Structure

Physi-Chem Properties

Molecular Weight:  418.14
Volume:  424.551
LogP:  5.429
LogD:  4.001
LogS:  -3.503
# Rotatable Bonds:  1
TPSA:  89.13
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.511
Synthetic Accessibility Score:  3.944
Fsp3:  0.24
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.762
MDCK Permeability:  1.4285887118603569e-05
Pgp-inhibitor:  0.92
Pgp-substrate:  0.02
Human Intestinal Absorption (HIA):  0.065
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.131

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  92.49626922607422%
Volume Distribution (VD):  0.671
Pgp-substrate:  7.328527450561523%

ADMET: Metabolism

CYP1A2-inhibitor:  0.451
CYP1A2-substrate:  0.503
CYP2C19-inhibitor:  0.931
CYP2C19-substrate:  0.085
CYP2C9-inhibitor:  0.908
CYP2C9-substrate:  0.941
CYP2D6-inhibitor:  0.843
CYP2D6-substrate:  0.308
CYP3A4-inhibitor:  0.523
CYP3A4-substrate:  0.195

ADMET: Excretion

Clearance (CL):  1.541
Half-life (T1/2):  0.143

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.986
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.863
Rat Oral Acute Toxicity:  0.807
Maximum Recommended Daily Dose:  0.771
Skin Sensitization:  0.349
Carcinogencity:  0.659
Eye Corrosion:  0.003
Eye Irritation:  0.372
Respiratory Toxicity:  0.774

Download Data

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

  Natural Product: NPC189087

Natural Product ID:  NPC189087
Common Name*:   Cyclomorusin
IUPAC Name:   n.a.
Synonyms:   Cyclomorusin
Standard InCHIKey:  GDQXJMLXEYSICD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C25H22O6/c1-12(2)9-19-21-22(28)20-16(27)11-18-15(7-8-25(3,4)31-18)23(20)30-24(21)14-6-5-13(26)10-17(14)29-19/h5-11,19,26-27H,1-4H3
SMILES:  CC(=CC1Oc2cc(O)ccc2c2c1c(=O)c1c(o2)c2C=CC(Oc2cc1O)(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1770313
PubChem CID:   5481969
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO8171 Artocarpus altilis Species Moraceae Eukaryota bud covers n.a. n.a. PMID[11975520]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. root n.a. PMID[12662107]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. root n.a. PMID[17396934]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. root n.a. PMID[17405024]
NPO19738 Morus nigra Species Moraceae Eukaryota n.a. bark n.a. PMID[18330242]
NPO23793 Morus lhou Species Moraceae Eukaryota n.a. bark n.a. PMID[18608767]
NPO28265.1 Morus alba var. atropurpurea Varieties Moraceae Eukaryota n.a. twig n.a. PMID[19149258]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO19738 Morus nigra Species Moraceae Eukaryota n.a. twig n.a. PMID[21401118]
NPO19738 Morus nigra Species Moraceae Eukaryota twigs Xinjiang Uygur Autonomous Region, China 2006-MAY PMID[21401118]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265.1 Morus alba var. atropurpurea Varieties Moraceae Eukaryota Fruits Zhenjiang, Jiangsu Province, China PMID[23060696]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO23540 Ficus hirta Species Moraceae Eukaryota n.a. root n.a. PMID[24494557]
NPO19738 Morus nigra Species Moraceae Eukaryota root bark Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO11796 Morus australis Species Moraceae Eukaryota Root Bark n.a. n.a. PMID[27908762]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9544568]
NPO19738 Morus nigra Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23793 Morus lhou Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8077 Artocarpus incisa Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23793 Morus lhou Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8077 Artocarpus incisa Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23540 Ficus hirta Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19738 Morus nigra Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23793 Morus lhou Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8171 Artocarpus altilis Species Moraceae 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
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 = 1700.0 nM PMID[555298]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Ki = 3100.0 nM PMID[555298]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 46.6 % PMID[555299]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 54.1 % PMID[555299]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 73.7 % PMID[555299]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 4.5 ug.mL-1 PMID[555299]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 = 101200.0 nM PMID[555297]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity < 60.0 % PMID[555299]
NPT32 Organism Mus musculus Mus musculus Activity = 86.3 % PMID[555299]
NPT32 Organism Mus musculus Mus musculus Activity = 86.2 % PMID[555299]
NPT32 Organism Mus musculus Mus musculus Activity = 81.9 % PMID[555299]
NPT32 Organism Mus musculus Mus musculus Activity = 57.6 % PMID[555299]
NPT32 Organism Mus musculus Mus musculus Activity = 14.0 % PMID[555299]

☑ 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 NPC189087 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 NPC321623
0.9859 High Similarity NPC161191
0.9787 High Similarity NPC319752
0.9718 High Similarity NPC54577
0.9718 High Similarity NPC214774
0.9718 High Similarity NPC195621
0.9718 High Similarity NPC176229
0.9718 High Similarity NPC142405
0.9718 High Similarity NPC267375
0.9718 High Similarity NPC301276
0.9718 High Similarity NPC312973
0.9718 High Similarity NPC20488
0.9718 High Similarity NPC476088
0.9718 High Similarity NPC475052
0.9718 High Similarity NPC83357
0.9718 High Similarity NPC67805
0.9718 High Similarity NPC246948
0.9718 High Similarity NPC111786
0.9718 High Similarity NPC474161
0.9718 High Similarity NPC88964
0.9718 High Similarity NPC470647
0.9653 High Similarity NPC5173
0.965 High Similarity NPC24673
0.965 High Similarity NPC23728
0.965 High Similarity NPC201731
0.965 High Similarity NPC473077
0.965 High Similarity NPC110303
0.965 High Similarity NPC283234
0.965 High Similarity NPC296998
0.965 High Similarity NPC104406
0.965 High Similarity NPC97716
0.965 High Similarity NPC237635
0.965 High Similarity NPC79469
0.9645 High Similarity NPC293852
0.9645 High Similarity NPC214236
0.9645 High Similarity NPC299080
0.9645 High Similarity NPC78803
0.9645 High Similarity NPC59739
0.9645 High Similarity NPC62840
0.9645 High Similarity NPC217083
0.9583 High Similarity NPC160821
0.9583 High Similarity NPC6511
0.9583 High Similarity NPC266572
0.9583 High Similarity NPC132592
0.9577 High Similarity NPC478086
0.9577 High Similarity NPC316816
0.9577 High Similarity NPC214166
0.951 High Similarity NPC131568
0.951 High Similarity NPC209040
0.951 High Similarity NPC131579
0.9507 High Similarity NPC324134
0.9507 High Similarity NPC10937
0.9507 High Similarity NPC40833
0.9507 High Similarity NPC125855
0.9507 High Similarity NPC182852
0.9507 High Similarity NPC161506
0.9507 High Similarity NPC296917
0.9507 High Similarity NPC37496
0.9507 High Similarity NPC226636
0.9507 High Similarity NPC166934
0.9507 High Similarity NPC194432
0.9507 High Similarity NPC306829
0.9507 High Similarity NPC1089
0.9507 High Similarity NPC32739
0.9507 High Similarity NPC227579
0.9507 High Similarity NPC223500
0.9507 High Similarity NPC228504
0.9507 High Similarity NPC107572
0.9507 High Similarity NPC78
0.9507 High Similarity NPC11561
0.9507 High Similarity NPC265040
0.9507 High Similarity NPC177354
0.9507 High Similarity NPC64915
0.9507 High Similarity NPC324436
0.9507 High Similarity NPC167624
0.9507 High Similarity NPC220998
0.9507 High Similarity NPC66515
0.9507 High Similarity NPC76372
0.9507 High Similarity NPC76338
0.9507 High Similarity NPC328164
0.9507 High Similarity NPC148757
0.9507 High Similarity NPC166482
0.9504 High Similarity NPC241100
0.9504 High Similarity NPC159275
0.9504 High Similarity NPC150522
0.9452 High Similarity NPC188403
0.9452 High Similarity NPC472633
0.9448 High Similarity NPC244407
0.9444 High Similarity NPC285630
0.9444 High Similarity NPC470131
0.9444 High Similarity NPC127059
0.9444 High Similarity NPC470133
0.9444 High Similarity NPC473078
0.9444 High Similarity NPC470132
0.9444 High Similarity NPC470134
0.9444 High Similarity NPC109183
0.9441 High Similarity NPC38219
0.9441 High Similarity NPC149026
0.9441 High Similarity NPC91560
0.9441 High Similarity NPC77794
0.9441 High Similarity NPC219915
0.9441 High Similarity NPC223812
0.9441 High Similarity NPC75049
0.9441 High Similarity NPC39329
0.9441 High Similarity NPC185276
0.9441 High Similarity NPC221432
0.9441 High Similarity NPC310130
0.9441 High Similarity NPC107177
0.9441 High Similarity NPC175504
0.9441 High Similarity NPC150408
0.9441 High Similarity NPC169591
0.9441 High Similarity NPC68104
0.9441 High Similarity NPC257097
0.9441 High Similarity NPC85162
0.9441 High Similarity NPC81697
0.9441 High Similarity NPC164980
0.9441 High Similarity NPC125894
0.9441 High Similarity NPC59522
0.9441 High Similarity NPC278249
0.9441 High Similarity NPC143896
0.9437 High Similarity NPC324386
0.9437 High Similarity NPC103362
0.9437 High Similarity NPC96408
0.9437 High Similarity NPC279650
0.9437 High Similarity NPC248372
0.9437 High Similarity NPC166689
0.9437 High Similarity NPC110969
0.9437 High Similarity NPC156590
0.9437 High Similarity NPC213322
0.9437 High Similarity NPC312391
0.9437 High Similarity NPC110038
0.9437 High Similarity NPC205006
0.9437 High Similarity NPC118840
0.9437 High Similarity NPC147688
0.9437 High Similarity NPC17170
0.9437 High Similarity NPC258630
0.9437 High Similarity NPC64908
0.9437 High Similarity NPC282300
0.9437 High Similarity NPC4743
0.9437 High Similarity NPC156190
0.9437 High Similarity NPC52576
0.9433 High Similarity NPC18260
0.9433 High Similarity NPC23257
0.9433 High Similarity NPC96565
0.9433 High Similarity NPC220062
0.9433 High Similarity NPC78913
0.9433 High Similarity NPC53181
0.9433 High Similarity NPC55018
0.9433 High Similarity NPC216978
0.9433 High Similarity NPC301217
0.9433 High Similarity NPC303633
0.9433 High Similarity NPC217186
0.9384 High Similarity NPC473016
0.9384 High Similarity NPC3642
0.9384 High Similarity NPC104236
0.9384 High Similarity NPC164205
0.9379 High Similarity NPC14001
0.9379 High Similarity NPC472627
0.9379 High Similarity NPC166757
0.9375 High Similarity NPC224714
0.9375 High Similarity NPC197252
0.9375 High Similarity NPC179970
0.9375 High Similarity NPC473014
0.9375 High Similarity NPC473013
0.9375 High Similarity NPC235217
0.9375 High Similarity NPC39045
0.9375 High Similarity NPC470136
0.9375 High Similarity NPC470135
0.9375 High Similarity NPC236766
0.9375 High Similarity NPC473015
0.9375 High Similarity NPC234629
0.9375 High Similarity NPC311741
0.9371 High Similarity NPC147145
0.9366 High Similarity NPC471587
0.9366 High Similarity NPC475680
0.9366 High Similarity NPC270883
0.9366 High Similarity NPC188243
0.9366 High Similarity NPC235239
0.9366 High Similarity NPC172986
0.9366 High Similarity NPC305355
0.9366 High Similarity NPC261227
0.9366 High Similarity NPC110228
0.9366 High Similarity NPC6407
0.9362 High Similarity NPC17848
0.9362 High Similarity NPC201395
0.9329 High Similarity NPC470681
0.932 High Similarity NPC61258
0.932 High Similarity NPC471115
0.932 High Similarity NPC29777
0.9315 High Similarity NPC296869
0.9315 High Similarity NPC168085
0.9315 High Similarity NPC122894
0.931 High Similarity NPC472629
0.931 High Similarity NPC124729
0.931 High Similarity NPC220418
0.931 High Similarity NPC57470
0.931 High Similarity NPC228779
0.9306 High Similarity NPC18585
0.9306 High Similarity NPC106985
0.9306 High Similarity NPC166138

  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 NPC189087 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
0.9241 High Similarity NPD7410 Clinical (unspecified phase)
0.9241 High Similarity NPD4378 Clinical (unspecified phase)
0.9155 High Similarity NPD1552 Clinical (unspecified phase)
0.9155 High Similarity NPD1550 Clinical (unspecified phase)
0.9091 High Similarity NPD1549 Phase 2
0.8951 High Similarity NPD2796 Approved
0.8947 High Similarity NPD8443 Clinical (unspecified phase)
0.8933 High Similarity NPD4380 Phase 2
0.8882 High Similarity NPD2393 Clinical (unspecified phase)
0.8881 High Similarity NPD1510 Phase 2
0.8874 High Similarity NPD7411 Suspended
0.8732 High Similarity NPD1240 Approved
0.871 High Similarity NPD7075 Discontinued
0.8693 High Similarity NPD6801 Discontinued
0.8636 High Similarity NPD7096 Clinical (unspecified phase)
0.8611 High Similarity NPD1607 Approved
0.859 High Similarity NPD4381 Clinical (unspecified phase)
0.8571 High Similarity NPD1934 Approved
0.8571 High Similarity NPD7804 Clinical (unspecified phase)
0.8544 High Similarity NPD6959 Discontinued
0.8516 High Similarity NPD7819 Suspended
0.85 High Similarity NPD7852 Clinical (unspecified phase)
0.8411 Intermediate Similarity NPD1511 Approved
0.8411 Intermediate Similarity NPD6799 Approved
0.8408 Intermediate Similarity NPD7768 Phase 2
0.8397 Intermediate Similarity NPD2801 Approved
0.8389 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD6166 Phase 2
0.8385 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD5403 Approved
0.8333 Intermediate Similarity NPD3750 Approved
0.8301 Intermediate Similarity NPD1512 Approved
0.8235 Intermediate Similarity NPD5401 Approved
0.8232 Intermediate Similarity NPD7054 Approved
0.8207 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8205 Intermediate Similarity NPD6599 Discontinued
0.8182 Intermediate Similarity NPD7074 Phase 3
0.8182 Intermediate Similarity NPD7472 Approved
0.8176 Intermediate Similarity NPD3882 Suspended
0.8146 Intermediate Similarity NPD2800 Approved
0.8137 Intermediate Similarity NPD5494 Approved
0.8133 Intermediate Similarity NPD6797 Phase 2
0.8125 Intermediate Similarity NPD3749 Approved
0.8113 Intermediate Similarity NPD3817 Phase 2
0.8108 Intermediate Similarity NPD6651 Approved
0.8084 Intermediate Similarity NPD7251 Discontinued
0.8079 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD1551 Phase 2
0.8061 Intermediate Similarity NPD3818 Discontinued
0.8041 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD5124 Phase 1
0.8036 Intermediate Similarity NPD7808 Phase 3
0.8036 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD1243 Approved
0.8013 Intermediate Similarity NPD920 Approved
0.8 Intermediate Similarity NPD3748 Approved
0.8 Intermediate Similarity NPD5402 Approved
0.8 Intermediate Similarity NPD7033 Discontinued
0.7987 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD2935 Discontinued
0.7917 Intermediate Similarity NPD5953 Discontinued
0.7904 Intermediate Similarity NPD7286 Phase 2
0.7885 Intermediate Similarity NPD2532 Approved
0.7885 Intermediate Similarity NPD2534 Approved
0.7885 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD2533 Approved
0.7881 Intermediate Similarity NPD2799 Discontinued
0.787 Intermediate Similarity NPD6559 Discontinued
0.7857 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD2313 Discontinued
0.7832 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD4908 Phase 1
0.7818 Intermediate Similarity NPD6232 Discontinued
0.7801 Intermediate Similarity NPD1548 Phase 1
0.7798 Intermediate Similarity NPD5844 Phase 1
0.7784 Intermediate Similarity NPD4360 Phase 2
0.7784 Intermediate Similarity NPD4363 Phase 3
0.7784 Intermediate Similarity NPD7473 Discontinued
0.7778 Intermediate Similarity NPD2344 Approved
0.7742 Intermediate Similarity NPD4628 Phase 3
0.774 Intermediate Similarity NPD1203 Approved
0.7718 Intermediate Similarity NPD3268 Approved
0.7712 Intermediate Similarity NPD6099 Approved
0.7712 Intermediate Similarity NPD6100 Approved
0.7707 Intermediate Similarity NPD7390 Discontinued
0.7703 Intermediate Similarity NPD6832 Phase 2
0.7697 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD3225 Approved
0.7647 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD919 Approved
0.7619 Intermediate Similarity NPD2797 Approved
0.7602 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD422 Phase 1
0.7586 Intermediate Similarity NPD1610 Phase 2
0.758 Intermediate Similarity NPD2309 Approved
0.7578 Intermediate Similarity NPD3226 Approved
0.7568 Intermediate Similarity NPD2798 Approved
0.7545 Intermediate Similarity NPD1247 Approved
0.7542 Intermediate Similarity NPD4361 Phase 2
0.7542 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD9717 Approved
0.7532 Intermediate Similarity NPD4308 Phase 3
0.7516 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD943 Approved
0.7472 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD7458 Discontinued
0.7452 Intermediate Similarity NPD2654 Approved
0.7442 Intermediate Similarity NPD1729 Discontinued
0.7438 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD2346 Discontinued
0.7419 Intermediate Similarity NPD7584 Approved
0.7417 Intermediate Similarity NPD4625 Phase 3
0.7412 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD3267 Approved
0.7383 Intermediate Similarity NPD3266 Approved
0.7378 Intermediate Similarity NPD5889 Approved
0.7378 Intermediate Similarity NPD5890 Approved
0.7375 Intermediate Similarity NPD7213 Phase 3
0.7375 Intermediate Similarity NPD7212 Phase 2
0.7368 Intermediate Similarity NPD6798 Discontinued
0.7362 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD3926 Phase 2
0.7349 Intermediate Similarity NPD4288 Approved
0.7326 Intermediate Similarity NPD3751 Discontinued
0.7317 Intermediate Similarity NPD6585 Discontinued
0.731 Intermediate Similarity NPD9545 Approved
0.7297 Intermediate Similarity NPD3972 Approved
0.7296 Intermediate Similarity NPD7003 Approved
0.7294 Intermediate Similarity NPD5710 Approved
0.7294 Intermediate Similarity NPD3787 Discontinued
0.7294 Intermediate Similarity NPD5711 Approved
0.7289 Intermediate Similarity NPD1465 Phase 2
0.7273 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD8313 Approved
0.7273 Intermediate Similarity NPD1613 Approved
0.7273 Intermediate Similarity NPD8312 Approved
0.7273 Intermediate Similarity NPD4307 Phase 2
0.7255 Intermediate Similarity NPD1296 Phase 2
0.7239 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6844 Discontinued
0.7226 Intermediate Similarity NPD1933 Approved
0.7226 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7447 Phase 1
0.7203 Intermediate Similarity NPD1241 Discontinued
0.7193 Intermediate Similarity NPD7229 Phase 3
0.7189 Intermediate Similarity NPD6779 Approved
0.7189 Intermediate Similarity NPD6781 Approved
0.7189 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD6777 Approved
0.7189 Intermediate Similarity NPD6778 Approved
0.7189 Intermediate Similarity NPD6782 Approved
0.7189 Intermediate Similarity NPD6776 Approved
0.7189 Intermediate Similarity NPD6780 Approved
0.7186 Intermediate Similarity NPD8455 Phase 2
0.7181 Intermediate Similarity NPD1608 Approved
0.7172 Intermediate Similarity NPD9493 Approved
0.717 Intermediate Similarity NPD2424 Discontinued
0.7167 Intermediate Similarity NPD4287 Approved
0.7167 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD6104 Discontinued
0.7152 Intermediate Similarity NPD5404 Approved
0.7152 Intermediate Similarity NPD5406 Approved
0.7152 Intermediate Similarity NPD5405 Approved
0.7152 Intermediate Similarity NPD5408 Approved
0.7143 Intermediate Similarity NPD3887 Approved
0.7143 Intermediate Similarity NPD3764 Approved
0.7143 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD4749 Approved
0.7126 Intermediate Similarity NPD7577 Discontinued
0.7126 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1652 Phase 2
0.7124 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4662 Approved
0.7117 Intermediate Similarity NPD4661 Approved
0.7115 Intermediate Similarity NPD230 Phase 1
0.7115 Intermediate Similarity NPD6355 Discontinued
0.7114 Intermediate Similarity NPD1201 Approved
0.7107 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD1019 Discontinued
0.7097 Intermediate Similarity NPD6233 Phase 2
0.7083 Intermediate Similarity NPD5760 Phase 2
0.7083 Intermediate Similarity NPD5761 Phase 2
0.7078 Intermediate Similarity NPD3027 Phase 3
0.7074 Intermediate Similarity NPD7697 Approved
0.7074 Intermediate Similarity NPD7698 Approved
0.7074 Intermediate Similarity NPD7435 Discontinued
0.7074 Intermediate Similarity NPD7696 Phase 3
0.7073 Intermediate Similarity NPD6273 Approved
0.7073 Intermediate Similarity NPD5049 Phase 3
0.7059 Intermediate Similarity NPD2861 Phase 2
0.7059 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD8150 Discontinued
0.7056 Intermediate Similarity NPD8434 Phase 2
0.7055 Intermediate Similarity NPD6143 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