Structure

Physi-Chem Properties

Molecular Weight:  510.19
Volume:  487.686
LogP:  2.193
LogD:  1.461
LogS:  -4.884
# Rotatable Bonds:  0
TPSA:  125.43
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  8
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.483
Synthetic Accessibility Score:  7.552
Fsp3:  0.714
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:  -5.308
MDCK Permeability:  1.659655390540138e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.98
30% Bioavailability (F30%):  0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.919
Plasma Protein Binding (PPB):  62.436668395996094%
Volume Distribution (VD):  1.006
Pgp-substrate:  37.206546783447266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.98
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.745
CYP2C9-inhibitor:  0.035
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.081
CYP3A4-inhibitor:  0.729
CYP3A4-substrate:  0.921

ADMET: Excretion

Clearance (CL):  6.814
Half-life (T1/2):  0.424

ADMET: Toxicity

hERG Blockers:  0.185
Human Hepatotoxicity (H-HT):  0.129
Drug-inuced Liver Injury (DILI):  0.239
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.988
Maximum Recommended Daily Dose:  0.932
Skin Sensitization:  0.304
Carcinogencity:  0.922
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.918

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

  Natural Product: NPC264192

Natural Product ID:  NPC264192
Common Name*:   Physalin B
IUPAC Name:   n.a.
Synonyms:   NSC-287088
Standard InCHIKey:  HVTFEHJSUSPQBK-DNJDGUCCSA-N
Standard InCHI:  InChI=1S/C28H30O9/c1-23-11-18-25(3)28-19(23)20(30)27(37-28,34-12-16(23)21(31)35-18)15-8-7-13-5-4-6-17(29)24(13,2)14(15)9-10-26(28,33)22(32)36-25/h4,6-7,14-16,18-19,33H,5,8-12H2,1-3H3/t14-,15+,16-,18+,19-,23+,24-,25-,26-,27+,28-/m0/s1
SMILES:  O=C1O[C@@H]2C[C@@]3([C@H]1CO[C@@]14C(=O)[C@@H]3[C@@]3([C@@]2(C)OC(=O)[C@@]3(O)CC[C@H]2[C@H]4CC=C3[C@]2(C)C(=O)C=CC3)O1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504404
PubChem CID:   11613161
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001671] Physalins and derivatives

*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
NPO24001 Witheringia solanacea Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[16562828]
NPO1680 Physalis angulata Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[17580910]
NPO14304.1 Physalis alkekengi var. franchetii Varieties Solanaceae Eukaryota calyces Yilan, Heilongjiang Province, China 2004-SEP PMID[18348534]
NPO1680 Physalis angulata Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[21954931]
NPO1680 Physalis angulata Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[23270478]
NPO1680 Physalis angulata Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[25396337]
NPO1680 Physalis angulata Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[27295506]
NPO40397 Witheringia coccoloboides Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[7320739]
NPO14304.1 Physalis alkekengi var. franchetii Varieties Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14304.1 Physalis alkekengi var. franchetii Varieties Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24001 Witheringia solanacea Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1680 Physalis angulata Species Solanaceae 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
NPT858 Cell Line LNCaP Homo sapiens EC50 = 5.3 ug.mL-1 PMID[478671]
NPT91 Cell Line KB Homo sapiens EC50 = 3.0 ug.mL-1 PMID[478671]
NPT762 Cell Line A-431 Homo sapiens EC50 = 1.8 ug.mL-1 PMID[478671]
NPT81 Cell Line A549 Homo sapiens EC50 = 5.9 ug.mL-1 PMID[478671]
NPT180 Cell Line HCT-8 Homo sapiens EC50 = 1.5 ug.mL-1 PMID[478671]
NPT306 Cell Line PC-3 Homo sapiens EC50 = 0.9 ug.mL-1 PMID[478671]
NPT133 Cell Line ZR-75-1 Homo sapiens EC50 = 2.6 ug.mL-1 PMID[478671]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 840.0 nM PMID[478672]
NPT1896 Individual Protein Zinc finger protein GLI1 Homo sapiens IC50 = 620.0 nM PMID[478674]
NPT461 Cell Line PANC-1 Homo sapiens Selectivity Index = 3.0 n.a. PMID[478674]
NPT165 Cell Line HeLa Homo sapiens IC50 = 2000.0 nM PMID[478675]
NPT15 Cell Line Jurkat Homo sapiens Activity = 1.83 % PMID[478675]
NPT15 Cell Line Jurkat Homo sapiens Activity = 2.08 % PMID[478675]
NPT15 Cell Line Jurkat Homo sapiens Activity = 6.27 % PMID[478675]
NPT15 Cell Line Jurkat Homo sapiens Activity = 49.7 % PMID[478675]
NPT15 Cell Line Jurkat Homo sapiens Activity = 50.0 % PMID[478675]
NPT2601 Individual Protein NF-kappaB inhibitor alpha Homo sapiens Inhibition = 7.0 % PMID[478678]
NPT2601 Individual Protein NF-kappaB inhibitor alpha Homo sapiens IC50 = 37500.0 nM PMID[478678]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 1.3 ug.mL-1 PMID[478671]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 3.1 ug ml-1 PMID[478673]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 1.0 10'-2 ug/ml PMID[478673]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. T/C = 137.0 % PMID[478673]
NPT2 Others Unspecified Ratio IC50 = 2.0 n.a. PMID[478674]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2800.0 nM PMID[478676]
NPT27 Others Unspecified LC50 = 33900.0 nM PMID[478676]
NPT2 Others Unspecified Ratio LC50/IC50 = 12.3 n.a. PMID[478676]
NPT2 Others Unspecified FC = 19.0 n.a. PMID[478677]
NPT2 Others Unspecified IC50 = 6070.0 nM PMID[478678]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens IC50 = 1260.0 nM PMID[478680]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens IC50 > 200000.0 nM PMID[478680]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Kd = 45300.0 nM PMID[478680]

☑ 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 NPC264192 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
0.9508 High Similarity NPC254146
0.9508 High Similarity NPC100390
0.9508 High Similarity NPC6274
0.9508 High Similarity NPC254614
0.9508 High Similarity NPC33378
0.936 High Similarity NPC243014
0.935 High Similarity NPC102316
0.9274 High Similarity NPC168879
0.9262 High Similarity NPC188291
0.92 High Similarity NPC242486
0.92 High Similarity NPC15215
0.8678 High Similarity NPC17772
0.8607 High Similarity NPC469488
0.8607 High Similarity NPC470777
0.8525 High Similarity NPC204552
0.8525 High Similarity NPC188667
0.8525 High Similarity NPC297179
0.8468 Intermediate Similarity NPC102822
0.8468 Intermediate Similarity NPC477046
0.8443 Intermediate Similarity NPC97908
0.8443 Intermediate Similarity NPC470854
0.8443 Intermediate Similarity NPC122033
0.8443 Intermediate Similarity NPC474654
0.8443 Intermediate Similarity NPC287343
0.843 Intermediate Similarity NPC45218
0.843 Intermediate Similarity NPC143268
0.843 Intermediate Similarity NPC323821
0.843 Intermediate Similarity NPC268238
0.8413 Intermediate Similarity NPC24651
0.84 Intermediate Similarity NPC312833
0.8387 Intermediate Similarity NPC112038
0.8361 Intermediate Similarity NPC40632
0.8361 Intermediate Similarity NPC134869
0.8361 Intermediate Similarity NPC16081
0.8361 Intermediate Similarity NPC96312
0.8361 Intermediate Similarity NPC328374
0.8361 Intermediate Similarity NPC173686
0.8361 Intermediate Similarity NPC152199
0.8361 Intermediate Similarity NPC235539
0.8361 Intermediate Similarity NPC251236
0.8361 Intermediate Similarity NPC207217
0.8359 Intermediate Similarity NPC295220
0.8359 Intermediate Similarity NPC475636
0.8347 Intermediate Similarity NPC49451
0.8346 Intermediate Similarity NPC181999
0.8333 Intermediate Similarity NPC265557
0.8333 Intermediate Similarity NPC105926
0.8333 Intermediate Similarity NPC18945
0.8333 Intermediate Similarity NPC91693
0.8295 Intermediate Similarity NPC309096
0.8295 Intermediate Similarity NPC54614
0.8279 Intermediate Similarity NPC18547
0.8279 Intermediate Similarity NPC473798
0.8279 Intermediate Similarity NPC474906
0.8268 Intermediate Similarity NPC476729
0.8268 Intermediate Similarity NPC470922
0.8264 Intermediate Similarity NPC289312
0.8264 Intermediate Similarity NPC474516
0.8264 Intermediate Similarity NPC11252
0.825 Intermediate Similarity NPC474567
0.8226 Intermediate Similarity NPC470776
0.8203 Intermediate Similarity NPC87662
0.8197 Intermediate Similarity NPC208998
0.8197 Intermediate Similarity NPC320118
0.8197 Intermediate Similarity NPC7921
0.8195 Intermediate Similarity NPC471089
0.8195 Intermediate Similarity NPC141215
0.8195 Intermediate Similarity NPC190065
0.8189 Intermediate Similarity NPC227397
0.8189 Intermediate Similarity NPC67251
0.8182 Intermediate Similarity NPC201992
0.8175 Intermediate Similarity NPC470779
0.816 Intermediate Similarity NPC268958
0.814 Intermediate Similarity NPC476008
0.8134 Intermediate Similarity NPC596
0.8134 Intermediate Similarity NPC140045
0.8134 Intermediate Similarity NPC295885
0.812 Intermediate Similarity NPC262813
0.8115 Intermediate Similarity NPC205534
0.8095 Intermediate Similarity NPC107338
0.8095 Intermediate Similarity NPC109607
0.808 Intermediate Similarity NPC251310
0.808 Intermediate Similarity NPC106644
0.8065 Intermediate Similarity NPC270478
0.8062 Intermediate Similarity NPC225049
0.8062 Intermediate Similarity NPC285091
0.8062 Intermediate Similarity NPC477745
0.806 Intermediate Similarity NPC251998
0.8049 Intermediate Similarity NPC51978
0.8049 Intermediate Similarity NPC194273
0.8049 Intermediate Similarity NPC198539
0.8033 Intermediate Similarity NPC146945
0.8033 Intermediate Similarity NPC171888
0.8031 Intermediate Similarity NPC275675
0.8017 Intermediate Similarity NPC250018
0.8016 Intermediate Similarity NPC476529
0.8016 Intermediate Similarity NPC475775
0.8 Intermediate Similarity NPC477116
0.8 Intermediate Similarity NPC27999
0.8 Intermediate Similarity NPC470775
0.8 Intermediate Similarity NPC176513
0.7984 Intermediate Similarity NPC299849
0.7984 Intermediate Similarity NPC243354
0.7984 Intermediate Similarity NPC6615
0.7984 Intermediate Similarity NPC7850
0.7984 Intermediate Similarity NPC473255
0.7969 Intermediate Similarity NPC471965
0.7955 Intermediate Similarity NPC476855
0.7955 Intermediate Similarity NPC476863
0.7955 Intermediate Similarity NPC476852
0.7955 Intermediate Similarity NPC476862
0.7937 Intermediate Similarity NPC318751
0.7934 Intermediate Similarity NPC293850
0.7923 Intermediate Similarity NPC198714
0.792 Intermediate Similarity NPC213084
0.792 Intermediate Similarity NPC474046
0.792 Intermediate Similarity NPC470628
0.792 Intermediate Similarity NPC190185
0.792 Intermediate Similarity NPC259306
0.792 Intermediate Similarity NPC474734
0.7907 Intermediate Similarity NPC202666
0.7907 Intermediate Similarity NPC262199
0.7907 Intermediate Similarity NPC471964
0.7907 Intermediate Similarity NPC14617
0.7907 Intermediate Similarity NPC471961
0.7895 Intermediate Similarity NPC180902
0.7895 Intermediate Similarity NPC475139
0.7895 Intermediate Similarity NPC478154
0.7886 Intermediate Similarity NPC471243
0.7879 Intermediate Similarity NPC476851
0.7879 Intermediate Similarity NPC476854
0.7874 Intermediate Similarity NPC279143
0.7874 Intermediate Similarity NPC319570
0.7874 Intermediate Similarity NPC127530
0.7874 Intermediate Similarity NPC473920
0.7869 Intermediate Similarity NPC474242
0.7863 Intermediate Similarity NPC470882
0.7863 Intermediate Similarity NPC470780
0.7857 Intermediate Similarity NPC470778
0.7857 Intermediate Similarity NPC218970
0.7857 Intermediate Similarity NPC146432
0.7857 Intermediate Similarity NPC309433
0.7857 Intermediate Similarity NPC473590
0.7851 Intermediate Similarity NPC3316
0.7851 Intermediate Similarity NPC144854
0.7846 Intermediate Similarity NPC247315
0.7846 Intermediate Similarity NPC471962
0.7846 Intermediate Similarity NPC177820
0.7846 Intermediate Similarity NPC30188
0.7846 Intermediate Similarity NPC471963
0.784 Intermediate Similarity NPC117712
0.784 Intermediate Similarity NPC470919
0.784 Intermediate Similarity NPC247069
0.784 Intermediate Similarity NPC469877
0.7836 Intermediate Similarity NPC478151
0.7829 Intermediate Similarity NPC249848
0.7829 Intermediate Similarity NPC235438
0.7829 Intermediate Similarity NPC107966
0.7829 Intermediate Similarity NPC275343
0.7829 Intermediate Similarity NPC216866
0.7829 Intermediate Similarity NPC313528
0.7829 Intermediate Similarity NPC40775
0.7823 Intermediate Similarity NPC302146
0.782 Intermediate Similarity NPC478155
0.782 Intermediate Similarity NPC25998
0.7805 Intermediate Similarity NPC210005
0.7805 Intermediate Similarity NPC85391
0.7803 Intermediate Similarity NPC476859
0.7803 Intermediate Similarity NPC473888
0.7795 Intermediate Similarity NPC176005
0.7795 Intermediate Similarity NPC286347
0.7787 Intermediate Similarity NPC154608
0.7787 Intermediate Similarity NPC192813
0.7787 Intermediate Similarity NPC277017
0.7787 Intermediate Similarity NPC272576
0.7786 Intermediate Similarity NPC217901
0.7786 Intermediate Similarity NPC174367
0.7786 Intermediate Similarity NPC47113
0.7778 Intermediate Similarity NPC473548
0.7778 Intermediate Similarity NPC89929
0.7778 Intermediate Similarity NPC471136
0.7778 Intermediate Similarity NPC100017
0.7778 Intermediate Similarity NPC475154
0.7778 Intermediate Similarity NPC223356
0.7778 Intermediate Similarity NPC471137
0.7778 Intermediate Similarity NPC475500
0.7778 Intermediate Similarity NPC182266
0.7769 Intermediate Similarity NPC238005
0.7769 Intermediate Similarity NPC1980
0.7769 Intermediate Similarity NPC235405
0.7769 Intermediate Similarity NPC478066
0.7769 Intermediate Similarity NPC141196
0.7769 Intermediate Similarity NPC30735
0.7769 Intermediate Similarity NPC181357
0.7769 Intermediate Similarity NPC281148
0.7769 Intermediate Similarity NPC120724
0.7761 Intermediate Similarity NPC478153
0.7761 Intermediate Similarity NPC471855
0.7761 Intermediate Similarity NPC478152
0.7761 Intermediate Similarity NPC478150

  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 NPC264192 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
0.7984 Intermediate Similarity NPD7492 Approved
0.7953 Intermediate Similarity NPD6054 Approved
0.7939 Intermediate Similarity NPD7736 Approved
0.7923 Intermediate Similarity NPD6616 Approved
0.7907 Intermediate Similarity NPD8328 Phase 3
0.7891 Intermediate Similarity NPD6016 Approved
0.7891 Intermediate Similarity NPD6015 Approved
0.7863 Intermediate Similarity NPD7078 Approved
0.7829 Intermediate Similarity NPD5988 Approved
0.7829 Intermediate Similarity NPD6370 Approved
0.7812 Intermediate Similarity NPD6319 Approved
0.7674 Intermediate Similarity NPD6059 Approved
0.7594 Intermediate Similarity NPD8293 Discontinued
0.7578 Intermediate Similarity NPD6009 Approved
0.754 Intermediate Similarity NPD6882 Approved
0.7442 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD8297 Approved
0.736 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7319 Approved
0.7344 Intermediate Similarity NPD4632 Approved
0.7323 Intermediate Similarity NPD6650 Approved
0.7323 Intermediate Similarity NPD6649 Approved
0.7302 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD5697 Approved
0.7222 Intermediate Similarity NPD6881 Approved
0.7222 Intermediate Similarity NPD6899 Approved
0.7165 Intermediate Similarity NPD6013 Approved
0.7165 Intermediate Similarity NPD6012 Approved
0.7165 Intermediate Similarity NPD6373 Approved
0.7165 Intermediate Similarity NPD6014 Approved
0.7165 Intermediate Similarity NPD6372 Approved
0.7153 Intermediate Similarity NPD6033 Approved
0.7132 Intermediate Similarity NPD7507 Approved
0.7109 Intermediate Similarity NPD7290 Approved
0.7109 Intermediate Similarity NPD4634 Approved
0.7109 Intermediate Similarity NPD6883 Approved
0.7109 Intermediate Similarity NPD7102 Approved
0.709 Intermediate Similarity NPD5983 Phase 2
0.7087 Intermediate Similarity NPD7320 Approved
0.7087 Intermediate Similarity NPD6011 Approved
0.7063 Intermediate Similarity NPD7128 Approved
0.7063 Intermediate Similarity NPD6675 Approved
0.7063 Intermediate Similarity NPD6402 Approved
0.7063 Intermediate Similarity NPD5739 Approved
0.7054 Intermediate Similarity NPD6847 Approved
0.7054 Intermediate Similarity NPD6617 Approved
0.7054 Intermediate Similarity NPD8130 Phase 1
0.7054 Intermediate Similarity NPD6869 Approved
0.7008 Intermediate Similarity NPD5701 Approved
0.7008 Intermediate Similarity NPD6412 Phase 2
0.6985 Remote Similarity NPD7604 Phase 2
0.6963 Remote Similarity NPD8513 Phase 3
0.6963 Remote Similarity NPD8517 Approved
0.6963 Remote Similarity NPD8516 Approved
0.6963 Remote Similarity NPD8515 Approved
0.6953 Remote Similarity NPD6686 Approved
0.6929 Remote Similarity NPD6008 Approved
0.6917 Remote Similarity NPD7115 Discovery
0.6884 Remote Similarity NPD6336 Discontinued
0.6855 Remote Similarity NPD5696 Approved
0.6846 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6838 Remote Similarity NPD6921 Approved
0.6815 Remote Similarity NPD7516 Approved
0.6809 Remote Similarity NPD5956 Approved
0.6803 Remote Similarity NPD5282 Discontinued
0.68 Remote Similarity NPD5286 Approved
0.68 Remote Similarity NPD5285 Approved
0.68 Remote Similarity NPD4696 Approved
0.6769 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6761 Remote Similarity NPD7260 Phase 2
0.6748 Remote Similarity NPD5695 Phase 3
0.6741 Remote Similarity NPD7328 Approved
0.6741 Remote Similarity NPD7327 Approved
0.6723 Remote Similarity NPD3573 Approved
0.6716 Remote Similarity NPD6274 Approved
0.6715 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6693 Remote Similarity NPD5211 Phase 2
0.6693 Remote Similarity NPD5225 Approved
0.6693 Remote Similarity NPD5226 Approved
0.6693 Remote Similarity NPD4633 Approved
0.6693 Remote Similarity NPD5224 Approved
0.6691 Remote Similarity NPD7100 Approved
0.6691 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6317 Approved
0.6641 Remote Similarity NPD5174 Approved
0.6641 Remote Similarity NPD5175 Approved
0.664 Remote Similarity NPD4755 Approved
0.664 Remote Similarity NPD7902 Approved
0.6618 Remote Similarity NPD6314 Approved
0.6618 Remote Similarity NPD6335 Approved
0.6618 Remote Similarity NPD6313 Approved
0.6615 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6615 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6614 Remote Similarity NPD5223 Approved
0.6597 Remote Similarity NPD6845 Suspended
0.6597 Remote Similarity NPD8338 Approved
0.6596 Remote Similarity NPD8074 Phase 3
0.6594 Remote Similarity NPD8378 Approved
0.6594 Remote Similarity NPD8296 Approved
0.6594 Remote Similarity NPD8379 Approved
0.6594 Remote Similarity NPD8335 Approved
0.6594 Remote Similarity NPD8380 Approved
0.6594 Remote Similarity NPD7503 Approved
0.6589 Remote Similarity NPD5141 Approved
0.6587 Remote Similarity NPD4225 Approved
0.6565 Remote Similarity NPD4729 Approved
0.6565 Remote Similarity NPD4730 Approved
0.656 Remote Similarity NPD5220 Clinical (unspecified phase)
0.656 Remote Similarity NPD5222 Approved
0.656 Remote Similarity NPD5221 Approved
0.6541 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6535 Remote Similarity NPD4700 Approved
0.6532 Remote Similarity NPD7748 Approved
0.6531 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6522 Remote Similarity NPD8377 Approved
0.6522 Remote Similarity NPD8294 Approved
0.6508 Remote Similarity NPD6083 Phase 2
0.6508 Remote Similarity NPD6084 Phase 2
0.6508 Remote Similarity NPD5173 Approved
0.6504 Remote Similarity NPD6411 Approved
0.6484 Remote Similarity NPD1700 Approved
0.648 Remote Similarity NPD1698 Clinical (unspecified phase)
0.648 Remote Similarity NPD5210 Approved
0.648 Remote Similarity NPD4629 Approved
0.6475 Remote Similarity NPD8033 Approved
0.6471 Remote Similarity NPD6868 Approved
0.6466 Remote Similarity NPD5248 Approved
0.6466 Remote Similarity NPD5251 Approved
0.6466 Remote Similarity NPD5250 Approved
0.6466 Remote Similarity NPD5247 Approved
0.6466 Remote Similarity NPD5249 Phase 3
0.6444 Remote Similarity NPD8133 Approved
0.6429 Remote Similarity NPD4697 Phase 3
0.6412 Remote Similarity NPD4767 Approved
0.6412 Remote Similarity NPD4768 Approved
0.64 Remote Similarity NPD7901 Clinical (unspecified phase)
0.64 Remote Similarity NPD7900 Approved
0.6383 Remote Similarity NPD6067 Discontinued
0.6376 Remote Similarity NPD6334 Approved
0.6376 Remote Similarity NPD6333 Approved
0.6371 Remote Similarity NPD7515 Phase 2
0.6371 Remote Similarity NPD6079 Approved
0.6357 Remote Similarity NPD6909 Approved
0.6357 Remote Similarity NPD6908 Approved
0.6341 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6341 Remote Similarity NPD6101 Approved
0.632 Remote Similarity NPD6399 Phase 3
0.6319 Remote Similarity NPD8337 Approved
0.6319 Remote Similarity NPD8336 Approved
0.6316 Remote Similarity NPD5128 Approved
0.6296 Remote Similarity NPD5217 Approved
0.6296 Remote Similarity NPD5215 Approved
0.6296 Remote Similarity NPD5216 Approved
0.626 Remote Similarity NPD5737 Approved
0.626 Remote Similarity NPD6672 Approved
0.626 Remote Similarity NPD4754 Approved
0.625 Remote Similarity NPD6053 Discontinued
0.624 Remote Similarity NPD5694 Approved
0.624 Remote Similarity NPD5281 Approved
0.624 Remote Similarity NPD5284 Approved
0.623 Remote Similarity NPD3618 Phase 1
0.623 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6222 Remote Similarity NPD6371 Approved
0.6222 Remote Similarity NPD5135 Approved
0.6222 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6222 Remote Similarity NPD5169 Approved
0.622 Remote Similarity NPD6356 Clinical (unspecified phase)
0.621 Remote Similarity NPD5328 Approved
0.6207 Remote Similarity NPD8407 Phase 2
0.6202 Remote Similarity NPD7638 Approved
0.619 Remote Similarity NPD5779 Approved
0.619 Remote Similarity NPD5778 Approved
0.6176 Remote Similarity NPD5127 Approved
0.6176 Remote Similarity NPD7799 Discontinued
0.616 Remote Similarity NPD5207 Approved
0.616 Remote Similarity NPD5692 Phase 3
0.6154 Remote Similarity NPD7640 Approved
0.6154 Remote Similarity NPD7639 Approved
0.6148 Remote Similarity NPD1694 Approved
0.6127 Remote Similarity NPD8368 Discontinued
0.6111 Remote Similarity NPD6050 Approved
0.6107 Remote Similarity NPD5344 Discontinued
0.6099 Remote Similarity NPD4522 Approved
0.6098 Remote Similarity NPD5690 Phase 2
0.609 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6084 Remote Similarity NPD8080 Discontinued
0.608 Remote Similarity NPD4753 Phase 2
0.608 Remote Similarity NPD6904 Approved
0.608 Remote Similarity NPD6080 Approved
0.608 Remote Similarity NPD6673 Approved
0.6074 Remote Similarity NPD5168 Approved
0.6063 Remote Similarity NPD4202 Approved
0.6043 Remote Similarity NPD5167 Approved
0.6016 Remote Similarity NPD6001 Approved
0.6 Remote Similarity NPD6614 Approved
0.6 Remote Similarity NPD6903 Approved
0.6 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5984 Remote Similarity NPD8035 Phase 2
0.5984 Remote Similarity NPD5693 Phase 1

  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