Structure

Physi-Chem Properties

Molecular Weight:  622.19
Volume:  578.119
LogP:  1.15
LogD:  0.057
LogS:  -2.667
# Rotatable Bonds:  8
TPSA:  234.29
# H-Bond Aceptor:  15
# H-Bond Donor:  8
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.111
Synthetic Accessibility Score:  4.999
Fsp3:  0.483
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:  -6.595
MDCK Permeability:  2.736472015385516e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.926
20% Bioavailability (F20%):  0.131
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.066
Plasma Protein Binding (PPB):  94.4111328125%
Volume Distribution (VD):  0.331
Pgp-substrate:  9.860479354858398%

ADMET: Metabolism

CYP1A2-inhibitor:  0.042
CYP1A2-substrate:  0.028
CYP2C19-inhibitor:  0.145
CYP2C19-substrate:  0.054
CYP2C9-inhibitor:  0.338
CYP2C9-substrate:  0.174
CYP2D6-inhibitor:  0.056
CYP2D6-substrate:  0.171
CYP3A4-inhibitor:  0.098
CYP3A4-substrate:  0.027

ADMET: Excretion

Clearance (CL):  1.681
Half-life (T1/2):  0.798

ADMET: Toxicity

hERG Blockers:  0.067
Human Hepatotoxicity (H-HT):  0.094
Drug-inuced Liver Injury (DILI):  0.48
AMES Toxicity:  0.714
Rat Oral Acute Toxicity:  0.392
Maximum Recommended Daily Dose:  0.067
Skin Sensitization:  0.975
Carcinogencity:  0.152
Eye Corrosion:  0.003
Eye Irritation:  0.753
Respiratory Toxicity:  0.052

Download Data

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

  Natural Product: NPC265648

Natural Product ID:  NPC265648
Common Name*:   Isocrenatoside
IUPAC Name:   [(2S,4aR,6R,7R,8S,8aR)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-6-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:   Isocrenatoside
Standard InCHIKey:  FYNJOHBQQZWZTB-WLLRULDYSA-N
Standard InCHI:  InChI=1S/C29H34O15/c1-12-22(35)24(37)25(38)28(41-12)44-26-23(36)20(11-39-21(34)7-3-13-2-5-15(30)17(32)8-13)43-29-27(26)42-19(10-40-29)14-4-6-16(31)18(33)9-14/h2-9,12,19-20,22-33,35-38H,10-11H2,1H3/b7-3+/t12-,19+,20+,22-,23+,24+,25+,26-,27+,28-,29+/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)O)O)O[C@@H]2[C@@H]1O[C@H](CO2)c1ccc(c(c1)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL402471
PubChem CID:   44559534
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric 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
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. stem n.a. PMID[12575075]
NPO21245 Microtoena prainiana Species Lamiaceae Eukaryota stems n.a. n.a. PMID[15217277]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15577255]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30188125]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21245 Microtoena prainiana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21245 Microtoena prainiana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29463 Pogostemon cablin Species Lamiaceae 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
NPT1166 Individual Protein Angiotensin-converting enzyme Homo sapiens Inhibition = 99.3 % PMID[534580]
NPT1166 Individual Protein Angiotensin-converting enzyme Homo sapiens Inhibition = 71.4 % PMID[534580]
NPT1166 Individual Protein Angiotensin-converting enzyme Homo sapiens Inhibition = 35.2 % PMID[534580]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 115.84 ug.mL-1 PMID[534582]
NPT493 Individual Protein Neuraminidase Influenza A virus Inhibition = 86.33 % PMID[534582]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 93110.0 nM PMID[534581]
NPT757 Organism Plasmodium falciparum 3D7 Plasmodium falciparum 3D7 IC50 > 50000.0 nM PMID[534581]
NPT2 Others Unspecified IC50 = 53120.0 nM PMID[534581]

☑ 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 NPC265648 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 NPC222433
0.9779 High Similarity NPC269141
0.9779 High Similarity NPC476378
0.9779 High Similarity NPC76406
0.9779 High Similarity NPC476384
0.9779 High Similarity NPC247032
0.9779 High Similarity NPC112
0.9779 High Similarity NPC476381
0.9779 High Similarity NPC476375
0.9779 High Similarity NPC96795
0.9779 High Similarity NPC205864
0.9779 High Similarity NPC298257
0.9779 High Similarity NPC476397
0.9779 High Similarity NPC264632
0.9779 High Similarity NPC175214
0.9779 High Similarity NPC476380
0.9779 High Similarity NPC119537
0.9778 High Similarity NPC476385
0.9778 High Similarity NPC134405
0.9776 High Similarity NPC89105
0.9776 High Similarity NPC81515
0.9776 High Similarity NPC197316
0.9776 High Similarity NPC68092
0.9776 High Similarity NPC64141
0.9776 High Similarity NPC476383
0.9776 High Similarity NPC472350
0.9708 High Similarity NPC64195
0.9701 High Similarity NPC260425
0.9701 High Similarity NPC78363
0.964 High Similarity NPC232992
0.9632 High Similarity NPC476377
0.9632 High Similarity NPC47471
0.963 High Similarity NPC205195
0.9568 High Similarity NPC229505
0.9559 High Similarity NPC473799
0.9559 High Similarity NPC475530
0.9556 High Similarity NPC476376
0.9504 High Similarity NPC476386
0.9504 High Similarity NPC94871
0.9504 High Similarity NPC473427
0.9504 High Similarity NPC306890
0.9504 High Similarity NPC259347
0.9504 High Similarity NPC470933
0.9504 High Similarity NPC471062
0.9504 High Similarity NPC476398
0.9496 High Similarity NPC252292
0.9496 High Similarity NPC476382
0.9496 High Similarity NPC100998
0.9496 High Similarity NPC34927
0.9496 High Similarity NPC34587
0.9478 High Similarity NPC886
0.9478 High Similarity NPC287597
0.9478 High Similarity NPC34293
0.9437 High Similarity NPC257970
0.9437 High Similarity NPC470927
0.9424 High Similarity NPC296954
0.9424 High Similarity NPC196063
0.9424 High Similarity NPC300894
0.9424 High Similarity NPC141455
0.9353 High Similarity NPC105005
0.9343 High Similarity NPC321184
0.9343 High Similarity NPC321638
0.9343 High Similarity NPC171134
0.9343 High Similarity NPC328273
0.9328 High Similarity NPC473285
0.9281 High Similarity NPC140502
0.9265 High Similarity NPC476870
0.9265 High Similarity NPC263829
0.9254 High Similarity NPC225384
0.9254 High Similarity NPC138777
0.9254 High Similarity NPC46137
0.9254 High Similarity NPC235294
0.9254 High Similarity NPC246869
0.9185 High Similarity NPC254275
0.9167 High Similarity NPC470934
0.9167 High Similarity NPC188393
0.9155 High Similarity NPC476865
0.9149 High Similarity NPC476867
0.9104 High Similarity NPC477294
0.9104 High Similarity NPC477293
0.9104 High Similarity NPC229784
0.9085 High Similarity NPC476864
0.9085 High Similarity NPC476866
0.9085 High Similarity NPC476869
0.9085 High Similarity NPC476868
0.9078 High Similarity NPC478239
0.9078 High Similarity NPC40305
0.9071 High Similarity NPC186406
0.9051 High Similarity NPC471883
0.9041 High Similarity NPC106818
0.903 High Similarity NPC232880
0.9014 High Similarity NPC110063
0.9007 High Similarity NPC157816
0.898 High Similarity NPC87403
0.8978 High Similarity NPC254398
0.8971 High Similarity NPC219677
0.8966 High Similarity NPC106138
0.8963 High Similarity NPC184092
0.8955 High Similarity NPC288416
0.8955 High Similarity NPC476873
0.8951 High Similarity NPC216819
0.8951 High Similarity NPC287615
0.8951 High Similarity NPC83743
0.8951 High Similarity NPC262182
0.8921 High Similarity NPC157554
0.8912 High Similarity NPC478268
0.8905 High Similarity NPC473924
0.8904 High Similarity NPC476871
0.8897 High Similarity NPC215095
0.8897 High Similarity NPC28651
0.8897 High Similarity NPC23677
0.8897 High Similarity NPC300262
0.8897 High Similarity NPC192763
0.8897 High Similarity NPC261122
0.8897 High Similarity NPC3460
0.8897 High Similarity NPC80732
0.8897 High Similarity NPC201148
0.8897 High Similarity NPC199311
0.8897 High Similarity NPC210611
0.8889 High Similarity NPC199928
0.8881 High Similarity NPC232228
0.8881 High Similarity NPC292443
0.8881 High Similarity NPC471157
0.8873 High Similarity NPC296643
0.8865 High Similarity NPC202700
0.8851 High Similarity NPC471874
0.8844 High Similarity NPC125823
0.8844 High Similarity NPC7145
0.8844 High Similarity NPC85192
0.8844 High Similarity NPC143480
0.8836 High Similarity NPC478242
0.8832 High Similarity NPC478255
0.8815 High Similarity NPC108659
0.8815 High Similarity NPC79715
0.8815 High Similarity NPC106677
0.8815 High Similarity NPC231607
0.8815 High Similarity NPC264900
0.8806 High Similarity NPC83218
0.8806 High Similarity NPC126991
0.8794 High Similarity NPC100389
0.8794 High Similarity NPC226005
0.8786 High Similarity NPC52277
0.8786 High Similarity NPC177035
0.8786 High Similarity NPC199459
0.8777 High Similarity NPC35731
0.8777 High Similarity NPC135127
0.8767 High Similarity NPC473138
0.8767 High Similarity NPC28776
0.875 High Similarity NPC225307
0.8741 High Similarity NPC94179
0.8732 High Similarity NPC106944
0.8723 High Similarity NPC126206
0.8723 High Similarity NPC470413
0.8723 High Similarity NPC138738
0.8714 High Similarity NPC123988
0.8707 High Similarity NPC283839
0.8707 High Similarity NPC90896
0.8681 High Similarity NPC113680
0.8681 High Similarity NPC278961
0.8675 High Similarity NPC11411
0.8662 High Similarity NPC220942
0.8658 High Similarity NPC289967
0.8658 High Similarity NPC53587
0.8658 High Similarity NPC472612
0.8658 High Similarity NPC472611
0.8658 High Similarity NPC215060
0.8658 High Similarity NPC476352
0.8658 High Similarity NPC169404
0.8658 High Similarity NPC176186
0.8652 High Similarity NPC471664
0.8652 High Similarity NPC37468
0.8652 High Similarity NPC186418
0.8652 High Similarity NPC471665
0.8652 High Similarity NPC470572
0.8639 High Similarity NPC478237
0.8636 High Similarity NPC246024
0.8621 High Similarity NPC297342
0.8613 High Similarity NPC148982
0.8611 High Similarity NPC473792
0.8611 High Similarity NPC473873
0.8609 High Similarity NPC131532
0.86 High Similarity NPC150442
0.8592 High Similarity NPC304152
0.8592 High Similarity NPC100558
0.8592 High Similarity NPC84789
0.8592 High Similarity NPC302583
0.8592 High Similarity NPC310252
0.8591 High Similarity NPC140151
0.8582 High Similarity NPC52097
0.8571 High Similarity NPC473480
0.8571 High Similarity NPC15538
0.8571 High Similarity NPC149873
0.8571 High Similarity NPC28637
0.8571 High Similarity NPC7191
0.8562 High Similarity NPC478269
0.8562 High Similarity NPC143120
0.8562 High Similarity NPC274960
0.8562 High Similarity NPC473909
0.8561 High Similarity NPC248307
0.8561 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 NPC265648 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
0.9776 High Similarity NPD7266 Discontinued
0.8212 Intermediate Similarity NPD1653 Approved
0.8086 Intermediate Similarity NPD7074 Phase 3
0.8054 Intermediate Similarity NPD6190 Approved
0.8025 Intermediate Similarity NPD7054 Approved
0.7975 Intermediate Similarity NPD7472 Approved
0.7963 Intermediate Similarity NPD7228 Approved
0.7879 Intermediate Similarity NPD7251 Discontinued
0.7879 Intermediate Similarity NPD7685 Pre-registration
0.7818 Intermediate Similarity NPD6797 Phase 2
0.7778 Intermediate Similarity NPD3027 Phase 3
0.7725 Intermediate Similarity NPD7808 Phase 3
0.7625 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1613 Approved
0.7619 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD8455 Phase 2
0.7597 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6234 Discontinued
0.753 Intermediate Similarity NPD3818 Discontinued
0.7516 Intermediate Similarity NPD8166 Discontinued
0.7485 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD7240 Approved
0.7451 Intermediate Similarity NPD6674 Discontinued
0.745 Intermediate Similarity NPD230 Phase 1
0.7438 Intermediate Similarity NPD37 Approved
0.741 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD6166 Phase 2
0.741 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4966 Approved
0.7407 Intermediate Similarity NPD4965 Approved
0.7407 Intermediate Similarity NPD4967 Phase 2
0.7396 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD8312 Approved
0.7368 Intermediate Similarity NPD8313 Approved
0.7347 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD1091 Approved
0.7279 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD6559 Discontinued
0.7237 Intermediate Similarity NPD7097 Phase 1
0.7237 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3705 Approved
0.7222 Intermediate Similarity NPD1934 Approved
0.7179 Intermediate Similarity NPD4628 Phase 3
0.7178 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD3022 Approved
0.7153 Intermediate Similarity NPD3021 Approved
0.7143 Intermediate Similarity NPD3455 Phase 2
0.7133 Intermediate Similarity NPD1357 Approved
0.7127 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7199 Phase 2
0.7099 Intermediate Similarity NPD4380 Phase 2
0.7097 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5125 Phase 3
0.7083 Intermediate Similarity NPD5126 Approved
0.7076 Intermediate Similarity NPD5844 Phase 1
0.7073 Intermediate Similarity NPD1465 Phase 2
0.7065 Intermediate Similarity NPD7680 Approved
0.705 Intermediate Similarity NPD228 Approved
0.7048 Intermediate Similarity NPD7075 Discontinued
0.7039 Intermediate Similarity NPD4060 Phase 1
0.703 Intermediate Similarity NPD3817 Phase 2
0.7024 Intermediate Similarity NPD8127 Discontinued
0.7006 Intermediate Similarity NPD1652 Phase 2
0.6993 Remote Similarity NPD4340 Discontinued
0.6993 Remote Similarity NPD5536 Phase 2
0.6981 Remote Similarity NPD5058 Phase 3
0.6974 Remote Similarity NPD6233 Phase 2
0.697 Remote Similarity NPD2977 Approved
0.697 Remote Similarity NPD2801 Approved
0.697 Remote Similarity NPD2978 Approved
0.6954 Remote Similarity NPD7095 Approved
0.6944 Remote Similarity NPD9545 Approved
0.6941 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6935 Remote Similarity NPD8320 Phase 1
0.6935 Remote Similarity NPD8319 Approved
0.6933 Remote Similarity NPD7458 Discontinued
0.6933 Remote Similarity NPD2861 Phase 2
0.6929 Remote Similarity NPD969 Suspended
0.6928 Remote Similarity NPD5402 Approved
0.6919 Remote Similarity NPD3751 Discontinued
0.6908 Remote Similarity NPD3764 Approved
0.6894 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6887 Remote Similarity NPD4908 Phase 1
0.6886 Remote Similarity NPD3882 Suspended
0.6884 Remote Similarity NPD1358 Approved
0.6883 Remote Similarity NPD5124 Phase 1
0.6883 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6854 Remote Similarity NPD8150 Discontinued
0.6839 Remote Similarity NPD6653 Approved
0.6832 Remote Similarity NPD1511 Approved
0.6831 Remote Similarity NPD5283 Phase 1
0.6818 Remote Similarity NPD3620 Phase 2
0.6818 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7549 Discontinued
0.6815 Remote Similarity NPD2935 Discontinued
0.681 Remote Similarity NPD5403 Approved
0.6807 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6803 Remote Similarity NPD3496 Discontinued
0.6797 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6797 Remote Similarity NPD6798 Discontinued
0.6797 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6795 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6795 Remote Similarity NPD4536 Approved
0.6795 Remote Similarity NPD4538 Approved
0.6793 Remote Similarity NPD7699 Phase 2
0.6793 Remote Similarity NPD7700 Phase 2
0.6792 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6791 Remote Similarity NPD7435 Discontinued
0.6789 Remote Similarity NPD8151 Discontinued
0.6784 Remote Similarity NPD6232 Discontinued
0.6784 Remote Similarity NPD3787 Discontinued
0.6779 Remote Similarity NPD2983 Phase 2
0.6779 Remote Similarity NPD2982 Phase 2
0.6774 Remote Similarity NPD6355 Discontinued
0.6774 Remote Similarity NPD1933 Approved
0.6772 Remote Similarity NPD5763 Approved
0.6772 Remote Similarity NPD5762 Approved
0.6768 Remote Similarity NPD3686 Approved
0.6768 Remote Similarity NPD3687 Approved
0.6766 Remote Similarity NPD7819 Suspended
0.6763 Remote Similarity NPD7473 Discontinued
0.6761 Remote Similarity NPD7843 Approved
0.6757 Remote Similarity NPD422 Phase 1
0.6748 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6748 Remote Similarity NPD1512 Approved
0.6747 Remote Similarity NPD6386 Approved
0.6747 Remote Similarity NPD6385 Approved
0.6742 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6736 Remote Similarity NPD7157 Approved
0.6731 Remote Similarity NPD5314 Approved
0.6722 Remote Similarity NPD6842 Approved
0.6722 Remote Similarity NPD6841 Approved
0.6722 Remote Similarity NPD6843 Phase 3
0.6721 Remote Similarity NPD6535 Approved
0.6721 Remote Similarity NPD6534 Approved
0.6719 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7783 Phase 2
0.6711 Remote Similarity NPD5736 Approved
0.6711 Remote Similarity NPD9269 Phase 2
0.6711 Remote Similarity NPD3018 Phase 2
0.6711 Remote Similarity NPD2981 Phase 2
0.6711 Remote Similarity NPD9494 Approved
0.671 Remote Similarity NPD3062 Approved
0.671 Remote Similarity NPD1558 Phase 1
0.671 Remote Similarity NPD3061 Approved
0.671 Remote Similarity NPD3059 Approved
0.6707 Remote Similarity NPD6801 Discontinued
0.6691 Remote Similarity NPD3134 Approved
0.6689 Remote Similarity NPD3094 Phase 2
0.6687 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6687 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3060 Approved
0.6687 Remote Similarity NPD5401 Approved
0.6687 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7038 Approved
0.6667 Remote Similarity NPD7039 Approved
0.6667 Remote Similarity NPD5494 Approved
0.6649 Remote Similarity NPD6823 Phase 2
0.6647 Remote Similarity NPD7411 Suspended
0.6647 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4108 Discontinued
0.6646 Remote Similarity NPD7033 Discontinued
0.6646 Remote Similarity NPD4110 Phase 3
0.6646 Remote Similarity NPD3750 Approved
0.6646 Remote Similarity NPD5960 Phase 3
0.6646 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5588 Approved
0.6645 Remote Similarity NPD4062 Phase 3
0.6644 Remote Similarity NPD1610 Phase 2
0.6643 Remote Similarity NPD5535 Approved
0.6631 Remote Similarity NPD6777 Approved
0.6631 Remote Similarity NPD6780 Approved
0.6631 Remote Similarity NPD6779 Approved
0.6631 Remote Similarity NPD6778 Approved
0.6631 Remote Similarity NPD6776 Approved
0.6631 Remote Similarity NPD6782 Approved
0.6631 Remote Similarity NPD6781 Approved
0.6626 Remote Similarity NPD6799 Approved
0.6626 Remote Similarity NPD4357 Discontinued
0.6623 Remote Similarity NPD3225 Approved
0.6622 Remote Similarity NPD9384 Approved
0.6622 Remote Similarity NPD4626 Approved
0.6622 Remote Similarity NPD9381 Approved
0.6614 Remote Similarity NPD7696 Phase 3
0.6614 Remote Similarity NPD7698 Approved
0.6614 Remote Similarity NPD7697 Approved
0.6604 Remote Similarity NPD9570 Approved
0.6603 Remote Similarity NPD825 Approved
0.6603 Remote Similarity NPD943 Approved
0.6603 Remote Similarity NPD7966 Clinical (unspecified phase)

  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