Structure

Physi-Chem Properties

Molecular Weight:  250.16
Volume:  263.425
LogP:  2.311
LogD:  2.374
LogS:  -3.52
# Rotatable Bonds:  0
TPSA:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.53
Synthetic Accessibility Score:  4.894
Fsp3:  0.8
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:  -4.644
MDCK Permeability:  1.7502426999271847e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.955
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.045
30% Bioavailability (F30%):  0.132

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.903
Plasma Protein Binding (PPB):  65.92171478271484%
Volume Distribution (VD):  1.674
Pgp-substrate:  47.20100784301758%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.936
CYP2C19-inhibitor:  0.199
CYP2C19-substrate:  0.884
CYP2C9-inhibitor:  0.033
CYP2C9-substrate:  0.068
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.214
CYP3A4-inhibitor:  0.119
CYP3A4-substrate:  0.803

ADMET: Excretion

Clearance (CL):  11.002
Half-life (T1/2):  0.623

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.645
Drug-inuced Liver Injury (DILI):  0.438
AMES Toxicity:  0.915
Rat Oral Acute Toxicity:  0.981
Maximum Recommended Daily Dose:  0.943
Skin Sensitization:  0.842
Carcinogencity:  0.954
Eye Corrosion:  0.169
Eye Irritation:  0.747
Respiratory Toxicity:  0.982

Download Data

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

  Natural Product: NPC109556

Natural Product ID:  NPC109556
Common Name*:   MWQWIKHVCLVRDU-HRTSBPGXSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MWQWIKHVCLVRDU-HRTSBPGXSA-N
Standard InCHI:  InChI=1S/C15H22O3/c1-9-7-14-12(17)13(3,4)8-15(14,18-14)10(2)5-6-11(9)16/h7,10-11,16H,5-6,8H2,1-4H3/b9-7-/t10-,11+,14-,15-/m1/s1
SMILES:  CC1=C[C@@]23O[C@]3(CC(C2=O)(C)C)[C@@H](CC[C@@H]1O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2419335
PubChem CID:   73349166
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002012] Oxanes

*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
NPO22108 Sinularia capillosa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[11087604]
NPO22108 Sinularia capillosa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[20155971]
NPO22108 Sinularia capillosa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[23964704]
NPO22108 Sinularia capillosa Species Alcyoniidae 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
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[551631]
NPT81 Cell Line A549 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[551631]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[551631]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[551631]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[551631]

☑ 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 NPC109556 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
0.8061 Intermediate Similarity NPC475488
0.8018 Intermediate Similarity NPC477092
0.8 Intermediate Similarity NPC475305
0.7928 Intermediate Similarity NPC475401
0.7879 Intermediate Similarity NPC37816
0.7843 Intermediate Similarity NPC212465
0.7843 Intermediate Similarity NPC177232
0.7843 Intermediate Similarity NPC470188
0.7788 Intermediate Similarity NPC118405
0.7788 Intermediate Similarity NPC105725
0.7788 Intermediate Similarity NPC25639
0.7757 Intermediate Similarity NPC117604
0.7706 Intermediate Similarity NPC475495
0.77 Intermediate Similarity NPC125180
0.7692 Intermediate Similarity NPC304738
0.7692 Intermediate Similarity NPC207885
0.7692 Intermediate Similarity NPC195192
0.7685 Intermediate Similarity NPC77089
0.7664 Intermediate Similarity NPC204884
0.7636 Intermediate Similarity NPC477093
0.7636 Intermediate Similarity NPC473522
0.7636 Intermediate Similarity NPC475277
0.7624 Intermediate Similarity NPC298919
0.7619 Intermediate Similarity NPC49393
0.7604 Intermediate Similarity NPC475796
0.76 Intermediate Similarity NPC20713
0.7579 Intermediate Similarity NPC133844
0.7573 Intermediate Similarity NPC477949
0.757 Intermediate Similarity NPC179891
0.757 Intermediate Similarity NPC314244
0.7547 Intermediate Similarity NPC123505
0.7545 Intermediate Similarity NPC287311
0.7525 Intermediate Similarity NPC200237
0.7524 Intermediate Similarity NPC471767
0.7524 Intermediate Similarity NPC477950
0.7524 Intermediate Similarity NPC112613
0.7524 Intermediate Similarity NPC477356
0.7524 Intermediate Similarity NPC475099
0.7524 Intermediate Similarity NPC171759
0.75 Intermediate Similarity NPC470541
0.75 Intermediate Similarity NPC226242
0.75 Intermediate Similarity NPC221615
0.75 Intermediate Similarity NPC301969
0.75 Intermediate Similarity NPC37607
0.7476 Intermediate Similarity NPC94337
0.7473 Intermediate Similarity NPC206875
0.7453 Intermediate Similarity NPC250594
0.7453 Intermediate Similarity NPC78127
0.7453 Intermediate Similarity NPC471757
0.7451 Intermediate Similarity NPC473331
0.7434 Intermediate Similarity NPC476711
0.7434 Intermediate Similarity NPC476710
0.7431 Intermediate Similarity NPC322903
0.7431 Intermediate Similarity NPC233379
0.7431 Intermediate Similarity NPC474664
0.7431 Intermediate Similarity NPC308191
0.7431 Intermediate Similarity NPC14862
0.7426 Intermediate Similarity NPC221282
0.7423 Intermediate Similarity NPC90446
0.7407 Intermediate Similarity NPC475802
0.7404 Intermediate Similarity NPC170143
0.7404 Intermediate Similarity NPC471916
0.7404 Intermediate Similarity NPC213947
0.7404 Intermediate Similarity NPC87090
0.7404 Intermediate Similarity NPC108475
0.7404 Intermediate Similarity NPC69385
0.74 Intermediate Similarity NPC170775
0.7383 Intermediate Similarity NPC472755
0.7383 Intermediate Similarity NPC474775
0.7379 Intermediate Similarity NPC469873
0.7379 Intermediate Similarity NPC261341
0.7379 Intermediate Similarity NPC52044
0.7368 Intermediate Similarity NPC239273
0.7368 Intermediate Similarity NPC476712
0.7368 Intermediate Similarity NPC476713
0.7364 Intermediate Similarity NPC15218
0.7364 Intermediate Similarity NPC471400
0.7358 Intermediate Similarity NPC472753
0.7358 Intermediate Similarity NPC201718
0.7353 Intermediate Similarity NPC153590
0.7347 Intermediate Similarity NPC96621
0.7345 Intermediate Similarity NPC238667
0.7339 Intermediate Similarity NPC72813
0.7339 Intermediate Similarity NPC474421
0.7339 Intermediate Similarity NPC194620
0.7339 Intermediate Similarity NPC326994
0.7339 Intermediate Similarity NPC324327
0.7333 Intermediate Similarity NPC222011
0.7333 Intermediate Similarity NPC477355
0.7327 Intermediate Similarity NPC71533
0.7327 Intermediate Similarity NPC106510
0.7327 Intermediate Similarity NPC477711
0.732 Intermediate Similarity NPC473629
0.7315 Intermediate Similarity NPC309190
0.7315 Intermediate Similarity NPC474741
0.7312 Intermediate Similarity NPC271070
0.7308 Intermediate Similarity NPC142529
0.7308 Intermediate Similarity NPC91771
0.73 Intermediate Similarity NPC477710
0.7297 Intermediate Similarity NPC161816
0.7297 Intermediate Similarity NPC76084
0.7297 Intermediate Similarity NPC115257
0.7297 Intermediate Similarity NPC257240
0.729 Intermediate Similarity NPC470840
0.729 Intermediate Similarity NPC70369
0.729 Intermediate Similarity NPC472754
0.7282 Intermediate Similarity NPC90453
0.7282 Intermediate Similarity NPC81386
0.7282 Intermediate Similarity NPC474035
0.7281 Intermediate Similarity NPC148458
0.7273 Intermediate Similarity NPC474045
0.7273 Intermediate Similarity NPC327286
0.7273 Intermediate Similarity NPC55972
0.7273 Intermediate Similarity NPC169888
0.7273 Intermediate Similarity NPC261253
0.7273 Intermediate Similarity NPC469676
0.7264 Intermediate Similarity NPC280963
0.7264 Intermediate Similarity NPC288876
0.7257 Intermediate Similarity NPC9848
0.7257 Intermediate Similarity NPC312017
0.7248 Intermediate Similarity NPC243998
0.7248 Intermediate Similarity NPC474101
0.7248 Intermediate Similarity NPC16313
0.7248 Intermediate Similarity NPC9303
0.7238 Intermediate Similarity NPC161493
0.7234 Intermediate Similarity NPC276769
0.7234 Intermediate Similarity NPC471454
0.7232 Intermediate Similarity NPC207689
0.7232 Intermediate Similarity NPC317107
0.7228 Intermediate Similarity NPC232747
0.7228 Intermediate Similarity NPC41217
0.7222 Intermediate Similarity NPC475871
0.7222 Intermediate Similarity NPC475945
0.7222 Intermediate Similarity NPC26478
0.7217 Intermediate Similarity NPC474518
0.7212 Intermediate Similarity NPC474947
0.7212 Intermediate Similarity NPC270013
0.7212 Intermediate Similarity NPC163228
0.7212 Intermediate Similarity NPC67584
0.7212 Intermediate Similarity NPC37408
0.7212 Intermediate Similarity NPC170120
0.7212 Intermediate Similarity NPC14961
0.7207 Intermediate Similarity NPC475922
0.7207 Intermediate Similarity NPC474901
0.7207 Intermediate Similarity NPC475941
0.7203 Intermediate Similarity NPC470419
0.72 Intermediate Similarity NPC471738
0.7196 Intermediate Similarity NPC164598
0.7196 Intermediate Similarity NPC471401
0.7196 Intermediate Similarity NPC116139
0.7196 Intermediate Similarity NPC476270
0.7196 Intermediate Similarity NPC474339
0.7196 Intermediate Similarity NPC474742
0.7184 Intermediate Similarity NPC60386
0.7184 Intermediate Similarity NPC473263
0.7184 Intermediate Similarity NPC473273
0.7184 Intermediate Similarity NPC308656
0.7184 Intermediate Similarity NPC473234
0.7182 Intermediate Similarity NPC470192
0.7182 Intermediate Similarity NPC477513
0.7174 Intermediate Similarity NPC92909
0.7174 Intermediate Similarity NPC107783
0.7172 Intermediate Similarity NPC36350
0.7168 Intermediate Similarity NPC123855
0.7168 Intermediate Similarity NPC76550
0.7168 Intermediate Similarity NPC317687
0.7168 Intermediate Similarity NPC471933
0.7157 Intermediate Similarity NPC469718
0.7157 Intermediate Similarity NPC2946
0.7157 Intermediate Similarity NPC246173
0.7157 Intermediate Similarity NPC329857
0.7156 Intermediate Similarity NPC472756
0.7156 Intermediate Similarity NPC258532
0.7156 Intermediate Similarity NPC100487
0.7156 Intermediate Similarity NPC475676
0.7156 Intermediate Similarity NPC220964
0.7155 Intermediate Similarity NPC474286
0.7155 Intermediate Similarity NPC475130
0.7143 Intermediate Similarity NPC49371
0.7143 Intermediate Similarity NPC230800
0.7143 Intermediate Similarity NPC213078
0.7143 Intermediate Similarity NPC206595
0.7143 Intermediate Similarity NPC477103
0.7143 Intermediate Similarity NPC41551
0.7143 Intermediate Similarity NPC476275
0.7143 Intermediate Similarity NPC476315
0.7143 Intermediate Similarity NPC50223
0.7143 Intermediate Similarity NPC477354
0.7143 Intermediate Similarity NPC126156
0.7143 Intermediate Similarity NPC473859
0.7143 Intermediate Similarity NPC99760
0.713 Intermediate Similarity NPC185530
0.713 Intermediate Similarity NPC66110
0.713 Intermediate Similarity NPC471148
0.713 Intermediate Similarity NPC474747
0.713 Intermediate Similarity NPC87351
0.7129 Intermediate Similarity NPC471941
0.7129 Intermediate Similarity NPC91248
0.7128 Intermediate Similarity NPC469646
0.7119 Intermediate Similarity NPC471999

  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 NPC109556 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
0.7327 Intermediate Similarity NPD5785 Approved
0.7297 Intermediate Similarity NPD6371 Approved
0.7273 Intermediate Similarity NPD5786 Approved
0.7041 Intermediate Similarity NPD4269 Approved
0.7041 Intermediate Similarity NPD4270 Approved
0.6952 Remote Similarity NPD5282 Discontinued
0.6939 Remote Similarity NPD5369 Approved
0.6893 Remote Similarity NPD1695 Approved
0.6887 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6837 Remote Similarity NPD4252 Approved
0.6832 Remote Similarity NPD5363 Approved
0.68 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD5211 Phase 2
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6639 Remote Similarity NPD7115 Discovery
0.6637 Remote Similarity NPD6402 Approved
0.6637 Remote Similarity NPD6008 Approved
0.6637 Remote Similarity NPD7128 Approved
0.6637 Remote Similarity NPD5739 Approved
0.6637 Remote Similarity NPD6675 Approved
0.6633 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6612 Remote Similarity NPD6059 Approved
0.6612 Remote Similarity NPD6054 Approved
0.6612 Remote Similarity NPD6319 Approved
0.6609 Remote Similarity NPD6372 Approved
0.6609 Remote Similarity NPD6373 Approved
0.6606 Remote Similarity NPD6084 Phase 2
0.6606 Remote Similarity NPD4755 Approved
0.6606 Remote Similarity NPD6083 Phase 2
0.6581 Remote Similarity NPD6053 Discontinued
0.6579 Remote Similarity NPD5697 Approved
0.6579 Remote Similarity NPD5701 Approved
0.6574 Remote Similarity NPD5695 Phase 3
0.6571 Remote Similarity NPD4753 Phase 2
0.6557 Remote Similarity NPD6016 Approved
0.6557 Remote Similarity NPD6015 Approved
0.6552 Remote Similarity NPD4634 Approved
0.6549 Remote Similarity NPD5141 Approved
0.6545 Remote Similarity NPD5696 Approved
0.6542 Remote Similarity NPD5779 Approved
0.6542 Remote Similarity NPD5778 Approved
0.6535 Remote Similarity NPD6435 Approved
0.6522 Remote Similarity NPD6899 Approved
0.6522 Remote Similarity NPD6011 Approved
0.6522 Remote Similarity NPD6881 Approved
0.6522 Remote Similarity NPD7320 Approved
0.6505 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6504 Remote Similarity NPD6370 Approved
0.6504 Remote Similarity NPD5988 Approved
0.6496 Remote Similarity NPD6650 Approved
0.6496 Remote Similarity NPD6649 Approved
0.6486 Remote Similarity NPD4696 Approved
0.6486 Remote Similarity NPD5285 Approved
0.6486 Remote Similarity NPD7640 Approved
0.6486 Remote Similarity NPD7639 Approved
0.6486 Remote Similarity NPD5286 Approved
0.6486 Remote Similarity NPD4700 Approved
0.6466 Remote Similarity NPD6012 Approved
0.6466 Remote Similarity NPD6014 Approved
0.6466 Remote Similarity NPD6013 Approved
0.6449 Remote Similarity NPD5693 Phase 1
0.6449 Remote Similarity NPD7637 Suspended
0.6449 Remote Similarity NPD7983 Approved
0.6442 Remote Similarity NPD5279 Phase 3
0.6442 Remote Similarity NPD4249 Approved
0.6429 Remote Similarity NPD5223 Approved
0.6422 Remote Similarity NPD4629 Approved
0.6422 Remote Similarity NPD5210 Approved
0.641 Remote Similarity NPD7102 Approved
0.641 Remote Similarity NPD7290 Approved
0.641 Remote Similarity NPD6883 Approved
0.6408 Remote Similarity NPD4786 Approved
0.6408 Remote Similarity NPD3665 Phase 1
0.6408 Remote Similarity NPD3133 Approved
0.6408 Remote Similarity NPD3666 Approved
0.6408 Remote Similarity NPD4197 Approved
0.64 Remote Similarity NPD7492 Approved
0.6396 Remote Similarity NPD7638 Approved
0.6387 Remote Similarity NPD4632 Approved
0.6381 Remote Similarity NPD4250 Approved
0.6381 Remote Similarity NPD4251 Approved
0.6373 Remote Similarity NPD3667 Approved
0.6372 Remote Similarity NPD4633 Approved
0.6372 Remote Similarity NPD5225 Approved
0.6372 Remote Similarity NPD5224 Approved
0.6372 Remote Similarity NPD5226 Approved
0.6364 Remote Similarity NPD6009 Approved
0.6364 Remote Similarity NPD4697 Phase 3
0.6356 Remote Similarity NPD6847 Approved
0.6356 Remote Similarity NPD6869 Approved
0.6356 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6356 Remote Similarity NPD6617 Approved
0.6356 Remote Similarity NPD8130 Phase 1
0.6355 Remote Similarity NPD6698 Approved
0.6355 Remote Similarity NPD46 Approved
0.6349 Remote Similarity NPD6616 Approved
0.6346 Remote Similarity NPD5329 Approved
0.6337 Remote Similarity NPD4822 Approved
0.6337 Remote Similarity NPD4820 Approved
0.6337 Remote Similarity NPD4821 Approved
0.6337 Remote Similarity NPD4819 Approved
0.6337 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5368 Approved
0.632 Remote Similarity NPD7604 Phase 2
0.6316 Remote Similarity NPD4754 Approved
0.6316 Remote Similarity NPD5174 Approved
0.6316 Remote Similarity NPD5175 Approved
0.6311 Remote Similarity NPD5332 Approved
0.6311 Remote Similarity NPD7154 Phase 3
0.6311 Remote Similarity NPD5331 Approved
0.6311 Remote Similarity NPD6695 Phase 3
0.6303 Remote Similarity NPD8297 Approved
0.6303 Remote Similarity NPD6882 Approved
0.6299 Remote Similarity NPD7078 Approved
0.6299 Remote Similarity NPD8293 Discontinued
0.629 Remote Similarity NPD5983 Phase 2
0.6286 Remote Similarity NPD5690 Phase 2
0.6286 Remote Similarity NPD4694 Approved
0.6286 Remote Similarity NPD6098 Approved
0.6286 Remote Similarity NPD5280 Approved
0.6275 Remote Similarity NPD4790 Discontinued
0.6262 Remote Similarity NPD5328 Approved
0.625 Remote Similarity NPD6033 Approved
0.625 Remote Similarity NPD7338 Clinical (unspecified phase)
0.625 Remote Similarity NPD7736 Approved
0.6239 Remote Similarity NPD6399 Phase 3
0.6239 Remote Similarity NPD4202 Approved
0.6226 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5221 Approved
0.6216 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5222 Approved
0.6214 Remote Similarity NPD4221 Approved
0.6214 Remote Similarity NPD4223 Phase 3
0.6214 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6207 Remote Similarity NPD4767 Approved
0.6207 Remote Similarity NPD4768 Approved
0.6202 Remote Similarity NPD7319 Approved
0.619 Remote Similarity NPD1696 Phase 3
0.6176 Remote Similarity NPD6930 Phase 2
0.6176 Remote Similarity NPD6931 Approved
0.6161 Remote Similarity NPD5173 Approved
0.6154 Remote Similarity NPD6110 Phase 1
0.6148 Remote Similarity NPD6274 Approved
0.6147 Remote Similarity NPD6079 Approved
0.6147 Remote Similarity NPD6411 Approved
0.6139 Remote Similarity NPD4271 Approved
0.6139 Remote Similarity NPD4268 Approved
0.6132 Remote Similarity NPD3618 Phase 1
0.6111 Remote Similarity NPD6673 Approved
0.6111 Remote Similarity NPD6080 Approved
0.6111 Remote Similarity NPD6904 Approved
0.6106 Remote Similarity NPD4225 Approved
0.6102 Remote Similarity NPD4729 Approved
0.6102 Remote Similarity NPD4730 Approved
0.6102 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6102 Remote Similarity NPD5128 Approved
0.6098 Remote Similarity NPD6317 Approved
0.6094 Remote Similarity NPD7507 Approved
0.6094 Remote Similarity NPD6336 Discontinued
0.6083 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6078 Remote Similarity NPD6929 Approved
0.6075 Remote Similarity NPD7750 Discontinued
0.6075 Remote Similarity NPD7524 Approved
0.6071 Remote Similarity NPD7839 Suspended
0.6058 Remote Similarity NPD5209 Approved
0.6055 Remote Similarity NPD5692 Phase 3
0.6048 Remote Similarity NPD6314 Approved
0.6048 Remote Similarity NPD6313 Approved
0.6048 Remote Similarity NPD6335 Approved
0.6038 Remote Similarity NPD1694 Approved
0.6019 Remote Similarity NPD5737 Approved
0.6019 Remote Similarity NPD4518 Approved
0.6019 Remote Similarity NPD7514 Phase 3
0.6019 Remote Similarity NPD6672 Approved
0.6017 Remote Similarity NPD6412 Phase 2
0.6 Remote Similarity NPD7100 Approved
0.6 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6 Remote Similarity NPD5135 Approved
0.6 Remote Similarity NPD7101 Approved
0.6 Remote Similarity NPD5250 Approved
0.6 Remote Similarity NPD5249 Phase 3
0.6 Remote Similarity NPD1700 Approved
0.6 Remote Similarity NPD5248 Approved
0.6 Remote Similarity NPD5694 Approved
0.6 Remote Similarity NPD6050 Approved
0.6 Remote Similarity NPD4788 Approved
0.6 Remote Similarity NPD5247 Approved
0.6 Remote Similarity NPD5251 Approved
0.6 Remote Similarity NPD5169 Approved
0.5981 Remote Similarity NPD5330 Approved
0.5981 Remote Similarity NPD4689 Approved
0.5981 Remote Similarity NPD4138 Approved
0.5981 Remote Similarity NPD4693 Phase 3
0.5981 Remote Similarity NPD5205 Approved
0.5981 Remote Similarity NPD6409 Approved
0.5981 Remote Similarity NPD7521 Approved
0.5981 Remote Similarity NPD7146 Approved
0.5981 Remote Similarity NPD4690 Approved
0.5981 Remote Similarity NPD6684 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