Structure

Physi-Chem Properties

Molecular Weight:  374.21
Volume:  388.248
LogP:  2.488
LogD:  2.245
LogS:  -3.581
# Rotatable Bonds:  2
TPSA:  61.83
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.52
Synthetic Accessibility Score:  6.24
Fsp3:  0.727
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:  -4.694
MDCK Permeability:  3.26E-05
Pgp-inhibitor:  0.743
Pgp-substrate:  0.943
Human Intestinal Absorption (HIA):  0.053
20% Bioavailability (F20%):  0.041
30% Bioavailability (F30%):  0.532

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.898
Plasma Protein Binding (PPB):  87.63%
Volume Distribution (VD):  1.934
Pgp-substrate:  5.76%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.091
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.654
CYP2C9-inhibitor:  0.077
CYP2C9-substrate:  0.035
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.233
CYP3A4-inhibitor:  0.438
CYP3A4-substrate:  0.45

ADMET: Excretion

Clearance (CL):  10.667
Half-life (T1/2):  0.648

ADMET: Toxicity

hERG Blockers:  0.096
Human Hepatotoxicity (H-HT):  0.699
Drug-inuced Liver Injury (DILI):  0.934
AMES Toxicity:  0.075
Rat Oral Acute Toxicity:  0.37
Maximum Recommended Daily Dose:  0.901
Skin Sensitization:  0.575
Carcinogencity:  0.281
Eye Corrosion:  0.787
Eye Irritation:  0.285
Respiratory Toxicity:  0.964

Download Data

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

  Natural Product: NPC477615

Natural Product ID:  NPC477615
Common Name*:   pachyclavulariaenone B
IUPAC Name:   [(1S,2R,3S,7R,8R,11S,12R,14Z,17R)-4,8,11,15-tetramethyl-6-oxo-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadeca-4,14-dien-12-yl] acetate
Synonyms:  
Standard InCHIKey:  GLBPZQWCAQTCDO-CTTKKIHVSA-N
Standard InCHI:  InChI=1S/C22H30O5/c1-11-6-7-17(26-14(4)23)22(5)21-20-18(13(3)10-25-22)15(24)9-12(2)19(20)16(8-11)27-21/h6,9,13,16-21H,7-8,10H2,1-5H3/b11-6-/t13-,16+,17+,18-,19-,20-,21-,22-/m0/s1
SMILES:  C[C@H]1CO[C@]2([C@@H](C/C=C(\C[C@@H]3[C@H]4[C@H]([C@@H]1C(=O)C=C4C)[C@@H]2O3)/C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   12011227
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001729] Oxepanes

*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
NPO32480 pachyclavularia violacea Species Clavulariidae Eukaryota n.a. n.a. n.a. PMID[12350166]
NPO32480 pachyclavularia violacea Species Clavulariidae Eukaryota n.a. n.a. n.a. PMID[12398546]
NPO32480 pachyclavularia violacea Species Clavulariidae Eukaryota n.a. n.a. n.a. PMID[12762802]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus IC50 > 1 ug/ml PMID[12350166]
NPT81 Cell Line A549 Homo sapiens IC50 > 1 ug/ml PMID[12350166]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 1 ug/ml PMID[12350166]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 > 1 ug/ml PMID[12350166]

☑ 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 NPC477615 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
0.8817 High Similarity NPC8803
0.8804 High Similarity NPC476716
0.8404 Intermediate Similarity NPC476722
0.8191 Intermediate Similarity NPC165180
0.8043 Intermediate Similarity NPC214315
0.79 Intermediate Similarity NPC101067
0.79 Intermediate Similarity NPC476134
0.7889 Intermediate Similarity NPC207188
0.7872 Intermediate Similarity NPC309656
0.7872 Intermediate Similarity NPC190718
0.783 Intermediate Similarity NPC474516
0.781 Intermediate Similarity NPC253906
0.7789 Intermediate Similarity NPC151770
0.7789 Intermediate Similarity NPC471222
0.7778 Intermediate Similarity NPC111348
0.7767 Intermediate Similarity NPC102352
0.7767 Intermediate Similarity NPC190867
0.7766 Intermediate Similarity NPC231889
0.7745 Intermediate Similarity NPC475321
0.7732 Intermediate Similarity NPC475657
0.7723 Intermediate Similarity NPC474742
0.7714 Intermediate Similarity NPC469370
0.7708 Intermediate Similarity NPC62815
0.7708 Intermediate Similarity NPC49342
0.7708 Intermediate Similarity NPC475748
0.7708 Intermediate Similarity NPC251385
0.7692 Intermediate Similarity NPC3316
0.7692 Intermediate Similarity NPC144854
0.7692 Intermediate Similarity NPC255580
0.7692 Intermediate Similarity NPC39411
0.767 Intermediate Similarity NPC228669
0.767 Intermediate Similarity NPC164835
0.7653 Intermediate Similarity NPC473330
0.7653 Intermediate Similarity NPC473316
0.7647 Intermediate Similarity NPC474747
0.7642 Intermediate Similarity NPC5103
0.7629 Intermediate Similarity NPC184463
0.7619 Intermediate Similarity NPC277017
0.7619 Intermediate Similarity NPC154608
0.7619 Intermediate Similarity NPC192813
0.7614 Intermediate Similarity NPC471491
0.7604 Intermediate Similarity NPC166919
0.7604 Intermediate Similarity NPC307411
0.76 Intermediate Similarity NPC27105
0.7596 Intermediate Similarity NPC291643
0.7596 Intermediate Similarity NPC96377
0.7593 Intermediate Similarity NPC49451
0.7582 Intermediate Similarity NPC474981
0.7579 Intermediate Similarity NPC475703
0.7573 Intermediate Similarity NPC475945
0.7573 Intermediate Similarity NPC475873
0.7573 Intermediate Similarity NPC475871
0.757 Intermediate Similarity NPC179798
0.757 Intermediate Similarity NPC304180
0.7553 Intermediate Similarity NPC50362
0.7553 Intermediate Similarity NPC38468
0.7553 Intermediate Similarity NPC319795
0.7551 Intermediate Similarity NPC212486
0.7551 Intermediate Similarity NPC476300
0.7551 Intermediate Similarity NPC475912
0.7549 Intermediate Similarity NPC477870
0.7549 Intermediate Similarity NPC476213
0.7549 Intermediate Similarity NPC476246
0.7549 Intermediate Similarity NPC477871
0.7527 Intermediate Similarity NPC475622
0.7527 Intermediate Similarity NPC272814
0.7527 Intermediate Similarity NPC108045
0.7527 Intermediate Similarity NPC193198
0.7526 Intermediate Similarity NPC152467
0.7526 Intermediate Similarity NPC51004
0.7526 Intermediate Similarity NPC80875
0.7525 Intermediate Similarity NPC203388
0.7525 Intermediate Similarity NPC471331
0.7525 Intermediate Similarity NPC471582
0.7525 Intermediate Similarity NPC471330
0.7525 Intermediate Similarity NPC222303
0.7525 Intermediate Similarity NPC472687
0.7525 Intermediate Similarity NPC471932
0.7525 Intermediate Similarity NPC99657
0.7525 Intermediate Similarity NPC23364
0.7524 Intermediate Similarity NPC133422
0.7524 Intermediate Similarity NPC180744
0.7523 Intermediate Similarity NPC473798
0.75 Intermediate Similarity NPC146731
0.75 Intermediate Similarity NPC58052
0.75 Intermediate Similarity NPC202672
0.75 Intermediate Similarity NPC255309
0.75 Intermediate Similarity NPC471775
0.75 Intermediate Similarity NPC234042
0.75 Intermediate Similarity NPC474741
0.75 Intermediate Similarity NPC111684
0.75 Intermediate Similarity NPC152117
0.75 Intermediate Similarity NPC258532
0.75 Intermediate Similarity NPC265391
0.75 Intermediate Similarity NPC472002
0.75 Intermediate Similarity NPC475665
0.7477 Intermediate Similarity NPC210005
0.7476 Intermediate Similarity NPC476126
0.7476 Intermediate Similarity NPC476235
0.7474 Intermediate Similarity NPC284902
0.7474 Intermediate Similarity NPC220478
0.7455 Intermediate Similarity NPC54739
0.7455 Intermediate Similarity NPC328374
0.7455 Intermediate Similarity NPC207217
0.7455 Intermediate Similarity NPC251236
0.7455 Intermediate Similarity NPC40632
0.7455 Intermediate Similarity NPC96312
0.7451 Intermediate Similarity NPC472972
0.7449 Intermediate Similarity NPC12172
0.7449 Intermediate Similarity NPC208839
0.7449 Intermediate Similarity NPC208886
0.7449 Intermediate Similarity NPC30515
0.7447 Intermediate Similarity NPC472957
0.7447 Intermediate Similarity NPC472958
0.7447 Intermediate Similarity NPC295799
0.7444 Intermediate Similarity NPC195785
0.7444 Intermediate Similarity NPC15975
0.7431 Intermediate Similarity NPC56448
0.7431 Intermediate Similarity NPC469454
0.7431 Intermediate Similarity NPC469496
0.7431 Intermediate Similarity NPC469463
0.7429 Intermediate Similarity NPC103088
0.7429 Intermediate Similarity NPC471333
0.7429 Intermediate Similarity NPC470979
0.7429 Intermediate Similarity NPC471332
0.7429 Intermediate Similarity NPC470975
0.7426 Intermediate Similarity NPC124246
0.7423 Intermediate Similarity NPC473564
0.7407 Intermediate Similarity NPC188738
0.7407 Intermediate Similarity NPC201992
0.7404 Intermediate Similarity NPC254202
0.74 Intermediate Similarity NPC14961
0.74 Intermediate Similarity NPC473369
0.74 Intermediate Similarity NPC36954
0.74 Intermediate Similarity NPC270013
0.7396 Intermediate Similarity NPC248602
0.7387 Intermediate Similarity NPC470854
0.7387 Intermediate Similarity NPC97908
0.7387 Intermediate Similarity NPC122033
0.7387 Intermediate Similarity NPC287343
0.7387 Intermediate Similarity NPC474654
0.7383 Intermediate Similarity NPC153239
0.7379 Intermediate Similarity NPC476270
0.7379 Intermediate Similarity NPC47880
0.7379 Intermediate Similarity NPC473384
0.7374 Intermediate Similarity NPC135776
0.7374 Intermediate Similarity NPC179746
0.7374 Intermediate Similarity NPC81419
0.7368 Intermediate Similarity NPC197903
0.7368 Intermediate Similarity NPC99395
0.7368 Intermediate Similarity NPC78089
0.7368 Intermediate Similarity NPC235792
0.7368 Intermediate Similarity NPC474547
0.7368 Intermediate Similarity NPC110405
0.7364 Intermediate Similarity NPC474181
0.7363 Intermediate Similarity NPC35574
0.7358 Intermediate Similarity NPC230541
0.7358 Intermediate Similarity NPC59530
0.7356 Intermediate Similarity NPC472955
0.7353 Intermediate Similarity NPC153792
0.7353 Intermediate Similarity NPC187268
0.7353 Intermediate Similarity NPC271387
0.7353 Intermediate Similarity NPC208233
0.7347 Intermediate Similarity NPC469595
0.7347 Intermediate Similarity NPC478003
0.7347 Intermediate Similarity NPC476004
0.7347 Intermediate Similarity NPC312042
0.7347 Intermediate Similarity NPC329857
0.7347 Intermediate Similarity NPC469718
0.7347 Intermediate Similarity NPC212679
0.7347 Intermediate Similarity NPC220454
0.7347 Intermediate Similarity NPC478004
0.7347 Intermediate Similarity NPC474761
0.7347 Intermediate Similarity NPC158388
0.734 Intermediate Similarity NPC257358
0.734 Intermediate Similarity NPC170286
0.734 Intermediate Similarity NPC474472
0.734 Intermediate Similarity NPC39588
0.734 Intermediate Similarity NPC318468
0.7339 Intermediate Similarity NPC289312
0.7339 Intermediate Similarity NPC269530
0.7339 Intermediate Similarity NPC11252
0.7333 Intermediate Similarity NPC470104
0.7333 Intermediate Similarity NPC296950
0.7333 Intermediate Similarity NPC169843
0.7333 Intermediate Similarity NPC100487
0.7333 Intermediate Similarity NPC471293
0.7333 Intermediate Similarity NPC65523
0.7333 Intermediate Similarity NPC472959
0.7333 Intermediate Similarity NPC203659
0.7327 Intermediate Similarity NPC476315
0.7327 Intermediate Similarity NPC472733
0.7327 Intermediate Similarity NPC301596
0.7327 Intermediate Similarity NPC472734
0.7327 Intermediate Similarity NPC299396
0.7321 Intermediate Similarity NPC17772
0.732 Intermediate Similarity NPC474471
0.732 Intermediate Similarity NPC281516
0.732 Intermediate Similarity NPC215831
0.732 Intermediate Similarity NPC227379

  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 NPC477615 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
0.7596 Intermediate Similarity NPD6008 Approved
0.7553 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6053 Discontinued
0.7113 Intermediate Similarity NPD7146 Approved
0.7113 Intermediate Similarity NPD6684 Approved
0.7113 Intermediate Similarity NPD5330 Approved
0.7113 Intermediate Similarity NPD6409 Approved
0.7113 Intermediate Similarity NPD7521 Approved
0.7113 Intermediate Similarity NPD7334 Approved
0.7071 Intermediate Similarity NPD1695 Approved
0.697 Remote Similarity NPD6672 Approved
0.697 Remote Similarity NPD6903 Approved
0.697 Remote Similarity NPD5737 Approved
0.697 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5282 Discontinued
0.6893 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6893 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6893 Remote Similarity NPD5695 Phase 3
0.6881 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6869 Remote Similarity NPD3573 Approved
0.6863 Remote Similarity NPD5778 Approved
0.6863 Remote Similarity NPD6399 Phase 3
0.6863 Remote Similarity NPD5779 Approved
0.6857 Remote Similarity NPD5696 Approved
0.6837 Remote Similarity NPD1694 Approved
0.6832 Remote Similarity NPD46 Approved
0.6832 Remote Similarity NPD5207 Approved
0.6832 Remote Similarity NPD6698 Approved
0.6814 Remote Similarity NPD4632 Approved
0.6796 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7900 Approved
0.6789 Remote Similarity NPD6675 Approved
0.6789 Remote Similarity NPD5739 Approved
0.6789 Remote Similarity NPD7128 Approved
0.6789 Remote Similarity NPD6402 Approved
0.6762 Remote Similarity NPD6084 Phase 2
0.6762 Remote Similarity NPD6083 Phase 2
0.6757 Remote Similarity NPD6372 Approved
0.6757 Remote Similarity NPD6373 Approved
0.6752 Remote Similarity NPD6319 Approved
0.6733 Remote Similarity NPD6673 Approved
0.6733 Remote Similarity NPD6080 Approved
0.6733 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6904 Approved
0.6733 Remote Similarity NPD6101 Approved
0.6727 Remote Similarity NPD5697 Approved
0.6727 Remote Similarity NPD5701 Approved
0.6727 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6412 Phase 2
0.6726 Remote Similarity NPD8297 Approved
0.6701 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD5692 Phase 3
0.6667 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD7320 Approved
0.6667 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD6899 Approved
0.6638 Remote Similarity NPD6009 Approved
0.6637 Remote Similarity NPD6649 Approved
0.6637 Remote Similarity NPD6650 Approved
0.6635 Remote Similarity NPD6001 Approved
0.6635 Remote Similarity NPD7748 Approved
0.6634 Remote Similarity NPD5208 Approved
0.6612 Remote Similarity NPD6616 Approved
0.661 Remote Similarity NPD6059 Approved
0.661 Remote Similarity NPD6054 Approved
0.6607 Remote Similarity NPD6014 Approved
0.6607 Remote Similarity NPD6013 Approved
0.6607 Remote Similarity NPD6012 Approved
0.6604 Remote Similarity NPD7902 Approved
0.6602 Remote Similarity NPD6050 Approved
0.6602 Remote Similarity NPD5694 Approved
0.6602 Remote Similarity NPD5693 Phase 1
0.6602 Remote Similarity NPD6411 Approved
0.6602 Remote Similarity NPD7983 Approved
0.6557 Remote Similarity NPD7078 Approved
0.6557 Remote Similarity NPD8293 Discontinued
0.6555 Remote Similarity NPD5983 Phase 2
0.6555 Remote Similarity NPD6016 Approved
0.6555 Remote Similarity NPD6015 Approved
0.6549 Remote Similarity NPD6883 Approved
0.6549 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6549 Remote Similarity NPD7102 Approved
0.6549 Remote Similarity NPD7290 Approved
0.6542 Remote Similarity NPD4225 Approved
0.6531 Remote Similarity NPD6435 Approved
0.6518 Remote Similarity NPD6686 Approved
0.6518 Remote Similarity NPD6011 Approved
0.6504 Remote Similarity NPD7736 Approved
0.65 Remote Similarity NPD6370 Approved
0.65 Remote Similarity NPD5988 Approved
0.6496 Remote Similarity NPD7115 Discovery
0.6491 Remote Similarity NPD6617 Approved
0.6491 Remote Similarity NPD8130 Phase 1
0.6491 Remote Similarity NPD6847 Approved
0.6491 Remote Similarity NPD6869 Approved
0.646 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6449 Remote Similarity NPD4755 Approved
0.6446 Remote Similarity NPD7604 Phase 2
0.6446 Remote Similarity NPD8328 Phase 3
0.6442 Remote Similarity NPD5281 Approved
0.6442 Remote Similarity NPD7515 Phase 2
0.6442 Remote Similarity NPD5284 Approved
0.6436 Remote Similarity NPD6098 Approved
0.6436 Remote Similarity NPD3618 Phase 1
0.6435 Remote Similarity NPD6882 Approved
0.6429 Remote Similarity NPD5369 Approved
0.6408 Remote Similarity NPD5328 Approved
0.6408 Remote Similarity NPD4753 Phase 2
0.64 Remote Similarity NPD3668 Phase 3
0.64 Remote Similarity NPD3666 Approved
0.64 Remote Similarity NPD3665 Phase 1
0.64 Remote Similarity NPD3133 Approved
0.6389 Remote Similarity NPD7638 Approved
0.6364 Remote Similarity NPD3667 Approved
0.6355 Remote Similarity NPD4697 Phase 3
0.6348 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6341 Remote Similarity NPD6336 Discontinued
0.6333 Remote Similarity NPD7331 Phase 2
0.633 Remote Similarity NPD7640 Approved
0.633 Remote Similarity NPD5285 Approved
0.633 Remote Similarity NPD4700 Approved
0.633 Remote Similarity NPD4696 Approved
0.633 Remote Similarity NPD7639 Approved
0.633 Remote Similarity NPD5286 Approved
0.6327 Remote Similarity NPD5368 Approved
0.6306 Remote Similarity NPD6052 Approved
0.6286 Remote Similarity NPD6079 Approved
0.6281 Remote Similarity NPD8517 Approved
0.6281 Remote Similarity NPD8516 Approved
0.6281 Remote Similarity NPD8515 Approved
0.6281 Remote Similarity NPD8513 Phase 3
0.6275 Remote Similarity NPD5786 Approved
0.6271 Remote Similarity NPD6274 Approved
0.6262 Remote Similarity NPD4629 Approved
0.6262 Remote Similarity NPD5210 Approved
0.6262 Remote Similarity NPD5654 Approved
0.6261 Remote Similarity NPD4634 Approved
0.6238 Remote Similarity NPD4786 Approved
0.6228 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6222 Remote Similarity NPD7341 Phase 2
0.622 Remote Similarity NPD7260 Phase 2
0.6216 Remote Similarity NPD5225 Approved
0.6216 Remote Similarity NPD5226 Approved
0.6216 Remote Similarity NPD5211 Phase 2
0.6216 Remote Similarity NPD4633 Approved
0.6216 Remote Similarity NPD5224 Approved
0.621 Remote Similarity NPD7507 Approved
0.6207 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5221 Approved
0.6204 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5222 Approved
0.62 Remote Similarity NPD4223 Phase 3
0.62 Remote Similarity NPD4221 Approved
0.619 Remote Similarity NPD7838 Discovery
0.6182 Remote Similarity NPD6648 Approved
0.6176 Remote Similarity NPD5363 Approved
0.6174 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6162 Remote Similarity NPD4695 Discontinued
0.6161 Remote Similarity NPD5175 Approved
0.6161 Remote Similarity NPD5174 Approved
0.6148 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6147 Remote Similarity NPD5173 Approved
0.6147 Remote Similarity NPD5959 Approved
0.6139 Remote Similarity NPD7154 Phase 3
0.6139 Remote Similarity NPD6110 Phase 1
0.6126 Remote Similarity NPD5344 Discontinued
0.6126 Remote Similarity NPD5223 Approved
0.6117 Remote Similarity NPD5279 Phase 3
0.6117 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6117 Remote Similarity NPD4249 Approved
0.6116 Remote Similarity NPD7100 Approved
0.6116 Remote Similarity NPD7101 Approved
0.6111 Remote Similarity NPD6033 Approved
0.6111 Remote Similarity NPD8336 Approved
0.6111 Remote Similarity NPD8337 Approved
0.6106 Remote Similarity NPD5141 Approved
0.61 Remote Similarity NPD1779 Approved
0.61 Remote Similarity NPD1780 Approved
0.6095 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6091 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6083 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6083 Remote Similarity NPD6317 Approved
0.6078 Remote Similarity NPD4197 Approved
0.6075 Remote Similarity NPD4202 Approved
0.6063 Remote Similarity NPD7319 Approved
0.6058 Remote Similarity NPD4250 Approved
0.6058 Remote Similarity NPD4251 Approved
0.6055 Remote Similarity NPD7732 Phase 3
0.6055 Remote Similarity NPD7839 Suspended
0.6055 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6053 Remote Similarity NPD4768 Approved
0.6053 Remote Similarity NPD4767 Approved
0.6047 Remote Similarity NPD6845 Suspended
0.604 Remote Similarity NPD4269 Approved
0.604 Remote Similarity NPD4270 Approved
0.6038 Remote Similarity NPD5785 Approved
0.6033 Remote Similarity NPD6313 Approved
0.6033 Remote Similarity NPD7641 Discontinued
0.6033 Remote Similarity NPD6314 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