Structure

Physi-Chem Properties

Molecular Weight:  566.2
Volume:  537.14
LogP:  0.917
LogD:  1.098
LogS:  -3.044
# Rotatable Bonds:  10
TPSA:  190.67
# H-Bond Aceptor:  13
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.192
Synthetic Accessibility Score:  4.845
Fsp3:  0.556
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.846
MDCK Permeability:  0.00011005862324964255
Pgp-inhibitor:  0.003
Pgp-substrate:  0.903
Human Intestinal Absorption (HIA):  0.891
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.106
Plasma Protein Binding (PPB):  47.24586486816406%
Volume Distribution (VD):  0.544
Pgp-substrate:  17.45179557800293%

ADMET: Metabolism

CYP1A2-inhibitor:  0.084
CYP1A2-substrate:  0.1
CYP2C19-inhibitor:  0.055
CYP2C19-substrate:  0.54
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.119
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.171
CYP3A4-inhibitor:  0.198
CYP3A4-substrate:  0.151

ADMET: Excretion

Clearance (CL):  1.874
Half-life (T1/2):  0.875

ADMET: Toxicity

hERG Blockers:  0.137
Human Hepatotoxicity (H-HT):  0.728
Drug-inuced Liver Injury (DILI):  0.853
AMES Toxicity:  0.085
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.287
Carcinogencity:  0.128
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.694

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

  Natural Product: NPC475379

Natural Product ID:  NPC475379
Common Name*:   Arbortristoside A
IUPAC Name:   methyl (1S,4aS,5S,6R,7R,7aR)-5-hydroxy-6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:  
Standard InCHIKey:  PSOYNZJMRVQTDR-OVEXURONSA-N
Standard InCHI:  InChI=1S/C27H34O13/c1-12-18-19(21(31)24(12)39-17(29)9-6-13-4-7-14(35-2)8-5-13)15(25(34)36-3)11-37-26(18)40-27-23(33)22(32)20(30)16(10-28)38-27/h4-9,11-12,16,18-24,26-28,30-33H,10H2,1-3H3/b9-6+/t12-,16-,18-,19-,20-,21+,22+,23-,24-,26+,27+/m1/s1
SMILES:  CC1C2C(C(C1OC(=O)C=CC3=CC=C(C=C3)OC)O)C(=COC2OC4C(C(C(C(O4)CO)O)O)O)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504519
PubChem CID:   15747852
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO33172 nyctanthes arbortristis Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[1791475]
NPO33172 nyctanthes arbortristis Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[22608855]

☑ 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
NPT71 Cell Line HEK293 Homo sapiens Activity = 71.25 % PMID[454987]
NPT71 Cell Line HEK293 Homo sapiens Activity = 95.46 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 41.87 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 65.77 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 73.43 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 97.87 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 33.82 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 60.09 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 63.72 % PMID[454987]
NPT6376 Individual Protein Trypanothione reductase Leishmania donovani Inhibition = 92.54 % PMID[454987]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 7.13 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 30.24 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 45.83 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 64.58 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 57.0 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 18.23 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 79.68 % PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani Survival = 38.0 day PMID[454986]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 7260.0 nM PMID[454987]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 3264.0 nM PMID[454987]
NPT633 Organism Leishmania donovani Leishmania donovani Activity = 2.13 % PMID[454987]
NPT633 Organism Leishmania donovani Leishmania donovani Activity = 10.33 % PMID[454987]
NPT633 Organism Leishmania donovani Leishmania donovani Activity = 26.3 % PMID[454987]
NPT633 Organism Leishmania donovani Leishmania donovani Activity = 61.24 % PMID[454987]

☑ 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 NPC475379 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
0.9586 High Similarity NPC96599
0.9388 High Similarity NPC240592
0.9388 High Similarity NPC117346
0.9276 High Similarity NPC179914
0.9267 High Similarity NPC478232
0.9241 High Similarity NPC296659
0.9241 High Similarity NPC202391
0.9205 High Similarity NPC475484
0.9195 High Similarity NPC289021
0.9195 High Similarity NPC158546
0.9172 High Similarity NPC475213
0.9172 High Similarity NPC152796
0.911 High Similarity NPC184464
0.911 High Similarity NPC251062
0.9091 High Similarity NPC474936
0.9054 High Similarity NPC473149
0.9041 High Similarity NPC186296
0.9041 High Similarity NPC88754
0.9041 High Similarity NPC302286
0.9041 High Similarity NPC263397
0.9041 High Similarity NPC116104
0.9041 High Similarity NPC237872
0.902 High Similarity NPC475378
0.898 High Similarity NPC478240
0.8974 High Similarity NPC206815
0.8933 High Similarity NPC478234
0.8933 High Similarity NPC478236
0.8904 High Similarity NPC154262
0.8904 High Similarity NPC7518
0.8904 High Similarity NPC159387
0.8904 High Similarity NPC137501
0.8882 High Similarity NPC194705
0.8859 High Similarity NPC37838
0.8854 High Similarity NPC476011
0.8824 High Similarity NPC229354
0.8812 High Similarity NPC21956
0.8805 High Similarity NPC130730
0.8805 High Similarity NPC282551
0.8805 High Similarity NPC301910
0.8767 High Similarity NPC220936
0.8767 High Similarity NPC31745
0.8765 High Similarity NPC195972
0.8758 High Similarity NPC203664
0.8758 High Similarity NPC478235
0.875 High Similarity NPC147224
0.8742 High Similarity NPC308178
0.8734 High Similarity NPC145847
0.8725 High Similarity NPC77922
0.8725 High Similarity NPC473281
0.8679 High Similarity NPC109990
0.8639 High Similarity NPC49597
0.8609 High Similarity NPC474268
0.8609 High Similarity NPC475539
0.8609 High Similarity NPC119773
0.8609 High Similarity NPC473147
0.8609 High Similarity NPC143246
0.8608 High Similarity NPC138993
0.86 High Similarity NPC194938
0.8589 High Similarity NPC470685
0.8571 High Similarity NPC478249
0.8571 High Similarity NPC269914
0.8552 High Similarity NPC470143
0.8552 High Similarity NPC322503
0.8544 High Similarity NPC469384
0.8543 High Similarity NPC475528
0.8535 High Similarity NPC478248
0.8533 High Similarity NPC469367
0.8533 High Similarity NPC293154
0.8523 High Similarity NPC46644
0.8523 High Similarity NPC80098
0.8509 High Similarity NPC318472
0.8506 High Similarity NPC35097
0.8506 High Similarity NPC229882
0.8506 High Similarity NPC158635
0.8497 Intermediate Similarity NPC120728
0.8493 Intermediate Similarity NPC169398
0.8491 Intermediate Similarity NPC208676
0.8491 Intermediate Similarity NPC130489
0.8487 Intermediate Similarity NPC212808
0.8481 Intermediate Similarity NPC286919
0.8481 Intermediate Similarity NPC187205
0.8481 Intermediate Similarity NPC475663
0.8477 Intermediate Similarity NPC63304
0.8476 Intermediate Similarity NPC222665
0.8476 Intermediate Similarity NPC271755
0.8476 Intermediate Similarity NPC254071
0.8476 Intermediate Similarity NPC149502
0.8462 Intermediate Similarity NPC478241
0.8462 Intermediate Similarity NPC89693
0.8462 Intermediate Similarity NPC229548
0.8447 Intermediate Similarity NPC327694
0.8442 Intermediate Similarity NPC161955
0.8408 Intermediate Similarity NPC476364
0.84 Intermediate Similarity NPC79908
0.8377 Intermediate Similarity NPC473428
0.8367 Intermediate Similarity NPC34456
0.8366 Intermediate Similarity NPC291153
0.8365 Intermediate Similarity NPC226759
0.8355 Intermediate Similarity NPC471028
0.8353 Intermediate Similarity NPC299855
0.8353 Intermediate Similarity NPC96194
0.8344 Intermediate Similarity NPC61604
0.8344 Intermediate Similarity NPC469699
0.8344 Intermediate Similarity NPC245615
0.8344 Intermediate Similarity NPC137813
0.8344 Intermediate Similarity NPC257847
0.8344 Intermediate Similarity NPC299706
0.8344 Intermediate Similarity NPC115466
0.8333 Intermediate Similarity NPC474620
0.8323 Intermediate Similarity NPC478242
0.8322 Intermediate Similarity NPC65262
0.8322 Intermediate Similarity NPC469364
0.8322 Intermediate Similarity NPC101686
0.8313 Intermediate Similarity NPC76211
0.8304 Intermediate Similarity NPC189704
0.8301 Intermediate Similarity NPC210330
0.8289 Intermediate Similarity NPC478250
0.8289 Intermediate Similarity NPC242756
0.8288 Intermediate Similarity NPC254819
0.8282 Intermediate Similarity NPC180586
0.828 Intermediate Similarity NPC36130
0.828 Intermediate Similarity NPC134905
0.8278 Intermediate Similarity NPC51181
0.8276 Intermediate Similarity NPC295970
0.8272 Intermediate Similarity NPC326278
0.8269 Intermediate Similarity NPC107197
0.8269 Intermediate Similarity NPC69367
0.8269 Intermediate Similarity NPC182350
0.8269 Intermediate Similarity NPC88886
0.8269 Intermediate Similarity NPC104172
0.8261 Intermediate Similarity NPC476337
0.8261 Intermediate Similarity NPC478265
0.8258 Intermediate Similarity NPC472339
0.8256 Intermediate Similarity NPC476067
0.8256 Intermediate Similarity NPC475121
0.8255 Intermediate Similarity NPC71638
0.8255 Intermediate Similarity NPC294470
0.8255 Intermediate Similarity NPC64230
0.825 Intermediate Similarity NPC329997
0.8247 Intermediate Similarity NPC474044
0.8239 Intermediate Similarity NPC38699
0.8239 Intermediate Similarity NPC10205
0.8235 Intermediate Similarity NPC473776
0.8235 Intermediate Similarity NPC473205
0.8231 Intermediate Similarity NPC269421
0.8228 Intermediate Similarity NPC44730
0.8224 Intermediate Similarity NPC284957
0.8224 Intermediate Similarity NPC296643
0.8221 Intermediate Similarity NPC120012
0.8199 Intermediate Similarity NPC43761
0.8199 Intermediate Similarity NPC209473
0.8194 Intermediate Similarity NPC469700
0.8194 Intermediate Similarity NPC175275
0.8194 Intermediate Similarity NPC18789
0.8194 Intermediate Similarity NPC476338
0.8194 Intermediate Similarity NPC97240
0.8194 Intermediate Similarity NPC476359
0.8187 Intermediate Similarity NPC471405
0.8187 Intermediate Similarity NPC163635
0.8176 Intermediate Similarity NPC327032
0.8176 Intermediate Similarity NPC114116
0.8176 Intermediate Similarity NPC194095
0.8176 Intermediate Similarity NPC191046
0.8171 Intermediate Similarity NPC294722
0.8148 Intermediate Similarity NPC73422
0.8148 Intermediate Similarity NPC310399
0.8141 Intermediate Similarity NPC220282
0.8141 Intermediate Similarity NPC189631
0.8141 Intermediate Similarity NPC95990
0.8137 Intermediate Similarity NPC472860
0.8137 Intermediate Similarity NPC49173
0.8133 Intermediate Similarity NPC472132
0.8133 Intermediate Similarity NPC471345
0.8125 Intermediate Similarity NPC186316
0.8121 Intermediate Similarity NPC476277
0.8121 Intermediate Similarity NPC471029
0.8114 Intermediate Similarity NPC475299
0.8113 Intermediate Similarity NPC157898
0.811 Intermediate Similarity NPC100420
0.8103 Intermediate Similarity NPC230670
0.8103 Intermediate Similarity NPC71385
0.8098 Intermediate Similarity NPC90336
0.8095 Intermediate Similarity NPC316539
0.8095 Intermediate Similarity NPC17567
0.8089 Intermediate Similarity NPC111785
0.8086 Intermediate Similarity NPC329743
0.8086 Intermediate Similarity NPC469654
0.8077 Intermediate Similarity NPC296377
0.8075 Intermediate Similarity NPC228357
0.8075 Intermediate Similarity NPC478055
0.8075 Intermediate Similarity NPC10945
0.8075 Intermediate Similarity NPC45165
0.8072 Intermediate Similarity NPC208818
0.8072 Intermediate Similarity NPC471860
0.8067 Intermediate Similarity NPC212729
0.8065 Intermediate Similarity NPC85624
0.8061 Intermediate Similarity NPC475738
0.8061 Intermediate Similarity NPC475979
0.8057 Intermediate Similarity NPC112708
0.805 Intermediate Similarity NPC476335

  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 NPC475379 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
0.865 High Similarity NPD7685 Pre-registration
0.7914 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD7199 Phase 2
0.7871 Intermediate Similarity NPD4628 Phase 3
0.784 Intermediate Similarity NPD8455 Phase 2
0.7803 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6355 Discontinued
0.7679 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD7266 Discontinued
0.7669 Intermediate Similarity NPD37 Approved
0.7647 Intermediate Similarity NPD7228 Approved
0.7647 Intermediate Similarity NPD6653 Approved
0.7647 Intermediate Similarity NPD3818 Discontinued
0.7636 Intermediate Similarity NPD4965 Approved
0.7636 Intermediate Similarity NPD4967 Phase 2
0.7636 Intermediate Similarity NPD4966 Approved
0.7602 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD5647 Approved
0.7564 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD6004 Phase 3
0.7564 Intermediate Similarity NPD6002 Phase 3
0.7564 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD6005 Phase 3
0.756 Intermediate Similarity NPD8127 Discontinued
0.7546 Intermediate Similarity NPD4380 Phase 2
0.7545 Intermediate Similarity NPD6234 Discontinued
0.7516 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7054 Approved
0.7485 Intermediate Similarity NPD7075 Discontinued
0.7485 Intermediate Similarity NPD7458 Discontinued
0.7484 Intermediate Similarity NPD7097 Phase 1
0.7471 Intermediate Similarity NPD7240 Approved
0.7469 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7472 Approved
0.7457 Intermediate Similarity NPD7074 Phase 3
0.7452 Intermediate Similarity NPD5762 Approved
0.7452 Intermediate Similarity NPD5763 Approved
0.7436 Intermediate Similarity NPD7033 Discontinued
0.7429 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD1653 Approved
0.7407 Intermediate Similarity NPD6273 Approved
0.74 Intermediate Similarity NPD6362 Approved
0.7389 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD8313 Approved
0.7386 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD8312 Approved
0.7375 Intermediate Similarity NPD6190 Approved
0.7371 Intermediate Similarity NPD7251 Discontinued
0.7371 Intermediate Similarity NPD6559 Discontinued
0.7349 Intermediate Similarity NPD6801 Discontinued
0.7346 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7799 Discontinued
0.7338 Intermediate Similarity NPD6233 Phase 2
0.7333 Intermediate Similarity NPD7028 Phase 2
0.733 Intermediate Similarity NPD7808 Phase 3
0.7314 Intermediate Similarity NPD6797 Phase 2
0.7305 Intermediate Similarity NPD7819 Suspended
0.7273 Intermediate Similarity NPD6798 Discontinued
0.725 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD1091 Approved
0.7205 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1608 Approved
0.7179 Intermediate Similarity NPD4140 Approved
0.7178 Intermediate Similarity NPD6799 Approved
0.7171 Intermediate Similarity NPD2797 Approved
0.7161 Intermediate Similarity NPD3268 Approved
0.716 Intermediate Similarity NPD3817 Phase 2
0.7143 Intermediate Similarity NPD1652 Phase 2
0.7134 Intermediate Similarity NPD5735 Approved
0.7134 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6599 Discontinued
0.7124 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD5844 Phase 1
0.7101 Intermediate Similarity NPD5760 Phase 2
0.7101 Intermediate Similarity NPD5761 Phase 2
0.7099 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4110 Phase 3
0.7099 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD9545 Approved
0.709 Intermediate Similarity NPD7497 Discontinued
0.7083 Intermediate Similarity NPD7411 Suspended
0.7081 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5958 Discontinued
0.7081 Intermediate Similarity NPD2424 Discontinued
0.7072 Intermediate Similarity NPD8434 Phase 2
0.7063 Intermediate Similarity NPD2796 Approved
0.7059 Intermediate Similarity NPD5402 Approved
0.7059 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD3764 Approved
0.7048 Intermediate Similarity NPD5403 Approved
0.7045 Intermediate Similarity NPD3751 Discontinued
0.7041 Intermediate Similarity NPD1934 Approved
0.7037 Intermediate Similarity NPD6674 Discontinued
0.703 Intermediate Similarity NPD5401 Approved
0.7025 Intermediate Similarity NPD5124 Phase 1
0.7025 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD230 Phase 1
0.7022 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7999 Approved
0.7013 Intermediate Similarity NPD2798 Approved
0.7012 Intermediate Similarity NPD7236 Approved
0.7012 Intermediate Similarity NPD5058 Phase 3
0.7012 Intermediate Similarity NPD6652 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3787 Discontinued
0.7007 Intermediate Similarity NPD7157 Approved
0.7006 Intermediate Similarity NPD4062 Phase 3
0.7006 Intermediate Similarity NPD6663 Approved
0.7 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD17 Approved
0.7 Intermediate Similarity NPD1510 Phase 2
0.7 Intermediate Similarity NPD7435 Discontinued
0.7 Intermediate Similarity NPD2799 Discontinued
0.6995 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6994 Remote Similarity NPD3750 Approved
0.6994 Remote Similarity NPD5494 Approved
0.6993 Remote Similarity NPD1876 Approved
0.6989 Remote Similarity NPD7473 Discontinued
0.6987 Remote Similarity NPD7095 Approved
0.6983 Remote Similarity NPD6765 Approved
0.6983 Remote Similarity NPD6764 Approved
0.6982 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1549 Phase 2
0.6968 Remote Similarity NPD2861 Phase 2
0.6968 Remote Similarity NPD5736 Approved
0.6959 Remote Similarity NPD5353 Approved
0.6957 Remote Similarity NPD2438 Suspended
0.6948 Remote Similarity NPD3267 Approved
0.6948 Remote Similarity NPD3266 Approved
0.6932 Remote Similarity NPD6166 Phase 2
0.6932 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6932 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2534 Approved
0.6928 Remote Similarity NPD2533 Approved
0.6928 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2532 Approved
0.6923 Remote Similarity NPD1358 Approved
0.6918 Remote Similarity NPD7843 Approved
0.6914 Remote Similarity NPD6232 Discontinued
0.6914 Remote Similarity NPD7229 Phase 3
0.6914 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6908 Remote Similarity NPD3705 Approved
0.6905 Remote Similarity NPD7239 Suspended
0.6904 Remote Similarity NPD7930 Approved
0.6901 Remote Similarity NPD1465 Phase 2
0.6901 Remote Similarity NPD2801 Approved
0.6899 Remote Similarity NPD8032 Phase 2
0.6894 Remote Similarity NPD3748 Approved
0.6891 Remote Similarity NPD7583 Approved
0.6882 Remote Similarity NPD6386 Approved
0.6882 Remote Similarity NPD6385 Approved
0.6878 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6871 Remote Similarity NPD4534 Discontinued
0.6856 Remote Similarity NPD7585 Approved
0.6853 Remote Similarity NPD3134 Approved
0.6852 Remote Similarity NPD2935 Discontinued
0.6845 Remote Similarity NPD920 Approved
0.6842 Remote Similarity NPD6777 Approved
0.6842 Remote Similarity NPD6780 Approved
0.6842 Remote Similarity NPD6779 Approved
0.6842 Remote Similarity NPD6776 Approved
0.6842 Remote Similarity NPD6778 Approved
0.6842 Remote Similarity NPD6782 Approved
0.6842 Remote Similarity NPD6781 Approved
0.6836 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6835 Remote Similarity NPD2313 Discontinued
0.6832 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6831 Remote Similarity NPD6784 Approved
0.6831 Remote Similarity NPD6785 Approved
0.6823 Remote Similarity NPD7680 Approved
0.6821 Remote Similarity NPD3882 Suspended
0.6821 Remote Similarity NPD7768 Phase 2
0.6821 Remote Similarity NPD8151 Discontinued
0.6818 Remote Similarity NPD7315 Approved
0.6815 Remote Similarity NPD6832 Phase 2
0.6813 Remote Similarity NPD1933 Approved
0.6813 Remote Similarity NPD4340 Discontinued
0.681 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6788 Remote Similarity NPD8166 Discontinued
0.6786 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7874 Approved
0.6782 Remote Similarity NPD3749 Approved
0.6776 Remote Similarity NPD5126 Approved
0.6776 Remote Similarity NPD5125 Phase 3
0.6776 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6774 Remote Similarity NPD3225 Approved
0.6774 Remote Similarity NPD8651 Approved
0.6774 Remote Similarity NPD1283 Approved
0.6772 Remote Similarity NPD3027 Phase 3
0.6765 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3226 Approved
0.6759 Remote Similarity NPD2684 Approved
0.6757 Remote Similarity NPD1241 Discontinued
0.6755 Remote Similarity NPD1894 Discontinued
0.6753 Remote Similarity NPD3972 Approved
0.6752 Remote Similarity NPD9494 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