Structure

Physi-Chem Properties

Molecular Weight:  680.33
Volume:  731.537
LogP:  8.842
LogD:  4.813
LogS:  -4.932
# Rotatable Bonds:  15
TPSA:  93.43
# H-Bond Aceptor:  8
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.091
Synthetic Accessibility Score:  3.489
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.838
MDCK Permeability:  1.3124910765327513e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.085
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.043
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  66.56458282470703%
Volume Distribution (VD):  0.847
Pgp-substrate:  36.16849899291992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.718
CYP2C19-inhibitor:  0.82
CYP2C19-substrate:  0.277
CYP2C9-inhibitor:  0.964
CYP2C9-substrate:  0.93
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.449
CYP3A4-inhibitor:  0.548
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  8.794
Half-life (T1/2):  0.035

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.981
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.059
Rat Oral Acute Toxicity:  0.035
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.179
Carcinogencity:  0.029
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.368

Download Data

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

  Natural Product: NPC475144

Natural Product ID:  NPC475144
Common Name*:   2-[3,4-Dimethoxy-2,6-Bis(3-Methylbut-2-Enyl)Phenyl]-5,7-Dimethoxy-8-(3-Methylbut-2-Enyl)-3-Phenacyloxychromen-4-One
IUPAC Name:   2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-5,7-dimethoxy-8-(3-methylbut-2-enyl)-3-phenacyloxychromen-4-one
Synonyms:  
Standard InCHIKey:  PIXAPMGONJHYEX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C42H48O8/c1-25(2)16-19-29-22-35(47-9)39(48-10)31(21-18-27(5)6)36(29)41-42(49-24-32(43)28-14-12-11-13-15-28)38(44)37-34(46-8)23-33(45-7)30(40(37)50-41)20-17-26(3)4/h11-18,22-23H,19-21,24H2,1-10H3
SMILES:  CC(=CCC1=CC(=C(C(=C1C2=C(C(=O)C3=C(C=C(C(=C3O2)CC=C(C)C)OC)OC)OCC(=O)C4=CC=CC=C4)CC=C(C)C)OC)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL499297
PubChem CID:   44584423
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003587] 2'-prenylated flavones

*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
NPO27127 Petalostemum purpureum n.a. n.a. n.a. n.a. n.a. n.a. PMID[8289060]
NPO27127 Petalostemum purpureum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT20 Organism Candida albicans Candida albicans MIC = 5.0 ug.mL-1 PMID[476354]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 5.0 ug.mL-1 PMID[476354]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare MIC = 5.0 ug.mL-1 PMID[476354]
NPT19 Organism Escherichia coli Escherichia coli MIC = 5.0 ug.mL-1 PMID[476354]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 5.0 ug.mL-1 PMID[476354]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 5.0 ug.mL-1 PMID[476354]

☑ 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 NPC475144 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
0.9542 High Similarity NPC473664
0.915 High Similarity NPC299923
0.9103 High Similarity NPC40033
0.9097 High Similarity NPC5840
0.9097 High Similarity NPC189270
0.9085 High Similarity NPC310259
0.9062 High Similarity NPC474239
0.902 High Similarity NPC471590
0.9018 High Similarity NPC150131
0.9 High Similarity NPC477164
0.9 High Similarity NPC299436
0.8974 High Similarity NPC201547
0.8974 High Similarity NPC259058
0.8968 High Similarity NPC476342
0.8954 High Similarity NPC113089
0.8951 High Similarity NPC474240
0.8931 High Similarity NPC248299
0.8931 High Similarity NPC474983
0.8924 High Similarity NPC128961
0.8924 High Similarity NPC472408
0.8917 High Similarity NPC474170
0.8917 High Similarity NPC474388
0.8917 High Similarity NPC472535
0.891 High Similarity NPC181250
0.891 High Similarity NPC69752
0.8903 High Similarity NPC474999
0.8903 High Similarity NPC470511
0.8903 High Similarity NPC117463
0.8896 High Similarity NPC475888
0.8896 High Similarity NPC280893
0.8896 High Similarity NPC136278
0.8889 High Similarity NPC70853
0.8889 High Similarity NPC201800
0.8889 High Similarity NPC9966
0.8889 High Similarity NPC302741
0.8889 High Similarity NPC476054
0.8875 High Similarity NPC19097
0.8875 High Similarity NPC273843
0.8868 High Similarity NPC471746
0.8862 High Similarity NPC99591
0.8861 High Similarity NPC166201
0.8854 High Similarity NPC177839
0.8848 High Similarity NPC188079
0.8846 High Similarity NPC261548
0.8841 High Similarity NPC477517
0.8834 High Similarity NPC186686
0.8831 High Similarity NPC293201
0.8827 High Similarity NPC474351
0.8827 High Similarity NPC474187
0.8827 High Similarity NPC165549
0.8827 High Similarity NPC475883
0.8824 High Similarity NPC185607
0.8824 High Similarity NPC29536
0.882 High Similarity NPC187792
0.8812 High Similarity NPC257277
0.8812 High Similarity NPC13779
0.8812 High Similarity NPC180340
0.8812 High Similarity NPC475799
0.881 High Similarity NPC156955
0.8797 High Similarity NPC236769
0.8797 High Similarity NPC76376
0.8795 High Similarity NPC279209
0.8795 High Similarity NPC102277
0.8788 High Similarity NPC260266
0.8788 High Similarity NPC218226
0.8782 High Similarity NPC85233
0.8782 High Similarity NPC205522
0.878 High Similarity NPC475369
0.878 High Similarity NPC303174
0.878 High Similarity NPC293319
0.8773 High Similarity NPC229632
0.8773 High Similarity NPC211107
0.8773 High Similarity NPC476247
0.8773 High Similarity NPC108767
0.8765 High Similarity NPC298093
0.8765 High Similarity NPC474287
0.8765 High Similarity NPC36217
0.8765 High Similarity NPC474960
0.8765 High Similarity NPC475886
0.8758 High Similarity NPC183851
0.8758 High Similarity NPC63454
0.8758 High Similarity NPC473272
0.8758 High Similarity NPC284820
0.8758 High Similarity NPC78071
0.875 High Similarity NPC56786
0.875 High Similarity NPC34725
0.875 High Similarity NPC241774
0.875 High Similarity NPC284353
0.875 High Similarity NPC122623
0.875 High Similarity NPC276059
0.875 High Similarity NPC133392
0.875 High Similarity NPC226025
0.875 High Similarity NPC80534
0.8743 High Similarity NPC476370
0.8742 High Similarity NPC134677
0.8735 High Similarity NPC475212
0.8734 High Similarity NPC166753
0.8734 High Similarity NPC219330
0.8734 High Similarity NPC50728
0.8727 High Similarity NPC272502
0.8727 High Similarity NPC475214
0.8727 High Similarity NPC39091
0.8727 High Similarity NPC43319
0.8727 High Similarity NPC470462
0.8727 High Similarity NPC471213
0.8726 High Similarity NPC10304
0.8726 High Similarity NPC63256
0.8726 High Similarity NPC476058
0.872 High Similarity NPC472625
0.872 High Similarity NPC470459
0.8718 High Similarity NPC302408
0.8718 High Similarity NPC216314
0.8718 High Similarity NPC215932
0.8718 High Similarity NPC120924
0.8718 High Similarity NPC106461
0.8718 High Similarity NPC40818
0.8718 High Similarity NPC195919
0.8718 High Similarity NPC110639
0.8718 High Similarity NPC14958
0.8718 High Similarity NPC283002
0.8712 High Similarity NPC26326
0.8712 High Similarity NPC289771
0.8712 High Similarity NPC158188
0.8712 High Similarity NPC474186
0.8712 High Similarity NPC34376
0.8712 High Similarity NPC142252
0.8712 High Similarity NPC471499
0.8706 High Similarity NPC104682
0.8704 High Similarity NPC172202
0.8704 High Similarity NPC476410
0.8704 High Similarity NPC184755
0.8704 High Similarity NPC284127
0.8704 High Similarity NPC210459
0.8704 High Similarity NPC280680
0.8704 High Similarity NPC113055
0.8704 High Similarity NPC74178
0.8698 High Similarity NPC216307
0.8696 High Similarity NPC265511
0.8696 High Similarity NPC153512
0.8696 High Similarity NPC178854
0.869 High Similarity NPC476374
0.8688 High Similarity NPC58382
0.8688 High Similarity NPC246204
0.8688 High Similarity NPC236223
0.8688 High Similarity NPC270620
0.8688 High Similarity NPC279930
0.8688 High Similarity NPC179126
0.8688 High Similarity NPC186507
0.8688 High Similarity NPC78326
0.8688 High Similarity NPC162351
0.8679 High Similarity NPC474414
0.8675 High Similarity NPC8965
0.8675 High Similarity NPC470456
0.8675 High Similarity NPC476306
0.8675 High Similarity NPC158761
0.8671 High Similarity NPC238366
0.8671 High Similarity NPC159103
0.8667 High Similarity NPC36916
0.8667 High Similarity NPC125039
0.8667 High Similarity NPC36
0.8667 High Similarity NPC470457
0.8667 High Similarity NPC7688
0.8667 High Similarity NPC472450
0.8667 High Similarity NPC72787
0.8667 High Similarity NPC58223
0.8667 High Similarity NPC275780
0.8667 High Similarity NPC239752
0.8667 High Similarity NPC7154
0.8667 High Similarity NPC62261
0.8659 High Similarity NPC78332
0.8659 High Similarity NPC474150
0.8659 High Similarity NPC474162
0.8659 High Similarity NPC472964
0.8654 High Similarity NPC165512
0.865 High Similarity NPC188967
0.865 High Similarity NPC192686
0.865 High Similarity NPC475784
0.865 High Similarity NPC470326
0.865 High Similarity NPC471973
0.865 High Similarity NPC246478
0.865 High Similarity NPC119209
0.865 High Similarity NPC287328
0.865 High Similarity NPC282009
0.865 High Similarity NPC118256
0.865 High Similarity NPC321399
0.865 High Similarity NPC297212
0.8642 High Similarity NPC165977
0.8642 High Similarity NPC67876
0.8642 High Similarity NPC183
0.8642 High Similarity NPC217677
0.8642 High Similarity NPC472963
0.8642 High Similarity NPC237418
0.8642 High Similarity NPC52889
0.8642 High Similarity NPC291508
0.8642 High Similarity NPC471479
0.8642 High Similarity NPC476981
0.8642 High Similarity NPC471515
0.8634 High Similarity NPC222185
0.8634 High Similarity NPC189960
0.8634 High Similarity NPC234255

  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 NPC475144 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
0.8868 High Similarity NPD3817 Phase 2
0.8765 High Similarity NPD5494 Approved
0.8688 High Similarity NPD7819 Suspended
0.8667 High Similarity NPD6166 Phase 2
0.8667 High Similarity NPD6168 Clinical (unspecified phase)
0.8667 High Similarity NPD6167 Clinical (unspecified phase)
0.8503 High Similarity NPD7473 Discontinued
0.8485 Intermediate Similarity NPD1247 Approved
0.8476 Intermediate Similarity NPD919 Approved
0.8466 Intermediate Similarity NPD3882 Suspended
0.8457 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD6232 Discontinued
0.8421 Intermediate Similarity NPD7808 Phase 3
0.8418 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD7075 Discontinued
0.8405 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD5844 Phase 1
0.8395 Intermediate Similarity NPD1934 Approved
0.8395 Intermediate Similarity NPD6801 Discontinued
0.8383 Intermediate Similarity NPD3926 Phase 2
0.8377 Intermediate Similarity NPD2796 Approved
0.8344 Intermediate Similarity NPD2801 Approved
0.8302 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8294 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8272 Intermediate Similarity NPD4380 Phase 2
0.8263 Intermediate Similarity NPD6959 Discontinued
0.8256 Intermediate Similarity NPD7251 Discontinued
0.825 Intermediate Similarity NPD1512 Approved
0.8239 Intermediate Similarity NPD6799 Approved
0.8221 Intermediate Similarity NPD7411 Suspended
0.8198 Intermediate Similarity NPD6797 Phase 2
0.8187 Intermediate Similarity NPD7054 Approved
0.816 Intermediate Similarity NPD6599 Discontinued
0.814 Intermediate Similarity NPD7074 Phase 3
0.814 Intermediate Similarity NPD7472 Approved
0.8133 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD3818 Discontinued
0.8125 Intermediate Similarity NPD1511 Approved
0.8103 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD5402 Approved
0.8024 Intermediate Similarity NPD7768 Phase 2
0.8012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD5403 Approved
0.7963 Intermediate Similarity NPD5401 Approved
0.7962 Intermediate Similarity NPD3748 Approved
0.7953 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD1510 Phase 2
0.7845 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD1549 Phase 2
0.7798 Intermediate Similarity NPD1465 Phase 2
0.7758 Intermediate Similarity NPD920 Approved
0.775 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD7199 Phase 2
0.7716 Intermediate Similarity NPD3750 Approved
0.7676 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD3226 Approved
0.7661 Intermediate Similarity NPD3749 Approved
0.7654 Intermediate Similarity NPD1243 Approved
0.7654 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD6559 Discontinued
0.7636 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD3751 Discontinued
0.76 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1240 Approved
0.7593 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD3787 Discontinued
0.7576 Intermediate Similarity NPD7390 Discontinued
0.7569 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD8312 Approved
0.7556 Intermediate Similarity NPD8313 Approved
0.753 Intermediate Similarity NPD2532 Approved
0.753 Intermediate Similarity NPD2533 Approved
0.753 Intermediate Similarity NPD2534 Approved
0.75 Intermediate Similarity NPD1607 Approved
0.7452 Intermediate Similarity NPD6832 Phase 2
0.7438 Intermediate Similarity NPD1933 Approved
0.7432 Intermediate Similarity NPD8150 Discontinued
0.7427 Intermediate Similarity NPD37 Approved
0.7423 Intermediate Similarity NPD1471 Phase 3
0.7423 Intermediate Similarity NPD2346 Discontinued
0.7407 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD4966 Approved
0.7399 Intermediate Similarity NPD4965 Approved
0.7399 Intermediate Similarity NPD4967 Phase 2
0.7396 Intermediate Similarity NPD7870 Phase 2
0.7396 Intermediate Similarity NPD7871 Phase 2
0.7386 Intermediate Similarity NPD7229 Phase 3
0.7362 Intermediate Similarity NPD2935 Discontinued
0.7358 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD5242 Approved
0.7344 Intermediate Similarity NPD7697 Approved
0.7344 Intermediate Similarity NPD7698 Approved
0.7344 Intermediate Similarity NPD7696 Phase 3
0.7344 Intermediate Similarity NPD7435 Discontinued
0.7337 Intermediate Similarity NPD8434 Phase 2
0.7333 Intermediate Similarity NPD2800 Approved
0.7333 Intermediate Similarity NPD8151 Discontinued
0.733 Intermediate Similarity NPD8127 Discontinued
0.7316 Intermediate Similarity NPD8285 Discontinued
0.7314 Intermediate Similarity NPD6234 Discontinued
0.7303 Intermediate Similarity NPD2403 Approved
0.7301 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2799 Discontinued
0.7277 Intermediate Similarity NPD6776 Approved
0.7277 Intermediate Similarity NPD6778 Approved
0.7277 Intermediate Similarity NPD6779 Approved
0.7277 Intermediate Similarity NPD6780 Approved
0.7277 Intermediate Similarity NPD6782 Approved
0.7277 Intermediate Similarity NPD6781 Approved
0.7277 Intermediate Similarity NPD6777 Approved
0.7267 Intermediate Similarity NPD943 Approved
0.7262 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2313 Discontinued
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7228 Approved
0.7222 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD447 Suspended
0.7219 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7874 Approved
0.7198 Intermediate Similarity NPD5953 Discontinued
0.7194 Intermediate Similarity NPD7701 Phase 2
0.7186 Intermediate Similarity NPD4628 Phase 3
0.7184 Intermediate Similarity NPD8455 Phase 2
0.7182 Intermediate Similarity NPD7286 Phase 2
0.7178 Intermediate Similarity NPD6651 Approved
0.7168 Intermediate Similarity NPD6385 Approved
0.7168 Intermediate Similarity NPD6386 Approved
0.7152 Intermediate Similarity NPD6100 Approved
0.7152 Intermediate Similarity NPD1551 Phase 2
0.7152 Intermediate Similarity NPD6099 Approved
0.7151 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD5353 Approved
0.7143 Intermediate Similarity NPD6190 Approved
0.7143 Intermediate Similarity NPD6798 Discontinued
0.7127 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4908 Phase 1
0.7108 Intermediate Similarity NPD2344 Approved
0.7107 Intermediate Similarity NPD2798 Approved
0.7085 Intermediate Similarity NPD7783 Phase 2
0.7085 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD7801 Approved
0.7083 Intermediate Similarity NPD7700 Phase 2
0.7083 Intermediate Similarity NPD7699 Phase 2
0.7065 Intermediate Similarity NPD7685 Pre-registration
0.7065 Intermediate Similarity NPD7240 Approved
0.7055 Intermediate Similarity NPD4060 Phase 1
0.7055 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD1613 Approved
0.7048 Intermediate Similarity NPD5406 Approved
0.7048 Intermediate Similarity NPD5404 Approved
0.7048 Intermediate Similarity NPD5405 Approved
0.7048 Intermediate Similarity NPD5408 Approved
0.7045 Intermediate Similarity NPD4288 Approved
0.7041 Intermediate Similarity NPD8319 Approved
0.7041 Intermediate Similarity NPD8320 Phase 1
0.7041 Intermediate Similarity NPD3887 Approved
0.7033 Intermediate Similarity NPD7177 Discontinued
0.7022 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6535 Approved
0.7016 Intermediate Similarity NPD4360 Phase 2
0.7016 Intermediate Similarity NPD4363 Phase 3
0.7016 Intermediate Similarity NPD6534 Approved
0.7013 Intermediate Similarity NPD5536 Phase 2
0.7012 Intermediate Similarity NPD230 Phase 1
0.7012 Intermediate Similarity NPD6355 Discontinued
0.7 Intermediate Similarity NPD5710 Approved
0.7 Intermediate Similarity NPD5711 Approved
0.6994 Remote Similarity NPD6233 Phase 2
0.6989 Remote Similarity NPD2971 Approved
0.6989 Remote Similarity NPD2968 Approved
0.6982 Remote Similarity NPD7003 Approved
0.6982 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6982 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6273 Approved
0.6975 Remote Similarity NPD3027 Phase 3
0.6971 Remote Similarity NPD5890 Approved
0.6971 Remote Similarity NPD5889 Approved
0.697 Remote Similarity NPD7584 Approved
0.6962 Remote Similarity NPD3972 Approved
0.6957 Remote Similarity NPD3018 Phase 2
0.6957 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6946 Remote Similarity NPD2438 Suspended
0.6943 Remote Similarity NPD2974 Approved
0.6943 Remote Similarity NPD2973 Approved
0.6943 Remote Similarity NPD2975 Approved
0.6942 Remote Similarity NPD8155 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