Structure

Physi-Chem Properties

Molecular Weight:  822.22
Volume:  758.683
LogP:  1.54
LogD:  1.401
LogS:  -2.832
# Rotatable Bonds:  17
TPSA:  305.35
# H-Bond Aceptor:  21
# H-Bond Donor:  8
# Rings:  5
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.087
Synthetic Accessibility Score:  4.746
Fsp3:  0.432
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.781
MDCK Permeability:  6.062788452254608e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.986
Human Intestinal Absorption (HIA):  0.966
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.146
Plasma Protein Binding (PPB):  61.211280822753906%
Volume Distribution (VD):  0.511
Pgp-substrate:  22.877445220947266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.14
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.094
CYP2D6-inhibitor:  0.046
CYP2D6-substrate:  0.113
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.01

ADMET: Excretion

Clearance (CL):  3.64
Half-life (T1/2):  0.96

ADMET: Toxicity

hERG Blockers:  0.744
Human Hepatotoxicity (H-HT):  0.039
Drug-inuced Liver Injury (DILI):  0.96
AMES Toxicity:  0.056
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.027
Carcinogencity:  0.053
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.004

Download Data

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

  Natural Product: NPC658

Natural Product ID:  NPC658
Common Name*:   4-O-{6-O-[4-O-(6-O-Syringyloyl-Beta-D-Glucopyranosyl)Vanilloyl]-Beta-D-Glucopyranosyl}-3-Methoxybenzoic Acid
IUPAC Name:   3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(4-hydroxy-3,5-dimethoxybenzoyl)oxymethyl]oxan-2-yl]oxybenzoyl]oxymethyl]oxan-2-yl]oxybenzoic acid
Synonyms:  
Standard InCHIKey:  MINRACKXAPJYCO-RAZBVJSASA-N
Standard InCHI:  InChI=1S/C37H42O21/c1-49-20-9-15(33(45)46)5-7-18(20)55-36-31(43)29(41)27(39)24(57-36)13-53-34(47)16-6-8-19(21(10-16)50-2)56-37-32(44)30(42)28(40)25(58-37)14-54-35(48)17-11-22(51-3)26(38)23(12-17)52-4/h5-12,24-25,27-32,36-44H,13-14H2,1-4H3,(H,45,46)/t24-,25-,27-,28-,29+,30+,31-,32-,36-,37-/m1/s1
SMILES:  COc1cc(ccc1O[C@@H]1O[C@H](COC(=O)c2cc(OC)c(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O)C(=O)OC[C@H]1O[C@@H](Oc2ccc(cc2OC)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL502708
PubChem CID:   24878904
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO21315 Adina polycephala Species Rubiaceae Eukaryota bark n.a. n.a. PMID[18303851]
NPO21315 Adina polycephala Species Rubiaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 60.2 % PMID[557970]

☑ 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 NPC658 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 NPC197708
0.9875 High Similarity NPC5786
0.9875 High Similarity NPC102851
0.9684 High Similarity NPC285108
0.9684 High Similarity NPC33298
0.9557 High Similarity NPC289346
0.9506 High Similarity NPC198125
0.9506 High Similarity NPC95421
0.9506 High Similarity NPC149300
0.9494 High Similarity NPC160780
0.9494 High Similarity NPC289811
0.9451 High Similarity NPC163165
0.9437 High Similarity NPC90905
0.9437 High Similarity NPC4013
0.9434 High Similarity NPC203020
0.9434 High Similarity NPC239966
0.943 High Similarity NPC133984
0.943 High Similarity NPC1913
0.9375 High Similarity NPC311803
0.9375 High Similarity NPC472859
0.9375 High Similarity NPC25389
0.9337 High Similarity NPC79736
0.9337 High Similarity NPC67629
0.9333 High Similarity NPC175230
0.9333 High Similarity NPC172033
0.9333 High Similarity NPC88560
0.9317 High Similarity NPC148273
0.9313 High Similarity NPC166277
0.9313 High Similarity NPC119125
0.9308 High Similarity NPC472860
0.929 High Similarity NPC21359
0.929 High Similarity NPC470713
0.929 High Similarity NPC25946
0.929 High Similarity NPC460984
0.929 High Similarity NPC470717
0.929 High Similarity NPC470720
0.9281 High Similarity NPC267549
0.9259 High Similarity NPC121290
0.925 High Similarity NPC287872
0.925 High Similarity NPC74319
0.9241 High Similarity NPC194095
0.9241 High Similarity NPC191046
0.9241 High Similarity NPC327032
0.9235 High Similarity NPC295625
0.9235 High Similarity NPC470719
0.9235 High Similarity NPC473554
0.9231 High Similarity NPC199172
0.9231 High Similarity NPC35924
0.9231 High Similarity NPC241781
0.9231 High Similarity NPC156785
0.9231 High Similarity NPC470718
0.9231 High Similarity NPC162394
0.9226 High Similarity NPC471030
0.9222 High Similarity NPC297574
0.9217 High Similarity NPC472993
0.9212 High Similarity NPC204937
0.9212 High Similarity NPC149011
0.9198 High Similarity NPC246024
0.9193 High Similarity NPC476373
0.9187 High Similarity NPC172419
0.9187 High Similarity NPC238419
0.9177 High Similarity NPC3746
0.9177 High Similarity NPC205037
0.9177 High Similarity NPC105827
0.9177 High Similarity NPC310661
0.9177 High Similarity NPC61152
0.9177 High Similarity NPC44260
0.9177 High Similarity NPC16024
0.9176 High Similarity NPC249560
0.9176 High Similarity NPC223860
0.9176 High Similarity NPC275977
0.9172 High Similarity NPC469371
0.9167 High Similarity NPC120952
0.9167 High Similarity NPC476618
0.9167 High Similarity NPC476619
0.9167 High Similarity NPC476622
0.9167 High Similarity NPC476623
0.9167 High Similarity NPC476621
0.9167 High Similarity NPC476620
0.9167 High Similarity NPC472387
0.9162 High Similarity NPC84482
0.9162 High Similarity NPC169645
0.9157 High Similarity NPC67134
0.9157 High Similarity NPC47140
0.9141 High Similarity NPC227297
0.913 High Similarity NPC141331
0.913 High Similarity NPC104222
0.913 High Similarity NPC210501
0.913 High Similarity NPC318826
0.913 High Similarity NPC114791
0.9125 High Similarity NPC239019
0.9125 High Similarity NPC247629
0.9125 High Similarity NPC471405
0.9123 High Similarity NPC104910
0.9123 High Similarity NPC33083
0.9123 High Similarity NPC474093
0.9114 High Similarity NPC134905
0.9114 High Similarity NPC36130
0.9112 High Similarity NPC80956
0.9107 High Similarity NPC472723
0.9107 High Similarity NPC472992
0.9107 High Similarity NPC472991
0.9091 High Similarity NPC473818
0.9091 High Similarity NPC116745
0.908 High Similarity NPC476371
0.908 High Similarity NPC476372
0.9074 High Similarity NPC53889
0.907 High Similarity NPC475179
0.907 High Similarity NPC97817
0.907 High Similarity NPC72554
0.907 High Similarity NPC30011
0.9064 High Similarity NPC470416
0.9064 High Similarity NPC470451
0.9064 High Similarity NPC470455
0.9062 High Similarity NPC10205
0.9053 High Similarity NPC293626
0.9053 High Similarity NPC217387
0.9053 High Similarity NPC37668
0.9053 High Similarity NPC477895
0.9053 High Similarity NPC267680
0.9053 High Similarity NPC35167
0.9053 High Similarity NPC196127
0.9053 High Similarity NPC253521
0.9053 High Similarity NPC217520
0.9053 High Similarity NPC113836
0.9053 High Similarity NPC173837
0.9053 High Similarity NPC258044
0.9053 High Similarity NPC139571
0.9048 High Similarity NPC198199
0.9042 High Similarity NPC180918
0.9036 High Similarity NPC195257
0.9036 High Similarity NPC86008
0.9036 High Similarity NPC229687
0.9036 High Similarity NPC209296
0.9023 High Similarity NPC264302
0.9017 High Similarity NPC142291
0.9017 High Similarity NPC7839
0.9012 High Similarity NPC87317
0.9006 High Similarity NPC470445
0.9006 High Similarity NPC470449
0.9006 High Similarity NPC36138
0.9006 High Similarity NPC97119
0.9006 High Similarity NPC135831
0.9006 High Similarity NPC470446
0.9006 High Similarity NPC470447
0.9006 High Similarity NPC297503
0.8994 High Similarity NPC471669
0.8994 High Similarity NPC61904
0.8994 High Similarity NPC473862
0.8994 High Similarity NPC144097
0.8994 High Similarity NPC75695
0.8994 High Similarity NPC89127
0.8988 High Similarity NPC166674
0.8988 High Similarity NPC219600
0.8988 High Similarity NPC473550
0.8988 High Similarity NPC46640
0.8988 High Similarity NPC263119
0.8988 High Similarity NPC204693
0.8988 High Similarity NPC316539
0.8988 High Similarity NPC34436
0.8982 High Similarity NPC105095
0.8982 High Similarity NPC43434
0.8982 High Similarity NPC177731
0.8982 High Similarity NPC231194
0.8982 High Similarity NPC79056
0.8982 High Similarity NPC44328
0.8982 High Similarity NPC51326
0.8982 High Similarity NPC472129
0.8976 High Similarity NPC128403
0.8976 High Similarity NPC45400
0.897 High Similarity NPC142614
0.8966 High Similarity NPC160543
0.8966 High Similarity NPC469652
0.8966 High Similarity NPC472721
0.8966 High Similarity NPC93065
0.8966 High Similarity NPC472724
0.8966 High Similarity NPC31208
0.8966 High Similarity NPC472720
0.8963 High Similarity NPC41009
0.896 High Similarity NPC65489
0.8957 High Similarity NPC24164
0.8953 High Similarity NPC231254
0.8951 High Similarity NPC114179
0.8951 High Similarity NPC156818
0.8951 High Similarity NPC68324
0.8951 High Similarity NPC160512
0.8951 High Similarity NPC289322
0.8951 High Similarity NPC226759
0.8951 High Similarity NPC38779
0.8947 High Similarity NPC8940
0.8947 High Similarity NPC208797
0.8947 High Similarity NPC53680
0.8941 High Similarity NPC89052
0.8941 High Similarity NPC251417
0.8938 High Similarity NPC157898
0.8938 High Similarity NPC137813
0.8935 High Similarity NPC476472
0.8935 High Similarity NPC102028
0.8935 High Similarity NPC473327
0.8935 High Similarity NPC19108

  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 NPC658 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
0.9096 High Similarity NPD7472 Approved
0.9036 High Similarity NPD7054 Approved
0.8982 High Similarity NPD7074 Phase 3
0.8935 High Similarity NPD7808 Phase 3
0.8889 High Similarity NPD4868 Clinical (unspecified phase)
0.8876 High Similarity NPD7251 Discontinued
0.8817 High Similarity NPD6797 Phase 2
0.8817 High Similarity NPD7993 Clinical (unspecified phase)
0.8713 High Similarity NPD4338 Clinical (unspecified phase)
0.8639 High Similarity NPD3818 Discontinued
0.8631 High Similarity NPD6167 Clinical (unspecified phase)
0.8631 High Similarity NPD6166 Phase 2
0.8631 High Similarity NPD6168 Clinical (unspecified phase)
0.8547 High Similarity NPD7685 Pre-registration
0.8421 Intermediate Similarity NPD7228 Approved
0.8383 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8372 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD5844 Phase 1
0.8253 Intermediate Similarity NPD1934 Approved
0.8232 Intermediate Similarity NPD1653 Approved
0.8204 Intermediate Similarity NPD1465 Phase 2
0.8176 Intermediate Similarity NPD7266 Discontinued
0.8136 Intermediate Similarity NPD8313 Approved
0.8136 Intermediate Similarity NPD8312 Approved
0.8095 Intermediate Similarity NPD2801 Approved
0.8095 Intermediate Similarity NPD8455 Phase 2
0.8095 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD3817 Phase 2
0.8045 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD6559 Discontinued
0.8023 Intermediate Similarity NPD7199 Phase 2
0.8023 Intermediate Similarity NPD7240 Approved
0.8012 Intermediate Similarity NPD6234 Discontinued
0.8 Intermediate Similarity NPD3882 Suspended
0.7988 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD6190 Approved
0.7975 Intermediate Similarity NPD230 Phase 1
0.7953 Intermediate Similarity NPD7075 Discontinued
0.7929 Intermediate Similarity NPD37 Approved
0.7923 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7912 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD4966 Approved
0.7895 Intermediate Similarity NPD4967 Phase 2
0.7895 Intermediate Similarity NPD4965 Approved
0.7874 Intermediate Similarity NPD6232 Discontinued
0.7865 Intermediate Similarity NPD8151 Discontinued
0.7841 Intermediate Similarity NPD7473 Discontinued
0.7829 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD4380 Phase 2
0.7778 Intermediate Similarity NPD7819 Suspended
0.7778 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD1511 Approved
0.7765 Intermediate Similarity NPD7411 Suspended
0.7759 Intermediate Similarity NPD5494 Approved
0.7733 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD5402 Approved
0.7697 Intermediate Similarity NPD4628 Phase 3
0.7696 Intermediate Similarity NPD7680 Approved
0.7684 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD1512 Approved
0.7616 Intermediate Similarity NPD6801 Discontinued
0.7614 Intermediate Similarity NPD6959 Discontinued
0.7602 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7783 Phase 2
0.7598 Intermediate Similarity NPD3751 Discontinued
0.7586 Intermediate Similarity NPD7768 Phase 2
0.7579 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD6799 Approved
0.7529 Intermediate Similarity NPD5353 Approved
0.7529 Intermediate Similarity NPD5403 Approved
0.75 Intermediate Similarity NPD3027 Phase 3
0.7472 Intermediate Similarity NPD3787 Discontinued
0.747 Intermediate Similarity NPD1549 Phase 2
0.7469 Intermediate Similarity NPD1613 Approved
0.7469 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD1933 Approved
0.7423 Intermediate Similarity NPD7435 Discontinued
0.7412 Intermediate Similarity NPD5401 Approved
0.7412 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD3750 Approved
0.7375 Intermediate Similarity NPD9494 Approved
0.7345 Intermediate Similarity NPD3749 Approved
0.7341 Intermediate Similarity NPD7458 Discontinued
0.7333 Intermediate Similarity NPD7697 Approved
0.7333 Intermediate Similarity NPD7696 Phase 3
0.7333 Intermediate Similarity NPD7698 Approved
0.7318 Intermediate Similarity NPD8127 Discontinued
0.7317 Intermediate Similarity NPD447 Suspended
0.731 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6599 Discontinued
0.7296 Intermediate Similarity NPD7871 Phase 2
0.7296 Intermediate Similarity NPD7870 Phase 2
0.7286 Intermediate Similarity NPD7874 Approved
0.7286 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD9269 Phase 2
0.7278 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7701 Phase 2
0.7273 Intermediate Similarity NPD7585 Approved
0.7268 Intermediate Similarity NPD6777 Approved
0.7268 Intermediate Similarity NPD6781 Approved
0.7268 Intermediate Similarity NPD6779 Approved
0.7268 Intermediate Similarity NPD6776 Approved
0.7268 Intermediate Similarity NPD6780 Approved
0.7268 Intermediate Similarity NPD6778 Approved
0.7268 Intermediate Similarity NPD6782 Approved
0.7257 Intermediate Similarity NPD6386 Approved
0.7257 Intermediate Similarity NPD6385 Approved
0.7246 Intermediate Similarity NPD1551 Phase 2
0.7246 Intermediate Similarity NPD2796 Approved
0.7243 Intermediate Similarity NPD7039 Approved
0.7243 Intermediate Similarity NPD7038 Approved
0.7238 Intermediate Similarity NPD5242 Approved
0.7234 Intermediate Similarity NPD8434 Phase 2
0.7222 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7583 Approved
0.7219 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD8320 Phase 1
0.7208 Intermediate Similarity NPD8319 Approved
0.7202 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6233 Phase 2
0.7186 Intermediate Similarity NPD1510 Phase 2
0.7165 Intermediate Similarity NPD7699 Phase 2
0.7165 Intermediate Similarity NPD7700 Phase 2
0.716 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3926 Phase 2
0.7143 Intermediate Similarity NPD8150 Discontinued
0.7136 Intermediate Similarity NPD7584 Approved
0.7126 Intermediate Similarity NPD7097 Phase 1
0.7125 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD6674 Discontinued
0.7111 Intermediate Similarity NPD919 Approved
0.7107 Intermediate Similarity NPD6823 Phase 2
0.7083 Intermediate Similarity NPD3748 Approved
0.7079 Intermediate Similarity NPD7801 Approved
0.7076 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD8166 Discontinued
0.7048 Intermediate Similarity NPD943 Approved
0.7048 Intermediate Similarity NPD1240 Approved
0.7041 Intermediate Similarity NPD2935 Discontinued
0.703 Intermediate Similarity NPD6798 Discontinued
0.7025 Intermediate Similarity NPD9268 Approved
0.7021 Intermediate Similarity NPD7549 Discontinued
0.7019 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4908 Phase 1
0.7011 Intermediate Similarity NPD2532 Approved
0.7011 Intermediate Similarity NPD2533 Approved
0.7011 Intermediate Similarity NPD2534 Approved
0.701 Intermediate Similarity NPD6534 Approved
0.701 Intermediate Similarity NPD6535 Approved
0.7 Intermediate Similarity NPD1091 Approved
0.6995 Remote Similarity NPD7229 Phase 3
0.6971 Remote Similarity NPD6273 Approved
0.6966 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6964 Remote Similarity NPD1607 Approved
0.6962 Remote Similarity NPD9545 Approved
0.6961 Remote Similarity NPD6971 Discontinued
0.6949 Remote Similarity NPD3226 Approved
0.694 Remote Similarity NPD1247 Approved
0.6928 Remote Similarity NPD3764 Approved
0.6928 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6919 Remote Similarity NPD1652 Phase 2
0.6915 Remote Similarity NPD5953 Discontinued
0.6909 Remote Similarity NPD6832 Phase 2
0.6898 Remote Similarity NPD7286 Phase 2
0.6897 Remote Similarity NPD7440 Discontinued
0.6872 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6857 Remote Similarity NPD4357 Discontinued
0.6854 Remote Similarity NPD3455 Phase 2
0.6852 Remote Similarity NPD1608 Approved
0.6842 Remote Similarity NPD6099 Approved
0.6842 Remote Similarity NPD6100 Approved
0.6836 Remote Similarity NPD920 Approved
0.6829 Remote Similarity NPD1203 Approved
0.6805 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6805 Remote Similarity NPD5124 Phase 1
0.6805 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6355 Discontinued
0.6786 Remote Similarity NPD6213 Phase 3
0.6786 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6212 Phase 3
0.6784 Remote Similarity NPD7033 Discontinued
0.6782 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4110 Phase 3
0.6768 Remote Similarity NPD3225 Approved
0.6766 Remote Similarity NPD7095 Approved
0.6753 Remote Similarity NPD6841 Approved
0.6753 Remote Similarity NPD6843 Phase 3
0.6753 Remote Similarity NPD6842 Approved
0.6749 Remote Similarity NPD7999 Approved
0.6738 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7930 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