Structure

Physi-Chem Properties

Molecular Weight:  767.3
Volume:  727.769
LogP:  -0.238
LogD:  0.096
LogS:  -3.812
# Rotatable Bonds:  15
TPSA:  275.78
# H-Bond Aceptor:  18
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.085
Synthetic Accessibility Score:  5.089
Fsp3:  0.583
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:  -6.329
MDCK Permeability:  4.5829761802451685e-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.99
Human Intestinal Absorption (HIA):  0.992
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.134
Plasma Protein Binding (PPB):  72.38005828857422%
Volume Distribution (VD):  0.42
Pgp-substrate:  10.524284362792969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.038
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.052
CYP2C19-substrate:  0.135
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.236
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.2
CYP3A4-inhibitor:  0.014
CYP3A4-substrate:  0.017

ADMET: Excretion

Clearance (CL):  0.901
Half-life (T1/2):  0.715

ADMET: Toxicity

hERG Blockers:  0.664
Human Hepatotoxicity (H-HT):  0.214
Drug-inuced Liver Injury (DILI):  0.455
AMES Toxicity:  0.095
Rat Oral Acute Toxicity:  0.018
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.373
Carcinogencity:  0.096
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.012

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

  Natural Product: NPC114659

Natural Product ID:  NPC114659
Common Name*:   (E)-N-4-Methoxycoumaroyltyramine 4-O-Beta-D-Glucopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->3)]-Alpha-L-Rhamnopyranoside
IUPAC Name:   (E)-N-[2-[4-[(2S,3R,4R,5S,6S)-5-hydroxy-6-methyl-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxyphenyl]ethyl]-3-(4-methoxyphenyl)prop-2-enamide
Synonyms:  
Standard InCHIKey:  YRGVFOFEUQMGQT-BZZIOBFNSA-N
Standard InCHI:  InChI=1S/C36H49NO17/c1-17-25(41)32(53-34-30(46)28(44)26(42)22(15-38)51-34)33(54-35-31(47)29(45)27(43)23(16-39)52-35)36(49-17)50-21-10-5-19(6-11-21)13-14-37-24(40)12-7-18-3-8-20(48-2)9-4-18/h3-12,17,22-23,25-36,38-39,41-47H,13-16H2,1-2H3,(H,37,40)/b12-7+/t17-,22+,23+,25-,26+,27+,28-,29-,30+,31+,32+,33+,34-,35-,36-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1ccc(cc1)CCN=C(/C=C/c1ccc(cc1)OC)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3109405
PubChem CID:   76324844
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 = 2.2 n.a. PMID[553510]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. FC = 2.5 n.a. PMID[553510]

☑ 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 NPC114659 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 NPC139699
0.9722 High Similarity NPC18249
0.9722 High Similarity NPC10221
0.9722 High Similarity NPC187028
0.9722 High Similarity NPC197741
0.9722 High Similarity NPC305700
0.9722 High Similarity NPC140915
0.9161 High Similarity NPC178466
0.9161 High Similarity NPC63628
0.8759 High Similarity NPC195814
0.8446 Intermediate Similarity NPC89686
0.8446 Intermediate Similarity NPC257095
0.8446 Intermediate Similarity NPC273932
0.8425 Intermediate Similarity NPC469383
0.8367 Intermediate Similarity NPC36434
0.8355 Intermediate Similarity NPC471032
0.8355 Intermediate Similarity NPC470935
0.8333 Intermediate Similarity NPC116922
0.8311 Intermediate Similarity NPC298821
0.8278 Intermediate Similarity NPC225445
0.8255 Intermediate Similarity NPC123761
0.8212 Intermediate Similarity NPC136951
0.8212 Intermediate Similarity NPC161155
0.8212 Intermediate Similarity NPC97004
0.8176 Intermediate Similarity NPC138350
0.8176 Intermediate Similarity NPC197723
0.8176 Intermediate Similarity NPC40664
0.8176 Intermediate Similarity NPC3293
0.8176 Intermediate Similarity NPC165482
0.8158 Intermediate Similarity NPC313414
0.8158 Intermediate Similarity NPC97282
0.8158 Intermediate Similarity NPC177597
0.8125 Intermediate Similarity NPC50380
0.8125 Intermediate Similarity NPC179250
0.8121 Intermediate Similarity NPC87777
0.8121 Intermediate Similarity NPC262328
0.8108 Intermediate Similarity NPC238243
0.8099 Intermediate Similarity NPC95733
0.8099 Intermediate Similarity NPC62101
0.8085 Intermediate Similarity NPC476142
0.8056 Intermediate Similarity NPC198798
0.8041 Intermediate Similarity NPC188555
0.8041 Intermediate Similarity NPC187194
0.8041 Intermediate Similarity NPC130496
0.8039 Intermediate Similarity NPC471063
0.8025 Intermediate Similarity NPC473621
0.8013 Intermediate Similarity NPC106944
0.8 Intermediate Similarity NPC60589
0.8 Intermediate Similarity NPC138738
0.8 Intermediate Similarity NPC263835
0.8 Intermediate Similarity NPC175275
0.8 Intermediate Similarity NPC469708
0.8 Intermediate Similarity NPC470413
0.7987 Intermediate Similarity NPC263829
0.7974 Intermediate Similarity NPC278961
0.7974 Intermediate Similarity NPC113680
0.7973 Intermediate Similarity NPC115022
0.7973 Intermediate Similarity NPC294166
0.7972 Intermediate Similarity NPC287429
0.7949 Intermediate Similarity NPC280945
0.7949 Intermediate Similarity NPC220282
0.7943 Intermediate Similarity NPC469412
0.7943 Intermediate Similarity NPC198734
0.7943 Intermediate Similarity NPC269242
0.7935 Intermediate Similarity NPC115144
0.7935 Intermediate Similarity NPC476743
0.7935 Intermediate Similarity NPC276753
0.7935 Intermediate Similarity NPC205796
0.7935 Intermediate Similarity NPC277857
0.7919 Intermediate Similarity NPC476411
0.7917 Intermediate Similarity NPC29477
0.7908 Intermediate Similarity NPC5253
0.7908 Intermediate Similarity NPC139976
0.7908 Intermediate Similarity NPC84207
0.7908 Intermediate Similarity NPC128337
0.7908 Intermediate Similarity NPC230718
0.7908 Intermediate Similarity NPC49542
0.7905 Intermediate Similarity NPC26080
0.7905 Intermediate Similarity NPC85799
0.7905 Intermediate Similarity NPC165686
0.7905 Intermediate Similarity NPC303422
0.7902 Intermediate Similarity NPC211218
0.7898 Intermediate Similarity NPC476398
0.7898 Intermediate Similarity NPC476386
0.7898 Intermediate Similarity NPC306890
0.7898 Intermediate Similarity NPC259347
0.7898 Intermediate Similarity NPC471062
0.7898 Intermediate Similarity NPC473427
0.7898 Intermediate Similarity NPC94871
0.7898 Intermediate Similarity NPC470933
0.7887 Intermediate Similarity NPC55608
0.7885 Intermediate Similarity NPC476744
0.7885 Intermediate Similarity NPC473480
0.7885 Intermediate Similarity NPC97240
0.7885 Intermediate Similarity NPC15538
0.7867 Intermediate Similarity NPC79957
0.7848 Intermediate Similarity NPC257970
0.7848 Intermediate Similarity NPC475224
0.7848 Intermediate Similarity NPC470927
0.7843 Intermediate Similarity NPC108674
0.7838 Intermediate Similarity NPC9912
0.7838 Intermediate Similarity NPC121376
0.7823 Intermediate Similarity NPC295970
0.7823 Intermediate Similarity NPC248355
0.7821 Intermediate Similarity NPC476865
0.7815 Intermediate Similarity NPC41473
0.7815 Intermediate Similarity NPC14600
0.7815 Intermediate Similarity NPC204848
0.7815 Intermediate Similarity NPC312770
0.7815 Intermediate Similarity NPC52277
0.7815 Intermediate Similarity NPC199459
0.7815 Intermediate Similarity NPC164857
0.7815 Intermediate Similarity NPC160607
0.7815 Intermediate Similarity NPC177035
0.7806 Intermediate Similarity NPC476867
0.7805 Intermediate Similarity NPC470936
0.78 Intermediate Similarity NPC35731
0.7799 Intermediate Similarity NPC259707
0.7792 Intermediate Similarity NPC472353
0.7792 Intermediate Similarity NPC469559
0.7785 Intermediate Similarity NPC476742
0.7771 Intermediate Similarity NPC232992
0.777 Intermediate Similarity NPC80600
0.777 Intermediate Similarity NPC472024
0.7763 Intermediate Similarity NPC299583
0.7763 Intermediate Similarity NPC124149
0.7762 Intermediate Similarity NPC57751
0.7758 Intermediate Similarity NPC90984
0.7756 Intermediate Similarity NPC476868
0.7756 Intermediate Similarity NPC476864
0.7756 Intermediate Similarity NPC476866
0.7756 Intermediate Similarity NPC476869
0.7755 Intermediate Similarity NPC302378
0.7748 Intermediate Similarity NPC470236
0.7742 Intermediate Similarity NPC46092
0.7742 Intermediate Similarity NPC185307
0.7742 Intermediate Similarity NPC470950
0.7742 Intermediate Similarity NPC469367
0.7736 Intermediate Similarity NPC476871
0.7736 Intermediate Similarity NPC476741
0.7727 Intermediate Similarity NPC210192
0.7718 Intermediate Similarity NPC225384
0.7718 Intermediate Similarity NPC475067
0.7718 Intermediate Similarity NPC46137
0.7718 Intermediate Similarity NPC246869
0.7718 Intermediate Similarity NPC138777
0.7718 Intermediate Similarity NPC235294
0.7712 Intermediate Similarity NPC98777
0.7712 Intermediate Similarity NPC212770
0.7707 Intermediate Similarity NPC107120
0.7707 Intermediate Similarity NPC125755
0.7707 Intermediate Similarity NPC74320
0.7703 Intermediate Similarity NPC166040
0.7703 Intermediate Similarity NPC270849
0.7703 Intermediate Similarity NPC218003
0.7703 Intermediate Similarity NPC26653
0.7697 Intermediate Similarity NPC254610
0.7697 Intermediate Similarity NPC203230
0.7697 Intermediate Similarity NPC242028
0.7697 Intermediate Similarity NPC166180
0.7692 Intermediate Similarity NPC160854
0.7692 Intermediate Similarity NPC129417
0.7692 Intermediate Similarity NPC471028
0.7692 Intermediate Similarity NPC470235
0.7692 Intermediate Similarity NPC469313
0.7692 Intermediate Similarity NPC469703
0.7692 Intermediate Similarity NPC138227
0.7692 Intermediate Similarity NPC469704
0.7692 Intermediate Similarity NPC76176
0.7692 Intermediate Similarity NPC201402
0.7692 Intermediate Similarity NPC283995
0.7692 Intermediate Similarity NPC168579
0.7677 Intermediate Similarity NPC246947
0.7677 Intermediate Similarity NPC60249
0.7677 Intermediate Similarity NPC476356
0.7677 Intermediate Similarity NPC189115
0.7673 Intermediate Similarity NPC55715
0.7673 Intermediate Similarity NPC35877
0.7673 Intermediate Similarity NPC95392
0.7671 Intermediate Similarity NPC470510
0.7667 Intermediate Similarity NPC254275
0.7661 Intermediate Similarity NPC314656
0.7654 Intermediate Similarity NPC160882
0.7651 Intermediate Similarity NPC198741
0.7647 Intermediate Similarity NPC65530
0.7647 Intermediate Similarity NPC296898
0.7647 Intermediate Similarity NPC59324
0.7647 Intermediate Similarity NPC304152
0.7643 Intermediate Similarity NPC43508
0.7643 Intermediate Similarity NPC476382
0.7643 Intermediate Similarity NPC475096
0.7643 Intermediate Similarity NPC38041
0.7643 Intermediate Similarity NPC18979
0.7643 Intermediate Similarity NPC252292
0.7643 Intermediate Similarity NPC34927
0.7643 Intermediate Similarity NPC34587
0.7643 Intermediate Similarity NPC277867
0.7643 Intermediate Similarity NPC279298
0.7643 Intermediate Similarity NPC161700
0.7643 Intermediate Similarity NPC100998

  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 NPC114659 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
0.7639 Intermediate Similarity NPD1091 Approved
0.7582 Intermediate Similarity NPD4108 Discontinued
0.7546 Intermediate Similarity NPD8455 Phase 2
0.7515 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7007 Discovery
0.7415 Intermediate Similarity NPD3685 Discontinued
0.7375 Intermediate Similarity NPD4123 Phase 3
0.7372 Intermediate Similarity NPD7266 Discontinued
0.7368 Intermediate Similarity NPD7477 Discontinued
0.7333 Intermediate Similarity NPD5772 Approved
0.7333 Intermediate Similarity NPD7089 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5773 Approved
0.732 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6072 Discontinued
0.7312 Intermediate Similarity NPD7213 Phase 3
0.7312 Intermediate Similarity NPD7212 Phase 2
0.7284 Intermediate Similarity NPD2122 Discontinued
0.7267 Intermediate Similarity NPD7447 Phase 1
0.7267 Intermediate Similarity NPD3536 Discontinued
0.7261 Intermediate Similarity NPD1375 Discontinued
0.7256 Intermediate Similarity NPD4678 Approved
0.7256 Intermediate Similarity NPD4675 Approved
0.7233 Intermediate Similarity NPD6331 Phase 2
0.7233 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3052 Approved
0.7226 Intermediate Similarity NPD3054 Approved
0.7215 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD7843 Approved
0.7143 Intermediate Similarity NPD5058 Phase 3
0.7143 Intermediate Similarity NPD5756 Phase 2
0.7126 Intermediate Similarity NPD2977 Approved
0.7126 Intermediate Similarity NPD2978 Approved
0.7126 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4993 Discontinued
0.7101 Intermediate Similarity NPD8031 Discontinued
0.7086 Intermediate Similarity NPD7074 Phase 3
0.7086 Intermediate Similarity NPD7472 Approved
0.7078 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD7097 Phase 1
0.7067 Intermediate Similarity NPD6583 Phase 3
0.7067 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD6582 Phase 2
0.7063 Intermediate Similarity NPD5062 Approved
0.7063 Intermediate Similarity NPD5061 Approved
0.7063 Intermediate Similarity NPD6674 Discontinued
0.7062 Intermediate Similarity NPD7808 Phase 3
0.7056 Intermediate Similarity NPD6843 Phase 3
0.7056 Intermediate Similarity NPD6842 Approved
0.7056 Intermediate Similarity NPD6841 Approved
0.7029 Intermediate Similarity NPD7054 Approved
0.7024 Intermediate Similarity NPD7972 Discontinued
0.702 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD3180 Approved
0.7013 Intermediate Similarity NPD3179 Approved
0.7012 Intermediate Similarity NPD7526 Approved
0.7012 Intermediate Similarity NPD52 Approved
0.7012 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7251 Discontinued
0.7 Intermediate Similarity NPD2231 Phase 2
0.7 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2235 Phase 2
0.7 Intermediate Similarity NPD5604 Discontinued
0.6988 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4005 Discontinued
0.6987 Remote Similarity NPD1613 Approved
0.6987 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6981 Remote Similarity NPD2161 Phase 2
0.6968 Remote Similarity NPD1048 Approved
0.6962 Remote Similarity NPD4538 Approved
0.6962 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6962 Remote Similarity NPD4536 Approved
0.6959 Remote Similarity NPD6382 Discontinued
0.6957 Remote Similarity NPD4162 Approved
0.6957 Remote Similarity NPD3060 Approved
0.6954 Remote Similarity NPD1669 Approved
0.6951 Remote Similarity NPD3985 Discontinued
0.6949 Remote Similarity NPD6797 Phase 2
0.6948 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6948 Remote Similarity NPD4908 Phase 1
0.6944 Remote Similarity NPD821 Approved
0.6941 Remote Similarity NPD7773 Phase 2
0.6937 Remote Similarity NPD3656 Approved
0.6933 Remote Similarity NPD6666 Approved
0.6933 Remote Similarity NPD6667 Approved
0.6928 Remote Similarity NPD3687 Approved
0.6928 Remote Similarity NPD3686 Approved
0.6928 Remote Similarity NPD6584 Phase 3
0.6923 Remote Similarity NPD839 Approved
0.6923 Remote Similarity NPD840 Approved
0.6923 Remote Similarity NPD2674 Phase 3
0.6923 Remote Similarity NPD1423 Approved
0.6923 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7157 Approved
0.6903 Remote Similarity NPD3027 Phase 3
0.6901 Remote Similarity NPD8070 Approved
0.6901 Remote Similarity NPD2684 Approved
0.6894 Remote Similarity NPD7153 Discontinued
0.6879 Remote Similarity NPD2238 Phase 2
0.6875 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6871 Remote Similarity NPD2677 Approved
0.6868 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6864 Remote Similarity NPD4433 Discontinued
0.6859 Remote Similarity NPD3144 Approved
0.6859 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6859 Remote Similarity NPD3145 Approved
0.6852 Remote Similarity NPD5177 Phase 3
0.6852 Remote Similarity NPD4236 Phase 3
0.6852 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4237 Approved
0.6848 Remote Similarity NPD4739 Approved
0.6848 Remote Similarity NPD6419 Discontinued
0.6846 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6502 Phase 2
0.6842 Remote Similarity NPD6669 Phase 2
0.6839 Remote Similarity NPD8151 Discontinued
0.6839 Remote Similarity NPD7608 Discontinued
0.6829 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3122 Phase 3
0.6829 Remote Similarity NPD5295 Discontinued
0.6826 Remote Similarity NPD1653 Approved
0.6815 Remote Similarity NPD6233 Phase 2
0.6813 Remote Similarity NPD5588 Approved
0.6813 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5960 Phase 3
0.6813 Remote Similarity NPD6029 Clinical (unspecified phase)
0.68 Remote Similarity NPD2668 Approved
0.68 Remote Similarity NPD5238 Clinical (unspecified phase)
0.68 Remote Similarity NPD2667 Approved
0.6797 Remote Similarity NPD8651 Approved
0.6784 Remote Similarity NPD6063 Approved
0.678 Remote Similarity NPD7228 Approved
0.6779 Remote Similarity NPD6581 Approved
0.6779 Remote Similarity NPD6580 Approved
0.6779 Remote Similarity NPD1548 Phase 1
0.6774 Remote Similarity NPD2861 Phase 2
0.6772 Remote Similarity NPD1558 Phase 1
0.6769 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6769 Remote Similarity NPD7783 Phase 2
0.6766 Remote Similarity NPD7131 Phase 3
0.676 Remote Similarity NPD7959 Clinical (unspecified phase)
0.676 Remote Similarity NPD3823 Discontinued
0.6757 Remote Similarity NPD3596 Phase 2
0.6753 Remote Similarity NPD1820 Approved
0.6753 Remote Similarity NPD3568 Approved
0.6753 Remote Similarity NPD1817 Approved
0.6753 Remote Similarity NPD3567 Approved
0.6753 Remote Similarity NPD4098 Discontinued
0.6753 Remote Similarity NPD1819 Approved
0.6753 Remote Similarity NPD3827 Clinical (unspecified phase)
0.6753 Remote Similarity NPD1818 Approved
0.675 Remote Similarity NPD7119 Phase 2
0.6748 Remote Similarity NPD5289 Phase 2
0.6748 Remote Similarity NPD6364 Approved
0.6748 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6748 Remote Similarity NPD44 Approved
0.6746 Remote Similarity NPD3296 Phase 1
0.674 Remote Similarity NPD8313 Approved
0.674 Remote Similarity NPD8312 Approved
0.6732 Remote Similarity NPD4659 Approved
0.6732 Remote Similarity NPD2428 Approved
0.6732 Remote Similarity NPD2429 Approved
0.6731 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6728 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6725 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6724 Remote Similarity NPD4666 Phase 3
0.6722 Remote Similarity NPD8014 Clinical (unspecified phase)
0.672 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6713 Remote Similarity NPD290 Approved
0.6711 Remote Similarity NPD1610 Phase 2
0.6711 Remote Similarity NPD776 Approved
0.671 Remote Similarity NPD558 Phase 2
0.6709 Remote Similarity NPD5745 Approved
0.6709 Remote Similarity NPD3530 Approved
0.6709 Remote Similarity NPD3532 Approved
0.6709 Remote Similarity NPD3531 Approved
0.6708 Remote Similarity NPD6380 Phase 1
0.6708 Remote Similarity NPD3846 Clinical (unspecified phase)
0.6707 Remote Similarity NPD7466 Approved
0.6706 Remote Similarity NPD3778 Approved
0.6705 Remote Similarity NPD2969 Approved
0.6705 Remote Similarity NPD2970 Approved
0.6703 Remote Similarity NPD8053 Approved
0.6703 Remote Similarity NPD8054 Approved
0.6702 Remote Similarity NPD6823 Phase 2
0.6689 Remote Similarity NPD5846 Approved
0.6689 Remote Similarity NPD6516 Phase 2
0.6689 Remote Similarity NPD2556 Approved
0.6689 Remote Similarity NPD2554 Approved
0.6688 Remote Similarity NPD3166 Approved
0.6688 Remote Similarity NPD3167 Approved
0.6688 Remote Similarity NPD3164 Approved
0.6688 Remote Similarity NPD3165 Approved
0.6688 Remote Similarity NPD5163 Phase 2
0.6687 Remote Similarity NPD2030 Discontinued
0.6687 Remote Similarity NPD2157 Approved
0.6686 Remote Similarity NPD6523 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