Structure

Physi-Chem Properties

Molecular Weight:  135.1
Volume:  158.751
LogP:  1.731
LogD:  1.543
LogS:  -0.259
# Rotatable Bonds:  3
TPSA:  12.03
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.661
Synthetic Accessibility Score:  1.376
Fsp3:  0.333
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:  -4.452
MDCK Permeability:  2.9325992727535777e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.271
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.969
Plasma Protein Binding (PPB):  24.81671142578125%
Volume Distribution (VD):  3.437
Pgp-substrate:  59.85129928588867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.186
CYP1A2-substrate:  0.611
CYP2C19-inhibitor:  0.04
CYP2C19-substrate:  0.916
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.237
CYP2D6-inhibitor:  0.727
CYP2D6-substrate:  0.872
CYP3A4-inhibitor:  0.069
CYP3A4-substrate:  0.528

ADMET: Excretion

Clearance (CL):  10.221
Half-life (T1/2):  0.663

ADMET: Toxicity

hERG Blockers:  0.117
Human Hepatotoxicity (H-HT):  0.32
Drug-inuced Liver Injury (DILI):  0.019
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.563
Maximum Recommended Daily Dose:  0.88
Skin Sensitization:  0.896
Carcinogencity:  0.04
Eye Corrosion:  0.127
Eye Irritation:  0.192
Respiratory Toxicity:  0.951

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC139658

Natural Product ID:  NPC139658
Common Name*:   N-Methylphenethylamine
IUPAC Name:   n.a.
Synonyms:   Methyl-Phenethyl-Amine; N-Methylphenethylamine
Standard InCHIKey:  SASNBVQSOZSTPD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H13N/c1-10-8-7-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3
SMILES:  CNCCc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000186] Phenethylamines

*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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. DOI[10.1021/jf00055a023]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1021/jf970571j]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. seed n.a. PMID[11539687]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[12713418]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[21080643]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. husk n.a. PMID[21574561]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. leaf n.a. PMID[21574561]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. seed n.a. PMID[23292602]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24014097]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. fruit n.a. PMID[240326]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24128451]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[29762032]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. pollen n.a. PMID[8987503]
NPO15810 Zea mays Species Poaceae Eukaryota Silk Essent. Oil n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Cob n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Husk Essent. Oil n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[USDA]

☑ 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
NPO16230 NPC139658 Raw Fruit 0.12 0.12 0.12 mg/100g Database [DUKE]
NPO7576 NPC139658 Raw Leaf 0.21 0.05 0.37 mg/100g Database [DUKE]
NPO16230 NPC139658 Raw Pericarp 0.13 0.13 0.13 mg/100g Database [DUKE]
NPO163 NPC139658 Raw Root 0.2 0.2 0.2 mg/100g Database [DUKE]
NPO15810 NPC139658 Raw Seed 0.11 0.11 0.11 mg/100g Database [DUKE]

☑ 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
NPT524 Individual Protein Serine-protein kinase ATM Homo sapiens Potency = 31622.8 nM PMID[464245]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 5.0 nM PMID[464245]
NPT976 Individual Protein Trace amine-associated receptor 1 Homo sapiens EC50 = 387.0 nM PMID[464244]
NPT976 Individual Protein Trace amine-associated receptor 1 Homo sapiens Emax = 69.0 % PMID[464244]
NPT976 Individual Protein Trace amine-associated receptor 1 Homo sapiens EC50 = 250.0 nM PMID[464244]
NPT976 Individual Protein Trace amine-associated receptor 1 Homo sapiens Emax = 93.4 % PMID[464244]

☑ 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 NPC139658 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
0.9286 High Similarity NPC229235
0.9189 High Similarity NPC12857
0.9167 High Similarity NPC122327
0.9167 High Similarity NPC112609
0.9167 High Similarity NPC113000
0.9041 High Similarity NPC276699
0.88 High Similarity NPC290638
0.88 High Similarity NPC325662
0.88 High Similarity NPC98269
0.8734 High Similarity NPC169016
0.8533 High Similarity NPC98976
0.8519 High Similarity NPC258046
0.8493 Intermediate Similarity NPC219246
0.8421 Intermediate Similarity NPC271642
0.8272 Intermediate Similarity NPC133162
0.8267 Intermediate Similarity NPC244738
0.7927 Intermediate Similarity NPC474088
0.7927 Intermediate Similarity NPC104070
0.7927 Intermediate Similarity NPC119677
0.7901 Intermediate Similarity NPC231986
0.7841 Intermediate Similarity NPC469330
0.7841 Intermediate Similarity NPC7067
0.7753 Intermediate Similarity NPC329430
0.7714 Intermediate Similarity NPC212114
0.7714 Intermediate Similarity NPC65873
0.7714 Intermediate Similarity NPC300345
0.7714 Intermediate Similarity NPC120441
0.7692 Intermediate Similarity NPC299134
0.7667 Intermediate Similarity NPC471320
0.7667 Intermediate Similarity NPC471319
0.7571 Intermediate Similarity NPC198841
0.7571 Intermediate Similarity NPC269586
0.7447 Intermediate Similarity NPC327226
0.7432 Intermediate Similarity NPC50266
0.7429 Intermediate Similarity NPC149436
0.7429 Intermediate Similarity NPC277704
0.7397 Intermediate Similarity NPC238023
0.7397 Intermediate Similarity NPC150196
0.7397 Intermediate Similarity NPC135924
0.7397 Intermediate Similarity NPC210849
0.7397 Intermediate Similarity NPC310758
0.7397 Intermediate Similarity NPC54368
0.7397 Intermediate Similarity NPC248705
0.7363 Intermediate Similarity NPC108339
0.7361 Intermediate Similarity NPC8235
0.7356 Intermediate Similarity NPC60408
0.7297 Intermediate Similarity NPC29680
0.7292 Intermediate Similarity NPC147000
0.7292 Intermediate Similarity NPC304761
0.7292 Intermediate Similarity NPC150254
0.7292 Intermediate Similarity NPC226778
0.726 Intermediate Similarity NPC147062
0.726 Intermediate Similarity NPC169110
0.7253 Intermediate Similarity NPC322040
0.7253 Intermediate Similarity NPC291070
0.7253 Intermediate Similarity NPC246757
0.7222 Intermediate Similarity NPC470926
0.7216 Intermediate Similarity NPC67043
0.72 Intermediate Similarity NPC88566
0.7179 Intermediate Similarity NPC200936
0.7162 Intermediate Similarity NPC246588
0.7159 Intermediate Similarity NPC473031
0.7143 Intermediate Similarity NPC475289
0.7143 Intermediate Similarity NPC475573
0.7143 Intermediate Similarity NPC473661
0.7123 Intermediate Similarity NPC36357
0.7123 Intermediate Similarity NPC64270
0.7123 Intermediate Similarity NPC114327
0.7105 Intermediate Similarity NPC198023
0.7105 Intermediate Similarity NPC155172
0.7105 Intermediate Similarity NPC32312
0.7079 Intermediate Similarity NPC12429
0.7079 Intermediate Similarity NPC30445
0.7067 Intermediate Similarity NPC66517
0.7067 Intermediate Similarity NPC71009
0.7067 Intermediate Similarity NPC22786
0.7045 Intermediate Similarity NPC203076
0.7013 Intermediate Similarity NPC178527
0.7 Intermediate Similarity NPC470877
0.6989 Remote Similarity NPC20142
0.6989 Remote Similarity NPC215351
0.6977 Remote Similarity NPC14326
0.6974 Remote Similarity NPC21211
0.6974 Remote Similarity NPC113670
0.6974 Remote Similarity NPC45756
0.6966 Remote Similarity NPC17497
0.6966 Remote Similarity NPC305602
0.6966 Remote Similarity NPC471638
0.6947 Remote Similarity NPC290515
0.6947 Remote Similarity NPC303611
0.6947 Remote Similarity NPC226096
0.6947 Remote Similarity NPC164514
0.6947 Remote Similarity NPC108606
0.6939 Remote Similarity NPC275467
0.6931 Remote Similarity NPC24777
0.6923 Remote Similarity NPC159178
0.6923 Remote Similarity NPC471307
0.6923 Remote Similarity NPC6107
0.6923 Remote Similarity NPC209764
0.6923 Remote Similarity NPC78041
0.6923 Remote Similarity NPC267443
0.6923 Remote Similarity NPC141139
0.6923 Remote Similarity NPC121872
0.6923 Remote Similarity NPC74936
0.6897 Remote Similarity NPC134825
0.6889 Remote Similarity NPC111233
0.6883 Remote Similarity NPC291066
0.6882 Remote Similarity NPC71140
0.6867 Remote Similarity NPC110264
0.6848 Remote Similarity NPC245259
0.6842 Remote Similarity NPC122493
0.6842 Remote Similarity NPC10781
0.6842 Remote Similarity NPC200745
0.6842 Remote Similarity NPC293628
0.6813 Remote Similarity NPC176858
0.6795 Remote Similarity NPC289915
0.6795 Remote Similarity NPC113837
0.679 Remote Similarity NPC121708
0.679 Remote Similarity NPC125144
0.6778 Remote Similarity NPC262295
0.6771 Remote Similarity NPC322598
0.675 Remote Similarity NPC246822
0.675 Remote Similarity NPC139416
0.675 Remote Similarity NPC213570
0.6744 Remote Similarity NPC192623
0.6742 Remote Similarity NPC3210
0.6739 Remote Similarity NPC316108
0.6739 Remote Similarity NPC191444
0.6711 Remote Similarity NPC45255
0.6709 Remote Similarity NPC52330
0.6702 Remote Similarity NPC471309
0.6701 Remote Similarity NPC125732
0.6667 Remote Similarity NPC77294
0.6667 Remote Similarity NPC226438
0.6667 Remote Similarity NPC35599
0.6667 Remote Similarity NPC324569
0.6635 Remote Similarity NPC275410
0.6634 Remote Similarity NPC327481
0.6633 Remote Similarity NPC214200
0.6633 Remote Similarity NPC289381
0.6633 Remote Similarity NPC228400
0.6633 Remote Similarity NPC155847
0.6632 Remote Similarity NPC256452
0.6632 Remote Similarity NPC161972
0.6632 Remote Similarity NPC303045
0.6632 Remote Similarity NPC58674
0.663 Remote Similarity NPC173991
0.6625 Remote Similarity NPC311343
0.6604 Remote Similarity NPC113099
0.6596 Remote Similarity NPC108800
0.6593 Remote Similarity NPC53492
0.6585 Remote Similarity NPC158028
0.6585 Remote Similarity NPC226999
0.6585 Remote Similarity NPC1008
0.6585 Remote Similarity NPC87099
0.6585 Remote Similarity NPC39799
0.6585 Remote Similarity NPC135433
0.6585 Remote Similarity NPC74458
0.6585 Remote Similarity NPC193578
0.6585 Remote Similarity NPC280135
0.6582 Remote Similarity NPC36440
0.6579 Remote Similarity NPC147578
0.6566 Remote Similarity NPC239854
0.6562 Remote Similarity NPC25565
0.6552 Remote Similarity NPC309279
0.6543 Remote Similarity NPC98880
0.6543 Remote Similarity NPC473206
0.6542 Remote Similarity NPC10286
0.6542 Remote Similarity NPC213
0.6535 Remote Similarity NPC42383
0.6526 Remote Similarity NPC474974
0.6506 Remote Similarity NPC212463
0.6506 Remote Similarity NPC54269
0.6506 Remote Similarity NPC285679
0.65 Remote Similarity NPC164859
0.65 Remote Similarity NPC68055
0.6495 Remote Similarity NPC475439
0.6495 Remote Similarity NPC472258
0.6495 Remote Similarity NPC473501
0.6494 Remote Similarity NPC200624
0.6471 Remote Similarity NPC473498
0.6465 Remote Similarity NPC474582
0.6463 Remote Similarity NPC72670
0.6463 Remote Similarity NPC95289
0.6463 Remote Similarity NPC251490
0.6463 Remote Similarity NPC263385
0.6456 Remote Similarity NPC264470
0.6422 Remote Similarity NPC137096
0.642 Remote Similarity NPC239931
0.642 Remote Similarity NPC22760
0.642 Remote Similarity NPC78954
0.642 Remote Similarity NPC82770
0.6408 Remote Similarity NPC186469
0.64 Remote Similarity NPC329375
0.64 Remote Similarity NPC291610
0.6392 Remote Similarity NPC317400
0.6389 Remote Similarity NPC101139
0.6386 Remote Similarity NPC208302
0.6386 Remote Similarity NPC326200
0.6383 Remote Similarity NPC78154

  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 NPC139658 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
0.9722 High Similarity NPD295 Approved
0.9722 High Similarity NPD296 Approved
0.9722 High Similarity NPD293 Approved
0.9324 High Similarity NPD590 Approved
0.9324 High Similarity NPD589 Approved
0.9167 High Similarity NPD9593 Approved
0.9167 High Similarity NPD9588 Approved
0.9167 High Similarity NPD9589 Approved
0.9167 High Similarity NPD9594 Approved
0.9167 High Similarity NPD80 Approved
0.9167 High Similarity NPD9590 Approved
0.9167 High Similarity NPD9591 Approved
0.9167 High Similarity NPD9592 Approved
0.9091 High Similarity NPD831 Approved
0.9091 High Similarity NPD830 Approved
0.8974 High Similarity NPD785 Approved
0.8642 High Similarity NPD782 Approved
0.8642 High Similarity NPD783 Approved
0.8642 High Similarity NPD781 Approved
0.8642 High Similarity NPD780 Approved
0.863 High Similarity NPD294 Approved
0.863 High Similarity NPD292 Approved
0.8519 High Similarity NPD304 Approved
0.8519 High Similarity NPD305 Approved
0.8442 Intermediate Similarity NPD9397 Approved
0.8442 Intermediate Similarity NPD9564 Approved
0.8442 Intermediate Similarity NPD79 Approved
0.8442 Intermediate Similarity NPD9563 Approved
0.8442 Intermediate Similarity NPD9393 Approved
0.8434 Intermediate Similarity NPD771 Phase 3
0.8415 Intermediate Similarity NPD2002 Discontinued
0.8415 Intermediate Similarity NPD3426 Approved
0.8415 Intermediate Similarity NPD4146 Approved
0.8415 Intermediate Similarity NPD3428 Approved
0.8415 Intermediate Similarity NPD4145 Approved
0.84 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD9505 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1051 Approved
0.8333 Intermediate Similarity NPD1052 Approved
0.8333 Intermediate Similarity NPD5915 Approved
0.8333 Intermediate Similarity NPD1053 Approved
0.8312 Intermediate Similarity NPD603 Approved
0.8312 Intermediate Similarity NPD4144 Approved
0.8312 Intermediate Similarity NPD4147 Approved
0.8272 Intermediate Similarity NPD3429 Approved
0.8272 Intermediate Similarity NPD3427 Approved
0.8267 Intermediate Similarity NPD9728 Phase 1
0.8228 Intermediate Similarity NPD5372 Approved
0.8228 Intermediate Similarity NPD260 Discontinued
0.8228 Intermediate Similarity NPD5371 Approved
0.8101 Intermediate Similarity NPD507 Approved
0.8101 Intermediate Similarity NPD508 Approved
0.8049 Intermediate Similarity NPD9395 Approved
0.8023 Intermediate Similarity NPD4543 Discontinued
0.8 Intermediate Similarity NPD297 Approved
0.8 Intermediate Similarity NPD1617 Discontinued
0.8 Intermediate Similarity NPD9 Approved
0.7955 Intermediate Similarity NPD5554 Approved
0.7927 Intermediate Similarity NPD2001 Discontinued
0.7901 Intermediate Similarity NPD4026 Approved
0.7901 Intermediate Similarity NPD4027 Approved
0.7901 Intermediate Similarity NPD3035 Approved
0.7865 Intermediate Similarity NPD1738 Approved
0.7865 Intermediate Similarity NPD2005 Discontinued
0.7841 Intermediate Similarity NPD2878 Approved
0.7841 Intermediate Similarity NPD199 Approved
0.7841 Intermediate Similarity NPD3982 Approved
0.7841 Intermediate Similarity NPD736 Approved
0.7841 Intermediate Similarity NPD735 Approved
0.7841 Intermediate Similarity NPD3980 Approved
0.7841 Intermediate Similarity NPD197 Approved
0.7831 Intermediate Similarity NPD2538 Approved
0.7831 Intermediate Similarity NPD2539 Approved
0.7816 Intermediate Similarity NPD7160 Approved
0.7805 Intermediate Similarity NPD4170 Approved
0.7805 Intermediate Similarity NPD4169 Approved
0.7805 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD9349 Approved
0.7791 Intermediate Similarity NPD9350 Approved
0.7791 Intermediate Similarity NPD9351 Phase 3
0.7791 Intermediate Similarity NPD9348 Approved
0.7711 Intermediate Similarity NPD4635 Approved
0.7683 Intermediate Similarity NPD472 Approved
0.7647 Intermediate Similarity NPD5252 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD5178 Approved
0.7609 Intermediate Similarity NPD1946 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD524 Approved
0.7609 Intermediate Similarity NPD523 Approved
0.7582 Intermediate Similarity NPD528 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD713 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD173 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD3981 Approved
0.7561 Intermediate Similarity NPD3979 Approved
0.7561 Intermediate Similarity NPD3904 Approved
0.7561 Intermediate Similarity NPD3903 Approved
0.7529 Intermediate Similarity NPD2208 Approved
0.7529 Intermediate Similarity NPD2205 Approved
0.7528 Intermediate Similarity NPD1812 Approved
0.7528 Intermediate Similarity NPD1814 Approved
0.75 Intermediate Similarity NPD1800 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD262 Approved
0.75 Intermediate Similarity NPD263 Approved
0.7471 Intermediate Similarity NPD5675 Discontinued
0.7471 Intermediate Similarity NPD3345 Approved
0.7442 Intermediate Similarity NPD4409 Approved
0.7442 Intermediate Similarity NPD4636 Approved
0.7442 Intermediate Similarity NPD4406 Approved
0.7386 Intermediate Similarity NPD5656 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD1916 Discontinued
0.7326 Intermediate Similarity NPD5916 Discontinued
0.7292 Intermediate Similarity NPD309 Approved
0.7292 Intermediate Similarity NPD4936 Approved
0.7292 Intermediate Similarity NPD310 Approved
0.7292 Intermediate Similarity NPD311 Approved
0.7292 Intermediate Similarity NPD4937 Approved
0.7292 Intermediate Similarity NPD314 Approved
0.7292 Intermediate Similarity NPD315 Approved
0.7292 Intermediate Similarity NPD10 Approved
0.7273 Intermediate Similarity NPD588 Approved
0.7273 Intermediate Similarity NPD587 Approved
0.7253 Intermediate Similarity NPD243 Approved
0.7253 Intermediate Similarity NPD8 Approved
0.7241 Intermediate Similarity NPD3099 Discontinued
0.7222 Intermediate Similarity NPD2998 Approved
0.7222 Intermediate Similarity NPD2997 Approved
0.7222 Intermediate Similarity NPD3000 Approved
0.7209 Intermediate Similarity NPD4544 Approved
0.7143 Intermediate Similarity NPD4405 Approved
0.7143 Intermediate Similarity NPD4408 Approved
0.7143 Intermediate Similarity NPD4407 Approved
0.7113 Intermediate Similarity NPD1028 Approved
0.7113 Intermediate Similarity NPD2980 Phase 2
0.7113 Intermediate Similarity NPD1026 Approved
0.7111 Intermediate Similarity NPD3346 Approved
0.7111 Intermediate Similarity NPD3344 Approved
0.7097 Intermediate Similarity NPD2507 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD4542 Approved
0.7065 Intermediate Similarity NPD4545 Approved
0.7053 Intermediate Similarity NPD787 Suspended
0.7041 Intermediate Similarity NPD1766 Approved
0.7041 Intermediate Similarity NPD1765 Approved
0.7041 Intermediate Similarity NPD1763 Approved
0.7041 Intermediate Similarity NPD1269 Approved
0.7041 Intermediate Similarity NPD1268 Approved
0.7041 Intermediate Similarity NPD1767 Approved
0.7041 Intermediate Similarity NPD1761 Approved
0.6989 Remote Similarity NPD2656 Approved
0.6989 Remote Similarity NPD2655 Approved
0.6979 Remote Similarity NPD5630 Phase 1
0.6974 Remote Similarity NPD675 Discontinued
0.697 Remote Similarity NPD449 Clinical (unspecified phase)
0.697 Remote Similarity NPD448 Clinical (unspecified phase)
0.6947 Remote Similarity NPD9612 Approved
0.6947 Remote Similarity NPD9609 Approved
0.6947 Remote Similarity NPD9611 Approved
0.6947 Remote Similarity NPD4117 Approved
0.6931 Remote Similarity NPD550 Approved
0.6931 Remote Similarity NPD551 Approved
0.69 Remote Similarity NPD2206 Approved
0.69 Remote Similarity NPD2207 Approved
0.6897 Remote Similarity NPD4000 Phase 3
0.6889 Remote Similarity NPD9186 Approved
0.6889 Remote Similarity NPD9184 Approved
0.6882 Remote Similarity NPD6549 Approved
0.6882 Remote Similarity NPD6548 Approved
0.6875 Remote Similarity NPD4737 Phase 2
0.6848 Remote Similarity NPD517 Discontinued
0.6842 Remote Similarity NPD1099 Approved
0.6842 Remote Similarity NPD5598 Approved
0.6842 Remote Similarity NPD1100 Approved
0.6842 Remote Similarity NPD5597 Approved
0.6842 Remote Similarity NPD9566 Approved
0.6809 Remote Similarity NPD4094 Approved
0.6796 Remote Similarity NPD2999 Approved
0.6796 Remote Similarity NPD3001 Approved
0.6778 Remote Similarity NPD187 Approved
0.6774 Remote Similarity NPD6690 Approved
0.6771 Remote Similarity NPD253 Approved
0.6765 Remote Similarity NPD1108 Approved
0.6765 Remote Similarity NPD1107 Approved
0.6737 Remote Similarity NPD6472 Discontinued
0.6737 Remote Similarity NPD157 Clinical (unspecified phase)
0.6737 Remote Similarity NPD5963 Phase 2
0.6737 Remote Similarity NPD5964 Phase 2
0.6735 Remote Similarity NPD5716 Approved
0.6735 Remote Similarity NPD2841 Approved
0.6735 Remote Similarity NPD4119 Approved
0.6667 Remote Similarity NPD1371 Approved
0.6667 Remote Similarity NPD4655 Approved
0.6667 Remote Similarity NPD4657 Approved
0.6667 Remote Similarity NPD1373 Approved
0.6667 Remote Similarity NPD1396 Approved
0.6667 Remote Similarity NPD2665 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1370 Approved
0.6667 Remote Similarity NPD1374 Approved
0.6633 Remote Similarity NPD1795 Discontinued
0.6632 Remote Similarity NPD1081 Clinical (unspecified phase)
0.6604 Remote Similarity NPD1074 Approved
0.6604 Remote Similarity NPD595 Approved
0.6604 Remote Similarity NPD1075 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