Structure

Physi-Chem Properties

Molecular Weight:  1075.71
Volume:  711.749
LogP:  4.573
LogD:  2.283
LogS:  -4.516
# Rotatable Bonds:  14
TPSA:  169.53
# H-Bond Aceptor:  13
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.195
Synthetic Accessibility Score:  5.812
Fsp3:  0.419
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.55
MDCK Permeability:  2.6889609216596e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.91
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.44
Plasma Protein Binding (PPB):  100.39769744873047%
Volume Distribution (VD):  1.621
Pgp-substrate:  4.3811845779418945%

ADMET: Metabolism

CYP1A2-inhibitor:  0.445
CYP1A2-substrate:  0.194
CYP2C19-inhibitor:  0.968
CYP2C19-substrate:  0.747
CYP2C9-inhibitor:  0.964
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.906
CYP2D6-substrate:  0.188
CYP3A4-inhibitor:  0.979
CYP3A4-substrate:  0.436

ADMET: Excretion

Clearance (CL):  0.454
Half-life (T1/2):  0.019

ADMET: Toxicity

hERG Blockers:  0.409
Human Hepatotoxicity (H-HT):  0.95
Drug-inuced Liver Injury (DILI):  0.87
AMES Toxicity:  0.422
Rat Oral Acute Toxicity:  0.981
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.858
Carcinogencity:  0.884
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.976

Download Data

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

  Natural Product: NPC202866

Natural Product ID:  NPC202866
Common Name*:   11,19-Dideoxyfistularin-3
IUPAC Name:   (5S,6R)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[[(5S,6R)-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carbonyl]amino]ethyl]phenoxy]propyl]-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:   11,19-Dideoxyfistularin-3
Standard InCHIKey:  SYYVXQOWLOEXDU-TUXGATLDSA-N
Standard InCHI:  InChI=1S/C31H30Br6N4O9/c1-46-24-17(34)10-30(26(42)21(24)36)12-19(40-49-30)28(44)38-5-3-7-48-23-15(32)8-14(9-16(23)33)4-6-39-29(45)20-13-31(50-41-20)11-18(35)25(47-2)22(37)27(31)43/h8-11,26-27,42-43H,3-7,12-13H2,1-2H3,(H,38,44)(H,39,45)/t26-,27-,30+,31+/m0/s1
SMILES:  COC1=C(Br)[C@@H]([C@]2(C=C1Br)ON=C(C2)C(=O)NCCCOc1c(Br)cc(cc1Br)CCNC(=O)C1=NO[C@@]2(C1)C=C(Br)C(=C([C@@H]2O)Br)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509471
PubChem CID:   44587506
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
NPO4817 Briareum excavatum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[10096858]
NPO4817 Briareum excavatum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[10543904]
NPO4817 Briareum excavatum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[11277747]
NPO4817 Briareum excavatum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[11720523]
NPO287 Wrightia javanica Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[12808258]
NPO29034 Suberea mollis Species Aplysinellidae Eukaryota n.a. red sea n.a. PMID[18656986]
NPO29034 Suberea mollis Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[21542602]
NPO29034 Suberea mollis Species Aplysinellidae Eukaryota n.a. Red Sea n.a. PMID[21542602]
NPO4817 Briareum excavatum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[9599257]
NPO9047.1 Brassica rapa subsp. oleifera Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO287 Wrightia javanica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9047.1 Brassica rapa subsp. oleifera Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4191 Thermococcus acidaminovorans Species Thermococcaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO29034 Suberea mollis Species Aplysinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8123 Aplysina cavernicola Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2651 Ceroplastes floridensis Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4817 Briareum excavatum Species Briareidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3266 Euryops sulcatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO287 Wrightia javanica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1594 [enterobacter] aerogenes Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1512 Cissampelos fasciculata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9047.1 Brassica rapa subsp. oleifera Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7223 Castela tortuosa Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27875 Fallopia convolvulus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6901 Lophosoria quadripinnata Species Dicksoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8290 Mycena megaspora Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3434 Thymus camphoratus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6725 Tulipa hybrid Species Liliaceae 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
NPT165 Cell Line HeLa Homo sapiens EC50 = 2600.0 nM PMID[516044]

☑ 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 NPC202866 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
0.9593 High Similarity NPC259071
0.9593 High Similarity NPC77435
0.927 High Similarity NPC227953
0.9096 High Similarity NPC174607
0.9045 High Similarity NPC147847
0.8722 High Similarity NPC121571
0.8722 High Similarity NPC8093
0.8541 High Similarity NPC474678
0.8541 High Similarity NPC471338
0.8523 High Similarity NPC477255
0.8495 Intermediate Similarity NPC475843
0.8407 Intermediate Similarity NPC477254
0.8368 Intermediate Similarity NPC123140
0.8368 Intermediate Similarity NPC471337
0.8163 Intermediate Similarity NPC470746
0.8163 Intermediate Similarity NPC471336
0.8071 Intermediate Similarity NPC471339
0.7882 Intermediate Similarity NPC471335
0.7654 Intermediate Similarity NPC156311
0.7486 Intermediate Similarity NPC469711
0.7398 Intermediate Similarity NPC248822
0.7374 Intermediate Similarity NPC76412
0.7356 Intermediate Similarity NPC128877
0.7333 Intermediate Similarity NPC109968
0.7333 Intermediate Similarity NPC258222
0.733 Intermediate Similarity NPC308571
0.7293 Intermediate Similarity NPC47672
0.7268 Intermediate Similarity NPC233926
0.7192 Intermediate Similarity NPC473450
0.7191 Intermediate Similarity NPC78530
0.7121 Intermediate Similarity NPC246591
0.7095 Intermediate Similarity NPC135349
0.7095 Intermediate Similarity NPC470472
0.7072 Intermediate Similarity NPC71629
0.703 Intermediate Similarity NPC80514
0.7006 Intermediate Similarity NPC470470
0.7006 Intermediate Similarity NPC474673
0.6989 Remote Similarity NPC470471
0.6978 Remote Similarity NPC296085
0.69 Remote Similarity NPC96275
0.69 Remote Similarity NPC471591
0.69 Remote Similarity NPC473892
0.69 Remote Similarity NPC475658
0.6889 Remote Similarity NPC474128
0.6879 Remote Similarity NPC477220
0.6866 Remote Similarity NPC141405
0.6866 Remote Similarity NPC82741
0.6866 Remote Similarity NPC473409
0.6847 Remote Similarity NPC102245
0.6837 Remote Similarity NPC143450
0.6837 Remote Similarity NPC226001
0.6814 Remote Similarity NPC65714
0.6802 Remote Similarity NPC158672
0.6802 Remote Similarity NPC298981
0.6802 Remote Similarity NPC1702
0.6802 Remote Similarity NPC207819
0.6802 Remote Similarity NPC272463
0.6802 Remote Similarity NPC110454
0.6802 Remote Similarity NPC126128
0.6802 Remote Similarity NPC473462
0.6766 Remote Similarity NPC49172
0.6765 Remote Similarity NPC64066
0.6763 Remote Similarity NPC110131
0.6751 Remote Similarity NPC469979
0.6734 Remote Similarity NPC475396
0.6715 Remote Similarity NPC471592
0.6701 Remote Similarity NPC225130
0.67 Remote Similarity NPC301941
0.67 Remote Similarity NPC74618
0.67 Remote Similarity NPC214188
0.6699 Remote Similarity NPC469721
0.6685 Remote Similarity NPC470886
0.6667 Remote Similarity NPC283207
0.6635 Remote Similarity NPC469731
0.6634 Remote Similarity NPC138083
0.663 Remote Similarity NPC473261
0.663 Remote Similarity NPC300912
0.663 Remote Similarity NPC202166
0.663 Remote Similarity NPC473262
0.66 Remote Similarity NPC290534
0.6585 Remote Similarity NPC230539
0.6569 Remote Similarity NPC80337
0.6569 Remote Similarity NPC144823
0.6536 Remote Similarity NPC247018
0.6536 Remote Similarity NPC97870
0.6536 Remote Similarity NPC307123
0.652 Remote Similarity NPC276120
0.6513 Remote Similarity NPC254700
0.6489 Remote Similarity NPC20755
0.6436 Remote Similarity NPC32064
0.6425 Remote Similarity NPC474087
0.6419 Remote Similarity NPC81845
0.6417 Remote Similarity NPC130714
0.6409 Remote Similarity NPC473683
0.64 Remote Similarity NPC164608
0.639 Remote Similarity NPC315542
0.639 Remote Similarity NPC299806
0.6389 Remote Similarity NPC473724
0.6389 Remote Similarity NPC475735
0.6385 Remote Similarity NPC242728
0.6382 Remote Similarity NPC89831
0.6373 Remote Similarity NPC56635
0.6368 Remote Similarity NPC50016
0.6359 Remote Similarity NPC213471
0.6354 Remote Similarity NPC235033
0.6354 Remote Similarity NPC471235
0.6354 Remote Similarity NPC73132
0.635 Remote Similarity NPC273755
0.6347 Remote Similarity NPC295795
0.6346 Remote Similarity NPC174122
0.6346 Remote Similarity NPC64140
0.6345 Remote Similarity NPC469479
0.6333 Remote Similarity NPC474091
0.6332 Remote Similarity NPC46009
0.6332 Remote Similarity NPC475204
0.6332 Remote Similarity NPC471568
0.6332 Remote Similarity NPC196091
0.6332 Remote Similarity NPC475123
0.6332 Remote Similarity NPC473693
0.6319 Remote Similarity NPC169766
0.6319 Remote Similarity NPC132308
0.6318 Remote Similarity NPC471165
0.6316 Remote Similarity NPC324081
0.6316 Remote Similarity NPC473378
0.6316 Remote Similarity NPC473407
0.6305 Remote Similarity NPC475615
0.6298 Remote Similarity NPC124626
0.6298 Remote Similarity NPC470951
0.6298 Remote Similarity NPC234069
0.6294 Remote Similarity NPC472923
0.6284 Remote Similarity NPC79130
0.6281 Remote Similarity NPC280022
0.6281 Remote Similarity NPC186617
0.6279 Remote Similarity NPC156055
0.6274 Remote Similarity NPC308709
0.627 Remote Similarity NPC197045
0.6269 Remote Similarity NPC123011
0.6269 Remote Similarity NPC476268
0.6269 Remote Similarity NPC256689
0.6269 Remote Similarity NPC306804
0.6268 Remote Similarity NPC61332
0.6268 Remote Similarity NPC240130
0.6264 Remote Similarity NPC474753
0.6257 Remote Similarity NPC204546
0.6256 Remote Similarity NPC319320
0.6256 Remote Similarity NPC287757
0.625 Remote Similarity NPC235633
0.625 Remote Similarity NPC40234
0.625 Remote Similarity NPC94862
0.625 Remote Similarity NPC56685
0.6244 Remote Similarity NPC92235
0.6244 Remote Similarity NPC144314
0.6238 Remote Similarity NPC473354
0.6237 Remote Similarity NPC40321
0.6233 Remote Similarity NPC477551
0.6232 Remote Similarity NPC206061
0.6227 Remote Similarity NPC293347
0.6225 Remote Similarity NPC97526
0.6225 Remote Similarity NPC45037
0.6225 Remote Similarity NPC119652
0.6219 Remote Similarity NPC328494
0.6216 Remote Similarity NPC470249
0.6216 Remote Similarity NPC470248
0.6215 Remote Similarity NPC477552
0.6215 Remote Similarity NPC477550
0.6215 Remote Similarity NPC50548
0.6214 Remote Similarity NPC475283
0.6214 Remote Similarity NPC152205
0.6212 Remote Similarity NPC63931
0.6205 Remote Similarity NPC67658
0.6204 Remote Similarity NPC214368
0.6201 Remote Similarity NPC320242
0.62 Remote Similarity NPC469505
0.6199 Remote Similarity NPC197125
0.6197 Remote Similarity NPC149962
0.6196 Remote Similarity NPC181086
0.6196 Remote Similarity NPC303993
0.6193 Remote Similarity NPC14339
0.6193 Remote Similarity NPC66855
0.619 Remote Similarity NPC29531
0.6188 Remote Similarity NPC326027
0.6188 Remote Similarity NPC137627
0.6186 Remote Similarity NPC123859
0.6186 Remote Similarity NPC470710
0.6179 Remote Similarity NPC302715
0.6175 Remote Similarity NPC470392
0.6172 Remote Similarity NPC4910
0.6171 Remote Similarity NPC326333
0.6165 Remote Similarity NPC477637
0.6165 Remote Similarity NPC473404
0.6162 Remote Similarity NPC196708
0.6162 Remote Similarity NPC67080
0.6158 Remote Similarity NPC476227
0.6158 Remote Similarity NPC26108
0.6154 Remote Similarity NPC135173
0.615 Remote Similarity NPC473502
0.615 Remote Similarity NPC184933
0.615 Remote Similarity NPC328649
0.615 Remote Similarity NPC59827
0.615 Remote Similarity NPC294516

  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 NPC202866 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
0.6734 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6683 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6582 Remote Similarity NPD7608 Discontinued
0.6546 Remote Similarity NPD8031 Discontinued
0.6536 Remote Similarity NPD1423 Approved
0.6531 Remote Similarity NPD7485 Phase 3
0.6531 Remote Similarity NPD7484 Phase 3
0.6503 Remote Similarity NPD2240 Approved
0.6503 Remote Similarity NPD2239 Approved
0.6486 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6421 Remote Similarity NPD7131 Phase 3
0.6408 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6394 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6324 Remote Similarity NPD1725 Approved
0.6324 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6316 Remote Similarity NPD3536 Discontinued
0.631 Remote Similarity NPD2458 Approved
0.631 Remote Similarity NPD4162 Approved
0.631 Remote Similarity NPD2460 Phase 3
0.631 Remote Similarity NPD2459 Approved
0.6296 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6289 Remote Similarity NPD2541 Clinical (unspecified phase)
0.625 Remote Similarity NPD3054 Approved
0.625 Remote Similarity NPD3052 Approved
0.6243 Remote Similarity NPD9718 Approved
0.623 Remote Similarity NPD3985 Discontinued
0.623 Remote Similarity NPD2874 Phase 2
0.623 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6212 Remote Similarity NPD1307 Phase 2
0.6212 Remote Similarity NPD1309 Phase 2
0.6209 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6205 Remote Similarity NPD6677 Suspended
0.6201 Remote Similarity NPD1770 Clinical (unspecified phase)
0.6201 Remote Similarity NPD1820 Approved
0.6201 Remote Similarity NPD1819 Approved
0.6201 Remote Similarity NPD1818 Approved
0.6201 Remote Similarity NPD1817 Approved
0.6198 Remote Similarity NPD1975 Clinical (unspecified phase)
0.6188 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6179 Remote Similarity NPD4466 Phase 1
0.6175 Remote Similarity NPD2245 Discovery
0.617 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6166 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6165 Remote Similarity NPD1298 Discontinued
0.6154 Remote Similarity NPD5163 Phase 2
0.6154 Remote Similarity NPD3164 Approved
0.6154 Remote Similarity NPD3180 Approved
0.6154 Remote Similarity NPD3167 Approved
0.6154 Remote Similarity NPD3179 Approved
0.6154 Remote Similarity NPD3166 Approved
0.6154 Remote Similarity NPD3165 Approved
0.615 Remote Similarity NPD2904 Discontinued
0.615 Remote Similarity NPD2042 Clinical (unspecified phase)
0.615 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6135 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6134 Remote Similarity NPD3686 Approved
0.6134 Remote Similarity NPD3687 Approved
0.6127 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6114 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7810 Phase 3
0.6111 Remote Similarity NPD7811 Phase 3
0.6108 Remote Similarity NPD4575 Clinical (unspecified phase)
0.61 Remote Similarity NPD6315 Phase 2
0.61 Remote Similarity NPD6862 Phase 2
0.61 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6098 Remote Similarity NPD42 Phase 2
0.6098 Remote Similarity NPD6042 Phase 2
0.6094 Remote Similarity NPD6087 Phase 1
0.6091 Remote Similarity NPD5355 Approved
0.6091 Remote Similarity NPD5356 Approved
0.6087 Remote Similarity NPD7038 Approved
0.6087 Remote Similarity NPD7039 Approved
0.6085 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5605 Phase 2
0.6077 Remote Similarity NPD6851 Approved
0.6077 Remote Similarity NPD6853 Approved
0.6075 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6071 Remote Similarity NPD2592 Discontinued
0.6068 Remote Similarity NPD5557 Phase 1
0.6064 Remote Similarity NPD2161 Phase 2
0.6062 Remote Similarity NPD7019 Approved
0.6062 Remote Similarity NPD7020 Approved
0.6062 Remote Similarity NPD6419 Discontinued
0.6061 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6061 Remote Similarity NPD7972 Discontinued
0.6061 Remote Similarity NPD5773 Approved
0.6061 Remote Similarity NPD5772 Approved
0.6053 Remote Similarity NPD3060 Approved
0.6051 Remote Similarity NPD4124 Clinical (unspecified phase)
0.6048 Remote Similarity NPD3153 Approved
0.6048 Remote Similarity NPD3154 Approved
0.6042 Remote Similarity NPD5295 Discontinued
0.6039 Remote Similarity NPD6297 Approved
0.6031 Remote Similarity NPD7613 Discontinued
0.6031 Remote Similarity NPD52 Approved
0.6031 Remote Similarity NPD7526 Approved
0.6031 Remote Similarity NPD7527 Clinical (unspecified phase)
0.603 Remote Similarity NPD5967 Approved
0.6022 Remote Similarity NPD1794 Approved
0.602 Remote Similarity NPD2651 Approved
0.602 Remote Similarity NPD824 Approved
0.602 Remote Similarity NPD2649 Approved
0.6019 Remote Similarity NPD6089 Clinical (unspecified phase)
0.601 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6009 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6009 Remote Similarity NPD8059 Phase 3
0.6 Remote Similarity NPD3162 Approved
0.6 Remote Similarity NPD3366 Approved
0.6 Remote Similarity NPD3163 Approved
0.6 Remote Similarity NPD1670 Discontinued
0.6 Remote Similarity NPD7153 Discontinued
0.5991 Remote Similarity NPD6608 Clinical (unspecified phase)
0.5991 Remote Similarity NPD3490 Discontinued
0.599 Remote Similarity NPD1337 Clinical (unspecified phase)
0.5979 Remote Similarity NPD5556 Clinical (unspecified phase)
0.5979 Remote Similarity NPD4662 Approved
0.5979 Remote Similarity NPD3157 Approved
0.5979 Remote Similarity NPD1771 Clinical (unspecified phase)
0.5979 Remote Similarity NPD3158 Phase 1
0.5979 Remote Similarity NPD4661 Approved
0.5971 Remote Similarity NPD6620 Discovery
0.5971 Remote Similarity NPD3909 Discontinued
0.5969 Remote Similarity NPD5062 Approved
0.5969 Remote Similarity NPD5061 Approved
0.5968 Remote Similarity NPD3597 Clinical (unspecified phase)
0.5962 Remote Similarity NPD3823 Discontinued
0.596 Remote Similarity NPD6072 Discontinued
0.5955 Remote Similarity NPD4971 Clinical (unspecified phase)
0.5955 Remote Similarity NPD6863 Phase 2
0.595 Remote Similarity NPD7318 Phase 3
0.5949 Remote Similarity NPD2184 Approved
0.5949 Remote Similarity NPD2183 Approved
0.5947 Remote Similarity NPD3656 Approved
0.5939 Remote Similarity NPD3866 Clinical (unspecified phase)
0.593 Remote Similarity NPD7577 Discontinued
0.593 Remote Similarity NPD8019 Approved
0.5926 Remote Similarity NPD7256 Discontinued
0.5924 Remote Similarity NPD2614 Approved
0.592 Remote Similarity NPD4581 Clinical (unspecified phase)
0.5919 Remote Similarity NPD7584 Approved
0.5918 Remote Similarity NPD6662 Clinical (unspecified phase)
0.5918 Remote Similarity NPD7523 Phase 3
0.5914 Remote Similarity NPD5745 Approved
0.5912 Remote Similarity NPD2429 Approved
0.5912 Remote Similarity NPD3676 Clinical (unspecified phase)
0.5912 Remote Similarity NPD2428 Approved
0.5911 Remote Similarity NPD4666 Phase 3
0.5907 Remote Similarity NPD2677 Approved
0.5907 Remote Similarity NPD5160 Discontinued
0.5905 Remote Similarity NPD7190 Clinical (unspecified phase)
0.5905 Remote Similarity NPD3936 Clinical (unspecified phase)
0.5904 Remote Similarity NPD2653 Approved
0.5902 Remote Similarity NPD2388 Discontinued
0.5902 Remote Similarity NPD5137 Approved
0.5902 Remote Similarity NPD8051 Clinical (unspecified phase)
0.5902 Remote Similarity NPD2215 Approved
0.5902 Remote Similarity NPD2216 Approved
0.59 Remote Similarity NPD2978 Approved
0.59 Remote Similarity NPD2977 Approved
0.5895 Remote Similarity NPD7450 Phase 2
0.5894 Remote Similarity NPD5940 Clinical (unspecified phase)
0.5892 Remote Similarity NPD3136 Phase 2
0.5888 Remote Similarity NPD5267 Discontinued
0.5882 Remote Similarity NPD3142 Approved
0.5882 Remote Similarity NPD3140 Approved
0.5879 Remote Similarity NPD7110 Phase 1
0.5879 Remote Similarity NPD7109 Clinical (unspecified phase)
0.5871 Remote Similarity NPD2296 Approved
0.587 Remote Similarity NPD2250 Discontinued
0.5867 Remote Similarity NPD2186 Approved
0.5866 Remote Similarity NPD2556 Approved
0.5866 Remote Similarity NPD2554 Approved
0.5865 Remote Similarity NPD3933 Discontinued
0.5865 Remote Similarity NPD5095 Phase 3
0.5865 Remote Similarity NPD5096 Phase 3
0.5864 Remote Similarity NPD7978 Discontinued
0.5862 Remote Similarity NPD5709 Phase 3
0.5862 Remote Similarity NPD8303 Discontinued
0.5859 Remote Similarity NPD7827 Phase 1
0.5859 Remote Similarity NPD6523 Clinical (unspecified phase)
0.5859 Remote Similarity NPD3336 Discovery
0.5856 Remote Similarity NPD2235 Phase 2
0.5856 Remote Similarity NPD2231 Phase 2
0.5856 Remote Similarity NPD5152 Clinical (unspecified phase)
0.5855 Remote Similarity NPD1662 Clinical (unspecified phase)
0.5854 Remote Similarity NPD4010 Discontinued
0.585 Remote Similarity NPD7317 Phase 3
0.5849 Remote Similarity NPD5946 Clinical (unspecified phase)
0.5849 Remote Similarity NPD6556 Clinical (unspecified phase)
0.5848 Remote Similarity NPD7583 Approved
0.5842 Remote Similarity NPD6380 Phase 1
0.5842 Remote Similarity NPD2155 Approved
0.5842 Remote Similarity NPD2156 Approved
0.5842 Remote Similarity NPD2154 Approved
0.5841 Remote Similarity NPD7693 Approved
0.584 Remote Similarity NPD4847 Phase 1
0.5838 Remote Similarity NPD6030 Approved
0.5838 Remote Similarity NPD6031 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