Structure

Physi-Chem Properties

Molecular Weight:  720.43
Volume:  754.145
LogP:  6.434
LogD:  4.952
LogS:  -3.787
# Rotatable Bonds:  8
TPSA:  104.92
# H-Bond Aceptor:  9
# H-Bond Donor:  3
# Rings:  10
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.189
Synthetic Accessibility Score:  7.176
Fsp3:  0.591
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:  -5.432
MDCK Permeability:  1.5275980331352912e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.983
Human Intestinal Absorption (HIA):  0.039
20% Bioavailability (F20%):  0.033
30% Bioavailability (F30%):  0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.26
Plasma Protein Binding (PPB):  92.80521392822266%
Volume Distribution (VD):  2.278
Pgp-substrate:  5.505155563354492%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.913
CYP2C19-inhibitor:  0.69
CYP2C19-substrate:  0.942
CYP2C9-inhibitor:  0.776
CYP2C9-substrate:  0.207
CYP2D6-inhibitor:  0.799
CYP2D6-substrate:  0.914
CYP3A4-inhibitor:  0.966
CYP3A4-substrate:  0.939

ADMET: Excretion

Clearance (CL):  4.814
Half-life (T1/2):  0.025

ADMET: Toxicity

hERG Blockers:  0.948
Human Hepatotoxicity (H-HT):  0.746
Drug-inuced Liver Injury (DILI):  0.407
AMES Toxicity:  0.097
Rat Oral Acute Toxicity:  0.975
Maximum Recommended Daily Dose:  0.99
Skin Sensitization:  0.039
Carcinogencity:  0.099
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.876

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

  Natural Product: NPC473540

Natural Product ID:  NPC473540
Common Name*:   Voacamine
IUPAC Name:   n.a.
Synonyms:   Voacamine
Standard InCHIKey:  YASZRXHHZSXNQI-VRHVUSBISA-N
Standard InCHI:  InChI=1S/C44H56N4O5/c1-7-24-16-31-28(24)17-32(39-33(26-11-9-10-12-34(26)46-39)19-36(45-3)38(31)42(49)52-5)30-18-35-29(20-37(30)51-4)27-13-14-48-22-23-15-25(8-2)41(48)44(21-23,40(27)47-35)43(50)53-6/h7,9-12,18,20,23,25,27-28,31-32,36,38,40-41,45-47H,8,13-17,19,21-22H2,1-6H3/b24-7-/t23-,25-,27?,28+,31?,32+,36?,38-,40?,41-,44+/m0/s1
SMILES:  COC(=O)[C@@H]1C(NC)Cc2c([C@H](C[C@H]3C1C/C/3=C/C)c1cc3NC4C(c3cc1OC)CCN1[C@@H]3[C@]4(C[C@H](C[C@@H]3CC)C1)C(=O)OC)[nH]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL445022
PubChem CID:   44559754
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
NPO32727 peschiera laeta Species n.a. n.a. n.a. n.a. n.a. PMID[7853002]

☑ 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
NPT762 Cell Line A-431 Homo sapiens ED50 = 5.0 ug ml-1 PMID[456058]
NPT1851 Cell Line Col2 Homo sapiens ED50 = 1.5 ug ml-1 PMID[456058]
NPT2049 Cell Line HT Homo sapiens ED50 = 6.6 ug ml-1 PMID[456058]
NPT91 Cell Line KB Homo sapiens ED50 = 9.6 ug ml-1 PMID[456058]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 12.6 ug ml-1 PMID[456058]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 11.2 ug ml-1 PMID[456058]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 3.8 ug ml-1 PMID[456058]
NPT168 Cell Line P388 Mus musculus ED50 = 3.0 ug ml-1 PMID[456058]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 2.8 ug ml-1 PMID[456058]
NPT91 Cell Line KB Homo sapiens ED50 = 2.6 ug ml-1 PMID[456059]
NPT232 Individual Protein Cannabinoid CB1 receptor Homo sapiens IC50 = 41.0 nM PMID[456060]
NPT1885 Individual Protein Transient receptor potential cation channel subfamily M member 8 Mus musculus IC50 > 100000.0 nM PMID[456062]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.9 ug ml-1 PMID[456058]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.0 ug ml-1 PMID[456058]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 15.3 ug ml-1 PMID[456058]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 1.3 ug ml-1 PMID[456058]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Survival = 50.0 % PMID[456061]

☑ 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 NPC473540 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
0.9364 High Similarity NPC478081
0.9318 High Similarity NPC477066
0.9283 High Similarity NPC17437
0.9189 High Similarity NPC477067
0.9189 High Similarity NPC478082
0.9123 High Similarity NPC478080
0.8972 High Similarity NPC96321
0.869 High Similarity NPC81939
0.8675 High Similarity NPC478083
0.8652 High Similarity NPC475666
0.8645 High Similarity NPC471304
0.861 High Similarity NPC311906
0.8578 High Similarity NPC475720
0.8578 High Similarity NPC474192
0.8539 High Similarity NPC473041
0.8447 Intermediate Similarity NPC469928
0.844 Intermediate Similarity NPC478074
0.8432 Intermediate Similarity NPC329982
0.8355 Intermediate Similarity NPC475816
0.814 Intermediate Similarity NPC329793
0.8079 Intermediate Similarity NPC478078
0.806 Intermediate Similarity NPC473105
0.8036 Intermediate Similarity NPC152768
0.8036 Intermediate Similarity NPC330009
0.8036 Intermediate Similarity NPC148183
0.8 Intermediate Similarity NPC477065
0.7974 Intermediate Similarity NPC472099
0.7968 Intermediate Similarity NPC471303
0.7905 Intermediate Similarity NPC237901
0.7905 Intermediate Similarity NPC195788
0.7902 Intermediate Similarity NPC472098
0.789 Intermediate Similarity NPC329747
0.786 Intermediate Similarity NPC280799
0.7804 Intermediate Similarity NPC329858
0.7793 Intermediate Similarity NPC300156
0.7782 Intermediate Similarity NPC260909
0.7699 Intermediate Similarity NPC208284
0.7686 Intermediate Similarity NPC305984
0.7682 Intermediate Similarity NPC21638
0.7658 Intermediate Similarity NPC474116
0.7658 Intermediate Similarity NPC162730
0.7644 Intermediate Similarity NPC475910
0.7639 Intermediate Similarity NPC314333
0.7617 Intermediate Similarity NPC157931
0.7611 Intermediate Similarity NPC476116
0.7588 Intermediate Similarity NPC475778
0.7588 Intermediate Similarity NPC473180
0.7588 Intermediate Similarity NPC94157
0.7573 Intermediate Similarity NPC39370
0.7563 Intermediate Similarity NPC473186
0.756 Intermediate Similarity NPC284685
0.7556 Intermediate Similarity NPC45190
0.7542 Intermediate Similarity NPC470126
0.7521 Intermediate Similarity NPC477531
0.7511 Intermediate Similarity NPC252251
0.7511 Intermediate Similarity NPC253580
0.7511 Intermediate Similarity NPC477533
0.751 Intermediate Similarity NPC469734
0.75 Intermediate Similarity NPC234999
0.75 Intermediate Similarity NPC131017
0.75 Intermediate Similarity NPC227908
0.7479 Intermediate Similarity NPC209174
0.7467 Intermediate Similarity NPC162484
0.7467 Intermediate Similarity NPC476098
0.746 Intermediate Similarity NPC191489
0.7457 Intermediate Similarity NPC169402
0.7456 Intermediate Similarity NPC201697
0.7448 Intermediate Similarity NPC475253
0.7447 Intermediate Similarity NPC280272
0.7445 Intermediate Similarity NPC4687
0.7445 Intermediate Similarity NPC193777
0.7442 Intermediate Similarity NPC176127
0.7436 Intermediate Similarity NPC86078
0.7425 Intermediate Similarity NPC46561
0.7425 Intermediate Similarity NPC303658
0.7414 Intermediate Similarity NPC170114
0.7412 Intermediate Similarity NPC88923
0.7412 Intermediate Similarity NPC315634
0.7412 Intermediate Similarity NPC100734
0.7409 Intermediate Similarity NPC55493
0.7407 Intermediate Similarity NPC41679
0.7397 Intermediate Similarity NPC473187
0.7395 Intermediate Similarity NPC473185
0.739 Intermediate Similarity NPC133609
0.7378 Intermediate Similarity NPC267423
0.7373 Intermediate Similarity NPC144452
0.7371 Intermediate Similarity NPC116238
0.7371 Intermediate Similarity NPC470549
0.7364 Intermediate Similarity NPC92111
0.7362 Intermediate Similarity NPC132642
0.736 Intermediate Similarity NPC189079
0.7348 Intermediate Similarity NPC199667
0.7342 Intermediate Similarity NPC276517
0.7339 Intermediate Similarity NPC74969
0.7333 Intermediate Similarity NPC214428
0.7331 Intermediate Similarity NPC60621
0.7331 Intermediate Similarity NPC477532
0.7328 Intermediate Similarity NPC39500
0.7318 Intermediate Similarity NPC76748
0.7316 Intermediate Similarity NPC87413
0.7313 Intermediate Similarity NPC223427
0.7304 Intermediate Similarity NPC473181
0.7303 Intermediate Similarity NPC474688
0.7302 Intermediate Similarity NPC303374
0.7297 Intermediate Similarity NPC307963
0.7295 Intermediate Similarity NPC184680
0.7295 Intermediate Similarity NPC15801
0.7292 Intermediate Similarity NPC274640
0.7292 Intermediate Similarity NPC471762
0.7288 Intermediate Similarity NPC174760
0.7284 Intermediate Similarity NPC48353
0.728 Intermediate Similarity NPC202503
0.728 Intermediate Similarity NPC319232
0.728 Intermediate Similarity NPC24370
0.7273 Intermediate Similarity NPC296527
0.7265 Intermediate Similarity NPC470785
0.7265 Intermediate Similarity NPC470784
0.7265 Intermediate Similarity NPC183407
0.7265 Intermediate Similarity NPC131486
0.7257 Intermediate Similarity NPC176538
0.7257 Intermediate Similarity NPC249040
0.7255 Intermediate Similarity NPC89549
0.7253 Intermediate Similarity NPC469592
0.7253 Intermediate Similarity NPC471080
0.7249 Intermediate Similarity NPC277350
0.7246 Intermediate Similarity NPC473179
0.7244 Intermediate Similarity NPC72211
0.7241 Intermediate Similarity NPC9894
0.724 Intermediate Similarity NPC469497
0.724 Intermediate Similarity NPC106833
0.7229 Intermediate Similarity NPC469743
0.7224 Intermediate Similarity NPC6786
0.722 Intermediate Similarity NPC194740
0.722 Intermediate Similarity NPC33949
0.7217 Intermediate Similarity NPC249583
0.7217 Intermediate Similarity NPC53344
0.7217 Intermediate Similarity NPC321428
0.7212 Intermediate Similarity NPC241024
0.721 Intermediate Similarity NPC310211
0.721 Intermediate Similarity NPC264176
0.721 Intermediate Similarity NPC308137
0.7206 Intermediate Similarity NPC81175
0.7205 Intermediate Similarity NPC285558
0.7203 Intermediate Similarity NPC184408
0.7203 Intermediate Similarity NPC469594
0.7202 Intermediate Similarity NPC49547
0.7202 Intermediate Similarity NPC101543
0.72 Intermediate Similarity NPC243834
0.72 Intermediate Similarity NPC70956
0.7198 Intermediate Similarity NPC126066
0.7195 Intermediate Similarity NPC111602
0.7195 Intermediate Similarity NPC63199
0.7195 Intermediate Similarity NPC196251
0.7195 Intermediate Similarity NPC102338
0.7195 Intermediate Similarity NPC101350
0.7195 Intermediate Similarity NPC128751
0.7194 Intermediate Similarity NPC244543
0.719 Intermediate Similarity NPC326363
0.7185 Intermediate Similarity NPC198503
0.7181 Intermediate Similarity NPC45459
0.7181 Intermediate Similarity NPC315491
0.7178 Intermediate Similarity NPC118559
0.7178 Intermediate Similarity NPC304307
0.7178 Intermediate Similarity NPC261251
0.7178 Intermediate Similarity NPC257851
0.7178 Intermediate Similarity NPC34580
0.7178 Intermediate Similarity NPC124920
0.7178 Intermediate Similarity NPC6215
0.7174 Intermediate Similarity NPC472111
0.7156 Intermediate Similarity NPC251090
0.7156 Intermediate Similarity NPC70259
0.7155 Intermediate Similarity NPC162748
0.7154 Intermediate Similarity NPC235685
0.7154 Intermediate Similarity NPC478010
0.7154 Intermediate Similarity NPC473183
0.7149 Intermediate Similarity NPC314954
0.7149 Intermediate Similarity NPC21425
0.7149 Intermediate Similarity NPC476044
0.7149 Intermediate Similarity NPC100547
0.7149 Intermediate Similarity NPC66777
0.7143 Intermediate Similarity NPC225279
0.7143 Intermediate Similarity NPC150239
0.7137 Intermediate Similarity NPC214142
0.7137 Intermediate Similarity NPC475844
0.7137 Intermediate Similarity NPC470018
0.713 Intermediate Similarity NPC475847
0.713 Intermediate Similarity NPC185742
0.7126 Intermediate Similarity NPC82472
0.7119 Intermediate Similarity NPC223409
0.7119 Intermediate Similarity NPC322135
0.7119 Intermediate Similarity NPC95240
0.7117 Intermediate Similarity NPC246700
0.7112 Intermediate Similarity NPC39679
0.7111 Intermediate Similarity NPC43787
0.7111 Intermediate Similarity NPC205934
0.7108 Intermediate Similarity NPC473312
0.7107 Intermediate Similarity NPC74575
0.7106 Intermediate Similarity NPC266931
0.7105 Intermediate Similarity NPC294909
0.7105 Intermediate Similarity NPC254240

  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 NPC473540 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
0.9283 High Similarity NPD8358 Approved
0.8263 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD8016 Phase 3
0.812 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.8097 Intermediate Similarity NPD8364 Approved
0.8097 Intermediate Similarity NPD8363 Approved
0.8032 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD8467 Approved
0.7905 Intermediate Similarity NPD8465 Approved
0.7905 Intermediate Similarity NPD8466 Approved
0.7782 Intermediate Similarity NPD8459 Approved
0.7782 Intermediate Similarity NPD8460 Approved
0.7713 Intermediate Similarity NPD8425 Approved
0.7713 Intermediate Similarity NPD8426 Approved
0.7712 Intermediate Similarity NPD4885 Approved
0.7695 Intermediate Similarity NPD8428 Approved
0.7695 Intermediate Similarity NPD8429 Approved
0.7695 Intermediate Similarity NPD8427 Approved
0.7639 Intermediate Similarity NPD4499 Approved
0.7566 Intermediate Similarity NPD5658 Approved
0.756 Intermediate Similarity NPD7955 Approved
0.756 Intermediate Similarity NPD7956 Approved
0.7511 Intermediate Similarity NPD6242 Discontinued
0.751 Intermediate Similarity NPD5488 Discontinued
0.7463 Intermediate Similarity NPD8489 Phase 1
0.746 Intermediate Similarity NPD7708 Approved
0.7457 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD5632 Approved
0.7421 Intermediate Similarity NPD4418 Discontinued
0.7412 Intermediate Similarity NPD7803 Approved
0.7412 Intermediate Similarity NPD2916 Discontinued
0.7398 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7373 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD5530 Phase 1
0.7322 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD7470 Discontinued
0.7298 Intermediate Similarity NPD8100 Phase 3
0.7297 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD1038 Approved
0.7292 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7276 Intermediate Similarity NPD7417 Discontinued
0.7251 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD3003 Approved
0.7244 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD7221 Approved
0.7227 Intermediate Similarity NPD7219 Approved
0.7217 Intermediate Similarity NPD7452 Approved
0.7217 Intermediate Similarity NPD7453 Approved
0.7217 Intermediate Similarity NPD7222 Phase 2
0.7211 Intermediate Similarity NPD8101 Phase 3
0.7205 Intermediate Similarity NPD4795 Phase 2
0.7194 Intermediate Similarity NPD8463 Approved
0.719 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD3006 Discontinued
0.7181 Intermediate Similarity NPD484 Approved
0.7174 Intermediate Similarity NPD8403 Phase 1
0.7173 Intermediate Similarity NPD7194 Discontinued
0.7171 Intermediate Similarity NPD8102 Discontinued
0.7166 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7688 Phase 1
0.7149 Intermediate Similarity NPD5903 Approved
0.7149 Intermediate Similarity NPD5559 Phase 2
0.7149 Intermediate Similarity NPD5902 Approved
0.7143 Intermediate Similarity NPD5930 Phase 3
0.7143 Intermediate Similarity NPD5482 Discontinued
0.7143 Intermediate Similarity NPD5429 Discontinued
0.7131 Intermediate Similarity NPD3354 Phase 2
0.7121 Intermediate Similarity NPD6531 Approved
0.7121 Intermediate Similarity NPD6530 Approved
0.7119 Intermediate Similarity NPD5612 Discontinued
0.7119 Intermediate Similarity NPD5479 Discontinued
0.7119 Intermediate Similarity NPD4952 Phase 3
0.7112 Intermediate Similarity NPD2510 Approved
0.7112 Intermediate Similarity NPD2509 Approved
0.7107 Intermediate Similarity NPD7994 Phase 2
0.7105 Intermediate Similarity NPD4501 Approved
0.7105 Intermediate Similarity NPD4500 Approved
0.7101 Intermediate Similarity NPD3763 Approved
0.7094 Intermediate Similarity NPD5416 Discontinued
0.7094 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD3257 Approved
0.7064 Intermediate Similarity NPD7069 Discontinued
0.7063 Intermediate Similarity NPD7868 Clinical (unspecified phase)
0.7061 Intermediate Similarity NPD7797 Approved
0.7061 Intermediate Similarity NPD7796 Approved
0.7059 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD8524 Approved
0.7054 Intermediate Similarity NPD7548 Discontinued
0.7054 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5003 Discontinued
0.7043 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD8091 Phase 3
0.704 Intermediate Similarity NPD6517 Phase 3
0.704 Intermediate Similarity NPD7392 Phase 2
0.7033 Intermediate Similarity NPD4373 Phase 2
0.7033 Intermediate Similarity NPD7558 Phase 2
0.7033 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD4600 Approved
0.7031 Intermediate Similarity NPD1739 Approved
0.7031 Intermediate Similarity NPD1740 Approved
0.7031 Intermediate Similarity NPD4601 Approved
0.7029 Intermediate Similarity NPD3258 Approved
0.7012 Intermediate Similarity NPD7592 Phase 2
0.7004 Intermediate Similarity NPD5293 Phase 2
0.7004 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.6987 Remote Similarity NPD7395 Discontinued
0.6987 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1768 Approved
0.6987 Remote Similarity NPD6985 Discontinued
0.6983 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6982 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6978 Remote Similarity NPD5913 Phase 3
0.6978 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6971 Remote Similarity NPD5506 Approved
0.6971 Remote Similarity NPD5507 Approved
0.6969 Remote Similarity NPD4558 Phase 2
0.6966 Remote Similarity NPD2189 Approved
0.6966 Remote Similarity NPD6376 Discontinued
0.6966 Remote Similarity NPD2187 Approved
0.6962 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6958 Remote Similarity NPD6770 Approved
0.6953 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6949 Remote Similarity NPD4502 Phase 2
0.6949 Remote Similarity NPD8525 Approved
0.6942 Remote Similarity NPD6995 Phase 1
0.6935 Remote Similarity NPD6963 Approved
0.6935 Remote Similarity NPD6964 Approved
0.6932 Remote Similarity NPD6790 Phase 1
0.693 Remote Similarity NPD5512 Phase 3
0.6926 Remote Similarity NPD7603 Discontinued
0.6926 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6917 Remote Similarity NPD4429 Discontinued
0.6916 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6913 Remote Similarity NPD3825 Phase 3
0.6913 Remote Similarity NPD8396 Approved
0.6913 Remote Similarity NPD8395 Approved
0.6911 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6911 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6716 Phase 1
0.6904 Remote Similarity NPD3389 Approved
0.6904 Remote Similarity NPD3393 Approved
0.6904 Remote Similarity NPD3394 Approved
0.69 Remote Similarity NPD7948 Phase 1
0.69 Remote Similarity NPD6769 Clinical (unspecified phase)
0.6895 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6892 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6878 Remote Similarity NPD6220 Phase 3
0.6878 Remote Similarity NPD8013 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3440 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6276 Discontinued
0.6862 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6862 Remote Similarity NPD4897 Phase 2
0.6856 Remote Similarity NPD6550 Discontinued
0.6853 Remote Similarity NPD4511 Phase 1
0.6849 Remote Similarity NPD3815 Phase 1
0.6849 Remote Similarity NPD3816 Phase 1
0.684 Remote Similarity NPD7853 Phase 2
0.683 Remote Similarity NPD7393 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4328 Approved
0.6829 Remote Similarity NPD6977 Clinical (unspecified phase)
0.6829 Remote Similarity NPD6978 Phase 2
0.6827 Remote Similarity NPD7790 Approved
0.6827 Remote Similarity NPD7951 Approved
0.6827 Remote Similarity NPD7950 Approved
0.6827 Remote Similarity NPD7791 Approved
0.6827 Remote Similarity NPD7789 Approved
0.6827 Remote Similarity NPD7952 Approved
0.6827 Remote Similarity NPD7953 Approved
0.6818 Remote Similarity NPD5450 Discontinued
0.6816 Remote Similarity NPD6976 Clinical (unspecified phase)
0.681 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6805 Remote Similarity NPD5164 Discontinued
0.6802 Remote Similarity NPD5014 Discontinued
0.6802 Remote Similarity NPD7555 Discontinued
0.6797 Remote Similarity NPD7946 Pre-registration
0.6797 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6795 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6176 Phase 1
0.6792 Remote Similarity NPD4442 Phase 2
0.6792 Remote Similarity NPD7673 Phase 3
0.679 Remote Similarity NPD7678 Clinical (unspecified phase)
0.679 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6789 Remote Similarity NPD7051 Phase 3
0.6789 Remote Similarity NPD7050 Clinical (unspecified phase)
0.6784 Remote Similarity NPD6230 Discontinued
0.678 Remote Similarity NPD1392 Approved
0.6777 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7567 Approved
0.6774 Remote Similarity NPD7824 Approved
0.6769 Remote Similarity NPD8442 Discontinued
0.6766 Remote Similarity NPD5901 Discontinued
0.6761 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6761 Remote Similarity NPD3259 Approved
0.6759 Remote Similarity NPD7025 Clinical (unspecified phase)

  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