Structure

Physi-Chem Properties

Molecular Weight:  420.18
Volume:  423.822
LogP:  0.948
LogD:  0.909
LogS:  -2.584
# Rotatable Bonds:  6
TPSA:  138.2
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.254
Synthetic Accessibility Score:  4.796
Fsp3:  0.545
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.178
MDCK Permeability:  9.770200267666951e-05
Pgp-inhibitor:  0.031
Pgp-substrate:  0.552
Human Intestinal Absorption (HIA):  0.861
20% Bioavailability (F20%):  0.535
30% Bioavailability (F30%):  0.545

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.694
Plasma Protein Binding (PPB):  71.89020538330078%
Volume Distribution (VD):  0.262
Pgp-substrate:  15.701677322387695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.116
CYP2C19-inhibitor:  0.056
CYP2C19-substrate:  0.578
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.079
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.061
CYP3A4-inhibitor:  0.08
CYP3A4-substrate:  0.511

ADMET: Excretion

Clearance (CL):  2.501
Half-life (T1/2):  0.778

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.298
Drug-inuced Liver Injury (DILI):  0.401
AMES Toxicity:  0.081
Rat Oral Acute Toxicity:  0.869
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.401
Carcinogencity:  0.66
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.752

Download Data

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

  Natural Product: NPC264819

Natural Product ID:  NPC264819
Common Name*:   Nigrospoxydon A
IUPAC Name:   [(1R,5R,6S)-5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl] (2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate
Synonyms:  
Standard InCHIKey:  DMBDZHVALRXOEF-OQNJJOTNSA-N
Standard InCHI:  InChI=1S/C22H28O8/c1-12(5-6-22(29)13(2)8-15(24)10-21(22,3)4)7-17(26)30-20-18(27)14(11-23)9-16(25)19(20)28/h5-9,16,19-20,23,25,28-29H,10-11H2,1-4H3/b6-5+,12-7-/t16-,19+,20+,22-/m1/s1
SMILES:  OCC1=C[C@@H](O)[C@@H]([C@H](C1=O)OC(=O)/C=C(C=C[C@@]1(O)C(=CC(=O)CC1(C)C)C)/C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL526455
PubChem CID:   25016662
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002245] Abscisic acids and derivatives

*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
NPO32983 nigrospora sp. psu-f5 Species Trichosphaeriaceae Eukaryota n.a. n.a. n.a. PMID[18646829]

☑ 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 64.0 ug.mL-1 PMID[489180]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128.0 ug.mL-1 PMID[489180]

☑ 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 NPC264819 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
0.8762 High Similarity NPC266514
0.8654 High Similarity NPC118902
0.8654 High Similarity NPC469980
0.8654 High Similarity NPC104161
0.8364 Intermediate Similarity NPC317687
0.8349 Intermediate Similarity NPC89408
0.8273 Intermediate Similarity NPC317107
0.8241 Intermediate Similarity NPC469853
0.8208 Intermediate Similarity NPC39996
0.8148 Intermediate Similarity NPC477125
0.8125 Intermediate Similarity NPC469454
0.8125 Intermediate Similarity NPC469463
0.8125 Intermediate Similarity NPC469496
0.8108 Intermediate Similarity NPC179798
0.8108 Intermediate Similarity NPC304180
0.8039 Intermediate Similarity NPC142838
0.8018 Intermediate Similarity NPC5103
0.8 Intermediate Similarity NPC151393
0.8 Intermediate Similarity NPC322903
0.7965 Intermediate Similarity NPC56448
0.7965 Intermediate Similarity NPC471204
0.7928 Intermediate Similarity NPC87335
0.7925 Intermediate Similarity NPC61630
0.7925 Intermediate Similarity NPC307517
0.7925 Intermediate Similarity NPC81483
0.7925 Intermediate Similarity NPC169468
0.7899 Intermediate Similarity NPC24651
0.7899 Intermediate Similarity NPC470922
0.789 Intermediate Similarity NPC146731
0.789 Intermediate Similarity NPC296950
0.7881 Intermediate Similarity NPC470265
0.7881 Intermediate Similarity NPC23786
0.7857 Intermediate Similarity NPC115257
0.7857 Intermediate Similarity NPC161816
0.7845 Intermediate Similarity NPC251310
0.7845 Intermediate Similarity NPC186525
0.783 Intermediate Similarity NPC474194
0.7826 Intermediate Similarity NPC64318
0.7826 Intermediate Similarity NPC270478
0.7818 Intermediate Similarity NPC469852
0.7815 Intermediate Similarity NPC67251
0.7798 Intermediate Similarity NPC473624
0.7798 Intermediate Similarity NPC472755
0.7798 Intermediate Similarity NPC159533
0.7797 Intermediate Similarity NPC67569
0.7797 Intermediate Similarity NPC472001
0.7778 Intermediate Similarity NPC207885
0.7778 Intermediate Similarity NPC268958
0.7778 Intermediate Similarity NPC112613
0.7768 Intermediate Similarity NPC475065
0.7768 Intermediate Similarity NPC42662
0.7768 Intermediate Similarity NPC475922
0.7759 Intermediate Similarity NPC27999
0.7759 Intermediate Similarity NPC477116
0.7759 Intermediate Similarity NPC23046
0.7757 Intermediate Similarity NPC159763
0.7757 Intermediate Similarity NPC316598
0.7757 Intermediate Similarity NPC124512
0.7757 Intermediate Similarity NPC278386
0.775 Intermediate Similarity NPC476729
0.7748 Intermediate Similarity NPC67321
0.7748 Intermediate Similarity NPC187435
0.7748 Intermediate Similarity NPC143609
0.7748 Intermediate Similarity NPC330011
0.7748 Intermediate Similarity NPC329048
0.7742 Intermediate Similarity NPC168879
0.7736 Intermediate Similarity NPC57664
0.7731 Intermediate Similarity NPC312833
0.7727 Intermediate Similarity NPC118911
0.7727 Intermediate Similarity NPC220964
0.7727 Intermediate Similarity NPC475676
0.7727 Intermediate Similarity NPC472756
0.7719 Intermediate Similarity NPC476801
0.7719 Intermediate Similarity NPC473877
0.7719 Intermediate Similarity NPC269530
0.7719 Intermediate Similarity NPC66108
0.7712 Intermediate Similarity NPC48692
0.7706 Intermediate Similarity NPC472754
0.7706 Intermediate Similarity NPC473596
0.7705 Intermediate Similarity NPC236999
0.7699 Intermediate Similarity NPC235014
0.7699 Intermediate Similarity NPC286880
0.7692 Intermediate Similarity NPC32552
0.7692 Intermediate Similarity NPC284707
0.7692 Intermediate Similarity NPC474286
0.7692 Intermediate Similarity NPC709
0.7692 Intermediate Similarity NPC50774
0.7692 Intermediate Similarity NPC475130
0.7692 Intermediate Similarity NPC21326
0.7686 Intermediate Similarity NPC181999
0.7679 Intermediate Similarity NPC318363
0.7679 Intermediate Similarity NPC474664
0.7679 Intermediate Similarity NPC233379
0.7679 Intermediate Similarity NPC473482
0.7679 Intermediate Similarity NPC102843
0.7679 Intermediate Similarity NPC475418
0.7679 Intermediate Similarity NPC14862
0.7679 Intermediate Similarity NPC327106
0.7672 Intermediate Similarity NPC477509
0.7667 Intermediate Similarity NPC265557
0.7667 Intermediate Similarity NPC18945
0.7667 Intermediate Similarity NPC120724
0.7667 Intermediate Similarity NPC469789
0.7667 Intermediate Similarity NPC105926
0.7667 Intermediate Similarity NPC91693
0.7664 Intermediate Similarity NPC287668
0.7661 Intermediate Similarity NPC476193
0.7658 Intermediate Similarity NPC1679
0.7658 Intermediate Similarity NPC111952
0.7658 Intermediate Similarity NPC472645
0.7652 Intermediate Similarity NPC477126
0.7652 Intermediate Similarity NPC198539
0.7652 Intermediate Similarity NPC159333
0.7647 Intermediate Similarity NPC46570
0.7636 Intermediate Similarity NPC474165
0.7636 Intermediate Similarity NPC99266
0.7636 Intermediate Similarity NPC4620
0.7636 Intermediate Similarity NPC69171
0.7636 Intermediate Similarity NPC8196
0.7632 Intermediate Similarity NPC324683
0.7632 Intermediate Similarity NPC188738
0.7627 Intermediate Similarity NPC77689
0.7627 Intermediate Similarity NPC472933
0.7627 Intermediate Similarity NPC473636
0.7623 Intermediate Similarity NPC471940
0.7623 Intermediate Similarity NPC476008
0.7615 Intermediate Similarity NPC472753
0.7615 Intermediate Similarity NPC244456
0.7615 Intermediate Similarity NPC470184
0.7615 Intermediate Similarity NPC469657
0.7611 Intermediate Similarity NPC20192
0.7611 Intermediate Similarity NPC15218
0.7607 Intermediate Similarity NPC286528
0.7607 Intermediate Similarity NPC20302
0.7607 Intermediate Similarity NPC98249
0.7607 Intermediate Similarity NPC469684
0.7607 Intermediate Similarity NPC470493
0.7607 Intermediate Similarity NPC470492
0.7607 Intermediate Similarity NPC183580
0.7607 Intermediate Similarity NPC134430
0.7607 Intermediate Similarity NPC312824
0.7607 Intermediate Similarity NPC167606
0.7607 Intermediate Similarity NPC140055
0.7607 Intermediate Similarity NPC53396
0.7603 Intermediate Similarity NPC8374
0.7603 Intermediate Similarity NPC145238
0.7593 Intermediate Similarity NPC278008
0.7593 Intermediate Similarity NPC475653
0.7593 Intermediate Similarity NPC161855
0.7589 Intermediate Similarity NPC473284
0.7589 Intermediate Similarity NPC112780
0.7589 Intermediate Similarity NPC474421
0.7589 Intermediate Similarity NPC324327
0.7589 Intermediate Similarity NPC72813
0.7589 Intermediate Similarity NPC326994
0.7589 Intermediate Similarity NPC194620
0.7586 Intermediate Similarity NPC67259
0.7586 Intermediate Similarity NPC147912
0.7583 Intermediate Similarity NPC107493
0.757 Intermediate Similarity NPC255410
0.757 Intermediate Similarity NPC202833
0.7568 Intermediate Similarity NPC258532
0.7565 Intermediate Similarity NPC236217
0.7563 Intermediate Similarity NPC19336
0.7563 Intermediate Similarity NPC185876
0.7563 Intermediate Similarity NPC107338
0.7563 Intermediate Similarity NPC475885
0.7563 Intermediate Similarity NPC474370
0.7563 Intermediate Similarity NPC109607
0.7547 Intermediate Similarity NPC469491
0.7545 Intermediate Similarity NPC478176
0.7545 Intermediate Similarity NPC183571
0.7545 Intermediate Similarity NPC137430
0.7544 Intermediate Similarity NPC210005
0.7544 Intermediate Similarity NPC29133
0.7544 Intermediate Similarity NPC281624
0.7542 Intermediate Similarity NPC17772
0.7542 Intermediate Similarity NPC234522
0.7542 Intermediate Similarity NPC470776
0.7541 Intermediate Similarity NPC293112
0.7541 Intermediate Similarity NPC471939
0.7541 Intermediate Similarity NPC477745
0.7541 Intermediate Similarity NPC225049
0.7522 Intermediate Similarity NPC476802
0.7522 Intermediate Similarity NPC476479
0.7522 Intermediate Similarity NPC55972
0.7522 Intermediate Similarity NPC327286
0.7522 Intermediate Similarity NPC306265
0.7522 Intermediate Similarity NPC169888
0.7522 Intermediate Similarity NPC469916
0.7522 Intermediate Similarity NPC89171
0.7522 Intermediate Similarity NPC472439
0.7521 Intermediate Similarity NPC478216
0.7521 Intermediate Similarity NPC472399
0.7521 Intermediate Similarity NPC474333
0.752 Intermediate Similarity NPC102316
0.75 Intermediate Similarity NPC470779
0.75 Intermediate Similarity NPC9303
0.75 Intermediate Similarity NPC120299
0.75 Intermediate Similarity NPC472751

  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 NPC264819 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
0.7757 Intermediate Similarity NPD4225 Approved
0.7607 Intermediate Similarity NPD7115 Discovery
0.7417 Intermediate Similarity NPD6319 Approved
0.729 Intermediate Similarity NPD5778 Approved
0.729 Intermediate Similarity NPD5779 Approved
0.7119 Intermediate Similarity NPD8297 Approved
0.7117 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD6371 Approved
0.7073 Intermediate Similarity NPD8515 Approved
0.7073 Intermediate Similarity NPD8513 Phase 3
0.7073 Intermediate Similarity NPD8516 Approved
0.7073 Intermediate Similarity NPD8517 Approved
0.7069 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7983 Approved
0.7034 Intermediate Similarity NPD6649 Approved
0.7034 Intermediate Similarity NPD6650 Approved
0.6991 Remote Similarity NPD5344 Discontinued
0.6983 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6983 Remote Similarity NPD5697 Approved
0.696 Remote Similarity NPD8328 Phase 3
0.6944 Remote Similarity NPD7838 Discovery
0.6944 Remote Similarity NPD6698 Approved
0.6944 Remote Similarity NPD46 Approved
0.6923 Remote Similarity NPD6686 Approved
0.6923 Remote Similarity NPD6899 Approved
0.6923 Remote Similarity NPD6881 Approved
0.6917 Remote Similarity NPD4632 Approved
0.6905 Remote Similarity NPD7492 Approved
0.6903 Remote Similarity NPD6648 Approved
0.6881 Remote Similarity NPD6411 Approved
0.6864 Remote Similarity NPD6014 Approved
0.6864 Remote Similarity NPD6013 Approved
0.6864 Remote Similarity NPD6372 Approved
0.6864 Remote Similarity NPD6012 Approved
0.6864 Remote Similarity NPD6373 Approved
0.6864 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6054 Approved
0.685 Remote Similarity NPD6616 Approved
0.6846 Remote Similarity NPD7260 Phase 2
0.6833 Remote Similarity NPD6882 Approved
0.6807 Remote Similarity NPD4634 Approved
0.6807 Remote Similarity NPD7102 Approved
0.6807 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6883 Approved
0.6807 Remote Similarity NPD7290 Approved
0.68 Remote Similarity NPD6016 Approved
0.68 Remote Similarity NPD6015 Approved
0.6797 Remote Similarity NPD7078 Approved
0.6797 Remote Similarity NPD8074 Phase 3
0.6796 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6789 Remote Similarity NPD5785 Approved
0.678 Remote Similarity NPD6011 Approved
0.6754 Remote Similarity NPD7639 Approved
0.6754 Remote Similarity NPD7640 Approved
0.6752 Remote Similarity NPD6675 Approved
0.6752 Remote Similarity NPD7128 Approved
0.6752 Remote Similarity NPD6402 Approved
0.6752 Remote Similarity NPD5739 Approved
0.675 Remote Similarity NPD6847 Approved
0.675 Remote Similarity NPD6617 Approved
0.675 Remote Similarity NPD8130 Phase 1
0.675 Remote Similarity NPD6869 Approved
0.6748 Remote Similarity NPD6009 Approved
0.6746 Remote Similarity NPD6370 Approved
0.6746 Remote Similarity NPD5988 Approved
0.6744 Remote Similarity NPD7736 Approved
0.6727 Remote Similarity NPD7637 Suspended
0.6697 Remote Similarity NPD6101 Approved
0.6697 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6696 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6695 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD5983 Phase 2
0.6667 Remote Similarity NPD7503 Approved
0.6639 Remote Similarity NPD7320 Approved
0.6638 Remote Similarity NPD5211 Phase 2
0.6636 Remote Similarity NPD1696 Phase 3
0.6613 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6612 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5282 Discontinued
0.6604 Remote Similarity NPD6110 Phase 1
0.6587 Remote Similarity NPD6059 Approved
0.6565 Remote Similarity NPD7319 Approved
0.6562 Remote Similarity NPD7604 Phase 2
0.6555 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5695 Phase 3
0.6538 Remote Similarity NPD8293 Discontinued
0.6535 Remote Similarity NPD6921 Approved
0.6525 Remote Similarity NPD5141 Approved
0.6509 Remote Similarity NPD5209 Approved
0.6505 Remote Similarity NPD4756 Discovery
0.6481 Remote Similarity NPD1694 Approved
0.6466 Remote Similarity NPD5285 Approved
0.6466 Remote Similarity NPD4696 Approved
0.6466 Remote Similarity NPD5286 Approved
0.6462 Remote Similarity NPD6336 Discontinued
0.6462 Remote Similarity NPD7507 Approved
0.6446 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6435 Remote Similarity NPD7902 Approved
0.6435 Remote Similarity NPD6084 Phase 2
0.6435 Remote Similarity NPD6083 Phase 2
0.6418 Remote Similarity NPD6845 Suspended
0.64 Remote Similarity NPD6274 Approved
0.6379 Remote Similarity NPD5696 Approved
0.6378 Remote Similarity NPD7100 Approved
0.6378 Remote Similarity NPD7101 Approved
0.6356 Remote Similarity NPD5224 Approved
0.6356 Remote Similarity NPD5226 Approved
0.6356 Remote Similarity NPD5225 Approved
0.6356 Remote Similarity NPD4633 Approved
0.635 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6349 Remote Similarity NPD6317 Approved
0.6348 Remote Similarity NPD7839 Suspended
0.6341 Remote Similarity NPD6401 Clinical (unspecified phase)
0.633 Remote Similarity NPD5363 Approved
0.6316 Remote Similarity NPD7748 Approved
0.6303 Remote Similarity NPD5174 Approved
0.6303 Remote Similarity NPD5175 Approved
0.6299 Remote Similarity NPD7328 Approved
0.6299 Remote Similarity NPD7327 Approved
0.6299 Remote Similarity NPD6314 Approved
0.6299 Remote Similarity NPD6313 Approved
0.6299 Remote Similarity NPD6335 Approved
0.6293 Remote Similarity NPD4755 Approved
0.6283 Remote Similarity NPD7515 Phase 2
0.6283 Remote Similarity NPD5694 Approved
0.6283 Remote Similarity NPD5281 Approved
0.6283 Remote Similarity NPD5284 Approved
0.6279 Remote Similarity NPD8033 Approved
0.6273 Remote Similarity NPD5279 Phase 3
0.6271 Remote Similarity NPD5223 Approved
0.625 Remote Similarity NPD7516 Approved
0.6239 Remote Similarity NPD6400 Clinical (unspecified phase)
0.623 Remote Similarity NPD4730 Approved
0.623 Remote Similarity NPD4729 Approved
0.6228 Remote Similarity NPD6399 Phase 3
0.6218 Remote Similarity NPD7632 Discontinued
0.6207 Remote Similarity NPD5221 Approved
0.6207 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6207 Remote Similarity NPD5222 Approved
0.6204 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6202 Remote Similarity NPD8377 Approved
0.6202 Remote Similarity NPD8294 Approved
0.6198 Remote Similarity NPD6008 Approved
0.6195 Remote Similarity NPD5692 Phase 3
0.6186 Remote Similarity NPD4700 Approved
0.6183 Remote Similarity NPD7830 Approved
0.6183 Remote Similarity NPD7829 Approved
0.6174 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6174 Remote Similarity NPD7900 Approved
0.616 Remote Similarity NPD6053 Discontinued
0.6154 Remote Similarity NPD8380 Approved
0.6154 Remote Similarity NPD8335 Approved
0.6154 Remote Similarity NPD8379 Approved
0.6154 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5173 Approved
0.6154 Remote Similarity NPD8264 Approved
0.6154 Remote Similarity NPD8378 Approved
0.6154 Remote Similarity NPD8039 Approved
0.6154 Remote Similarity NPD8296 Approved
0.6148 Remote Similarity NPD6412 Phase 2
0.6142 Remote Similarity NPD6868 Approved
0.614 Remote Similarity NPD5693 Phase 1
0.614 Remote Similarity NPD6050 Approved
0.6129 Remote Similarity NPD5250 Approved
0.6129 Remote Similarity NPD5247 Approved
0.6129 Remote Similarity NPD5249 Phase 3
0.6129 Remote Similarity NPD5248 Approved
0.6129 Remote Similarity NPD5251 Approved
0.6126 Remote Similarity NPD3618 Phase 1
0.6121 Remote Similarity NPD5210 Approved
0.6121 Remote Similarity NPD4629 Approved
0.6119 Remote Similarity NPD6033 Approved
0.6106 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6094 Remote Similarity NPD7500 Approved
0.6071 Remote Similarity NPD3573 Approved
0.6071 Remote Similarity NPD7524 Approved
0.6068 Remote Similarity NPD4697 Phase 3
0.6066 Remote Similarity NPD4767 Approved
0.6066 Remote Similarity NPD4768 Approved
0.6061 Remote Similarity NPD7642 Approved
0.6055 Remote Similarity NPD4270 Approved
0.6055 Remote Similarity NPD4269 Approved
0.6031 Remote Similarity NPD6909 Approved
0.6031 Remote Similarity NPD6908 Approved
0.6029 Remote Similarity NPD5956 Approved
0.6019 Remote Similarity NPD4695 Discontinued
0.6019 Remote Similarity NPD4252 Approved
0.6019 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6018 Remote Similarity NPD6672 Approved
0.6018 Remote Similarity NPD5737 Approved
0.6 Remote Similarity NPD6079 Approved
0.6 Remote Similarity NPD4522 Approved
0.5986 Remote Similarity NPD7236 Approved
0.5984 Remote Similarity NPD8133 Approved
0.5982 Remote Similarity NPD5786 Approved
0.5982 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5982 Remote Similarity NPD4249 Approved
0.597 Remote Similarity NPD8273 Phase 1
0.597 Remote Similarity NPD8451 Approved

  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