Structure

Physi-Chem Properties

Molecular Weight:  492.25
Volume:  522.223
LogP:  7.739
LogD:  4.343
LogS:  -2.774
# Rotatable Bonds:  6
TPSA:  96.22
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.382
Synthetic Accessibility Score:  4.141
Fsp3:  0.433
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:  -4.835
MDCK Permeability:  1.7595220924704336e-05
Pgp-inhibitor:  0.853
Pgp-substrate:  0.818
Human Intestinal Absorption (HIA):  0.047
20% Bioavailability (F20%):  0.896
30% Bioavailability (F30%):  0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  93.91736602783203%
Volume Distribution (VD):  2.137
Pgp-substrate:  9.460991859436035%

ADMET: Metabolism

CYP1A2-inhibitor:  0.269
CYP1A2-substrate:  0.536
CYP2C19-inhibitor:  0.931
CYP2C19-substrate:  0.131
CYP2C9-inhibitor:  0.847
CYP2C9-substrate:  0.965
CYP2D6-inhibitor:  0.642
CYP2D6-substrate:  0.426
CYP3A4-inhibitor:  0.266
CYP3A4-substrate:  0.181

ADMET: Excretion

Clearance (CL):  13.705
Half-life (T1/2):  0.088

ADMET: Toxicity

hERG Blockers:  0.062
Human Hepatotoxicity (H-HT):  0.956
Drug-inuced Liver Injury (DILI):  0.805
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.868
Maximum Recommended Daily Dose:  0.519
Skin Sensitization:  0.89
Carcinogencity:  0.157
Eye Corrosion:  0.003
Eye Irritation:  0.395
Respiratory Toxicity:  0.935

Download Data

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

  Natural Product: NPC293319

Natural Product ID:  NPC293319
Common Name*:   Macaflavanone G
IUPAC Name:   (2S)-5,7-dihydroxy-2-[(2R)-8-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-3,4-dihydrochromen-5-yl]-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:   Macaflavanone G
Standard InCHIKey:  YDKQMGVESZZFGP-SETSBSEESA-N
Standard InCHI:  InChI=1S/C30H36O6/c1-17(2)7-6-13-30(5)14-12-20-19(10-11-22(31)29(20)36-30)25-16-24(33)27-26(35-25)15-23(32)21(28(27)34)9-8-18(3)4/h7-8,10-11,15,25,31-32,34H,6,9,12-14,16H2,1-5H3/t25-,30+/m0/s1
SMILES:  CC(=CCC[C@]1(C)CCc2c(ccc(c2O1)O)[C@@H]1CC(=O)c2c(cc(c(CC=C(C)C)c2O)O)O1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL575434
PubChem CID:   25155335
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0003645] 2'-prenylated flavans
            • [CHEMONTID:0003588] 2'-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
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[11087590]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[11421757]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11975480]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[15620255]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[15974621]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota leaves Krachong waterfall area, Trang Province, Thailand 2001-APR PMID[15974621]
NPO3453 Elaeocarpus fuscoides Species Elaeocarpaceae Eukaryota leaves n.a. n.a. PMID[17451272]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota leaves n.a. n.a. PMID[18844422]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[18844422]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota epidermis of the sclerotia n.a. n.a. PMID[19746919]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[27808511]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[28972755]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[8984162]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1209 Swartzia madagascariensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8543 Meconopsis horridula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO477 Lepraria xanthina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7087 Oxera splendida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO305 Vitex pinnata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8543 Meconopsis horridula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3453 Elaeocarpus fuscoides Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1209 Swartzia madagascariensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5508 Stevia purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15164 Jacobaea adonidifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO896 Streptomyces kanamyceticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5344 Calodendrum capense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6330 Croton caudatus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12330 Pseudophryne coriacea Species Myobatrachidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3280 Penicillium crustaceum Species Aspergillaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 12300.0 nM PMID[513173]
NPT81 Cell Line A549 Homo sapiens IC50 = 13400.0 nM PMID[513173]

☑ 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 NPC293319 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
0.9808 High Similarity NPC186686
0.9806 High Similarity NPC471210
0.9747 High Similarity NPC218226
0.9744 High Similarity NPC201800
0.9742 High Similarity NPC36217
0.9684 High Similarity NPC43319
0.9679 High Similarity NPC471212
0.9679 High Similarity NPC472632
0.9679 High Similarity NPC471211
0.9677 High Similarity NPC210459
0.9623 High Similarity NPC477154
0.9623 High Similarity NPC6588
0.9623 High Similarity NPC474024
0.9623 High Similarity NPC117854
0.962 High Similarity NPC62261
0.9618 High Similarity NPC474033
0.9618 High Similarity NPC474034
0.9618 High Similarity NPC472964
0.9615 High Similarity NPC321399
0.9615 High Similarity NPC119209
0.9615 High Similarity NPC118256
0.9615 High Similarity NPC299436
0.9615 High Similarity NPC174953
0.9615 High Similarity NPC192686
0.9613 High Similarity NPC27337
0.9613 High Similarity NPC471209
0.956 High Similarity NPC39091
0.956 High Similarity NPC471213
0.9557 High Similarity NPC236521
0.9557 High Similarity NPC152659
0.9557 High Similarity NPC248638
0.9554 High Similarity NPC474038
0.9554 High Similarity NPC472634
0.9554 High Similarity NPC134783
0.9551 High Similarity NPC473990
0.9548 High Similarity NPC291878
0.9548 High Similarity NPC35038
0.9548 High Similarity NPC195796
0.9548 High Similarity NPC209614
0.9548 High Similarity NPC470328
0.9548 High Similarity NPC24640
0.9548 High Similarity NPC278778
0.9548 High Similarity NPC472626
0.9497 High Similarity NPC239752
0.9497 High Similarity NPC472450
0.9497 High Similarity NPC275780
0.9497 High Similarity NPC475888
0.9494 High Similarity NPC474150
0.9494 High Similarity NPC211107
0.9494 High Similarity NPC474162
0.9494 High Similarity NPC25152
0.949 High Similarity NPC474960
0.949 High Similarity NPC471973
0.949 High Similarity NPC472902
0.949 High Similarity NPC472624
0.949 High Similarity NPC472631
0.949 High Similarity NPC475784
0.949 High Similarity NPC472630
0.9487 High Similarity NPC472598
0.9487 High Similarity NPC284820
0.9487 High Similarity NPC474055
0.9487 High Similarity NPC472963
0.9487 High Similarity NPC291508
0.9487 High Similarity NPC136674
0.9487 High Similarity NPC473272
0.9484 High Similarity NPC67396
0.9484 High Similarity NPC477503
0.9484 High Similarity NPC470327
0.9484 High Similarity NPC226025
0.9484 High Similarity NPC45849
0.9484 High Similarity NPC200761
0.9437 High Similarity NPC477517
0.9437 High Similarity NPC272502
0.9437 High Similarity NPC472449
0.9437 High Similarity NPC170245
0.9434 High Similarity NPC472625
0.9434 High Similarity NPC189473
0.9434 High Similarity NPC474240
0.9434 High Similarity NPC23298
0.9434 High Similarity NPC7483
0.943 High Similarity NPC278052
0.943 High Similarity NPC474186
0.943 High Similarity NPC40491
0.943 High Similarity NPC474187
0.943 High Similarity NPC173137
0.943 High Similarity NPC61010
0.943 High Similarity NPC26326
0.9427 High Similarity NPC85121
0.9423 High Similarity NPC472907
0.9419 High Similarity NPC192083
0.9419 High Similarity NPC74924
0.9419 High Similarity NPC298692
0.9419 High Similarity NPC18727
0.9419 High Similarity NPC213896
0.9379 High Similarity NPC150131
0.9375 High Similarity NPC224280
0.9375 High Similarity NPC303174
0.9375 High Similarity NPC326520
0.9371 High Similarity NPC472635
0.9371 High Similarity NPC476247
0.9371 High Similarity NPC229632
0.9367 High Similarity NPC287328
0.9367 High Similarity NPC470183
0.9367 High Similarity NPC56085
0.9367 High Similarity NPC320359
0.9367 High Similarity NPC282009
0.9367 High Similarity NPC475886
0.9367 High Similarity NPC200746
0.9367 High Similarity NPC228785
0.9367 High Similarity NPC474287
0.9367 High Similarity NPC14353
0.9363 High Similarity NPC52889
0.9363 High Similarity NPC223787
0.9359 High Similarity NPC321779
0.9355 High Similarity NPC106976
0.9355 High Similarity NPC302950
0.9355 High Similarity NPC236637
0.9355 High Similarity NPC219582
0.9325 High Similarity NPC4200
0.9321 High Similarity NPC288813
0.9317 High Similarity NPC120593
0.9317 High Similarity NPC37870
0.9313 High Similarity NPC475985
0.9313 High Similarity NPC236132
0.9313 High Similarity NPC146134
0.9313 High Similarity NPC220313
0.9313 High Similarity NPC124038
0.9308 High Similarity NPC474351
0.9308 High Similarity NPC142252
0.9308 High Similarity NPC474239
0.9308 High Similarity NPC475883
0.9308 High Similarity NPC158188
0.9308 High Similarity NPC471499
0.9304 High Similarity NPC184755
0.9304 High Similarity NPC100123
0.9304 High Similarity NPC250214
0.9304 High Similarity NPC95936
0.9304 High Similarity NPC235448
0.9304 High Similarity NPC22192
0.9304 High Similarity NPC204879
0.9304 High Similarity NPC53545
0.9304 High Similarity NPC117418
0.9304 High Similarity NPC476242
0.9304 High Similarity NPC74178
0.9299 High Similarity NPC471985
0.9299 High Similarity NPC470600
0.9295 High Similarity NPC472905
0.9255 High Similarity NPC234052
0.9255 High Similarity NPC472277
0.9255 High Similarity NPC300053
0.9255 High Similarity NPC108433
0.925 High Similarity NPC83922
0.925 High Similarity NPC52204
0.925 High Similarity NPC329760
0.925 High Similarity NPC472448
0.9245 High Similarity NPC470326
0.9245 High Similarity NPC204290
0.9245 High Similarity NPC139036
0.9245 High Similarity NPC328102
0.9241 High Similarity NPC162869
0.9241 High Similarity NPC236796
0.9241 High Similarity NPC299520
0.9241 High Similarity NPC273843
0.9241 High Similarity NPC67876
0.9241 High Similarity NPC156057
0.9241 High Similarity NPC474208
0.9241 High Similarity NPC471515
0.9241 High Similarity NPC165977
0.9241 High Similarity NPC48208
0.9241 High Similarity NPC474681
0.9241 High Similarity NPC217677
0.9241 High Similarity NPC78225
0.9241 High Similarity NPC300727
0.9241 High Similarity NPC475267
0.9241 High Similarity NPC218313
0.9241 High Similarity NPC474836
0.9241 High Similarity NPC471479
0.9241 High Similarity NPC129684
0.9241 High Similarity NPC241904
0.9236 High Similarity NPC230149
0.9236 High Similarity NPC168247
0.9236 High Similarity NPC256925
0.9236 High Similarity NPC234255
0.9236 High Similarity NPC117992
0.9236 High Similarity NPC477958
0.9236 High Similarity NPC152951
0.9236 High Similarity NPC57674
0.9231 High Similarity NPC471982
0.9231 High Similarity NPC475790
0.9231 High Similarity NPC472912
0.9231 High Similarity NPC260979
0.9226 High Similarity NPC338131
0.9212 High Similarity NPC108202
0.9202 High Similarity NPC177480
0.9202 High Similarity NPC165456
0.9202 High Similarity NPC152477
0.9202 High Similarity NPC300307
0.9198 High Similarity NPC235610
0.9198 High Similarity NPC173292
0.9193 High Similarity NPC207690

  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 NPC293319 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
0.9419 High Similarity NPD2393 Clinical (unspecified phase)
0.9355 High Similarity NPD1934 Approved
0.9136 High Similarity NPD6167 Clinical (unspecified phase)
0.9136 High Similarity NPD6168 Clinical (unspecified phase)
0.9136 High Similarity NPD6166 Phase 2
0.903 High Similarity NPD7074 Phase 3
0.897 High Similarity NPD7054 Approved
0.8931 High Similarity NPD2801 Approved
0.8916 High Similarity NPD7472 Approved
0.8889 High Similarity NPD5494 Approved
0.8742 High Similarity NPD4380 Phase 2
0.872 High Similarity NPD6959 Discontinued
0.8718 High Similarity NPD1511 Approved
0.8704 High Similarity NPD3882 Suspended
0.8698 High Similarity NPD7251 Discontinued
0.8696 High Similarity NPD7819 Suspended
0.865 High Similarity NPD7075 Discontinued
0.8647 High Similarity NPD7808 Phase 3
0.8642 High Similarity NPD8443 Clinical (unspecified phase)
0.8639 High Similarity NPD6797 Phase 2
0.8631 High Similarity NPD5844 Phase 1
0.8623 High Similarity NPD7473 Discontinued
0.8608 High Similarity NPD1512 Approved
0.8589 High Similarity NPD4868 Clinical (unspecified phase)
0.858 High Similarity NPD7096 Clinical (unspecified phase)
0.8571 High Similarity NPD3818 Discontinued
0.8554 High Similarity NPD6232 Discontinued
0.8544 High Similarity NPD4378 Clinical (unspecified phase)
0.8528 High Similarity NPD3817 Phase 2
0.8521 High Similarity NPD7804 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD1465 Phase 2
0.8452 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD1549 Phase 2
0.8313 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD7411 Suspended
0.8208 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD6801 Discontinued
0.8153 Intermediate Similarity NPD2796 Approved
0.8089 Intermediate Similarity NPD1510 Phase 2
0.8057 Intermediate Similarity NPD6559 Discontinued
0.8045 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD7768 Phase 2
0.8025 Intermediate Similarity NPD6799 Approved
0.8023 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD3749 Approved
0.7975 Intermediate Similarity NPD2532 Approved
0.7975 Intermediate Similarity NPD2534 Approved
0.7975 Intermediate Similarity NPD2533 Approved
0.7956 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD6599 Discontinued
0.795 Intermediate Similarity NPD3750 Approved
0.7949 Intermediate Similarity NPD1240 Approved
0.7949 Intermediate Similarity NPD1613 Approved
0.7949 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7946 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD7228 Approved
0.7877 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD5402 Approved
0.7865 Intermediate Similarity NPD8313 Approved
0.7865 Intermediate Similarity NPD8312 Approved
0.7849 Intermediate Similarity NPD1247 Approved
0.7848 Intermediate Similarity NPD1607 Approved
0.7836 Intermediate Similarity NPD6234 Discontinued
0.7836 Intermediate Similarity NPD919 Approved
0.7834 Intermediate Similarity NPD943 Approved
0.7829 Intermediate Similarity NPD3751 Discontinued
0.7812 Intermediate Similarity NPD6100 Approved
0.7812 Intermediate Similarity NPD6099 Approved
0.7806 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD3787 Discontinued
0.7778 Intermediate Similarity NPD2800 Approved
0.7771 Intermediate Similarity NPD5403 Approved
0.7759 Intermediate Similarity NPD3926 Phase 2
0.7756 Intermediate Similarity NPD3027 Phase 3
0.7746 Intermediate Similarity NPD7199 Phase 2
0.7742 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD2935 Discontinued
0.7697 Intermediate Similarity NPD7390 Discontinued
0.7679 Intermediate Similarity NPD3226 Approved
0.7669 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD2346 Discontinued
0.7651 Intermediate Similarity NPD5401 Approved
0.7647 Intermediate Similarity NPD37 Approved
0.764 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD3748 Approved
0.764 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD8150 Discontinued
0.7622 Intermediate Similarity NPD4628 Phase 3
0.7617 Intermediate Similarity NPD8151 Discontinued
0.7616 Intermediate Similarity NPD4966 Approved
0.7616 Intermediate Similarity NPD4967 Phase 2
0.7616 Intermediate Similarity NPD4965 Approved
0.7595 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD6782 Approved
0.7566 Intermediate Similarity NPD6776 Approved
0.7566 Intermediate Similarity NPD6778 Approved
0.7566 Intermediate Similarity NPD6777 Approved
0.7566 Intermediate Similarity NPD6781 Approved
0.7566 Intermediate Similarity NPD6780 Approved
0.7566 Intermediate Similarity NPD6779 Approved
0.7562 Intermediate Similarity NPD230 Phase 1
0.756 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD7685 Pre-registration
0.7545 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD7696 Phase 3
0.7539 Intermediate Similarity NPD7435 Discontinued
0.7539 Intermediate Similarity NPD7697 Approved
0.7539 Intermediate Similarity NPD7698 Approved
0.7538 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD7783 Phase 2
0.7532 Intermediate Similarity NPD4625 Phase 3
0.7516 Intermediate Similarity NPD6651 Approved
0.7515 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5711 Approved
0.75 Intermediate Similarity NPD5710 Approved
0.7487 Intermediate Similarity NPD4363 Phase 3
0.7487 Intermediate Similarity NPD4360 Phase 2
0.7486 Intermediate Similarity NPD7286 Phase 2
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7474 Intermediate Similarity NPD7701 Phase 2
0.7471 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD4908 Phase 1
0.7459 Intermediate Similarity NPD7240 Approved
0.7456 Intermediate Similarity NPD920 Approved
0.7453 Intermediate Similarity NPD447 Suspended
0.7446 Intermediate Similarity NPD8434 Phase 2
0.7423 Intermediate Similarity NPD7584 Approved
0.7423 Intermediate Similarity NPD2799 Discontinued
0.7412 Intermediate Similarity NPD1653 Approved
0.7409 Intermediate Similarity NPD7871 Phase 2
0.7409 Intermediate Similarity NPD7870 Phase 2
0.7407 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD5953 Discontinued
0.7401 Intermediate Similarity NPD7229 Phase 3
0.7399 Intermediate Similarity NPD8455 Phase 2
0.7396 Intermediate Similarity NPD6823 Phase 2
0.7381 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7699 Phase 2
0.7368 Intermediate Similarity NPD7700 Phase 2
0.7365 Intermediate Similarity NPD6190 Approved
0.7349 Intermediate Similarity NPD1243 Approved
0.7349 Intermediate Similarity NPD6674 Discontinued
0.7346 Intermediate Similarity NPD1933 Approved
0.7337 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2344 Approved
0.7321 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7874 Approved
0.7302 Intermediate Similarity NPD6535 Approved
0.7302 Intermediate Similarity NPD6534 Approved
0.7296 Intermediate Similarity NPD9494 Approved
0.7284 Intermediate Similarity NPD4060 Phase 1
0.7283 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7801 Approved
0.7267 Intermediate Similarity NPD2313 Discontinued
0.7267 Intermediate Similarity NPD7458 Discontinued
0.7261 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD2493 Approved
0.7254 Intermediate Similarity NPD2494 Approved
0.7247 Intermediate Similarity NPD8127 Discontinued
0.7246 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD1610 Phase 2
0.7239 Intermediate Similarity NPD5124 Phase 1
0.7239 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD8320 Phase 1
0.7231 Intermediate Similarity NPD8319 Approved
0.7229 Intermediate Similarity NPD7266 Discontinued
0.7212 Intermediate Similarity NPD7033 Discontinued
0.7206 Intermediate Similarity NPD7907 Approved
0.7202 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2424 Discontinued
0.7169 Intermediate Similarity NPD5405 Approved
0.7169 Intermediate Similarity NPD5406 Approved
0.7169 Intermediate Similarity NPD5404 Approved
0.7169 Intermediate Similarity NPD5408 Approved
0.7167 Intermediate Similarity NPD5242 Approved
0.7165 Intermediate Similarity NPD3450 Approved
0.7165 Intermediate Similarity NPD3452 Approved
0.716 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2309 Approved
0.7159 Intermediate Similarity NPD5353 Approved
0.715 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4583 Approved
0.7143 Intermediate Similarity NPD4582 Approved
0.7143 Intermediate Similarity NPD6832 Phase 2
0.7143 Intermediate Similarity NPD6844 Discontinued
0.7134 Intermediate Similarity NPD6355 Discontinued
0.7134 Intermediate Similarity NPD1201 Approved
0.7108 Intermediate Similarity NPD4111 Phase 1
0.7108 Intermediate Similarity NPD4665 Approved
0.7102 Intermediate Similarity NPD5760 Phase 2

  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