Structure

Physi-Chem Properties

Molecular Weight:  954.39
Volume:  919.701
LogP:  5.271
LogD:  2.93
LogS:  -7.398
# Rotatable Bonds:  10
TPSA:  268.05
# H-Bond Aceptor:  19
# H-Bond Donor:  7
# Rings:  9
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.12
Synthetic Accessibility Score:  6.338
Fsp3:  0.633
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.901
MDCK Permeability:  0.00014090974582359195
Pgp-inhibitor:  0.0
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  94.650634765625%
Volume Distribution (VD):  0.274
Pgp-substrate:  6.846213340759277%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.959
CYP2C19-inhibitor:  0.053
CYP2C19-substrate:  0.492
CYP2C9-inhibitor:  0.146
CYP2C9-substrate:  0.04
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.125
CYP3A4-inhibitor:  0.113
CYP3A4-substrate:  0.905

ADMET: Excretion

Clearance (CL):  2.38
Half-life (T1/2):  0.025

ADMET: Toxicity

hERG Blockers:  0.564
Human Hepatotoxicity (H-HT):  0.231
Drug-inuced Liver Injury (DILI):  0.989
AMES Toxicity:  0.797
Rat Oral Acute Toxicity:  0.575
Maximum Recommended Daily Dose:  0.989
Skin Sensitization:  0.902
Carcinogencity:  0.94
Eye Corrosion:  0.003
Eye Irritation:  0.047
Respiratory Toxicity:  0.284

Download Data

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

  Natural Product: NPC224557

Natural Product ID:  NPC224557
Common Name*:   Landomycin W
IUPAC Name:   8-[(2S,4R,5S,6R)-5-[(2S,4R,5R,6R)-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-5-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-1,11-dihydroxy-3-methylbenzo[a]anthracene-7,12-dione
Synonyms:   Landomycin W
Standard InCHIKey:  OTNJSUYMCMBLIA-LJGUJNJOSA-N
Standard InCHI:  InChI=1S/C49H62O19/c1-19-13-25-7-8-26-41(40(25)28(51)14-19)47(58)42-27(50)9-10-33(43(42)46(26)57)65-37-17-31(54)49(24(6)63-37)68-39-18-34(45(56)22(4)61-39)66-35-12-11-32(20(2)59-35)64-36-16-30(53)48(23(5)62-36)67-38-15-29(52)44(55)21(3)60-38/h7-10,13-14,20-24,29-32,34-39,44-45,48-56H,11-12,15-18H2,1-6H3/t20-,21+,22+,23+,24+,29+,30+,31+,32-,34+,35-,36-,37-,38-,39-,44+,45+,48+,49+/m0/s1
SMILES:  Cc1cc(O)c2c(c1)ccc1c2C(=O)c2c(C1=O)c(ccc2O)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@H]1CC[C@@H]([C@@H](O1)C)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1668761
PubChem CID:   50993663
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003415] Angucyclines

*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
NPO19685 Streptomyces cyanogenus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21188999]
NPO19685 Streptomyces cyanogenus Species Streptomycetaceae Bacteria 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 6900.0 nM PMID[494390]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2650.0 nM PMID[494390]

☑ 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 NPC224557 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 NPC292706
0.9881 High Similarity NPC197357
0.9881 High Similarity NPC85316
0.9821 High Similarity NPC58538
0.9702 High Similarity NPC102053
0.9702 High Similarity NPC289876
0.9583 High Similarity NPC203751
0.9471 High Similarity NPC314489
0.9471 High Similarity NPC198893
0.9471 High Similarity NPC232818
0.9412 High Similarity NPC223735
0.9412 High Similarity NPC307754
0.9368 High Similarity NPC87583
0.9353 High Similarity NPC85368
0.9294 High Similarity NPC315619
0.9257 High Similarity NPC241847
0.9176 High Similarity NPC246274
0.9138 High Similarity NPC299149
0.9138 High Similarity NPC277710
0.9138 High Similarity NPC153578
0.9138 High Similarity NPC114257
0.9133 High Similarity NPC66820
0.9133 High Similarity NPC92403
0.9133 High Similarity NPC76112
0.9133 High Similarity NPC170018
0.9118 High Similarity NPC63470
0.9107 High Similarity NPC278329
0.9107 High Similarity NPC101116
0.9107 High Similarity NPC146837
0.9107 High Similarity NPC212099
0.9075 High Similarity NPC186800
0.9075 High Similarity NPC470667
0.9034 High Similarity NPC476203
0.9023 High Similarity NPC475246
0.9023 High Similarity NPC46958
0.9 High Similarity NPC178281
0.8977 High Similarity NPC475161
0.8977 High Similarity NPC477860
0.8966 High Similarity NPC3718
0.8962 High Similarity NPC131405
0.892 High Similarity NPC72783
0.8914 High Similarity NPC176246
0.8908 High Similarity NPC199357
0.8895 High Similarity NPC314459
0.8895 High Similarity NPC470199
0.8882 High Similarity NPC216752
0.887 High Similarity NPC164047
0.887 High Similarity NPC470453
0.887 High Similarity NPC470448
0.887 High Similarity NPC470452
0.8851 High Similarity NPC111536
0.8851 High Similarity NPC30432
0.8851 High Similarity NPC5029
0.8851 High Similarity NPC76128
0.8851 High Similarity NPC271385
0.884 High Similarity NPC264302
0.8833 High Similarity NPC473618
0.8833 High Similarity NPC205721
0.883 High Similarity NPC17432
0.8827 High Similarity NPC475220
0.8827 High Similarity NPC229817
0.8827 High Similarity NPC475352
0.8827 High Similarity NPC473686
0.8827 High Similarity NPC221140
0.8817 High Similarity NPC53139
0.8814 High Similarity NPC84494
0.8814 High Similarity NPC245059
0.88 High Similarity NPC213052
0.88 High Similarity NPC65118
0.8798 High Similarity NPC314687
0.8798 High Similarity NPC470198
0.8798 High Similarity NPC470193
0.8798 High Similarity NPC316274
0.8798 High Similarity NPC470196
0.8798 High Similarity NPC470197
0.8798 High Similarity NPC470200
0.8798 High Similarity NPC470194
0.8798 High Similarity NPC470195
0.8798 High Similarity NPC282474
0.8785 High Similarity NPC314672
0.8779 High Similarity NPC478020
0.8779 High Similarity NPC478022
0.8778 High Similarity NPC105591
0.8778 High Similarity NPC179947
0.8772 High Similarity NPC187934
0.8772 High Similarity NPC97637
0.875 High Similarity NPC68381
0.8743 High Similarity NPC183441
0.8736 High Similarity NPC222455
0.8715 High Similarity NPC478001
0.8715 High Similarity NPC293227
0.8715 High Similarity NPC473631
0.8715 High Similarity NPC473717
0.8715 High Similarity NPC475662
0.8708 High Similarity NPC187441
0.8708 High Similarity NPC283980
0.8701 High Similarity NPC475233
0.8693 High Similarity NPC168789
0.8678 High Similarity NPC103633
0.8671 High Similarity NPC99216
0.8667 High Similarity NPC318119
0.8647 High Similarity NPC177742
0.8644 High Similarity NPC470454
0.8644 High Similarity NPC63105
0.8644 High Similarity NPC70862
0.8644 High Similarity NPC199533
0.8636 High Similarity NPC288152
0.8636 High Similarity NPC137871
0.8636 High Similarity NPC9002
0.8636 High Similarity NPC257011
0.8634 High Similarity NPC48474
0.8629 High Similarity NPC259905
0.8621 High Similarity NPC178851
0.8621 High Similarity NPC70441
0.8611 High Similarity NPC313452
0.8611 High Similarity NPC321916
0.8605 High Similarity NPC132737
0.8605 High Similarity NPC73148
0.8603 High Similarity NPC212290
0.8603 High Similarity NPC473895
0.8588 High Similarity NPC98776
0.8588 High Similarity NPC470438
0.858 High Similarity NPC52598
0.858 High Similarity NPC199079
0.858 High Similarity NPC313304
0.858 High Similarity NPC298778
0.858 High Similarity NPC478021
0.858 High Similarity NPC210808
0.8579 High Similarity NPC472720
0.8579 High Similarity NPC160543
0.8579 High Similarity NPC93065
0.8579 High Similarity NPC472721
0.8579 High Similarity NPC469652
0.8579 High Similarity NPC472724
0.8579 High Similarity NPC187632
0.8579 High Similarity NPC31208
0.8571 High Similarity NPC65489
0.8564 High Similarity NPC49690
0.8564 High Similarity NPC231254
0.8563 High Similarity NPC11608
0.8563 High Similarity NPC297404
0.8556 High Similarity NPC315221
0.8556 High Similarity NPC174140
0.8547 High Similarity NPC83331
0.8547 High Similarity NPC475261
0.8547 High Similarity NPC470581
0.8547 High Similarity NPC470582
0.8547 High Similarity NPC115447
0.8547 High Similarity NPC47191
0.8547 High Similarity NPC471789
0.8541 High Similarity NPC477082
0.8539 High Similarity NPC102028
0.8539 High Similarity NPC146803
0.8538 High Similarity NPC208651
0.8538 High Similarity NPC206641
0.8531 High Similarity NPC294501
0.8531 High Similarity NPC478002
0.8525 High Similarity NPC158214
0.8525 High Similarity NPC240200
0.8525 High Similarity NPC223534
0.8525 High Similarity NPC477083
0.8525 High Similarity NPC477081
0.8525 High Similarity NPC290289
0.8523 High Similarity NPC175477
0.8516 High Similarity NPC261623
0.8516 High Similarity NPC111490
0.8508 High Similarity NPC132111
0.85 High Similarity NPC185275
0.8483 Intermediate Similarity NPC472054
0.848 Intermediate Similarity NPC283480
0.848 Intermediate Similarity NPC148323
0.8475 Intermediate Similarity NPC280385
0.8475 Intermediate Similarity NPC76047
0.847 Intermediate Similarity NPC469649
0.847 Intermediate Similarity NPC260521
0.8462 Intermediate Similarity NPC75574
0.8457 Intermediate Similarity NPC478026
0.8457 Intermediate Similarity NPC280923
0.8448 Intermediate Similarity NPC61594
0.8448 Intermediate Similarity NPC56735
0.8448 Intermediate Similarity NPC190450
0.8444 Intermediate Similarity NPC472387
0.8444 Intermediate Similarity NPC265380
0.8444 Intermediate Similarity NPC478000
0.8444 Intermediate Similarity NPC266513
0.8441 Intermediate Similarity NPC316412
0.8441 Intermediate Similarity NPC315351
0.8439 Intermediate Similarity NPC328093
0.8436 Intermediate Similarity NPC470583
0.8436 Intermediate Similarity NPC474345
0.8436 Intermediate Similarity NPC142996
0.8436 Intermediate Similarity NPC19056
0.8432 Intermediate Similarity NPC40078
0.8432 Intermediate Similarity NPC321046
0.8432 Intermediate Similarity NPC471091
0.8432 Intermediate Similarity NPC97924
0.8427 Intermediate Similarity NPC156977
0.8427 Intermediate Similarity NPC267254
0.8427 Intermediate Similarity NPC270027
0.8427 Intermediate Similarity NPC301683

  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 NPC224557 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
0.9133 High Similarity NPD8312 Approved
0.9133 High Similarity NPD8313 Approved
0.8883 High Similarity NPD7879 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8413 Intermediate Similarity NPD7697 Approved
0.8413 Intermediate Similarity NPD7698 Approved
0.8413 Intermediate Similarity NPD7696 Phase 3
0.8394 Intermediate Similarity NPD7783 Phase 2
0.8394 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.8368 Intermediate Similarity NPD7870 Phase 2
0.8368 Intermediate Similarity NPD7871 Phase 2
0.8351 Intermediate Similarity NPD6778 Approved
0.8351 Intermediate Similarity NPD6776 Approved
0.8351 Intermediate Similarity NPD6781 Approved
0.8351 Intermediate Similarity NPD6779 Approved
0.8351 Intermediate Similarity NPD6782 Approved
0.8351 Intermediate Similarity NPD6780 Approved
0.8351 Intermediate Similarity NPD6777 Approved
0.8333 Intermediate Similarity NPD7701 Phase 2
0.8316 Intermediate Similarity NPD7435 Discontinued
0.8315 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.829 Intermediate Similarity NPD8151 Discontinued
0.8286 Intermediate Similarity NPD6959 Discontinued
0.8268 Intermediate Similarity NPD7074 Phase 3
0.8245 Intermediate Similarity NPD7700 Phase 2
0.8245 Intermediate Similarity NPD7699 Phase 2
0.8177 Intermediate Similarity NPD6559 Discontinued
0.8167 Intermediate Similarity NPD7472 Approved
0.8154 Intermediate Similarity NPD7874 Approved
0.8154 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.815 Intermediate Similarity NPD8455 Phase 2
0.8132 Intermediate Similarity NPD7808 Phase 3
0.8114 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD7801 Approved
0.8111 Intermediate Similarity NPD7054 Approved
0.8085 Intermediate Similarity NPD6535 Approved
0.8085 Intermediate Similarity NPD6534 Approved
0.8077 Intermediate Similarity NPD7251 Discontinued
0.8073 Intermediate Similarity NPD6823 Phase 2
0.8032 Intermediate Similarity NPD6213 Phase 3
0.8032 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.8032 Intermediate Similarity NPD6212 Phase 3
0.8022 Intermediate Similarity NPD6797 Phase 2
0.8011 Intermediate Similarity NPD5844 Phase 1
0.799 Intermediate Similarity NPD8320 Phase 1
0.799 Intermediate Similarity NPD8319 Approved
0.7919 Intermediate Similarity NPD3226 Approved
0.7901 Intermediate Similarity NPD7473 Discontinued
0.7861 Intermediate Similarity NPD8150 Discontinued
0.7857 Intermediate Similarity NPD3751 Discontinued
0.7857 Intermediate Similarity NPD3818 Discontinued
0.7845 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD6166 Phase 2
0.7845 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD7819 Suspended
0.7838 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD6232 Discontinued
0.7797 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD4380 Phase 2
0.7747 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD3787 Discontinued
0.773 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD7075 Discontinued
0.764 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD5494 Approved
0.7614 Intermediate Similarity NPD7458 Discontinued
0.7614 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD5402 Approved
0.7588 Intermediate Similarity NPD2346 Discontinued
0.7571 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD8059 Phase 3
0.7556 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD7768 Phase 2
0.7542 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD7411 Suspended
0.7526 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD8434 Phase 2
0.7486 Intermediate Similarity NPD1934 Approved
0.7473 Intermediate Similarity NPD7228 Approved
0.7444 Intermediate Similarity NPD2801 Approved
0.7389 Intermediate Similarity NPD6801 Discontinued
0.7386 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD4628 Phase 3
0.733 Intermediate Similarity NPD7390 Discontinued
0.7322 Intermediate Similarity NPD3749 Approved
0.7316 Intermediate Similarity NPD7685 Pre-registration
0.7299 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD7177 Discontinued
0.7286 Intermediate Similarity NPD8285 Discontinued
0.7253 Intermediate Similarity NPD1465 Phase 2
0.7241 Intermediate Similarity NPD1549 Phase 2
0.7225 Intermediate Similarity NPD7240 Approved
0.7225 Intermediate Similarity NPD2935 Discontinued
0.7207 Intermediate Similarity NPD5403 Approved
0.72 Intermediate Similarity NPD6674 Discontinued
0.7191 Intermediate Similarity NPD2532 Approved
0.7191 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD2534 Approved
0.7191 Intermediate Similarity NPD2533 Approved
0.7184 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6599 Discontinued
0.7174 Intermediate Similarity NPD3882 Suspended
0.7159 Intermediate Similarity NPD7003 Approved
0.7126 Intermediate Similarity NPD5405 Approved
0.7126 Intermediate Similarity NPD5406 Approved
0.7126 Intermediate Similarity NPD5404 Approved
0.7126 Intermediate Similarity NPD5408 Approved
0.7122 Intermediate Similarity NPD7584 Approved
0.712 Intermediate Similarity NPD3817 Phase 2
0.7112 Intermediate Similarity NPD7199 Phase 2
0.7104 Intermediate Similarity NPD6844 Discontinued
0.7104 Intermediate Similarity NPD37 Approved
0.7097 Intermediate Similarity NPD6234 Discontinued
0.7095 Intermediate Similarity NPD5401 Approved
0.7086 Intermediate Similarity NPD2344 Approved
0.7081 Intermediate Similarity NPD4966 Approved
0.7081 Intermediate Similarity NPD4967 Phase 2
0.7081 Intermediate Similarity NPD4965 Approved
0.7069 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7930 Approved
0.7039 Intermediate Similarity NPD1511 Approved
0.7039 Intermediate Similarity NPD6799 Approved
0.7029 Intermediate Similarity NPD2796 Approved
0.7024 Intermediate Similarity NPD1470 Approved
0.7018 Intermediate Similarity NPD2313 Discontinued
0.7016 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7266 Discontinued
0.6971 Remote Similarity NPD1510 Phase 2
0.6971 Remote Similarity NPD2799 Discontinued
0.6966 Remote Similarity NPD3750 Approved
0.6961 Remote Similarity NPD6273 Approved
0.6961 Remote Similarity NPD1512 Approved
0.6954 Remote Similarity NPD1607 Approved
0.6947 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6932 Remote Similarity NPD1551 Phase 2
0.6932 Remote Similarity NPD6099 Approved
0.6932 Remote Similarity NPD6100 Approved
0.6931 Remote Similarity NPD8127 Discontinued
0.6927 Remote Similarity NPD2309 Approved
0.6923 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7097 Phase 1
0.6908 Remote Similarity NPD7999 Approved
0.6893 Remote Similarity NPD7680 Approved
0.6893 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6885 Remote Similarity NPD1653 Approved
0.6882 Remote Similarity NPD2798 Approved
0.6872 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6866 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6859 Remote Similarity NPD3926 Phase 2
0.6854 Remote Similarity NPD970 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1247 Approved
0.6839 Remote Similarity NPD1240 Approved
0.6839 Remote Similarity NPD7799 Discontinued
0.6829 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6821 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6821 Remote Similarity NPD5953 Discontinued
0.6821 Remote Similarity NPD7985 Registered
0.6816 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6806 Remote Similarity NPD5710 Approved
0.6806 Remote Similarity NPD5711 Approved
0.6806 Remote Similarity NPD7229 Phase 3
0.6802 Remote Similarity NPD6832 Phase 2
0.68 Remote Similarity NPD1933 Approved
0.6791 Remote Similarity NPD5761 Phase 2
0.6791 Remote Similarity NPD5760 Phase 2
0.6786 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1201 Approved
0.678 Remote Similarity NPD7237 Clinical (unspecified phase)
0.678 Remote Similarity NPD7033 Discontinued
0.6763 Remote Similarity NPD4625 Phase 3
0.6762 Remote Similarity NPD7585 Approved
0.6744 Remote Similarity NPD8404 Phase 2
0.674 Remote Similarity NPD6190 Approved
0.6739 Remote Similarity NPD920 Approved
0.6722 Remote Similarity NPD2800 Approved
0.6718 Remote Similarity NPD7286 Phase 2
0.6714 Remote Similarity NPD7583 Approved
0.6705 Remote Similarity NPD447 Suspended
0.6704 Remote Similarity NPD1471 Phase 3
0.6686 Remote Similarity NPD1091 Approved
0.6686 Remote Similarity NPD6233 Phase 2
0.6685 Remote Similarity NPD8166 Discontinued
0.6685 Remote Similarity NPD3748 Approved
0.6682 Remote Similarity NPD8067 Phase 3
0.6667 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6649 Remote Similarity NPD919 Approved
0.6648 Remote Similarity NPD2438 Suspended
0.6648 Remote Similarity NPD4060 Phase 1
0.663 Remote Similarity NPD642 Clinical (unspecified phase)
0.6629 Remote Similarity NPD3764 Approved
0.6629 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6798 Discontinued

  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