Structure

Physi-Chem Properties

Molecular Weight:  454.2
Volume:  470.386
LogP:  5.36
LogD:  3.363
LogS:  -3.151
# Rotatable Bonds:  7
TPSA:  116.45
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.447
Synthetic Accessibility Score:  3.766
Fsp3:  0.346
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.955
MDCK Permeability:  9.547116860630922e-06
Pgp-inhibitor:  0.451
Pgp-substrate:  0.047
Human Intestinal Absorption (HIA):  0.081
20% Bioavailability (F20%):  0.875
30% Bioavailability (F30%):  0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  93.8349380493164%
Volume Distribution (VD):  0.633
Pgp-substrate:  5.885175704956055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.135
CYP1A2-substrate:  0.707
CYP2C19-inhibitor:  0.66
CYP2C19-substrate:  0.1
CYP2C9-inhibitor:  0.896
CYP2C9-substrate:  0.923
CYP2D6-inhibitor:  0.908
CYP2D6-substrate:  0.393
CYP3A4-inhibitor:  0.433
CYP3A4-substrate:  0.197

ADMET: Excretion

Clearance (CL):  7.716
Half-life (T1/2):  0.229

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.452
Drug-inuced Liver Injury (DILI):  0.658
AMES Toxicity:  0.053
Rat Oral Acute Toxicity:  0.178
Maximum Recommended Daily Dose:  0.026
Skin Sensitization:  0.649
Carcinogencity:  0.122
Eye Corrosion:  0.003
Eye Irritation:  0.142
Respiratory Toxicity:  0.212

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

  Natural Product: NPC287328

Natural Product ID:  NPC287328
Common Name*:   3'-O-Methyldiplacol
IUPAC Name:   (2R,3R)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:   3'-O-Methyldiplacol
Standard InCHIKey:  YHOYRZLJSAAOGW-WFQOKMFZSA-N
Standard InCHI:  InChI=1S/C26H30O7/c1-14(2)6-5-7-15(3)8-10-17-19(28)13-21-22(23(17)29)24(30)25(31)26(33-21)16-9-11-18(27)20(12-16)32-4/h6,8-9,11-13,25-29,31H,5,7,10H2,1-4H3/b15-8+/t25-,26+/m0/s1
SMILES:  COc1cc(ccc1O)[C@H]1Oc2cc(O)c(c(c2C(=O)[C@@H]1O)O)C/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL459258
PubChem CID:   21607150
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0003646] 6-prenylated flavans
            • [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[17625893]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[18293924]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. PMID[20192247]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. fruit n.a. PMID[21319773]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[22445674]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[23623680]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[25735399]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[28322565]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[28968119]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22079 Paulownia tomentosa Species Paulowniaceae 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
NPT83 Cell Line MCF7 Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT404 Cell Line CCRF-CEM Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT389 Cell Line RPMI-8226 Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT2015 Cell Line U-266 Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT165 Cell Line HeLa Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT1160 Cell Line BJ Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT1970 Cell Line THP-1 Homo sapiens EC50 > 10000.0 nM PMID[508406]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 48500.0 nM PMID[508407]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Ki = 68200.0 nM PMID[508407]
NPT2569 Individual Protein Butyrylcholinesterase Equus caballus IC50 = 11200.0 nM PMID[508407]
NPT2569 Individual Protein Butyrylcholinesterase Equus caballus Ki = 18200.0 nM PMID[508407]
NPT1970 Cell Line THP-1 Homo sapiens IC50 < 10000.0 nM PMID[508409]
NPT19 Organism Escherichia coli Escherichia coli MIC > 32.0 ug.mL-1 PMID[508405]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 32.0 ug.mL-1 PMID[508405]
NPT3608 Organism Salmonella enteritidis Salmonella enterica subsp. enterica serovar Enteritidis MIC > 32.0 ug.mL-1 PMID[508405]
NPT20 Organism Candida albicans Candida albicans MIC > 32.0 ug.mL-1 PMID[508405]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 2.0 ug.mL-1 PMID[508405]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 4.0 ug.mL-1 PMID[508405]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 4.0 ug.mL-1 PMID[508405]
NPT564 Organism Listeria monocytogenes Listeria monocytogenes MIC = 2.0 ug.mL-1 PMID[508405]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 2.0 ug.mL-1 PMID[508405]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 2.0 ug.mL-1 PMID[508405]
NPT2 Others Unspecified Ki = 6600.0 nM PMID[508408]
NPT2 Others Unspecified IC50 = 9500.0 nM PMID[508408]

☑ 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 NPC287328 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 NPC282009
0.9934 High Similarity NPC22192
0.9934 High Similarity NPC471499
0.9868 High Similarity NPC470326
0.9868 High Similarity NPC472598
0.9868 High Similarity NPC474055
0.9805 High Similarity NPC472625
0.9801 High Similarity NPC320825
0.9801 High Similarity NPC326037
0.9801 High Similarity NPC195796
0.9801 High Similarity NPC13858
0.9801 High Similarity NPC35038
0.9801 High Similarity NPC278778
0.9801 High Similarity NPC291878
0.9737 High Similarity NPC27337
0.9737 High Similarity NPC52530
0.9737 High Similarity NPC471515
0.9737 High Similarity NPC291508
0.9737 High Similarity NPC471479
0.9735 High Similarity NPC200761
0.9735 High Similarity NPC477503
0.9735 High Similarity NPC321779
0.9735 High Similarity NPC45849
0.9735 High Similarity NPC470327
0.9679 High Similarity NPC471213
0.9675 High Similarity NPC474038
0.9675 High Similarity NPC472634
0.9675 High Similarity NPC26326
0.9675 High Similarity NPC289771
0.9675 High Similarity NPC472632
0.9671 High Similarity NPC471500
0.9671 High Similarity NPC470328
0.9671 High Similarity NPC209614
0.9671 High Similarity NPC250922
0.9671 High Similarity NPC472626
0.9669 High Similarity NPC192083
0.9669 High Similarity NPC18727
0.9669 High Similarity NPC213896
0.9615 High Similarity NPC475888
0.9615 High Similarity NPC62261
0.9613 High Similarity NPC211107
0.9613 High Similarity NPC474033
0.9613 High Similarity NPC472635
0.9613 High Similarity NPC474034
0.9613 High Similarity NPC476247
0.961 High Similarity NPC36217
0.961 High Similarity NPC119209
0.961 High Similarity NPC472624
0.961 High Similarity NPC472631
0.961 High Similarity NPC174953
0.961 High Similarity NPC475784
0.961 High Similarity NPC263449
0.961 High Similarity NPC472630
0.961 High Similarity NPC192686
0.961 High Similarity NPC118256
0.961 High Similarity NPC470183
0.9608 High Similarity NPC67876
0.9608 High Similarity NPC223787
0.9605 High Similarity NPC226025
0.9603 High Similarity NPC302950
0.9603 High Similarity NPC36835
0.9603 High Similarity NPC240476
0.9603 High Similarity NPC219582
0.9603 High Similarity NPC246162
0.9603 High Similarity NPC61506
0.9603 High Similarity NPC260491
0.9603 High Similarity NPC106976
0.9603 High Similarity NPC236637
0.9603 High Similarity NPC9743
0.9551 High Similarity NPC474240
0.9551 High Similarity NPC124038
0.9548 High Similarity NPC142252
0.9548 High Similarity NPC471210
0.9548 High Similarity NPC308992
0.9545 High Similarity NPC473990
0.9545 High Similarity NPC250214
0.9545 High Similarity NPC53545
0.9545 High Similarity NPC117418
0.9545 High Similarity NPC95936
0.9539 High Similarity NPC246328
0.9539 High Similarity NPC74924
0.9539 High Similarity NPC325028
0.9539 High Similarity NPC298692
0.9539 High Similarity NPC256346
0.9539 High Similarity NPC27532
0.9536 High Similarity NPC262038
0.9536 High Similarity NPC254412
0.9536 High Similarity NPC319910
0.9536 High Similarity NPC262039
0.9536 High Similarity NPC278476
0.9497 High Similarity NPC102277
0.9497 High Similarity NPC279209
0.949 High Similarity NPC7154
0.949 High Similarity NPC470457
0.949 High Similarity NPC36916
0.949 High Similarity NPC58223
0.949 High Similarity NPC36
0.949 High Similarity NPC7688
0.949 High Similarity NPC125039
0.949 High Similarity NPC72787
0.9487 High Similarity NPC201800
0.9484 High Similarity NPC321399
0.9481 High Similarity NPC162869
0.9481 High Similarity NPC284820
0.9481 High Similarity NPC471209
0.9481 High Similarity NPC156057
0.9481 High Similarity NPC78225
0.9481 High Similarity NPC474208
0.9481 High Similarity NPC475267
0.9481 High Similarity NPC474836
0.9481 High Similarity NPC48208
0.9481 High Similarity NPC473272
0.9477 High Similarity NPC117992
0.9477 High Similarity NPC230149
0.9477 High Similarity NPC57674
0.9477 High Similarity NPC152951
0.9477 High Similarity NPC168247
0.9477 High Similarity NPC133392
0.9474 High Similarity NPC471982
0.9474 High Similarity NPC138288
0.9474 High Similarity NPC171651
0.9474 High Similarity NPC63187
0.9474 High Similarity NPC157784
0.9474 High Similarity NPC217149
0.9474 High Similarity NPC37684
0.9474 High Similarity NPC216035
0.9474 High Similarity NPC35567
0.9474 High Similarity NPC243171
0.9474 High Similarity NPC472912
0.9474 High Similarity NPC19721
0.947 High Similarity NPC338131
0.947 High Similarity NPC105136
0.9427 High Similarity NPC41301
0.9427 High Similarity NPC186686
0.9427 High Similarity NPC470459
0.9423 High Similarity NPC471211
0.9423 High Similarity NPC173137
0.9423 High Similarity NPC134783
0.9423 High Similarity NPC158188
0.9423 High Similarity NPC471212
0.9423 High Similarity NPC266314
0.9423 High Similarity NPC112418
0.9423 High Similarity NPC474239
0.9419 High Similarity NPC210459
0.9419 High Similarity NPC152904
0.9419 High Similarity NPC55738
0.9416 High Similarity NPC201837
0.9416 High Similarity NPC191146
0.9416 High Similarity NPC255106
0.9416 High Similarity NPC474638
0.9416 High Similarity NPC68093
0.9416 High Similarity NPC235165
0.9412 High Similarity NPC227337
0.9412 High Similarity NPC236223
0.9412 High Similarity NPC78326
0.9412 High Similarity NPC273462
0.9412 High Similarity NPC49402
0.9412 High Similarity NPC179126
0.9412 High Similarity NPC70433
0.9412 High Similarity NPC270620
0.9412 High Similarity NPC293286
0.9412 High Similarity NPC33051
0.9412 High Similarity NPC141212
0.9408 High Similarity NPC252933
0.9408 High Similarity NPC54394
0.9408 High Similarity NPC304295
0.9408 High Similarity NPC205046
0.9408 High Similarity NPC59162
0.9408 High Similarity NPC200740
0.9408 High Similarity NPC125062
0.9371 High Similarity NPC470456
0.9371 High Similarity NPC260266
0.9371 High Similarity NPC158761
0.9367 High Similarity NPC293319
0.9367 High Similarity NPC300053
0.9367 High Similarity NPC108433
0.9367 High Similarity NPC472277
0.9367 High Similarity NPC224280
0.9363 High Similarity NPC472964
0.9363 High Similarity NPC474150
0.9363 High Similarity NPC471745
0.9363 High Similarity NPC474162
0.9359 High Similarity NPC328102
0.9359 High Similarity NPC471744
0.9359 High Similarity NPC472902
0.9359 High Similarity NPC299436
0.9359 High Similarity NPC246478
0.9355 High Similarity NPC470402
0.9355 High Similarity NPC472911
0.9355 High Similarity NPC472910
0.9355 High Similarity NPC262286
0.9355 High Similarity NPC299520
0.9355 High Similarity NPC36852
0.9355 High Similarity NPC52889
0.9355 High Similarity NPC96167
0.9355 High Similarity NPC472914
0.9355 High Similarity NPC245758
0.9355 High Similarity NPC210084
0.9355 High Similarity NPC99597
0.9355 High Similarity NPC129684

  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 NPC287328 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
0.9669 High Similarity NPD2393 Clinical (unspecified phase)
0.9603 High Similarity NPD1934 Approved
0.949 High Similarity NPD6168 Clinical (unspecified phase)
0.949 High Similarity NPD6167 Clinical (unspecified phase)
0.949 High Similarity NPD6166 Phase 2
0.9167 High Similarity NPD3882 Suspended
0.9161 High Similarity NPD2801 Approved
0.9079 High Similarity NPD1512 Approved
0.9018 High Similarity NPD7074 Phase 3
0.9013 High Similarity NPD4378 Clinical (unspecified phase)
0.8987 High Similarity NPD7075 Discontinued
0.8981 High Similarity NPD3817 Phase 2
0.8968 High Similarity NPD4380 Phase 2
0.8963 High Similarity NPD6797 Phase 2
0.8957 High Similarity NPD7054 Approved
0.8947 High Similarity NPD1511 Approved
0.8917 High Similarity NPD7096 Clinical (unspecified phase)
0.8909 High Similarity NPD7251 Discontinued
0.8902 High Similarity NPD7472 Approved
0.8896 High Similarity NPD3818 Discontinued
0.8855 High Similarity NPD7808 Phase 3
0.8855 High Similarity NPD4338 Clinical (unspecified phase)
0.8758 High Similarity NPD5494 Approved
0.8734 High Similarity NPD6801 Discontinued
0.8727 High Similarity NPD7804 Clinical (unspecified phase)
0.8688 High Similarity NPD4868 Clinical (unspecified phase)
0.8675 High Similarity NPD1552 Clinical (unspecified phase)
0.8675 High Similarity NPD1550 Clinical (unspecified phase)
0.8634 High Similarity NPD4381 Clinical (unspecified phase)
0.8618 High Similarity NPD1549 Phase 2
0.8512 High Similarity NPD7993 Clinical (unspecified phase)
0.8509 High Similarity NPD8443 Clinical (unspecified phase)
0.8503 High Similarity NPD5844 Phase 1
0.8462 Intermediate Similarity NPD6799 Approved
0.8447 Intermediate Similarity NPD7819 Suspended
0.8424 Intermediate Similarity NPD6232 Discontinued
0.8383 Intermediate Similarity NPD7473 Discontinued
0.8366 Intermediate Similarity NPD2796 Approved
0.8364 Intermediate Similarity NPD6959 Discontinued
0.8353 Intermediate Similarity NPD6559 Discontinued
0.8323 Intermediate Similarity NPD7411 Suspended
0.8301 Intermediate Similarity NPD1510 Phase 2
0.8291 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD5402 Approved
0.8278 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD1613 Approved
0.8261 Intermediate Similarity NPD6599 Discontinued
0.8253 Intermediate Similarity NPD1247 Approved
0.8242 Intermediate Similarity NPD919 Approved
0.8187 Intermediate Similarity NPD5403 Approved
0.8158 Intermediate Similarity NPD1240 Approved
0.811 Intermediate Similarity NPD1465 Phase 2
0.8079 Intermediate Similarity NPD3027 Phase 3
0.8063 Intermediate Similarity NPD5401 Approved
0.8052 Intermediate Similarity NPD1607 Approved
0.8047 Intermediate Similarity NPD3926 Phase 2
0.8039 Intermediate Similarity NPD943 Approved
0.8013 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7768 Phase 2
0.7898 Intermediate Similarity NPD2935 Discontinued
0.7862 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD2800 Approved
0.784 Intermediate Similarity NPD2533 Approved
0.784 Intermediate Similarity NPD2532 Approved
0.784 Intermediate Similarity NPD2534 Approved
0.7833 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD4628 Phase 3
0.7803 Intermediate Similarity NPD3751 Discontinued
0.7799 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3787 Discontinued
0.7764 Intermediate Similarity NPD6190 Approved
0.7756 Intermediate Similarity NPD230 Phase 1
0.7753 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7199 Phase 2
0.7706 Intermediate Similarity NPD6234 Discontinued
0.7702 Intermediate Similarity NPD3750 Approved
0.7697 Intermediate Similarity NPD1653 Approved
0.7684 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1551 Phase 2
0.7663 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3749 Approved
0.7643 Intermediate Similarity NPD447 Suspended
0.7636 Intermediate Similarity NPD920 Approved
0.7619 Intermediate Similarity NPD37 Approved
0.76 Intermediate Similarity NPD7228 Approved
0.7595 Intermediate Similarity NPD6651 Approved
0.7588 Intermediate Similarity NPD4965 Approved
0.7588 Intermediate Similarity NPD4966 Approved
0.7588 Intermediate Similarity NPD4967 Phase 2
0.7571 Intermediate Similarity NPD5953 Discontinued
0.7564 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6099 Approved
0.7562 Intermediate Similarity NPD6100 Approved
0.7561 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD7286 Phase 2
0.7554 Intermediate Similarity NPD4360 Phase 2
0.7554 Intermediate Similarity NPD4363 Phase 3
0.7545 Intermediate Similarity NPD3226 Approved
0.7542 Intermediate Similarity NPD8313 Approved
0.7542 Intermediate Similarity NPD8312 Approved
0.754 Intermediate Similarity NPD6782 Approved
0.754 Intermediate Similarity NPD6777 Approved
0.754 Intermediate Similarity NPD6779 Approved
0.754 Intermediate Similarity NPD6780 Approved
0.754 Intermediate Similarity NPD6776 Approved
0.754 Intermediate Similarity NPD6781 Approved
0.754 Intermediate Similarity NPD6778 Approved
0.7532 Intermediate Similarity NPD1933 Approved
0.7531 Intermediate Similarity NPD1243 Approved
0.7516 Intermediate Similarity NPD2346 Discontinued
0.7515 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8150 Discontinued
0.7514 Intermediate Similarity NPD8434 Phase 2
0.75 Intermediate Similarity NPD2799 Discontinued
0.75 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD9494 Approved
0.7455 Intermediate Similarity NPD7390 Discontinued
0.7452 Intermediate Similarity NPD2313 Discontinued
0.7452 Intermediate Similarity NPD6798 Discontinued
0.7451 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4908 Phase 1
0.7434 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD7685 Pre-registration
0.7421 Intermediate Similarity NPD7435 Discontinued
0.741 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD2344 Approved
0.7396 Intermediate Similarity NPD7584 Approved
0.7391 Intermediate Similarity NPD7033 Discontinued
0.7391 Intermediate Similarity NPD3748 Approved
0.7378 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD5711 Approved
0.7371 Intermediate Similarity NPD5710 Approved
0.7362 Intermediate Similarity NPD2424 Discontinued
0.7358 Intermediate Similarity NPD4060 Phase 1
0.7353 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7697 Approved
0.733 Intermediate Similarity NPD7696 Phase 3
0.733 Intermediate Similarity NPD7698 Approved
0.732 Intermediate Similarity NPD1610 Phase 2
0.732 Intermediate Similarity NPD8151 Discontinued
0.7312 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5124 Phase 1
0.7312 Intermediate Similarity NPD6355 Discontinued
0.7305 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6233 Phase 2
0.7292 Intermediate Similarity NPD7871 Phase 2
0.7292 Intermediate Similarity NPD7870 Phase 2
0.7278 Intermediate Similarity NPD4625 Phase 3
0.7273 Intermediate Similarity NPD6535 Approved
0.7273 Intermediate Similarity NPD6534 Approved
0.7268 Intermediate Similarity NPD7701 Phase 2
0.7267 Intermediate Similarity NPD8455 Phase 2
0.7244 Intermediate Similarity NPD1203 Approved
0.7234 Intermediate Similarity NPD4361 Phase 2
0.7234 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD5242 Approved
0.7229 Intermediate Similarity NPD2309 Approved
0.7225 Intermediate Similarity NPD5353 Approved
0.7215 Intermediate Similarity NPD6832 Phase 2
0.7212 Intermediate Similarity NPD1652 Phase 2
0.7212 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6844 Discontinued
0.7207 Intermediate Similarity NPD2163 Approved
0.7205 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7266 Discontinued
0.7194 Intermediate Similarity NPD7874 Approved
0.7194 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD2403 Approved
0.7182 Intermediate Similarity NPD3823 Discontinued
0.7175 Intermediate Similarity NPD7229 Phase 3
0.7171 Intermediate Similarity NPD1548 Phase 1
0.7158 Intermediate Similarity NPD7699 Phase 2
0.7158 Intermediate Similarity NPD7700 Phase 2
0.7157 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7783 Phase 2
0.7157 Intermediate Similarity NPD7801 Approved
0.7152 Intermediate Similarity NPD2861 Phase 2
0.7143 Intermediate Similarity NPD7240 Approved
0.7135 Intermediate Similarity NPD7458 Discontinued
0.7135 Intermediate Similarity NPD2494 Approved
0.7135 Intermediate Similarity NPD2493 Approved
0.7125 Intermediate Similarity NPD3268 Approved
0.7125 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD8127 Discontinued
0.7108 Intermediate Similarity NPD6674 Discontinued
0.7101 Intermediate Similarity NPD4662 Approved
0.7101 Intermediate Similarity NPD4661 Approved
0.7098 Intermediate Similarity NPD6823 Phase 2
0.7095 Intermediate Similarity NPD7784 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