Structure

Physi-Chem Properties

Molecular Weight:  566.12
Volume:  556.408
LogP:  6.44
LogD:  2.4
LogS:  -3.857
# Rotatable Bonds:  5
TPSA:  159.8
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.203
Synthetic Accessibility Score:  2.981
Fsp3:  0.062
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:  -5.081
MDCK Permeability:  1.3097357623337302e-05
Pgp-inhibitor:  0.711
Pgp-substrate:  0.206
Human Intestinal Absorption (HIA):  0.176
20% Bioavailability (F20%):  0.686
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  95.86739349365234%
Volume Distribution (VD):  0.436
Pgp-substrate:  6.057016372680664%

ADMET: Metabolism

CYP1A2-inhibitor:  0.748
CYP1A2-substrate:  0.731
CYP2C19-inhibitor:  0.801
CYP2C19-substrate:  0.047
CYP2C9-inhibitor:  0.621
CYP2C9-substrate:  0.944
CYP2D6-inhibitor:  0.129
CYP2D6-substrate:  0.909
CYP3A4-inhibitor:  0.276
CYP3A4-substrate:  0.106

ADMET: Excretion

Clearance (CL):  3.041
Half-life (T1/2):  0.173

ADMET: Toxicity

hERG Blockers:  0.097
Human Hepatotoxicity (H-HT):  0.088
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.219
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.893
Skin Sensitization:  0.678
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.867
Respiratory Toxicity:  0.083

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

  Natural Product: NPC205026

Natural Product ID:  NPC205026
Common Name*:   Robustaflavone-7,4'-Dimethyl Ether
IUPAC Name:   5,7-dihydroxy-6-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:   Robustaflavone-7,4'-Dimethyl Ether
Standard InCHIKey:  JPWWBJLDWCIZJM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C32H22O10/c1-39-18-10-20(34)30-22(36)12-26(42-27(30)11-18)16-5-8-24(40-2)19(9-16)29-21(35)14-28-31(32(29)38)23(37)13-25(41-28)15-3-6-17(33)7-4-15/h3-14,33-35,38H,1-2H3
SMILES:  COc1cc(c2c(=O)cc(c3ccc(c(c3)c3c(cc4c(c(=O)cc(c5ccc(cc5)O)o4)c3O)O)OC)oc2c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453554
PubChem CID:   10816812
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO2508 Selaginella delicatula Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[10843573]
NPO5878 Etlingera elatior Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[15730265]
NPO5878 Etlingera elatior Species Zingiberaceae Eukaryota Flowers Johor, Malaysia PMID[26399961]
NPO5878 Etlingera elatior Species Zingiberaceae Eukaryota Flowers Kelantan, Malaysia PMID[26399961]
NPO5878 Etlingera elatior Species Zingiberaceae Eukaryota Flowers Pahang, Malaysia PMID[26399961]
NPO5878 Etlingera elatior Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4071 Cytisus uniflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7573 Psidium araca Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4367 Actinobacillus equuli Species Pasteurellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5878 Etlingera elatior Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8576 Cissus rheifolia Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4437 Hymenoxys lemmoni Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2508 Selaginella delicatula Species Selaginellaceae 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
NPT80 Cell Line Raji Homo sapiens IC50 > 100000.0 nM PMID[465110]
NPT1307 Cell Line Calu-1 Homo sapiens IC50 > 100000.0 nM PMID[465110]
NPT111 Cell Line K562 Homo sapiens IC50 > 100000.0 nM PMID[465110]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 100000.0 nM PMID[465110]
NPT1306 Cell Line WISH Homo sapiens IC50 > 100000.0 nM PMID[465110]
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000.0 nM PMID[465110]

☑ 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 NPC205026 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 NPC265624
1.0 High Similarity NPC121649
1.0 High Similarity NPC158027
1.0 High Similarity NPC100049
1.0 High Similarity NPC248739
1.0 High Similarity NPC52611
1.0 High Similarity NPC215203
1.0 High Similarity NPC14606
1.0 High Similarity NPC186227
1.0 High Similarity NPC159707
1.0 High Similarity NPC150908
0.9932 High Similarity NPC71061
0.9932 High Similarity NPC194593
0.9932 High Similarity NPC290830
0.9932 High Similarity NPC303485
0.9932 High Similarity NPC72425
0.9796 High Similarity NPC222713
0.9796 High Similarity NPC111112
0.9796 High Similarity NPC138299
0.9796 High Similarity NPC67322
0.9669 High Similarity NPC18699
0.9669 High Similarity NPC55443
0.96 High Similarity NPC66441
0.96 High Similarity NPC182555
0.9542 High Similarity NPC189552
0.9542 High Similarity NPC273467
0.9527 High Similarity NPC288840
0.9527 High Similarity NPC291746
0.9477 High Similarity NPC121647
0.9477 High Similarity NPC312993
0.9477 High Similarity NPC186325
0.947 High Similarity NPC134171
0.947 High Similarity NPC254351
0.947 High Similarity NPC300668
0.9412 High Similarity NPC51760
0.9412 High Similarity NPC177650
0.9408 High Similarity NPC32867
0.9408 High Similarity NPC56049
0.9408 High Similarity NPC54830
0.9404 High Similarity NPC324447
0.9359 High Similarity NPC469664
0.9346 High Similarity NPC1796
0.9346 High Similarity NPC475184
0.9346 High Similarity NPC257166
0.9338 High Similarity NPC174086
0.929 High Similarity NPC301256
0.929 High Similarity NPC312273
0.9286 High Similarity NPC15815
0.9286 High Similarity NPC51247
0.9286 High Similarity NPC105584
0.9286 High Similarity NPC295090
0.9281 High Similarity NPC69531
0.9276 High Similarity NPC121568
0.9267 High Similarity NPC3642
0.9262 High Similarity NPC261271
0.9262 High Similarity NPC475348
0.9257 High Similarity NPC194949
0.9257 High Similarity NPC282957
0.9231 High Similarity NPC473012
0.9226 High Similarity NPC195136
0.9226 High Similarity NPC42965
0.9226 High Similarity NPC98023
0.9226 High Similarity NPC226462
0.9221 High Similarity NPC271741
0.9221 High Similarity NPC287789
0.9216 High Similarity NPC79375
0.9216 High Similarity NPC37253
0.9211 High Similarity NPC39154
0.9211 High Similarity NPC78324
0.9211 High Similarity NPC208011
0.9211 High Similarity NPC115601
0.92 High Similarity NPC244407
0.92 High Similarity NPC152233
0.92 High Similarity NPC122894
0.9184 High Similarity NPC14871
0.9184 High Similarity NPC26238
0.9172 High Similarity NPC473009
0.9161 High Similarity NPC90497
0.9156 High Similarity NPC61112
0.9156 High Similarity NPC198489
0.9156 High Similarity NPC192587
0.9145 High Similarity NPC178484
0.9139 High Similarity NPC5173
0.9133 High Similarity NPC97716
0.9133 High Similarity NPC237635
0.9133 High Similarity NPC104406
0.9133 High Similarity NPC24673
0.9133 High Similarity NPC166757
0.9133 High Similarity NPC201731
0.9133 High Similarity NPC79469
0.9133 High Similarity NPC14001
0.9128 High Similarity NPC319752
0.9128 High Similarity NPC257236
0.9128 High Similarity NPC273538
0.9128 High Similarity NPC278175
0.9128 High Similarity NPC216538
0.9122 High Similarity NPC299080
0.9122 High Similarity NPC217083
0.9122 High Similarity NPC78803
0.9122 High Similarity NPC59739
0.9122 High Similarity NPC214236
0.9122 High Similarity NPC293852
0.9122 High Similarity NPC62840
0.9116 High Similarity NPC241100
0.9116 High Similarity NPC159275
0.9114 High Similarity NPC473010
0.9114 High Similarity NPC259757
0.9097 High Similarity NPC208258
0.9097 High Similarity NPC324358
0.9097 High Similarity NPC318527
0.9097 High Similarity NPC183
0.9097 High Similarity NPC322459
0.9097 High Similarity NPC323627
0.9091 High Similarity NPC201227
0.9091 High Similarity NPC258474
0.9085 High Similarity NPC43345
0.9079 High Similarity NPC29777
0.9079 High Similarity NPC471115
0.9073 High Similarity NPC161191
0.9073 High Similarity NPC266572
0.9073 High Similarity NPC296869
0.9073 High Similarity NPC6511
0.9073 High Similarity NPC321623
0.9073 High Similarity NPC189087
0.9067 High Similarity NPC470133
0.9067 High Similarity NPC178343
0.9067 High Similarity NPC5820
0.9067 High Similarity NPC124729
0.9067 High Similarity NPC470134
0.9067 High Similarity NPC109183
0.9067 High Similarity NPC470132
0.9067 High Similarity NPC473078
0.9067 High Similarity NPC228779
0.9067 High Similarity NPC474161
0.9067 High Similarity NPC306488
0.9067 High Similarity NPC470131
0.9067 High Similarity NPC476088
0.9067 High Similarity NPC220418
0.906 High Similarity NPC212932
0.906 High Similarity NPC293053
0.906 High Similarity NPC219915
0.906 High Similarity NPC24821
0.906 High Similarity NPC190637
0.906 High Similarity NPC11700
0.906 High Similarity NPC9117
0.9057 High Similarity NPC251336
0.9054 High Similarity NPC282300
0.9054 High Similarity NPC110969
0.9051 High Similarity NPC38591
0.9048 High Similarity NPC217186
0.9048 High Similarity NPC55018
0.9048 High Similarity NPC96565
0.9048 High Similarity NPC78913
0.9048 High Similarity NPC216978
0.9048 High Similarity NPC220062
0.9048 High Similarity NPC18260
0.9048 High Similarity NPC301217
0.9048 High Similarity NPC303633
0.9048 High Similarity NPC53181
0.9045 High Similarity NPC18380
0.9038 High Similarity NPC123544
0.9032 High Similarity NPC309648
0.9026 High Similarity NPC329844
0.902 High Similarity NPC476553
0.902 High Similarity NPC476551
0.902 High Similarity NPC476552
0.9013 High Similarity NPC132345
0.9007 High Similarity NPC473077
0.9007 High Similarity NPC308200
0.9007 High Similarity NPC296998
0.9 High Similarity NPC471523
0.9 High Similarity NPC271288
0.9 High Similarity NPC471524
0.9 High Similarity NPC311741
0.9 High Similarity NPC471473
0.9 High Similarity NPC224714
0.9 High Similarity NPC39045
0.9 High Similarity NPC470135
0.9 High Similarity NPC470136
0.9 High Similarity NPC234629
0.9 High Similarity NPC286230
0.9 High Similarity NPC253730
0.9 High Similarity NPC326500
0.8994 High Similarity NPC169471
0.8993 High Similarity NPC200694
0.8993 High Similarity NPC226636
0.8993 High Similarity NPC473042
0.8993 High Similarity NPC11561
0.8987 High Similarity NPC473011
0.8987 High Similarity NPC15374
0.8986 High Similarity NPC150522
0.8986 High Similarity NPC270883
0.8986 High Similarity NPC172986
0.8986 High Similarity NPC261227
0.8981 High Similarity NPC472052
0.8981 High Similarity NPC472060
0.8981 High Similarity NPC184326
0.8981 High Similarity NPC292863
0.8981 High Similarity NPC470342
0.898 High Similarity NPC243528

  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 NPC205026 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
0.9128 High Similarity NPD4378 Clinical (unspecified phase)
0.9128 High Similarity NPD7410 Clinical (unspecified phase)
0.9114 High Similarity NPD7852 Clinical (unspecified phase)
0.9091 High Similarity NPD8443 Clinical (unspecified phase)
0.9045 High Similarity NPD6959 Discontinued
0.891 High Similarity NPD7768 Phase 2
0.8774 High Similarity NPD7411 Suspended
0.871 High Similarity NPD4380 Phase 2
0.8544 High Similarity NPD2393 Clinical (unspecified phase)
0.8544 High Similarity NPD7819 Suspended
0.8533 High Similarity NPD1552 Clinical (unspecified phase)
0.8533 High Similarity NPD1550 Clinical (unspecified phase)
0.8523 High Similarity NPD1510 Phase 2
0.8485 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8477 Intermediate Similarity NPD1549 Phase 2
0.8467 Intermediate Similarity NPD2796 Approved
0.8442 Intermediate Similarity NPD7390 Discontinued
0.8415 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD6166 Phase 2
0.8415 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD3749 Approved
0.8385 Intermediate Similarity NPD7075 Discontinued
0.8378 Intermediate Similarity NPD1240 Approved
0.8323 Intermediate Similarity NPD1511 Approved
0.8313 Intermediate Similarity NPD2801 Approved
0.8293 Intermediate Similarity NPD6232 Discontinued
0.8267 Intermediate Similarity NPD1607 Approved
0.8253 Intermediate Similarity NPD7473 Discontinued
0.825 Intermediate Similarity NPD1934 Approved
0.825 Intermediate Similarity NPD6801 Discontinued
0.8247 Intermediate Similarity NPD3750 Approved
0.8217 Intermediate Similarity NPD1512 Approved
0.8199 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD2800 Approved
0.8182 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD7054 Approved
0.8037 Intermediate Similarity NPD3817 Phase 2
0.8 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7472 Approved
0.8 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7074 Phase 3
0.7988 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD6799 Approved
0.7965 Intermediate Similarity NPD7808 Phase 3
0.7953 Intermediate Similarity NPD6797 Phase 2
0.7953 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD5494 Approved
0.7949 Intermediate Similarity NPD1243 Approved
0.7941 Intermediate Similarity NPD5844 Phase 1
0.7937 Intermediate Similarity NPD5403 Approved
0.7937 Intermediate Similarity NPD920 Approved
0.7935 Intermediate Similarity NPD2344 Approved
0.7922 Intermediate Similarity NPD3748 Approved
0.7908 Intermediate Similarity NPD6651 Approved
0.7907 Intermediate Similarity NPD6559 Discontinued
0.7907 Intermediate Similarity NPD7251 Discontinued
0.7901 Intermediate Similarity NPD6599 Discontinued
0.7882 Intermediate Similarity NPD3818 Discontinued
0.7879 Intermediate Similarity NPD3882 Suspended
0.7871 Intermediate Similarity NPD2935 Discontinued
0.7867 Intermediate Similarity NPD4908 Phase 1
0.7861 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD3226 Approved
0.7818 Intermediate Similarity NPD5402 Approved
0.7812 Intermediate Similarity NPD2533 Approved
0.7812 Intermediate Similarity NPD5401 Approved
0.7812 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD2532 Approved
0.7812 Intermediate Similarity NPD2534 Approved
0.7806 Intermediate Similarity NPD2799 Discontinued
0.7799 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD2313 Discontinued
0.7758 Intermediate Similarity NPD8455 Phase 2
0.7756 Intermediate Similarity NPD1551 Phase 2
0.7746 Intermediate Similarity NPD5953 Discontinued
0.7736 Intermediate Similarity NPD2309 Approved
0.7714 Intermediate Similarity NPD8312 Approved
0.7714 Intermediate Similarity NPD8313 Approved
0.7697 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD7003 Approved
0.7657 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD5405 Approved
0.7643 Intermediate Similarity NPD5404 Approved
0.7643 Intermediate Similarity NPD5406 Approved
0.7643 Intermediate Similarity NPD5408 Approved
0.7637 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD7286 Phase 2
0.7624 Intermediate Similarity NPD4360 Phase 2
0.7624 Intermediate Similarity NPD4363 Phase 3
0.7611 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD3926 Phase 2
0.7562 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD1465 Phase 2
0.7532 Intermediate Similarity NPD6100 Approved
0.7532 Intermediate Similarity NPD6099 Approved
0.7532 Intermediate Similarity NPD3268 Approved
0.7515 Intermediate Similarity NPD7458 Discontinued
0.75 Intermediate Similarity NPD2798 Approved
0.7485 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1247 Approved
0.7484 Intermediate Similarity NPD2346 Discontinued
0.7471 Intermediate Similarity NPD919 Approved
0.7453 Intermediate Similarity NPD4628 Phase 3
0.7442 Intermediate Similarity NPD7229 Phase 3
0.7434 Intermediate Similarity NPD1203 Approved
0.7434 Intermediate Similarity NPD2797 Approved
0.741 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6832 Phase 2
0.7403 Intermediate Similarity NPD4287 Approved
0.74 Intermediate Similarity NPD1610 Phase 2
0.7394 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD4361 Phase 2
0.7391 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5124 Phase 1
0.7382 Intermediate Similarity NPD8151 Discontinued
0.7378 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7177 Discontinued
0.7368 Intermediate Similarity NPD3225 Approved
0.7365 Intermediate Similarity NPD1548 Phase 1
0.7358 Intermediate Similarity NPD7033 Discontinued
0.7355 Intermediate Similarity NPD4625 Phase 3
0.7346 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD3787 Discontinued
0.7325 Intermediate Similarity NPD943 Approved
0.7294 Intermediate Similarity NPD4288 Approved
0.7285 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD422 Phase 1
0.7273 Intermediate Similarity NPD3751 Discontinued
0.7267 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7870 Phase 2
0.7263 Intermediate Similarity NPD7871 Phase 2
0.725 Intermediate Similarity NPD4308 Phase 3
0.7241 Intermediate Similarity NPD5711 Approved
0.7241 Intermediate Similarity NPD5710 Approved
0.7237 Intermediate Similarity NPD9717 Approved
0.7234 Intermediate Similarity NPD6782 Approved
0.7234 Intermediate Similarity NPD6778 Approved
0.7234 Intermediate Similarity NPD6781 Approved
0.7234 Intermediate Similarity NPD6780 Approved
0.7234 Intermediate Similarity NPD6777 Approved
0.7234 Intermediate Similarity NPD6776 Approved
0.7234 Intermediate Similarity NPD6779 Approved
0.7219 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7783 Phase 2
0.7216 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7698 Approved
0.7211 Intermediate Similarity NPD7697 Approved
0.7211 Intermediate Similarity NPD7696 Phase 3
0.7208 Intermediate Similarity NPD3267 Approved
0.7208 Intermediate Similarity NPD3266 Approved
0.7197 Intermediate Similarity NPD3764 Approved
0.7193 Intermediate Similarity NPD2296 Approved
0.7188 Intermediate Similarity NPD7584 Approved
0.7184 Intermediate Similarity NPD7199 Phase 2
0.7178 Intermediate Similarity NPD2654 Approved
0.7175 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1201 Approved
0.7169 Intermediate Similarity NPD7447 Phase 1
0.7159 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD3972 Approved
0.7124 Intermediate Similarity NPD1608 Approved
0.712 Intermediate Similarity NPD7435 Discontinued
0.7108 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7213 Phase 3
0.7108 Intermediate Similarity NPD7212 Phase 2
0.7104 Intermediate Similarity NPD8150 Discontinued
0.7102 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1164 Approved
0.7097 Intermediate Similarity NPD1470 Approved
0.7095 Intermediate Similarity NPD1729 Discontinued
0.7089 Intermediate Similarity NPD6798 Discontinued
0.707 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7701 Phase 2
0.7024 Intermediate Similarity NPD6273 Approved
0.7018 Intermediate Similarity NPD5889 Approved
0.7018 Intermediate Similarity NPD5890 Approved
0.7011 Intermediate Similarity NPD8434 Phase 2
0.7006 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4307 Phase 2
0.7 Intermediate Similarity NPD1613 Approved
0.699 Remote Similarity NPD7875 Clinical (unspecified phase)
0.699 Remote Similarity NPD7874 Approved
0.6981 Remote Similarity NPD1296 Phase 2
0.6979 Remote Similarity NPD6823 Phase 2
0.6977 Remote Similarity NPD37 Approved
0.6977 Remote Similarity NPD6279 Approved
0.6977 Remote Similarity NPD6844 Discontinued
0.6977 Remote Similarity NPD6280 Approved
0.6977 Remote Similarity NPD7577 Discontinued
0.6971 Remote Similarity NPD6234 Discontinued
0.6968 Remote Similarity NPD6534 Approved
0.6968 Remote Similarity NPD6535 Approved
0.6968 Remote Similarity NPD4749 Approved

  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