Structure

Physi-Chem Properties

Molecular Weight:  511.23
Volume:  500.276
LogP:  3.599
LogD:  2.815
LogS:  -3.998
# Rotatable Bonds:  2
TPSA:  113.7
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.471
Synthetic Accessibility Score:  5.011
Fsp3:  0.556
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.716
MDCK Permeability:  1.6280242562061176e-05
Pgp-inhibitor:  0.986
Pgp-substrate:  0.157
Human Intestinal Absorption (HIA):  0.077
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.172
Plasma Protein Binding (PPB):  84.45874786376953%
Volume Distribution (VD):  1.313
Pgp-substrate:  7.906439304351807%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.118
CYP2C19-inhibitor:  0.51
CYP2C19-substrate:  0.912
CYP2C9-inhibitor:  0.661
CYP2C9-substrate:  0.758
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.157
CYP3A4-inhibitor:  0.504
CYP3A4-substrate:  0.935

ADMET: Excretion

Clearance (CL):  9.345
Half-life (T1/2):  0.214

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.983
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.161
Maximum Recommended Daily Dose:  0.997
Skin Sensitization:  0.187
Carcinogencity:  0.893
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.903

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

  Natural Product: NPC474183

Natural Product ID:  NPC474183
Common Name*:   Verruculogen
IUPAC Name:   n.a.
Synonyms:   Verruculogen
Standard InCHIKey:  LRXYHMMJJCTUMY-KZXQSYCZSA-N
Standard InCHI:  InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20-,23-,27+/m0/s1
SMILES:  CC(=CC1N2C3=C(C=CC(=C3)OC)C4=C2C(CC(OO1)(C)C)N5C(=O)C6CCCN6C(=O)C5(C4O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463268
PubChem CID:   9806407
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0001213] Pyridoindoles
          • [CHEMONTID:0001914] Beta carbolines

*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
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17616609]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17929896]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19113967]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19159274]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19256529]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu 2003 PMID[20303767]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21954885]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22106303]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota stem bark of Melia azedarach n.a. n.a. PMID[22409377]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23557488]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23563483]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[7622436]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT111 Cell Line K562 Homo sapiens IC50 = 41000.0 nM PMID[468357]
NPT470 Individual Protein Rhodesain Trypanosoma brucei rhodesiense IC50 = 45000.0 nM PMID[468358]
NPT15 Cell Line Jurkat Homo sapiens IC50 = 97000.0 nM PMID[468358]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 1.5 % PMID[468359]
NPT32 Organism Mus musculus Mus musculus ED50 = 0.39 mg.kg-1 PMID[468356]
NPT548 Tissue Ileum Cavia porcellus Activity = 127.0 % PMID[468356]
NPT548 Tissue Ileum Cavia porcellus Activity = 123.0 % PMID[468356]
NPT548 Tissue Ileum Cavia porcellus Activity = 109.0 % PMID[468356]
NPT548 Tissue Ileum Cavia porcellus Activity = 7.0 % PMID[468356]
NPT548 Tissue Ileum Cavia porcellus Activity = 11.0 % PMID[468356]
NPT548 Tissue Ileum Cavia porcellus Activity = 14.0 % PMID[468356]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 12900.0 nM PMID[468358]
NPT2 Others Unspecified IC50 > 50000.0 nM PMID[468358]
NPT2 Others Unspecified Ratio IC50 = 7.5 n.a. PMID[468358]
NPT610 Others Molecular identity unknown MIC = 12200.0 nM PMID[468358]
NPT27 Others Unspecified Activity = 1.0 uM PMID[468358]
NPT32 Organism Mus musculus Mus musculus Activity = 0.78 mg kg-1 PMID[468358]
NPT32 Organism Mus musculus Mus musculus LD50 = 2.4 mg.kg-1 PMID[468358]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 17.99 % PMID[468359]
NPT1769 Organism Mythimna separata Mythimna separata AFI = 55.0 % PMID[468360]
NPT176 Organism Artemia salina Artemia salina LC50 = 15.8 ug.mL-1 PMID[468360]
NPT1203 Organism Fusarium graminearum Fusarium graminearum MIC = 6.25 ug.mL-1 PMID[468360]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum MIC = 25.0 ug.mL-1 PMID[468360]
NPT5164 Organism Fusarium oxysporum f. sp. niveum Fusarium oxysporum f. sp. niveum MIC = 12.5 ug.mL-1 PMID[468360]
NPT2600 Organism Fusarium solani Fusarium solani MIC = 50.0 ug.mL-1 PMID[468360]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides MIC = 6.25 ug.mL-1 PMID[468360]
NPT962 Organism Alternaria alternata Alternaria alternata MIC = 6.25 ug.mL-1 PMID[468360]
NPT2705 Organism Alternaria solani Alternaria solani MIC = 12.5 ug.mL-1 PMID[468360]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC = 6.25 ug.mL-1 PMID[468360]

☑ 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 NPC474183 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
0.9355 High Similarity NPC470784
0.9178 High Similarity NPC470785
0.9132 High Similarity NPC184680
0.881 High Similarity NPC469589
0.8525 High Similarity NPC305984
0.8402 Intermediate Similarity NPC303658
0.8402 Intermediate Similarity NPC469594
0.8387 Intermediate Similarity NPC471080
0.8387 Intermediate Similarity NPC469592
0.823 Intermediate Similarity NPC194740
0.8174 Intermediate Similarity NPC264176
0.808 Intermediate Similarity NPC128115
0.8009 Intermediate Similarity NPC472098
0.7958 Intermediate Similarity NPC189079
0.7842 Intermediate Similarity NPC133609
0.7822 Intermediate Similarity NPC152768
0.7822 Intermediate Similarity NPC148183
0.7783 Intermediate Similarity NPC21638
0.7763 Intermediate Similarity NPC295898
0.7738 Intermediate Similarity NPC472111
0.7627 Intermediate Similarity NPC473105
0.7609 Intermediate Similarity NPC472099
0.7593 Intermediate Similarity NPC204970
0.7589 Intermediate Similarity NPC475910
0.7577 Intermediate Similarity NPC151781
0.7577 Intermediate Similarity NPC316181
0.7577 Intermediate Similarity NPC74562
0.7553 Intermediate Similarity NPC220852
0.7531 Intermediate Similarity NPC285343
0.7529 Intermediate Similarity NPC260909
0.75 Intermediate Similarity NPC60621
0.75 Intermediate Similarity NPC472286
0.75 Intermediate Similarity NPC472287
0.75 Intermediate Similarity NPC131486
0.7489 Intermediate Similarity NPC146418
0.7479 Intermediate Similarity NPC323752
0.7478 Intermediate Similarity NPC174758
0.7468 Intermediate Similarity NPC14288
0.7467 Intermediate Similarity NPC53344
0.7447 Intermediate Similarity NPC24370
0.7447 Intermediate Similarity NPC319232
0.7442 Intermediate Similarity NPC237901
0.7442 Intermediate Similarity NPC195788
0.7438 Intermediate Similarity NPC99891
0.7415 Intermediate Similarity NPC261251
0.7406 Intermediate Similarity NPC323198
0.7404 Intermediate Similarity NPC122886
0.7398 Intermediate Similarity NPC91868
0.7398 Intermediate Similarity NPC63971
0.7397 Intermediate Similarity NPC475816
0.7388 Intermediate Similarity NPC469734
0.7384 Intermediate Similarity NPC311906
0.7384 Intermediate Similarity NPC100547
0.7373 Intermediate Similarity NPC214142
0.7371 Intermediate Similarity NPC472436
0.7371 Intermediate Similarity NPC15840
0.7371 Intermediate Similarity NPC473041
0.7364 Intermediate Similarity NPC289299
0.7364 Intermediate Similarity NPC57994
0.7353 Intermediate Similarity NPC95240
0.7353 Intermediate Similarity NPC223409
0.7353 Intermediate Similarity NPC322135
0.7353 Intermediate Similarity NPC326363
0.7349 Intermediate Similarity NPC244543
0.7349 Intermediate Similarity NPC314882
0.7347 Intermediate Similarity NPC81939
0.7342 Intermediate Similarity NPC472284
0.7342 Intermediate Similarity NPC124920
0.7342 Intermediate Similarity NPC304307
0.7342 Intermediate Similarity NPC34580
0.7342 Intermediate Similarity NPC118559
0.7339 Intermediate Similarity NPC14812
0.7333 Intermediate Similarity NPC315467
0.7325 Intermediate Similarity NPC174672
0.7317 Intermediate Similarity NPC475666
0.7314 Intermediate Similarity NPC28945
0.7311 Intermediate Similarity NPC33949
0.7311 Intermediate Similarity NPC471762
0.7306 Intermediate Similarity NPC188400
0.7305 Intermediate Similarity NPC478009
0.7302 Intermediate Similarity NPC284685
0.7301 Intermediate Similarity NPC14339
0.7292 Intermediate Similarity NPC54803
0.7292 Intermediate Similarity NPC321592
0.7284 Intermediate Similarity NPC82472
0.7284 Intermediate Similarity NPC274982
0.7281 Intermediate Similarity NPC478077
0.7265 Intermediate Similarity NPC213530
0.7265 Intermediate Similarity NPC193267
0.7265 Intermediate Similarity NPC306376
0.7257 Intermediate Similarity NPC476098
0.7257 Intermediate Similarity NPC97746
0.7251 Intermediate Similarity NPC472435
0.7251 Intermediate Similarity NPC478080
0.7248 Intermediate Similarity NPC472323
0.7235 Intermediate Similarity NPC472107
0.7235 Intermediate Similarity NPC79062
0.7234 Intermediate Similarity NPC150239
0.7233 Intermediate Similarity NPC478006
0.7231 Intermediate Similarity NPC471303
0.7231 Intermediate Similarity NPC325976
0.7229 Intermediate Similarity NPC127996
0.7225 Intermediate Similarity NPC47059
0.7225 Intermediate Similarity NPC165349
0.7225 Intermediate Similarity NPC118832
0.7225 Intermediate Similarity NPC264166
0.7225 Intermediate Similarity NPC274291
0.7225 Intermediate Similarity NPC329708
0.722 Intermediate Similarity NPC475720
0.722 Intermediate Similarity NPC474192
0.7213 Intermediate Similarity NPC101350
0.721 Intermediate Similarity NPC330009
0.7206 Intermediate Similarity NPC472434
0.7202 Intermediate Similarity NPC473187
0.72 Intermediate Similarity NPC67904
0.72 Intermediate Similarity NPC329747
0.7197 Intermediate Similarity NPC110151
0.7197 Intermediate Similarity NPC473185
0.7194 Intermediate Similarity NPC258048
0.7191 Intermediate Similarity NPC315804
0.7191 Intermediate Similarity NPC313804
0.719 Intermediate Similarity NPC284888
0.7189 Intermediate Similarity NPC472119
0.7189 Intermediate Similarity NPC258480
0.7188 Intermediate Similarity NPC152620
0.7185 Intermediate Similarity NPC473449
0.7182 Intermediate Similarity NPC174629
0.7181 Intermediate Similarity NPC53144
0.7174 Intermediate Similarity NPC477160
0.7173 Intermediate Similarity NPC280272
0.7172 Intermediate Similarity NPC235685
0.7171 Intermediate Similarity NPC478010
0.7167 Intermediate Similarity NPC66777
0.7165 Intermediate Similarity NPC478011
0.7163 Intermediate Similarity NPC133261
0.7162 Intermediate Similarity NPC279401
0.7162 Intermediate Similarity NPC270918
0.7162 Intermediate Similarity NPC79293
0.7161 Intermediate Similarity NPC323969
0.716 Intermediate Similarity NPC165964
0.716 Intermediate Similarity NPC88923
0.716 Intermediate Similarity NPC253675
0.716 Intermediate Similarity NPC33064
0.716 Intermediate Similarity NPC245055
0.716 Intermediate Similarity NPC315634
0.716 Intermediate Similarity NPC100734
0.7155 Intermediate Similarity NPC112206
0.7155 Intermediate Similarity NPC202605
0.7149 Intermediate Similarity NPC247803
0.7143 Intermediate Similarity NPC122436
0.7143 Intermediate Similarity NPC329982
0.7143 Intermediate Similarity NPC471304
0.7137 Intermediate Similarity NPC78609
0.7137 Intermediate Similarity NPC314176
0.713 Intermediate Similarity NPC470931
0.713 Intermediate Similarity NPC287208
0.713 Intermediate Similarity NPC82548
0.7125 Intermediate Similarity NPC478078
0.7124 Intermediate Similarity NPC249040
0.7123 Intermediate Similarity NPC66210
0.7119 Intermediate Similarity NPC288110
0.7119 Intermediate Similarity NPC141053
0.7119 Intermediate Similarity NPC298436
0.7118 Intermediate Similarity NPC474145
0.7118 Intermediate Similarity NPC475841
0.7117 Intermediate Similarity NPC473004
0.7112 Intermediate Similarity NPC87413
0.711 Intermediate Similarity NPC470003
0.711 Intermediate Similarity NPC62069
0.7108 Intermediate Similarity NPC58209
0.7107 Intermediate Similarity NPC260434
0.7106 Intermediate Similarity NPC312645
0.7105 Intermediate Similarity NPC475774
0.7102 Intermediate Similarity NPC184225
0.7102 Intermediate Similarity NPC473183
0.7093 Intermediate Similarity NPC314056
0.7089 Intermediate Similarity NPC132642
0.7089 Intermediate Similarity NPC477533
0.7089 Intermediate Similarity NPC174760
0.7076 Intermediate Similarity NPC264285
0.7076 Intermediate Similarity NPC96321
0.7073 Intermediate Similarity NPC41679
0.7072 Intermediate Similarity NPC129909
0.7069 Intermediate Similarity NPC123976
0.7069 Intermediate Similarity NPC167860
0.7064 Intermediate Similarity NPC143533
0.7063 Intermediate Similarity NPC67401
0.7061 Intermediate Similarity NPC477549
0.7061 Intermediate Similarity NPC272549
0.7059 Intermediate Similarity NPC198503
0.7054 Intermediate Similarity NPC186351
0.7051 Intermediate Similarity NPC89508
0.7049 Intermediate Similarity NPC329631
0.7047 Intermediate Similarity NPC303374
0.7046 Intermediate Similarity NPC219397
0.7043 Intermediate Similarity NPC476106
0.7037 Intermediate Similarity NPC477177
0.7037 Intermediate Similarity NPC475969
0.7037 Intermediate Similarity NPC475859
0.7035 Intermediate Similarity NPC149708

  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 NPC474183 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
0.8009 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7915 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD4885 Approved
0.7826 Intermediate Similarity NPD7426 Phase 1
0.7811 Intermediate Similarity NPD7797 Approved
0.7811 Intermediate Similarity NPD7796 Approved
0.7764 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD8016 Phase 3
0.7725 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7621 Intermediate Similarity NPD4897 Phase 2
0.76 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7583 Intermediate Similarity NPD6790 Phase 1
0.7578 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD4373 Phase 2
0.7545 Intermediate Similarity NPD7222 Phase 2
0.7529 Intermediate Similarity NPD8460 Approved
0.7529 Intermediate Similarity NPD8459 Approved
0.7529 Intermediate Similarity NPD8425 Approved
0.7529 Intermediate Similarity NPD8426 Approved
0.751 Intermediate Similarity NPD8429 Approved
0.751 Intermediate Similarity NPD8427 Approved
0.751 Intermediate Similarity NPD8428 Approved
0.749 Intermediate Similarity NPD8463 Approved
0.7479 Intermediate Similarity NPD6716 Phase 1
0.7459 Intermediate Similarity NPD8359 Phase 2
0.7442 Intermediate Similarity NPD8465 Approved
0.7442 Intermediate Similarity NPD8466 Approved
0.7442 Intermediate Similarity NPD8467 Approved
0.7434 Intermediate Similarity NPD2916 Discontinued
0.7426 Intermediate Similarity NPD4952 Phase 3
0.7425 Intermediate Similarity NPD5506 Approved
0.7425 Intermediate Similarity NPD5507 Approved
0.7407 Intermediate Similarity NPD6517 Phase 3
0.7395 Intermediate Similarity NPD7284 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD7453 Approved
0.7389 Intermediate Similarity NPD7452 Approved
0.7384 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD4602 Approved
0.736 Intermediate Similarity NPD8255 Phase 2
0.7345 Intermediate Similarity NPD3003 Approved
0.7344 Intermediate Similarity NPD8363 Approved
0.7344 Intermediate Similarity NPD8364 Approved
0.7342 Intermediate Similarity NPD3259 Approved
0.7328 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD5293 Phase 2
0.7302 Intermediate Similarity NPD7955 Approved
0.7302 Intermediate Similarity NPD7956 Approved
0.7298 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6568 Discontinued
0.7296 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7031 Phase 1
0.7287 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7281 Intermediate Similarity NPD5658 Approved
0.7265 Intermediate Similarity NPD7194 Discontinued
0.7261 Intermediate Similarity NPD7558 Phase 2
0.7256 Intermediate Similarity NPD4203 Approved
0.7256 Intermediate Similarity NPD4204 Approved
0.7254 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8246 Approved
0.7251 Intermediate Similarity NPD8247 Approved
0.725 Intermediate Similarity NPD6962 Phase 2
0.7248 Intermediate Similarity NPD6393 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD1768 Approved
0.7227 Intermediate Similarity NPD5640 Discontinued
0.7225 Intermediate Similarity NPD4035 Approved
0.7225 Intermediate Similarity NPD32 Approved
0.7225 Intermediate Similarity NPD4033 Approved
0.7225 Intermediate Similarity NPD31 Approved
0.7225 Intermediate Similarity NPD4122 Approved
0.7225 Intermediate Similarity NPD4034 Approved
0.7225 Intermediate Similarity NPD4038 Approved
0.7225 Intermediate Similarity NPD4039 Approved
0.7225 Intermediate Similarity NPD4037 Approved
0.7225 Intermediate Similarity NPD4036 Approved
0.7175 Intermediate Similarity NPD5512 Phase 3
0.7167 Intermediate Similarity NPD5903 Approved
0.7167 Intermediate Similarity NPD5902 Approved
0.7161 Intermediate Similarity NPD8479 Phase 2
0.716 Intermediate Similarity NPD7803 Approved
0.7155 Intermediate Similarity NPD7603 Discontinued
0.7143 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD4418 Discontinued
0.7125 Intermediate Similarity NPD4328 Approved
0.7118 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD7470 Discontinued
0.7103 Intermediate Similarity NPD7859 Phase 2
0.7101 Intermediate Similarity NPD8356 Approved
0.7092 Intermediate Similarity NPD5482 Discontinued
0.709 Intermediate Similarity NPD7807 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD1392 Approved
0.7083 Intermediate Similarity NPD7674 Phase 3
0.7083 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7675 Phase 3
0.7082 Intermediate Similarity NPD7069 Discontinued
0.7072 Intermediate Similarity NPD3785 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD8091 Phase 3
0.7054 Intermediate Similarity NPD7944 Discontinued
0.7054 Intermediate Similarity NPD8430 Approved
0.7049 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7046 Intermediate Similarity NPD3258 Approved
0.7043 Intermediate Similarity NPD7001 Phase 3
0.7043 Intermediate Similarity NPD3507 Phase 2
0.704 Intermediate Similarity NPD6569 Phase 2
0.704 Intermediate Similarity NPD5488 Discontinued
0.7039 Intermediate Similarity NPD4502 Phase 2
0.7033 Intermediate Similarity NPD8489 Phase 1
0.7029 Intermediate Similarity NPD6209 Approved
0.7029 Intermediate Similarity NPD6995 Phase 1
0.7016 Intermediate Similarity NPD7417 Discontinued
0.7014 Intermediate Similarity NPD2383 Phase 1
0.7012 Intermediate Similarity NPD3263 Phase 3
0.7004 Intermediate Similarity NPD6985 Discontinued
0.7004 Intermediate Similarity NPD6249 Phase 2
0.7004 Intermediate Similarity NPD7708 Approved
0.7004 Intermediate Similarity NPD6248 Phase 2
0.7004 Intermediate Similarity NPD5632 Approved
0.7 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.6992 Remote Similarity NPD7181 Phase 3
0.6991 Remote Similarity NPD6206 Phase 1
0.6984 Remote Similarity NPD8324 Phase 2
0.6984 Remote Similarity NPD8102 Discontinued
0.6983 Remote Similarity NPD7665 Phase 2
0.6983 Remote Similarity NPD7666 Phase 3
0.6982 Remote Similarity NPD4334 Discontinued
0.6979 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6974 Remote Similarity NPD4600 Approved
0.6974 Remote Similarity NPD4601 Approved
0.697 Remote Similarity NPD5530 Phase 1
0.6967 Remote Similarity NPD7688 Phase 1
0.6964 Remote Similarity NPD4368 Phase 2
0.696 Remote Similarity NPD6261 Phase 3
0.696 Remote Similarity NPD7777 Approved
0.696 Remote Similarity NPD7778 Approved
0.696 Remote Similarity NPD53 Approved
0.6957 Remote Similarity NPD8101 Phase 3
0.6955 Remote Similarity NPD5559 Phase 2
0.6955 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6953 Remote Similarity NPD4520 Approved
0.6949 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6944 Remote Similarity NPD8358 Approved
0.6944 Remote Similarity NPD6276 Discontinued
0.6936 Remote Similarity NPD5866 Approved
0.6936 Remote Similarity NPD3816 Phase 1
0.6936 Remote Similarity NPD3815 Phase 1
0.6935 Remote Similarity NPD7729 Clinical (unspecified phase)
0.6926 Remote Similarity NPD4795 Phase 2
0.692 Remote Similarity NPD5612 Discontinued
0.692 Remote Similarity NPD2433 Clinical (unspecified phase)
0.692 Remote Similarity NPD8117 Approved
0.692 Remote Similarity NPD8116 Phase 3
0.6917 Remote Similarity NPD4558 Phase 2
0.6906 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6246 Approved
0.6901 Remote Similarity NPD6247 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6897 Remote Similarity NPD8284 Discontinued
0.6897 Remote Similarity NPD5601 Phase 2
0.6895 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6894 Remote Similarity NPD5922 Phase 3
0.6886 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6883 Remote Similarity NPD5487 Phase 1
0.6878 Remote Similarity NPD3257 Approved
0.6875 Remote Similarity NPD7180 Phase 3
0.6875 Remote Similarity NPD8370 Discontinued
0.6872 Remote Similarity NPD8289 Discontinued
0.6867 Remote Similarity NPD5429 Discontinued
0.6866 Remote Similarity NPD8107 Approved
0.6862 Remote Similarity NPD7395 Discontinued
0.6862 Remote Similarity NPD3354 Phase 2
0.6861 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5479 Discontinued
0.6856 Remote Similarity NPD4118 Clinical (unspecified phase)
0.6856 Remote Similarity NPD6999 Discontinued
0.6856 Remote Similarity NPD3800 Clinical (unspecified phase)
0.6856 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6855 Remote Similarity NPD7853 Phase 2
0.6854 Remote Similarity NPD8108 Approved
0.6853 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6846 Remote Similarity NPD7556 Discontinued
0.6844 Remote Similarity NPD7924 Phase 2
0.6844 Remote Similarity NPD7994 Phase 2
0.6844 Remote Similarity NPD7925 Phase 2
0.6842 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5003 Discontinued
0.684 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6838 Remote Similarity NPD8100 Phase 3
0.6832 Remote Similarity NPD5450 Discontinued
0.683 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6828 Remote Similarity NPD6590 Discontinued
0.6826 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6826 Remote Similarity NPD4500 Approved
0.6826 Remote Similarity NPD4501 Approved
0.6822 Remote Similarity NPD3570 Phase 2
0.6822 Remote Similarity NPD2540 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