Structure

Physi-Chem Properties

Molecular Weight:  300.18
Volume:  326.526
LogP:  2.761
LogD:  3.36
LogS:  -4.053
# Rotatable Bonds:  7
TPSA:  49.41
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.85
Synthetic Accessibility Score:  3.045
Fsp3:  0.444
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.685
MDCK Permeability:  2.9083706976962276e-05
Pgp-inhibitor:  0.749
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.927
Plasma Protein Binding (PPB):  90.21662139892578%
Volume Distribution (VD):  0.59
Pgp-substrate:  7.853959560394287%

ADMET: Metabolism

CYP1A2-inhibitor:  0.59
CYP1A2-substrate:  0.355
CYP2C19-inhibitor:  0.699
CYP2C19-substrate:  0.552
CYP2C9-inhibitor:  0.329
CYP2C9-substrate:  0.836
CYP2D6-inhibitor:  0.04
CYP2D6-substrate:  0.184
CYP3A4-inhibitor:  0.134
CYP3A4-substrate:  0.198

ADMET: Excretion

Clearance (CL):  2.95
Half-life (T1/2):  0.641

ADMET: Toxicity

hERG Blockers:  0.083
Human Hepatotoxicity (H-HT):  0.591
Drug-inuced Liver Injury (DILI):  0.31
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.071
Maximum Recommended Daily Dose:  0.566
Skin Sensitization:  0.88
Carcinogencity:  0.058
Eye Corrosion:  0.008
Eye Irritation:  0.064
Respiratory Toxicity:  0.669

Download Data

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

  Natural Product: NPC130898

Natural Product ID:  NPC130898
Common Name*:   Odorine
IUPAC Name:   (2S)-2-methyl-N-[(2R)-1-[(E)-3-phenylprop-2-enoyl]pyrrolidin-2-yl]butanamide
Synonyms:   Odorine
Standard InCHIKey:  KZAOEMMZRGEBST-IXVOVUJJSA-N
Standard InCHI:  InChI=1S/C18H24N2O2/c1-3-14(2)18(22)19-16-10-7-13-20(16)17(21)12-11-15-8-5-4-6-9-15/h4-6,8-9,11-12,14,16H,3,7,10,13H2,1-2H3,(H,19,22)/b12-11+/t14-,16+/m0/s1
SMILES:  CC[C@@H](C(=N[C@H]1CCCN1C(=O)/C=C/c1ccccc1)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL521297
PubChem CID:   23242585
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids 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
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94986-0]
NPO32616 aglaia sp. Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[10775404]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. flower n.a. PMID[17679444]
NPO32616 aglaia sp. Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[8496701]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[8759160]
NPO32616 aglaia sp. Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[9868148]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8565 Dioscorea dumetorum Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO292 Aglaia elliptica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3839 Aglaia roxburghiana Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8565 Dioscorea dumetorum Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8565 Dioscorea dumetorum Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8409 Galium semiamictum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1356 Bacillus circulans Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO292 Aglaia elliptica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15626 Alternaria japonica Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2867 Cotula coronopifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13865 Cucumaria chronhjelmi Species Cucumariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7567 Parmelia rigida Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3839 Aglaia roxburghiana Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4528 Penicillium lapatayae Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8281 Epimedium davidi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1360 Penicillium nordicum Species Aspergillaceae 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 > 20.0 ug ml-1 PMID[548078]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[548078]
NPT91 Cell Line KB Homo sapiens ED50 > 20.0 ug ml-1 PMID[548078]
NPT762 Cell Line A-431 Homo sapiens ED50 > 20.0 ug ml-1 PMID[548078]
NPT858 Cell Line LNCaP Homo sapiens ED50 > 20.0 ug ml-1 PMID[548078]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[548078]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 35481.3 nM PMID[548079]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 39810.7 nM PMID[548079]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[548079]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 112201.8 nM PMID[548079]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[548078]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 6.4 ug ml-1 PMID[548078]
NPT2 Others Unspecified Potency = 517.4 nM PMID[548079]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 7375.3 nM PMID[548079]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 100000.0 nM PMID[548079]

☑ 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 NPC130898 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 NPC474804
1.0 High Similarity NPC474973
0.9898 High Similarity NPC143516
0.9223 High Similarity NPC473676
0.8785 High Similarity NPC475013
0.8624 High Similarity NPC476048
0.8148 Intermediate Similarity NPC471447
0.8137 Intermediate Similarity NPC474974
0.7913 Intermediate Similarity NPC239357
0.7778 Intermediate Similarity NPC329375
0.7549 Intermediate Similarity NPC305602
0.7549 Intermediate Similarity NPC17497
0.75 Intermediate Similarity NPC476990
0.75 Intermediate Similarity NPC200964
0.7438 Intermediate Similarity NPC202521
0.7407 Intermediate Similarity NPC472258
0.7377 Intermediate Similarity NPC252878
0.735 Intermediate Similarity NPC276949
0.735 Intermediate Similarity NPC35850
0.7345 Intermediate Similarity NPC45033
0.7317 Intermediate Similarity NPC46427
0.7317 Intermediate Similarity NPC6975
0.7311 Intermediate Similarity NPC315276
0.7311 Intermediate Similarity NPC285926
0.7311 Intermediate Similarity NPC470544
0.7311 Intermediate Similarity NPC14672
0.7288 Intermediate Similarity NPC33742
0.7258 Intermediate Similarity NPC22746
0.725 Intermediate Similarity NPC470545
0.7232 Intermediate Similarity NPC202613
0.7196 Intermediate Similarity NPC473661
0.719 Intermediate Similarity NPC470546
0.7075 Intermediate Similarity NPC470877
0.7064 Intermediate Similarity NPC256452
0.7048 Intermediate Similarity NPC471638
0.7031 Intermediate Similarity NPC473322
0.7016 Intermediate Similarity NPC71684
0.7009 Intermediate Similarity NPC172128
0.7009 Intermediate Similarity NPC121872
0.7009 Intermediate Similarity NPC159178
0.7009 Intermediate Similarity NPC471307
0.7009 Intermediate Similarity NPC78041
0.7009 Intermediate Similarity NPC209764
0.7009 Intermediate Similarity NPC141139
0.7009 Intermediate Similarity NPC74936
0.7 Intermediate Similarity NPC25565
0.6981 Remote Similarity NPC12429
0.6977 Remote Similarity NPC200589
0.6977 Remote Similarity NPC300315
0.6944 Remote Similarity NPC245259
0.6937 Remote Similarity NPC473501
0.6937 Remote Similarity NPC475439
0.6923 Remote Similarity NPC255447
0.6923 Remote Similarity NPC130309
0.6909 Remote Similarity NPC303045
0.6909 Remote Similarity NPC161972
0.6905 Remote Similarity NPC474082
0.6905 Remote Similarity NPC175726
0.6893 Remote Similarity NPC14326
0.687 Remote Similarity NPC325479
0.6822 Remote Similarity NPC325441
0.6818 Remote Similarity NPC471309
0.6818 Remote Similarity NPC287401
0.68 Remote Similarity NPC27833
0.6797 Remote Similarity NPC101719
0.6783 Remote Similarity NPC471317
0.6767 Remote Similarity NPC141050
0.6763 Remote Similarity NPC311658
0.6757 Remote Similarity NPC58674
0.6729 Remote Similarity NPC473031
0.6729 Remote Similarity NPC53492
0.6724 Remote Similarity NPC275467
0.6721 Remote Similarity NPC246904
0.6719 Remote Similarity NPC222466
0.6698 Remote Similarity NPC3210
0.6697 Remote Similarity NPC258627
0.6695 Remote Similarity NPC55529
0.6692 Remote Similarity NPC319766
0.6667 Remote Similarity NPC471265
0.6667 Remote Similarity NPC235421
0.6667 Remote Similarity NPC471264
0.6642 Remote Similarity NPC248283
0.6637 Remote Similarity NPC311242
0.6637 Remote Similarity NPC33168
0.6636 Remote Similarity NPC226438
0.6635 Remote Similarity NPC231986
0.6618 Remote Similarity NPC476133
0.6618 Remote Similarity NPC92784
0.6618 Remote Similarity NPC98424
0.6618 Remote Similarity NPC122553
0.6618 Remote Similarity NPC470884
0.6618 Remote Similarity NPC89489
0.6618 Remote Similarity NPC178662
0.661 Remote Similarity NPC327481
0.6581 Remote Similarity NPC88267
0.6581 Remote Similarity NPC113326
0.6581 Remote Similarity NPC194390
0.6581 Remote Similarity NPC224610
0.6545 Remote Similarity NPC316108
0.6544 Remote Similarity NPC43755
0.6525 Remote Similarity NPC473418
0.6522 Remote Similarity NPC269398
0.6522 Remote Similarity NPC263493
0.6522 Remote Similarity NPC476989
0.6515 Remote Similarity NPC165726
0.6515 Remote Similarity NPC111428
0.6515 Remote Similarity NPC213969
0.6509 Remote Similarity NPC474088
0.6508 Remote Similarity NPC220698
0.6493 Remote Similarity NPC194857
0.6493 Remote Similarity NPC32858
0.6493 Remote Similarity NPC246079
0.6481 Remote Similarity NPC203076
0.6475 Remote Similarity NPC161069
0.6475 Remote Similarity NPC468984
0.6471 Remote Similarity NPC191215
0.6471 Remote Similarity NPC274089
0.6466 Remote Similarity NPC469457
0.6429 Remote Similarity NPC476978
0.6429 Remote Similarity NPC52748
0.6423 Remote Similarity NPC474584
0.6423 Remote Similarity NPC273814
0.6404 Remote Similarity NPC471319
0.6404 Remote Similarity NPC471320
0.6383 Remote Similarity NPC209509
0.6383 Remote Similarity NPC313867
0.6383 Remote Similarity NPC322878
0.6383 Remote Similarity NPC5620
0.6383 Remote Similarity NPC477217
0.6383 Remote Similarity NPC316008
0.6383 Remote Similarity NPC201244
0.6383 Remote Similarity NPC315266
0.6379 Remote Similarity NPC12730
0.6377 Remote Similarity NPC132636
0.6372 Remote Similarity NPC71140
0.637 Remote Similarity NPC473002
0.637 Remote Similarity NPC207428
0.6356 Remote Similarity NPC471310
0.6341 Remote Similarity NPC275410
0.6338 Remote Similarity NPC314358
0.6338 Remote Similarity NPC262077
0.6333 Remote Similarity NPC473498
0.6333 Remote Similarity NPC68650
0.6327 Remote Similarity NPC469903
0.6316 Remote Similarity NPC218323
0.6312 Remote Similarity NPC315283
0.6312 Remote Similarity NPC314388
0.6311 Remote Similarity NPC271642
0.6304 Remote Similarity NPC127741
0.6304 Remote Similarity NPC68865
0.6294 Remote Similarity NPC135121
0.6294 Remote Similarity NPC145113
0.6294 Remote Similarity NPC329761
0.6294 Remote Similarity NPC138775
0.6294 Remote Similarity NPC16188
0.6294 Remote Similarity NPC225648
0.6288 Remote Similarity NPC171372
0.6273 Remote Similarity NPC198747
0.627 Remote Similarity NPC188010
0.6269 Remote Similarity NPC469666
0.6268 Remote Similarity NPC471680
0.6261 Remote Similarity NPC3371
0.626 Remote Similarity NPC319579
0.6259 Remote Similarity NPC313694
0.6259 Remote Similarity NPC242159
0.6259 Remote Similarity NPC77992
0.6258 Remote Similarity NPC355
0.625 Remote Similarity NPC324445
0.625 Remote Similarity NPC471821
0.625 Remote Similarity NPC167336
0.625 Remote Similarity NPC240848
0.625 Remote Similarity NPC471820
0.6241 Remote Similarity NPC77905
0.6226 Remote Similarity NPC475289
0.6226 Remote Similarity NPC192623
0.6226 Remote Similarity NPC475573
0.6222 Remote Similarity NPC314431
0.6218 Remote Similarity NPC164859
0.6214 Remote Similarity NPC46098
0.6214 Remote Similarity NPC476259
0.6214 Remote Similarity NPC98976
0.6214 Remote Similarity NPC307357
0.6214 Remote Similarity NPC239762
0.6214 Remote Similarity NPC469560
0.6214 Remote Similarity NPC268841
0.6214 Remote Similarity NPC163392
0.6207 Remote Similarity NPC2501
0.6207 Remote Similarity NPC472788
0.6207 Remote Similarity NPC283783
0.6207 Remote Similarity NPC129666
0.62 Remote Similarity NPC469898
0.6198 Remote Similarity NPC231705
0.619 Remote Similarity NPC471318
0.6174 Remote Similarity NPC108339
0.6172 Remote Similarity NPC169328
0.6172 Remote Similarity NPC254088
0.617 Remote Similarity NPC469427
0.617 Remote Similarity NPC168113
0.617 Remote Similarity NPC469426
0.6165 Remote Similarity NPC79698

  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 NPC130898 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
0.7391 Intermediate Similarity NPD2583 Phase 2
0.7315 Intermediate Similarity NPD157 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD2584 Suspended
0.7167 Intermediate Similarity NPD1344 Phase 2
0.7119 Intermediate Similarity NPD4165 Phase 2
0.7119 Intermediate Similarity NPD3066 Phase 2
0.7117 Intermediate Similarity NPD787 Suspended
0.7109 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD1576 Approved
0.7087 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD4791 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3632 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4125 Approved
0.6917 Remote Similarity NPD4782 Clinical (unspecified phase)
0.6917 Remote Similarity NPD3598 Phase 3
0.6911 Remote Similarity NPD998 Approved
0.6894 Remote Similarity NPD5272 Discontinued
0.6881 Remote Similarity NPD6690 Approved
0.6875 Remote Similarity NPD466 Approved
0.6842 Remote Similarity NPD813 Approved
0.6842 Remote Similarity NPD6588 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2196 Discontinued
0.6838 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6833 Remote Similarity NPD480 Approved
0.6818 Remote Similarity NPD941 Approved
0.6818 Remote Similarity NPD1080 Approved
0.6803 Remote Similarity NPD2622 Approved
0.6788 Remote Similarity NPD5341 Clinical (unspecified phase)
0.678 Remote Similarity NPD2679 Approved
0.678 Remote Similarity NPD2678 Approved
0.6769 Remote Similarity NPD3040 Approved
0.6769 Remote Similarity NPD3626 Phase 3
0.6767 Remote Similarity NPD8416 Discontinued
0.6757 Remote Similarity NPD4814 Discontinued
0.6754 Remote Similarity NPD4760 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7130 Phase 3
0.6748 Remote Similarity NPD3123 Discovery
0.6742 Remote Similarity NPD2078 Clinical (unspecified phase)
0.6741 Remote Similarity NPD4214 Discontinued
0.6727 Remote Similarity NPD1812 Approved
0.6727 Remote Similarity NPD1814 Approved
0.6723 Remote Similarity NPD4063 Clinical (unspecified phase)
0.6716 Remote Similarity NPD8643 Discontinued
0.6696 Remote Similarity NPD4119 Approved
0.6692 Remote Similarity NPD3588 Discontinued
0.6691 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6691 Remote Similarity NPD4158 Clinical (unspecified phase)
0.6667 Remote Similarity NPD21 Approved
0.6667 Remote Similarity NPD2044 Approved
0.6667 Remote Similarity NPD2047 Approved
0.6667 Remote Similarity NPD2046 Approved
0.6667 Remote Similarity NPD2048 Approved
0.6667 Remote Similarity NPD8173 Phase 2
0.6667 Remote Similarity NPD8172 Phase 2
0.6667 Remote Similarity NPD2031 Discontinued
0.6667 Remote Similarity NPD6631 Clinical (unspecified phase)
0.6667 Remote Similarity NPD742 Approved
0.6667 Remote Similarity NPD2043 Approved
0.6667 Remote Similarity NPD2051 Approved
0.6667 Remote Similarity NPD2050 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2045 Approved
0.6667 Remote Similarity NPD2049 Clinical (unspecified phase)
0.6636 Remote Similarity NPD530 Approved
0.6618 Remote Similarity NPD6901 Phase 3
0.6617 Remote Similarity NPD2846 Clinical (unspecified phase)
0.661 Remote Similarity NPD1064 Approved
0.661 Remote Similarity NPD1065 Approved
0.6609 Remote Similarity NPD5630 Phase 1
0.6604 Remote Similarity NPD5178 Approved
0.6593 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6593 Remote Similarity NPD4757 Clinical (unspecified phase)
0.6587 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6574 Remote Similarity NPD9538 Approved
0.6574 Remote Similarity NPD187 Approved
0.6567 Remote Similarity NPD4540 Clinical (unspecified phase)
0.6565 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6552 Remote Similarity NPD4803 Discontinued
0.6538 Remote Similarity NPD6792 Phase 3
0.6538 Remote Similarity NPD5577 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3125 Approved
0.6538 Remote Similarity NPD5578 Approved
0.6525 Remote Similarity NPD2192 Approved
0.6525 Remote Similarity NPD1677 Discontinued
0.6525 Remote Similarity NPD2197 Approved
0.6525 Remote Similarity NPD999 Phase 2
0.6525 Remote Similarity NPD5717 Approved
0.6522 Remote Similarity NPD1067 Discontinued
0.6519 Remote Similarity NPD4153 Approved
0.6518 Remote Similarity NPD720 Approved
0.6518 Remote Similarity NPD719 Approved
0.6515 Remote Similarity NPD1781 Discontinued
0.6512 Remote Similarity NPD5335 Discontinued
0.6512 Remote Similarity NPD3071 Approved
0.6512 Remote Similarity NPD3072 Approved
0.6512 Remote Similarity NPD3073 Approved
0.6504 Remote Similarity NPD3150 Approved
0.6504 Remote Similarity NPD2658 Approved
0.6504 Remote Similarity NPD3149 Approved
0.6504 Remote Similarity NPD2659 Approved
0.6504 Remote Similarity NPD3147 Approved
0.6504 Remote Similarity NPD3148 Approved
0.6496 Remote Similarity NPD5103 Approved
0.6496 Remote Similarity NPD4077 Clinical (unspecified phase)
0.6496 Remote Similarity NPD3682 Approved
0.6496 Remote Similarity NPD3680 Approved
0.6496 Remote Similarity NPD2244 Clinical (unspecified phase)
0.6493 Remote Similarity NPD6076 Approved
0.6493 Remote Similarity NPD6075 Approved
0.6491 Remote Similarity NPD2487 Clinical (unspecified phase)
0.648 Remote Similarity NPD4431 Clinical (unspecified phase)
0.6475 Remote Similarity NPD2022 Approved
0.6475 Remote Similarity NPD8076 Discontinued
0.6475 Remote Similarity NPD753 Approved
0.6475 Remote Similarity NPD2088 Approved
0.6475 Remote Similarity NPD2087 Approved
0.6475 Remote Similarity NPD7720 Phase 2
0.6475 Remote Similarity NPD2124 Approved
0.646 Remote Similarity NPD1081 Clinical (unspecified phase)
0.6452 Remote Similarity NPD2508 Discontinued
0.6449 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6446 Remote Similarity NPD3581 Discontinued
0.6441 Remote Similarity NPD3407 Phase 3
0.6435 Remote Similarity NPD1724 Approved
0.6435 Remote Similarity NPD4117 Approved
0.6434 Remote Similarity NPD4762 Approved
0.6434 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6434 Remote Similarity NPD4761 Approved
0.6429 Remote Similarity NPD7522 Discontinued
0.6429 Remote Similarity NPD5991 Approved
0.6429 Remote Similarity NPD5990 Approved
0.6429 Remote Similarity NPD752 Approved
0.6423 Remote Similarity NPD1762 Approved
0.6423 Remote Similarity NPD1764 Approved
0.6412 Remote Similarity NPD2634 Clinical (unspecified phase)
0.641 Remote Similarity NPD2171 Approved
0.641 Remote Similarity NPD1417 Approved
0.641 Remote Similarity NPD2648 Phase 3
0.641 Remote Similarity NPD1419 Approved
0.641 Remote Similarity NPD2193 Phase 2
0.6408 Remote Similarity NPD603 Approved
0.6408 Remote Similarity NPD4147 Approved
0.6408 Remote Similarity NPD4144 Approved
0.6406 Remote Similarity NPD7342 Discontinued
0.6406 Remote Similarity NPD4733 Approved
0.6404 Remote Similarity NPD2507 Clinical (unspecified phase)
0.64 Remote Similarity NPD1323 Discontinued
0.6395 Remote Similarity NPD7267 Clinical (unspecified phase)
0.6393 Remote Similarity NPD3643 Approved
0.6393 Remote Similarity NPD3642 Approved
0.6393 Remote Similarity NPD3644 Approved
0.6387 Remote Similarity NPD1766 Approved
0.6387 Remote Similarity NPD1761 Approved
0.6387 Remote Similarity NPD1767 Approved
0.6387 Remote Similarity NPD1765 Approved
0.6387 Remote Similarity NPD1763 Approved
0.6381 Remote Similarity NPD5371 Approved
0.6381 Remote Similarity NPD5372 Approved
0.6371 Remote Similarity NPD5064 Approved
0.6371 Remote Similarity NPD23 Approved
0.6371 Remote Similarity NPD5063 Approved
0.637 Remote Similarity NPD1329 Clinical (unspecified phase)
0.637 Remote Similarity NPD1330 Phase 2
0.6364 Remote Similarity NPD1101 Approved
0.6364 Remote Similarity NPD8290 Clinical (unspecified phase)
0.6357 Remote Similarity NPD4152 Approved
0.6356 Remote Similarity NPD5655 Clinical (unspecified phase)
0.6348 Remote Similarity NPD1875 Phase 1
0.6348 Remote Similarity NPD1100 Approved
0.6348 Remote Similarity NPD1099 Approved
0.6343 Remote Similarity NPD4676 Approved
0.6343 Remote Similarity NPD4207 Discontinued
0.6343 Remote Similarity NPD5263 Approved
0.6336 Remote Similarity NPD2371 Approved
0.6331 Remote Similarity NPD3480 Approved
0.6331 Remote Similarity NPD5301 Clinical (unspecified phase)
0.6328 Remote Similarity NPD2212 Approved
0.6328 Remote Similarity NPD2210 Approved
0.632 Remote Similarity NPD3867 Phase 2
0.6319 Remote Similarity NPD5614 Approved
0.6319 Remote Similarity NPD3988 Approved
0.6319 Remote Similarity NPD3987 Approved
0.6319 Remote Similarity NPD3282 Phase 1
0.6319 Remote Similarity NPD3283 Phase 3
0.6319 Remote Similarity NPD5613 Approved
0.6316 Remote Similarity NPD6259 Discontinued
0.6316 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6312 Remote Similarity NPD2436 Approved
0.6312 Remote Similarity NPD2437 Approved
0.6311 Remote Similarity NPD1108 Approved
0.6311 Remote Similarity NPD1107 Approved
0.6308 Remote Similarity NPD3529 Phase 2
0.6304 Remote Similarity NPD5004 Approved
0.6296 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6294 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6288 Remote Similarity NPD2961 Approved
0.6288 Remote Similarity NPD2962 Approved
0.6288 Remote Similarity NPD6325 Discontinued
0.6281 Remote Similarity NPD2243 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