Structure

Physi-Chem Properties

Molecular Weight:  1030.37
Volume:  981.362
LogP:  -1.076
LogD:  -0.575
LogS:  -2.246
# Rotatable Bonds:  19
TPSA:  389.81
# H-Bond Aceptor:  23
# H-Bond Donor:  14
# Rings:  7
# Heavy Atoms:  23

MedChem Properties

QED Drug-Likeness Score:  0.024
Synthetic Accessibility Score:  6.837
Fsp3:  0.54
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  3
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.884
MDCK Permeability:  3.0779610824538395e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.995
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.184
Plasma Protein Binding (PPB):  69.92051696777344%
Volume Distribution (VD):  0.395
Pgp-substrate:  29.75373649597168%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.045
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.045
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.032
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.024
CYP3A4-inhibitor:  0.25
CYP3A4-substrate:  0.01

ADMET: Excretion

Clearance (CL):  1.197
Half-life (T1/2):  0.637

ADMET: Toxicity

hERG Blockers:  0.19
Human Hepatotoxicity (H-HT):  0.152
Drug-inuced Liver Injury (DILI):  0.024
AMES Toxicity:  0.085
Rat Oral Acute Toxicity:  0.002
Maximum Recommended Daily Dose:  0.965
Skin Sensitization:  0.947
Carcinogencity:  0.321
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.92

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

  Natural Product: NPC471870

Natural Product ID:  NPC471870
Common Name*:   Canangalignan Ii
IUPAC Name:   bis[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[(Z)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] (1R,2S)-6,7-dihydroxy-1-(4-hydroxyphenyl)-1,2-dihydronaphthalene-2,3-dicarboxylate
Synonyms:  
Standard InCHIKey:  WJXUWXFVYVROPE-FEXGQHPCSA-N
Standard InCHI:  InChI=1S/C50H62O23/c51-18-33-39(60)41(62)43(64)47(72-33)68-11-9-49(22-53)7-5-24(13-35(49)58)20-70-45(66)30-15-27-16-31(56)32(57)17-29(27)37(26-1-3-28(55)4-2-26)38(30)46(67)71-21-25-6-8-50(23-54,36(59)14-25)10-12-69-48-44(65)42(63)40(61)34(19-52)73-48/h1-4,9-12,15-17,22-25,33-44,47-48,51-52,55-65H,5-8,13-14,18-21H2/b11-9-,12-10-/t24-,25-,33+,34+,35-,36-,37+,38+,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
SMILES:  OC[C@H]1O[C@@H](O/C=C[C@@]2(C=O)CC[C@@H](C[C@@H]2O)COC(=O)C2=Cc3cc(O)c(cc3[C@H]([C@@H]2C(=O)OC[C@H]2CC[C@]([C@H](C2)O)(C=O)/C=CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3262192
PubChem CID:   90676278
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan 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
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9348 Cananga odorata Species Annonaceae 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
NPT2 Others Unspecified Inhibition = 9.2 % PMID[480508]
NPT2 Others Unspecified Inhibition = 8.7 % PMID[480508]
NPT2 Others Unspecified Inhibition = 3.6 % PMID[480508]
NPT2 Others Unspecified Inhibition = 2.9 % PMID[480508]
NPT2 Others Unspecified Inhibition > 100.0 % PMID[480508]
NPT27 Others Unspecified Activity > 80.3 % PMID[480508]

☑ 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 NPC471870 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
0.9814 High Similarity NPC471871
0.9684 High Similarity NPC471873
0.962 High Similarity NPC471869
0.9177 High Similarity NPC471874
0.8987 High Similarity NPC12006
0.8929 High Similarity NPC295941
0.8929 High Similarity NPC135334
0.8929 High Similarity NPC32723
0.8929 High Similarity NPC469772
0.8929 High Similarity NPC469774
0.8929 High Similarity NPC469776
0.8929 High Similarity NPC469775
0.8929 High Similarity NPC469778
0.8929 High Similarity NPC469773
0.8929 High Similarity NPC100925
0.8929 High Similarity NPC469777
0.8824 High Similarity NPC473630
0.882 High Similarity NPC87403
0.8758 High Similarity NPC106818
0.872 High Similarity NPC471878
0.8655 High Similarity NPC124828
0.8625 High Similarity NPC473138
0.8625 High Similarity NPC28776
0.8589 High Similarity NPC475216
0.8589 High Similarity NPC475595
0.8589 High Similarity NPC266084
0.8589 High Similarity NPC475162
0.8589 High Similarity NPC475145
0.8589 High Similarity NPC473544
0.8589 High Similarity NPC83663
0.8488 Intermediate Similarity NPC13989
0.8462 Intermediate Similarity NPC25889
0.8438 Intermediate Similarity NPC53520
0.843 Intermediate Similarity NPC179240
0.84 Intermediate Similarity NPC469418
0.8385 Intermediate Similarity NPC320734
0.8373 Intermediate Similarity NPC131532
0.8363 Intermediate Similarity NPC469419
0.8354 Intermediate Similarity NPC471875
0.8343 Intermediate Similarity NPC170018
0.8343 Intermediate Similarity NPC76112
0.8343 Intermediate Similarity NPC92403
0.8343 Intermediate Similarity NPC66820
0.8343 Intermediate Similarity NPC475299
0.8333 Intermediate Similarity NPC471750
0.8324 Intermediate Similarity NPC472803
0.8314 Intermediate Similarity NPC311389
0.8314 Intermediate Similarity NPC185498
0.8314 Intermediate Similarity NPC470271
0.8313 Intermediate Similarity NPC298257
0.8313 Intermediate Similarity NPC477873
0.8313 Intermediate Similarity NPC476397
0.8313 Intermediate Similarity NPC247032
0.8313 Intermediate Similarity NPC476375
0.8313 Intermediate Similarity NPC112
0.8313 Intermediate Similarity NPC476380
0.8313 Intermediate Similarity NPC264632
0.8313 Intermediate Similarity NPC476378
0.8313 Intermediate Similarity NPC175214
0.8313 Intermediate Similarity NPC205864
0.8313 Intermediate Similarity NPC204644
0.8313 Intermediate Similarity NPC119537
0.8313 Intermediate Similarity NPC76406
0.8313 Intermediate Similarity NPC476381
0.8313 Intermediate Similarity NPC269141
0.8313 Intermediate Similarity NPC96795
0.8313 Intermediate Similarity NPC476384
0.8313 Intermediate Similarity NPC469447
0.8303 Intermediate Similarity NPC475579
0.8303 Intermediate Similarity NPC473773
0.8302 Intermediate Similarity NPC476377
0.8302 Intermediate Similarity NPC47471
0.8291 Intermediate Similarity NPC205195
0.8287 Intermediate Similarity NPC264302
0.8282 Intermediate Similarity NPC23677
0.8276 Intermediate Similarity NPC477617
0.8268 Intermediate Similarity NPC299855
0.8268 Intermediate Similarity NPC96194
0.8261 Intermediate Similarity NPC25491
0.8261 Intermediate Similarity NPC64195
0.8258 Intermediate Similarity NPC476203
0.8256 Intermediate Similarity NPC175793
0.8256 Intermediate Similarity NPC306475
0.8249 Intermediate Similarity NPC195114
0.8246 Intermediate Similarity NPC100420
0.8242 Intermediate Similarity NPC118033
0.8242 Intermediate Similarity NPC77310
0.8239 Intermediate Similarity NPC473799
0.8239 Intermediate Similarity NPC475530
0.8239 Intermediate Similarity NPC475613
0.8239 Intermediate Similarity NPC469397
0.8235 Intermediate Similarity NPC266365
0.8228 Intermediate Similarity NPC260425
0.8222 Intermediate Similarity NPC105591
0.8222 Intermediate Similarity NPC65489
0.8222 Intermediate Similarity NPC189704
0.8221 Intermediate Similarity NPC470330
0.8218 Intermediate Similarity NPC470272
0.8212 Intermediate Similarity NPC231254
0.8208 Intermediate Similarity NPC43918
0.8208 Intermediate Similarity NPC261411
0.8208 Intermediate Similarity NPC190204
0.8208 Intermediate Similarity NPC128403
0.8208 Intermediate Similarity NPC286809
0.8202 Intermediate Similarity NPC188217
0.8199 Intermediate Similarity NPC105005
0.8197 Intermediate Similarity NPC476358
0.8192 Intermediate Similarity NPC80360
0.8192 Intermediate Similarity NPC260300
0.8187 Intermediate Similarity NPC291957
0.8187 Intermediate Similarity NPC27518
0.8187 Intermediate Similarity NPC14030
0.8187 Intermediate Similarity NPC476385
0.8187 Intermediate Similarity NPC134405
0.8187 Intermediate Similarity NPC304110
0.8187 Intermediate Similarity NPC187934
0.8187 Intermediate Similarity NPC97637
0.8182 Intermediate Similarity NPC69367
0.8177 Intermediate Similarity NPC7839
0.8177 Intermediate Similarity NPC476067
0.8177 Intermediate Similarity NPC475121
0.8177 Intermediate Similarity NPC142291
0.8177 Intermediate Similarity NPC205721
0.8176 Intermediate Similarity NPC64141
0.8176 Intermediate Similarity NPC89105
0.8176 Intermediate Similarity NPC44507
0.8176 Intermediate Similarity NPC472350
0.8176 Intermediate Similarity NPC476383
0.8176 Intermediate Similarity NPC81515
0.8176 Intermediate Similarity NPC68092
0.8176 Intermediate Similarity NPC197316
0.8166 Intermediate Similarity NPC187205
0.8161 Intermediate Similarity NPC266545
0.8161 Intermediate Similarity NPC472133
0.8161 Intermediate Similarity NPC202428
0.816 Intermediate Similarity NPC229505
0.8156 Intermediate Similarity NPC473776
0.8156 Intermediate Similarity NPC473205
0.8155 Intermediate Similarity NPC474501
0.8148 Intermediate Similarity NPC196063
0.8148 Intermediate Similarity NPC296954
0.8148 Intermediate Similarity NPC141455
0.8148 Intermediate Similarity NPC26045
0.8148 Intermediate Similarity NPC300894
0.8146 Intermediate Similarity NPC198902
0.814 Intermediate Similarity NPC470898
0.814 Intermediate Similarity NPC14294
0.814 Intermediate Similarity NPC116759
0.814 Intermediate Similarity NPC227297
0.8137 Intermediate Similarity NPC222433
0.8137 Intermediate Similarity NPC265648
0.8136 Intermediate Similarity NPC472723
0.8136 Intermediate Similarity NPC475054
0.8133 Intermediate Similarity NPC473680
0.8133 Intermediate Similarity NPC475311
0.8133 Intermediate Similarity NPC473579
0.8133 Intermediate Similarity NPC475454
0.8132 Intermediate Similarity NPC472720
0.8132 Intermediate Similarity NPC201814
0.8132 Intermediate Similarity NPC31208
0.8132 Intermediate Similarity NPC93065
0.8132 Intermediate Similarity NPC472724
0.8132 Intermediate Similarity NPC472721
0.8132 Intermediate Similarity NPC160543
0.8132 Intermediate Similarity NPC469652
0.8129 Intermediate Similarity NPC477627
0.8129 Intermediate Similarity NPC478267
0.8125 Intermediate Similarity NPC473591
0.8125 Intermediate Similarity NPC316539
0.8125 Intermediate Similarity NPC155192
0.8125 Intermediate Similarity NPC199357
0.8125 Intermediate Similarity NPC271494
0.8121 Intermediate Similarity NPC473427
0.8121 Intermediate Similarity NPC476398
0.8121 Intermediate Similarity NPC259347
0.8121 Intermediate Similarity NPC476386
0.8121 Intermediate Similarity NPC94871
0.8121 Intermediate Similarity NPC471062
0.8121 Intermediate Similarity NPC329657
0.8121 Intermediate Similarity NPC470933
0.8121 Intermediate Similarity NPC306890
0.8118 Intermediate Similarity NPC469654
0.8118 Intermediate Similarity NPC53139
0.8114 Intermediate Similarity NPC47521
0.8114 Intermediate Similarity NPC472129
0.8114 Intermediate Similarity NPC43434
0.8113 Intermediate Similarity NPC78363
0.8107 Intermediate Similarity NPC148323
0.8107 Intermediate Similarity NPC283480
0.8103 Intermediate Similarity NPC31034
0.8103 Intermediate Similarity NPC298847
0.8103 Intermediate Similarity NPC177362
0.8103 Intermediate Similarity NPC63470
0.8101 Intermediate Similarity NPC477860
0.8101 Intermediate Similarity NPC475161
0.8095 Intermediate Similarity NPC160882
0.8095 Intermediate Similarity NPC472127
0.8095 Intermediate Similarity NPC472128
0.8092 Intermediate Similarity NPC478022
0.8092 Intermediate Similarity NPC478020

  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 NPC471870 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
0.8343 Intermediate Similarity NPD8313 Approved
0.8343 Intermediate Similarity NPD8312 Approved
0.8314 Intermediate Similarity NPD7228 Approved
0.8176 Intermediate Similarity NPD7266 Discontinued
0.8137 Intermediate Similarity NPD8166 Discontinued
0.8011 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD7240 Approved
0.7907 Intermediate Similarity NPD6234 Discontinued
0.7882 Intermediate Similarity NPD8455 Phase 2
0.7845 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD37 Approved
0.7791 Intermediate Similarity NPD4965 Approved
0.7791 Intermediate Similarity NPD4966 Approved
0.7791 Intermediate Similarity NPD4967 Phase 2
0.7709 Intermediate Similarity NPD7074 Phase 3
0.7709 Intermediate Similarity NPD7472 Approved
0.7654 Intermediate Similarity NPD7054 Approved
0.7651 Intermediate Similarity NPD6190 Approved
0.7624 Intermediate Similarity NPD7251 Discontinued
0.7624 Intermediate Similarity NPD7685 Pre-registration
0.7614 Intermediate Similarity NPD8127 Discontinued
0.759 Intermediate Similarity NPD8151 Discontinued
0.7582 Intermediate Similarity NPD7808 Phase 3
0.7569 Intermediate Similarity NPD6797 Phase 2
0.7569 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD8320 Phase 1
0.7565 Intermediate Similarity NPD8319 Approved
0.7515 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8434 Phase 2
0.7514 Intermediate Similarity NPD8150 Discontinued
0.7513 Intermediate Similarity NPD7680 Approved
0.75 Intermediate Similarity NPD3818 Discontinued
0.7487 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD7473 Discontinued
0.7435 Intermediate Similarity NPD7700 Phase 2
0.7435 Intermediate Similarity NPD7699 Phase 2
0.7432 Intermediate Similarity NPD6559 Discontinued
0.7423 Intermediate Similarity NPD7435 Discontinued
0.7403 Intermediate Similarity NPD3751 Discontinued
0.7374 Intermediate Similarity NPD6232 Discontinued
0.7363 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7458 Discontinued
0.7333 Intermediate Similarity NPD7697 Approved
0.7333 Intermediate Similarity NPD7696 Phase 3
0.7333 Intermediate Similarity NPD7698 Approved
0.7293 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD6166 Phase 2
0.7286 Intermediate Similarity NPD7874 Approved
0.7286 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6535 Approved
0.7277 Intermediate Similarity NPD6534 Approved
0.7273 Intermediate Similarity NPD7701 Phase 2
0.7268 Intermediate Similarity NPD6781 Approved
0.7268 Intermediate Similarity NPD6779 Approved
0.7268 Intermediate Similarity NPD6777 Approved
0.7268 Intermediate Similarity NPD5844 Phase 1
0.7268 Intermediate Similarity NPD6776 Approved
0.7268 Intermediate Similarity NPD6778 Approved
0.7268 Intermediate Similarity NPD6780 Approved
0.7268 Intermediate Similarity NPD6782 Approved
0.7222 Intermediate Similarity NPD7199 Phase 2
0.7219 Intermediate Similarity NPD6674 Discontinued
0.7208 Intermediate Similarity NPD7870 Phase 2
0.7208 Intermediate Similarity NPD7871 Phase 2
0.7194 Intermediate Similarity NPD6823 Phase 2
0.7184 Intermediate Similarity NPD1653 Approved
0.7182 Intermediate Similarity NPD3787 Discontinued
0.7175 Intermediate Similarity NPD1465 Phase 2
0.7164 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7783 Phase 2
0.7164 Intermediate Similarity NPD7801 Approved
0.7151 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6213 Phase 3
0.7135 Intermediate Similarity NPD6212 Phase 3
0.7135 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7097 Phase 1
0.7115 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD4380 Phase 2
0.7079 Intermediate Similarity NPD7819 Suspended
0.7079 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4628 Phase 3
0.7069 Intermediate Similarity NPD6273 Approved
0.7049 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5405 Approved
0.7041 Intermediate Similarity NPD5406 Approved
0.7041 Intermediate Similarity NPD5404 Approved
0.7041 Intermediate Similarity NPD5408 Approved
0.7037 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD6959 Discontinued
0.7027 Intermediate Similarity NPD7799 Discontinued
0.7022 Intermediate Similarity NPD1934 Approved
0.7011 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6988 Remote Similarity NPD6663 Approved
0.6977 Remote Similarity NPD7003 Approved
0.6977 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7075 Discontinued
0.6951 Remote Similarity NPD5736 Approved
0.6949 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6949 Remote Similarity NPD3226 Approved
0.6938 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6928 Remote Similarity NPD3764 Approved
0.6914 Remote Similarity NPD4160 Clinical (unspecified phase)
0.691 Remote Similarity NPD7028 Phase 2
0.6906 Remote Similarity NPD7768 Phase 2
0.6885 Remote Similarity NPD5494 Approved
0.6878 Remote Similarity NPD8368 Discontinued
0.6851 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6851 Remote Similarity NPD5402 Approved
0.6845 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6836 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1470 Approved
0.6828 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6805 Remote Similarity NPD230 Phase 1
0.6804 Remote Similarity NPD8361 Approved
0.6804 Remote Similarity NPD8360 Approved
0.6796 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6796 Remote Similarity NPD2801 Approved
0.6782 Remote Similarity NPD3750 Approved
0.6771 Remote Similarity NPD8407 Phase 2
0.6766 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6758 Remote Similarity NPD3817 Phase 2
0.675 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6749 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6746 Remote Similarity NPD1613 Approved
0.6746 Remote Similarity NPD3620 Phase 2
0.6746 Remote Similarity NPD8404 Phase 2
0.6746 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6746 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6744 Remote Similarity NPD2935 Discontinued
0.6721 Remote Similarity NPD3882 Suspended
0.6718 Remote Similarity NPD8435 Approved
0.6705 Remote Similarity NPD2346 Discontinued
0.6686 Remote Similarity NPD4110 Phase 3
0.6686 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7411 Suspended
0.6667 Remote Similarity NPD7390 Discontinued
0.6667 Remote Similarity NPD1511 Approved
0.6667 Remote Similarity NPD3027 Phase 3
0.6651 Remote Similarity NPD7930 Approved
0.6648 Remote Similarity NPD6801 Discontinued
0.6648 Remote Similarity NPD5403 Approved
0.6647 Remote Similarity NPD943 Approved
0.6647 Remote Similarity NPD2438 Suspended
0.6647 Remote Similarity NPD4060 Phase 1
0.663 Remote Similarity NPD6599 Discontinued
0.6629 Remote Similarity NPD2532 Approved
0.6629 Remote Similarity NPD2534 Approved
0.6629 Remote Similarity NPD2533 Approved
0.6628 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6627 Remote Similarity NPD3094 Phase 2
0.662 Remote Similarity NPD8059 Phase 3
0.662 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6615 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6612 Remote Similarity NPD5760 Phase 2
0.6612 Remote Similarity NPD5761 Phase 2
0.6608 Remote Similarity NPD6355 Discontinued
0.66 Remote Similarity NPD8485 Approved
0.6595 Remote Similarity NPD3749 Approved
0.6592 Remote Similarity NPD1512 Approved
0.6591 Remote Similarity NPD1878 Clinical (unspecified phase)
0.659 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6588 Remote Similarity NPD8032 Phase 2
0.6585 Remote Similarity NPD1201 Approved
0.6571 Remote Similarity NPD970 Clinical (unspecified phase)
0.6568 Remote Similarity NPD7095 Approved
0.6564 Remote Similarity NPD3019 Approved
0.6564 Remote Similarity NPD2932 Approved
0.6552 Remote Similarity NPD1551 Phase 2
0.655 Remote Similarity NPD4140 Approved
0.6536 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6536 Remote Similarity NPD5401 Approved
0.6534 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6529 Remote Similarity NPD6798 Discontinued
0.6517 Remote Similarity NPD7236 Approved
0.6514 Remote Similarity NPD5762 Approved
0.6514 Remote Similarity NPD5763 Approved
0.6514 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6512 Remote Similarity NPD1933 Approved
0.6509 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6506 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6505 Remote Similarity NPD7999 Approved
0.6494 Remote Similarity NPD2799 Discontinued
0.6494 Remote Similarity NPD3748 Approved
0.6494 Remote Similarity NPD651 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6233 Phase 2
0.6488 Remote Similarity NPD7497 Discontinued
0.6485 Remote Similarity NPD3092 Approved
0.6484 Remote Similarity NPD3455 Phase 2
0.6482 Remote Similarity NPD7296 Approved
0.6477 Remote Similarity NPD1549 Phase 2
0.6471 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6467 Remote Similarity NPD1283 Approved
0.6465 Remote Similarity NPD7907 Approved
0.6463 Remote Similarity NPD5126 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