Structure

Physi-Chem Properties

Molecular Weight:  260.16
Volume:  266.162
LogP:  0.247
LogD:  -0.531
LogS:  -2.013
# Rotatable Bonds:  2
TPSA:  101.15
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.433
Synthetic Accessibility Score:  4.828
Fsp3:  0.846
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.325
MDCK Permeability:  0.00016238450189121068
Pgp-inhibitor:  0.0
Pgp-substrate:  0.426
Human Intestinal Absorption (HIA):  0.333
20% Bioavailability (F20%):  0.919
30% Bioavailability (F30%):  0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.341
Plasma Protein Binding (PPB):  70.79446411132812%
Volume Distribution (VD):  0.842
Pgp-substrate:  40.9453010559082%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.243
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.798
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.494
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.225

ADMET: Excretion

Clearance (CL):  2.048
Half-life (T1/2):  0.618

ADMET: Toxicity

hERG Blockers:  0.046
Human Hepatotoxicity (H-HT):  0.102
Drug-inuced Liver Injury (DILI):  0.022
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.256
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.098
Carcinogencity:  0.016
Eye Corrosion:  0.003
Eye Irritation:  0.026
Respiratory Toxicity:  0.132

Download Data

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

  Natural Product: NPC236707

Natural Product ID:  NPC236707
Common Name*:   Wilsonol H
IUPAC Name:   (1R,2R,3R,4S)-1-[(E,3R)-3-hydroxybut-1-enyl]-2,6,6-trimethylcyclohexane-1,2,3,4-tetrol
Synonyms:  
Standard InCHIKey:  OPHSNQSZCRVYBC-SARQSPIOSA-N
Standard InCHI:  InChI=1S/C13H24O5/c1-8(14)5-6-13(18)11(2,3)7-9(15)10(16)12(13,4)17/h5-6,8-10,14-18H,7H2,1-4H3/b6-5+/t8-,9+,10-,12-,13-/m1/s1
SMILES:  C[C@H](/C=C/[C@@]1(O)C(C)(C)C[C@@H]([C@H]([C@@]1(C)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2407698
PubChem CID:   71746620
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
NPO32875 cinnamomum wilsonii Species Lauraceae Eukaryota Leaves n.a. n.a. PMID[23822611]

☑ 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
NPT660 Cell Line SW480 Homo sapiens IC50 > 10000.0 nM PMID[514301]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[514301]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[514301]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000.0 nM PMID[514301]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[514301]

☑ 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 NPC236707 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
0.9867 High Similarity NPC471270
0.9733 High Similarity NPC471266
0.9733 High Similarity NPC95124
0.8889 High Similarity NPC471267
0.8875 High Similarity NPC185605
0.8875 High Similarity NPC471987
0.875 High Similarity NPC259858
0.8667 High Similarity NPC471268
0.8667 High Similarity NPC471271
0.8667 High Similarity NPC471272
0.8276 Intermediate Similarity NPC41554
0.8276 Intermediate Similarity NPC97404
0.8267 Intermediate Similarity NPC471238
0.8256 Intermediate Similarity NPC115607
0.8222 Intermediate Similarity NPC120446
0.8171 Intermediate Similarity NPC249423
0.8161 Intermediate Similarity NPC3345
0.8161 Intermediate Similarity NPC11216
0.8161 Intermediate Similarity NPC80561
0.8161 Intermediate Similarity NPC204188
0.8161 Intermediate Similarity NPC329596
0.8161 Intermediate Similarity NPC291484
0.8095 Intermediate Similarity NPC83702
0.8068 Intermediate Similarity NPC275671
0.8049 Intermediate Similarity NPC287749
0.8049 Intermediate Similarity NPC96362
0.8046 Intermediate Similarity NPC470361
0.8046 Intermediate Similarity NPC97103
0.8046 Intermediate Similarity NPC259875
0.8046 Intermediate Similarity NPC187785
0.7978 Intermediate Similarity NPC310013
0.7978 Intermediate Similarity NPC119379
0.7955 Intermediate Similarity NPC191323
0.7955 Intermediate Similarity NPC475751
0.7955 Intermediate Similarity NPC473956
0.7952 Intermediate Similarity NPC476646
0.7949 Intermediate Similarity NPC477792
0.7931 Intermediate Similarity NPC133588
0.7931 Intermediate Similarity NPC474668
0.7912 Intermediate Similarity NPC103165
0.7912 Intermediate Similarity NPC288970
0.7912 Intermediate Similarity NPC210717
0.7907 Intermediate Similarity NPC299068
0.7907 Intermediate Similarity NPC255143
0.7901 Intermediate Similarity NPC85105
0.7901 Intermediate Similarity NPC149550
0.7848 Intermediate Similarity NPC265485
0.7848 Intermediate Similarity NPC95165
0.7848 Intermediate Similarity NPC220939
0.7841 Intermediate Similarity NPC109744
0.7841 Intermediate Similarity NPC473100
0.7826 Intermediate Similarity NPC477226
0.7805 Intermediate Similarity NPC475980
0.7791 Intermediate Similarity NPC298595
0.7791 Intermediate Similarity NPC470360
0.7791 Intermediate Similarity NPC290731
0.7778 Intermediate Similarity NPC253190
0.7778 Intermediate Similarity NPC265588
0.7753 Intermediate Similarity NPC473099
0.775 Intermediate Similarity NPC306727
0.7742 Intermediate Similarity NPC312325
0.7727 Intermediate Similarity NPC475664
0.7722 Intermediate Similarity NPC23954
0.7722 Intermediate Similarity NPC242992
0.7722 Intermediate Similarity NPC164022
0.7701 Intermediate Similarity NPC261266
0.7701 Intermediate Similarity NPC6391
0.7701 Intermediate Similarity NPC237344
0.7701 Intermediate Similarity NPC476217
0.7692 Intermediate Similarity NPC65402
0.7692 Intermediate Similarity NPC127718
0.7683 Intermediate Similarity NPC477924
0.7662 Intermediate Similarity NPC476650
0.7662 Intermediate Similarity NPC82337
0.7654 Intermediate Similarity NPC32832
0.764 Intermediate Similarity NPC49783
0.7634 Intermediate Similarity NPC261807
0.7632 Intermediate Similarity NPC287339
0.7614 Intermediate Similarity NPC470620
0.7614 Intermediate Similarity NPC474657
0.7614 Intermediate Similarity NPC186145
0.7614 Intermediate Similarity NPC476948
0.7609 Intermediate Similarity NPC8774
0.7595 Intermediate Similarity NPC283316
0.7595 Intermediate Similarity NPC92801
0.759 Intermediate Similarity NPC167891
0.759 Intermediate Similarity NPC83351
0.7561 Intermediate Similarity NPC477925
0.7561 Intermediate Similarity NPC63958
0.7561 Intermediate Similarity NPC274079
0.7558 Intermediate Similarity NPC477978
0.7558 Intermediate Similarity NPC320548
0.7556 Intermediate Similarity NPC470390
0.7556 Intermediate Similarity NPC270511
0.7556 Intermediate Similarity NPC245410
0.7556 Intermediate Similarity NPC192437
0.7556 Intermediate Similarity NPC14380
0.7532 Intermediate Similarity NPC267027
0.7531 Intermediate Similarity NPC476366
0.7531 Intermediate Similarity NPC201048
0.7528 Intermediate Similarity NPC212596
0.7528 Intermediate Similarity NPC280556
0.7528 Intermediate Similarity NPC67872
0.7528 Intermediate Similarity NPC4574
0.7528 Intermediate Similarity NPC475605
0.7527 Intermediate Similarity NPC12103
0.7527 Intermediate Similarity NPC227583
0.7527 Intermediate Similarity NPC471903
0.7527 Intermediate Similarity NPC98457
0.75 Intermediate Similarity NPC214277
0.75 Intermediate Similarity NPC475069
0.75 Intermediate Similarity NPC477605
0.75 Intermediate Similarity NPC473258
0.75 Intermediate Similarity NPC139724
0.75 Intermediate Similarity NPC196227
0.75 Intermediate Similarity NPC6605
0.75 Intermediate Similarity NPC175145
0.7474 Intermediate Similarity NPC38855
0.7473 Intermediate Similarity NPC114389
0.7473 Intermediate Similarity NPC230623
0.7473 Intermediate Similarity NPC116726
0.7471 Intermediate Similarity NPC238992
0.7471 Intermediate Similarity NPC205845
0.7471 Intermediate Similarity NPC185568
0.747 Intermediate Similarity NPC470711
0.747 Intermediate Similarity NPC471798
0.747 Intermediate Similarity NPC470758
0.747 Intermediate Similarity NPC31037
0.747 Intermediate Similarity NPC91594
0.747 Intermediate Similarity NPC130136
0.7468 Intermediate Similarity NPC234511
0.7468 Intermediate Similarity NPC473893
0.7447 Intermediate Similarity NPC476893
0.7447 Intermediate Similarity NPC316604
0.7447 Intermediate Similarity NPC476021
0.7447 Intermediate Similarity NPC476040
0.7447 Intermediate Similarity NPC474994
0.7444 Intermediate Similarity NPC128066
0.7444 Intermediate Similarity NPC314727
0.7444 Intermediate Similarity NPC101886
0.7442 Intermediate Similarity NPC471408
0.7439 Intermediate Similarity NPC66566
0.7439 Intermediate Similarity NPC477923
0.7439 Intermediate Similarity NPC133580
0.7439 Intermediate Similarity NPC291503
0.7436 Intermediate Similarity NPC163290
0.7416 Intermediate Similarity NPC189777
0.7416 Intermediate Similarity NPC304083
0.7381 Intermediate Similarity NPC11908
0.7381 Intermediate Similarity NPC68119
0.7381 Intermediate Similarity NPC13823
0.7381 Intermediate Similarity NPC148977
0.7375 Intermediate Similarity NPC189745
0.7368 Intermediate Similarity NPC476895
0.7368 Intermediate Similarity NPC83200
0.7363 Intermediate Similarity NPC295668
0.7356 Intermediate Similarity NPC216420
0.7356 Intermediate Similarity NPC207013
0.7356 Intermediate Similarity NPC251475
0.7356 Intermediate Similarity NPC85095
0.7356 Intermediate Similarity NPC79945
0.7356 Intermediate Similarity NPC159168
0.7356 Intermediate Similarity NPC253402
0.7356 Intermediate Similarity NPC474634
0.7356 Intermediate Similarity NPC211135
0.7356 Intermediate Similarity NPC169941
0.7356 Intermediate Similarity NPC317458
0.7349 Intermediate Similarity NPC170148
0.7349 Intermediate Similarity NPC470749
0.7349 Intermediate Similarity NPC167873
0.7349 Intermediate Similarity NPC1973
0.7347 Intermediate Similarity NPC194941
0.7342 Intermediate Similarity NPC244790
0.7342 Intermediate Similarity NPC276616
0.7342 Intermediate Similarity NPC266578
0.7342 Intermediate Similarity NPC245795
0.7342 Intermediate Similarity NPC96484
0.734 Intermediate Similarity NPC90583
0.734 Intermediate Similarity NPC156912
0.734 Intermediate Similarity NPC72204
0.7326 Intermediate Similarity NPC320525
0.7317 Intermediate Similarity NPC477138
0.7317 Intermediate Similarity NPC243342
0.7317 Intermediate Similarity NPC91858
0.7308 Intermediate Similarity NPC311736
0.7308 Intermediate Similarity NPC326310
0.7303 Intermediate Similarity NPC472379
0.7303 Intermediate Similarity NPC201273
0.7303 Intermediate Similarity NPC94462
0.7303 Intermediate Similarity NPC71520
0.7303 Intermediate Similarity NPC152808
0.7303 Intermediate Similarity NPC269058
0.7303 Intermediate Similarity NPC281316
0.7303 Intermediate Similarity NPC121981
0.7303 Intermediate Similarity NPC293287
0.7294 Intermediate Similarity NPC476367
0.7294 Intermediate Similarity NPC72755
0.7292 Intermediate Similarity NPC475877
0.7284 Intermediate Similarity NPC167706
0.7273 Intermediate Similarity NPC102048

  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 NPC236707 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
0.7416 Intermediate Similarity NPD7524 Approved
0.7396 Intermediate Similarity NPD5344 Discontinued
0.7273 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6930 Phase 2
0.7209 Intermediate Similarity NPD6931 Approved
0.7209 Intermediate Similarity NPD7514 Phase 3
0.7209 Intermediate Similarity NPD7332 Phase 2
0.7159 Intermediate Similarity NPD6695 Phase 3
0.7093 Intermediate Similarity NPD6929 Approved
0.7024 Intermediate Similarity NPD8264 Approved
0.7011 Intermediate Similarity NPD7525 Registered
0.6988 Remote Similarity NPD4732 Discontinued
0.6977 Remote Similarity NPD7145 Approved
0.6939 Remote Similarity NPD6648 Approved
0.6932 Remote Similarity NPD6902 Approved
0.686 Remote Similarity NPD5776 Phase 2
0.686 Remote Similarity NPD6925 Approved
0.686 Remote Similarity NPD6932 Approved
0.6848 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7750 Discontinued
0.6813 Remote Similarity NPD6893 Approved
0.6809 Remote Similarity NPD3168 Discontinued
0.6795 Remote Similarity NPD368 Approved
0.6744 Remote Similarity NPD6933 Approved
0.6742 Remote Similarity NPD6898 Phase 1
0.6705 Remote Similarity NPD7645 Phase 2
0.6667 Remote Similarity NPD4225 Approved
0.6591 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7087 Discontinued
0.6552 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6517 Remote Similarity NPD6683 Phase 2
0.6512 Remote Similarity NPD6926 Approved
0.6512 Remote Similarity NPD6924 Approved
0.6444 Remote Similarity NPD7509 Discontinued
0.6437 Remote Similarity NPD7339 Approved
0.6437 Remote Similarity NPD6942 Approved
0.642 Remote Similarity NPD371 Approved
0.6415 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6392 Remote Similarity NPD7637 Suspended
0.6339 Remote Similarity NPD7516 Approved
0.6321 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5211 Phase 2
0.6289 Remote Similarity NPD7136 Phase 2
0.6279 Remote Similarity NPD7150 Approved
0.6279 Remote Similarity NPD7152 Approved
0.6279 Remote Similarity NPD7151 Approved
0.6275 Remote Similarity NPD7639 Approved
0.6275 Remote Similarity NPD7640 Approved
0.6264 Remote Similarity NPD4821 Approved
0.6264 Remote Similarity NPD4819 Approved
0.6264 Remote Similarity NPD4820 Approved
0.6264 Remote Similarity NPD4822 Approved
0.625 Remote Similarity NPD7328 Approved
0.625 Remote Similarity NPD7327 Approved
0.6214 Remote Similarity NPD4159 Approved
0.6204 Remote Similarity NPD4634 Approved
0.619 Remote Similarity NPD5141 Approved
0.6176 Remote Similarity NPD7638 Approved
0.6163 Remote Similarity NPD7143 Approved
0.6163 Remote Similarity NPD7144 Approved
0.6162 Remote Similarity NPD5779 Approved
0.6162 Remote Similarity NPD5778 Approved
0.6154 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5357 Phase 1
0.6129 Remote Similarity NPD3667 Approved
0.6117 Remote Similarity NPD5286 Approved
0.6117 Remote Similarity NPD4696 Approved
0.6117 Remote Similarity NPD5285 Approved
0.6105 Remote Similarity NPD1696 Phase 3
0.6087 Remote Similarity NPD4748 Discontinued
0.6078 Remote Similarity NPD4755 Approved
0.6055 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6047 Remote Similarity NPD6923 Approved
0.6047 Remote Similarity NPD6922 Approved
0.6047 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6044 Remote Similarity NPD4268 Approved
0.6044 Remote Similarity NPD4271 Approved
0.6042 Remote Similarity NPD3618 Phase 1
0.6026 Remote Similarity NPD342 Phase 1
0.6018 Remote Similarity NPD7115 Discovery
0.6 Remote Similarity NPD4202 Approved
0.6 Remote Similarity NPD5226 Approved
0.6 Remote Similarity NPD4633 Approved
0.6 Remote Similarity NPD5225 Approved
0.6 Remote Similarity NPD5224 Approved
0.6 Remote Similarity NPD4786 Approved
0.5981 Remote Similarity NPD6640 Phase 3
0.5962 Remote Similarity NPD4700 Approved
0.596 Remote Similarity NPD7838 Discovery
0.5955 Remote Similarity NPD4785 Approved
0.5955 Remote Similarity NPD4784 Approved
0.5949 Remote Similarity NPD4219 Approved
0.5948 Remote Similarity NPD8033 Approved
0.5948 Remote Similarity NPD8296 Approved
0.5948 Remote Similarity NPD8335 Approved
0.5948 Remote Similarity NPD8380 Approved
0.5948 Remote Similarity NPD8379 Approved
0.5948 Remote Similarity NPD8378 Approved
0.5943 Remote Similarity NPD5175 Approved
0.5943 Remote Similarity NPD5174 Approved
0.5914 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5905 Remote Similarity NPD5223 Approved
0.59 Remote Similarity NPD7515 Phase 2
0.59 Remote Similarity NPD7983 Approved
0.59 Remote Similarity NPD6079 Approved
0.5893 Remote Similarity NPD4632 Approved
0.5876 Remote Similarity NPD4249 Approved
0.5872 Remote Similarity NPD6686 Approved
0.587 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5862 Remote Similarity NPD8377 Approved
0.5862 Remote Similarity NPD8294 Approved
0.5859 Remote Similarity NPD5328 Approved
0.5825 Remote Similarity NPD5222 Approved
0.5825 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5825 Remote Similarity NPD5221 Approved
0.5816 Remote Similarity NPD4250 Approved
0.5816 Remote Similarity NPD4251 Approved
0.5812 Remote Similarity NPD7503 Approved
0.58 Remote Similarity NPD6698 Approved
0.58 Remote Similarity NPD46 Approved
0.5795 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5784 Remote Similarity NPD5282 Discontinued
0.578 Remote Similarity NPD5697 Approved
0.578 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5173 Approved
0.5745 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5743 Remote Similarity NPD6411 Approved
0.573 Remote Similarity NPD4243 Approved
0.5727 Remote Similarity NPD6899 Approved
0.5727 Remote Similarity NPD4730 Approved
0.5727 Remote Similarity NPD4729 Approved
0.5727 Remote Similarity NPD6881 Approved
0.5726 Remote Similarity NPD6319 Approved
0.5714 Remote Similarity NPD4519 Discontinued
0.5714 Remote Similarity NPD4623 Approved
0.5701 Remote Similarity NPD7632 Discontinued
0.57 Remote Similarity NPD4753 Phase 2
0.5688 Remote Similarity NPD5739 Approved
0.5688 Remote Similarity NPD6402 Approved
0.5688 Remote Similarity NPD4768 Approved
0.5688 Remote Similarity NPD6675 Approved
0.5688 Remote Similarity NPD7128 Approved
0.5688 Remote Similarity NPD4767 Approved
0.5686 Remote Similarity NPD6399 Phase 3
0.5678 Remote Similarity NPD6921 Approved
0.5676 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5676 Remote Similarity NPD6012 Approved
0.5676 Remote Similarity NPD6013 Approved
0.5676 Remote Similarity NPD6014 Approved
0.5673 Remote Similarity NPD4697 Phase 3
0.567 Remote Similarity NPD6400 Clinical (unspecified phase)
0.567 Remote Similarity NPD3668 Phase 3
0.567 Remote Similarity NPD3133 Approved
0.567 Remote Similarity NPD3666 Approved
0.567 Remote Similarity NPD3665 Phase 1
0.5664 Remote Similarity NPD8297 Approved
0.5648 Remote Similarity NPD4754 Approved
0.5638 Remote Similarity NPD4195 Approved
0.5636 Remote Similarity NPD6412 Phase 2
0.5636 Remote Similarity NPD5701 Approved
0.5631 Remote Similarity NPD7748 Approved
0.5625 Remote Similarity NPD4270 Approved
0.5625 Remote Similarity NPD6371 Approved
0.5625 Remote Similarity NPD5247 Approved
0.5625 Remote Similarity NPD5248 Approved
0.5625 Remote Similarity NPD6883 Approved
0.5625 Remote Similarity NPD4269 Approved
0.5625 Remote Similarity NPD5250 Approved
0.5625 Remote Similarity NPD5249 Phase 3
0.5625 Remote Similarity NPD7102 Approved
0.5625 Remote Similarity NPD7290 Approved
0.5625 Remote Similarity NPD5251 Approved
0.562 Remote Similarity NPD7507 Approved
0.5619 Remote Similarity NPD7902 Approved
0.561 Remote Similarity NPD7319 Approved
0.5603 Remote Similarity NPD6009 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