Structure

Physi-Chem Properties

Molecular Weight:  338.2
Volume:  355.382
LogP:  3.968
LogD:  4.043
LogS:  -3.623
# Rotatable Bonds:  3
TPSA:  45.33
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.855
Synthetic Accessibility Score:  5.003
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.068
MDCK Permeability:  2.77706694760127e-05
Pgp-inhibitor:  0.032
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.834
30% Bioavailability (F30%):  0.579

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.994
Plasma Protein Binding (PPB):  79.40180206298828%
Volume Distribution (VD):  2.12
Pgp-substrate:  16.08002471923828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.9
CYP1A2-substrate:  0.949
CYP2C19-inhibitor:  0.794
CYP2C19-substrate:  0.849
CYP2C9-inhibitor:  0.292
CYP2C9-substrate:  0.641
CYP2D6-inhibitor:  0.947
CYP2D6-substrate:  0.903
CYP3A4-inhibitor:  0.905
CYP3A4-substrate:  0.774

ADMET: Excretion

Clearance (CL):  11.882
Half-life (T1/2):  0.113

ADMET: Toxicity

hERG Blockers:  0.64
Human Hepatotoxicity (H-HT):  0.628
Drug-inuced Liver Injury (DILI):  0.081
AMES Toxicity:  0.101
Rat Oral Acute Toxicity:  0.974
Maximum Recommended Daily Dose:  0.939
Skin Sensitization:  0.227
Carcinogencity:  0.845
Eye Corrosion:  0.004
Eye Irritation:  0.049
Respiratory Toxicity:  0.964

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

  Natural Product: NPC329858

Natural Product ID:  NPC329858
Common Name*:   Coronaridine
IUPAC Name:   n.a.
Synonyms:   Coronaridine
Standard InCHIKey:  NVVDQMVGALBDGE-KSWFMABOSA-N
Standard InCHI:  InChI=1S/C21H26N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14-,19-,21+/m0/s1
SMILES:  CC[C@H]1C[C@H]2C[C@]3(c4c(CCN(C2)[C@@H]13)c1ccccc1[nH]4)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL364613
PubChem CID:   73489
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO32495 tabernaemontana calcarea Species Apocynaceae Eukaryota n.a. Madagascar rainforest n.a. PMID[12713407]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18778099]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[18778099]
NPO31010 Ervatamia hainanensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[20850311]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[23944995]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota Leaves n.a. n.a. PMID[24773071]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota stem-bark Pahang, Malaysia 2003-JUN PMID[25919190]
NPO6246 Ervatamia hainanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26024020]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26231157]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26918761]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[27077800]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[29319316]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[30169038]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[30869890]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[32356659]
NPO32727 peschiera laeta Species n.a. n.a. n.a. n.a. n.a. PMID[7853002]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31010 Ervatamia hainanensis n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6246 Ervatamia hainanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25727 Tabernaemontana divaricata Species Apocynaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 11.5 ug.mL-1 PMID[567121]
NPT91 Cell Line KB Homo sapiens IC50 = 2.6 ug.mL-1 PMID[567121]
NPT762 Cell Line A-431 Homo sapiens ED50 = 19.1 ug ml-1 PMID[567122]
NPT1851 Cell Line Col2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[567122]
NPT2049 Cell Line HT Homo sapiens ED50 > 20.0 ug ml-1 PMID[567122]
NPT91 Cell Line KB Homo sapiens ED50 = 13.6 ug ml-1 PMID[567122]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 10.7 ug ml-1 PMID[567122]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 10.9 ug ml-1 PMID[567122]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[567122]
NPT168 Cell Line P388 Mus musculus ED50 = 3.8 ug ml-1 PMID[567122]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[567122]
NPT179 Cell Line A2780 Homo sapiens IC50 = 9.9 ug.mL-1 PMID[567123]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 8600.0 nM PMID[567124]
NPT1885 Individual Protein Transient receptor potential cation channel subfamily M member 8 Mus musculus IC50 = 16000.0 nM PMID[567125]
NPT1885 Individual Protein Transient receptor potential cation channel subfamily M member 8 Mus musculus IC50 = 3000.0 nM PMID[567125]
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens Activity = 75.0 % PMID[567125]
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens EC50 = 16000.0 nM PMID[567125]
NPT472 Individual Protein Vanilloid receptor Homo sapiens IC50 = 170000.0 nM PMID[567125]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 25500.0 nM PMID[567126]
NPT2615 Cell Line HEK-293T Homo sapiens IC50 > 40000.0 nM PMID[567127]
NPT71 Cell Line HEK293 Homo sapiens IC50 = 31700.0 nM PMID[567127]
NPT2170 Cell Line RKO Homo sapiens IC50 > 40000.0 nM PMID[567127]
NPT660 Cell Line SW480 Homo sapiens IC50 = 10400.0 nM PMID[567127]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 11600.0 nM PMID[567127]
NPT165 Cell Line HeLa Homo sapiens EC50 > 40000.0 nM PMID[567128]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 7.5 ug ml-1 PMID[567122]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 1.9 ug ml-1 PMID[567122]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 11.2 ug ml-1 PMID[567122]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 12.0 ug ml-1 PMID[567122]
NPT2 Others Unspecified IC50 = 5800.0 nM PMID[567127]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 24400.0 nM PMID[567127]

☑ 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 NPC329858 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
0.9765 High Similarity NPC314333
0.9278 High Similarity NPC162730
0.9171 High Similarity NPC474116
0.8989 High Similarity NPC55493
0.8796 High Similarity NPC469928
0.8796 High Similarity NPC330009
0.8705 High Similarity NPC96321
0.8705 High Similarity NPC473041
0.8696 High Similarity NPC241024
0.867 High Similarity NPC477065
0.8542 High Similarity NPC475778
0.8541 High Similarity NPC52557
0.8525 High Similarity NPC269886
0.8525 High Similarity NPC472210
0.8525 High Similarity NPC472295
0.8525 High Similarity NPC81802
0.8525 High Similarity NPC247735
0.8466 Intermediate Similarity NPC475847
0.8466 Intermediate Similarity NPC185742
0.8449 Intermediate Similarity NPC214428
0.8438 Intermediate Similarity NPC234999
0.8427 Intermediate Similarity NPC469896
0.8409 Intermediate Similarity NPC189812
0.8409 Intermediate Similarity NPC329688
0.8407 Intermediate Similarity NPC111602
0.8407 Intermediate Similarity NPC63199
0.8407 Intermediate Similarity NPC175474
0.8407 Intermediate Similarity NPC196251
0.8407 Intermediate Similarity NPC102338
0.8385 Intermediate Similarity NPC469743
0.8325 Intermediate Similarity NPC277350
0.828 Intermediate Similarity NPC474121
0.8263 Intermediate Similarity NPC137589
0.8261 Intermediate Similarity NPC472112
0.8254 Intermediate Similarity NPC313985
0.8254 Intermediate Similarity NPC195461
0.8254 Intermediate Similarity NPC49196
0.8254 Intermediate Similarity NPC249150
0.8254 Intermediate Similarity NPC79129
0.8254 Intermediate Similarity NPC81654
0.8247 Intermediate Similarity NPC471304
0.8232 Intermediate Similarity NPC19679
0.8227 Intermediate Similarity NPC311906
0.8195 Intermediate Similarity NPC474192
0.8195 Intermediate Similarity NPC475720
0.8182 Intermediate Similarity NPC19692
0.8182 Intermediate Similarity NPC220151
0.8172 Intermediate Similarity NPC472292
0.8172 Intermediate Similarity NPC472113
0.8167 Intermediate Similarity NPC213468
0.8167 Intermediate Similarity NPC219336
0.8148 Intermediate Similarity NPC50503
0.8111 Intermediate Similarity NPC15573
0.8111 Intermediate Similarity NPC14113
0.8111 Intermediate Similarity NPC145885
0.8111 Intermediate Similarity NPC183662
0.8111 Intermediate Similarity NPC84827
0.8111 Intermediate Similarity NPC217372
0.8087 Intermediate Similarity NPC472119
0.8068 Intermediate Similarity NPC473105
0.8063 Intermediate Similarity NPC254240
0.8063 Intermediate Similarity NPC128265
0.8063 Intermediate Similarity NPC294909
0.8063 Intermediate Similarity NPC199851
0.8063 Intermediate Similarity NPC312870
0.8042 Intermediate Similarity NPC245916
0.8042 Intermediate Similarity NPC472293
0.8011 Intermediate Similarity NPC271797
0.8011 Intermediate Similarity NPC234987
0.8011 Intermediate Similarity NPC21174
0.8 Intermediate Similarity NPC160381
0.8 Intermediate Similarity NPC21605
0.7962 Intermediate Similarity NPC475816
0.7956 Intermediate Similarity NPC267885
0.7935 Intermediate Similarity NPC143533
0.7917 Intermediate Similarity NPC473868
0.7917 Intermediate Similarity NPC63157
0.7917 Intermediate Similarity NPC472297
0.7917 Intermediate Similarity NPC472296
0.7903 Intermediate Similarity NPC235684
0.7901 Intermediate Similarity NPC203468
0.7901 Intermediate Similarity NPC110500
0.7901 Intermediate Similarity NPC149155
0.7877 Intermediate Similarity NPC317430
0.7877 Intermediate Similarity NPC78020
0.7876 Intermediate Similarity NPC329747
0.7869 Intermediate Similarity NPC248041
0.7869 Intermediate Similarity NPC126709
0.7861 Intermediate Similarity NPC472323
0.7853 Intermediate Similarity NPC16667
0.7845 Intermediate Similarity NPC472123
0.7829 Intermediate Similarity NPC285469
0.7826 Intermediate Similarity NPC15840
0.7819 Intermediate Similarity NPC321708
0.7814 Intermediate Similarity NPC111275
0.7814 Intermediate Similarity NPC81939
0.7804 Intermediate Similarity NPC473540
0.7803 Intermediate Similarity NPC33421
0.7796 Intermediate Similarity NPC258480
0.779 Intermediate Similarity NPC6982
0.7784 Intermediate Similarity NPC113626
0.7778 Intermediate Similarity NPC95783
0.7778 Intermediate Similarity NPC475666
0.7772 Intermediate Similarity NPC283219
0.7761 Intermediate Similarity NPC472291
0.7754 Intermediate Similarity NPC472107
0.7754 Intermediate Similarity NPC79062
0.7747 Intermediate Similarity NPC161861
0.7742 Intermediate Similarity NPC472108
0.7742 Intermediate Similarity NPC17437
0.7742 Intermediate Similarity NPC139291
0.774 Intermediate Similarity NPC478078
0.7737 Intermediate Similarity NPC472097
0.7713 Intermediate Similarity NPC66210
0.7704 Intermediate Similarity NPC260900
0.7701 Intermediate Similarity NPC472294
0.7692 Intermediate Similarity NPC329793
0.7685 Intermediate Similarity NPC152768
0.7685 Intermediate Similarity NPC148183
0.7676 Intermediate Similarity NPC55772
0.7674 Intermediate Similarity NPC477066
0.767 Intermediate Similarity NPC207726
0.7668 Intermediate Similarity NPC472116
0.766 Intermediate Similarity NPC133003
0.7656 Intermediate Similarity NPC469720
0.765 Intermediate Similarity NPC34508
0.7641 Intermediate Similarity NPC74413
0.764 Intermediate Similarity NPC67056
0.7639 Intermediate Similarity NPC478082
0.7639 Intermediate Similarity NPC478081
0.7639 Intermediate Similarity NPC477067
0.7637 Intermediate Similarity NPC280548
0.7634 Intermediate Similarity NPC91179
0.7619 Intermediate Similarity NPC62749
0.7619 Intermediate Similarity NPC315555
0.7617 Intermediate Similarity NPC289299
0.7617 Intermediate Similarity NPC57994
0.7617 Intermediate Similarity NPC85066
0.7617 Intermediate Similarity NPC181502
0.7614 Intermediate Similarity NPC476874
0.7614 Intermediate Similarity NPC193761
0.7602 Intermediate Similarity NPC252338
0.76 Intermediate Similarity NPC475910
0.7594 Intermediate Similarity NPC71037
0.7592 Intermediate Similarity NPC469470
0.7592 Intermediate Similarity NPC469501
0.759 Intermediate Similarity NPC67288
0.7569 Intermediate Similarity NPC470508
0.7565 Intermediate Similarity NPC88315
0.7563 Intermediate Similarity NPC471944
0.7556 Intermediate Similarity NPC282339
0.7556 Intermediate Similarity NPC99632
0.7553 Intermediate Similarity NPC472104
0.7552 Intermediate Similarity NPC138370
0.7549 Intermediate Similarity NPC474412
0.7549 Intermediate Similarity NPC478157
0.7544 Intermediate Similarity NPC2949
0.7544 Intermediate Similarity NPC59084
0.7538 Intermediate Similarity NPC227582
0.7536 Intermediate Similarity NPC33949
0.7527 Intermediate Similarity NPC49954
0.7527 Intermediate Similarity NPC474561
0.7526 Intermediate Similarity NPC276517
0.7524 Intermediate Similarity NPC281049
0.75 Intermediate Similarity NPC306376
0.75 Intermediate Similarity NPC255229
0.75 Intermediate Similarity NPC471191
0.75 Intermediate Similarity NPC221100
0.75 Intermediate Similarity NPC81229
0.75 Intermediate Similarity NPC234078
0.7487 Intermediate Similarity NPC270009
0.7487 Intermediate Similarity NPC476098
0.7486 Intermediate Similarity NPC201700
0.7486 Intermediate Similarity NPC154293
0.7486 Intermediate Similarity NPC63751
0.7476 Intermediate Similarity NPC21638
0.7475 Intermediate Similarity NPC478158
0.7473 Intermediate Similarity NPC84347
0.7471 Intermediate Similarity NPC470440
0.746 Intermediate Similarity NPC470205
0.746 Intermediate Similarity NPC472109
0.746 Intermediate Similarity NPC472110
0.746 Intermediate Similarity NPC159125
0.7459 Intermediate Similarity NPC194881
0.7455 Intermediate Similarity NPC478080
0.745 Intermediate Similarity NPC132539
0.7449 Intermediate Similarity NPC262898
0.7449 Intermediate Similarity NPC141454
0.7435 Intermediate Similarity NPC99428
0.7435 Intermediate Similarity NPC141612
0.7435 Intermediate Similarity NPC17273
0.7435 Intermediate Similarity NPC135601
0.7433 Intermediate Similarity NPC151939
0.7432 Intermediate Similarity NPC160105
0.7427 Intermediate Similarity NPC74969
0.7426 Intermediate Similarity NPC266249
0.7421 Intermediate Similarity NPC228835
0.7419 Intermediate Similarity NPC472586
0.7415 Intermediate Similarity NPC478074
0.7415 Intermediate Similarity NPC229348

  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 NPC329858 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
0.9765 High Similarity NPD4499 Approved
0.8254 Intermediate Similarity NPD4600 Approved
0.8254 Intermediate Similarity NPD4601 Approved
0.8245 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.8216 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD4500 Approved
0.8063 Intermediate Similarity NPD4501 Approved
0.8031 Intermediate Similarity NPD6176 Phase 1
0.7935 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD482 Approved
0.7857 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD2094 Phase 2
0.7838 Intermediate Similarity NPD2095 Phase 2
0.7838 Intermediate Similarity NPD2092 Phase 2
0.7826 Intermediate Similarity NPD5473 Discontinued
0.7824 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD5901 Discontinued
0.7796 Intermediate Similarity NPD2091 Phase 2
0.7796 Intermediate Similarity NPD2096 Phase 2
0.7795 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2844 Phase 3
0.7766 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD4948 Discontinued
0.7765 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7747 Intermediate Similarity NPD750 Phase 2
0.7742 Intermediate Similarity NPD8358 Approved
0.772 Intermediate Similarity NPD5003 Discontinued
0.7716 Intermediate Similarity NPD5426 Phase 3
0.7688 Intermediate Similarity NPD2510 Approved
0.7688 Intermediate Similarity NPD2509 Approved
0.767 Intermediate Similarity NPD5257 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD7470 Discontinued
0.7662 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD1326 Approved
0.7637 Intermediate Similarity NPD1325 Approved
0.7617 Intermediate Similarity NPD4602 Approved
0.7598 Intermediate Similarity NPD3393 Approved
0.7598 Intermediate Similarity NPD3394 Approved
0.7598 Intermediate Similarity NPD3389 Approved
0.7577 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD1534 Approved
0.7538 Intermediate Similarity NPD6664 Approved
0.7526 Intermediate Similarity NPD7619 Phase 3
0.7526 Intermediate Similarity NPD7618 Phase 3
0.7525 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5065 Approved
0.75 Intermediate Similarity NPD4397 Phase 1
0.7488 Intermediate Similarity NPD6770 Approved
0.7487 Intermediate Similarity NPD8072 Approved
0.7473 Intermediate Similarity NPD4075 Phase 2
0.7451 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD7957 Phase 1
0.7409 Intermediate Similarity NPD2565 Phase 2
0.7409 Intermediate Similarity NPD2564 Approved
0.7405 Intermediate Similarity NPD5472 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD4076 Approved
0.7394 Intermediate Similarity NPD4079 Approved
0.7394 Intermediate Similarity NPD8386 Phase 2
0.7389 Intermediate Similarity NPD4506 Discontinued
0.7376 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3320 Approved
0.7368 Intermediate Similarity NPD3319 Phase 1
0.7368 Intermediate Similarity NPD3318 Approved
0.7366 Intermediate Similarity NPD7454 Approved
0.7366 Intermediate Similarity NPD7455 Approved
0.7366 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD6987 Phase 1
0.7356 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD8073 Approved
0.7344 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD3505 Approved
0.734 Intermediate Similarity NPD3506 Approved
0.734 Intermediate Similarity NPD2144 Approved
0.7317 Intermediate Similarity NPD5475 Discontinued
0.7316 Intermediate Similarity NPD3038 Discontinued
0.7316 Intermediate Similarity NPD4383 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD5471 Phase 3
0.7287 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD5913 Phase 3
0.7282 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD5592 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD3947 Discontinued
0.7277 Intermediate Similarity NPD4345 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7234 Approved
0.7268 Intermediate Similarity NPD7233 Approved
0.7263 Intermediate Similarity NPD6595 Phase 3
0.7255 Intermediate Similarity NPD2916 Discontinued
0.725 Intermediate Similarity NPD484 Approved
0.7241 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7778 Approved
0.7236 Intermediate Similarity NPD7777 Approved
0.7236 Intermediate Similarity NPD53 Approved
0.7232 Intermediate Similarity NPD1683 Approved
0.7228 Intermediate Similarity NPD3323 Discontinued
0.7216 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5254 Discontinued
0.7207 Intermediate Similarity NPD4463 Approved
0.7207 Intermediate Similarity NPD4462 Approved
0.72 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6999 Discontinued
0.7198 Intermediate Similarity NPD4326 Phase 2
0.7193 Intermediate Similarity NPD3385 Approved
0.7192 Intermediate Similarity NPD8098 Approved
0.719 Intermediate Similarity NPD7878 Phase 2
0.7189 Intermediate Similarity NPD2915 Discontinued
0.7179 Intermediate Similarity NPD4334 Discontinued
0.7174 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD6376 Discontinued
0.7171 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD2882 Phase 1
0.7164 Intermediate Similarity NPD6479 Discontinued
0.7163 Intermediate Similarity NPD8094 Discontinued
0.7158 Intermediate Similarity NPD2213 Approved
0.7158 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD1630 Approved
0.7158 Intermediate Similarity NPD2214 Approved
0.7157 Intermediate Similarity NPD7010 Phase 3
0.7151 Intermediate Similarity NPD4554 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6178 Phase 3
0.7143 Intermediate Similarity NPD6281 Approved
0.7136 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD4520 Approved
0.7129 Intermediate Similarity NPD5293 Phase 2
0.7128 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD8431 Approved
0.7128 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD8093 Discontinued
0.7114 Intermediate Similarity NPD6248 Phase 2
0.7114 Intermediate Similarity NPD6249 Phase 2
0.7105 Intermediate Similarity NPD5104 Approved
0.7102 Intermediate Similarity NPD1722 Approved
0.7098 Intermediate Similarity NPD5596 Phase 2
0.7097 Intermediate Similarity NPD7824 Approved
0.7095 Intermediate Similarity NPD4702 Approved
0.7095 Intermediate Similarity NPD4703 Approved
0.7092 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6292 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5897 Approved
0.7083 Intermediate Similarity NPD5898 Approved
0.7083 Intermediate Similarity NPD5899 Approved
0.7083 Intermediate Similarity NPD6452 Discontinued
0.7079 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD5809 Phase 3
0.7072 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD6158 Phase 2
0.7071 Intermediate Similarity NPD3404 Approved
0.7068 Intermediate Similarity NPD4181 Approved
0.7068 Intermediate Similarity NPD4398 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD7865 Approved
0.7062 Intermediate Similarity NPD7564 Discontinued
0.7062 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4643 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2920 Discontinued
0.7056 Intermediate Similarity NPD3100 Discontinued
0.7053 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5322 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD6226 Phase 3
0.7043 Intermediate Similarity NPD5140 Approved
0.7043 Intermediate Similarity NPD1631 Approved
0.7043 Intermediate Similarity NPD5138 Approved
0.7042 Intermediate Similarity NPD6242 Discontinued
0.7041 Intermediate Similarity NPD3961 Discontinued
0.7037 Intermediate Similarity NPD3609 Approved
0.7037 Intermediate Similarity NPD3610 Approved
0.7033 Intermediate Similarity NPD2837 Discontinued
0.7032 Intermediate Similarity NPD4885 Approved
0.7032 Intermediate Similarity NPD6263 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD5398 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7308 Discontinued
0.7028 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD5632 Approved
0.7027 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD8114 Approved
0.7024 Intermediate Similarity NPD8283 Approved
0.7024 Intermediate Similarity NPD8115 Approved
0.7024 Intermediate Similarity NPD7103 Approved
0.7024 Intermediate Similarity NPD56 Approved
0.7024 Intermediate Similarity NPD8282 Approved
0.7021 Intermediate Similarity NPD4639 Approved
0.7021 Intermediate Similarity NPD4638 Approved
0.7021 Intermediate Similarity NPD2640 Approved
0.7021 Intermediate Similarity NPD2641 Approved
0.7021 Intermediate Similarity NPD4640 Approved
0.7017 Intermediate Similarity NPD2172 Phase 1
0.7005 Intermediate Similarity NPD7665 Phase 2

  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