Structure

Physi-Chem Properties

Molecular Weight:  148.09
Volume:  171.204
LogP:  3.275
LogD:  3.258
LogS:  -3.558
# Rotatable Bonds:  2
TPSA:  9.23
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.626
Synthetic Accessibility Score:  1.653
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.44
MDCK Permeability:  2.1642912543029524e-05
Pgp-inhibitor:  0.051
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.643
Plasma Protein Binding (PPB):  94.9951171875%
Volume Distribution (VD):  2.879
Pgp-substrate:  5.23119592666626%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.957
CYP2C19-inhibitor:  0.707
CYP2C19-substrate:  0.832
CYP2C9-inhibitor:  0.173
CYP2C9-substrate:  0.92
CYP2D6-inhibitor:  0.442
CYP2D6-substrate:  0.929
CYP3A4-inhibitor:  0.105
CYP3A4-substrate:  0.556

ADMET: Excretion

Clearance (CL):  11.146
Half-life (T1/2):  0.638

ADMET: Toxicity

hERG Blockers:  0.095
Human Hepatotoxicity (H-HT):  0.57
Drug-inuced Liver Injury (DILI):  0.222
AMES Toxicity:  0.145
Rat Oral Acute Toxicity:  0.025
Maximum Recommended Daily Dose:  0.052
Skin Sensitization:  0.958
Carcinogencity:  0.482
Eye Corrosion:  0.879
Eye Irritation:  0.991
Respiratory Toxicity:  0.221

Download Data

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

  Natural Product: NPC8002

Natural Product ID:  NPC8002
Common Name*:   1-Methoxy-4-Prop-1-Enylbenzene
IUPAC Name:   1-methoxy-4-prop-1-enylbenzene
Synonyms:  
Standard InCHIKey:  RUVINXPYWBROJD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3
SMILES:  CC=Cc1ccc(cc1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3185908
PubChem CID:   7703
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002341] Phenol ethers
        • [CHEMONTID:0000138] Anisoles

*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
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10079 Chloropyron maritimum Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12940 Briareum stechei Species Briareidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5531 Protoceratium reticulatum Species Gonyaulacaceae 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
NPT2 Others Unspecified Potency n.a. 899.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 506 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 94.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1426.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10590.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2391.4 nM PubChem BioAssay data set
NPT2 Others Unspecified AC50 n.a. 631.0 nM PMID[513575]
NPT2 Others Unspecified Ac50 n.a. 0.631 uM PMID[513575]
NPT2 Others Unspecified Ac50 n.a. 44.67 uM PMID[513575]
NPT2 Others Unspecified Ac50 n.a. 1.259 uM PMID[513575]
NPT2 Others Unspecified AC50 n.a. 44668.4 nM PMID[513575]
NPT2 Others Unspecified AC50 n.a. 1258.9 nM PMID[513575]

☑ 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 NPC8002 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 NPC259134
1.0 High Similarity NPC177844
1.0 High Similarity NPC99886
0.9882 High Similarity NPC71853
0.9767 High Similarity NPC321956
0.9545 High Similarity NPC471581
0.9231 High Similarity NPC175298
0.913 High Similarity NPC100870
0.913 High Similarity NPC471576
0.9032 High Similarity NPC13755
0.8936 High Similarity NPC12714
0.8936 High Similarity NPC300166
0.8936 High Similarity NPC310905
0.8936 High Similarity NPC51633
0.8842 High Similarity NPC192596
0.8842 High Similarity NPC298224
0.8842 High Similarity NPC179686
0.8842 High Similarity NPC305205
0.883 High Similarity NPC107101
0.8817 High Similarity NPC470161
0.881 High Similarity NPC124576
0.875 High Similarity NPC241224
0.875 High Similarity NPC474603
0.875 High Similarity NPC2518
0.875 High Similarity NPC283546
0.875 High Similarity NPC108875
0.875 High Similarity NPC38209
0.875 High Similarity NPC12987
0.875 High Similarity NPC109637
0.875 High Similarity NPC292792
0.875 High Similarity NPC38079
0.8737 High Similarity NPC307425
0.866 High Similarity NPC473855
0.866 High Similarity NPC470393
0.866 High Similarity NPC42383
0.866 High Similarity NPC238115
0.866 High Similarity NPC128730
0.8617 High Similarity NPC95755
0.8571 High Similarity NPC1065
0.8571 High Similarity NPC176971
0.8571 High Similarity NPC113457
0.8571 High Similarity NPC326447
0.8542 High Similarity NPC84325
0.8523 High Similarity NPC23837
0.8485 Intermediate Similarity NPC258171
0.8485 Intermediate Similarity NPC251306
0.8485 Intermediate Similarity NPC157473
0.8485 Intermediate Similarity NPC151530
0.8485 Intermediate Similarity NPC227894
0.8469 Intermediate Similarity NPC473393
0.8469 Intermediate Similarity NPC8302
0.8454 Intermediate Similarity NPC24327
0.8454 Intermediate Similarity NPC12870
0.8427 Intermediate Similarity NPC248817
0.84 Intermediate Similarity NPC291837
0.84 Intermediate Similarity NPC97811
0.84 Intermediate Similarity NPC146530
0.84 Intermediate Similarity NPC201959
0.84 Intermediate Similarity NPC75440
0.84 Intermediate Similarity NPC309982
0.8333 Intermediate Similarity NPC197783
0.8317 Intermediate Similarity NPC82016
0.8317 Intermediate Similarity NPC127326
0.8317 Intermediate Similarity NPC474272
0.8317 Intermediate Similarity NPC36108
0.8317 Intermediate Similarity NPC233731
0.8317 Intermediate Similarity NPC234639
0.8317 Intermediate Similarity NPC246358
0.8317 Intermediate Similarity NPC7097
0.8315 Intermediate Similarity NPC265146
0.8315 Intermediate Similarity NPC124436
0.8283 Intermediate Similarity NPC227255
0.8283 Intermediate Similarity NPC288760
0.8242 Intermediate Similarity NPC206876
0.8242 Intermediate Similarity NPC184169
0.8242 Intermediate Similarity NPC23167
0.8235 Intermediate Similarity NPC88868
0.8235 Intermediate Similarity NPC473809
0.8235 Intermediate Similarity NPC475852
0.8235 Intermediate Similarity NPC231251
0.8235 Intermediate Similarity NPC179309
0.8235 Intermediate Similarity NPC25067
0.8235 Intermediate Similarity NPC46844
0.8235 Intermediate Similarity NPC137685
0.8235 Intermediate Similarity NPC183648
0.8235 Intermediate Similarity NPC106141
0.8222 Intermediate Similarity NPC175313
0.8155 Intermediate Similarity NPC139617
0.8155 Intermediate Similarity NPC90520
0.8155 Intermediate Similarity NPC8547
0.8155 Intermediate Similarity NPC23332
0.8155 Intermediate Similarity NPC173746
0.8155 Intermediate Similarity NPC245552
0.8155 Intermediate Similarity NPC257124
0.8155 Intermediate Similarity NPC57879
0.8155 Intermediate Similarity NPC55300
0.8155 Intermediate Similarity NPC78918
0.8155 Intermediate Similarity NPC166837
0.8155 Intermediate Similarity NPC156840
0.8155 Intermediate Similarity NPC296920
0.8155 Intermediate Similarity NPC203924
0.8152 Intermediate Similarity NPC104216
0.8152 Intermediate Similarity NPC25493
0.8152 Intermediate Similarity NPC113460
0.8144 Intermediate Similarity NPC171843
0.8137 Intermediate Similarity NPC259554
0.8137 Intermediate Similarity NPC165386
0.8119 Intermediate Similarity NPC233320
0.8119 Intermediate Similarity NPC186469
0.8119 Intermediate Similarity NPC194034
0.8119 Intermediate Similarity NPC35543
0.8111 Intermediate Similarity NPC125306
0.8077 Intermediate Similarity NPC115379
0.8077 Intermediate Similarity NPC165646
0.8077 Intermediate Similarity NPC280606
0.8077 Intermediate Similarity NPC199462
0.8065 Intermediate Similarity NPC318325
0.8065 Intermediate Similarity NPC302546
0.8065 Intermediate Similarity NPC98772
0.8065 Intermediate Similarity NPC258219
0.8065 Intermediate Similarity NPC242240
0.8065 Intermediate Similarity NPC177420
0.8065 Intermediate Similarity NPC280347
0.8065 Intermediate Similarity NPC123273
0.8061 Intermediate Similarity NPC253746
0.8058 Intermediate Similarity NPC31279
0.8039 Intermediate Similarity NPC245115
0.8039 Intermediate Similarity NPC241549
0.802 Intermediate Similarity NPC164576
0.802 Intermediate Similarity NPC30416
0.802 Intermediate Similarity NPC326801
0.8 Intermediate Similarity NPC165106
0.8 Intermediate Similarity NPC303522
0.8 Intermediate Similarity NPC26524
0.8 Intermediate Similarity NPC90903
0.8 Intermediate Similarity NPC109241
0.8 Intermediate Similarity NPC35344
0.8 Intermediate Similarity NPC204120
0.8 Intermediate Similarity NPC325292
0.8 Intermediate Similarity NPC141003
0.8 Intermediate Similarity NPC138117
0.7981 Intermediate Similarity NPC470723
0.7981 Intermediate Similarity NPC266932
0.7979 Intermediate Similarity NPC300017
0.7979 Intermediate Similarity NPC55561
0.7957 Intermediate Similarity NPC47422
0.7957 Intermediate Similarity NPC157213
0.7925 Intermediate Similarity NPC294941
0.7925 Intermediate Similarity NPC180508
0.7925 Intermediate Similarity NPC235250
0.7925 Intermediate Similarity NPC252004
0.7925 Intermediate Similarity NPC228287
0.7925 Intermediate Similarity NPC161696
0.7921 Intermediate Similarity NPC475269
0.7921 Intermediate Similarity NPC127676
0.79 Intermediate Similarity NPC304638
0.7895 Intermediate Similarity NPC270547
0.7895 Intermediate Similarity NPC155908
0.7895 Intermediate Similarity NPC204210
0.7895 Intermediate Similarity NPC304541
0.7885 Intermediate Similarity NPC303521
0.7885 Intermediate Similarity NPC94045
0.7885 Intermediate Similarity NPC2682
0.785 Intermediate Similarity NPC303370
0.785 Intermediate Similarity NPC475815
0.785 Intermediate Similarity NPC185541
0.785 Intermediate Similarity NPC296526
0.785 Intermediate Similarity NPC473264
0.785 Intermediate Similarity NPC464
0.785 Intermediate Similarity NPC220540
0.785 Intermediate Similarity NPC47194
0.7849 Intermediate Similarity NPC407
0.7849 Intermediate Similarity NPC307235
0.7835 Intermediate Similarity NPC313650
0.783 Intermediate Similarity NPC301735
0.7826 Intermediate Similarity NPC150837
0.7826 Intermediate Similarity NPC286904
0.7812 Intermediate Similarity NPC181709
0.781 Intermediate Similarity NPC195873
0.781 Intermediate Similarity NPC275627
0.781 Intermediate Similarity NPC21890
0.781 Intermediate Similarity NPC54626
0.7789 Intermediate Similarity NPC300478
0.7789 Intermediate Similarity NPC318429
0.7788 Intermediate Similarity NPC149545
0.7778 Intermediate Similarity NPC33900
0.7778 Intermediate Similarity NPC258992
0.7778 Intermediate Similarity NPC229147
0.7778 Intermediate Similarity NPC268317
0.7778 Intermediate Similarity NPC54507
0.7778 Intermediate Similarity NPC123948
0.7778 Intermediate Similarity NPC9341
0.7778 Intermediate Similarity NPC85292
0.7778 Intermediate Similarity NPC141090
0.7778 Intermediate Similarity NPC203113
0.7778 Intermediate Similarity NPC19290
0.7778 Intermediate Similarity NPC81067
0.7778 Intermediate Similarity NPC312105
0.7778 Intermediate Similarity NPC221049
0.7778 Intermediate Similarity NPC106313

  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 NPC8002 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
0.8571 High Similarity NPD3134 Approved
0.8485 Intermediate Similarity NPD1358 Approved
0.84 Intermediate Similarity NPD2684 Approved
0.8317 Intermediate Similarity NPD5451 Approved
0.8315 Intermediate Similarity NPD111 Approved
0.8155 Intermediate Similarity NPD228 Approved
0.8119 Intermediate Similarity NPD290 Approved
0.8077 Intermediate Similarity NPD7843 Approved
0.8077 Intermediate Similarity NPD821 Approved
0.802 Intermediate Similarity NPD968 Approved
0.8 Intermediate Similarity NPD5283 Phase 1
0.8 Intermediate Similarity NPD1241 Discontinued
0.7957 Intermediate Similarity NPD9295 Approved
0.7905 Intermediate Similarity NPD5535 Approved
0.785 Intermediate Similarity NPD7157 Approved
0.7789 Intermediate Similarity NPD9365 Approved
0.7778 Intermediate Similarity NPD3596 Phase 2
0.7745 Intermediate Similarity NPD9697 Approved
0.7732 Intermediate Similarity NPD2934 Approved
0.7732 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7732 Intermediate Similarity NPD2933 Approved
0.7706 Intermediate Similarity NPD5536 Phase 2
0.7653 Intermediate Similarity NPD2859 Approved
0.7653 Intermediate Similarity NPD2860 Approved
0.7642 Intermediate Similarity NPD1137 Approved
0.7642 Intermediate Similarity NPD1139 Approved
0.7636 Intermediate Similarity NPD6581 Approved
0.7636 Intermediate Similarity NPD6580 Approved
0.7593 Intermediate Similarity NPD595 Approved
0.7593 Intermediate Similarity NPD593 Approved
0.757 Intermediate Similarity NPD1138 Approved
0.7568 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD5691 Approved
0.7568 Intermediate Similarity NPD1357 Approved
0.7568 Intermediate Similarity NPD1651 Approved
0.7551 Intermediate Similarity NPD9296 Approved
0.7523 Intermediate Similarity NPD2557 Approved
0.75 Intermediate Similarity NPD2667 Approved
0.75 Intermediate Similarity NPD594 Approved
0.75 Intermediate Similarity NPD592 Approved
0.75 Intermediate Similarity NPD4626 Approved
0.75 Intermediate Similarity NPD2668 Approved
0.7477 Intermediate Similarity NPD1548 Phase 1
0.7477 Intermediate Similarity NPD1182 Approved
0.7434 Intermediate Similarity NPD3847 Discontinued
0.7426 Intermediate Similarity NPD3020 Approved
0.7368 Intermediate Similarity NPD1281 Approved
0.7364 Intermediate Similarity NPD6671 Approved
0.7364 Intermediate Similarity NPD709 Approved
0.7353 Intermediate Similarity NPD3028 Approved
0.7345 Intermediate Similarity NPD6516 Phase 2
0.7345 Intermediate Similarity NPD5846 Approved
0.7321 Intermediate Similarity NPD1894 Discontinued
0.7304 Intermediate Similarity NPD2981 Phase 2
0.7304 Intermediate Similarity NPD3972 Approved
0.73 Intermediate Similarity NPD844 Approved
0.73 Intermediate Similarity NPD1809 Phase 2
0.7282 Intermediate Similarity NPD940 Approved
0.7282 Intermediate Similarity NPD291 Approved
0.7282 Intermediate Similarity NPD846 Approved
0.7273 Intermediate Similarity NPD845 Approved
0.7257 Intermediate Similarity NPD5585 Approved
0.7257 Intermediate Similarity NPD3443 Approved
0.7257 Intermediate Similarity NPD3445 Approved
0.7257 Intermediate Similarity NPD2594 Approved
0.7257 Intermediate Similarity NPD3444 Approved
0.7257 Intermediate Similarity NPD3049 Approved
0.7257 Intermediate Similarity NPD2595 Approved
0.7241 Intermediate Similarity NPD2429 Approved
0.7241 Intermediate Similarity NPD6582 Phase 2
0.7241 Intermediate Similarity NPD6542 Approved
0.7241 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD2428 Approved
0.7241 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD1669 Approved
0.7241 Intermediate Similarity NPD5327 Phase 3
0.7241 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD2982 Phase 2
0.7241 Intermediate Similarity NPD6543 Approved
0.7241 Intermediate Similarity NPD6540 Phase 3
0.7241 Intermediate Similarity NPD2983 Phase 2
0.7241 Intermediate Similarity NPD6583 Phase 3
0.7241 Intermediate Similarity NPD3685 Discontinued
0.7241 Intermediate Similarity NPD6539 Approved
0.7228 Intermediate Similarity NPD288 Approved
0.7217 Intermediate Similarity NPD1610 Phase 2
0.7217 Intermediate Similarity NPD422 Phase 1
0.7217 Intermediate Similarity NPD3705 Approved
0.7207 Intermediate Similarity NPD6387 Discontinued
0.7193 Intermediate Similarity NPD2554 Approved
0.7193 Intermediate Similarity NPD2556 Approved
0.7193 Intermediate Similarity NPD1778 Approved
0.7184 Intermediate Similarity NPD1242 Phase 1
0.7179 Intermediate Similarity NPD6538 Approved
0.7179 Intermediate Similarity NPD1876 Approved
0.7179 Intermediate Similarity NPD6541 Approved
0.7179 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1283 Approved
0.7168 Intermediate Similarity NPD2486 Discontinued
0.7155 Intermediate Similarity NPD1840 Phase 2
0.7143 Intermediate Similarity NPD9608 Approved
0.7143 Intermediate Similarity NPD9610 Approved
0.713 Intermediate Similarity NPD3496 Discontinued
0.7119 Intermediate Similarity NPD1820 Approved
0.7119 Intermediate Similarity NPD1819 Approved
0.7119 Intermediate Similarity NPD1817 Approved
0.7119 Intermediate Similarity NPD1818 Approved
0.7105 Intermediate Similarity NPD6382 Discontinued
0.7103 Intermediate Similarity NPD5373 Approved
0.7103 Intermediate Similarity NPD5374 Approved
0.7094 Intermediate Similarity NPD4129 Approved
0.7079 Intermediate Similarity NPD9087 Approved
0.7069 Intermediate Similarity NPD1535 Discovery
0.7059 Intermediate Similarity NPD3691 Phase 2
0.7059 Intermediate Similarity NPD4624 Approved
0.7059 Intermediate Similarity NPD3690 Phase 2
0.7059 Intermediate Similarity NPD7018 Phase 2
0.7059 Intermediate Similarity NPD6584 Phase 3
0.7043 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD17 Approved
0.7034 Intermediate Similarity NPD196 Phase 1
0.7033 Intermediate Similarity NPD9294 Approved
0.7019 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD9545 Approved
0.7009 Intermediate Similarity NPD2230 Approved
0.7009 Intermediate Similarity NPD2233 Approved
0.7009 Intermediate Similarity NPD2232 Approved
0.7009 Intermediate Similarity NPD1481 Phase 2
0.7 Intermediate Similarity NPD9494 Approved
0.7 Intermediate Similarity NPD3018 Phase 2
0.7 Intermediate Similarity NPD4993 Discontinued
0.6983 Remote Similarity NPD3294 Phase 2
0.6981 Remote Similarity NPD9501 Approved
0.6975 Remote Similarity NPD3568 Approved
0.6975 Remote Similarity NPD987 Approved
0.6975 Remote Similarity NPD3567 Approved
0.6949 Remote Similarity NPD4359 Approved
0.6944 Remote Similarity NPD9624 Approved
0.6942 Remote Similarity NPD4908 Phase 1
0.6942 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1091 Approved
0.6923 Remote Similarity NPD776 Approved
0.6923 Remote Similarity NPD1611 Approved
0.6897 Remote Similarity NPD2107 Clinical (unspecified phase)
0.6891 Remote Similarity NPD2922 Phase 1
0.6891 Remote Similarity NPD8651 Approved
0.6885 Remote Similarity NPD3165 Approved
0.6885 Remote Similarity NPD3164 Approved
0.6885 Remote Similarity NPD3167 Approved
0.6885 Remote Similarity NPD3166 Approved
0.6885 Remote Similarity NPD3179 Approved
0.6885 Remote Similarity NPD5746 Approved
0.6885 Remote Similarity NPD5163 Phase 2
0.6885 Remote Similarity NPD3027 Phase 3
0.6885 Remote Similarity NPD3180 Approved
0.6864 Remote Similarity NPD2231 Phase 2
0.6864 Remote Similarity NPD1608 Approved
0.6864 Remote Similarity NPD2235 Phase 2
0.6864 Remote Similarity NPD1244 Clinical (unspecified phase)
0.6864 Remote Similarity NPD9717 Approved
0.686 Remote Similarity NPD2861 Phase 2
0.686 Remote Similarity NPD454 Approved
0.6842 Remote Similarity NPD9493 Approved
0.6837 Remote Similarity NPD1282 Approved
0.6833 Remote Similarity NPD1770 Clinical (unspecified phase)
0.6833 Remote Similarity NPD4098 Discontinued
0.6833 Remote Similarity NPD1232 Clinical (unspecified phase)
0.6833 Remote Similarity NPD1794 Approved
0.6829 Remote Similarity NPD3144 Approved
0.6829 Remote Similarity NPD5718 Phase 2
0.6829 Remote Similarity NPD7294 Phase 1
0.6829 Remote Similarity NPD5109 Approved
0.6829 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6829 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5110 Phase 2
0.6829 Remote Similarity NPD1039 Discontinued
0.6829 Remote Similarity NPD5111 Phase 2
0.6829 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3145 Approved
0.6829 Remote Similarity NPD6798 Discontinued
0.6818 Remote Similarity NPD3022 Approved
0.6818 Remote Similarity NPD556 Approved
0.6818 Remote Similarity NPD3021 Approved
0.6818 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6807 Remote Similarity NPD1421 Approved
0.6807 Remote Similarity NPD1420 Approved
0.6803 Remote Similarity NPD682 Discontinued
0.6803 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6789 Remote Similarity NPD9552 Approved
0.6786 Remote Similarity NPD769 Approved
0.6777 Remote Similarity NPD1019 Discontinued
0.6777 Remote Similarity NPD2987 Approved
0.6777 Remote Similarity NPD7905 Discontinued
0.6777 Remote Similarity NPD2990 Approved
0.6774 Remote Similarity NPD9088 Approved
0.6774 Remote Similarity NPD3058 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4062 Phase 3
0.6774 Remote Similarity NPD7265 Discontinued

  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