Structure

Physi-Chem Properties

Molecular Weight:  180.14
Volume:  203.452
LogP:  -0.279
LogD:  -0.449
LogS:  0.576
# Rotatable Bonds:  4
TPSA:  9.23
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.642
Synthetic Accessibility Score:  1.917
Fsp3:  0.455
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.433
MDCK Permeability:  5.0001628551399335e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.776
Human Intestinal Absorption (HIA):  0.943
20% Bioavailability (F20%):  0.998
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.254
Plasma Protein Binding (PPB):  21.36777114868164%
Volume Distribution (VD):  1.031
Pgp-substrate:  59.21101379394531%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.937
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.213
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.934
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.177

ADMET: Excretion

Clearance (CL):  6.321
Half-life (T1/2):  0.93

ADMET: Toxicity

hERG Blockers:  0.07
Human Hepatotoxicity (H-HT):  0.04
Drug-inuced Liver Injury (DILI):  0.006
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.604
Maximum Recommended Daily Dose:  0.619
Skin Sensitization:  0.097
Carcinogencity:  0.035
Eye Corrosion:  0.04
Eye Irritation:  0.324
Respiratory Toxicity:  0.826

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

  Natural Product: NPC313918

Natural Product ID:  NPC313918
Common Name*:   Trimethyl(2-Phenoxyethyl)Azanium
IUPAC Name:   trimethyl(2-phenoxyethyl)azanium
Synonyms:  
Standard InCHIKey:  VCXBSHBJVUIQHJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H18NO/c1-12(2,3)9-10-13-11-7-5-4-6-8-11/h4-8H,9-10H2,1-3H3/q+1
SMILES:  C[N+](C)(C)CCOC1=CC=CC=C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL209891
PubChem CID:   9725
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002341] Phenol ethers

*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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[1402962]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Flower Buds n.a. n.a. PMID[26977531]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[8904847]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22216 Chimonanthus fragrans Species Calycanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9942.1 Narcissus tazetta var. chinensis Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8859 Fructus caryophylli n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8859 Fructus caryophylli n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO22216 Chimonanthus fragrans Species Calycanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9942.1 Narcissus tazetta var. chinensis Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22216 Chimonanthus fragrans Species Calycanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22216 Chimonanthus fragrans Species Calycanthaceae 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
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 1100.0 nM PMID[517867]

☑ 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 NPC313918 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
0.8922 High Similarity NPC95977
0.8132 Intermediate Similarity NPC124576
0.8085 Intermediate Similarity NPC125306
0.7959 Intermediate Similarity NPC318429
0.7895 Intermediate Similarity NPC23837
0.7845 Intermediate Similarity NPC255253
0.783 Intermediate Similarity NPC41594
0.7767 Intermediate Similarity NPC471576
0.7658 Intermediate Similarity NPC26524
0.7653 Intermediate Similarity NPC206876
0.7619 Intermediate Similarity NPC51633
0.7547 Intermediate Similarity NPC192596
0.75 Intermediate Similarity NPC8002
0.75 Intermediate Similarity NPC259134
0.75 Intermediate Similarity NPC302546
0.75 Intermediate Similarity NPC177844
0.75 Intermediate Similarity NPC95755
0.75 Intermediate Similarity NPC99886
0.7477 Intermediate Similarity NPC38079
0.7477 Intermediate Similarity NPC108875
0.7429 Intermediate Similarity NPC314803
0.7429 Intermediate Similarity NPC132725
0.7426 Intermediate Similarity NPC71853
0.7417 Intermediate Similarity NPC320242
0.7417 Intermediate Similarity NPC136112
0.7417 Intermediate Similarity NPC141739
0.7414 Intermediate Similarity NPC256369
0.7407 Intermediate Similarity NPC473855
0.7407 Intermediate Similarity NPC470393
0.7407 Intermediate Similarity NPC42383
0.74 Intermediate Similarity NPC157213
0.74 Intermediate Similarity NPC47422
0.7379 Intermediate Similarity NPC471581
0.7364 Intermediate Similarity NPC146530
0.7358 Intermediate Similarity NPC316797
0.7353 Intermediate Similarity NPC321956
0.735 Intermediate Similarity NPC263835
0.7339 Intermediate Similarity NPC473653
0.7339 Intermediate Similarity NPC274732
0.7339 Intermediate Similarity NPC176971
0.7321 Intermediate Similarity NPC166837
0.7317 Intermediate Similarity NPC195902
0.7315 Intermediate Similarity NPC283546
0.7273 Intermediate Similarity NPC157473
0.7273 Intermediate Similarity NPC151530
0.7273 Intermediate Similarity NPC258171
0.7273 Intermediate Similarity NPC186469
0.7264 Intermediate Similarity NPC307039
0.725 Intermediate Similarity NPC328267
0.7248 Intermediate Similarity NPC128730
0.7248 Intermediate Similarity NPC17537
0.7207 Intermediate Similarity NPC97811
0.7207 Intermediate Similarity NPC309982
0.7196 Intermediate Similarity NPC107101
0.7182 Intermediate Similarity NPC326801
0.717 Intermediate Similarity NPC470161
0.7154 Intermediate Similarity NPC280736
0.713 Intermediate Similarity NPC307425
0.7117 Intermediate Similarity NPC194034
0.7103 Intermediate Similarity NPC100870
0.7091 Intermediate Similarity NPC473393
0.7091 Intermediate Similarity NPC8302
0.708 Intermediate Similarity NPC46844
0.7069 Intermediate Similarity NPC303370
0.7064 Intermediate Similarity NPC179686
0.7063 Intermediate Similarity NPC307123
0.7063 Intermediate Similarity NPC97870
0.7063 Intermediate Similarity NPC247018
0.7059 Intermediate Similarity NPC321133
0.7054 Intermediate Similarity NPC291837
0.7048 Intermediate Similarity NPC16649
0.7048 Intermediate Similarity NPC114325
0.7037 Intermediate Similarity NPC13755
0.7027 Intermediate Similarity NPC326447
0.7018 Intermediate Similarity NPC21890
0.7018 Intermediate Similarity NPC55300
0.7009 Intermediate Similarity NPC175298
0.6992 Remote Similarity NPC110131
0.6984 Remote Similarity NPC70485
0.6972 Remote Similarity NPC84325
0.6967 Remote Similarity NPC211218
0.6957 Remote Similarity NPC165646
0.6947 Remote Similarity NPC83289
0.6947 Remote Similarity NPC212850
0.6947 Remote Similarity NPC189724
0.6937 Remote Similarity NPC238115
0.693 Remote Similarity NPC231251
0.693 Remote Similarity NPC25067
0.693 Remote Similarity NPC88868
0.6929 Remote Similarity NPC471953
0.6909 Remote Similarity NPC12870
0.6909 Remote Similarity NPC305205
0.6909 Remote Similarity NPC24327
0.6882 Remote Similarity NPC215445
0.6864 Remote Similarity NPC258992
0.6847 Remote Similarity NPC109637
0.6842 Remote Similarity NPC149545
0.6833 Remote Similarity NPC43275
0.6825 Remote Similarity NPC283079
0.6818 Remote Similarity NPC300166
0.6818 Remote Similarity NPC12714
0.6818 Remote Similarity NPC310905
0.681 Remote Similarity NPC115379
0.6807 Remote Similarity NPC323948
0.6797 Remote Similarity NPC470392
0.6794 Remote Similarity NPC318591
0.6794 Remote Similarity NPC231163
0.6786 Remote Similarity NPC475269
0.6783 Remote Similarity NPC106141
0.6777 Remote Similarity NPC53596
0.6777 Remote Similarity NPC17388
0.6777 Remote Similarity NPC289330
0.6777 Remote Similarity NPC471308
0.6777 Remote Similarity NPC160120
0.6774 Remote Similarity NPC62101
0.6774 Remote Similarity NPC95733
0.6757 Remote Similarity NPC298224
0.6757 Remote Similarity NPC319933
0.6752 Remote Similarity NPC90903
0.6752 Remote Similarity NPC264782
0.6748 Remote Similarity NPC298486
0.6741 Remote Similarity NPC247298
0.6727 Remote Similarity NPC156768
0.6727 Remote Similarity NPC289381
0.6727 Remote Similarity NPC155847
0.6726 Remote Similarity NPC113457
0.6724 Remote Similarity NPC266932
0.6724 Remote Similarity NPC245552
0.6721 Remote Similarity NPC83279
0.672 Remote Similarity NPC124776
0.672 Remote Similarity NPC29477
0.6718 Remote Similarity NPC307682
0.6696 Remote Similarity NPC2518
0.6696 Remote Similarity NPC241224
0.6696 Remote Similarity NPC292792
0.6696 Remote Similarity NPC474272
0.6696 Remote Similarity NPC474603
0.6696 Remote Similarity NPC38209
0.6696 Remote Similarity NPC259554
0.6696 Remote Similarity NPC12987
0.6695 Remote Similarity NPC235250
0.6695 Remote Similarity NPC161696
0.6695 Remote Similarity NPC142319
0.6695 Remote Similarity NPC252004
0.6694 Remote Similarity NPC315632
0.6667 Remote Similarity NPC280760
0.6667 Remote Similarity NPC227894
0.6667 Remote Similarity NPC474920
0.6667 Remote Similarity NPC251306
0.6667 Remote Similarity NPC35543
0.6667 Remote Similarity NPC233320
0.6667 Remote Similarity NPC120075
0.6667 Remote Similarity NPC218323
0.6642 Remote Similarity NPC245974
0.6639 Remote Similarity NPC41801
0.6638 Remote Similarity NPC226914
0.6638 Remote Similarity NPC137685
0.6637 Remote Similarity NPC139891
0.6637 Remote Similarity NPC227255
0.6637 Remote Similarity NPC288760
0.6637 Remote Similarity NPC307875
0.6636 Remote Similarity NPC233791
0.6614 Remote Similarity NPC172403
0.6613 Remote Similarity NPC471314
0.6613 Remote Similarity NPC471315
0.6612 Remote Similarity NPC5932
0.6612 Remote Similarity NPC293424
0.6612 Remote Similarity NPC283616
0.6612 Remote Similarity NPC159916
0.661 Remote Similarity NPC301735
0.661 Remote Similarity NPC303522
0.6609 Remote Similarity NPC245115
0.6609 Remote Similarity NPC201959
0.6609 Remote Similarity NPC241549
0.6609 Remote Similarity NPC75440
0.6591 Remote Similarity NPC469808
0.6585 Remote Similarity NPC318357
0.6583 Remote Similarity NPC290470
0.6583 Remote Similarity NPC154256
0.6579 Remote Similarity NPC42471
0.6579 Remote Similarity NPC1065
0.6579 Remote Similarity NPC30416
0.6565 Remote Similarity NPC29650
0.6562 Remote Similarity NPC100980
0.656 Remote Similarity NPC217277
0.6557 Remote Similarity NPC234956
0.6557 Remote Similarity NPC163036
0.6557 Remote Similarity NPC59561
0.6557 Remote Similarity NPC172253
0.6557 Remote Similarity NPC37858
0.6557 Remote Similarity NPC98748
0.6555 Remote Similarity NPC87563
0.6552 Remote Similarity NPC24777
0.6552 Remote Similarity NPC82016
0.6532 Remote Similarity NPC211992
0.6529 Remote Similarity NPC9248
0.6529 Remote Similarity NPC161768
0.6519 Remote Similarity NPC476462
0.6519 Remote Similarity NPC204546
0.6515 Remote Similarity NPC138365

  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 NPC313918 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
0.9192 High Similarity NPD5374 Approved
0.9192 High Similarity NPD5373 Approved
0.8922 High Similarity NPD2673 Approved
0.8922 High Similarity NPD2671 Approved
0.8505 High Similarity NPD2557 Approved
0.8426 Intermediate Similarity NPD3596 Phase 2
0.8349 Intermediate Similarity NPD1408 Clinical (unspecified phase)
0.8273 Intermediate Similarity NPD7533 Approved
0.8273 Intermediate Similarity NPD6581 Approved
0.8273 Intermediate Similarity NPD6580 Approved
0.8273 Intermediate Similarity NPD7534 Approved
0.8269 Intermediate Similarity NPD9624 Approved
0.8198 Intermediate Similarity NPD2594 Approved
0.8198 Intermediate Similarity NPD2595 Approved
0.8198 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1102 Approved
0.8182 Intermediate Similarity NPD1103 Approved
0.7959 Intermediate Similarity NPD9365 Approved
0.7876 Intermediate Similarity NPD1798 Approved
0.7876 Intermediate Similarity NPD1797 Approved
0.7845 Intermediate Similarity NPD6539 Approved
0.7845 Intermediate Similarity NPD6583 Phase 3
0.7845 Intermediate Similarity NPD6543 Approved
0.7845 Intermediate Similarity NPD6540 Phase 3
0.7845 Intermediate Similarity NPD6582 Phase 2
0.7845 Intermediate Similarity NPD6542 Approved
0.7818 Intermediate Similarity NPD592 Approved
0.7818 Intermediate Similarity NPD594 Approved
0.7778 Intermediate Similarity NPD6541 Approved
0.7778 Intermediate Similarity NPD6538 Approved
0.7719 Intermediate Similarity NPD3445 Approved
0.7719 Intermediate Similarity NPD3443 Approved
0.7719 Intermediate Similarity NPD3444 Approved
0.7647 Intermediate Similarity NPD6584 Phase 3
0.7647 Intermediate Similarity NPD2987 Approved
0.7647 Intermediate Similarity NPD7018 Phase 2
0.7647 Intermediate Similarity NPD2990 Approved
0.7586 Intermediate Similarity NPD155 Clinical (unspecified phase)
0.7583 Intermediate Similarity NPD4993 Discontinued
0.7565 Intermediate Similarity NPD6382 Discontinued
0.7565 Intermediate Similarity NPD3049 Approved
0.75 Intermediate Similarity NPD1010 Approved
0.75 Intermediate Similarity NPD2556 Approved
0.75 Intermediate Similarity NPD2554 Approved
0.7478 Intermediate Similarity NPD2486 Discontinued
0.7453 Intermediate Similarity NPD291 Approved
0.7438 Intermediate Similarity NPD2237 Approved
0.7438 Intermediate Similarity NPD5266 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD1819 Approved
0.7417 Intermediate Similarity NPD1818 Approved
0.7417 Intermediate Similarity NPD1817 Approved
0.7417 Intermediate Similarity NPD1820 Approved
0.7417 Intermediate Similarity NPD1794 Approved
0.7411 Intermediate Similarity NPD821 Approved
0.74 Intermediate Similarity NPD9295 Approved
0.7398 Intermediate Similarity NPD7294 Phase 1
0.7395 Intermediate Similarity NPD3685 Discontinued
0.7377 Intermediate Similarity NPD3537 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD2549 Approved
0.7358 Intermediate Similarity NPD2550 Approved
0.7358 Intermediate Similarity NPD2553 Approved
0.7358 Intermediate Similarity NPD2558 Approved
0.7358 Intermediate Similarity NPD2555 Approved
0.7358 Intermediate Similarity NPD2552 Approved
0.7339 Intermediate Similarity NPD7265 Discontinued
0.7317 Intermediate Similarity NPD5746 Approved
0.7297 Intermediate Similarity NPD556 Approved
0.7295 Intermediate Similarity NPD2250 Discontinued
0.7295 Intermediate Similarity NPD455 Discontinued
0.729 Intermediate Similarity NPD4188 Approved
0.729 Intermediate Similarity NPD4189 Approved
0.7288 Intermediate Similarity NPD3447 Discontinued
0.7288 Intermediate Similarity NPD3294 Phase 2
0.7281 Intermediate Similarity NPD593 Approved
0.7281 Intermediate Similarity NPD595 Approved
0.7273 Intermediate Similarity NPD4098 Discontinued
0.7258 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2429 Approved
0.725 Intermediate Similarity NPD2428 Approved
0.7227 Intermediate Similarity NPD776 Approved
0.7222 Intermediate Similarity NPD4622 Approved
0.7222 Intermediate Similarity NPD4618 Approved
0.7207 Intermediate Similarity NPD2684 Approved
0.7203 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD5745 Approved
0.72 Intermediate Similarity NPD3530 Approved
0.72 Intermediate Similarity NPD3531 Approved
0.72 Intermediate Similarity NPD3532 Approved
0.7177 Intermediate Similarity NPD3164 Approved
0.7177 Intermediate Similarity NPD6179 Discontinued
0.7177 Intermediate Similarity NPD3179 Approved
0.7177 Intermediate Similarity NPD3180 Approved
0.7177 Intermediate Similarity NPD3165 Approved
0.7177 Intermediate Similarity NPD3166 Approved
0.7177 Intermediate Similarity NPD3167 Approved
0.7156 Intermediate Similarity NPD3047 Approved
0.7156 Intermediate Similarity NPD3046 Approved
0.7156 Intermediate Similarity NPD3048 Approved
0.7156 Intermediate Similarity NPD9501 Approved
0.7143 Intermediate Similarity NPD4101 Phase 1
0.7131 Intermediate Similarity NPD1770 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD1336 Approved
0.7117 Intermediate Similarity NPD290 Approved
0.7109 Intermediate Similarity NPD5689 Approved
0.7109 Intermediate Similarity NPD5688 Approved
0.7109 Intermediate Similarity NPD2200 Suspended
0.7097 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD254 Approved
0.7063 Intermediate Similarity NPD1423 Approved
0.7063 Intermediate Similarity NPD3162 Approved
0.7063 Intermediate Similarity NPD3163 Approved
0.7059 Intermediate Similarity NPD2667 Approved
0.7059 Intermediate Similarity NPD2668 Approved
0.7054 Intermediate Similarity NPD2164 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD9296 Approved
0.7031 Intermediate Similarity NPD2223 Approved
0.7031 Intermediate Similarity NPD2224 Approved
0.7031 Intermediate Similarity NPD3052 Approved
0.7031 Intermediate Similarity NPD3054 Approved
0.7027 Intermediate Similarity NPD810 Approved
0.7027 Intermediate Similarity NPD968 Approved
0.7027 Intermediate Similarity NPD3134 Approved
0.7027 Intermediate Similarity NPD2559 Approved
0.7027 Intermediate Similarity NPD812 Approved
0.7027 Intermediate Similarity NPD811 Approved
0.7027 Intermediate Similarity NPD2551 Approved
0.7008 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD1393 Approved
0.7 Intermediate Similarity NPD6032 Approved
0.7 Intermediate Similarity NPD1725 Approved
0.6992 Remote Similarity NPD2082 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6984 Remote Similarity NPD1048 Approved
0.6977 Remote Similarity NPD7119 Phase 2
0.6964 Remote Similarity NPD9552 Approved
0.6964 Remote Similarity NPD1358 Approved
0.6957 Remote Similarity NPD7843 Approved
0.6929 Remote Similarity NPD4475 Approved
0.6929 Remote Similarity NPD4474 Approved
0.6929 Remote Similarity NPD2245 Discovery
0.6929 Remote Similarity NPD481 Phase 3
0.6923 Remote Similarity NPD3152 Clinical (unspecified phase)
0.6905 Remote Similarity NPD5163 Phase 2
0.6894 Remote Similarity NPD2897 Discontinued
0.6885 Remote Similarity NPD2235 Phase 2
0.6885 Remote Similarity NPD2232 Approved
0.6885 Remote Similarity NPD2230 Approved
0.6885 Remote Similarity NPD2231 Phase 2
0.6885 Remote Similarity NPD2233 Approved
0.688 Remote Similarity NPD1712 Approved
0.6875 Remote Similarity NPD3142 Approved
0.6875 Remote Similarity NPD3140 Approved
0.6855 Remote Similarity NPD9549 Phase 2
0.6842 Remote Similarity NPD5289 Phase 2
0.6822 Remote Similarity NPD1341 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7030 Discontinued
0.6818 Remote Similarity NPD5865 Clinical (unspecified phase)
0.681 Remote Similarity NPD769 Approved
0.68 Remote Similarity NPD558 Phase 2
0.6794 Remote Similarity NPD2661 Clinical (unspecified phase)
0.6794 Remote Similarity NPD2155 Approved
0.6794 Remote Similarity NPD2156 Approved
0.6794 Remote Similarity NPD2154 Approved
0.6791 Remote Similarity NPD7466 Approved
0.678 Remote Similarity NPD191 Approved
0.678 Remote Similarity NPD7157 Approved
0.6767 Remote Similarity NPD7037 Approved
0.6767 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6767 Remote Similarity NPD1391 Approved
0.6752 Remote Similarity NPD1241 Discontinued
0.675 Remote Similarity NPD1182 Approved
0.6746 Remote Similarity NPD2407 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2040 Clinical (unspecified phase)
0.6742 Remote Similarity NPD2240 Approved
0.6742 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6742 Remote Similarity NPD2239 Approved
0.6742 Remote Similarity NPD1422 Approved
0.6742 Remote Similarity NPD3454 Phase 3
0.6742 Remote Similarity NPD729 Discontinued
0.6741 Remote Similarity NPD3692 Discontinued
0.672 Remote Similarity NPD3827 Clinical (unspecified phase)
0.6716 Remote Similarity NPD4487 Clinical (unspecified phase)
0.6694 Remote Similarity NPD1421 Approved
0.6694 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6694 Remote Similarity NPD1420 Approved
0.6691 Remote Similarity NPD5756 Phase 2
0.6691 Remote Similarity NPD6815 Approved
0.6667 Remote Similarity NPD2496 Approved
0.6667 Remote Similarity NPD3690 Phase 2
0.6667 Remote Similarity NPD7905 Discontinued
0.6667 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2497 Approved
0.6667 Remote Similarity NPD7477 Discontinued
0.6667 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3691 Phase 2
0.6667 Remote Similarity NPD5535 Approved
0.6642 Remote Similarity NPD7213 Phase 3
0.6642 Remote Similarity NPD7212 Phase 2

  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