Structure

Physi-Chem Properties

Molecular Weight:  250.13
Volume:  260.03
LogP:  0.671
LogD:  0.745
LogS:  -1.572
# Rotatable Bonds:  8
TPSA:  81.92
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.299
Synthetic Accessibility Score:  2.138
Fsp3:  0.385
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.784
MDCK Permeability:  2.3842707378207706e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.222
Human Intestinal Absorption (HIA):  0.438
20% Bioavailability (F20%):  0.927
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.883
Plasma Protein Binding (PPB):  41.50090789794922%
Volume Distribution (VD):  0.479
Pgp-substrate:  53.69211959838867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.077
CYP1A2-substrate:  0.057
CYP2C19-inhibitor:  0.088
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.046
CYP2C9-substrate:  0.798
CYP2D6-inhibitor:  0.055
CYP2D6-substrate:  0.139
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.153

ADMET: Excretion

Clearance (CL):  3.818
Half-life (T1/2):  0.781

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.983
Drug-inuced Liver Injury (DILI):  0.037
AMES Toxicity:  0.913
Rat Oral Acute Toxicity:  0.018
Maximum Recommended Daily Dose:  0.337
Skin Sensitization:  0.505
Carcinogencity:  0.762
Eye Corrosion:  0.004
Eye Irritation:  0.113
Respiratory Toxicity:  0.036

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

  Natural Product: NPC471638

Natural Product ID:  NPC471638
Common Name*:   N1-Hydroxy-N5-Phenethylglutaramide
IUPAC Name:   N'-hydroxy-N-(2-phenylethyl)pentanediamide
Synonyms:  
Standard InCHIKey:  MNMBNWINDLRVJD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H18N2O3/c16-12(7-4-8-13(17)15-18)14-10-9-11-5-2-1-3-6-11/h1-3,5-6,18H,4,7-10H2,(H,14,16)(H,15,17)
SMILES:  C1=CC=C(C=C1)CCNC(=O)CCCC(=O)NO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3086768
PubChem CID:   72734543
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000331] Fatty amides
          • [CHEMONTID:0001096] N-acyl amines

*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
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. n.a. n.a. PMID[12350160]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. n.a. n.a. PMID[12762794]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. Sunday Island, Papua New Guinea n.a. PMID[18163584]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. Papua New Guinea n.a. PMID[20687534]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. Panamanian n.a. PMID[24164245]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. n.a. n.a. PMID[24588245]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. n.a. n.a. PMID[28055219]
NPO33200 symploca sp. Species Microcoleaceae Bacteria n.a. n.a. n.a. PMID[29808677]

☑ 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
NPT708 Cell Line HuT78 Homo sapiens GI50 = 700.0 nM PMID[485957]
NPT393 Cell Line HCT-116 Homo sapiens GI50 = 2300.0 nM PMID[485957]
NPT393 Cell Line HCT-116 Homo sapiens GI50 > 50000.0 nM PMID[485958]
NPT83 Cell Line MCF7 Homo sapiens GI50 > 50000.0 nM PMID[485958]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 > 50000.0 nM PMID[485958]
NPT708 Cell Line HuT78 Homo sapiens GI50 > 50000.0 nM PMID[485958]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 > 50000.0 nM PMID[485958]
NPT927 Cell Line PBMC Homo sapiens GI50 > 50000.0 nM PMID[485958]
NPT5649 Individual Protein Histone deacetylase 10 Homo sapiens Inhibition = 82.0 % PMID[485958]
NPT5648 Individual Protein Histone deacetylase 11 Homo sapiens Inhibition = 72.0 % PMID[485958]
NPT5649 Individual Protein Histone deacetylase 10 Homo sapiens Inhibition = 35.0 % PMID[485958]
NPT5648 Individual Protein Histone deacetylase 11 Homo sapiens Inhibition = 24.0 % PMID[485958]
NPT5649 Individual Protein Histone deacetylase 10 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT5648 Individual Protein Histone deacetylase 11 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT27 Others Unspecified GI50 > 100000.0 nM PMID[485957]
NPT2 Others Unspecified Ratio IC50 = 110.0 n.a. PMID[485957]
NPT692 Individual Protein Histone deacetylase 6 Homo sapiens IC50 = 385.8 nM PMID[485957]
NPT688 Individual Protein Histone deacetylase 4 Homo sapiens IC50 > 1000.0 nM PMID[485957]
NPT685 Individual Protein Histone deacetylase 2 Homo sapiens IC50 = 3.5 nM PMID[485957]
NPT685 Individual Protein Histone deacetylase 2 Homo sapiens IC50 > 1000.0 nM PMID[485958]
NPT2 Others Unspecified Activity = 113.0 % PMID[485958]
NPT684 Individual Protein Histone deacetylase 1 Homo sapiens Inhibition = 86.0 % PMID[485958]
NPT685 Individual Protein Histone deacetylase 2 Homo sapiens Inhibition = 76.0 % PMID[485958]
NPT4345 Protein Complex Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) Homo sapiens Inhibition = 86.0 % PMID[485958]
NPT688 Individual Protein Histone deacetylase 4 Homo sapiens Inhibition = 80.0 % PMID[485958]
NPT689 Individual Protein Histone deacetylase 5 Homo sapiens Inhibition = 49.0 % PMID[485958]
NPT692 Individual Protein Histone deacetylase 6 Homo sapiens Inhibition = 85.0 % PMID[485958]
NPT690 Individual Protein Histone deacetylase 7 Homo sapiens Inhibition = 47.0 % PMID[485958]
NPT687 Individual Protein Histone deacetylase 8 Homo sapiens Inhibition = 70.0 % PMID[485958]
NPT691 Individual Protein Histone deacetylase 9 Homo sapiens Inhibition = 70.0 % PMID[485958]
NPT684 Individual Protein Histone deacetylase 1 Homo sapiens Inhibition = 31.0 % PMID[485958]
NPT685 Individual Protein Histone deacetylase 2 Homo sapiens Inhibition = 17.0 % PMID[485958]
NPT4345 Protein Complex Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) Homo sapiens Inhibition = 36.0 % PMID[485958]
NPT688 Individual Protein Histone deacetylase 4 Homo sapiens Inhibition = 6.0 % PMID[485958]
NPT689 Individual Protein Histone deacetylase 5 Homo sapiens Inhibition = 0.0 % PMID[485958]
NPT692 Individual Protein Histone deacetylase 6 Homo sapiens Inhibition = 59.0 % PMID[485958]
NPT690 Individual Protein Histone deacetylase 7 Homo sapiens Inhibition = 29.0 % PMID[485958]
NPT687 Individual Protein Histone deacetylase 8 Homo sapiens Inhibition = 0.0 % PMID[485958]
NPT691 Individual Protein Histone deacetylase 9 Homo sapiens Inhibition = 14.0 % PMID[485958]
NPT684 Individual Protein Histone deacetylase 1 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT685 Individual Protein Histone deacetylase 2 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT4345 Protein Complex Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT688 Individual Protein Histone deacetylase 4 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT689 Individual Protein Histone deacetylase 5 Homo sapiens IC50 > 10000.0 nM PMID[485958]
NPT690 Individual Protein Histone deacetylase 7 Homo sapiens IC50 > 10000.0 nM PMID[485958]
NPT687 Individual Protein Histone deacetylase 8 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT691 Individual Protein Histone deacetylase 9 Homo sapiens IC50 = 5000.0 nM PMID[485958]
NPT692 Individual Protein Histone deacetylase 6 Homo sapiens IC50 < 5000.0 nM PMID[485958]

☑ 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 NPC471638 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
0.8652 High Similarity NPC226438
0.8652 High Similarity NPC245259
0.8636 High Similarity NPC470877
0.8571 High Similarity NPC303045
0.8571 High Similarity NPC161972
0.8539 High Similarity NPC78041
0.8539 High Similarity NPC121872
0.8539 High Similarity NPC159178
0.8539 High Similarity NPC209764
0.8539 High Similarity NPC74936
0.8539 High Similarity NPC141139
0.8539 High Similarity NPC471307
0.8539 High Similarity NPC172128
0.8523 High Similarity NPC12429
0.8478 Intermediate Similarity NPC25565
0.8387 Intermediate Similarity NPC311242
0.8387 Intermediate Similarity NPC473501
0.8387 Intermediate Similarity NPC475439
0.837 Intermediate Similarity NPC58674
0.8333 Intermediate Similarity NPC316108
0.8261 Intermediate Similarity NPC471309
0.8111 Intermediate Similarity NPC325441
0.809 Intermediate Similarity NPC203076
0.8 Intermediate Similarity NPC473031
0.7935 Intermediate Similarity NPC258627
0.7879 Intermediate Similarity NPC113326
0.7879 Intermediate Similarity NPC224610
0.7879 Intermediate Similarity NPC88267
0.7879 Intermediate Similarity NPC194390
0.7841 Intermediate Similarity NPC14326
0.7816 Intermediate Similarity NPC192623
0.7812 Intermediate Similarity NPC33168
0.7778 Intermediate Similarity NPC202613
0.7778 Intermediate Similarity NPC471317
0.7778 Intermediate Similarity NPC3210
0.7755 Intermediate Similarity NPC469457
0.7723 Intermediate Similarity NPC327481
0.7653 Intermediate Similarity NPC12730
0.7619 Intermediate Similarity NPC244738
0.76 Intermediate Similarity NPC471310
0.76 Intermediate Similarity NPC164859
0.7549 Intermediate Similarity NPC231705
0.75 Intermediate Similarity NPC476483
0.7451 Intermediate Similarity NPC211551
0.7429 Intermediate Similarity NPC319579
0.7426 Intermediate Similarity NPC178902
0.7419 Intermediate Similarity NPC198747
0.7396 Intermediate Similarity NPC323164
0.7396 Intermediate Similarity NPC265521
0.7379 Intermediate Similarity NPC191215
0.7379 Intermediate Similarity NPC274089
0.7358 Intermediate Similarity NPC329011
0.7333 Intermediate Similarity NPC258056
0.7308 Intermediate Similarity NPC142297
0.7294 Intermediate Similarity NPC125144
0.7294 Intermediate Similarity NPC121708
0.729 Intermediate Similarity NPC474584
0.7264 Intermediate Similarity NPC474149
0.7238 Intermediate Similarity NPC24101
0.7238 Intermediate Similarity NPC96224
0.7222 Intermediate Similarity NPC35850
0.7222 Intermediate Similarity NPC276949
0.7176 Intermediate Similarity NPC229235
0.7172 Intermediate Similarity NPC3371
0.7156 Intermediate Similarity NPC118202
0.7156 Intermediate Similarity NPC33742
0.7126 Intermediate Similarity NPC299134
0.7093 Intermediate Similarity NPC208302
0.7091 Intermediate Similarity NPC317254
0.7091 Intermediate Similarity NPC197470
0.7075 Intermediate Similarity NPC153690
0.7048 Intermediate Similarity NPC474973
0.7048 Intermediate Similarity NPC474804
0.7048 Intermediate Similarity NPC130898
0.7033 Intermediate Similarity NPC309279
0.7027 Intermediate Similarity NPC470544
0.7027 Intermediate Similarity NPC2265
0.7027 Intermediate Similarity NPC285926
0.7027 Intermediate Similarity NPC14672
0.7027 Intermediate Similarity NPC315276
0.7027 Intermediate Similarity NPC82963
0.701 Intermediate Similarity NPC78154
0.7 Intermediate Similarity NPC471318
0.7 Intermediate Similarity NPC471319
0.7 Intermediate Similarity NPC471320
0.699 Remote Similarity NPC318154
0.699 Remote Similarity NPC329375
0.6966 Remote Similarity NPC139658
0.6966 Remote Similarity NPC271642
0.6964 Remote Similarity NPC38458
0.6964 Remote Similarity NPC169328
0.6964 Remote Similarity NPC254088
0.6964 Remote Similarity NPC311737
0.6964 Remote Similarity NPC470545
0.6952 Remote Similarity NPC143516
0.6932 Remote Similarity NPC112609
0.6932 Remote Similarity NPC122327
0.6932 Remote Similarity NPC113000
0.6932 Remote Similarity NPC108218
0.6931 Remote Similarity NPC293628
0.6931 Remote Similarity NPC10781
0.6931 Remote Similarity NPC122493
0.6923 Remote Similarity NPC178681
0.6903 Remote Similarity NPC314992
0.6903 Remote Similarity NPC237420
0.6903 Remote Similarity NPC470546
0.6903 Remote Similarity NPC310467
0.69 Remote Similarity NPC215351
0.69 Remote Similarity NPC20142
0.69 Remote Similarity NPC108339
0.6893 Remote Similarity NPC214200
0.6893 Remote Similarity NPC228400
0.6887 Remote Similarity NPC45033
0.6857 Remote Similarity NPC275467
0.6854 Remote Similarity NPC276699
0.6854 Remote Similarity NPC189371
0.6854 Remote Similarity NPC98976
0.6842 Remote Similarity NPC283760
0.6818 Remote Similarity NPC273814
0.6809 Remote Similarity NPC146703
0.6809 Remote Similarity NPC474088
0.6804 Remote Similarity NPC262393
0.68 Remote Similarity NPC7067
0.6786 Remote Similarity NPC188010
0.6783 Remote Similarity NPC476990
0.6783 Remote Similarity NPC200964
0.6783 Remote Similarity NPC478014
0.6783 Remote Similarity NPC478015
0.6783 Remote Similarity NPC477061
0.6783 Remote Similarity NPC45777
0.6783 Remote Similarity NPC478016
0.6782 Remote Similarity NPC219246
0.6765 Remote Similarity NPC324569
0.6765 Remote Similarity NPC472258
0.6757 Remote Similarity NPC474544
0.6757 Remote Similarity NPC1986
0.6731 Remote Similarity NPC289381
0.6731 Remote Similarity NPC155847
0.6727 Remote Similarity NPC275410
0.6726 Remote Similarity NPC239357
0.6724 Remote Similarity NPC202521
0.6724 Remote Similarity NPC71684
0.6705 Remote Similarity NPC155429
0.6703 Remote Similarity NPC290638
0.6703 Remote Similarity NPC325662
0.6703 Remote Similarity NPC98269
0.6702 Remote Similarity NPC73637
0.6702 Remote Similarity NPC121478
0.6699 Remote Similarity NPC290515
0.6699 Remote Similarity NPC107619
0.6699 Remote Similarity NPC303611
0.6699 Remote Similarity NPC108606
0.6699 Remote Similarity NPC322598
0.6699 Remote Similarity NPC164514
0.6699 Remote Similarity NPC226096
0.6696 Remote Similarity NPC268572
0.6696 Remote Similarity NPC142599
0.6696 Remote Similarity NPC470550
0.6696 Remote Similarity NPC205652
0.6667 Remote Similarity NPC184030
0.6667 Remote Similarity NPC283468
0.6667 Remote Similarity NPC252878
0.6667 Remote Similarity NPC127343
0.6667 Remote Similarity NPC327226
0.6667 Remote Similarity NPC317400
0.6667 Remote Similarity NPC164449
0.6638 Remote Similarity NPC17388
0.6638 Remote Similarity NPC53596
0.6638 Remote Similarity NPC471308
0.6638 Remote Similarity NPC160120
0.6638 Remote Similarity NPC289330
0.6636 Remote Similarity NPC67043
0.6635 Remote Similarity NPC125732
0.6632 Remote Similarity NPC44830
0.6632 Remote Similarity NPC15839
0.6632 Remote Similarity NPC119677
0.6632 Remote Similarity NPC477770
0.663 Remote Similarity NPC224544
0.663 Remote Similarity NPC12857
0.661 Remote Similarity NPC35996
0.661 Remote Similarity NPC6975
0.661 Remote Similarity NPC175726
0.661 Remote Similarity NPC46427
0.661 Remote Similarity NPC474082
0.6609 Remote Similarity NPC122009
0.6606 Remote Similarity NPC473676
0.6596 Remote Similarity NPC231986
0.6581 Remote Similarity NPC273830
0.6574 Remote Similarity NPC471447
0.6562 Remote Similarity NPC169016
0.6552 Remote Similarity NPC43275
0.6552 Remote Similarity NPC239931
0.6552 Remote Similarity NPC82770
0.6552 Remote Similarity NPC78954
0.6543 Remote Similarity NPC198841
0.6542 Remote Similarity NPC304761
0.6542 Remote Similarity NPC147000
0.6542 Remote Similarity NPC226778
0.6542 Remote Similarity NPC150254
0.6535 Remote Similarity NPC473661

  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 NPC471638 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
0.8556 High Similarity NPD1814 Approved
0.8556 High Similarity NPD1812 Approved
0.8511 High Similarity NPD4760 Clinical (unspecified phase)
0.837 Intermediate Similarity NPD1081 Clinical (unspecified phase)
0.8352 Intermediate Similarity NPD6690 Approved
0.8065 Intermediate Similarity NPD1080 Approved
0.8 Intermediate Similarity NPD2487 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD9538 Approved
0.8 Intermediate Similarity NPD187 Approved
0.7912 Intermediate Similarity NPD1101 Approved
0.7789 Intermediate Similarity NPD4814 Discontinued
0.766 Intermediate Similarity NPD530 Approved
0.7619 Intermediate Similarity NPD9728 Phase 1
0.7579 Intermediate Similarity NPD752 Approved
0.7526 Intermediate Similarity NPD2507 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1066 Discontinued
0.75 Intermediate Similarity NPD1394 Approved
0.7475 Intermediate Similarity NPD1067 Discontinued
0.7451 Intermediate Similarity NPD999 Phase 2
0.7451 Intermediate Similarity NPD1040 Phase 2
0.7396 Intermediate Similarity NPD159 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD2895 Discontinued
0.7327 Intermediate Similarity NPD4119 Approved
0.732 Intermediate Similarity NPD719 Approved
0.732 Intermediate Similarity NPD720 Approved
0.7308 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6360 Discontinued
0.7264 Intermediate Similarity NPD3644 Approved
0.7264 Intermediate Similarity NPD3643 Approved
0.7264 Intermediate Similarity NPD3642 Approved
0.7255 Intermediate Similarity NPD1542 Approved
0.7228 Intermediate Similarity NPD1275 Phase 2
0.72 Intermediate Similarity NPD1724 Approved
0.7196 Intermediate Similarity NPD3651 Discontinued
0.7184 Intermediate Similarity NPD179 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD1540 Approved
0.7143 Intermediate Similarity NPD1409 Phase 3
0.7143 Intermediate Similarity NPD472 Approved
0.713 Intermediate Similarity NPD3066 Phase 2
0.713 Intermediate Similarity NPD4165 Phase 2
0.7115 Intermediate Similarity NPD5717 Approved
0.7115 Intermediate Similarity NPD1018 Approved
0.7115 Intermediate Similarity NPD563 Approved
0.7115 Intermediate Similarity NPD564 Approved
0.7113 Intermediate Similarity NPD517 Discontinued
0.71 Intermediate Similarity NPD528 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD1875 Phase 1
0.7091 Intermediate Similarity NPD1348 Approved
0.7087 Intermediate Similarity NPD5103 Approved
0.7075 Intermediate Similarity NPD2678 Approved
0.7075 Intermediate Similarity NPD2679 Approved
0.703 Intermediate Similarity NPD4117 Approved
0.7019 Intermediate Similarity NPD3407 Phase 3
0.699 Remote Similarity NPD1735 Approved
0.699 Remote Similarity NPD1417 Approved
0.699 Remote Similarity NPD1419 Approved
0.699 Remote Similarity NPD1737 Approved
0.699 Remote Similarity NPD1736 Approved
0.6981 Remote Similarity NPD6406 Approved
0.6972 Remote Similarity NPD1764 Approved
0.6972 Remote Similarity NPD1762 Approved
0.6961 Remote Similarity NPD9712 Approved
0.6944 Remote Similarity NPD2583 Phase 2
0.6932 Remote Similarity NPD9590 Approved
0.6932 Remote Similarity NPD9589 Approved
0.6932 Remote Similarity NPD9588 Approved
0.6932 Remote Similarity NPD9593 Approved
0.6932 Remote Similarity NPD80 Approved
0.6932 Remote Similarity NPD9594 Approved
0.6932 Remote Similarity NPD9591 Approved
0.6932 Remote Similarity NPD9592 Approved
0.6931 Remote Similarity NPD9566 Approved
0.6923 Remote Similarity NPD1052 Approved
0.6923 Remote Similarity NPD2244 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1053 Approved
0.6923 Remote Similarity NPD1051 Approved
0.6909 Remote Similarity NPD3150 Approved
0.6909 Remote Similarity NPD3148 Approved
0.6909 Remote Similarity NPD3147 Approved
0.6909 Remote Similarity NPD2658 Approved
0.6909 Remote Similarity NPD2659 Approved
0.6909 Remote Similarity NPD3149 Approved
0.6903 Remote Similarity NPD2218 Phase 2
0.6903 Remote Similarity NPD2217 Approved
0.6897 Remote Similarity NPD5702 Clinical (unspecified phase)
0.6889 Remote Similarity NPD4147 Approved
0.6889 Remote Similarity NPD603 Approved
0.6889 Remote Similarity NPD4144 Approved
0.687 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6863 Remote Similarity NPD9710 Approved
0.6863 Remote Similarity NPD253 Approved
0.6863 Remote Similarity NPD9711 Approved
0.6852 Remote Similarity NPD1107 Approved
0.6852 Remote Similarity NPD1108 Approved
0.6848 Remote Similarity NPD5372 Approved
0.6848 Remote Similarity NPD5371 Approved
0.6842 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6838 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6827 Remote Similarity NPD855 Approved
0.6827 Remote Similarity NPD9721 Approved
0.6827 Remote Similarity NPD9722 Approved
0.6827 Remote Similarity NPD5716 Approved
0.6827 Remote Similarity NPD854 Approved
0.6814 Remote Similarity NPD7522 Discontinued
0.6813 Remote Similarity NPD9397 Approved
0.6813 Remote Similarity NPD295 Approved
0.6813 Remote Similarity NPD293 Approved
0.6813 Remote Similarity NPD9393 Approved
0.6813 Remote Similarity NPD296 Approved
0.68 Remote Similarity NPD199 Approved
0.68 Remote Similarity NPD3719 Approved
0.68 Remote Similarity NPD197 Approved
0.68 Remote Similarity NPD3718 Approved
0.6786 Remote Similarity NPD2622 Approved
0.6783 Remote Similarity NPD7342 Discontinued
0.6765 Remote Similarity NPD1076 Approved
0.6742 Remote Similarity NPD505 Clinical (unspecified phase)
0.6739 Remote Similarity NPD590 Approved
0.6739 Remote Similarity NPD589 Approved
0.6737 Remote Similarity NPD785 Approved
0.6705 Remote Similarity NPD294 Approved
0.6705 Remote Similarity NPD292 Approved
0.6699 Remote Similarity NPD9609 Approved
0.6699 Remote Similarity NPD9611 Approved
0.6699 Remote Similarity NPD9612 Approved
0.6696 Remote Similarity NPD2212 Approved
0.6696 Remote Similarity NPD2210 Approved
0.6696 Remote Similarity NPD5981 Approved
0.6667 Remote Similarity NPD4818 Approved
0.6667 Remote Similarity NPD4817 Approved
0.6667 Remote Similarity NPD838 Approved
0.6667 Remote Similarity NPD2243 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1401 Approved
0.6667 Remote Similarity NPD4719 Phase 2
0.6637 Remote Similarity NPD7508 Discontinued
0.6633 Remote Similarity NPD531 Approved
0.6632 Remote Similarity NPD831 Approved
0.6632 Remote Similarity NPD830 Approved
0.663 Remote Similarity NPD9564 Approved
0.663 Remote Similarity NPD9563 Approved
0.663 Remote Similarity NPD79 Approved
0.661 Remote Similarity NPD2584 Suspended
0.661 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6607 Remote Similarity NPD456 Approved
0.6607 Remote Similarity NPD23 Approved
0.6604 Remote Similarity NPD4231 Approved
0.6604 Remote Similarity NPD3680 Approved
0.6604 Remote Similarity NPD1396 Approved
0.6604 Remote Similarity NPD3682 Approved
0.6604 Remote Similarity NPD3681 Approved
0.6604 Remote Similarity NPD4656 Approved
0.6604 Remote Similarity NPD3683 Approved
0.6604 Remote Similarity NPD4658 Approved
0.6604 Remote Similarity NPD1415 Approved
0.6604 Remote Similarity NPD4229 Approved
0.6598 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6598 Remote Similarity NPD305 Approved
0.6598 Remote Similarity NPD304 Approved
0.6596 Remote Similarity NPD226 Approved
0.6596 Remote Similarity NPD3035 Approved
0.6596 Remote Similarity NPD4026 Approved
0.6596 Remote Similarity NPD4027 Approved
0.6588 Remote Similarity NPD173 Clinical (unspecified phase)
0.6579 Remote Similarity NPD3123 Discovery
0.6574 Remote Similarity NPD467 Phase 1
0.6569 Remote Similarity NPD3772 Phase 3
0.6566 Remote Similarity NPD1628 Approved
0.6566 Remote Similarity NPD1629 Approved
0.6562 Remote Similarity NPD2538 Approved
0.6562 Remote Similarity NPD2539 Approved
0.6559 Remote Similarity NPD507 Approved
0.6559 Remote Similarity NPD508 Approved
0.6545 Remote Similarity NPD9713 Approved
0.6542 Remote Similarity NPD311 Approved
0.6542 Remote Similarity NPD315 Approved
0.6542 Remote Similarity NPD309 Approved
0.6542 Remote Similarity NPD10 Approved
0.6542 Remote Similarity NPD310 Approved
0.6542 Remote Similarity NPD314 Approved
0.6526 Remote Similarity NPD4701 Clinical (unspecified phase)
0.6526 Remote Similarity NPD4170 Approved
0.6526 Remote Similarity NPD4169 Approved
0.6522 Remote Similarity NPD1758 Phase 1
0.6522 Remote Similarity NPD1359 Approved
0.6518 Remote Similarity NPD181 Approved
0.6514 Remote Similarity NPD4095 Clinical (unspecified phase)
0.6509 Remote Similarity NPD2841 Approved
0.6504 Remote Similarity NPD4738 Phase 2
0.65 Remote Similarity NPD5578 Approved
0.65 Remote Similarity NPD5367 Discontinued
0.65 Remote Similarity NPD5577 Clinical (unspecified phase)
0.65 Remote Similarity NPD6325 Discontinued
0.6496 Remote Similarity NPD1525 Approved
0.6495 Remote Similarity NPD2205 Approved
0.6495 Remote Similarity NPD2208 Approved
0.6491 Remote Similarity NPD4031 Approved
0.6491 Remote Similarity NPD4032 Approved
0.6489 Remote Similarity NPD260 Discontinued
0.6486 Remote Similarity NPD4253 Approved
0.6486 Remote Similarity NPD4254 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