Structure

Physi-Chem Properties

Molecular Weight:  794.23
Volume:  735.233
LogP:  1.404
LogD:  1.079
LogS:  -3.146
# Rotatable Bonds:  16
TPSA:  288.28
# H-Bond Aceptor:  20
# H-Bond Donor:  8
# Rings:  5
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.093
Synthetic Accessibility Score:  4.795
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.674
MDCK Permeability:  6.11543728155084e-05
Pgp-inhibitor:  0.036
Pgp-substrate:  0.98
Human Intestinal Absorption (HIA):  0.944
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.13
Plasma Protein Binding (PPB):  68.9154281616211%
Volume Distribution (VD):  0.42
Pgp-substrate:  26.341354370117188%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.377
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.197
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.626
CYP2D6-inhibitor:  0.284
CYP2D6-substrate:  0.281
CYP3A4-inhibitor:  0.059
CYP3A4-substrate:  0.033

ADMET: Excretion

Clearance (CL):  5.667
Half-life (T1/2):  0.941

ADMET: Toxicity

hERG Blockers:  0.669
Human Hepatotoxicity (H-HT):  0.048
Drug-inuced Liver Injury (DILI):  0.567
AMES Toxicity:  0.088
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.443
Carcinogencity:  0.156
Eye Corrosion:  0.003
Eye Irritation:  0.121
Respiratory Toxicity:  0.006

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

  Natural Product: NPC5786

Natural Product ID:  NPC5786
Common Name*:   4-O-{6-O-[4-O-(6-O-Syringyloyl-Beta-D-Glucopyranosyl)Vanilloyl]-Beta-D-Glucopyranosyl}-2-Methoxy-P-Hydroxyquinone
IUPAC Name:   [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-methoxy-4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxycarbonyl]phenoxy]oxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate
Synonyms:  
Standard InCHIKey:  OCULIFYKQDFJQQ-JRGOIJCHSA-N
Standard InCHI:  InChI=1S/C36H42O20/c1-47-20-12-17(6-7-18(20)37)53-35-31(43)29(41)27(39)24(55-35)13-51-33(45)15-5-8-19(21(9-15)48-2)54-36-32(44)30(42)28(40)25(56-36)14-52-34(46)16-10-22(49-3)26(38)23(11-16)50-4/h5-12,24-25,27-32,35-44H,13-14H2,1-4H3/t24-,25-,27-,28-,29+,30+,31-,32-,35-,36-/m1/s1
SMILES:  COc1cc(ccc1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c2ccc(c(c2)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c3cc(c(c(c3)OC)O)OC)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507011
PubChem CID:   24878851
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 = 25.2 % PMID[535660]

☑ 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 NPC5786 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 NPC102851
0.9875 High Similarity NPC658
0.9875 High Similarity NPC197708
0.963 High Similarity NPC95421
0.963 High Similarity NPC198125
0.9573 High Similarity NPC163165
0.9563 High Similarity NPC90905
0.9563 High Similarity NPC285108
0.9563 High Similarity NPC4013
0.9563 High Similarity NPC33298
0.95 High Similarity NPC472859
0.95 High Similarity NPC311803
0.95 High Similarity NPC25389
0.9437 High Similarity NPC166277
0.9437 High Similarity NPC289346
0.9437 High Similarity NPC119125
0.939 High Similarity NPC149300
0.9375 High Similarity NPC74319
0.9375 High Similarity NPC160780
0.9375 High Similarity NPC289811
0.9375 High Similarity NPC287872
0.9317 High Similarity NPC203020
0.9317 High Similarity NPC239966
0.9313 High Similarity NPC1913
0.9313 High Similarity NPC133984
0.9286 High Similarity NPC476619
0.9286 High Similarity NPC476620
0.9286 High Similarity NPC476622
0.9286 High Similarity NPC472387
0.9286 High Similarity NPC476621
0.9286 High Similarity NPC476618
0.9286 High Similarity NPC476623
0.9281 High Similarity NPC169645
0.9281 High Similarity NPC84482
0.9226 High Similarity NPC67629
0.9226 High Similarity NPC472992
0.9226 High Similarity NPC472991
0.9226 High Similarity NPC79736
0.9222 High Similarity NPC175230
0.9222 High Similarity NPC88560
0.9222 High Similarity NPC172033
0.9202 High Similarity NPC148273
0.9193 High Similarity NPC472860
0.9181 High Similarity NPC470451
0.9181 High Similarity NPC470416
0.9181 High Similarity NPC25946
0.9181 High Similarity NPC470455
0.9181 High Similarity NPC21359
0.9181 High Similarity NPC470717
0.9181 High Similarity NPC470713
0.9181 High Similarity NPC460984
0.9181 High Similarity NPC470720
0.9172 High Similarity NPC267549
0.9146 High Similarity NPC121290
0.9146 High Similarity NPC227297
0.9128 High Similarity NPC295625
0.9128 High Similarity NPC473554
0.9128 High Similarity NPC470719
0.9125 High Similarity NPC327032
0.9125 High Similarity NPC191046
0.9125 High Similarity NPC194095
0.9123 High Similarity NPC156785
0.9123 High Similarity NPC470447
0.9123 High Similarity NPC162394
0.9123 High Similarity NPC35924
0.9123 High Similarity NPC241781
0.9123 High Similarity NPC470446
0.9123 High Similarity NPC470718
0.9123 High Similarity NPC470449
0.9123 High Similarity NPC36138
0.9123 High Similarity NPC470445
0.9123 High Similarity NPC199172
0.9118 High Similarity NPC471030
0.9112 High Similarity NPC297574
0.9107 High Similarity NPC472993
0.9107 High Similarity NPC204693
0.9102 High Similarity NPC149011
0.9102 High Similarity NPC204937
0.9091 High Similarity NPC142614
0.9085 High Similarity NPC246024
0.908 High Similarity NPC472721
0.908 High Similarity NPC476373
0.908 High Similarity NPC160543
0.908 High Similarity NPC31208
0.908 High Similarity NPC469652
0.908 High Similarity NPC93065
0.908 High Similarity NPC472720
0.908 High Similarity NPC472724
0.9074 High Similarity NPC238419
0.9074 High Similarity NPC172419
0.907 High Similarity NPC223860
0.907 High Similarity NPC275977
0.907 High Similarity NPC249560
0.9064 High Similarity NPC8940
0.9064 High Similarity NPC469371
0.9062 High Similarity NPC44260
0.9062 High Similarity NPC310661
0.9062 High Similarity NPC105827
0.9062 High Similarity NPC61152
0.9062 High Similarity NPC205037
0.9062 High Similarity NPC16024
0.9062 High Similarity NPC3746
0.9059 High Similarity NPC120952
0.9053 High Similarity NPC142996
0.9053 High Similarity NPC102028
0.9048 High Similarity NPC259152
0.9048 High Similarity NPC3583
0.9048 High Similarity NPC172807
0.9048 High Similarity NPC47140
0.9048 High Similarity NPC472386
0.9048 High Similarity NPC67134
0.9048 High Similarity NPC254540
0.9048 High Similarity NPC211594
0.9023 High Similarity NPC158214
0.9023 High Similarity NPC240200
0.9023 High Similarity NPC290289
0.9023 High Similarity NPC223534
0.9018 High Similarity NPC114791
0.9018 High Similarity NPC141331
0.9018 High Similarity NPC104222
0.9018 High Similarity NPC318826
0.9018 High Similarity NPC210501
0.9017 High Similarity NPC33083
0.9017 High Similarity NPC261623
0.9017 High Similarity NPC111490
0.9017 High Similarity NPC104910
0.9017 High Similarity NPC474093
0.9012 High Similarity NPC471405
0.9012 High Similarity NPC247629
0.9012 High Similarity NPC239019
0.9006 High Similarity NPC80956
0.9006 High Similarity NPC473571
0.9006 High Similarity NPC241423
0.9006 High Similarity NPC470444
0.9006 High Similarity NPC110941
0.9006 High Similarity NPC470443
0.9006 High Similarity NPC126784
0.9006 High Similarity NPC473682
0.9 High Similarity NPC36130
0.9 High Similarity NPC472723
0.9 High Similarity NPC134905
0.9 High Similarity NPC169733
0.8994 High Similarity NPC239549
0.8994 High Similarity NPC51774
0.8994 High Similarity NPC236191
0.8988 High Similarity NPC471416
0.8988 High Similarity NPC22195
0.8988 High Similarity NPC474434
0.8988 High Similarity NPC44558
0.8988 High Similarity NPC34287
0.8988 High Similarity NPC183357
0.8988 High Similarity NPC21190
0.8982 High Similarity NPC128403
0.8982 High Similarity NPC116745
0.8982 High Similarity NPC473818
0.8971 High Similarity NPC187632
0.897 High Similarity NPC476372
0.897 High Similarity NPC476371
0.8966 High Similarity NPC260521
0.8966 High Similarity NPC469649
0.8966 High Similarity NPC30011
0.8966 High Similarity NPC97817
0.8966 High Similarity NPC72554
0.8966 High Similarity NPC475179
0.8963 High Similarity NPC53889
0.8951 High Similarity NPC10205
0.8947 High Similarity NPC267680
0.8947 High Similarity NPC293626
0.8947 High Similarity NPC477895
0.8947 High Similarity NPC253521
0.8947 High Similarity NPC217520
0.8947 High Similarity NPC196127
0.8947 High Similarity NPC173837
0.8947 High Similarity NPC217387
0.8947 High Similarity NPC475261
0.8947 High Similarity NPC37668
0.8947 High Similarity NPC113836
0.8947 High Similarity NPC139571
0.8947 High Similarity NPC258044
0.8947 High Similarity NPC35167
0.8941 High Similarity NPC198199
0.8941 High Similarity NPC477848
0.8935 High Similarity NPC137871
0.8935 High Similarity NPC156977
0.8935 High Similarity NPC205076
0.8935 High Similarity NPC48773
0.8935 High Similarity NPC288152
0.8935 High Similarity NPC257011
0.8935 High Similarity NPC267254
0.8935 High Similarity NPC180918
0.8935 High Similarity NPC301683
0.8935 High Similarity NPC9002
0.8935 High Similarity NPC307518
0.8935 High Similarity NPC475155
0.8929 High Similarity NPC469931
0.8929 High Similarity NPC112755
0.8929 High Similarity NPC45638
0.8929 High Similarity NPC226294
0.8929 High Similarity NPC95855
0.8929 High Similarity NPC201292

  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 NPC5786 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
0.8988 High Similarity NPD7472 Approved
0.8929 High Similarity NPD7054 Approved
0.8876 High Similarity NPD7074 Phase 3
0.883 High Similarity NPD7808 Phase 3
0.883 High Similarity NPD4338 Clinical (unspecified phase)
0.878 High Similarity NPD4868 Clinical (unspecified phase)
0.8772 High Similarity NPD7251 Discontinued
0.8713 High Similarity NPD7993 Clinical (unspecified phase)
0.8713 High Similarity NPD6797 Phase 2
0.8538 High Similarity NPD3818 Discontinued
0.8529 High Similarity NPD6166 Phase 2
0.8529 High Similarity NPD6168 Clinical (unspecified phase)
0.8529 High Similarity NPD6167 Clinical (unspecified phase)
0.8448 Intermediate Similarity NPD7685 Pre-registration
0.8382 Intermediate Similarity NPD5844 Phase 1
0.8354 Intermediate Similarity NPD1653 Approved
0.8324 Intermediate Similarity NPD7228 Approved
0.8284 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD2801 Approved
0.8182 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD1934 Approved
0.8107 Intermediate Similarity NPD1465 Phase 2
0.8075 Intermediate Similarity NPD7266 Discontinued
0.8056 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD8312 Approved
0.8045 Intermediate Similarity NPD8313 Approved
0.8033 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8022 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8455 Phase 2
0.7988 Intermediate Similarity NPD6190 Approved
0.7953 Intermediate Similarity NPD3817 Phase 2
0.7933 Intermediate Similarity NPD6559 Discontinued
0.7933 Intermediate Similarity NPD7240 Approved
0.7931 Intermediate Similarity NPD7199 Phase 2
0.7919 Intermediate Similarity NPD6234 Discontinued
0.7907 Intermediate Similarity NPD3882 Suspended
0.7892 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD230 Phase 1
0.7874 Intermediate Similarity NPD5494 Approved
0.7861 Intermediate Similarity NPD7075 Discontinued
0.7849 Intermediate Similarity NPD5402 Approved
0.7836 Intermediate Similarity NPD37 Approved
0.7803 Intermediate Similarity NPD4965 Approved
0.7803 Intermediate Similarity NPD4967 Phase 2
0.7803 Intermediate Similarity NPD4966 Approved
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7784 Intermediate Similarity NPD8151 Discontinued
0.7753 Intermediate Similarity NPD7473 Discontinued
0.774 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD4380 Phase 2
0.7704 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7704 Intermediate Similarity NPD7783 Phase 2
0.7688 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7819 Suspended
0.7679 Intermediate Similarity NPD1511 Approved
0.7674 Intermediate Similarity NPD7411 Suspended
0.7644 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD7680 Approved
0.7611 Intermediate Similarity NPD3751 Discontinued
0.7605 Intermediate Similarity NPD4628 Phase 3
0.7598 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD1512 Approved
0.7529 Intermediate Similarity NPD6801 Discontinued
0.7528 Intermediate Similarity NPD6959 Discontinued
0.7526 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7768 Phase 2
0.7486 Intermediate Similarity NPD3787 Discontinued
0.7471 Intermediate Similarity NPD6799 Approved
0.7443 Intermediate Similarity NPD5353 Approved
0.7442 Intermediate Similarity NPD5403 Approved
0.7436 Intermediate Similarity NPD7697 Approved
0.7436 Intermediate Similarity NPD7698 Approved
0.7436 Intermediate Similarity NPD7696 Phase 3
0.7407 Intermediate Similarity NPD3027 Phase 3
0.7398 Intermediate Similarity NPD7870 Phase 2
0.7398 Intermediate Similarity NPD7871 Phase 2
0.7387 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD7874 Approved
0.7381 Intermediate Similarity NPD1549 Phase 2
0.7378 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD1613 Approved
0.7374 Intermediate Similarity NPD7701 Phase 2
0.7371 Intermediate Similarity NPD6782 Approved
0.7371 Intermediate Similarity NPD6778 Approved
0.7371 Intermediate Similarity NPD6779 Approved
0.7371 Intermediate Similarity NPD6781 Approved
0.7371 Intermediate Similarity NPD6777 Approved
0.7371 Intermediate Similarity NPD6780 Approved
0.7371 Intermediate Similarity NPD6776 Approved
0.7362 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1933 Approved
0.7326 Intermediate Similarity NPD5401 Approved
0.7326 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6233 Phase 2
0.7294 Intermediate Similarity NPD3750 Approved
0.7284 Intermediate Similarity NPD9494 Approved
0.7268 Intermediate Similarity NPD7699 Phase 2
0.7268 Intermediate Similarity NPD7700 Phase 2
0.7263 Intermediate Similarity NPD3749 Approved
0.7257 Intermediate Similarity NPD7458 Discontinued
0.7249 Intermediate Similarity NPD8434 Phase 2
0.7238 Intermediate Similarity NPD8127 Discontinued
0.7229 Intermediate Similarity NPD447 Suspended
0.7225 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD6599 Discontinued
0.7208 Intermediate Similarity NPD6823 Phase 2
0.72 Intermediate Similarity NPD7585 Approved
0.7193 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD9269 Phase 2
0.7178 Intermediate Similarity NPD7801 Approved
0.7175 Intermediate Similarity NPD6386 Approved
0.7175 Intermediate Similarity NPD6385 Approved
0.7166 Intermediate Similarity NPD7039 Approved
0.7166 Intermediate Similarity NPD7038 Approved
0.716 Intermediate Similarity NPD2796 Approved
0.716 Intermediate Similarity NPD1551 Phase 2
0.716 Intermediate Similarity NPD2935 Discontinued
0.7158 Intermediate Similarity NPD8150 Discontinued
0.7158 Intermediate Similarity NPD5242 Approved
0.715 Intermediate Similarity NPD7583 Approved
0.7143 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD8319 Approved
0.7136 Intermediate Similarity NPD8320 Phase 1
0.7134 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7549 Discontinued
0.7128 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD6534 Approved
0.7113 Intermediate Similarity NPD6535 Approved
0.7101 Intermediate Similarity NPD1510 Phase 2
0.7076 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD3926 Phase 2
0.7065 Intermediate Similarity NPD7584 Approved
0.7062 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD1247 Approved
0.7041 Intermediate Similarity NPD7097 Phase 1
0.7037 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6674 Discontinued
0.7033 Intermediate Similarity NPD919 Approved
0.7 Intermediate Similarity NPD3748 Approved
0.6994 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6994 Remote Similarity NPD8166 Discontinued
0.6964 Remote Similarity NPD943 Approved
0.6964 Remote Similarity NPD1240 Approved
0.6946 Remote Similarity NPD6798 Discontinued
0.6937 Remote Similarity NPD9268 Approved
0.6932 Remote Similarity NPD2532 Approved
0.6932 Remote Similarity NPD2534 Approved
0.6932 Remote Similarity NPD2533 Approved
0.6928 Remote Similarity NPD4908 Phase 1
0.6919 Remote Similarity NPD7229 Phase 3
0.6914 Remote Similarity NPD1091 Approved
0.6893 Remote Similarity NPD6273 Approved
0.6889 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6888 Remote Similarity NPD6213 Phase 3
0.6888 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6888 Remote Similarity NPD6212 Phase 3
0.6885 Remote Similarity NPD6971 Discontinued
0.6882 Remote Similarity NPD1607 Approved
0.6875 Remote Similarity NPD9545 Approved
0.6872 Remote Similarity NPD3226 Approved
0.685 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3764 Approved
0.6845 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5953 Discontinued
0.6839 Remote Similarity NPD1652 Phase 2
0.6826 Remote Similarity NPD6832 Phase 2
0.6825 Remote Similarity NPD7286 Phase 2
0.6818 Remote Similarity NPD7440 Discontinued
0.6808 Remote Similarity NPD5619 Clinical (unspecified phase)
0.678 Remote Similarity NPD4357 Discontinued
0.6778 Remote Similarity NPD3455 Phase 2
0.6768 Remote Similarity NPD1608 Approved
0.6763 Remote Similarity NPD6100 Approved
0.6763 Remote Similarity NPD6099 Approved
0.676 Remote Similarity NPD920 Approved
0.6758 Remote Similarity NPD6844 Discontinued
0.6747 Remote Similarity NPD1203 Approved
0.6725 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6725 Remote Similarity NPD5124 Phase 1
0.6725 Remote Similarity NPD6355 Discontinued
0.6725 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6713 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6713 Remote Similarity NPD8059 Phase 3
0.6705 Remote Similarity NPD7033 Discontinued
0.6705 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6705 Remote Similarity NPD4110 Phase 3
0.6687 Remote Similarity NPD3225 Approved
0.6686 Remote Similarity NPD7095 Approved
0.6684 Remote Similarity NPD6843 Phase 3
0.6684 Remote Similarity NPD6842 Approved
0.6684 Remote Similarity NPD6841 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