Structure

Physi-Chem Properties

Molecular Weight:  914.15
Volume:  841.784
LogP:  2.88
LogD:  1.058
LogS:  -4.794
# Rotatable Bonds:  9
TPSA:  394.74
# H-Bond Aceptor:  22
# H-Bond Donor:  16
# Rings:  8
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.078
Synthetic Accessibility Score:  5.271
Fsp3:  0.136
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -7.386
MDCK Permeability:  2.4392088562308345e-06
Pgp-inhibitor:  0.142
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  82.19661712646484%
Volume Distribution (VD):  0.194
Pgp-substrate:  34.0068359375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.191
CYP1A2-substrate:  0.04
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.017
CYP2C9-inhibitor:  0.249
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.096
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.042

ADMET: Excretion

Clearance (CL):  12.634
Half-life (T1/2):  0.928

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.427
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.072
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.749
Skin Sensitization:  0.984
Carcinogencity:  0.009
Eye Corrosion:  0.003
Eye Irritation:  0.955
Respiratory Toxicity:  0.001

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

  Natural Product: NPC100251

Natural Product ID:  NPC100251
Common Name*:   Prodelphinidin B-2 3,3'-Di-O-Gallate
IUPAC Name:   [(2R,3R)-8-[(2R,3R,4R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:  
Standard InCHIKey:  OBAZBWUNTJYECH-SHHRIEJHSA-N
Standard InCHI:  InChI=1S/C44H34O22/c45-17-9-20(47)32-30(10-17)63-40(14-3-24(51)36(58)25(52)4-14)42(66-44(62)16-7-28(55)38(60)29(56)8-16)34(32)33-21(48)12-19(46)18-11-31(64-43(61)15-5-26(53)37(59)27(54)6-15)39(65-41(18)33)13-1-22(49)35(57)23(50)2-13/h1-10,12,31,34,39-40,42,45-60H,11H2/t31-,34-,39-,40-,42-/m1/s1
SMILES:  c1c(cc(c(c1O)O)O)[C@@H]1[C@@H](Cc2c(cc(c([C@H]3c4c(cc(cc4O[C@H](c4cc(c(c(c4)O)O)O)[C@@H]3OC(=O)c3cc(c(c(c3)O)O)O)O)O)c2O1)O)O)OC(=O)c1cc(c(c(c1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL422711
PubChem CID:   467306
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO31026 Myrica rubra Species Myricaceae Eukaryota barks n.a. n.a. PMID[23066712]
NPO31026 Myrica rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31026 Myrica rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT759 Cell Line H9 Homo sapiens IC50 = 40.0 ug.mL-1 PMID[518465]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 19.2 ug.mL-1 PMID[518466]

☑ 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 NPC100251 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
0.9938 High Similarity NPC98583
0.9876 High Similarity NPC65333
0.9353 High Similarity NPC112380
0.9333 High Similarity NPC180768
0.929 High Similarity NPC117668
0.929 High Similarity NPC125352
0.9268 High Similarity NPC9309
0.925 High Similarity NPC300845
0.925 High Similarity NPC250436
0.925 High Similarity NPC291948
0.925 High Similarity NPC104983
0.925 High Similarity NPC88803
0.9193 High Similarity NPC160512
0.9193 High Similarity NPC68324
0.9193 High Similarity NPC114179
0.9193 High Similarity NPC38779
0.9193 High Similarity NPC156818
0.9193 High Similarity NPC289322
0.9152 High Similarity NPC224851
0.9136 High Similarity NPC87317
0.9133 High Similarity NPC269046
0.913 High Similarity NPC318432
0.9123 High Similarity NPC129533
0.9123 High Similarity NPC123259
0.9102 High Similarity NPC476365
0.9096 High Similarity NPC473818
0.9096 High Similarity NPC217781
0.9085 High Similarity NPC476372
0.9085 High Similarity NPC476371
0.908 High Similarity NPC24164
0.908 High Similarity NPC53889
0.9075 High Similarity NPC237202
0.9064 High Similarity NPC8940
0.9059 High Similarity NPC471789
0.9059 High Similarity NPC265380
0.9048 High Similarity NPC81332
0.9048 High Similarity NPC262580
0.9048 High Similarity NPC257667
0.9048 High Similarity NPC289396
0.9048 High Similarity NPC271848
0.9048 High Similarity NPC186847
0.9048 High Similarity NPC212038
0.9048 High Similarity NPC472454
0.9042 High Similarity NPC149300
0.9036 High Similarity NPC317671
0.9036 High Similarity NPC26536
0.9036 High Similarity NPC49983
0.9036 High Similarity NPC171985
0.9036 High Similarity NPC142707
0.9036 High Similarity NPC320741
0.903 High Similarity NPC45943
0.9029 High Similarity NPC264302
0.9023 High Similarity NPC158214
0.9023 High Similarity NPC142291
0.9023 High Similarity NPC240200
0.9023 High Similarity NPC290289
0.9023 High Similarity NPC223534
0.9023 High Similarity NPC7839
0.9018 High Similarity NPC166456
0.9018 High Similarity NPC7543
0.9018 High Similarity NPC94220
0.9018 High Similarity NPC24339
0.9018 High Similarity NPC98083
0.9012 High Similarity NPC132111
0.9006 High Similarity NPC185275
0.9006 High Similarity NPC80956
0.9 High Similarity NPC67629
0.9 High Similarity NPC79736
0.8976 High Similarity NPC166851
0.8976 High Similarity NPC162169
0.8971 High Similarity NPC472724
0.8971 High Similarity NPC31208
0.8971 High Similarity NPC187632
0.8971 High Similarity NPC472720
0.8971 High Similarity NPC160543
0.8971 High Similarity NPC469652
0.8971 High Similarity NPC472721
0.8971 High Similarity NPC93065
0.8966 High Similarity NPC260521
0.8966 High Similarity NPC65489
0.8966 High Similarity NPC469649
0.8963 High Similarity NPC476373
0.896 High Similarity NPC318119
0.8947 High Similarity NPC267549
0.8944 High Similarity NPC474656
0.8929 High Similarity NPC107627
0.8927 High Similarity NPC476358
0.8927 High Similarity NPC477082
0.8922 High Similarity NPC207575
0.8922 High Similarity NPC13481
0.892 High Similarity NPC471091
0.892 High Similarity NPC40078
0.892 High Similarity NPC97924
0.8914 High Similarity NPC119094
0.8914 High Similarity NPC173872
0.8909 High Similarity NPC216916
0.8909 High Similarity NPC155754
0.8909 High Similarity NPC124747
0.8909 High Similarity NPC109061
0.8908 High Similarity NPC469650
0.8902 High Similarity NPC321916
0.8902 High Similarity NPC150977
0.8896 High Similarity NPC165483
0.8895 High Similarity NPC324742
0.8889 High Similarity NPC297574
0.8889 High Similarity NPC472723
0.8869 High Similarity NPC190204
0.8869 High Similarity NPC43918
0.8869 High Similarity NPC261411
0.8864 High Similarity NPC201814
0.8862 High Similarity NPC477840
0.8862 High Similarity NPC142614
0.8862 High Similarity NPC471788
0.8857 High Similarity NPC269625
0.8855 High Similarity NPC477841
0.8855 High Similarity NPC12326
0.8851 High Similarity NPC231254
0.8848 High Similarity NPC24627
0.8844 High Similarity NPC208797
0.8844 High Similarity NPC53680
0.8834 High Similarity NPC222185
0.8833 High Similarity NPC174140
0.8827 High Similarity NPC3474
0.8824 High Similarity NPC476370
0.8817 High Similarity NPC658
0.8817 High Similarity NPC197708
0.8817 High Similarity NPC198125
0.8817 High Similarity NPC475212
0.8817 High Similarity NPC95421
0.881 High Similarity NPC43065
0.881 High Similarity NPC175793
0.8807 High Similarity NPC477083
0.8807 High Similarity NPC477081
0.8802 High Similarity NPC121290
0.88 High Similarity NPC221140
0.88 High Similarity NPC475352
0.88 High Similarity NPC111490
0.88 High Similarity NPC473686
0.88 High Similarity NPC475220
0.88 High Similarity NPC229817
0.88 High Similarity NPC261623
0.8795 High Similarity NPC177100
0.8795 High Similarity NPC139540
0.8788 High Similarity NPC141331
0.8788 High Similarity NPC104222
0.8788 High Similarity NPC114791
0.8788 High Similarity NPC318826
0.8788 High Similarity NPC210501
0.8773 High Similarity NPC469888
0.8772 High Similarity NPC476374
0.8772 High Similarity NPC316539
0.8765 High Similarity NPC47521
0.8757 High Similarity NPC260266
0.8757 High Similarity NPC470271
0.8757 High Similarity NPC311389
0.875 High Similarity NPC179947
0.8743 High Similarity NPC219927
0.8736 High Similarity NPC469371
0.8735 High Similarity NPC98023
0.8735 High Similarity NPC226462
0.8727 High Similarity NPC322459
0.8727 High Similarity NPC324358
0.8727 High Similarity NPC125495
0.8727 High Similarity NPC318527
0.8727 High Similarity NPC323627
0.8713 High Similarity NPC5786
0.8713 High Similarity NPC102851
0.8713 High Similarity NPC4200
0.8713 High Similarity NPC67134
0.8713 High Similarity NPC47140
0.8706 High Similarity NPC300307
0.8701 High Similarity NPC473618
0.8698 High Similarity NPC272560
0.8698 High Similarity NPC471823
0.8693 High Similarity NPC304322
0.869 High Similarity NPC63438
0.869 High Similarity NPC67959
0.8686 High Similarity NPC293227
0.8686 High Similarity NPC97119
0.8686 High Similarity NPC135831
0.8686 High Similarity NPC473717
0.8686 High Similarity NPC475662
0.8686 High Similarity NPC473631
0.8686 High Similarity NPC297503
0.8683 High Similarity NPC471211
0.8683 High Similarity NPC134783
0.8683 High Similarity NPC228383
0.8683 High Similarity NPC471212
0.8683 High Similarity NPC266365
0.8683 High Similarity NPC142252
0.8683 High Similarity NPC469889
0.8683 High Similarity NPC97812
0.8678 High Similarity NPC471030
0.8678 High Similarity NPC473785
0.8675 High Similarity NPC267627
0.8675 High Similarity NPC37502
0.8675 High Similarity NPC40702
0.8667 High Similarity NPC69531
0.8667 High Similarity NPC239019
0.8667 High Similarity NPC134925

  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 NPC100251 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
0.9277 High Similarity NPD7993 Clinical (unspecified phase)
0.925 High Similarity NPD4868 Clinical (unspecified phase)
0.8545 High Similarity NPD1465 Phase 2
0.8529 High Similarity NPD6166 Phase 2
0.8529 High Similarity NPD6168 Clinical (unspecified phase)
0.8529 High Similarity NPD6167 Clinical (unspecified phase)
0.8488 Intermediate Similarity NPD5844 Phase 1
0.8457 Intermediate Similarity NPD8312 Approved
0.8457 Intermediate Similarity NPD8313 Approved
0.8434 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8353 Intermediate Similarity NPD6959 Discontinued
0.8333 Intermediate Similarity NPD7074 Phase 3
0.8333 Intermediate Similarity NPD7472 Approved
0.8314 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD7075 Discontinued
0.8276 Intermediate Similarity NPD7054 Approved
0.8274 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD7473 Discontinued
0.8263 Intermediate Similarity NPD1934 Approved
0.8239 Intermediate Similarity NPD7251 Discontinued
0.8225 Intermediate Similarity NPD7768 Phase 2
0.8222 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD8455 Phase 2
0.8214 Intermediate Similarity NPD7819 Suspended
0.8198 Intermediate Similarity NPD6232 Discontinued
0.8192 Intermediate Similarity NPD7808 Phase 3
0.8187 Intermediate Similarity NPD5494 Approved
0.8182 Intermediate Similarity NPD6797 Phase 2
0.8144 Intermediate Similarity NPD4380 Phase 2
0.8114 Intermediate Similarity NPD3818 Discontinued
0.8114 Intermediate Similarity NPD7228 Approved
0.8107 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD7411 Suspended
0.809 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2801 Approved
0.7969 Intermediate Similarity NPD8151 Discontinued
0.7965 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD3817 Phase 2
0.7919 Intermediate Similarity NPD6234 Discontinued
0.7907 Intermediate Similarity NPD3882 Suspended
0.7892 Intermediate Similarity NPD1511 Approved
0.7838 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD6801 Discontinued
0.7798 Intermediate Similarity NPD1512 Approved
0.7764 Intermediate Similarity NPD230 Phase 1
0.7759 Intermediate Similarity NPD3749 Approved
0.7758 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD5402 Approved
0.7738 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7685 Pre-registration
0.7735 Intermediate Similarity NPD6559 Discontinued
0.7735 Intermediate Similarity NPD7240 Approved
0.7733 Intermediate Similarity NPD37 Approved
0.7727 Intermediate Similarity NPD7199 Phase 2
0.7711 Intermediate Similarity NPD3750 Approved
0.7701 Intermediate Similarity NPD4966 Approved
0.7701 Intermediate Similarity NPD4965 Approved
0.7701 Intermediate Similarity NPD4967 Phase 2
0.7697 Intermediate Similarity NPD1549 Phase 2
0.7665 Intermediate Similarity NPD6190 Approved
0.7661 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7458 Discontinued
0.7647 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD4628 Phase 3
0.7593 Intermediate Similarity NPD1613 Approved
0.7593 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6799 Approved
0.7544 Intermediate Similarity NPD5403 Approved
0.7529 Intermediate Similarity NPD2533 Approved
0.7529 Intermediate Similarity NPD2534 Approved
0.7529 Intermediate Similarity NPD2532 Approved
0.7528 Intermediate Similarity NPD8127 Discontinued
0.7527 Intermediate Similarity NPD8150 Discontinued
0.7514 Intermediate Similarity NPD6599 Discontinued
0.75 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1653 Approved
0.75 Intermediate Similarity NPD8166 Discontinued
0.7486 Intermediate Similarity NPD7229 Phase 3
0.7485 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7390 Discontinued
0.7469 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7437 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7437 Intermediate Similarity NPD7783 Phase 2
0.7433 Intermediate Similarity NPD8434 Phase 2
0.7427 Intermediate Similarity NPD5401 Approved
0.7427 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD3751 Discontinued
0.741 Intermediate Similarity NPD3748 Approved
0.741 Intermediate Similarity NPD1510 Phase 2
0.7396 Intermediate Similarity NPD7003 Approved
0.7396 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD3787 Discontinued
0.7371 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD2796 Approved
0.7365 Intermediate Similarity NPD2935 Discontinued
0.7356 Intermediate Similarity NPD3226 Approved
0.7347 Intermediate Similarity NPD7680 Approved
0.7347 Intermediate Similarity NPD7435 Discontinued
0.7346 Intermediate Similarity NPD4908 Phase 1
0.7345 Intermediate Similarity NPD5353 Approved
0.7321 Intermediate Similarity NPD7266 Discontinued
0.732 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD919 Approved
0.731 Intermediate Similarity NPD7871 Phase 2
0.731 Intermediate Similarity NPD7870 Phase 2
0.7273 Intermediate Similarity NPD943 Approved
0.7262 Intermediate Similarity NPD1551 Phase 2
0.7262 Intermediate Similarity NPD6100 Approved
0.7262 Intermediate Similarity NPD6099 Approved
0.7259 Intermediate Similarity NPD7698 Approved
0.7259 Intermediate Similarity NPD7696 Phase 3
0.7259 Intermediate Similarity NPD7697 Approved
0.7253 Intermediate Similarity NPD3926 Phase 2
0.7246 Intermediate Similarity NPD7097 Phase 1
0.7228 Intermediate Similarity NPD7177 Discontinued
0.7222 Intermediate Similarity NPD8319 Approved
0.7222 Intermediate Similarity NPD8320 Phase 1
0.7219 Intermediate Similarity NPD7549 Discontinued
0.7214 Intermediate Similarity NPD7874 Approved
0.7214 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD5953 Discontinued
0.7202 Intermediate Similarity NPD2799 Discontinued
0.72 Intermediate Similarity NPD7701 Phase 2
0.7195 Intermediate Similarity NPD3027 Phase 3
0.7194 Intermediate Similarity NPD6778 Approved
0.7194 Intermediate Similarity NPD6776 Approved
0.7194 Intermediate Similarity NPD6777 Approved
0.7194 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD6782 Approved
0.7194 Intermediate Similarity NPD6779 Approved
0.7194 Intermediate Similarity NPD6780 Approved
0.7194 Intermediate Similarity NPD6781 Approved
0.7189 Intermediate Similarity NPD7286 Phase 2
0.7188 Intermediate Similarity NPD9269 Phase 2
0.7184 Intermediate Similarity NPD6273 Approved
0.7169 Intermediate Similarity NPD1240 Approved
0.716 Intermediate Similarity NPD5405 Approved
0.716 Intermediate Similarity NPD5406 Approved
0.716 Intermediate Similarity NPD5408 Approved
0.716 Intermediate Similarity NPD5404 Approved
0.7158 Intermediate Similarity NPD5242 Approved
0.7152 Intermediate Similarity NPD6798 Discontinued
0.7143 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD1247 Approved
0.7135 Intermediate Similarity NPD2800 Approved
0.7126 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5124 Phase 1
0.7126 Intermediate Similarity NPD6355 Discontinued
0.7126 Intermediate Similarity NPD447 Suspended
0.7118 Intermediate Similarity NPD2346 Discontinued
0.7104 Intermediate Similarity NPD5710 Approved
0.7104 Intermediate Similarity NPD5711 Approved
0.7094 Intermediate Similarity NPD7801 Approved
0.7092 Intermediate Similarity NPD7700 Phase 2
0.7092 Intermediate Similarity NPD7699 Phase 2
0.7083 Intermediate Similarity NPD1607 Approved
0.7066 Intermediate Similarity NPD4060 Phase 1
0.7053 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD2313 Discontinued
0.7048 Intermediate Similarity NPD3764 Approved
0.7035 Intermediate Similarity NPD6674 Discontinued
0.7035 Intermediate Similarity NPD6823 Phase 2
0.7035 Intermediate Similarity NPD1243 Approved
0.7033 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7585 Approved
0.7019 Intermediate Similarity NPD1610 Phase 2
0.7018 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6233 Phase 2
0.7 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6385 Approved
0.6983 Remote Similarity NPD6386 Approved
0.6982 Remote Similarity NPD6651 Approved
0.698 Remote Similarity NPD7583 Approved
0.6975 Remote Similarity NPD1608 Approved
0.697 Remote Similarity NPD9494 Approved
0.6961 Remote Similarity NPD4288 Approved
0.6951 Remote Similarity NPD2797 Approved
0.6946 Remote Similarity NPD3268 Approved
0.6939 Remote Similarity NPD6535 Approved
0.6939 Remote Similarity NPD6534 Approved
0.6937 Remote Similarity NPD9268 Approved
0.6928 Remote Similarity NPD6832 Phase 2
0.6923 Remote Similarity NPD1933 Approved
0.6907 Remote Similarity NPD4287 Approved
0.6904 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6901 Remote Similarity NPD651 Clinical (unspecified phase)
0.6897 Remote Similarity NPD1878 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