Structure

Physi-Chem Properties

Molecular Weight:  231.05
Volume:  226.698
LogP:  1.392
LogD:  0.767
LogS:  -2.588
# Rotatable Bonds:  1
TPSA:  95.29
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.704
Synthetic Accessibility Score:  3.284
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.025
MDCK Permeability:  1.3923097867518663e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.989
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.53
Plasma Protein Binding (PPB):  88.03922271728516%
Volume Distribution (VD):  0.597
Pgp-substrate:  18.024452209472656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.604
CYP1A2-substrate:  0.361
CYP2C19-inhibitor:  0.071
CYP2C19-substrate:  0.081
CYP2C9-inhibitor:  0.229
CYP2C9-substrate:  0.474
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.182
CYP3A4-inhibitor:  0.211
CYP3A4-substrate:  0.182

ADMET: Excretion

Clearance (CL):  1.456
Half-life (T1/2):  0.296

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.081
Drug-inuced Liver Injury (DILI):  0.957
AMES Toxicity:  0.383
Rat Oral Acute Toxicity:  0.306
Maximum Recommended Daily Dose:  0.026
Skin Sensitization:  0.813
Carcinogencity:  0.28
Eye Corrosion:  0.061
Eye Irritation:  0.403
Respiratory Toxicity:  0.893

Download Data

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

  Natural Product: NPC238108

Natural Product ID:  NPC238108
Common Name*:   5-Hydroxy-3-Amino-2-Aceto-1,4-Naphthoquinone
IUPAC Name:   2-acetyl-3-amino-5-hydroxynaphthalene-1,4-dione
Synonyms:  
Standard InCHIKey:  GADBCXPEZFEVON-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H9NO4/c1-5(14)8-10(13)12(17)9-6(11(8)16)3-2-4-7(9)15/h2-4,15H,13H2,1H3
SMILES:  CC(=O)C1=C(N)C(=O)c2c(C1=O)cccc2O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL480849
PubChem CID:   10609537
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*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
NPO27762 Goniothalamus marcanii Species Annonaceae Eukaryota stem bark n.a. n.a. PMID[10543899]
NPO27762 Goniothalamus marcanii Species Annonaceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 2.6 uM PMID[504815]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 2.6 uM PMID[504815]
NPT380 Cell Line U-251 Homo sapiens ED50 = 3.03 uM PMID[504815]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 3.03 uM PMID[504815]

☑ 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 NPC238108 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
0.8615 High Similarity NPC285829
0.8615 High Similarity NPC206778
0.8561 High Similarity NPC307174
0.8444 Intermediate Similarity NPC231774
0.8444 Intermediate Similarity NPC306765
0.8444 Intermediate Similarity NPC3224
0.8433 Intermediate Similarity NPC310540
0.8358 Intermediate Similarity NPC375356
0.8308 Intermediate Similarity NPC108288
0.8284 Intermediate Similarity NPC300274
0.8261 Intermediate Similarity NPC34414
0.8261 Intermediate Similarity NPC146647
0.8235 Intermediate Similarity NPC103540
0.8188 Intermediate Similarity NPC237225
0.8188 Intermediate Similarity NPC282923
0.8175 Intermediate Similarity NPC96915
0.8162 Intermediate Similarity NPC142956
0.8143 Intermediate Similarity NPC244699
0.8141 Intermediate Similarity NPC314693
0.8129 Intermediate Similarity NPC99731
0.812 Intermediate Similarity NPC232178
0.8092 Intermediate Similarity NPC161304
0.8085 Intermediate Similarity NPC246693
0.8085 Intermediate Similarity NPC242358
0.8085 Intermediate Similarity NPC110609
0.8071 Intermediate Similarity NPC55949
0.8071 Intermediate Similarity NPC117609
0.8071 Intermediate Similarity NPC198305
0.8058 Intermediate Similarity NPC48248
0.8043 Intermediate Similarity NPC1991
0.8043 Intermediate Similarity NPC51037
0.803 Intermediate Similarity NPC477453
0.8029 Intermediate Similarity NPC234890
0.8029 Intermediate Similarity NPC74507
0.8028 Intermediate Similarity NPC171968
0.8028 Intermediate Similarity NPC53896
0.8014 Intermediate Similarity NPC205992
0.8 Intermediate Similarity NPC278928
0.7986 Intermediate Similarity NPC471530
0.7972 Intermediate Similarity NPC50924
0.7962 Intermediate Similarity NPC101207
0.7958 Intermediate Similarity NPC309430
0.7958 Intermediate Similarity NPC58685
0.7943 Intermediate Similarity NPC475741
0.7943 Intermediate Similarity NPC136588
0.7943 Intermediate Similarity NPC199253
0.7929 Intermediate Similarity NPC165257
0.7917 Intermediate Similarity NPC281513
0.7917 Intermediate Similarity NPC283088
0.7917 Intermediate Similarity NPC22222
0.7902 Intermediate Similarity NPC225051
0.7902 Intermediate Similarity NPC115458
0.7899 Intermediate Similarity NPC173978
0.7899 Intermediate Similarity NPC152525
0.7899 Intermediate Similarity NPC68756
0.7862 Intermediate Similarity NPC193358
0.7832 Intermediate Similarity NPC70622
0.7826 Intermediate Similarity NPC135062
0.782 Intermediate Similarity NPC240163
0.7817 Intermediate Similarity NPC31799
0.7812 Intermediate Similarity NPC12890
0.7806 Intermediate Similarity NPC96160
0.7806 Intermediate Similarity NPC4331
0.7794 Intermediate Similarity NPC473662
0.7794 Intermediate Similarity NPC7151
0.7794 Intermediate Similarity NPC216297
0.7793 Intermediate Similarity NPC80035
0.7793 Intermediate Similarity NPC161632
0.7786 Intermediate Similarity NPC160499
0.7778 Intermediate Similarity NPC254603
0.7778 Intermediate Similarity NPC41567
0.7778 Intermediate Similarity NPC294226
0.7778 Intermediate Similarity NPC52407
0.7762 Intermediate Similarity NPC17083
0.7762 Intermediate Similarity NPC205360
0.7755 Intermediate Similarity NPC173980
0.7755 Intermediate Similarity NPC61590
0.7754 Intermediate Similarity NPC91478
0.7754 Intermediate Similarity NPC282577
0.7746 Intermediate Similarity NPC25736
0.774 Intermediate Similarity NPC155211
0.774 Intermediate Similarity NPC141934
0.774 Intermediate Similarity NPC272268
0.774 Intermediate Similarity NPC315275
0.774 Intermediate Similarity NPC474813
0.7724 Intermediate Similarity NPC44437
0.7724 Intermediate Similarity NPC288089
0.7708 Intermediate Similarity NPC477406
0.7704 Intermediate Similarity NPC269414
0.7704 Intermediate Similarity NPC125252
0.7703 Intermediate Similarity NPC299405
0.7703 Intermediate Similarity NPC306835
0.7703 Intermediate Similarity NPC256463
0.7703 Intermediate Similarity NPC111422
0.7703 Intermediate Similarity NPC216312
0.7703 Intermediate Similarity NPC29771
0.7703 Intermediate Similarity NPC471602
0.7703 Intermediate Similarity NPC476477
0.7703 Intermediate Similarity NPC295339
0.7702 Intermediate Similarity NPC163924
0.7702 Intermediate Similarity NPC54661
0.7698 Intermediate Similarity NPC182646
0.7698 Intermediate Similarity NPC477153
0.7692 Intermediate Similarity NPC224584
0.7692 Intermediate Similarity NPC31539
0.7687 Intermediate Similarity NPC53206
0.7687 Intermediate Similarity NPC53414
0.7687 Intermediate Similarity NPC305060
0.7687 Intermediate Similarity NPC245923
0.7681 Intermediate Similarity NPC120545
0.7671 Intermediate Similarity NPC258502
0.7669 Intermediate Similarity NPC315406
0.766 Intermediate Similarity NPC49647
0.766 Intermediate Similarity NPC136342
0.766 Intermediate Similarity NPC295202
0.766 Intermediate Similarity NPC227741
0.766 Intermediate Similarity NPC15837
0.7651 Intermediate Similarity NPC241349
0.7651 Intermediate Similarity NPC327916
0.7651 Intermediate Similarity NPC32749
0.7651 Intermediate Similarity NPC37992
0.7651 Intermediate Similarity NPC42262
0.7651 Intermediate Similarity NPC220496
0.7651 Intermediate Similarity NPC147542
0.7643 Intermediate Similarity NPC236189
0.7635 Intermediate Similarity NPC4214
0.7635 Intermediate Similarity NPC61398
0.7635 Intermediate Similarity NPC13715
0.7635 Intermediate Similarity NPC416
0.7626 Intermediate Similarity NPC283514
0.7619 Intermediate Similarity NPC86524
0.7619 Intermediate Similarity NPC254847
0.7619 Intermediate Similarity NPC474311
0.7615 Intermediate Similarity NPC34715
0.7609 Intermediate Similarity NPC115188
0.7609 Intermediate Similarity NPC35856
0.7609 Intermediate Similarity NPC472046
0.7609 Intermediate Similarity NPC179092
0.7609 Intermediate Similarity NPC190971
0.7609 Intermediate Similarity NPC26433
0.7609 Intermediate Similarity NPC244994
0.7609 Intermediate Similarity NPC292665
0.7609 Intermediate Similarity NPC159760
0.7609 Intermediate Similarity NPC178395
0.7609 Intermediate Similarity NPC222876
0.7609 Intermediate Similarity NPC301987
0.7609 Intermediate Similarity NPC272454
0.7606 Intermediate Similarity NPC45537
0.7603 Intermediate Similarity NPC166480
0.7603 Intermediate Similarity NPC282780
0.76 Intermediate Similarity NPC297322
0.76 Intermediate Similarity NPC257003
0.76 Intermediate Similarity NPC471444
0.7591 Intermediate Similarity NPC184579
0.7591 Intermediate Similarity NPC233165
0.7589 Intermediate Similarity NPC123506
0.7589 Intermediate Similarity NPC131799
0.7584 Intermediate Similarity NPC114620
0.7584 Intermediate Similarity NPC1268
0.7584 Intermediate Similarity NPC26924
0.7584 Intermediate Similarity NPC103337
0.7584 Intermediate Similarity NPC477408
0.7584 Intermediate Similarity NPC242994
0.7584 Intermediate Similarity NPC13696
0.7584 Intermediate Similarity NPC138099
0.7576 Intermediate Similarity NPC313708
0.7571 Intermediate Similarity NPC275145
0.7568 Intermediate Similarity NPC471452
0.7568 Intermediate Similarity NPC471905
0.7554 Intermediate Similarity NPC198336
0.7552 Intermediate Similarity NPC179898
0.7552 Intermediate Similarity NPC95537
0.7552 Intermediate Similarity NPC96024
0.755 Intermediate Similarity NPC474300
0.7535 Intermediate Similarity NPC254492
0.7534 Intermediate Similarity NPC314048
0.7533 Intermediate Similarity NPC315578
0.7533 Intermediate Similarity NPC181560
0.7533 Intermediate Similarity NPC169452
0.7518 Intermediate Similarity NPC199273
0.7517 Intermediate Similarity NPC85342
0.7517 Intermediate Similarity NPC93015
0.7517 Intermediate Similarity NPC72669
0.7517 Intermediate Similarity NPC474517
0.75 Intermediate Similarity NPC21873
0.75 Intermediate Similarity NPC476473
0.75 Intermediate Similarity NPC164947
0.75 Intermediate Similarity NPC244351
0.75 Intermediate Similarity NPC217756
0.7483 Intermediate Similarity NPC287604
0.7483 Intermediate Similarity NPC124365
0.7483 Intermediate Similarity NPC72667
0.7483 Intermediate Similarity NPC161964
0.7483 Intermediate Similarity NPC84273
0.7483 Intermediate Similarity NPC12070
0.7483 Intermediate Similarity NPC472262
0.7482 Intermediate Similarity NPC165197
0.7467 Intermediate Similarity NPC143438
0.7466 Intermediate Similarity NPC88864
0.7465 Intermediate Similarity NPC167055

  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 NPC238108 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
0.8308 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD1470 Approved
0.7941 Intermediate Similarity NPD1201 Approved
0.774 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD3300 Phase 2
0.7203 Intermediate Similarity NPD182 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD256 Approved
0.7174 Intermediate Similarity NPD255 Approved
0.7171 Intermediate Similarity NPD2346 Discontinued
0.7118 Intermediate Similarity NPD5029 Approved
0.7118 Intermediate Similarity NPD5031 Approved
0.7118 Intermediate Similarity NPD5027 Approved
0.7114 Intermediate Similarity NPD943 Approved
0.7105 Intermediate Similarity NPD5408 Approved
0.7105 Intermediate Similarity NPD5405 Approved
0.7105 Intermediate Similarity NPD5404 Approved
0.7105 Intermediate Similarity NPD5406 Approved
0.7103 Intermediate Similarity NPD1164 Approved
0.7086 Intermediate Similarity NPD9279 Approved
0.7076 Intermediate Similarity NPD36 Approved
0.7076 Intermediate Similarity NPD4954 Approved
0.7076 Intermediate Similarity NPD4955 Approved
0.7076 Intermediate Similarity NPD5028 Approved
0.7076 Intermediate Similarity NPD5034 Approved
0.7076 Intermediate Similarity NPD5026 Approved
0.7055 Intermediate Similarity NPD257 Approved
0.7055 Intermediate Similarity NPD258 Approved
0.7042 Intermediate Similarity NPD2932 Approved
0.7039 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD74 Approved
0.7037 Intermediate Similarity NPD9266 Approved
0.7032 Intermediate Similarity NPD1196 Approved
0.7024 Intermediate Similarity NPD5033 Approved
0.7018 Intermediate Similarity NPD5030 Phase 2
0.7006 Intermediate Similarity NPD1543 Discontinued
0.7 Intermediate Similarity NPD3226 Approved
0.7 Intermediate Similarity NPD9493 Approved
0.6968 Remote Similarity NPD1195 Approved
0.6966 Remote Similarity NPD1755 Approved
0.6963 Remote Similarity NPD9264 Approved
0.6963 Remote Similarity NPD9267 Approved
0.6963 Remote Similarity NPD9263 Approved
0.6948 Remote Similarity NPD2344 Approved
0.6923 Remote Similarity NPD3019 Approved
0.6914 Remote Similarity NPD5038 Approved
0.6914 Remote Similarity NPD2672 Discontinued
0.6914 Remote Similarity NPD5037 Approved
0.691 Remote Similarity NPD6213 Phase 3
0.691 Remote Similarity NPD6214 Clinical (unspecified phase)
0.691 Remote Similarity NPD6212 Phase 3
0.6903 Remote Similarity NPD75 Approved
0.6903 Remote Similarity NPD9277 Approved
0.6901 Remote Similarity NPD4956 Approved
0.6899 Remote Similarity NPD7390 Discontinued
0.6883 Remote Similarity NPD2935 Discontinued
0.6879 Remote Similarity NPD9568 Approved
0.6857 Remote Similarity NPD5036 Approved
0.6854 Remote Similarity NPD5968 Phase 3
0.6853 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6839 Remote Similarity NPD1471 Phase 3
0.6839 Remote Similarity NPD9276 Approved
0.6839 Remote Similarity NPD9274 Approved
0.6839 Remote Similarity NPD9278 Suspended
0.6839 Remote Similarity NPD9275 Approved
0.6835 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6824 Remote Similarity NPD2798 Approved
0.6821 Remote Similarity NPD5039 Approved
0.6818 Remote Similarity NPD2799 Discontinued
0.6796 Remote Similarity NPD5195 Discontinued
0.6786 Remote Similarity NPD3286 Discontinued
0.6783 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6782 Remote Similarity NPD5032 Approved
0.6779 Remote Similarity NPD9569 Approved
0.6776 Remote Similarity NPD826 Approved
0.6776 Remote Similarity NPD825 Approved
0.6772 Remote Similarity NPD2309 Approved
0.6755 Remote Similarity NPD2313 Discontinued
0.675 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6743 Remote Similarity NPD5035 Approved
0.6738 Remote Similarity NPD9281 Approved
0.6732 Remote Similarity NPD274 Approved
0.6732 Remote Similarity NPD275 Approved
0.6711 Remote Similarity NPD259 Phase 1
0.6711 Remote Similarity NPD520 Approved
0.6703 Remote Similarity NPD7282 Approved
0.6688 Remote Similarity NPD1607 Approved
0.6688 Remote Similarity NPD970 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3455 Phase 2
0.6686 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1240 Approved
0.6667 Remote Similarity NPD9261 Approved
0.6667 Remote Similarity NPD5197 Approved
0.6667 Remote Similarity NPD9717 Approved
0.6667 Remote Similarity NPD5194 Approved
0.6667 Remote Similarity NPD288 Approved
0.6667 Remote Similarity NPD5196 Approved
0.6648 Remote Similarity NPD6836 Approved
0.6646 Remote Similarity NPD3684 Discontinued
0.6645 Remote Similarity NPD411 Approved
0.6645 Remote Similarity NPD3764 Approved
0.6644 Remote Similarity NPD1203 Approved
0.6643 Remote Similarity NPD9508 Approved
0.663 Remote Similarity NPD5610 Approved
0.663 Remote Similarity NPD5609 Approved
0.663 Remote Similarity NPD5608 Approved
0.6629 Remote Similarity NPD5637 Discontinued
0.6629 Remote Similarity NPD8150 Discontinued
0.6623 Remote Similarity NPD555 Phase 2
0.6623 Remote Similarity NPD447 Suspended
0.6619 Remote Similarity NPD1792 Phase 2
0.6608 Remote Similarity NPD1913 Phase 1
0.6604 Remote Similarity NPD3400 Discontinued
0.6604 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6603 Remote Similarity NPD1510 Phase 2
0.66 Remote Similarity NPD2195 Approved
0.66 Remote Similarity NPD2194 Approved
0.6592 Remote Similarity NPD6835 Approved
0.6591 Remote Similarity NPD844 Approved
0.6585 Remote Similarity NPD2649 Approved
0.6585 Remote Similarity NPD2651 Approved
0.6579 Remote Similarity NPD9537 Phase 1
0.6579 Remote Similarity NPD9536 Phase 1
0.6577 Remote Similarity NPD1876 Approved
0.6577 Remote Similarity NPD1574 Approved
0.6568 Remote Similarity NPD3252 Approved
0.6566 Remote Similarity NPD6844 Discontinued
0.6561 Remote Similarity NPD9570 Approved
0.6552 Remote Similarity NPD1759 Phase 1
0.6547 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6533 Remote Similarity NPD1593 Approved
0.6532 Remote Similarity NPD3446 Phase 1
0.6531 Remote Similarity NPD3026 Approved
0.6531 Remote Similarity NPD3023 Approved
0.6525 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6522 Remote Similarity NPD1445 Approved
0.6522 Remote Similarity NPD1444 Approved
0.6519 Remote Similarity NPD289 Clinical (unspecified phase)
0.6519 Remote Similarity NPD7283 Approved
0.6509 Remote Similarity NPD955 Approved
0.6507 Remote Similarity NPD3025 Approved
0.6507 Remote Similarity NPD3024 Approved
0.6507 Remote Similarity NPD4093 Discontinued
0.6505 Remote Similarity NPD4914 Approved
0.6503 Remote Similarity NPD9618 Approved
0.6503 Remote Similarity NPD9614 Approved
0.6503 Remote Similarity NPD5951 Approved
0.6503 Remote Similarity NPD6534 Approved
0.6503 Remote Similarity NPD6535 Approved
0.65 Remote Similarity NPD3750 Approved
0.6496 Remote Similarity NPD9608 Approved
0.6496 Remote Similarity NPD9610 Approved
0.6488 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4974 Approved
0.6486 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4975 Approved
0.6483 Remote Similarity NPD1758 Phase 1
0.6479 Remote Similarity NPD7635 Approved
0.6475 Remote Similarity NPD2342 Discontinued
0.6475 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6467 Remote Similarity NPD1283 Approved
0.6463 Remote Similarity NPD1751 Approved
0.6457 Remote Similarity NPD6020 Phase 2
0.6453 Remote Similarity NPD1839 Phase 1
0.6453 Remote Similarity NPD6232 Discontinued
0.6447 Remote Similarity NPD4208 Discontinued
0.6442 Remote Similarity NPD2532 Approved
0.6442 Remote Similarity NPD2534 Approved
0.6442 Remote Similarity NPD2533 Approved
0.6438 Remote Similarity NPD2800 Approved
0.6437 Remote Similarity NPD7324 Discontinued
0.6437 Remote Similarity NPD7473 Discontinued
0.6429 Remote Similarity NPD7819 Suspended
0.642 Remote Similarity NPD5190 Phase 2
0.6417 Remote Similarity NPD6781 Approved
0.6417 Remote Similarity NPD6778 Approved
0.6417 Remote Similarity NPD6779 Approved
0.6417 Remote Similarity NPD6780 Approved
0.6417 Remote Similarity NPD6782 Approved
0.6417 Remote Similarity NPD6777 Approved
0.6417 Remote Similarity NPD6776 Approved
0.641 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6407 Remote Similarity NPD2366 Approved
0.6402 Remote Similarity NPD9509 Clinical (unspecified phase)
0.64 Remote Similarity NPD2361 Approved
0.64 Remote Similarity NPD7177 Discontinued
0.6398 Remote Similarity NPD7699 Phase 2
0.6398 Remote Similarity NPD7700 Phase 2
0.6398 Remote Similarity NPD7003 Approved
0.6398 Remote Similarity NPD4668 Phase 2
0.6398 Remote Similarity NPD8166 Discontinued
0.6395 Remote Similarity NPD1651 Approved
0.6392 Remote Similarity NPD7301 Phase 3
0.6384 Remote Similarity NPD1252 Clinical (unspecified phase)
0.6383 Remote Similarity NPD4750 Phase 3
0.6379 Remote Similarity NPD6894 Phase 1
0.6377 Remote Similarity NPD1237 Approved
0.6375 Remote Similarity NPD4256 Phase 2
0.6375 Remote Similarity NPD4257 Approved
0.6375 Remote Similarity NPD1549 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