Structure

Physi-Chem Properties

Molecular Weight:  320.13
Volume:  316.478
LogP:  0.941
LogD:  1.226
LogS:  -2.963
# Rotatable Bonds:  3
TPSA:  85.22
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.884
Synthetic Accessibility Score:  3.819
Fsp3:  0.471
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.69
MDCK Permeability:  1.5112640539882705e-05
Pgp-inhibitor:  0.063
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.676
Plasma Protein Binding (PPB):  91.5656967163086%
Volume Distribution (VD):  0.901
Pgp-substrate:  9.661376953125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.948
CYP2C19-inhibitor:  0.053
CYP2C19-substrate:  0.816
CYP2C9-inhibitor:  0.064
CYP2C9-substrate:  0.748
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.356
CYP3A4-inhibitor:  0.079
CYP3A4-substrate:  0.784

ADMET: Excretion

Clearance (CL):  7.334
Half-life (T1/2):  0.796

ADMET: Toxicity

hERG Blockers:  0.06
Human Hepatotoxicity (H-HT):  0.768
Drug-inuced Liver Injury (DILI):  0.145
AMES Toxicity:  0.093
Rat Oral Acute Toxicity:  0.66
Maximum Recommended Daily Dose:  0.962
Skin Sensitization:  0.417
Carcinogencity:  0.903
Eye Corrosion:  0.003
Eye Irritation:  0.031
Respiratory Toxicity:  0.528

Download Data

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

  Natural Product: NPC30720

Natural Product ID:  NPC30720
Common Name*:   Oxytropisoflavan B
IUPAC Name:   (3R,4aS)-4a-hydroxy-3-(2-hydroxy-3,4-dimethoxyphenyl)-3,4,5,6-tetrahydro-2H-chromen-7-one
Synonyms:  
Standard InCHIKey:  WOKRCELVQNEUAD-BTDLBPIBSA-N
Standard InCHI:  InChI=1S/C17H20O6/c1-21-13-4-3-12(15(19)16(13)22-2)10-8-17(20)6-5-11(18)7-14(17)23-9-10/h3-4,7,10,19-20H,5-6,8-9H2,1-2H3/t10-,17-/m0/s1
SMILES:  COc1ccc([C@H]2C[C@]3(CCC(=O)C=C3OC2)O)c(c1OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1215436
PubChem CID:   46918734
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans

*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
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. seed n.a. DOI[10.1007/s11418-005-0009-z]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[10691704]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[16378371]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[16643065]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[18257536]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19177635]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19433363]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. Sunan County, Gansu Province, China 2006-JUN PMID[20684529]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[22032651]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[22032651]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota whole plant Guide County, Qinghai Province, China 2008-AUG PMID[22775441]
NPO8257 Carpha glomerata Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[30219526]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[32705864]
NPO784 Sinapis alba Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2131 Dactylorhiza viridis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO373 Viburnum erubescens Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8938 Halobacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7032 Marasmiellus troyanus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4536 Remirea maritima Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13474 Euphrasia genargentea Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21472 Pterolobium hexapetalum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10132 Schizophyllum lobatum Species Schizophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO593 Wikstroemia viridiflora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9998 Abies excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7418 Eucalyptus resinifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3838 Chrysosporum ovalisporum Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1293 Streptomyces matensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6807 Ranunculus asiaticus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5857 Achlya heterosexualis Species Saprolegniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4123 Trididemnum cyanophorum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9091 Orthosiphon spicatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2670 Maytenus chuchuhuasha Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO373 Viburnum erubescens Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4901 Arnica mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9594 Lysimachia fordiana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2439 Diplopterygium glaucum Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3151 Solanum lanceolatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2131 Dactylorhiza viridis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9737 Ampelocera edentula Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10038.1 Abies pinsapo var. marocana Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6065 Brassica carinata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8257 Carpha glomerata Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5086 Alternaria macrospora Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9867 Ixeris debilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1086 Botrytis cinerea Species Sclerotiniaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 50000.0 nM PMID[535844]
NPT1 Others Radical scavenging activity IC20 > 50.0 uM PMID[535844]

☑ 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 NPC30720 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
0.9103 High Similarity NPC212697
0.9073 High Similarity NPC299520
0.9073 High Similarity NPC129684
0.898 High Similarity NPC77598
0.8966 High Similarity NPC16353
0.8961 High Similarity NPC474162
0.8961 High Similarity NPC474150
0.8947 High Similarity NPC472914
0.8947 High Similarity NPC472911
0.8947 High Similarity NPC245758
0.8947 High Similarity NPC222814
0.8947 High Similarity NPC96167
0.8947 High Similarity NPC469584
0.8947 High Similarity NPC472910
0.8947 High Similarity NPC472913
0.894 High Similarity NPC31018
0.894 High Similarity NPC255807
0.8933 High Similarity NPC260979
0.8933 High Similarity NPC472912
0.8904 High Similarity NPC207732
0.8889 High Similarity NPC19158
0.8889 High Similarity NPC55738
0.8874 High Similarity NPC469550
0.8874 High Similarity NPC18727
0.8828 High Similarity NPC472335
0.8828 High Similarity NPC472332
0.8824 High Similarity NPC162869
0.8824 High Similarity NPC48208
0.8824 High Similarity NPC474836
0.8824 High Similarity NPC475267
0.8824 High Similarity NPC156057
0.8824 High Similarity NPC27337
0.8824 High Similarity NPC181960
0.8824 High Similarity NPC67876
0.8824 High Similarity NPC474208
0.8816 High Similarity NPC472909
0.8808 High Similarity NPC219582
0.8808 High Similarity NPC236637
0.8808 High Similarity NPC302950
0.8808 High Similarity NPC477231
0.8808 High Similarity NPC257648
0.8792 High Similarity NPC474903
0.879 High Similarity NPC235610
0.8784 High Similarity NPC165389
0.8774 High Similarity NPC173137
0.8774 High Similarity NPC266314
0.8767 High Similarity NPC106920
0.8767 High Similarity NPC273657
0.8767 High Similarity NPC312256
0.8766 High Similarity NPC476242
0.8766 High Similarity NPC152904
0.8758 High Similarity NPC255106
0.8758 High Similarity NPC474638
0.8758 High Similarity NPC195796
0.8758 High Similarity NPC235165
0.8758 High Similarity NPC470762
0.8758 High Similarity NPC472916
0.8758 High Similarity NPC474167
0.8758 High Similarity NPC291878
0.8758 High Similarity NPC278778
0.8758 High Similarity NPC317383
0.8758 High Similarity NPC24640
0.8758 High Similarity NPC35038
0.875 High Similarity NPC124714
0.875 High Similarity NPC25127
0.8742 High Similarity NPC272566
0.8742 High Similarity NPC31363
0.8742 High Similarity NPC475076
0.8742 High Similarity NPC476434
0.8741 High Similarity NPC162659
0.8741 High Similarity NPC248727
0.8741 High Similarity NPC270456
0.8741 High Similarity NPC265433
0.8733 High Similarity NPC69430
0.8733 High Similarity NPC200060
0.8733 High Similarity NPC139293
0.8733 High Similarity NPC142876
0.8733 High Similarity NPC40290
0.8733 High Similarity NPC195763
0.8733 High Similarity NPC264550
0.8733 High Similarity NPC264289
0.8733 High Similarity NPC333691
0.8726 High Similarity NPC62261
0.8726 High Similarity NPC224280
0.8718 High Similarity NPC472964
0.8716 High Similarity NPC157133
0.8716 High Similarity NPC472560
0.8716 High Similarity NPC474799
0.871 High Similarity NPC119209
0.871 High Similarity NPC36217
0.871 High Similarity NPC118256
0.871 High Similarity NPC470183
0.871 High Similarity NPC192686
0.871 High Similarity NPC472902
0.871 High Similarity NPC474960
0.871 High Similarity NPC472624
0.8701 High Similarity NPC210084
0.8701 High Similarity NPC291508
0.8701 High Similarity NPC471515
0.8701 High Similarity NPC471479
0.8701 High Similarity NPC241904
0.8701 High Similarity NPC99597
0.8701 High Similarity NPC220462
0.8701 High Similarity NPC472598
0.8701 High Similarity NPC472963
0.8701 High Similarity NPC474055
0.8701 High Similarity NPC300727
0.8701 High Similarity NPC136674
0.8701 High Similarity NPC78225
0.8699 High Similarity NPC110419
0.8693 High Similarity NPC82592
0.8693 High Similarity NPC2928
0.8693 High Similarity NPC45849
0.8693 High Similarity NPC200761
0.8693 High Similarity NPC152951
0.8693 High Similarity NPC256925
0.8693 High Similarity NPC230149
0.8693 High Similarity NPC213622
0.8693 High Similarity NPC470327
0.8693 High Similarity NPC477503
0.8693 High Similarity NPC37392
0.8693 High Similarity NPC57674
0.8693 High Similarity NPC117992
0.8693 High Similarity NPC16082
0.8693 High Similarity NPC67396
0.8693 High Similarity NPC168247
0.869 High Similarity NPC144284
0.869 High Similarity NPC322021
0.8684 High Similarity NPC180234
0.8684 High Similarity NPC60972
0.8684 High Similarity NPC100263
0.8684 High Similarity NPC327225
0.8684 High Similarity NPC120537
0.8684 High Similarity NPC181209
0.8684 High Similarity NPC245382
0.8684 High Similarity NPC199100
0.8684 High Similarity NPC35763
0.8684 High Similarity NPC100971
0.8684 High Similarity NPC131266
0.8684 High Similarity NPC269451
0.8684 High Similarity NPC291802
0.8684 High Similarity NPC39732
0.8684 High Similarity NPC121522
0.8684 High Similarity NPC209487
0.8684 High Similarity NPC216769
0.8675 High Similarity NPC338131
0.8675 High Similarity NPC472279
0.8675 High Similarity NPC29231
0.8667 High Similarity NPC80710
0.8667 High Similarity NPC3036
0.8667 High Similarity NPC254702
0.8667 High Similarity NPC203747
0.8667 High Similarity NPC139364
0.8667 High Similarity NPC194653
0.8662 High Similarity NPC124038
0.8662 High Similarity NPC475985
0.8662 High Similarity NPC327410
0.8662 High Similarity NPC186686
0.8662 High Similarity NPC41301
0.8658 High Similarity NPC472333
0.8658 High Similarity NPC208507
0.8654 High Similarity NPC472634
0.8654 High Similarity NPC61010
0.8654 High Similarity NPC134783
0.8654 High Similarity NPC471210
0.8654 High Similarity NPC472632
0.8654 High Similarity NPC474038
0.8649 High Similarity NPC474982
0.8649 High Similarity NPC105213
0.8649 High Similarity NPC232883
0.8645 High Similarity NPC204879
0.8645 High Similarity NPC474290
0.8645 High Similarity NPC95936
0.8645 High Similarity NPC250214
0.8639 High Similarity NPC470811
0.8639 High Similarity NPC477697
0.8639 High Similarity NPC477696
0.8636 High Similarity NPC227062
0.8636 High Similarity NPC150227
0.8636 High Similarity NPC68093
0.8636 High Similarity NPC472455
0.8636 High Similarity NPC209614
0.8636 High Similarity NPC471500
0.8636 High Similarity NPC326037
0.8636 High Similarity NPC274730
0.8636 High Similarity NPC470328
0.8636 High Similarity NPC303255
0.8636 High Similarity NPC472907
0.8636 High Similarity NPC472626
0.8636 High Similarity NPC13858
0.8636 High Similarity NPC320825
0.8636 High Similarity NPC191146
0.8627 High Similarity NPC167091
0.8627 High Similarity NPC144801
0.8627 High Similarity NPC33051
0.8627 High Similarity NPC116850
0.8627 High Similarity NPC227337
0.8627 High Similarity NPC292214
0.8627 High Similarity NPC176775
0.8627 High Similarity NPC274327

  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 NPC30720 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
0.8808 High Similarity NPD1934 Approved
0.8627 High Similarity NPD2393 Clinical (unspecified phase)
0.8627 High Similarity NPD2801 Approved
0.8397 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD3882 Suspended
0.8375 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD6166 Phase 2
0.8278 Intermediate Similarity NPD1511 Approved
0.8252 Intermediate Similarity NPD3027 Phase 3
0.8207 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8207 Intermediate Similarity NPD1613 Approved
0.8182 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD6234 Discontinued
0.8171 Intermediate Similarity NPD7074 Phase 3
0.817 Intermediate Similarity NPD1512 Approved
0.816 Intermediate Similarity NPD3818 Discontinued
0.8125 Intermediate Similarity NPD5494 Approved
0.8112 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD7054 Approved
0.8101 Intermediate Similarity NPD3817 Phase 2
0.8098 Intermediate Similarity NPD7473 Discontinued
0.8079 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD4380 Phase 2
0.8061 Intermediate Similarity NPD7472 Approved
0.8054 Intermediate Similarity NPD6099 Approved
0.8054 Intermediate Similarity NPD6100 Approved
0.8038 Intermediate Similarity NPD1465 Phase 2
0.8027 Intermediate Similarity NPD230 Phase 1
0.8025 Intermediate Similarity NPD6232 Discontinued
0.7975 Intermediate Similarity NPD37 Approved
0.7939 Intermediate Similarity NPD7228 Approved
0.7937 Intermediate Similarity NPD4965 Approved
0.7937 Intermediate Similarity NPD4966 Approved
0.7937 Intermediate Similarity NPD4967 Phase 2
0.7917 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD6797 Phase 2
0.7904 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD5844 Phase 1
0.7882 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD1510 Phase 2
0.7857 Intermediate Similarity NPD7251 Discontinued
0.7853 Intermediate Similarity NPD7199 Phase 2
0.7834 Intermediate Similarity NPD1653 Approved
0.7832 Intermediate Similarity NPD4749 Approved
0.7832 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD1549 Phase 2
0.7829 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD7808 Phase 3
0.7808 Intermediate Similarity NPD4908 Phase 1
0.7792 Intermediate Similarity NPD6190 Approved
0.7778 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7075 Discontinued
0.7764 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD9494 Approved
0.7727 Intermediate Similarity NPD3750 Approved
0.7718 Intermediate Similarity NPD943 Approved
0.7718 Intermediate Similarity NPD1240 Approved
0.7703 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD7819 Suspended
0.7692 Intermediate Similarity NPD1610 Phase 2
0.7692 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD2534 Approved
0.7643 Intermediate Similarity NPD2533 Approved
0.7643 Intermediate Similarity NPD2532 Approved
0.7619 Intermediate Similarity NPD3751 Discontinued
0.7616 Intermediate Similarity NPD1607 Approved
0.7582 Intermediate Similarity NPD2796 Approved
0.758 Intermediate Similarity NPD6799 Approved
0.7548 Intermediate Similarity NPD2800 Approved
0.7544 Intermediate Similarity NPD7685 Pre-registration
0.7532 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD6959 Discontinued
0.7516 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6599 Discontinued
0.75 Intermediate Similarity NPD8166 Discontinued
0.7485 Intermediate Similarity NPD3787 Discontinued
0.7484 Intermediate Similarity NPD2424 Discontinued
0.7471 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD7411 Suspended
0.7467 Intermediate Similarity NPD3268 Approved
0.7443 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD6559 Discontinued
0.7442 Intermediate Similarity NPD7240 Approved
0.744 Intermediate Similarity NPD3926 Phase 2
0.7439 Intermediate Similarity NPD5402 Approved
0.7439 Intermediate Similarity NPD5353 Approved
0.7434 Intermediate Similarity NPD5124 Phase 1
0.7434 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD447 Suspended
0.7425 Intermediate Similarity NPD1247 Approved
0.7423 Intermediate Similarity NPD6801 Discontinued
0.741 Intermediate Similarity NPD228 Approved
0.7403 Intermediate Similarity NPD3748 Approved
0.74 Intermediate Similarity NPD4625 Phase 3
0.7389 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD4628 Phase 3
0.7386 Intermediate Similarity NPD6651 Approved
0.7383 Intermediate Similarity NPD3018 Phase 2
0.7383 Intermediate Similarity NPD2861 Phase 2
0.7365 Intermediate Similarity NPD2797 Approved
0.7362 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4357 Discontinued
0.7355 Intermediate Similarity NPD2935 Discontinued
0.7349 Intermediate Similarity NPD3749 Approved
0.7343 Intermediate Similarity NPD5536 Phase 2
0.7337 Intermediate Similarity NPD5242 Approved
0.7329 Intermediate Similarity NPD422 Phase 1
0.7325 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1652 Phase 2
0.732 Intermediate Similarity NPD6355 Discontinued
0.7315 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7266 Discontinued
0.7305 Intermediate Similarity NPD5283 Phase 1
0.7305 Intermediate Similarity NPD919 Approved
0.7301 Intermediate Similarity NPD7028 Phase 2
0.7299 Intermediate Similarity NPD7549 Discontinued
0.7294 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD1548 Phase 1
0.7289 Intermediate Similarity NPD7768 Phase 2
0.7279 Intermediate Similarity NPD9269 Phase 2
0.7278 Intermediate Similarity NPD4110 Phase 3
0.7278 Intermediate Similarity NPD7229 Phase 3
0.7278 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD4060 Phase 1
0.7237 Intermediate Similarity NPD6798 Discontinued
0.723 Intermediate Similarity NPD2983 Phase 2
0.723 Intermediate Similarity NPD2982 Phase 2
0.7222 Intermediate Similarity NPD5403 Approved
0.7219 Intermediate Similarity NPD8127 Discontinued
0.7176 Intermediate Similarity NPD5711 Approved
0.7176 Intermediate Similarity NPD5710 Approved
0.7174 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD2981 Phase 2
0.7162 Intermediate Similarity NPD1608 Approved
0.7159 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3620 Phase 2
0.7143 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2493 Approved
0.7135 Intermediate Similarity NPD2494 Approved
0.7134 Intermediate Similarity NPD1551 Phase 2
0.7133 Intermediate Similarity NPD3266 Approved
0.7133 Intermediate Similarity NPD3267 Approved
0.712 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD4582 Approved
0.7112 Intermediate Similarity NPD4583 Approved
0.7107 Intermediate Similarity NPD6674 Discontinued
0.7099 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD5401 Approved
0.7095 Intermediate Similarity NPD3705 Approved
0.7093 Intermediate Similarity NPD2403 Approved
0.7083 Intermediate Similarity NPD6671 Approved
0.7078 Intermediate Similarity NPD6233 Phase 2
0.707 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2799 Discontinued
0.707 Intermediate Similarity NPD7033 Discontinued
0.7067 Intermediate Similarity NPD8651 Approved
0.7063 Intermediate Similarity NPD1241 Discontinued
0.7059 Intermediate Similarity NPD7095 Approved
0.7059 Intermediate Similarity NPD4002 Approved
0.7059 Intermediate Similarity NPD7680 Approved
0.7059 Intermediate Similarity NPD4004 Approved
0.7048 Intermediate Similarity NPD5090 Approved
0.7048 Intermediate Similarity NPD6386 Approved
0.7048 Intermediate Similarity NPD5089 Approved
0.7048 Intermediate Similarity NPD6385 Approved
0.7043 Intermediate Similarity NPD3452 Approved
0.7043 Intermediate Similarity NPD3450 Approved
0.7039 Intermediate Similarity NPD8434 Phase 2
0.7039 Intermediate Similarity NPD8150 Discontinued
0.703 Intermediate Similarity NPD3226 Approved
0.703 Intermediate Similarity NPD7458 Discontinued
0.7021 Intermediate Similarity NPD4750 Phase 3
0.7021 Intermediate Similarity NPD3022 Approved
0.7021 Intermediate Similarity NPD3021 Approved
0.7019 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD1296 Phase 2
0.7013 Intermediate Similarity NPD3764 Approved
0.7012 Intermediate Similarity NPD920 Approved
0.7007 Intermediate Similarity NPD9268 Approved
0.7006 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7097 Phase 1
0.7 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1933 Approved
0.6981 Remote Similarity NPD2346 Discontinued
0.6981 Remote Similarity NPD6005 Phase 3
0.6981 Remote Similarity NPD6002 Phase 3
0.6981 Remote Similarity NPD2344 Approved
0.6981 Remote Similarity NPD6006 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