Structure

Physi-Chem Properties

Molecular Weight:  718.36
Volume:  718.839
LogP:  1.256
LogD:  1.286
LogS:  -4.123
# Rotatable Bonds:  9
TPSA:  217.35
# H-Bond Aceptor:  13
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.154
Synthetic Accessibility Score:  6.016
Fsp3:  0.737
Lipinski Rule-of-5:  Rejected
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:  -5.225
MDCK Permeability:  1.1392453416192438e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.876
20% Bioavailability (F20%):  0.764
30% Bioavailability (F30%):  0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.113
Plasma Protein Binding (PPB):  70.19371032714844%
Volume Distribution (VD):  0.6
Pgp-substrate:  17.92827606201172%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.288
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.601
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.1
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.49
CYP3A4-substrate:  0.589

ADMET: Excretion

Clearance (CL):  1.54
Half-life (T1/2):  0.736

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.19
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.062
Rat Oral Acute Toxicity:  0.717
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.029
Carcinogencity:  0.67
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.781

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

  Natural Product: NPC213634

Natural Product ID:  NPC213634
Common Name*:   Cucurbitacin E 2-O-Beta-D-Glucopyranoside
IUPAC Name:   [(E,6R)-6-hydroxy-6-[(8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxohept-3-en-2-yl] acetate
Synonyms:  
Standard InCHIKey:  QKEJRKXVLGOJMB-YYBMGDPWSA-N
Standard InCHI:  InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+/t20-,21-,23-,24+,27-,28+,29-,30+,32-,35+,36-,37+,38+/m1/s1
SMILES:  CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(C(=O)C4(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)[C@]3(C)C(=O)C[C@]12C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1765381
PubChem CID:   54584209
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides
          • [CHEMONTID:0002364] Steroidal saponins
            • [CHEMONTID:0001687] Cucurbitacin 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
NPO30742 Machilus yaoshansis Species Lauraceae Eukaryota n.a. root n.a. PMID[22044245]
NPO30742 Machilus yaoshansis Species Lauraceae Eukaryota root Dayao Mountain, Guangxi, China 2007-DEC PMID[22044245]
NPO30742 Machilus yaoshansis Species Lauraceae Eukaryota Roots n.a. n.a. PMID[22779787]
NPO8970 Citrullus lanatus Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8970 Citrullus lanatus Species Cucurbitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8970 Citrullus lanatus Species Cucurbitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8970 Citrullus lanatus Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8970 Citrullus lanatus Species Cucurbitaceae 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
NPT65 Cell Line HepG2 Homo sapiens EC50 = 45330.0 nM PMID[486740]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 226670.0 nM PMID[486740]
NPT165 Cell Line HeLa Homo sapiens IC50 = 37000.0 nM PMID[486740]
NPT65 Cell Line HepG2 Homo sapiens Ratio IC50 = 6.0 n.a. PMID[486740]
NPT65 Cell Line HepG2 Homo sapiens Ratio IC50/EC50 = 5.0 n.a. PMID[486740]
NPT65 Cell Line HepG2 Homo sapiens Activity = 40.0 % PMID[486740]
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000.0 nM PMID[486741]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10000.0 nM PMID[486741]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10000.0 nM PMID[486741]
NPT81 Cell Line A549 Homo sapiens IC50 = 3200.0 nM PMID[486741]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 3280.0 nM PMID[486740]
NPT27 Others Unspecified IC50 = 102000.0 nM PMID[486740]
NPT2 Others Unspecified Ratio IC50/EC50 = 31.0 n.a. PMID[486740]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4980.0 nM PMID[486741]

☑ 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 NPC213634 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
0.9583 High Similarity NPC152091
0.9339 High Similarity NPC93368
0.9328 High Similarity NPC42675
0.9274 High Similarity NPC471855
0.9174 High Similarity NPC141196
0.9174 High Similarity NPC238005
0.9174 High Similarity NPC1980
0.9113 High Similarity NPC471407
0.9024 High Similarity NPC198714
0.8943 High Similarity NPC277191
0.8943 High Similarity NPC190846
0.879 High Similarity NPC475194
0.878 High Similarity NPC216866
0.876 High Similarity NPC158350
0.873 High Similarity NPC245094
0.873 High Similarity NPC69273
0.873 High Similarity NPC293623
0.873 High Similarity NPC168899
0.8699 High Similarity NPC202051
0.8689 High Similarity NPC319570
0.8672 High Similarity NPC155529
0.8655 High Similarity NPC221144
0.8594 High Similarity NPC173347
0.8594 High Similarity NPC241008
0.8583 High Similarity NPC311534
0.8561 High Similarity NPC79250
0.8561 High Similarity NPC290746
0.855 High Similarity NPC127656
0.8537 High Similarity NPC5292
0.8537 High Similarity NPC474179
0.8537 High Similarity NPC475834
0.8516 High Similarity NPC476966
0.8492 Intermediate Similarity NPC7850
0.8492 Intermediate Similarity NPC6615
0.8492 Intermediate Similarity NPC318135
0.8487 Intermediate Similarity NPC114961
0.8487 Intermediate Similarity NPC27551
0.8485 Intermediate Similarity NPC596
0.848 Intermediate Similarity NPC28532
0.8468 Intermediate Similarity NPC48692
0.8468 Intermediate Similarity NPC79579
0.8468 Intermediate Similarity NPC471406
0.8455 Intermediate Similarity NPC153440
0.8455 Intermediate Similarity NPC475913
0.8455 Intermediate Similarity NPC291564
0.8443 Intermediate Similarity NPC190286
0.8443 Intermediate Similarity NPC148458
0.8443 Intermediate Similarity NPC31797
0.843 Intermediate Similarity NPC73455
0.843 Intermediate Similarity NPC200944
0.8413 Intermediate Similarity NPC27363
0.8409 Intermediate Similarity NPC471089
0.8409 Intermediate Similarity NPC141215
0.8409 Intermediate Similarity NPC190065
0.8403 Intermediate Similarity NPC304495
0.84 Intermediate Similarity NPC46570
0.8397 Intermediate Similarity NPC471234
0.8385 Intermediate Similarity NPC231240
0.8374 Intermediate Similarity NPC239273
0.8361 Intermediate Similarity NPC471398
0.8359 Intermediate Similarity NPC240070
0.8359 Intermediate Similarity NPC329784
0.8347 Intermediate Similarity NPC100267
0.8347 Intermediate Similarity NPC475524
0.8347 Intermediate Similarity NPC236217
0.8346 Intermediate Similarity NPC30188
0.8346 Intermediate Similarity NPC140045
0.8346 Intermediate Similarity NPC295885
0.8346 Intermediate Similarity NPC177820
0.8333 Intermediate Similarity NPC107493
0.8333 Intermediate Similarity NPC473627
0.8333 Intermediate Similarity NPC262813
0.8321 Intermediate Similarity NPC316915
0.832 Intermediate Similarity NPC107338
0.832 Intermediate Similarity NPC109607
0.832 Intermediate Similarity NPC474585
0.8306 Intermediate Similarity NPC45475
0.8306 Intermediate Similarity NPC257457
0.8306 Intermediate Similarity NPC311554
0.8295 Intermediate Similarity NPC473620
0.8284 Intermediate Similarity NPC75616
0.8281 Intermediate Similarity NPC174367
0.8281 Intermediate Similarity NPC250556
0.8281 Intermediate Similarity NPC469750
0.8281 Intermediate Similarity NPC47113
0.8281 Intermediate Similarity NPC222307
0.8279 Intermediate Similarity NPC477944
0.8271 Intermediate Similarity NPC62172
0.8271 Intermediate Similarity NPC289700
0.8271 Intermediate Similarity NPC251998
0.8254 Intermediate Similarity NPC278163
0.8254 Intermediate Similarity NPC187950
0.825 Intermediate Similarity NPC118225
0.825 Intermediate Similarity NPC246205
0.824 Intermediate Similarity NPC305260
0.824 Intermediate Similarity NPC232258
0.824 Intermediate Similarity NPC476529
0.824 Intermediate Similarity NPC475775
0.824 Intermediate Similarity NPC270850
0.824 Intermediate Similarity NPC477071
0.8231 Intermediate Similarity NPC125077
0.8231 Intermediate Similarity NPC140092
0.8231 Intermediate Similarity NPC188234
0.8231 Intermediate Similarity NPC232785
0.8231 Intermediate Similarity NPC276838
0.8231 Intermediate Similarity NPC329986
0.8226 Intermediate Similarity NPC23046
0.8217 Intermediate Similarity NPC42399
0.8217 Intermediate Similarity NPC471357
0.8217 Intermediate Similarity NPC287423
0.8217 Intermediate Similarity NPC470882
0.8217 Intermediate Similarity NPC473265
0.8217 Intermediate Similarity NPC117702
0.8217 Intermediate Similarity NPC146456
0.8217 Intermediate Similarity NPC179412
0.8217 Intermediate Similarity NPC471356
0.8217 Intermediate Similarity NPC469757
0.8211 Intermediate Similarity NPC220293
0.8211 Intermediate Similarity NPC474181
0.8203 Intermediate Similarity NPC130229
0.8203 Intermediate Similarity NPC469842
0.8203 Intermediate Similarity NPC470922
0.8203 Intermediate Similarity NPC469841
0.8197 Intermediate Similarity NPC170487
0.8197 Intermediate Similarity NPC130427
0.8195 Intermediate Similarity NPC171619
0.8189 Intermediate Similarity NPC473231
0.8189 Intermediate Similarity NPC475431
0.8188 Intermediate Similarity NPC48813
0.8188 Intermediate Similarity NPC194854
0.8182 Intermediate Similarity NPC142756
0.8182 Intermediate Similarity NPC37116
0.8182 Intermediate Similarity NPC298783
0.8182 Intermediate Similarity NPC478151
0.8182 Intermediate Similarity NPC475487
0.8182 Intermediate Similarity NPC83005
0.8182 Intermediate Similarity NPC157817
0.8182 Intermediate Similarity NPC477709
0.8182 Intermediate Similarity NPC104585
0.8182 Intermediate Similarity NPC476221
0.8182 Intermediate Similarity NPC225385
0.8175 Intermediate Similarity NPC470312
0.8168 Intermediate Similarity NPC253456
0.8168 Intermediate Similarity NPC16569
0.8168 Intermediate Similarity NPC159338
0.8168 Intermediate Similarity NPC477197
0.816 Intermediate Similarity NPC473828
0.816 Intermediate Similarity NPC473617
0.816 Intermediate Similarity NPC176005
0.8154 Intermediate Similarity NPC473888
0.8154 Intermediate Similarity NPC270109
0.8151 Intermediate Similarity NPC162033
0.8145 Intermediate Similarity NPC176840
0.814 Intermediate Similarity NPC179261
0.813 Intermediate Similarity NPC260665
0.813 Intermediate Similarity NPC75167
0.813 Intermediate Similarity NPC311592
0.813 Intermediate Similarity NPC194100
0.8129 Intermediate Similarity NPC16729
0.8129 Intermediate Similarity NPC475462
0.8125 Intermediate Similarity NPC227397
0.8125 Intermediate Similarity NPC476542
0.8125 Intermediate Similarity NPC473979
0.8125 Intermediate Similarity NPC41129
0.8116 Intermediate Similarity NPC471172
0.8115 Intermediate Similarity NPC214797
0.8115 Intermediate Similarity NPC118860
0.8115 Intermediate Similarity NPC231589
0.811 Intermediate Similarity NPC129434
0.811 Intermediate Similarity NPC473228
0.811 Intermediate Similarity NPC470829
0.811 Intermediate Similarity NPC275675
0.811 Intermediate Similarity NPC133506
0.811 Intermediate Similarity NPC473250
0.811 Intermediate Similarity NPC472000
0.811 Intermediate Similarity NPC471999
0.8106 Intermediate Similarity NPC473805
0.8106 Intermediate Similarity NPC42670
0.8106 Intermediate Similarity NPC19124
0.8106 Intermediate Similarity NPC93416
0.8106 Intermediate Similarity NPC478152
0.8106 Intermediate Similarity NPC473519
0.8106 Intermediate Similarity NPC478153
0.8106 Intermediate Similarity NPC478154
0.8106 Intermediate Similarity NPC478150
0.8099 Intermediate Similarity NPC470257
0.8095 Intermediate Similarity NPC475041
0.8095 Intermediate Similarity NPC127530
0.8095 Intermediate Similarity NPC258592
0.8095 Intermediate Similarity NPC178548
0.8095 Intermediate Similarity NPC161738
0.8092 Intermediate Similarity NPC471361
0.8092 Intermediate Similarity NPC10823
0.8092 Intermediate Similarity NPC221414
0.8092 Intermediate Similarity NPC471352
0.8092 Intermediate Similarity NPC70542
0.8092 Intermediate Similarity NPC197707
0.8092 Intermediate Similarity NPC219085
0.8092 Intermediate Similarity NPC473593
0.8092 Intermediate Similarity NPC17896

  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 NPC213634 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
0.8295 Intermediate Similarity NPD7736 Approved
0.8281 Intermediate Similarity NPD7507 Approved
0.8254 Intermediate Similarity NPD7503 Approved
0.8092 Intermediate Similarity NPD7319 Approved
0.8083 Intermediate Similarity NPD6412 Phase 2
0.8049 Intermediate Similarity NPD6882 Approved
0.8049 Intermediate Similarity NPD8297 Approved
0.8047 Intermediate Similarity NPD6370 Approved
0.8017 Intermediate Similarity NPD6686 Approved
0.7939 Intermediate Similarity NPD8293 Discontinued
0.7937 Intermediate Similarity NPD6009 Approved
0.7923 Intermediate Similarity NPD7492 Approved
0.7891 Intermediate Similarity NPD6054 Approved
0.7891 Intermediate Similarity NPD6319 Approved
0.7863 Intermediate Similarity NPD6616 Approved
0.7846 Intermediate Similarity NPD8328 Phase 3
0.7829 Intermediate Similarity NPD8033 Approved
0.7823 Intermediate Similarity NPD6649 Approved
0.7823 Intermediate Similarity NPD6650 Approved
0.7803 Intermediate Similarity NPD7078 Approved
0.7752 Intermediate Similarity NPD8294 Approved
0.7752 Intermediate Similarity NPD8377 Approved
0.7734 Intermediate Similarity NPD7327 Approved
0.7734 Intermediate Similarity NPD7328 Approved
0.7724 Intermediate Similarity NPD6881 Approved
0.7724 Intermediate Similarity NPD6899 Approved
0.7698 Intermediate Similarity NPD4632 Approved
0.7692 Intermediate Similarity NPD6015 Approved
0.7692 Intermediate Similarity NPD8379 Approved
0.7692 Intermediate Similarity NPD8378 Approved
0.7692 Intermediate Similarity NPD8335 Approved
0.7692 Intermediate Similarity NPD6016 Approved
0.7692 Intermediate Similarity NPD8296 Approved
0.7692 Intermediate Similarity NPD8380 Approved
0.768 Intermediate Similarity NPD8130 Phase 1
0.7674 Intermediate Similarity NPD7516 Approved
0.7661 Intermediate Similarity NPD6372 Approved
0.7661 Intermediate Similarity NPD6373 Approved
0.7642 Intermediate Similarity NPD5697 Approved
0.7634 Intermediate Similarity NPD5988 Approved
0.7619 Intermediate Similarity NPD6053 Discontinued
0.7615 Intermediate Similarity NPD6059 Approved
0.76 Intermediate Similarity NPD7290 Approved
0.76 Intermediate Similarity NPD6883 Approved
0.76 Intermediate Similarity NPD7102 Approved
0.7561 Intermediate Similarity NPD6402 Approved
0.7561 Intermediate Similarity NPD7128 Approved
0.7561 Intermediate Similarity NPD5739 Approved
0.7561 Intermediate Similarity NPD6675 Approved
0.7559 Intermediate Similarity NPD8133 Approved
0.754 Intermediate Similarity NPD6847 Approved
0.754 Intermediate Similarity NPD6617 Approved
0.754 Intermediate Similarity NPD6869 Approved
0.752 Intermediate Similarity NPD6013 Approved
0.752 Intermediate Similarity NPD6014 Approved
0.752 Intermediate Similarity NPD6012 Approved
0.7519 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD7115 Discovery
0.7445 Intermediate Similarity NPD7260 Phase 2
0.7444 Intermediate Similarity NPD7604 Phase 2
0.744 Intermediate Similarity NPD6011 Approved
0.744 Intermediate Similarity NPD7320 Approved
0.7424 Intermediate Similarity NPD5983 Phase 2
0.7424 Intermediate Similarity NPD8513 Phase 3
0.7424 Intermediate Similarity NPD8517 Approved
0.7424 Intermediate Similarity NPD8515 Approved
0.7424 Intermediate Similarity NPD8516 Approved
0.7417 Intermediate Similarity NPD6083 Phase 2
0.7417 Intermediate Similarity NPD6084 Phase 2
0.7402 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5695 Phase 3
0.7381 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD5701 Approved
0.7333 Intermediate Similarity NPD6336 Discontinued
0.7222 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5696 Approved
0.7188 Intermediate Similarity NPD4634 Approved
0.7177 Intermediate Similarity NPD5211 Phase 2
0.7154 Intermediate Similarity NPD5285 Approved
0.7154 Intermediate Similarity NPD5286 Approved
0.7154 Intermediate Similarity NPD4696 Approved
0.7143 Intermediate Similarity NPD7100 Approved
0.7143 Intermediate Similarity NPD7101 Approved
0.7132 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6033 Approved
0.7068 Intermediate Similarity NPD6335 Approved
0.7063 Intermediate Similarity NPD5141 Approved
0.7054 Intermediate Similarity NPD6371 Approved
0.7045 Intermediate Similarity NPD6274 Approved
0.704 Intermediate Similarity NPD5224 Approved
0.704 Intermediate Similarity NPD5225 Approved
0.704 Intermediate Similarity NPD5226 Approved
0.704 Intermediate Similarity NPD4633 Approved
0.7031 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6845 Suspended
0.7008 Intermediate Similarity NPD6008 Approved
0.7 Intermediate Similarity NPD5956 Approved
0.7 Intermediate Similarity NPD5693 Phase 1
0.6992 Remote Similarity NPD6317 Approved
0.6992 Remote Similarity NPD4755 Approved
0.6984 Remote Similarity NPD5175 Approved
0.6984 Remote Similarity NPD5174 Approved
0.6967 Remote Similarity NPD5210 Approved
0.6967 Remote Similarity NPD4629 Approved
0.696 Remote Similarity NPD5223 Approved
0.694 Remote Similarity NPD6314 Approved
0.694 Remote Similarity NPD6313 Approved
0.6935 Remote Similarity NPD7638 Approved
0.6935 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7799 Discontinued
0.6899 Remote Similarity NPD4730 Approved
0.6899 Remote Similarity NPD4729 Approved
0.688 Remote Similarity NPD4700 Approved
0.688 Remote Similarity NPD7639 Approved
0.688 Remote Similarity NPD7640 Approved
0.686 Remote Similarity NPD5694 Approved
0.686 Remote Similarity NPD5284 Approved
0.686 Remote Similarity NPD6050 Approved
0.686 Remote Similarity NPD5281 Approved
0.6833 Remote Similarity NPD6673 Approved
0.6833 Remote Similarity NPD6080 Approved
0.6833 Remote Similarity NPD4753 Phase 2
0.6833 Remote Similarity NPD6904 Approved
0.6828 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6803 Remote Similarity NPD6399 Phase 3
0.6797 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6794 Remote Similarity NPD5250 Approved
0.6794 Remote Similarity NPD5249 Phase 3
0.6794 Remote Similarity NPD5251 Approved
0.6794 Remote Similarity NPD5248 Approved
0.6794 Remote Similarity NPD5247 Approved
0.6788 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6909 Approved
0.6788 Remote Similarity NPD6908 Approved
0.6786 Remote Similarity NPD8074 Phase 3
0.6777 Remote Similarity NPD6698 Approved
0.6777 Remote Similarity NPD5692 Phase 3
0.6777 Remote Similarity NPD46 Approved
0.675 Remote Similarity NPD5737 Approved
0.675 Remote Similarity NPD6672 Approved
0.6744 Remote Similarity NPD4768 Approved
0.6744 Remote Similarity NPD4767 Approved
0.6739 Remote Similarity NPD8080 Discontinued
0.6723 Remote Similarity NPD5690 Phase 2
0.6718 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6691 Remote Similarity NPD6067 Discontinued
0.6667 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6868 Approved
0.6641 Remote Similarity NPD5128 Approved
0.664 Remote Similarity NPD5220 Clinical (unspecified phase)
0.664 Remote Similarity NPD5222 Approved
0.664 Remote Similarity NPD5221 Approved
0.6639 Remote Similarity NPD5785 Approved
0.662 Remote Similarity NPD8336 Approved
0.662 Remote Similarity NPD8337 Approved
0.6617 Remote Similarity NPD5216 Approved
0.6617 Remote Similarity NPD5215 Approved
0.6617 Remote Similarity NPD5217 Approved
0.6613 Remote Similarity NPD5282 Discontinued
0.6612 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6589 Remote Similarity NPD4754 Approved
0.6587 Remote Similarity NPD5173 Approved
0.6585 Remote Similarity NPD6079 Approved
0.6583 Remote Similarity NPD6409 Approved
0.6583 Remote Similarity NPD6098 Approved
0.6583 Remote Similarity NPD7334 Approved
0.6583 Remote Similarity NPD7146 Approved
0.6583 Remote Similarity NPD6684 Approved
0.6583 Remote Similarity NPD7521 Approved
0.6583 Remote Similarity NPD5330 Approved
0.6571 Remote Similarity NPD7829 Approved
0.6571 Remote Similarity NPD7830 Approved
0.6571 Remote Similarity NPD7642 Approved
0.6558 Remote Similarity NPD7236 Approved
0.6547 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6547 Remote Similarity NPD6921 Approved
0.6541 Remote Similarity NPD5169 Approved
0.6541 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6541 Remote Similarity NPD5135 Approved
0.6535 Remote Similarity NPD4225 Approved
0.6522 Remote Similarity NPD4522 Approved
0.6508 Remote Similarity NPD4697 Phase 3
0.6504 Remote Similarity NPD7838 Discovery
0.6504 Remote Similarity NPD5207 Approved
0.65 Remote Similarity NPD5329 Approved
0.6493 Remote Similarity NPD5127 Approved
0.6479 Remote Similarity NPD8451 Approved
0.6475 Remote Similarity NPD6903 Approved
0.6457 Remote Similarity NPD7902 Approved
0.6456 Remote Similarity NPD7239 Suspended
0.6452 Remote Similarity NPD6411 Approved
0.6452 Remote Similarity NPD7983 Approved
0.6449 Remote Similarity NPD7641 Discontinued
0.6446 Remote Similarity NPD5280 Approved
0.6446 Remote Similarity NPD5279 Phase 3
0.6446 Remote Similarity NPD4694 Approved
0.6439 Remote Similarity NPD6614 Approved
0.6439 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6434 Remote Similarity NPD8448 Approved
0.6429 Remote Similarity NPD6356 Clinical (unspecified phase)

  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