Structure

Physi-Chem Properties

Molecular Weight:  470.34
Volume:  511.905
LogP:  5.445
LogD:  4.196
LogS:  -3.821
# Rotatable Bonds:  1
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.464
Synthetic Accessibility Score:  4.764
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.474
MDCK Permeability:  2.027051232289523e-05
Pgp-inhibitor:  0.264
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.067
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.505
Plasma Protein Binding (PPB):  91.60527801513672%
Volume Distribution (VD):  0.653
Pgp-substrate:  7.363980293273926%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.709
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.872
CYP2C9-inhibitor:  0.133
CYP2C9-substrate:  0.075
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.04
CYP3A4-inhibitor:  0.444
CYP3A4-substrate:  0.487

ADMET: Excretion

Clearance (CL):  2.764
Half-life (T1/2):  0.048

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.286
Drug-inuced Liver Injury (DILI):  0.009
AMES Toxicity:  0.034
Rat Oral Acute Toxicity:  0.359
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.048
Carcinogencity:  0.338
Eye Corrosion:  0.006
Eye Irritation:  0.024
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC4036

Natural Product ID:  NPC4036
Common Name*:   18Beta-Glycyrrhetic Acid
IUPAC Name:   (2S,4aS,6aR,6aS,6bR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms:   18Beta-Glycyrrhetic Acid
Standard InCHIKey:  MPDGHEJMBKOTSU-AWOGJAJBSA-N
Standard InCHI:  InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21?,22-,23+,26+,27-,28-,29+,30+/m0/s1
SMILES:  CC1(C)C2CC[C@]3(C)[C@H](C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(=O)O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL208873
PubChem CID:   9897771
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 13800.0 nM PMID[452115]

☑ 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 NPC4036 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
1.0 High Similarity NPC145067
1.0 High Similarity NPC158030
1.0 High Similarity NPC233455
1.0 High Similarity NPC65120
0.9884 High Similarity NPC214756
0.9884 High Similarity NPC272075
0.9884 High Similarity NPC295643
0.9659 High Similarity NPC139570
0.9659 High Similarity NPC148523
0.9651 High Similarity NPC291028
0.9647 High Similarity NPC182797
0.9647 High Similarity NPC52169
0.9551 High Similarity NPC98874
0.9545 High Similarity NPC74751
0.954 High Similarity NPC105189
0.954 High Similarity NPC474525
0.9535 High Similarity NPC225585
0.9535 High Similarity NPC234346
0.9535 High Similarity NPC127689
0.9535 High Similarity NPC121798
0.9535 High Similarity NPC263393
0.9535 High Similarity NPC59263
0.9535 High Similarity NPC274330
0.9535 High Similarity NPC293048
0.9535 High Similarity NPC270768
0.9535 High Similarity NPC143232
0.9535 High Similarity NPC290972
0.9535 High Similarity NPC61543
0.9535 High Similarity NPC25906
0.9535 High Similarity NPC198664
0.9535 High Similarity NPC64872
0.9535 High Similarity NPC130520
0.9529 High Similarity NPC130577
0.9529 High Similarity NPC98442
0.9529 High Similarity NPC293564
0.9529 High Similarity NPC88716
0.9529 High Similarity NPC142415
0.9529 High Similarity NPC68160
0.9529 High Similarity NPC307426
0.9529 High Similarity NPC102683
0.9529 High Similarity NPC51700
0.9529 High Similarity NPC171203
0.9529 High Similarity NPC242468
0.9529 High Similarity NPC18064
0.9425 High Similarity NPC120968
0.9425 High Similarity NPC470589
0.9425 High Similarity NPC227467
0.9425 High Similarity NPC210037
0.9425 High Similarity NPC477872
0.9425 High Similarity NPC111110
0.9425 High Similarity NPC18872
0.9425 High Similarity NPC7260
0.9425 High Similarity NPC273621
0.9425 High Similarity NPC46441
0.9425 High Similarity NPC290614
0.9425 High Similarity NPC126369
0.9425 High Similarity NPC193750
0.9425 High Similarity NPC130278
0.9419 High Similarity NPC246708
0.9419 High Similarity NPC470629
0.9419 High Similarity NPC290690
0.9419 High Similarity NPC473242
0.9419 High Similarity NPC17733
0.9419 High Similarity NPC40552
0.9419 High Similarity NPC474512
0.9419 High Similarity NPC181225
0.9412 High Similarity NPC72638
0.9341 High Similarity NPC471966
0.9326 High Similarity NPC474529
0.9318 High Similarity NPC235884
0.9318 High Similarity NPC472149
0.9318 High Similarity NPC25299
0.9318 High Similarity NPC6255
0.9318 High Similarity NPC282616
0.9318 High Similarity NPC52021
0.9318 High Similarity NPC84319
0.9318 High Similarity NPC38754
0.9318 High Similarity NPC187722
0.9318 High Similarity NPC155120
0.9318 High Similarity NPC228784
0.9318 High Similarity NPC471588
0.9318 High Similarity NPC288833
0.9318 High Similarity NPC306541
0.9318 High Similarity NPC324341
0.9318 High Similarity NPC71074
0.9318 High Similarity NPC300351
0.9318 High Similarity NPC966
0.931 High Similarity NPC474972
0.931 High Similarity NPC161751
0.931 High Similarity NPC470588
0.931 High Similarity NPC95246
0.9294 High Similarity NPC133954
0.9231 High Similarity NPC26413
0.9213 High Similarity NPC86368
0.9213 High Similarity NPC158059
0.9213 High Similarity NPC275809
0.9213 High Similarity NPC74855
0.9213 High Similarity NPC307335
0.9213 High Similarity NPC229281
0.9213 High Similarity NPC298554
0.9213 High Similarity NPC136313
0.9213 High Similarity NPC118519
0.9213 High Similarity NPC202728
0.9213 High Similarity NPC118490
0.9205 High Similarity NPC86372
0.9205 High Similarity NPC474728
0.9205 High Similarity NPC172361
0.9205 High Similarity NPC49320
0.9205 High Similarity NPC113989
0.9205 High Similarity NPC120840
0.9186 High Similarity NPC74363
0.9186 High Similarity NPC213412
0.9186 High Similarity NPC475862
0.9176 High Similarity NPC96095
0.9121 High Similarity NPC157113
0.9121 High Similarity NPC472806
0.9121 High Similarity NPC167193
0.9121 High Similarity NPC62516
0.9111 High Similarity NPC20235
0.9111 High Similarity NPC32407
0.9111 High Similarity NPC231063
0.9111 High Similarity NPC263548
0.9111 High Similarity NPC299996
0.9111 High Similarity NPC209868
0.9111 High Similarity NPC145667
0.9111 High Similarity NPC282395
0.9111 High Similarity NPC159365
0.9111 High Similarity NPC88116
0.9111 High Similarity NPC114159
0.9111 High Similarity NPC191412
0.9111 High Similarity NPC6818
0.9111 High Similarity NPC222047
0.9111 High Similarity NPC91010
0.9101 High Similarity NPC475708
0.9101 High Similarity NPC285184
0.9101 High Similarity NPC60755
0.9101 High Similarity NPC470590
0.9101 High Similarity NPC77099
0.9091 High Similarity NPC30522
0.9091 High Similarity NPC281524
0.9091 High Similarity NPC474686
0.908 High Similarity NPC158141
0.908 High Similarity NPC173089
0.908 High Similarity NPC73064
0.908 High Similarity NPC71507
0.9022 High Similarity NPC89225
0.9011 High Similarity NPC474727
0.9011 High Similarity NPC96916
0.9011 High Similarity NPC473240
0.9011 High Similarity NPC198245
0.9 High Similarity NPC49776
0.9 High Similarity NPC474806
0.9 High Similarity NPC474436
0.9 High Similarity NPC63118
0.9 High Similarity NPC133579
0.8977 High Similarity NPC230387
0.8977 High Similarity NPC1753
0.8977 High Similarity NPC474511
0.8977 High Similarity NPC472802
0.8966 High Similarity NPC73038
0.8966 High Similarity NPC158393
0.8966 High Similarity NPC477579
0.8966 High Similarity NPC235341
0.8966 High Similarity NPC56588
0.8966 High Similarity NPC95594
0.8953 High Similarity NPC180834
0.8953 High Similarity NPC171789
0.8913 High Similarity NPC132824
0.8913 High Similarity NPC158371
0.8913 High Similarity NPC327179
0.8913 High Similarity NPC19376
0.8913 High Similarity NPC173744
0.8913 High Similarity NPC230151
0.8913 High Similarity NPC305464
0.8913 High Similarity NPC25848
0.8913 High Similarity NPC73004
0.8913 High Similarity NPC476327
0.8913 High Similarity NPC116457
0.8913 High Similarity NPC259733
0.8913 High Similarity NPC204961
0.8913 High Similarity NPC307282
0.8913 High Similarity NPC476318
0.8913 High Similarity NPC207922
0.8913 High Similarity NPC201657
0.8901 High Similarity NPC80365
0.8901 High Similarity NPC60692
0.8901 High Similarity NPC296164
0.8901 High Similarity NPC23170
0.8901 High Similarity NPC78580
0.8901 High Similarity NPC188102
0.8901 High Similarity NPC148964
0.8901 High Similarity NPC23621
0.8901 High Similarity NPC184006
0.8901 High Similarity NPC87095
0.8889 High Similarity NPC301244
0.8876 High Similarity NPC69627
0.8876 High Similarity NPC477973
0.8864 High Similarity NPC162107
0.8864 High Similarity NPC46912
0.8842 High Similarity NPC476890

  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 NPC4036 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
1.0 High Similarity NPD7515 Phase 2
0.9545 High Similarity NPD7748 Approved
0.9231 High Similarity NPD7902 Approved
0.8901 High Similarity NPD7901 Clinical (unspecified phase)
0.8901 High Similarity NPD7900 Approved
0.8539 High Similarity NPD3618 Phase 1
0.8462 Intermediate Similarity NPD5328 Approved
0.8427 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD6079 Approved
0.8261 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD7645 Phase 2
0.8152 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8111 Intermediate Similarity NPD3133 Approved
0.8111 Intermediate Similarity NPD3666 Approved
0.8111 Intermediate Similarity NPD3665 Phase 1
0.8111 Intermediate Similarity NPD4786 Approved
0.809 Intermediate Similarity NPD3667 Approved
0.802 Intermediate Similarity NPD6675 Approved
0.802 Intermediate Similarity NPD5739 Approved
0.802 Intermediate Similarity NPD6402 Approved
0.802 Intermediate Similarity NPD7128 Approved
0.8 Intermediate Similarity NPD4202 Approved
0.8 Intermediate Similarity NPD6399 Phase 3
0.7959 Intermediate Similarity NPD7638 Approved
0.7938 Intermediate Similarity NPD5221 Approved
0.7938 Intermediate Similarity NPD5222 Approved
0.7938 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7938 Intermediate Similarity NPD4697 Phase 3
0.7935 Intermediate Similarity NPD6684 Approved
0.7935 Intermediate Similarity NPD7146 Approved
0.7935 Intermediate Similarity NPD7521 Approved
0.7935 Intermediate Similarity NPD5330 Approved
0.7935 Intermediate Similarity NPD6409 Approved
0.7935 Intermediate Similarity NPD7334 Approved
0.7895 Intermediate Similarity NPD8034 Phase 2
0.7895 Intermediate Similarity NPD8035 Phase 2
0.7879 Intermediate Similarity NPD7640 Approved
0.7879 Intermediate Similarity NPD7639 Approved
0.7864 Intermediate Similarity NPD6899 Approved
0.7864 Intermediate Similarity NPD6881 Approved
0.7864 Intermediate Similarity NPD7320 Approved
0.7857 Intermediate Similarity NPD6083 Phase 2
0.7857 Intermediate Similarity NPD4755 Approved
0.7857 Intermediate Similarity NPD5173 Approved
0.7857 Intermediate Similarity NPD6084 Phase 2
0.7849 Intermediate Similarity NPD3573 Approved
0.7788 Intermediate Similarity NPD6372 Approved
0.7788 Intermediate Similarity NPD6373 Approved
0.7767 Intermediate Similarity NPD5697 Approved
0.7767 Intermediate Similarity NPD5701 Approved
0.7766 Intermediate Similarity NPD5737 Approved
0.7766 Intermediate Similarity NPD6672 Approved
0.7766 Intermediate Similarity NPD6903 Approved
0.7755 Intermediate Similarity NPD7614 Phase 1
0.7714 Intermediate Similarity NPD6883 Approved
0.7714 Intermediate Similarity NPD7102 Approved
0.7714 Intermediate Similarity NPD7290 Approved
0.77 Intermediate Similarity NPD5286 Approved
0.77 Intermediate Similarity NPD4700 Approved
0.77 Intermediate Similarity NPD4696 Approved
0.77 Intermediate Similarity NPD5285 Approved
0.7692 Intermediate Similarity NPD6011 Approved
0.7684 Intermediate Similarity NPD4753 Phase 2
0.7667 Intermediate Similarity NPD4695 Discontinued
0.7642 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD8130 Phase 1
0.7642 Intermediate Similarity NPD6650 Approved
0.7642 Intermediate Similarity NPD6617 Approved
0.7642 Intermediate Similarity NPD6869 Approved
0.7642 Intermediate Similarity NPD6847 Approved
0.7642 Intermediate Similarity NPD6649 Approved
0.7624 Intermediate Similarity NPD5223 Approved
0.7619 Intermediate Similarity NPD6012 Approved
0.7619 Intermediate Similarity NPD6013 Approved
0.7619 Intermediate Similarity NPD6014 Approved
0.757 Intermediate Similarity NPD8297 Approved
0.757 Intermediate Similarity NPD6882 Approved
0.7553 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD5279 Phase 3
0.7549 Intermediate Similarity NPD4633 Approved
0.7549 Intermediate Similarity NPD5226 Approved
0.7549 Intermediate Similarity NPD5224 Approved
0.7549 Intermediate Similarity NPD5211 Phase 2
0.7549 Intermediate Similarity NPD5225 Approved
0.7527 Intermediate Similarity NPD3668 Phase 3
0.7522 Intermediate Similarity NPD8328 Phase 3
0.75 Intermediate Similarity NPD4221 Approved
0.75 Intermediate Similarity NPD4223 Phase 3
0.7476 Intermediate Similarity NPD5174 Approved
0.7476 Intermediate Similarity NPD4754 Approved
0.7476 Intermediate Similarity NPD5175 Approved
0.7475 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD5695 Phase 3
0.7473 Intermediate Similarity NPD7525 Registered
0.7455 Intermediate Similarity NPD7115 Discovery
0.7447 Intermediate Similarity NPD5329 Approved
0.7426 Intermediate Similarity NPD5696 Approved
0.7416 Intermediate Similarity NPD6117 Approved
0.7404 Intermediate Similarity NPD5141 Approved
0.74 Intermediate Similarity NPD7732 Phase 3
0.7364 Intermediate Similarity NPD6868 Approved
0.7347 Intermediate Similarity NPD5284 Approved
0.7347 Intermediate Similarity NPD6411 Approved
0.7347 Intermediate Similarity NPD5281 Approved
0.734 Intermediate Similarity NPD4197 Approved
0.7339 Intermediate Similarity NPD4632 Approved
0.7333 Intermediate Similarity NPD4767 Approved
0.7333 Intermediate Similarity NPD6116 Phase 1
0.7333 Intermediate Similarity NPD4768 Approved
0.732 Intermediate Similarity NPD6080 Approved
0.732 Intermediate Similarity NPD6904 Approved
0.732 Intermediate Similarity NPD6673 Approved
0.73 Intermediate Similarity NPD4629 Approved
0.73 Intermediate Similarity NPD5210 Approved
0.729 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD6412 Phase 2
0.7253 Intermediate Similarity NPD6115 Approved
0.7253 Intermediate Similarity NPD6118 Approved
0.7253 Intermediate Similarity NPD6114 Approved
0.7253 Intermediate Similarity NPD3617 Approved
0.7253 Intermediate Similarity NPD6697 Approved
0.7234 Intermediate Similarity NPD4788 Approved
0.7232 Intermediate Similarity NPD6335 Approved
0.7212 Intermediate Similarity NPD7632 Discontinued
0.7207 Intermediate Similarity NPD6274 Approved
0.7196 Intermediate Similarity NPD5168 Approved
0.7196 Intermediate Similarity NPD4729 Approved
0.7196 Intermediate Similarity NPD4730 Approved
0.7196 Intermediate Similarity NPD5128 Approved
0.7191 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4623 Approved
0.7188 Intermediate Similarity NPD4688 Approved
0.7188 Intermediate Similarity NPD4519 Discontinued
0.7188 Intermediate Similarity NPD4693 Phase 3
0.7188 Intermediate Similarity NPD4690 Approved
0.7188 Intermediate Similarity NPD4138 Approved
0.7188 Intermediate Similarity NPD4689 Approved
0.7188 Intermediate Similarity NPD5205 Approved
0.717 Intermediate Similarity NPD6008 Approved
0.7168 Intermediate Similarity NPD7100 Approved
0.7168 Intermediate Similarity NPD7101 Approved
0.7143 Intermediate Similarity NPD6317 Approved
0.7143 Intermediate Similarity NPD6101 Approved
0.7143 Intermediate Similarity NPD6009 Approved
0.7143 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7339 Approved
0.7111 Intermediate Similarity NPD6942 Approved
0.7097 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD4225 Approved
0.7083 Intermediate Similarity NPD1694 Approved
0.708 Intermediate Similarity NPD6314 Approved
0.708 Intermediate Similarity NPD6313 Approved
0.7064 Intermediate Similarity NPD5169 Approved
0.7064 Intermediate Similarity NPD5250 Approved
0.7064 Intermediate Similarity NPD5249 Phase 3
0.7064 Intermediate Similarity NPD5251 Approved
0.7064 Intermediate Similarity NPD5135 Approved
0.7064 Intermediate Similarity NPD4634 Approved
0.7064 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5247 Approved
0.7064 Intermediate Similarity NPD5248 Approved
0.7043 Intermediate Similarity NPD6908 Approved
0.7043 Intermediate Similarity NPD6909 Approved
0.7041 Intermediate Similarity NPD5208 Approved
0.7033 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6001 Approved
0.701 Intermediate Similarity NPD6098 Approved
0.701 Intermediate Similarity NPD5690 Phase 2
0.701 Intermediate Similarity NPD5280 Approved
0.701 Intermediate Similarity NPD4694 Approved
0.7 Intermediate Similarity NPD5215 Approved
0.7 Intermediate Similarity NPD5216 Approved
0.7 Intermediate Similarity NPD6050 Approved
0.7 Intermediate Similarity NPD5127 Approved
0.7 Intermediate Similarity NPD5693 Phase 1
0.7 Intermediate Similarity NPD5217 Approved
0.6991 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6975 Remote Similarity NPD7736 Approved
0.6972 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6319 Approved
0.6932 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4137 Phase 3
0.6932 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7604 Phase 2
0.69 Remote Similarity NPD5692 Phase 3
0.6897 Remote Similarity NPD5983 Phase 2
0.6897 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6881 Remote Similarity NPD6686 Approved
0.6864 Remote Similarity NPD7492 Approved
0.6854 Remote Similarity NPD4747 Approved
0.6854 Remote Similarity NPD4691 Approved
0.6832 Remote Similarity NPD5694 Approved
0.6814 Remote Similarity NPD5167 Approved
0.681 Remote Similarity NPD6054 Approved
0.681 Remote Similarity NPD6059 Approved
0.6809 Remote Similarity NPD4195 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