Structure

Physi-Chem Properties

Molecular Weight:  834.26
Volume:  790.405
LogP:  2.445
LogD:  1.391
LogS:  -3.684
# Rotatable Bonds:  21
TPSA:  275.64
# H-Bond Aceptor:  20
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.086
Synthetic Accessibility Score:  5.182
Fsp3:  0.487
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.886
MDCK Permeability:  0.00013067903637420386
Pgp-inhibitor:  0.096
Pgp-substrate:  0.571
Human Intestinal Absorption (HIA):  0.982
20% Bioavailability (F20%):  0.032
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  60.249481201171875%
Volume Distribution (VD):  0.292
Pgp-substrate:  32.90043640136719%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.094
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.336
CYP2C9-substrate:  0.057
CYP2D6-inhibitor:  0.928
CYP2D6-substrate:  0.089
CYP3A4-inhibitor:  0.853
CYP3A4-substrate:  0.133

ADMET: Excretion

Clearance (CL):  2.019
Half-life (T1/2):  0.98

ADMET: Toxicity

hERG Blockers:  0.203
Human Hepatotoxicity (H-HT):  0.991
Drug-inuced Liver Injury (DILI):  0.976
AMES Toxicity:  0.156
Rat Oral Acute Toxicity:  0.043
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.788
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC475530

Natural Product ID:  NPC475530
Common Name*:   [(2R,3R,4S,5R,6R)-5-Acetyloxy-2-(Acetyloxymethyl)-6-[2-(3,4-Dihydroxyphenyl)Ethoxy]-4-[(2S,3R,4R,5S,6S)-3,4,5-Triacetyloxy-6-Methyloxan-2-Yl]Oxyoxan-3-Yl] (E)-3-(3,4-Dihydroxyphenyl)Prop-2-Enoate
IUPAC Name:   [(2R,3R,4S,5R,6R)-5-acetyloxy-2-(acetyloxymethyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  XZKKILCLQIINLY-MXJIFSESSA-N
Standard InCHI:  InChI=1S/C39H46O20/c1-18-32(53-20(3)41)34(54-21(4)42)37(56-23(6)44)39(52-18)59-35-33(58-31(49)12-9-24-7-10-26(45)28(47)15-24)30(17-51-19(2)40)57-38(36(35)55-22(5)43)50-14-13-25-8-11-27(46)29(48)16-25/h7-12,15-16,18,30,32-39,45-48H,13-14,17H2,1-6H3/b12-9+/t18-,30+,32-,33+,34+,35-,36+,37+,38+,39-/m0/s1
SMILES:  CC(=O)OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507401
PubChem CID:   10605522
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

*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
NPO6610 Markhamia lutea Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[9599250]
NPO6610 Markhamia lutea Species Bignoniaceae 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
NPT70 Organism Respiratory syncytial virus Respiratory syncytial virus EC50 = 5.87 ug.mL-1 PMID[548474]
NPT27 Others Unspecified IC50 = 26.2 ug.mL-1 PMID[548474]
NPT2 Others Unspecified Ratio IC50/EC50 = 4.4 n.a. PMID[548474]

☑ 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 NPC475530 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
1.0 High Similarity NPC473799
0.9925 High Similarity NPC47471
0.9925 High Similarity NPC476377
0.9778 High Similarity NPC269141
0.9778 High Similarity NPC76406
0.9778 High Similarity NPC476384
0.9778 High Similarity NPC247032
0.9778 High Similarity NPC112
0.9778 High Similarity NPC476375
0.9778 High Similarity NPC96795
0.9778 High Similarity NPC476378
0.9778 High Similarity NPC476380
0.9778 High Similarity NPC205864
0.9778 High Similarity NPC298257
0.9778 High Similarity NPC476397
0.9778 High Similarity NPC264632
0.9778 High Similarity NPC175214
0.9778 High Similarity NPC119537
0.9778 High Similarity NPC476381
0.9776 High Similarity NPC476385
0.9776 High Similarity NPC134405
0.9774 High Similarity NPC476383
0.9774 High Similarity NPC81515
0.9774 High Similarity NPC472350
0.9774 High Similarity NPC197316
0.9774 High Similarity NPC68092
0.9774 High Similarity NPC205195
0.9774 High Similarity NPC89105
0.9774 High Similarity NPC64141
0.9706 High Similarity NPC196063
0.9706 High Similarity NPC64195
0.9706 High Similarity NPC296954
0.9706 High Similarity NPC300894
0.9706 High Similarity NPC141455
0.9699 High Similarity NPC260425
0.9632 High Similarity NPC105005
0.9565 High Similarity NPC229505
0.9559 High Similarity NPC222433
0.9559 High Similarity NPC265648
0.9552 High Similarity NPC78363
0.9552 High Similarity NPC476376
0.9474 High Similarity NPC886
0.9474 High Similarity NPC287597
0.9474 High Similarity NPC34293
0.9362 High Similarity NPC471062
0.9362 High Similarity NPC476386
0.9362 High Similarity NPC473427
0.9362 High Similarity NPC259347
0.9362 High Similarity NPC306890
0.9362 High Similarity NPC470933
0.9362 High Similarity NPC94871
0.9362 High Similarity NPC476398
0.9353 High Similarity NPC34927
0.9353 High Similarity NPC100998
0.9353 High Similarity NPC34587
0.9353 High Similarity NPC252292
0.9353 High Similarity NPC476382
0.9348 High Similarity NPC40305
0.9338 High Similarity NPC321638
0.9338 High Similarity NPC171134
0.9338 High Similarity NPC328273
0.9338 High Similarity NPC321184
0.9323 High Similarity NPC473285
0.9296 High Similarity NPC470927
0.9296 High Similarity NPC470934
0.9296 High Similarity NPC188393
0.9296 High Similarity NPC257970
0.9259 High Similarity NPC263829
0.9259 High Similarity NPC476870
0.9248 High Similarity NPC235294
0.9248 High Similarity NPC46137
0.922 High Similarity NPC232992
0.9185 High Similarity NPC471883
0.9167 High Similarity NPC106818
0.9149 High Similarity NPC476865
0.9143 High Similarity NPC476867
0.9137 High Similarity NPC140502
0.9104 High Similarity NPC225384
0.9104 High Similarity NPC246869
0.9104 High Similarity NPC138777
0.9103 High Similarity NPC87403
0.9098 High Similarity NPC477293
0.9098 High Similarity NPC229784
0.9098 High Similarity NPC477294
0.9078 High Similarity NPC476866
0.9078 High Similarity NPC476869
0.9078 High Similarity NPC83743
0.9078 High Similarity NPC287615
0.9078 High Similarity NPC216819
0.9078 High Similarity NPC262182
0.9078 High Similarity NPC476864
0.9078 High Similarity NPC476868
0.9037 High Similarity NPC254275
0.9023 High Similarity NPC232880
0.9021 High Similarity NPC199311
0.9021 High Similarity NPC28651
0.9021 High Similarity NPC80732
0.9021 High Similarity NPC3460
0.9021 High Similarity NPC300262
0.9021 High Similarity NPC201148
0.9021 High Similarity NPC210611
0.9021 High Similarity NPC192763
0.9021 High Similarity NPC215095
0.9021 High Similarity NPC23677
0.9021 High Similarity NPC261122
0.8973 High Similarity NPC471874
0.8971 High Similarity NPC254398
0.8963 High Similarity NPC219677
0.8955 High Similarity NPC184092
0.8947 High Similarity NPC476873
0.8947 High Similarity NPC288416
0.8936 High Similarity NPC478239
0.8929 High Similarity NPC186406
0.8904 High Similarity NPC478268
0.8897 High Similarity NPC476871
0.8897 High Similarity NPC473924
0.8889 High Similarity NPC28776
0.8889 High Similarity NPC473138
0.8873 High Similarity NPC110063
0.8872 High Similarity NPC471157
0.8865 High Similarity NPC473873
0.8865 High Similarity NPC473792
0.8865 High Similarity NPC157816
0.8865 High Similarity NPC296643
0.8836 High Similarity NPC143480
0.8836 High Similarity NPC7145
0.8836 High Similarity NPC125823
0.8836 High Similarity NPC85192
0.8832 High Similarity NPC28637
0.8828 High Similarity NPC283839
0.8828 High Similarity NPC106138
0.8828 High Similarity NPC90896
0.8824 High Similarity NPC478255
0.8806 High Similarity NPC264900
0.8806 High Similarity NPC106677
0.8806 High Similarity NPC108659
0.8806 High Similarity NPC79715
0.8806 High Similarity NPC231607
0.8803 High Similarity NPC113680
0.8803 High Similarity NPC278961
0.8797 High Similarity NPC126991
0.8797 High Similarity NPC83218
0.8777 High Similarity NPC157554
0.8776 High Similarity NPC289967
0.8776 High Similarity NPC472611
0.8776 High Similarity NPC472612
0.8767 High Similarity NPC69367
0.875 High Similarity NPC199928
0.8741 High Similarity NPC232228
0.8741 High Similarity NPC225307
0.8741 High Similarity NPC292443
0.8731 High Similarity NPC94179
0.8723 High Similarity NPC202700
0.8705 High Similarity NPC123988
0.8699 High Similarity NPC478242
0.8667 High Similarity NPC173150
0.8667 High Similarity NPC156692
0.8667 High Similarity NPC471881
0.8667 High Similarity NPC471882
0.8667 High Similarity NPC103533
0.8667 High Similarity NPC35288
0.8667 High Similarity NPC11411
0.8667 High Similarity NPC45224
0.8652 High Similarity NPC100389
0.8652 High Similarity NPC220942
0.8652 High Similarity NPC226005
0.8643 High Similarity NPC52277
0.8643 High Similarity NPC470572
0.8643 High Similarity NPC199459
0.8643 High Similarity NPC177035
0.8636 High Similarity NPC147654
0.8633 High Similarity NPC35731
0.8633 High Similarity NPC135127
0.8603 High Similarity NPC148982
0.86 High Similarity NPC131532
0.8593 High Similarity NPC61181
0.8592 High Similarity NPC106944
0.8582 High Similarity NPC310252
0.8582 High Similarity NPC469364
0.8582 High Similarity NPC470413
0.8582 High Similarity NPC100558
0.8582 High Similarity NPC65262
0.8582 High Similarity NPC302583
0.8582 High Similarity NPC126206
0.8582 High Similarity NPC84789
0.8582 High Similarity NPC138738
0.8582 High Similarity NPC101686
0.8571 High Similarity NPC52097
0.8562 High Similarity NPC7191
0.8562 High Similarity NPC149873
0.8561 High Similarity NPC470848
0.8561 High Similarity NPC470849
0.8553 High Similarity NPC478269
0.8552 High Similarity NPC274960
0.8552 High Similarity NPC143120
0.8552 High Similarity NPC473909
0.8542 High Similarity NPC204644
0.8523 High Similarity NPC169404
0.8523 High Similarity NPC53587
0.8523 High Similarity NPC176186

  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 NPC475530 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
0.9774 High Similarity NPD7266 Discontinued
0.8079 Intermediate Similarity NPD1653 Approved
0.8041 Intermediate Similarity NPD6190 Approved
0.7866 Intermediate Similarity NPD7685 Pre-registration
0.7853 Intermediate Similarity NPD7472 Approved
0.7791 Intermediate Similarity NPD7054 Approved
0.7758 Intermediate Similarity NPD7251 Discontinued
0.7744 Intermediate Similarity NPD7074 Phase 3
0.773 Intermediate Similarity NPD7228 Approved
0.7711 Intermediate Similarity NPD7808 Phase 3
0.7697 Intermediate Similarity NPD6797 Phase 2
0.7639 Intermediate Similarity NPD3027 Phase 3
0.7616 Intermediate Similarity NPD8166 Discontinued
0.761 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD8455 Phase 2
0.7582 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1613 Approved
0.7483 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD230 Phase 1
0.741 Intermediate Similarity NPD3818 Discontinued
0.7381 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD8312 Approved
0.7353 Intermediate Similarity NPD8313 Approved
0.7346 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7240 Approved
0.7329 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD6674 Discontinued
0.7312 Intermediate Similarity NPD37 Approved
0.7284 Intermediate Similarity NPD4965 Approved
0.7284 Intermediate Similarity NPD4967 Phase 2
0.7284 Intermediate Similarity NPD4966 Approved
0.7262 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD3022 Approved
0.7259 Intermediate Similarity NPD3021 Approved
0.7241 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD1934 Approved
0.7203 Intermediate Similarity NPD1091 Approved
0.7203 Intermediate Similarity NPD3705 Approved
0.7186 Intermediate Similarity NPD6166 Phase 2
0.7186 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6559 Discontinued
0.7125 Intermediate Similarity NPD3455 Phase 2
0.7105 Intermediate Similarity NPD7097 Phase 1
0.7078 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD1465 Phase 2
0.7051 Intermediate Similarity NPD4628 Phase 3
0.703 Intermediate Similarity NPD7075 Discontinued
0.7029 Intermediate Similarity NPD228 Approved
0.702 Intermediate Similarity NPD4060 Phase 1
0.7012 Intermediate Similarity NPD3817 Phase 2
0.7006 Intermediate Similarity NPD8127 Discontinued
0.7006 Intermediate Similarity NPD7199 Phase 2
0.6993 Remote Similarity NPD1357 Approved
0.6975 Remote Similarity NPD4380 Phase 2
0.6974 Remote Similarity NPD4340 Discontinued
0.6972 Remote Similarity NPD5536 Phase 2
0.6959 Remote Similarity NPD5844 Phase 1
0.6957 Remote Similarity NPD7680 Approved
0.6954 Remote Similarity NPD6233 Phase 2
0.6951 Remote Similarity NPD2801 Approved
0.6944 Remote Similarity NPD5126 Approved
0.6944 Remote Similarity NPD5125 Phase 3
0.6933 Remote Similarity NPD7095 Approved
0.6923 Remote Similarity NPD9545 Approved
0.6923 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6913 Remote Similarity NPD2861 Phase 2
0.6906 Remote Similarity NPD969 Suspended
0.689 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6887 Remote Similarity NPD3764 Approved
0.6879 Remote Similarity NPD1652 Phase 2
0.6867 Remote Similarity NPD4908 Phase 1
0.6867 Remote Similarity NPD3882 Suspended
0.6861 Remote Similarity NPD1358 Approved
0.6855 Remote Similarity NPD5058 Phase 3
0.6848 Remote Similarity NPD2978 Approved
0.6848 Remote Similarity NPD7819 Suspended
0.6848 Remote Similarity NPD2977 Approved
0.6848 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1511 Approved
0.681 Remote Similarity NPD7458 Discontinued
0.6809 Remote Similarity NPD5283 Phase 1
0.6807 Remote Similarity NPD5402 Approved
0.6803 Remote Similarity NPD9269 Phase 2
0.68 Remote Similarity NPD5736 Approved
0.6795 Remote Similarity NPD2935 Discontinued
0.6781 Remote Similarity NPD3496 Discontinued
0.6776 Remote Similarity NPD6798 Discontinued
0.6776 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6776 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6772 Remote Similarity NPD8151 Discontinued
0.677 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6232 Discontinued
0.6757 Remote Similarity NPD2982 Phase 2
0.6757 Remote Similarity NPD2983 Phase 2
0.6753 Remote Similarity NPD5124 Phase 1
0.6753 Remote Similarity NPD1933 Approved
0.6753 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6753 Remote Similarity NPD6355 Discontinued
0.6744 Remote Similarity NPD7473 Discontinued
0.6742 Remote Similarity NPD8150 Discontinued
0.6738 Remote Similarity NPD8320 Phase 1
0.6738 Remote Similarity NPD8319 Approved
0.6738 Remote Similarity NPD7843 Approved
0.6735 Remote Similarity NPD422 Phase 1
0.6728 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6728 Remote Similarity NPD1512 Approved
0.6727 Remote Similarity NPD6386 Approved
0.6727 Remote Similarity NPD6385 Approved
0.6723 Remote Similarity NPD7090 Clinical (unspecified phase)
0.671 Remote Similarity NPD6653 Approved
0.671 Remote Similarity NPD5314 Approved
0.6705 Remote Similarity NPD7549 Discontinued
0.6705 Remote Similarity NPD3751 Discontinued
0.6689 Remote Similarity NPD2981 Phase 2
0.6689 Remote Similarity NPD3018 Phase 2
0.6689 Remote Similarity NPD9494 Approved
0.6688 Remote Similarity NPD3062 Approved
0.6688 Remote Similarity NPD826 Approved
0.6688 Remote Similarity NPD1558 Phase 1
0.6688 Remote Similarity NPD3061 Approved
0.6688 Remote Similarity NPD943 Approved
0.6688 Remote Similarity NPD3620 Phase 2
0.6688 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6688 Remote Similarity NPD825 Approved
0.6688 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6688 Remote Similarity NPD3059 Approved
0.6687 Remote Similarity NPD5403 Approved
0.6685 Remote Similarity NPD7700 Phase 2
0.6685 Remote Similarity NPD7699 Phase 2
0.6667 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2933 Approved
0.6667 Remote Similarity NPD3094 Phase 2
0.6667 Remote Similarity NPD4536 Approved
0.6667 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7768 Phase 2
0.6667 Remote Similarity NPD2934 Approved
0.6667 Remote Similarity NPD3134 Approved
0.6667 Remote Similarity NPD4538 Approved
0.6667 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6647 Remote Similarity NPD5494 Approved
0.6646 Remote Similarity NPD5763 Approved
0.6646 Remote Similarity NPD5762 Approved
0.6646 Remote Similarity NPD3686 Approved
0.6646 Remote Similarity NPD3687 Approved
0.6627 Remote Similarity NPD7411 Suspended
0.6627 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6625 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6625 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6625 Remote Similarity NPD3750 Approved
0.6625 Remote Similarity NPD4110 Phase 3
0.6624 Remote Similarity NPD4108 Discontinued
0.6623 Remote Similarity NPD6663 Approved
0.6623 Remote Similarity NPD4062 Phase 3
0.6622 Remote Similarity NPD1610 Phase 2
0.662 Remote Similarity NPD5535 Approved
0.6617 Remote Similarity NPD2859 Approved
0.6617 Remote Similarity NPD2860 Approved
0.6611 Remote Similarity NPD6842 Approved
0.6611 Remote Similarity NPD6843 Phase 3
0.6611 Remote Similarity NPD6841 Approved
0.6607 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6605 Remote Similarity NPD6799 Approved
0.6605 Remote Similarity NPD4357 Discontinued
0.66 Remote Similarity NPD3225 Approved
0.6599 Remote Similarity NPD9384 Approved
0.6599 Remote Similarity NPD4626 Approved
0.6599 Remote Similarity NPD9381 Approved
0.6597 Remote Similarity NPD7157 Approved
0.6596 Remote Similarity NPD7435 Discontinued
0.6593 Remote Similarity NPD3020 Approved
0.6587 Remote Similarity NPD6801 Discontinued
0.6582 Remote Similarity NPD9570 Approved
0.6575 Remote Similarity NPD1548 Phase 1
0.6571 Remote Similarity NPD8470 Clinical (unspecified phase)
0.657 Remote Similarity NPD3787 Discontinued
0.6566 Remote Similarity NPD7028 Phase 2
0.6564 Remote Similarity NPD5401 Approved
0.6564 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6562 Remote Similarity NPD3060 Approved
0.6554 Remote Similarity NPD7039 Approved
0.6554 Remote Similarity NPD7038 Approved
0.6548 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6544 Remote Similarity NPD1242 Phase 1
0.6538 Remote Similarity NPD555 Phase 2
0.6538 Remote Similarity NPD447 Suspended
0.6533 Remote Similarity NPD9622 Approved
0.6531 Remote Similarity NPD5691 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