Structure

Physi-Chem Properties

Molecular Weight:  758.26
Volume:  708.317
LogP:  -0.064
LogD:  -0.098
LogS:  -2.105
# Rotatable Bonds:  16
TPSA:  279.05
# H-Bond Aceptor:  19
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.073
Synthetic Accessibility Score:  5.448
Fsp3:  0.588
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.103
MDCK Permeability:  0.00022872115368954837
Pgp-inhibitor:  0.002
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.944
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.205
Plasma Protein Binding (PPB):  39.361228942871094%
Volume Distribution (VD):  0.371
Pgp-substrate:  27.659061431884766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.223
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.346
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.035
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.091
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.068

ADMET: Excretion

Clearance (CL):  1.482
Half-life (T1/2):  0.809

ADMET: Toxicity

hERG Blockers:  0.057
Human Hepatotoxicity (H-HT):  0.473
Drug-inuced Liver Injury (DILI):  0.93
AMES Toxicity:  0.645
Rat Oral Acute Toxicity:  0.197
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.141
Carcinogencity:  0.629
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.914

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

  Natural Product: NPC246893

Natural Product ID:  NPC246893
Common Name*:   Reticuloside
IUPAC Name:   methyl (4S,5E,6S)-5-ethylidene-4-[2-oxo-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms:   Reticuloside
Standard InCHIKey:  UUUCHDSMSNBEBE-FFAJWEQASA-N
Standard InCHI:  InChI=1S/C34H46O19/c1-5-16-17(18(31(44)47-4)13-49-32(16)53-34-29(43)26(40)24(38)21(12-36)50-34)11-23(37)48-14-22-25(39)27(41)28(42)33(51-22)52-30-19(45-2)9-15(7-6-8-35)10-20(30)46-3/h5-7,9-10,13,17,21-22,24-29,32-36,38-43H,8,11-12,14H2,1-4H3/b7-6+,16-5+/t17-,21+,22+,24+,25+,26-,27-,28+,29+,32-,33-,34-/m0/s1
SMILES:  OC/C=C/c1cc(OC)c(c(c1)OC)O[C@@H]1O[C@H](COC(=O)C[C@H]2/C(=CC)/[C@@H](OC=C2C(=O)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1911051
PubChem CID:   57390293
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003918] Saccharolipids

*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
NPO16259 Syringa reticulata Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[21955940]
NPO16259 Syringa reticulata Species Oleaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 64140.0 nM PMID[524743]
NPT1 Others Radical scavenging activity EC50 > 100000.0 nM PMID[524743]

☑ 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 NPC246893 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
0.8933 High Similarity NPC52740
0.8919 High Similarity NPC469367
0.8897 High Similarity NPC164857
0.8882 High Similarity NPC114740
0.8874 High Similarity NPC23677
0.8867 High Similarity NPC476865
0.8828 High Similarity NPC470236
0.882 High Similarity NPC658
0.882 High Similarity NPC197708
0.8816 High Similarity NPC106138
0.8816 High Similarity NPC283839
0.8816 High Similarity NPC90896
0.88 High Similarity NPC476864
0.88 High Similarity NPC476868
0.88 High Similarity NPC476866
0.88 High Similarity NPC476869
0.8767 High Similarity NPC37468
0.8766 High Similarity NPC476352
0.8766 High Similarity NPC472612
0.8766 High Similarity NPC215060
0.8766 High Similarity NPC289967
0.8766 High Similarity NPC472611
0.8758 High Similarity NPC476871
0.875 High Similarity NPC96294
0.875 High Similarity NPC478237
0.8733 High Similarity NPC476867
0.8733 High Similarity NPC297342
0.8725 High Similarity NPC296643
0.8716 High Similarity NPC210478
0.8716 High Similarity NPC202700
0.8712 High Similarity NPC5786
0.8712 High Similarity NPC102851
0.8712 High Similarity NPC470685
0.8701 High Similarity NPC213197
0.869 High Similarity NPC49074
0.8684 High Similarity NPC41844
0.8671 High Similarity NPC289811
0.8671 High Similarity NPC173726
0.8671 High Similarity NPC241600
0.8671 High Similarity NPC160780
0.8659 High Similarity NPC163165
0.8649 High Similarity NPC100389
0.8645 High Similarity NPC203664
0.8636 High Similarity NPC69367
0.8627 High Similarity NPC93924
0.8625 High Similarity NPC285108
0.8625 High Similarity NPC33298
0.8625 High Similarity NPC148273
0.8621 High Similarity NPC162093
0.8616 High Similarity NPC203020
0.8616 High Similarity NPC239966
0.8608 High Similarity NPC1913
0.86 High Similarity NPC157816
0.859 High Similarity NPC310661
0.859 High Similarity NPC150442
0.859 High Similarity NPC105827
0.8581 High Similarity NPC469364
0.8581 High Similarity NPC124149
0.8581 High Similarity NPC65262
0.8581 High Similarity NPC101686
0.8571 High Similarity NPC206264
0.8571 High Similarity NPC94871
0.8571 High Similarity NPC306890
0.8571 High Similarity NPC476398
0.8571 High Similarity NPC313334
0.8571 High Similarity NPC470933
0.8571 High Similarity NPC471062
0.8571 High Similarity NPC185778
0.8571 High Similarity NPC476386
0.8571 High Similarity NPC473427
0.8571 High Similarity NPC259347
0.8571 High Similarity NPC212670
0.8571 High Similarity NPC111785
0.8562 High Similarity NPC25389
0.8562 High Similarity NPC311803
0.8562 High Similarity NPC472859
0.8553 High Similarity NPC34927
0.8553 High Similarity NPC34587
0.8553 High Similarity NPC476382
0.8553 High Similarity NPC252292
0.8553 High Similarity NPC216819
0.8553 High Similarity NPC83743
0.8553 High Similarity NPC262182
0.8553 High Similarity NPC100998
0.8553 High Similarity NPC287615
0.8543 High Similarity NPC478239
0.8533 High Similarity NPC257095
0.8533 High Similarity NPC273932
0.8533 High Similarity NPC89686
0.8526 High Similarity NPC176186
0.8526 High Similarity NPC134905
0.8526 High Similarity NPC169404
0.8526 High Similarity NPC36130
0.8526 High Similarity NPC53587
0.8523 High Similarity NPC98777
0.8523 High Similarity NPC212770
0.8516 High Similarity NPC470934
0.8516 High Similarity NPC188393
0.8516 High Similarity NPC470927
0.8516 High Similarity NPC257970
0.8514 High Similarity NPC157554
0.8514 High Similarity NPC186418
0.8514 High Similarity NPC197723
0.8514 High Similarity NPC138350
0.8514 High Similarity NPC40664
0.8514 High Similarity NPC165482
0.8514 High Similarity NPC3293
0.8509 High Similarity NPC41009
0.8506 High Similarity NPC261122
0.8506 High Similarity NPC300262
0.8506 High Similarity NPC192763
0.8506 High Similarity NPC28651
0.8506 High Similarity NPC3460
0.8506 High Similarity NPC210611
0.8506 High Similarity NPC201148
0.8506 High Similarity NPC199311
0.8506 High Similarity NPC80732
0.8506 High Similarity NPC215095
0.8503 High Similarity NPC120952
0.8503 High Similarity NPC13745
0.8503 High Similarity NPC48863
0.8503 High Similarity NPC251981
0.85 High Similarity NPC166277
0.85 High Similarity NPC289346
0.85 High Similarity NPC119125
0.8497 Intermediate Similarity NPC199928
0.8494 Intermediate Similarity NPC169645
0.8494 Intermediate Similarity NPC84482
0.8493 Intermediate Similarity NPC299144
0.8491 Intermediate Similarity NPC472860
0.8477 Intermediate Similarity NPC473873
0.8477 Intermediate Similarity NPC473792
0.8477 Intermediate Similarity NPC469559
0.8466 Intermediate Similarity NPC282551
0.8466 Intermediate Similarity NPC59516
0.8457 Intermediate Similarity NPC227297
0.8456 Intermediate Similarity NPC59324
0.8456 Intermediate Similarity NPC65530
0.8452 Intermediate Similarity NPC95392
0.8452 Intermediate Similarity NPC55715
0.8452 Intermediate Similarity NPC478242
0.8452 Intermediate Similarity NPC35877
0.8446 Intermediate Similarity NPC55040
0.8446 Intermediate Similarity NPC238243
0.8442 Intermediate Similarity NPC232992
0.8438 Intermediate Similarity NPC74319
0.8438 Intermediate Similarity NPC287872
0.8435 Intermediate Similarity NPC132895
0.8435 Intermediate Similarity NPC215833
0.8435 Intermediate Similarity NPC69513
0.8428 Intermediate Similarity NPC284810
0.8424 Intermediate Similarity NPC43434
0.8424 Intermediate Similarity NPC472129
0.8418 Intermediate Similarity NPC327032
0.8418 Intermediate Similarity NPC191046
0.8418 Intermediate Similarity NPC194095
0.8414 Intermediate Similarity NPC248355
0.8412 Intermediate Similarity NPC21359
0.8412 Intermediate Similarity NPC460984
0.8412 Intermediate Similarity NPC470713
0.8412 Intermediate Similarity NPC25946
0.8412 Intermediate Similarity NPC470720
0.8412 Intermediate Similarity NPC470717
0.8411 Intermediate Similarity NPC186406
0.8408 Intermediate Similarity NPC302610
0.8408 Intermediate Similarity NPC470264
0.8405 Intermediate Similarity NPC472131
0.8405 Intermediate Similarity NPC475497
0.8405 Intermediate Similarity NPC284277
0.8405 Intermediate Similarity NPC472130
0.8405 Intermediate Similarity NPC15358
0.8405 Intermediate Similarity NPC475366
0.84 Intermediate Similarity NPC226005
0.8397 Intermediate Similarity NPC229882
0.8397 Intermediate Similarity NPC158635
0.8397 Intermediate Similarity NPC107197
0.8395 Intermediate Similarity NPC90905
0.8395 Intermediate Similarity NPC4013
0.8393 Intermediate Similarity NPC173837
0.8389 Intermediate Similarity NPC242028
0.8389 Intermediate Similarity NPC203230
0.8389 Intermediate Similarity NPC471719
0.8387 Intermediate Similarity NPC187398
0.8387 Intermediate Similarity NPC116229
0.8387 Intermediate Similarity NPC476348
0.8383 Intermediate Similarity NPC198199
0.8378 Intermediate Similarity NPC169398
0.8378 Intermediate Similarity NPC188555
0.8378 Intermediate Similarity NPC130496
0.8377 Intermediate Similarity NPC125755
0.8375 Intermediate Similarity NPC471878
0.8375 Intermediate Similarity NPC133984
0.8373 Intermediate Similarity NPC180918
0.8366 Intermediate Similarity NPC232228
0.8366 Intermediate Similarity NPC110063
0.8366 Intermediate Similarity NPC292443
0.8366 Intermediate Similarity NPC471063
0.8365 Intermediate Similarity NPC10205
0.8364 Intermediate Similarity NPC198125
0.8364 Intermediate Similarity NPC195257

  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 NPC246893 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
0.8571 High Similarity NPD1653 Approved
0.8424 Intermediate Similarity NPD7472 Approved
0.8383 Intermediate Similarity NPD7808 Phase 3
0.8364 Intermediate Similarity NPD7054 Approved
0.8214 Intermediate Similarity NPD7251 Discontinued
0.8204 Intermediate Similarity NPD7074 Phase 3
0.8158 Intermediate Similarity NPD7266 Discontinued
0.8155 Intermediate Similarity NPD6797 Phase 2
0.8084 Intermediate Similarity NPD7228 Approved
0.8059 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7685 Pre-registration
0.7976 Intermediate Similarity NPD3818 Discontinued
0.7927 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD37 Approved
0.7895 Intermediate Similarity NPD7240 Approved
0.7892 Intermediate Similarity NPD7199 Phase 2
0.7866 Intermediate Similarity NPD4965 Approved
0.7866 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD4967 Phase 2
0.7866 Intermediate Similarity NPD4966 Approved
0.7824 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6234 Discontinued
0.7744 Intermediate Similarity NPD8455 Phase 2
0.7733 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD3817 Phase 2
0.7692 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6166 Phase 2
0.7616 Intermediate Similarity NPD5844 Phase 1
0.7593 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD1934 Approved
0.7566 Intermediate Similarity NPD3027 Phase 3
0.7532 Intermediate Similarity NPD1613 Approved
0.7532 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1091 Approved
0.7486 Intermediate Similarity NPD6559 Discontinued
0.7484 Intermediate Similarity NPD6674 Discontinued
0.7425 Intermediate Similarity NPD1465 Phase 2
0.7425 Intermediate Similarity NPD2801 Approved
0.7425 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD8312 Approved
0.7401 Intermediate Similarity NPD8313 Approved
0.7396 Intermediate Similarity NPD7075 Discontinued
0.7391 Intermediate Similarity NPD6190 Approved
0.7381 Intermediate Similarity NPD5402 Approved
0.7375 Intermediate Similarity NPD1652 Phase 2
0.7372 Intermediate Similarity NPD5124 Phase 1
0.7372 Intermediate Similarity NPD230 Phase 1
0.7372 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD8127 Discontinued
0.7349 Intermediate Similarity NPD4380 Phase 2
0.7321 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7819 Suspended
0.731 Intermediate Similarity NPD5494 Approved
0.7287 Intermediate Similarity NPD7680 Approved
0.7278 Intermediate Similarity NPD5353 Approved
0.7278 Intermediate Similarity NPD7097 Phase 1
0.7273 Intermediate Similarity NPD5403 Approved
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6801 Discontinued
0.7258 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD3882 Suspended
0.7222 Intermediate Similarity NPD4628 Phase 3
0.7222 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6653 Approved
0.7208 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7411 Suspended
0.7195 Intermediate Similarity NPD1511 Approved
0.7181 Intermediate Similarity NPD1357 Approved
0.7176 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD3751 Discontinued
0.7152 Intermediate Similarity NPD5401 Approved
0.7126 Intermediate Similarity NPD3787 Discontinued
0.7124 Intermediate Similarity NPD3225 Approved
0.712 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD1512 Approved
0.7102 Intermediate Similarity NPD7473 Discontinued
0.7091 Intermediate Similarity NPD6799 Approved
0.7059 Intermediate Similarity NPD2982 Phase 2
0.7059 Intermediate Similarity NPD2983 Phase 2
0.7056 Intermediate Similarity NPD7549 Discontinued
0.7051 Intermediate Similarity NPD4908 Phase 1
0.7049 Intermediate Similarity NPD6843 Phase 3
0.7049 Intermediate Similarity NPD6841 Approved
0.7049 Intermediate Similarity NPD6842 Approved
0.7048 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1933 Approved
0.7044 Intermediate Similarity NPD447 Suspended
0.7039 Intermediate Similarity NPD422 Phase 1
0.7039 Intermediate Similarity NPD3705 Approved
0.7029 Intermediate Similarity NPD6232 Discontinued
0.7025 Intermediate Similarity NPD6233 Phase 2
0.7012 Intermediate Similarity NPD3750 Approved
0.7012 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4110 Phase 3
0.7011 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD8151 Discontinued
0.7 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.6994 Remote Similarity NPD970 Clinical (unspecified phase)
0.6993 Remote Similarity NPD2981 Phase 2
0.6988 Remote Similarity NPD4357 Discontinued
0.6978 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6962 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6949 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6355 Discontinued
0.6936 Remote Similarity NPD7768 Phase 2
0.6933 Remote Similarity NPD5536 Phase 2
0.6923 Remote Similarity NPD3687 Approved
0.6923 Remote Similarity NPD3686 Approved
0.6914 Remote Similarity NPD7033 Discontinued
0.6908 Remote Similarity NPD1778 Approved
0.6907 Remote Similarity NPD7583 Approved
0.6902 Remote Similarity NPD8434 Phase 2
0.6899 Remote Similarity NPD7095 Approved
0.6897 Remote Similarity NPD7975 Clinical (unspecified phase)
0.689 Remote Similarity NPD1549 Phase 2
0.6879 Remote Similarity NPD9494 Approved
0.6879 Remote Similarity NPD3018 Phase 2
0.6872 Remote Similarity NPD7585 Approved
0.6871 Remote Similarity NPD6100 Approved
0.6871 Remote Similarity NPD2796 Approved
0.6871 Remote Similarity NPD6099 Approved
0.6857 Remote Similarity NPD919 Approved
0.6855 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6798 Discontinued
0.6855 Remote Similarity NPD3268 Approved
0.6848 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6845 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6599 Discontinued
0.6829 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7843 Approved
0.6818 Remote Similarity NPD1610 Phase 2
0.681 Remote Similarity NPD3748 Approved
0.6807 Remote Similarity NPD8166 Discontinued
0.6784 Remote Similarity NPD7458 Discontinued
0.678 Remote Similarity NPD6959 Discontinued
0.6776 Remote Similarity NPD1548 Phase 1
0.6774 Remote Similarity NPD1608 Approved
0.677 Remote Similarity NPD4060 Phase 1
0.6768 Remote Similarity NPD7783 Phase 2
0.6768 Remote Similarity NPD1551 Phase 2
0.6768 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6752 Remote Similarity NPD2797 Approved
0.6746 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7229 Phase 3
0.6735 Remote Similarity NPD7584 Approved
0.6732 Remote Similarity NPD5585 Approved
0.6731 Remote Similarity NPD4749 Approved
0.6728 Remote Similarity NPD4340 Discontinued
0.6727 Remote Similarity NPD5762 Approved
0.6727 Remote Similarity NPD5763 Approved
0.6726 Remote Similarity NPD5058 Phase 3
0.6721 Remote Similarity NPD7038 Approved
0.6721 Remote Similarity NPD7039 Approved
0.6712 Remote Similarity NPD1358 Approved
0.6709 Remote Similarity NPD5647 Approved
0.6708 Remote Similarity NPD4062 Phase 3
0.6707 Remote Similarity NPD1510 Phase 2
0.6706 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6385 Approved
0.6705 Remote Similarity NPD6386 Approved
0.6704 Remote Similarity NPD5242 Approved
0.6689 Remote Similarity NPD7157 Approved
0.6687 Remote Similarity NPD2424 Discontinued
0.6686 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6685 Remote Similarity NPD1247 Approved
0.6667 Remote Similarity NPD2861 Phase 2
0.6667 Remote Similarity NPD9269 Phase 2
0.6667 Remote Similarity NPD7435 Discontinued
0.6647 Remote Similarity NPD3146 Approved
0.6647 Remote Similarity NPD4678 Approved
0.6647 Remote Similarity NPD4675 Approved
0.6647 Remote Similarity NPD7028 Phase 2
0.6647 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6647 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6362 Approved
0.6646 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6645 Remote Similarity NPD3496 Discontinued
0.6644 Remote Similarity NPD3134 Approved
0.6644 Remote Similarity NPD228 Approved
0.6627 Remote Similarity NPD6002 Phase 3
0.6627 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6005 Phase 3
0.6627 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6004 Phase 3
0.6623 Remote Similarity NPD9268 Approved
0.6615 Remote Similarity NPD8090 Clinical (unspecified phase)
0.661 Remote Similarity NPD6971 Discontinued
0.6608 Remote Similarity NPD6273 Approved
0.6608 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6374 Clinical (unspecified phase)
0.659 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6582 Remote Similarity NPD7696 Phase 3

  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