Structure

Physi-Chem Properties

Molecular Weight:  331.25
Volume:  378.611
LogP:  5.885
LogD:  4.421
LogS:  -3.462
# Rotatable Bonds:  13
TPSA:  49.33
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.411
Synthetic Accessibility Score:  2.239
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.696
MDCK Permeability:  1.9736296962946653e-05
Pgp-inhibitor:  0.37
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.403
Plasma Protein Binding (PPB):  97.56324005126953%
Volume Distribution (VD):  0.93
Pgp-substrate:  0.952062726020813%

ADMET: Metabolism

CYP1A2-inhibitor:  0.813
CYP1A2-substrate:  0.291
CYP2C19-inhibitor:  0.934
CYP2C19-substrate:  0.129
CYP2C9-inhibitor:  0.832
CYP2C9-substrate:  0.96
CYP2D6-inhibitor:  0.893
CYP2D6-substrate:  0.192
CYP3A4-inhibitor:  0.885
CYP3A4-substrate:  0.228

ADMET: Excretion

Clearance (CL):  10.189
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.192
Human Hepatotoxicity (H-HT):  0.103
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.033
Maximum Recommended Daily Dose:  0.047
Skin Sensitization:  0.954
Carcinogencity:  0.161
Eye Corrosion:  0.011
Eye Irritation:  0.668
Respiratory Toxicity:  0.353

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Similar NPs/Drugs  

  Natural Product: NPC142297

Natural Product ID:  NPC142297
Common Name*:   N-(4-Hydroxyphenethyl)-3-Methyldodec-2-Enamide
IUPAC Name:   (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide
Synonyms:  
Standard InCHIKey:  NBUAIVBXANEDGZ-ZCXUNETKSA-N
Standard InCHI:  InChI=1S/C21H33NO2/c1-3-4-5-6-7-8-9-10-18(2)17-21(24)22-16-15-19-11-13-20(23)14-12-19/h11-14,17,23H,3-10,15-16H2,1-2H3,(H,22,24)/b18-17-
SMILES:  CCCCCCCCC/C(=CC(=NCCc1ccc(cc1)O)O)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464613
PubChem CID:   21773786
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO28209 Muricea austera Species Plexauridae Eukaryota n.a. Pacific coast of Panama n.a. PMID[17067146]
NPO27465 Sinularia erecta Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[27142697]
NPO28209 Muricea austera Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27465 Sinularia erecta Species Alcyoniidae 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
NPT2740 Cell Line Neutrophils IC50 > 10000.0 nM PMID[543099]
NPT2740 Cell Line Neutrophils Inhibition = 48.0 % PMID[543099]
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 = 6300.0 nM PMID[543099]
NPT112 Cell Line MOLT-4 Homo sapiens IC50 = 9700.0 nM PMID[543099]
NPT2740 Cell Line Neutrophils Inhibition = 102.0 % PMID[543099]
NPT2740 Cell Line Neutrophils IC50 = 1000.0 nM PMID[543099]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 36000.0 nM PMID[543098]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 50000.0 nM PMID[543098]

☑ 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 NPC142297 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
0.97 High Similarity NPC231705
0.9608 High Similarity NPC258056
0.9596 High Similarity NPC178902
0.9515 High Similarity NPC474149
0.951 High Similarity NPC24101
0.951 High Similarity NPC96224
0.9074 High Similarity NPC317254
0.8952 High Similarity NPC153690
0.8824 High Similarity NPC289381
0.8824 High Similarity NPC155847
0.8807 High Similarity NPC118202
0.875 High Similarity NPC283760
0.8739 High Similarity NPC283468
0.8661 High Similarity NPC122009
0.8649 High Similarity NPC82963
0.8636 High Similarity NPC142599
0.8571 High Similarity NPC38458
0.8571 High Similarity NPC311737
0.8544 High Similarity NPC125732
0.8532 High Similarity NPC166837
0.8522 High Similarity NPC474862
0.8447 Intermediate Similarity NPC107619
0.8421 Intermediate Similarity NPC43275
0.8421 Intermediate Similarity NPC268572
0.84 Intermediate Similarity NPC55561
0.8348 Intermediate Similarity NPC263835
0.83 Intermediate Similarity NPC280347
0.83 Intermediate Similarity NPC177420
0.8261 Intermediate Similarity NPC319950
0.825 Intermediate Similarity NPC296712
0.823 Intermediate Similarity NPC37302
0.82 Intermediate Similarity NPC113460
0.82 Intermediate Similarity NPC25493
0.8182 Intermediate Similarity NPC197783
0.8151 Intermediate Similarity NPC62101
0.8151 Intermediate Similarity NPC95733
0.8137 Intermediate Similarity NPC270547
0.8119 Intermediate Similarity NPC318325
0.8119 Intermediate Similarity NPC242240
0.8119 Intermediate Similarity NPC98772
0.8119 Intermediate Similarity NPC123273
0.8113 Intermediate Similarity NPC29601
0.81 Intermediate Similarity NPC184169
0.81 Intermediate Similarity NPC23167
0.8099 Intermediate Similarity NPC153990
0.8099 Intermediate Similarity NPC251571
0.8081 Intermediate Similarity NPC248817
0.8081 Intermediate Similarity NPC175313
0.8077 Intermediate Similarity NPC26244
0.807 Intermediate Similarity NPC303370
0.8067 Intermediate Similarity NPC211218
0.8034 Intermediate Similarity NPC17388
0.8034 Intermediate Similarity NPC471308
0.8034 Intermediate Similarity NPC289330
0.8034 Intermediate Similarity NPC160120
0.8034 Intermediate Similarity NPC53596
0.8033 Intermediate Similarity NPC155838
0.8018 Intermediate Similarity NPC145638
0.8018 Intermediate Similarity NPC290566
0.8 Intermediate Similarity NPC473388
0.7981 Intermediate Similarity NPC151715
0.798 Intermediate Similarity NPC265146
0.798 Intermediate Similarity NPC124436
0.7967 Intermediate Similarity NPC35961
0.7967 Intermediate Similarity NPC195749
0.7967 Intermediate Similarity NPC52029
0.7966 Intermediate Similarity NPC284078
0.7963 Intermediate Similarity NPC68055
0.7941 Intermediate Similarity NPC258219
0.7934 Intermediate Similarity NPC29477
0.7913 Intermediate Similarity NPC213
0.7913 Intermediate Similarity NPC10286
0.7903 Intermediate Similarity NPC326966
0.7899 Intermediate Similarity NPC142577
0.7899 Intermediate Similarity NPC27581
0.7886 Intermediate Similarity NPC478147
0.7885 Intermediate Similarity NPC94139
0.7885 Intermediate Similarity NPC210497
0.7885 Intermediate Similarity NPC325292
0.7885 Intermediate Similarity NPC147284
0.7885 Intermediate Similarity NPC162314
0.7885 Intermediate Similarity NPC138117
0.7885 Intermediate Similarity NPC306884
0.7885 Intermediate Similarity NPC3358
0.7869 Intermediate Similarity NPC301713
0.7864 Intermediate Similarity NPC300017
0.7843 Intermediate Similarity NPC104216
0.784 Intermediate Similarity NPC214869
0.784 Intermediate Similarity NPC244866
0.783 Intermediate Similarity NPC82664
0.783 Intermediate Similarity NPC292730
0.783 Intermediate Similarity NPC132271
0.783 Intermediate Similarity NPC216520
0.783 Intermediate Similarity NPC33168
0.7815 Intermediate Similarity NPC83279
0.781 Intermediate Similarity NPC58674
0.781 Intermediate Similarity NPC27323
0.781 Intermediate Similarity NPC316301
0.7807 Intermediate Similarity NPC146422
0.7798 Intermediate Similarity NPC196479
0.7797 Intermediate Similarity NPC256369
0.7788 Intermediate Similarity NPC304541
0.7788 Intermediate Similarity NPC45040
0.7788 Intermediate Similarity NPC155908
0.7778 Intermediate Similarity NPC285078
0.7778 Intermediate Similarity NPC313737
0.7778 Intermediate Similarity NPC6854
0.776 Intermediate Similarity NPC114102
0.776 Intermediate Similarity NPC45191
0.7745 Intermediate Similarity NPC307235
0.7745 Intermediate Similarity NPC407
0.7742 Intermediate Similarity NPC325651
0.7736 Intermediate Similarity NPC313650
0.7724 Intermediate Similarity NPC476353
0.7719 Intermediate Similarity NPC227553
0.7719 Intermediate Similarity NPC163674
0.7714 Intermediate Similarity NPC181709
0.7712 Intermediate Similarity NPC85276
0.7698 Intermediate Similarity NPC130595
0.7698 Intermediate Similarity NPC328070
0.7698 Intermediate Similarity NPC93882
0.7692 Intermediate Similarity NPC192
0.7692 Intermediate Similarity NPC151764
0.7686 Intermediate Similarity NPC471314
0.7686 Intermediate Similarity NPC471315
0.7685 Intermediate Similarity NPC92730
0.7685 Intermediate Similarity NPC78119
0.7685 Intermediate Similarity NPC260775
0.7685 Intermediate Similarity NPC132078
0.7685 Intermediate Similarity NPC128723
0.7685 Intermediate Similarity NPC216468
0.7685 Intermediate Similarity NPC51333
0.768 Intermediate Similarity NPC474091
0.767 Intermediate Similarity NPC27974
0.7667 Intermediate Similarity NPC473050
0.7667 Intermediate Similarity NPC473051
0.7661 Intermediate Similarity NPC186898
0.7658 Intermediate Similarity NPC211551
0.7656 Intermediate Similarity NPC64205
0.7656 Intermediate Similarity NPC6570
0.7647 Intermediate Similarity NPC155393
0.7647 Intermediate Similarity NPC198747
0.7647 Intermediate Similarity NPC473031
0.7642 Intermediate Similarity NPC128062
0.7638 Intermediate Similarity NPC267237
0.7624 Intermediate Similarity NPC3210
0.7623 Intermediate Similarity NPC307020
0.7619 Intermediate Similarity NPC204210
0.7619 Intermediate Similarity NPC255550
0.7619 Intermediate Similarity NPC308885
0.7619 Intermediate Similarity NPC473724
0.7615 Intermediate Similarity NPC248396
0.7615 Intermediate Similarity NPC213730
0.7615 Intermediate Similarity NPC70677
0.7615 Intermediate Similarity NPC12931
0.7615 Intermediate Similarity NPC48730
0.7615 Intermediate Similarity NPC225506
0.7615 Intermediate Similarity NPC130756
0.7615 Intermediate Similarity NPC129373
0.7611 Intermediate Similarity NPC146530
0.76 Intermediate Similarity NPC271808
0.7596 Intermediate Similarity NPC141139
0.7596 Intermediate Similarity NPC471307
0.7596 Intermediate Similarity NPC159178
0.7596 Intermediate Similarity NPC209764
0.7596 Intermediate Similarity NPC74936
0.7596 Intermediate Similarity NPC121872
0.7596 Intermediate Similarity NPC78041
0.7593 Intermediate Similarity NPC201967
0.7593 Intermediate Similarity NPC260000
0.7593 Intermediate Similarity NPC225464
0.7593 Intermediate Similarity NPC152097
0.7593 Intermediate Similarity NPC315921
0.7593 Intermediate Similarity NPC77492
0.7586 Intermediate Similarity NPC59387
0.7583 Intermediate Similarity NPC321133
0.7578 Intermediate Similarity NPC218530
0.757 Intermediate Similarity NPC274678
0.757 Intermediate Similarity NPC8392
0.757 Intermediate Similarity NPC32714
0.7549 Intermediate Similarity NPC203076
0.7549 Intermediate Similarity NPC286904
0.7549 Intermediate Similarity NPC150837
0.7545 Intermediate Similarity NPC472585
0.7545 Intermediate Similarity NPC471578
0.7545 Intermediate Similarity NPC91461
0.7545 Intermediate Similarity NPC7686
0.7545 Intermediate Similarity NPC101025
0.7545 Intermediate Similarity NPC40258
0.7544 Intermediate Similarity NPC316052
0.7542 Intermediate Similarity NPC281686
0.7542 Intermediate Similarity NPC106551
0.7542 Intermediate Similarity NPC258992
0.7542 Intermediate Similarity NPC188867
0.7538 Intermediate Similarity NPC312770
0.7538 Intermediate Similarity NPC322526
0.7538 Intermediate Similarity NPC14600
0.7538 Intermediate Similarity NPC41473
0.7538 Intermediate Similarity NPC160607
0.7538 Intermediate Similarity NPC471201

  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 NPC142297 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
0.8396 Intermediate Similarity NPD9610 Approved
0.8396 Intermediate Similarity NPD9608 Approved
0.8378 Intermediate Similarity NPD2228 Approved
0.8378 Intermediate Similarity NPD2234 Approved
0.8378 Intermediate Similarity NPD2229 Approved
0.8167 Intermediate Similarity NPD7451 Discontinued
0.8155 Intermediate Similarity NPD2934 Approved
0.8155 Intermediate Similarity NPD2933 Approved
0.8077 Intermediate Similarity NPD2860 Approved
0.8077 Intermediate Similarity NPD2859 Approved
0.8073 Intermediate Similarity NPD1444 Approved
0.8073 Intermediate Similarity NPD1445 Approved
0.8018 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.798 Intermediate Similarity NPD111 Approved
0.7966 Intermediate Similarity NPD3421 Phase 3
0.7931 Intermediate Similarity NPD856 Approved
0.7931 Intermediate Similarity NPD16 Approved
0.7917 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7863 Intermediate Similarity NPD1759 Phase 1
0.7857 Intermediate Similarity NPD1792 Phase 2
0.785 Intermediate Similarity NPD3020 Approved
0.784 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD3136 Phase 2
0.781 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7807 Intermediate Similarity NPD9377 Approved
0.7807 Intermediate Similarity NPD9379 Approved
0.7797 Intermediate Similarity NPD4093 Discontinued
0.7778 Intermediate Similarity NPD1758 Phase 1
0.7778 Intermediate Similarity NPD317 Approved
0.7778 Intermediate Similarity NPD318 Approved
0.7731 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD5304 Approved
0.7712 Intermediate Similarity NPD5303 Approved
0.7698 Intermediate Similarity NPD2674 Phase 3
0.7686 Intermediate Similarity NPD2562 Approved
0.7686 Intermediate Similarity NPD2561 Approved
0.7672 Intermediate Similarity NPD1793 Approved
0.7672 Intermediate Similarity NPD1791 Approved
0.7623 Intermediate Similarity NPD4659 Approved
0.7623 Intermediate Similarity NPD1669 Approved
0.7619 Intermediate Similarity NPD3145 Approved
0.7619 Intermediate Similarity NPD3144 Approved
0.7593 Intermediate Similarity NPD9273 Approved
0.7583 Intermediate Similarity NPD2668 Approved
0.7583 Intermediate Similarity NPD2667 Approved
0.7563 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD5310 Approved
0.7561 Intermediate Similarity NPD5311 Approved
0.7545 Intermediate Similarity NPD846 Approved
0.7545 Intermediate Similarity NPD940 Approved
0.7542 Intermediate Similarity NPD9568 Approved
0.7538 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD9614 Approved
0.7521 Intermediate Similarity NPD9618 Approved
0.7521 Intermediate Similarity NPD3143 Discontinued
0.75 Intermediate Similarity NPD3055 Approved
0.75 Intermediate Similarity NPD821 Approved
0.75 Intermediate Similarity NPD3053 Approved
0.75 Intermediate Similarity NPD4103 Phase 2
0.75 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD7450 Phase 2
0.7479 Intermediate Similarity NPD9613 Approved
0.7479 Intermediate Similarity NPD9616 Approved
0.7479 Intermediate Similarity NPD9615 Approved
0.7459 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD256 Approved
0.7458 Intermediate Similarity NPD255 Approved
0.7453 Intermediate Similarity NPD6690 Approved
0.7438 Intermediate Similarity NPD1751 Approved
0.7424 Intermediate Similarity NPD7978 Discontinued
0.7417 Intermediate Similarity NPD316 Approved
0.7411 Intermediate Similarity NPD179 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD1809 Phase 2
0.7407 Intermediate Similarity NPD844 Approved
0.7387 Intermediate Similarity NPD4818 Approved
0.7387 Intermediate Similarity NPD4817 Approved
0.7383 Intermediate Similarity NPD845 Approved
0.7377 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD6346 Approved
0.736 Intermediate Similarity NPD1129 Approved
0.736 Intermediate Similarity NPD1134 Approved
0.736 Intermediate Similarity NPD1133 Approved
0.736 Intermediate Similarity NPD1135 Approved
0.736 Intermediate Similarity NPD1131 Approved
0.7328 Intermediate Similarity NPD3555 Approved
0.7328 Intermediate Similarity NPD3552 Approved
0.7328 Intermediate Similarity NPD3553 Approved
0.7328 Intermediate Similarity NPD3554 Approved
0.7295 Intermediate Similarity NPD9384 Approved
0.7295 Intermediate Similarity NPD9381 Approved
0.7287 Intermediate Similarity NPD7477 Discontinued
0.728 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD2372 Approved
0.7259 Intermediate Similarity NPD7066 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD3070 Discontinued
0.7244 Intermediate Similarity NPD3636 Approved
0.7244 Intermediate Similarity NPD3635 Approved
0.7244 Intermediate Similarity NPD3637 Approved
0.7241 Intermediate Similarity NPD3021 Approved
0.7241 Intermediate Similarity NPD3022 Approved
0.7232 Intermediate Similarity NPD855 Approved
0.7232 Intermediate Similarity NPD854 Approved
0.7227 Intermediate Similarity NPD475 Phase 2
0.7217 Intermediate Similarity NPD9507 Approved
0.7213 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD3685 Discontinued
0.72 Intermediate Similarity NPD6582 Phase 2
0.72 Intermediate Similarity NPD6583 Phase 3
0.72 Intermediate Similarity NPD9622 Approved
0.7188 Intermediate Similarity NPD2606 Approved
0.7188 Intermediate Similarity NPD2605 Approved
0.7182 Intermediate Similarity NPD288 Approved
0.7179 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD9620 Approved
0.7165 Intermediate Similarity NPD9619 Approved
0.7165 Intermediate Similarity NPD2195 Approved
0.7165 Intermediate Similarity NPD9621 Approved
0.7165 Intermediate Similarity NPD2194 Approved
0.7164 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD840 Approved
0.7154 Intermediate Similarity NPD6405 Approved
0.7154 Intermediate Similarity NPD839 Approved
0.7154 Intermediate Similarity NPD6407 Approved
0.7143 Intermediate Similarity NPD3028 Approved
0.7143 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1242 Phase 1
0.7132 Intermediate Similarity NPD5156 Approved
0.7132 Intermediate Similarity NPD5155 Approved
0.713 Intermediate Similarity NPD1814 Approved
0.713 Intermediate Similarity NPD1812 Approved
0.7121 Intermediate Similarity NPD2157 Approved
0.7121 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD2230 Approved
0.712 Intermediate Similarity NPD2233 Approved
0.712 Intermediate Similarity NPD2232 Approved
0.7117 Intermediate Similarity NPD9612 Approved
0.7117 Intermediate Similarity NPD9609 Approved
0.7117 Intermediate Similarity NPD9611 Approved
0.7111 Intermediate Similarity NPD7153 Discontinued
0.7109 Intermediate Similarity NPD1712 Approved
0.7109 Intermediate Similarity NPD4993 Discontinued
0.7107 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6682 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1980 Approved
0.7097 Intermediate Similarity NPD1981 Approved
0.7097 Intermediate Similarity NPD1671 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1983 Approved
0.709 Intermediate Similarity NPD2161 Phase 2
0.7077 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD601 Approved
0.7077 Intermediate Similarity NPD597 Approved
0.7077 Intermediate Similarity NPD598 Approved
0.7069 Intermediate Similarity NPD6406 Approved
0.7063 Intermediate Similarity NPD1755 Approved
0.7054 Intermediate Similarity NPD9712 Approved
0.7054 Intermediate Similarity NPD3594 Approved
0.7054 Intermediate Similarity NPD3595 Approved
0.7034 Intermediate Similarity NPD4253 Approved
0.7034 Intermediate Similarity NPD4254 Approved
0.7031 Intermediate Similarity NPD6584 Phase 3
0.7023 Intermediate Similarity NPD1136 Approved
0.7023 Intermediate Similarity NPD1132 Approved
0.7023 Intermediate Similarity NPD829 Discontinued
0.7023 Intermediate Similarity NPD1130 Approved
0.7018 Intermediate Similarity NPD4658 Approved
0.7018 Intermediate Similarity NPD3682 Approved
0.7018 Intermediate Similarity NPD4229 Approved
0.7018 Intermediate Similarity NPD3681 Approved
0.7018 Intermediate Similarity NPD4656 Approved
0.7018 Intermediate Similarity NPD3680 Approved
0.7018 Intermediate Similarity NPD4231 Approved
0.7018 Intermediate Similarity NPD3683 Approved
0.7 Intermediate Similarity NPD1024 Discontinued
0.7 Intermediate Similarity NPD7303 Discontinued
0.7 Intermediate Similarity NPD4814 Discontinued
0.6992 Remote Similarity NPD3054 Approved
0.6992 Remote Similarity NPD5314 Approved
0.6992 Remote Similarity NPD3052 Approved
0.6992 Remote Similarity NPD2568 Approved
0.6991 Remote Similarity NPD4760 Clinical (unspecified phase)
0.6985 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6124 Clinical (unspecified phase)
0.6972 Remote Similarity NPD159 Clinical (unspecified phase)
0.697 Remote Similarity NPD3062 Approved
0.697 Remote Similarity NPD3061 Approved
0.697 Remote Similarity NPD3059 Approved
0.6964 Remote Similarity NPD9711 Approved
0.6964 Remote Similarity NPD9710 Approved
0.6957 Remote Similarity NPD311 Approved
0.6957 Remote Similarity NPD10 Approved
0.6957 Remote Similarity NPD310 Approved
0.6957 Remote Similarity NPD314 Approved
0.6957 Remote Similarity NPD315 Approved
0.6957 Remote Similarity NPD309 Approved
0.695 Remote Similarity NPD7523 Phase 3
0.6942 Remote Similarity NPD593 Approved
0.6942 Remote Similarity NPD595 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