Structure

Physi-Chem Properties

Molecular Weight:  160.06
Volume:  164.709
LogP:  0.813
LogD:  0.947
LogS:  -2.083
# 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:  0.63
Synthetic Accessibility Score:  1.819
Fsp3:  0.111
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:  -4.634
MDCK Permeability:  2.5323872250737622e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.903
Plasma Protein Binding (PPB):  64.03870391845703%
Volume Distribution (VD):  0.905
Pgp-substrate:  22.68962860107422%

ADMET: Metabolism

CYP1A2-inhibitor:  0.891
CYP1A2-substrate:  0.966
CYP2C19-inhibitor:  0.173
CYP2C19-substrate:  0.119
CYP2C9-inhibitor:  0.041
CYP2C9-substrate:  0.146
CYP2D6-inhibitor:  0.083
CYP2D6-substrate:  0.16
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.43

ADMET: Excretion

Clearance (CL):  4.109
Half-life (T1/2):  0.75

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.731
Drug-inuced Liver Injury (DILI):  0.933
AMES Toxicity:  0.731
Rat Oral Acute Toxicity:  0.965
Maximum Recommended Daily Dose:  0.162
Skin Sensitization:  0.516
Carcinogencity:  0.866
Eye Corrosion:  0.038
Eye Irritation:  0.896
Respiratory Toxicity:  0.969

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

  Natural Product: NPC278874

Natural Product ID:  NPC278874
Common Name*:   2-Methyl-1H-Quinazolin-4-One
IUPAC Name:   2-methyl-1H-quinazolin-4-one
Synonyms:  
Standard InCHIKey:  FIEYHAAMDAPVCH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H8N2O/c1-6-10-8-5-3-2-4-7(8)9(12)11-6/h2-5H,1H3,(H,10,11,12)
SMILES:  Cc1nc2ccccc2c(n1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL395092
PubChem CID:   15674
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
NPO1520 Callyspongia pseudoreticulata Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[12828480]
NPO24252 Uvaria hamiltonii Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[14552774]
NPO33632 Bacillus cereus 041381 Species n.a. n.a. isolated from the Coastal mud Baimajin, Danzhou, Hainan province of China n.a. PMID[21612927]
NPO24252 Uvaria hamiltonii Species Annonaceae Eukaryota leaf and stem n.a. n.a. PMID[9584399]
NPO24252 Uvaria hamiltonii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28694 Sanguisorba tenuifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23819 Baccharis peruviana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1520 Callyspongia pseudoreticulata Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23277 Lobophora papenfussii Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24585 Ocotea macropoda Species Lauraceae 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 = 5600.0 nM PMID[495762]
NPT682 Cell Line SK-N-MC Homo sapiens IC50 > 6250.0 nM PMID[495763]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 79432.8 nM PMID[495764]
NPT2562 Individual Protein Poly [ADP-ribose] polymerase-1 Homo sapiens IC50 = 1210.0 nM PMID[495766]
NPT2562 Individual Protein Poly [ADP-ribose] polymerase-1 Homo sapiens Inhibition > 60.0 % PMID[495766]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT1635 Cell Line H9c2 Rattus norvegicus IC50 > 79000.0 nM PMID[495764]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 37068.07 nM PMID[495767]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[495767]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 8199.5 nM PMID[495764]
NPT5106 Individual Protein Phosphodiesterase 10A Homo sapiens Ki = 990000.0 nM PMID[495769]
NPT35 Others n.a. log K = 0.1515 n.a. PMID[495763]
NPT2 Others Unspecified Potency = 461.1 nM PMID[495764]
NPT20 Organism Candida albicans Candida albicans MIC = 15600.0 nM PMID[495765]
NPT2 Others Unspecified IC50 > 79000.0 nM PMID[495764]
NPT2 Others Unspecified IC50 = 5000.0 nM PMID[495768]

☑ 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 NPC278874 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
0.987 High Similarity NPC105758
0.987 High Similarity NPC476686
0.987 High Similarity NPC476688
0.9679 High Similarity NPC208060
0.9608 High Similarity NPC224632
0.9321 High Similarity NPC477891
0.9321 High Similarity NPC144114
0.9304 High Similarity NPC164664
0.8876 High Similarity NPC230805
0.8382 Intermediate Similarity NPC254762
0.8333 Intermediate Similarity NPC472289
0.8153 Intermediate Similarity NPC60553
0.75 Intermediate Similarity NPC26872
0.7458 Intermediate Similarity NPC288943
0.7416 Intermediate Similarity NPC283152
0.741 Intermediate Similarity NPC161292
0.7371 Intermediate Similarity NPC44161
0.7368 Intermediate Similarity NPC26850
0.7341 Intermediate Similarity NPC315214
0.7341 Intermediate Similarity NPC47298
0.7327 Intermediate Similarity NPC130570
0.7321 Intermediate Similarity NPC288445
0.7299 Intermediate Similarity NPC159319
0.7299 Intermediate Similarity NPC97367
0.7299 Intermediate Similarity NPC32028
0.7256 Intermediate Similarity NPC280853
0.7241 Intermediate Similarity NPC177404
0.7235 Intermediate Similarity NPC153769
0.7213 Intermediate Similarity NPC62069
0.7212 Intermediate Similarity NPC285016
0.7212 Intermediate Similarity NPC245657
0.7195 Intermediate Similarity NPC471596
0.7182 Intermediate Similarity NPC72980
0.7174 Intermediate Similarity NPC42591
0.7172 Intermediate Similarity NPC471603
0.7151 Intermediate Similarity NPC474409
0.715 Intermediate Similarity NPC62995
0.7135 Intermediate Similarity NPC473764
0.7135 Intermediate Similarity NPC314940
0.7111 Intermediate Similarity NPC303225
0.7097 Intermediate Similarity NPC66083
0.7083 Intermediate Similarity NPC471598
0.7056 Intermediate Similarity NPC471294
0.7056 Intermediate Similarity NPC259545
0.7044 Intermediate Similarity NPC48317
0.7039 Intermediate Similarity NPC126481
0.7029 Intermediate Similarity NPC84508
0.7006 Intermediate Similarity NPC118511
0.6973 Remote Similarity NPC212535
0.6957 Remote Similarity NPC478032
0.6952 Remote Similarity NPC314573
0.6952 Remote Similarity NPC194040
0.6949 Remote Similarity NPC471177
0.6949 Remote Similarity NPC59779
0.6949 Remote Similarity NPC124542
0.6935 Remote Similarity NPC190007
0.6927 Remote Similarity NPC242209
0.6923 Remote Similarity NPC2497
0.6914 Remote Similarity NPC141353
0.6902 Remote Similarity NPC232340
0.6902 Remote Similarity NPC88363
0.6898 Remote Similarity NPC94943
0.6897 Remote Similarity NPC36168
0.6893 Remote Similarity NPC25899
0.6886 Remote Similarity NPC471594
0.6872 Remote Similarity NPC471178
0.6839 Remote Similarity NPC148140
0.6818 Remote Similarity NPC477889
0.6816 Remote Similarity NPC473057
0.6813 Remote Similarity NPC252590
0.6798 Remote Similarity NPC131718
0.6798 Remote Similarity NPC322644
0.6795 Remote Similarity NPC81561
0.6791 Remote Similarity NPC133306
0.6787 Remote Similarity NPC472066
0.6787 Remote Similarity NPC472031
0.6787 Remote Similarity NPC472067
0.6774 Remote Similarity NPC168486
0.6774 Remote Similarity NPC222592
0.6768 Remote Similarity NPC476685
0.6768 Remote Similarity NPC476687
0.6768 Remote Similarity NPC476689
0.6763 Remote Similarity NPC114209
0.6762 Remote Similarity NPC103687
0.6762 Remote Similarity NPC132631
0.676 Remote Similarity NPC48192
0.6757 Remote Similarity NPC96890
0.6755 Remote Similarity NPC204717
0.6754 Remote Similarity NPC144381
0.6753 Remote Similarity NPC472193
0.6753 Remote Similarity NPC248627
0.6739 Remote Similarity NPC312872
0.6737 Remote Similarity NPC46580
0.6736 Remote Similarity NPC329541
0.6725 Remote Similarity NPC470403
0.6725 Remote Similarity NPC470404
0.6725 Remote Similarity NPC470394
0.6721 Remote Similarity NPC158129
0.672 Remote Similarity NPC314002
0.6718 Remote Similarity NPC474188
0.6715 Remote Similarity NPC250178
0.6704 Remote Similarity NPC120798
0.6702 Remote Similarity NPC220765
0.6687 Remote Similarity NPC184437
0.6684 Remote Similarity NPC171171
0.6684 Remote Similarity NPC324149
0.6667 Remote Similarity NPC184964
0.6667 Remote Similarity NPC320394
0.6667 Remote Similarity NPC79911
0.6667 Remote Similarity NPC120070
0.6667 Remote Similarity NPC243850
0.6667 Remote Similarity NPC215519
0.6649 Remote Similarity NPC79293
0.6649 Remote Similarity NPC317054
0.6649 Remote Similarity NPC230403
0.6649 Remote Similarity NPC279401
0.6647 Remote Similarity NPC470395
0.6646 Remote Similarity NPC54102
0.6646 Remote Similarity NPC226662
0.6646 Remote Similarity NPC162689
0.663 Remote Similarity NPC102423
0.6629 Remote Similarity NPC314440
0.6629 Remote Similarity NPC118135
0.6622 Remote Similarity NPC472068
0.6616 Remote Similarity NPC249040
0.6615 Remote Similarity NPC246700
0.6615 Remote Similarity NPC128751
0.6615 Remote Similarity NPC183805
0.6613 Remote Similarity NPC150048
0.6613 Remote Similarity NPC203754
0.6606 Remote Similarity NPC30540
0.6599 Remote Similarity NPC306376
0.6597 Remote Similarity NPC204385
0.6596 Remote Similarity NPC249662
0.6591 Remote Similarity NPC39092
0.6585 Remote Similarity NPC278451
0.658 Remote Similarity NPC106833
0.658 Remote Similarity NPC469497
0.6579 Remote Similarity NPC84478
0.6578 Remote Similarity NPC219848
0.6571 Remote Similarity NPC257142
0.6566 Remote Similarity NPC280714
0.6566 Remote Similarity NPC476167
0.6561 Remote Similarity NPC314394
0.6552 Remote Similarity NPC18348
0.6552 Remote Similarity NPC477111
0.6548 Remote Similarity NPC153042
0.6548 Remote Similarity NPC208751
0.6548 Remote Similarity NPC243834
0.6548 Remote Similarity NPC70956
0.6543 Remote Similarity NPC256268
0.6538 Remote Similarity NPC476118
0.6537 Remote Similarity NPC242923
0.6535 Remote Similarity NPC477113
0.6531 Remote Similarity NPC276517
0.6526 Remote Similarity NPC243058
0.6526 Remote Similarity NPC48938
0.6524 Remote Similarity NPC134586
0.6517 Remote Similarity NPC53144
0.6517 Remote Similarity NPC200836
0.6516 Remote Similarity NPC295452
0.6516 Remote Similarity NPC171393
0.6515 Remote Similarity NPC192315
0.6513 Remote Similarity NPC99666
0.6512 Remote Similarity NPC116622
0.651 Remote Similarity NPC61350
0.6505 Remote Similarity NPC313791
0.6503 Remote Similarity NPC122718
0.6494 Remote Similarity NPC242556
0.6492 Remote Similarity NPC203635
0.6492 Remote Similarity NPC285923
0.6489 Remote Similarity NPC211997
0.6488 Remote Similarity NPC309845
0.6486 Remote Similarity NPC477888
0.6485 Remote Similarity NPC475070
0.6485 Remote Similarity NPC212125
0.648 Remote Similarity NPC45850
0.6477 Remote Similarity NPC206186
0.6474 Remote Similarity NPC206201
0.6471 Remote Similarity NPC216159
0.6467 Remote Similarity NPC108469
0.6467 Remote Similarity NPC49217
0.6465 Remote Similarity NPC77555
0.6465 Remote Similarity NPC90229
0.6463 Remote Similarity NPC63109
0.6462 Remote Similarity NPC220851
0.6461 Remote Similarity NPC284348
0.6458 Remote Similarity NPC476341
0.6455 Remote Similarity NPC42979
0.6447 Remote Similarity NPC280638
0.6442 Remote Similarity NPC237740
0.6441 Remote Similarity NPC37548
0.644 Remote Similarity NPC176127
0.6436 Remote Similarity NPC476098
0.6436 Remote Similarity NPC224764
0.6436 Remote Similarity NPC223427
0.6429 Remote Similarity NPC256893
0.6429 Remote Similarity NPC141915
0.6429 Remote Similarity NPC280964
0.6429 Remote Similarity NPC114335

  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 NPC278874 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
0.8876 High Similarity NPD9714 Clinical (unspecified phase)
0.8696 High Similarity NPD444 Approved
0.8079 Intermediate Similarity NPD2410 Phase 2
0.7956 Intermediate Similarity NPD6594 Discontinued
0.7912 Intermediate Similarity NPD4673 Phase 2
0.7869 Intermediate Similarity NPD7419 Discontinued
0.7814 Intermediate Similarity NPD3261 Phase 1
0.7747 Intermediate Similarity NPD5428 Discontinued
0.7746 Intermediate Similarity NPD3224 Phase 2
0.7638 Intermediate Similarity NPD4403 Phase 3
0.7638 Intermediate Similarity NPD4401 Phase 2
0.7554 Intermediate Similarity NPD3403 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD1043 Phase 3
0.746 Intermediate Similarity NPD6307 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1954 Phase 1
0.744 Intermediate Similarity NPD2882 Phase 1
0.7421 Intermediate Similarity NPD6132 Phase 1
0.7407 Intermediate Similarity NPD852 Discontinued
0.7399 Intermediate Similarity NPD5925 Phase 1
0.7358 Intermediate Similarity NPD9187 Approved
0.7358 Intermediate Similarity NPD1197 Approved
0.7354 Intermediate Similarity NPD3814 Phase 1
0.7341 Intermediate Similarity NPD1685 Approved
0.7341 Intermediate Similarity NPD1684 Approved
0.7337 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD6158 Phase 2
0.7278 Intermediate Similarity NPD1503 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD3234 Phase 3
0.7277 Intermediate Similarity NPD3233 Phase 2
0.7267 Intermediate Similarity NPD639 Discontinued
0.7241 Intermediate Similarity NPD983 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD1838 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6159 Phase 2
0.7216 Intermediate Similarity NPD6403 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD5885 Approved
0.7174 Intermediate Similarity NPD2762 Phase 2
0.7172 Intermediate Similarity NPD2794 Discontinued
0.7171 Intermediate Similarity NPD1273 Discontinued
0.7159 Intermediate Similarity NPD926 Approved
0.7159 Intermediate Similarity NPD925 Approved
0.7143 Intermediate Similarity NPD5529 Phase 1
0.7143 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD6490 Phase 2
0.7135 Intermediate Similarity NPD2524 Discontinued
0.7128 Intermediate Similarity NPD1234 Discontinued
0.7128 Intermediate Similarity NPD4615 Phase 2
0.7119 Intermediate Similarity NPD1215 Discontinued
0.7112 Intermediate Similarity NPD3439 Approved
0.7105 Intermediate Similarity NPD7935 Phase 2
0.7074 Intermediate Similarity NPD6022 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD7112 Discontinued
0.7062 Intermediate Similarity NPD509 Phase 3
0.7053 Intermediate Similarity NPD6327 Phase 1
0.7053 Intermediate Similarity NPD1912 Approved
0.7053 Intermediate Similarity NPD6326 Phase 2
0.7044 Intermediate Similarity NPD4312 Approved
0.7043 Intermediate Similarity NPD2591 Phase 2
0.7037 Intermediate Similarity NPD6887 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD2127 Suspended
0.7022 Intermediate Similarity NPD4213 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD9690 Approved
0.7015 Intermediate Similarity NPD4358 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD2757 Phase 2
0.7011 Intermediate Similarity NPD4203 Approved
0.7011 Intermediate Similarity NPD4204 Approved
0.701 Intermediate Similarity NPD6145 Phase 1
0.7005 Intermediate Similarity NPD2383 Phase 1
0.6989 Remote Similarity NPD6074 Clinical (unspecified phase)
0.698 Remote Similarity NPD6957 Approved
0.698 Remote Similarity NPD6958 Approved
0.6974 Remote Similarity NPD3765 Approved
0.6971 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6971 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6971 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1313 Approved
0.6964 Remote Similarity NPD1592 Phase 3
0.6963 Remote Similarity NPD4998 Phase 3
0.6963 Remote Similarity NPD3810 Clinical (unspecified phase)
0.6963 Remote Similarity NPD4999 Phase 3
0.6961 Remote Similarity NPD1599 Approved
0.6961 Remote Similarity NPD5996 Clinical (unspecified phase)
0.6957 Remote Similarity NPD702 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7758 Approved
0.6952 Remote Similarity NPD7757 Approved
0.6946 Remote Similarity NPD7423 Phase 2
0.6942 Remote Similarity NPD4945 Discontinued
0.6935 Remote Similarity NPD7409 Clinical (unspecified phase)
0.6927 Remote Similarity NPD425 Approved
0.6927 Remote Similarity NPD424 Approved
0.691 Remote Similarity NPD404 Discontinued
0.69 Remote Similarity NPD3013 Phase 3
0.69 Remote Similarity NPD3014 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6711 Approved
0.6893 Remote Similarity NPD112 Approved
0.6893 Remote Similarity NPD9705 Discontinued
0.6891 Remote Similarity NPD3830 Phase 1
0.6884 Remote Similarity NPD5905 Phase 1
0.6878 Remote Similarity NPD6724 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6491 Clinical (unspecified phase)
0.6868 Remote Similarity NPD966 Clinical (unspecified phase)
0.6866 Remote Similarity NPD1468 Clinical (unspecified phase)
0.6865 Remote Similarity NPD2601 Approved
0.6865 Remote Similarity NPD2600 Approved
0.6865 Remote Similarity NPD2599 Approved
0.6862 Remote Similarity NPD706 Phase 1
0.6859 Remote Similarity NPD4950 Approved
0.6856 Remote Similarity NPD3084 Phase 3
0.6848 Remote Similarity NPD1272 Clinical (unspecified phase)
0.6847 Remote Similarity NPD7188 Phase 3
0.6845 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6845 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6839 Remote Similarity NPD3262 Approved
0.6837 Remote Similarity NPD6605 Phase 3
0.6837 Remote Similarity NPD4511 Phase 1
0.6833 Remote Similarity NPD6794 Approved
0.6832 Remote Similarity NPD3976 Clinical (unspecified phase)
0.6831 Remote Similarity NPD6492 Phase 2
0.6831 Remote Similarity NPD3799 Suspended
0.6828 Remote Similarity NPD1570 Approved
0.6825 Remote Similarity NPD1900 Clinical (unspecified phase)
0.6824 Remote Similarity NPD3525 Discontinued
0.6823 Remote Similarity NPD38 Approved
0.6823 Remote Similarity NPD9695 Approved
0.6823 Remote Similarity NPD5176 Approved
0.6816 Remote Similarity NPD4438 Approved
0.6813 Remote Similarity NPD2993 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1567 Clinical (unspecified phase)
0.6809 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6802 Remote Similarity NPD3931 Approved
0.6802 Remote Similarity NPD3928 Approved
0.6798 Remote Similarity NPD4457 Phase 2
0.6793 Remote Similarity NPD5943 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4995 Approved
0.6792 Remote Similarity NPD4996 Approved
0.6786 Remote Similarity NPD6458 Discontinued
0.6784 Remote Similarity NPD3932 Clinical (unspecified phase)
0.6778 Remote Similarity NPD3889 Approved
0.6772 Remote Similarity NPD6047 Phase 1
0.6772 Remote Similarity NPD3315 Phase 3
0.6769 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5413 Phase 2
0.6761 Remote Similarity NPD1572 Phase 2
0.6761 Remote Similarity NPD6285 Phase 2
0.6761 Remote Similarity NPD3960 Clinical (unspecified phase)
0.6751 Remote Similarity NPD6592 Clinical (unspecified phase)
0.675 Remote Similarity NPD3930 Clinical (unspecified phase)
0.6745 Remote Similarity NPD4925 Approved
0.6743 Remote Similarity NPD2128 Phase 1
0.6743 Remote Similarity NPD5873 Phase 3
0.6743 Remote Similarity NPD5874 Phase 3
0.6739 Remote Similarity NPD5065 Approved
0.6734 Remote Similarity NPD3500 Clinical (unspecified phase)
0.6734 Remote Similarity NPD5425 Phase 1
0.6729 Remote Similarity NPD4306 Phase 1
0.672 Remote Similarity NPD2814 Clinical (unspecified phase)
0.672 Remote Similarity NPD443 Clinical (unspecified phase)
0.6716 Remote Similarity NPD4612 Discontinued
0.6714 Remote Similarity NPD4932 Clinical (unspecified phase)
0.6713 Remote Similarity NPD5804 Clinical (unspecified phase)
0.6702 Remote Similarity NPD408 Approved
0.6702 Remote Similarity NPD2391 Clinical (unspecified phase)
0.6698 Remote Similarity NPD1571 Phase 2
0.6697 Remote Similarity NPD3872 Phase 3
0.6684 Remote Similarity NPD6469 Phase 3
0.6684 Remote Similarity NPD7722 Suspended
0.6684 Remote Similarity NPD6468 Clinical (unspecified phase)
0.6684 Remote Similarity NPD2917 Approved
0.6683 Remote Similarity NPD6545 Clinical (unspecified phase)
0.6682 Remote Similarity NPD6750 Phase 2
0.6667 Remote Similarity NPD1259 Discontinued
0.6667 Remote Similarity NPD1326 Approved
0.6667 Remote Similarity NPD3504 Approved
0.6667 Remote Similarity NPD3503 Approved
0.6667 Remote Similarity NPD5833 Phase 1
0.6667 Remote Similarity NPD1325 Approved
0.6667 Remote Similarity NPD5045 Phase 2
0.6667 Remote Similarity NPD6202 Discontinued
0.6651 Remote Similarity NPD6589 Phase 1
0.6651 Remote Similarity NPD7726 Phase 1
0.665 Remote Similarity NPD2176 Approved
0.665 Remote Similarity NPD5828 Phase 2
0.665 Remote Similarity NPD2175 Phase 3
0.665 Remote Similarity NPD6643 Discontinued
0.665 Remote Similarity NPD1915 Phase 1
0.665 Remote Similarity NPD2177 Approved
0.665 Remote Similarity NPD8321 Discontinued
0.6649 Remote Similarity NPD5153 Clinical (unspecified phase)
0.6649 Remote Similarity NPD7006 Approved
0.6649 Remote Similarity NPD3002 Clinical (unspecified phase)
0.6648 Remote Similarity NPD5255 Approved
0.6636 Remote Similarity NPD5139 Phase 1
0.6636 Remote Similarity NPD7067 Approved
0.6636 Remote Similarity NPD7068 Approved
0.6635 Remote Similarity NPD537 Phase 2
0.6635 Remote Similarity NPD534 Phase 2
0.6633 Remote Similarity NPD1842 Approved
0.6632 Remote Similarity NPD1235 Phase 3
0.6632 Remote Similarity NPD459 Clinical (unspecified phase)
0.6629 Remote Similarity NPD5546 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