Structure

Physi-Chem Properties

Molecular Weight:  726.43
Volume:  779.413
LogP:  7.16
LogD:  5.513
LogS:  -5.527
# Rotatable Bonds:  20
TPSA:  139.32
# H-Bond Aceptor:  10
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.088
Synthetic Accessibility Score:  5.504
Fsp3:  0.643
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:  -4.963
MDCK Permeability:  1.191164119518362e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.378
Human Intestinal Absorption (HIA):  0.126
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  92.06916046142578%
Volume Distribution (VD):  1.877
Pgp-substrate:  2.8153955936431885%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.459
CYP2C19-inhibitor:  0.552
CYP2C19-substrate:  0.886
CYP2C9-inhibitor:  0.893
CYP2C9-substrate:  0.028
CYP2D6-inhibitor:  0.126
CYP2D6-substrate:  0.067
CYP3A4-inhibitor:  0.931
CYP3A4-substrate:  0.918

ADMET: Excretion

Clearance (CL):  2.641
Half-life (T1/2):  0.032

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.999
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.577
Maximum Recommended Daily Dose:  0.248
Skin Sensitization:  0.114
Carcinogencity:  0.004
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.056

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

  Natural Product: NPC123908

Natural Product ID:  NPC123908
Common Name*:   3-Acetyl-11-(3-Methylbutanoyl)-13-Propanoylilikonapyrone
IUPAC Name:   [(E,2R,3R,4R,5R,8R)-2-[6-[(2S,3S)-3-acetyloxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]-8-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)-4,6-dimethyl-5-propanoyloxynon-6-en-3-yl] 3-methylbutanoate
Synonyms:  
Standard InCHIKey:  YBYLWJQWQYRXKJ-JIBIURQTSA-N
Standard InCHI:  InChI=1S/C42H62O10/c1-16-32-24(8)36(46)26(10)38(49-32)22(6)20-23(7)39(50-34(44)18-3)29(13)42(51-35(45)19-21(4)5)30(14)41-28(12)37(47)27(11)40(52-41)25(9)33(17-2)48-31(15)43/h20-22,25,29-30,33,39,42H,16-19H2,1-15H3/b23-20+/t22-,25+,29+,30+,33+,39+,42-/m1/s1
SMILES:  CCc1c(C)c(=O)c(C)c([C@H](C)/C=C(C)/[C@@H]([C@H](C)[C@H]([C@@H](C)c2c(C)c(=O)c(C)c([C@@H](C)[C@H](CC)OC(=O)C)o2)OC(=O)CC(C)C)OC(=O)CC)o1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3087306
PubChem CID:   72946417
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32933 pulmonate mollusks Species n.a. n.a. n.a. n.a. n.a. PMID[24180210]

☑ 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
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 7000.0 nM PMID[551597]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 2000.0 nM PMID[551597]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4000.0 nM PMID[551597]
NPT81 Cell Line A549 Homo sapiens IC50 = 3000.0 nM PMID[551597]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9000.0 nM PMID[551597]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3000.0 nM PMID[551597]

☑ 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 NPC123908 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 NPC10080
0.95 High Similarity NPC47220
0.95 High Similarity NPC186332
0.9136 High Similarity NPC242233
0.8025 Intermediate Similarity NPC469880
0.8023 Intermediate Similarity NPC92633
0.8 Intermediate Similarity NPC477204
0.8 Intermediate Similarity NPC159092
0.7952 Intermediate Similarity NPC139712
0.7927 Intermediate Similarity NPC471225
0.7889 Intermediate Similarity NPC114172
0.7889 Intermediate Similarity NPC471324
0.7889 Intermediate Similarity NPC206679
0.7816 Intermediate Similarity NPC67081
0.7816 Intermediate Similarity NPC471223
0.7802 Intermediate Similarity NPC109406
0.7778 Intermediate Similarity NPC177668
0.7765 Intermediate Similarity NPC184208
0.7765 Intermediate Similarity NPC8538
0.775 Intermediate Similarity NPC477084
0.7711 Intermediate Similarity NPC477203
0.7692 Intermediate Similarity NPC476084
0.7692 Intermediate Similarity NPC476075
0.7667 Intermediate Similarity NPC133450
0.764 Intermediate Similarity NPC199382
0.764 Intermediate Similarity NPC74139
0.7634 Intermediate Similarity NPC300710
0.7625 Intermediate Similarity NPC469660
0.759 Intermediate Similarity NPC477202
0.7586 Intermediate Similarity NPC107498
0.7586 Intermediate Similarity NPC185949
0.7582 Intermediate Similarity NPC3952
0.7561 Intermediate Similarity NPC474758
0.7558 Intermediate Similarity NPC471325
0.7558 Intermediate Similarity NPC315731
0.7553 Intermediate Similarity NPC255410
0.7531 Intermediate Similarity NPC477087
0.7531 Intermediate Similarity NPC477086
0.7529 Intermediate Similarity NPC178277
0.7527 Intermediate Similarity NPC256368
0.75 Intermediate Similarity NPC269841
0.75 Intermediate Similarity NPC97516
0.75 Intermediate Similarity NPC315394
0.75 Intermediate Similarity NPC473944
0.7474 Intermediate Similarity NPC120299
0.7474 Intermediate Similarity NPC475332
0.747 Intermediate Similarity NPC285840
0.747 Intermediate Similarity NPC327041
0.7468 Intermediate Similarity NPC472266
0.7439 Intermediate Similarity NPC477085
0.7419 Intermediate Similarity NPC238090
0.7419 Intermediate Similarity NPC472196
0.7419 Intermediate Similarity NPC320552
0.7419 Intermediate Similarity NPC472195
0.7396 Intermediate Similarity NPC124181
0.7396 Intermediate Similarity NPC475653
0.7386 Intermediate Similarity NPC318468
0.7386 Intermediate Similarity NPC170377
0.7386 Intermediate Similarity NPC170286
0.7368 Intermediate Similarity NPC288350
0.7368 Intermediate Similarity NPC173329
0.7363 Intermediate Similarity NPC69713
0.7363 Intermediate Similarity NPC473151
0.7363 Intermediate Similarity NPC233997
0.7349 Intermediate Similarity NPC476355
0.7349 Intermediate Similarity NPC140287
0.7349 Intermediate Similarity NPC259599
0.7349 Intermediate Similarity NPC474551
0.7349 Intermediate Similarity NPC15499
0.7349 Intermediate Similarity NPC294434
0.7349 Intermediate Similarity NPC117746
0.734 Intermediate Similarity NPC159698
0.7333 Intermediate Similarity NPC474045
0.7333 Intermediate Similarity NPC261253
0.7333 Intermediate Similarity NPC220478
0.7333 Intermediate Similarity NPC471480
0.7326 Intermediate Similarity NPC471299
0.7326 Intermediate Similarity NPC270126
0.7317 Intermediate Similarity NPC475762
0.7317 Intermediate Similarity NPC133098
0.7294 Intermediate Similarity NPC84360
0.7294 Intermediate Similarity NPC316324
0.7294 Intermediate Similarity NPC57744
0.7292 Intermediate Similarity NPC100912
0.7292 Intermediate Similarity NPC153559
0.7284 Intermediate Similarity NPC151481
0.7284 Intermediate Similarity NPC101622
0.7263 Intermediate Similarity NPC281134
0.7253 Intermediate Similarity NPC316138
0.7253 Intermediate Similarity NPC313658
0.7253 Intermediate Similarity NPC478144
0.7253 Intermediate Similarity NPC102640
0.7245 Intermediate Similarity NPC219038
0.7241 Intermediate Similarity NPC469802
0.7241 Intermediate Similarity NPC474510
0.7241 Intermediate Similarity NPC474739
0.7234 Intermediate Similarity NPC248193
0.7229 Intermediate Similarity NPC474543
0.7229 Intermediate Similarity NPC238425
0.7229 Intermediate Similarity NPC472018
0.7229 Intermediate Similarity NPC222244
0.7229 Intermediate Similarity NPC185186
0.7229 Intermediate Similarity NPC16349
0.7229 Intermediate Similarity NPC327383
0.7222 Intermediate Similarity NPC474547
0.7222 Intermediate Similarity NPC471494
0.7222 Intermediate Similarity NPC197903
0.7222 Intermediate Similarity NPC215364
0.7222 Intermediate Similarity NPC99395
0.7216 Intermediate Similarity NPC473307
0.7216 Intermediate Similarity NPC72647
0.7216 Intermediate Similarity NPC107806
0.7209 Intermediate Similarity NPC128276
0.7204 Intermediate Similarity NPC475748
0.7204 Intermediate Similarity NPC179394
0.7204 Intermediate Similarity NPC144133
0.7204 Intermediate Similarity NPC327253
0.7195 Intermediate Similarity NPC4299
0.7195 Intermediate Similarity NPC316029
0.7195 Intermediate Similarity NPC37929
0.7195 Intermediate Similarity NPC64234
0.7195 Intermediate Similarity NPC315285
0.7191 Intermediate Similarity NPC16488
0.7191 Intermediate Similarity NPC116543
0.7191 Intermediate Similarity NPC44261
0.7191 Intermediate Similarity NPC474193
0.7191 Intermediate Similarity NPC12283
0.7188 Intermediate Similarity NPC301596
0.7188 Intermediate Similarity NPC299396
0.7188 Intermediate Similarity NPC172998
0.7176 Intermediate Similarity NPC123360
0.7174 Intermediate Similarity NPC106051
0.7174 Intermediate Similarity NPC106332
0.7172 Intermediate Similarity NPC471599
0.7172 Intermediate Similarity NPC473596
0.716 Intermediate Similarity NPC313444
0.716 Intermediate Similarity NPC470256
0.7159 Intermediate Similarity NPC301477
0.7159 Intermediate Similarity NPC79277
0.7159 Intermediate Similarity NPC471552
0.7159 Intermediate Similarity NPC112868
0.7159 Intermediate Similarity NPC475481
0.7159 Intermediate Similarity NPC281949
0.7159 Intermediate Similarity NPC25684
0.7159 Intermediate Similarity NPC473339
0.7157 Intermediate Similarity NPC473807
0.7143 Intermediate Similarity NPC204048
0.7143 Intermediate Similarity NPC284902
0.7143 Intermediate Similarity NPC315395
0.7143 Intermediate Similarity NPC316426
0.7143 Intermediate Similarity NPC50637
0.7143 Intermediate Similarity NPC54705
0.7143 Intermediate Similarity NPC102996
0.7128 Intermediate Similarity NPC221282
0.7128 Intermediate Similarity NPC166110
0.7126 Intermediate Similarity NPC477088
0.7126 Intermediate Similarity NPC271632
0.7125 Intermediate Similarity NPC469446
0.7113 Intermediate Similarity NPC475446
0.7113 Intermediate Similarity NPC311241
0.7111 Intermediate Similarity NPC160517
0.7111 Intermediate Similarity NPC186155
0.7111 Intermediate Similarity NPC78673
0.7108 Intermediate Similarity NPC163003
0.71 Intermediate Similarity NPC197736
0.7097 Intermediate Similarity NPC166919
0.7097 Intermediate Similarity NPC280833
0.7093 Intermediate Similarity NPC171204
0.7093 Intermediate Similarity NPC141789
0.7093 Intermediate Similarity NPC41780
0.7093 Intermediate Similarity NPC476028
0.7093 Intermediate Similarity NPC187568
0.7089 Intermediate Similarity NPC34883
0.7083 Intermediate Similarity NPC291709
0.7083 Intermediate Similarity NPC273197
0.7083 Intermediate Similarity NPC234339
0.7083 Intermediate Similarity NPC241407
0.7079 Intermediate Similarity NPC173609
0.7079 Intermediate Similarity NPC35556
0.7079 Intermediate Similarity NPC471218
0.7073 Intermediate Similarity NPC88877
0.7073 Intermediate Similarity NPC476591
0.7073 Intermediate Similarity NPC232812
0.7065 Intermediate Similarity NPC476600
0.7065 Intermediate Similarity NPC471056
0.7065 Intermediate Similarity NPC477959
0.7065 Intermediate Similarity NPC471055
0.7065 Intermediate Similarity NPC160138
0.7065 Intermediate Similarity NPC475087
0.7065 Intermediate Similarity NPC241054
0.7065 Intermediate Similarity NPC478145
0.7065 Intermediate Similarity NPC475703
0.7059 Intermediate Similarity NPC244166
0.7059 Intermediate Similarity NPC329852
0.7053 Intermediate Similarity NPC476300
0.7053 Intermediate Similarity NPC61201
0.7053 Intermediate Similarity NPC475657
0.7051 Intermediate Similarity NPC15193
0.7045 Intermediate Similarity NPC281132
0.7045 Intermediate Similarity NPC133226

  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 NPC123908 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
0.7582 Intermediate Similarity NPD6698 Approved
0.7582 Intermediate Similarity NPD46 Approved
0.7391 Intermediate Similarity NPD7838 Discovery
0.7216 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6053 Discontinued
0.6813 Remote Similarity NPD7154 Phase 3
0.6771 Remote Similarity NPD7983 Approved
0.6739 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4250 Approved
0.6702 Remote Similarity NPD4251 Approved
0.67 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8039 Approved
0.6634 Remote Similarity NPD7640 Approved
0.6634 Remote Similarity NPD7639 Approved
0.6596 Remote Similarity NPD4249 Approved
0.6571 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5778 Approved
0.6531 Remote Similarity NPD5779 Approved
0.6522 Remote Similarity NPD5209 Approved
0.6509 Remote Similarity NPD6686 Approved
0.65 Remote Similarity NPD7839 Suspended
0.6489 Remote Similarity NPD1694 Approved
0.6481 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6648 Approved
0.6452 Remote Similarity NPD6110 Phase 1
0.6429 Remote Similarity NPD7637 Suspended
0.6408 Remote Similarity NPD5344 Discontinued
0.6392 Remote Similarity NPD1695 Approved
0.6373 Remote Similarity NPD4225 Approved
0.6327 Remote Similarity NPD5785 Approved
0.6316 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6304 Remote Similarity NPD5790 Clinical (unspecified phase)
0.63 Remote Similarity NPD5282 Discontinued
0.625 Remote Similarity NPD6409 Approved
0.625 Remote Similarity NPD5330 Approved
0.625 Remote Similarity NPD7521 Approved
0.625 Remote Similarity NPD6684 Approved
0.625 Remote Similarity NPD7334 Approved
0.625 Remote Similarity NPD7146 Approved
0.6239 Remote Similarity NPD6371 Approved
0.6184 Remote Similarity NPD6927 Phase 3
0.6154 Remote Similarity NPD4756 Discovery
0.6146 Remote Similarity NPD5363 Approved
0.6139 Remote Similarity NPD7900 Approved
0.6139 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6139 Remote Similarity NPD7748 Approved
0.6129 Remote Similarity NPD4820 Approved
0.6129 Remote Similarity NPD4819 Approved
0.6129 Remote Similarity NPD4821 Approved
0.6129 Remote Similarity NPD4822 Approved
0.6125 Remote Similarity NPD8779 Phase 3
0.6122 Remote Similarity NPD6903 Approved
0.6122 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6122 Remote Similarity NPD6672 Approved
0.6122 Remote Similarity NPD5737 Approved
0.6105 Remote Similarity NPD5362 Discontinued
0.6087 Remote Similarity NPD4271 Approved
0.6087 Remote Similarity NPD4268 Approved
0.6078 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6061 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6061 Remote Similarity NPD6101 Approved
0.6061 Remote Similarity NPD6051 Approved
0.6038 Remote Similarity NPD7632 Discontinued
0.6 Remote Similarity NPD6435 Approved
0.6 Remote Similarity NPD4269 Approved
0.6 Remote Similarity NPD4270 Approved
0.5983 Remote Similarity NPD7503 Approved
0.5983 Remote Similarity NPD8513 Phase 3
0.5963 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5962 Remote Similarity NPD7902 Approved
0.5941 Remote Similarity NPD5693 Phase 1
0.5941 Remote Similarity NPD6411 Approved
0.5938 Remote Similarity NPD5332 Approved
0.5938 Remote Similarity NPD5331 Approved
0.593 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5918 Remote Similarity NPD5786 Approved
0.5918 Remote Similarity NPD6422 Discontinued
0.5914 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5913 Remote Similarity NPD7115 Discovery
0.5895 Remote Similarity NPD4790 Discontinued
0.5895 Remote Similarity NPD5369 Approved
0.5882 Remote Similarity NPD6399 Phase 3
0.5882 Remote Similarity NPD7829 Approved
0.5882 Remote Similarity NPD7830 Approved
0.5872 Remote Similarity NPD6008 Approved
0.5859 Remote Similarity NPD1282 Approved
0.5847 Remote Similarity NPD8033 Approved
0.5847 Remote Similarity NPD8517 Approved
0.5847 Remote Similarity NPD8515 Approved
0.5847 Remote Similarity NPD8516 Approved
0.581 Remote Similarity NPD6083 Phase 2
0.581 Remote Similarity NPD6084 Phase 2
0.5804 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4252 Approved
0.5789 Remote Similarity NPD5368 Approved
0.5789 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5784 Remote Similarity NPD7515 Phase 2
0.5773 Remote Similarity NPD6695 Phase 3
0.5769 Remote Similarity NPD5695 Phase 3
0.5763 Remote Similarity NPD8377 Approved
0.5763 Remote Similarity NPD8294 Approved
0.5747 Remote Similarity NPD7331 Phase 2
0.5743 Remote Similarity NPD6080 Approved
0.5743 Remote Similarity NPD6904 Approved
0.5743 Remote Similarity NPD6673 Approved
0.5726 Remote Similarity NPD7328 Approved
0.5726 Remote Similarity NPD7327 Approved
0.5714 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8444 Approved
0.5714 Remote Similarity NPD8378 Approved
0.5714 Remote Similarity NPD8380 Approved
0.5714 Remote Similarity NPD8296 Approved
0.5714 Remote Similarity NPD8379 Approved
0.5714 Remote Similarity NPD8335 Approved
0.57 Remote Similarity NPD7750 Discontinued
0.5682 Remote Similarity NPD4247 Clinical (unspecified phase)
0.568 Remote Similarity NPD7260 Phase 2
0.5678 Remote Similarity NPD7516 Approved
0.5676 Remote Similarity NPD6412 Phase 2
0.5664 Remote Similarity NPD2067 Discontinued
0.5656 Remote Similarity NPD7507 Approved
0.5641 Remote Similarity NPD7500 Approved
0.5636 Remote Similarity NPD5909 Discontinued
0.5631 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5631 Remote Similarity NPD6050 Approved
0.5625 Remote Similarity NPD4695 Discontinued
0.562 Remote Similarity NPD7642 Approved
0.5619 Remote Similarity NPD6356 Clinical (unspecified phase)
0.561 Remote Similarity NPD8074 Phase 3
0.5607 Remote Similarity NPD5696 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