Structure

Physi-Chem Properties

Molecular Weight:  556.1
Volume:  533.243
LogP:  4.473
LogD:  2.42
LogS:  -4.745
# Rotatable Bonds:  3
TPSA:  198.12
# H-Bond Aceptor:  11
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.154
Synthetic Accessibility Score:  3.867
Fsp3:  0.067
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.923
MDCK Permeability:  5.750113814428914e-06
Pgp-inhibitor:  0.033
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.883
20% Bioavailability (F20%):  0.973
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  95.19388580322266%
Volume Distribution (VD):  0.358
Pgp-substrate:  5.050673961639404%

ADMET: Metabolism

CYP1A2-inhibitor:  0.676
CYP1A2-substrate:  0.131
CYP2C19-inhibitor:  0.326
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.723
CYP2C9-substrate:  0.894
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.254
CYP3A4-inhibitor:  0.267
CYP3A4-substrate:  0.097

ADMET: Excretion

Clearance (CL):  5.429
Half-life (T1/2):  0.5

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.129
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.634
Rat Oral Acute Toxicity:  0.814
Maximum Recommended Daily Dose:  0.121
Skin Sensitization:  0.95
Carcinogencity:  0.061
Eye Corrosion:  0.003
Eye Irritation:  0.905
Respiratory Toxicity:  0.022

Download Data

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

  Natural Product: NPC171985

Natural Product ID:  NPC171985
Common Name*:   Morelloflavone
IUPAC Name:   8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:   (+)-Morelloflavone; Morelloflavone
Standard InCHIKey:  GFWPWSNIXRDQJC-LMSSTIIKSA-N
Standard InCHI:  InChI=1S/C30H20O11/c31-14-4-1-12(2-5-14)29-27(28(39)25-18(35)8-15(32)9-23(25)41-29)26-20(37)10-19(36)24-21(38)11-22(40-30(24)26)13-3-6-16(33)17(34)7-13/h1-11,27,29,31-37H/t27-,29+/m0/s1
SMILES:  Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1c1c(O)cc(c2c1oc(cc2=O)c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1215433
PubChem CID:   5464454
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
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4020(01)89039-6]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(00)90246-6]
NPO32446 calophyllum panciflorum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[10654415]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO6617 Chirita eburnea Species Gesneriaceae Eukaryota whole plant Guangxi Province, China 2002-AUG PMID[15921435]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota root bark n.a. n.a. PMID[16562837]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. PMID[21028890]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5523 Picria felterrae Species Linderniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6202 Aglaomorpha coronans Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5523 Picria felterrae Species Linderniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5660 Scleropyrum maingayi Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6617 Chirita eburnea Species Gesneriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1917 Prosopis nigra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO64 Lysidice brevicalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4723 Phanerochaete velutina Species Phanerochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6202 Aglaomorpha coronans Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3806 Garcinia morella Species Clusiaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 116000.0 nM PMID[501673]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 99.2 % PMID[501673]
NPT927 Cell Line PBMC Homo sapiens IC50 = 82000.0 nM PMID[501673]
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[501674]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[501674]
NPT171 Cell Line MRC5 Homo sapiens IC50 > 64000.0 nM PMID[501675]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 6900.0 nM PMID[501673]
NPT2 Others Unspecified Selectivity Index = 12.0 n.a. PMID[501673]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 30.0 % PMID[501674]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 69.5 % PMID[501674]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 88.7 % PMID[501674]
NPT2 Others Unspecified Ratio > 3.0 n.a. PMID[501676]
NPT2 Others Unspecified IC50 = 1300.0 nM PMID[501677]

☑ 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 NPC171985 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 NPC320741
0.9873 High Similarity NPC107627
0.9873 High Similarity NPC224851
0.9627 High Similarity NPC186847
0.9627 High Similarity NPC257667
0.9627 High Similarity NPC472454
0.9557 High Similarity NPC219927
0.9503 High Similarity NPC475212
0.9487 High Similarity NPC32867
0.9441 High Similarity NPC260266
0.9437 High Similarity NPC259757
0.9434 High Similarity NPC477841
0.9383 High Similarity NPC300307
0.9371 High Similarity NPC142252
0.9367 High Similarity NPC295090
0.9367 High Similarity NPC53545
0.9367 High Similarity NPC117418
0.9363 High Similarity NPC69531
0.9341 High Similarity NPC132111
0.9337 High Similarity NPC324742
0.9317 High Similarity NPC477840
0.9313 High Similarity NPC474162
0.9313 High Similarity NPC474150
0.9299 High Similarity NPC66441
0.9299 High Similarity NPC182555
0.9295 High Similarity NPC174086
0.9268 High Similarity NPC4200
0.9259 High Similarity NPC272560
0.9255 High Similarity NPC63438
0.9255 High Similarity NPC12461
0.9255 High Similarity NPC476295
0.925 High Similarity NPC26326
0.925 High Similarity NPC113163
0.925 High Similarity NPC84324
0.925 High Similarity NPC301256
0.925 High Similarity NPC165970
0.925 High Similarity NPC289771
0.925 High Similarity NPC312273
0.925 High Similarity NPC66618
0.925 High Similarity NPC305987
0.925 High Similarity NPC288131
0.9236 High Similarity NPC213896
0.9236 High Similarity NPC192083
0.9207 High Similarity NPC102277
0.9207 High Similarity NPC279209
0.9202 High Similarity NPC243877
0.9193 High Similarity NPC476247
0.9193 High Similarity NPC473012
0.9193 High Similarity NPC473011
0.9193 High Similarity NPC206605
0.9187 High Similarity NPC192686
0.9187 High Similarity NPC119209
0.9187 High Similarity NPC101731
0.9187 High Similarity NPC118256
0.9187 High Similarity NPC297212
0.9182 High Similarity NPC471209
0.9182 High Similarity NPC475184
0.9182 High Similarity NPC112954
0.9177 High Similarity NPC300668
0.9177 High Similarity NPC321779
0.9177 High Similarity NPC134171
0.9177 High Similarity NPC258474
0.9177 High Similarity NPC201227
0.9172 High Similarity NPC106976
0.9162 High Similarity NPC265380
0.9152 High Similarity NPC271848
0.9152 High Similarity NPC262580
0.9152 High Similarity NPC289396
0.9152 High Similarity NPC81332
0.9152 High Similarity NPC212038
0.9146 High Similarity NPC188079
0.9141 High Similarity NPC120593
0.9141 High Similarity NPC13481
0.9141 High Similarity NPC207575
0.9136 High Similarity NPC473009
0.9136 High Similarity NPC186686
0.9136 High Similarity NPC272064
0.913 High Similarity NPC158188
0.913 High Similarity NPC196179
0.913 High Similarity NPC266314
0.913 High Similarity NPC474038
0.913 High Similarity NPC34089
0.9125 High Similarity NPC476410
0.9125 High Similarity NPC210459
0.9125 High Similarity NPC46736
0.9125 High Similarity NPC284127
0.9125 High Similarity NPC123544
0.9125 High Similarity NPC172202
0.9119 High Similarity NPC195796
0.9119 High Similarity NPC35038
0.9119 High Similarity NPC198489
0.9119 High Similarity NPC278778
0.9119 High Similarity NPC61112
0.9119 High Similarity NPC291878
0.9119 High Similarity NPC309648
0.9114 High Similarity NPC74924
0.9114 High Similarity NPC121568
0.9114 High Similarity NPC298692
0.9112 High Similarity NPC321916
0.9112 High Similarity NPC150977
0.9107 High Similarity NPC185275
0.9096 High Similarity NPC98583
0.9091 High Similarity NPC476365
0.9085 High Similarity NPC14662
0.9085 High Similarity NPC295082
0.908 High Similarity NPC58223
0.908 High Similarity NPC36916
0.908 High Similarity NPC473010
0.908 High Similarity NPC72787
0.908 High Similarity NPC36
0.908 High Similarity NPC62261
0.908 High Similarity NPC7688
0.908 High Similarity NPC125039
0.908 High Similarity NPC7154
0.908 High Similarity NPC471788
0.9074 High Similarity NPC194427
0.9068 High Similarity NPC476283
0.9068 High Similarity NPC321399
0.9068 High Similarity NPC476280
0.9068 High Similarity NPC292863
0.9068 High Similarity NPC36217
0.9068 High Similarity NPC184326
0.9068 High Similarity NPC475784
0.9064 High Similarity NPC73929
0.9064 High Similarity NPC47905
0.9064 High Similarity NPC139683
0.9062 High Similarity NPC183
0.9062 High Similarity NPC183851
0.9062 High Similarity NPC299520
0.9062 High Similarity NPC129684
0.9062 High Similarity NPC271741
0.9062 High Similarity NPC287789
0.9062 High Similarity NPC291508
0.9062 High Similarity NPC1796
0.9062 High Similarity NPC472598
0.9062 High Similarity NPC284820
0.9062 High Similarity NPC63454
0.9062 High Similarity NPC27337
0.9062 High Similarity NPC473272
0.9062 High Similarity NPC257166
0.9062 High Similarity NPC474055
0.9059 High Similarity NPC318119
0.9057 High Similarity NPC67396
0.9057 High Similarity NPC477503
0.9057 High Similarity NPC45849
0.9057 High Similarity NPC200761
0.9057 High Similarity NPC470327
0.9048 High Similarity NPC471789
0.9045 High Similarity NPC3825
0.9045 High Similarity NPC88804
0.9042 High Similarity NPC99591
0.9038 High Similarity NPC188679
0.9038 High Similarity NPC122894
0.9038 High Similarity NPC3036
0.9038 High Similarity NPC294852
0.9038 High Similarity NPC321011
0.9036 High Similarity NPC65333
0.9036 High Similarity NPC28589
0.9036 High Similarity NPC248593
0.9036 High Similarity NPC100251
0.903 High Similarity NPC177480
0.903 High Similarity NPC288813
0.9024 High Similarity NPC43319
0.9024 High Similarity NPC251336
0.9018 High Similarity NPC472625
0.9012 High Similarity NPC471211
0.9012 High Similarity NPC471210
0.9012 High Similarity NPC471499
0.9012 High Similarity NPC134783
0.9012 High Similarity NPC18380
0.9012 High Similarity NPC228383
0.9012 High Similarity NPC472632
0.9012 High Similarity NPC137232
0.9012 High Similarity NPC472634
0.9012 High Similarity NPC472275
0.9012 High Similarity NPC97812
0.9012 High Similarity NPC198829
0.9012 High Similarity NPC471212
0.9006 High Similarity NPC250214
0.9006 High Similarity NPC51760
0.9006 High Similarity NPC197856
0.9006 High Similarity NPC95936
0.9006 High Similarity NPC469658
0.9006 High Similarity NPC22192
0.9006 High Similarity NPC304322
0.9006 High Similarity NPC195167
0.9006 High Similarity NPC105584
0.9006 High Similarity NPC15815
0.9006 High Similarity NPC85121
0.9006 High Similarity NPC51247
0.9006 High Similarity NPC204879
0.9 High Similarity NPC78492
0.9 High Similarity NPC282307
0.9 High Similarity NPC209614
0.9 High Similarity NPC208152
0.9 High Similarity NPC472626
0.9 High Similarity NPC24640
0.9 High Similarity NPC170026
0.9 High Similarity NPC470328
0.8994 High Similarity NPC303485

  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 NPC171985 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
0.9236 High Similarity NPD2393 Clinical (unspecified phase)
0.908 High Similarity NPD6166 Phase 2
0.908 High Similarity NPD6167 Clinical (unspecified phase)
0.908 High Similarity NPD6168 Clinical (unspecified phase)
0.8931 High Similarity NPD1934 Approved
0.8896 High Similarity NPD6959 Discontinued
0.8882 High Similarity NPD4868 Clinical (unspecified phase)
0.882 High Similarity NPD8443 Clinical (unspecified phase)
0.8805 High Similarity NPD4380 Phase 2
0.8782 High Similarity NPD1511 Approved
0.8758 High Similarity NPD2801 Approved
0.8698 High Similarity NPD7993 Clinical (unspecified phase)
0.869 High Similarity NPD7054 Approved
0.8671 High Similarity NPD1512 Approved
0.8639 High Similarity NPD7074 Phase 3
0.8639 High Similarity NPD7472 Approved
0.8631 High Similarity NPD3818 Discontinued
0.8606 High Similarity NPD5494 Approved
0.8588 High Similarity NPD6797 Phase 2
0.8538 High Similarity NPD7251 Discontinued
0.8512 High Similarity NPD7852 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8488 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD7473 Discontinued
0.8424 Intermediate Similarity NPD3882 Suspended
0.8405 Intermediate Similarity NPD7411 Suspended
0.8397 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD6232 Discontinued
0.8382 Intermediate Similarity NPD7808 Phase 3
0.8373 Intermediate Similarity NPD7075 Discontinued
0.8364 Intermediate Similarity NPD3817 Phase 2
0.8363 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD1549 Phase 2
0.8303 Intermediate Similarity NPD7819 Suspended
0.8256 Intermediate Similarity NPD5844 Phase 1
0.8204 Intermediate Similarity NPD7768 Phase 2
0.8193 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD1510 Phase 2
0.8133 Intermediate Similarity NPD6801 Discontinued
0.8125 Intermediate Similarity NPD8312 Approved
0.8125 Intermediate Similarity NPD8313 Approved
0.8101 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD2796 Approved
0.8084 Intermediate Similarity NPD1465 Phase 2
0.8047 Intermediate Similarity NPD3749 Approved
0.8036 Intermediate Similarity NPD5402 Approved
0.8011 Intermediate Similarity NPD6559 Discontinued
0.7975 Intermediate Similarity NPD7390 Discontinued
0.7927 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD943 Approved
0.7831 Intermediate Similarity NPD5403 Approved
0.7814 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD3750 Approved
0.7785 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1240 Approved
0.7785 Intermediate Similarity NPD1613 Approved
0.7778 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD3787 Discontinued
0.7758 Intermediate Similarity NPD6799 Approved
0.773 Intermediate Similarity NPD2800 Approved
0.773 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD3926 Phase 2
0.7711 Intermediate Similarity NPD2534 Approved
0.7711 Intermediate Similarity NPD5401 Approved
0.7711 Intermediate Similarity NPD2533 Approved
0.7711 Intermediate Similarity NPD2532 Approved
0.7701 Intermediate Similarity NPD1247 Approved
0.7692 Intermediate Similarity NPD6599 Discontinued
0.7688 Intermediate Similarity NPD6234 Discontinued
0.7688 Intermediate Similarity NPD1607 Approved
0.7684 Intermediate Similarity NPD3751 Discontinued
0.7684 Intermediate Similarity NPD7228 Approved
0.7661 Intermediate Similarity NPD8455 Phase 2
0.7643 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD4908 Phase 1
0.7637 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD3226 Approved
0.7605 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7199 Phase 2
0.7586 Intermediate Similarity NPD919 Approved
0.758 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7577 Intermediate Similarity NPD8151 Discontinued
0.7569 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD2935 Discontinued
0.754 Intermediate Similarity NPD4360 Phase 2
0.754 Intermediate Similarity NPD4363 Phase 3
0.7529 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD6778 Approved
0.7526 Intermediate Similarity NPD6776 Approved
0.7526 Intermediate Similarity NPD6782 Approved
0.7526 Intermediate Similarity NPD6777 Approved
0.7526 Intermediate Similarity NPD6779 Approved
0.7526 Intermediate Similarity NPD6780 Approved
0.7526 Intermediate Similarity NPD6781 Approved
0.7516 Intermediate Similarity NPD230 Phase 1
0.7515 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD920 Approved
0.7514 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD37 Approved
0.75 Intermediate Similarity NPD8150 Discontinued
0.7485 Intermediate Similarity NPD2799 Discontinued
0.7485 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3748 Approved
0.7485 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD4965 Approved
0.7471 Intermediate Similarity NPD4967 Phase 2
0.7471 Intermediate Similarity NPD4966 Approved
0.7469 Intermediate Similarity NPD6651 Approved
0.746 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD5953 Discontinued
0.7439 Intermediate Similarity NPD1551 Phase 2
0.7439 Intermediate Similarity NPD6099 Approved
0.7439 Intermediate Similarity NPD6100 Approved
0.7438 Intermediate Similarity NPD2313 Discontinued
0.7425 Intermediate Similarity NPD6190 Approved
0.7418 Intermediate Similarity NPD7685 Pre-registration
0.7409 Intermediate Similarity NPD7435 Discontinued
0.7394 Intermediate Similarity NPD2344 Approved
0.7394 Intermediate Similarity NPD2346 Discontinued
0.7381 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD3027 Phase 3
0.7371 Intermediate Similarity NPD7871 Phase 2
0.7371 Intermediate Similarity NPD7870 Phase 2
0.7368 Intermediate Similarity NPD1653 Approved
0.7365 Intermediate Similarity NPD4628 Phase 3
0.736 Intermediate Similarity NPD7229 Phase 3
0.7348 Intermediate Similarity NPD7286 Phase 2
0.7333 Intermediate Similarity NPD5405 Approved
0.7333 Intermediate Similarity NPD5406 Approved
0.7333 Intermediate Similarity NPD5408 Approved
0.7333 Intermediate Similarity NPD5404 Approved
0.7329 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7458 Discontinued
0.7323 Intermediate Similarity NPD7783 Phase 2
0.7323 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7697 Approved
0.732 Intermediate Similarity NPD7696 Phase 3
0.732 Intermediate Similarity NPD7698 Approved
0.7308 Intermediate Similarity NPD1610 Phase 2
0.7305 Intermediate Similarity NPD1243 Approved
0.7268 Intermediate Similarity NPD6823 Phase 2
0.7263 Intermediate Similarity NPD6535 Approved
0.7263 Intermediate Similarity NPD5710 Approved
0.7263 Intermediate Similarity NPD5711 Approved
0.7263 Intermediate Similarity NPD6534 Approved
0.7262 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD7701 Phase 2
0.7241 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7801 Approved
0.7235 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD7240 Approved
0.7219 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD2309 Approved
0.7208 Intermediate Similarity NPD7584 Approved
0.7197 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD447 Suspended
0.7195 Intermediate Similarity NPD5124 Phase 1
0.7195 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7874 Approved
0.716 Intermediate Similarity NPD8166 Discontinued
0.716 Intermediate Similarity NPD7003 Approved
0.715 Intermediate Similarity NPD7700 Phase 2
0.715 Intermediate Similarity NPD7699 Phase 2
0.7143 Intermediate Similarity NPD2861 Phase 2
0.7143 Intermediate Similarity NPD4287 Approved
0.7135 Intermediate Similarity NPD4361 Phase 2
0.7135 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3268 Approved
0.7111 Intermediate Similarity NPD8127 Discontinued
0.7107 Intermediate Similarity NPD8320 Phase 1
0.7107 Intermediate Similarity NPD8319 Approved
0.7104 Intermediate Similarity NPD7177 Discontinued
0.7102 Intermediate Similarity NPD6844 Discontinued
0.7097 Intermediate Similarity NPD7549 Discontinued
0.7081 Intermediate Similarity NPD2798 Approved
0.7066 Intermediate Similarity NPD7033 Discontinued
0.7055 Intermediate Similarity NPD4625 Phase 3
0.7052 Intermediate Similarity NPD6273 Approved
0.7051 Intermediate Similarity NPD1548 Phase 1
0.7037 Intermediate Similarity NPD9494 Approved
0.7031 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6212 Phase 3
0.7031 Intermediate Similarity NPD6213 Phase 3
0.7019 Intermediate Similarity NPD2797 Approved
0.7019 Intermediate Similarity NPD1203 Approved
0.7019 Intermediate Similarity NPD1470 Approved
0.7012 Intermediate Similarity NPD6798 Discontinued
0.7006 Intermediate Similarity NPD7097 Phase 1
0.6994 Remote Similarity NPD6832 Phase 2
0.6988 Remote Similarity NPD1933 Approved
0.6982 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6981 Remote Similarity NPD1201 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