Structure

Physi-Chem Properties

Molecular Weight:  456.17
Volume:  472.993
LogP:  3.037
LogD:  3.136
LogS:  -4.913
# Rotatable Bonds:  8
TPSA:  104.53
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.438
Synthetic Accessibility Score:  3.124
Fsp3:  0.148
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.984
MDCK Permeability:  1.574983798491303e-05
Pgp-inhibitor:  0.748
Pgp-substrate:  0.919
Human Intestinal Absorption (HIA):  0.037
20% Bioavailability (F20%):  0.955
30% Bioavailability (F30%):  0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.188
Plasma Protein Binding (PPB):  100.39521789550781%
Volume Distribution (VD):  0.639
Pgp-substrate:  0.6721891760826111%

ADMET: Metabolism

CYP1A2-inhibitor:  0.243
CYP1A2-substrate:  0.71
CYP2C19-inhibitor:  0.923
CYP2C19-substrate:  0.076
CYP2C9-inhibitor:  0.938
CYP2C9-substrate:  0.855
CYP2D6-inhibitor:  0.075
CYP2D6-substrate:  0.672
CYP3A4-inhibitor:  0.897
CYP3A4-substrate:  0.834

ADMET: Excretion

Clearance (CL):  10.686
Half-life (T1/2):  0.158

ADMET: Toxicity

hERG Blockers:  0.449
Human Hepatotoxicity (H-HT):  0.653
Drug-inuced Liver Injury (DILI):  0.979
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.136
Maximum Recommended Daily Dose:  0.971
Skin Sensitization:  0.032
Carcinogencity:  0.274
Eye Corrosion:  0.003
Eye Irritation:  0.009
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: NPC77992

Natural Product ID:  NPC77992
Common Name*:   Aspernigrin B
IUPAC Name:   4-benzyl-1-[(1S)-1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]-6-oxopyridine-3-carboxamide
Synonyms:  
Standard InCHIKey:  ZLLURFBMQBIVMQ-QHCPKHFHSA-N
Standard InCHI:  InChI=1S/C27H24N2O5/c1-33-21-15-24(34-26(31)16-21)23(13-19-10-6-3-7-11-19)29-17-22(27(28)32)20(14-25(29)30)12-18-8-4-2-5-9-18/h2-11,14-17,23H,12-13H2,1H3,(H2,28,32)/t23-/m0/s1
SMILES:  COc1cc(=O)oc(c1)[C@@H](n1cc(C(=N)O)c(cc1=O)Cc1ccccc1)Cc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463758
PubChem CID:   11775447
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001761] Kavalactones

*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. sponge-derived n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. 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]
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. n.a. n.a. Database[Article]
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[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
NPT2 Others Unspecified Activity = 25.5 % PMID[479236]
NPT2 Others Unspecified Activity = 55.0 % PMID[479236]
NPT2 Others Unspecified Activity = 33.6 % PMID[479236]
NPT2 Others Unspecified Activity = 23.5 % PMID[479236]

☑ 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 NPC77992 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
0.7552 Intermediate Similarity NPC246079
0.731 Intermediate Similarity NPC325479
0.7208 Intermediate Similarity NPC13470
0.7161 Intermediate Similarity NPC7817
0.7161 Intermediate Similarity NPC475168
0.7152 Intermediate Similarity NPC248670
0.7143 Intermediate Similarity NPC9373
0.7133 Intermediate Similarity NPC4974
0.7133 Intermediate Similarity NPC474479
0.7122 Intermediate Similarity NPC220698
0.7114 Intermediate Similarity NPC127741
0.7103 Intermediate Similarity NPC103605
0.7103 Intermediate Similarity NPC81092
0.7101 Intermediate Similarity NPC470544
0.708 Intermediate Similarity NPC33742
0.7078 Intermediate Similarity NPC135121
0.7059 Intermediate Similarity NPC201244
0.7059 Intermediate Similarity NPC477217
0.7059 Intermediate Similarity NPC266741
0.7059 Intermediate Similarity NPC473922
0.705 Intermediate Similarity NPC470545
0.7042 Intermediate Similarity NPC160493
0.7034 Intermediate Similarity NPC210950
0.7034 Intermediate Similarity NPC199738
0.7034 Intermediate Similarity NPC218323
0.7025 Intermediate Similarity NPC470902
0.7013 Intermediate Similarity NPC81026
0.7 Intermediate Similarity NPC138365
0.7 Intermediate Similarity NPC470546
0.6972 Remote Similarity NPC71684
0.6966 Remote Similarity NPC136453
0.6962 Remote Similarity NPC473341
0.6944 Remote Similarity NPC22746
0.6933 Remote Similarity NPC29650
0.6928 Remote Similarity NPC161069
0.6918 Remote Similarity NPC89923
0.6918 Remote Similarity NPC71933
0.6918 Remote Similarity NPC239990
0.6918 Remote Similarity NPC105114
0.6918 Remote Similarity NPC152850
0.6905 Remote Similarity NPC158277
0.6901 Remote Similarity NPC190663
0.6883 Remote Similarity NPC315283
0.6883 Remote Similarity NPC314388
0.6871 Remote Similarity NPC213969
0.6871 Remote Similarity NPC111428
0.6871 Remote Similarity NPC165726
0.6867 Remote Similarity NPC474473
0.6839 Remote Similarity NPC316008
0.6839 Remote Similarity NPC313867
0.6839 Remote Similarity NPC209509
0.6821 Remote Similarity NPC470441
0.6818 Remote Similarity NPC212850
0.6818 Remote Similarity NPC83289
0.6818 Remote Similarity NPC189724
0.6815 Remote Similarity NPC246412
0.6813 Remote Similarity NPC39431
0.6797 Remote Similarity NPC163392
0.6797 Remote Similarity NPC239762
0.6795 Remote Similarity NPC314358
0.6788 Remote Similarity NPC323007
0.6784 Remote Similarity NPC194671
0.6784 Remote Similarity NPC269750
0.6783 Remote Similarity NPC45777
0.6783 Remote Similarity NPC477061
0.6779 Remote Similarity NPC157311
0.6776 Remote Similarity NPC43755
0.6776 Remote Similarity NPC471265
0.6776 Remote Similarity NPC471264
0.6776 Remote Similarity NPC68865
0.6772 Remote Similarity NPC245974
0.6769 Remote Similarity NPC311242
0.6766 Remote Similarity NPC315388
0.6765 Remote Similarity NPC182549
0.6765 Remote Similarity NPC114741
0.6763 Remote Similarity NPC35850
0.6763 Remote Similarity NPC276949
0.6757 Remote Similarity NPC469666
0.6753 Remote Similarity NPC476989
0.6752 Remote Similarity NPC247298
0.6752 Remote Similarity NPC138775
0.6748 Remote Similarity NPC319320
0.6748 Remote Similarity NPC287757
0.6747 Remote Similarity NPC254700
0.6746 Remote Similarity NPC273755
0.6746 Remote Similarity NPC306804
0.6739 Remote Similarity NPC269340
0.6733 Remote Similarity NPC44805
0.6733 Remote Similarity NPC8761
0.6732 Remote Similarity NPC132636
0.6731 Remote Similarity NPC471680
0.673 Remote Similarity NPC324081
0.6727 Remote Similarity NPC471052
0.6727 Remote Similarity NPC471053
0.6727 Remote Similarity NPC471051
0.6709 Remote Similarity NPC105717
0.6707 Remote Similarity NPC471527
0.6707 Remote Similarity NPC294516
0.6707 Remote Similarity NPC107938
0.6706 Remote Similarity NPC279871
0.6706 Remote Similarity NPC473354
0.6691 Remote Similarity NPC273814
0.669 Remote Similarity NPC38458
0.669 Remote Similarity NPC311737
0.669 Remote Similarity NPC252878
0.6687 Remote Similarity NPC189116
0.6686 Remote Similarity NPC89831
0.6686 Remote Similarity NPC230611
0.6686 Remote Similarity NPC45037
0.6667 Remote Similarity NPC256689
0.6667 Remote Similarity NPC211551
0.6667 Remote Similarity NPC476990
0.6667 Remote Similarity NPC254798
0.6667 Remote Similarity NPC123011
0.6667 Remote Similarity NPC235421
0.6667 Remote Similarity NPC319579
0.6667 Remote Similarity NPC80150
0.6667 Remote Similarity NPC50016
0.6647 Remote Similarity NPC304074
0.6647 Remote Similarity NPC290755
0.6647 Remote Similarity NPC471771
0.6646 Remote Similarity NPC122590
0.6645 Remote Similarity NPC469427
0.6645 Remote Similarity NPC269398
0.6645 Remote Similarity NPC469426
0.6645 Remote Similarity NPC263493
0.6644 Remote Similarity NPC46427
0.6644 Remote Similarity NPC473322
0.6644 Remote Similarity NPC35996
0.6629 Remote Similarity NPC294951
0.6627 Remote Similarity NPC40234
0.6623 Remote Similarity NPC257390
0.6623 Remote Similarity NPC326966
0.6623 Remote Similarity NPC45191
0.6621 Remote Similarity NPC202521
0.662 Remote Similarity NPC82963
0.662 Remote Similarity NPC239357
0.6619 Remote Similarity NPC275410
0.6618 Remote Similarity NPC45033
0.6618 Remote Similarity NPC477251
0.6608 Remote Similarity NPC476227
0.6608 Remote Similarity NPC159767
0.6608 Remote Similarity NPC473402
0.6608 Remote Similarity NPC471165
0.6608 Remote Similarity NPC477462
0.6608 Remote Similarity NPC155506
0.6606 Remote Similarity NPC469243
0.6606 Remote Similarity NPC114806
0.6606 Remote Similarity NPC475544
0.6603 Remote Similarity NPC139326
0.66 Remote Similarity NPC325651
0.6599 Remote Similarity NPC222466
0.6594 Remote Similarity NPC65855
0.6594 Remote Similarity NPC292758
0.6591 Remote Similarity NPC315542
0.6587 Remote Similarity NPC472923
0.6587 Remote Similarity NPC223207
0.6582 Remote Similarity NPC473804
0.6582 Remote Similarity NPC262077
0.6579 Remote Similarity NPC244866
0.6573 Remote Similarity NPC169328
0.6564 Remote Similarity NPC469903
0.6562 Remote Similarity NPC132771
0.6561 Remote Similarity NPC204546
0.6561 Remote Similarity NPC476978
0.6556 Remote Similarity NPC255447
0.6556 Remote Similarity NPC231382
0.6554 Remote Similarity NPC101719
0.6552 Remote Similarity NPC476183
0.655 Remote Similarity NPC137627
0.6549 Remote Similarity NPC197470
0.6545 Remote Similarity NPC24617
0.6543 Remote Similarity NPC286551
0.6541 Remote Similarity NPC119569
0.6541 Remote Similarity NPC16188
0.6541 Remote Similarity NPC311658
0.6538 Remote Similarity NPC168113
0.6536 Remote Similarity NPC90693
0.6536 Remote Similarity NPC64897
0.6531 Remote Similarity NPC477163
0.6531 Remote Similarity NPC6975
0.6529 Remote Similarity NPC475123
0.6529 Remote Similarity NPC475204
0.6529 Remote Similarity NPC46009
0.6528 Remote Similarity NPC310467
0.6528 Remote Similarity NPC237420
0.6528 Remote Similarity NPC314992
0.6525 Remote Similarity NPC1986
0.6525 Remote Similarity NPC474544
0.6522 Remote Similarity NPC473491
0.6519 Remote Similarity NPC315266
0.6519 Remote Similarity NPC5620
0.6516 Remote Similarity NPC178662
0.6516 Remote Similarity NPC470884
0.6516 Remote Similarity NPC313694
0.6516 Remote Similarity NPC92784
0.6516 Remote Similarity NPC98424
0.6516 Remote Similarity NPC242159
0.6516 Remote Similarity NPC476133
0.6514 Remote Similarity NPC476321

  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 NPC77992 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
0.7484 Intermediate Similarity NPD2891 Approved
0.7361 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD1967 Approved
0.7237 Intermediate Similarity NPD1968 Approved
0.7208 Intermediate Similarity NPD2013 Approved
0.7208 Intermediate Similarity NPD2016 Approved
0.7208 Intermediate Similarity NPD2014 Approved
0.7181 Intermediate Similarity NPD6295 Approved
0.7181 Intermediate Similarity NPD6294 Approved
0.7124 Intermediate Similarity NPD5481 Discontinued
0.7123 Intermediate Similarity NPD5454 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD3820 Approved
0.7115 Intermediate Similarity NPD3821 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD3822 Approved
0.7101 Intermediate Similarity NPD4431 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD7131 Phase 3
0.7032 Intermediate Similarity NPD6609 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.6993 Remote Similarity NPD6681 Discovery
0.6993 Remote Similarity NPD2584 Suspended
0.6987 Remote Similarity NPD3283 Phase 3
0.6987 Remote Similarity NPD3282 Phase 1
0.698 Remote Similarity NPD6623 Phase 3
0.6959 Remote Similarity NPD5581 Approved
0.6944 Remote Similarity NPD4677 Discontinued
0.6928 Remote Similarity NPD2174 Clinical (unspecified phase)
0.6912 Remote Similarity NPD2583 Phase 2
0.6899 Remote Similarity NPD7613 Discontinued
0.6887 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1582 Approved
0.6879 Remote Similarity NPD1581 Approved
0.6871 Remote Similarity NPD4175 Approved
0.6871 Remote Similarity NPD4177 Approved
0.6859 Remote Similarity NPD8323 Discontinued
0.6839 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7463 Clinical (unspecified phase)
0.6831 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6359 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4152 Approved
0.6795 Remote Similarity NPD6676 Phase 2
0.6788 Remote Similarity NPD8031 Discontinued
0.6786 Remote Similarity NPD7508 Discontinued
0.6781 Remote Similarity NPD3125 Approved
0.6781 Remote Similarity NPD2199 Approved
0.6781 Remote Similarity NPD2198 Approved
0.6776 Remote Similarity NPD6073 Approved
0.6766 Remote Similarity NPD2017 Approved
0.6766 Remote Similarity NPD2889 Approved
0.6766 Remote Similarity NPD2888 Approved
0.6766 Remote Similarity NPD2890 Approved
0.6753 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6738 Remote Similarity NPD3123 Discovery
0.6733 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6733 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6733 Remote Similarity NPD1330 Phase 2
0.6732 Remote Similarity NPD6852 Discontinued
0.6727 Remote Similarity NPD4871 Phase 2
0.6726 Remote Similarity NPD7608 Discontinued
0.6711 Remote Similarity NPD2791 Discontinued
0.669 Remote Similarity NPD5338 Clinical (unspecified phase)
0.669 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6689 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6689 Remote Similarity NPD5745 Approved
0.6687 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6685 Remote Similarity NPD5042 Phase 1
0.6667 Remote Similarity NPD7441 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5717 Approved
0.6667 Remote Similarity NPD5723 Approved
0.6667 Remote Similarity NPD7484 Phase 3
0.6667 Remote Similarity NPD7485 Phase 3
0.6645 Remote Similarity NPD6346 Approved
0.6645 Remote Similarity NPD3373 Approved
0.6645 Remote Similarity NPD4153 Approved
0.6645 Remote Similarity NPD5296 Approved
0.6644 Remote Similarity NPD3072 Approved
0.6644 Remote Similarity NPD3071 Approved
0.6644 Remote Similarity NPD3073 Approved
0.6644 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6644 Remote Similarity NPD4993 Discontinued
0.6627 Remote Similarity NPD4565 Clinical (unspecified phase)
0.6627 Remote Similarity NPD4564 Clinical (unspecified phase)
0.6625 Remote Similarity NPD5941 Approved
0.6625 Remote Similarity NPD5942 Approved
0.6625 Remote Similarity NPD3536 Discontinued
0.6624 Remote Similarity NPD4430 Phase 2
0.6624 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6623 Remote Similarity NPD4619 Approved
0.6623 Remote Similarity NPD4621 Approved
0.662 Remote Similarity NPD5291 Approved
0.662 Remote Similarity NPD6775 Clinical (unspecified phase)
0.662 Remote Similarity NPD5292 Approved
0.6618 Remote Similarity NPD5704 Approved
0.6618 Remote Similarity NPD810 Approved
0.6618 Remote Similarity NPD812 Approved
0.6618 Remote Similarity NPD5705 Approved
0.6618 Remote Similarity NPD5706 Approved
0.6618 Remote Similarity NPD811 Approved
0.6605 Remote Similarity NPD8315 Phase 1
0.6603 Remote Similarity NPD7720 Phase 2
0.66 Remote Similarity NPD5201 Approved
0.66 Remote Similarity NPD4617 Approved
0.66 Remote Similarity NPD4620 Approved
0.66 Remote Similarity NPD5203 Approved
0.66 Remote Similarity NPD5263 Approved
0.6597 Remote Similarity NPD770 Discontinued
0.6594 Remote Similarity NPD5237 Approved
0.6594 Remote Similarity NPD5239 Approved
0.6594 Remote Similarity NPD5236 Approved
0.6594 Remote Similarity NPD5240 Approved
0.6594 Remote Similarity NPD5235 Approved
0.6588 Remote Similarity NPD2388 Discontinued
0.6587 Remote Similarity NPD3368 Phase 2
0.6585 Remote Similarity NPD7105 Phase 1
0.6584 Remote Similarity NPD7303 Discontinued
0.6575 Remote Similarity NPD4762 Approved
0.6575 Remote Similarity NPD4761 Approved
0.6567 Remote Similarity NPD4119 Approved
0.6567 Remote Similarity NPD854 Approved
0.6567 Remote Similarity NPD855 Approved
0.6562 Remote Similarity NPD3950 Discontinued
0.6562 Remote Similarity NPD6088 Approved
0.6558 Remote Similarity NPD3054 Approved
0.6558 Remote Similarity NPD3052 Approved
0.6558 Remote Similarity NPD5725 Approved
0.6556 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6556 Remote Similarity NPD5746 Approved
0.6554 Remote Similarity NPD2079 Discontinued
0.655 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6549 Remote Similarity NPD1348 Approved
0.6545 Remote Similarity NPD7011 Discontinued
0.6541 Remote Similarity NPD3692 Discontinued
0.6541 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7939 Discontinued
0.6538 Remote Similarity NPD1725 Approved
0.6536 Remote Similarity NPD5121 Approved
0.6536 Remote Similarity NPD8265 Approved
0.6536 Remote Similarity NPD5120 Approved
0.6536 Remote Similarity NPD5119 Approved
0.6531 Remote Similarity NPD7249 Approved
0.6531 Remote Similarity NPD7250 Approved
0.6528 Remote Similarity NPD2217 Approved
0.6528 Remote Similarity NPD2218 Phase 2
0.6522 Remote Similarity NPD7811 Phase 3
0.6522 Remote Similarity NPD7810 Phase 3
0.6519 Remote Similarity NPD2460 Phase 3
0.6519 Remote Similarity NPD2458 Approved
0.6519 Remote Similarity NPD2459 Approved
0.651 Remote Similarity NPD2585 Clinical (unspecified phase)
0.6507 Remote Similarity NPD4106 Approved
0.6507 Remote Similarity NPD4136 Approved
0.6507 Remote Similarity NPD4135 Approved
0.6503 Remote Similarity NPD4648 Approved
0.6503 Remote Similarity NPD4574 Approved
0.6503 Remote Similarity NPD4576 Approved
0.6503 Remote Similarity NPD4647 Approved
0.6503 Remote Similarity NPD4646 Approved
0.6497 Remote Similarity NPD2087 Approved
0.6497 Remote Similarity NPD6853 Approved
0.6497 Remote Similarity NPD2088 Approved
0.6497 Remote Similarity NPD6851 Approved
0.6496 Remote Similarity NPD7130 Phase 3
0.6494 Remote Similarity NPD8643 Discontinued
0.649 Remote Similarity NPD4125 Approved
0.649 Remote Similarity NPD2985 Phase 3
0.6488 Remote Similarity NPD8007 Approved
0.6488 Remote Similarity NPD8008 Approved
0.6485 Remote Similarity NPD6570 Approved
0.6485 Remote Similarity NPD6571 Approved
0.6483 Remote Similarity NPD4102 Approved
0.6483 Remote Similarity NPD4105 Approved
0.6481 Remote Similarity NPD5229 Approved
0.6481 Remote Similarity NPD6078 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5230 Approved
0.6475 Remote Similarity NPD551 Approved
0.6475 Remote Similarity NPD550 Approved
0.6474 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5909 Discontinued
0.6467 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6467 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6463 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6463 Remote Similarity NPD4480 Approved
0.6458 Remote Similarity NPD7522 Discontinued
0.6457 Remote Similarity NPD6297 Approved
0.6456 Remote Similarity NPD5170 Discontinued
0.6453 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6452 Remote Similarity NPD4579 Clinical (unspecified phase)
0.645 Remote Similarity NPD7035 Approved
0.645 Remote Similarity NPD7036 Phase 3
0.645 Remote Similarity NPD7591 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5979 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6447 Remote Similarity NPD6039 Approved
0.6447 Remote Similarity NPD3136 Phase 2
0.6447 Remote Similarity NPD5163 Phase 2
0.6446 Remote Similarity NPD3311 Phase 1
0.6446 Remote Similarity NPD3312 Phase 1
0.6444 Remote Similarity NPD4188 Approved
0.6444 Remote Similarity NPD4189 Approved
0.6444 Remote Similarity NPD5716 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