Structure

Physi-Chem Properties

Molecular Weight:  809.31
Volume:  768.514
LogP:  0.23
LogD:  0.442
LogS:  -4.049
# Rotatable Bonds:  17
TPSA:  281.85
# H-Bond Aceptor:  19
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.066
Synthetic Accessibility Score:  5.192
Fsp3:  0.579
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.398
MDCK Permeability:  9.227216651197523e-05
Pgp-inhibitor:  0.013
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.994
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.108
Plasma Protein Binding (PPB):  63.40068817138672%
Volume Distribution (VD):  0.532
Pgp-substrate:  12.167235374450684%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.009
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.114
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.094
CYP2D6-inhibitor:  0.053
CYP2D6-substrate:  0.147
CYP3A4-inhibitor:  0.028
CYP3A4-substrate:  0.025

ADMET: Excretion

Clearance (CL):  1.029
Half-life (T1/2):  0.718

ADMET: Toxicity

hERG Blockers:  0.721
Human Hepatotoxicity (H-HT):  0.253
Drug-inuced Liver Injury (DILI):  0.929
AMES Toxicity:  0.092
Rat Oral Acute Toxicity:  0.014
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.254
Carcinogencity:  0.065
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.019

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

  Natural Product: NPC140915

Natural Product ID:  NPC140915
Common Name*:   (E)-N-4-Methoxycoumaroyltyramine 4-O-Beta-D-Glucopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->3)]-4-O-Acetyl-Alpha-L-Rhamnopyranoside
IUPAC Name:   [(2S,3S,4R,5R,6S)-6-[4-[2-[[(E)-3-(4-methoxyphenyl)prop-2-enoyl]amino]ethyl]phenoxy]-2-methyl-4,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-3-yl] acetate
Synonyms:  
Standard InCHIKey:  GFQSYSIECYVTSY-OACIPGCZSA-N
Standard InCHI:  InChI=1S/C38H51NO18/c1-18-33(52-19(2)42)34(56-36-31(48)29(46)27(44)24(16-40)54-36)35(57-37-32(49)30(47)28(45)25(17-41)55-37)38(51-18)53-23-11-6-21(7-12-23)14-15-39-26(43)13-8-20-4-9-22(50-3)10-5-20/h4-13,18,24-25,27-38,40-41,44-49H,14-17H2,1-3H3,(H,39,43)/b13-8+/t18-,24+,25+,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,38-/m0/s1
SMILES:  COc1ccc(cc1)/C=C/C(=NCCc1ccc(cc1)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3109406
PubChem CID:   76324845
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

*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
NPO1371 Teucrium viscidum Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[23337296]
NPO1371 Teucrium viscidum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24484201]
NPO1371 Teucrium viscidum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25739048]
NPO1371 Teucrium viscidum 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
NPT65 Cell Line HepG2 Homo sapiens FC = 2.1 n.a. PMID[517710]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. FC = 2.1 n.a. PMID[517710]

☑ 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 NPC140915 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 NPC197741
1.0 High Similarity NPC305700
1.0 High Similarity NPC187028
1.0 High Similarity NPC10221
1.0 High Similarity NPC18249
0.9722 High Similarity NPC139699
0.9722 High Similarity NPC114659
0.8912 High Similarity NPC63628
0.8912 High Similarity NPC178466
0.8523 High Similarity NPC195814
0.8477 Intermediate Similarity NPC161155
0.8477 Intermediate Similarity NPC136951
0.8477 Intermediate Similarity NPC97004
0.8421 Intermediate Similarity NPC97282
0.8421 Intermediate Similarity NPC313414
0.8258 Intermediate Similarity NPC175275
0.8255 Intermediate Similarity NPC263829
0.8224 Intermediate Similarity NPC273932
0.8224 Intermediate Similarity NPC89686
0.8224 Intermediate Similarity NPC257095
0.8205 Intermediate Similarity NPC220282
0.82 Intermediate Similarity NPC469383
0.8153 Intermediate Similarity NPC470933
0.8153 Intermediate Similarity NPC471062
0.8153 Intermediate Similarity NPC306890
0.8153 Intermediate Similarity NPC473427
0.8153 Intermediate Similarity NPC476398
0.8153 Intermediate Similarity NPC259347
0.8153 Intermediate Similarity NPC476386
0.8153 Intermediate Similarity NPC94871
0.8146 Intermediate Similarity NPC36434
0.8141 Intermediate Similarity NPC97240
0.8141 Intermediate Similarity NPC470935
0.8141 Intermediate Similarity NPC471032
0.8117 Intermediate Similarity NPC116922
0.8101 Intermediate Similarity NPC470927
0.8101 Intermediate Similarity NPC257970
0.8095 Intermediate Similarity NPC295970
0.8092 Intermediate Similarity NPC298821
0.8077 Intermediate Similarity NPC476865
0.8065 Intermediate Similarity NPC476867
0.8065 Intermediate Similarity NPC225445
0.8039 Intermediate Similarity NPC123761
0.8026 Intermediate Similarity NPC124149
0.8025 Intermediate Similarity NPC232992
0.8013 Intermediate Similarity NPC476869
0.8013 Intermediate Similarity NPC476868
0.8013 Intermediate Similarity NPC476866
0.8013 Intermediate Similarity NPC476864
0.8 Intermediate Similarity NPC469367
0.7987 Intermediate Similarity NPC46137
0.7987 Intermediate Similarity NPC225384
0.7987 Intermediate Similarity NPC246869
0.7987 Intermediate Similarity NPC476871
0.7987 Intermediate Similarity NPC138777
0.7987 Intermediate Similarity NPC235294
0.7962 Intermediate Similarity NPC107120
0.7962 Intermediate Similarity NPC74320
0.7961 Intermediate Similarity NPC166180
0.7961 Intermediate Similarity NPC197723
0.7961 Intermediate Similarity NPC165482
0.7961 Intermediate Similarity NPC138350
0.7961 Intermediate Similarity NPC40664
0.7961 Intermediate Similarity NPC3293
0.7949 Intermediate Similarity NPC471028
0.7949 Intermediate Similarity NPC177597
0.7927 Intermediate Similarity NPC179250
0.7927 Intermediate Similarity NPC50380
0.7908 Intermediate Similarity NPC262328
0.7908 Intermediate Similarity NPC87777
0.7901 Intermediate Similarity NPC160882
0.7898 Intermediate Similarity NPC34927
0.7898 Intermediate Similarity NPC252292
0.7898 Intermediate Similarity NPC100998
0.7898 Intermediate Similarity NPC34587
0.7898 Intermediate Similarity NPC226722
0.7898 Intermediate Similarity NPC476382
0.7895 Intermediate Similarity NPC314656
0.7895 Intermediate Similarity NPC238243
0.7885 Intermediate Similarity NPC264632
0.7885 Intermediate Similarity NPC476380
0.7885 Intermediate Similarity NPC476384
0.7885 Intermediate Similarity NPC205864
0.7885 Intermediate Similarity NPC175214
0.7885 Intermediate Similarity NPC96795
0.7885 Intermediate Similarity NPC298257
0.7885 Intermediate Similarity NPC247032
0.7885 Intermediate Similarity NPC476375
0.7885 Intermediate Similarity NPC476397
0.7885 Intermediate Similarity NPC476381
0.7885 Intermediate Similarity NPC76406
0.7885 Intermediate Similarity NPC112
0.7885 Intermediate Similarity NPC476378
0.7885 Intermediate Similarity NPC269141
0.7885 Intermediate Similarity NPC119537
0.7877 Intermediate Similarity NPC62101
0.7877 Intermediate Similarity NPC95733
0.7875 Intermediate Similarity NPC188393
0.7875 Intermediate Similarity NPC470934
0.7862 Intermediate Similarity NPC476142
0.7838 Intermediate Similarity NPC198798
0.7834 Intermediate Similarity NPC471063
0.7834 Intermediate Similarity NPC64195
0.7829 Intermediate Similarity NPC188555
0.7829 Intermediate Similarity NPC130496
0.7829 Intermediate Similarity NPC187194
0.7826 Intermediate Similarity NPC473621
0.7821 Intermediate Similarity NPC157816
0.7821 Intermediate Similarity NPC265648
0.7821 Intermediate Similarity NPC473873
0.7821 Intermediate Similarity NPC222433
0.7821 Intermediate Similarity NPC473792
0.7806 Intermediate Similarity NPC106944
0.7792 Intermediate Similarity NPC470413
0.7792 Intermediate Similarity NPC138738
0.7785 Intermediate Similarity NPC83743
0.7785 Intermediate Similarity NPC138915
0.7785 Intermediate Similarity NPC262182
0.7785 Intermediate Similarity NPC287615
0.7785 Intermediate Similarity NPC216819
0.7778 Intermediate Similarity NPC60589
0.7778 Intermediate Similarity NPC263835
0.7778 Intermediate Similarity NPC56635
0.7778 Intermediate Similarity NPC469708
0.7771 Intermediate Similarity NPC113680
0.7771 Intermediate Similarity NPC478239
0.7771 Intermediate Similarity NPC278961
0.7764 Intermediate Similarity NPC182350
0.7763 Intermediate Similarity NPC115022
0.7763 Intermediate Similarity NPC28637
0.7763 Intermediate Similarity NPC294166
0.7756 Intermediate Similarity NPC476377
0.7756 Intermediate Similarity NPC134405
0.7756 Intermediate Similarity NPC47471
0.7756 Intermediate Similarity NPC476385
0.7756 Intermediate Similarity NPC186406
0.7755 Intermediate Similarity NPC287429
0.775 Intermediate Similarity NPC80732
0.775 Intermediate Similarity NPC201148
0.775 Intermediate Similarity NPC280945
0.775 Intermediate Similarity NPC28651
0.775 Intermediate Similarity NPC3460
0.775 Intermediate Similarity NPC300262
0.775 Intermediate Similarity NPC192763
0.775 Intermediate Similarity NPC199311
0.775 Intermediate Similarity NPC215095
0.775 Intermediate Similarity NPC210611
0.775 Intermediate Similarity NPC261122
0.775 Intermediate Similarity NPC182119
0.7736 Intermediate Similarity NPC291153
0.7736 Intermediate Similarity NPC115144
0.7736 Intermediate Similarity NPC476743
0.7736 Intermediate Similarity NPC229505
0.7736 Intermediate Similarity NPC205796
0.7736 Intermediate Similarity NPC277857
0.7736 Intermediate Similarity NPC276753
0.7733 Intermediate Similarity NPC314025
0.7727 Intermediate Similarity NPC37468
0.7724 Intermediate Similarity NPC469412
0.7724 Intermediate Similarity NPC198734
0.7724 Intermediate Similarity NPC269242
0.7718 Intermediate Similarity NPC288416
0.7718 Intermediate Similarity NPC106677
0.7716 Intermediate Similarity NPC125823
0.7716 Intermediate Similarity NPC7145
0.7716 Intermediate Similarity NPC143480
0.7716 Intermediate Similarity NPC85192
0.7712 Intermediate Similarity NPC476411
0.7712 Intermediate Similarity NPC471029
0.7707 Intermediate Similarity NPC145319
0.7707 Intermediate Similarity NPC139976
0.7707 Intermediate Similarity NPC49542
0.7707 Intermediate Similarity NPC140502
0.7707 Intermediate Similarity NPC128337
0.7707 Intermediate Similarity NPC230718
0.7707 Intermediate Similarity NPC84207
0.7707 Intermediate Similarity NPC5253
0.7703 Intermediate Similarity NPC29477
0.7702 Intermediate Similarity NPC106138
0.7697 Intermediate Similarity NPC26080
0.7697 Intermediate Similarity NPC165686
0.7697 Intermediate Similarity NPC303422
0.7697 Intermediate Similarity NPC85799
0.7692 Intermediate Similarity NPC473799
0.7692 Intermediate Similarity NPC475530
0.7692 Intermediate Similarity NPC202700
0.7688 Intermediate Similarity NPC15538
0.7688 Intermediate Similarity NPC314213
0.7688 Intermediate Similarity NPC473480
0.7688 Intermediate Similarity NPC476744
0.7687 Intermediate Similarity NPC211218
0.7677 Intermediate Similarity NPC469364
0.7677 Intermediate Similarity NPC65262
0.7677 Intermediate Similarity NPC101686
0.7673 Intermediate Similarity NPC132771
0.7671 Intermediate Similarity NPC55608
0.7669 Intermediate Similarity NPC212699
0.7669 Intermediate Similarity NPC207675
0.7669 Intermediate Similarity NPC215060
0.7669 Intermediate Similarity NPC476352

  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 NPC140915 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
0.7791 Intermediate Similarity NPD8455 Phase 2
0.7628 Intermediate Similarity NPD7266 Discontinued
0.7516 Intermediate Similarity NPD3536 Discontinued
0.7515 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD1091 Approved
0.7389 Intermediate Similarity NPD4108 Discontinued
0.7337 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD7097 Phase 1
0.7273 Intermediate Similarity NPD7007 Discovery
0.7262 Intermediate Similarity NPD7972 Discontinued
0.7229 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1048 Approved
0.7219 Intermediate Similarity NPD3685 Discontinued
0.7195 Intermediate Similarity NPD4123 Phase 3
0.7188 Intermediate Similarity NPD3656 Approved
0.7179 Intermediate Similarity NPD7477 Discontinued
0.7178 Intermediate Similarity NPD6666 Approved
0.7178 Intermediate Similarity NPD6667 Approved
0.7169 Intermediate Similarity NPD3687 Approved
0.7169 Intermediate Similarity NPD3686 Approved
0.716 Intermediate Similarity NPD7089 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5773 Approved
0.716 Intermediate Similarity NPD5772 Approved
0.7159 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6072 Discontinued
0.7135 Intermediate Similarity NPD8031 Discontinued
0.7134 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7213 Phase 3
0.7134 Intermediate Similarity NPD7212 Phase 2
0.7119 Intermediate Similarity NPD7074 Phase 3
0.7119 Intermediate Similarity NPD7472 Approved
0.7108 Intermediate Similarity NPD2122 Discontinued
0.7101 Intermediate Similarity NPD4433 Discontinued
0.7099 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7808 Phase 3
0.7091 Intermediate Similarity NPD7447 Phase 1
0.7088 Intermediate Similarity NPD6842 Approved
0.7088 Intermediate Similarity NPD6841 Approved
0.7088 Intermediate Similarity NPD6843 Phase 3
0.7083 Intermediate Similarity NPD4678 Approved
0.7083 Intermediate Similarity NPD6502 Phase 2
0.7083 Intermediate Similarity NPD4675 Approved
0.7081 Intermediate Similarity NPD1375 Discontinued
0.707 Intermediate Similarity NPD6233 Phase 2
0.7069 Intermediate Similarity NPD7608 Discontinued
0.7066 Intermediate Similarity NPD1653 Approved
0.7062 Intermediate Similarity NPD7054 Approved
0.7055 Intermediate Similarity NPD6331 Phase 2
0.7055 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD8151 Discontinued
0.7044 Intermediate Similarity NPD3052 Approved
0.7044 Intermediate Similarity NPD3054 Approved
0.7039 Intermediate Similarity NPD7251 Discontinued
0.7035 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7228 Approved
0.6986 Remote Similarity NPD7843 Approved
0.6983 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6797 Phase 2
0.6977 Remote Similarity NPD7773 Phase 2
0.6974 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7783 Phase 2
0.697 Remote Similarity NPD5058 Phase 3
0.697 Remote Similarity NPD5756 Phase 2
0.6962 Remote Similarity NPD5745 Approved
0.6961 Remote Similarity NPD8312 Approved
0.6961 Remote Similarity NPD8313 Approved
0.6959 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6959 Remote Similarity NPD2978 Approved
0.6959 Remote Similarity NPD2977 Approved
0.6954 Remote Similarity NPD4666 Phase 3
0.6944 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6943 Remote Similarity NPD5163 Phase 2
0.6937 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6933 Remote Similarity NPD2030 Discontinued
0.6931 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4993 Discontinued
0.6914 Remote Similarity NPD6032 Approved
0.6901 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6899 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6798 Discontinued
0.6899 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6897 Remote Similarity NPD5709 Phase 3
0.689 Remote Similarity NPD6674 Discontinued
0.689 Remote Similarity NPD5062 Approved
0.689 Remote Similarity NPD5061 Approved
0.689 Remote Similarity NPD1652 Phase 2
0.6886 Remote Similarity NPD4739 Approved
0.6886 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6582 Phase 2
0.6883 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6583 Phase 3
0.6875 Remote Similarity NPD4340 Discontinued
0.6875 Remote Similarity NPD6669 Phase 2
0.6871 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6871 Remote Similarity NPD7978 Discontinued
0.6867 Remote Similarity NPD5295 Discontinued
0.6864 Remote Similarity NPD4003 Phase 3
0.686 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6746 Phase 2
0.6856 Remote Similarity NPD7583 Approved
0.6851 Remote Similarity NPD7240 Approved
0.6848 Remote Similarity NPD4628 Phase 3
0.6845 Remote Similarity NPD52 Approved
0.6845 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6845 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7526 Approved
0.6839 Remote Similarity NPD5604 Discontinued
0.6839 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7874 Approved
0.6835 Remote Similarity NPD3179 Approved
0.6835 Remote Similarity NPD3180 Approved
0.6835 Remote Similarity NPD5746 Approved
0.6824 Remote Similarity NPD4005 Discontinued
0.6821 Remote Similarity NPD7585 Approved
0.6818 Remote Similarity NPD2231 Phase 2
0.6818 Remote Similarity NPD2235 Phase 2
0.6813 Remote Similarity NPD1613 Approved
0.6813 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7549 Discontinued
0.681 Remote Similarity NPD2239 Approved
0.681 Remote Similarity NPD2161 Phase 2
0.681 Remote Similarity NPD2240 Approved
0.6805 Remote Similarity NPD7131 Phase 3
0.6796 Remote Similarity NPD3823 Discontinued
0.679 Remote Similarity NPD4537 Clinical (unspecified phase)
0.679 Remote Similarity NPD4536 Approved
0.679 Remote Similarity NPD4538 Approved
0.6788 Remote Similarity NPD4162 Approved
0.6788 Remote Similarity NPD3060 Approved
0.6786 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3985 Discontinued
0.678 Remote Similarity NPD7315 Approved
0.6776 Remote Similarity NPD6382 Discontinued
0.6774 Remote Similarity NPD1669 Approved
0.6772 Remote Similarity NPD2614 Approved
0.6772 Remote Similarity NPD4908 Phase 1
0.6772 Remote Similarity NPD5752 Clinical (unspecified phase)
0.677 Remote Similarity NPD6355 Discontinued
0.677 Remote Similarity NPD5124 Phase 1
0.677 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6763 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6758 Remote Similarity NPD7038 Approved
0.6758 Remote Similarity NPD7685 Pre-registration
0.6758 Remote Similarity NPD7039 Approved
0.6757 Remote Similarity NPD5535 Approved
0.6757 Remote Similarity NPD821 Approved
0.6752 Remote Similarity NPD6584 Phase 3
0.675 Remote Similarity NPD2674 Phase 3
0.675 Remote Similarity NPD1423 Approved
0.675 Remote Similarity NPD839 Approved
0.675 Remote Similarity NPD840 Approved
0.675 Remote Similarity NPD4062 Phase 3
0.6748 Remote Similarity NPD7033 Discontinued
0.6744 Remote Similarity NPD6677 Suspended
0.6743 Remote Similarity NPD8070 Approved
0.6736 Remote Similarity NPD6823 Phase 2
0.6733 Remote Similarity NPD7157 Approved
0.673 Remote Similarity NPD7095 Approved
0.673 Remote Similarity NPD3027 Phase 3
0.6727 Remote Similarity NPD7153 Discontinued
0.6724 Remote Similarity NPD2415 Discontinued
0.6721 Remote Similarity NPD4338 Clinical (unspecified phase)
0.672 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6717 Remote Similarity NPD7801 Approved
0.6712 Remote Similarity NPD2684 Approved
0.6708 Remote Similarity NPD2238 Phase 2
0.6708 Remote Similarity NPD4060 Phase 1
0.6707 Remote Similarity NPD2677 Approved
0.6707 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6705 Remote Similarity NPD37 Approved
0.6688 Remote Similarity NPD3847 Discontinued
0.6688 Remote Similarity NPD3827 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3145 Approved
0.6687 Remote Similarity NPD4236 Phase 3
0.6687 Remote Similarity NPD3144 Approved
0.6687 Remote Similarity NPD5177 Phase 3
0.6687 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6687 Remote Similarity NPD4237 Approved
0.6686 Remote Similarity NPD4966 Approved
0.6686 Remote Similarity NPD4965 Approved
0.6686 Remote Similarity NPD4967 Phase 2
0.6686 Remote Similarity NPD6419 Discontinued
0.6684 Remote Similarity NPD7584 Approved
0.6667 Remote Similarity NPD7811 Phase 3
0.6667 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6559 Discontinued
0.6667 Remote Similarity NPD7810 Phase 3
0.6667 Remote Similarity NPD3122 Phase 3
0.6667 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6649 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6648 Remote Similarity NPD5557 Phase 1
0.6648 Remote Similarity NPD7075 Discontinued
0.6647 Remote Similarity NPD6386 Approved
0.6647 Remote Similarity NPD2541 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