Structure

Physi-Chem Properties

Molecular Weight:  138.07
Volume:  148.039
LogP:  2.162
LogD:  2.425
LogS:  -1.317
# Rotatable Bonds:  1
TPSA:  29.46
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.64
Synthetic Accessibility Score:  1.777
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.489
MDCK Permeability:  1.8929729776573367e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.808
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.709
30% Bioavailability (F30%):  0.222

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.153
Plasma Protein Binding (PPB):  78.4961166381836%
Volume Distribution (VD):  1.236
Pgp-substrate:  11.882574081420898%

ADMET: Metabolism

CYP1A2-inhibitor:  0.943
CYP1A2-substrate:  0.897
CYP2C19-inhibitor:  0.466
CYP2C19-substrate:  0.753
CYP2C9-inhibitor:  0.073
CYP2C9-substrate:  0.935
CYP2D6-inhibitor:  0.685
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.18
CYP3A4-substrate:  0.282

ADMET: Excretion

Clearance (CL):  13.19
Half-life (T1/2):  0.871

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.139
Drug-inuced Liver Injury (DILI):  0.047
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.062
Maximum Recommended Daily Dose:  0.303
Skin Sensitization:  0.915
Carcinogencity:  0.087
Eye Corrosion:  0.972
Eye Irritation:  0.992
Respiratory Toxicity:  0.365

Download Data

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

  Natural Product: NPC164576

Natural Product ID:  NPC164576
Common Name*:   3-Methoxy-5-Methylphenol
IUPAC Name:   3-methoxy-5-methylphenol
Synonyms:  
Standard InCHIKey:  NOTCZLKDULMKBR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H10O2/c1-6-3-7(9)5-8(4-6)10-2/h3-5,9H,1-2H3
SMILES:  Cc1cc(cc(c1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3187650
PubChem CID:   76674
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. root n.a. PMID[22233034]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota Flowers Muyang, China n.a. PMID[24621197]
NPO40388 Umbilicaria sp. Species Umbilicariaceae Eukaryota n.a. n.a. n.a. PMID[32394716]
NPO3729 Cetraria islandica Species Parmeliaceae Eukaryota n.a. n.a. n.a. PMID[7561895]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25424 Putterlickia verrucosa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6513 Vernonia condensata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3729 Cetraria islandica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4633 Calypogeia integristipula Species Calypogeiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2777 Cirsium brevistylum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5786 Desmodium oxyphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25424 Putterlickia verrucosa Species Celastraceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[513904]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[513904]
NPT91 Cell Line KB Homo sapiens IC50 > 40000.0 nM PMID[513904]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 30899.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24547.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10963.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21875.1 nM PubChem BioAssay data set

☑ 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 NPC164576 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
0.9608 High Similarity NPC94045
0.9608 High Similarity NPC168657
0.9423 High Similarity NPC280606
0.9327 High Similarity NPC296920
0.9327 High Similarity NPC255068
0.9327 High Similarity NPC90520
0.9245 High Similarity NPC180508
0.9245 High Similarity NPC22610
0.9245 High Similarity NPC276737
0.9245 High Similarity NPC228287
0.9159 High Similarity NPC167934
0.9159 High Similarity NPC53906
0.9074 High Similarity NPC141090
0.9074 High Similarity NPC193067
0.9074 High Similarity NPC114064
0.9074 High Similarity NPC150624
0.9074 High Similarity NPC203113
0.8991 High Similarity NPC50521
0.8991 High Similarity NPC221549
0.8991 High Similarity NPC474933
0.8991 High Similarity NPC69261
0.8991 High Similarity NPC195466
0.8991 High Similarity NPC33270
0.8991 High Similarity NPC15860
0.8991 High Similarity NPC259638
0.8991 High Similarity NPC244816
0.8991 High Similarity NPC219070
0.8991 High Similarity NPC470759
0.8991 High Similarity NPC127894
0.8981 High Similarity NPC808
0.8942 High Similarity NPC35543
0.8878 High Similarity NPC295295
0.8857 High Similarity NPC245115
0.8829 High Similarity NPC184302
0.8829 High Similarity NPC226629
0.8829 High Similarity NPC20674
0.8788 High Similarity NPC16649
0.8774 High Similarity NPC82016
0.8774 High Similarity NPC165386
0.875 High Similarity NPC229401
0.8739 High Similarity NPC190514
0.8692 High Similarity NPC2682
0.8692 High Similarity NPC303521
0.8673 High Similarity NPC102639
0.8673 High Similarity NPC166759
0.8661 High Similarity NPC85895
0.8661 High Similarity NPC137294
0.8654 High Similarity NPC12987
0.8654 High Similarity NPC474603
0.8636 High Similarity NPC185541
0.8636 High Similarity NPC464
0.8611 High Similarity NPC203924
0.8596 High Similarity NPC476633
0.8596 High Similarity NPC285289
0.8596 High Similarity NPC75713
0.8596 High Similarity NPC212965
0.8596 High Similarity NPC49341
0.8584 High Similarity NPC232084
0.8584 High Similarity NPC10932
0.8584 High Similarity NPC474565
0.8584 High Similarity NPC247364
0.8584 High Similarity NPC61516
0.8571 High Similarity NPC63083
0.8559 High Similarity NPC54507
0.8559 High Similarity NPC85292
0.8559 High Similarity NPC229147
0.8558 High Similarity NPC305205
0.8544 High Similarity NPC166761
0.8529 High Similarity NPC291789
0.8522 High Similarity NPC262253
0.8522 High Similarity NPC120638
0.8522 High Similarity NPC474864
0.8522 High Similarity NPC71579
0.8522 High Similarity NPC18128
0.8522 High Similarity NPC77789
0.8522 High Similarity NPC473411
0.8509 High Similarity NPC218753
0.8505 High Similarity NPC241549
0.8469 Intermediate Similarity NPC47422
0.8462 Intermediate Similarity NPC137415
0.8462 Intermediate Similarity NPC166313
0.8462 Intermediate Similarity NPC24407
0.8462 Intermediate Similarity NPC294186
0.8462 Intermediate Similarity NPC192032
0.8462 Intermediate Similarity NPC11280
0.8462 Intermediate Similarity NPC147310
0.8455 Intermediate Similarity NPC204120
0.8448 Intermediate Similarity NPC238810
0.8448 Intermediate Similarity NPC84086
0.8448 Intermediate Similarity NPC136319
0.8448 Intermediate Similarity NPC220598
0.8448 Intermediate Similarity NPC95168
0.8448 Intermediate Similarity NPC165375
0.8448 Intermediate Similarity NPC282496
0.8448 Intermediate Similarity NPC233526
0.8435 Intermediate Similarity NPC145780
0.8411 Intermediate Similarity NPC233320
0.8407 Intermediate Similarity NPC131118
0.8384 Intermediate Similarity NPC302546
0.8381 Intermediate Similarity NPC249828
0.8381 Intermediate Similarity NPC302219
0.8381 Intermediate Similarity NPC106396
0.8381 Intermediate Similarity NPC222522
0.8381 Intermediate Similarity NPC53051
0.8381 Intermediate Similarity NPC24404
0.8381 Intermediate Similarity NPC242342
0.8381 Intermediate Similarity NPC146798
0.8381 Intermediate Similarity NPC313030
0.8381 Intermediate Similarity NPC85479
0.8381 Intermediate Similarity NPC94351
0.8381 Intermediate Similarity NPC168303
0.8381 Intermediate Similarity NPC71002
0.8376 Intermediate Similarity NPC228503
0.8376 Intermediate Similarity NPC5796
0.8376 Intermediate Similarity NPC206487
0.8376 Intermediate Similarity NPC138248
0.8376 Intermediate Similarity NPC270030
0.8376 Intermediate Similarity NPC183446
0.8365 Intermediate Similarity NPC248573
0.8365 Intermediate Similarity NPC275053
0.8365 Intermediate Similarity NPC10588
0.8365 Intermediate Similarity NPC161571
0.8362 Intermediate Similarity NPC135414
0.8362 Intermediate Similarity NPC246967
0.8362 Intermediate Similarity NPC74137
0.8362 Intermediate Similarity NPC57199
0.8362 Intermediate Similarity NPC41562
0.8349 Intermediate Similarity NPC242178
0.8348 Intermediate Similarity NPC199023
0.8333 Intermediate Similarity NPC75440
0.8318 Intermediate Similarity NPC473653
0.8305 Intermediate Similarity NPC251855
0.8305 Intermediate Similarity NPC113495
0.8305 Intermediate Similarity NPC117214
0.8305 Intermediate Similarity NPC58279
0.8305 Intermediate Similarity NPC105031
0.8305 Intermediate Similarity NPC278955
0.8305 Intermediate Similarity NPC12308
0.8305 Intermediate Similarity NPC60885
0.8305 Intermediate Similarity NPC271985
0.8305 Intermediate Similarity NPC472093
0.8305 Intermediate Similarity NPC300326
0.8305 Intermediate Similarity NPC193544
0.8305 Intermediate Similarity NPC233410
0.8305 Intermediate Similarity NPC208950
0.8305 Intermediate Similarity NPC17943
0.8305 Intermediate Similarity NPC82483
0.8305 Intermediate Similarity NPC476254
0.8305 Intermediate Similarity NPC265483
0.8305 Intermediate Similarity NPC203133
0.8305 Intermediate Similarity NPC299584
0.8305 Intermediate Similarity NPC131397
0.8305 Intermediate Similarity NPC221077
0.8305 Intermediate Similarity NPC293801
0.8305 Intermediate Similarity NPC475169
0.8305 Intermediate Similarity NPC57490
0.8305 Intermediate Similarity NPC116907
0.8305 Intermediate Similarity NPC234400
0.8305 Intermediate Similarity NPC298757
0.8305 Intermediate Similarity NPC105925
0.8305 Intermediate Similarity NPC105718
0.8302 Intermediate Similarity NPC227458
0.8302 Intermediate Similarity NPC130817
0.8302 Intermediate Similarity NPC244513
0.8302 Intermediate Similarity NPC218879
0.8291 Intermediate Similarity NPC197757
0.8291 Intermediate Similarity NPC121115
0.8291 Intermediate Similarity NPC96940
0.8291 Intermediate Similarity NPC228922
0.8286 Intermediate Similarity NPC100340
0.8286 Intermediate Similarity NPC72947
0.8286 Intermediate Similarity NPC143659
0.8286 Intermediate Similarity NPC284011
0.8276 Intermediate Similarity NPC310373
0.8257 Intermediate Similarity NPC246358
0.8257 Intermediate Similarity NPC233731
0.8257 Intermediate Similarity NPC36108
0.8257 Intermediate Similarity NPC7097
0.8246 Intermediate Similarity NPC74821
0.8241 Intermediate Similarity NPC251306
0.8241 Intermediate Similarity NPC61033
0.8241 Intermediate Similarity NPC305603
0.8235 Intermediate Similarity NPC18924
0.8235 Intermediate Similarity NPC245060
0.8235 Intermediate Similarity NPC214406
0.8235 Intermediate Similarity NPC44748
0.8235 Intermediate Similarity NPC76451
0.8235 Intermediate Similarity NPC82299
0.8235 Intermediate Similarity NPC28730
0.8235 Intermediate Similarity NPC170485
0.8235 Intermediate Similarity NPC78974
0.8235 Intermediate Similarity NPC223136
0.8235 Intermediate Similarity NPC112596
0.8235 Intermediate Similarity NPC223953
0.8235 Intermediate Similarity NPC103823
0.823 Intermediate Similarity NPC123948
0.823 Intermediate Similarity NPC221049
0.8224 Intermediate Similarity NPC8302
0.8224 Intermediate Similarity NPC288760
0.8224 Intermediate Similarity NPC307875

  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 NPC164576 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
0.8365 Intermediate Similarity NPD1242 Phase 1
0.8291 Intermediate Similarity NPD4749 Approved
0.8246 Intermediate Similarity NPD1548 Phase 1
0.812 Intermediate Similarity NPD1610 Phase 2
0.8108 Intermediate Similarity NPD228 Approved
0.8083 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8033 Intermediate Similarity NPD3027 Phase 3
0.7967 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD422 Phase 1
0.7944 Intermediate Similarity NPD846 Approved
0.7944 Intermediate Similarity NPD940 Approved
0.7928 Intermediate Similarity NPD4750 Phase 3
0.7886 Intermediate Similarity NPD4625 Phase 3
0.7869 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD2983 Phase 2
0.7833 Intermediate Similarity NPD2982 Phase 2
0.7818 Intermediate Similarity NPD968 Approved
0.7805 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD4908 Phase 1
0.775 Intermediate Similarity NPD2981 Phase 2
0.7748 Intermediate Similarity NPD290 Approved
0.7745 Intermediate Similarity NPD9295 Approved
0.7698 Intermediate Similarity NPD1613 Approved
0.7698 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD6671 Approved
0.7653 Intermediate Similarity NPD9093 Approved
0.7581 Intermediate Similarity NPD3018 Phase 2
0.7576 Intermediate Similarity NPD9089 Approved
0.7525 Intermediate Similarity NPD111 Approved
0.75 Intermediate Similarity NPD1778 Approved
0.7477 Intermediate Similarity NPD844 Approved
0.7424 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD1240 Approved
0.7417 Intermediate Similarity NPD1357 Approved
0.7407 Intermediate Similarity NPD288 Approved
0.7405 Intermediate Similarity NPD6100 Approved
0.7405 Intermediate Similarity NPD6099 Approved
0.7383 Intermediate Similarity NPD9296 Approved
0.7377 Intermediate Similarity NPD1091 Approved
0.7368 Intermediate Similarity NPD2684 Approved
0.7364 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD6696 Suspended
0.7317 Intermediate Similarity NPD1608 Approved
0.7308 Intermediate Similarity NPD1607 Approved
0.7302 Intermediate Similarity NPD2861 Phase 2
0.7266 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD821 Approved
0.7258 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD230 Phase 1
0.7227 Intermediate Similarity NPD709 Approved
0.7222 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2933 Approved
0.7222 Intermediate Similarity NPD2934 Approved
0.7213 Intermediate Similarity NPD4626 Approved
0.7203 Intermediate Similarity NPD5283 Phase 1
0.7197 Intermediate Similarity NPD1510 Phase 2
0.7193 Intermediate Similarity NPD3134 Approved
0.7185 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD2233 Approved
0.7177 Intermediate Similarity NPD2230 Approved
0.7177 Intermediate Similarity NPD2232 Approved
0.7156 Intermediate Similarity NPD2859 Approved
0.7156 Intermediate Similarity NPD2860 Approved
0.7154 Intermediate Similarity NPD3496 Discontinued
0.7154 Intermediate Similarity NPD2238 Phase 2
0.7143 Intermediate Similarity NPD1551 Phase 2
0.7143 Intermediate Similarity NPD9094 Approved
0.7132 Intermediate Similarity NPD2219 Phase 1
0.713 Intermediate Similarity NPD1358 Approved
0.7119 Intermediate Similarity NPD7843 Approved
0.7117 Intermediate Similarity NPD3020 Approved
0.7109 Intermediate Similarity NPD596 Approved
0.7109 Intermediate Similarity NPD600 Approved
0.7103 Intermediate Similarity NPD9365 Approved
0.7097 Intermediate Similarity NPD3705 Approved
0.7087 Intermediate Similarity NPD6584 Phase 3
0.7083 Intermediate Similarity NPD7157 Approved
0.708 Intermediate Similarity NPD9500 Approved
0.7073 Intermediate Similarity NPD17 Approved
0.7059 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD9545 Approved
0.704 Intermediate Similarity NPD2235 Phase 2
0.704 Intermediate Similarity NPD2231 Phase 2
0.7031 Intermediate Similarity NPD9494 Approved
0.7029 Intermediate Similarity NPD4357 Discontinued
0.7025 Intermediate Similarity NPD9493 Approved
0.7023 Intermediate Similarity NPD1558 Phase 1
0.7009 Intermediate Similarity NPD5451 Approved
0.6992 Remote Similarity NPD6111 Discontinued
0.6991 Remote Similarity NPD291 Approved
0.6978 Remote Similarity NPD3157 Approved
0.6978 Remote Similarity NPD3158 Phase 1
0.6972 Remote Similarity NPD845 Approved
0.6967 Remote Similarity NPD5536 Phase 2
0.6963 Remote Similarity NPD3540 Phase 1
0.6963 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6963 Remote Similarity NPD1550 Clinical (unspecified phase)
0.696 Remote Similarity NPD776 Approved
0.6953 Remote Similarity NPD599 Approved
0.6953 Remote Similarity NPD859 Approved
0.6953 Remote Similarity NPD602 Approved
0.6953 Remote Similarity NPD858 Approved
0.6947 Remote Similarity NPD840 Approved
0.6947 Remote Similarity NPD839 Approved
0.6935 Remote Similarity NPD2668 Approved
0.6935 Remote Similarity NPD2667 Approved
0.6934 Remote Similarity NPD3892 Phase 2
0.6929 Remote Similarity NPD3225 Approved
0.6929 Remote Similarity NPD1283 Approved
0.6917 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6917 Remote Similarity NPD1398 Phase 1
0.6912 Remote Similarity NPD1549 Phase 2
0.6911 Remote Similarity NPD1182 Approved
0.6906 Remote Similarity NPD1511 Approved
0.6905 Remote Similarity NPD9717 Approved
0.6897 Remote Similarity NPD1445 Approved
0.6897 Remote Similarity NPD1444 Approved
0.6889 Remote Similarity NPD3539 Phase 1
0.6875 Remote Similarity NPD9273 Approved
0.687 Remote Similarity NPD3144 Approved
0.687 Remote Similarity NPD3145 Approved
0.6864 Remote Similarity NPD3022 Approved
0.6864 Remote Similarity NPD3021 Approved
0.6857 Remote Similarity NPD7447 Phase 1
0.6857 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6855 Remote Similarity NPD5585 Approved
0.6855 Remote Similarity NPD5691 Approved
0.6855 Remote Similarity NPD1651 Approved
0.685 Remote Similarity NPD6583 Phase 3
0.685 Remote Similarity NPD6582 Phase 2
0.685 Remote Similarity NPD1669 Approved
0.6847 Remote Similarity NPD1809 Phase 2
0.6846 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5124 Phase 1
0.6833 Remote Similarity NPD1138 Approved
0.6831 Remote Similarity NPD1653 Approved
0.6822 Remote Similarity NPD558 Phase 2
0.6822 Remote Similarity NPD4624 Approved
0.6818 Remote Similarity NPD2674 Phase 3
0.6812 Remote Similarity NPD3750 Approved
0.681 Remote Similarity NPD9697 Approved
0.6809 Remote Similarity NPD1512 Approved
0.68 Remote Similarity NPD2423 Clinical (unspecified phase)
0.6791 Remote Similarity NPD4097 Suspended
0.6786 Remote Similarity NPD7213 Phase 3
0.6786 Remote Similarity NPD7212 Phase 2
0.6777 Remote Similarity NPD1241 Discontinued
0.6769 Remote Similarity NPD1712 Approved
0.6768 Remote Similarity NPD9087 Approved
0.6767 Remote Similarity NPD3620 Phase 2
0.6767 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6767 Remote Similarity NPD4060 Phase 1
0.6765 Remote Similarity NPD2935 Discontinued
0.6759 Remote Similarity NPD1934 Approved
0.675 Remote Similarity NPD1137 Approved
0.675 Remote Similarity NPD1139 Approved
0.6748 Remote Similarity NPD7340 Approved
0.6746 Remote Similarity NPD3847 Discontinued
0.6744 Remote Similarity NPD1203 Approved
0.6744 Remote Similarity NPD2797 Approved
0.6742 Remote Similarity NPD411 Approved
0.6739 Remote Similarity NPD1652 Phase 2
0.6738 Remote Similarity NPD2532 Approved
0.6738 Remote Similarity NPD2534 Approved
0.6738 Remote Similarity NPD2533 Approved
0.6736 Remote Similarity NPD4675 Approved
0.6736 Remote Similarity NPD4678 Approved
0.6723 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6723 Remote Similarity NPD1792 Phase 2
0.6721 Remote Similarity NPD9614 Approved
0.6721 Remote Similarity NPD9618 Approved
0.6719 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6716 Remote Similarity NPD447 Suspended
0.6712 Remote Similarity NPD2801 Approved
0.6712 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5535 Approved
0.6694 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6693 Remote Similarity NPD1281 Approved
0.6693 Remote Similarity NPD1535 Discovery
0.6692 Remote Similarity NPD3691 Phase 2
0.6692 Remote Similarity NPD3690 Phase 2
0.6667 Remote Similarity NPD9088 Approved
0.6667 Remote Similarity NPD4005 Discontinued
0.6667 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8651 Approved
0.6667 Remote Similarity NPD6653 Approved
0.6644 Remote Similarity NPD37 Approved
0.6643 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6642 Remote Similarity NPD2796 Approved
0.6641 Remote Similarity NPD9269 Phase 2
0.6641 Remote Similarity NPD1481 Phase 2
0.6641 Remote Similarity NPD1840 Phase 2
0.664 Remote Similarity NPD7534 Approved
0.664 Remote Similarity NPD1894 Discontinued
0.664 Remote Similarity NPD7533 Approved
0.6622 Remote Similarity NPD3882 Suspended
0.6619 Remote Similarity NPD5698 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