407
0.9895 High Similarity NPC106396
0.9895 High Similarity NPC71002
0.9895 High Similarity NPC168303
0.9895 High Similarity NPC242342
0.9895 High Similarity NPC222522
0.9895 High Similarity NPC24404
0.9895 High Similarity NPC94351
0.9895 High Similarity NPC249828
0.9895 High Similarity NPC146798
0.9895 High Similarity NPC53051
0.9895 High Similarity NPC302219
0.9895 High Similarity NPC313030
0.9895 High Similarity NPC85479
0.9789 High Similarity NPC72947
0.9789 High Similarity NPC284011
0.9684 High Similarity NPC166761
0.9684 High Similarity NPC10588
0.9592 High Similarity NPC99836
0.9592 High Similarity NPC12640
0.9592 High Similarity NPC201662
0.9495 High Similarity NPC232523
0.9495 High Similarity NPC305603
0.9495 High Similarity NPC61033
0.9495 High Similarity NPC204901
0.9495 High Similarity NPC158253
0.949 High Similarity NPC37802
0.949 High Similarity NPC134829
0.949 High Similarity NPC246056
0.9394 High Similarity NPC109691
0.9394 High Similarity NPC39664
0.9394 High Similarity NPC118286
0.9394 High Similarity NPC470700
0.9394 High Similarity NPC302681
0.9394 High Similarity NPC39097
0.9388 High Similarity NPC227458
0.9388 High Similarity NPC241891
0.9388 High Similarity NPC218879
0.9388 High Similarity NPC244513
0.93 High Similarity NPC54844
0.9255 High Similarity NPC295295
0.9184 High Similarity NPC100340
0.9184 High Similarity NPC143659
0.9118 High Similarity NPC299568
0.9118 High Similarity NPC186385
0.9118 High Similarity NPC19808
0.9118 High Similarity NPC33728
0.9053 High Similarity NPC3358
0.9053 High Similarity NPC162314
0.9053 High Similarity NPC147284
0.9053 High Similarity NPC94139
0.9053 High Similarity NPC210497
0.9053 High Similarity NPC306884
0.9038 High Similarity NPC166995
0.902 High Similarity NPC174981
0.9 High Similarity NPC102216
0.9 High Similarity NPC30506
0.8952 High Similarity NPC62546
0.8952 High Similarity NPC263753
0.8952 High Similarity NPC162113
0.8952 High Similarity NPC23804
0.8942 High Similarity NPC225679
0.8942 High Similarity NPC4493
0.8942 High Similarity NPC165770
0.8942 High Similarity NPC224527
0.8942 High Similarity NPC476632
0.89 High Similarity NPC315022
0.8878 High Similarity NPC291789
0.8857 High Similarity NPC43525
0.8846 High Similarity NPC168657
0.8842 High Similarity NPC192
0.8812 High Similarity NPC315936
0.8788 High Similarity NPC80027
0.8774 High Similarity NPC319803
0.8774 High Similarity NPC117846
0.8725 High Similarity NPC474839
0.8704 High Similarity NPC114064
0.8704 High Similarity NPC123559
0.87 High Similarity NPC275053
0.87 High Similarity NPC48730
0.87 High Similarity NPC248573
0.87 High Similarity NPC161571
0.87 High Similarity NPC248396
0.87 High Similarity NPC129373
0.8692 High Similarity NPC107240
0.8679 High Similarity NPC473521
0.8673 High Similarity NPC32714
0.8667 High Similarity NPC224870
0.8654 High Similarity NPC61885
0.8654 High Similarity NPC63698
0.8641 High Similarity NPC469913
0.8632 High Similarity NPC27974
0.8627 High Similarity NPC119860
0.8624 High Similarity NPC15860
0.8624 High Similarity NPC127894
0.8624 High Similarity NPC219070
0.8624 High Similarity NPC470759
0.8614 High Similarity NPC477685
0.8611 High Similarity NPC53906
0.8611 High Similarity NPC246760
0.8611 High Similarity NPC84999
0.86 High Similarity NPC260775
0.8598 High Similarity NPC261343
0.8571 High Similarity NPC76938
0.8545 High Similarity NPC206
0.8545 High Similarity NPC9592
0.8545 High Similarity NPC48781
0.8544 High Similarity NPC292452
0.8532 High Similarity NPC115808
0.8519 High Similarity NPC276737
0.8519 High Similarity NPC22610
0.8515 High Similarity NPC130756
0.8515 High Similarity NPC12931
0.8515 High Similarity NPC70677
0.85 High Similarity NPC152097
0.85 High Similarity NPC474073
0.8491 Intermediate Similarity NPC242178
0.8485 Intermediate Similarity NPC222146
0.8469 Intermediate Similarity NPC55903
0.8462 Intermediate Similarity NPC248904
0.8462 Intermediate Similarity NPC164576
0.8455 Intermediate Similarity NPC33270
0.8455 Intermediate Similarity NPC69261
0.8455 Intermediate Similarity NPC470760
0.8455 Intermediate Similarity NPC277588
0.8455 Intermediate Similarity NPC474933
0.8454 Intermediate Similarity NPC55561
0.844 Intermediate Similarity NPC808
0.8438 Intermediate Similarity NPC19680
0.8431 Intermediate Similarity NPC252105
0.8411 Intermediate Similarity NPC268032
0.8396 Intermediate Similarity NPC202647
0.8378 Intermediate Similarity NPC190514
0.8378 Intermediate Similarity NPC144343
0.8365 Intermediate Similarity NPC471350
0.8364 Intermediate Similarity NPC141090
0.8364 Intermediate Similarity NPC150624
0.8351 Intermediate Similarity NPC242240
0.8351 Intermediate Similarity NPC318325
0.8351 Intermediate Similarity NPC280347
0.8351 Intermediate Similarity NPC123273
0.8351 Intermediate Similarity NPC177420
0.835 Intermediate Similarity NPC196479
0.835 Intermediate Similarity NPC108497
0.8333 Intermediate Similarity NPC72729
0.8333 Intermediate Similarity NPC294741
0.8319 Intermediate Similarity NPC24125
0.8318 Intermediate Similarity NPC475018
0.8317 Intermediate Similarity NPC79241
0.8317 Intermediate Similarity NPC6597
0.8317 Intermediate Similarity NPC475078
0.8316 Intermediate Similarity NPC150837
0.8304 Intermediate Similarity NPC184302
0.8304 Intermediate Similarity NPC191866
0.8304 Intermediate Similarity NPC217174
0.83 Intermediate Similarity NPC26244
0.83 Intermediate Similarity NPC274678
0.8286 Intermediate Similarity NPC155072
0.8273 Intermediate Similarity NPC472893
0.8273 Intermediate Similarity NPC167934
0.8252 Intermediate Similarity NPC80800
0.8247 Intermediate Similarity NPC113460
0.8247 Intermediate Similarity NPC25493
0.8246 Intermediate Similarity NPC39029
0.8246 Intermediate Similarity NPC237667
0.8241 Intermediate Similarity NPC469912
0.8235 Intermediate Similarity NPC33675
0.8235 Intermediate Similarity NPC299762
0.823 Intermediate Similarity NPC223451
0.8218 Intermediate Similarity NPC312132
0.8218 Intermediate Similarity NPC259512
0.8218 Intermediate Similarity NPC473388
0.8208 Intermediate Similarity NPC66834
0.8208 Intermediate Similarity NPC176527
0.82 Intermediate Similarity NPC245187
0.82 Intermediate Similarity NPC27323
0.82 Intermediate Similarity NPC152415
0.82 Intermediate Similarity NPC316301
0.82 Intermediate Similarity NPC151715
0.819 Intermediate Similarity NPC47284
0.8182 Intermediate Similarity NPC304541
0.8182 Intermediate Similarity NPC231150
0.8182 Intermediate Similarity NPC228287
0.8182 Intermediate Similarity NPC180508
0.8174 Intermediate Similarity NPC122175
0.8173 Intermediate Similarity NPC471228
0.8173 Intermediate Similarity NPC269212
0.8173 Intermediate Similarity NPC235762
0.8173 Intermediate Similarity NPC168393
0.8163 Intermediate Similarity NPC258219
0.8158 Intermediate Similarity NPC218753
0.8155 Intermediate Similarity NPC211885
0.8155 Intermediate Similarity NPC174911
0.8155 Intermediate Similarity NPC130103
0.8148 Intermediate Similarity NPC2682

  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 NPC166313 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
0.9118 High Similarity NPD4750 Phase 3
0.899 High Similarity NPD940 Approved
0.899 High Similarity NPD846 Approved
0.87 High Similarity NPD1242 Phase 1
0.8485 Intermediate Similarity NPD844 Approved
0.83 Intermediate Similarity NPD2859 Approved
0.83 Intermediate Similarity NPD2860 Approved
0.8235 Intermediate Similarity NPD3020 Approved
0.8218 Intermediate Similarity NPD288 Approved
0.82 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.82 Intermediate Similarity NPD2934 Approved
0.82 Intermediate Similarity NPD2933 Approved
0.8155 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7979 Intermediate Similarity NPD9093 Approved
0.7949 Intermediate Similarity NPD4749 Approved
0.7921 Intermediate Similarity NPD845 Approved
0.7895 Intermediate Similarity NPD9089 Approved
0.789 Intermediate Similarity NPD3021 Approved
0.789 Intermediate Similarity NPD3022 Approved
0.7835 Intermediate Similarity NPD111 Approved
0.7778 Intermediate Similarity NPD1444 Approved
0.7778 Intermediate Similarity NPD1445 Approved
0.7767 Intermediate Similarity NPD1809 Phase 2
0.775 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD7635 Approved
0.7642 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6671 Approved
0.7568 Intermediate Similarity NPD1792 Phase 2
0.7561 Intermediate Similarity NPD4625 Phase 3
0.7561 Intermediate Similarity NPD3027 Phase 3
0.75 Intermediate Similarity NPD9500 Approved
0.7459 Intermediate Similarity NPD599 Approved
0.7459 Intermediate Similarity NPD602 Approved
0.7459 Intermediate Similarity NPD858 Approved
0.7459 Intermediate Similarity NPD859 Approved
0.7426 Intermediate Similarity NPD9094 Approved
0.7387 Intermediate Similarity NPD2342 Discontinued
0.7339 Intermediate Similarity NPD4908 Phase 1
0.7333 Intermediate Similarity NPD1610 Phase 2
0.7304 Intermediate Similarity NPD2228 Approved
0.7304 Intermediate Similarity NPD2234 Approved
0.7304 Intermediate Similarity NPD2229 Approved
0.729 Intermediate Similarity NPD9273 Approved
0.7288 Intermediate Similarity NPD1548 Phase 1
0.7288 Intermediate Similarity NPD3091 Approved
0.7281 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7281 Intermediate Similarity NPD228 Approved
0.7258 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD1791 Approved
0.7241 Intermediate Similarity NPD1793 Approved
0.7231 Intermediate Similarity NPD6099 Approved
0.7231 Intermediate Similarity NPD6100 Approved
0.7222 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD422 Phase 1
0.719 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD3092 Approved
0.7167 Intermediate Similarity NPD3019 Approved
0.7167 Intermediate Similarity NPD2932 Approved
0.7167 Intermediate Similarity NPD4059 Approved
0.7156 Intermediate Similarity NPD3028 Approved
0.7155 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD6696 Suspended
0.7132 Intermediate Similarity NPD2568 Approved
0.7117 Intermediate Similarity NPD9610 Approved
0.7117 Intermediate Similarity NPD9608 Approved
0.7105 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3094 Phase 2
0.7097 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD9618 Approved
0.7094 Intermediate Similarity NPD9614 Approved
0.7083 Intermediate Similarity NPD4093 Discontinued
0.7069 Intermediate Similarity NPD9379 Approved
0.7069 Intermediate Similarity NPD9377 Approved
0.7053 Intermediate Similarity NPD9087 Approved
0.7043 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2684 Approved
0.7015 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.6992 Remote Similarity NPD9269 Phase 2
0.6977 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6977 Remote Similarity NPD943 Approved
0.6977 Remote Similarity NPD1613 Approved
0.6949 Remote Similarity NPD1476 Clinical (unspecified phase)
0.6942 Remote Similarity NPD9268 Approved
0.6939 Remote Similarity NPD9088 Approved
0.6935 Remote Similarity NPD2983 Phase 2
0.6935 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6935 Remote Similarity NPD2982 Phase 2
0.6923 Remote Similarity NPD7843 Approved
0.6917 Remote Similarity NPD9616 Approved
0.6917 Remote Similarity NPD9615 Approved
0.6917 Remote Similarity NPD9613 Approved
0.6917 Remote Similarity NPD16 Approved
0.6917 Remote Similarity NPD856 Approved
0.6911 Remote Similarity NPD1201 Approved
0.6894 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6891 Remote Similarity NPD7157 Approved
0.6885 Remote Similarity NPD2286 Discontinued
0.6885 Remote Similarity NPD3095 Discontinued
0.6885 Remote Similarity NPD9381 Approved
0.6885 Remote Similarity NPD9384 Approved
0.6885 Remote Similarity NPD1751 Approved
0.6885 Remote Similarity NPD4626 Approved
0.6864 Remote Similarity NPD5283 Phase 1
0.686 Remote Similarity NPD7330 Discontinued
0.686 Remote Similarity NPD316 Approved
0.6855 Remote Similarity NPD2233 Approved
0.6855 Remote Similarity NPD2981 Phase 2
0.6855 Remote Similarity NPD2232 Approved
0.6855 Remote Similarity NPD2230 Approved
0.685 Remote Similarity NPD5736 Approved
0.685 Remote Similarity NPD2861 Phase 2
0.685 Remote Similarity NPD3018 Phase 2
0.6846 Remote Similarity NPD2238 Phase 2
0.6842 Remote Similarity NPD968 Approved
0.6837 Remote Similarity NPD9294 Approved
0.6833 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6825 Remote Similarity NPD1129 Approved
0.6825 Remote Similarity NPD1133 Approved
0.6825 Remote Similarity NPD1131 Approved
0.6825 Remote Similarity NPD1135 Approved
0.6825 Remote Similarity NPD1134 Approved
0.6822 Remote Similarity NPD6859 Clinical (unspecified phase)
0.68 Remote Similarity NPD9622 Approved
0.68 Remote Similarity NPD4659 Approved
0.68 Remote Similarity NPD1755 Approved
0.6794 Remote Similarity NPD230 Phase 1
0.6783 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6783 Remote Similarity NPD290 Approved
0.6777 Remote Similarity NPD318 Approved
0.6777 Remote Similarity NPD317 Approved
0.6772 Remote Similarity NPD6584 Phase 3
0.6769 Remote Similarity NPD6405 Approved
0.6769 Remote Similarity NPD6407 Approved
0.675 Remote Similarity NPD255 Approved
0.675 Remote Similarity NPD256 Approved
0.6748 Remote Similarity NPD4589 Approved
0.6746 Remote Similarity NPD5311 Approved
0.6746 Remote Similarity NPD5310 Approved
0.6739 Remote Similarity NPD7390 Discontinued
0.6724 Remote Similarity NPD74 Approved
0.6724 Remote Similarity NPD9266 Approved
0.6721 Remote Similarity NPD1759 Phase 1
0.6721 Remote Similarity NPD5304 Approved
0.6721 Remote Similarity NPD5303 Approved
0.672 Remote Similarity NPD1608 Approved
0.672 Remote Similarity NPD2562 Approved
0.672 Remote Similarity NPD2561 Approved
0.6718 Remote Similarity NPD1240 Approved
0.6694 Remote Similarity NPD9493 Approved
0.6694 Remote Similarity NPD3496 Discontinued
0.6694 Remote Similarity NPD7636 Approved
0.6694 Remote Similarity NPD405 Clinical (unspecified phase)
0.6694 Remote Similarity NPD7340 Approved
0.6693 Remote Similarity NPD1470 Approved
0.6693 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6693 Remote Similarity NPD4103 Phase 2
0.6693 Remote Similarity NPD3053 Approved
0.6693 Remote Similarity NPD3055 Approved
0.6692 Remote Similarity NPD6111 Discontinued
0.6667 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6667 Remote Similarity NPD475 Phase 2
0.6667 Remote Similarity NPD9244 Approved
0.6667 Remote Similarity NPD4235 Clinical (unspecified phase)
0.6667 Remote Similarity NPD497 Approved
0.6667 Remote Similarity NPD5451 Approved
0.6642 Remote Similarity NPD651 Clinical (unspecified phase)
0.6641 Remote Similarity NPD2195 Approved
0.6641 Remote Similarity NPD2194 Approved
0.6641 Remote Similarity NPD9619 Approved
0.6641 Remote Similarity NPD9621 Approved
0.6641 Remote Similarity NPD6663 Approved
0.6641 Remote Similarity NPD9620 Approved
0.6639 Remote Similarity NPD1758 Phase 1
0.6639 Remote Similarity NPD821 Approved
0.6638 Remote Similarity NPD9263 Approved
0.6638 Remote Similarity NPD9264 Approved
0.6638 Remote Similarity NPD9267 Approved
0.6637 Remote Similarity NPD4818 Approved
0.6637 Remote Similarity NPD4817 Approved
0.6618 Remote Similarity NPD970 Clinical (unspecified phase)
0.6617 Remote Similarity NPD1607 Approved
0.6613 Remote Similarity NPD1778 Approved
0.6613 Remote Similarity NPD2667 Approved
0.6613 Remote Similarity NPD2668 Approved
0.6612 Remote Similarity NPD709 Approved
0.6591 Remote Similarity NPD6346 Approved
0.6591 Remote Similarity NPD1555 Discontinued
0.6589 Remote Similarity NPD3636 Approved
0.6589 Remote Similarity NPD3637 Approved
0.6589 Remote Similarity NPD3635 Approved
0.6587 Remote Similarity NPD2231 Phase 2
0.6587 Remote Similarity NPD2235 Phase 2
0.6585 Remote Similarity NPD9545 Approved
0.6585 Remote Similarity NPD7741 Discontinued
0.6583 Remote Similarity NPD495 Approved
0.6583 Remote Similarity NPD1398 Phase 1

  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