Structure

Physi-Chem Properties

Molecular Weight:  764.4
Volume:  764.858
LogP:  2.238
LogD:  2.082
LogS:  -3.791
# Rotatable Bonds:  11
TPSA:  226.58
# H-Bond Aceptor:  14
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.112
Synthetic Accessibility Score:  6.015
Fsp3:  0.8
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:  -5.375
MDCK Permeability:  7.625761645613238e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.72
Human Intestinal Absorption (HIA):  0.913
20% Bioavailability (F20%):  0.631
30% Bioavailability (F30%):  0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.08
Plasma Protein Binding (PPB):  54.65837097167969%
Volume Distribution (VD):  0.499
Pgp-substrate:  21.384042739868164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.076
CYP2C19-inhibitor:  0.005
CYP2C19-substrate:  0.494
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.07
CYP3A4-inhibitor:  0.335
CYP3A4-substrate:  0.454

ADMET: Excretion

Clearance (CL):  1.435
Half-life (T1/2):  0.731

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.189
Drug-inuced Liver Injury (DILI):  0.566
AMES Toxicity:  0.058
Rat Oral Acute Toxicity:  0.385
Maximum Recommended Daily Dose:  0.768
Skin Sensitization:  0.048
Carcinogencity:  0.692
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.244

Download Data

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

  Natural Product: NPC471855

Natural Product ID:  NPC471855
Common Name*:   2Beta,3Alpha,20-Trihydroxycucurbita-5,23(E)-Diene-11,22-Dione-16,25-Diacetyl-2-O-Beta-D-Glucopyranoside
IUPAC Name:   [(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(E)-6-acetyloxy-2-hydroxy-6-methyl-3-oxohept-4-en-2-yl]-3-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms:  
Standard InCHIKey:  IEXHKZSJOVHXGQ-SJONZPOXSA-N
Standard InCHI:  InChI=1S/C40H60O14/c1-19(42)51-24-16-37(7)26-12-11-21-22(15-23(33(49)36(21,5)6)52-34-31(48)30(47)29(46)25(18-41)53-34)39(26,9)28(45)17-38(37,8)32(24)40(10,50)27(44)13-14-35(3,4)54-20(2)43/h11,13-14,22-26,29-34,41,46-50H,12,15-18H2,1-10H3/b14-13+/t22-,23+,24-,25-,26+,29-,30+,31-,32+,33-,34-,37+,38-,39+,40?/m1/s1
SMILES:  CC(=O)OC1CC2(C3CC=C4C(C3(C(=O)CC2(C1C(C)(C(=O)C=CC(C)(C)OC(=O)C)O)C)C)CC(C(C4(C)C)O)OC5C(C(C(C(O5)CO)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3261681
PubChem CID:   90676076
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
NPO33474 hemsleya penxianensis Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[24717151]

☑ 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
NPT323 Cell Line SW-620 Homo sapiens IC50 = 6.63 ug.mL-1 PMID[523299]
NPT407 Cell Line COLO 205 Homo sapiens IC50 = 24.94 ug.mL-1 PMID[523299]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 8.55 ug.mL-1 PMID[523299]

☑ 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 NPC471855 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
0.9833 High Similarity NPC471407
0.9274 High Similarity NPC213634
0.9219 High Similarity NPC79250
0.9219 High Similarity NPC290746
0.9194 High Similarity NPC476966
0.9174 High Similarity NPC28532
0.9167 High Similarity NPC471406
0.912 High Similarity NPC173347
0.9113 High Similarity NPC311534
0.9 High Similarity NPC257457
0.9 High Similarity NPC311554
0.896 High Similarity NPC245094
0.8943 High Similarity NPC27363
0.8934 High Similarity NPC202051
0.8926 High Similarity NPC475775
0.8926 High Similarity NPC476529
0.8898 High Similarity NPC231240
0.888 High Similarity NPC240070
0.888 High Similarity NPC470882
0.888 High Similarity NPC329784
0.888 High Similarity NPC152091
0.8852 High Similarity NPC48692
0.8852 High Similarity NPC109607
0.8852 High Similarity NPC107338
0.8837 High Similarity NPC158350
0.8828 High Similarity NPC142756
0.8828 High Similarity NPC225385
0.8828 High Similarity NPC316915
0.8828 High Similarity NPC157817
0.8828 High Similarity NPC298783
0.8828 High Similarity NPC104585
0.8828 High Similarity NPC477709
0.8828 High Similarity NPC476221
0.8819 High Similarity NPC159338
0.8819 High Similarity NPC253456
0.8819 High Similarity NPC16569
0.881 High Similarity NPC473620
0.88 High Similarity NPC250556
0.88 High Similarity NPC469750
0.88 High Similarity NPC47113
0.88 High Similarity NPC174367
0.877 High Similarity NPC475041
0.877 High Similarity NPC477071
0.876 High Similarity NPC471854
0.875 High Similarity NPC155529
0.875 High Similarity NPC19124
0.875 High Similarity NPC473805
0.875 High Similarity NPC93416
0.875 High Similarity NPC42670
0.875 High Similarity NPC473519
0.874 High Similarity NPC329986
0.874 High Similarity NPC140092
0.874 High Similarity NPC231529
0.874 High Similarity NPC232785
0.874 High Similarity NPC125077
0.874 High Similarity NPC276838
0.874 High Similarity NPC188234
0.874 High Similarity NPC91
0.873 High Similarity NPC471357
0.873 High Similarity NPC473265
0.873 High Similarity NPC471356
0.873 High Similarity NPC146456
0.873 High Similarity NPC287423
0.873 High Similarity NPC42399
0.873 High Similarity NPC469757
0.873 High Similarity NPC117702
0.873 High Similarity NPC179412
0.872 High Similarity NPC318135
0.872 High Similarity NPC473255
0.872 High Similarity NPC470922
0.872 High Similarity NPC475194
0.871 High Similarity NPC269642
0.8702 High Similarity NPC596
0.8699 High Similarity NPC470312
0.8692 High Similarity NPC171619
0.8689 High Similarity NPC45475
0.8689 High Similarity NPC473828
0.8689 High Similarity NPC473617
0.8682 High Similarity NPC102015
0.8682 High Similarity NPC478151
0.8682 High Similarity NPC88668
0.8678 High Similarity NPC148458
0.8672 High Similarity NPC477197
0.8667 High Similarity NPC260665
0.8661 High Similarity NPC293623
0.8661 High Similarity NPC69273
0.8661 High Similarity NPC473888
0.8661 High Similarity NPC168899
0.8661 High Similarity NPC270109
0.8661 High Similarity NPC477490
0.8661 High Similarity NPC114306
0.8651 High Similarity NPC93368
0.8651 High Similarity NPC222307
0.8651 High Similarity NPC473635
0.864 High Similarity NPC41129
0.864 High Similarity NPC473979
0.8629 High Similarity NPC42675
0.8626 High Similarity NPC190065
0.8626 High Similarity NPC471089
0.8626 High Similarity NPC127656
0.8626 High Similarity NPC141215
0.8618 High Similarity NPC5292
0.8618 High Similarity NPC319570
0.8607 High Similarity NPC473968
0.8607 High Similarity NPC203862
0.8607 High Similarity NPC309433
0.8607 High Similarity NPC239273
0.8605 High Similarity NPC478153
0.8605 High Similarity NPC478150
0.8605 High Similarity NPC478152
0.8605 High Similarity NPC478154
0.8594 High Similarity NPC473593
0.8594 High Similarity NPC89514
0.8594 High Similarity NPC477196
0.8594 High Similarity NPC469751
0.8594 High Similarity NPC9499
0.8594 High Similarity NPC471359
0.8594 High Similarity NPC471360
0.8594 High Similarity NPC284406
0.8594 High Similarity NPC471352
0.8594 High Similarity NPC470913
0.8594 High Similarity NPC86159
0.8594 High Similarity NPC70542
0.8594 High Similarity NPC477076
0.8594 High Similarity NPC469753
0.8594 High Similarity NPC180079
0.8594 High Similarity NPC469752
0.8594 High Similarity NPC471361
0.8594 High Similarity NPC10823
0.8594 High Similarity NPC251866
0.8594 High Similarity NPC470880
0.8594 High Similarity NPC477077
0.8594 High Similarity NPC469755
0.8594 High Similarity NPC197707
0.8594 High Similarity NPC219085
0.8594 High Similarity NPC6108
0.8594 High Similarity NPC471358
0.8594 High Similarity NPC17896
0.8594 High Similarity NPC469754
0.8594 High Similarity NPC477079
0.8583 High Similarity NPC280782
0.8583 High Similarity NPC475524
0.8583 High Similarity NPC100267
0.8583 High Similarity NPC470780
0.8583 High Similarity NPC130427
0.8583 High Similarity NPC473253
0.8571 High Similarity NPC241456
0.8571 High Similarity NPC32868
0.8561 High Similarity NPC140045
0.8561 High Similarity NPC295885
0.856 High Similarity NPC222688
0.855 High Similarity NPC262813
0.8548 High Similarity NPC476961
0.8548 High Similarity NPC79579
0.8538 High Similarity NPC247190
0.8538 High Similarity NPC116075
0.8538 High Similarity NPC32793
0.8538 High Similarity NPC469749
0.8538 High Similarity NPC146857
0.8538 High Similarity NPC225791
0.8537 High Similarity NPC291564
0.8537 High Similarity NPC153440
0.8527 High Similarity NPC475167
0.8527 High Similarity NPC478065
0.8527 High Similarity NPC25998
0.8527 High Similarity NPC173435
0.8527 High Similarity NPC264566
0.8527 High Similarity NPC301639
0.8527 High Similarity NPC478064
0.8527 High Similarity NPC476074
0.8527 High Similarity NPC134914
0.8527 High Similarity NPC329993
0.8527 High Similarity NPC478155
0.8527 High Similarity NPC241008
0.8527 High Similarity NPC471170
0.8527 High Similarity NPC262796
0.8527 High Similarity NPC172374
0.8527 High Similarity NPC475377
0.8527 High Similarity NPC477493
0.8527 High Similarity NPC45346
0.8525 High Similarity NPC134869
0.8525 High Similarity NPC152199
0.8525 High Similarity NPC190286
0.8525 High Similarity NPC235539
0.8516 High Similarity NPC477194
0.8516 High Similarity NPC475281
0.8516 High Similarity NPC477193
0.8516 High Similarity NPC329923
0.8516 High Similarity NPC477078
0.8516 High Similarity NPC477192
0.8516 High Similarity NPC477075
0.8516 High Similarity NPC477191
0.8512 High Similarity NPC255017
0.8512 High Similarity NPC75167
0.8512 High Similarity NPC194100
0.8512 High Similarity NPC311592
0.8512 High Similarity NPC962
0.8512 High Similarity NPC250109
0.8504 High Similarity NPC293112
0.85 High Similarity NPC285410

  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 NPC471855 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
0.88 High Similarity NPD7507 Approved
0.8661 High Similarity NPD7736 Approved
0.8594 High Similarity NPD7319 Approved
0.843 Intermediate Similarity NPD8297 Approved
0.843 Intermediate Similarity NPD6882 Approved
0.8413 Intermediate Similarity NPD6370 Approved
0.8333 Intermediate Similarity NPD8033 Approved
0.8333 Intermediate Similarity NPD7503 Approved
0.832 Intermediate Similarity NPD7516 Approved
0.8306 Intermediate Similarity NPD6009 Approved
0.8295 Intermediate Similarity NPD8293 Discontinued
0.8281 Intermediate Similarity NPD7492 Approved
0.8254 Intermediate Similarity NPD6054 Approved
0.8254 Intermediate Similarity NPD6319 Approved
0.8254 Intermediate Similarity NPD8377 Approved
0.8254 Intermediate Similarity NPD8294 Approved
0.824 Intermediate Similarity NPD7328 Approved
0.824 Intermediate Similarity NPD7327 Approved
0.8217 Intermediate Similarity NPD6616 Approved
0.8211 Intermediate Similarity NPD4632 Approved
0.8203 Intermediate Similarity NPD8328 Phase 3
0.8197 Intermediate Similarity NPD6650 Approved
0.8197 Intermediate Similarity NPD6649 Approved
0.8189 Intermediate Similarity NPD8379 Approved
0.8189 Intermediate Similarity NPD8378 Approved
0.8189 Intermediate Similarity NPD8296 Approved
0.8189 Intermediate Similarity NPD8380 Approved
0.8189 Intermediate Similarity NPD8335 Approved
0.8167 Intermediate Similarity NPD6412 Phase 2
0.8154 Intermediate Similarity NPD7078 Approved
0.8099 Intermediate Similarity NPD6686 Approved
0.8099 Intermediate Similarity NPD6881 Approved
0.8099 Intermediate Similarity NPD6899 Approved
0.8049 Intermediate Similarity NPD8130 Phase 1
0.8047 Intermediate Similarity NPD6015 Approved
0.8047 Intermediate Similarity NPD6016 Approved
0.8033 Intermediate Similarity NPD6372 Approved
0.8033 Intermediate Similarity NPD6373 Approved
0.8017 Intermediate Similarity NPD5697 Approved
0.8016 Intermediate Similarity NPD7115 Discovery
0.7984 Intermediate Similarity NPD5988 Approved
0.7969 Intermediate Similarity NPD6059 Approved
0.7967 Intermediate Similarity NPD7102 Approved
0.7967 Intermediate Similarity NPD7290 Approved
0.7967 Intermediate Similarity NPD6883 Approved
0.7934 Intermediate Similarity NPD5739 Approved
0.7934 Intermediate Similarity NPD7128 Approved
0.7934 Intermediate Similarity NPD6675 Approved
0.7934 Intermediate Similarity NPD6402 Approved
0.792 Intermediate Similarity NPD8133 Approved
0.7903 Intermediate Similarity NPD6869 Approved
0.7903 Intermediate Similarity NPD6847 Approved
0.7903 Intermediate Similarity NPD6617 Approved
0.7886 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD6012 Approved
0.7886 Intermediate Similarity NPD6013 Approved
0.7886 Intermediate Similarity NPD6014 Approved
0.7874 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD7320 Approved
0.7805 Intermediate Similarity NPD6011 Approved
0.7786 Intermediate Similarity NPD7604 Phase 2
0.7769 Intermediate Similarity NPD5983 Phase 2
0.7769 Intermediate Similarity NPD8513 Phase 3
0.7769 Intermediate Similarity NPD8515 Approved
0.7769 Intermediate Similarity NPD8517 Approved
0.7769 Intermediate Similarity NPD8516 Approved
0.7724 Intermediate Similarity NPD5701 Approved
0.7686 Intermediate Similarity NPD5211 Phase 2
0.768 Intermediate Similarity NPD4634 Approved
0.7669 Intermediate Similarity NPD6336 Discontinued
0.7667 Intermediate Similarity NPD5285 Approved
0.7667 Intermediate Similarity NPD5286 Approved
0.7667 Intermediate Similarity NPD4696 Approved
0.7661 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD5141 Approved
0.7541 Intermediate Similarity NPD4633 Approved
0.7541 Intermediate Similarity NPD5226 Approved
0.7541 Intermediate Similarity NPD5224 Approved
0.7541 Intermediate Similarity NPD5225 Approved
0.75 Intermediate Similarity NPD4755 Approved
0.75 Intermediate Similarity NPD6008 Approved
0.7481 Intermediate Similarity NPD7101 Approved
0.7481 Intermediate Similarity NPD7100 Approved
0.748 Intermediate Similarity NPD5175 Approved
0.748 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD5174 Approved
0.7459 Intermediate Similarity NPD5223 Approved
0.7438 Intermediate Similarity NPD7638 Approved
0.7426 Intermediate Similarity NPD6033 Approved
0.7405 Intermediate Similarity NPD6335 Approved
0.7385 Intermediate Similarity NPD6274 Approved
0.7381 Intermediate Similarity NPD4729 Approved
0.7381 Intermediate Similarity NPD4730 Approved
0.7377 Intermediate Similarity NPD7639 Approved
0.7377 Intermediate Similarity NPD4700 Approved
0.7377 Intermediate Similarity NPD7640 Approved
0.7355 Intermediate Similarity NPD6083 Phase 2
0.7355 Intermediate Similarity NPD6084 Phase 2
0.7344 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD6317 Approved
0.7323 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD6053 Discontinued
0.7273 Intermediate Similarity NPD6314 Approved
0.7273 Intermediate Similarity NPD6313 Approved
0.7266 Intermediate Similarity NPD5250 Approved
0.7266 Intermediate Similarity NPD5248 Approved
0.7266 Intermediate Similarity NPD5251 Approved
0.7266 Intermediate Similarity NPD5247 Approved
0.7266 Intermediate Similarity NPD5249 Phase 3
0.7266 Intermediate Similarity NPD7260 Phase 2
0.7266 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4768 Approved
0.7222 Intermediate Similarity NPD4767 Approved
0.7205 Intermediate Similarity NPD7799 Discontinued
0.7165 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD5696 Approved
0.7143 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD6067 Discontinued
0.7131 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD5221 Approved
0.7131 Intermediate Similarity NPD5222 Approved
0.7111 Intermediate Similarity NPD6908 Approved
0.7111 Intermediate Similarity NPD6909 Approved
0.7111 Intermediate Similarity NPD6921 Approved
0.7109 Intermediate Similarity NPD5128 Approved
0.7101 Intermediate Similarity NPD8074 Phase 3
0.7083 Intermediate Similarity NPD6079 Approved
0.7077 Intermediate Similarity NPD5215 Approved
0.7077 Intermediate Similarity NPD5217 Approved
0.7077 Intermediate Similarity NPD5216 Approved
0.7073 Intermediate Similarity NPD5173 Approved
0.7063 Intermediate Similarity NPD4754 Approved
0.7049 Intermediate Similarity NPD4629 Approved
0.7049 Intermediate Similarity NPD5210 Approved
0.7049 Intermediate Similarity NPD5695 Phase 3
0.7031 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6399 Phase 3
0.7016 Intermediate Similarity NPD4225 Approved
0.7 Intermediate Similarity NPD5135 Approved
0.7 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6371 Approved
0.7 Intermediate Similarity NPD5169 Approved
0.6992 Remote Similarity NPD6868 Approved
0.6992 Remote Similarity NPD4697 Phase 3
0.695 Remote Similarity NPD5956 Approved
0.6947 Remote Similarity NPD5127 Approved
0.6942 Remote Similarity NPD5693 Phase 1
0.6935 Remote Similarity NPD7902 Approved
0.6917 Remote Similarity NPD4753 Phase 2
0.6917 Remote Similarity NPD5328 Approved
0.6885 Remote Similarity NPD4202 Approved
0.688 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6845 Suspended
0.685 Remote Similarity NPD7632 Discontinued
0.6842 Remote Similarity NPD7236 Approved
0.6829 Remote Similarity NPD7748 Approved
0.6821 Remote Similarity NPD7625 Phase 1
0.6791 Remote Similarity NPD5167 Approved
0.6777 Remote Similarity NPD6080 Approved
0.6777 Remote Similarity NPD6904 Approved
0.6777 Remote Similarity NPD6673 Approved
0.6774 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6772 Remote Similarity NPD5344 Discontinued
0.675 Remote Similarity NPD3573 Approved
0.6736 Remote Similarity NPD8338 Approved
0.6731 Remote Similarity NPD7239 Suspended
0.6721 Remote Similarity NPD46 Approved
0.6721 Remote Similarity NPD6698 Approved
0.6694 Remote Similarity NPD7900 Approved
0.6694 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6694 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5737 Approved
0.6694 Remote Similarity NPD6672 Approved
0.6667 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7521 Approved
0.6667 Remote Similarity NPD8035 Phase 2
0.6667 Remote Similarity NPD7515 Phase 2
0.6667 Remote Similarity NPD5284 Approved
0.6667 Remote Similarity NPD8034 Phase 2
0.6667 Remote Similarity NPD7146 Approved
0.6667 Remote Similarity NPD5330 Approved
0.6667 Remote Similarity NPD3618 Phase 1
0.6667 Remote Similarity NPD7334 Approved
0.6667 Remote Similarity NPD6684 Approved
0.6667 Remote Similarity NPD5281 Approved
0.6667 Remote Similarity NPD6409 Approved
0.6622 Remote Similarity NPD6333 Approved
0.6622 Remote Similarity NPD6334 Approved
0.6594 Remote Similarity NPD4522 Approved
0.6591 Remote Similarity NPD5168 Approved
0.6585 Remote Similarity NPD5785 Approved
0.6583 Remote Similarity NPD5329 Approved
0.6573 Remote Similarity NPD8337 Approved
0.6573 Remote Similarity NPD8336 Approved
0.6557 Remote Similarity NPD6903 Approved
0.6548 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6050 Approved
0.6532 Remote Similarity NPD5694 Approved
0.6529 Remote Similarity NPD6098 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