Structure

Physi-Chem Properties

Molecular Weight:  297.14
Volume:  319.047
LogP:  2.481
LogD:  3.071
LogS:  -3.685
# Rotatable Bonds:  7
TPSA:  58.56
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.806
Synthetic Accessibility Score:  2.279
Fsp3:  0.167
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:  -4.825
MDCK Permeability:  1.2537124348455109e-05
Pgp-inhibitor:  0.37
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.872
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.555
Plasma Protein Binding (PPB):  93.78873443603516%
Volume Distribution (VD):  0.657
Pgp-substrate:  2.3651864528656006%

ADMET: Metabolism

CYP1A2-inhibitor:  0.776
CYP1A2-substrate:  0.106
CYP2C19-inhibitor:  0.87
CYP2C19-substrate:  0.519
CYP2C9-inhibitor:  0.665
CYP2C9-substrate:  0.961
CYP2D6-inhibitor:  0.37
CYP2D6-substrate:  0.889
CYP3A4-inhibitor:  0.521
CYP3A4-substrate:  0.23

ADMET: Excretion

Clearance (CL):  11.141
Half-life (T1/2):  0.424

ADMET: Toxicity

hERG Blockers:  0.442
Human Hepatotoxicity (H-HT):  0.304
Drug-inuced Liver Injury (DILI):  0.285
AMES Toxicity:  0.366
Rat Oral Acute Toxicity:  0.015
Maximum Recommended Daily Dose:  0.809
Skin Sensitization:  0.678
Carcinogencity:  0.251
Eye Corrosion:  0.005
Eye Irritation:  0.353
Respiratory Toxicity:  0.327

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Similar NPs/Drugs  

  Natural Product: NPC95733

Natural Product ID:  NPC95733
Common Name*:   (-)-Aegeline
IUPAC Name:   (E)-N-[(2S)-2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
Synonyms:   (-)-Aegeline
Standard InCHIKey:  QRFDENJATPJOKG-SNQZOLJRSA-N
Standard InCHI:  InChI=1S/C18H19NO3/c1-22-16-10-8-15(9-11-16)17(20)13-19-18(21)12-7-14-5-3-2-4-6-14/h2-12,17,20H,13H2,1H3,(H,19,21)/b12-7+/t17-/m1/s1
SMILES:  COc1ccc(cc1)[C@@H](CN=C(/C=C/c1ccccc1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL490882
PubChem CID:   11403749
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0002810] Cinnamic acid amides

*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
NPO5045 Aegle marmelos Species Rutaceae Eukaryota leaves n.a. n.a. PMID[18760601]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. bark n.a. PMID[21875114]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[23434131]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. fruit n.a. PMID[26247834]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[30579794]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 153000.0 nM PMID[492908]
NPT2 Others Unspecified Inhibition = 5.3 % PMID[492907]
NPT2 Others Unspecified Inhibition = 11.2 % PMID[492907]
NPT2 Others Unspecified Inhibition = 20.9 % PMID[492907]
NPT2 Others Unspecified Inhibition = 36.0 % PMID[492907]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 6820.0 nM PMID[492908]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 7260.0 nM PMID[492908]
NPT2 Others Unspecified Ratio CC50/IC50 = 22.43 n.a. PMID[492908]

☑ 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 NPC95733 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 NPC62101
0.9748 High Similarity NPC29477
0.9746 High Similarity NPC211218
0.916 High Similarity NPC43275
0.9083 High Similarity NPC263835
0.8923 High Similarity NPC14600
0.8923 High Similarity NPC41473
0.8923 High Similarity NPC312770
0.8923 High Similarity NPC204848
0.8923 High Similarity NPC160607
0.8855 High Similarity NPC299583
0.8731 High Similarity NPC178466
0.8731 High Similarity NPC63628
0.8667 High Similarity NPC303370
0.8644 High Similarity NPC166837
0.8583 High Similarity NPC301713
0.8537 High Similarity NPC256369
0.8516 High Similarity NPC251571
0.845 Intermediate Similarity NPC155838
0.8413 Intermediate Similarity NPC471314
0.8413 Intermediate Similarity NPC471315
0.8397 Intermediate Similarity NPC214869
0.839 Intermediate Similarity NPC96224
0.839 Intermediate Similarity NPC24101
0.8385 Intermediate Similarity NPC52029
0.8385 Intermediate Similarity NPC35961
0.8385 Intermediate Similarity NPC195749
0.8333 Intermediate Similarity NPC313414
0.8321 Intermediate Similarity NPC114102
0.8296 Intermediate Similarity NPC296898
0.8286 Intermediate Similarity NPC470935
0.8286 Intermediate Similarity NPC471032
0.8258 Intermediate Similarity NPC471953
0.8254 Intermediate Similarity NPC83279
0.8231 Intermediate Similarity NPC153990
0.8214 Intermediate Similarity NPC115144
0.8214 Intermediate Similarity NPC277857
0.8175 Intermediate Similarity NPC289330
0.8175 Intermediate Similarity NPC53596
0.8175 Intermediate Similarity NPC321133
0.8175 Intermediate Similarity NPC160120
0.8175 Intermediate Similarity NPC17388
0.8175 Intermediate Similarity NPC471308
0.8167 Intermediate Similarity NPC474272
0.8151 Intermediate Similarity NPC142297
0.8151 Intermediate Similarity NPC251306
0.812 Intermediate Similarity NPC305205
0.8102 Intermediate Similarity NPC212850
0.8102 Intermediate Similarity NPC83289
0.8102 Intermediate Similarity NPC189724
0.8099 Intermediate Similarity NPC139699
0.8099 Intermediate Similarity NPC182119
0.8099 Intermediate Similarity NPC114659
0.8092 Intermediate Similarity NPC186898
0.8088 Intermediate Similarity NPC254610
0.8083 Intermediate Similarity NPC153690
0.8067 Intermediate Similarity NPC113457
0.8067 Intermediate Similarity NPC231705
0.8031 Intermediate Similarity NPC41801
0.8017 Intermediate Similarity NPC258056
0.8014 Intermediate Similarity NPC132771
0.8014 Intermediate Similarity NPC245974
0.8 Intermediate Similarity NPC258992
0.8 Intermediate Similarity NPC82963
0.7985 Intermediate Similarity NPC470392
0.7966 Intermediate Similarity NPC178902
0.7951 Intermediate Similarity NPC474149
0.7943 Intermediate Similarity NPC5462
0.7937 Intermediate Similarity NPC323948
0.7937 Intermediate Similarity NPC311737
0.7937 Intermediate Similarity NPC38458
0.7934 Intermediate Similarity NPC146530
0.7923 Intermediate Similarity NPC307020
0.792 Intermediate Similarity NPC464
0.792 Intermediate Similarity NPC185541
0.7914 Intermediate Similarity NPC195814
0.7907 Intermediate Similarity NPC474862
0.7879 Intermediate Similarity NPC218323
0.7877 Intermediate Similarity NPC305700
0.7877 Intermediate Similarity NPC140915
0.7877 Intermediate Similarity NPC18249
0.7877 Intermediate Similarity NPC187028
0.7877 Intermediate Similarity NPC10221
0.7877 Intermediate Similarity NPC197741
0.7872 Intermediate Similarity NPC247298
0.7869 Intermediate Similarity NPC306045
0.7869 Intermediate Similarity NPC145638
0.7869 Intermediate Similarity NPC265211
0.7869 Intermediate Similarity NPC290566
0.7863 Intermediate Similarity NPC100870
0.7857 Intermediate Similarity NPC85292
0.7857 Intermediate Similarity NPC229147
0.7857 Intermediate Similarity NPC54507
0.7852 Intermediate Similarity NPC130595
0.7852 Intermediate Similarity NPC93882
0.784 Intermediate Similarity NPC118202
0.7833 Intermediate Similarity NPC470393
0.7833 Intermediate Similarity NPC8302
0.7833 Intermediate Similarity NPC154899
0.7833 Intermediate Similarity NPC233396
0.7823 Intermediate Similarity NPC290353
0.7823 Intermediate Similarity NPC42911
0.7823 Intermediate Similarity NPC153795
0.7795 Intermediate Similarity NPC474933
0.7795 Intermediate Similarity NPC283468
0.7794 Intermediate Similarity NPC6854
0.7794 Intermediate Similarity NPC313737
0.7794 Intermediate Similarity NPC285078
0.7787 Intermediate Similarity NPC201959
0.7787 Intermediate Similarity NPC75440
0.7786 Intermediate Similarity NPC471693
0.7786 Intermediate Similarity NPC474128
0.7778 Intermediate Similarity NPC317254
0.7778 Intermediate Similarity NPC326599
0.7778 Intermediate Similarity NPC329595
0.7778 Intermediate Similarity NPC10286
0.7778 Intermediate Similarity NPC213
0.7778 Intermediate Similarity NPC37302
0.7769 Intermediate Similarity NPC92623
0.7769 Intermediate Similarity NPC135464
0.776 Intermediate Similarity NPC123175
0.776 Intermediate Similarity NPC176730
0.775 Intermediate Similarity NPC38079
0.775 Intermediate Similarity NPC108875
0.774 Intermediate Similarity NPC127402
0.7737 Intermediate Similarity NPC218530
0.7734 Intermediate Similarity NPC131118
0.7734 Intermediate Similarity NPC122009
0.7727 Intermediate Similarity NPC109822
0.7727 Intermediate Similarity NPC94276
0.7717 Intermediate Similarity NPC141090
0.7714 Intermediate Similarity NPC477838
0.7714 Intermediate Similarity NPC477837
0.771 Intermediate Similarity NPC100099
0.771 Intermediate Similarity NPC150026
0.771 Intermediate Similarity NPC36016
0.771 Intermediate Similarity NPC71090
0.7704 Intermediate Similarity NPC470706
0.7698 Intermediate Similarity NPC180508
0.7698 Intermediate Similarity NPC228287
0.7698 Intermediate Similarity NPC235250
0.7687 Intermediate Similarity NPC99798
0.7687 Intermediate Similarity NPC157740
0.7686 Intermediate Similarity NPC211551
0.7686 Intermediate Similarity NPC42383
0.7676 Intermediate Similarity NPC78530
0.7674 Intermediate Similarity NPC268572
0.7669 Intermediate Similarity NPC81641
0.7669 Intermediate Similarity NPC194519
0.7669 Intermediate Similarity NPC148627
0.7667 Intermediate Similarity NPC192596
0.7656 Intermediate Similarity NPC476266
0.7652 Intermediate Similarity NPC328267
0.7652 Intermediate Similarity NPC474160
0.7652 Intermediate Similarity NPC38761
0.7652 Intermediate Similarity NPC76465
0.7647 Intermediate Similarity NPC255550
0.7647 Intermediate Similarity NPC45191
0.7647 Intermediate Similarity NPC308885
0.7643 Intermediate Similarity NPC36434
0.7642 Intermediate Similarity NPC309982
0.7642 Intermediate Similarity NPC97811
0.7638 Intermediate Similarity NPC53906
0.7635 Intermediate Similarity NPC212699
0.7635 Intermediate Similarity NPC207675
0.763 Intermediate Similarity NPC246974
0.763 Intermediate Similarity NPC147247
0.7619 Intermediate Similarity NPC26524
0.7619 Intermediate Similarity NPC35344
0.7619 Intermediate Similarity NPC141003
0.7612 Intermediate Similarity NPC191037
0.7612 Intermediate Similarity NPC58607
0.7612 Intermediate Similarity NPC178284
0.7612 Intermediate Similarity NPC156944
0.7612 Intermediate Similarity NPC251466
0.7612 Intermediate Similarity NPC276212
0.7606 Intermediate Similarity NPC222039
0.7606 Intermediate Similarity NPC100478
0.7603 Intermediate Similarity NPC12987
0.7603 Intermediate Similarity NPC474603
0.7597 Intermediate Similarity NPC474214
0.7594 Intermediate Similarity NPC114901
0.7594 Intermediate Similarity NPC48990
0.7594 Intermediate Similarity NPC293701
0.7594 Intermediate Similarity NPC86502
0.7594 Intermediate Similarity NPC246648
0.7594 Intermediate Similarity NPC197351
0.7594 Intermediate Similarity NPC134195
0.7594 Intermediate Similarity NPC106914
0.7591 Intermediate Similarity NPC97870
0.7591 Intermediate Similarity NPC274732
0.7591 Intermediate Similarity NPC247018
0.7591 Intermediate Similarity NPC307123
0.7589 Intermediate Similarity NPC298821
0.7589 Intermediate Similarity NPC314113
0.7584 Intermediate Similarity NPC107602
0.7583 Intermediate Similarity NPC51633
0.7578 Intermediate Similarity NPC473556
0.7578 Intermediate Similarity NPC301651
0.7571 Intermediate Similarity NPC471316

  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 NPC95733 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
0.8346 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.8346 Intermediate Similarity NPD3052 Approved
0.8346 Intermediate Similarity NPD3054 Approved
0.8346 Intermediate Similarity NPD1669 Approved
0.8175 Intermediate Similarity NPD2668 Approved
0.8175 Intermediate Similarity NPD2667 Approved
0.8062 Intermediate Similarity NPD3685 Discontinued
0.8062 Intermediate Similarity NPD6583 Phase 3
0.8062 Intermediate Similarity NPD6582 Phase 2
0.8045 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD3060 Approved
0.7985 Intermediate Similarity NPD839 Approved
0.7985 Intermediate Similarity NPD7477 Discontinued
0.7985 Intermediate Similarity NPD840 Approved
0.7984 Intermediate Similarity NPD2561 Approved
0.7984 Intermediate Similarity NPD2562 Approved
0.7967 Intermediate Similarity NPD821 Approved
0.7958 Intermediate Similarity NPD4123 Phase 3
0.7955 Intermediate Similarity NPD4993 Discontinued
0.7926 Intermediate Similarity NPD2238 Phase 2
0.7923 Intermediate Similarity NPD4659 Approved
0.7891 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD6584 Phase 3
0.7869 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD3596 Phase 2
0.7852 Intermediate Similarity NPD2674 Phase 3
0.7846 Intermediate Similarity NPD2235 Phase 2
0.7846 Intermediate Similarity NPD2231 Phase 2
0.781 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD4103 Phase 2
0.7803 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD6331 Phase 2
0.7795 Intermediate Similarity NPD856 Approved
0.7795 Intermediate Similarity NPD16 Approved
0.7794 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD4005 Discontinued
0.7734 Intermediate Similarity NPD6580 Approved
0.7734 Intermediate Similarity NPD6581 Approved
0.773 Intermediate Similarity NPD4236 Phase 3
0.773 Intermediate Similarity NPD4237 Approved
0.7727 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.771 Intermediate Similarity NPD2233 Approved
0.771 Intermediate Similarity NPD2230 Approved
0.771 Intermediate Similarity NPD2232 Approved
0.7708 Intermediate Similarity NPD3536 Discontinued
0.7687 Intermediate Similarity NPD4675 Approved
0.7687 Intermediate Similarity NPD4678 Approved
0.7674 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD318 Approved
0.7656 Intermediate Similarity NPD317 Approved
0.7652 Intermediate Similarity NPD2428 Approved
0.7652 Intermediate Similarity NPD2429 Approved
0.7651 Intermediate Similarity NPD5772 Approved
0.7651 Intermediate Similarity NPD5773 Approved
0.7647 Intermediate Similarity NPD3145 Approved
0.7647 Intermediate Similarity NPD3144 Approved
0.7643 Intermediate Similarity NPD2161 Phase 2
0.7639 Intermediate Similarity NPD7213 Phase 3
0.7639 Intermediate Similarity NPD7212 Phase 2
0.7638 Intermediate Similarity NPD2557 Approved
0.7635 Intermediate Similarity NPD6072 Discontinued
0.7626 Intermediate Similarity NPD3554 Approved
0.7626 Intermediate Similarity NPD3555 Approved
0.7626 Intermediate Similarity NPD3552 Approved
0.7626 Intermediate Similarity NPD3553 Approved
0.7622 Intermediate Similarity NPD5241 Discontinued
0.7616 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD2556 Approved
0.7615 Intermediate Similarity NPD2554 Approved
0.7606 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD2458 Approved
0.7606 Intermediate Similarity NPD2460 Phase 3
0.7606 Intermediate Similarity NPD2459 Approved
0.7603 Intermediate Similarity NPD7131 Phase 3
0.7591 Intermediate Similarity NPD1423 Approved
0.7574 Intermediate Similarity NPD3180 Approved
0.7574 Intermediate Similarity NPD3179 Approved
0.7574 Intermediate Similarity NPD1024 Discontinued
0.7571 Intermediate Similarity NPD4108 Discontinued
0.7569 Intermediate Similarity NPD6667 Approved
0.7569 Intermediate Similarity NPD6666 Approved
0.7557 Intermediate Similarity NPD3421 Phase 3
0.7556 Intermediate Similarity NPD1712 Approved
0.7554 Intermediate Similarity NPD2157 Approved
0.7552 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD2594 Approved
0.7538 Intermediate Similarity NPD2595 Approved
0.7537 Intermediate Similarity NPD3568 Approved
0.7537 Intermediate Similarity NPD3567 Approved
0.7535 Intermediate Similarity NPD7153 Discontinued
0.7518 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD596 Approved
0.75 Intermediate Similarity NPD2684 Approved
0.75 Intermediate Similarity NPD600 Approved
0.7483 Intermediate Similarity NPD3560 Approved
0.7483 Intermediate Similarity NPD3557 Approved
0.7483 Intermediate Similarity NPD3559 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3556 Approved
0.7483 Intermediate Similarity NPD3558 Approved
0.7483 Intermediate Similarity NPD4162 Approved
0.7481 Intermediate Similarity NPD7451 Discontinued
0.748 Intermediate Similarity NPD2229 Approved
0.748 Intermediate Similarity NPD2228 Approved
0.748 Intermediate Similarity NPD2234 Approved
0.7466 Intermediate Similarity NPD7447 Phase 1
0.7466 Intermediate Similarity NPD3985 Discontinued
0.7465 Intermediate Similarity NPD1375 Discontinued
0.7464 Intermediate Similarity NPD6407 Approved
0.7464 Intermediate Similarity NPD6405 Approved
0.7464 Intermediate Similarity NPD3058 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD2486 Discontinued
0.7462 Intermediate Similarity NPD1548 Phase 1
0.7445 Intermediate Similarity NPD5163 Phase 2
0.7445 Intermediate Similarity NPD3027 Phase 3
0.7445 Intermediate Similarity NPD6179 Discontinued
0.7424 Intermediate Similarity NPD3847 Discontinued
0.7417 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD1820 Approved
0.7407 Intermediate Similarity NPD1819 Approved
0.7407 Intermediate Similarity NPD1817 Approved
0.7407 Intermediate Similarity NPD1818 Approved
0.7405 Intermediate Similarity NPD3049 Approved
0.7405 Intermediate Similarity NPD6382 Discontinued
0.7394 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1048 Approved
0.7388 Intermediate Similarity NPD6539 Approved
0.7388 Intermediate Similarity NPD6543 Approved
0.7388 Intermediate Similarity NPD4129 Approved
0.7388 Intermediate Similarity NPD6540 Phase 3
0.7388 Intermediate Similarity NPD6542 Approved
0.7383 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD3692 Discontinued
0.7373 Intermediate Similarity NPD2933 Approved
0.7373 Intermediate Similarity NPD2934 Approved
0.7364 Intermediate Similarity NPD709 Approved
0.7361 Intermediate Similarity NPD5177 Phase 3
0.7353 Intermediate Similarity NPD558 Phase 2
0.7353 Intermediate Similarity NPD3691 Phase 2
0.7353 Intermediate Similarity NPD7018 Phase 2
0.7353 Intermediate Similarity NPD3690 Phase 2
0.7347 Intermediate Similarity NPD2874 Phase 2
0.7343 Intermediate Similarity NPD5865 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD968 Approved
0.7338 Intermediate Similarity NPD5745 Approved
0.7333 Intermediate Similarity NPD2922 Phase 1
0.7333 Intermediate Similarity NPD6541 Approved
0.7333 Intermediate Similarity NPD6538 Approved
0.7329 Intermediate Similarity NPD6815 Approved
0.7324 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD3166 Approved
0.7319 Intermediate Similarity NPD3167 Approved
0.7319 Intermediate Similarity NPD3136 Phase 2
0.7319 Intermediate Similarity NPD3164 Approved
0.7319 Intermediate Similarity NPD3165 Approved
0.7315 Intermediate Similarity NPD3686 Approved
0.7315 Intermediate Similarity NPD3687 Approved
0.7311 Intermediate Similarity NPD2860 Approved
0.7311 Intermediate Similarity NPD2859 Approved
0.7305 Intermediate Similarity NPD2568 Approved
0.7305 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD2977 Approved
0.7303 Intermediate Similarity NPD2978 Approved
0.7302 Intermediate Similarity NPD5451 Approved
0.7299 Intermediate Similarity NPD2861 Phase 2
0.7297 Intermediate Similarity NPD7526 Approved
0.7297 Intermediate Similarity NPD52 Approved
0.7297 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD3294 Phase 2
0.7287 Intermediate Similarity NPD593 Approved
0.7287 Intermediate Similarity NPD595 Approved
0.7286 Intermediate Similarity NPD3059 Approved
0.7286 Intermediate Similarity NPD1558 Phase 1
0.7286 Intermediate Similarity NPD3061 Approved
0.7286 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD3062 Approved
0.7285 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD3796 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD4098 Discontinued
0.7279 Intermediate Similarity NPD1135 Approved
0.7279 Intermediate Similarity NPD1129 Approved
0.7279 Intermediate Similarity NPD1133 Approved
0.7279 Intermediate Similarity NPD1134 Approved
0.7279 Intermediate Similarity NPD1131 Approved
0.7273 Intermediate Similarity NPD3445 Approved
0.7273 Intermediate Similarity NPD3444 Approved
0.7273 Intermediate Similarity NPD3443 Approved
0.7266 Intermediate Similarity NPD5718 Phase 2
0.7266 Intermediate Similarity NPD7843 Approved
0.726 Intermediate Similarity NPD2677 Approved
0.7248 Intermediate Similarity NPD2122 Discontinued
0.7246 Intermediate Similarity NPD4908 Phase 1
0.7239 Intermediate Similarity NPD1610 Phase 2
0.7237 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD4739 Approved
0.7226 Intermediate Similarity NPD7905 Discontinued
0.7219 Intermediate Similarity NPD6502 Phase 2

  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