Structure

Physi-Chem Properties

Molecular Weight:  133.09
Volume:  150.195
LogP:  1.534
LogD:  1.155
LogS:  -0.216
# Rotatable Bonds:  0
TPSA:  12.03
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.563
Synthetic Accessibility Score:  1.924
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:  -4.524
MDCK Permeability:  2.6196104954578914e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.138
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.707
30% Bioavailability (F30%):  0.331

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.96
Plasma Protein Binding (PPB):  25.442323684692383%
Volume Distribution (VD):  2.973
Pgp-substrate:  60.227317810058594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.504
CYP1A2-substrate:  0.608
CYP2C19-inhibitor:  0.169
CYP2C19-substrate:  0.791
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.251
CYP2D6-inhibitor:  0.952
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.041
CYP3A4-substrate:  0.378

ADMET: Excretion

Clearance (CL):  10.42
Half-life (T1/2):  0.643

ADMET: Toxicity

hERG Blockers:  0.062
Human Hepatotoxicity (H-HT):  0.567
Drug-inuced Liver Injury (DILI):  0.058
AMES Toxicity:  0.071
Rat Oral Acute Toxicity:  0.674
Maximum Recommended Daily Dose:  0.775
Skin Sensitization:  0.668
Carcinogencity:  0.072
Eye Corrosion:  0.205
Eye Irritation:  0.217
Respiratory Toxicity:  0.82

Download Data

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

  Natural Product: NPC258046

Natural Product ID:  NPC258046
Common Name*:   1,2,3,4-Tetrahydroisoquinoline
IUPAC Name:   1,2,3,4-tetrahydroisoquinoline
Synonyms:   1,2,3,4-Tetrahydro-Isoquinoline; 1,2,3,4-Tetrahydroisoquinoline
Standard InCHIKey:  UWYZHKAOTLEWKK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
SMILES:  N1CCc2c(C1)cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL14346
PubChem CID:   7046
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota flower buds and leaves Khon Kaen province, Thailand 2010 PMID[23270663]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Leaves n.a. n.a. PMID[23642481]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3478 Nelumbo nucifera Species Nelumbonaceae 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
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10300.0 nM PMID[490121]
NPT1529 Individual Protein Phenylethanolamine N-methyltransferase Homo sapiens Inhibition = 73.0 % PMID[490122]
NPT1529 Individual Protein Phenylethanolamine N-methyltransferase Homo sapiens Inhibition = 3.0 % PMID[490122]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10000.0 nM PMID[490123]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 102329299228075.36 nM PMID[490124]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10000.0 nM PMID[490125]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens Ki = 210000.0 nM PMID[490126]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens Ki = 15000.0 nM PMID[490126]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10000.0 nM PMID[490127]
NPT1529 Individual Protein Phenylethanolamine N-methyltransferase Homo sapiens Ki = 15000.0 nM PMID[490128]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 9700.0 nM PMID[490128]
NPT288 Individual Protein Serotonin 1a (5-HT1a) receptor Rattus norvegicus Ki > 50000.0 nM PMID[490129]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 9670.0 nM PMID[490130]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10300.0 nM PMID[490131]
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus DA release = 1.51 % PMID[490132]
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus DA release = 20.0 % PMID[490132]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10300.0 nM PMID[490133]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 10000.0 nM PMID[490134]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 9700.0 nM PMID[490135]
NPT1529 Individual Protein Phenylethanolamine N-methyltransferase Homo sapiens Ki = 5800.0 nM PMID[490136]
NPT1529 Individual Protein Phenylethanolamine N-methyltransferase Homo sapiens Ki = 5800.0 nM PMID[490137]
NPT1528 Individual Protein Phenylethanolamine N-methyltransferase Bos taurus Ki = 5000.0 nM PMID[490138]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 7943.3 nM PMID[490139]
NPT6527 Individual Protein CD44 antigen Homo sapiens Kd = 6900000.0 nM PMID[490141]
NPT6526 Individual Protein CD44 antigen Mus musculus Kd = 11200000.0 nM PMID[490141]
NPT6527 Individual Protein CD44 antigen Homo sapiens IC50 = 27000000.0 nM PMID[490141]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 2818382931264449.0 nM PMID[490124]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490125]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490127]
NPT2 Others Unspecified Selectivity = 0.035 n.a. PMID[490127]
NPT2 Others Unspecified Ratio = 1.5 n.a. PMID[490128]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490130]
NPT2 Others Unspecified Ratio = 0.036 n.a. PMID[490130]
NPT29 Organism Rattus norvegicus Rattus norvegicus Basal = 98.0 % PMID[490132]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490134]
NPT2 Others Unspecified Selectivity = 0.35 n.a. PMID[490134]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490135]
NPT2 Others Unspecified Selectivity = 0.036 n.a. PMID[490135]
NPT2 Others Unspecified Selectivity ratio = 0.06 n.a. PMID[490136]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490136]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 350.0 nM PMID[490137]
NPT2 Others Unspecified Ratio Ki = 0.06 n.a. PMID[490137]
NPT2 Others Unspecified Ratio Ki = 0.06 n.a. PMID[490138]
NPT2 Others Unspecified Ki = 350.0 nM PMID[490138]
NPT2 Others Unspecified Inhibition = -41.5 % PMID[490140]
NPT2 Others Unspecified Inhibition = -12.6 % PMID[490140]
NPT27 Others Unspecified Inhibition = 46.0 % PMID[490140]
NPT27 Others Unspecified Inhibition = 86.0 % PMID[490140]
NPT2 Others Unspecified Inhibition = 26.1 % PMID[490140]
NPT2 Others Unspecified Inhibition = 2.8 % PMID[490140]
NPT2 Others Unspecified Inhibition = -54.2 % PMID[490140]
NPT35 Others n.a. LogP = 1.71 n.a. PMID[490142]
NPT2 Others Unspecified Potency n.a. 399.1 nM PMID[19555121]
NPT2 Others Unspecified Potency n.a. 31418.4 nM DOI[10.1271/bbb.56.1835]
NPT2 Others Unspecified Potency n.a. 3955.3 nM PMID[20350950]

☑ 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 NPC258046 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
0.9146 High Similarity NPC104070
0.9091 High Similarity NPC329430
0.9036 High Similarity NPC169016
0.8765 High Similarity NPC12857
0.8556 High Similarity NPC322040
0.8519 High Similarity NPC139658
0.8333 Intermediate Similarity NPC470926
0.8193 Intermediate Similarity NPC98269
0.8193 Intermediate Similarity NPC325662
0.8171 Intermediate Similarity NPC98976
0.8125 Intermediate Similarity NPC229235
0.8125 Intermediate Similarity NPC219246
0.8072 Intermediate Similarity NPC271642
0.7955 Intermediate Similarity NPC133162
0.7841 Intermediate Similarity NPC119677
0.7831 Intermediate Similarity NPC112609
0.7831 Intermediate Similarity NPC113000
0.7831 Intermediate Similarity NPC122327
0.7766 Intermediate Similarity NPC469330
0.7738 Intermediate Similarity NPC276699
0.7576 Intermediate Similarity NPC239854
0.7558 Intermediate Similarity NPC290638
0.75 Intermediate Similarity NPC108339
0.7423 Intermediate Similarity NPC471320
0.7423 Intermediate Similarity NPC471319
0.7412 Intermediate Similarity NPC299134
0.7294 Intermediate Similarity NPC244738
0.7216 Intermediate Similarity NPC7067
0.7128 Intermediate Similarity NPC305602
0.7128 Intermediate Similarity NPC60408
0.7128 Intermediate Similarity NPC17497
0.7113 Intermediate Similarity NPC108800
0.708 Intermediate Similarity NPC475915
0.7048 Intermediate Similarity NPC79618
0.7048 Intermediate Similarity NPC434
0.7037 Intermediate Similarity NPC71009
0.7033 Intermediate Similarity NPC231986
0.6979 Remote Similarity NPC176858
0.6914 Remote Similarity NPC238023
0.6914 Remote Similarity NPC310758
0.6907 Remote Similarity NPC191444
0.6897 Remote Similarity NPC217277
0.6893 Remote Similarity NPC291610
0.6882 Remote Similarity NPC474088
0.6875 Remote Similarity NPC30445
0.6867 Remote Similarity NPC291066
0.6857 Remote Similarity NPC474695
0.6829 Remote Similarity NPC66517
0.6822 Remote Similarity NPC302790
0.6814 Remote Similarity NPC320656
0.6771 Remote Similarity NPC473031
0.6759 Remote Similarity NPC24777
0.6747 Remote Similarity NPC21211
0.6744 Remote Similarity NPC200936
0.6702 Remote Similarity NPC134825
0.6696 Remote Similarity NPC326232
0.6667 Remote Similarity NPC155172
0.6637 Remote Similarity NPC313673
0.6633 Remote Similarity NPC470877
0.6625 Remote Similarity NPC198841
0.66 Remote Similarity NPC473661
0.6571 Remote Similarity NPC327226
0.6566 Remote Similarity NPC74936
0.6566 Remote Similarity NPC159178
0.6566 Remote Similarity NPC209764
0.6566 Remote Similarity NPC141139
0.6566 Remote Similarity NPC471307
0.6566 Remote Similarity NPC78041
0.6566 Remote Similarity NPC121872
0.6562 Remote Similarity NPC229477
0.6552 Remote Similarity NPC213570
0.6552 Remote Similarity NPC139416
0.6552 Remote Similarity NPC246822
0.6549 Remote Similarity NPC101139
0.6548 Remote Similarity NPC113670
0.6548 Remote Similarity NPC50266
0.6543 Remote Similarity NPC65873
0.6543 Remote Similarity NPC212114
0.6543 Remote Similarity NPC300345
0.6543 Remote Similarity NPC120441
0.6531 Remote Similarity NPC111233
0.6512 Remote Similarity NPC6107
0.6506 Remote Similarity NPC246588
0.6506 Remote Similarity NPC135924
0.65 Remote Similarity NPC149436
0.65 Remote Similarity NPC252794
0.6495 Remote Similarity NPC203076
0.6484 Remote Similarity NPC110264
0.6477 Remote Similarity NPC251490
0.6477 Remote Similarity NPC263385
0.6477 Remote Similarity NPC72670
0.6471 Remote Similarity NPC256452
0.6463 Remote Similarity NPC36357
0.6463 Remote Similarity NPC114327
0.6449 Remote Similarity NPC226778
0.6449 Remote Similarity NPC275467
0.6449 Remote Similarity NPC147000
0.6449 Remote Similarity NPC304761
0.6449 Remote Similarity NPC150254
0.6429 Remote Similarity NPC262295
0.6429 Remote Similarity NPC29680
0.6429 Remote Similarity NPC22786
0.6422 Remote Similarity NPC55529
0.642 Remote Similarity NPC269586
0.6404 Remote Similarity NPC39799
0.6404 Remote Similarity NPC280135
0.6404 Remote Similarity NPC135433
0.6404 Remote Similarity NPC158028
0.6404 Remote Similarity NPC226999
0.6404 Remote Similarity NPC193578
0.6404 Remote Similarity NPC1008
0.6404 Remote Similarity NPC87099
0.6395 Remote Similarity NPC113837
0.6395 Remote Similarity NPC289915
0.6389 Remote Similarity NPC67043
0.6373 Remote Similarity NPC471309
0.6373 Remote Similarity NPC246757
0.6373 Remote Similarity NPC291070
0.6364 Remote Similarity NPC77294
0.6356 Remote Similarity NPC314192
0.6353 Remote Similarity NPC88566
0.6333 Remote Similarity NPC54269
0.6333 Remote Similarity NPC1901
0.6325 Remote Similarity NPC143603
0.6322 Remote Similarity NPC267443
0.6321 Remote Similarity NPC474582
0.632 Remote Similarity NPC302171
0.632 Remote Similarity NPC33338
0.632 Remote Similarity NPC300020
0.6311 Remote Similarity NPC20142
0.6311 Remote Similarity NPC215351
0.631 Remote Similarity NPC210849
0.631 Remote Similarity NPC150196
0.631 Remote Similarity NPC54368
0.631 Remote Similarity NPC248705
0.63 Remote Similarity NPC173991
0.6296 Remote Similarity NPC469974
0.6296 Remote Similarity NPC277704
0.6279 Remote Similarity NPC32312
0.6279 Remote Similarity NPC198023
0.627 Remote Similarity NPC160692
0.6265 Remote Similarity NPC8235
0.6264 Remote Similarity NPC96835
0.6264 Remote Similarity NPC258492
0.6263 Remote Similarity NPC471638
0.624 Remote Similarity NPC282398
0.6239 Remote Similarity NPC476198
0.6239 Remote Similarity NPC473418
0.6235 Remote Similarity NPC200745
0.623 Remote Similarity NPC146373
0.623 Remote Similarity NPC166424
0.623 Remote Similarity NPC245244
0.6216 Remote Similarity NPC164802
0.6211 Remote Similarity NPC475289
0.6211 Remote Similarity NPC475573
0.6207 Remote Similarity NPC178527
0.62 Remote Similarity NPC12429
0.6196 Remote Similarity NPC307195
0.6195 Remote Similarity NPC275410
0.619 Remote Similarity NPC293628
0.619 Remote Similarity NPC147062
0.619 Remote Similarity NPC472258
0.619 Remote Similarity NPC10781
0.619 Remote Similarity NPC169110
0.619 Remote Similarity NPC122493
0.6186 Remote Similarity NPC91958
0.618 Remote Similarity NPC473206
0.6179 Remote Similarity NPC145754
0.6176 Remote Similarity NPC226438
0.6163 Remote Similarity NPC45756
0.616 Remote Similarity NPC126458
0.6154 Remote Similarity NPC170170
0.6154 Remote Similarity NPC219233
0.6154 Remote Similarity NPC313449
0.6154 Remote Similarity NPC211468
0.6148 Remote Similarity NPC27740
0.6132 Remote Similarity NPC290515
0.6132 Remote Similarity NPC164514
0.6132 Remote Similarity NPC303611
0.6132 Remote Similarity NPC108606
0.6132 Remote Similarity NPC226096
0.6129 Remote Similarity NPC40488
0.6111 Remote Similarity NPC271732
0.6107 Remote Similarity NPC323123
0.6102 Remote Similarity NPC264580
0.6098 Remote Similarity NPC318965
0.6091 Remote Similarity NPC167336
0.6087 Remote Similarity NPC314141
0.6083 Remote Similarity NPC273830
0.6082 Remote Similarity NPC14326
0.6078 Remote Similarity NPC78154
0.6078 Remote Similarity NPC316108
0.6077 Remote Similarity NPC253429
0.6075 Remote Similarity NPC323726
0.6075 Remote Similarity NPC125732
0.6071 Remote Similarity NPC64270
0.6066 Remote Similarity NPC192533
0.6064 Remote Similarity NPC3190
0.6064 Remote Similarity NPC249018
0.6063 Remote Similarity NPC101165

  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 NPC258046 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
0.9157 High Similarity NPD9505 Clinical (unspecified phase)
0.8989 High Similarity NPD2005 Discontinued
0.8696 High Similarity NPD1946 Clinical (unspecified phase)
0.8602 High Similarity NPD1916 Discontinued
0.8556 High Similarity NPD735 Approved
0.8556 High Similarity NPD736 Approved
0.8556 High Similarity NPD8 Approved
0.8556 High Similarity NPD243 Approved
0.8313 Intermediate Similarity NPD296 Approved
0.8313 Intermediate Similarity NPD295 Approved
0.8313 Intermediate Similarity NPD293 Approved
0.8261 Intermediate Similarity NPD5554 Approved
0.8193 Intermediate Similarity NPD603 Approved
0.8118 Intermediate Similarity NPD5371 Approved
0.8118 Intermediate Similarity NPD5372 Approved
0.809 Intermediate Similarity NPD3428 Approved
0.809 Intermediate Similarity NPD3426 Approved
0.8085 Intermediate Similarity NPD713 Clinical (unspecified phase)
0.8046 Intermediate Similarity NPD831 Approved
0.8046 Intermediate Similarity NPD830 Approved
0.8 Intermediate Similarity NPD590 Approved
0.8 Intermediate Similarity NPD589 Approved
0.8 Intermediate Similarity NPD508 Approved
0.8 Intermediate Similarity NPD507 Approved
0.7959 Intermediate Similarity NPD4936 Approved
0.7959 Intermediate Similarity NPD4937 Approved
0.7955 Intermediate Similarity NPD3427 Approved
0.7955 Intermediate Similarity NPD2539 Approved
0.7955 Intermediate Similarity NPD2538 Approved
0.7955 Intermediate Similarity NPD3429 Approved
0.7955 Intermediate Similarity NPD785 Approved
0.7935 Intermediate Similarity NPD7160 Approved
0.7907 Intermediate Similarity NPD260 Discontinued
0.7889 Intermediate Similarity NPD4146 Approved
0.7889 Intermediate Similarity NPD4145 Approved
0.7849 Intermediate Similarity NPD4405 Approved
0.7849 Intermediate Similarity NPD4408 Approved
0.7849 Intermediate Similarity NPD4407 Approved
0.7831 Intermediate Similarity NPD9589 Approved
0.7831 Intermediate Similarity NPD9590 Approved
0.7831 Intermediate Similarity NPD9588 Approved
0.7831 Intermediate Similarity NPD80 Approved
0.7831 Intermediate Similarity NPD9591 Approved
0.7831 Intermediate Similarity NPD9593 Approved
0.7831 Intermediate Similarity NPD9592 Approved
0.7831 Intermediate Similarity NPD9594 Approved
0.7826 Intermediate Similarity NPD5915 Approved
0.7778 Intermediate Similarity NPD4406 Approved
0.7778 Intermediate Similarity NPD4409 Approved
0.7766 Intermediate Similarity NPD4545 Approved
0.7766 Intermediate Similarity NPD4542 Approved
0.7742 Intermediate Similarity NPD2998 Approved
0.7742 Intermediate Similarity NPD2997 Approved
0.7742 Intermediate Similarity NPD4543 Discontinued
0.7742 Intermediate Similarity NPD3000 Approved
0.7717 Intermediate Similarity NPD9351 Phase 3
0.7717 Intermediate Similarity NPD5656 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD771 Phase 3
0.7717 Intermediate Similarity NPD9 Approved
0.7717 Intermediate Similarity NPD9349 Approved
0.7717 Intermediate Similarity NPD9348 Approved
0.7717 Intermediate Similarity NPD297 Approved
0.7717 Intermediate Similarity NPD9350 Approved
0.7692 Intermediate Similarity NPD782 Approved
0.7692 Intermediate Similarity NPD781 Approved
0.7692 Intermediate Similarity NPD2002 Discontinued
0.7692 Intermediate Similarity NPD780 Approved
0.7692 Intermediate Similarity NPD783 Approved
0.7674 Intermediate Similarity NPD9564 Approved
0.7674 Intermediate Similarity NPD79 Approved
0.7674 Intermediate Similarity NPD9563 Approved
0.7619 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD4027 Approved
0.7614 Intermediate Similarity NPD4026 Approved
0.7609 Intermediate Similarity NPD3345 Approved
0.7582 Intermediate Similarity NPD304 Approved
0.7582 Intermediate Similarity NPD305 Approved
0.7579 Intermediate Similarity NPD6549 Approved
0.7579 Intermediate Similarity NPD3980 Approved
0.7579 Intermediate Similarity NPD6548 Approved
0.7579 Intermediate Similarity NPD3982 Approved
0.7579 Intermediate Similarity NPD2878 Approved
0.7558 Intermediate Similarity NPD4144 Approved
0.7558 Intermediate Similarity NPD4147 Approved
0.7556 Intermediate Similarity NPD9395 Approved
0.7526 Intermediate Similarity NPD5597 Approved
0.7526 Intermediate Similarity NPD528 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD5598 Approved
0.75 Intermediate Similarity NPD5103 Approved
0.75 Intermediate Similarity NPD1617 Discontinued
0.7471 Intermediate Similarity NPD9393 Approved
0.7471 Intermediate Similarity NPD9397 Approved
0.7444 Intermediate Similarity NPD4635 Approved
0.7429 Intermediate Similarity NPD2039 Approved
0.7429 Intermediate Similarity NPD2038 Approved
0.7423 Intermediate Similarity NPD1738 Approved
0.7391 Intermediate Similarity NPD5252 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD4636 Approved
0.7386 Intermediate Similarity NPD1051 Approved
0.7386 Intermediate Similarity NPD1052 Approved
0.7386 Intermediate Similarity NPD1053 Approved
0.7381 Intermediate Similarity NPD292 Approved
0.7381 Intermediate Similarity NPD294 Approved
0.7374 Intermediate Similarity NPD523 Approved
0.7374 Intermediate Similarity NPD524 Approved
0.7353 Intermediate Similarity NPD959 Discontinued
0.7333 Intermediate Similarity NPD4170 Approved
0.7333 Intermediate Similarity NPD4169 Approved
0.7333 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD3979 Approved
0.7303 Intermediate Similarity NPD3904 Approved
0.7303 Intermediate Similarity NPD3981 Approved
0.7303 Intermediate Similarity NPD3903 Approved
0.7294 Intermediate Similarity NPD9728 Phase 1
0.7292 Intermediate Similarity NPD9361 Approved
0.7282 Intermediate Similarity NPD7170 Discontinued
0.7273 Intermediate Similarity NPD6499 Approved
0.7273 Intermediate Similarity NPD6498 Approved
0.7263 Intermediate Similarity NPD3346 Approved
0.7263 Intermediate Similarity NPD3344 Approved
0.7255 Intermediate Similarity NPD1028 Approved
0.7255 Intermediate Similarity NPD1026 Approved
0.7253 Intermediate Similarity NPD1800 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD2001 Discontinued
0.7234 Intermediate Similarity NPD588 Approved
0.7234 Intermediate Similarity NPD587 Approved
0.7222 Intermediate Similarity NPD3035 Approved
0.7216 Intermediate Similarity NPD197 Approved
0.7216 Intermediate Similarity NPD199 Approved
0.7207 Intermediate Similarity NPD1922 Discontinued
0.7207 Intermediate Similarity NPD5517 Phase 2
0.7207 Intermediate Similarity NPD5516 Phase 2
0.7204 Intermediate Similarity NPD3099 Discontinued
0.72 Intermediate Similarity NPD787 Suspended
0.7184 Intermediate Similarity NPD1268 Approved
0.7184 Intermediate Similarity NPD1269 Approved
0.7174 Intermediate Similarity NPD5178 Approved
0.7156 Intermediate Similarity NPD1723 Phase 2
0.7156 Intermediate Similarity NPD1720 Phase 2
0.7097 Intermediate Similarity NPD5916 Discontinued
0.7091 Intermediate Similarity NPD5162 Approved
0.7087 Intermediate Similarity NPD2980 Phase 2
0.7071 Intermediate Similarity NPD2507 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5675 Discontinued
0.7 Intermediate Similarity NPD9489 Approved
0.7 Intermediate Similarity NPD9488 Approved
0.6989 Remote Similarity NPD4544 Approved
0.6964 Remote Similarity NPD5511 Discontinued
0.6961 Remote Similarity NPD5630 Phase 1
0.6944 Remote Similarity NPD2999 Approved
0.6944 Remote Similarity NPD3001 Approved
0.6931 Remote Similarity NPD5832 Phase 3
0.6923 Remote Similarity NPD2939 Approved
0.6923 Remote Similarity NPD2937 Phase 1
0.6909 Remote Similarity NPD4674 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5253 Approved
0.6847 Remote Similarity NPD1323 Discontinued
0.6842 Remote Similarity NPD4416 Clinical (unspecified phase)
0.6822 Remote Similarity NPD1721 Clinical (unspecified phase)
0.6822 Remote Similarity NPD8009 Approved
0.6822 Remote Similarity NPD8010 Approved
0.6818 Remote Similarity NPD2913 Approved
0.6818 Remote Similarity NPD6562 Approved
0.6818 Remote Similarity NPD6561 Approved
0.6818 Remote Similarity NPD2914 Approved
0.6814 Remote Similarity NPD2396 Approved
0.6814 Remote Similarity NPD2395 Approved
0.6759 Remote Similarity NPD551 Approved
0.6759 Remote Similarity NPD4116 Approved
0.6759 Remote Similarity NPD550 Approved
0.6757 Remote Similarity NPD5629 Discontinued
0.6757 Remote Similarity NPD7062 Discontinued
0.6757 Remote Similarity NPD3551 Approved
0.6737 Remote Similarity NPD2205 Approved
0.6737 Remote Similarity NPD2208 Approved
0.6733 Remote Similarity NPD6472 Discontinued
0.6733 Remote Similarity NPD5963 Phase 2
0.6733 Remote Similarity NPD5964 Phase 2
0.6729 Remote Similarity NPD2206 Approved
0.6729 Remote Similarity NPD2207 Approved
0.6702 Remote Similarity NPD4000 Phase 3
0.6701 Remote Similarity NPD9184 Approved
0.6701 Remote Similarity NPD9186 Approved
0.6695 Remote Similarity NPD2962 Approved
0.6695 Remote Similarity NPD2961 Approved
0.6667 Remote Similarity NPD1371 Approved
0.6667 Remote Similarity NPD1373 Approved
0.6667 Remote Similarity NPD173 Clinical (unspecified phase)
0.6667 Remote Similarity NPD517 Discontinued
0.6667 Remote Similarity NPD1370 Approved
0.6667 Remote Similarity NPD1374 Approved
0.6667 Remote Similarity NPD1396 Approved
0.6667 Remote Similarity NPD472 Approved
0.6667 Remote Similarity NPD3357 Discontinued
0.6637 Remote Similarity NPD4660 Discontinued
0.6636 Remote Similarity NPD990 Approved
0.6636 Remote Similarity NPD448 Clinical (unspecified phase)
0.6636 Remote Similarity NPD449 Clinical (unspecified phase)
0.6636 Remote Similarity NPD993 Approved
0.6635 Remote Similarity NPD1795 Discontinued

  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