Structure

Physi-Chem Properties

Molecular Weight:  490.39
Volume:  554.143
LogP:  7.009
LogD:  5.366
LogS:  -5.548
# Rotatable Bonds:  6
TPSA:  23.55
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.41
Synthetic Accessibility Score:  4.436
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.673
MDCK Permeability:  1.4473878763965331e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.208
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.11
30% Bioavailability (F30%):  0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.286
Plasma Protein Binding (PPB):  88.62287139892578%
Volume Distribution (VD):  2.271
Pgp-substrate:  3.614027738571167%

ADMET: Metabolism

CYP1A2-inhibitor:  0.333
CYP1A2-substrate:  0.378
CYP2C19-inhibitor:  0.162
CYP2C19-substrate:  0.968
CYP2C9-inhibitor:  0.321
CYP2C9-substrate:  0.184
CYP2D6-inhibitor:  0.91
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.944
CYP3A4-substrate:  0.871

ADMET: Excretion

Clearance (CL):  14.125
Half-life (T1/2):  0.038

ADMET: Toxicity

hERG Blockers:  0.999
Human Hepatotoxicity (H-HT):  0.345
Drug-inuced Liver Injury (DILI):  0.836
AMES Toxicity:  0.16
Rat Oral Acute Toxicity:  0.792
Maximum Recommended Daily Dose:  0.338
Skin Sensitization:  0.978
Carcinogencity:  0.496
Eye Corrosion:  0.978
Eye Irritation:  0.206
Respiratory Toxicity:  0.845

Download Data

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

  Natural Product: NPC246904

Natural Product ID:  NPC246904
Common Name*:   Saligcinnamide
IUPAC Name:   (E)-N-[(3S,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N-methyl-3-phenylprop-2-enamide
Synonyms:   saligcinnamide
Standard InCHIKey:  QRUDUXILSDZJOY-URJXLLGMSA-N
Standard InCHI:  InChI=1S/C33H50N2O/c1-23(34(4)5)28-15-16-29-27-14-13-25-22-26(18-20-32(25,2)30(27)19-21-33(28,29)3)35(6)31(36)17-12-24-10-8-7-9-11-24/h7-12,17,23,25-30H,13-16,18-22H2,1-6H3/b17-12+/t23-,25-,26-,27-,28+,29-,30-,32-,33+/m0/s1
SMILES:  CN([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2)N(C(=O)/C=C/c1ccccc1)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL409854
PubChem CID:   10255032
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0002340] Azasteroids and derivatives

*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
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14584959]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14643329]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[9548847]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27888 Sarcococca saligna Species Buxaceae 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
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica IC50 = 19900.0 nM PMID[484519]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Ki = 12200.0 nM PMID[484519]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 = 4840.0 nM PMID[484519]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens Ki = 6600.0 nM PMID[484519]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 19498.45 nM PMID[484520]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae IZ = 9.0 mm PMID[484521]
NPT172 Organism Proteus mirabilis Proteus mirabilis IZ = 7.0 mm PMID[484521]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa IZ = 6.0 mm PMID[484521]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 12.0 mm PMID[484521]
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes IZ = 8.0 mm PMID[484521]
NPT1242 Organism Salmonella typhi Salmonella enterica subsp. enterica serovar Typhi IZ = 6.0 mm PMID[484521]
NPT2912 Organism Shigella boydii Shigella boydii IZ = 6.0 mm PMID[484521]

☑ 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 NPC246904 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
0.9189 High Similarity NPC473573
0.8898 High Similarity NPC79698
0.8774 High Similarity NPC474582
0.8537 High Similarity NPC126458
0.8468 Intermediate Similarity NPC473962
0.8455 Intermediate Similarity NPC474695
0.746 Intermediate Similarity NPC109151
0.7453 Intermediate Similarity NPC147513
0.7383 Intermediate Similarity NPC157479
0.7315 Intermediate Similarity NPC17497
0.7315 Intermediate Similarity NPC305602
0.7211 Intermediate Similarity NPC73644
0.7094 Intermediate Similarity NPC239854
0.7075 Intermediate Similarity NPC90150
0.7009 Intermediate Similarity NPC215474
0.6991 Remote Similarity NPC473661
0.693 Remote Similarity NPC474974
0.6917 Remote Similarity NPC473418
0.6906 Remote Similarity NPC153007
0.687 Remote Similarity NPC256452
0.6861 Remote Similarity NPC132847
0.6842 Remote Similarity NPC475057
0.6777 Remote Similarity NPC143516
0.6777 Remote Similarity NPC167336
0.6759 Remote Similarity NPC231986
0.6754 Remote Similarity NPC475023
0.6754 Remote Similarity NPC475059
0.6754 Remote Similarity NPC470926
0.6752 Remote Similarity NPC472258
0.6752 Remote Similarity NPC475427
0.6721 Remote Similarity NPC474804
0.6721 Remote Similarity NPC474973
0.6721 Remote Similarity NPC130898
0.6719 Remote Similarity NPC239357
0.6696 Remote Similarity NPC60408
0.6667 Remote Similarity NPC472696
0.6667 Remote Similarity NPC3202
0.6667 Remote Similarity NPC472701
0.6667 Remote Similarity NPC472683
0.6667 Remote Similarity NPC472695
0.6645 Remote Similarity NPC63047
0.6645 Remote Similarity NPC475248
0.6644 Remote Similarity NPC212799
0.662 Remote Similarity NPC130251
0.6612 Remote Similarity NPC474866
0.6612 Remote Similarity NPC471829
0.6612 Remote Similarity NPC475939
0.6612 Remote Similarity NPC472691
0.661 Remote Similarity NPC133135
0.661 Remote Similarity NPC251579
0.6593 Remote Similarity NPC119326
0.6585 Remote Similarity NPC472699
0.6585 Remote Similarity NPC472700
0.6585 Remote Similarity NPC471447
0.6573 Remote Similarity NPC301760
0.6549 Remote Similarity NPC43308
0.6496 Remote Similarity NPC40488
0.6489 Remote Similarity NPC470546
0.6483 Remote Similarity NPC473922
0.648 Remote Similarity NPC473676
0.6467 Remote Similarity NPC275839
0.6466 Remote Similarity NPC314192
0.6462 Remote Similarity NPC470544
0.6452 Remote Similarity NPC45033
0.6444 Remote Similarity NPC22746
0.6412 Remote Similarity NPC470545
0.6408 Remote Similarity NPC478140
0.64 Remote Similarity NPC66936
0.64 Remote Similarity NPC55529
0.6387 Remote Similarity NPC219573
0.6387 Remote Similarity NPC185208
0.6387 Remote Similarity NPC476750
0.6377 Remote Similarity NPC473322
0.6372 Remote Similarity NPC182106
0.6372 Remote Similarity NPC311769
0.6357 Remote Similarity NPC32858
0.6357 Remote Similarity NPC53044
0.6357 Remote Similarity NPC194857
0.6345 Remote Similarity NPC22082
0.6345 Remote Similarity NPC186284
0.6339 Remote Similarity NPC474088
0.6331 Remote Similarity NPC124802
0.6328 Remote Similarity NPC475013
0.6319 Remote Similarity NPC286994
0.6311 Remote Similarity NPC476993
0.6308 Remote Similarity NPC33742
0.6304 Remote Similarity NPC239990
0.6304 Remote Similarity NPC105114
0.6304 Remote Similarity NPC152850
0.6304 Remote Similarity NPC89923
0.6304 Remote Similarity NPC71933
0.6303 Remote Similarity NPC329430
0.6299 Remote Similarity NPC104345
0.6293 Remote Similarity NPC298115
0.6289 Remote Similarity NPC476749
0.6286 Remote Similarity NPC126859
0.6286 Remote Similarity NPC259665
0.6286 Remote Similarity NPC89769
0.6286 Remote Similarity NPC255447
0.6284 Remote Similarity NPC475578
0.6269 Remote Similarity NPC200964
0.6262 Remote Similarity NPC476904
0.6261 Remote Similarity NPC53492
0.626 Remote Similarity NPC58200
0.6259 Remote Similarity NPC8305
0.6259 Remote Similarity NPC469537
0.6259 Remote Similarity NPC268763
0.6259 Remote Similarity NPC66177
0.6241 Remote Similarity NPC264580
0.6241 Remote Similarity NPC220698
0.6239 Remote Similarity NPC3190
0.6239 Remote Similarity NPC249018
0.6232 Remote Similarity NPC136453
0.6231 Remote Similarity NPC476048
0.6231 Remote Similarity NPC35850
0.6231 Remote Similarity NPC276949
0.6222 Remote Similarity NPC71684
0.6214 Remote Similarity NPC179224
0.6211 Remote Similarity NPC473743
0.6207 Remote Similarity NPC259252
0.6198 Remote Similarity NPC239185
0.6195 Remote Similarity NPC104070
0.619 Remote Similarity NPC471516
0.6187 Remote Similarity NPC478079
0.6186 Remote Similarity NPC125226
0.6184 Remote Similarity NPC154602
0.6184 Remote Similarity NPC243756
0.6174 Remote Similarity NPC328824
0.617 Remote Similarity NPC157311
0.6164 Remote Similarity NPC150712
0.616 Remote Similarity NPC275467
0.6159 Remote Similarity NPC109787
0.6154 Remote Similarity NPC325568
0.6148 Remote Similarity NPC27833
0.6148 Remote Similarity NPC476990
0.6148 Remote Similarity NPC134882
0.6144 Remote Similarity NPC285381
0.6144 Remote Similarity NPC122106
0.6143 Remote Similarity NPC111428
0.6134 Remote Similarity NPC59677
0.6134 Remote Similarity NPC323420
0.6132 Remote Similarity NPC473442
0.6132 Remote Similarity NPC120167
0.6131 Remote Similarity NPC46427
0.6129 Remote Similarity NPC329375
0.6127 Remote Similarity NPC8761
0.6127 Remote Similarity NPC44805
0.6126 Remote Similarity NPC159661
0.6119 Remote Similarity NPC472698
0.6119 Remote Similarity NPC472697
0.6103 Remote Similarity NPC202521
0.6102 Remote Similarity NPC26224
0.6099 Remote Similarity NPC200589
0.6093 Remote Similarity NPC476757
0.609 Remote Similarity NPC222029
0.6087 Remote Similarity NPC222466
0.6083 Remote Similarity NPC476754
0.6083 Remote Similarity NPC71140
0.6075 Remote Similarity NPC21773
0.6067 Remote Similarity NPC116519
0.6066 Remote Similarity NPC265220
0.6063 Remote Similarity NPC473498
0.6058 Remote Similarity NPC252878
0.6054 Remote Similarity NPC243162
0.6053 Remote Similarity NPC171639
0.6048 Remote Similarity NPC474001
0.6048 Remote Similarity NPC472879
0.6048 Remote Similarity NPC109514
0.6043 Remote Similarity NPC101719
0.6032 Remote Similarity NPC56168
0.6028 Remote Similarity NPC116057
0.6028 Remote Similarity NPC213969
0.6028 Remote Similarity NPC165726
0.6016 Remote Similarity NPC120393
0.6016 Remote Similarity NPC75724
0.6014 Remote Similarity NPC161069
0.6014 Remote Similarity NPC6975
0.6013 Remote Similarity NPC470274
0.6013 Remote Similarity NPC225319
0.6 Remote Similarity NPC143173
0.6 Remote Similarity NPC271642
0.6 Remote Similarity NPC133162
0.6 Remote Similarity NPC311330
0.6 Remote Similarity NPC1682
0.6 Remote Similarity NPC188844
0.6 Remote Similarity NPC7214
0.5986 Remote Similarity NPC469560
0.5982 Remote Similarity NPC211322
0.5975 Remote Similarity NPC469741
0.5972 Remote Similarity NPC313663
0.5972 Remote Similarity NPC149379
0.597 Remote Similarity NPC285926
0.597 Remote Similarity NPC315276
0.597 Remote Similarity NPC14672
0.5969 Remote Similarity NPC470252
0.596 Remote Similarity NPC44649
0.5959 Remote Similarity NPC471123
0.5957 Remote Similarity NPC470648
0.5956 Remote Similarity NPC226143
0.5948 Remote Similarity NPC152684

  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 NPC246904 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 NPD7679 Phase 2
0.7311 Intermediate Similarity NPD8010 Approved
0.7311 Intermediate Similarity NPD8009 Approved
0.7259 Intermediate Similarity NPD8125 Discontinued
0.725 Intermediate Similarity NPD4063 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4803 Discontinued
0.7154 Intermediate Similarity NPD6330 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3346 Approved
0.7117 Intermediate Similarity NPD3344 Approved
0.7099 Intermediate Similarity NPD5653 Discontinued
0.708 Intermediate Similarity NPD3982 Approved
0.708 Intermediate Similarity NPD3980 Approved
0.708 Intermediate Similarity NPD2878 Approved
0.7077 Intermediate Similarity NPD3550 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD3547 Approved
0.7077 Intermediate Similarity NPD3549 Approved
0.7037 Intermediate Similarity NPD4544 Approved
0.7009 Intermediate Similarity NPD4170 Approved
0.7009 Intermediate Similarity NPD5630 Phase 1
0.7009 Intermediate Similarity NPD4169 Approved
0.7009 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD6345 Approved
0.7008 Intermediate Similarity NPD6343 Approved
0.696 Remote Similarity NPD3551 Approved
0.6957 Remote Similarity NPD5964 Phase 2
0.6957 Remote Similarity NPD5963 Phase 2
0.6957 Remote Similarity NPD2895 Discontinued
0.6949 Remote Similarity NPD6588 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6024 Approved
0.6949 Remote Similarity NPD6027 Approved
0.6916 Remote Similarity NPD3035 Approved
0.6909 Remote Similarity NPD4636 Approved
0.6897 Remote Similarity NPD4655 Approved
0.6897 Remote Similarity NPD5598 Approved
0.6897 Remote Similarity NPD4657 Approved
0.6897 Remote Similarity NPD5597 Approved
0.6881 Remote Similarity NPD5178 Approved
0.686 Remote Similarity NPD7130 Phase 3
0.6825 Remote Similarity NPD2508 Discontinued
0.6818 Remote Similarity NPD5916 Discontinued
0.6818 Remote Similarity NPD2205 Approved
0.6818 Remote Similarity NPD7464 Phase 3
0.6818 Remote Similarity NPD2208 Approved
0.6807 Remote Similarity NPD5716 Approved
0.6807 Remote Similarity NPD813 Approved
0.6797 Remote Similarity NPD5990 Approved
0.6797 Remote Similarity NPD5991 Approved
0.6786 Remote Similarity NPD5675 Discontinued
0.6777 Remote Similarity NPD1767 Approved
0.6777 Remote Similarity NPD1766 Approved
0.6777 Remote Similarity NPD1763 Approved
0.6777 Remote Similarity NPD1765 Approved
0.6777 Remote Similarity NPD1761 Approved
0.6754 Remote Similarity NPD4543 Discontinued
0.6736 Remote Similarity NPD8239 Clinical (unspecified phase)
0.6724 Remote Similarity NPD4094 Approved
0.6718 Remote Similarity NPD1302 Clinical (unspecified phase)
0.6696 Remote Similarity NPD4407 Approved
0.6696 Remote Similarity NPD4408 Approved
0.6696 Remote Similarity NPD4405 Approved
0.6695 Remote Similarity NPD4263 Approved
0.6695 Remote Similarity NPD4813 Approved
0.6694 Remote Similarity NPD3581 Discontinued
0.669 Remote Similarity NPD7720 Phase 2
0.6667 Remote Similarity NPD2193 Phase 2
0.6667 Remote Similarity NPD5915 Approved
0.6667 Remote Similarity NPD2648 Phase 3
0.6667 Remote Similarity NPD5753 Discontinued
0.6667 Remote Similarity NPD2196 Discontinued
0.6667 Remote Similarity NPD1738 Approved
0.6642 Remote Similarity NPD2754 Discontinued
0.6642 Remote Similarity NPD6792 Phase 3
0.6641 Remote Similarity NPD6806 Phase 1
0.6639 Remote Similarity NPD2192 Approved
0.6639 Remote Similarity NPD2197 Approved
0.6639 Remote Similarity NPD5717 Approved
0.6639 Remote Similarity NPD742 Approved
0.6638 Remote Similarity NPD6548 Approved
0.6638 Remote Similarity NPD6549 Approved
0.6637 Remote Similarity NPD3345 Approved
0.6636 Remote Similarity NPD4635 Approved
0.6621 Remote Similarity NPD8131 Suspended
0.6614 Remote Similarity NPD5181 Approved
0.6614 Remote Similarity NPD5179 Approved
0.6614 Remote Similarity NPD5180 Approved
0.6609 Remote Similarity NPD3000 Approved
0.6609 Remote Similarity NPD2998 Approved
0.6609 Remote Similarity NPD2997 Approved
0.6607 Remote Similarity NPD4409 Approved
0.6607 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6607 Remote Similarity NPD3099 Discontinued
0.6607 Remote Similarity NPD4406 Approved
0.6606 Remote Similarity NPD4026 Approved
0.6606 Remote Similarity NPD4027 Approved
0.6581 Remote Similarity NPD5554 Approved
0.6579 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6577 Remote Similarity NPD2539 Approved
0.6577 Remote Similarity NPD2538 Approved
0.6567 Remote Similarity NPD6025 Phase 1
0.6555 Remote Similarity NPD5832 Phase 3
0.6555 Remote Similarity NPD466 Approved
0.6555 Remote Similarity NPD4117 Approved
0.6549 Remote Similarity NPD4145 Approved
0.6549 Remote Similarity NPD4146 Approved
0.6549 Remote Similarity NPD7254 Discontinued
0.6547 Remote Similarity NPD7578 Phase 2
0.6542 Remote Similarity NPD4147 Approved
0.6542 Remote Similarity NPD4144 Approved
0.6538 Remote Similarity NPD3806 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6531 Remote Similarity NPD8165 Discontinued
0.6531 Remote Similarity NPD7794 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6472 Discontinued
0.6522 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6515 Remote Similarity NPD5836 Discontinued
0.6512 Remote Similarity NPD4032 Approved
0.6512 Remote Similarity NPD4031 Approved
0.65 Remote Similarity NPD787 Suspended
0.6496 Remote Similarity NPD7582 Discontinued
0.6496 Remote Similarity NPD4542 Approved
0.6496 Remote Similarity NPD4545 Approved
0.6484 Remote Similarity NPD7059 Approved
0.6484 Remote Similarity NPD3598 Phase 3
0.6484 Remote Similarity NPD7060 Approved
0.6475 Remote Similarity NPD3357 Discontinued
0.6471 Remote Similarity NPD1099 Approved
0.6471 Remote Similarity NPD1100 Approved
0.6466 Remote Similarity NPD5576 Approved
0.6466 Remote Similarity NPD5579 Approved
0.6452 Remote Similarity NPD1064 Approved
0.6452 Remote Similarity NPD1065 Approved
0.6452 Remote Similarity NPD5706 Approved
0.6452 Remote Similarity NPD5705 Approved
0.6452 Remote Similarity NPD7170 Discontinued
0.6452 Remote Similarity NPD5704 Approved
0.6439 Remote Similarity NPD5517 Phase 2
0.6439 Remote Similarity NPD5516 Phase 2
0.6438 Remote Similarity NPD7949 Clinical (unspecified phase)
0.6434 Remote Similarity NPD3867 Phase 2
0.6429 Remote Similarity NPD6740 Clinical (unspecified phase)
0.6418 Remote Similarity NPD3529 Phase 2
0.6417 Remote Similarity NPD6499 Approved
0.6417 Remote Similarity NPD6498 Approved
0.6408 Remote Similarity NPD7192 Discontinued
0.6395 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6395 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6393 Remote Similarity NPD2171 Approved
0.6393 Remote Similarity NPD4719 Phase 2
0.6393 Remote Similarity NPD4119 Approved
0.6391 Remote Similarity NPD4416 Clinical (unspecified phase)
0.6385 Remote Similarity NPD1323 Discontinued
0.6371 Remote Similarity NPD1677 Discontinued
0.6371 Remote Similarity NPD959 Discontinued
0.637 Remote Similarity NPD5335 Discontinued
0.637 Remote Similarity NPD7082 Approved
0.637 Remote Similarity NPD6408 Phase 1
0.6364 Remote Similarity NPD5372 Approved
0.6364 Remote Similarity NPD5371 Approved
0.6364 Remote Similarity NPD3979 Approved
0.6364 Remote Similarity NPD8148 Approved
0.6364 Remote Similarity NPD3904 Approved
0.6364 Remote Similarity NPD4705 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8147 Approved
0.6364 Remote Similarity NPD3981 Approved
0.6364 Remote Similarity NPD7541 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3903 Approved
0.6357 Remote Similarity NPD6075 Approved
0.6357 Remote Similarity NPD6076 Approved
0.635 Remote Similarity NPD6563 Approved
0.635 Remote Similarity NPD6564 Approved
0.635 Remote Similarity NPD6565 Approved
0.6345 Remote Similarity NPD2010 Phase 3
0.6343 Remote Similarity NPD5187 Clinical (unspecified phase)
0.6338 Remote Similarity NPD7733 Phase 2
0.6338 Remote Similarity NPD8643 Discontinued
0.6331 Remote Similarity NPD2606 Approved
0.6331 Remote Similarity NPD3595 Approved
0.6331 Remote Similarity NPD2605 Approved
0.6331 Remote Similarity NPD3594 Approved
0.6328 Remote Similarity NPD2124 Approved
0.6327 Remote Similarity NPD7487 Discontinued
0.6327 Remote Similarity NPD7259 Approved
0.6319 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6308 Remote Similarity NPD851 Approved
0.6308 Remote Similarity NPD853 Approved
0.6308 Remote Similarity NPD4766 Approved
0.6299 Remote Similarity NPD7633 Discontinued
0.6296 Remote Similarity NPD3624 Phase 2
0.6296 Remote Similarity NPD4478 Clinical (unspecified phase)
0.629 Remote Similarity NPD4937 Approved
0.629 Remote Similarity NPD2577 Clinical (unspecified phase)
0.629 Remote Similarity NPD4936 Approved
0.6289 Remote Similarity NPD7795 Phase 2
0.6288 Remote Similarity NPD5130 Phase 3
0.6288 Remote Similarity NPD7522 Discontinued
0.6288 Remote Similarity NPD7610 Discontinued
0.6286 Remote Similarity NPD5155 Approved
0.6286 Remote Similarity NPD5156 Approved
0.6284 Remote Similarity NPD7295 Approved
0.6277 Remote Similarity NPD2962 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