Structure

Physi-Chem Properties

Molecular Weight:  290.12
Volume:  284.472
LogP:  1.594
LogD:  1.198
LogS:  -3.682
# Rotatable Bonds:  0
TPSA:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.684
Synthetic Accessibility Score:  5.093
Fsp3:  0.625
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:  -5.283
MDCK Permeability:  2.995636168634519e-05
Pgp-inhibitor:  0.628
Pgp-substrate:  0.794
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.275

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.936
Plasma Protein Binding (PPB):  55.45220184326172%
Volume Distribution (VD):  0.651
Pgp-substrate:  62.532596588134766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.021
CYP1A2-substrate:  0.312
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.64
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.053
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.06
CYP3A4-inhibitor:  0.23
CYP3A4-substrate:  0.582

ADMET: Excretion

Clearance (CL):  10.501
Half-life (T1/2):  0.474

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.143
Drug-inuced Liver Injury (DILI):  0.278
AMES Toxicity:  0.317
Rat Oral Acute Toxicity:  0.657
Maximum Recommended Daily Dose:  0.21
Skin Sensitization:  0.907
Carcinogencity:  0.845
Eye Corrosion:  0.973
Eye Irritation:  0.809
Respiratory Toxicity:  0.961

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC469607

Natural Product ID:  NPC469607
Common Name*:   GIKKNHSLWAXIMY-NEYPUQFUSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GIKKNHSLWAXIMY-NEYPUQFUSA-N
Standard InCHI:  InChI=1S/C16H18O5/c1-15-4-3-11(17)16(2)9-6-12(18)20-7-8(9)5-10(13(15)16)21-14(15)19/h5-6,10-11,13,17H,3-4,7H2,1-2H3/t10-,11-,13?,15+,16+/m1/s1
SMILES:  O=C1OCC2=C[C@@H]3C4[C@](C2=C1)(C)[C@H](O)CC[C@]4(C)C(=O)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1094048
PubChem CID:   44613790
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans

*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
NPO13187 Sclerotinia homoeocarpa Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[19928902]
NPO13187 Sclerotinia homoeocarpa Species Sclerotiniaceae 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 4.76 ug.mL-1 PMID[515384]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[515384]
NPT457 Cell Line BT-549 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[515384]
NPT91 Cell Line KB Homo sapiens IC50 > 10.0 ug.mL-1 PMID[515384]
NPT916 Cell Line SK-MEL Homo sapiens IC50 = 3.3 ug.mL-1 PMID[515384]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.9 ug.mL-1 PMID[515384]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.67 ug.mL-1 PMID[515384]
NPT854 Organism Lemna paucicostata Lemna paucicostata IC50 = 547000.0 nM PMID[515384]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10.0 ug.mL-1 PMID[515384]
NPT2 Others Unspecified Ratio IC50 = 7.1 n.a. PMID[515384]
NPT2 Others Unspecified Ratio IC50 = 5.3 n.a. PMID[515384]

☑ 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 NPC469607 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
0.9691 High Similarity NPC469606
0.9691 High Similarity NPC273005
0.9691 High Similarity NPC31058
0.94 High Similarity NPC478208
0.9216 High Similarity NPC189075
0.9216 High Similarity NPC275539
0.9126 High Similarity NPC478210
0.9118 High Similarity NPC110496
0.91 High Similarity NPC235369
0.9065 High Similarity NPC53396
0.9065 High Similarity NPC98249
0.9038 High Similarity NPC478211
0.9038 High Similarity NPC478209
0.8981 High Similarity NPC284707
0.8969 High Similarity NPC250075
0.8952 High Similarity NPC188738
0.8952 High Similarity NPC97939
0.8952 High Similarity NPC100329
0.8952 High Similarity NPC247031
0.8952 High Similarity NPC132790
0.8868 High Similarity NPC12046
0.8868 High Similarity NPC194951
0.8824 High Similarity NPC254202
0.8812 High Similarity NPC472637
0.88 High Similarity NPC23364
0.88 High Similarity NPC216478
0.8785 High Similarity NPC475966
0.8785 High Similarity NPC478212
0.8785 High Similarity NPC157441
0.8785 High Similarity NPC25909
0.8774 High Similarity NPC469655
0.8774 High Similarity NPC469656
0.8774 High Similarity NPC474846
0.8716 High Similarity NPC469684
0.8713 High Similarity NPC47024
0.8687 High Similarity NPC183012
0.8679 High Similarity NPC210005
0.8667 High Similarity NPC89171
0.8667 High Similarity NPC476802
0.866 High Similarity NPC220454
0.866 High Similarity NPC212679
0.866 High Similarity NPC469595
0.8654 High Similarity NPC102352
0.8627 High Similarity NPC471412
0.8624 High Similarity NPC478216
0.8611 High Similarity NPC469496
0.8611 High Similarity NPC469463
0.8611 High Similarity NPC471204
0.8611 High Similarity NPC469454
0.8598 High Similarity NPC179798
0.8598 High Similarity NPC304180
0.8586 High Similarity NPC477129
0.8586 High Similarity NPC477130
0.8585 High Similarity NPC469370
0.8571 High Similarity NPC133422
0.8571 High Similarity NPC230541
0.8571 High Similarity NPC186363
0.8571 High Similarity NPC233345
0.8571 High Similarity NPC3316
0.8571 High Similarity NPC144854
0.8545 High Similarity NPC478204
0.8544 High Similarity NPC476081
0.8544 High Similarity NPC295791
0.8544 High Similarity NPC165250
0.8544 High Similarity NPC162973
0.8529 High Similarity NPC474012
0.8529 High Similarity NPC471413
0.8529 High Similarity NPC476299
0.8519 High Similarity NPC269530
0.8515 High Similarity NPC474343
0.8505 High Similarity NPC5103
0.8505 High Similarity NPC286880
0.8491 Intermediate Similarity NPC154608
0.8491 Intermediate Similarity NPC192813
0.8491 Intermediate Similarity NPC476479
0.8491 Intermediate Similarity NPC277017
0.8476 Intermediate Similarity NPC34768
0.8476 Intermediate Similarity NPC252296
0.8469 Intermediate Similarity NPC158488
0.8468 Intermediate Similarity NPC478206
0.8468 Intermediate Similarity NPC478205
0.8468 Intermediate Similarity NPC108581
0.8462 Intermediate Similarity NPC36688
0.8447 Intermediate Similarity NPC81530
0.8447 Intermediate Similarity NPC244456
0.8447 Intermediate Similarity NPC469657
0.844 Intermediate Similarity NPC56448
0.8411 Intermediate Similarity NPC141350
0.8411 Intermediate Similarity NPC474243
0.8411 Intermediate Similarity NPC112457
0.84 Intermediate Similarity NPC57117
0.8396 Intermediate Similarity NPC180744
0.8396 Intermediate Similarity NPC302788
0.8396 Intermediate Similarity NPC184512
0.8393 Intermediate Similarity NPC475041
0.8381 Intermediate Similarity NPC470297
0.8381 Intermediate Similarity NPC258532
0.8378 Intermediate Similarity NPC473968
0.8378 Intermediate Similarity NPC58662
0.8378 Intermediate Similarity NPC13713
0.8365 Intermediate Similarity NPC137430
0.8365 Intermediate Similarity NPC136289
0.835 Intermediate Similarity NPC476767
0.835 Intermediate Similarity NPC117685
0.835 Intermediate Similarity NPC472972
0.8349 Intermediate Similarity NPC277769
0.8349 Intermediate Similarity NPC476801
0.8349 Intermediate Similarity NPC472002
0.8333 Intermediate Similarity NPC175351
0.8333 Intermediate Similarity NPC253906
0.8333 Intermediate Similarity NPC121402
0.8333 Intermediate Similarity NPC224356
0.8333 Intermediate Similarity NPC472666
0.8333 Intermediate Similarity NPC91695
0.8333 Intermediate Similarity NPC151681
0.8333 Intermediate Similarity NPC132753
0.8333 Intermediate Similarity NPC70145
0.8317 Intermediate Similarity NPC259042
0.8317 Intermediate Similarity NPC157686
0.8317 Intermediate Similarity NPC316215
0.8302 Intermediate Similarity NPC127609
0.8302 Intermediate Similarity NPC477125
0.8302 Intermediate Similarity NPC478052
0.83 Intermediate Similarity NPC475657
0.8286 Intermediate Similarity NPC8196
0.8286 Intermediate Similarity NPC120321
0.8286 Intermediate Similarity NPC159442
0.8286 Intermediate Similarity NPC134270
0.8286 Intermediate Similarity NPC99266
0.8286 Intermediate Similarity NPC159533
0.8286 Intermediate Similarity NPC471208
0.8286 Intermediate Similarity NPC275583
0.8283 Intermediate Similarity NPC221111
0.8283 Intermediate Similarity NPC469372
0.8283 Intermediate Similarity NPC280149
0.8283 Intermediate Similarity NPC152467
0.8273 Intermediate Similarity NPC474271
0.8265 Intermediate Similarity NPC477128
0.8265 Intermediate Similarity NPC277771
0.8252 Intermediate Similarity NPC476806
0.8252 Intermediate Similarity NPC476807
0.8247 Intermediate Similarity NPC250981
0.8247 Intermediate Similarity NPC6979
0.8241 Intermediate Similarity NPC228477
0.8241 Intermediate Similarity NPC153239
0.8241 Intermediate Similarity NPC137911
0.8241 Intermediate Similarity NPC143706
0.8241 Intermediate Similarity NPC472534
0.8235 Intermediate Similarity NPC165528
0.8235 Intermediate Similarity NPC234993
0.8235 Intermediate Similarity NPC284518
0.8235 Intermediate Similarity NPC112654
0.8235 Intermediate Similarity NPC29952
0.8235 Intermediate Similarity NPC228766
0.8235 Intermediate Similarity NPC472362
0.8235 Intermediate Similarity NPC134072
0.8235 Intermediate Similarity NPC472363
0.8235 Intermediate Similarity NPC202833
0.8235 Intermediate Similarity NPC154526
0.823 Intermediate Similarity NPC305260
0.823 Intermediate Similarity NPC476529
0.823 Intermediate Similarity NPC270850
0.823 Intermediate Similarity NPC475775
0.8224 Intermediate Similarity NPC179380
0.8224 Intermediate Similarity NPC187435
0.8224 Intermediate Similarity NPC143609
0.8224 Intermediate Similarity NPC67321
0.8218 Intermediate Similarity NPC225474
0.8218 Intermediate Similarity NPC469596
0.8218 Intermediate Similarity NPC148000
0.8214 Intermediate Similarity NPC23046
0.8214 Intermediate Similarity NPC476959
0.8214 Intermediate Similarity NPC473590
0.8214 Intermediate Similarity NPC284068
0.8208 Intermediate Similarity NPC264867
0.8208 Intermediate Similarity NPC470321
0.8208 Intermediate Similarity NPC146731
0.8208 Intermediate Similarity NPC96268
0.8208 Intermediate Similarity NPC473207
0.8208 Intermediate Similarity NPC81567
0.8208 Intermediate Similarity NPC118911
0.8208 Intermediate Similarity NPC222161
0.8208 Intermediate Similarity NPC201880
0.8208 Intermediate Similarity NPC296950
0.82 Intermediate Similarity NPC477574
0.82 Intermediate Similarity NPC72845
0.8198 Intermediate Similarity NPC474181
0.819 Intermediate Similarity NPC164551
0.819 Intermediate Similarity NPC238397
0.819 Intermediate Similarity NPC32577
0.819 Intermediate Similarity NPC475320
0.819 Intermediate Similarity NPC155332
0.819 Intermediate Similarity NPC114540
0.819 Intermediate Similarity NPC471363
0.819 Intermediate Similarity NPC476769
0.819 Intermediate Similarity NPC58329
0.8182 Intermediate Similarity NPC4573
0.8182 Intermediate Similarity NPC90952
0.8182 Intermediate Similarity NPC116620
0.8182 Intermediate Similarity NPC168131

  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 NPC469607 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
0.8252 Intermediate Similarity NPD7638 Approved
0.8173 Intermediate Similarity NPD7640 Approved
0.8173 Intermediate Similarity NPD7639 Approved
0.7963 Intermediate Similarity NPD6008 Approved
0.7748 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD4225 Approved
0.7699 Intermediate Similarity NPD6053 Discontinued
0.7679 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD7902 Approved
0.7636 Intermediate Similarity NPD6402 Approved
0.7636 Intermediate Similarity NPD5739 Approved
0.7636 Intermediate Similarity NPD7128 Approved
0.7636 Intermediate Similarity NPD6675 Approved
0.76 Intermediate Similarity NPD1694 Approved
0.7596 Intermediate Similarity NPD5779 Approved
0.7596 Intermediate Similarity NPD5778 Approved
0.7596 Intermediate Similarity NPD6399 Phase 3
0.7589 Intermediate Similarity NPD6373 Approved
0.7589 Intermediate Similarity NPD6372 Approved
0.7586 Intermediate Similarity NPD7115 Discovery
0.7568 Intermediate Similarity NPD5701 Approved
0.7568 Intermediate Similarity NPD5697 Approved
0.7525 Intermediate Similarity NPD3618 Phase 1
0.7524 Intermediate Similarity NPD7748 Approved
0.7523 Intermediate Similarity NPD7632 Discontinued
0.75 Intermediate Similarity NPD6011 Approved
0.75 Intermediate Similarity NPD7515 Phase 2
0.75 Intermediate Similarity NPD6881 Approved
0.75 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD6411 Approved
0.75 Intermediate Similarity NPD6899 Approved
0.75 Intermediate Similarity NPD6686 Approved
0.7479 Intermediate Similarity NPD8513 Phase 3
0.7478 Intermediate Similarity NPD4632 Approved
0.7476 Intermediate Similarity NPD5328 Approved
0.7456 Intermediate Similarity NPD6650 Approved
0.7456 Intermediate Similarity NPD6649 Approved
0.7434 Intermediate Similarity NPD6013 Approved
0.7434 Intermediate Similarity NPD6012 Approved
0.7434 Intermediate Similarity NPD6014 Approved
0.7411 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD4697 Phase 3
0.7377 Intermediate Similarity NPD7507 Approved
0.7368 Intermediate Similarity NPD7102 Approved
0.7368 Intermediate Similarity NPD7290 Approved
0.7368 Intermediate Similarity NPD6883 Approved
0.7358 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD7900 Approved
0.7333 Intermediate Similarity NPD8515 Approved
0.7333 Intermediate Similarity NPD6079 Approved
0.7333 Intermediate Similarity NPD8517 Approved
0.7333 Intermediate Similarity NPD8516 Approved
0.7315 Intermediate Similarity NPD4755 Approved
0.7308 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6101 Approved
0.7304 Intermediate Similarity NPD6869 Approved
0.7304 Intermediate Similarity NPD6847 Approved
0.7304 Intermediate Similarity NPD8130 Phase 1
0.7304 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD6617 Approved
0.73 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD6009 Approved
0.725 Intermediate Similarity NPD6319 Approved
0.7241 Intermediate Similarity NPD8297 Approved
0.7241 Intermediate Similarity NPD6882 Approved
0.7222 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5222 Approved
0.7222 Intermediate Similarity NPD7260 Phase 2
0.7222 Intermediate Similarity NPD5221 Approved
0.7207 Intermediate Similarity NPD5211 Phase 2
0.72 Intermediate Similarity NPD7319 Approved
0.7193 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD5983 Phase 2
0.7182 Intermediate Similarity NPD5286 Approved
0.7182 Intermediate Similarity NPD4696 Approved
0.7182 Intermediate Similarity NPD5285 Approved
0.7182 Intermediate Similarity NPD4700 Approved
0.717 Intermediate Similarity NPD5284 Approved
0.717 Intermediate Similarity NPD5281 Approved
0.7156 Intermediate Similarity NPD5173 Approved
0.7154 Intermediate Similarity NPD7492 Approved
0.7129 Intermediate Similarity NPD3667 Approved
0.7117 Intermediate Similarity NPD5223 Approved
0.7115 Intermediate Similarity NPD3573 Approved
0.7107 Intermediate Similarity NPD6059 Approved
0.7107 Intermediate Similarity NPD6054 Approved
0.7103 Intermediate Similarity NPD4202 Approved
0.7097 Intermediate Similarity NPD6616 Approved
0.708 Intermediate Similarity NPD5141 Approved
0.7075 Intermediate Similarity NPD46 Approved
0.7075 Intermediate Similarity NPD6698 Approved
0.7073 Intermediate Similarity NPD8328 Phase 3
0.7073 Intermediate Similarity NPD7604 Phase 2
0.7059 Intermediate Similarity NPD6274 Approved
0.7054 Intermediate Similarity NPD5225 Approved
0.7054 Intermediate Similarity NPD4633 Approved
0.7054 Intermediate Similarity NPD5224 Approved
0.7054 Intermediate Similarity NPD5226 Approved
0.7049 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD6015 Approved
0.7049 Intermediate Similarity NPD7503 Approved
0.7049 Intermediate Similarity NPD6016 Approved
0.704 Intermediate Similarity NPD8074 Phase 3
0.704 Intermediate Similarity NPD7078 Approved
0.704 Intermediate Similarity NPD8293 Discontinued
0.7031 Intermediate Similarity NPD6845 Suspended
0.7019 Intermediate Similarity NPD5279 Phase 3
0.7019 Intermediate Similarity NPD7521 Approved
0.7019 Intermediate Similarity NPD7334 Approved
0.7019 Intermediate Similarity NPD6409 Approved
0.7019 Intermediate Similarity NPD7146 Approved
0.7019 Intermediate Similarity NPD6684 Approved
0.7019 Intermediate Similarity NPD5330 Approved
0.7009 Intermediate Similarity NPD8035 Phase 2
0.7009 Intermediate Similarity NPD8034 Phase 2
0.7 Intermediate Similarity NPD6083 Phase 2
0.7 Intermediate Similarity NPD6084 Phase 2
0.7 Intermediate Similarity NPD6317 Approved
0.6992 Remote Similarity NPD6370 Approved
0.6992 Remote Similarity NPD5988 Approved
0.6991 Remote Similarity NPD4754 Approved
0.6991 Remote Similarity NPD5174 Approved
0.6991 Remote Similarity NPD5175 Approved
0.699 Remote Similarity NPD3666 Approved
0.699 Remote Similarity NPD3133 Approved
0.699 Remote Similarity NPD4786 Approved
0.699 Remote Similarity NPD3665 Phase 1
0.6984 Remote Similarity NPD7736 Approved
0.6972 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5695 Phase 3
0.696 Remote Similarity NPD6336 Discontinued
0.6957 Remote Similarity NPD6412 Phase 2
0.6942 Remote Similarity NPD6335 Approved
0.6942 Remote Similarity NPD6314 Approved
0.6942 Remote Similarity NPD6313 Approved
0.6937 Remote Similarity NPD5696 Approved
0.6923 Remote Similarity NPD4634 Approved
0.6917 Remote Similarity NPD6868 Approved
0.6916 Remote Similarity NPD5207 Approved
0.6887 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6672 Approved
0.6887 Remote Similarity NPD5737 Approved
0.6887 Remote Similarity NPD6903 Approved
0.6885 Remote Similarity NPD7101 Approved
0.6885 Remote Similarity NPD7100 Approved
0.6875 Remote Similarity NPD6648 Approved
0.687 Remote Similarity NPD4767 Approved
0.687 Remote Similarity NPD4768 Approved
0.686 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7637 Suspended
0.6852 Remote Similarity NPD5693 Phase 1
0.6852 Remote Similarity NPD7983 Approved
0.6838 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6814 Remote Similarity NPD5344 Discontinued
0.6803 Remote Similarity NPD7327 Approved
0.6803 Remote Similarity NPD7328 Approved
0.6786 Remote Similarity NPD8029 Clinical (unspecified phase)
0.678 Remote Similarity NPD6371 Approved
0.6774 Remote Similarity NPD6908 Approved
0.6774 Remote Similarity NPD8033 Approved
0.6774 Remote Similarity NPD6909 Approved
0.6762 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7838 Discovery
0.6759 Remote Similarity NPD5785 Approved
0.6759 Remote Similarity NPD5692 Phase 3
0.6752 Remote Similarity NPD4730 Approved
0.6752 Remote Similarity NPD4729 Approved
0.6752 Remote Similarity NPD5128 Approved
0.6748 Remote Similarity NPD7516 Approved
0.6727 Remote Similarity NPD6001 Approved
0.6727 Remote Similarity NPD5282 Discontinued
0.6723 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6719 Remote Similarity NPD6033 Approved
0.6698 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6697 Remote Similarity NPD5694 Approved
0.6697 Remote Similarity NPD6050 Approved
0.6694 Remote Similarity NPD8377 Approved
0.6694 Remote Similarity NPD8294 Approved
0.6667 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6067 Discontinued
0.6667 Remote Similarity NPD3668 Phase 3
0.6667 Remote Similarity NPD7899 Clinical (unspecified phase)
0.664 Remote Similarity NPD8380 Approved
0.664 Remote Similarity NPD8379 Approved
0.664 Remote Similarity NPD8378 Approved
0.664 Remote Similarity NPD8335 Approved
0.664 Remote Similarity NPD8296 Approved
0.6639 Remote Similarity NPD5135 Approved
0.6639 Remote Similarity NPD5250 Approved
0.6639 Remote Similarity NPD5248 Approved
0.6639 Remote Similarity NPD5169 Approved
0.6639 Remote Similarity NPD5249 Phase 3
0.6639 Remote Similarity NPD5247 Approved
0.6639 Remote Similarity NPD5251 Approved
0.6639 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6612 Remote Similarity NPD8133 Approved
0.661 Remote Similarity NPD5168 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