Structure

Physi-Chem Properties

Molecular Weight:  1038.43
Volume:  997.828
LogP:  -0.292
LogD:  -0.098
LogS:  -2.851
# Rotatable Bonds:  23
TPSA:  392.97
# H-Bond Aceptor:  23
# H-Bond Donor:  15
# Rings:  6
# Heavy Atoms:  23

MedChem Properties

QED Drug-Likeness Score:  0.028
Synthetic Accessibility Score:  6.427
Fsp3:  0.64
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.621
MDCK Permeability:  6.893071258673444e-06
Pgp-inhibitor:  0.021
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.322
Plasma Protein Binding (PPB):  78.8272476196289%
Volume Distribution (VD):  0.29
Pgp-substrate:  8.53600025177002%

ADMET: Metabolism

CYP1A2-inhibitor:  0.038
CYP1A2-substrate:  0.006
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.047
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.014
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.056
CYP3A4-inhibitor:  0.206
CYP3A4-substrate:  0.012

ADMET: Excretion

Clearance (CL):  0.916
Half-life (T1/2):  0.931

ADMET: Toxicity

hERG Blockers:  0.392
Human Hepatotoxicity (H-HT):  0.367
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.096
Rat Oral Acute Toxicity:  0.003
Maximum Recommended Daily Dose:  0.984
Skin Sensitization:  0.951
Carcinogencity:  0.262
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.067

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

  Natural Product: NPC471874

Natural Product ID:  NPC471874
Common Name*:   Bis(((1S,3S,4R)-3-Hydroxy-4-(Hydroxymethyl)-4-(2-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-Yloxy)Ethyl)Cyclohexyl)Methyl)-2-(3,4-Dihydroxybenzylidene)-3-(4-Hydroxybenzylidene)Succinate
IUPAC Name:   bis[[(1S,3S,4R)-3-hydroxy-4-(hydroxymethyl)-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]cyclohexyl]methyl] (2E,3E)-2-[(3,4-dihydroxyphenyl)methylidene]-3-[(4-hydroxyphenyl)methylidene]butanedioate
Synonyms:  
Standard InCHIKey:  FNWONUVTZXJTAU-KCZGFTMTSA-N
Standard InCHI:  InChI=1S/C50H70O23/c51-20-35-39(60)41(62)43(64)47(72-35)68-13-11-49(24-53)9-7-28(18-37(49)58)22-70-45(66)31(15-26-1-4-30(55)5-2-26)32(16-27-3-6-33(56)34(57)17-27)46(67)71-23-29-8-10-50(25-54,38(59)19-29)12-14-69-48-44(65)42(63)40(61)36(21-52)73-48/h1-6,15-17,28-29,35-44,47-48,51-65H,7-14,18-25H2/b31-15+,32-16+/t28-,29-,35+,36+,37-,38-,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
SMILES:  C1CC(C(CC1COC(=O)C(=CC2=CC=C(C=C2)O)C(=CC3=CC(=C(C=C3)O)O)C(=O)OCC4CCC(C(C4)O)(CCOC5C(C(C(C(O5)CO)O)O)O)CO)O)(CCOC6C(C(C(C(O6)CO)O)O)O)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3262203
PubChem CID:   90676286
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 = 22.3 % PMID[454406]
NPT2 Others Unspecified Inhibition = 27.2 % PMID[454406]
NPT2 Others Unspecified Inhibition = 27.3 % PMID[454406]
NPT2 Others Unspecified Inhibition = 32.3 % PMID[454406]
NPT2 Others Unspecified Inhibition = 25.3 % PMID[454406]
NPT2 Others Unspecified Inhibition > 100.0 % PMID[454406]
NPT27 Others Unspecified Activity > 80.3 % PMID[454406]

☑ 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 NPC471874 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
0.9477 High Similarity NPC471873
0.9412 High Similarity NPC471869
0.9342 High Similarity NPC471878
0.9177 High Similarity NPC471870
0.9103 High Similarity NPC471875
0.9048 High Similarity NPC476375
0.9048 High Similarity NPC476378
0.9048 High Similarity NPC476397
0.9048 High Similarity NPC112
0.9048 High Similarity NPC205864
0.9048 High Similarity NPC269141
0.9048 High Similarity NPC175214
0.9048 High Similarity NPC476381
0.9048 High Similarity NPC76406
0.9048 High Similarity NPC298257
0.9048 High Similarity NPC119537
0.9048 High Similarity NPC264632
0.9048 High Similarity NPC476384
0.9048 High Similarity NPC247032
0.9048 High Similarity NPC96795
0.9048 High Similarity NPC476380
0.9041 High Similarity NPC476377
0.9041 High Similarity NPC47471
0.9034 High Similarity NPC205195
0.9006 High Similarity NPC471871
0.8986 High Similarity NPC64195
0.8973 High Similarity NPC475530
0.8973 High Similarity NPC473799
0.8966 High Similarity NPC260425
0.8954 High Similarity NPC87403
0.8919 High Similarity NPC105005
0.8912 High Similarity NPC134405
0.8912 High Similarity NPC476385
0.8904 High Similarity NPC197316
0.8904 High Similarity NPC64141
0.8904 High Similarity NPC476383
0.8904 High Similarity NPC81515
0.8904 High Similarity NPC68092
0.8904 High Similarity NPC472350
0.8904 High Similarity NPC89105
0.8889 High Similarity NPC106818
0.8867 High Similarity NPC229505
0.8859 High Similarity NPC300894
0.8859 High Similarity NPC296954
0.8859 High Similarity NPC196063
0.8859 High Similarity NPC141455
0.8851 High Similarity NPC265648
0.8851 High Similarity NPC222433
0.8836 High Similarity NPC78363
0.8759 High Similarity NPC287597
0.8759 High Similarity NPC886
0.8759 High Similarity NPC34293
0.8758 High Similarity NPC12006
0.875 High Similarity NPC23677
0.875 High Similarity NPC28776
0.875 High Similarity NPC473138
0.8712 High Similarity NPC100925
0.8712 High Similarity NPC32723
0.8712 High Similarity NPC469772
0.8712 High Similarity NPC469776
0.8712 High Similarity NPC135334
0.8712 High Similarity NPC469773
0.8712 High Similarity NPC469774
0.8712 High Similarity NPC469775
0.8712 High Similarity NPC469777
0.8712 High Similarity NPC469778
0.8712 High Similarity NPC295941
0.8707 High Similarity NPC476376
0.8693 High Similarity NPC473427
0.8693 High Similarity NPC471062
0.8693 High Similarity NPC306890
0.8693 High Similarity NPC259347
0.8693 High Similarity NPC476398
0.8693 High Similarity NPC476386
0.8693 High Similarity NPC470933
0.8693 High Similarity NPC94871
0.8667 High Similarity NPC40305
0.8649 High Similarity NPC171134
0.8649 High Similarity NPC321638
0.8649 High Similarity NPC321184
0.8649 High Similarity NPC328273
0.8636 High Similarity NPC257970
0.8636 High Similarity NPC470927
0.8618 High Similarity NPC320734
0.8571 High Similarity NPC476870
0.8571 High Similarity NPC263829
0.8562 High Similarity NPC232992
0.8553 High Similarity NPC34927
0.8553 High Similarity NPC34587
0.8553 High Similarity NPC476382
0.8553 High Similarity NPC252292
0.8553 High Similarity NPC100998
0.8543 High Similarity NPC204644
0.8526 High Similarity NPC478268
0.8516 High Similarity NPC470934
0.8516 High Similarity NPC476871
0.8516 High Similarity NPC188393
0.8514 High Similarity NPC471872
0.8514 High Similarity NPC154485
0.8494 Intermediate Similarity NPC473630
0.8493 Intermediate Similarity NPC254275
0.8493 Intermediate Similarity NPC473285
0.8487 Intermediate Similarity NPC476867
0.8487 Intermediate Similarity NPC471876
0.8477 Intermediate Similarity NPC296643
0.8462 Intermediate Similarity NPC143480
0.8462 Intermediate Similarity NPC77310
0.8462 Intermediate Similarity NPC125823
0.8462 Intermediate Similarity NPC85192
0.8462 Intermediate Similarity NPC7145
0.8447 Intermediate Similarity NPC7191
0.8447 Intermediate Similarity NPC149873
0.8431 Intermediate Similarity NPC476869
0.8431 Intermediate Similarity NPC476868
0.8431 Intermediate Similarity NPC476864
0.8431 Intermediate Similarity NPC476866
0.8425 Intermediate Similarity NPC235294
0.8425 Intermediate Similarity NPC46137
0.8415 Intermediate Similarity NPC286809
0.8414 Intermediate Similarity NPC477294
0.8414 Intermediate Similarity NPC229784
0.8414 Intermediate Similarity NPC184092
0.8414 Intermediate Similarity NPC477293
0.8397 Intermediate Similarity NPC69367
0.8389 Intermediate Similarity NPC470572
0.8387 Intermediate Similarity NPC300262
0.8387 Intermediate Similarity NPC192763
0.8387 Intermediate Similarity NPC28651
0.8387 Intermediate Similarity NPC210611
0.8387 Intermediate Similarity NPC261122
0.8387 Intermediate Similarity NPC199311
0.8387 Intermediate Similarity NPC201148
0.8387 Intermediate Similarity NPC80732
0.8387 Intermediate Similarity NPC215095
0.8387 Intermediate Similarity NPC3460
0.8385 Intermediate Similarity NPC269668
0.8378 Intermediate Similarity NPC471883
0.8377 Intermediate Similarity NPC476865
0.8375 Intermediate Similarity NPC172419
0.8375 Intermediate Similarity NPC238419
0.8366 Intermediate Similarity NPC26045
0.8365 Intermediate Similarity NPC131532
0.8355 Intermediate Similarity NPC140502
0.8354 Intermediate Similarity NPC266084
0.8354 Intermediate Similarity NPC473544
0.8354 Intermediate Similarity NPC475145
0.8354 Intermediate Similarity NPC475162
0.8354 Intermediate Similarity NPC475216
0.8354 Intermediate Similarity NPC83663
0.8354 Intermediate Similarity NPC475595
0.8345 Intermediate Similarity NPC232880
0.8344 Intermediate Similarity NPC271494
0.8344 Intermediate Similarity NPC227297
0.8344 Intermediate Similarity NPC473591
0.8344 Intermediate Similarity NPC155192
0.8333 Intermediate Similarity NPC478242
0.8323 Intermediate Similarity NPC210501
0.8323 Intermediate Similarity NPC104222
0.8323 Intermediate Similarity NPC114791
0.8323 Intermediate Similarity NPC478269
0.8323 Intermediate Similarity NPC141331
0.8323 Intermediate Similarity NPC318826
0.8322 Intermediate Similarity NPC123988
0.8313 Intermediate Similarity NPC11411
0.8313 Intermediate Similarity NPC247629
0.8313 Intermediate Similarity NPC228357
0.8313 Intermediate Similarity NPC239019
0.8312 Intermediate Similarity NPC216819
0.8312 Intermediate Similarity NPC287615
0.8312 Intermediate Similarity NPC83743
0.8312 Intermediate Similarity NPC53520
0.8312 Intermediate Similarity NPC262182
0.8311 Intermediate Similarity NPC28637
0.8303 Intermediate Similarity NPC470271
0.8303 Intermediate Similarity NPC311389
0.8301 Intermediate Similarity NPC113680
0.8301 Intermediate Similarity NPC235557
0.8301 Intermediate Similarity NPC278961
0.8299 Intermediate Similarity NPC138777
0.8299 Intermediate Similarity NPC225384
0.8299 Intermediate Similarity NPC246869
0.8299 Intermediate Similarity NPC219677
0.8289 Intermediate Similarity NPC186406
0.8282 Intermediate Similarity NPC246024
0.8278 Intermediate Similarity NPC220942
0.8278 Intermediate Similarity NPC182249
0.8276 Intermediate Similarity NPC476873
0.8276 Intermediate Similarity NPC288416
0.8276 Intermediate Similarity NPC108659
0.8276 Intermediate Similarity NPC264900
0.8276 Intermediate Similarity NPC79715
0.8276 Intermediate Similarity NPC231607
0.8263 Intermediate Similarity NPC477617
0.8261 Intermediate Similarity NPC187205
0.8247 Intermediate Similarity NPC292443
0.8247 Intermediate Similarity NPC232228
0.8243 Intermediate Similarity NPC473924
0.8242 Intermediate Similarity NPC59516
0.8242 Intermediate Similarity NPC175793
0.8239 Intermediate Similarity NPC205037

  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 NPC471874 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
0.8904 High Similarity NPD7266 Discontinued
0.8084 Intermediate Similarity NPD7228 Approved
0.8 Intermediate Similarity NPD8166 Discontinued
0.7949 Intermediate Similarity NPD6190 Approved
0.7907 Intermediate Similarity NPD8312 Approved
0.7907 Intermediate Similarity NPD8313 Approved
0.7853 Intermediate Similarity NPD8455 Phase 2
0.7733 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7240 Approved
0.7688 Intermediate Similarity NPD7685 Pre-registration
0.7674 Intermediate Similarity NPD7472 Approved
0.7674 Intermediate Similarity NPD7074 Phase 3
0.7665 Intermediate Similarity NPD6234 Discontinued
0.7654 Intermediate Similarity NPD1653 Approved
0.7651 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7054 Approved
0.7586 Intermediate Similarity NPD7251 Discontinued
0.7576 Intermediate Similarity NPD37 Approved
0.7545 Intermediate Similarity NPD4965 Approved
0.7545 Intermediate Similarity NPD4966 Approved
0.7545 Intermediate Similarity NPD4967 Phase 2
0.7543 Intermediate Similarity NPD7808 Phase 3
0.7529 Intermediate Similarity NPD6797 Phase 2
0.75 Intermediate Similarity NPD7097 Phase 1
0.75 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD8127 Discontinued
0.7457 Intermediate Similarity NPD3818 Discontinued
0.7443 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7458 Discontinued
0.7287 Intermediate Similarity NPD7680 Approved
0.7267 Intermediate Similarity NPD6674 Discontinued
0.7258 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD8320 Phase 1
0.7249 Intermediate Similarity NPD8319 Approved
0.7241 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6166 Phase 2
0.7241 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1613 Approved
0.7197 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8151 Discontinued
0.717 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4628 Phase 3
0.7115 Intermediate Similarity NPD3027 Phase 3
0.7112 Intermediate Similarity NPD7699 Phase 2
0.7112 Intermediate Similarity NPD7700 Phase 2
0.7095 Intermediate Similarity NPD6559 Discontinued
0.7088 Intermediate Similarity NPD8150 Discontinued
0.7069 Intermediate Similarity NPD7199 Phase 2
0.7048 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD230 Phase 1
0.7022 Intermediate Similarity NPD5844 Phase 1
0.7018 Intermediate Similarity NPD1465 Phase 2
0.7016 Intermediate Similarity NPD7435 Discontinued
0.7006 Intermediate Similarity NPD7473 Discontinued
0.6987 Remote Similarity NPD5736 Approved
0.6966 Remote Similarity NPD3751 Discontinued
0.6964 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1934 Approved
0.6952 Remote Similarity NPD6534 Approved
0.6952 Remote Similarity NPD6535 Approved
0.6948 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6943 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6941 Remote Similarity NPD4380 Phase 2
0.6932 Remote Similarity NPD6232 Discontinued
0.6927 Remote Similarity NPD7698 Approved
0.6927 Remote Similarity NPD7696 Phase 3
0.6927 Remote Similarity NPD7697 Approved
0.6919 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6902 Remote Similarity NPD8434 Phase 2
0.6899 Remote Similarity NPD7095 Approved
0.6893 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6888 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6888 Remote Similarity NPD7874 Approved
0.6879 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6872 Remote Similarity NPD7701 Phase 2
0.6859 Remote Similarity NPD6780 Approved
0.6859 Remote Similarity NPD6782 Approved
0.6859 Remote Similarity NPD6777 Approved
0.6859 Remote Similarity NPD6778 Approved
0.6859 Remote Similarity NPD6779 Approved
0.6859 Remote Similarity NPD6781 Approved
0.6859 Remote Similarity NPD6776 Approved
0.6855 Remote Similarity NPD3764 Approved
0.6836 Remote Similarity NPD3787 Discontinued
0.6833 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1091 Approved
0.6813 Remote Similarity NPD6663 Approved
0.6809 Remote Similarity NPD6212 Phase 3
0.6809 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6809 Remote Similarity NPD6213 Phase 3
0.6807 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6273 Approved
0.6804 Remote Similarity NPD7871 Phase 2
0.6804 Remote Similarity NPD7870 Phase 2
0.68 Remote Similarity NPD7075 Discontinued
0.6793 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6823 Phase 2
0.6782 Remote Similarity NPD5402 Approved
0.677 Remote Similarity NPD7966 Clinical (unspecified phase)
0.677 Remote Similarity NPD3620 Phase 2
0.677 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7783 Phase 2
0.6768 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7801 Approved
0.6752 Remote Similarity NPD3094 Phase 2
0.6735 Remote Similarity NPD3021 Approved
0.6735 Remote Similarity NPD3022 Approved
0.6727 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6724 Remote Similarity NPD2801 Approved
0.6707 Remote Similarity NPD7003 Approved
0.6707 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4110 Phase 3
0.6686 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6686 Remote Similarity NPD3455 Phase 2
0.6686 Remote Similarity NPD3817 Phase 2
0.6685 Remote Similarity NPD7799 Discontinued
0.6667 Remote Similarity NPD4060 Phase 1
0.6667 Remote Similarity NPD943 Approved
0.6667 Remote Similarity NPD5408 Approved
0.6667 Remote Similarity NPD5404 Approved
0.6667 Remote Similarity NPD2861 Phase 2
0.6667 Remote Similarity NPD5405 Approved
0.6667 Remote Similarity NPD5406 Approved
0.6648 Remote Similarity NPD7768 Phase 2
0.6648 Remote Similarity NPD3882 Suspended
0.6647 Remote Similarity NPD7028 Phase 2
0.6646 Remote Similarity NPD6798 Discontinued
0.6629 Remote Similarity NPD5494 Approved
0.6629 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7819 Suspended
0.6626 Remote Similarity NPD6355 Discontinued
0.6625 Remote Similarity NPD4908 Phase 1
0.6623 Remote Similarity NPD1357 Approved
0.6605 Remote Similarity NPD6233 Phase 2
0.6603 Remote Similarity NPD3092 Approved
0.6595 Remote Similarity NPD7549 Discontinued
0.6592 Remote Similarity NPD6959 Discontinued
0.6591 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6588 Remote Similarity NPD1511 Approved
0.6584 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6581 Remote Similarity NPD5125 Phase 3
0.6581 Remote Similarity NPD5126 Approved
0.6575 Remote Similarity NPD7852 Clinical (unspecified phase)
0.657 Remote Similarity NPD5403 Approved
0.6566 Remote Similarity NPD2935 Discontinued
0.6564 Remote Similarity NPD4140 Approved
0.6561 Remote Similarity NPD9269 Phase 2
0.6553 Remote Similarity NPD8155 Clinical (unspecified phase)
0.655 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6548 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6543 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6541 Remote Similarity NPD8368 Discontinued
0.6527 Remote Similarity NPD5762 Approved
0.6527 Remote Similarity NPD5763 Approved
0.6524 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5124 Phase 1
0.6514 Remote Similarity NPD7411 Suspended
0.6512 Remote Similarity NPD1512 Approved
0.6509 Remote Similarity NPD3750 Approved
0.6509 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6497 Remote Similarity NPD3705 Approved
0.6494 Remote Similarity NPD3226 Approved
0.6494 Remote Similarity NPD5536 Phase 2
0.649 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6485 Remote Similarity NPD6653 Approved
0.6477 Remote Similarity NPD6801 Discontinued
0.6477 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6474 Remote Similarity NPD8361 Approved
0.6474 Remote Similarity NPD8360 Approved
0.6471 Remote Similarity NPD4198 Discontinued
0.6467 Remote Similarity NPD6032 Approved
0.6457 Remote Similarity NPD6599 Discontinued
0.6455 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6453 Remote Similarity NPD5401 Approved
0.6452 Remote Similarity NPD7039 Approved
0.6452 Remote Similarity NPD7038 Approved
0.6452 Remote Similarity NPD9545 Approved
0.6452 Remote Similarity NPD3091 Approved
0.645 Remote Similarity NPD1652 Phase 2
0.645 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6438 Remote Similarity NPD1470 Approved
0.6436 Remote Similarity NPD8407 Phase 2
0.6433 Remote Similarity NPD5058 Phase 3
0.6432 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6425 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6424 Remote Similarity NPD5735 Approved
0.6424 Remote Similarity NPD4340 Discontinued
0.6424 Remote Similarity NPD1933 Approved
0.642 Remote Similarity NPD7615 Clinical (unspecified phase)
0.642 Remote Similarity NPD6385 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