Structure

Physi-Chem Properties

Molecular Weight:  632.41
Volume:  683.343
LogP:  7.594
LogD:  5.951
LogS:  -5.257
# Rotatable Bonds:  7
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.185
Synthetic Accessibility Score:  4.907
Fsp3:  0.7
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.359
MDCK Permeability:  2.3298920496017672e-05
Pgp-inhibitor:  0.064
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.12
30% Bioavailability (F30%):  0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  99.19063568115234%
Volume Distribution (VD):  0.536
Pgp-substrate:  3.38832950592041%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.811
CYP2C19-inhibitor:  0.136
CYP2C19-substrate:  0.889
CYP2C9-inhibitor:  0.141
CYP2C9-substrate:  0.96
CYP2D6-inhibitor:  0.1
CYP2D6-substrate:  0.862
CYP3A4-inhibitor:  0.288
CYP3A4-substrate:  0.404

ADMET: Excretion

Clearance (CL):  2.157
Half-life (T1/2):  0.2

ADMET: Toxicity

hERG Blockers:  0.331
Human Hepatotoxicity (H-HT):  0.364
Drug-inuced Liver Injury (DILI):  0.008
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.079
Maximum Recommended Daily Dose:  0.922
Skin Sensitization:  0.896
Carcinogencity:  0.009
Eye Corrosion:  0.015
Eye Irritation:  0.09
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: NPC105942

Natural Product ID:  NPC105942
Common Name*:   3Beta-E-Feruloylbetulinic Acid
IUPAC Name:   (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:   3Beta-E-Feruloylbetulinic Acid
Standard InCHIKey:  UXUVZTGGSMRNDQ-YMUSRRSASA-N
Standard InCHI:  InChI=1S/C40H56O6/c1-24(2)26-15-20-40(35(43)44)22-21-38(6)27(34(26)40)11-13-31-37(5)18-17-32(36(3,4)30(37)16-19-39(31,38)7)46-33(42)14-10-25-9-12-28(41)29(23-25)45-8/h9-10,12,14,23,26-27,30-32,34,41H,1,11,13,15-22H2,2-8H3,(H,43,44)/b14-10+/t26-,27+,30-,31+,32-,34+,37-,38+,39+,40-/m0/s1
SMILES:  C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)/C=C/c3ccc(c(c3)OC)O)[C@@H]12)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451046
PubChem CID:   636595
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
NPO18999 Strychnos vanprukii Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[15217281]
NPO19887 Ceriops tagal Species Rhizophoraceae Eukaryota fruits n.a. n.a. PMID[16378377]
NPO19887 Ceriops tagal Species Rhizophoraceae Eukaryota stems and twigs mangrove wetlands of Hainan Island, China 2002-JUL PMID[20886837]
NPO19887 Ceriops tagal Species Rhizophoraceae Eukaryota stems and twigs the mangrove wetlands of Hainan Island, China 2002-JUL PMID[20886837]
NPO40939 Syzygium corticosum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[30057155]
NPO18999 Strychnos vanprukii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19887 Ceriops tagal Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18999 Strychnos vanprukii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19887 Ceriops tagal Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18999 Strychnos vanprukii Species Loganiaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 3.8 ug.mL-1 PMID[546545]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 1.8 ug.mL-1 PMID[546545]
NPT315 Cell Line CEM-SS Homo sapiens CC50 < 1600.0 nM PMID[546546]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 8.5 uM PMID[546546]
NPT1851 Cell Line Col2 Homo sapiens ED50 = 5.4 uM PMID[546546]
NPT91 Cell Line KB Homo sapiens ED50 = 2.5 uM PMID[546546]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 3.2 uM PMID[546546]
NPT737 Cell Line HUVEC Homo sapiens ED50 = 9.5 uM PMID[546546]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 3.8 uM PMID[546546]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10000.0 nM PMID[546547]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 10000.0 nM PMID[546547]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 510.0 nM PMID[546547]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3.0 ug.mL-1 PMID[546545]
NPT27 Others Unspecified CC50 = 13400.0 nM PMID[546546]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 5100.0 nM PMID[546546]
NPT2 Others Unspecified Ratio CC50/IC50 = 3.0 n.a. PMID[546546]
NPT721 Individual Protein Nuclear factor NF-kappa-B p65 subunit Homo sapiens IC50 = 5400.0 nM PMID[546547]

☑ 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 NPC105942 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 NPC205392
0.9592 High Similarity NPC118033
0.9527 High Similarity NPC473773
0.9527 High Similarity NPC475579
0.9517 High Similarity NPC66894
0.9517 High Similarity NPC8102
0.9459 High Similarity NPC475454
0.9459 High Similarity NPC475311
0.9459 High Similarity NPC473680
0.9459 High Similarity NPC473579
0.9448 High Similarity NPC19862
0.9448 High Similarity NPC235195
0.9388 High Similarity NPC96930
0.9388 High Similarity NPC32017
0.9324 High Similarity NPC292206
0.9324 High Similarity NPC298647
0.9324 High Similarity NPC273358
0.9315 High Similarity NPC280717
0.9315 High Similarity NPC307205
0.9315 High Similarity NPC271607
0.9295 High Similarity NPC200726
0.9262 High Similarity NPC208785
0.9262 High Similarity NPC470619
0.9262 High Similarity NPC470618
0.9262 High Similarity NPC145527
0.9236 High Similarity NPC177362
0.9178 High Similarity NPC252133
0.9178 High Similarity NPC469447
0.9178 High Similarity NPC477873
0.9177 High Similarity NPC266545
0.9177 High Similarity NPC202428
0.9172 High Similarity NPC473612
0.911 High Similarity NPC35212
0.9054 High Similarity NPC53520
0.9048 High Similarity NPC310621
0.9034 High Similarity NPC248287
0.9034 High Similarity NPC234548
0.8912 High Similarity NPC304110
0.8912 High Similarity NPC27518
0.8904 High Similarity NPC132723
0.8904 High Similarity NPC76032
0.8859 High Similarity NPC26045
0.8792 High Similarity NPC235557
0.8776 High Similarity NPC182249
0.8733 High Similarity NPC25491
0.8716 High Similarity NPC271494
0.8716 High Similarity NPC155192
0.8716 High Similarity NPC473591
0.8707 High Similarity NPC471152
0.8699 High Similarity NPC173569
0.8699 High Similarity NPC477874
0.8658 High Similarity NPC29599
0.865 High Similarity NPC472803
0.8639 High Similarity NPC249817
0.863 High Similarity NPC11266
0.8598 High Similarity NPC469775
0.8598 High Similarity NPC469774
0.8598 High Similarity NPC469777
0.8598 High Similarity NPC469772
0.8598 High Similarity NPC100925
0.8598 High Similarity NPC469773
0.8598 High Similarity NPC135334
0.8598 High Similarity NPC32723
0.8598 High Similarity NPC469776
0.8598 High Similarity NPC469778
0.8598 High Similarity NPC295941
0.8591 High Similarity NPC470616
0.8591 High Similarity NPC470617
0.8581 High Similarity NPC198621
0.8581 High Similarity NPC22676
0.8581 High Similarity NPC216940
0.8581 High Similarity NPC475482
0.8571 High Similarity NPC279442
0.8571 High Similarity NPC252343
0.8571 High Similarity NPC43353
0.8528 High Similarity NPC286809
0.8523 High Similarity NPC139243
0.8523 High Similarity NPC116742
0.8514 High Similarity NPC90431
0.8487 Intermediate Similarity NPC471876
0.8477 Intermediate Similarity NPC472410
0.8467 Intermediate Similarity NPC106055
0.8467 Intermediate Similarity NPC110699
0.8462 Intermediate Similarity NPC178048
0.8435 Intermediate Similarity NPC475468
0.8418 Intermediate Similarity NPC62051
0.8414 Intermediate Similarity NPC30174
0.8411 Intermediate Similarity NPC172311
0.8408 Intermediate Similarity NPC124842
0.8397 Intermediate Similarity NPC261322
0.8397 Intermediate Similarity NPC327962
0.8389 Intermediate Similarity NPC476699
0.8378 Intermediate Similarity NPC4982
0.8378 Intermediate Similarity NPC5310
0.8378 Intermediate Similarity NPC68779
0.8378 Intermediate Similarity NPC300776
0.8378 Intermediate Similarity NPC471110
0.8378 Intermediate Similarity NPC176814
0.8366 Intermediate Similarity NPC209085
0.8366 Intermediate Similarity NPC224884
0.8344 Intermediate Similarity NPC100420
0.8333 Intermediate Similarity NPC216916
0.8323 Intermediate Similarity NPC472937
0.8323 Intermediate Similarity NPC475197
0.8323 Intermediate Similarity NPC472936
0.8323 Intermediate Similarity NPC472938
0.8323 Intermediate Similarity NPC473467
0.8311 Intermediate Similarity NPC475457
0.8311 Intermediate Similarity NPC18982
0.8311 Intermediate Similarity NPC475627
0.8311 Intermediate Similarity NPC475346
0.8289 Intermediate Similarity NPC78987
0.8289 Intermediate Similarity NPC472801
0.8289 Intermediate Similarity NPC82336
0.8288 Intermediate Similarity NPC475138
0.8288 Intermediate Similarity NPC86257
0.8267 Intermediate Similarity NPC120852
0.8239 Intermediate Similarity NPC115203
0.8232 Intermediate Similarity NPC45943
0.8228 Intermediate Similarity NPC261659
0.8224 Intermediate Similarity NPC471875
0.8221 Intermediate Similarity NPC266365
0.8217 Intermediate Similarity NPC253591
0.8217 Intermediate Similarity NPC477206
0.8188 Intermediate Similarity NPC476282
0.8187 Intermediate Similarity NPC305710
0.8182 Intermediate Similarity NPC169214
0.8182 Intermediate Similarity NPC229218
0.8182 Intermediate Similarity NPC141817
0.8182 Intermediate Similarity NPC176030
0.8182 Intermediate Similarity NPC192597
0.8176 Intermediate Similarity NPC476434
0.8176 Intermediate Similarity NPC267091
0.8171 Intermediate Similarity NPC140346
0.817 Intermediate Similarity NPC100675
0.817 Intermediate Similarity NPC470035
0.8165 Intermediate Similarity NPC237441
0.8165 Intermediate Similarity NPC142654
0.8165 Intermediate Similarity NPC472939
0.8163 Intermediate Similarity NPC83062
0.816 Intermediate Similarity NPC185617
0.8153 Intermediate Similarity NPC477483
0.8153 Intermediate Similarity NPC470757
0.8153 Intermediate Similarity NPC325032
0.8141 Intermediate Similarity NPC189054
0.814 Intermediate Similarity NPC473776
0.814 Intermediate Similarity NPC473205
0.8138 Intermediate Similarity NPC137416
0.8138 Intermediate Similarity NPC280767
0.8137 Intermediate Similarity NPC472807
0.8133 Intermediate Similarity NPC471913
0.8129 Intermediate Similarity NPC469615
0.8129 Intermediate Similarity NPC474599
0.8129 Intermediate Similarity NPC477207
0.8125 Intermediate Similarity NPC65591
0.8125 Intermediate Similarity NPC178574
0.8121 Intermediate Similarity NPC25889
0.8121 Intermediate Similarity NPC321502
0.8117 Intermediate Similarity NPC67467
0.8113 Intermediate Similarity NPC243891
0.8113 Intermediate Similarity NPC119252
0.8105 Intermediate Similarity NPC79372
0.8105 Intermediate Similarity NPC288452
0.8105 Intermediate Similarity NPC289690
0.8098 Intermediate Similarity NPC179914
0.8095 Intermediate Similarity NPC180768
0.8092 Intermediate Similarity NPC281780
0.8089 Intermediate Similarity NPC58752
0.8089 Intermediate Similarity NPC39361
0.8086 Intermediate Similarity NPC213401
0.8082 Intermediate Similarity NPC213552
0.8082 Intermediate Similarity NPC120225
0.8079 Intermediate Similarity NPC113295
0.8077 Intermediate Similarity NPC309169
0.8077 Intermediate Similarity NPC469683
0.8077 Intermediate Similarity NPC196941
0.8077 Intermediate Similarity NPC91694
0.8077 Intermediate Similarity NPC300603
0.8075 Intermediate Similarity NPC469888
0.8069 Intermediate Similarity NPC20443
0.8069 Intermediate Similarity NPC60517
0.8069 Intermediate Similarity NPC146886
0.8065 Intermediate Similarity NPC470273
0.8061 Intermediate Similarity NPC473445
0.8059 Intermediate Similarity NPC475244
0.8054 Intermediate Similarity NPC243305
0.8052 Intermediate Similarity NPC282291
0.8052 Intermediate Similarity NPC166137
0.8041 Intermediate Similarity NPC241354
0.8041 Intermediate Similarity NPC304622
0.8039 Intermediate Similarity NPC265335
0.8039 Intermediate Similarity NPC284409
0.8038 Intermediate Similarity NPC102934
0.8038 Intermediate Similarity NPC252402
0.8038 Intermediate Similarity NPC236166
0.8038 Intermediate Similarity NPC52692
0.8038 Intermediate Similarity NPC1580
0.8037 Intermediate Similarity NPC471878
0.8037 Intermediate Similarity NPC143328
0.8037 Intermediate Similarity NPC268602

  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 NPC105942 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
0.898 High Similarity NPD8166 Discontinued
0.8797 High Similarity NPD8127 Discontinued
0.8205 Intermediate Similarity NPD6273 Approved
0.8121 Intermediate Similarity NPD3620 Phase 2
0.8121 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD4110 Phase 3
0.8117 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD7458 Discontinued
0.8023 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7003 Approved
0.8 Intermediate Similarity NPD7028 Phase 2
0.7933 Intermediate Similarity NPD8032 Phase 2
0.7933 Intermediate Similarity NPD6663 Approved
0.7905 Intermediate Similarity NPD5736 Approved
0.7886 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD6234 Discontinued
0.787 Intermediate Similarity NPD7228 Approved
0.7829 Intermediate Similarity NPD6355 Discontinued
0.7763 Intermediate Similarity NPD4140 Approved
0.7688 Intermediate Similarity NPD7685 Pre-registration
0.7683 Intermediate Similarity NPD37 Approved
0.7658 Intermediate Similarity NPD4628 Phase 3
0.7651 Intermediate Similarity NPD4965 Approved
0.7651 Intermediate Similarity NPD4966 Approved
0.7651 Intermediate Similarity NPD4967 Phase 2
0.7635 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD5762 Approved
0.758 Intermediate Similarity NPD5763 Approved
0.7574 Intermediate Similarity NPD7199 Phase 2
0.7566 Intermediate Similarity NPD7095 Approved
0.7545 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD4060 Phase 1
0.7516 Intermediate Similarity NPD6798 Discontinued
0.7514 Intermediate Similarity NPD5844 Phase 1
0.75 Intermediate Similarity NPD7097 Phase 1
0.7485 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD5735 Approved
0.7483 Intermediate Similarity NPD3019 Approved
0.7469 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD8313 Approved
0.7401 Intermediate Similarity NPD8312 Approved
0.74 Intermediate Similarity NPD5327 Phase 3
0.7399 Intermediate Similarity NPD7473 Discontinued
0.7396 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7833 Phase 2
0.7396 Intermediate Similarity NPD7831 Phase 2
0.7394 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7240 Approved
0.7372 Intermediate Similarity NPD3657 Discovery
0.7365 Intermediate Similarity NPD2932 Approved
0.7351 Intermediate Similarity NPD1283 Approved
0.733 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD6232 Discontinued
0.7325 Intermediate Similarity NPD6353 Approved
0.7325 Intermediate Similarity NPD6653 Approved
0.732 Intermediate Similarity NPD9494 Approved
0.7296 Intermediate Similarity NPD2438 Suspended
0.7296 Intermediate Similarity NPD2935 Discontinued
0.7284 Intermediate Similarity NPD6190 Approved
0.7262 Intermediate Similarity NPD1934 Approved
0.7255 Intermediate Similarity NPD4624 Approved
0.725 Intermediate Similarity NPD7266 Discontinued
0.7248 Intermediate Similarity NPD4626 Approved
0.7244 Intermediate Similarity NPD6233 Phase 2
0.7241 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6166 Phase 2
0.7241 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD7236 Approved
0.7235 Intermediate Similarity NPD7768 Phase 2
0.7219 Intermediate Similarity NPD8455 Phase 2
0.7219 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD6873 Phase 2
0.7202 Intermediate Similarity NPD6677 Suspended
0.7197 Intermediate Similarity NPD2979 Phase 3
0.7196 Intermediate Similarity NPD7497 Discontinued
0.719 Intermediate Similarity NPD2797 Approved
0.7181 Intermediate Similarity NPD5691 Approved
0.7175 Intermediate Similarity NPD7074 Phase 3
0.7167 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD5536 Phase 2
0.716 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6674 Discontinued
0.7152 Intermediate Similarity NPD3092 Approved
0.7152 Intermediate Similarity NPD1281 Approved
0.7152 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5647 Approved
0.7135 Intermediate Similarity NPD3882 Suspended
0.7125 Intermediate Similarity NPD2799 Discontinued
0.7124 Intermediate Similarity NPD1876 Approved
0.7123 Intermediate Similarity NPD5283 Phase 1
0.712 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7054 Approved
0.7118 Intermediate Similarity NPD1465 Phase 2
0.7118 Intermediate Similarity NPD7819 Suspended
0.7115 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD3027 Phase 3
0.7114 Intermediate Similarity NPD3091 Approved
0.7105 Intermediate Similarity NPD7680 Approved
0.7103 Intermediate Similarity NPD228 Approved
0.7099 Intermediate Similarity NPD5958 Discontinued
0.7099 Intermediate Similarity NPD4534 Discontinued
0.7093 Intermediate Similarity NPD7075 Discontinued
0.7088 Intermediate Similarity NPD8434 Phase 2
0.7086 Intermediate Similarity NPD3026 Approved
0.7086 Intermediate Similarity NPD3023 Approved
0.7083 Intermediate Similarity NPD3455 Phase 2
0.7079 Intermediate Similarity NPD7472 Approved
0.7078 Intermediate Similarity NPD3094 Phase 2
0.7074 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3268 Approved
0.707 Intermediate Similarity NPD3764 Approved
0.7067 Intermediate Similarity NPD3024 Approved
0.7067 Intermediate Similarity NPD3025 Approved
0.7066 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD2488 Approved
0.7065 Intermediate Similarity NPD2490 Approved
0.7062 Intermediate Similarity NPD3818 Discontinued
0.7048 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD447 Suspended
0.7037 Intermediate Similarity NPD2346 Discontinued
0.7025 Intermediate Similarity NPD4062 Phase 3
0.7024 Intermediate Similarity NPD7239 Suspended
0.7018 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2801 Approved
0.7012 Intermediate Similarity NPD3750 Approved
0.7011 Intermediate Similarity NPD5494 Approved
0.6987 Remote Similarity NPD2861 Phase 2
0.6977 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6977 Remote Similarity NPD3817 Phase 2
0.6977 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6099 Approved
0.6975 Remote Similarity NPD6100 Approved
0.6975 Remote Similarity NPD2531 Phase 2
0.697 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7808 Phase 3
0.6954 Remote Similarity NPD1651 Approved
0.6954 Remote Similarity NPD5585 Approved
0.6954 Remote Similarity NPD1357 Approved
0.6949 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6949 Remote Similarity NPD2898 Approved
0.6946 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6941 Remote Similarity NPD4380 Phase 2
0.6941 Remote Similarity NPD6599 Discontinued
0.6937 Remote Similarity NPD230 Phase 1
0.6933 Remote Similarity NPD6002 Phase 3
0.6933 Remote Similarity NPD6004 Phase 3
0.6933 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6005 Phase 3
0.6933 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7315 Approved
0.6923 Remote Similarity NPD1653 Approved
0.6919 Remote Similarity NPD5760 Phase 2
0.6919 Remote Similarity NPD5761 Phase 2
0.6913 Remote Similarity NPD7157 Approved
0.6908 Remote Similarity NPD1778 Approved
0.6908 Remote Similarity NPD3095 Discontinued
0.6906 Remote Similarity NPD6764 Approved
0.6906 Remote Similarity NPD7251 Discontinued
0.6906 Remote Similarity NPD6765 Approved
0.6902 Remote Similarity NPD8150 Discontinued
0.6899 Remote Similarity NPD7008 Discontinued
0.6893 Remote Similarity NPD8051 Clinical (unspecified phase)
0.689 Remote Similarity NPD970 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1608 Approved
0.6883 Remote Similarity NPD3972 Approved
0.6882 Remote Similarity NPD3226 Approved
0.6879 Remote Similarity NPD5978 Approved
0.6879 Remote Similarity NPD5977 Approved
0.6875 Remote Similarity NPD6959 Discontinued
0.6875 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1613 Approved
0.6872 Remote Similarity NPD6620 Discovery
0.6871 Remote Similarity NPD5406 Approved
0.6871 Remote Similarity NPD5404 Approved
0.6871 Remote Similarity NPD5408 Approved
0.6871 Remote Similarity NPD4476 Approved
0.6871 Remote Similarity NPD4477 Approved
0.6871 Remote Similarity NPD5405 Approved
0.6868 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6863 Remote Similarity NPD3496 Discontinued
0.6857 Remote Similarity NPD6315 Phase 2
0.6855 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6854 Remote Similarity NPD27 Approved
0.6854 Remote Similarity NPD2489 Approved
0.6851 Remote Similarity NPD6797 Phase 2
0.6849 Remote Similarity NPD3021 Approved
0.6849 Remote Similarity NPD3022 Approved
0.6846 Remote Similarity NPD2629 Approved
0.6845 Remote Similarity NPD2532 Approved
0.6845 Remote Similarity NPD2534 Approved
0.6845 Remote Similarity NPD2533 Approved
0.6839 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6832 Remote Similarity NPD1933 Approved
0.6829 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6828 Remote Similarity NPD1358 Approved
0.6815 Remote Similarity NPD2798 Approved
0.6813 Remote Similarity NPD7038 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