Structure

Physi-Chem Properties

Molecular Weight:  850.83
Volume:  601.558
LogP:  3.455
LogD:  1.595
LogS:  -3.237
# Rotatable Bonds:  12
TPSA:  161.85
# H-Bond Aceptor:  12
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.171
Synthetic Accessibility Score:  5.545
Fsp3:  0.37
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.186
MDCK Permeability:  1.7197093256982043e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.749
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.052
Plasma Protein Binding (PPB):  96.54279327392578%
Volume Distribution (VD):  1.279
Pgp-substrate:  4.9616379737854%

ADMET: Metabolism

CYP1A2-inhibitor:  0.087
CYP1A2-substrate:  0.502
CYP2C19-inhibitor:  0.704
CYP2C19-substrate:  0.586
CYP2C9-inhibitor:  0.597
CYP2C9-substrate:  0.054
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.109
CYP3A4-inhibitor:  0.925
CYP3A4-substrate:  0.841

ADMET: Excretion

Clearance (CL):  1.002
Half-life (T1/2):  0.129

ADMET: Toxicity

hERG Blockers:  0.122
Human Hepatotoxicity (H-HT):  0.266
Drug-inuced Liver Injury (DILI):  0.83
AMES Toxicity:  0.435
Rat Oral Acute Toxicity:  0.356
Maximum Recommended Daily Dose:  0.97
Skin Sensitization:  0.372
Carcinogencity:  0.927
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.941

Download Data

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

  Natural Product: NPC470746

Natural Product ID:  NPC470746
Common Name*:   19-Hydroxypsammaplysin E
IUPAC Name:   (4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[(2,5-dioxocyclopent-3-en-1-ylidene)methylamino]-1-hydroxyethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:   19-Hydroxypsammaplysin E
Standard InCHIKey:  ALQMQVUOKZVSGT-SLCPUWTHSA-N
Standard InCHI:  InChI=1S/C27H25Br4N3O9/c1-40-23-17(30)9-27(42-12-18(23)31)25(38)22(34-43-27)26(39)33-5-2-6-41-24-15(28)7-13(8-16(24)29)21(37)11-32-10-14-19(35)3-4-20(14)36/h3-4,7-8,10,12,21,25,32,37-38H,2,5-6,9,11H2,1H3,(H,33,39)/t21?,25-,27-/m0/s1
SMILES:  COC1=C(Br)C[C@]2(OC=C1Br)ON=C([C@@H]2O)C(=O)NCCCOc1c(Br)cc(cc1Br)C(CNC=C1C(=O)C=CC1=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2208225
PubChem CID:   71459809
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002341] Phenol ethers

*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
NPO32476 aplysinella strongylata Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[23215158]

☑ 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 6400.0 nM PMID[488850]

☑ 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 NPC470746 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 NPC471336
0.962 High Similarity NPC123140
0.9348 High Similarity NPC475843
0.933 High Similarity NPC471335
0.9293 High Similarity NPC471338
0.9293 High Similarity NPC474678
0.9101 High Similarity NPC471337
0.8969 High Similarity NPC471339
0.8967 High Similarity NPC8093
0.8967 High Similarity NPC121571
0.837 Intermediate Similarity NPC477255
0.8272 Intermediate Similarity NPC77435
0.8272 Intermediate Similarity NPC259071
0.8168 Intermediate Similarity NPC477254
0.8163 Intermediate Similarity NPC202866
0.8112 Intermediate Similarity NPC227953
0.7857 Intermediate Similarity NPC174607
0.7817 Intermediate Similarity NPC147847
0.7473 Intermediate Similarity NPC469711
0.7354 Intermediate Similarity NPC156311
0.71 Intermediate Similarity NPC143450
0.7083 Intermediate Similarity NPC233926
0.7053 Intermediate Similarity NPC258222
0.7016 Intermediate Similarity NPC47672
0.7011 Intermediate Similarity NPC474673
0.6971 Remote Similarity NPC248822
0.6911 Remote Similarity NPC76412
0.6895 Remote Similarity NPC71629
0.6882 Remote Similarity NPC128877
0.6875 Remote Similarity NPC109968
0.6869 Remote Similarity NPC473450
0.6862 Remote Similarity NPC308571
0.6827 Remote Similarity NPC475658
0.6827 Remote Similarity NPC473892
0.6806 Remote Similarity NPC296085
0.6794 Remote Similarity NPC82741
0.6794 Remote Similarity NPC473409
0.6794 Remote Similarity NPC141405
0.6737 Remote Similarity NPC78530
0.6714 Remote Similarity NPC246591
0.6699 Remote Similarity NPC49172
0.6683 Remote Similarity NPC471568
0.6683 Remote Similarity NPC473693
0.6682 Remote Similarity NPC214368
0.6667 Remote Similarity NPC471591
0.6651 Remote Similarity NPC469731
0.6649 Remote Similarity NPC135349
0.6636 Remote Similarity NPC469721
0.6636 Remote Similarity NPC80514
0.6633 Remote Similarity NPC235033
0.6633 Remote Similarity NPC73132
0.6633 Remote Similarity NPC471235
0.6632 Remote Similarity NPC474128
0.6631 Remote Similarity NPC470471
0.662 Remote Similarity NPC102245
0.6617 Remote Similarity NPC469479
0.6601 Remote Similarity NPC196091
0.6589 Remote Similarity NPC65714
0.6588 Remote Similarity NPC96275
0.6578 Remote Similarity NPC326027
0.6571 Remote Similarity NPC299806
0.6562 Remote Similarity NPC470472
0.6562 Remote Similarity NPC326333
0.6561 Remote Similarity NPC470470
0.6559 Remote Similarity NPC97870
0.6559 Remote Similarity NPC307123
0.6559 Remote Similarity NPC247018
0.6552 Remote Similarity NPC186617
0.6542 Remote Similarity NPC64066
0.6526 Remote Similarity NPC283207
0.6507 Remote Similarity NPC475396
0.6498 Remote Similarity NPC471592
0.6476 Remote Similarity NPC301941
0.6476 Remote Similarity NPC214188
0.6476 Remote Similarity NPC74618
0.6471 Remote Similarity NPC469505
0.6442 Remote Similarity NPC469979
0.6429 Remote Similarity NPC324081
0.6411 Remote Similarity NPC110454
0.6411 Remote Similarity NPC298981
0.6411 Remote Similarity NPC207819
0.6411 Remote Similarity NPC126128
0.6411 Remote Similarity NPC473462
0.6404 Remote Similarity NPC158900
0.6393 Remote Similarity NPC477550
0.6393 Remote Similarity NPC323662
0.6393 Remote Similarity NPC477552
0.6381 Remote Similarity NPC290534
0.6373 Remote Similarity NPC204546
0.6372 Remote Similarity NPC230539
0.6364 Remote Similarity NPC123859
0.6364 Remote Similarity NPC226001
0.6359 Remote Similarity NPC272463
0.6355 Remote Similarity NPC144823
0.6355 Remote Similarity NPC80337
0.6338 Remote Similarity NPC315542
0.6335 Remote Similarity NPC477551
0.6335 Remote Similarity NPC242728
0.6333 Remote Similarity NPC475421
0.6324 Remote Similarity NPC110131
0.6321 Remote Similarity NPC470112
0.6321 Remote Similarity NPC470903
0.6321 Remote Similarity NPC167763
0.6316 Remote Similarity NPC225130
0.6308 Remote Similarity NPC276120
0.6302 Remote Similarity NPC213471
0.63 Remote Similarity NPC470710
0.63 Remote Similarity NPC123011
0.63 Remote Similarity NPC197125
0.63 Remote Similarity NPC256689
0.6293 Remote Similarity NPC254700
0.6284 Remote Similarity NPC328763
0.6273 Remote Similarity NPC144314
0.6272 Remote Similarity NPC92235
0.6268 Remote Similarity NPC471165
0.6263 Remote Similarity NPC20755
0.6262 Remote Similarity NPC209463
0.6261 Remote Similarity NPC476661
0.6256 Remote Similarity NPC476194
0.6256 Remote Similarity NPC471203
0.6244 Remote Similarity NPC50548
0.6244 Remote Similarity NPC472923
0.6238 Remote Similarity NPC56635
0.6237 Remote Similarity NPC320242
0.6234 Remote Similarity NPC67658
0.6233 Remote Similarity NPC476662
0.623 Remote Similarity NPC470441
0.6227 Remote Similarity NPC149962
0.6211 Remote Similarity NPC474753
0.6205 Remote Similarity NPC311357
0.6199 Remote Similarity NPC281629
0.6193 Remote Similarity NPC477526
0.6186 Remote Similarity NPC138083
0.6186 Remote Similarity NPC40321
0.6182 Remote Similarity NPC184933
0.6182 Remote Similarity NPC59827
0.6178 Remote Similarity NPC132308
0.6178 Remote Similarity NPC169766
0.6175 Remote Similarity NPC124626
0.6172 Remote Similarity NPC328494
0.6172 Remote Similarity NPC89831
0.6166 Remote Similarity NPC473055
0.6166 Remote Similarity NPC473052
0.6165 Remote Similarity NPC63931
0.6158 Remote Similarity NPC475735
0.6158 Remote Similarity NPC473724
0.6157 Remote Similarity NPC14390
0.615 Remote Similarity NPC14339
0.6146 Remote Similarity NPC303993
0.6144 Remote Similarity NPC175150
0.6144 Remote Similarity NPC243633
0.6143 Remote Similarity NPC248670
0.6134 Remote Similarity NPC322526
0.6126 Remote Similarity NPC470392
0.6116 Remote Similarity NPC471031
0.6116 Remote Similarity NPC469689
0.6114 Remote Similarity NPC477160
0.6114 Remote Similarity NPC196708
0.6111 Remote Similarity NPC235194
0.6108 Remote Similarity NPC471073
0.6108 Remote Similarity NPC270811
0.6106 Remote Similarity NPC473502
0.6105 Remote Similarity NPC474091
0.6105 Remote Similarity NPC474087
0.6103 Remote Similarity NPC475615
0.6101 Remote Similarity NPC471395
0.6099 Remote Similarity NPC477527
0.6089 Remote Similarity NPC156055
0.6089 Remote Similarity NPC39431
0.6085 Remote Similarity NPC477115
0.608 Remote Similarity NPC313414
0.6079 Remote Similarity NPC81845
0.6075 Remote Similarity NPC32064
0.6073 Remote Similarity NPC29531
0.6073 Remote Similarity NPC11449
0.6071 Remote Similarity NPC470709
0.6066 Remote Similarity NPC273755
0.6064 Remote Similarity NPC141739
0.6064 Remote Similarity NPC136112
0.6059 Remote Similarity NPC476268
0.6059 Remote Similarity NPC244509
0.6058 Remote Similarity NPC71205
0.6055 Remote Similarity NPC94862
0.6055 Remote Similarity NPC34780
0.6051 Remote Similarity NPC471201
0.6051 Remote Similarity NPC197045
0.605 Remote Similarity NPC132771
0.6049 Remote Similarity NPC319320
0.6049 Remote Similarity NPC287757
0.6048 Remote Similarity NPC46009
0.6047 Remote Similarity NPC28368
0.6045 Remote Similarity NPC473407
0.6045 Remote Similarity NPC473378
0.6043 Remote Similarity NPC293347
0.6041 Remote Similarity NPC314702
0.6038 Remote Similarity NPC26108
0.6038 Remote Similarity NPC164608
0.603 Remote Similarity NPC119569
0.6027 Remote Similarity NPC470951
0.6026 Remote Similarity NPC257266

  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 NPC470746 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
0.6748 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6619 Remote Similarity NPD3153 Approved
0.6619 Remote Similarity NPD3154 Approved
0.6614 Remote Similarity NPD2240 Approved
0.6614 Remote Similarity NPD2239 Approved
0.6559 Remote Similarity NPD1423 Approved
0.6513 Remote Similarity NPD3536 Discontinued
0.6465 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6456 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6452 Remote Similarity NPD3180 Approved
0.6452 Remote Similarity NPD3179 Approved
0.6439 Remote Similarity NPD7608 Discontinued
0.6429 Remote Similarity NPD4662 Approved
0.6429 Remote Similarity NPD4661 Approved
0.6425 Remote Similarity NPD6863 Phase 2
0.6425 Remote Similarity NPD2976 Clinical (unspecified phase)
0.64 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6383 Remote Similarity NPD8059 Phase 3
0.6383 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6377 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6359 Remote Similarity NPD4466 Phase 1
0.6355 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6351 Remote Similarity NPD7038 Approved
0.6351 Remote Similarity NPD7039 Approved
0.6332 Remote Similarity NPD3687 Approved
0.6332 Remote Similarity NPD3686 Approved
0.6324 Remote Similarity NPD8031 Discontinued
0.6305 Remote Similarity NPD7318 Phase 3
0.63 Remote Similarity NPD2649 Approved
0.63 Remote Similarity NPD2651 Approved
0.629 Remote Similarity NPD7811 Phase 3
0.629 Remote Similarity NPD7810 Phase 3
0.6283 Remote Similarity NPD3052 Approved
0.6283 Remote Similarity NPD3054 Approved
0.6281 Remote Similarity NPD7131 Phase 3
0.6269 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6267 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6256 Remote Similarity NPD7256 Discontinued
0.6244 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6237 Remote Similarity NPD1819 Approved
0.6237 Remote Similarity NPD1817 Approved
0.6237 Remote Similarity NPD1818 Approved
0.6237 Remote Similarity NPD1820 Approved
0.6232 Remote Similarity NPD7485 Phase 3
0.6232 Remote Similarity NPD7484 Phase 3
0.6221 Remote Similarity NPD4258 Approved
0.6221 Remote Similarity NPD4259 Approved
0.6207 Remote Similarity NPD7317 Phase 3
0.6197 Remote Similarity NPD1298 Discontinued
0.619 Remote Similarity NPD3165 Approved
0.619 Remote Similarity NPD3167 Approved
0.619 Remote Similarity NPD3164 Approved
0.619 Remote Similarity NPD3166 Approved
0.6181 Remote Similarity NPD3985 Discontinued
0.6176 Remote Similarity NPD7972 Discontinued
0.6167 Remote Similarity NPD7584 Approved
0.6161 Remote Similarity NPD2163 Approved
0.6161 Remote Similarity NPD7476 Discontinued
0.6158 Remote Similarity NPD6072 Discontinued
0.6158 Remote Similarity NPD6677 Suspended
0.6147 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6143 Remote Similarity NPD7565 Approved
0.6135 Remote Similarity NPD6315 Phase 2
0.6111 Remote Similarity NPD2677 Approved
0.6106 Remote Similarity NPD4666 Phase 3
0.6105 Remote Similarity NPD9718 Approved
0.6103 Remote Similarity NPD1725 Approved
0.61 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6098 Remote Similarity NPD5773 Approved
0.6098 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6098 Remote Similarity NPD5772 Approved
0.6095 Remote Similarity NPD2215 Approved
0.6095 Remote Similarity NPD2216 Approved
0.6095 Remote Similarity NPD2388 Discontinued
0.6091 Remote Similarity NPD4162 Approved
0.6078 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6073 Remote Similarity NPD3056 Clinical (unspecified phase)
0.607 Remote Similarity NPD1975 Clinical (unspecified phase)
0.607 Remote Similarity NPD2186 Approved
0.6064 Remote Similarity NPD1770 Clinical (unspecified phase)
0.6064 Remote Similarity NPD1794 Approved
0.6058 Remote Similarity NPD5709 Phase 3
0.6049 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6045 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6042 Remote Similarity NPD3162 Approved
0.6042 Remote Similarity NPD3163 Approved
0.604 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6029 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6029 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6028 Remote Similarity NPD5557 Phase 1
0.6026 Remote Similarity NPD7583 Approved
0.602 Remote Similarity NPD3157 Approved
0.602 Remote Similarity NPD6419 Discontinued
0.602 Remote Similarity NPD3158 Phase 1
0.6019 Remote Similarity NPD2978 Approved
0.6019 Remote Similarity NPD2977 Approved
0.601 Remote Similarity NPD3060 Approved
0.601 Remote Similarity NPD2460 Phase 3
0.601 Remote Similarity NPD2458 Approved
0.601 Remote Similarity NPD2459 Approved
0.6009 Remote Similarity NPD7880 Clinical (unspecified phase)
0.6009 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6009 Remote Similarity NPD6620 Discovery
0.6 Remote Similarity NPD7585 Approved
0.5991 Remote Similarity NPD6823 Phase 2
0.599 Remote Similarity NPD2183 Approved
0.599 Remote Similarity NPD2184 Approved
0.599 Remote Similarity NPD2296 Approved
0.5982 Remote Similarity NPD6793 Clinical (unspecified phase)
0.5982 Remote Similarity NPD3857 Clinical (unspecified phase)
0.5971 Remote Similarity NPD5356 Approved
0.5971 Remote Similarity NPD5355 Approved
0.597 Remote Similarity NPD1774 Approved
0.5964 Remote Similarity NPD4413 Clinical (unspecified phase)
0.5964 Remote Similarity NPD3473 Clinical (unspecified phase)
0.5962 Remote Similarity NPD3366 Approved
0.5959 Remote Similarity NPD5745 Approved
0.5955 Remote Similarity NPD4157 Discontinued
0.5952 Remote Similarity NPD2904 Discontinued
0.5945 Remote Similarity NPD4419 Clinical (unspecified phase)
0.5943 Remote Similarity NPD644 Clinical (unspecified phase)
0.5943 Remote Similarity NPD5137 Approved
0.5941 Remote Similarity NPD2874 Phase 2
0.5939 Remote Similarity NPD7891 Discontinued
0.5938 Remote Similarity NPD5163 Phase 2
0.5935 Remote Similarity NPD3909 Discontinued
0.5935 Remote Similarity NPD5940 Clinical (unspecified phase)
0.5931 Remote Similarity NPD4210 Discontinued
0.5928 Remote Similarity NPD3597 Clinical (unspecified phase)
0.5917 Remote Similarity NPD7547 Clinical (unspecified phase)
0.5916 Remote Similarity NPD2250 Discontinued
0.5915 Remote Similarity NPD7930 Approved
0.5913 Remote Similarity NPD7999 Approved
0.5911 Remote Similarity NPD7527 Clinical (unspecified phase)
0.5911 Remote Similarity NPD52 Approved
0.5911 Remote Similarity NPD7526 Approved
0.5909 Remote Similarity NPD7978 Discontinued
0.5909 Remote Similarity NPD8469 Approved
0.5907 Remote Similarity NPD6042 Phase 2
0.5907 Remote Similarity NPD42 Phase 2
0.5905 Remote Similarity NPD6862 Phase 2
0.5903 Remote Similarity NPD6519 Phase 2
0.5903 Remote Similarity NPD5457 Discontinued
0.5903 Remote Similarity NPD7501 Clinical (unspecified phase)
0.5902 Remote Similarity NPD3866 Clinical (unspecified phase)
0.5897 Remote Similarity NPD7827 Phase 1
0.589 Remote Similarity NPD6853 Approved
0.589 Remote Similarity NPD6851 Approved
0.5888 Remote Similarity NPD5605 Phase 2
0.5887 Remote Similarity NPD6973 Clinical (unspecified phase)
0.5882 Remote Similarity NPD3490 Discontinued
0.5879 Remote Similarity NPD6681 Discovery
0.5879 Remote Similarity NPD7596 Clinical (unspecified phase)
0.5879 Remote Similarity NPD7153 Discontinued
0.5874 Remote Similarity NPD7296 Approved
0.5874 Remote Similarity NPD3269 Clinical (unspecified phase)
0.5872 Remote Similarity NPD3936 Clinical (unspecified phase)
0.5868 Remote Similarity NPD3263 Phase 3
0.5865 Remote Similarity NPD6668 Clinical (unspecified phase)
0.5862 Remote Similarity NPD3146 Approved
0.5862 Remote Similarity NPD3688 Clinical (unspecified phase)
0.5861 Remote Similarity NPD4898 Clinical (unspecified phase)
0.5859 Remote Similarity NPD2161 Phase 2
0.5857 Remote Similarity NPD1307 Phase 2
0.5857 Remote Similarity NPD1309 Phase 2
0.5855 Remote Similarity NPD7801 Approved
0.5855 Remote Similarity NPD5746 Approved
0.5855 Remote Similarity NPD3136 Phase 2
0.5854 Remote Similarity NPD4124 Clinical (unspecified phase)
0.5853 Remote Similarity NPD3823 Discontinued
0.5853 Remote Similarity NPD6297 Approved
0.5852 Remote Similarity NPD8163 Clinical (unspecified phase)
0.5852 Remote Similarity NPD8162 Phase 2
0.585 Remote Similarity NPD5062 Approved
0.585 Remote Similarity NPD5061 Approved
0.585 Remote Similarity NPD4237 Approved
0.585 Remote Similarity NPD4236 Phase 3
0.5849 Remote Similarity NPD2247 Approved
0.5849 Remote Similarity NPD2249 Approved
0.5845 Remote Similarity NPD6386 Approved
0.5845 Remote Similarity NPD6385 Approved
0.5842 Remote Similarity NPD5295 Discontinued
0.5842 Remote Similarity NPD3122 Phase 3
0.5841 Remote Similarity NPD7784 Clinical (unspecified phase)
0.5837 Remote Similarity NPD3556 Approved
0.5837 Remote Similarity NPD3558 Approved
0.5837 Remote Similarity NPD3559 Clinical (unspecified phase)
0.5837 Remote Similarity NPD3557 Approved
0.5837 Remote Similarity NPD3560 Approved
0.5833 Remote Similarity NPD7613 Discontinued
0.5833 Remote Similarity NPD4186 Clinical (unspecified phase)
0.5829 Remote Similarity NPD3656 Approved
0.5826 Remote Similarity NPD3802 Phase 3
0.5818 Remote Similarity NPD5946 Clinical (unspecified phase)
0.5817 Remote Similarity NPD6844 Discontinued
0.5813 Remote Similarity NPD6087 Phase 1
0.5813 Remote Similarity NPD4357 Discontinued
0.5812 Remote Similarity NPD5726 Clinical (unspecified phase)
0.5811 Remote Similarity NPD7693 Approved
0.581 Remote Similarity NPD8398 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