Structure

Physi-Chem Properties

Molecular Weight:  343.11
Volume:  342.781
LogP:  1.095
LogD:  0.609
LogS:  -2.602
# Rotatable Bonds:  8
TPSA:  113.68
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.823
Synthetic Accessibility Score:  2.919
Fsp3:  0.222
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:  -5.541
MDCK Permeability:  3.3941250876523554e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.036
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.111
Plasma Protein Binding (PPB):  93.6845932006836%
Volume Distribution (VD):  0.196
Pgp-substrate:  2.6670174598693848%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.046
CYP2C19-inhibitor:  0.058
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.135
CYP2C9-substrate:  0.932
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.126
CYP3A4-inhibitor:  0.011
CYP3A4-substrate:  0.249

ADMET: Excretion

Clearance (CL):  1.092
Half-life (T1/2):  0.909

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.328
Drug-inuced Liver Injury (DILI):  0.961
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.817
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.123
Carcinogencity:  0.086
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.013

Download Data

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

  Natural Product: NPC235421

Natural Product ID:  NPC235421
Common Name*:   Pestalamide A
IUPAC Name:   (2S)-4-[(6-benzyl-4-oxopyran-3-carbonyl)amino]-2-methyl-4-oxobutanoic acid
Synonyms:  
Standard InCHIKey:  JBQPQUZBAGHRDN-NSHDSACASA-N
Standard InCHI:  InChI=1S/C18H17NO6/c1-11(18(23)24)7-16(21)19-17(22)14-10-25-13(9-15(14)20)8-12-5-3-2-4-6-12/h2-6,9-11H,7-8H2,1H3,(H,23,24)(H,19,21,22)/t11-/m0/s1
SMILES:  C[C@@H](CC(=NC(=O)c1coc(Cc2ccccc2)cc1=O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL574520
PubChem CID:   25158704
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans
        • [CHEMONTID:0000481] Pyranones 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
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)88611-1]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np058103o]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/JR9620000040]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1966.10858561]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1972.10860562]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1985.10867263]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[10695672]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12458767]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12542363]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. sponge-derived n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15556711]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15620260]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17653510]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17827758]
NPO30915 Pestalotiopsis theae Species Sporocadaceae Eukaryota n.a. n.a. n.a. PMID[18303847]
NPO30915 Pestalotiopsis theae Species Sporocadaceae Eukaryota n.a. n.a. n.a. PMID[18855443]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20014861]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20028011]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21176790]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21543515]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21774474]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22921072]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24684908]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25044953]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25062661]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25293978]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26040782]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26132344]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26414728]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[27245874]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32159958]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[6073032]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. Database[Article]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO14234 Aspergillus niger Species Aspergillaceae 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
NPT1452 Cell Line C8166 Homo sapiens CC50 > 100000.0 nM PMID[515138]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 64200.0 nM PMID[515138]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus IC50 = 1500.0 nM PMID[515138]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 57800.0 nM PMID[515138]

☑ 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 NPC235421 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
0.7414 Intermediate Similarity NPC202613
0.7364 Intermediate Similarity NPC47667
0.7273 Intermediate Similarity NPC323007
0.7257 Intermediate Similarity NPC58674
0.725 Intermediate Similarity NPC469511
0.725 Intermediate Similarity NPC182549
0.725 Intermediate Similarity NPC114741
0.7227 Intermediate Similarity NPC477251
0.7207 Intermediate Similarity NPC258627
0.7143 Intermediate Similarity NPC169328
0.713 Intermediate Similarity NPC265662
0.712 Intermediate Similarity NPC197470
0.7119 Intermediate Similarity NPC471317
0.7099 Intermediate Similarity NPC474479
0.7087 Intermediate Similarity NPC310467
0.7087 Intermediate Similarity NPC237420
0.7069 Intermediate Similarity NPC179411
0.7054 Intermediate Similarity NPC172128
0.7037 Intermediate Similarity NPC270507
0.7027 Intermediate Similarity NPC325441
0.7016 Intermediate Similarity NPC273814
0.7 Intermediate Similarity NPC474862
0.6977 Remote Similarity NPC477061
0.6977 Remote Similarity NPC476183
0.6977 Remote Similarity NPC190663
0.6977 Remote Similarity NPC45777
0.6953 Remote Similarity NPC314992
0.6944 Remote Similarity NPC323103
0.6944 Remote Similarity NPC103387
0.6942 Remote Similarity NPC327481
0.6935 Remote Similarity NPC329011
0.6934 Remote Similarity NPC477680
0.6929 Remote Similarity NPC2265
0.6923 Remote Similarity NPC145052
0.6923 Remote Similarity NPC476120
0.6923 Remote Similarity NPC476184
0.6923 Remote Similarity NPC476281
0.6917 Remote Similarity NPC113326
0.6917 Remote Similarity NPC224610
0.6917 Remote Similarity NPC88267
0.6917 Remote Similarity NPC194390
0.6885 Remote Similarity NPC20485
0.688 Remote Similarity NPC474584
0.6875 Remote Similarity NPC477693
0.6875 Remote Similarity NPC477704
0.687 Remote Similarity NPC23453
0.687 Remote Similarity NPC160493
0.6864 Remote Similarity NPC12730
0.6846 Remote Similarity NPC475827
0.6846 Remote Similarity NPC478015
0.6846 Remote Similarity NPC80150
0.6846 Remote Similarity NPC474223
0.6846 Remote Similarity NPC478016
0.6846 Remote Similarity NPC478014
0.6842 Remote Similarity NPC4974
0.6838 Remote Similarity NPC289201
0.6838 Remote Similarity NPC278228
0.6835 Remote Similarity NPC43755
0.6835 Remote Similarity NPC127741
0.6833 Remote Similarity NPC329556
0.6829 Remote Similarity NPC40178
0.6825 Remote Similarity NPC1986
0.6825 Remote Similarity NPC153053
0.6825 Remote Similarity NPC474544
0.6818 Remote Similarity NPC35996
0.6818 Remote Similarity NPC476278
0.6815 Remote Similarity NPC81092
0.6815 Remote Similarity NPC103605
0.6814 Remote Similarity NPC470877
0.681 Remote Similarity NPC303045
0.681 Remote Similarity NPC161972
0.6803 Remote Similarity NPC51174
0.6803 Remote Similarity NPC472316
0.6803 Remote Similarity NPC475203
0.6803 Remote Similarity NPC474376
0.6803 Remote Similarity NPC472315
0.6803 Remote Similarity NPC136962
0.68 Remote Similarity NPC477250
0.6786 Remote Similarity NPC96625
0.6783 Remote Similarity NPC323164
0.6777 Remote Similarity NPC329282
0.6772 Remote Similarity NPC210092
0.6772 Remote Similarity NPC469509
0.6767 Remote Similarity NPC476241
0.6767 Remote Similarity NPC476260
0.6759 Remote Similarity NPC121800
0.6754 Remote Similarity NPC471307
0.6754 Remote Similarity NPC78041
0.6754 Remote Similarity NPC159178
0.6754 Remote Similarity NPC209764
0.6754 Remote Similarity NPC108026
0.6754 Remote Similarity NPC141139
0.6754 Remote Similarity NPC121872
0.6754 Remote Similarity NPC213156
0.6754 Remote Similarity NPC240108
0.6754 Remote Similarity NPC74936
0.6752 Remote Similarity NPC25565
0.6748 Remote Similarity NPC47536
0.6748 Remote Similarity NPC470007
0.6746 Remote Similarity NPC477476
0.6746 Remote Similarity NPC477475
0.6744 Remote Similarity NPC254088
0.6744 Remote Similarity NPC471553
0.6723 Remote Similarity NPC474308
0.672 Remote Similarity NPC319579
0.6719 Remote Similarity NPC188010
0.6719 Remote Similarity NPC471616
0.6716 Remote Similarity NPC476125
0.6716 Remote Similarity NPC476179
0.6696 Remote Similarity NPC245259
0.6696 Remote Similarity NPC476484
0.6696 Remote Similarity NPC110704
0.6695 Remote Similarity NPC475439
0.6695 Remote Similarity NPC472788
0.6695 Remote Similarity NPC103048
0.6695 Remote Similarity NPC473501
0.6695 Remote Similarity NPC477767
0.6694 Remote Similarity NPC82426
0.6694 Remote Similarity NPC301943
0.6694 Remote Similarity NPC474365
0.6694 Remote Similarity NPC475282
0.6694 Remote Similarity NPC281604
0.6694 Remote Similarity NPC91820
0.6692 Remote Similarity NPC474254
0.6692 Remote Similarity NPC474159
0.6691 Remote Similarity NPC213969
0.6691 Remote Similarity NPC296712
0.6691 Remote Similarity NPC169766
0.6691 Remote Similarity NPC165726
0.669 Remote Similarity NPC168113
0.6667 Remote Similarity NPC321852
0.6667 Remote Similarity NPC191215
0.6667 Remote Similarity NPC246913
0.6667 Remote Similarity NPC246079
0.6667 Remote Similarity NPC234376
0.6667 Remote Similarity NPC470544
0.6667 Remote Similarity NPC37115
0.6667 Remote Similarity NPC44546
0.6667 Remote Similarity NPC325479
0.6667 Remote Similarity NPC130898
0.6667 Remote Similarity NPC474804
0.6667 Remote Similarity NPC9822
0.6667 Remote Similarity NPC239357
0.6667 Remote Similarity NPC274089
0.6667 Remote Similarity NPC77992
0.6667 Remote Similarity NPC474973
0.6667 Remote Similarity NPC170484
0.6645 Remote Similarity NPC471203
0.6644 Remote Similarity NPC39431
0.6643 Remote Similarity NPC197682
0.6642 Remote Similarity NPC318067
0.6642 Remote Similarity NPC478147
0.6642 Remote Similarity NPC328107
0.6641 Remote Similarity NPC197513
0.6641 Remote Similarity NPC472164
0.6641 Remote Similarity NPC202015
0.6641 Remote Similarity NPC204784
0.6641 Remote Similarity NPC33742
0.664 Remote Similarity NPC214067
0.664 Remote Similarity NPC196246
0.6639 Remote Similarity NPC154517
0.6639 Remote Similarity NPC135951
0.6639 Remote Similarity NPC171831
0.6639 Remote Similarity NPC280616
0.6639 Remote Similarity NPC329387
0.6639 Remote Similarity NPC242913
0.6639 Remote Similarity NPC317280
0.6638 Remote Similarity NPC77273
0.6637 Remote Similarity NPC322387
0.6622 Remote Similarity NPC300443
0.662 Remote Similarity NPC471316
0.6619 Remote Similarity NPC470392
0.6615 Remote Similarity NPC470545
0.6614 Remote Similarity NPC272524
0.6614 Remote Similarity NPC265002
0.6613 Remote Similarity NPC156648
0.6613 Remote Similarity NPC21929
0.6612 Remote Similarity NPC318154
0.661 Remote Similarity NPC3371
0.661 Remote Similarity NPC12695
0.6609 Remote Similarity NPC274455
0.6609 Remote Similarity NPC70940
0.6609 Remote Similarity NPC86670
0.6607 Remote Similarity NPC475710
0.6607 Remote Similarity NPC294134
0.6607 Remote Similarity NPC53299
0.6606 Remote Similarity NPC192623
0.6596 Remote Similarity NPC6570
0.6596 Remote Similarity NPC208725
0.6596 Remote Similarity NPC471265
0.6596 Remote Similarity NPC471264
0.6593 Remote Similarity NPC472414
0.6587 Remote Similarity NPC133308
0.6587 Remote Similarity NPC1082
0.6587 Remote Similarity NPC260818
0.6587 Remote Similarity NPC474157
0.6587 Remote Similarity NPC183700
0.6587 Remote Similarity NPC305912
0.6587 Remote Similarity NPC477247
0.6585 Remote Similarity NPC321670

  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 NPC235421 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
0.7321 Intermediate Similarity NPD1066 Discontinued
0.7302 Intermediate Similarity NPD5981 Approved
0.7168 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD2066 Phase 3
0.712 Intermediate Similarity NPD1348 Approved
0.7119 Intermediate Similarity NPD6647 Phase 2
0.7009 Intermediate Similarity NPD1067 Discontinued
0.7 Intermediate Similarity NPD1040 Phase 2
0.7 Intermediate Similarity NPD999 Phase 2
0.6992 Remote Similarity NPD3642 Approved
0.6992 Remote Similarity NPD3644 Approved
0.6992 Remote Similarity NPD3643 Approved
0.6963 Remote Similarity NPD4738 Phase 2
0.6953 Remote Similarity NPD4479 Discontinued
0.6953 Remote Similarity NPD2217 Approved
0.6953 Remote Similarity NPD2218 Phase 2
0.687 Remote Similarity NPD720 Approved
0.687 Remote Similarity NPD719 Approved
0.6861 Remote Similarity NPD5729 Clinical (unspecified phase)
0.686 Remote Similarity NPD1018 Approved
0.6842 Remote Similarity NPD6325 Discontinued
0.6833 Remote Similarity NPD1930 Approved
0.6833 Remote Similarity NPD1929 Approved
0.6833 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5108 Clinical (unspecified phase)
0.681 Remote Similarity NPD4814 Discontinued
0.6777 Remote Similarity NPD5909 Discontinued
0.6774 Remote Similarity NPD2067 Discontinued
0.6769 Remote Similarity NPD4209 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6406 Approved
0.6742 Remote Similarity NPD5618 Discontinued
0.6742 Remote Similarity NPD4480 Approved
0.6726 Remote Similarity NPD1101 Approved
0.6715 Remote Similarity NPD3136 Phase 2
0.6715 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6696 Remote Similarity NPD530 Approved
0.6695 Remote Similarity NPD1875 Phase 1
0.6693 Remote Similarity NPD2652 Approved
0.6693 Remote Similarity NPD2650 Approved
0.6691 Remote Similarity NPD8416 Discontinued
0.6667 Remote Similarity NPD800 Approved
0.6667 Remote Similarity NPD1693 Approved
0.6667 Remote Similarity NPD4760 Clinical (unspecified phase)
0.6639 Remote Similarity NPD5926 Approved
0.6638 Remote Similarity NPD752 Approved
0.6638 Remote Similarity NPD6690 Approved
0.6637 Remote Similarity NPD9538 Approved
0.6617 Remote Similarity NPD6287 Discontinued
0.6615 Remote Similarity NPD1758 Phase 1
0.6614 Remote Similarity NPD181 Approved
0.6614 Remote Similarity NPD2607 Approved
0.6609 Remote Similarity NPD1089 Approved
0.6609 Remote Similarity NPD1090 Approved
0.6609 Remote Similarity NPD1086 Approved
0.6577 Remote Similarity NPD9491 Approved
0.6567 Remote Similarity NPD2584 Suspended
0.6565 Remote Similarity NPD6093 Discontinued
0.6565 Remote Similarity NPD1759 Phase 1
0.656 Remote Similarity NPD2182 Approved
0.6557 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6544 Remote Similarity NPD6302 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3123 Discovery
0.6532 Remote Similarity NPD5705 Approved
0.6532 Remote Similarity NPD5704 Approved
0.6532 Remote Similarity NPD5706 Approved
0.6532 Remote Similarity NPD467 Phase 1
0.6532 Remote Similarity NPD6685 Approved
0.6525 Remote Similarity NPD8643 Discontinued
0.6522 Remote Similarity NPD5346 Phase 2
0.6522 Remote Similarity NPD5347 Phase 2
0.6515 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6496 Remote Similarity NPD1088 Approved
0.6493 Remote Similarity NPD3132 Approved
0.6493 Remote Similarity NPD2610 Approved
0.6493 Remote Similarity NPD3131 Approved
0.6493 Remote Similarity NPD4217 Approved
0.6493 Remote Similarity NPD2612 Approved
0.6493 Remote Similarity NPD2608 Approved
0.6493 Remote Similarity NPD4216 Approved
0.6493 Remote Similarity NPD4218 Approved
0.6493 Remote Similarity NPD2609 Approved
0.6493 Remote Similarity NPD4215 Approved
0.6493 Remote Similarity NPD2611 Approved
0.6491 Remote Similarity NPD1282 Approved
0.6483 Remote Similarity NPD6681 Discovery
0.6475 Remote Similarity NPD1932 Approved
0.6471 Remote Similarity NPD1989 Approved
0.6466 Remote Similarity NPD5306 Approved
0.6466 Remote Similarity NPD3672 Approved
0.6466 Remote Similarity NPD3673 Approved
0.6466 Remote Similarity NPD5305 Approved
0.6449 Remote Similarity NPD4208 Discontinued
0.6446 Remote Similarity NPD9712 Approved
0.6444 Remote Similarity NPD6624 Discontinued
0.6441 Remote Similarity NPD1409 Phase 3
0.6439 Remote Similarity NPD2617 Discontinued
0.6435 Remote Similarity NPD531 Approved
0.6434 Remote Similarity NPD4214 Discontinued
0.6434 Remote Similarity NPD1682 Approved
0.6434 Remote Similarity NPD1681 Approved
0.6434 Remote Similarity NPD3598 Phase 3
0.6434 Remote Similarity NPD1680 Approved
0.6429 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6429 Remote Similarity NPD2329 Discontinued
0.6423 Remote Similarity NPD5765 Approved
0.6418 Remote Similarity NPD3847 Discontinued
0.6412 Remote Similarity NPD4576 Approved
0.6412 Remote Similarity NPD4431 Clinical (unspecified phase)
0.6412 Remote Similarity NPD4574 Approved
0.6403 Remote Similarity NPD2613 Approved
0.64 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6397 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6397 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6397 Remote Similarity NPD5159 Phase 2
0.6397 Remote Similarity NPD5157 Phase 1
0.6396 Remote Similarity NPD226 Approved
0.6395 Remote Similarity NPD1968 Approved
0.6395 Remote Similarity NPD1967 Approved
0.6389 Remote Similarity NPD6864 Phase 2
0.6389 Remote Similarity NPD6865 Phase 2
0.6378 Remote Similarity NPD5240 Approved
0.6378 Remote Similarity NPD1317 Discontinued
0.6378 Remote Similarity NPD5237 Approved
0.6378 Remote Similarity NPD5239 Approved
0.6378 Remote Similarity NPD1756 Approved
0.6378 Remote Similarity NPD5235 Approved
0.6378 Remote Similarity NPD1752 Approved
0.6378 Remote Similarity NPD5236 Approved
0.6377 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6371 Remote Similarity NPD164 Approved
0.637 Remote Similarity NPD3603 Phase 3
0.637 Remote Similarity NPD4807 Approved
0.637 Remote Similarity NPD4806 Approved
0.637 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6364 Remote Similarity NPD9711 Approved
0.6364 Remote Similarity NPD9710 Approved
0.6357 Remote Similarity NPD2043 Approved
0.6357 Remote Similarity NPD2045 Approved
0.6357 Remote Similarity NPD2051 Approved
0.6357 Remote Similarity NPD5454 Clinical (unspecified phase)
0.6357 Remote Similarity NPD2048 Approved
0.6357 Remote Similarity NPD21 Approved
0.6357 Remote Similarity NPD2050 Clinical (unspecified phase)
0.6357 Remote Similarity NPD2046 Approved
0.6357 Remote Similarity NPD2044 Approved
0.6357 Remote Similarity NPD2049 Clinical (unspecified phase)
0.6357 Remote Similarity NPD2047 Approved
0.635 Remote Similarity NPD3125 Approved
0.6349 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6348 Remote Similarity NPD1087 Approved
0.6348 Remote Similarity NPD4793 Discontinued
0.6343 Remote Similarity NPD1362 Clinical (unspecified phase)
0.634 Remote Similarity NPD2891 Approved
0.6333 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6328 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6328 Remote Similarity NPD2201 Approved
0.6328 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6328 Remote Similarity NPD2583 Phase 2
0.6324 Remote Similarity NPD6637 Approved
0.632 Remote Similarity NPD5048 Discontinued
0.6319 Remote Similarity NPD6852 Discontinued
0.6316 Remote Similarity NPD998 Approved
0.6308 Remote Similarity NPD1374 Approved
0.6308 Remote Similarity NPD1371 Approved
0.6308 Remote Similarity NPD1373 Approved
0.6308 Remote Similarity NPD1370 Approved
0.6304 Remote Similarity NPD2585 Clinical (unspecified phase)
0.6303 Remote Similarity NPD1080 Approved
0.6301 Remote Similarity NPD4152 Approved
0.6301 Remote Similarity NPD7978 Discontinued
0.6296 Remote Similarity NPD4136 Approved
0.6296 Remote Similarity NPD4135 Approved
0.6296 Remote Similarity NPD4106 Approved
0.6296 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6286 Remote Similarity NPD4125 Approved
0.6281 Remote Similarity NPD1564 Approved
0.6281 Remote Similarity NPD1566 Phase 3
0.6281 Remote Similarity NPD1565 Approved
0.6279 Remote Similarity NPD6912 Phase 3
0.6276 Remote Similarity NPD3480 Approved
0.6276 Remote Similarity NPD4158 Clinical (unspecified phase)
0.6271 Remote Similarity NPD1239 Approved
0.627 Remote Similarity NPD3134 Approved
0.6268 Remote Similarity NPD2574 Discontinued
0.6268 Remote Similarity NPD3616 Approved
0.6268 Remote Similarity NPD2566 Approved
0.6268 Remote Similarity NPD3088 Approved
0.6268 Remote Similarity NPD3090 Approved
0.6268 Remote Similarity NPD3614 Approved
0.6268 Remote Similarity NPD2573 Approved
0.6268 Remote Similarity NPD3615 Approved
0.6268 Remote Similarity NPD2570 Approved
0.6268 Remote Similarity NPD2571 Approved
0.6268 Remote Similarity NPD3087 Approved
0.6268 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6268 Remote Similarity NPD4745 Approved
0.6268 Remote Similarity NPD3089 Approved
0.6268 Remote Similarity NPD4746 Phase 3
0.6267 Remote Similarity NPD2014 Approved
0.6267 Remote Similarity NPD2016 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