Structure

Physi-Chem Properties

Molecular Weight:  882.26
Volume:  843.123
LogP:  3.121
LogD:  1.942
LogS:  -3.591
# Rotatable Bonds:  21
TPSA:  292.96
# H-Bond Aceptor:  20
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.057
Synthetic Accessibility Score:  5.272
Fsp3:  0.349
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.357
MDCK Permeability:  5.986250835121609e-05
Pgp-inhibitor:  0.055
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.994
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  100.73570251464844%
Volume Distribution (VD):  0.417
Pgp-substrate:  3.633655548095703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.067
CYP2C19-inhibitor:  0.281
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.799
CYP2C9-substrate:  0.639
CYP2D6-inhibitor:  0.321
CYP2D6-substrate:  0.25
CYP3A4-inhibitor:  0.778
CYP3A4-substrate:  0.264

ADMET: Excretion

Clearance (CL):  4.088
Half-life (T1/2):  0.947

ADMET: Toxicity

hERG Blockers:  0.223
Human Hepatotoxicity (H-HT):  0.061
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.59
Rat Oral Acute Toxicity:  0.064
Maximum Recommended Daily Dose:  0.114
Skin Sensitization:  0.978
Carcinogencity:  0.129
Eye Corrosion:  0.003
Eye Irritation:  0.028
Respiratory Toxicity:  0.012

Download Data

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

  Natural Product: NPC201148

Natural Product ID:  NPC201148
Common Name*:   Smilaside E
IUPAC Name:   [(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:   smilaside E
Standard InCHIKey:  OEURWVSBRKOOJG-OVPSZRCZSA-N
Standard InCHI:  InChI=1S/C43H46O20/c1-23(44)57-20-32-37(51)39(53)40(54)42(60-32)63-43(22-59-35(49)15-8-24-4-11-27(45)12-5-24)41(61-36(50)17-10-26-7-14-29(47)31(19-26)56-3)38(52)33(62-43)21-58-34(48)16-9-25-6-13-28(46)30(18-25)55-2/h4-19,32-33,37-42,45-47,51-54H,20-22H2,1-3H3/b15-8+,16-9+,17-10+/t32-,33-,37-,38-,39+,40-,41+,42-,43+/m1/s1
SMILES:  COc1cc(/C=C/C(=O)O[C@H]2[C@H](O)[C@H](O[C@@]2(COC(=O)/C=C/c2ccc(cc2)O)O[C@H]2O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]2O)O)O)COC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507530
PubChem CID:   11722056
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0003002] Hydroxycinnamic acid esters
            • [CHEMONTID:0000465] Coumaric acid esters

*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
NPO25611 Smilax china Species Smilacaceae Eukaryota stems n.a. n.a. PMID[16252910]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7132 Smilax glabra Species Smilacaceae 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
NPT91 Cell Line KB Homo sapiens ED50 = 5.5 ug ml-1 PMID[527723]
NPT165 Cell Line HeLa Homo sapiens ED50 = 5.1 ug ml-1 PMID[527723]
NPT579 Cell Line DLD-1 Homo sapiens ED50 = 4.5 ug ml-1 PMID[527723]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 13.0 ug ml-1 PMID[527723]
NPT81 Cell Line A549 Homo sapiens ED50 = 12.4 ug ml-1 PMID[527723]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 12.2 ug ml-1 PMID[527723]

☑ 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 NPC201148 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 NPC215095
1.0 High Similarity NPC80732
1.0 High Similarity NPC28651
1.0 High Similarity NPC210611
1.0 High Similarity NPC192763
1.0 High Similarity NPC300262
1.0 High Similarity NPC261122
1.0 High Similarity NPC199311
1.0 High Similarity NPC3460
0.979 High Similarity NPC7145
0.979 High Similarity NPC143480
0.979 High Similarity NPC85192
0.979 High Similarity NPC125823
0.9786 High Similarity NPC216819
0.9786 High Similarity NPC287615
0.9786 High Similarity NPC83743
0.9786 High Similarity NPC262182
0.9722 High Similarity NPC472611
0.9722 High Similarity NPC472612
0.9722 High Similarity NPC289967
0.9586 High Similarity NPC478268
0.9583 High Similarity NPC188393
0.9583 High Similarity NPC470934
0.9574 High Similarity NPC110063
0.9514 High Similarity NPC283839
0.9514 High Similarity NPC90896
0.9448 High Similarity NPC476871
0.9441 High Similarity NPC476865
0.9379 High Similarity NPC259347
0.9379 High Similarity NPC470933
0.9379 High Similarity NPC94871
0.9379 High Similarity NPC476398
0.9379 High Similarity NPC471062
0.9379 High Similarity NPC476386
0.9379 High Similarity NPC473427
0.9379 High Similarity NPC306890
0.9371 High Similarity NPC100998
0.9371 High Similarity NPC476868
0.9371 High Similarity NPC476866
0.9371 High Similarity NPC34927
0.9371 High Similarity NPC476864
0.9371 High Similarity NPC34587
0.9371 High Similarity NPC476869
0.9371 High Similarity NPC252292
0.9371 High Similarity NPC476382
0.9357 High Similarity NPC226005
0.9329 High Similarity NPC11411
0.9315 High Similarity NPC257970
0.9315 High Similarity NPC470927
0.9301 High Similarity NPC476867
0.9296 High Similarity NPC157816
0.9296 High Similarity NPC140502
0.9241 High Similarity NPC232992
0.9231 High Similarity NPC478239
0.9214 High Similarity NPC157554
0.9211 High Similarity NPC7191
0.9211 High Similarity NPC149873
0.9205 High Similarity NPC478269
0.9167 High Similarity NPC296954
0.9167 High Similarity NPC300894
0.9167 High Similarity NPC196063
0.9167 High Similarity NPC297342
0.9167 High Similarity NPC141455
0.915 High Similarity NPC246024
0.9097 High Similarity NPC105005
0.9091 High Similarity NPC476385
0.9091 High Similarity NPC186406
0.9091 High Similarity NPC47471
0.9091 High Similarity NPC476377
0.9091 High Similarity NPC134405
0.9085 High Similarity NPC478267
0.9085 High Similarity NPC100389
0.9071 High Similarity NPC471883
0.9041 High Similarity NPC229505
0.9041 High Similarity NPC199928
0.9034 High Similarity NPC232228
0.9021 High Similarity NPC473799
0.9021 High Similarity NPC202700
0.9021 High Similarity NPC475530
0.9007 High Similarity NPC131532
0.9007 High Similarity NPC476870
0.9 High Similarity NPC28637
0.8986 High Similarity NPC106138
0.8974 High Similarity NPC59516
0.8973 High Similarity NPC473909
0.8973 High Similarity NPC143120
0.8973 High Similarity NPC274960
0.8966 High Similarity NPC247032
0.8966 High Similarity NPC76406
0.8966 High Similarity NPC40305
0.8966 High Similarity NPC476378
0.8966 High Similarity NPC96795
0.8966 High Similarity NPC205864
0.8966 High Similarity NPC476380
0.8966 High Similarity NPC476397
0.8966 High Similarity NPC476384
0.8966 High Similarity NPC476375
0.8966 High Similarity NPC119537
0.8966 High Similarity NPC269141
0.8966 High Similarity NPC112
0.8966 High Similarity NPC298257
0.8966 High Similarity NPC264632
0.8966 High Similarity NPC175214
0.8966 High Similarity NPC476381
0.8951 High Similarity NPC81515
0.8951 High Similarity NPC476383
0.8951 High Similarity NPC68092
0.8951 High Similarity NPC472350
0.8951 High Similarity NPC328273
0.8951 High Similarity NPC321638
0.8951 High Similarity NPC89105
0.8951 High Similarity NPC197316
0.8951 High Similarity NPC171134
0.8951 High Similarity NPC64141
0.8951 High Similarity NPC205195
0.8951 High Similarity NPC321184
0.8947 High Similarity NPC478266
0.8944 High Similarity NPC186418
0.8944 High Similarity NPC37468
0.8919 High Similarity NPC478237
0.8904 High Similarity NPC64195
0.8904 High Similarity NPC292443
0.8897 High Similarity NPC67467
0.8897 High Similarity NPC265648
0.8897 High Similarity NPC222433
0.8896 High Similarity NPC478265
0.8881 High Similarity NPC476376
0.8881 High Similarity NPC78363
0.8881 High Similarity NPC260425
0.8865 High Similarity NPC254398
0.8859 High Similarity NPC478242
0.8857 High Similarity NPC219677
0.8844 High Similarity NPC138915
0.8836 High Similarity NPC278961
0.8836 High Similarity NPC113680
0.8828 High Similarity NPC472711
0.8811 High Similarity NPC199459
0.8811 High Similarity NPC177035
0.8811 High Similarity NPC52277
0.8803 High Similarity NPC886
0.8803 High Similarity NPC287597
0.8803 High Similarity NPC135127
0.8803 High Similarity NPC34293
0.8794 High Similarity NPC473924
0.8794 High Similarity NPC473285
0.8794 High Similarity NPC252833
0.8792 High Similarity NPC252402
0.8792 High Similarity NPC102934
0.8767 High Similarity NPC473873
0.8767 High Similarity NPC473792
0.8766 High Similarity NPC226759
0.8766 High Similarity NPC133984
0.875 High Similarity NPC470413
0.875 High Similarity NPC126206
0.875 High Similarity NPC138738
0.8742 High Similarity NPC478249
0.8742 High Similarity NPC269914
0.8733 High Similarity NPC475250
0.8732 High Similarity NPC6836
0.8714 High Similarity NPC229784
0.8714 High Similarity NPC307110
0.8714 High Similarity NPC477293
0.8714 High Similarity NPC477294
0.8707 High Similarity NPC477898
0.8707 High Similarity NPC185307
0.8707 High Similarity NPC46092
0.8707 High Similarity NPC470950
0.8701 High Similarity NPC228357
0.8684 High Similarity NPC203664
0.8681 High Similarity NPC471665
0.8681 High Similarity NPC471664
0.8675 High Similarity NPC475224
0.8671 High Similarity NPC470881
0.8671 High Similarity NPC35731
0.8649 High Similarity NPC129417
0.8649 High Similarity NPC84181
0.8649 High Similarity NPC470235
0.8649 High Similarity NPC283995
0.8649 High Similarity NPC471063
0.8645 High Similarity NPC471878
0.8643 High Similarity NPC232880
0.8643 High Similarity NPC225307
0.8639 High Similarity NPC476356
0.863 High Similarity NPC106944
0.8627 High Similarity NPC115203
0.8627 High Similarity NPC61604
0.8627 High Similarity NPC150442
0.8627 High Similarity NPC44730
0.8627 High Similarity NPC245615
0.8627 High Similarity NPC299706
0.8627 High Similarity NPC115466
0.8625 High Similarity NPC658
0.8625 High Similarity NPC197708
0.8621 High Similarity NPC195196
0.8611 High Similarity NPC55040
0.8609 High Similarity NPC111785
0.8608 High Similarity NPC227297
0.8592 High Similarity NPC248307
0.8592 High Similarity NPC246869
0.8592 High Similarity NPC65942

  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 NPC201148 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
0.8951 High Similarity NPD7266 Discontinued
0.8366 Intermediate Similarity NPD1653 Approved
0.8242 Intermediate Similarity NPD7685 Pre-registration
0.811 Intermediate Similarity NPD7228 Approved
0.8105 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7472 Approved
0.7901 Intermediate Similarity NPD6234 Discontinued
0.7844 Intermediate Similarity NPD7054 Approved
0.7823 Intermediate Similarity NPD3027 Phase 3
0.7812 Intermediate Similarity NPD37 Approved
0.7798 Intermediate Similarity NPD7074 Phase 3
0.7784 Intermediate Similarity NPD3818 Discontinued
0.7778 Intermediate Similarity NPD4967 Phase 2
0.7778 Intermediate Similarity NPD4965 Approved
0.7778 Intermediate Similarity NPD4966 Approved
0.7778 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7808 Phase 3
0.7764 Intermediate Similarity NPD8455 Phase 2
0.7742 Intermediate Similarity NPD6190 Approved
0.7722 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD7240 Approved
0.7706 Intermediate Similarity NPD7251 Discontinued
0.7676 Intermediate Similarity NPD1357 Approved
0.7661 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6797 Phase 2
0.7613 Intermediate Similarity NPD6674 Discontinued
0.759 Intermediate Similarity NPD7199 Phase 2
0.755 Intermediate Similarity NPD1613 Approved
0.755 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD3705 Approved
0.7514 Intermediate Similarity NPD8313 Approved
0.7514 Intermediate Similarity NPD8312 Approved
0.75 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6559 Discontinued
0.7456 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD6166 Phase 2
0.741 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD1091 Approved
0.7396 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7680 Approved
0.7381 Intermediate Similarity NPD8127 Discontinued
0.7326 Intermediate Similarity NPD5844 Phase 1
0.7292 Intermediate Similarity NPD5536 Phase 2
0.7285 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1934 Approved
0.7268 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD2977 Approved
0.7229 Intermediate Similarity NPD2978 Approved
0.7225 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7097 Phase 1
0.7169 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6233 Phase 2
0.7143 Intermediate Similarity NPD3882 Suspended
0.7143 Intermediate Similarity NPD5058 Phase 3
0.7126 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4628 Phase 3
0.7125 Intermediate Similarity NPD8166 Discontinued
0.7113 Intermediate Similarity NPD228 Approved
0.7097 Intermediate Similarity NPD3620 Phase 2
0.7097 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3817 Phase 2
0.7079 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD1358 Approved
0.7067 Intermediate Similarity NPD2983 Phase 2
0.7067 Intermediate Similarity NPD2982 Phase 2
0.7059 Intermediate Similarity NPD4908 Phase 1
0.7051 Intermediate Similarity NPD230 Phase 1
0.7048 Intermediate Similarity NPD4380 Phase 2
0.7035 Intermediate Similarity NPD6232 Discontinued
0.7024 Intermediate Similarity NPD1465 Phase 2
0.7024 Intermediate Similarity NPD2801 Approved
0.7013 Intermediate Similarity NPD7095 Approved
0.7011 Intermediate Similarity NPD7473 Discontinued
0.7 Intermediate Similarity NPD2981 Phase 2
0.7 Intermediate Similarity NPD7075 Discontinued
0.6994 Remote Similarity NPD4357 Discontinued
0.6993 Remote Similarity NPD9494 Approved
0.6993 Remote Similarity NPD2861 Phase 2
0.6987 Remote Similarity NPD4060 Phase 1
0.6968 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6798 Discontinued
0.6966 Remote Similarity NPD7549 Discontinued
0.6957 Remote Similarity NPD1652 Phase 2
0.6951 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6943 Remote Similarity NPD1933 Approved
0.6943 Remote Similarity NPD4340 Discontinued
0.6933 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6927 Remote Similarity NPD8151 Discontinued
0.691 Remote Similarity NPD7038 Approved
0.691 Remote Similarity NPD7039 Approved
0.6899 Remote Similarity NPD6653 Approved
0.6899 Remote Similarity NPD2492 Phase 1
0.6897 Remote Similarity NPD5283 Phase 1
0.6886 Remote Similarity NPD7458 Discontinued
0.6883 Remote Similarity NPD3018 Phase 2
0.6882 Remote Similarity NPD5402 Approved
0.6879 Remote Similarity NPD3134 Approved
0.6875 Remote Similarity NPD3751 Discontinued
0.6859 Remote Similarity NPD3764 Approved
0.6852 Remote Similarity NPD4237 Approved
0.6852 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4236 Phase 3
0.6845 Remote Similarity NPD7028 Phase 2
0.6842 Remote Similarity NPD7768 Phase 2
0.6835 Remote Similarity NPD6355 Discontinued
0.6835 Remote Similarity NPD5124 Phase 1
0.6835 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5762 Approved
0.6832 Remote Similarity NPD5763 Approved
0.6828 Remote Similarity NPD7843 Approved
0.6826 Remote Similarity NPD3686 Approved
0.6826 Remote Similarity NPD3687 Approved
0.6824 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7819 Suspended
0.6821 Remote Similarity NPD5494 Approved
0.6813 Remote Similarity NPD5588 Approved
0.681 Remote Similarity NPD4110 Phase 3
0.681 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6805 Remote Similarity NPD7411 Suspended
0.6805 Remote Similarity NPD6386 Approved
0.6805 Remote Similarity NPD6385 Approved
0.6802 Remote Similarity NPD7975 Clinical (unspecified phase)
0.68 Remote Similarity NPD5125 Phase 3
0.68 Remote Similarity NPD5126 Approved
0.6788 Remote Similarity NPD1511 Approved
0.6784 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6776 Remote Similarity NPD6841 Approved
0.6776 Remote Similarity NPD6843 Phase 3
0.6776 Remote Similarity NPD6842 Approved
0.6772 Remote Similarity NPD4140 Approved
0.6772 Remote Similarity NPD1558 Phase 1
0.677 Remote Similarity NPD2935 Discontinued
0.6766 Remote Similarity NPD5403 Approved
0.6759 Remote Similarity NPD969 Suspended
0.6755 Remote Similarity NPD3496 Discontinued
0.6754 Remote Similarity NPD7435 Discontinued
0.6752 Remote Similarity NPD6859 Clinical (unspecified phase)
0.675 Remote Similarity NPD4536 Approved
0.675 Remote Similarity NPD4537 Clinical (unspecified phase)
0.675 Remote Similarity NPD4538 Approved
0.675 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6748 Remote Similarity NPD3060 Approved
0.6748 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6743 Remote Similarity NPD3787 Discontinued
0.673 Remote Similarity NPD447 Suspended
0.6721 Remote Similarity NPD8434 Phase 2
0.6712 Remote Similarity NPD5535 Approved
0.6711 Remote Similarity NPD422 Phase 1
0.6708 Remote Similarity NPD7033 Discontinued
0.6707 Remote Similarity NPD6273 Approved
0.6707 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6707 Remote Similarity NPD1512 Approved
0.6689 Remote Similarity NPD7157 Approved
0.6688 Remote Similarity NPD3225 Approved
0.6686 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6686 Remote Similarity NPD3455 Phase 2
0.6686 Remote Similarity NPD5353 Approved
0.6685 Remote Similarity NPD7906 Approved
0.6684 Remote Similarity NPD7783 Phase 2
0.6684 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6801 Discontinued
0.6647 Remote Similarity NPD5401 Approved
0.6633 Remote Similarity NPD7874 Approved
0.6633 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6632 Remote Similarity NPD7870 Phase 2
0.6632 Remote Similarity NPD7871 Phase 2
0.6628 Remote Similarity NPD5772 Approved
0.6628 Remote Similarity NPD5773 Approved
0.6626 Remote Similarity NPD1375 Discontinued
0.6626 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6625 Remote Similarity NPD5735 Approved
0.6621 Remote Similarity NPD3021 Approved
0.6621 Remote Similarity NPD3022 Approved
0.6615 Remote Similarity NPD6823 Phase 2
0.6609 Remote Similarity NPD5604 Discontinued
0.6606 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6606 Remote Similarity NPD3750 Approved
0.6606 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6605 Remote Similarity NPD5960 Phase 3
0.6605 Remote Similarity NPD4108 Discontinued
0.6604 Remote Similarity NPD4062 Phase 3
0.6603 Remote Similarity NPD6584 Phase 3
0.6601 Remote Similarity NPD1610 Phase 2
0.6598 Remote Similarity NPD7999 Approved
0.6597 Remote Similarity NPD6782 Approved
0.6597 Remote Similarity NPD6779 Approved
0.6597 Remote Similarity NPD6781 Approved
0.6597 Remote Similarity NPD6776 Approved
0.6597 Remote Similarity NPD6778 Approved
0.6597 Remote Similarity NPD6777 Approved
0.6597 Remote Similarity NPD6780 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