Structure

Physi-Chem Properties

Molecular Weight:  172.1
Volume:  184.591
LogP:  1.501
LogD:  1.799
LogS:  -1.589
# Rotatable Bonds:  0
TPSA:  15.6
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.586
Synthetic Accessibility Score:  2.443
Fsp3:  0.364
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:  -4.583
MDCK Permeability:  2.9307035219972022e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.979
Plasma Protein Binding (PPB):  82.79859161376953%
Volume Distribution (VD):  1.671
Pgp-substrate:  24.636886596679688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.637
CYP1A2-substrate:  0.925
CYP2C19-inhibitor:  0.154
CYP2C19-substrate:  0.403
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.25
CYP2D6-inhibitor:  0.628
CYP2D6-substrate:  0.91
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.33

ADMET: Excretion

Clearance (CL):  6.957
Half-life (T1/2):  0.663

ADMET: Toxicity

hERG Blockers:  0.042
Human Hepatotoxicity (H-HT):  0.881
Drug-inuced Liver Injury (DILI):  0.251
AMES Toxicity:  0.074
Rat Oral Acute Toxicity:  0.57
Maximum Recommended Daily Dose:  0.299
Skin Sensitization:  0.808
Carcinogencity:  0.924
Eye Corrosion:  0.023
Eye Irritation:  0.575
Respiratory Toxicity:  0.943

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

  Natural Product: NPC164802

Natural Product ID:  NPC164802
Common Name*:   1,2,3,9-Tetrahydropyrrolo[2,1-B]Quinazoline
IUPAC Name:   1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline
Synonyms:  
Standard InCHIKey:  WUFQLZTXIWKION-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H12N2/c1-2-5-10-9(4-1)8-13-7-3-6-11(13)12-10/h1-2,4-5H,3,6-8H2
SMILES:  C1CC2=Nc3c(CN2C1)cccc3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL355821
PubChem CID:   442894
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
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. aerial part n.a. PMID[12033510]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. root n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota aerial parts purchased in Juhuacun herbal market, Kunming, Yunnan Province, China 2002-Oct PMID[16562826]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[18357994]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[21598983]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[22026410]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota Seeds n.a. n.a. PMID[28128938]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. PMID[28165740]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. PMID[6736972]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8377022]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota Pericarp n.a. n.a. PMID[9748380]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3578 Andrographis paniculata Species Acanthaceae 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
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 18000.0 nM PMID[560073]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 3720.0 nM PMID[560073]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[560074]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[560074]

☑ 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 NPC164802 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
0.8696 High Similarity NPC328683
0.8696 High Similarity NPC283130
0.8482 Intermediate Similarity NPC288232
0.8264 Intermediate Similarity NPC226662
0.813 Intermediate Similarity NPC207428
0.7826 Intermediate Similarity NPC296163
0.7672 Intermediate Similarity NPC314141
0.7672 Intermediate Similarity NPC187036
0.7563 Intermediate Similarity NPC192209
0.7417 Intermediate Similarity NPC313449
0.7385 Intermediate Similarity NPC300299
0.7358 Intermediate Similarity NPC78154
0.7355 Intermediate Similarity NPC264580
0.7353 Intermediate Similarity NPC324445
0.7321 Intermediate Similarity NPC291610
0.7244 Intermediate Similarity NPC476950
0.7164 Intermediate Similarity NPC207554
0.709 Intermediate Similarity NPC125746
0.7 Intermediate Similarity NPC7067
0.7 Intermediate Similarity NPC469330
0.6949 Remote Similarity NPC302790
0.6916 Remote Similarity NPC262295
0.6897 Remote Similarity NPC469974
0.6894 Remote Similarity NPC22079
0.687 Remote Similarity NPC9856
0.6861 Remote Similarity NPC2823
0.6847 Remote Similarity NPC322040
0.6846 Remote Similarity NPC478079
0.6838 Remote Similarity NPC83214
0.6814 Remote Similarity NPC472258
0.681 Remote Similarity NPC178681
0.6786 Remote Similarity NPC108339
0.6774 Remote Similarity NPC313673
0.6772 Remote Similarity NPC475915
0.6748 Remote Similarity NPC205652
0.6739 Remote Similarity NPC471574
0.6733 Remote Similarity NPC98976
0.6719 Remote Similarity NPC48564
0.6719 Remote Similarity NPC265605
0.6719 Remote Similarity NPC182570
0.6697 Remote Similarity NPC111233
0.6691 Remote Similarity NPC198988
0.669 Remote Similarity NPC143872
0.6667 Remote Similarity NPC184437
0.6667 Remote Similarity NPC474430
0.6667 Remote Similarity NPC271642
0.6642 Remote Similarity NPC476685
0.6642 Remote Similarity NPC122553
0.6642 Remote Similarity NPC476687
0.6642 Remote Similarity NPC476689
0.662 Remote Similarity NPC204141
0.6607 Remote Similarity NPC108800
0.6599 Remote Similarity NPC84317
0.6596 Remote Similarity NPC20144
0.6596 Remote Similarity NPC136002
0.6593 Remote Similarity NPC101165
0.6591 Remote Similarity NPC145754
0.6587 Remote Similarity NPC148140
0.6579 Remote Similarity NPC471320
0.6579 Remote Similarity NPC471319
0.6577 Remote Similarity NPC191444
0.6577 Remote Similarity NPC476160
0.6575 Remote Similarity NPC295021
0.6571 Remote Similarity NPC59084
0.6571 Remote Similarity NPC238499
0.6542 Remote Similarity NPC15839
0.6542 Remote Similarity NPC104070
0.6538 Remote Similarity NPC41174
0.6535 Remote Similarity NPC81561
0.6525 Remote Similarity NPC63157
0.6525 Remote Similarity NPC473868
0.6522 Remote Similarity NPC325252
0.651 Remote Similarity NPC154478
0.6509 Remote Similarity NPC307456
0.6503 Remote Similarity NPC469735
0.65 Remote Similarity NPC110126
0.65 Remote Similarity NPC104483
0.65 Remote Similarity NPC88097
0.6489 Remote Similarity NPC46358
0.6486 Remote Similarity NPC176858
0.6484 Remote Similarity NPC177684
0.6484 Remote Similarity NPC291962
0.6484 Remote Similarity NPC162689
0.6484 Remote Similarity NPC54102
0.648 Remote Similarity NPC470550
0.6475 Remote Similarity NPC150259
0.6475 Remote Similarity NPC105127
0.6466 Remote Similarity NPC250361
0.6463 Remote Similarity NPC232798
0.6463 Remote Similarity NPC471132
0.6458 Remote Similarity NPC469740
0.6454 Remote Similarity NPC2949
0.6446 Remote Similarity NPC79618
0.6439 Remote Similarity NPC27740
0.6434 Remote Similarity NPC161956
0.6434 Remote Similarity NPC317564
0.6434 Remote Similarity NPC112373
0.6434 Remote Similarity NPC258531
0.6429 Remote Similarity NPC243162
0.6403 Remote Similarity NPC218268
0.6403 Remote Similarity NPC96102
0.6396 Remote Similarity NPC30445
0.6385 Remote Similarity NPC215519
0.6385 Remote Similarity NPC257490
0.6383 Remote Similarity NPC73767
0.6381 Remote Similarity NPC12857
0.6378 Remote Similarity NPC147957
0.637 Remote Similarity NPC473762
0.6357 Remote Similarity NPC84911
0.6355 Remote Similarity NPC231986
0.635 Remote Similarity NPC82295
0.6339 Remote Similarity NPC173991
0.6338 Remote Similarity NPC115611
0.6333 Remote Similarity NPC275467
0.633 Remote Similarity NPC169016
0.6328 Remote Similarity NPC476566
0.6325 Remote Similarity NPC317642
0.6324 Remote Similarity NPC473587
0.6316 Remote Similarity NPC88970
0.6312 Remote Similarity NPC130251
0.6311 Remote Similarity NPC299134
0.6311 Remote Similarity NPC66775
0.6301 Remote Similarity NPC21605
0.6294 Remote Similarity NPC277157
0.6286 Remote Similarity NPC261195
0.6286 Remote Similarity NPC29886
0.6284 Remote Similarity NPC117032
0.6277 Remote Similarity NPC53044
0.6277 Remote Similarity NPC475428
0.6276 Remote Similarity NPC470440
0.6273 Remote Similarity NPC229477
0.6269 Remote Similarity NPC252794
0.6268 Remote Similarity NPC22082
0.6268 Remote Similarity NPC186284
0.6268 Remote Similarity NPC301760
0.6261 Remote Similarity NPC476483
0.626 Remote Similarity NPC77294
0.625 Remote Similarity NPC122141
0.625 Remote Similarity NPC187231
0.6242 Remote Similarity NPC281094
0.6241 Remote Similarity NPC314102
0.6241 Remote Similarity NPC251722
0.6239 Remote Similarity NPC134825
0.6234 Remote Similarity NPC471130
0.6232 Remote Similarity NPC475450
0.6232 Remote Similarity NPC179365
0.6231 Remote Similarity NPC91958
0.6228 Remote Similarity NPC470926
0.6228 Remote Similarity NPC226438
0.6224 Remote Similarity NPC469767
0.6224 Remote Similarity NPC469761
0.6224 Remote Similarity NPC469779
0.6224 Remote Similarity NPC469784
0.6224 Remote Similarity NPC469768
0.6224 Remote Similarity NPC469780
0.6224 Remote Similarity NPC279081
0.6224 Remote Similarity NPC469783
0.6216 Remote Similarity NPC206592
0.6216 Remote Similarity NPC148592
0.6216 Remote Similarity NPC258046
0.6216 Remote Similarity NPC40070
0.6214 Remote Similarity NPC325599
0.6214 Remote Similarity NPC471123
0.6209 Remote Similarity NPC225018
0.62 Remote Similarity NPC476219
0.62 Remote Similarity NPC476297
0.6194 Remote Similarity NPC122718
0.619 Remote Similarity NPC321617
0.619 Remote Similarity NPC114209
0.6187 Remote Similarity NPC316104
0.6187 Remote Similarity NPC313352
0.6187 Remote Similarity NPC162417
0.6187 Remote Similarity NPC473930
0.6181 Remote Similarity NPC469766
0.6179 Remote Similarity NPC434
0.6179 Remote Similarity NPC37584
0.6164 Remote Similarity NPC285731
0.6159 Remote Similarity NPC51054
0.6159 Remote Similarity NPC282398
0.6154 Remote Similarity NPC240136
0.6154 Remote Similarity NPC471402
0.6154 Remote Similarity NPC471164
0.6154 Remote Similarity NPC297486
0.6149 Remote Similarity NPC37548
0.6148 Remote Similarity NPC250476
0.6148 Remote Similarity NPC146373
0.6148 Remote Similarity NPC245244
0.6148 Remote Similarity NPC166424
0.6144 Remote Similarity NPC68650
0.6144 Remote Similarity NPC470204
0.6138 Remote Similarity NPC190296
0.6135 Remote Similarity NPC21429
0.6134 Remote Similarity NPC323726
0.6129 Remote Similarity NPC17751
0.6129 Remote Similarity NPC280864
0.6127 Remote Similarity NPC469560
0.6122 Remote Similarity NPC478186
0.6122 Remote Similarity NPC288838
0.6122 Remote Similarity NPC63545
0.6118 Remote Similarity NPC104345

  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 NPC164802 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
1.0 High Similarity NPD477 Phase 1
0.8696 High Similarity NPD478 Approved
0.7966 Intermediate Similarity NPD2340 Discontinued
0.7934 Intermediate Similarity NPD986 Discontinued
0.7931 Intermediate Similarity NPD2467 Approved
0.7931 Intermediate Similarity NPD2464 Approved
0.7931 Intermediate Similarity NPD2463 Approved
0.7818 Intermediate Similarity NPD1728 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD3622 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD3623 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD4985 Clinical (unspecified phase)
0.7563 Intermediate Similarity NPD153 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2143 Discontinued
0.748 Intermediate Similarity NPD1001 Discontinued
0.7417 Intermediate Similarity NPD7481 Approved
0.7417 Intermediate Similarity NPD7480 Approved
0.7368 Intermediate Similarity NPD993 Approved
0.7368 Intermediate Similarity NPD3545 Approved
0.7368 Intermediate Similarity NPD3546 Approved
0.7368 Intermediate Similarity NPD990 Approved
0.7333 Intermediate Similarity NPD6660 Discontinued
0.7333 Intermediate Similarity NPD4047 Discontinued
0.7328 Intermediate Similarity NPD1107 Approved
0.7328 Intermediate Similarity NPD1539 Approved
0.7328 Intermediate Similarity NPD1108 Approved
0.7321 Intermediate Similarity NPD1417 Approved
0.7321 Intermediate Similarity NPD1419 Approved
0.7311 Intermediate Similarity NPD1813 Discontinued
0.7304 Intermediate Similarity NPD4115 Approved
0.7304 Intermediate Similarity NPD4114 Approved
0.7257 Intermediate Similarity NPD2244 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2622 Approved
0.7241 Intermediate Similarity NPD2679 Approved
0.7241 Intermediate Similarity NPD2678 Approved
0.7241 Intermediate Similarity NPD1721 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1524 Phase 1
0.7213 Intermediate Similarity NPD1216 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4116 Approved
0.7167 Intermediate Similarity NPD5631 Phase 3
0.7165 Intermediate Similarity NPD1949 Approved
0.7165 Intermediate Similarity NPD1950 Approved
0.7155 Intermediate Similarity NPD5253 Approved
0.7155 Intermediate Similarity NPD6300 Approved
0.7155 Intermediate Similarity NPD6299 Approved
0.7154 Intermediate Similarity NPD1919 Approved
0.7154 Intermediate Similarity NPD1920 Approved
0.7143 Intermediate Similarity NPD1764 Approved
0.7143 Intermediate Similarity NPD1762 Approved
0.7132 Intermediate Similarity NPD3424 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD3629 Approved
0.7101 Intermediate Similarity NPD3630 Approved
0.7083 Intermediate Similarity NPD2658 Approved
0.7083 Intermediate Similarity NPD3149 Approved
0.7083 Intermediate Similarity NPD3147 Approved
0.7083 Intermediate Similarity NPD2659 Approved
0.7083 Intermediate Similarity NPD3150 Approved
0.7083 Intermediate Similarity NPD3148 Approved
0.7077 Intermediate Similarity NPD4867 Approved
0.7077 Intermediate Similarity NPD3841 Phase 3
0.7077 Intermediate Similarity NPD4866 Approved
0.7068 Intermediate Similarity NPD406 Approved
0.7068 Intermediate Similarity NPD407 Approved
0.7059 Intermediate Similarity NPD2039 Approved
0.7059 Intermediate Similarity NPD3001 Approved
0.7059 Intermediate Similarity NPD2038 Approved
0.7059 Intermediate Similarity NPD2999 Approved
0.7049 Intermediate Similarity NPD1344 Phase 2
0.7031 Intermediate Similarity NPD6900 Discontinued
0.7031 Intermediate Similarity NPD2840 Approved
0.7016 Intermediate Similarity NPD2210 Approved
0.7016 Intermediate Similarity NPD2212 Approved
0.7016 Intermediate Similarity NPD1479 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD2243 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD199 Approved
0.7 Intermediate Similarity NPD197 Approved
0.6947 Remote Similarity NPD3654 Approved
0.6944 Remote Similarity NPD297 Approved
0.6944 Remote Similarity NPD9 Approved
0.6923 Remote Similarity NPD1064 Approved
0.6923 Remote Similarity NPD1065 Approved
0.6897 Remote Similarity NPD489 Approved
0.6897 Remote Similarity NPD488 Approved
0.6891 Remote Similarity NPD3548 Approved
0.6891 Remote Similarity NPD7633 Discontinued
0.6866 Remote Similarity NPD3385 Approved
0.6847 Remote Similarity NPD463 Approved
0.6847 Remote Similarity NPD8 Approved
0.6847 Remote Similarity NPD243 Approved
0.6847 Remote Similarity NPD462 Approved
0.6847 Remote Similarity NPD464 Approved
0.6838 Remote Similarity NPD563 Approved
0.6838 Remote Similarity NPD564 Approved
0.681 Remote Similarity NPD1396 Approved
0.6803 Remote Similarity NPD2914 Approved
0.6803 Remote Similarity NPD2913 Approved
0.68 Remote Similarity NPD18 Approved
0.6794 Remote Similarity NPD7582 Discontinued
0.6786 Remote Similarity NPD665 Phase 2
0.6783 Remote Similarity NPD6575 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6069 Approved
0.6774 Remote Similarity NPD6070 Approved
0.6765 Remote Similarity NPD603 Approved
0.6761 Remote Similarity NPD4939 Clinical (unspecified phase)
0.6746 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6724 Remote Similarity NPD4734 Approved
0.6724 Remote Similarity NPD4735 Approved
0.6719 Remote Similarity NPD270 Clinical (unspecified phase)
0.6719 Remote Similarity NPD2131 Approved
0.6719 Remote Similarity NPD268 Approved
0.6719 Remote Similarity NPD271 Approved
0.6715 Remote Similarity NPD544 Clinical (unspecified phase)
0.6714 Remote Similarity NPD2866 Approved
0.6694 Remote Similarity NPD1720 Phase 2
0.6694 Remote Similarity NPD1723 Phase 2
0.6693 Remote Similarity NPD6892 Discontinued
0.6692 Remote Similarity NPD4857 Phase 1
0.6692 Remote Similarity NPD1937 Approved
0.6667 Remote Similarity NPD1903 Approved
0.6667 Remote Similarity NPD1598 Discontinued
0.6667 Remote Similarity NPD5179 Approved
0.6667 Remote Similarity NPD23 Approved
0.6667 Remote Similarity NPD5181 Approved
0.6667 Remote Similarity NPD5657 Phase 3
0.6667 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5180 Approved
0.6643 Remote Similarity NPD6301 Phase 2
0.6643 Remote Similarity NPD2129 Approved
0.6641 Remote Similarity NPD678 Discontinued
0.6636 Remote Similarity NPD9348 Approved
0.6636 Remote Similarity NPD9350 Approved
0.6636 Remote Similarity NPD2539 Approved
0.6636 Remote Similarity NPD9349 Approved
0.6636 Remote Similarity NPD9351 Phase 3
0.6636 Remote Similarity NPD2538 Approved
0.6635 Remote Similarity NPD507 Approved
0.6635 Remote Similarity NPD508 Approved
0.6619 Remote Similarity NPD1902 Approved
0.6619 Remote Similarity NPD1904 Approved
0.6614 Remote Similarity NPD3499 Approved
0.6614 Remote Similarity NPD3498 Approved
0.6613 Remote Similarity NPD5629 Discontinued
0.661 Remote Similarity NPD1028 Approved
0.661 Remote Similarity NPD1026 Approved
0.6599 Remote Similarity NPD2150 Discontinued
0.6597 Remote Similarity NPD5546 Clinical (unspecified phase)
0.6593 Remote Similarity NPD1316 Discontinued
0.6581 Remote Similarity NPD708 Approved
0.6581 Remote Similarity NPD707 Approved
0.6574 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6571 Remote Similarity NPD5371 Approved
0.6571 Remote Similarity NPD5372 Approved
0.6565 Remote Similarity NPD3080 Clinical (unspecified phase)
0.656 Remote Similarity NPD224 Phase 2
0.6555 Remote Similarity NPD414 Discontinued
0.6555 Remote Similarity NPD1269 Approved
0.6555 Remote Similarity NPD1268 Approved
0.6549 Remote Similarity NPD4711 Clinical (unspecified phase)
0.6533 Remote Similarity NPD5551 Clinical (unspecified phase)
0.6532 Remote Similarity NPD1377 Approved
0.6532 Remote Similarity NPD6562 Approved
0.6532 Remote Similarity NPD6561 Approved
0.6532 Remote Similarity NPD1378 Approved
0.6528 Remote Similarity NPD979 Approved
0.6519 Remote Similarity NPD1186 Clinical (unspecified phase)
0.6519 Remote Similarity NPD3476 Approved
0.6519 Remote Similarity NPD3475 Approved
0.6515 Remote Similarity NPD3240 Phase 2
0.6493 Remote Similarity NPD4019 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4595 Approved
0.6481 Remote Similarity NPD5178 Approved
0.6479 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6475 Remote Similarity NPD45 Approved
0.6475 Remote Similarity NPD6554 Approved
0.6475 Remote Similarity NPD1262 Discovery
0.6471 Remote Similarity NPD3137 Clinical (unspecified phase)
0.6467 Remote Similarity NPD5989 Phase 1
0.6462 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6454 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6449 Remote Similarity NPD1515 Discontinued
0.6449 Remote Similarity NPD2142 Approved
0.6449 Remote Similarity NPD2140 Approved
0.6449 Remote Similarity NPD2141 Approved
0.6444 Remote Similarity NPD4300 Clinical (unspecified phase)
0.6434 Remote Similarity NPD1525 Approved
0.6434 Remote Similarity NPD6017 Discontinued
0.6423 Remote Similarity NPD7200 Approved
0.6419 Remote Similarity NPD6285 Phase 2
0.6419 Remote Similarity NPD7072 Phase 2
0.6414 Remote Similarity NPD4942 Approved
0.6412 Remote Similarity NPD7461 Approved
0.6403 Remote Similarity NPD198 Clinical (unspecified phase)
0.64 Remote Similarity NPD456 Approved
0.64 Remote Similarity NPD452 Phase 1
0.64 Remote Similarity NPD1656 Phase 2
0.64 Remote Similarity NPD453 Phase 1
0.6389 Remote Similarity NPD2529 Approved
0.6389 Remote Similarity NPD5839 Clinical (unspecified phase)
0.6387 Remote Similarity NPD154 Discontinued
0.6383 Remote Similarity NPD2093 Discontinued
0.6372 Remote Similarity NPD3000 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