Structure

Physi-Chem Properties

Molecular Weight:  524.23
Volume:  513.456
LogP:  0.58
LogD:  0.554
LogS:  -2.316
# Rotatable Bonds:  12
TPSA:  189.53
# H-Bond Aceptor:  11
# H-Bond Donor:  8
# Rings:  3
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.178
Synthetic Accessibility Score:  4.203
Fsp3:  0.538
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.3
MDCK Permeability:  7.3389910539845005e-06
Pgp-inhibitor:  0.007
Pgp-substrate:  0.98
Human Intestinal Absorption (HIA):  0.952
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.065
Plasma Protein Binding (PPB):  90.23702239990234%
Volume Distribution (VD):  0.423
Pgp-substrate:  7.182234764099121%

ADMET: Metabolism

CYP1A2-inhibitor:  0.088
CYP1A2-substrate:  0.061
CYP2C19-inhibitor:  0.05
CYP2C19-substrate:  0.108
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.621
CYP2D6-inhibitor:  0.217
CYP2D6-substrate:  0.282
CYP3A4-inhibitor:  0.033
CYP3A4-substrate:  0.147

ADMET: Excretion

Clearance (CL):  10.43
Half-life (T1/2):  0.927

ADMET: Toxicity

hERG Blockers:  0.206
Human Hepatotoxicity (H-HT):  0.28
Drug-inuced Liver Injury (DILI):  0.024
AMES Toxicity:  0.486
Rat Oral Acute Toxicity:  0.019
Maximum Recommended Daily Dose:  0.975
Skin Sensitization:  0.956
Carcinogencity:  0.057
Eye Corrosion:  0.003
Eye Irritation:  0.139
Respiratory Toxicity:  0.037

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

  Natural Product: NPC177035

Natural Product ID:  NPC177035
Common Name*:   (3R,5R)-3,5-Dihydroxy-1-(4-Hydroxy-3-Methoxyphenyl)-7-(3,4-Dihydroxyphenyl)Heptane 3-O-Beta-D-Glucopyranoside
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[(3R,5R)-7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  REBVNKVLUNZIRF-VZDPZUTLSA-N
Standard InCHI:  InChI=1S/C26H36O11/c1-35-21-11-15(5-9-19(21)30)3-7-17(36-26-25(34)24(33)23(32)22(13-27)37-26)12-16(28)6-2-14-4-8-18(29)20(31)10-14/h4-5,8-11,16-17,22-34H,2-3,6-7,12-13H2,1H3/t16-,17-,22-,23-,24+,25-,26-/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H](C[C@@H](CCc2ccc(c(c2)O)O)O)CCc2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518704
PubChem CID:   11005885
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]
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]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13831 Cephalotaxus oliveri Species Taxaceae 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]
NPO13831 Cephalotaxus oliveri Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12093 Papaver orientale Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9126 Stevia maimarensis 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]
NPO12093 Papaver orientale Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12268 Aloe littoralis Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12186 Oplopanax chironium Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13723 Salvia eriophora Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13527 Solanum ecuadorense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10695 Pelargonium zonale Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10094 Daphne gnidioides Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11585 Geijera salicifolia Species Rutaceae 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]
NPO7143 Acacia jacquemontii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11157 Corydalis saxicola Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14634 Artemisia balchanorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11753 Sideroxylon foetidissimum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6266 Anzia hypoleucoides Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1133 Zieria laevigata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5551 Podocarpus sylvestris Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9487 Penicillium flexuosum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11396 Metzgeria furcata Species Metzgeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13831 Cephalotaxus oliveri Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11909 Othonna arborescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14018 Pleurotus salmoneostramineus Species Pleurotaceae 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 = 4.5 ug.mL-1 PMID[496974]
NPT924 Cell Line HSC-2 Homo sapiens IC50 = 209.0 ug.mL-1 PMID[496974]
NPT27 Others Unspecified IC50 > 250.0 ug.mL-1 PMID[496974]

☑ 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 NPC177035 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 NPC199459
1.0 High Similarity NPC52277
0.9771 High Similarity NPC470413
0.9771 High Similarity NPC138738
0.9699 High Similarity NPC472711
0.9692 High Similarity NPC35731
0.9624 High Similarity NPC106944
0.9621 High Similarity NPC304152
0.9612 High Similarity NPC248307
0.9612 High Similarity NPC65942
0.9556 High Similarity NPC477898
0.9556 High Similarity NPC185307
0.9556 High Similarity NPC470950
0.9556 High Similarity NPC46092
0.9556 High Similarity NPC113680
0.9556 High Similarity NPC278961
0.9542 High Similarity NPC476411
0.9542 High Similarity NPC187194
0.9485 High Similarity NPC283995
0.9485 High Similarity NPC129417
0.9485 High Similarity NPC84181
0.9485 High Similarity NPC470235
0.9481 High Similarity NPC48309
0.9481 High Similarity NPC469559
0.9481 High Similarity NPC5262
0.9481 High Similarity NPC472714
0.9481 High Similarity NPC189115
0.9481 High Similarity NPC476356
0.9457 High Similarity NPC307110
0.9416 High Similarity NPC22150
0.9416 High Similarity NPC38041
0.9416 High Similarity NPC18979
0.9416 High Similarity NPC475096
0.9416 High Similarity NPC286245
0.9416 High Similarity NPC279298
0.9416 High Similarity NPC272619
0.9407 High Similarity NPC469661
0.9394 High Similarity NPC470881
0.9389 High Similarity NPC254275
0.938 High Similarity NPC245826
0.938 High Similarity NPC252307
0.938 High Similarity NPC474178
0.9348 High Similarity NPC112861
0.9343 High Similarity NPC25292
0.9343 High Similarity NPC253015
0.9343 High Similarity NPC472712
0.9343 High Similarity NPC473046
0.9343 High Similarity NPC471065
0.9343 High Similarity NPC118385
0.9343 High Similarity NPC472713
0.9343 High Similarity NPC187774
0.9343 High Similarity NPC473045
0.9338 High Similarity NPC140502
0.9323 High Similarity NPC101624
0.9323 High Similarity NPC184938
0.9318 High Similarity NPC6836
0.9302 High Similarity NPC108659
0.9302 High Similarity NPC231607
0.9302 High Similarity NPC79715
0.9302 High Similarity NPC264900
0.9281 High Similarity NPC39657
0.9281 High Similarity NPC31325
0.9281 High Similarity NPC15956
0.9281 High Similarity NPC193473
0.9281 High Similarity NPC275284
0.9281 High Similarity NPC114505
0.9281 High Similarity NPC213074
0.9281 High Similarity NPC224674
0.9281 High Similarity NPC227902
0.9275 High Similarity NPC34927
0.9275 High Similarity NPC252292
0.9275 High Similarity NPC34587
0.9275 High Similarity NPC476382
0.9275 High Similarity NPC100998
0.927 High Similarity NPC473044
0.9259 High Similarity NPC98777
0.9259 High Similarity NPC156376
0.9259 High Similarity NPC212770
0.9248 High Similarity NPC107478
0.9242 High Similarity NPC252833
0.9237 High Similarity NPC80600
0.9237 High Similarity NPC472024
0.9225 High Similarity NPC94179
0.9209 High Similarity NPC99515
0.9209 High Similarity NPC190714
0.9209 High Similarity NPC125755
0.9197 High Similarity NPC60249
0.9197 High Similarity NPC475084
0.9197 High Similarity NPC246947
0.9185 High Similarity NPC65530
0.9185 High Similarity NPC59324
0.9173 High Similarity NPC132895
0.9167 High Similarity NPC9912
0.916 High Similarity NPC86030
0.916 High Similarity NPC166040
0.916 High Similarity NPC248355
0.916 High Similarity NPC184092
0.916 High Similarity NPC270849
0.916 High Similarity NPC26653
0.916 High Similarity NPC5851
0.9149 High Similarity NPC44452
0.9149 High Similarity NPC286235
0.9149 High Similarity NPC55158
0.9149 High Similarity NPC51328
0.9143 High Similarity NPC232992
0.9137 High Similarity NPC43508
0.9137 High Similarity NPC161700
0.9137 High Similarity NPC277867
0.9137 High Similarity NPC476301
0.9137 High Similarity NPC469586
0.913 High Similarity NPC478239
0.9124 High Similarity NPC76871
0.9124 High Similarity NPC471908
0.9111 High Similarity NPC242028
0.9111 High Similarity NPC203230
0.9098 High Similarity NPC471505
0.9098 High Similarity NPC106739
0.9098 High Similarity NPC201587
0.9098 High Similarity NPC253105
0.9098 High Similarity NPC470270
0.9085 High Similarity NPC98624
0.9085 High Similarity NPC475224
0.9084 High Similarity NPC72529
0.9084 High Similarity NPC302378
0.9078 High Similarity NPC116229
0.9078 High Similarity NPC175976
0.9078 High Similarity NPC248132
0.9078 High Similarity NPC130449
0.9065 High Similarity NPC469313
0.9065 High Similarity NPC138227
0.9065 High Similarity NPC110063
0.9065 High Similarity NPC471667
0.9065 High Similarity NPC217635
0.9065 High Similarity NPC76176
0.9065 High Similarity NPC79429
0.9065 High Similarity NPC168579
0.9065 High Similarity NPC471063
0.9058 High Similarity NPC157816
0.9044 High Similarity NPC195196
0.9037 High Similarity NPC135777
0.9037 High Similarity NPC142547
0.903 High Similarity NPC25821
0.9023 High Similarity NPC476345
0.9023 High Similarity NPC470096
0.9023 High Similarity NPC470095
0.9023 High Similarity NPC475067
0.9014 High Similarity NPC94871
0.9014 High Similarity NPC306890
0.9014 High Similarity NPC476386
0.9014 High Similarity NPC471062
0.9014 High Similarity NPC470933
0.9014 High Similarity NPC476398
0.9014 High Similarity NPC106138
0.9014 High Similarity NPC259347
0.9014 High Similarity NPC473427
0.9008 High Similarity NPC165045
0.9008 High Similarity NPC163332
0.9008 High Similarity NPC147821
0.9008 High Similarity NPC118533
0.9008 High Similarity NPC41706
0.9008 High Similarity NPC292056
0.9008 High Similarity NPC111247
0.9008 High Similarity NPC183181
0.9008 High Similarity NPC319625
0.9008 High Similarity NPC118787
0.9007 High Similarity NPC15538
0.9007 High Similarity NPC473480
0.9 High Similarity NPC287615
0.9 High Similarity NPC83743
0.9 High Similarity NPC216819
0.9 High Similarity NPC262182
0.8993 High Similarity NPC252169
0.8993 High Similarity NPC37793
0.8992 High Similarity NPC471693
0.8986 High Similarity NPC186406
0.8978 High Similarity NPC193666
0.8978 High Similarity NPC123526
0.8978 High Similarity NPC88640
0.8971 High Similarity NPC157554
0.8971 High Similarity NPC164857
0.8963 High Similarity NPC48863
0.8963 High Similarity NPC170694
0.8963 High Similarity NPC13745
0.8963 High Similarity NPC251981
0.8963 High Similarity NPC87696
0.8958 High Similarity NPC478268
0.8951 High Similarity NPC145979
0.8951 High Similarity NPC469707
0.8951 High Similarity NPC472709
0.8951 High Similarity NPC470927
0.8951 High Similarity NPC225815
0.8951 High Similarity NPC469706
0.8951 High Similarity NPC185955
0.8951 High Similarity NPC472710
0.8951 High Similarity NPC260781
0.8951 High Similarity NPC218041
0.8951 High Similarity NPC257970
0.8951 High Similarity NPC9933
0.8951 High Similarity NPC188393
0.8951 High Similarity NPC470934

  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 NPC177035 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
0.8872 High Similarity NPD3027 Phase 3
0.8841 High Similarity NPD7266 Discontinued
0.854 High Similarity NPD1612 Clinical (unspecified phase)
0.854 High Similarity NPD1613 Approved
0.8322 Intermediate Similarity NPD6674 Discontinued
0.8248 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8243 Intermediate Similarity NPD1653 Approved
0.8175 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8134 Intermediate Similarity NPD1091 Approved
0.8134 Intermediate Similarity NPD3705 Approved
0.8113 Intermediate Similarity NPD7074 Phase 3
0.8101 Intermediate Similarity NPD7228 Approved
0.805 Intermediate Similarity NPD7054 Approved
0.8045 Intermediate Similarity NPD1357 Approved
0.8 Intermediate Similarity NPD7472 Approved
0.8 Intermediate Similarity NPD6234 Discontinued
0.7984 Intermediate Similarity NPD228 Approved
0.7908 Intermediate Similarity NPD37 Approved
0.7875 Intermediate Similarity NPD3818 Discontinued
0.7871 Intermediate Similarity NPD4965 Approved
0.7871 Intermediate Similarity NPD4966 Approved
0.7871 Intermediate Similarity NPD4967 Phase 2
0.7863 Intermediate Similarity NPD5283 Phase 1
0.7852 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD7685 Pre-registration
0.7791 Intermediate Similarity NPD7251 Discontinued
0.7786 Intermediate Similarity NPD2861 Phase 2
0.7785 Intermediate Similarity NPD5058 Phase 3
0.7762 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD3620 Phase 2
0.7754 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7808 Phase 3
0.7742 Intermediate Similarity NPD2978 Approved
0.7742 Intermediate Similarity NPD2977 Approved
0.773 Intermediate Similarity NPD6797 Phase 2
0.7677 Intermediate Similarity NPD1934 Approved
0.7652 Intermediate Similarity NPD7843 Approved
0.7636 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD8455 Phase 2
0.7626 Intermediate Similarity NPD2982 Phase 2
0.7626 Intermediate Similarity NPD2983 Phase 2
0.7612 Intermediate Similarity NPD7157 Approved
0.7606 Intermediate Similarity NPD4908 Phase 1
0.7603 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD4538 Approved
0.7603 Intermediate Similarity NPD4536 Approved
0.7595 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7240 Approved
0.7562 Intermediate Similarity NPD7199 Phase 2
0.7557 Intermediate Similarity NPD3022 Approved
0.7557 Intermediate Similarity NPD3021 Approved
0.7554 Intermediate Similarity NPD2981 Phase 2
0.7535 Intermediate Similarity NPD3018 Phase 2
0.7532 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6166 Phase 2
0.7531 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD1558 Phase 1
0.7516 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6190 Approved
0.7482 Intermediate Similarity NPD1610 Phase 2
0.7481 Intermediate Similarity NPD2684 Approved
0.7467 Intermediate Similarity NPD3060 Approved
0.7464 Intermediate Similarity NPD5125 Phase 3
0.7464 Intermediate Similarity NPD5126 Approved
0.745 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD5588 Approved
0.7432 Intermediate Similarity NPD5960 Phase 3
0.7432 Intermediate Similarity NPD4108 Discontinued
0.7397 Intermediate Similarity NPD4060 Phase 1
0.7394 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD6559 Discontinued
0.7365 Intermediate Similarity NPD7097 Phase 1
0.7362 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD6671 Approved
0.7351 Intermediate Similarity NPD4236 Phase 3
0.7351 Intermediate Similarity NPD4237 Approved
0.7351 Intermediate Similarity NPD5177 Phase 3
0.7342 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1375 Discontinued
0.7324 Intermediate Similarity NPD8651 Approved
0.7319 Intermediate Similarity NPD1548 Phase 1
0.731 Intermediate Similarity NPD7095 Approved
0.7296 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD2801 Approved
0.726 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5536 Phase 2
0.7232 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD5735 Approved
0.7222 Intermediate Similarity NPD6584 Phase 3
0.7215 Intermediate Similarity NPD4380 Phase 2
0.7214 Intermediate Similarity NPD6516 Phase 2
0.7214 Intermediate Similarity NPD5846 Approved
0.7211 Intermediate Similarity NPD6233 Phase 2
0.7208 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD4625 Phase 3
0.719 Intermediate Similarity NPD4628 Phase 3
0.7168 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7680 Approved
0.7143 Intermediate Similarity NPD290 Approved
0.7143 Intermediate Similarity NPD3817 Phase 2
0.7143 Intermediate Similarity NPD6798 Discontinued
0.7143 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD4749 Approved
0.7133 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD4162 Approved
0.7123 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD4123 Phase 3
0.7114 Intermediate Similarity NPD6355 Discontinued
0.7105 Intermediate Similarity NPD5762 Approved
0.7105 Intermediate Similarity NPD5763 Approved
0.7101 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD3882 Suspended
0.7095 Intermediate Similarity NPD2674 Phase 3
0.7089 Intermediate Similarity NPD3687 Approved
0.7089 Intermediate Similarity NPD3686 Approved
0.7083 Intermediate Similarity NPD5844 Phase 1
0.7081 Intermediate Similarity NPD5773 Approved
0.7081 Intermediate Similarity NPD5772 Approved
0.7078 Intermediate Similarity NPD4110 Phase 3
0.7078 Intermediate Similarity NPD4535 Phase 3
0.7078 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6331 Phase 2
0.7076 Intermediate Similarity NPD8312 Approved
0.7076 Intermediate Similarity NPD8313 Approved
0.7068 Intermediate Similarity NPD968 Approved
0.7067 Intermediate Similarity NPD6653 Approved
0.7055 Intermediate Similarity NPD7075 Discontinued
0.7051 Intermediate Similarity NPD1511 Approved
0.7047 Intermediate Similarity NPD2238 Phase 2
0.7044 Intermediate Similarity NPD4005 Discontinued
0.7044 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD3094 Phase 2
0.7032 Intermediate Similarity NPD2677 Approved
0.7032 Intermediate Similarity NPD5241 Discontinued
0.703 Intermediate Similarity NPD8127 Discontinued
0.7027 Intermediate Similarity NPD5718 Phase 2
0.7027 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD291 Approved
0.7014 Intermediate Similarity NPD3685 Discontinued
0.7014 Intermediate Similarity NPD6582 Phase 2
0.7014 Intermediate Similarity NPD6583 Phase 3
0.7013 Intermediate Similarity NPD1652 Phase 2
0.7011 Intermediate Similarity NPD6843 Phase 3
0.7011 Intermediate Similarity NPD6841 Approved
0.7011 Intermediate Similarity NPD6842 Approved
0.7007 Intermediate Similarity NPD5535 Approved
0.7006 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4678 Approved
0.7 Intermediate Similarity NPD4675 Approved
0.7 Intermediate Similarity NPD4340 Discontinued
0.6993 Remote Similarity NPD3540 Phase 1
0.6989 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6988 Remote Similarity NPD3787 Discontinued
0.6988 Remote Similarity NPD6232 Discontinued
0.6986 Remote Similarity NPD6917 Clinical (unspecified phase)
0.698 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1465 Phase 2
0.6974 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7033 Discontinued
0.6974 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7473 Discontinued
0.6962 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6962 Remote Similarity NPD52 Approved
0.6962 Remote Similarity NPD7526 Approved
0.6962 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6962 Remote Similarity NPD1512 Approved
0.6954 Remote Similarity NPD5314 Approved
0.6951 Remote Similarity NPD5604 Discontinued
0.6944 Remote Similarity NPD2235 Phase 2
0.6944 Remote Similarity NPD2231 Phase 2
0.6943 Remote Similarity NPD1774 Approved
0.6939 Remote Similarity NPD9494 Approved
0.6933 Remote Similarity NPD3062 Approved
0.6933 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6933 Remote Similarity NPD3059 Approved
0.6933 Remote Similarity NPD4140 Approved
0.6933 Remote Similarity NPD3061 Approved
0.6928 Remote Similarity NPD3539 Phase 1
0.6914 Remote Similarity NPD7906 Approved
0.6914 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6913 Remote Similarity NPD3144 Approved
0.6913 Remote Similarity NPD5111 Phase 2
0.6913 Remote Similarity NPD5110 Phase 2
0.6913 Remote Similarity NPD5109 Approved
0.6913 Remote Similarity NPD3145 Approved
0.6912 Remote Similarity NPD556 Approved
0.6912 Remote Similarity NPD5451 Approved
0.6905 Remote Similarity NPD2489 Approved
0.6905 Remote Similarity NPD27 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