Structure

Physi-Chem Properties

Molecular Weight:  734.26
Volume:  696.87
LogP:  3.153
LogD:  1.347
LogS:  -4.291
# Rotatable Bonds:  0
TPSA:  212.42
# H-Bond Aceptor:  14
# H-Bond Donor:  4
# Rings:  10
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.156
Synthetic Accessibility Score:  6.951
Fsp3:  0.667
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.35
MDCK Permeability:  9.18734585866332e-05
Pgp-inhibitor:  0.993
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.651
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.249
Plasma Protein Binding (PPB):  44.03331756591797%
Volume Distribution (VD):  0.48
Pgp-substrate:  42.013065338134766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.562
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.082
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.013
CYP3A4-inhibitor:  0.724
CYP3A4-substrate:  0.687

ADMET: Excretion

Clearance (CL):  2.136
Half-life (T1/2):  0.093

ADMET: Toxicity

hERG Blockers:  0.112
Human Hepatotoxicity (H-HT):  0.075
Drug-inuced Liver Injury (DILI):  0.662
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.094
Maximum Recommended Daily Dose:  0.977
Skin Sensitization:  0.307
Carcinogencity:  0.239
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.904

Download Data

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

  Natural Product: NPC327664

Natural Product ID:  NPC327664
Common Name*:   Chloramultilide C
IUPAC Name:   n.a.
Synonyms:   Chloramultilide C
Standard InCHIKey:  VAOZXVGMCZGLOH-BQPKVCGRSA-N
Standard InCHI:  InChI=1S/C39H42O14/c1-15-7-8-49-25(40)5-6-26(41)50-13-17-18-11-23-34(3,19-9-22(19)37(23,47)14-51-30(15)42)24-12-36(46)21-10-20(21)35(4)29(36)28(38(18,24)52-32(17)44)27-16(2)31(43)53-39(27,48)33(35)45/h7,19-24,33,45-48H,5-6,8-14H2,1-4H3/b15-7+/t19-,20-,21+,22+,23-,24+,33-,34+,35+,36+,37+,38+,39+/m1/s1
SMILES:  C/C/1=CCOC(=O)CCC(=O)OCC2=C3C[C@@H]4[C@](C)([C@@H]5C[C@@H]5[C@]4(COC1=O)O)[C@@H]1C[C@@]4([C@H]5C[C@H]5[C@@]5(C)C4=C(C4=C(C)C(=O)O[C@@]4([C@@H]5O)O)[C@]31OC2=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097992
PubChem CID:   24763324
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. DOI[10.1016/j.phytol.2016.01.005]
NPO14995 Chloranthus spicatus Species Chloranthaceae Eukaryota whole plant n.a. n.a. PMID[18044839]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[18451544]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota Whole plant Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota whole plants Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[21650224]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[21650224]
NPO15190 Chloranthus fortunei Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[27997206]
NPO14995 Chloranthus spicatus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14995 Chloranthus spicatus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14995 Chloranthus spicatus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15190 Chloranthus fortunei Species Chloranthaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[571155]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[571155]
NPT461 Cell Line PANC-1 Homo sapiens IC50 > 10000.0 nM PMID[571155]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000.0 nM PMID[571155]
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 > 10000.0 nM PMID[571155]
NPT20 Organism Candida albicans Candida albicans MIC > 157.0 nM PMID[571154]
NPT188 Organism Candida parapsilosis Candida parapsilosis MIC > 157.0 nM PMID[571154]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 25000.0 nM PMID[571156]

☑ 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 NPC327664 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC470427
1.0 High Similarity NPC476097
0.9918 High Similarity NPC60150
0.9918 High Similarity NPC192334
0.9917 High Similarity NPC476824
0.9836 High Similarity NPC24599
0.9752 High Similarity NPC134902
0.9672 High Similarity NPC254823
0.9421 High Similarity NPC226049
0.9339 High Similarity NPC84865
0.9154 High Similarity NPC25887
0.9098 High Similarity NPC27335
0.9084 High Similarity NPC470426
0.9077 High Similarity NPC476825
0.876 High Similarity NPC469674
0.876 High Similarity NPC469673
0.8692 High Similarity NPC476823
0.8682 High Similarity NPC34963
0.8615 High Similarity NPC58029
0.8605 High Similarity NPC220757
0.8605 High Similarity NPC279478
0.8605 High Similarity NPC241935
0.8605 High Similarity NPC196921
0.8527 High Similarity NPC35109
0.8295 Intermediate Similarity NPC15095
0.8154 Intermediate Similarity NPC63186
0.8016 Intermediate Similarity NPC470075
0.8 Intermediate Similarity NPC129992
0.7955 Intermediate Similarity NPC287423
0.7953 Intermediate Similarity NPC203862
0.7939 Intermediate Similarity NPC8374
0.7923 Intermediate Similarity NPC23786
0.7923 Intermediate Similarity NPC470265
0.7907 Intermediate Similarity NPC17938
0.7895 Intermediate Similarity NPC311534
0.7852 Intermediate Similarity NPC231240
0.7851 Intermediate Similarity NPC85742
0.7846 Intermediate Similarity NPC67569
0.7846 Intermediate Similarity NPC46570
0.7836 Intermediate Similarity NPC473593
0.7836 Intermediate Similarity NPC231529
0.7829 Intermediate Similarity NPC29639
0.7829 Intermediate Similarity NPC44899
0.7829 Intermediate Similarity NPC304260
0.7829 Intermediate Similarity NPC5883
0.782 Intermediate Similarity NPC42399
0.7812 Intermediate Similarity NPC93883
0.7795 Intermediate Similarity NPC106446
0.7794 Intermediate Similarity NPC316915
0.7786 Intermediate Similarity NPC88326
0.7786 Intermediate Similarity NPC153700
0.7786 Intermediate Similarity NPC269642
0.7786 Intermediate Similarity NPC107493
0.7786 Intermediate Similarity NPC115349
0.7769 Intermediate Similarity NPC107607
0.7769 Intermediate Similarity NPC474370
0.7761 Intermediate Similarity NPC470850
0.7761 Intermediate Similarity NPC473888
0.7752 Intermediate Similarity NPC475372
0.7752 Intermediate Similarity NPC218093
0.7746 Intermediate Similarity NPC471172
0.7737 Intermediate Similarity NPC471234
0.7737 Intermediate Similarity NPC478072
0.7734 Intermediate Similarity NPC5311
0.7734 Intermediate Similarity NPC193382
0.7734 Intermediate Similarity NPC310341
0.7734 Intermediate Similarity NPC199428
0.7734 Intermediate Similarity NPC99620
0.773 Intermediate Similarity NPC48414
0.773 Intermediate Similarity NPC5153
0.7727 Intermediate Similarity NPC469789
0.7717 Intermediate Similarity NPC264153
0.771 Intermediate Similarity NPC470418
0.771 Intermediate Similarity NPC475219
0.771 Intermediate Similarity NPC231518
0.771 Intermediate Similarity NPC312481
0.771 Intermediate Similarity NPC40749
0.7704 Intermediate Similarity NPC470880
0.7704 Intermediate Similarity NPC471407
0.7704 Intermediate Similarity NPC104382
0.7704 Intermediate Similarity NPC476966
0.7698 Intermediate Similarity NPC470076
0.7692 Intermediate Similarity NPC291820
0.7692 Intermediate Similarity NPC236973
0.7692 Intermediate Similarity NPC292467
0.7692 Intermediate Similarity NPC30483
0.7692 Intermediate Similarity NPC81222
0.7692 Intermediate Similarity NPC32177
0.7692 Intermediate Similarity NPC469756
0.7692 Intermediate Similarity NPC264954
0.7692 Intermediate Similarity NPC268326
0.7692 Intermediate Similarity NPC55532
0.7692 Intermediate Similarity NPC153085
0.7692 Intermediate Similarity NPC312536
0.7692 Intermediate Similarity NPC470897
0.7687 Intermediate Similarity NPC470882
0.7687 Intermediate Similarity NPC117702
0.7687 Intermediate Similarity NPC473265
0.7687 Intermediate Similarity NPC473253
0.7687 Intermediate Similarity NPC471357
0.7687 Intermediate Similarity NPC469757
0.7687 Intermediate Similarity NPC146456
0.7674 Intermediate Similarity NPC290693
0.7674 Intermediate Similarity NPC471355
0.7674 Intermediate Similarity NPC84987
0.7674 Intermediate Similarity NPC471353
0.7674 Intermediate Similarity NPC87250
0.7674 Intermediate Similarity NPC244402
0.7674 Intermediate Similarity NPC99728
0.7674 Intermediate Similarity NPC243196
0.7674 Intermediate Similarity NPC50305
0.7674 Intermediate Similarity NPC27507
0.7674 Intermediate Similarity NPC473656
0.7674 Intermediate Similarity NPC471354
0.7674 Intermediate Similarity NPC196429
0.7674 Intermediate Similarity NPC158344
0.7674 Intermediate Similarity NPC473852
0.7674 Intermediate Similarity NPC474418
0.7674 Intermediate Similarity NPC475323
0.7674 Intermediate Similarity NPC142066
0.7674 Intermediate Similarity NPC152615
0.7674 Intermediate Similarity NPC471351
0.7674 Intermediate Similarity NPC309034
0.7674 Intermediate Similarity NPC34390
0.7674 Intermediate Similarity NPC157376
0.7674 Intermediate Similarity NPC77319
0.7669 Intermediate Similarity NPC3381
0.7669 Intermediate Similarity NPC8369
0.7664 Intermediate Similarity NPC88668
0.7661 Intermediate Similarity NPC472820
0.7656 Intermediate Similarity NPC84949
0.7656 Intermediate Similarity NPC69576
0.7656 Intermediate Similarity NPC305044
0.7656 Intermediate Similarity NPC216665
0.7656 Intermediate Similarity NPC265290
0.7656 Intermediate Similarity NPC43213
0.7656 Intermediate Similarity NPC471633
0.7656 Intermediate Similarity NPC31354
0.7652 Intermediate Similarity NPC471082
0.7652 Intermediate Similarity NPC193893
0.7647 Intermediate Similarity NPC173347
0.7647 Intermediate Similarity NPC471170
0.7642 Intermediate Similarity NPC474550
0.7642 Intermediate Similarity NPC161775
0.7642 Intermediate Similarity NPC473543
0.7642 Intermediate Similarity NPC473577
0.7642 Intermediate Similarity NPC475585
0.7638 Intermediate Similarity NPC317460
0.7638 Intermediate Similarity NPC321272
0.7638 Intermediate Similarity NPC328074
0.7638 Intermediate Similarity NPC470063
0.7638 Intermediate Similarity NPC470025
0.7634 Intermediate Similarity NPC475556
0.7634 Intermediate Similarity NPC72260
0.7634 Intermediate Similarity NPC475629
0.7634 Intermediate Similarity NPC470312
0.763 Intermediate Similarity NPC473620
0.763 Intermediate Similarity NPC245094
0.763 Intermediate Similarity NPC236999
0.7619 Intermediate Similarity NPC179642
0.7619 Intermediate Similarity NPC177047
0.7615 Intermediate Similarity NPC83287
0.7615 Intermediate Similarity NPC186525
0.7615 Intermediate Similarity NPC709
0.7615 Intermediate Similarity NPC50774
0.7612 Intermediate Similarity NPC47113
0.7612 Intermediate Similarity NPC174367
0.7612 Intermediate Similarity NPC473635
0.7612 Intermediate Similarity NPC293112
0.76 Intermediate Similarity NPC88701
0.7597 Intermediate Similarity NPC106228
0.7597 Intermediate Similarity NPC138372
0.7594 Intermediate Similarity NPC473979
0.7594 Intermediate Similarity NPC27363
0.7594 Intermediate Similarity NPC41129
0.7591 Intermediate Similarity NPC472769
0.7591 Intermediate Similarity NPC471855
0.7581 Intermediate Similarity NPC470980
0.7581 Intermediate Similarity NPC220217
0.7581 Intermediate Similarity NPC119855
0.7581 Intermediate Similarity NPC472818
0.7581 Intermediate Similarity NPC475290
0.7578 Intermediate Similarity NPC471204
0.7578 Intermediate Similarity NPC470027
0.7576 Intermediate Similarity NPC173555
0.7576 Intermediate Similarity NPC473256
0.7576 Intermediate Similarity NPC314535
0.7576 Intermediate Similarity NPC474908
0.7576 Intermediate Similarity NPC170084
0.7576 Intermediate Similarity NPC233500
0.7576 Intermediate Similarity NPC475419
0.7576 Intermediate Similarity NPC129434
0.7576 Intermediate Similarity NPC202051
0.7576 Intermediate Similarity NPC475590
0.7576 Intermediate Similarity NPC470878
0.7576 Intermediate Similarity NPC476204
0.7576 Intermediate Similarity NPC120390
0.7574 Intermediate Similarity NPC175186
0.7574 Intermediate Similarity NPC6108
0.7574 Intermediate Similarity NPC469752

  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 NPC327664 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
0.771 Intermediate Similarity NPD8033 Approved
0.7634 Intermediate Similarity NPD8377 Approved
0.7634 Intermediate Similarity NPD8294 Approved
0.7615 Intermediate Similarity NPD7328 Approved
0.7615 Intermediate Similarity NPD7327 Approved
0.7576 Intermediate Similarity NPD8296 Approved
0.7576 Intermediate Similarity NPD8380 Approved
0.7576 Intermediate Similarity NPD8335 Approved
0.7576 Intermediate Similarity NPD8379 Approved
0.7576 Intermediate Similarity NPD8378 Approved
0.7576 Intermediate Similarity NPD7503 Approved
0.7574 Intermediate Similarity NPD7319 Approved
0.7557 Intermediate Similarity NPD7516 Approved
0.7538 Intermediate Similarity NPD7115 Discovery
0.7481 Intermediate Similarity NPD7507 Approved
0.7299 Intermediate Similarity NPD7078 Approved
0.7236 Intermediate Similarity NPD4225 Approved
0.7177 Intermediate Similarity NPD7639 Approved
0.7177 Intermediate Similarity NPD7640 Approved
0.7153 Intermediate Similarity NPD7492 Approved
0.7122 Intermediate Similarity NPD7736 Approved
0.7111 Intermediate Similarity NPD6319 Approved
0.7111 Intermediate Similarity NPD6054 Approved
0.7101 Intermediate Similarity NPD6616 Approved
0.7097 Intermediate Similarity NPD7638 Approved
0.7077 Intermediate Similarity NPD6371 Approved
0.7077 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6686 Approved
0.705 Intermediate Similarity NPD8293 Discontinued
0.7007 Intermediate Similarity NPD6370 Approved
0.7 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.6985 Remote Similarity NPD6059 Approved
0.697 Remote Similarity NPD8297 Approved
0.696 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6934 Remote Similarity NPD8517 Approved
0.6934 Remote Similarity NPD6016 Approved
0.6934 Remote Similarity NPD6015 Approved
0.6934 Remote Similarity NPD8516 Approved
0.6934 Remote Similarity NPD8513 Phase 3
0.6934 Remote Similarity NPD8515 Approved
0.6894 Remote Similarity NPD6649 Approved
0.6894 Remote Similarity NPD6650 Approved
0.6884 Remote Similarity NPD5988 Approved
0.687 Remote Similarity NPD6372 Approved
0.687 Remote Similarity NPD6373 Approved
0.685 Remote Similarity NPD5344 Discontinued
0.6846 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6846 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6053 Discontinued
0.6842 Remote Similarity NPD6882 Approved
0.6794 Remote Similarity NPD7320 Approved
0.6791 Remote Similarity NPD4632 Approved
0.6772 Remote Similarity NPD6648 Approved
0.6769 Remote Similarity NPD6008 Approved
0.6765 Remote Similarity NPD6009 Approved
0.6718 Remote Similarity NPD6412 Phase 2
0.6714 Remote Similarity NPD7604 Phase 2
0.669 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD8133 Approved
0.6667 Remote Similarity NPD7838 Discovery
0.6642 Remote Similarity NPD8130 Phase 1
0.6641 Remote Similarity NPD6402 Approved
0.6641 Remote Similarity NPD5739 Approved
0.6641 Remote Similarity NPD7128 Approved
0.6641 Remote Similarity NPD6675 Approved
0.6617 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6613 Remote Similarity NPD7637 Suspended
0.6596 Remote Similarity NPD8328 Phase 3
0.6591 Remote Similarity NPD5697 Approved
0.6567 Remote Similarity NPD6883 Approved
0.6567 Remote Similarity NPD7290 Approved
0.6567 Remote Similarity NPD7102 Approved
0.6567 Remote Similarity NPD4634 Approved
0.6528 Remote Similarity NPD6033 Approved
0.6519 Remote Similarity NPD6869 Approved
0.6519 Remote Similarity NPD6847 Approved
0.6519 Remote Similarity NPD6617 Approved
0.6493 Remote Similarity NPD6012 Approved
0.6493 Remote Similarity NPD6013 Approved
0.6493 Remote Similarity NPD6014 Approved
0.6466 Remote Similarity NPD5701 Approved
0.6457 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6454 Remote Similarity NPD5983 Phase 2
0.6452 Remote Similarity NPD7625 Phase 1
0.6429 Remote Similarity NPD6399 Phase 3
0.6418 Remote Similarity NPD6011 Approved
0.6412 Remote Similarity NPD5211 Phase 2
0.6403 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6395 Remote Similarity NPD7260 Phase 2
0.6389 Remote Similarity NPD6336 Discontinued
0.6378 Remote Similarity NPD6001 Approved
0.6357 Remote Similarity NPD6084 Phase 2
0.6357 Remote Similarity NPD6083 Phase 2
0.6349 Remote Similarity NPD5281 Approved
0.6349 Remote Similarity NPD5284 Approved
0.6328 Remote Similarity NPD5695 Phase 3
0.6316 Remote Similarity NPD5141 Approved
0.6299 Remote Similarity NPD5779 Approved
0.6299 Remote Similarity NPD5778 Approved
0.6296 Remote Similarity NPD5345 Clinical (unspecified phase)
0.629 Remote Similarity NPD7524 Approved
0.6277 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6277 Remote Similarity NPD6401 Clinical (unspecified phase)
0.627 Remote Similarity NPD46 Approved
0.627 Remote Similarity NPD6698 Approved
0.627 Remote Similarity NPD5785 Approved
0.626 Remote Similarity NPD5285 Approved
0.626 Remote Similarity NPD4696 Approved
0.626 Remote Similarity NPD5286 Approved
0.6257 Remote Similarity NPD7799 Discontinued
0.625 Remote Similarity NPD6067 Discontinued
0.6242 Remote Similarity NPD6845 Suspended
0.6231 Remote Similarity NPD7902 Approved
0.6231 Remote Similarity NPD4755 Approved
0.622 Remote Similarity NPD7983 Approved
0.6216 Remote Similarity NPD5956 Approved
0.6214 Remote Similarity NPD6274 Approved
0.6197 Remote Similarity NPD7101 Approved
0.6197 Remote Similarity NPD7100 Approved
0.619 Remote Similarity NPD6051 Approved
0.6183 Remote Similarity NPD5696 Approved
0.6179 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6172 Remote Similarity NPD4202 Approved
0.6165 Remote Similarity NPD5226 Approved
0.6165 Remote Similarity NPD4633 Approved
0.6165 Remote Similarity NPD5224 Approved
0.6165 Remote Similarity NPD5225 Approved
0.6142 Remote Similarity NPD5207 Approved
0.6136 Remote Similarity NPD4700 Approved
0.6129 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6127 Remote Similarity NPD6335 Approved
0.6119 Remote Similarity NPD5174 Approved
0.6119 Remote Similarity NPD5175 Approved
0.6111 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6903 Approved
0.6098 Remote Similarity NPD6695 Phase 3
0.6094 Remote Similarity NPD6050 Approved
0.6094 Remote Similarity NPD8034 Phase 2
0.6094 Remote Similarity NPD6411 Approved
0.6094 Remote Similarity NPD8035 Phase 2
0.609 Remote Similarity NPD5223 Approved
0.6078 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6058 Remote Similarity NPD4730 Approved
0.6058 Remote Similarity NPD4729 Approved
0.6056 Remote Similarity NPD6317 Approved
0.6048 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6032 Remote Similarity NPD7750 Discontinued
0.6032 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6029 Remote Similarity NPD4767 Approved
0.6029 Remote Similarity NPD4768 Approved
0.6016 Remote Similarity NPD5692 Phase 3
0.6014 Remote Similarity NPD6314 Approved
0.6014 Remote Similarity NPD6313 Approved
0.6 Remote Similarity NPD6908 Approved
0.6 Remote Similarity NPD7900 Approved
0.6 Remote Similarity NPD6909 Approved
0.6 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6 Remote Similarity NPD7748 Approved
0.5971 Remote Similarity NPD5250 Approved
0.5971 Remote Similarity NPD5247 Approved
0.5971 Remote Similarity NPD5251 Approved
0.5971 Remote Similarity NPD5248 Approved
0.5971 Remote Similarity NPD5249 Phase 3
0.597 Remote Similarity NPD4159 Approved
0.5969 Remote Similarity NPD5693 Phase 1
0.5969 Remote Similarity NPD5694 Approved
0.5969 Remote Similarity NPD6079 Approved
0.5954 Remote Similarity NPD5210 Approved
0.5954 Remote Similarity NPD4629 Approved
0.5952 Remote Similarity NPD6684 Approved
0.5952 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5952 Remote Similarity NPD7334 Approved
0.5952 Remote Similarity NPD6409 Approved
0.5952 Remote Similarity NPD5330 Approved
0.5952 Remote Similarity NPD7146 Approved
0.5952 Remote Similarity NPD3618 Phase 1
0.5952 Remote Similarity NPD7521 Approved
0.5942 Remote Similarity NPD5128 Approved
0.5938 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6101 Approved
0.5938 Remote Similarity NPD4753 Phase 2
0.5938 Remote Similarity NPD5328 Approved
0.5935 Remote Similarity NPD6334 Approved
0.5935 Remote Similarity NPD6333 Approved
0.5918 Remote Similarity NPD7829 Approved
0.5918 Remote Similarity NPD7830 Approved
0.5909 Remote Similarity NPD4697 Phase 3
0.5906 Remote Similarity NPD4251 Approved
0.5906 Remote Similarity NPD4250 Approved
0.589 Remote Similarity NPD6921 Approved
0.5882 Remote Similarity NPD4754 Approved
0.5873 Remote Similarity NPD5363 Approved
0.5867 Remote Similarity NPD8336 Approved
0.5867 Remote Similarity NPD8337 Approved
0.5865 Remote Similarity NPD5959 Approved
0.5864 Remote Similarity NPD7236 Approved
0.5862 Remote Similarity NPD4522 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