Structure

Physi-Chem Properties

Molecular Weight:  179.13
Volume:  202.133
LogP:  2.213
LogD:  2.06
LogS:  -3.158
# Rotatable Bonds:  4
TPSA:  35.25
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.767
Synthetic Accessibility Score:  1.997
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:  -4.626
MDCK Permeability:  3.71293535863515e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.152
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.254

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.956
Plasma Protein Binding (PPB):  61.46580505371094%
Volume Distribution (VD):  4.504
Pgp-substrate:  45.36784744262695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.916
CYP1A2-substrate:  0.872
CYP2C19-inhibitor:  0.267
CYP2C19-substrate:  0.89
CYP2C9-inhibitor:  0.047
CYP2C9-substrate:  0.31
CYP2D6-inhibitor:  0.937
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.064
CYP3A4-substrate:  0.479

ADMET: Excretion

Clearance (CL):  10.359
Half-life (T1/2):  0.231

ADMET: Toxicity

hERG Blockers:  0.588
Human Hepatotoxicity (H-HT):  0.191
Drug-inuced Liver Injury (DILI):  0.047
AMES Toxicity:  0.167
Rat Oral Acute Toxicity:  0.794
Maximum Recommended Daily Dose:  0.786
Skin Sensitization:  0.093
Carcinogencity:  0.229
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.919

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

  Natural Product: NPC26524

Natural Product ID:  NPC26524
Common Name*:   1-(4-Ethoxyphenyl)Propan-2-Amine
IUPAC Name:   1-(4-ethoxyphenyl)propan-2-amine
Synonyms:  
Standard InCHIKey:  CCAMEVFYMFXHEN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H17NO/c1-3-13-11-6-4-10(5-7-11)8-9(2)12/h4-7,9H,3,8,12H2,1-2H3
SMILES:  CCOc1ccc(cc1)CC(C)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL161985
PubChem CID:   125379
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000186] Phenethylamines
          • [CHEMONTID:0000188] Amphetamines and derivatives

*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
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12935 Thymus quinquecostatus Species Lamiaceae 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
NPT438 Individual Protein Serotonin 2c (5-HT2c) receptor Rattus norvegicus Ki > 10000.0 nM PMID[531206]
NPT1488 Individual Protein Monoamine oxidase A Rattus norvegicus IC50 = 200.0 nM PMID[531207]
NPT1488 Individual Protein Monoamine oxidase A Rattus norvegicus Ki = 220.0 nM PMID[531208]
NPT1487 Individual Protein Monoamine oxidase B Rattus norvegicus Ki > 100000.0 nM PMID[531208]
NPT1777 Protein Family Serotonin 2 (5-HT2) receptor Rattus norvegicus Ki > 10000.0 nM PMID[531206]

☑ 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 NPC26524 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
0.9524 High Similarity NPC97811
0.9238 High Similarity NPC42383
0.8909 High Similarity NPC21890
0.8889 High Similarity NPC186469
0.8571 High Similarity NPC328267
0.8448 Intermediate Similarity NPC120075
0.843 Intermediate Similarity NPC320242
0.8273 Intermediate Similarity NPC108875
0.8273 Intermediate Similarity NPC38079
0.825 Intermediate Similarity NPC211992
0.8241 Intermediate Similarity NPC471576
0.8235 Intermediate Similarity NPC263835
0.8198 Intermediate Similarity NPC470393
0.8198 Intermediate Similarity NPC473855
0.819 Intermediate Similarity NPC321956
0.8182 Intermediate Similarity NPC298486
0.8167 Intermediate Similarity NPC318357
0.813 Intermediate Similarity NPC136112
0.813 Intermediate Similarity NPC141739
0.8095 Intermediate Similarity NPC71853
0.8091 Intermediate Similarity NPC51633
0.8049 Intermediate Similarity NPC272463
0.8031 Intermediate Similarity NPC247018
0.8031 Intermediate Similarity NPC307123
0.8031 Intermediate Similarity NPC97870
0.8018 Intermediate Similarity NPC192596
0.8 Intermediate Similarity NPC99886
0.8 Intermediate Similarity NPC177844
0.8 Intermediate Similarity NPC259134
0.8 Intermediate Similarity NPC291847
0.8 Intermediate Similarity NPC8002
0.7982 Intermediate Similarity NPC95755
0.7967 Intermediate Similarity NPC13020
0.7967 Intermediate Similarity NPC140359
0.7909 Intermediate Similarity NPC125732
0.7909 Intermediate Similarity NPC100870
0.7903 Intermediate Similarity NPC105513
0.7891 Intermediate Similarity NPC470392
0.787 Intermediate Similarity NPC471581
0.7851 Intermediate Similarity NPC43275
0.7823 Intermediate Similarity NPC217277
0.7807 Intermediate Similarity NPC176971
0.7788 Intermediate Similarity NPC283546
0.7787 Intermediate Similarity NPC321133
0.7778 Intermediate Similarity NPC166837
0.7768 Intermediate Similarity NPC307425
0.7759 Intermediate Similarity NPC145638
0.7759 Intermediate Similarity NPC290566
0.7739 Intermediate Similarity NPC157473
0.7739 Intermediate Similarity NPC258171
0.7739 Intermediate Similarity NPC151530
0.7719 Intermediate Similarity NPC128730
0.7719 Intermediate Similarity NPC8302
0.7705 Intermediate Similarity NPC256369
0.7692 Intermediate Similarity NPC88868
0.7692 Intermediate Similarity NPC231251
0.7692 Intermediate Similarity NPC25067
0.7687 Intermediate Similarity NPC204546
0.768 Intermediate Similarity NPC211218
0.768 Intermediate Similarity NPC255253
0.7679 Intermediate Similarity NPC107101
0.7674 Intermediate Similarity NPC329595
0.7674 Intermediate Similarity NPC326599
0.7672 Intermediate Similarity NPC309982
0.7672 Intermediate Similarity NPC146530
0.7672 Intermediate Similarity NPC291837
0.7658 Intermediate Similarity NPC313918
0.7658 Intermediate Similarity NPC470161
0.7652 Intermediate Similarity NPC326801
0.7619 Intermediate Similarity NPC62101
0.7619 Intermediate Similarity NPC95733
0.7611 Intermediate Similarity NPC300166
0.7607 Intermediate Similarity NPC24777
0.7597 Intermediate Similarity NPC262641
0.7565 Intermediate Similarity NPC473393
0.7565 Intermediate Similarity NPC238115
0.7559 Intermediate Similarity NPC29477
0.7559 Intermediate Similarity NPC110131
0.7544 Intermediate Similarity NPC179686
0.7544 Intermediate Similarity NPC68055
0.7544 Intermediate Similarity NPC298224
0.7544 Intermediate Similarity NPC305205
0.7542 Intermediate Similarity NPC46844
0.7537 Intermediate Similarity NPC282087
0.7537 Intermediate Similarity NPC259800
0.7537 Intermediate Similarity NPC318984
0.7537 Intermediate Similarity NPC328137
0.7537 Intermediate Similarity NPC318028
0.7537 Intermediate Similarity NPC317741
0.7537 Intermediate Similarity NPC241086
0.7522 Intermediate Similarity NPC13755
0.7521 Intermediate Similarity NPC10286
0.7521 Intermediate Similarity NPC213
0.7519 Intermediate Similarity NPC283079
0.75 Intermediate Similarity NPC303611
0.75 Intermediate Similarity NPC113457
0.75 Intermediate Similarity NPC289330
0.75 Intermediate Similarity NPC326447
0.75 Intermediate Similarity NPC226096
0.75 Intermediate Similarity NPC17388
0.75 Intermediate Similarity NPC290515
0.75 Intermediate Similarity NPC108606
0.75 Intermediate Similarity NPC471308
0.75 Intermediate Similarity NPC164514
0.75 Intermediate Similarity NPC160120
0.75 Intermediate Similarity NPC175298
0.75 Intermediate Similarity NPC53596
0.7481 Intermediate Similarity NPC212850
0.7481 Intermediate Similarity NPC83289
0.7481 Intermediate Similarity NPC189724
0.7479 Intermediate Similarity NPC55300
0.7478 Intermediate Similarity NPC292792
0.7478 Intermediate Similarity NPC38209
0.7478 Intermediate Similarity NPC241224
0.7463 Intermediate Similarity NPC231163
0.7463 Intermediate Similarity NPC318591
0.7463 Intermediate Similarity NPC474673
0.7463 Intermediate Similarity NPC253429
0.7458 Intermediate Similarity NPC474272
0.7458 Intermediate Similarity NPC259554
0.7447 Intermediate Similarity NPC47672
0.7445 Intermediate Similarity NPC78530
0.7438 Intermediate Similarity NPC235250
0.7436 Intermediate Similarity NPC251306
0.7436 Intermediate Similarity NPC194034
0.7422 Intermediate Similarity NPC124776
0.7419 Intermediate Similarity NPC283760
0.7417 Intermediate Similarity NPC115379
0.7417 Intermediate Similarity NPC165646
0.7407 Intermediate Similarity NPC326860
0.7407 Intermediate Similarity NPC197239
0.7395 Intermediate Similarity NPC106141
0.7395 Intermediate Similarity NPC137685
0.7391 Intermediate Similarity NPC12870
0.7391 Intermediate Similarity NPC24327
0.7377 Intermediate Similarity NPC303370
0.7373 Intermediate Similarity NPC75440
0.7368 Intermediate Similarity NPC29601
0.7368 Intermediate Similarity NPC155847
0.7368 Intermediate Similarity NPC289381
0.7364 Intermediate Similarity NPC301713
0.7355 Intermediate Similarity NPC90903
0.7355 Intermediate Similarity NPC303522
0.735 Intermediate Similarity NPC1065
0.7348 Intermediate Similarity NPC274732
0.7348 Intermediate Similarity NPC471953
0.7348 Intermediate Similarity NPC118419
0.7343 Intermediate Similarity NPC203424
0.7343 Intermediate Similarity NPC206372
0.7339 Intermediate Similarity NPC293424
0.7328 Intermediate Similarity NPC109637
0.7323 Intermediate Similarity NPC471315
0.7323 Intermediate Similarity NPC471314
0.7317 Intermediate Similarity NPC106551
0.7317 Intermediate Similarity NPC188867
0.7317 Intermediate Similarity NPC281686
0.7308 Intermediate Similarity NPC153990
0.7304 Intermediate Similarity NPC12714
0.7304 Intermediate Similarity NPC84325
0.7304 Intermediate Similarity NPC310905
0.7299 Intermediate Similarity NPC66518
0.7295 Intermediate Similarity NPC161696
0.7293 Intermediate Similarity NPC160692
0.7293 Intermediate Similarity NPC325568
0.7292 Intermediate Similarity NPC233926
0.728 Intermediate Similarity NPC59561
0.728 Intermediate Similarity NPC172253
0.7273 Intermediate Similarity NPC146422
0.7266 Intermediate Similarity NPC247298
0.7265 Intermediate Similarity NPC475269
0.7259 Intermediate Similarity NPC307682
0.7258 Intermediate Similarity NPC323948
0.7252 Intermediate Similarity NPC471321
0.7252 Intermediate Similarity NPC471306
0.725 Intermediate Similarity NPC473809
0.725 Intermediate Similarity NPC475852
0.7241 Intermediate Similarity NPC178902
0.7232 Intermediate Similarity NPC20142
0.7232 Intermediate Similarity NPC215351
0.7231 Intermediate Similarity NPC218323
0.7227 Intermediate Similarity NPC201959
0.7214 Intermediate Similarity NPC17760
0.7213 Intermediate Similarity NPC301735
0.7203 Intermediate Similarity NPC231705
0.719 Intermediate Similarity NPC266932
0.719 Intermediate Similarity NPC245552
0.7185 Intermediate Similarity NPC11147
0.7185 Intermediate Similarity NPC237227
0.7179 Intermediate Similarity NPC12987
0.7179 Intermediate Similarity NPC474603
0.7179 Intermediate Similarity NPC2518
0.7179 Intermediate Similarity NPC226778
0.7179 Intermediate Similarity NPC304761
0.7179 Intermediate Similarity NPC147000
0.7179 Intermediate Similarity NPC150254
0.7177 Intermediate Similarity NPC258992
0.7176 Intermediate Similarity NPC172403
0.7176 Intermediate Similarity NPC251571
0.7174 Intermediate Similarity NPC323204
0.7172 Intermediate Similarity NPC156311

  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 NPC26524 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
0.8839 High Similarity NPD595 Approved
0.8839 High Similarity NPD593 Approved
0.875 High Similarity NPD592 Approved
0.875 High Similarity NPD594 Approved
0.8571 High Similarity NPD2428 Approved
0.8571 High Similarity NPD2429 Approved
0.8547 High Similarity NPD2554 Approved
0.8547 High Similarity NPD2556 Approved
0.8462 Intermediate Similarity NPD3049 Approved
0.843 Intermediate Similarity NPD1819 Approved
0.843 Intermediate Similarity NPD1820 Approved
0.843 Intermediate Similarity NPD1817 Approved
0.843 Intermediate Similarity NPD1818 Approved
0.8273 Intermediate Similarity NPD9608 Approved
0.8273 Intermediate Similarity NPD9610 Approved
0.8268 Intermediate Similarity NPD3054 Approved
0.8268 Intermediate Similarity NPD3052 Approved
0.824 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.8205 Intermediate Similarity NPD3596 Phase 2
0.8182 Intermediate Similarity NPD2231 Phase 2
0.8182 Intermediate Similarity NPD2235 Phase 2
0.8174 Intermediate Similarity NPD821 Approved
0.816 Intermediate Similarity NPD3167 Approved
0.816 Intermediate Similarity NPD3164 Approved
0.816 Intermediate Similarity NPD3165 Approved
0.816 Intermediate Similarity NPD3166 Approved
0.813 Intermediate Similarity NPD1794 Approved
0.813 Intermediate Similarity NPD1770 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD6581 Approved
0.8067 Intermediate Similarity NPD6580 Approved
0.8065 Intermediate Similarity NPD558 Phase 2
0.8065 Intermediate Similarity NPD3690 Phase 2
0.8065 Intermediate Similarity NPD3691 Phase 2
0.8049 Intermediate Similarity NPD196 Phase 1
0.8031 Intermediate Similarity NPD1423 Approved
0.8016 Intermediate Similarity NPD5746 Approved
0.8016 Intermediate Similarity NPD3179 Approved
0.8016 Intermediate Similarity NPD3180 Approved
0.8 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7982 Intermediate Similarity NPD2684 Approved
0.7966 Intermediate Similarity NPD2557 Approved
0.7939 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD596 Approved
0.7937 Intermediate Similarity NPD600 Approved
0.7917 Intermediate Similarity NPD2486 Discontinued
0.7895 Intermediate Similarity NPD9624 Approved
0.7891 Intermediate Similarity NPD5745 Approved
0.7891 Intermediate Similarity NPD2245 Discovery
0.7874 Intermediate Similarity NPD5163 Phase 2
0.7851 Intermediate Similarity NPD2595 Approved
0.7851 Intermediate Similarity NPD2594 Approved
0.7823 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD2614 Approved
0.7787 Intermediate Similarity NPD2667 Approved
0.7787 Intermediate Similarity NPD2668 Approved
0.7761 Intermediate Similarity NPD2459 Approved
0.7761 Intermediate Similarity NPD2460 Phase 3
0.7761 Intermediate Similarity NPD2458 Approved
0.7759 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7752 Intermediate Similarity NPD3532 Approved
0.7752 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7752 Intermediate Similarity NPD3531 Approved
0.7752 Intermediate Similarity NPD3530 Approved
0.7739 Intermediate Similarity NPD5373 Approved
0.7739 Intermediate Similarity NPD5374 Approved
0.7734 Intermediate Similarity NPD6179 Discontinued
0.7727 Intermediate Similarity NPD7425 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD3294 Phase 2
0.7712 Intermediate Similarity NPD7843 Approved
0.771 Intermediate Similarity NPD2653 Approved
0.7705 Intermediate Similarity NPD3443 Approved
0.7705 Intermediate Similarity NPD6382 Discontinued
0.7705 Intermediate Similarity NPD3445 Approved
0.7705 Intermediate Similarity NPD3444 Approved
0.7687 Intermediate Similarity NPD7153 Discontinued
0.7686 Intermediate Similarity NPD318 Approved
0.7686 Intermediate Similarity NPD317 Approved
0.768 Intermediate Similarity NPD6542 Approved
0.768 Intermediate Similarity NPD6582 Phase 2
0.768 Intermediate Similarity NPD3685 Discontinued
0.768 Intermediate Similarity NPD6543 Approved
0.768 Intermediate Similarity NPD6540 Phase 3
0.768 Intermediate Similarity NPD6583 Phase 3
0.768 Intermediate Similarity NPD6539 Approved
0.768 Intermediate Similarity NPD4129 Approved
0.7669 Intermediate Similarity NPD2240 Approved
0.7669 Intermediate Similarity NPD2239 Approved
0.7652 Intermediate Similarity NPD1536 Approved
0.7638 Intermediate Similarity NPD2990 Approved
0.7638 Intermediate Similarity NPD2987 Approved
0.7638 Intermediate Similarity NPD7018 Phase 2
0.763 Intermediate Similarity NPD4162 Approved
0.7619 Intermediate Similarity NPD6538 Approved
0.7619 Intermediate Similarity NPD6541 Approved
0.7619 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD4474 Approved
0.7615 Intermediate Similarity NPD3162 Approved
0.7615 Intermediate Similarity NPD7477 Discontinued
0.7615 Intermediate Similarity NPD3163 Approved
0.7615 Intermediate Similarity NPD4475 Approved
0.7609 Intermediate Similarity NPD3536 Discontinued
0.7609 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD550 Approved
0.7607 Intermediate Similarity NPD551 Approved
0.7583 Intermediate Similarity NPD9614 Approved
0.7583 Intermediate Similarity NPD9618 Approved
0.7559 Intermediate Similarity NPD4098 Discontinued
0.7559 Intermediate Similarity NPD3568 Approved
0.7559 Intermediate Similarity NPD3567 Approved
0.7557 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD856 Approved
0.7541 Intermediate Similarity NPD16 Approved
0.754 Intermediate Similarity NPD1669 Approved
0.7538 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD1537 Approved
0.7537 Intermediate Similarity NPD1538 Phase 1
0.7537 Intermediate Similarity NPD1519 Approved
0.7521 Intermediate Similarity NPD7157 Approved
0.7519 Intermediate Similarity NPD1521 Approved
0.7519 Intermediate Similarity NPD1520 Approved
0.75 Intermediate Similarity NPD9609 Approved
0.75 Intermediate Similarity NPD1241 Discontinued
0.75 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9611 Approved
0.75 Intermediate Similarity NPD9612 Approved
0.75 Intermediate Similarity NPD6584 Phase 3
0.75 Intermediate Similarity NPD3134 Approved
0.7482 Intermediate Similarity NPD2874 Phase 2
0.7463 Intermediate Similarity NPD2155 Approved
0.7463 Intermediate Similarity NPD2156 Approved
0.7463 Intermediate Similarity NPD2154 Approved
0.746 Intermediate Similarity NPD2561 Approved
0.746 Intermediate Similarity NPD2562 Approved
0.7444 Intermediate Similarity NPD2986 Phase 2
0.7444 Intermediate Similarity NPD2989 Phase 2
0.7442 Intermediate Similarity NPD1712 Approved
0.7436 Intermediate Similarity NPD290 Approved
0.7436 Intermediate Similarity NPD1358 Approved
0.7429 Intermediate Similarity NPD52 Approved
0.7429 Intermediate Similarity NPD7526 Approved
0.7429 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD4597 Approved
0.7426 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD4598 Approved
0.7426 Intermediate Similarity NPD2030 Discontinued
0.7424 Intermediate Similarity NPD3140 Approved
0.7424 Intermediate Similarity NPD3142 Approved
0.7417 Intermediate Similarity NPD5535 Approved
0.7407 Intermediate Similarity NPD1522 Approved
0.7407 Intermediate Similarity NPD1523 Approved
0.7405 Intermediate Similarity NPD1336 Approved
0.7402 Intermediate Similarity NPD1421 Approved
0.7402 Intermediate Similarity NPD1420 Approved
0.7391 Intermediate Similarity NPD5160 Discontinued
0.7388 Intermediate Similarity NPD2200 Suspended
0.7376 Intermediate Similarity NPD6030 Approved
0.7376 Intermediate Similarity NPD6031 Approved
0.735 Intermediate Similarity NPD811 Approved
0.735 Intermediate Similarity NPD968 Approved
0.735 Intermediate Similarity NPD810 Approved
0.735 Intermediate Similarity NPD812 Approved
0.7348 Intermediate Similarity NPD839 Approved
0.7348 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD840 Approved
0.7343 Intermediate Similarity NPD4180 Approved
0.7343 Intermediate Similarity NPD4179 Approved
0.7339 Intermediate Similarity NPD1182 Approved
0.7333 Intermediate Similarity NPD2661 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD9568 Approved
0.7313 Intermediate Similarity NPD2157 Approved
0.7311 Intermediate Similarity NPD5451 Approved
0.7308 Intermediate Similarity NPD4993 Discontinued
0.7305 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD3110 Approved
0.7293 Intermediate Similarity NPD3109 Approved
0.728 Intermediate Similarity NPD1798 Approved
0.728 Intermediate Similarity NPD1797 Approved
0.7279 Intermediate Similarity NPD2161 Phase 2
0.7279 Intermediate Similarity NPD3156 Discontinued
0.7273 Intermediate Similarity NPD9379 Approved
0.7273 Intermediate Similarity NPD9377 Approved
0.7273 Intermediate Similarity NPD1039 Discontinued
0.7266 Intermediate Similarity NPD9622 Approved
0.7246 Intermediate Similarity NPD3060 Approved
0.7241 Intermediate Similarity NPD4018 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD5356 Approved
0.7241 Intermediate Similarity NPD5355 Approved
0.7226 Intermediate Similarity NPD1375 Discontinued
0.7218 Intermediate Similarity NPD7265 Discontinued
0.7206 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD6380 Phase 1
0.7203 Intermediate Similarity NPD3687 Approved
0.7203 Intermediate Similarity NPD3686 Approved
0.7203 Intermediate Similarity NPD814 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD2559 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