Structure

Physi-Chem Properties

Molecular Weight:  491.22
Volume:  469.18
LogP:  1.646
LogD:  0.658
LogS:  -3.295
# Rotatable Bonds:  4
TPSA:  172.7
# H-Bond Aceptor:  10
# H-Bond Donor:  7
# Rings:  7
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.222
Synthetic Accessibility Score:  7.334
Fsp3:  0.72
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.136
MDCK Permeability:  8.943933607952204e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.197
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.378
Plasma Protein Binding (PPB):  47.49517059326172%
Volume Distribution (VD):  0.571
Pgp-substrate:  50.933753967285156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.995
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.24
CYP2C9-inhibitor:  0.031
CYP2C9-substrate:  0.009
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.074
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.215

ADMET: Excretion

Clearance (CL):  1.746
Half-life (T1/2):  0.097

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.947
Drug-inuced Liver Injury (DILI):  0.966
AMES Toxicity:  0.968
Rat Oral Acute Toxicity:  0.757
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.918
Carcinogencity:  0.998
Eye Corrosion:  0.003
Eye Irritation:  0.048
Respiratory Toxicity:  0.986

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

  Natural Product: NPC37473

Natural Product ID:  NPC37473
Common Name*:   Dehydroryanodine
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BPFNBBLVUYSFRK-OHEPIYSBSA-N
Standard InCHI:  InChI=1S/C25H33NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12,15,17,26-27,29-33H,3,8-9,11H2,1-2,4-5H3/t15-,17-,18+,19+,20+,21+,22-,23-,24-,25-/m1/s1
SMILES:  CC(C)[C@]1([C@H]([C@]2([C@@]3(C)C[C@]4([C@]1(C)[C@@]2([C@]1([C@@H](C(=C)CC[C@]31O)O)O4)O)O)O)OC(=O)c1ccc[nH]1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2273036
PubChem CID:   125168
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16155 Hymenoxys odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14180 Pieris rapae Species Pieridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11793 Neuropogon trachycarpus Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16155 Hymenoxys odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16503 Tovaria pendula Species Tovariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9348 Cananga odorata Species Annonaceae 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
NPT2699 Individual Protein Ryanodine receptor 1 Oryctolagus cuniculus IC50 = 13.0 nM PMID[554407]
NPT2699 Individual Protein Ryanodine receptor 1 Oryctolagus cuniculus Ratio = 91.0 n.a. PMID[554408]
NPT2700 Individual Protein Ryanodine receptor 3 Mus musculus Ratio = 77.0 n.a. PMID[554408]
NPT2699 Individual Protein Ryanodine receptor 1 Oryctolagus cuniculus Ratio = 112.0 n.a. PMID[554408]
NPT734 Organism Musca domestica Musca domestica KD50 = 0.03 ug/g PMID[554407]
NPT32 Organism Mus musculus Mus musculus LD50 = 0.1 mg.kg-1 PMID[554407]
NPT734 Organism Musca domestica Musca domestica Ratio = 136.0 n.a. PMID[554408]
NPT734 Organism Musca domestica Musca domestica Ratio = 90.0 n.a. PMID[554408]

☑ 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 NPC37473 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
0.8248 Intermediate Similarity NPC476090
0.808 Intermediate Similarity NPC141385
0.787 Intermediate Similarity NPC475498
0.787 Intermediate Similarity NPC473850
0.787 Intermediate Similarity NPC475137
0.7826 Intermediate Similarity NPC76565
0.7826 Intermediate Similarity NPC57797
0.7826 Intermediate Similarity NPC250807
0.7797 Intermediate Similarity NPC475408
0.7797 Intermediate Similarity NPC471014
0.7768 Intermediate Similarity NPC475362
0.7768 Intermediate Similarity NPC470486
0.7768 Intermediate Similarity NPC475644
0.7768 Intermediate Similarity NPC471190
0.7768 Intermediate Similarity NPC471977
0.7763 Intermediate Similarity NPC144779
0.7763 Intermediate Similarity NPC294579
0.7753 Intermediate Similarity NPC470306
0.7737 Intermediate Similarity NPC476516
0.7725 Intermediate Similarity NPC122968
0.7725 Intermediate Similarity NPC475631
0.7725 Intermediate Similarity NPC146824
0.7725 Intermediate Similarity NPC87152
0.7725 Intermediate Similarity NPC228377
0.7725 Intermediate Similarity NPC475600
0.7725 Intermediate Similarity NPC477787
0.7725 Intermediate Similarity NPC328186
0.7725 Intermediate Similarity NPC476110
0.7719 Intermediate Similarity NPC6981
0.7719 Intermediate Similarity NPC471016
0.7699 Intermediate Similarity NPC472553
0.7682 Intermediate Similarity NPC473506
0.7675 Intermediate Similarity NPC477910
0.7669 Intermediate Similarity NPC30456
0.7652 Intermediate Similarity NPC216428
0.7652 Intermediate Similarity NPC84815
0.7652 Intermediate Similarity NPC301368
0.7644 Intermediate Similarity NPC48042
0.7644 Intermediate Similarity NPC304179
0.7644 Intermediate Similarity NPC472550
0.7637 Intermediate Similarity NPC237702
0.7627 Intermediate Similarity NPC473689
0.7627 Intermediate Similarity NPC316841
0.7627 Intermediate Similarity NPC292416
0.7627 Intermediate Similarity NPC475596
0.7627 Intermediate Similarity NPC475303
0.7621 Intermediate Similarity NPC476467
0.7609 Intermediate Similarity NPC62367
0.7605 Intermediate Similarity NPC170751
0.76 Intermediate Similarity NPC63041
0.7597 Intermediate Similarity NPC471980
0.7595 Intermediate Similarity NPC244839
0.7595 Intermediate Similarity NPC319880
0.7595 Intermediate Similarity NPC320324
0.7555 Intermediate Similarity NPC228331
0.7555 Intermediate Similarity NPC319128
0.7554 Intermediate Similarity NPC127026
0.7554 Intermediate Similarity NPC477788
0.7554 Intermediate Similarity NPC127720
0.7545 Intermediate Similarity NPC477043
0.7531 Intermediate Similarity NPC327769
0.7531 Intermediate Similarity NPC475406
0.7531 Intermediate Similarity NPC35208
0.7531 Intermediate Similarity NPC475426
0.7522 Intermediate Similarity NPC477907
0.7522 Intermediate Similarity NPC477909
0.7522 Intermediate Similarity NPC42678
0.7511 Intermediate Similarity NPC477912
0.7511 Intermediate Similarity NPC477044
0.7511 Intermediate Similarity NPC477041
0.75 Intermediate Similarity NPC327904
0.75 Intermediate Similarity NPC472555
0.75 Intermediate Similarity NPC38959
0.749 Intermediate Similarity NPC238278
0.7489 Intermediate Similarity NPC477902
0.7489 Intermediate Similarity NPC328154
0.7478 Intermediate Similarity NPC4421
0.7477 Intermediate Similarity NPC477045
0.7465 Intermediate Similarity NPC209917
0.7458 Intermediate Similarity NPC148860
0.7429 Intermediate Similarity NPC476517
0.7426 Intermediate Similarity NPC475601
0.7426 Intermediate Similarity NPC211920
0.7426 Intermediate Similarity NPC124029
0.7415 Intermediate Similarity NPC233727
0.7414 Intermediate Similarity NPC206343
0.7414 Intermediate Similarity NPC477908
0.7407 Intermediate Similarity NPC253482
0.7406 Intermediate Similarity NPC96801
0.7406 Intermediate Similarity NPC150698
0.7404 Intermediate Similarity NPC477911
0.7382 Intermediate Similarity NPC158020
0.7382 Intermediate Similarity NPC473115
0.7382 Intermediate Similarity NPC6576
0.7382 Intermediate Similarity NPC473089
0.7382 Intermediate Similarity NPC212768
0.7382 Intermediate Similarity NPC75600
0.7375 Intermediate Similarity NPC469748
0.7359 Intermediate Similarity NPC51008
0.7359 Intermediate Similarity NPC41724
0.7353 Intermediate Similarity NPC14116
0.7353 Intermediate Similarity NPC285411
0.7344 Intermediate Similarity NPC70155
0.7328 Intermediate Similarity NPC264674
0.7322 Intermediate Similarity NPC134384
0.7322 Intermediate Similarity NPC311196
0.7317 Intermediate Similarity NPC475648
0.7316 Intermediate Similarity NPC323551
0.7316 Intermediate Similarity NPC280473
0.7303 Intermediate Similarity NPC213143
0.7269 Intermediate Similarity NPC235885
0.7265 Intermediate Similarity NPC162812
0.7261 Intermediate Similarity NPC477906
0.7215 Intermediate Similarity NPC477903
0.721 Intermediate Similarity NPC165837
0.7205 Intermediate Similarity NPC476514
0.7197 Intermediate Similarity NPC141428
0.7167 Intermediate Similarity NPC472762
0.7149 Intermediate Similarity NPC204491
0.7149 Intermediate Similarity NPC193361
0.7149 Intermediate Similarity NPC30570
0.7149 Intermediate Similarity NPC62844
0.7137 Intermediate Similarity NPC470279
0.7137 Intermediate Similarity NPC57690
0.7126 Intermediate Similarity NPC85879
0.7126 Intermediate Similarity NPC326930
0.7126 Intermediate Similarity NPC475301
0.7126 Intermediate Similarity NPC53255
0.7125 Intermediate Similarity NPC477900
0.7125 Intermediate Similarity NPC477899
0.7124 Intermediate Similarity NPC470189
0.7124 Intermediate Similarity NPC40919
0.7113 Intermediate Similarity NPC235364
0.7112 Intermediate Similarity NPC472752
0.7098 Intermediate Similarity NPC13603
0.7094 Intermediate Similarity NPC292517
0.708 Intermediate Similarity NPC180668
0.708 Intermediate Similarity NPC471013
0.708 Intermediate Similarity NPC148896
0.7071 Intermediate Similarity NPC2395
0.7064 Intermediate Similarity NPC229348
0.7054 Intermediate Similarity NPC26881
0.7052 Intermediate Similarity NPC475533
0.7036 Intermediate Similarity NPC10904
0.7029 Intermediate Similarity NPC477901
0.7027 Intermediate Similarity NPC471978
0.7026 Intermediate Similarity NPC475835
0.7024 Intermediate Similarity NPC324619
0.7024 Intermediate Similarity NPC475315
0.7017 Intermediate Similarity NPC319556
0.7017 Intermediate Similarity NPC187494
0.7016 Intermediate Similarity NPC473833
0.7008 Intermediate Similarity NPC471634
0.7008 Intermediate Similarity NPC473806
0.7004 Intermediate Similarity NPC203614
0.7004 Intermediate Similarity NPC36405
0.7 Intermediate Similarity NPC470843
0.7 Intermediate Similarity NPC94541
0.6996 Remote Similarity NPC470280
0.6996 Remote Similarity NPC470190
0.6987 Remote Similarity NPC242446
0.6987 Remote Similarity NPC475476
0.6962 Remote Similarity NPC328928
0.6962 Remote Similarity NPC471284
0.6958 Remote Similarity NPC54066
0.6955 Remote Similarity NPC79107
0.6955 Remote Similarity NPC267926
0.6955 Remote Similarity NPC475424
0.6953 Remote Similarity NPC131273
0.6953 Remote Similarity NPC473441
0.6953 Remote Similarity NPC471015
0.6949 Remote Similarity NPC151976
0.6949 Remote Similarity NPC235900
0.6947 Remote Similarity NPC471979
0.6942 Remote Similarity NPC266192
0.6941 Remote Similarity NPC476515
0.6939 Remote Similarity NPC91125
0.6935 Remote Similarity NPC57453
0.6933 Remote Similarity NPC207531
0.6926 Remote Similarity NPC470873
0.6923 Remote Similarity NPC127677
0.6911 Remote Similarity NPC290529
0.6908 Remote Similarity NPC15801
0.6904 Remote Similarity NPC472285
0.6891 Remote Similarity NPC473650
0.6891 Remote Similarity NPC313640
0.6891 Remote Similarity NPC160527
0.6891 Remote Similarity NPC97388
0.688 Remote Similarity NPC46225
0.6872 Remote Similarity NPC147446
0.687 Remote Similarity NPC103361
0.6867 Remote Similarity NPC289086
0.6849 Remote Similarity NPC473547
0.6835 Remote Similarity NPC250129
0.6835 Remote Similarity NPC82370
0.6833 Remote Similarity NPC477042
0.6833 Remote Similarity NPC312645
0.6833 Remote Similarity NPC96131
0.6818 Remote Similarity NPC470874
0.6811 Remote Similarity NPC311451

  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 NPC37473 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
0.7398 Intermediate Similarity NPD8468 Phase 2
0.711 Intermediate Similarity NPD3178 Discontinued
0.6835 Remote Similarity NPD7470 Discontinued
0.6766 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6709 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6681 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6639 Remote Similarity NPD2510 Approved
0.6639 Remote Similarity NPD2509 Approved
0.6639 Remote Similarity NPD3795 Approved
0.6639 Remote Similarity NPD3794 Approved
0.6584 Remote Similarity NPD3394 Approved
0.6584 Remote Similarity NPD3393 Approved
0.6584 Remote Similarity NPD3389 Approved
0.6582 Remote Similarity NPD5901 Discontinued
0.6577 Remote Similarity NPD5482 Discontinued
0.6574 Remote Similarity NPD7688 Phase 1
0.6557 Remote Similarity NPD8325 Phase 3
0.6557 Remote Similarity NPD8326 Phase 3
0.6557 Remote Similarity NPD8327 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7957 Phase 1
0.6496 Remote Similarity NPD5003 Discontinued
0.6488 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6486 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6481 Remote Similarity NPD4427 Phase 2
0.6459 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6454 Remote Similarity NPD4086 Phase 1
0.6446 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3947 Discontinued
0.6444 Remote Similarity NPD7396 Approved
0.6437 Remote Similarity NPD6770 Approved
0.6432 Remote Similarity NPD8423 Phase 2
0.6432 Remote Similarity NPD8399 Phase 1
0.6417 Remote Similarity NPD7010 Phase 3
0.6416 Remote Similarity NPD8304 Clinical (unspecified phase)
0.6414 Remote Similarity NPD8289 Discontinued
0.6411 Remote Similarity NPD1996 Discontinued
0.641 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6408 Remote Similarity NPD7707 Approved
0.6406 Remote Similarity NPD3006 Discontinued
0.6406 Remote Similarity NPD5891 Approved
0.6405 Remote Similarity NPD6529 Discontinued
0.6381 Remote Similarity NPD7708 Approved
0.6379 Remote Similarity NPD8063 Discontinued
0.6376 Remote Similarity NPD1096 Discontinued
0.636 Remote Similarity NPD6995 Phase 1
0.636 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6349 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6347 Remote Similarity NPD5450 Discontinued
0.6345 Remote Similarity NPD3280 Approved
0.6341 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6337 Remote Similarity NPD4506 Discontinued
0.6333 Remote Similarity NPD8072 Approved
0.6327 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6327 Remote Similarity NPD5866 Approved
0.6316 Remote Similarity NPD8160 Phase 2
0.6316 Remote Similarity NPD5612 Discontinued
0.6309 Remote Similarity NPD2565 Phase 2
0.6309 Remote Similarity NPD2564 Approved
0.6292 Remote Similarity NPD8073 Approved
0.6287 Remote Similarity NPD7803 Approved
0.6286 Remote Similarity NPD5475 Discontinued
0.6281 Remote Similarity NPD7001 Phase 3
0.6279 Remote Similarity NPD4454 Phase 2
0.6275 Remote Similarity NPD7824 Approved
0.6275 Remote Similarity NPD4667 Clinical (unspecified phase)
0.627 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6266 Remote Similarity NPD7234 Approved
0.6266 Remote Similarity NPD7233 Approved
0.6265 Remote Similarity NPD7558 Phase 2
0.6265 Remote Similarity NPD5632 Approved
0.6261 Remote Similarity NPD2095 Phase 2
0.6261 Remote Similarity NPD2094 Phase 2
0.6261 Remote Similarity NPD2092 Phase 2
0.6261 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6261 Remote Similarity NPD6635 Approved
0.626 Remote Similarity NPD7069 Discontinued
0.625 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6241 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6234 Remote Similarity NPD2096 Phase 2
0.6234 Remote Similarity NPD2091 Phase 2
0.623 Remote Similarity NPD6376 Discontinued
0.6224 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6222 Remote Similarity NPD7956 Approved
0.6222 Remote Similarity NPD7955 Approved
0.622 Remote Similarity NPD5066 Phase 2
0.622 Remote Similarity NPD5067 Phase 2
0.6218 Remote Similarity NPD8364 Approved
0.6218 Remote Similarity NPD8363 Approved
0.6217 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6211 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6211 Remote Similarity NPD5022 Discontinued
0.6208 Remote Similarity NPD484 Approved
0.6207 Remote Similarity NPD7886 Phase 2
0.6207 Remote Similarity NPD7885 Phase 2
0.6206 Remote Similarity NPD7547 Clinical (unspecified phase)
0.62 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6176 Phase 1
0.6196 Remote Similarity NPD7731 Approved
0.6196 Remote Similarity NPD7730 Approved
0.6195 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6194 Remote Similarity NPD8097 Phase 3
0.6194 Remote Similarity NPD8096 Phase 3
0.6184 Remote Similarity NPD749 Clinical (unspecified phase)
0.6181 Remote Similarity NPD7271 Approved
0.6179 Remote Similarity NPD7825 Clinical (unspecified phase)
0.6173 Remote Similarity NPD8283 Approved
0.6173 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6173 Remote Similarity NPD56 Approved
0.6173 Remote Similarity NPD8282 Approved
0.616 Remote Similarity NPD1483 Discontinued
0.6157 Remote Similarity NPD2144 Approved
0.6154 Remote Similarity NPD2582 Approved
0.6154 Remote Similarity NPD2581 Approved
0.6151 Remote Similarity NPD6242 Discontinued
0.6147 Remote Similarity NPD3038 Discontinued
0.6143 Remote Similarity NPD8466 Approved
0.6143 Remote Similarity NPD8429 Approved
0.6143 Remote Similarity NPD8467 Approved
0.6143 Remote Similarity NPD8428 Approved
0.6143 Remote Similarity NPD8465 Approved
0.6143 Remote Similarity NPD8427 Approved
0.6142 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6141 Remote Similarity NPD4601 Approved
0.6141 Remote Similarity NPD4600 Approved
0.614 Remote Similarity NPD482 Approved
0.6135 Remote Similarity NPD7878 Phase 2
0.6135 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6132 Remote Similarity NPD2920 Discontinued
0.6125 Remote Similarity NPD7946 Pre-registration
0.6122 Remote Similarity NPD7417 Discontinued
0.6121 Remote Similarity NPD5596 Phase 2
0.6118 Remote Similarity NPD4376 Phase 3
0.6118 Remote Similarity NPD6665 Discontinued
0.6107 Remote Similarity NPD8098 Approved
0.6104 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6102 Remote Similarity NPD8356 Approved
0.6096 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6094 Remote Similarity NPD3263 Phase 3
0.6092 Remote Similarity NPD4526 Approved
0.6092 Remote Similarity NPD4528 Approved
0.6092 Remote Similarity NPD7853 Phase 2
0.6092 Remote Similarity NPD4529 Approved
0.6091 Remote Similarity NPD7187 Phase 2
0.6087 Remote Similarity NPD8479 Phase 2
0.6081 Remote Similarity NPD6531 Approved
0.6081 Remote Similarity NPD6530 Approved
0.6077 Remote Similarity NPD7953 Approved
0.6077 Remote Similarity NPD7951 Approved
0.6077 Remote Similarity NPD7789 Approved
0.6077 Remote Similarity NPD7952 Approved
0.6077 Remote Similarity NPD7791 Approved
0.6077 Remote Similarity NPD7790 Approved
0.6077 Remote Similarity NPD7950 Approved
0.6073 Remote Similarity NPD6456 Discontinued
0.6071 Remote Similarity NPD7395 Discontinued
0.607 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6065 Remote Similarity NPD7393 Clinical (unspecified phase)
0.6064 Remote Similarity NPD3916 Clinical (unspecified phase)
0.6064 Remote Similarity NPD3918 Approved
0.6064 Remote Similarity NPD8093 Discontinued
0.6064 Remote Similarity NPD3917 Approved
0.6063 Remote Similarity NPD4301 Approved
0.6058 Remote Similarity NPD7777 Approved
0.6058 Remote Similarity NPD7778 Approved
0.6058 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6058 Remote Similarity NPD53 Approved
0.6057 Remote Similarity NPD7689 Approved
0.6057 Remote Similarity NPD1392 Approved
0.6056 Remote Similarity NPD8460 Approved
0.6056 Remote Similarity NPD8459 Approved
0.6056 Remote Similarity NPD8426 Approved
0.6056 Remote Similarity NPD8425 Approved
0.6053 Remote Similarity NPD7967 Discontinued
0.6049 Remote Similarity NPD7727 Phase 2
0.6048 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6047 Remote Similarity NPD8105 Discontinued
0.6041 Remote Similarity NPD5426 Phase 3
0.6038 Remote Similarity NPD6517 Phase 3
0.6036 Remote Similarity NPD6026 Approved
0.6033 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6032 Remote Similarity NPD8406 Clinical (unspecified phase)
0.6031 Remote Similarity NPD7603 Discontinued
0.6031 Remote Similarity NPD5640 Discontinued
0.6024 Remote Similarity NPD3915 Approved
0.6024 Remote Similarity NPD8013 Clinical (unspecified phase)
0.6017 Remote Similarity NPD6642 Approved
0.6017 Remote Similarity NPD6641 Approved
0.6017 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6017 Remote Similarity NPD7948 Phase 1
0.6016 Remote Similarity NPD6752 Phase 1
0.6016 Remote Similarity NPD2715 Clinical (unspecified phase)
0.6016 Remote Similarity NPD6753 Phase 1
0.6015 Remote Similarity NPD5532 Phase 2
0.6009 Remote Similarity NPD820 Phase 3
0.6008 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6008 Remote Similarity NPD8430 Approved
0.6008 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6008 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6008 Remote Similarity NPD6292 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