Structure

Physi-Chem Properties

Molecular Weight:  591.41
Volume:  615.173
LogP:  3.547
LogD:  4.107
LogS:  -4.187
# Rotatable Bonds:  5
TPSA:  119.69
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.36
Synthetic Accessibility Score:  5.295
Fsp3:  0.971
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.062
MDCK Permeability:  3.581757846404798e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.94
Human Intestinal Absorption (HIA):  0.811
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.058
Plasma Protein Binding (PPB):  69.38751220703125%
Volume Distribution (VD):  0.727
Pgp-substrate:  15.254892349243164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.011
CYP1A2-substrate:  0.293
CYP2C19-inhibitor:  0.008
CYP2C19-substrate:  0.89
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.496
CYP3A4-inhibitor:  0.181
CYP3A4-substrate:  0.397

ADMET: Excretion

Clearance (CL):  9.231
Half-life (T1/2):  0.665

ADMET: Toxicity

hERG Blockers:  0.921
Human Hepatotoxicity (H-HT):  0.294
Drug-inuced Liver Injury (DILI):  0.31
AMES Toxicity:  0.056
Rat Oral Acute Toxicity:  0.367
Maximum Recommended Daily Dose:  0.748
Skin Sensitization:  0.917
Carcinogencity:  0.336
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.971

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  Natural Product: NPC28224

Natural Product ID:  NPC28224
Common Name*:   Puqietinonoside
IUPAC Name:   (3S,5S,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(2R,5S)-1,5-dimethylpiperidin-2-yl]ethyl]-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
Synonyms:   puqietinonoside
Standard InCHIKey:  GRPUWGWLJURVLD-BFSGSYDSSA-N
Standard InCHI:  InChI=1S/C34H57NO7/c1-18-6-9-26(35(5)16-18)19(2)22-7-8-23-21-15-27(37)25-14-20(10-12-34(25,4)24(21)11-13-33(22,23)3)41-32-31(40)30(39)29(38)28(17-36)42-32/h18-26,28-32,36,38-40H,6-17H2,1-5H3/t18-,19-,20-,21-,22+,23-,24-,25+,26+,28+,29+,30-,31+,32+,33+,34+/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2)C(=O)C[C@@H]2[C@@H]3CC[C@]3([C@H]2CC[C@@H]3[C@@H]([C@H]2CC[C@@H](CN2C)C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504751
PubChem CID:   21575476
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*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
NPO20194 Fritillaria puqiensis Species Liliaceae Eukaryota bulbs n.a. n.a. PMID[15730259]
NPO14849 Fritillaria unibracteata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12273 Fritillaria delavayi Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22292 Fritillaria przewalskii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20194 Fritillaria puqiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18644 Fritillaria walujewii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14849 Fritillaria unibracteata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22292 Fritillaria przewalskii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12273 Fritillaria delavayi Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20194 Fritillaria puqiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18644 Fritillaria walujewii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12273 Fritillaria delavayi Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22292 Fritillaria przewalskii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14849 Fritillaria unibracteata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18644 Fritillaria walujewii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12556 Fritillaria verticillata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12273 Fritillaria delavayi Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12556 Fritillaria verticillata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14135 Fritillaria prezewalskii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14849 Fritillaria unibracteata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22292 Fritillaria przewalskii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25808 Fritillaria taipaiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18644 Fritillaria walujewii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20194 Fritillaria puqiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14849 Fritillaria unibracteata Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18644 Fritillaria walujewii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12273 Fritillaria delavayi Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25808 Fritillaria taipaiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22292 Fritillaria przewalskii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12556 Fritillaria verticillata Species Liliaceae 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
NPT32 Organism Mus musculus Mus musculus Activity = 13.0 n.a. PMID[480727]
NPT32 Organism Mus musculus Mus musculus Activity = 17.0 n.a. PMID[480727]

☑ 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 NPC28224 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
0.8318 Intermediate Similarity NPC20028
0.8165 Intermediate Similarity NPC80191
0.8165 Intermediate Similarity NPC310031
0.8077 Intermediate Similarity NPC312637
0.7946 Intermediate Similarity NPC215408
0.7909 Intermediate Similarity NPC477172
0.789 Intermediate Similarity NPC220111
0.7818 Intermediate Similarity NPC41843
0.7807 Intermediate Similarity NPC202898
0.7807 Intermediate Similarity NPC92890
0.7807 Intermediate Similarity NPC475319
0.7768 Intermediate Similarity NPC34562
0.7768 Intermediate Similarity NPC107385
0.7739 Intermediate Similarity NPC233433
0.7739 Intermediate Similarity NPC92297
0.7739 Intermediate Similarity NPC220836
0.7739 Intermediate Similarity NPC94086
0.7739 Intermediate Similarity NPC273002
0.7739 Intermediate Similarity NPC473817
0.7731 Intermediate Similarity NPC39485
0.7731 Intermediate Similarity NPC221196
0.7719 Intermediate Similarity NPC203974
0.7699 Intermediate Similarity NPC469827
0.7679 Intermediate Similarity NPC80640
0.7652 Intermediate Similarity NPC472079
0.7636 Intermediate Similarity NPC472273
0.7619 Intermediate Similarity NPC309249
0.7615 Intermediate Similarity NPC174117
0.7607 Intermediate Similarity NPC246399
0.7607 Intermediate Similarity NPC274833
0.7607 Intermediate Similarity NPC34977
0.7586 Intermediate Similarity NPC469825
0.7586 Intermediate Similarity NPC236753
0.7586 Intermediate Similarity NPC228190
0.7544 Intermediate Similarity NPC267637
0.7544 Intermediate Similarity NPC470167
0.7542 Intermediate Similarity NPC472719
0.7542 Intermediate Similarity NPC477489
0.7542 Intermediate Similarity NPC477492
0.7542 Intermediate Similarity NPC207845
0.75 Intermediate Similarity NPC80417
0.75 Intermediate Similarity NPC469826
0.7478 Intermediate Similarity NPC184805
0.7478 Intermediate Similarity NPC273189
0.7477 Intermediate Similarity NPC131466
0.7458 Intermediate Similarity NPC469824
0.7455 Intermediate Similarity NPC215570
0.7455 Intermediate Similarity NPC94582
0.7455 Intermediate Similarity NPC57964
0.7436 Intermediate Similarity NPC8431
0.7436 Intermediate Similarity NPC51947
0.7436 Intermediate Similarity NPC473844
0.7414 Intermediate Similarity NPC471430
0.7414 Intermediate Similarity NPC317534
0.7407 Intermediate Similarity NPC65550
0.7387 Intermediate Similarity NPC203434
0.7387 Intermediate Similarity NPC296936
0.7387 Intermediate Similarity NPC238796
0.7387 Intermediate Similarity NPC237071
0.7381 Intermediate Similarity NPC94881
0.7381 Intermediate Similarity NPC265275
0.7381 Intermediate Similarity NPC48886
0.7355 Intermediate Similarity NPC472718
0.7355 Intermediate Similarity NPC476502
0.735 Intermediate Similarity NPC88744
0.7339 Intermediate Similarity NPC473830
0.7339 Intermediate Similarity NPC307167
0.7339 Intermediate Similarity NPC204881
0.7339 Intermediate Similarity NPC229801
0.7339 Intermediate Similarity NPC210759
0.7321 Intermediate Similarity NPC470591
0.7321 Intermediate Similarity NPC210157
0.7311 Intermediate Similarity NPC204392
0.7311 Intermediate Similarity NPC473062
0.7311 Intermediate Similarity NPC11035
0.7311 Intermediate Similarity NPC240734
0.7311 Intermediate Similarity NPC1876
0.7311 Intermediate Similarity NPC275668
0.7311 Intermediate Similarity NPC91838
0.7308 Intermediate Similarity NPC262050
0.7302 Intermediate Similarity NPC296686
0.729 Intermediate Similarity NPC43912
0.729 Intermediate Similarity NPC140446
0.7288 Intermediate Similarity NPC87393
0.7288 Intermediate Similarity NPC240125
0.7288 Intermediate Similarity NPC91583
0.7281 Intermediate Similarity NPC178853
0.7273 Intermediate Similarity NPC249204
0.7273 Intermediate Similarity NPC297348
0.7273 Intermediate Similarity NPC477451
0.7273 Intermediate Similarity NPC172838
0.7273 Intermediate Similarity NPC137004
0.7273 Intermediate Similarity NPC473726
0.7273 Intermediate Similarity NPC144790
0.7273 Intermediate Similarity NPC325828
0.7273 Intermediate Similarity NPC161035
0.7273 Intermediate Similarity NPC88962
0.7273 Intermediate Similarity NPC177834
0.7273 Intermediate Similarity NPC149400
0.7273 Intermediate Similarity NPC141769
0.7273 Intermediate Similarity NPC234352
0.7273 Intermediate Similarity NPC48339
0.7273 Intermediate Similarity NPC250393
0.7273 Intermediate Similarity NPC477547
0.7265 Intermediate Similarity NPC287269
0.7264 Intermediate Similarity NPC290612
0.7252 Intermediate Similarity NPC477072
0.725 Intermediate Similarity NPC470543
0.7227 Intermediate Similarity NPC470622
0.7227 Intermediate Similarity NPC66513
0.7222 Intermediate Similarity NPC281004
0.7217 Intermediate Similarity NPC227622
0.7217 Intermediate Similarity NPC94919
0.7217 Intermediate Similarity NPC470172
0.7207 Intermediate Similarity NPC151214
0.7207 Intermediate Similarity NPC179859
0.7207 Intermediate Similarity NPC264101
0.7207 Intermediate Similarity NPC45959
0.7207 Intermediate Similarity NPC252253
0.7207 Intermediate Similarity NPC309866
0.7207 Intermediate Similarity NPC475436
0.7207 Intermediate Similarity NPC312678
0.7207 Intermediate Similarity NPC471464
0.7207 Intermediate Similarity NPC253268
0.7207 Intermediate Similarity NPC294686
0.7207 Intermediate Similarity NPC24960
0.7207 Intermediate Similarity NPC291547
0.7207 Intermediate Similarity NPC291203
0.7207 Intermediate Similarity NPC473774
0.7207 Intermediate Similarity NPC174024
0.7207 Intermediate Similarity NPC222731
0.7207 Intermediate Similarity NPC305418
0.7207 Intermediate Similarity NPC473851
0.7207 Intermediate Similarity NPC191915
0.7207 Intermediate Similarity NPC217205
0.7207 Intermediate Similarity NPC131693
0.7203 Intermediate Similarity NPC207693
0.719 Intermediate Similarity NPC146563
0.7179 Intermediate Similarity NPC119628
0.7179 Intermediate Similarity NPC158051
0.7179 Intermediate Similarity NPC158367
0.7168 Intermediate Similarity NPC471241
0.7156 Intermediate Similarity NPC82955
0.7156 Intermediate Similarity NPC473472
0.7156 Intermediate Similarity NPC102725
0.7155 Intermediate Similarity NPC473406
0.7154 Intermediate Similarity NPC477252
0.7154 Intermediate Similarity NPC179429
0.7143 Intermediate Similarity NPC92196
0.7143 Intermediate Similarity NPC107962
0.7143 Intermediate Similarity NPC107188
0.7143 Intermediate Similarity NPC475351
0.7143 Intermediate Similarity NPC19400
0.7143 Intermediate Similarity NPC473610
0.7143 Intermediate Similarity NPC211354
0.7143 Intermediate Similarity NPC22709
0.7143 Intermediate Similarity NPC206003
0.7143 Intermediate Similarity NPC473727
0.7143 Intermediate Similarity NPC477494
0.7143 Intermediate Similarity NPC227879
0.7143 Intermediate Similarity NPC208333
0.7143 Intermediate Similarity NPC474399
0.7143 Intermediate Similarity NPC6295
0.7131 Intermediate Similarity NPC54395
0.7131 Intermediate Similarity NPC469821
0.7131 Intermediate Similarity NPC79193
0.713 Intermediate Similarity NPC472081
0.713 Intermediate Similarity NPC476839
0.713 Intermediate Similarity NPC108227
0.713 Intermediate Similarity NPC476512
0.713 Intermediate Similarity NPC475574
0.713 Intermediate Similarity NPC476838
0.712 Intermediate Similarity NPC108072
0.7119 Intermediate Similarity NPC138219
0.7119 Intermediate Similarity NPC40716
0.7119 Intermediate Similarity NPC126753
0.7119 Intermediate Similarity NPC475234
0.7119 Intermediate Similarity NPC475630
0.7111 Intermediate Similarity NPC180770
0.7111 Intermediate Similarity NPC302276
0.7111 Intermediate Similarity NPC265908
0.7107 Intermediate Similarity NPC474265
0.7107 Intermediate Similarity NPC145625
0.7107 Intermediate Similarity NPC477253
0.7107 Intermediate Similarity NPC210420
0.7099 Intermediate Similarity NPC139585
0.7094 Intermediate Similarity NPC475239
0.7091 Intermediate Similarity NPC223143
0.7091 Intermediate Similarity NPC473542
0.7091 Intermediate Similarity NPC279329
0.708 Intermediate Similarity NPC184617
0.708 Intermediate Similarity NPC232037
0.708 Intermediate Similarity NPC470864
0.708 Intermediate Similarity NPC475785
0.708 Intermediate Similarity NPC470866
0.708 Intermediate Similarity NPC116756
0.708 Intermediate Similarity NPC475643
0.708 Intermediate Similarity NPC128572
0.708 Intermediate Similarity NPC287483
0.708 Intermediate Similarity NPC470863

  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 NPC28224 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
0.7857 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6940 Discontinued
0.7478 Intermediate Similarity NPD6920 Discontinued
0.7297 Intermediate Similarity NPD7991 Discontinued
0.7273 Intermediate Similarity NPD8171 Discontinued
0.7217 Intermediate Similarity NPD8083 Approved
0.7217 Intermediate Similarity NPD8139 Approved
0.7217 Intermediate Similarity NPD8085 Approved
0.7217 Intermediate Similarity NPD8084 Approved
0.7217 Intermediate Similarity NPD8138 Approved
0.7217 Intermediate Similarity NPD8086 Approved
0.7217 Intermediate Similarity NPD8082 Approved
0.7203 Intermediate Similarity NPD6415 Discontinued
0.7155 Intermediate Similarity NPD8275 Approved
0.7155 Intermediate Similarity NPD8276 Approved
0.7094 Intermediate Similarity NPD8081 Approved
0.7049 Intermediate Similarity NPD8133 Approved
0.7034 Intermediate Similarity NPD8393 Approved
0.6975 Remote Similarity NPD8140 Approved
0.6917 Remote Similarity NPD8174 Phase 2
0.6897 Remote Similarity NPD8418 Phase 2
0.686 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6833 Remote Similarity NPD8307 Discontinued
0.6833 Remote Similarity NPD7646 Clinical (unspecified phase)
0.6791 Remote Similarity NPD8449 Approved
0.675 Remote Similarity NPD8040 Discontinued
0.6741 Remote Similarity NPD8450 Suspended
0.6694 Remote Similarity NPD6412 Phase 2
0.6667 Remote Similarity NPD8087 Discontinued
0.664 Remote Similarity NPD8298 Phase 2
0.6614 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6589 Remote Similarity NPD8347 Approved
0.6589 Remote Similarity NPD8345 Approved
0.6589 Remote Similarity NPD8346 Approved
0.6585 Remote Similarity NPD8306 Approved
0.6585 Remote Similarity NPD8305 Approved
0.6583 Remote Similarity NPD7912 Approved
0.6583 Remote Similarity NPD7986 Approved
0.6583 Remote Similarity NPD7987 Approved
0.6583 Remote Similarity NPD7911 Approved
0.6484 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6928 Phase 2
0.6449 Remote Similarity NPD6114 Approved
0.6449 Remote Similarity NPD6118 Approved
0.6449 Remote Similarity NPD6115 Approved
0.6449 Remote Similarity NPD6697 Approved
0.6439 Remote Similarity NPD8328 Phase 3
0.6423 Remote Similarity NPD7989 Approved
0.6423 Remote Similarity NPD7990 Approved
0.6412 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6412 Remote Similarity NPD6921 Approved
0.637 Remote Similarity NPD8337 Approved
0.637 Remote Similarity NPD8336 Approved
0.6364 Remote Similarity NPD8300 Approved
0.6364 Remote Similarity NPD8301 Approved
0.6355 Remote Similarity NPD6116 Phase 1
0.6346 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6346 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6299 Remote Similarity NPD8078 Approved
0.6299 Remote Similarity NPD8077 Approved
0.6283 Remote Similarity NPD8308 Discontinued
0.6279 Remote Similarity NPD7755 Approved
0.6279 Remote Similarity NPD7754 Approved
0.6262 Remote Similarity NPD6117 Approved
0.626 Remote Similarity NPD7518 Approved
0.626 Remote Similarity NPD7517 Approved
0.626 Remote Similarity NPD7519 Approved
0.6241 Remote Similarity NPD8080 Discontinued
0.6226 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6222 Remote Similarity NPD7507 Approved
0.6212 Remote Similarity NPD8377 Approved
0.6212 Remote Similarity NPD8294 Approved
0.6168 Remote Similarity NPD3703 Phase 2
0.6165 Remote Similarity NPD8296 Approved
0.6165 Remote Similarity NPD8380 Approved
0.6165 Remote Similarity NPD8335 Approved
0.6165 Remote Similarity NPD8379 Approved
0.6165 Remote Similarity NPD8033 Approved
0.6165 Remote Similarity NPD8378 Approved
0.6154 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8034 Phase 2
0.6154 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8035 Phase 2
0.6131 Remote Similarity NPD7736 Approved
0.6087 Remote Similarity NPD7319 Approved
0.6083 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6074 Remote Similarity NPD7122 Discontinued
0.6071 Remote Similarity NPD8338 Approved
0.6056 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6033 Remote Similarity NPD7920 Phase 3
0.6033 Remote Similarity NPD7919 Phase 3
0.6029 Remote Similarity NPD8299 Approved
0.6029 Remote Similarity NPD8341 Approved
0.6029 Remote Similarity NPD8340 Approved
0.6029 Remote Similarity NPD8342 Approved
0.6018 Remote Similarity NPD3669 Approved
0.6018 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6 Remote Similarity NPD6370 Approved
0.5986 Remote Similarity NPD8415 Approved
0.5985 Remote Similarity NPD8451 Approved
0.5984 Remote Similarity NPD8088 Phase 1
0.5984 Remote Similarity NPD6686 Approved
0.5982 Remote Similarity NPD1780 Approved
0.5982 Remote Similarity NPD1779 Approved
0.5952 Remote Similarity NPD7333 Discontinued
0.5943 Remote Similarity NPD4245 Approved
0.5943 Remote Similarity NPD4244 Approved
0.5943 Remote Similarity NPD4789 Approved
0.5942 Remote Similarity NPD8448 Approved
0.5942 Remote Similarity NPD8293 Discontinued
0.594 Remote Similarity NPD7328 Approved
0.594 Remote Similarity NPD7641 Discontinued
0.594 Remote Similarity NPD7327 Approved
0.5929 Remote Similarity NPD7751 Phase 1
0.5929 Remote Similarity NPD8391 Approved
0.5929 Remote Similarity NPD8390 Approved
0.5929 Remote Similarity NPD8392 Approved
0.5926 Remote Similarity NPD6909 Approved
0.5926 Remote Similarity NPD6908 Approved
0.5905 Remote Similarity NPD5360 Phase 3
0.5905 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5896 Remote Similarity NPD7516 Approved
0.5873 Remote Similarity NPD3710 Phase 2
0.5859 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5852 Remote Similarity NPD6054 Approved
0.5852 Remote Similarity NPD6059 Approved
0.5849 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5849 Remote Similarity NPD3698 Phase 2
0.578 Remote Similarity NPD1811 Approved
0.578 Remote Similarity NPD1810 Approved
0.5776 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5769 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5763 Remote Similarity NPD4264 Clinical (unspecified phase)
0.5741 Remote Similarity NPD6081 Approved
0.5741 Remote Similarity NPD5777 Approved
0.5734 Remote Similarity NPD6845 Suspended
0.5727 Remote Similarity NPD2257 Approved
0.5727 Remote Similarity NPD3702 Approved
0.5725 Remote Similarity NPD6067 Discontinued
0.5725 Remote Similarity NPD2690 Discontinued
0.5725 Remote Similarity NPD7642 Approved
0.5714 Remote Similarity NPD3671 Phase 1
0.5702 Remote Similarity NPD6399 Phase 3
0.5693 Remote Similarity NPD7503 Approved
0.5693 Remote Similarity NPD6016 Approved
0.5693 Remote Similarity NPD6015 Approved
0.5683 Remote Similarity NPD7492 Approved
0.5664 Remote Similarity NPD7155 Clinical (unspecified phase)
0.5658 Remote Similarity NPD7625 Phase 1
0.5652 Remote Similarity NPD882 Phase 2
0.5652 Remote Similarity NPD5988 Approved
0.5652 Remote Similarity NPD883 Phase 2
0.5645 Remote Similarity NPD7902 Approved
0.5643 Remote Similarity NPD6616 Approved
0.563 Remote Similarity NPD6009 Approved
0.5612 Remote Similarity NPD7604 Phase 2
0.561 Remote Similarity NPD7844 Discontinued
0.5603 Remote Similarity NPD7078 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