Structure

Physi-Chem Properties

Molecular Weight:  506.19
Volume:  511.315
LogP:  3.773
LogD:  3.495
LogS:  -5.067
# Rotatable Bonds:  8
TPSA:  92.68
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.484
Synthetic Accessibility Score:  4.089
Fsp3:  0.345
Lipinski Rule-of-5:  Accepted
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:  -5.246
MDCK Permeability:  6.880534056108445e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.035
30% Bioavailability (F30%):  0.658

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.618
Plasma Protein Binding (PPB):  83.65341186523438%
Volume Distribution (VD):  1.201
Pgp-substrate:  9.149179458618164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.038
CYP1A2-substrate:  0.924
CYP2C19-inhibitor:  0.768
CYP2C19-substrate:  0.866
CYP2C9-inhibitor:  0.717
CYP2C9-substrate:  0.726
CYP2D6-inhibitor:  0.095
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.965
CYP3A4-substrate:  0.916

ADMET: Excretion

Clearance (CL):  9.494
Half-life (T1/2):  0.16

ADMET: Toxicity

hERG Blockers:  0.664
Human Hepatotoxicity (H-HT):  0.527
Drug-inuced Liver Injury (DILI):  0.505
AMES Toxicity:  0.421
Rat Oral Acute Toxicity:  0.726
Maximum Recommended Daily Dose:  0.61
Skin Sensitization:  0.049
Carcinogencity:  0.138
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.765

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

  Natural Product: NPC209463

Natural Product ID:  NPC209463
Common Name*:   (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-Amino-10-Chloro-2-Hydroxydecanoyl]Amino]-3-Hydroxypropanoyl]-Methylamino]-3-Methylbutanoyl]Amino]-4-(4-Hydroxyphenyl)Butanoic Acid
IUPAC Name:   (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-amino-10-chloro-2-hydroxydecanoyl]amino]-3-hydroxypropanoyl]-methylamino]-3-methylbutanoyl]amino]-4-(4-hydroxyphenyl)butanoic acid
Synonyms:  
Standard InCHIKey:  QYOGCHNVZHLFTR-RYWAYVEBSA-N
Standard InCHI:  InChI=1S/C29H47ClN4O8/c1-18(2)24(26(38)32-22(29(41)42)15-12-19-10-13-20(36)14-11-19)34(3)28(40)23(17-35)33-27(39)25(37)21(31)9-7-5-4-6-8-16-30/h10-11,13-14,18,21-25,35-37H,4-9,12,15-17,31H2,1-3H3,(H,32,38)(H,33,39)(H,41,42)/t21-,22+,23+,24+,25+/m1/s1
SMILES:  ClCCCCCCC[C@H]([C@@H](C(=N[C@H](C(=O)N([C@H](C(=N[C@H](C(=O)O)CCc1ccc(cc1)O)O)C(C)C)C)CO)O)O)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3188512
PubChem CID:   46902107
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0002010] Hybrid peptides

*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
NPO15753 Pterocarpus angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11854 Romalea microptera Species Romaleidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4232 Rabdosia coetsoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16841 Elsholtzia bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4232 Rabdosia coetsoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12128 Ipomoea purpurea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15753 Pterocarpus angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19977 Desmanthus illinoensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12128 Ipomoea purpurea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15753 Pterocarpus angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16276 Croton hieronymi Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12128 Ipomoea purpurea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9159 Narcissus serotinus Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4232 Rabdosia coetsoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11854 Romalea microptera Species Romaleidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15508 Ambrosia cordifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12412 Ormosia cinerea Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1443 Monomorium fieldi Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19977 Desmanthus illinoensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO911 Sistotrema raduloides Species Corticiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16841 Elsholtzia bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14714 Equisetum silvaticum Species Equisetaceae 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
NPT3904 Individual Protein Endoplasmic reticulum aminopeptidase 1 Homo sapiens AC50 = 682.0 nM PMID[458771]
NPT3903 Individual Protein Endoplasmic reticulum aminopeptidase 2 Homo sapiens AC50 = 1470.0 nM PMID[458771]
NPT2 Others Unspecified AC50 = 44.9 nM PMID[458771]

☑ 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 NPC209463 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
0.875 High Similarity NPC63931
0.8523 High Similarity NPC323662
0.84 Intermediate Similarity NPC328763
0.8313 Intermediate Similarity NPC473580
0.8263 Intermediate Similarity NPC89831
0.8221 Intermediate Similarity NPC475544
0.8199 Intermediate Similarity NPC476268
0.8144 Intermediate Similarity NPC280022
0.811 Intermediate Similarity NPC469243
0.8107 Intermediate Similarity NPC248670
0.8095 Intermediate Similarity NPC196091
0.8059 Intermediate Similarity NPC471165
0.8047 Intermediate Similarity NPC328494
0.8038 Intermediate Similarity NPC81026
0.8024 Intermediate Similarity NPC290755
0.8024 Intermediate Similarity NPC304074
0.8024 Intermediate Similarity NPC471771
0.8012 Intermediate Similarity NPC50016
0.8 Intermediate Similarity NPC273755
0.7988 Intermediate Similarity NPC46009
0.7975 Intermediate Similarity NPC244509
0.7975 Intermediate Similarity NPC266741
0.7964 Intermediate Similarity NPC223207
0.7953 Intermediate Similarity NPC26108
0.795 Intermediate Similarity NPC473491
0.791 Intermediate Similarity NPC94862
0.7895 Intermediate Similarity NPC306804
0.7882 Intermediate Similarity NPC473693
0.7882 Intermediate Similarity NPC475204
0.7882 Intermediate Similarity NPC471568
0.7882 Intermediate Similarity NPC276506
0.7882 Intermediate Similarity NPC475123
0.7849 Intermediate Similarity NPC473354
0.7849 Intermediate Similarity NPC158277
0.7831 Intermediate Similarity NPC244336
0.7821 Intermediate Similarity NPC51047
0.7821 Intermediate Similarity NPC6570
0.7816 Intermediate Similarity NPC45037
0.7816 Intermediate Similarity NPC119652
0.7816 Intermediate Similarity NPC97526
0.7814 Intermediate Similarity NPC477550
0.7814 Intermediate Similarity NPC477552
0.7805 Intermediate Similarity NPC39431
0.7802 Intermediate Similarity NPC473371
0.7801 Intermediate Similarity NPC326027
0.7797 Intermediate Similarity NPC299806
0.7789 Intermediate Similarity NPC326333
0.7778 Intermediate Similarity NPC198254
0.7778 Intermediate Similarity NPC274198
0.7764 Intermediate Similarity NPC16188
0.7746 Intermediate Similarity NPC476227
0.7744 Intermediate Similarity NPC56685
0.7744 Intermediate Similarity NPC262166
0.774 Intermediate Similarity NPC294951
0.773 Intermediate Similarity NPC477551
0.773 Intermediate Similarity NPC469443
0.7719 Intermediate Similarity NPC186617
0.7714 Intermediate Similarity NPC194671
0.7714 Intermediate Similarity NPC269750
0.7706 Intermediate Similarity NPC61004
0.7701 Intermediate Similarity NPC196243
0.7692 Intermediate Similarity NPC302715
0.7688 Intermediate Similarity NPC137627
0.7683 Intermediate Similarity NPC233702
0.7677 Intermediate Similarity NPC326966
0.7674 Intermediate Similarity NPC40234
0.7673 Intermediate Similarity NPC469426
0.7673 Intermediate Similarity NPC469427
0.7667 Intermediate Similarity NPC102959
0.7661 Intermediate Similarity NPC294516
0.7661 Intermediate Similarity NPC107938
0.7661 Intermediate Similarity NPC328649
0.7644 Intermediate Similarity NPC159767
0.7644 Intermediate Similarity NPC136797
0.7644 Intermediate Similarity NPC155506
0.7644 Intermediate Similarity NPC279871
0.7636 Intermediate Similarity NPC202198
0.7633 Intermediate Similarity NPC241794
0.7627 Intermediate Similarity NPC473404
0.7627 Intermediate Similarity NPC476321
0.7625 Intermediate Similarity NPC251439
0.7625 Intermediate Similarity NPC91953
0.7624 Intermediate Similarity NPC60516
0.7624 Intermediate Similarity NPC61332
0.7624 Intermediate Similarity NPC240130
0.7614 Intermediate Similarity NPC475421
0.7584 Intermediate Similarity NPC471526
0.7582 Intermediate Similarity NPC470728
0.7562 Intermediate Similarity NPC197921
0.756 Intermediate Similarity NPC326349
0.756 Intermediate Similarity NPC323336
0.7558 Intermediate Similarity NPC473502
0.7548 Intermediate Similarity NPC325651
0.7542 Intermediate Similarity NPC471050
0.7542 Intermediate Similarity NPC471048
0.7542 Intermediate Similarity NPC471049
0.7531 Intermediate Similarity NPC315266
0.7529 Intermediate Similarity NPC230611
0.7528 Intermediate Similarity NPC477637
0.7527 Intermediate Similarity NPC163961
0.7527 Intermediate Similarity NPC473305
0.7516 Intermediate Similarity NPC469360
0.7515 Intermediate Similarity NPC324081
0.75 Intermediate Similarity NPC315542
0.75 Intermediate Similarity NPC476259
0.7487 Intermediate Similarity NPC220060
0.7486 Intermediate Similarity NPC470903
0.7486 Intermediate Similarity NPC470112
0.7486 Intermediate Similarity NPC167763
0.7453 Intermediate Similarity NPC476989
0.7448 Intermediate Similarity NPC469444
0.7443 Intermediate Similarity NPC473402
0.7442 Intermediate Similarity NPC472923
0.7438 Intermediate Similarity NPC313694
0.7438 Intermediate Similarity NPC242159
0.7434 Intermediate Similarity NPC27581
0.7425 Intermediate Similarity NPC5194
0.7425 Intermediate Similarity NPC261934
0.7418 Intermediate Similarity NPC96275
0.7414 Intermediate Similarity NPC129486
0.7412 Intermediate Similarity NPC319320
0.7412 Intermediate Similarity NPC287757
0.7405 Intermediate Similarity NPC65714
0.7391 Intermediate Similarity NPC307357
0.7391 Intermediate Similarity NPC268841
0.7391 Intermediate Similarity NPC46098
0.7375 Intermediate Similarity NPC127741
0.7374 Intermediate Similarity NPC153554
0.7372 Intermediate Similarity NPC296712
0.7363 Intermediate Similarity NPC276120
0.7356 Intermediate Similarity NPC302597
0.7333 Intermediate Similarity NPC135121
0.7333 Intermediate Similarity NPC469445
0.732 Intermediate Similarity NPC474862
0.7317 Intermediate Similarity NPC201244
0.7317 Intermediate Similarity NPC477217
0.7306 Intermediate Similarity NPC219350
0.7306 Intermediate Similarity NPC194699
0.7301 Intermediate Similarity NPC176226
0.7301 Intermediate Similarity NPC168861
0.7297 Intermediate Similarity NPC473407
0.7297 Intermediate Similarity NPC473378
0.7296 Intermediate Similarity NPC244866
0.7288 Intermediate Similarity NPC475532
0.7287 Intermediate Similarity NPC471592
0.7284 Intermediate Similarity NPC471201
0.7273 Intermediate Similarity NPC477632
0.7273 Intermediate Similarity NPC477638
0.7262 Intermediate Similarity NPC162104
0.7256 Intermediate Similarity NPC52748
0.7247 Intermediate Similarity NPC165285
0.7247 Intermediate Similarity NPC17698
0.7246 Intermediate Similarity NPC2501
0.7237 Intermediate Similarity NPC319950
0.7237 Intermediate Similarity NPC283760
0.7233 Intermediate Similarity NPC45191
0.7233 Intermediate Similarity NPC257390
0.7219 Intermediate Similarity NPC314083
0.7215 Intermediate Similarity NPC478147
0.7202 Intermediate Similarity NPC475168
0.7202 Intermediate Similarity NPC7817
0.7197 Intermediate Similarity NPC319766
0.7195 Intermediate Similarity NPC197682
0.7189 Intermediate Similarity NPC246591
0.7179 Intermediate Similarity NPC478005
0.7178 Intermediate Similarity NPC322526
0.7178 Intermediate Similarity NPC48202
0.7171 Intermediate Similarity NPC314992
0.7166 Intermediate Similarity NPC477631
0.7161 Intermediate Similarity NPC35996
0.716 Intermediate Similarity NPC68865
0.716 Intermediate Similarity NPC64205
0.7159 Intermediate Similarity NPC141957
0.7157 Intermediate Similarity NPC277306
0.7157 Intermediate Similarity NPC469442
0.7151 Intermediate Similarity NPC56635
0.7151 Intermediate Similarity NPC477636
0.7143 Intermediate Similarity NPC477639
0.7134 Intermediate Similarity NPC168113
0.7126 Intermediate Similarity NPC311658
0.7126 Intermediate Similarity NPC145113
0.712 Intermediate Similarity NPC138083
0.7119 Intermediate Similarity NPC66490
0.7118 Intermediate Similarity NPC473341
0.7118 Intermediate Similarity NPC122590
0.7117 Intermediate Similarity NPC473055
0.7117 Intermediate Similarity NPC473052
0.7113 Intermediate Similarity NPC81845
0.7112 Intermediate Similarity NPC248822
0.709 Intermediate Similarity NPC80514
0.7088 Intermediate Similarity NPC32064
0.7086 Intermediate Similarity NPC289776
0.7086 Intermediate Similarity NPC133470
0.7086 Intermediate Similarity NPC191863
0.7085 Intermediate Similarity NPC25539
0.7081 Intermediate Similarity NPC328070
0.7077 Intermediate Similarity NPC246303
0.7076 Intermediate Similarity NPC470902
0.7066 Intermediate Similarity NPC314358
0.7059 Intermediate Similarity NPC174122

  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 NPC209463 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
0.8098 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD7978 Discontinued
0.7843 Intermediate Similarity NPD3136 Phase 2
0.7706 Intermediate Similarity NPD8303 Discontinued
0.753 Intermediate Similarity NPD7523 Phase 3
0.7516 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD6682 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD7450 Phase 2
0.7429 Intermediate Similarity NPD5137 Approved
0.7412 Intermediate Similarity NPD7495 Discontinued
0.7371 Intermediate Similarity NPD7608 Discontinued
0.7365 Intermediate Similarity NPD7303 Discontinued
0.7273 Intermediate Similarity NPD4652 Approved
0.7219 Intermediate Similarity NPD7131 Phase 3
0.7209 Intermediate Similarity NPD8019 Approved
0.7178 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD2217 Approved
0.7171 Intermediate Similarity NPD2218 Phase 2
0.7143 Intermediate Similarity NPD2098 Approved
0.7134 Intermediate Similarity NPD2240 Approved
0.7134 Intermediate Similarity NPD9570 Approved
0.7134 Intermediate Similarity NPD2239 Approved
0.712 Intermediate Similarity NPD5946 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7485 Phase 3
0.7119 Intermediate Similarity NPD7484 Phase 3
0.7066 Intermediate Similarity NPD1968 Approved
0.7066 Intermediate Similarity NPD3400 Discontinued
0.7066 Intermediate Similarity NPD6676 Phase 2
0.7066 Intermediate Similarity NPD1967 Approved
0.7039 Intermediate Similarity NPD9568 Approved
0.7029 Intermediate Similarity NPD2097 Approved
0.6994 Remote Similarity NPD555 Phase 2
0.6975 Remote Similarity NPD259 Phase 1
0.6957 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6951 Remote Similarity NPD8172 Phase 2
0.6951 Remote Similarity NPD8173 Phase 2
0.6946 Remote Similarity NPD6681 Discovery
0.6937 Remote Similarity NPD9569 Approved
0.6933 Remote Similarity NPD6346 Approved
0.6927 Remote Similarity NPD2889 Approved
0.6927 Remote Similarity NPD2888 Approved
0.6927 Remote Similarity NPD2017 Approved
0.6927 Remote Similarity NPD2890 Approved
0.6901 Remote Similarity NPD5348 Clinical (unspecified phase)
0.686 Remote Similarity NPD7613 Discontinued
0.686 Remote Similarity NPD6078 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6677 Suspended
0.6835 Remote Similarity NPD2561 Approved
0.6835 Remote Similarity NPD2562 Approved
0.6829 Remote Similarity NPD8416 Discontinued
0.681 Remote Similarity NPD1330 Phase 2
0.681 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6901 Phase 3
0.6805 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4677 Discontinued
0.6788 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8076 Discontinued
0.6782 Remote Similarity NPD6670 Clinical (unspecified phase)
0.678 Remote Similarity NPD3465 Clinical (unspecified phase)
0.678 Remote Similarity NPD7972 Discontinued
0.6774 Remote Similarity NPD318 Approved
0.6774 Remote Similarity NPD16 Approved
0.6774 Remote Similarity NPD317 Approved
0.6774 Remote Similarity NPD856 Approved
0.677 Remote Similarity NPD7451 Discontinued
0.6769 Remote Similarity NPD7811 Phase 3
0.6769 Remote Similarity NPD7810 Phase 3
0.6768 Remote Similarity NPD5745 Approved
0.6768 Remote Similarity NPD1423 Approved
0.6768 Remote Similarity NPD829 Discontinued
0.676 Remote Similarity NPD8031 Discontinued
0.6755 Remote Similarity NPD6851 Approved
0.6755 Remote Similarity NPD6853 Approved
0.6753 Remote Similarity NPD255 Approved
0.6753 Remote Similarity NPD256 Approved
0.675 Remote Similarity NPD3125 Approved
0.6748 Remote Similarity NPD9536 Phase 1
0.6748 Remote Similarity NPD9537 Phase 1
0.673 Remote Similarity NPD3071 Approved
0.673 Remote Similarity NPD3073 Approved
0.673 Remote Similarity NPD3072 Approved
0.6728 Remote Similarity NPD3626 Phase 3
0.6728 Remote Similarity NPD4177 Approved
0.6728 Remote Similarity NPD4175 Approved
0.6727 Remote Similarity NPD826 Approved
0.6727 Remote Similarity NPD825 Approved
0.6725 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6723 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6723 Remote Similarity NPD5355 Approved
0.6723 Remote Similarity NPD5356 Approved
0.672 Remote Similarity NPD6297 Approved
0.6707 Remote Similarity NPD3555 Approved
0.6707 Remote Similarity NPD3554 Approved
0.6707 Remote Similarity NPD3552 Approved
0.6707 Remote Similarity NPD601 Approved
0.6707 Remote Similarity NPD3553 Approved
0.6707 Remote Similarity NPD597 Approved
0.6707 Remote Similarity NPD598 Approved
0.6706 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6705 Remote Similarity NPD3536 Discontinued
0.6702 Remote Similarity NPD7617 Discontinued
0.6667 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1132 Approved
0.6667 Remote Similarity NPD4731 Phase 3
0.6667 Remote Similarity NPD6390 Discontinued
0.6667 Remote Similarity NPD4761 Approved
0.6667 Remote Similarity NPD1136 Approved
0.6667 Remote Similarity NPD4762 Approved
0.6667 Remote Similarity NPD1130 Approved
0.6667 Remote Similarity NPD5339 Clinical (unspecified phase)
0.6667 Remote Similarity NPD258 Approved
0.6667 Remote Similarity NPD257 Approved
0.6667 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6648 Remote Similarity NPD3455 Phase 2
0.6648 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6073 Approved
0.6647 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6647 Remote Similarity NPD5314 Approved
0.6647 Remote Similarity NPD5725 Approved
0.6646 Remote Similarity NPD5746 Approved
0.6631 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6628 Remote Similarity NPD8323 Discontinued
0.6627 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6627 Remote Similarity NPD5323 Approved
0.6627 Remote Similarity NPD4153 Approved
0.6626 Remote Similarity NPD3040 Approved
0.6624 Remote Similarity NPD1759 Phase 1
0.661 Remote Similarity NPD8417 Discontinued
0.6609 Remote Similarity NPD3985 Discontinued
0.6609 Remote Similarity NPD6419 Discontinued
0.6607 Remote Similarity NPD6852 Discontinued
0.6603 Remote Similarity NPD3123 Discovery
0.6597 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6596 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6595 Remote Similarity NPD5200 Clinical (unspecified phase)
0.659 Remote Similarity NPD5308 Clinical (unspecified phase)
0.6587 Remote Similarity NPD4757 Clinical (unspecified phase)
0.6585 Remote Similarity NPD5263 Approved
0.6585 Remote Similarity NPD4676 Approved
0.6584 Remote Similarity NPD4659 Approved
0.6582 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6582 Remote Similarity NPD7282 Approved
0.6578 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6564 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6561 Remote Similarity NPD3936 Clinical (unspecified phase)
0.6561 Remote Similarity NPD4954 Approved
0.6561 Remote Similarity NPD5026 Approved
0.6561 Remote Similarity NPD1758 Phase 1
0.6561 Remote Similarity NPD36 Approved
0.6561 Remote Similarity NPD5034 Approved
0.6561 Remote Similarity NPD4955 Approved
0.6561 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6561 Remote Similarity NPD5028 Approved
0.6548 Remote Similarity NPD2568 Approved
0.6545 Remote Similarity NPD4738 Phase 2
0.6543 Remote Similarity NPD196 Phase 1
0.6538 Remote Similarity NPD6315 Phase 2
0.6532 Remote Similarity NPD5309 Clinical (unspecified phase)
0.6527 Remote Similarity NPD3061 Approved
0.6527 Remote Similarity NPD3059 Approved
0.6527 Remote Similarity NPD3062 Approved
0.6527 Remote Similarity NPD6623 Phase 3
0.6526 Remote Similarity NPD5035 Approved
0.6522 Remote Similarity NPD2584 Suspended
0.652 Remote Similarity NPD3803 Clinical (unspecified phase)
0.6519 Remote Similarity NPD316 Approved
0.6515 Remote Similarity NPD7565 Approved
0.6508 Remote Similarity NPD5030 Phase 2
0.6506 Remote Similarity NPD5299 Approved
0.6503 Remote Similarity NPD1131 Approved
0.6503 Remote Similarity NPD2626 Approved
0.6503 Remote Similarity NPD1134 Approved
0.6503 Remote Similarity NPD1133 Approved
0.6503 Remote Similarity NPD2160 Approved
0.6503 Remote Similarity NPD2627 Approved
0.6503 Remote Similarity NPD2159 Approved
0.6503 Remote Similarity NPD1129 Approved
0.6503 Remote Similarity NPD4103 Phase 2
0.6503 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6503 Remote Similarity NPD1135 Approved
0.6503 Remote Similarity NPD2628 Approved
0.6503 Remote Similarity NPD2625 Approved
0.6494 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4152 Approved
0.6489 Remote Similarity NPD5484 Approved
0.6489 Remote Similarity NPD5485 Approved
0.6488 Remote Similarity NPD275 Approved
0.6488 Remote Similarity NPD8643 Discontinued
0.6488 Remote Similarity NPD274 Approved
0.6484 Remote Similarity NPD5218 Approved
0.6484 Remote Similarity NPD5219 Approved
0.6482 Remote Similarity NPD4914 Approved
0.6477 Remote Similarity NPD52 Approved
0.6477 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6477 Remote Similarity NPD7526 Approved
0.6477 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6620 Discovery
0.6467 Remote Similarity NPD5747 Discontinued
0.6467 Remote Similarity NPD6405 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