Structure

Physi-Chem Properties

Molecular Weight:  210.08
Volume:  220.063
LogP:  2.874
LogD:  2.57
LogS:  -3.378
# Rotatable Bonds:  1
TPSA:  48.91
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.648
Synthetic Accessibility Score:  2.743
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.982
MDCK Permeability:  1.8244410966872238e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.92
30% Bioavailability (F30%):  0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.494
Plasma Protein Binding (PPB):  91.67760467529297%
Volume Distribution (VD):  0.751
Pgp-substrate:  6.356071472167969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.99
CYP1A2-substrate:  0.749
CYP2C19-inhibitor:  0.351
CYP2C19-substrate:  0.153
CYP2C9-inhibitor:  0.654
CYP2C9-substrate:  0.879
CYP2D6-inhibitor:  0.859
CYP2D6-substrate:  0.87
CYP3A4-inhibitor:  0.499
CYP3A4-substrate:  0.254

ADMET: Excretion

Clearance (CL):  6.088
Half-life (T1/2):  0.495

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.815
Drug-inuced Liver Injury (DILI):  0.97
AMES Toxicity:  0.444
Rat Oral Acute Toxicity:  0.966
Maximum Recommended Daily Dose:  0.327
Skin Sensitization:  0.898
Carcinogencity:  0.475
Eye Corrosion:  0.199
Eye Irritation:  0.985
Respiratory Toxicity:  0.987

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

  Natural Product: NPC192315

Natural Product ID:  NPC192315
Common Name*:   1-Vinyl-8-Hydroxy-Beta-Carboline
IUPAC Name:   1-ethenyl-9H-pyrido[3,4-b]indol-8-ol
Synonyms:  
Standard InCHIKey:  RZWQZVWQFRVQCI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H10N2O/c1-2-10-12-9(6-7-14-10)8-4-3-5-11(16)13(8)15-12/h2-7,15-16H,1H2
SMILES:  C=Cc1nccc2c1[nH]c1c2cccc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444237
PubChem CID:   5353368
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001140] Harmala 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
NPO2833 Cribricellina cribraria Species Catenicellidae Eukaryota n.a. n.a. n.a. PMID[1791472]
NPO25419 Pterocella vesiculosa Species n.a. n.a. n.a. New Zealand n.a. PMID[18052329]
NPO25419 Pterocella vesiculosa Species n.a. n.a. n.a. Alderman Islands off the North Island of New Zealand n.a. PMID[18052329]
NPO25419 Pterocella vesiculosa Species n.a. n.a. n.a. New Zealand n.a. PMID[19220033]
NPO25419 Pterocella vesiculosa Species n.a. n.a. n.a. n.a. n.a. PMID[19220033]
NPO21386 Catenicella cribraria Species Catenicellidae Eukaryota n.a. n.a. n.a. PMID[8277321]
NPO25419 Pterocella vesiculosa Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21386 Catenicella cribraria Species Catenicellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2833 Cribricellina cribraria Species Catenicellidae 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
NPT168 Cell Line P388 Mus musculus IC50 = 0.1 ug.mL-1 PMID[513267]
NPT168 Cell Line P388 Mus musculus IC50 = 0.1 ug.mL-1 PMID[513269]
NPT19 Organism Escherichia coli Escherichia coli MIC > 60.0 ug PMID[513267]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 7.5 ug PMID[513267]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 60.0 ug PMID[513267]
NPT20 Organism Candida albicans Candida albicans MIC = 15.0 ug PMID[513267]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 0.45 ug PMID[513267]
NPT1223 Organism Amorphotheca resinae Amorphotheca resinae MIC = 3.7 ug PMID[513267]
NPT3574 Organism Herpes simplex virus (type 1 / strain F) Herpes simplex virus (type 1 / strain F) IZ = 1.0 mm PMID[513267]
NPT1106 Organism Human poliovirus 1 Human poliovirus 1 IZ = 1.0 mm PMID[513267]
NPT27 Others Unspecified IZ = 2.0 mm PMID[513267]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 1800.0 nM PMID[513268]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI = 5800.0 nM PMID[513268]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LC50 = 19000.0 nM PMID[513268]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MID = 0.45 ug ml-1 PMID[513269]
NPT20 Organism Candida albicans Candida albicans MID = 15.0 ug ml-1 PMID[513269]
NPT79 Organism Bacillus subtilis Bacillus subtilis MID = 7.5 ug ml-1 PMID[513269]

☑ 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 NPC192315 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
0.9943 High Similarity NPC476167
0.9086 High Similarity NPC476138
0.9086 High Similarity NPC245816
0.8964 High Similarity NPC470799
0.8964 High Similarity NPC8022
0.8901 High Similarity NPC5145
0.8852 High Similarity NPC324149
0.8836 High Similarity NPC475070
0.8743 High Similarity NPC314940
0.8743 High Similarity NPC473764
0.8737 High Similarity NPC470500
0.8722 High Similarity NPC48938
0.8667 High Similarity NPC476287
0.8653 High Similarity NPC185782
0.8619 High Similarity NPC220765
0.8578 High Similarity NPC476451
0.8571 High Similarity NPC204717
0.8526 High Similarity NPC19872
0.8526 High Similarity NPC176538
0.8525 High Similarity NPC314002
0.852 High Similarity NPC26679
0.8478 Intermediate Similarity NPC171171
0.8449 Intermediate Similarity NPC99666
0.8398 Intermediate Similarity NPC184964
0.838 Intermediate Similarity NPC252590
0.8358 Intermediate Similarity NPC292958
0.835 Intermediate Similarity NPC476041
0.835 Intermediate Similarity NPC304926
0.8342 Intermediate Similarity NPC211813
0.8333 Intermediate Similarity NPC46580
0.8308 Intermediate Similarity NPC477113
0.829 Intermediate Similarity NPC232727
0.8272 Intermediate Similarity NPC77555
0.827 Intermediate Similarity NPC284678
0.8223 Intermediate Similarity NPC477111
0.8216 Intermediate Similarity NPC473312
0.8164 Intermediate Similarity NPC6215
0.8122 Intermediate Similarity NPC476121
0.8122 Intermediate Similarity NPC476124
0.8112 Intermediate Similarity NPC53144
0.8098 Intermediate Similarity NPC96890
0.8088 Intermediate Similarity NPC213530
0.8088 Intermediate Similarity NPC193267
0.8083 Intermediate Similarity NPC156704
0.8083 Intermediate Similarity NPC267928
0.8065 Intermediate Similarity NPC471891
0.8065 Intermediate Similarity NPC314394
0.8058 Intermediate Similarity NPC470501
0.8054 Intermediate Similarity NPC42979
0.8051 Intermediate Similarity NPC315491
0.8051 Intermediate Similarity NPC45459
0.8043 Intermediate Similarity NPC224764
0.8031 Intermediate Similarity NPC242209
0.803 Intermediate Similarity NPC477110
0.802 Intermediate Similarity NPC475774
0.802 Intermediate Similarity NPC200836
0.801 Intermediate Similarity NPC470502
0.8009 Intermediate Similarity NPC469554
0.8009 Intermediate Similarity NPC101543
0.7989 Intermediate Similarity NPC131718
0.7981 Intermediate Similarity NPC245348
0.798 Intermediate Similarity NPC470505
0.796 Intermediate Similarity NPC123976
0.796 Intermediate Similarity NPC167860
0.7959 Intermediate Similarity NPC213308
0.7957 Intermediate Similarity NPC72980
0.7957 Intermediate Similarity NPC88363
0.7953 Intermediate Similarity NPC477861
0.7943 Intermediate Similarity NPC60006
0.7938 Intermediate Similarity NPC251090
0.7934 Intermediate Similarity NPC182222
0.7933 Intermediate Similarity NPC470503
0.7929 Intermediate Similarity NPC223427
0.7929 Intermediate Similarity NPC476098
0.7927 Intermediate Similarity NPC307963
0.7921 Intermediate Similarity NPC141353
0.7914 Intermediate Similarity NPC478032
0.7906 Intermediate Similarity NPC296527
0.7902 Intermediate Similarity NPC27041
0.7887 Intermediate Similarity NPC326634
0.7871 Intermediate Similarity NPC85273
0.7868 Intermediate Similarity NPC249040
0.7865 Intermediate Similarity NPC76748
0.7861 Intermediate Similarity NPC18348
0.7843 Intermediate Similarity NPC477610
0.784 Intermediate Similarity NPC207686
0.7838 Intermediate Similarity NPC474409
0.7837 Intermediate Similarity NPC310118
0.7837 Intermediate Similarity NPC60621
0.7835 Intermediate Similarity NPC329541
0.7824 Intermediate Similarity NPC92111
0.7824 Intermediate Similarity NPC41679
0.7817 Intermediate Similarity NPC128823
0.7812 Intermediate Similarity NPC242928
0.7812 Intermediate Similarity NPC32771
0.7802 Intermediate Similarity NPC102423
0.7794 Intermediate Similarity NPC471603
0.7789 Intermediate Similarity NPC470678
0.7778 Intermediate Similarity NPC474798
0.7767 Intermediate Similarity NPC142901
0.7766 Intermediate Similarity NPC212213
0.7762 Intermediate Similarity NPC167908
0.7755 Intermediate Similarity NPC222018
0.7752 Intermediate Similarity NPC81175
0.7734 Intermediate Similarity NPC476116
0.7731 Intermediate Similarity NPC295228
0.7727 Intermediate Similarity NPC63545
0.7723 Intermediate Similarity NPC88008
0.7723 Intermediate Similarity NPC283117
0.7717 Intermediate Similarity NPC171393
0.7717 Intermediate Similarity NPC295452
0.7711 Intermediate Similarity NPC472259
0.7711 Intermediate Similarity NPC285558
0.7708 Intermediate Similarity NPC314573
0.7708 Intermediate Similarity NPC62749
0.7704 Intermediate Similarity NPC276517
0.77 Intermediate Similarity NPC314954
0.77 Intermediate Similarity NPC473761
0.7692 Intermediate Similarity NPC25899
0.7692 Intermediate Similarity NPC279918
0.7689 Intermediate Similarity NPC132631
0.7689 Intermediate Similarity NPC103687
0.7685 Intermediate Similarity NPC82548
0.7685 Intermediate Similarity NPC97902
0.7685 Intermediate Similarity NPC287208
0.7684 Intermediate Similarity NPC201380
0.7684 Intermediate Similarity NPC179787
0.7684 Intermediate Similarity NPC469811
0.7677 Intermediate Similarity NPC265576
0.767 Intermediate Similarity NPC266931
0.7659 Intermediate Similarity NPC208284
0.7656 Intermediate Similarity NPC15102
0.7653 Intermediate Similarity NPC110151
0.7653 Intermediate Similarity NPC106937
0.765 Intermediate Similarity NPC282231
0.765 Intermediate Similarity NPC48192
0.7644 Intermediate Similarity NPC212535
0.764 Intermediate Similarity NPC321911
0.7637 Intermediate Similarity NPC230869
0.7635 Intermediate Similarity NPC270918
0.7629 Intermediate Similarity NPC246700
0.7629 Intermediate Similarity NPC128751
0.7619 Intermediate Similarity NPC132642
0.7612 Intermediate Similarity NPC57398
0.7608 Intermediate Similarity NPC477609
0.7594 Intermediate Similarity NPC130570
0.759 Intermediate Similarity NPC469497
0.759 Intermediate Similarity NPC106833
0.7588 Intermediate Similarity NPC239954
0.7581 Intermediate Similarity NPC63751
0.7573 Intermediate Similarity NPC294375
0.7571 Intermediate Similarity NPC159856
0.7565 Intermediate Similarity NPC94943
0.7563 Intermediate Similarity NPC198673
0.7557 Intermediate Similarity NPC39092
0.7553 Intermediate Similarity NPC313791
0.7552 Intermediate Similarity NPC176127
0.7549 Intermediate Similarity NPC166492
0.7549 Intermediate Similarity NPC473362
0.7546 Intermediate Similarity NPC260434
0.7536 Intermediate Similarity NPC276657
0.7536 Intermediate Similarity NPC94157
0.7536 Intermediate Similarity NPC316981
0.7536 Intermediate Similarity NPC219087
0.7534 Intermediate Similarity NPC184225
0.7527 Intermediate Similarity NPC54988
0.7527 Intermediate Similarity NPC49954
0.7527 Intermediate Similarity NPC474561
0.7524 Intermediate Similarity NPC264285
0.7523 Intermediate Similarity NPC24370
0.7523 Intermediate Similarity NPC319232
0.7514 Intermediate Similarity NPC469763
0.7514 Intermediate Similarity NPC469786
0.7514 Intermediate Similarity NPC259644
0.7514 Intermediate Similarity NPC469765
0.7514 Intermediate Similarity NPC469760
0.7514 Intermediate Similarity NPC25008
0.7514 Intermediate Similarity NPC325903
0.7514 Intermediate Similarity NPC73952
0.7514 Intermediate Similarity NPC97367
0.7513 Intermediate Similarity NPC190007
0.7512 Intermediate Similarity NPC122436
0.7512 Intermediate Similarity NPC121772
0.7512 Intermediate Similarity NPC229893
0.7512 Intermediate Similarity NPC315957
0.7512 Intermediate Similarity NPC171787
0.7511 Intermediate Similarity NPC148889
0.7511 Intermediate Similarity NPC26543
0.75 Intermediate Similarity NPC120798
0.75 Intermediate Similarity NPC161887
0.75 Intermediate Similarity NPC60553
0.7489 Intermediate Similarity NPC477549
0.7488 Intermediate Similarity NPC473185
0.7487 Intermediate Similarity NPC44161
0.7487 Intermediate Similarity NPC13880
0.7486 Intermediate Similarity NPC236711
0.7476 Intermediate Similarity NPC174758
0.7474 Intermediate Similarity NPC42591
0.7473 Intermediate Similarity NPC211572
0.7473 Intermediate Similarity NPC75540

  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 NPC192315 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
0.8492 Intermediate Similarity NPD9690 Approved
0.8404 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD9705 Discontinued
0.84 Intermediate Similarity NPD112 Approved
0.8293 Intermediate Similarity NPD7603 Discontinued
0.8212 Intermediate Similarity NPD425 Approved
0.8212 Intermediate Similarity NPD424 Approved
0.8177 Intermediate Similarity NPD7948 Phase 1
0.8051 Intermediate Similarity NPD484 Approved
0.8021 Intermediate Similarity NPD9695 Approved
0.7989 Intermediate Similarity NPD5065 Approved
0.7927 Intermediate Similarity NPD1038 Approved
0.7908 Intermediate Similarity NPD2177 Approved
0.7908 Intermediate Similarity NPD2175 Phase 3
0.7908 Intermediate Similarity NPD2176 Approved
0.7876 Intermediate Similarity NPD9689 Approved
0.7835 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD706 Phase 1
0.7767 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7767 Intermediate Similarity NPD5612 Discontinued
0.7753 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD6159 Phase 2
0.7692 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD2615 Phase 3
0.767 Intermediate Similarity NPD2616 Phase 3
0.7663 Intermediate Similarity NPD925 Approved
0.7663 Intermediate Similarity NPD926 Approved
0.7659 Intermediate Similarity NPD5939 Approved
0.7659 Intermediate Similarity NPD5936 Approved
0.7656 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7653 Intermediate Similarity NPD802 Phase 2
0.7638 Intermediate Similarity NPD9688 Approved
0.7638 Intermediate Similarity NPD9687 Approved
0.7637 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD6290 Phase 2
0.7621 Intermediate Similarity NPD3330 Phase 1
0.7596 Intermediate Similarity NPD7112 Discontinued
0.755 Intermediate Similarity NPD3825 Phase 3
0.7547 Intermediate Similarity NPD1856 Discontinued
0.7537 Intermediate Similarity NPD4795 Phase 2
0.7512 Intermediate Similarity NPD1739 Approved
0.7512 Intermediate Similarity NPD1740 Approved
0.7488 Intermediate Similarity NPD4886 Phase 2
0.7488 Intermediate Similarity NPD4502 Phase 2
0.7476 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD4511 Phase 1
0.7447 Intermediate Similarity NPD1325 Approved
0.7447 Intermediate Similarity NPD1326 Approved
0.7413 Intermediate Similarity NPD712 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD1213 Phase 3
0.7405 Intermediate Similarity NPD9398 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD2383 Phase 1
0.7395 Intermediate Similarity NPD7586 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD2762 Phase 2
0.7385 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6595 Phase 3
0.7358 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD5255 Approved
0.735 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD5066 Phase 2
0.7321 Intermediate Similarity NPD5067 Phase 2
0.7318 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7309 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD2781 Approved
0.7302 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD7222 Phase 2
0.7295 Intermediate Similarity NPD1197 Approved
0.7295 Intermediate Similarity NPD1392 Approved
0.7294 Intermediate Similarity NPD5559 Phase 2
0.7291 Intermediate Similarity NPD4548 Discontinued
0.7291 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD8395 Approved
0.7291 Intermediate Similarity NPD8396 Approved
0.7287 Intermediate Similarity NPD2780 Approved
0.7287 Intermediate Similarity NPD2782 Approved
0.7282 Intermediate Similarity NPD4033 Approved
0.7282 Intermediate Similarity NPD31 Approved
0.7282 Intermediate Similarity NPD4036 Approved
0.7282 Intermediate Similarity NPD4037 Approved
0.7282 Intermediate Similarity NPD4122 Approved
0.7282 Intermediate Similarity NPD4034 Approved
0.7282 Intermediate Similarity NPD4039 Approved
0.7282 Intermediate Similarity NPD4038 Approved
0.7282 Intermediate Similarity NPD4035 Approved
0.7282 Intermediate Similarity NPD32 Approved
0.7277 Intermediate Similarity NPD1229 Phase 2
0.7273 Intermediate Similarity NPD3746 Discontinued
0.726 Intermediate Similarity NPD2189 Approved
0.726 Intermediate Similarity NPD5658 Approved
0.726 Intermediate Similarity NPD2187 Approved
0.7252 Intermediate Similarity NPD4454 Phase 2
0.725 Intermediate Similarity NPD3404 Approved
0.7246 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD534 Phase 2
0.7243 Intermediate Similarity NPD537 Phase 2
0.724 Intermediate Similarity NPD7558 Phase 2
0.724 Intermediate Similarity NPD482 Approved
0.7212 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD1722 Approved
0.7206 Intermediate Similarity NPD3814 Phase 1
0.7204 Intermediate Similarity NPD9382 Approved
0.7204 Intermediate Similarity NPD9383 Approved
0.7202 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD3931 Approved
0.7184 Intermediate Similarity NPD6975 Discontinued
0.7184 Intermediate Similarity NPD3928 Approved
0.7174 Intermediate Similarity NPD2882 Phase 1
0.717 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD6569 Phase 2
0.7164 Intermediate Similarity NPD996 Phase 2
0.7164 Intermediate Similarity NPD994 Phase 2
0.715 Intermediate Similarity NPD5164 Discontinued
0.7143 Intermediate Similarity NPD4203 Approved
0.7143 Intermediate Similarity NPD4204 Approved
0.7136 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD2951 Discontinued
0.7129 Intermediate Similarity NPD7452 Approved
0.7129 Intermediate Similarity NPD7453 Approved
0.7129 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD1273 Discontinued
0.7119 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7116 Intermediate Similarity NPD4429 Discontinued
0.7115 Intermediate Similarity NPD5901 Discontinued
0.7114 Intermediate Similarity NPD459 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5100 Phase 3
0.7103 Intermediate Similarity NPD6643 Discontinued
0.71 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD408 Approved
0.7097 Intermediate Similarity NPD7726 Phase 1
0.7097 Intermediate Similarity NPD4881 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD1685 Approved
0.709 Intermediate Similarity NPD1684 Approved
0.7083 Intermediate Similarity NPD3402 Phase 1
0.7081 Intermediate Similarity NPD3003 Approved
0.7081 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6158 Phase 2
0.7081 Intermediate Similarity NPD5530 Phase 1
0.7075 Intermediate Similarity NPD4131 Phase 3
0.7075 Intermediate Similarity NPD949 Phase 1
0.7071 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD6492 Phase 2
0.7062 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7061 Intermediate Similarity NPD7068 Approved
0.7061 Intermediate Similarity NPD7067 Approved
0.7061 Intermediate Similarity NPD4440 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3477 Phase 2
0.7059 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD5482 Discontinued
0.7053 Intermediate Similarity NPD5140 Approved
0.7053 Intermediate Similarity NPD5138 Approved
0.7051 Intermediate Similarity NPD6242 Discontinued
0.705 Intermediate Similarity NPD8431 Approved
0.7043 Intermediate Similarity NPD2837 Discontinued
0.7039 Intermediate Similarity NPD5999 Phase 2
0.7033 Intermediate Similarity NPD3813 Approved
0.7031 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD2381 Approved
0.7026 Intermediate Similarity NPD2382 Approved
0.7026 Intermediate Similarity NPD2380 Approved
0.7022 Intermediate Similarity NPD3006 Discontinued
0.7021 Intermediate Similarity NPD2581 Approved
0.7021 Intermediate Similarity NPD2582 Approved
0.702 Intermediate Similarity NPD2092 Phase 2
0.702 Intermediate Similarity NPD2095 Phase 2
0.702 Intermediate Similarity NPD2094 Phase 2
0.702 Intermediate Similarity NPD2391 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD1592 Phase 3
0.7015 Intermediate Similarity NPD9714 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD4845 Discontinued
0.7011 Intermediate Similarity NPD4703 Approved
0.7011 Intermediate Similarity NPD1661 Suspended
0.7011 Intermediate Similarity NPD4702 Approved
0.7 Intermediate Similarity NPD786 Approved
0.6995 Remote Similarity NPD3922 Approved
0.6995 Remote Similarity NPD3921 Approved
0.6995 Remote Similarity NPD3924 Approved
0.6995 Remote Similarity NPD3923 Approved
0.6987 Remote Similarity NPD3343 Phase 3
0.6985 Remote Similarity NPD2091 Phase 2
0.6985 Remote Similarity NPD2096 Phase 2
0.698 Remote Similarity NPD3321 Discontinued
0.6979 Remote Similarity NPD6961 Discontinued
0.6967 Remote Similarity NPD796 Phase 2
0.6965 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6965 Remote Similarity NPD1034 Phase 3
0.6963 Remote Similarity NPD863 Approved
0.6963 Remote Similarity NPD862 Approved
0.6963 Remote Similarity NPD861 Approved
0.6959 Remote Similarity NPD2123 Phase 3
0.6958 Remote Similarity NPD4442 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