Structure

Physi-Chem Properties

Molecular Weight:  183.09
Volume:  185.122
LogP:  -0.537
LogD:  -0.412
LogS:  -2.492
# Rotatable Bonds:  3
TPSA:  75.71
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.633
Synthetic Accessibility Score:  2.485
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.146
MDCK Permeability:  7.683601143071428e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.481
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.131
Plasma Protein Binding (PPB):  14.635885238647461%
Volume Distribution (VD):  1.328
Pgp-substrate:  78.67802429199219%

ADMET: Metabolism

CYP1A2-inhibitor:  0.083
CYP1A2-substrate:  0.743
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.501
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.826
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.859
CYP3A4-inhibitor:  0.024
CYP3A4-substrate:  0.189

ADMET: Excretion

Clearance (CL):  9.194
Half-life (T1/2):  0.843

ADMET: Toxicity

hERG Blockers:  0.039
Human Hepatotoxicity (H-HT):  0.15
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.319
Rat Oral Acute Toxicity:  0.777
Maximum Recommended Daily Dose:  0.941
Skin Sensitization:  0.692
Carcinogencity:  0.047
Eye Corrosion:  0.657
Eye Irritation:  0.169
Respiratory Toxicity:  0.914

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC326599

Natural Product ID:  NPC326599
Common Name*:   4-[(1R)-2-Amino-1-Hydroxyethyl]-2-Methoxyphenol
IUPAC Name:   4-[(1R)-2-amino-1-hydroxyethyl]-2-methoxyphenol
Synonyms:  
Standard InCHIKey:  YNYAYWLBAHXHLL-QMMMGPOBSA-N
Standard InCHI:  InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3/t8-/m0/s1
SMILES:  NC[C@@H](c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1559460
PubChem CID:   688100
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1172/JCI16309]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1371/journal.pone.0115359]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[10557354]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11034610]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11419736]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11530998]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1175644]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12391014]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12812989]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12840027]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12878451]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15084647]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1521032]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15230696]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15314235]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16112079]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16770722]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1687010]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17116739]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17190852]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17875433]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18311922]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18544912]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18799520]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19425150]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19961175]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20506249]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20601097]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. faeces n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. bile n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. urine n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20876113]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[21798258]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[2268561]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[22711758]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23315938]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23717534]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23752203]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23810710]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23811455]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23868375]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23919613]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24101735]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24399466]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24494566]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24558969]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24816727]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25114169]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25181601]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25293588]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25644343]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[26236990]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[27471436]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[3179836]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[347637]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[4696527]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[5432584]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6121420]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6780563]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8600370]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8987136]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9192820]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9800648]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO20338 Mus musculus Species Muridae 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
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency = 5011.9 nM PMID[482728]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Potency = 89.1 nM PMID[482728]
NPT2 Others Unspecified Potency n.a. 29081.0 nM PMID[482728]

☑ 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 NPC326599 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 NPC329595
0.9431 High Similarity NPC140359
0.9431 High Similarity NPC13020
0.9106 High Similarity NPC118522
0.9106 High Similarity NPC169207
0.9106 High Similarity NPC115627
0.8862 High Similarity NPC120075
0.876 High Similarity NPC236347
0.876 High Similarity NPC323775
0.872 High Similarity NPC181969
0.872 High Similarity NPC320987
0.8667 High Similarity NPC14600
0.8667 High Similarity NPC312770
0.8667 High Similarity NPC41473
0.8667 High Similarity NPC160607
0.8667 High Similarity NPC204848
0.8651 High Similarity NPC35071
0.8651 High Similarity NPC177475
0.8651 High Similarity NPC148615
0.864 High Similarity NPC255675
0.8629 High Similarity NPC221049
0.855 High Similarity NPC153990
0.8516 High Similarity NPC470804
0.8516 High Similarity NPC476343
0.8478 Intermediate Similarity NPC66518
0.8467 Intermediate Similarity NPC299583
0.8462 Intermediate Similarity NPC105513
0.8455 Intermediate Similarity NPC146422
0.845 Intermediate Similarity NPC209567
0.845 Intermediate Similarity NPC298486
0.8425 Intermediate Similarity NPC135961
0.8425 Intermediate Similarity NPC37205
0.8425 Intermediate Similarity NPC160931
0.8413 Intermediate Similarity NPC164386
0.8374 Intermediate Similarity NPC8547
0.8374 Intermediate Similarity NPC139617
0.8374 Intermediate Similarity NPC257124
0.8374 Intermediate Similarity NPC156840
0.8374 Intermediate Similarity NPC78918
0.8374 Intermediate Similarity NPC173746
0.8296 Intermediate Similarity NPC130595
0.8296 Intermediate Similarity NPC214869
0.8296 Intermediate Similarity NPC93882
0.8295 Intermediate Similarity NPC183262
0.8281 Intermediate Similarity NPC24474
0.8281 Intermediate Similarity NPC311595
0.8271 Intermediate Similarity NPC291847
0.8252 Intermediate Similarity NPC115144
0.8252 Intermediate Similarity NPC277857
0.8244 Intermediate Similarity NPC471693
0.8244 Intermediate Similarity NPC165375
0.8244 Intermediate Similarity NPC220598
0.8235 Intermediate Similarity NPC285078
0.8235 Intermediate Similarity NPC6854
0.8235 Intermediate Similarity NPC313737
0.8231 Intermediate Similarity NPC211992
0.8222 Intermediate Similarity NPC114102
0.8211 Intermediate Similarity NPC246358
0.8211 Intermediate Similarity NPC233731
0.8211 Intermediate Similarity NPC145638
0.8211 Intermediate Similarity NPC290566
0.8211 Intermediate Similarity NPC36108
0.8211 Intermediate Similarity NPC7097
0.8209 Intermediate Similarity NPC155838
0.8203 Intermediate Similarity NPC85276
0.8195 Intermediate Similarity NPC191037
0.8195 Intermediate Similarity NPC58607
0.8195 Intermediate Similarity NPC178284
0.8175 Intermediate Similarity NPC218530
0.8154 Intermediate Similarity NPC207613
0.8148 Intermediate Similarity NPC262641
0.8148 Intermediate Similarity NPC35961
0.8148 Intermediate Similarity NPC195749
0.8148 Intermediate Similarity NPC52029
0.8145 Intermediate Similarity NPC137685
0.814 Intermediate Similarity NPC20674
0.8134 Intermediate Similarity NPC292056
0.8134 Intermediate Similarity NPC165045
0.8134 Intermediate Similarity NPC183181
0.8134 Intermediate Similarity NPC319625
0.8134 Intermediate Similarity NPC118533
0.8134 Intermediate Similarity NPC111247
0.8134 Intermediate Similarity NPC118787
0.8134 Intermediate Similarity NPC41706
0.8134 Intermediate Similarity NPC163332
0.8134 Intermediate Similarity NPC147821
0.812 Intermediate Similarity NPC194519
0.812 Intermediate Similarity NPC148627
0.8092 Intermediate Similarity NPC312675
0.8092 Intermediate Similarity NPC470212
0.8092 Intermediate Similarity NPC473853
0.8092 Intermediate Similarity NPC184651
0.8092 Intermediate Similarity NPC49341
0.8092 Intermediate Similarity NPC113865
0.8092 Intermediate Similarity NPC54872
0.8092 Intermediate Similarity NPC324571
0.8092 Intermediate Similarity NPC262156
0.8092 Intermediate Similarity NPC343720
0.8088 Intermediate Similarity NPC255550
0.8088 Intermediate Similarity NPC308885
0.808 Intermediate Similarity NPC195873
0.8077 Intermediate Similarity NPC229401
0.8074 Intermediate Similarity NPC252307
0.8074 Intermediate Similarity NPC474178
0.8074 Intermediate Similarity NPC245826
0.8069 Intermediate Similarity NPC470935
0.8069 Intermediate Similarity NPC471032
0.806 Intermediate Similarity NPC301713
0.8049 Intermediate Similarity NPC227894
0.8045 Intermediate Similarity NPC114901
0.8045 Intermediate Similarity NPC293701
0.8045 Intermediate Similarity NPC48990
0.8045 Intermediate Similarity NPC109822
0.8045 Intermediate Similarity NPC94276
0.8042 Intermediate Similarity NPC294249
0.803 Intermediate Similarity NPC85488
0.8015 Intermediate Similarity NPC170844
0.8015 Intermediate Similarity NPC476968
0.8015 Intermediate Similarity NPC86030
0.8015 Intermediate Similarity NPC5851
0.8015 Intermediate Similarity NPC475875
0.8 Intermediate Similarity NPC251571
0.8 Intermediate Similarity NPC5428
0.7984 Intermediate Similarity NPC259638
0.7984 Intermediate Similarity NPC137096
0.7984 Intermediate Similarity NPC293619
0.797 Intermediate Similarity NPC318777
0.797 Intermediate Similarity NPC280704
0.7969 Intermediate Similarity NPC10286
0.7969 Intermediate Similarity NPC213
0.7956 Intermediate Similarity NPC143483
0.7956 Intermediate Similarity NPC187998
0.7956 Intermediate Similarity NPC195292
0.7956 Intermediate Similarity NPC145305
0.7956 Intermediate Similarity NPC153739
0.7956 Intermediate Similarity NPC257582
0.7956 Intermediate Similarity NPC242807
0.7956 Intermediate Similarity NPC64201
0.7956 Intermediate Similarity NPC92164
0.7956 Intermediate Similarity NPC241522
0.7956 Intermediate Similarity NPC42300
0.7956 Intermediate Similarity NPC174495
0.7956 Intermediate Similarity NPC77040
0.7955 Intermediate Similarity NPC127389
0.7955 Intermediate Similarity NPC290451
0.7943 Intermediate Similarity NPC296898
0.7941 Intermediate Similarity NPC98631
0.7941 Intermediate Similarity NPC45774
0.7941 Intermediate Similarity NPC470213
0.7941 Intermediate Similarity NPC11258
0.7941 Intermediate Similarity NPC282703
0.7941 Intermediate Similarity NPC21867
0.7941 Intermediate Similarity NPC206615
0.7941 Intermediate Similarity NPC72529
0.7941 Intermediate Similarity NPC186843
0.7941 Intermediate Similarity NPC184733
0.7941 Intermediate Similarity NPC129570
0.7941 Intermediate Similarity NPC128208
0.7937 Intermediate Similarity NPC21890
0.7929 Intermediate Similarity NPC131204
0.7929 Intermediate Similarity NPC301050
0.7923 Intermediate Similarity NPC470626
0.7907 Intermediate Similarity NPC193067
0.7903 Intermediate Similarity NPC251306
0.7899 Intermediate Similarity NPC474017
0.7899 Intermediate Similarity NPC277804
0.7899 Intermediate Similarity NPC472597
0.7899 Intermediate Similarity NPC65942
0.7899 Intermediate Similarity NPC470096
0.7899 Intermediate Similarity NPC470095
0.7899 Intermediate Similarity NPC248307
0.7895 Intermediate Similarity NPC41562
0.7895 Intermediate Similarity NPC71090
0.7891 Intermediate Similarity NPC142599
0.7886 Intermediate Similarity NPC42383
0.7883 Intermediate Similarity NPC212015
0.7868 Intermediate Similarity NPC186898
0.7863 Intermediate Similarity NPC281298
0.7863 Intermediate Similarity NPC310338
0.7863 Intermediate Similarity NPC477803
0.7863 Intermediate Similarity NPC299406
0.7846 Intermediate Similarity NPC39793
0.7842 Intermediate Similarity NPC253105
0.7842 Intermediate Similarity NPC7903
0.7842 Intermediate Similarity NPC35932
0.7842 Intermediate Similarity NPC160991
0.7842 Intermediate Similarity NPC106739
0.7842 Intermediate Similarity NPC16208
0.7842 Intermediate Similarity NPC184447
0.7842 Intermediate Similarity NPC201587
0.784 Intermediate Similarity NPC97811
0.7836 Intermediate Similarity NPC228922
0.7836 Intermediate Similarity NPC197757
0.7826 Intermediate Similarity NPC142985
0.7826 Intermediate Similarity NPC472338
0.782 Intermediate Similarity NPC285289
0.781 Intermediate Similarity NPC472968
0.781 Intermediate Similarity NPC470084
0.7805 Intermediate Similarity NPC292792
0.7805 Intermediate Similarity NPC12278

  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 NPC326599 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
0.9106 High Similarity NPD9384 Approved
0.9106 High Similarity NPD9381 Approved
0.8968 High Similarity NPD9622 Approved
0.8824 High Similarity NPD3060 Approved
0.876 High Similarity NPD9620 Approved
0.876 High Similarity NPD9619 Approved
0.876 High Similarity NPD9621 Approved
0.8496 Intermediate Similarity NPD601 Approved
0.8496 Intermediate Similarity NPD598 Approved
0.8496 Intermediate Similarity NPD597 Approved
0.8455 Intermediate Similarity NPD9377 Approved
0.8455 Intermediate Similarity NPD9379 Approved
0.8433 Intermediate Similarity NPD1130 Approved
0.8433 Intermediate Similarity NPD1136 Approved
0.8433 Intermediate Similarity NPD1132 Approved
0.8425 Intermediate Similarity NPD2977 Approved
0.8425 Intermediate Similarity NPD2978 Approved
0.8374 Intermediate Similarity NPD228 Approved
0.8333 Intermediate Similarity NPD3686 Approved
0.8333 Intermediate Similarity NPD3687 Approved
0.8296 Intermediate Similarity NPD2674 Phase 3
0.8286 Intermediate Similarity NPD4162 Approved
0.8273 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD3061 Approved
0.8235 Intermediate Similarity NPD3062 Approved
0.8235 Intermediate Similarity NPD3059 Approved
0.8211 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD600 Approved
0.8209 Intermediate Similarity NPD596 Approved
0.8175 Intermediate Similarity NPD9618 Approved
0.8175 Intermediate Similarity NPD9614 Approved
0.8116 Intermediate Similarity NPD823 Approved
0.8116 Intermediate Similarity NPD5314 Approved
0.8116 Intermediate Similarity NPD817 Approved
0.8088 Intermediate Similarity NPD3144 Approved
0.8088 Intermediate Similarity NPD3145 Approved
0.8085 Intermediate Similarity NPD7153 Discontinued
0.806 Intermediate Similarity NPD558 Phase 2
0.803 Intermediate Similarity NPD2231 Phase 2
0.803 Intermediate Similarity NPD2235 Phase 2
0.8015 Intermediate Similarity NPD3027 Phase 3
0.7984 Intermediate Similarity NPD9615 Approved
0.7984 Intermediate Similarity NPD9613 Approved
0.7984 Intermediate Similarity NPD9616 Approved
0.7945 Intermediate Similarity NPD7526 Approved
0.7945 Intermediate Similarity NPD52 Approved
0.7945 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD9570 Approved
0.7923 Intermediate Similarity NPD316 Approved
0.7899 Intermediate Similarity NPD839 Approved
0.7899 Intermediate Similarity NPD840 Approved
0.7899 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD1375 Discontinued
0.7877 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD3052 Approved
0.7857 Intermediate Similarity NPD3054 Approved
0.7846 Intermediate Similarity NPD317 Approved
0.7846 Intermediate Similarity NPD318 Approved
0.7846 Intermediate Similarity NPD16 Approved
0.7846 Intermediate Similarity NPD856 Approved
0.7842 Intermediate Similarity NPD1558 Phase 1
0.7793 Intermediate Similarity NPD5241 Discontinued
0.7786 Intermediate Similarity NPD555 Phase 2
0.7778 Intermediate Similarity NPD4236 Phase 3
0.7778 Intermediate Similarity NPD4237 Approved
0.7778 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD259 Phase 1
0.7721 Intermediate Similarity NPD3053 Approved
0.7721 Intermediate Similarity NPD1820 Approved
0.7721 Intermediate Similarity NPD1818 Approved
0.7721 Intermediate Similarity NPD1817 Approved
0.7721 Intermediate Similarity NPD3055 Approved
0.7721 Intermediate Similarity NPD1819 Approved
0.7703 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD2161 Phase 2
0.7687 Intermediate Similarity NPD1774 Approved
0.7681 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD2677 Approved
0.7647 Intermediate Similarity NPD5310 Approved
0.7647 Intermediate Similarity NPD5311 Approved
0.7635 Intermediate Similarity NPD4123 Phase 3
0.7635 Intermediate Similarity NPD3536 Discontinued
0.7626 Intermediate Similarity NPD3179 Approved
0.7626 Intermediate Similarity NPD3180 Approved
0.7609 Intermediate Similarity NPD9569 Approved
0.7606 Intermediate Similarity NPD2653 Approved
0.7594 Intermediate Similarity NPD1357 Approved
0.7589 Intermediate Similarity NPD1613 Approved
0.7589 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD2238 Phase 2
0.7582 Intermediate Similarity NPD5772 Approved
0.7582 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD5773 Approved
0.755 Intermediate Similarity NPD3455 Phase 2
0.7536 Intermediate Similarity NPD602 Approved
0.7536 Intermediate Similarity NPD599 Approved
0.7536 Intermediate Similarity NPD858 Approved
0.7536 Intermediate Similarity NPD859 Approved
0.7534 Intermediate Similarity NPD5177 Phase 3
0.752 Intermediate Similarity NPD9610 Approved
0.752 Intermediate Similarity NPD9608 Approved
0.7518 Intermediate Similarity NPD1423 Approved
0.7517 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3165 Approved
0.75 Intermediate Similarity NPD3166 Approved
0.75 Intermediate Similarity NPD3164 Approved
0.75 Intermediate Similarity NPD2562 Approved
0.75 Intermediate Similarity NPD2561 Approved
0.75 Intermediate Similarity NPD3167 Approved
0.7483 Intermediate Similarity NPD6331 Phase 2
0.7483 Intermediate Similarity NPD2568 Approved
0.7466 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD825 Approved
0.7465 Intermediate Similarity NPD826 Approved
0.7464 Intermediate Similarity NPD1794 Approved
0.7447 Intermediate Similarity NPD5718 Phase 2
0.7447 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD257 Approved
0.741 Intermediate Similarity NPD258 Approved
0.74 Intermediate Similarity NPD3158 Phase 1
0.74 Intermediate Similarity NPD3157 Approved
0.7394 Intermediate Similarity NPD3532 Approved
0.7394 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD3530 Approved
0.7394 Intermediate Similarity NPD3531 Approved
0.7391 Intermediate Similarity NPD196 Phase 1
0.7386 Intermediate Similarity NPD4678 Approved
0.7386 Intermediate Similarity NPD4675 Approved
0.7376 Intermediate Similarity NPD9537 Phase 1
0.7376 Intermediate Similarity NPD9536 Phase 1
0.7376 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD3620 Phase 2
0.7342 Intermediate Similarity NPD4666 Phase 3
0.7338 Intermediate Similarity NPD1134 Approved
0.7338 Intermediate Similarity NPD1129 Approved
0.7338 Intermediate Similarity NPD1133 Approved
0.7338 Intermediate Similarity NPD1131 Approved
0.7338 Intermediate Similarity NPD1135 Approved
0.7329 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4005 Discontinued
0.7319 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7038 Approved
0.7317 Intermediate Similarity NPD7039 Approved
0.7315 Intermediate Similarity NPD302 Approved
0.7308 Intermediate Similarity NPD2560 Approved
0.7308 Intermediate Similarity NPD2563 Approved
0.7305 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD2684 Approved
0.7286 Intermediate Similarity NPD6584 Phase 3
0.7286 Intermediate Similarity NPD3691 Phase 2
0.7286 Intermediate Similarity NPD3690 Phase 2
0.7285 Intermediate Similarity NPD4739 Approved
0.7285 Intermediate Similarity NPD1424 Approved
0.7279 Intermediate Similarity NPD2667 Approved
0.7279 Intermediate Similarity NPD2668 Approved
0.7278 Intermediate Similarity NPD5709 Phase 3
0.7273 Intermediate Similarity NPD5283 Phase 1
0.7267 Intermediate Similarity NPD3122 Phase 3
0.7267 Intermediate Similarity NPD27 Approved
0.7267 Intermediate Similarity NPD2489 Approved
0.726 Intermediate Similarity NPD2156 Approved
0.726 Intermediate Similarity NPD2154 Approved
0.726 Intermediate Similarity NPD2155 Approved
0.7246 Intermediate Similarity NPD2232 Approved
0.7246 Intermediate Similarity NPD2233 Approved
0.7246 Intermediate Similarity NPD2230 Approved
0.7234 Intermediate Similarity NPD9494 Approved
0.7234 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD593 Approved
0.7218 Intermediate Similarity NPD595 Approved
0.7209 Intermediate Similarity NPD290 Approved
0.7208 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD1798 Approved
0.7206 Intermediate Similarity NPD1797 Approved
0.72 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD1669 Approved
0.7192 Intermediate Similarity NPD6895 Approved
0.7192 Intermediate Similarity NPD6896 Approved
0.719 Intermediate Similarity NPD6031 Approved
0.719 Intermediate Similarity NPD6030 Approved
0.719 Intermediate Similarity NPD5976 Discontinued
0.7176 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD3705 Approved
0.7154 Intermediate Similarity NPD9296 Approved
0.7153 Intermediate Similarity NPD6405 Approved
0.7153 Intermediate Similarity NPD3162 Approved
0.7153 Intermediate Similarity NPD6407 Approved
0.7153 Intermediate Similarity NPD3163 Approved
0.7143 Intermediate Similarity NPD4210 Discontinued
0.7143 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD9611 Approved
0.712 Intermediate Similarity NPD9612 Approved
0.712 Intermediate Similarity NPD9609 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