Structure

Physi-Chem Properties

Molecular Weight:  742.47
Volume:  787.505
LogP:  4.213
LogD:  3.176
LogS:  -4.523
# Rotatable Bonds:  5
TPSA:  153.5
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.233
Synthetic Accessibility Score:  6.875
Fsp3:  0.791
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.928
MDCK Permeability:  1.4605820979340933e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.863
Human Intestinal Absorption (HIA):  0.595
20% Bioavailability (F20%):  0.305
30% Bioavailability (F30%):  0.767

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.566
Plasma Protein Binding (PPB):  87.89724731445312%
Volume Distribution (VD):  1.224
Pgp-substrate:  4.374597072601318%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.085
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.815
CYP2C9-inhibitor:  0.156
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.035
CYP3A4-inhibitor:  0.88
CYP3A4-substrate:  0.664

ADMET: Excretion

Clearance (CL):  7.62
Half-life (T1/2):  0.091

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.971
Drug-inuced Liver Injury (DILI):  0.743
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.99
Maximum Recommended Daily Dose:  0.901
Skin Sensitization:  0.061
Carcinogencity:  0.029
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.057

Download Data

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

  Natural Product: NPC470104

Natural Product ID:  NPC470104
Common Name*:   Ximaolide F
IUPAC Name:   n.a.
Synonyms:   Ximaolide F
Standard InCHIKey:  MUOXKHZNCZBPQL-ZOLTTXMASA-N
Standard InCHI:  InChI=1S/C43H66O10/c1-24(2)30-21-33(45)27(5)13-11-12-25(3)19-34(46)31-20-28(6)39-32(43(31,23-35(30)47)40(49)51-10)18-26(4)14-15-38-42(9,53-29(7)44)17-16-37(52-38)41(8,50)22-36(39)48/h18,24-25,27,30-32,36-38,48,50H,11-17,19-23H2,1-10H3/b26-18+/t25-,27+,30-,31?,32?,36-,37?,38?,41-,42+,43+/m1/s1
SMILES:  CC1CCCC(C(=O)CC(C(=O)CC2(C(CC(=C3C2C=C(CCC4C(CCC(O4)C(CC3O)(C)O)(C)OC(=O)C)C)C)C(=O)C1)C(=O)OC)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1765189
PubChem CID:   52920792
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0000357] Sesquaterpenoids

*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
NPO9888 Lobophytum laevigatum Species Alcyoniidae Eukaryota n.a. Vietnamese n.a. PMID[21458279]
NPO9888 Lobophytum laevigatum Species Alcyoniidae Eukaryota n.a. Vietnamese soft coral n.a. PMID[21507644]
NPO9888 Lobophytum laevigatum Species Alcyoniidae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 9000.0 nM PMID[523872]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 16400.0 nM PMID[523872]
NPT81 Cell Line A549 Homo sapiens IC50 = 28400.0 nM PMID[523872]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[523872]
NPT2 Others Unspecified IC50 = 6900.0 nM PMID[523872]

☑ 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 NPC470104 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
0.9175 High Similarity NPC124246
0.91 High Similarity NPC475321
0.9 High Similarity NPC476235
0.9 High Similarity NPC476126
0.89 High Similarity NPC477871
0.89 High Similarity NPC477870
0.89 High Similarity NPC476213
0.89 High Similarity NPC476246
0.8812 High Similarity NPC283567
0.8529 High Similarity NPC101067
0.8529 High Similarity NPC476134
0.8426 Intermediate Similarity NPC174836
0.8302 Intermediate Similarity NPC112780
0.8302 Intermediate Similarity NPC230541
0.8286 Intermediate Similarity NPC258532
0.8273 Intermediate Similarity NPC181145
0.8269 Intermediate Similarity NPC223834
0.8252 Intermediate Similarity NPC167974
0.8241 Intermediate Similarity NPC83005
0.8214 Intermediate Similarity NPC234522
0.8198 Intermediate Similarity NPC474734
0.8182 Intermediate Similarity NPC75167
0.8182 Intermediate Similarity NPC471204
0.8182 Intermediate Similarity NPC311592
0.8173 Intermediate Similarity NPC97435
0.8148 Intermediate Similarity NPC141350
0.8108 Intermediate Similarity NPC117712
0.8108 Intermediate Similarity NPC473898
0.8095 Intermediate Similarity NPC473928
0.8091 Intermediate Similarity NPC472002
0.8073 Intermediate Similarity NPC5103
0.807 Intermediate Similarity NPC48692
0.8056 Intermediate Similarity NPC151393
0.8053 Intermediate Similarity NPC251310
0.8053 Intermediate Similarity NPC470776
0.8039 Intermediate Similarity NPC134067
0.8036 Intermediate Similarity NPC474046
0.8036 Intermediate Similarity NPC259306
0.8036 Intermediate Similarity NPC470628
0.8019 Intermediate Similarity NPC8196
0.8019 Intermediate Similarity NPC69171
0.8019 Intermediate Similarity NPC99266
0.8019 Intermediate Similarity NPC474165
0.8018 Intermediate Similarity NPC250109
0.8018 Intermediate Similarity NPC469454
0.8018 Intermediate Similarity NPC962
0.8018 Intermediate Similarity NPC469463
0.8018 Intermediate Similarity NPC469496
0.8 Intermediate Similarity NPC472000
0.8 Intermediate Similarity NPC188738
0.8 Intermediate Similarity NPC471999
0.8 Intermediate Similarity NPC214844
0.8 Intermediate Similarity NPC232202
0.7982 Intermediate Similarity NPC472534
0.7982 Intermediate Similarity NPC143706
0.7982 Intermediate Similarity NPC118225
0.7965 Intermediate Similarity NPC472934
0.7965 Intermediate Similarity NPC470775
0.7965 Intermediate Similarity NPC473590
0.7965 Intermediate Similarity NPC176513
0.7963 Intermediate Similarity NPC143609
0.7949 Intermediate Similarity NPC476729
0.7946 Intermediate Similarity NPC470919
0.7946 Intermediate Similarity NPC469877
0.7944 Intermediate Similarity NPC65523
0.7941 Intermediate Similarity NPC470958
0.7941 Intermediate Similarity NPC470957
0.7928 Intermediate Similarity NPC317687
0.7928 Intermediate Similarity NPC302146
0.7928 Intermediate Similarity NPC126691
0.7925 Intermediate Similarity NPC137430
0.7925 Intermediate Similarity NPC183571
0.7913 Intermediate Similarity NPC109973
0.7909 Intermediate Similarity NPC286880
0.7909 Intermediate Similarity NPC50223
0.7905 Intermediate Similarity NPC218383
0.7905 Intermediate Similarity NPC241221
0.789 Intermediate Similarity NPC472219
0.789 Intermediate Similarity NPC476479
0.789 Intermediate Similarity NPC293850
0.789 Intermediate Similarity NPC472217
0.789 Intermediate Similarity NPC473288
0.789 Intermediate Similarity NPC472218
0.7885 Intermediate Similarity NPC285513
0.7885 Intermediate Similarity NPC254496
0.7885 Intermediate Similarity NPC40812
0.7876 Intermediate Similarity NPC266728
0.7876 Intermediate Similarity NPC96312
0.7876 Intermediate Similarity NPC49492
0.7876 Intermediate Similarity NPC179626
0.7876 Intermediate Similarity NPC40632
0.7876 Intermediate Similarity NPC328374
0.7876 Intermediate Similarity NPC251236
0.787 Intermediate Similarity NPC196528
0.787 Intermediate Similarity NPC102352
0.787 Intermediate Similarity NPC472935
0.787 Intermediate Similarity NPC477877
0.787 Intermediate Similarity NPC284365
0.787 Intermediate Similarity NPC123726
0.787 Intermediate Similarity NPC111952
0.7864 Intermediate Similarity NPC108141
0.7864 Intermediate Similarity NPC266899
0.7864 Intermediate Similarity NPC36954
0.7863 Intermediate Similarity NPC91693
0.7863 Intermediate Similarity NPC18945
0.7863 Intermediate Similarity NPC265557
0.7863 Intermediate Similarity NPC105926
0.7863 Intermediate Similarity NPC67251
0.7857 Intermediate Similarity NPC49451
0.785 Intermediate Similarity NPC270046
0.785 Intermediate Similarity NPC478057
0.785 Intermediate Similarity NPC474775
0.7845 Intermediate Similarity NPC202051
0.7845 Intermediate Similarity NPC472001
0.7843 Intermediate Similarity NPC476416
0.7838 Intermediate Similarity NPC317107
0.7838 Intermediate Similarity NPC179798
0.7838 Intermediate Similarity NPC304180
0.783 Intermediate Similarity NPC115862
0.783 Intermediate Similarity NPC154127
0.7826 Intermediate Similarity NPC472933
0.7818 Intermediate Similarity NPC310546
0.7818 Intermediate Similarity NPC153239
0.781 Intermediate Similarity NPC222303
0.781 Intermediate Similarity NPC308567
0.781 Intermediate Similarity NPC70733
0.781 Intermediate Similarity NPC187761
0.781 Intermediate Similarity NPC83895
0.781 Intermediate Similarity NPC56071
0.781 Intermediate Similarity NPC261377
0.781 Intermediate Similarity NPC23364
0.781 Intermediate Similarity NPC255592
0.7807 Intermediate Similarity NPC473968
0.7798 Intermediate Similarity NPC293512
0.7798 Intermediate Similarity NPC59530
0.7798 Intermediate Similarity NPC67321
0.7798 Intermediate Similarity NPC187435
0.7788 Intermediate Similarity NPC469528
0.7788 Intermediate Similarity NPC472274
0.7788 Intermediate Similarity NPC220293
0.7788 Intermediate Similarity NPC469369
0.7788 Intermediate Similarity NPC473798
0.7788 Intermediate Similarity NPC475633
0.7778 Intermediate Similarity NPC296950
0.7778 Intermediate Similarity NPC471293
0.7778 Intermediate Similarity NPC118911
0.7778 Intermediate Similarity NPC312833
0.7778 Intermediate Similarity NPC220964
0.7778 Intermediate Similarity NPC475676
0.7778 Intermediate Similarity NPC146731
0.7778 Intermediate Similarity NPC28532
0.7778 Intermediate Similarity NPC475036
0.7768 Intermediate Similarity NPC280782
0.7768 Intermediate Similarity NPC37739
0.7768 Intermediate Similarity NPC269530
0.7768 Intermediate Similarity NPC46388
0.7768 Intermediate Similarity NPC236217
0.7767 Intermediate Similarity NPC196227
0.7757 Intermediate Similarity NPC473163
0.7757 Intermediate Similarity NPC295791
0.7748 Intermediate Similarity NPC161816
0.7748 Intermediate Similarity NPC114961
0.7748 Intermediate Similarity NPC27551
0.7748 Intermediate Similarity NPC41551
0.7748 Intermediate Similarity NPC206595
0.7748 Intermediate Similarity NPC115257
0.7745 Intermediate Similarity NPC472197
0.7745 Intermediate Similarity NPC475441
0.7745 Intermediate Similarity NPC475972
0.7739 Intermediate Similarity NPC18233
0.7739 Intermediate Similarity NPC17772
0.7739 Intermediate Similarity NPC276758
0.7739 Intermediate Similarity NPC106644
0.7736 Intermediate Similarity NPC51370
0.7736 Intermediate Similarity NPC476274
0.7727 Intermediate Similarity NPC154608
0.7727 Intermediate Similarity NPC469916
0.7727 Intermediate Similarity NPC258323
0.7727 Intermediate Similarity NPC137286
0.7727 Intermediate Similarity NPC192813
0.7727 Intermediate Similarity NPC472439
0.7727 Intermediate Similarity NPC277017
0.7727 Intermediate Similarity NPC71220
0.7727 Intermediate Similarity NPC19412
0.7719 Intermediate Similarity NPC235539
0.7719 Intermediate Similarity NPC152199
0.7719 Intermediate Similarity NPC134869
0.7708 Intermediate Similarity NPC103634
0.7706 Intermediate Similarity NPC162033
0.7706 Intermediate Similarity NPC210178
0.7706 Intermediate Similarity NPC292588
0.7706 Intermediate Similarity NPC471333
0.7706 Intermediate Similarity NPC472751
0.7706 Intermediate Similarity NPC472749
0.7706 Intermediate Similarity NPC127609
0.7706 Intermediate Similarity NPC471332
0.7706 Intermediate Similarity NPC96377
0.7705 Intermediate Similarity NPC476193
0.7705 Intermediate Similarity NPC102316
0.7699 Intermediate Similarity NPC474410

  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 NPC470104 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
0.7745 Intermediate Similarity NPD7983 Approved
0.7658 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD6686 Approved
0.75 Intermediate Similarity NPD5779 Approved
0.75 Intermediate Similarity NPD5778 Approved
0.7476 Intermediate Similarity NPD6698 Approved
0.7476 Intermediate Similarity NPD46 Approved
0.7417 Intermediate Similarity NPD8328 Phase 3
0.7411 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD6373 Approved
0.7345 Intermediate Similarity NPD6372 Approved
0.7333 Intermediate Similarity NPD6399 Phase 3
0.7321 Intermediate Similarity NPD6412 Phase 2
0.7304 Intermediate Similarity NPD8297 Approved
0.725 Intermediate Similarity NPD8517 Approved
0.725 Intermediate Similarity NPD8515 Approved
0.725 Intermediate Similarity NPD8516 Approved
0.725 Intermediate Similarity NPD8513 Phase 3
0.7238 Intermediate Similarity NPD6411 Approved
0.7222 Intermediate Similarity NPD7902 Approved
0.7217 Intermediate Similarity NPD6650 Approved
0.7217 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD6649 Approved
0.7203 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6319 Approved
0.7156 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD7507 Approved
0.713 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6371 Approved
0.7094 Intermediate Similarity NPD4632 Approved
0.708 Intermediate Similarity NPD6402 Approved
0.708 Intermediate Similarity NPD5739 Approved
0.708 Intermediate Similarity NPD6675 Approved
0.708 Intermediate Similarity NPD7128 Approved
0.7059 Intermediate Similarity NPD7115 Discovery
0.7048 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6101 Approved
0.7043 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6053 Discontinued
0.7008 Intermediate Similarity NPD7260 Phase 2
0.7 Intermediate Similarity NPD5696 Approved
0.6984 Remote Similarity NPD7319 Approved
0.6972 Remote Similarity NPD7839 Suspended
0.696 Remote Similarity NPD8074 Phase 3
0.6957 Remote Similarity NPD6881 Approved
0.6957 Remote Similarity NPD7320 Approved
0.6957 Remote Similarity NPD6899 Approved
0.6949 Remote Similarity NPD8133 Approved
0.6944 Remote Similarity NPD7748 Approved
0.6944 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7900 Approved
0.6937 Remote Similarity NPD7640 Approved
0.6937 Remote Similarity NPD7639 Approved
0.6923 Remote Similarity NPD8130 Phase 1
0.6909 Remote Similarity NPD6083 Phase 2
0.6909 Remote Similarity NPD6084 Phase 2
0.687 Remote Similarity NPD5697 Approved
0.687 Remote Similarity NPD5954 Clinical (unspecified phase)
0.687 Remote Similarity NPD5701 Approved
0.687 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6882 Approved
0.6847 Remote Similarity NPD4225 Approved
0.6847 Remote Similarity NPD7638 Approved
0.6838 Remote Similarity NPD7290 Approved
0.6838 Remote Similarity NPD7102 Approved
0.6838 Remote Similarity NPD6883 Approved
0.6829 Remote Similarity NPD6921 Approved
0.6825 Remote Similarity NPD8293 Discontinued
0.6822 Remote Similarity NPD7838 Discovery
0.68 Remote Similarity NPD7492 Approved
0.6783 Remote Similarity NPD6008 Approved
0.678 Remote Similarity NPD6847 Approved
0.678 Remote Similarity NPD6617 Approved
0.678 Remote Similarity NPD6869 Approved
0.6777 Remote Similarity NPD6009 Approved
0.6772 Remote Similarity NPD7736 Approved
0.6762 Remote Similarity NPD5786 Approved
0.6759 Remote Similarity NPD7515 Phase 2
0.6752 Remote Similarity NPD6014 Approved
0.6752 Remote Similarity NPD6012 Approved
0.6752 Remote Similarity NPD6013 Approved
0.6748 Remote Similarity NPD6054 Approved
0.6748 Remote Similarity NPD6059 Approved
0.6746 Remote Similarity NPD6616 Approved
0.6727 Remote Similarity NPD5695 Phase 3
0.672 Remote Similarity NPD7604 Phase 2
0.6699 Remote Similarity NPD6435 Approved
0.6694 Remote Similarity NPD5983 Phase 2
0.6693 Remote Similarity NPD7078 Approved
0.6692 Remote Similarity NPD6845 Suspended
0.6667 Remote Similarity NPD5211 Phase 2
0.6667 Remote Similarity NPD8299 Approved
0.6667 Remote Similarity NPD8342 Approved
0.6667 Remote Similarity NPD8341 Approved
0.6667 Remote Similarity NPD8340 Approved
0.6667 Remote Similarity NPD6011 Approved
0.664 Remote Similarity NPD6370 Approved
0.6639 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5282 Discontinued
0.6635 Remote Similarity NPD6110 Phase 1
0.6634 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6614 Remote Similarity NPD6336 Discontinued
0.6613 Remote Similarity NPD8377 Approved
0.6613 Remote Similarity NPD8294 Approved
0.6607 Remote Similarity NPD4755 Approved
0.6606 Remote Similarity NPD8035 Phase 2
0.6606 Remote Similarity NPD8034 Phase 2
0.6606 Remote Similarity NPD7637 Suspended
0.6604 Remote Similarity NPD7334 Approved
0.6604 Remote Similarity NPD6684 Approved
0.6604 Remote Similarity NPD6409 Approved
0.6604 Remote Similarity NPD5330 Approved
0.6604 Remote Similarity NPD7521 Approved
0.6604 Remote Similarity NPD7146 Approved
0.6585 Remote Similarity NPD7328 Approved
0.6585 Remote Similarity NPD7327 Approved
0.6579 Remote Similarity NPD5344 Discontinued
0.6577 Remote Similarity NPD5210 Approved
0.6577 Remote Similarity NPD4629 Approved
0.6577 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6574 Remote Similarity NPD5328 Approved
0.6571 Remote Similarity NPD4786 Approved
0.656 Remote Similarity NPD7503 Approved
0.656 Remote Similarity NPD8335 Approved
0.656 Remote Similarity NPD8380 Approved
0.656 Remote Similarity NPD8379 Approved
0.656 Remote Similarity NPD6016 Approved
0.656 Remote Similarity NPD8033 Approved
0.656 Remote Similarity NPD8444 Approved
0.656 Remote Similarity NPD6015 Approved
0.656 Remote Similarity NPD8296 Approved
0.656 Remote Similarity NPD8378 Approved
0.6555 Remote Similarity NPD4634 Approved
0.6552 Remote Similarity NPD5141 Approved
0.6542 Remote Similarity NPD7524 Approved
0.6542 Remote Similarity NPD3573 Approved
0.6538 Remote Similarity NPD3667 Approved
0.6532 Remote Similarity NPD7516 Approved
0.6518 Remote Similarity NPD4697 Phase 3
0.6508 Remote Similarity NPD5988 Approved
0.6505 Remote Similarity NPD5368 Approved
0.6493 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4700 Approved
0.6491 Remote Similarity NPD4696 Approved
0.6491 Remote Similarity NPD5285 Approved
0.6491 Remote Similarity NPD5286 Approved
0.6484 Remote Similarity NPD8451 Approved
0.6481 Remote Similarity NPD6672 Approved
0.6481 Remote Similarity NPD6903 Approved
0.6481 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5737 Approved
0.6476 Remote Similarity NPD7154 Phase 3
0.6455 Remote Similarity NPD5281 Approved
0.6455 Remote Similarity NPD5284 Approved
0.6455 Remote Similarity NPD6079 Approved
0.6449 Remote Similarity NPD3618 Phase 1
0.6434 Remote Similarity NPD8448 Approved
0.6423 Remote Similarity NPD6274 Approved
0.6422 Remote Similarity NPD4753 Phase 2
0.6415 Remote Similarity NPD3666 Approved
0.6415 Remote Similarity NPD3665 Phase 1
0.6415 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6415 Remote Similarity NPD3133 Approved
0.64 Remote Similarity NPD7101 Approved
0.64 Remote Similarity NPD7100 Approved
0.6389 Remote Similarity NPD4251 Approved
0.6389 Remote Similarity NPD4250 Approved
0.6381 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6381 Remote Similarity NPD4269 Approved
0.6381 Remote Similarity NPD4270 Approved
0.6379 Remote Similarity NPD5226 Approved
0.6379 Remote Similarity NPD4633 Approved
0.6379 Remote Similarity NPD5225 Approved
0.6379 Remote Similarity NPD7632 Discontinued
0.6379 Remote Similarity NPD5224 Approved
0.6364 Remote Similarity NPD5785 Approved
0.6356 Remote Similarity NPD4767 Approved
0.6356 Remote Similarity NPD4768 Approved
0.6355 Remote Similarity NPD1694 Approved
0.6355 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6346 Remote Similarity NPD4822 Approved
0.6346 Remote Similarity NPD4819 Approved
0.6346 Remote Similarity NPD4821 Approved
0.6346 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6346 Remote Similarity NPD4820 Approved
0.6337 Remote Similarity NPD8039 Approved
0.6325 Remote Similarity NPD5175 Approved
0.6325 Remote Similarity NPD5174 Approved
0.6321 Remote Similarity NPD5362 Discontinued
0.6321 Remote Similarity NPD6695 Phase 3
0.632 Remote Similarity NPD6335 Approved
0.632 Remote Similarity NPD7641 Discontinued
0.6299 Remote Similarity NPD6908 Approved
0.6299 Remote Similarity NPD6909 Approved
0.6296 Remote Similarity NPD4249 Approved
0.6296 Remote Similarity NPD4623 Approved
0.6296 Remote Similarity NPD4519 Discontinued
0.6296 Remote Similarity NPD6098 Approved
0.6293 Remote Similarity NPD5223 Approved
0.6288 Remote Similarity NPD8390 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