Structure

Physi-Chem Properties

Molecular Weight:  510.21
Volume:  496.16
LogP:  0.012
LogD:  0.055
LogS:  -1.95
# Rotatable Bonds:  11
TPSA:  200.53
# H-Bond Aceptor:  11
# H-Bond Donor:  9
# Rings:  3
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.184
Synthetic Accessibility Score:  4.248
Fsp3:  0.52
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:  -6.336
MDCK Permeability:  5.468585186463315e-06
Pgp-inhibitor:  0.006
Pgp-substrate:  0.94
Human Intestinal Absorption (HIA):  0.988
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.037
Plasma Protein Binding (PPB):  87.33538055419922%
Volume Distribution (VD):  0.366
Pgp-substrate:  11.255926132202148%

ADMET: Metabolism

CYP1A2-inhibitor:  0.145
CYP1A2-substrate:  0.026
CYP2C19-inhibitor:  0.059
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.056
CYP2C9-substrate:  0.461
CYP2D6-inhibitor:  0.154
CYP2D6-substrate:  0.204
CYP3A4-inhibitor:  0.032
CYP3A4-substrate:  0.066

ADMET: Excretion

Clearance (CL):  11.353
Half-life (T1/2):  0.919

ADMET: Toxicity

hERG Blockers:  0.11
Human Hepatotoxicity (H-HT):  0.256
Drug-inuced Liver Injury (DILI):  0.025
AMES Toxicity:  0.566
Rat Oral Acute Toxicity:  0.036
Maximum Recommended Daily Dose:  0.972
Skin Sensitization:  0.967
Carcinogencity:  0.069
Eye Corrosion:  0.003
Eye Irritation:  0.667
Respiratory Toxicity:  0.027

Download Data

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

  Natural Product: NPC231607

Natural Product ID:  NPC231607
Common Name*:   (3R,5R)-3,5-Dihydroxy-1,7-Bis(3,4-Dihydroxyphenyl)Heptane3-O-Beta-D-Glucopyranoside
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[(3R,5R)-1,7-bis(3,4-dihydroxyphenyl)-5-hydroxyheptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  RMPZSLTVINHQDZ-NWKFWMDCSA-N
Standard InCHI:  InChI=1S/C25H34O11/c26-12-21-22(32)23(33)24(34)25(36-21)35-16(6-2-14-4-8-18(29)20(31)10-14)11-15(27)5-1-13-3-7-17(28)19(30)9-13/h3-4,7-10,15-16,21-34H,1-2,5-6,11-12H2/t15-,16-,21-,22-,23+,24-,25-/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H](C[C@@H](CCc2ccc(c(c2)O)O)O)CCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465800
PubChem CID:   10896495
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002650] Diarylheptanoids
        • [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. root n.a. PMID[10230514]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota rhizomes SiMao City, Yunnan Province, China 1996-OCT PMID[11908966]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota Rhizomes n.a. n.a. PMID[12350150]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[12956064]
NPO12186 Oplopanax chironium Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[15104479]
NPO11157 Corydalis saxicola Species Papaveraceae Eukaryota n.a. root n.a. PMID[17611928]
NPO11157 Corydalis saxicola Species Papaveraceae Eukaryota n.a. leaf n.a. PMID[18649321]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[20715765]
NPO7143 Acacia jacquemontii Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21894904]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[23031596]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25608854]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[33253561]
NPO13831 Cephalotaxus oliveri Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13831 Cephalotaxus oliveri Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12093 Papaver orientale Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12093 Papaver orientale Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12186 Oplopanax chironium Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13527 Solanum ecuadorense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13723 Salvia eriophora Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11585 Geijera salicifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10094 Daphne gnidioides Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3227 Androsace umbellata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8399 Psiadia trinervia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11157 Corydalis saxicola Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7143 Acacia jacquemontii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6266 Anzia hypoleucoides Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14634 Artemisia balchanorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9487 Penicillium flexuosum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1133 Zieria laevigata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11753 Sideroxylon foetidissimum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13831 Cephalotaxus oliveri Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5551 Podocarpus sylvestris Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14018 Pleurotus salmoneostramineus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11396 Metzgeria furcata Species Metzgeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11909 Othonna arborescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14308 Coleonema pulchrum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9126 Stevia maimarensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12268 Aloe littoralis Species Asphodelaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 3.0 ug.mL-1 PMID[571079]
NPT924 Cell Line HSC-2 Homo sapiens IC50 = 92.0 ug.mL-1 PMID[571079]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens EC50 = 23100.0 nM PMID[571080]
NPT27 Others Unspecified IC50 = 189.0 ug.mL-1 PMID[571079]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens EC50 > 50000.0 nM PMID[571080]
NPT866 Individual Protein Peroxisome proliferator-activated receptor alpha Homo sapiens EC50 > 50000.0 nM PMID[571080]
NPT866 Individual Protein Peroxisome proliferator-activated receptor alpha Homo sapiens FC = 1.3 n.a. PMID[571080]
NPT3942 Protein Family Peroxisome proliferator-activated receptor Homo sapiens EC50 = 9900.0 nM PMID[571080]
NPT2 Others Unspecified IC50 = 9400.0 nM PMID[571080]

☑ 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 NPC231607 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 NPC79715
1.0 High Similarity NPC264900
1.0 High Similarity NPC108659
0.9917 High Similarity NPC94179
0.9836 High Similarity NPC184092
0.96 High Similarity NPC254275
0.9593 High Similarity NPC148982
0.95 High Similarity NPC266045
0.9417 High Similarity NPC469703
0.9417 High Similarity NPC469704
0.9417 High Similarity NPC160854
0.9417 High Similarity NPC201402
0.935 High Similarity NPC90318
0.9339 High Similarity NPC469686
0.9302 High Similarity NPC177035
0.9302 High Similarity NPC199459
0.9302 High Similarity NPC52277
0.9262 High Similarity NPC471067
0.9187 High Similarity NPC232454
0.9187 High Similarity NPC178449
0.9187 High Similarity NPC470907
0.9147 High Similarity NPC287597
0.9147 High Similarity NPC34293
0.9147 High Similarity NPC886
0.9091 High Similarity NPC106944
0.9084 High Similarity NPC260425
0.9084 High Similarity NPC470413
0.9084 High Similarity NPC138738
0.9077 High Similarity NPC180171
0.9077 High Similarity NPC158325
0.9077 High Similarity NPC103398
0.9077 High Similarity NPC123988
0.9023 High Similarity NPC472711
0.9015 High Similarity NPC89105
0.9015 High Similarity NPC472350
0.9015 High Similarity NPC328273
0.9015 High Similarity NPC68092
0.9015 High Similarity NPC64141
0.9015 High Similarity NPC321638
0.9015 High Similarity NPC197316
0.9015 High Similarity NPC476383
0.9015 High Similarity NPC81515
0.9015 High Similarity NPC321184
0.9015 High Similarity NPC171134
0.9015 High Similarity NPC205195
0.9 High Similarity NPC35731
0.9 High Similarity NPC476411
0.8939 High Similarity NPC84789
0.8939 High Similarity NPC304152
0.8939 High Similarity NPC100558
0.8939 High Similarity NPC78363
0.8939 High Similarity NPC310252
0.8939 High Similarity NPC302583
0.8915 High Similarity NPC248307
0.8915 High Similarity NPC65942
0.8898 High Similarity NPC469687
0.8889 High Similarity NPC113680
0.8889 High Similarity NPC46092
0.8889 High Similarity NPC470950
0.8889 High Similarity NPC185307
0.8889 High Similarity NPC477898
0.8889 High Similarity NPC278961
0.8881 High Similarity NPC134405
0.8881 High Similarity NPC476385
0.8881 High Similarity NPC476377
0.8881 High Similarity NPC47471
0.8881 High Similarity NPC469661
0.8871 High Similarity NPC55608
0.8862 High Similarity NPC469702
0.8862 High Similarity NPC282409
0.8855 High Similarity NPC187194
0.8843 High Similarity NPC148055
0.8833 High Similarity NPC157338
0.8824 High Similarity NPC129417
0.8824 High Similarity NPC470235
0.8824 High Similarity NPC84181
0.8824 High Similarity NPC283995
0.8815 High Similarity NPC476356
0.8815 High Similarity NPC469559
0.8815 High Similarity NPC189115
0.8815 High Similarity NPC48309
0.8815 High Similarity NPC5262
0.8815 High Similarity NPC472714
0.8815 High Similarity NPC222433
0.8815 High Similarity NPC265648
0.8806 High Similarity NPC473799
0.8806 High Similarity NPC475530
0.879 High Similarity NPC476448
0.879 High Similarity NPC476445
0.879 High Similarity NPC469548
0.8788 High Similarity NPC476870
0.8769 High Similarity NPC476407
0.876 High Similarity NPC477294
0.876 High Similarity NPC307110
0.876 High Similarity NPC229784
0.876 High Similarity NPC477293
0.8759 High Similarity NPC18979
0.8759 High Similarity NPC475096
0.8759 High Similarity NPC22150
0.8759 High Similarity NPC279298
0.8759 High Similarity NPC272619
0.8759 High Similarity NPC38041
0.8759 High Similarity NPC286245
0.875 High Similarity NPC247032
0.875 High Similarity NPC175214
0.875 High Similarity NPC112
0.875 High Similarity NPC476380
0.875 High Similarity NPC105005
0.875 High Similarity NPC476397
0.875 High Similarity NPC476384
0.875 High Similarity NPC298257
0.875 High Similarity NPC264632
0.875 High Similarity NPC269141
0.875 High Similarity NPC96795
0.875 High Similarity NPC205864
0.875 High Similarity NPC476375
0.875 High Similarity NPC76406
0.875 High Similarity NPC476381
0.875 High Similarity NPC476378
0.875 High Similarity NPC473044
0.875 High Similarity NPC119537
0.875 High Similarity NPC40305
0.8731 High Similarity NPC156376
0.8722 High Similarity NPC203230
0.8722 High Similarity NPC242028
0.8712 High Similarity NPC470881
0.8702 High Similarity NPC473285
0.8696 High Similarity NPC112861
0.8692 High Similarity NPC469705
0.8692 High Similarity NPC470122
0.8692 High Similarity NPC17968
0.8686 High Similarity NPC118385
0.8686 High Similarity NPC300894
0.8686 High Similarity NPC141455
0.8686 High Similarity NPC471065
0.8686 High Similarity NPC196063
0.8686 High Similarity NPC76176
0.8686 High Similarity NPC473045
0.8686 High Similarity NPC296954
0.8686 High Similarity NPC472713
0.8686 High Similarity NPC472712
0.8686 High Similarity NPC138227
0.8686 High Similarity NPC469313
0.8686 High Similarity NPC64195
0.8686 High Similarity NPC187774
0.8686 High Similarity NPC168579
0.8686 High Similarity NPC253015
0.8686 High Similarity NPC25292
0.8686 High Similarity NPC473046
0.8682 High Similarity NPC252307
0.8682 High Similarity NPC245826
0.8682 High Similarity NPC474178
0.8682 High Similarity NPC232880
0.8676 High Similarity NPC140502
0.8657 High Similarity NPC65530
0.8657 High Similarity NPC59324
0.8657 High Similarity NPC476376
0.8647 High Similarity NPC101624
0.8647 High Similarity NPC184938
0.8636 High Similarity NPC6836
0.8633 High Similarity NPC193473
0.8633 High Similarity NPC15956
0.8633 High Similarity NPC31325
0.8633 High Similarity NPC224674
0.8633 High Similarity NPC213074
0.8633 High Similarity NPC275284
0.8633 High Similarity NPC39657
0.8633 High Similarity NPC227902
0.8633 High Similarity NPC114505
0.8629 High Similarity NPC477803
0.8626 High Similarity NPC9912
0.8626 High Similarity NPC219677
0.8623 High Similarity NPC34587
0.8623 High Similarity NPC100998
0.8623 High Similarity NPC252292
0.8623 High Similarity NPC34927
0.8623 High Similarity NPC476382
0.8623 High Similarity NPC469586
0.8613 High Similarity NPC37793
0.8605 High Similarity NPC476873
0.8605 High Similarity NPC288416
0.8603 High Similarity NPC471908
0.8603 High Similarity NPC186406
0.8593 High Similarity NPC212770
0.8593 High Similarity NPC98777
0.8583 High Similarity NPC187583
0.8583 High Similarity NPC473451
0.8583 High Similarity NPC179002
0.8583 High Similarity NPC257430
0.8571 High Similarity NPC280945
0.8571 High Similarity NPC107478
0.8571 High Similarity NPC471883
0.8571 High Similarity NPC116229
0.8561 High Similarity NPC99515
0.8561 High Similarity NPC190714
0.8561 High Similarity NPC229505
0.8561 High Similarity NPC125755
0.8561 High Similarity NPC252833
0.8561 High Similarity NPC471095
0.8561 High Similarity NPC471066

  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 NPC231607 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
0.9015 High Similarity NPD7266 Discontinued
0.8195 Intermediate Similarity NPD3027 Phase 3
0.8148 Intermediate Similarity NPD1613 Approved
0.8148 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7967 Intermediate Similarity NPD3022 Approved
0.7967 Intermediate Similarity NPD3021 Approved
0.7852 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD1653 Approved
0.7727 Intermediate Similarity NPD1091 Approved
0.7708 Intermediate Similarity NPD6190 Approved
0.7692 Intermediate Similarity NPD6674 Discontinued
0.7552 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD7074 Phase 3
0.7532 Intermediate Similarity NPD7228 Approved
0.7484 Intermediate Similarity NPD7054 Approved
0.7463 Intermediate Similarity NPD3705 Approved
0.7444 Intermediate Similarity NPD5125 Phase 3
0.7444 Intermediate Similarity NPD5126 Approved
0.7438 Intermediate Similarity NPD7472 Approved
0.7421 Intermediate Similarity NPD3818 Discontinued
0.7419 Intermediate Similarity NPD6234 Discontinued
0.7394 Intermediate Similarity NPD5314 Approved
0.7391 Intermediate Similarity NPD2861 Phase 2
0.7376 Intermediate Similarity NPD3061 Approved
0.7376 Intermediate Similarity NPD3062 Approved
0.7376 Intermediate Similarity NPD3059 Approved
0.7372 Intermediate Similarity NPD3094 Phase 2
0.7368 Intermediate Similarity NPD1357 Approved
0.7346 Intermediate Similarity NPD7251 Discontinued
0.732 Intermediate Similarity NPD37 Approved
0.7313 Intermediate Similarity NPD9384 Approved
0.7313 Intermediate Similarity NPD9381 Approved
0.7297 Intermediate Similarity NPD5058 Phase 3
0.729 Intermediate Similarity NPD4966 Approved
0.729 Intermediate Similarity NPD4965 Approved
0.729 Intermediate Similarity NPD4967 Phase 2
0.7287 Intermediate Similarity NPD228 Approved
0.7284 Intermediate Similarity NPD6797 Phase 2
0.7273 Intermediate Similarity NPD2860 Approved
0.7273 Intermediate Similarity NPD2859 Approved
0.7273 Intermediate Similarity NPD8455 Phase 2
0.7248 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD7685 Pre-registration
0.7236 Intermediate Similarity NPD3020 Approved
0.7222 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD3092 Approved
0.7195 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7808 Phase 3
0.719 Intermediate Similarity NPD2933 Approved
0.719 Intermediate Similarity NPD2934 Approved
0.7179 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD1242 Phase 1
0.7176 Intermediate Similarity NPD5283 Phase 1
0.7161 Intermediate Similarity NPD2978 Approved
0.7161 Intermediate Similarity NPD2977 Approved
0.7133 Intermediate Similarity NPD3620 Phase 2
0.7133 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4538 Approved
0.7103 Intermediate Similarity NPD4536 Approved
0.7101 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD9622 Approved
0.7099 Intermediate Similarity NPD7843 Approved
0.7097 Intermediate Similarity NPD1934 Approved
0.7095 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD4908 Phase 1
0.7086 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD1610 Phase 2
0.7077 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD7157 Approved
0.7059 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD5960 Phase 3
0.7055 Intermediate Similarity NPD5588 Approved
0.7051 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3091 Approved
0.7034 Intermediate Similarity NPD817 Approved
0.7034 Intermediate Similarity NPD823 Approved
0.703 Intermediate Similarity NPD7240 Approved
0.7 Intermediate Similarity NPD7199 Phase 2
0.6993 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6978 Remote Similarity NPD2983 Phase 2
0.6978 Remote Similarity NPD2982 Phase 2
0.6975 Remote Similarity NPD6166 Phase 2
0.6975 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6964 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6951 Remote Similarity NPD7804 Clinical (unspecified phase)
0.695 Remote Similarity NPD9621 Approved
0.695 Remote Similarity NPD9619 Approved
0.695 Remote Similarity NPD9620 Approved
0.6944 Remote Similarity NPD6405 Approved
0.6944 Remote Similarity NPD6407 Approved
0.6939 Remote Similarity NPD4108 Discontinued
0.6933 Remote Similarity NPD8166 Discontinued
0.6929 Remote Similarity NPD5310 Approved
0.6929 Remote Similarity NPD5311 Approved
0.6928 Remote Similarity NPD6559 Discontinued
0.6923 Remote Similarity NPD2684 Approved
0.6918 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6912 Remote Similarity NPD1548 Phase 1
0.6906 Remote Similarity NPD2981 Phase 2
0.6901 Remote Similarity NPD5736 Approved
0.6901 Remote Similarity NPD3018 Phase 2
0.6897 Remote Similarity NPD4060 Phase 1
0.6897 Remote Similarity NPD1558 Phase 1
0.6875 Remote Similarity NPD601 Approved
0.6875 Remote Similarity NPD597 Approved
0.6875 Remote Similarity NPD598 Approved
0.6871 Remote Similarity NPD7097 Phase 1
0.6867 Remote Similarity NPD3060 Approved
0.6859 Remote Similarity NPD4380 Phase 2
0.6857 Remote Similarity NPD4659 Approved
0.685 Remote Similarity NPD940 Approved
0.685 Remote Similarity NPD846 Approved
0.6849 Remote Similarity NPD230 Phase 1
0.6842 Remote Similarity NPD9377 Approved
0.6842 Remote Similarity NPD9379 Approved
0.6835 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6835 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6828 Remote Similarity NPD1130 Approved
0.6828 Remote Similarity NPD1132 Approved
0.6828 Remote Similarity NPD1136 Approved
0.6815 Remote Similarity NPD6671 Approved
0.6812 Remote Similarity NPD6516 Phase 2
0.6812 Remote Similarity NPD3095 Discontinued
0.6812 Remote Similarity NPD5846 Approved
0.681 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6809 Remote Similarity NPD8651 Approved
0.6806 Remote Similarity NPD7095 Approved
0.6781 Remote Similarity NPD825 Approved
0.6781 Remote Similarity NPD826 Approved
0.6781 Remote Similarity NPD943 Approved
0.6779 Remote Similarity NPD9570 Approved
0.6774 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6774 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6772 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6761 Remote Similarity NPD3055 Approved
0.6761 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6761 Remote Similarity NPD4103 Phase 2
0.6761 Remote Similarity NPD3053 Approved
0.6759 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6755 Remote Similarity NPD4236 Phase 3
0.6755 Remote Similarity NPD4237 Approved
0.6755 Remote Similarity NPD5177 Phase 3
0.6746 Remote Similarity NPD8312 Approved
0.6746 Remote Similarity NPD8313 Approved
0.6742 Remote Similarity NPD4750 Phase 3
0.6735 Remote Similarity NPD5735 Approved
0.6733 Remote Similarity NPD1375 Discontinued
0.6732 Remote Similarity NPD6783 Clinical (unspecified phase)
0.673 Remote Similarity NPD6818 Clinical (unspecified phase)
0.673 Remote Similarity NPD2801 Approved
0.6723 Remote Similarity NPD7237 Clinical (unspecified phase)
0.672 Remote Similarity NPD844 Approved
0.6716 Remote Similarity NPD7635 Approved
0.6713 Remote Similarity NPD6584 Phase 3
0.6712 Remote Similarity NPD6663 Approved
0.6712 Remote Similarity NPD6233 Phase 2
0.6711 Remote Similarity NPD4628 Phase 3
0.669 Remote Similarity NPD4625 Phase 3
0.6689 Remote Similarity NPD2568 Approved
0.6688 Remote Similarity NPD1511 Approved
0.6667 Remote Similarity NPD7680 Approved
0.6667 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6647 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6646 Remote Similarity NPD3787 Discontinued
0.6645 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6644 Remote Similarity NPD2028 Clinical (unspecified phase)
0.6644 Remote Similarity NPD6798 Discontinued
0.6643 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6641 Remote Similarity NPD968 Approved
0.6641 Remote Similarity NPD289 Clinical (unspecified phase)
0.6641 Remote Similarity NPD3028 Approved
0.6623 Remote Similarity NPD5763 Approved
0.6623 Remote Similarity NPD5762 Approved
0.6622 Remote Similarity NPD4340 Discontinued
0.6622 Remote Similarity NPD6355 Discontinued
0.662 Remote Similarity NPD4749 Approved
0.662 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6617 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6608 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6605 Remote Similarity NPD7075 Discontinued
0.6603 Remote Similarity NPD1512 Approved
0.6601 Remote Similarity NPD4535 Phase 3
0.6594 Remote Similarity NPD5536 Phase 2
0.6591 Remote Similarity NPD2342 Discontinued
0.6591 Remote Similarity NPD290 Approved
0.6584 Remote Similarity NPD3817 Phase 2
0.6584 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6582 Remote Similarity NPD3455 Phase 2
0.6577 Remote Similarity NPD6653 Approved
0.6571 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6558 Remote Similarity NPD2677 Approved
0.6558 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6554 Remote Similarity NPD2238 Phase 2
0.6549 Remote Similarity NPD2562 Approved
0.6549 Remote Similarity NPD2231 Phase 2

  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