Structure

Physi-Chem Properties

Molecular Weight:  146.05
Volume:  147.413
LogP:  0.597
LogD:  0.814
LogS:  -2.006
# Rotatable Bonds:  0
TPSA:  45.75
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.6
Synthetic Accessibility Score:  2.02
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.457
MDCK Permeability:  1.5481708032893948e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.062
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.551
Plasma Protein Binding (PPB):  34.87890625%
Volume Distribution (VD):  0.892
Pgp-substrate:  54.218482971191406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.882
CYP1A2-substrate:  0.531
CYP2C19-inhibitor:  0.136
CYP2C19-substrate:  0.321
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.798
CYP2D6-inhibitor:  0.064
CYP2D6-substrate:  0.129
CYP3A4-inhibitor:  0.102
CYP3A4-substrate:  0.227

ADMET: Excretion

Clearance (CL):  9.693
Half-life (T1/2):  0.894

ADMET: Toxicity

hERG Blockers:  0.057
Human Hepatotoxicity (H-HT):  0.401
Drug-inuced Liver Injury (DILI):  0.952
AMES Toxicity:  0.228
Rat Oral Acute Toxicity:  0.855
Maximum Recommended Daily Dose:  0.02
Skin Sensitization:  0.48
Carcinogencity:  0.096
Eye Corrosion:  0.034
Eye Irritation:  0.981
Respiratory Toxicity:  0.574

Download Data

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

  Natural Product: NPC164664

Natural Product ID:  NPC164664
Common Name*:   Quinazolinone
IUPAC Name:   1H-quinazolin-4-one
Synonyms:   4-quinazolone; Quinazolin-4-ol
Standard InCHIKey:  QMNUDYFKZYBWQX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)
SMILES:  Oc1ncnc2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL266540
PubChem CID:   63112
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004788] Diazanaphthalenes
        • [CHEMONTID:0004789] Benzodiazines
          • [CHEMONTID:0000485] Quinazolines

*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
NPO22018 Hydrangea chinensis Species Hydrangeaceae Eukaryota Roots n.a. n.a. PMID[11473431]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[11678654]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15787451]
NPO11394 Dichroa febrifuga Species Hydrangeaceae Eukaryota n.a. n.a. n.a. PMID[19467876]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota Roots Anhui, China n.a. PMID[22694318]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[32004936]
NPO22018 Hydrangea chinensis Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11394 Dichroa febrifuga Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22018 Hydrangea chinensis Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11394 Dichroa febrifuga Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11394 Dichroa febrifuga Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22018 Hydrangea chinensis Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11394 Dichroa febrifuga Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4554 Isatis tinctoria Species Brassicaceae 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
NPT2562 Individual Protein Poly [ADP-ribose] polymerase-1 Homo sapiens IC50 = 9500.0 nM PMID[544269]
NPT4896 Individual Protein Purine nucleoside phosphorylase Mycobacterium tuberculosis Kd = 316227.77 nM PMID[544271]
NPT2562 Individual Protein Poly [ADP-ribose] polymerase-1 Homo sapiens IC50 = 15800.0 nM PMID[544272]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 79432.8 nM PMID[544274]
NPT1699 Individual Protein 3-phosphoinositide dependent protein kinase-1 Homo sapiens IC50 = 345000.0 nM PMID[544276]
NPT2562 Individual Protein Poly [ADP-ribose] polymerase-1 Homo sapiens IC50 = 5750.0 nM PMID[544277]
NPT2562 Individual Protein Poly [ADP-ribose] polymerase-1 Homo sapiens Inhibition > 60.0 % PMID[544277]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 6513.1 nM PMID[544273]
NPT2818 Individual Protein Dihydrofolate reductase Homo sapiens log(1/C) = 3.62 n.a. PMID[544279]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki > 500000.0 nM PMID[544280]
NPT5106 Individual Protein Phosphodiesterase 10A Homo sapiens Ki = 910000.0 nM PMID[544283]
NPT2 Others Unspecified Potency n.a. 630.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1411.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 35462.8 nM PubChem BioAssay data set
NPT610 Others Molecular identity unknown Activity = 29.0 % PMID[544270]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 1122.0 nM PMID[544273]
NPT2 Others Unspecified Potency = 730.8 nM PMID[544273]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 39810.7 nM PMID[544275]
NPT2 Others Unspecified Potency n.a. 290.9 nM PMID[544273]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.81 mmol/L PMID[544278]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Ki = 10460.0 nM PMID[544280]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 15700.0 nM PMID[544280]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki > 500000.0 nM PMID[544280]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -10.42 % PMID[544282]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 37.21 % PMID[544284]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.24 % PMID[544285]
NPT27633 SINGLE PROTEIN Dihydrofolate reductase Rattus norvegicus Log 1/C = 3.62 n.a. PMID[544268]

☑ 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 NPC164664 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
0.9545 High Similarity NPC224632
0.9304 High Similarity NPC278874
0.9187 High Similarity NPC105758
0.9187 High Similarity NPC476686
0.9187 High Similarity NPC476688
0.913 High Similarity NPC208060
0.8876 High Similarity NPC254762
0.8802 High Similarity NPC477891
0.8802 High Similarity NPC144114
0.8713 High Similarity NPC472289
0.8286 Intermediate Similarity NPC230805
0.7987 Intermediate Similarity NPC60553
0.7661 Intermediate Similarity NPC97367
0.7586 Intermediate Similarity NPC473764
0.7586 Intermediate Similarity NPC314940
0.7463 Intermediate Similarity NPC130570
0.731 Intermediate Similarity NPC471603
0.7299 Intermediate Similarity NPC59779
0.7299 Intermediate Similarity NPC124542
0.7299 Intermediate Similarity NPC471177
0.7286 Intermediate Similarity NPC62995
0.7249 Intermediate Similarity NPC242209
0.7247 Intermediate Similarity NPC252590
0.7216 Intermediate Similarity NPC471178
0.7182 Intermediate Similarity NPC96890
0.7151 Intermediate Similarity NPC26872
0.7143 Intermediate Similarity NPC131718
0.7143 Intermediate Similarity NPC25899
0.7127 Intermediate Similarity NPC288943
0.7102 Intermediate Similarity NPC177404
0.7102 Intermediate Similarity NPC48192
0.7088 Intermediate Similarity NPC283152
0.7088 Intermediate Similarity NPC184964
0.7076 Intermediate Similarity NPC288445
0.7062 Intermediate Similarity NPC473057
0.7059 Intermediate Similarity NPC46580
0.7059 Intermediate Similarity NPC161292
0.7053 Intermediate Similarity NPC329541
0.7039 Intermediate Similarity NPC44161
0.7029 Intermediate Similarity NPC26850
0.7027 Intermediate Similarity NPC220765
0.7006 Intermediate Similarity NPC47298
0.7006 Intermediate Similarity NPC315214
0.7 Intermediate Similarity NPC324149
0.6989 Remote Similarity NPC204717
0.6989 Remote Similarity NPC84508
0.6978 Remote Similarity NPC303225
0.6966 Remote Similarity NPC32028
0.6966 Remote Similarity NPC102423
0.6966 Remote Similarity NPC159319
0.6957 Remote Similarity NPC72980
0.6952 Remote Similarity NPC314002
0.694 Remote Similarity NPC203754
0.694 Remote Similarity NPC150048
0.6923 Remote Similarity NPC474409
0.6923 Remote Similarity NPC471294
0.6923 Remote Similarity NPC259545
0.6915 Remote Similarity NPC171171
0.6905 Remote Similarity NPC280853
0.6898 Remote Similarity NPC62069
0.6897 Remote Similarity NPC153769
0.689 Remote Similarity NPC132631
0.689 Remote Similarity NPC103687
0.6865 Remote Similarity NPC42979
0.6864 Remote Similarity NPC285016
0.6864 Remote Similarity NPC245657
0.6862 Remote Similarity NPC42591
0.6856 Remote Similarity NPC90229
0.685 Remote Similarity NPC18348
0.6848 Remote Similarity NPC224764
0.6845 Remote Similarity NPC250178
0.6845 Remote Similarity NPC471596
0.6845 Remote Similarity NPC48938
0.6834 Remote Similarity NPC477113
0.6832 Remote Similarity NPC151489
0.6823 Remote Similarity NPC99666
0.6821 Remote Similarity NPC192315
0.6818 Remote Similarity NPC200836
0.6818 Remote Similarity NPC53144
0.6818 Remote Similarity NPC120070
0.6813 Remote Similarity NPC126481
0.6813 Remote Similarity NPC46358
0.681 Remote Similarity NPC2497
0.6806 Remote Similarity NPC30540
0.6789 Remote Similarity NPC295452
0.6789 Remote Similarity NPC39092
0.6789 Remote Similarity NPC66083
0.6789 Remote Similarity NPC171393
0.6788 Remote Similarity NPC256893
0.6786 Remote Similarity NPC476167
0.6782 Remote Similarity NPC309845
0.678 Remote Similarity NPC141353
0.6774 Remote Similarity NPC232340
0.6769 Remote Similarity NPC77555
0.6766 Remote Similarity NPC477111
0.6753 Remote Similarity NPC326634
0.6748 Remote Similarity NPC212125
0.6748 Remote Similarity NPC306397
0.6744 Remote Similarity NPC471598
0.6739 Remote Similarity NPC313791
0.6738 Remote Similarity NPC478032
0.6732 Remote Similarity NPC237740
0.6718 Remote Similarity NPC472193
0.6716 Remote Similarity NPC128084
0.6703 Remote Similarity NPC317054
0.6703 Remote Similarity NPC49217
0.6703 Remote Similarity NPC108469
0.67 Remote Similarity NPC470500
0.67 Remote Similarity NPC475070
0.6686 Remote Similarity NPC282531
0.6685 Remote Similarity NPC158129
0.6685 Remote Similarity NPC477889
0.6685 Remote Similarity NPC118511
0.6683 Remote Similarity NPC282247
0.6683 Remote Similarity NPC48317
0.6683 Remote Similarity NPC211813
0.6667 Remote Similarity NPC36168
0.6667 Remote Similarity NPC212535
0.6667 Remote Similarity NPC322644
0.6667 Remote Similarity NPC242923
0.6667 Remote Similarity NPC133306
0.665 Remote Similarity NPC80596
0.6649 Remote Similarity NPC222592
0.6649 Remote Similarity NPC168486
0.6649 Remote Similarity NPC194040
0.6649 Remote Similarity NPC314573
0.6648 Remote Similarity NPC129721
0.6646 Remote Similarity NPC165370
0.6636 Remote Similarity NPC116622
0.6632 Remote Similarity NPC144381
0.6632 Remote Similarity NPC190007
0.6627 Remote Similarity NPC476687
0.6627 Remote Similarity NPC476689
0.6627 Remote Similarity NPC476685
0.6618 Remote Similarity NPC477110
0.6618 Remote Similarity NPC85273
0.6609 Remote Similarity NPC159856
0.6607 Remote Similarity NPC472067
0.6607 Remote Similarity NPC472066
0.6607 Remote Similarity NPC472031
0.6603 Remote Similarity NPC248627
0.6599 Remote Similarity NPC267928
0.6599 Remote Similarity NPC156704
0.6597 Remote Similarity NPC94943
0.6596 Remote Similarity NPC88363
0.6592 Remote Similarity NPC472068
0.6587 Remote Similarity NPC324611
0.6579 Remote Similarity NPC63109
0.6573 Remote Similarity NPC469760
0.6573 Remote Similarity NPC25008
0.6573 Remote Similarity NPC469765
0.6573 Remote Similarity NPC73952
0.6573 Remote Similarity NPC469786
0.6573 Remote Similarity NPC259644
0.6573 Remote Similarity NPC469763
0.6571 Remote Similarity NPC220523
0.6555 Remote Similarity NPC173080
0.655 Remote Similarity NPC471594
0.6548 Remote Similarity NPC184437
0.6548 Remote Similarity NPC222018
0.6545 Remote Similarity NPC471311
0.6545 Remote Similarity NPC284559
0.6545 Remote Similarity NPC471313
0.6537 Remote Similarity NPC5145
0.6536 Remote Similarity NPC212376
0.6536 Remote Similarity NPC63562
0.6536 Remote Similarity NPC75540
0.6536 Remote Similarity NPC211572
0.6536 Remote Similarity NPC80597
0.6536 Remote Similarity NPC70922
0.6535 Remote Similarity NPC329708
0.6535 Remote Similarity NPC47059
0.6535 Remote Similarity NPC274291
0.6535 Remote Similarity NPC264166
0.6535 Remote Similarity NPC118832
0.6535 Remote Similarity NPC165349
0.6531 Remote Similarity NPC106937
0.6529 Remote Similarity NPC328029
0.6529 Remote Similarity NPC29702
0.6526 Remote Similarity NPC161887
0.6526 Remote Similarity NPC266551
0.6526 Remote Similarity NPC219963
0.6519 Remote Similarity NPC230869
0.6508 Remote Similarity NPC164340
0.6507 Remote Similarity NPC469727
0.6506 Remote Similarity NPC226662
0.6505 Remote Similarity NPC121658
0.6505 Remote Similarity NPC14651
0.6502 Remote Similarity NPC476121
0.6502 Remote Similarity NPC476124
0.65 Remote Similarity NPC315957
0.65 Remote Similarity NPC315491
0.65 Remote Similarity NPC469785
0.65 Remote Similarity NPC19872
0.65 Remote Similarity NPC45459
0.65 Remote Similarity NPC121772
0.65 Remote Similarity NPC249040
0.6497 Remote Similarity NPC118135
0.6497 Remote Similarity NPC314440
0.6495 Remote Similarity NPC32771

  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 NPC164664 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
0.8528 High Similarity NPD444 Approved
0.8286 Intermediate Similarity NPD9714 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5428 Discontinued
0.7844 Intermediate Similarity NPD639 Discontinued
0.7765 Intermediate Similarity NPD5925 Phase 1
0.7735 Intermediate Similarity NPD2410 Phase 2
0.766 Intermediate Similarity NPD6132 Phase 1
0.7588 Intermediate Similarity NPD1954 Phase 1
0.7581 Intermediate Similarity NPD4673 Phase 2
0.7458 Intermediate Similarity NPD9690 Approved
0.7447 Intermediate Similarity NPD5885 Approved
0.7433 Intermediate Similarity NPD6594 Discontinued
0.7414 Intermediate Similarity NPD926 Approved
0.7414 Intermediate Similarity NPD925 Approved
0.7409 Intermediate Similarity NPD1197 Approved
0.7401 Intermediate Similarity NPD3224 Phase 2
0.738 Intermediate Similarity NPD1912 Approved
0.7371 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD5529 Phase 1
0.7366 Intermediate Similarity NPD1234 Discontinued
0.7366 Intermediate Similarity NPD4615 Phase 2
0.7354 Intermediate Similarity NPD7419 Discontinued
0.7341 Intermediate Similarity NPD112 Approved
0.7341 Intermediate Similarity NPD9705 Discontinued
0.734 Intermediate Similarity NPD4403 Phase 3
0.734 Intermediate Similarity NPD4401 Phase 2
0.7327 Intermediate Similarity NPD3233 Phase 2
0.7327 Intermediate Similarity NPD3234 Phase 3
0.7326 Intermediate Similarity NPD3403 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD4358 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD3261 Phase 1
0.7294 Intermediate Similarity NPD2882 Phase 1
0.7273 Intermediate Similarity NPD425 Approved
0.7273 Intermediate Similarity NPD424 Approved
0.7258 Intermediate Similarity NPD3439 Approved
0.7256 Intermediate Similarity NPD852 Discontinued
0.7234 Intermediate Similarity NPD9695 Approved
0.7225 Intermediate Similarity NPD3814 Phase 1
0.722 Intermediate Similarity NPD1273 Discontinued
0.7219 Intermediate Similarity NPD6022 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3830 Phase 1
0.7207 Intermediate Similarity NPD966 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6957 Approved
0.72 Intermediate Similarity NPD7112 Discontinued
0.72 Intermediate Similarity NPD6958 Approved
0.7189 Intermediate Similarity NPD7758 Approved
0.7189 Intermediate Similarity NPD7757 Approved
0.7189 Intermediate Similarity NPD706 Phase 1
0.7181 Intermediate Similarity NPD6887 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD1043 Phase 3
0.7164 Intermediate Similarity NPD7423 Phase 2
0.7151 Intermediate Similarity NPD2993 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6307 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD1313 Approved
0.7114 Intermediate Similarity NPD6711 Approved
0.7111 Intermediate Similarity NPD1599 Approved
0.7105 Intermediate Similarity NPD4998 Phase 3
0.7105 Intermediate Similarity NPD4999 Phase 3
0.7099 Intermediate Similarity NPD9187 Approved
0.7093 Intermediate Similarity NPD6158 Phase 2
0.7093 Intermediate Similarity NPD3262 Approved
0.7093 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD2127 Suspended
0.7088 Intermediate Similarity NPD1272 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD1215 Discontinued
0.7073 Intermediate Similarity NPD4945 Discontinued
0.7072 Intermediate Similarity NPD5065 Approved
0.7065 Intermediate Similarity NPD7188 Phase 3
0.7062 Intermediate Similarity NPD2757 Phase 2
0.7049 Intermediate Similarity NPD443 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD1503 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD3960 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD459 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD3013 Phase 3
0.7035 Intermediate Similarity NPD3014 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD2391 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD3931 Approved
0.7026 Intermediate Similarity NPD3928 Approved
0.7022 Intermediate Similarity NPD509 Phase 3
0.7011 Intermediate Similarity NPD2601 Approved
0.7011 Intermediate Similarity NPD2599 Approved
0.7011 Intermediate Similarity NPD2600 Approved
0.701 Intermediate Similarity NPD1838 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5905 Phase 1
0.7006 Intermediate Similarity NPD1684 Approved
0.7006 Intermediate Similarity NPD1685 Approved
0.7005 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.6995 Remote Similarity NPD6159 Phase 2
0.6994 Remote Similarity NPD9706 Clinical (unspecified phase)
0.698 Remote Similarity NPD5413 Phase 2
0.6978 Remote Similarity NPD3799 Suspended
0.6973 Remote Similarity NPD1570 Approved
0.697 Remote Similarity NPD3930 Clinical (unspecified phase)
0.6968 Remote Similarity NPD3002 Clinical (unspecified phase)
0.6965 Remote Similarity NPD3976 Clinical (unspecified phase)
0.6963 Remote Similarity NPD6605 Phase 3
0.6954 Remote Similarity NPD5425 Phase 1
0.6952 Remote Similarity NPD1900 Clinical (unspecified phase)
0.6952 Remote Similarity NPD4925 Approved
0.6952 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3813 Approved
0.6938 Remote Similarity NPD2714 Clinical (unspecified phase)
0.6935 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6927 Remote Similarity NPD537 Phase 2
0.6927 Remote Similarity NPD534 Phase 2
0.6919 Remote Similarity NPD4995 Approved
0.6919 Remote Similarity NPD4996 Approved
0.6919 Remote Similarity NPD6403 Clinical (unspecified phase)
0.6916 Remote Similarity NPD5804 Clinical (unspecified phase)
0.6911 Remote Similarity NPD9689 Approved
0.6893 Remote Similarity NPD5255 Approved
0.6891 Remote Similarity NPD7935 Phase 2
0.6889 Remote Similarity NPD6794 Approved
0.6887 Remote Similarity NPD1572 Phase 2
0.6884 Remote Similarity NPD796 Phase 2
0.6882 Remote Similarity NPD4204 Approved
0.6882 Remote Similarity NPD4203 Approved
0.6881 Remote Similarity NPD3330 Phase 1
0.6878 Remote Similarity NPD2383 Phase 1
0.6872 Remote Similarity NPD2805 Phase 2
0.6869 Remote Similarity NPD3500 Clinical (unspecified phase)
0.6869 Remote Similarity NPD1915 Phase 1
0.6868 Remote Similarity NPD1567 Clinical (unspecified phase)
0.6866 Remote Similarity NPD5873 Phase 3
0.6866 Remote Similarity NPD6490 Phase 2
0.6866 Remote Similarity NPD8321 Discontinued
0.6866 Remote Similarity NPD5874 Phase 3
0.6866 Remote Similarity NPD5833 Phase 1
0.6863 Remote Similarity NPD6643 Discontinued
0.6862 Remote Similarity NPD2762 Phase 2
0.6859 Remote Similarity NPD1235 Phase 3
0.6854 Remote Similarity NPD4306 Phase 1
0.6848 Remote Similarity NPD5100 Phase 3
0.6835 Remote Similarity NPD7068 Approved
0.6835 Remote Similarity NPD7067 Approved
0.6833 Remote Similarity NPD3889 Approved
0.6832 Remote Similarity NPD949 Phase 1
0.683 Remote Similarity NPD6458 Discontinued
0.6825 Remote Similarity NPD2591 Phase 2
0.6825 Remote Similarity NPD1571 Phase 2
0.6823 Remote Similarity NPD3404 Approved
0.6821 Remote Similarity NPD4703 Approved
0.6821 Remote Similarity NPD4702 Approved
0.6812 Remote Similarity NPD6856 Discontinued
0.681 Remote Similarity NPD7051 Phase 3
0.681 Remote Similarity NPD7050 Clinical (unspecified phase)
0.6806 Remote Similarity NPD6750 Phase 2
0.6804 Remote Similarity NPD3962 Phase 2
0.6804 Remote Similarity NPD3959 Phase 2
0.6796 Remote Similarity NPD4213 Clinical (unspecified phase)
0.6794 Remote Similarity NPD5045 Phase 2
0.6794 Remote Similarity NPD983 Clinical (unspecified phase)
0.6793 Remote Similarity NPD2829 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5176 Approved
0.6788 Remote Similarity NPD1173 Approved
0.6788 Remote Similarity NPD38 Approved
0.6786 Remote Similarity NPD5828 Phase 2
0.6779 Remote Similarity NPD6589 Phase 1
0.6777 Remote Similarity NPD6327 Phase 1
0.6777 Remote Similarity NPD6326 Phase 2
0.6772 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6766 Remote Similarity NPD4612 Discontinued
0.6758 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6758 Remote Similarity NPD2781 Approved
0.6757 Remote Similarity NPD2751 Phase 1
0.6753 Remote Similarity NPD3810 Clinical (unspecified phase)
0.6748 Remote Similarity NPD9080 Approved
0.6748 Remote Similarity NPD9284 Approved
0.6744 Remote Similarity NPD1988 Phase 1
0.6743 Remote Similarity NPD3872 Phase 3
0.6742 Remote Similarity NPD5876 Phase 3
0.6742 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6742 Remote Similarity NPD5877 Phase 3
0.6742 Remote Similarity NPD4671 Clinical (unspecified phase)
0.674 Remote Similarity NPD2782 Approved
0.674 Remote Similarity NPD2780 Approved
0.6739 Remote Similarity NPD5996 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6721 Phase 1
0.6736 Remote Similarity NPD3406 Suspended
0.6736 Remote Similarity NPD994 Phase 2
0.6736 Remote Similarity NPD996 Phase 2
0.6733 Remote Similarity NPD6545 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7409 Clinical (unspecified phase)
0.6724 Remote Similarity NPD1661 Suspended
0.6716 Remote Similarity NPD2794 Discontinued
0.6713 Remote Similarity NPD1259 Discontinued
0.6712 Remote Similarity NPD3886 Phase 1
0.6704 Remote Similarity NPD604 Clinical (unspecified phase)
0.6703 Remote Similarity NPD7006 Approved
0.6701 Remote Similarity NPD9687 Approved
0.6701 Remote Similarity NPD9688 Approved
0.6698 Remote Similarity NPD2349 Phase 3
0.6698 Remote Similarity NPD6165 Phase 2
0.6698 Remote Similarity NPD6164 Phase 2
0.6685 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6684 Remote Similarity NPD7948 Phase 1
0.6684 Remote Similarity NPD2952 Discontinued
0.6684 Remote Similarity NPD3409 Phase 1

  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