Structure

Physi-Chem Properties

Molecular Weight:  346.18
Volume:  353.656
LogP:  1.236
LogD:  0.471
LogS:  -4.314
# Rotatable Bonds:  1
TPSA:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.632
Synthetic Accessibility Score:  5.407
Fsp3:  0.65
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:  -4.867
MDCK Permeability:  2.8870288588223048e-05
Pgp-inhibitor:  0.98
Pgp-substrate:  0.582
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.251
30% Bioavailability (F30%):  0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.967
Plasma Protein Binding (PPB):  84.3277816772461%
Volume Distribution (VD):  0.94
Pgp-substrate:  14.850096702575684%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.925
CYP2C19-inhibitor:  0.036
CYP2C19-substrate:  0.775
CYP2C9-inhibitor:  0.051
CYP2C9-substrate:  0.054
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.041
CYP3A4-inhibitor:  0.754
CYP3A4-substrate:  0.817

ADMET: Excretion

Clearance (CL):  2.322
Half-life (T1/2):  0.706

ADMET: Toxicity

hERG Blockers:  0.11
Human Hepatotoxicity (H-HT):  0.639
Drug-inuced Liver Injury (DILI):  0.042
AMES Toxicity:  0.948
Rat Oral Acute Toxicity:  0.993
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.764
Carcinogencity:  0.974
Eye Corrosion:  0.003
Eye Irritation:  0.034
Respiratory Toxicity:  0.964

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

  Natural Product: NPC261330

Natural Product ID:  NPC261330
Common Name*:   Libertellenone E
IUPAC Name:   n.a.
Synonyms:   Libertellenone E
Standard InCHIKey:  HLWYVYSGPCXCSB-ROEDYFHJSA-N
Standard InCHI:  InChI=1S/C20H26O5/c1-5-17(2)8-9-20(24)11(10-17)13(22)14-15-18(3,16(23)25-14)7-6-12(21)19(15,20)4/h5,10,12,16,21,23-24H,1,6-9H2,2-4H3/t12-,16+,17+,18-,19+,20-/m1/s1
SMILES:  C=C[C@@]1(C)CC[C@]2(C(=C1)C(=O)C1=C3[C@]2(C)[C@H](O)CC[C@]3([C@H](O1)O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1812031
PubChem CID:   53468287
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO19108 Arthrinium sacchari Species Apiosporaceae Eukaryota n.a. n.a. n.a. PMID[21718054]
NPO19108 Arthrinium sacchari Species Apiosporaceae 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
NPT737 Cell Line HUVEC Homo sapiens IC50 = 236400.0 nM PMID[452134]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 237700.0 nM PMID[452134]

☑ 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 NPC261330 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
0.9524 High Similarity NPC20192
0.8857 High Similarity NPC470184
0.8761 High Similarity NPC477116
0.8761 High Similarity NPC27999
0.8609 High Similarity NPC268958
0.8198 Intermediate Similarity NPC472645
0.8182 Intermediate Similarity NPC225049
0.8142 Intermediate Similarity NPC220705
0.8065 Intermediate Similarity NPC476863
0.8065 Intermediate Similarity NPC476862
0.8049 Intermediate Similarity NPC476859
0.8018 Intermediate Similarity NPC320154
0.8017 Intermediate Similarity NPC472926
0.8016 Intermediate Similarity NPC478072
0.7983 Intermediate Similarity NPC472933
0.7967 Intermediate Similarity NPC152091
0.7951 Intermediate Similarity NPC470922
0.7949 Intermediate Similarity NPC247069
0.792 Intermediate Similarity NPC476852
0.792 Intermediate Similarity NPC476855
0.7917 Intermediate Similarity NPC48692
0.7917 Intermediate Similarity NPC478051
0.7917 Intermediate Similarity NPC112038
0.7899 Intermediate Similarity NPC21326
0.7899 Intermediate Similarity NPC176005
0.7857 Intermediate Similarity NPC230918
0.7857 Intermediate Similarity NPC131366
0.784 Intermediate Similarity NPC476851
0.784 Intermediate Similarity NPC476854
0.7838 Intermediate Similarity NPC472643
0.7833 Intermediate Similarity NPC469488
0.7826 Intermediate Similarity NPC31522
0.7815 Intermediate Similarity NPC472927
0.781 Intermediate Similarity NPC58271
0.7807 Intermediate Similarity NPC472925
0.7778 Intermediate Similarity NPC174836
0.7778 Intermediate Similarity NPC90769
0.7759 Intermediate Similarity NPC235014
0.7759 Intermediate Similarity NPC42776
0.775 Intermediate Similarity NPC204552
0.775 Intermediate Similarity NPC188667
0.775 Intermediate Similarity NPC234522
0.775 Intermediate Similarity NPC297179
0.775 Intermediate Similarity NPC251310
0.7748 Intermediate Similarity NPC472972
0.7748 Intermediate Similarity NPC472644
0.7742 Intermediate Similarity NPC93368
0.7739 Intermediate Similarity NPC272576
0.7739 Intermediate Similarity NPC90946
0.7739 Intermediate Similarity NPC300614
0.7731 Intermediate Similarity NPC302471
0.7724 Intermediate Similarity NPC238005
0.7724 Intermediate Similarity NPC1980
0.7724 Intermediate Similarity NPC141196
0.7717 Intermediate Similarity NPC102316
0.7712 Intermediate Similarity NPC198539
0.7712 Intermediate Similarity NPC51978
0.7712 Intermediate Similarity NPC321496
0.7712 Intermediate Similarity NPC25909
0.7705 Intermediate Similarity NPC202051
0.7692 Intermediate Similarity NPC146945
0.7692 Intermediate Similarity NPC171888
0.7692 Intermediate Similarity NPC596
0.7692 Intermediate Similarity NPC140045
0.7692 Intermediate Similarity NPC295885
0.7686 Intermediate Similarity NPC279143
0.7686 Intermediate Similarity NPC473920
0.7686 Intermediate Similarity NPC470777
0.7672 Intermediate Similarity NPC87335
0.7667 Intermediate Similarity NPC472934
0.7667 Intermediate Similarity NPC218970
0.7661 Intermediate Similarity NPC24651
0.7656 Intermediate Similarity NPC168879
0.7647 Intermediate Similarity NPC181145
0.7642 Intermediate Similarity NPC470419
0.7642 Intermediate Similarity NPC216866
0.7642 Intermediate Similarity NPC53454
0.7642 Intermediate Similarity NPC313528
0.7638 Intermediate Similarity NPC213634
0.7627 Intermediate Similarity NPC269530
0.7627 Intermediate Similarity NPC472002
0.7627 Intermediate Similarity NPC12046
0.7627 Intermediate Similarity NPC194951
0.7627 Intermediate Similarity NPC90952
0.7627 Intermediate Similarity NPC277769
0.7623 Intermediate Similarity NPC107338
0.7623 Intermediate Similarity NPC109607
0.7619 Intermediate Similarity NPC245094
0.7619 Intermediate Similarity NPC295220
0.7619 Intermediate Similarity NPC475636
0.7615 Intermediate Similarity NPC141215
0.7615 Intermediate Similarity NPC471089
0.7615 Intermediate Similarity NPC251998
0.7615 Intermediate Similarity NPC190065
0.7607 Intermediate Similarity NPC478209
0.7607 Intermediate Similarity NPC5103
0.7607 Intermediate Similarity NPC46407
0.7603 Intermediate Similarity NPC240509
0.76 Intermediate Similarity NPC198714
0.7597 Intermediate Similarity NPC471234
0.7593 Intermediate Similarity NPC73457
0.7589 Intermediate Similarity NPC306856
0.7586 Intermediate Similarity NPC325054
0.7586 Intermediate Similarity NPC476765
0.7586 Intermediate Similarity NPC322903
0.7583 Intermediate Similarity NPC259306
0.7583 Intermediate Similarity NPC235539
0.7583 Intermediate Similarity NPC179626
0.7583 Intermediate Similarity NPC152199
0.7583 Intermediate Similarity NPC134869
0.7583 Intermediate Similarity NPC470628
0.7583 Intermediate Similarity NPC471816
0.7583 Intermediate Similarity NPC474046
0.7581 Intermediate Similarity NPC227397
0.7581 Intermediate Similarity NPC120724
0.7568 Intermediate Similarity NPC471916
0.7568 Intermediate Similarity NPC273269
0.7565 Intermediate Similarity NPC32006
0.7565 Intermediate Similarity NPC85529
0.7563 Intermediate Similarity NPC311592
0.7563 Intermediate Similarity NPC159333
0.7563 Intermediate Similarity NPC157441
0.7563 Intermediate Similarity NPC471173
0.7563 Intermediate Similarity NPC208998
0.7563 Intermediate Similarity NPC7921
0.7563 Intermediate Similarity NPC75167
0.7563 Intermediate Similarity NPC474271
0.7563 Intermediate Similarity NPC471627
0.7561 Intermediate Similarity NPC477046
0.7561 Intermediate Similarity NPC102822
0.7561 Intermediate Similarity NPC472001
0.7561 Intermediate Similarity NPC42675
0.7561 Intermediate Similarity NPC46570
0.7561 Intermediate Similarity NPC275675
0.7561 Intermediate Similarity NPC470418
0.7559 Intermediate Similarity NPC221414
0.7559 Intermediate Similarity NPC54614
0.7559 Intermediate Similarity NPC309096
0.7545 Intermediate Similarity NPC272617
0.7544 Intermediate Similarity NPC159442
0.7544 Intermediate Similarity NPC95899
0.7542 Intermediate Similarity NPC207689
0.7542 Intermediate Similarity NPC201992
0.7542 Intermediate Similarity NPC471243
0.7542 Intermediate Similarity NPC472928
0.7542 Intermediate Similarity NPC324683
0.7541 Intermediate Similarity NPC161065
0.7541 Intermediate Similarity NPC476529
0.7541 Intermediate Similarity NPC475775
0.7541 Intermediate Similarity NPC476107
0.7541 Intermediate Similarity NPC127530
0.754 Intermediate Similarity NPC42399
0.7538 Intermediate Similarity NPC262813
0.7522 Intermediate Similarity NPC207885
0.7522 Intermediate Similarity NPC112613
0.7521 Intermediate Similarity NPC286174
0.7521 Intermediate Similarity NPC97908
0.7521 Intermediate Similarity NPC77947
0.7521 Intermediate Similarity NPC469684
0.7521 Intermediate Similarity NPC122033
0.7521 Intermediate Similarity NPC470775
0.7521 Intermediate Similarity NPC23046
0.7521 Intermediate Similarity NPC176513
0.7521 Intermediate Similarity NPC470854
0.7521 Intermediate Similarity NPC287343
0.7521 Intermediate Similarity NPC474654
0.7521 Intermediate Similarity NPC470615
0.752 Intermediate Similarity NPC475194
0.752 Intermediate Similarity NPC6615
0.752 Intermediate Similarity NPC476729
0.752 Intermediate Similarity NPC7850
0.75 Intermediate Similarity NPC312833
0.75 Intermediate Similarity NPC469877
0.75 Intermediate Similarity NPC18547
0.75 Intermediate Similarity NPC469746
0.75 Intermediate Similarity NPC474906
0.75 Intermediate Similarity NPC230332
0.75 Intermediate Similarity NPC287236
0.75 Intermediate Similarity NPC300584
0.75 Intermediate Similarity NPC470919
0.75 Intermediate Similarity NPC470953
0.75 Intermediate Similarity NPC107493
0.75 Intermediate Similarity NPC238667
0.75 Intermediate Similarity NPC44063
0.748 Intermediate Similarity NPC311534
0.748 Intermediate Similarity NPC293623
0.748 Intermediate Similarity NPC241192
0.748 Intermediate Similarity NPC168899
0.748 Intermediate Similarity NPC473620
0.748 Intermediate Similarity NPC69273
0.7479 Intermediate Similarity NPC289312
0.7479 Intermediate Similarity NPC302146
0.7479 Intermediate Similarity NPC11252
0.7479 Intermediate Similarity NPC4573
0.7478 Intermediate Similarity NPC222161
0.7478 Intermediate Similarity NPC96268
0.7478 Intermediate Similarity NPC118911
0.7478 Intermediate Similarity NPC40170
0.746 Intermediate Similarity NPC477745
0.746 Intermediate Similarity NPC87662

  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 NPC261330 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
0.7934 Intermediate Similarity NPD6370 Approved
0.7769 Intermediate Similarity NPD6054 Approved
0.7705 Intermediate Similarity NPD6016 Approved
0.7705 Intermediate Similarity NPD6015 Approved
0.7642 Intermediate Similarity NPD5988 Approved
0.7619 Intermediate Similarity NPD7736 Approved
0.752 Intermediate Similarity NPD7492 Approved
0.75 Intermediate Similarity NPD5697 Approved
0.748 Intermediate Similarity NPD6059 Approved
0.748 Intermediate Similarity NPD6319 Approved
0.7479 Intermediate Similarity NPD6882 Approved
0.746 Intermediate Similarity NPD6616 Approved
0.7456 Intermediate Similarity NPD5211 Phase 2
0.7436 Intermediate Similarity NPD6881 Approved
0.7436 Intermediate Similarity NPD6899 Approved
0.7402 Intermediate Similarity NPD8293 Discontinued
0.7402 Intermediate Similarity NPD7078 Approved
0.7377 Intermediate Similarity NPD6009 Approved
0.7373 Intermediate Similarity NPD6012 Approved
0.7373 Intermediate Similarity NPD6013 Approved
0.7373 Intermediate Similarity NPD6014 Approved
0.7328 Intermediate Similarity NPD5141 Approved
0.7311 Intermediate Similarity NPD6883 Approved
0.7311 Intermediate Similarity NPD7102 Approved
0.7311 Intermediate Similarity NPD4634 Approved
0.7311 Intermediate Similarity NPD7290 Approved
0.7302 Intermediate Similarity NPD8328 Phase 3
0.7288 Intermediate Similarity NPD6011 Approved
0.7281 Intermediate Similarity NPD5286 Approved
0.7281 Intermediate Similarity NPD5285 Approved
0.7281 Intermediate Similarity NPD4696 Approved
0.7265 Intermediate Similarity NPD7128 Approved
0.7265 Intermediate Similarity NPD6675 Approved
0.7265 Intermediate Similarity NPD6402 Approved
0.7265 Intermediate Similarity NPD5739 Approved
0.725 Intermediate Similarity NPD6650 Approved
0.725 Intermediate Similarity NPD6869 Approved
0.725 Intermediate Similarity NPD6617 Approved
0.725 Intermediate Similarity NPD8130 Phase 1
0.725 Intermediate Similarity NPD6649 Approved
0.725 Intermediate Similarity NPD6847 Approved
0.7203 Intermediate Similarity NPD5701 Approved
0.719 Intermediate Similarity NPD8297 Approved
0.7155 Intermediate Similarity NPD5225 Approved
0.7155 Intermediate Similarity NPD4633 Approved
0.7155 Intermediate Similarity NPD5226 Approved
0.7155 Intermediate Similarity NPD5224 Approved
0.7143 Intermediate Similarity NPD6686 Approved
0.7143 Intermediate Similarity NPD5282 Discontinued
0.7143 Intermediate Similarity NPD7320 Approved
0.7131 Intermediate Similarity NPD4632 Approved
0.7105 Intermediate Similarity NPD4755 Approved
0.7097 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD5174 Approved
0.7094 Intermediate Similarity NPD5175 Approved
0.7083 Intermediate Similarity NPD6373 Approved
0.7083 Intermediate Similarity NPD6372 Approved
0.7069 Intermediate Similarity NPD5223 Approved
0.7054 Intermediate Similarity NPD5778 Approved
0.7054 Intermediate Similarity NPD5779 Approved
0.7023 Intermediate Similarity NPD7319 Approved
0.7018 Intermediate Similarity NPD5222 Approved
0.7018 Intermediate Similarity NPD5221 Approved
0.7018 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD5983 Phase 2
0.7 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.6983 Remote Similarity NPD4700 Approved
0.696 Remote Similarity NPD7115 Discovery
0.6957 Remote Similarity NPD5173 Approved
0.6947 Remote Similarity NPD6033 Approved
0.6942 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7507 Approved
0.6917 Remote Similarity NPD6412 Phase 2
0.6899 Remote Similarity NPD7604 Phase 2
0.688 Remote Similarity NPD6274 Approved
0.686 Remote Similarity NPD4729 Approved
0.686 Remote Similarity NPD4730 Approved
0.685 Remote Similarity NPD7101 Approved
0.685 Remote Similarity NPD7100 Approved
0.6829 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6317 Approved
0.6814 Remote Similarity NPD6411 Approved
0.6814 Remote Similarity NPD6079 Approved
0.6794 Remote Similarity NPD6336 Discontinued
0.6783 Remote Similarity NPD5695 Phase 3
0.6772 Remote Similarity NPD6313 Approved
0.6772 Remote Similarity NPD6335 Approved
0.6772 Remote Similarity NPD6314 Approved
0.6752 Remote Similarity NPD4225 Approved
0.6748 Remote Similarity NPD5249 Phase 3
0.6748 Remote Similarity NPD5248 Approved
0.6748 Remote Similarity NPD5250 Approved
0.6748 Remote Similarity NPD5251 Approved
0.6748 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6748 Remote Similarity NPD5247 Approved
0.6744 Remote Similarity NPD8513 Phase 3
0.6744 Remote Similarity NPD8517 Approved
0.6744 Remote Similarity NPD8515 Approved
0.6744 Remote Similarity NPD8516 Approved
0.6724 Remote Similarity NPD4697 Phase 3
0.6721 Remote Similarity NPD5128 Approved
0.6695 Remote Similarity NPD7640 Approved
0.6695 Remote Similarity NPD7639 Approved
0.6694 Remote Similarity NPD6008 Approved
0.6694 Remote Similarity NPD5217 Approved
0.6694 Remote Similarity NPD5216 Approved
0.6694 Remote Similarity NPD4767 Approved
0.6694 Remote Similarity NPD4768 Approved
0.6694 Remote Similarity NPD5215 Approved
0.6667 Remote Similarity NPD6084 Phase 2
0.6667 Remote Similarity NPD6083 Phase 2
0.6667 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD8132 Clinical (unspecified phase)
0.664 Remote Similarity NPD6053 Discontinued
0.6637 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6101 Approved
0.6637 Remote Similarity NPD5328 Approved
0.6615 Remote Similarity NPD7503 Approved
0.6614 Remote Similarity NPD6868 Approved
0.6613 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6613 Remote Similarity NPD5135 Approved
0.6613 Remote Similarity NPD5169 Approved
0.661 Remote Similarity NPD7638 Approved
0.6593 Remote Similarity NPD5956 Approved
0.6593 Remote Similarity NPD6914 Discontinued
0.6577 Remote Similarity NPD1696 Phase 3
0.6574 Remote Similarity NPD4695 Discontinued
0.656 Remote Similarity NPD5127 Approved
0.6518 Remote Similarity NPD3618 Phase 1
0.6518 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6518 Remote Similarity NPD5279 Phase 3
0.6512 Remote Similarity NPD7328 Approved
0.6512 Remote Similarity NPD7327 Approved
0.6504 Remote Similarity NPD5954 Clinical (unspecified phase)
0.65 Remote Similarity NPD6334 Approved
0.65 Remote Similarity NPD6333 Approved
0.6496 Remote Similarity NPD5210 Approved
0.6496 Remote Similarity NPD4629 Approved
0.6496 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4753 Phase 2
0.6489 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6909 Approved
0.6489 Remote Similarity NPD6908 Approved
0.6471 Remote Similarity NPD5696 Approved
0.6466 Remote Similarity NPD4202 Approved
0.6462 Remote Similarity NPD7516 Approved
0.646 Remote Similarity NPD3573 Approved
0.6452 Remote Similarity NPD5168 Approved
0.6439 Remote Similarity NPD8080 Discontinued
0.6423 Remote Similarity NPD7260 Phase 2
0.641 Remote Similarity NPD7748 Approved
0.6406 Remote Similarity NPD5167 Approved
0.6391 Remote Similarity NPD6067 Discontinued
0.6387 Remote Similarity NPD7902 Approved
0.6379 Remote Similarity NPD7515 Phase 2
0.6372 Remote Similarity NPD5690 Phase 2
0.6364 Remote Similarity NPD6921 Approved
0.6364 Remote Similarity NPD8033 Approved
0.6364 Remote Similarity NPD5344 Discontinued
0.6349 Remote Similarity NPD6371 Approved
0.6339 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6399 Phase 3
0.6311 Remote Similarity NPD7632 Discontinued
0.6306 Remote Similarity NPD3667 Approved
0.6288 Remote Similarity NPD8377 Approved
0.6288 Remote Similarity NPD8294 Approved
0.6283 Remote Similarity NPD1694 Approved
0.6273 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6261 Remote Similarity NPD6672 Approved
0.6261 Remote Similarity NPD5737 Approved
0.625 Remote Similarity NPD8074 Phase 3
0.6241 Remote Similarity NPD8335 Approved
0.6241 Remote Similarity NPD8379 Approved
0.6241 Remote Similarity NPD8378 Approved
0.6241 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6241 Remote Similarity NPD8296 Approved
0.6241 Remote Similarity NPD8380 Approved
0.6239 Remote Similarity NPD5694 Approved
0.6239 Remote Similarity NPD7637 Suspended
0.6239 Remote Similarity NPD7983 Approved
0.6228 Remote Similarity NPD4519 Discontinued
0.6228 Remote Similarity NPD4623 Approved
0.6212 Remote Similarity NPD4522 Approved
0.6207 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6195 Remote Similarity NPD3666 Approved
0.6195 Remote Similarity NPD3665 Phase 1
0.6195 Remote Similarity NPD3133 Approved
0.6195 Remote Similarity NPD4786 Approved
0.6172 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7839 Suspended
0.6161 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5785 Approved
0.6154 Remote Similarity NPD5692 Phase 3
0.6148 Remote Similarity NPD6648 Approved
0.6143 Remote Similarity NPD6845 Suspended
0.6134 Remote Similarity NPD7900 Approved
0.6134 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6106 Remote Similarity NPD6110 Phase 1
0.6102 Remote Similarity NPD5281 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