Structure

Physi-Chem Properties

Molecular Weight:  324.18
Volume:  338.086
LogP:  3.86
LogD:  3.844
LogS:  -4.713
# Rotatable Bonds:  2
TPSA:  45.33
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.918
Synthetic Accessibility Score:  5.205
Fsp3:  0.55
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:  -4.978
MDCK Permeability:  1.6185744243557565e-05
Pgp-inhibitor:  0.095
Pgp-substrate:  0.695
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.027
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.978
Plasma Protein Binding (PPB):  84.39222717285156%
Volume Distribution (VD):  2.076
Pgp-substrate:  10.637593269348145%

ADMET: Metabolism

CYP1A2-inhibitor:  0.936
CYP1A2-substrate:  0.92
CYP2C19-inhibitor:  0.851
CYP2C19-substrate:  0.818
CYP2C9-inhibitor:  0.801
CYP2C9-substrate:  0.593
CYP2D6-inhibitor:  0.889
CYP2D6-substrate:  0.903
CYP3A4-inhibitor:  0.698
CYP3A4-substrate:  0.639

ADMET: Excretion

Clearance (CL):  9.954
Half-life (T1/2):  0.315

ADMET: Toxicity

hERG Blockers:  0.383
Human Hepatotoxicity (H-HT):  0.413
Drug-inuced Liver Injury (DILI):  0.838
AMES Toxicity:  0.715
Rat Oral Acute Toxicity:  0.947
Maximum Recommended Daily Dose:  0.965
Skin Sensitization:  0.097
Carcinogencity:  0.942
Eye Corrosion:  0.004
Eye Irritation:  0.031
Respiratory Toxicity:  0.973

Download Data

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

  Natural Product: NPC478078

Natural Product ID:  NPC478078
Common Name*:   (1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-11-one
IUPAC Name:   (1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-11-one
Synonyms:  
Standard InCHIKey:  KQABPFRLIMUVDP-CFOBNSSQSA-N
Standard InCHI:  InChI=1S/C20H24N2O2/c1-3-12-6-11-7-15-19-18(17(23)10-22(9-11)20(12)15)14-8-13(24-2)4-5-16(14)21-19/h4-5,8,11-12,15,20-21H,3,6-7,9-10H2,1-2H3/t11-,12-,15-,20-/m0/s1
SMILES:  CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CC(=O)C4=C3NC5=C4C=C(C=C5)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   122179182
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
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[18778099]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18778099]
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]
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]
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]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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 > 25 ug/ml PMID[25919190]

☑ 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 NPC478078 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
0.9158 High Similarity NPC471304
0.8942 High Similarity NPC96321
0.892 High Similarity NPC311906
0.8806 High Similarity NPC329793
0.8624 High Similarity NPC474192
0.8624 High Similarity NPC475720
0.8498 Intermediate Similarity NPC473041
0.8478 Intermediate Similarity NPC478083
0.8475 Intermediate Similarity NPC475816
0.8419 Intermediate Similarity NPC472099
0.8404 Intermediate Similarity NPC469928
0.8356 Intermediate Similarity NPC157931
0.8333 Intermediate Similarity NPC473105
0.8325 Intermediate Similarity NPC300156
0.8325 Intermediate Similarity NPC45190
0.8274 Intermediate Similarity NPC477066
0.8238 Intermediate Similarity NPC477067
0.8238 Intermediate Similarity NPC478081
0.8238 Intermediate Similarity NPC478082
0.8233 Intermediate Similarity NPC152768
0.8233 Intermediate Similarity NPC148183
0.8194 Intermediate Similarity NPC305984
0.8178 Intermediate Similarity NPC472098
0.8174 Intermediate Similarity NPC17437
0.8173 Intermediate Similarity NPC329747
0.816 Intermediate Similarity NPC475910
0.814 Intermediate Similarity NPC478074
0.81 Intermediate Similarity NPC21638
0.8082 Intermediate Similarity NPC323969
0.8079 Intermediate Similarity NPC473540
0.8045 Intermediate Similarity NPC280799
0.8037 Intermediate Similarity NPC288987
0.8028 Intermediate Similarity NPC321428
0.8 Intermediate Similarity NPC329982
0.7982 Intermediate Similarity NPC330009
0.7973 Intermediate Similarity NPC122436
0.7944 Intermediate Similarity NPC270918
0.7944 Intermediate Similarity NPC53344
0.7931 Intermediate Similarity NPC81939
0.7926 Intermediate Similarity NPC264176
0.7911 Intermediate Similarity NPC471762
0.7911 Intermediate Similarity NPC66777
0.7911 Intermediate Similarity NPC194740
0.7909 Intermediate Similarity NPC46561
0.7897 Intermediate Similarity NPC475666
0.7895 Intermediate Similarity NPC39370
0.789 Intermediate Similarity NPC478080
0.7885 Intermediate Similarity NPC473186
0.7882 Intermediate Similarity NPC176127
0.787 Intermediate Similarity NPC101350
0.7867 Intermediate Similarity NPC257851
0.786 Intermediate Similarity NPC4687
0.786 Intermediate Similarity NPC249583
0.786 Intermediate Similarity NPC477549
0.7857 Intermediate Similarity NPC53534
0.7851 Intermediate Similarity NPC329631
0.7826 Intermediate Similarity NPC235685
0.7808 Intermediate Similarity NPC39500
0.7804 Intermediate Similarity NPC476098
0.7798 Intermediate Similarity NPC187501
0.7793 Intermediate Similarity NPC74360
0.7778 Intermediate Similarity NPC478075
0.7763 Intermediate Similarity NPC474688
0.7763 Intermediate Similarity NPC219087
0.7759 Intermediate Similarity NPC191489
0.7758 Intermediate Similarity NPC276657
0.7741 Intermediate Similarity NPC303374
0.774 Intermediate Similarity NPC472112
0.774 Intermediate Similarity NPC329858
0.7729 Intermediate Similarity NPC207686
0.7717 Intermediate Similarity NPC87413
0.7714 Intermediate Similarity NPC81802
0.7714 Intermediate Similarity NPC247735
0.7714 Intermediate Similarity NPC472210
0.7714 Intermediate Similarity NPC269886
0.7714 Intermediate Similarity NPC472295
0.7703 Intermediate Similarity NPC92111
0.7692 Intermediate Similarity NPC196251
0.7692 Intermediate Similarity NPC102338
0.7692 Intermediate Similarity NPC111602
0.7692 Intermediate Similarity NPC63199
0.7689 Intermediate Similarity NPC144452
0.7686 Intermediate Similarity NPC260434
0.7682 Intermediate Similarity NPC310211
0.7682 Intermediate Similarity NPC308137
0.7679 Intermediate Similarity NPC225279
0.7672 Intermediate Similarity NPC184680
0.7668 Intermediate Similarity NPC303658
0.7668 Intermediate Similarity NPC184408
0.7667 Intermediate Similarity NPC472113
0.7664 Intermediate Similarity NPC152620
0.7664 Intermediate Similarity NPC249040
0.7661 Intermediate Similarity NPC171787
0.766 Intermediate Similarity NPC142385
0.7656 Intermediate Similarity NPC76748
0.7656 Intermediate Similarity NPC314333
0.7655 Intermediate Similarity NPC322482
0.7652 Intermediate Similarity NPC49547
0.765 Intermediate Similarity NPC148889
0.7644 Intermediate Similarity NPC198503
0.7639 Intermediate Similarity NPC470785
0.7639 Intermediate Similarity NPC470784
0.7636 Intermediate Similarity NPC208284
0.7636 Intermediate Similarity NPC9894
0.7634 Intermediate Similarity NPC208084
0.7633 Intermediate Similarity NPC315634
0.7633 Intermediate Similarity NPC88923
0.7633 Intermediate Similarity NPC100734
0.7632 Intermediate Similarity NPC74575
0.763 Intermediate Similarity NPC307963
0.7623 Intermediate Similarity NPC169402
0.7613 Intermediate Similarity NPC116238
0.7611 Intermediate Similarity NPC280272
0.7608 Intermediate Similarity NPC296527
0.7605 Intermediate Similarity NPC63971
0.7605 Intermediate Similarity NPC91868
0.7604 Intermediate Similarity NPC132539
0.76 Intermediate Similarity NPC150239
0.7588 Intermediate Similarity NPC470018
0.7581 Intermediate Similarity NPC254240
0.7581 Intermediate Similarity NPC128265
0.7581 Intermediate Similarity NPC176538
0.7581 Intermediate Similarity NPC312870
0.7581 Intermediate Similarity NPC199851
0.7581 Intermediate Similarity NPC294909
0.7569 Intermediate Similarity NPC472111
0.7558 Intermediate Similarity NPC223427
0.7542 Intermediate Similarity NPC72905
0.7534 Intermediate Similarity NPC193238
0.7533 Intermediate Similarity NPC216612
0.7522 Intermediate Similarity NPC274640
0.7521 Intermediate Similarity NPC15801
0.7521 Intermediate Similarity NPC6786
0.7512 Intermediate Similarity NPC131017
0.7512 Intermediate Similarity NPC160381
0.7512 Intermediate Similarity NPC276517
0.7512 Intermediate Similarity NPC162730
0.7511 Intermediate Similarity NPC247803
0.7511 Intermediate Similarity NPC470020
0.75 Intermediate Similarity NPC475844
0.75 Intermediate Similarity NPC322064
0.75 Intermediate Similarity NPC39679
0.7489 Intermediate Similarity NPC471080
0.7489 Intermediate Similarity NPC236668
0.7489 Intermediate Similarity NPC60621
0.7489 Intermediate Similarity NPC469592
0.7479 Intermediate Similarity NPC473187
0.7477 Intermediate Similarity NPC251090
0.7477 Intermediate Similarity NPC220337
0.7477 Intermediate Similarity NPC162484
0.7477 Intermediate Similarity NPC472116
0.7467 Intermediate Similarity NPC179287
0.7466 Intermediate Similarity NPC476116
0.7455 Intermediate Similarity NPC146976
0.7455 Intermediate Similarity NPC118228
0.7445 Intermediate Similarity NPC174760
0.7444 Intermediate Similarity NPC94157
0.7431 Intermediate Similarity NPC295898
0.7431 Intermediate Similarity NPC474116
0.743 Intermediate Similarity NPC19692
0.743 Intermediate Similarity NPC220151
0.7429 Intermediate Similarity NPC284685
0.7419 Intermediate Similarity NPC213308
0.7418 Intermediate Similarity NPC55493
0.7418 Intermediate Similarity NPC472292
0.7416 Intermediate Similarity NPC84478
0.7407 Intermediate Similarity NPC244543
0.7406 Intermediate Similarity NPC208522
0.7399 Intermediate Similarity NPC294375
0.7397 Intermediate Similarity NPC134848
0.7397 Intermediate Similarity NPC137353
0.7397 Intermediate Similarity NPC473800
0.7395 Intermediate Similarity NPC245916
0.7395 Intermediate Similarity NPC472293
0.7389 Intermediate Similarity NPC27041
0.7386 Intermediate Similarity NPC270515
0.7382 Intermediate Similarity NPC474701
0.738 Intermediate Similarity NPC210434
0.7373 Intermediate Similarity NPC280714
0.7362 Intermediate Similarity NPC253675
0.7357 Intermediate Similarity NPC469594
0.7354 Intermediate Similarity NPC309845
0.7352 Intermediate Similarity NPC471303
0.735 Intermediate Similarity NPC196718
0.735 Intermediate Similarity NPC102593
0.7348 Intermediate Similarity NPC51388
0.7342 Intermediate Similarity NPC82548
0.7342 Intermediate Similarity NPC41679
0.7339 Intermediate Similarity NPC315491
0.7339 Intermediate Similarity NPC45459
0.7333 Intermediate Similarity NPC258480
0.7333 Intermediate Similarity NPC472291
0.733 Intermediate Similarity NPC475841
0.733 Intermediate Similarity NPC474145
0.7317 Intermediate Similarity NPC258048
0.7304 Intermediate Similarity NPC220851
0.7303 Intermediate Similarity NPC178858
0.7301 Intermediate Similarity NPC16066
0.7297 Intermediate Similarity NPC193777
0.7295 Intermediate Similarity NPC84347

  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 NPC478078 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
0.8663 High Similarity NPD4118 Clinical (unspecified phase)
0.8249 Intermediate Similarity NPD6242 Discontinued
0.8174 Intermediate Similarity NPD8358 Approved
0.8047 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD5293 Phase 2
0.7965 Intermediate Similarity NPD4885 Approved
0.7854 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7851 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.783 Intermediate Similarity NPD4558 Phase 2
0.7828 Intermediate Similarity NPD4429 Discontinued
0.782 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD3393 Approved
0.7818 Intermediate Similarity NPD3389 Approved
0.7818 Intermediate Similarity NPD3394 Approved
0.7797 Intermediate Similarity NPD4952 Phase 3
0.7768 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD7708 Approved
0.7742 Intermediate Similarity NPD5658 Approved
0.7725 Intermediate Similarity NPD6790 Phase 1
0.7706 Intermediate Similarity NPD3006 Discontinued
0.7696 Intermediate Similarity NPD4373 Phase 2
0.7656 Intermediate Similarity NPD4499 Approved
0.7633 Intermediate Similarity NPD7803 Approved
0.763 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD1038 Approved
0.7611 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD4958 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD4501 Approved
0.7581 Intermediate Similarity NPD4500 Approved
0.7565 Intermediate Similarity NPD5479 Discontinued
0.7534 Intermediate Similarity NPD3257 Approved
0.7531 Intermediate Similarity NPD8091 Phase 3
0.7512 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7511 Intermediate Similarity NPD5632 Approved
0.75 Intermediate Similarity NPD2509 Approved
0.75 Intermediate Similarity NPD6376 Discontinued
0.75 Intermediate Similarity NPD2510 Approved
0.7489 Intermediate Similarity NPD5022 Discontinued
0.7489 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7478 Intermediate Similarity NPD3258 Approved
0.7478 Intermediate Similarity NPD4845 Discontinued
0.7478 Intermediate Similarity NPD7994 Phase 2
0.7429 Intermediate Similarity NPD7956 Approved
0.7429 Intermediate Similarity NPD7955 Approved
0.7427 Intermediate Similarity NPD5482 Discontinued
0.7403 Intermediate Similarity NPD3259 Approved
0.7399 Intermediate Similarity NPD5416 Discontinued
0.7398 Intermediate Similarity NPD6530 Approved
0.7398 Intermediate Similarity NPD6531 Approved
0.7397 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD4418 Discontinued
0.7339 Intermediate Similarity NPD484 Approved
0.7336 Intermediate Similarity NPD8463 Approved
0.7325 Intermediate Similarity NPD6770 Approved
0.7319 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7309 Intermediate Similarity NPD4506 Discontinued
0.7304 Intermediate Similarity NPD6209 Approved
0.7301 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7453 Approved
0.7297 Intermediate Similarity NPD7452 Approved
0.7285 Intermediate Similarity NPD3947 Discontinued
0.7253 Intermediate Similarity NPD4328 Approved
0.7252 Intermediate Similarity NPD3507 Phase 2
0.7243 Intermediate Similarity NPD8102 Discontinued
0.7241 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD8016 Phase 3
0.7238 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD5488 Discontinued
0.7222 Intermediate Similarity NPD5559 Phase 2
0.722 Intermediate Similarity NPD7222 Phase 2
0.7212 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD4795 Phase 2
0.7195 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD1659 Phase 1
0.7188 Intermediate Similarity NPD2189 Approved
0.7188 Intermediate Similarity NPD2187 Approved
0.7188 Intermediate Similarity NPD2916 Discontinued
0.7182 Intermediate Similarity NPD4601 Approved
0.7182 Intermediate Similarity NPD4600 Approved
0.7175 Intermediate Similarity NPD3003 Approved
0.7161 Intermediate Similarity NPD6962 Phase 2
0.7155 Intermediate Similarity NPD4368 Phase 2
0.713 Intermediate Similarity NPD4038 Approved
0.713 Intermediate Similarity NPD4122 Approved
0.713 Intermediate Similarity NPD4034 Approved
0.713 Intermediate Similarity NPD4036 Approved
0.713 Intermediate Similarity NPD4039 Approved
0.713 Intermediate Similarity NPD32 Approved
0.713 Intermediate Similarity NPD4035 Approved
0.713 Intermediate Similarity NPD4037 Approved
0.713 Intermediate Similarity NPD5901 Discontinued
0.713 Intermediate Similarity NPD31 Approved
0.713 Intermediate Similarity NPD4033 Approved
0.7126 Intermediate Similarity NPD8364 Approved
0.7126 Intermediate Similarity NPD8363 Approved
0.7123 Intermediate Similarity NPD5003 Discontinued
0.712 Intermediate Similarity NPD6228 Discontinued
0.7118 Intermediate Similarity NPD5612 Discontinued
0.7113 Intermediate Similarity NPD7853 Phase 2
0.7109 Intermediate Similarity NPD5473 Discontinued
0.7107 Intermediate Similarity NPD6716 Phase 1
0.7106 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD3945 Discontinued
0.7104 Intermediate Similarity NPD1739 Approved
0.7104 Intermediate Similarity NPD1740 Approved
0.7082 Intermediate Similarity NPD2285 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD5450 Discontinued
0.7074 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7690 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7796 Approved
0.7059 Intermediate Similarity NPD1768 Approved
0.7059 Intermediate Similarity NPD7797 Approved
0.7059 Intermediate Similarity NPD3825 Phase 3
0.7056 Intermediate Similarity NPD3354 Phase 2
0.7054 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.7046 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD4850 Phase 1
0.7027 Intermediate Similarity NPD8465 Approved
0.7027 Intermediate Similarity NPD8467 Approved
0.7027 Intermediate Similarity NPD8466 Approved
0.702 Intermediate Similarity NPD7393 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5186 Approved
0.7019 Intermediate Similarity NPD5183 Approved
0.7009 Intermediate Similarity NPD6176 Phase 1
0.7004 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2951 Discontinued
0.7 Intermediate Similarity NPD5512 Phase 3
0.6996 Remote Similarity NPD7417 Discontinued
0.6995 Remote Similarity NPD4203 Approved
0.6995 Remote Similarity NPD4204 Approved
0.6991 Remote Similarity NPD4948 Discontinued
0.6987 Remote Similarity NPD7455 Approved
0.6987 Remote Similarity NPD5866 Approved
0.6987 Remote Similarity NPD7454 Approved
0.6986 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7395 Discontinued
0.6972 Remote Similarity NPD5913 Phase 3
0.6972 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6953 Remote Similarity NPD7194 Discontinued
0.6953 Remote Similarity NPD3402 Phase 1
0.6951 Remote Similarity NPD8100 Phase 3
0.6947 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5601 Phase 2
0.6947 Remote Similarity NPD5530 Phase 1
0.6944 Remote Similarity NPD5256 Discontinued
0.6936 Remote Similarity NPD6995 Phase 1
0.6935 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6927 Remote Similarity NPD2564 Approved
0.6927 Remote Similarity NPD2565 Phase 2
0.6926 Remote Similarity NPD5902 Approved
0.6926 Remote Similarity NPD5903 Approved
0.6926 Remote Similarity NPD4897 Phase 2
0.6923 Remote Similarity NPD6276 Discontinued
0.6923 Remote Similarity NPD5930 Phase 3
0.6923 Remote Similarity NPD5070 Clinical (unspecified phase)
0.692 Remote Similarity NPD8459 Approved
0.692 Remote Similarity NPD8426 Approved
0.692 Remote Similarity NPD8425 Approved
0.692 Remote Similarity NPD8460 Approved
0.6917 Remote Similarity NPD7031 Phase 1
0.6916 Remote Similarity NPD5429 Discontinued
0.691 Remote Similarity NPD8405 Clinical (unspecified phase)
0.691 Remote Similarity NPD6568 Discontinued
0.691 Remote Similarity NPD7878 Phase 2
0.6907 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6901 Remote Similarity NPD3920 Phase 2
0.6901 Remote Similarity NPD5891 Approved
0.6898 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6897 Remote Similarity NPD8429 Approved
0.6897 Remote Similarity NPD8428 Approved
0.6897 Remote Similarity NPD8427 Approved
0.6895 Remote Similarity NPD4369 Phase 2
0.6887 Remote Similarity NPD7925 Phase 2
0.6887 Remote Similarity NPD7924 Phase 2
0.6885 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6883 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6881 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6878 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6878 Remote Similarity NPD3925 Approved
0.6875 Remote Similarity NPD5497 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7688 Phase 1
0.6872 Remote Similarity NPD8403 Phase 1
0.687 Remote Similarity NPD4502 Phase 2
0.687 Remote Similarity NPD7470 Discontinued
0.687 Remote Similarity NPD5475 Discontinued
0.6867 Remote Similarity NPD8101 Phase 3
0.6867 Remote Similarity NPD3986 Discontinued
0.6867 Remote Similarity NPD3440 Clinical (unspecified phase)
0.6853 Remote Similarity NPD2311 Clinical (unspecified phase)
0.6851 Remote Similarity NPD5850 Phase 3

  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