Structure

Physi-Chem Properties

Molecular Weight:  202.07
Volume:  199.535
LogP:  0.524
LogD:  0.594
LogS:  -1.644
# Rotatable Bonds:  0
TPSA:  55.12
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.688
Synthetic Accessibility Score:  2.687
Fsp3:  0.273
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.7
MDCK Permeability:  1.5599252947140485e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.036
Human Intestinal Absorption (HIA):  0.07
20% Bioavailability (F20%):  0.928
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.953
Plasma Protein Binding (PPB):  59.81969451904297%
Volume Distribution (VD):  1.135
Pgp-substrate:  40.68177795410156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.549
CYP1A2-substrate:  0.629
CYP2C19-inhibitor:  0.089
CYP2C19-substrate:  0.706
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.233
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.525
CYP3A4-inhibitor:  0.014
CYP3A4-substrate:  0.528

ADMET: Excretion

Clearance (CL):  5.072
Half-life (T1/2):  0.345

ADMET: Toxicity

hERG Blockers:  0.053
Human Hepatotoxicity (H-HT):  0.133
Drug-inuced Liver Injury (DILI):  0.174
AMES Toxicity:  0.085
Rat Oral Acute Toxicity:  0.054
Maximum Recommended Daily Dose:  0.45
Skin Sensitization:  0.317
Carcinogencity:  0.949
Eye Corrosion:  0.004
Eye Irritation:  0.68
Respiratory Toxicity:  0.729

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

  Natural Product: NPC324445

Natural Product ID:  NPC324445
Common Name*:   3-Hydroxy-2,3-Dihydro-1H-Pyrrolo[2,1-B]Quinazolin-9-One
IUPAC Name:   3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
Synonyms:  
Standard InCHIKey:  SDIVYZXRQHWCKF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2
SMILES:  C1CN2C(=NC3=CC=CC=C3C2=O)C1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1864065
PubChem CID:   10242
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
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota Seeds n.a. n.a. PMID[28128938]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. PMID[6736972]
NPO31531 Adhatoda vasica n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31531 Adhatoda vasica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1085 Peganum harmala Species Nitrariaceae 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
NPT65 Cell Line HepG2 Homo sapiens INHIBITION = 7.68 % PMID[485644]
NPT3565 Individual Protein Lysine--tRNA ligase Plasmodium falciparum (isolate 3D7) Percent Effect = 5.908 % PMID[485642]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[485640]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[485640]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 8275.3 nM PMID[485640]
NPT2 Others Unspecified Inhibition = -12.85 % PMID[485641]
NPT21962 SINGLE PROTEIN Methionyl-tRNA synthetase, putative Leishmania donovani (strain BPK282A1) Inhibition = 10.44 % PMID[485642]
NPT2 Others Unspecified IC50 = 25320.0 nM PMID[485643]
NPT2 Others Unspecified IC50 = 19200.0 nM PMID[485643]
NPT474 Organism Plasmodium berghei Plasmodium berghei INHIBITION = -17.93 % PMID[485644]
NPT474 Organism Plasmodium berghei Plasmodium berghei INHIBITION = -40.5 % PMID[485644]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum INHIBITION = 1.17 % PMID[485644]
NPT21966 SINGLE PROTEIN Polyketide synthase Pks13 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Percent Effect = -27.2 % PMID[485642]
NPT21963 SINGLE PROTEIN Coenzyme A biosynthesis bifunctional protein CoaBC Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Percent Effect = 24.15 % PMID[485642]
NPT2 Others Unspecified Percent Effect = 4.576 % PMID[485642]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Percent Effect = -10.06 % PMID[485642]
NPT21964 SINGLE PROTEIN Histidine--tRNA ligase Trypanosoma cruzi (strain CL Brener) Percent Effect = -0.9901 % PMID[485642]
NPT2 Others Unspecified Percent Effect = 15.06 % PMID[485642]
NPT2 Others Unspecified Percent Effect = -5.235 % PMID[485642]
NPT2 Others Unspecified Percent Effect = 12.79 % PMID[485642]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei Percent Effect = -6.633 % PMID[485642]
NPT633 Organism Leishmania donovani Leishmania donovani Percent Effect = 18.2 % PMID[485642]
NPT21965 SINGLE PROTEIN Tryptophan--tRNA ligase Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Percent Effect = 3.84 % PMID[485642]
NPT21967 PROTEIN COMPLEX ClpP1P2 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Percent Effect = -6.219 % PMID[485642]
NPT21970 ORGANISM Wolbachia pipientis Wolbachia pipientis Percent Effect = 1.424 % PMID[485642]
NPT21963 SINGLE PROTEIN Coenzyme A biosynthesis bifunctional protein CoaBC Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Percent Effect = 15.87 % PMID[485642]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Percent Effect = -64.78 % PMID[485642]
NPT21968 SINGLE PROTEIN Histidine--tRNA ligase Leishmania infantum Percent Effect = 25.0 % PMID[485642]
NPT21963 SINGLE PROTEIN Coenzyme A biosynthesis bifunctional protein CoaBC Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) IC50 > 30199.52 nM PMID[485642]

☑ 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 NPC324445 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
0.9044 High Similarity NPC207428
0.8456 Intermediate Similarity NPC283130
0.8456 Intermediate Similarity NPC328683
0.8333 Intermediate Similarity NPC122553
0.8312 Intermediate Similarity NPC154478
0.8219 Intermediate Similarity NPC207554
0.8182 Intermediate Similarity NPC84317
0.8069 Intermediate Similarity NPC300299
0.8038 Intermediate Similarity NPC113056
0.8038 Intermediate Similarity NPC138293
0.7697 Intermediate Similarity NPC475594
0.7667 Intermediate Similarity NPC83214
0.7651 Intermediate Similarity NPC475607
0.764 Intermediate Similarity NPC88970
0.7605 Intermediate Similarity NPC474081
0.7595 Intermediate Similarity NPC295021
0.7566 Intermediate Similarity NPC2823
0.756 Intermediate Similarity NPC474041
0.756 Intermediate Similarity NPC475761
0.7546 Intermediate Similarity NPC471130
0.7483 Intermediate Similarity NPC226662
0.7471 Intermediate Similarity NPC471196
0.7471 Intermediate Similarity NPC471195
0.7356 Intermediate Similarity NPC473815
0.7353 Intermediate Similarity NPC164802
0.7338 Intermediate Similarity NPC471164
0.7338 Intermediate Similarity NPC471574
0.7262 Intermediate Similarity NPC355
0.7209 Intermediate Similarity NPC475685
0.7205 Intermediate Similarity NPC117032
0.7197 Intermediate Similarity NPC136002
0.7171 Intermediate Similarity NPC162417
0.7171 Intermediate Similarity NPC316104
0.7153 Intermediate Similarity NPC177684
0.7153 Intermediate Similarity NPC291962
0.7127 Intermediate Similarity NPC471199
0.7103 Intermediate Similarity NPC258531
0.7103 Intermediate Similarity NPC112373
0.7103 Intermediate Similarity NPC161956
0.7081 Intermediate Similarity NPC295548
0.7075 Intermediate Similarity NPC474082
0.7075 Intermediate Similarity NPC175726
0.7059 Intermediate Similarity NPC470786
0.7055 Intermediate Similarity NPC257490
0.7049 Intermediate Similarity NPC106118
0.7022 Intermediate Similarity NPC18890
0.7006 Intermediate Similarity NPC150308
0.7005 Intermediate Similarity NPC225400
0.6989 Remote Similarity NPC21429
0.6978 Remote Similarity NPC472540
0.6978 Remote Similarity NPC472539
0.6978 Remote Similarity NPC470787
0.6968 Remote Similarity NPC472538
0.6968 Remote Similarity NPC471155
0.6964 Remote Similarity NPC189116
0.6959 Remote Similarity NPC254698
0.6954 Remote Similarity NPC475094
0.6944 Remote Similarity NPC92803
0.694 Remote Similarity NPC472542
0.694 Remote Similarity NPC472541
0.6933 Remote Similarity NPC322433
0.6931 Remote Similarity NPC270241
0.6928 Remote Similarity NPC40364
0.6923 Remote Similarity NPC198401
0.6918 Remote Similarity NPC314287
0.6899 Remote Similarity NPC470301
0.6892 Remote Similarity NPC39818
0.6879 Remote Similarity NPC470548
0.6863 Remote Similarity NPC316746
0.6856 Remote Similarity NPC471192
0.6848 Remote Similarity NPC471132
0.6826 Remote Similarity NPC104345
0.6825 Remote Similarity NPC471191
0.6821 Remote Similarity NPC244425
0.6821 Remote Similarity NPC15384
0.6818 Remote Similarity NPC88110
0.6805 Remote Similarity NPC472117
0.6797 Remote Similarity NPC194562
0.6797 Remote Similarity NPC187231
0.6792 Remote Similarity NPC316202
0.6782 Remote Similarity NPC469529
0.678 Remote Similarity NPC270301
0.6757 Remote Similarity NPC179605
0.6757 Remote Similarity NPC279385
0.6735 Remote Similarity NPC471197
0.6732 Remote Similarity NPC209389
0.6712 Remote Similarity NPC285926
0.6712 Remote Similarity NPC14672
0.6712 Remote Similarity NPC315276
0.6711 Remote Similarity NPC103292
0.6707 Remote Similarity NPC237649
0.6707 Remote Similarity NPC300596
0.6702 Remote Similarity NPC16249
0.6701 Remote Similarity NPC248601
0.6701 Remote Similarity NPC471198
0.6688 Remote Similarity NPC314431
0.6686 Remote Similarity NPC114637
0.6649 Remote Similarity NPC72956
0.6647 Remote Similarity NPC309531
0.6647 Remote Similarity NPC472102
0.6647 Remote Similarity NPC27904
0.6625 Remote Similarity NPC315051
0.6623 Remote Similarity NPC150863
0.6615 Remote Similarity NPC153980
0.6615 Remote Similarity NPC471194
0.6615 Remote Similarity NPC471193
0.6615 Remote Similarity NPC6865
0.6609 Remote Similarity NPC472118
0.6608 Remote Similarity NPC472120
0.6608 Remote Similarity NPC472101
0.6603 Remote Similarity NPC325479
0.6591 Remote Similarity NPC248862
0.6585 Remote Similarity NPC259678
0.6584 Remote Similarity NPC43477
0.6573 Remote Similarity NPC182057
0.6573 Remote Similarity NPC147298
0.6573 Remote Similarity NPC131450
0.6564 Remote Similarity NPC314186
0.6564 Remote Similarity NPC470822
0.6558 Remote Similarity NPC72473
0.6558 Remote Similarity NPC58827
0.6558 Remote Similarity NPC307437
0.6549 Remote Similarity NPC172170
0.6532 Remote Similarity NPC472106
0.6517 Remote Similarity NPC14849
0.6516 Remote Similarity NPC313722
0.6514 Remote Similarity NPC471943
0.6507 Remote Similarity NPC57051
0.6497 Remote Similarity NPC328611
0.6484 Remote Similarity NPC476341
0.6481 Remote Similarity NPC22082
0.6481 Remote Similarity NPC186284
0.6474 Remote Similarity NPC280807
0.6474 Remote Similarity NPC472245
0.6471 Remote Similarity NPC94167
0.6471 Remote Similarity NPC172937
0.6463 Remote Similarity NPC33742
0.646 Remote Similarity NPC469560
0.6453 Remote Similarity NPC68650
0.6447 Remote Similarity NPC268534
0.6442 Remote Similarity NPC238499
0.6429 Remote Similarity NPC314223
0.6419 Remote Similarity NPC288232
0.6416 Remote Similarity NPC476231
0.6415 Remote Similarity NPC253476
0.64 Remote Similarity NPC182131
0.6369 Remote Similarity NPC144691
0.6358 Remote Similarity NPC315368
0.6358 Remote Similarity NPC226143
0.6348 Remote Similarity NPC177261
0.6347 Remote Similarity NPC254798
0.6339 Remote Similarity NPC285923
0.6339 Remote Similarity NPC470003
0.6331 Remote Similarity NPC154602
0.6327 Remote Similarity NPC285192
0.6324 Remote Similarity NPC220851
0.6323 Remote Similarity NPC474926
0.6322 Remote Similarity NPC242116
0.6319 Remote Similarity NPC130251
0.6319 Remote Similarity NPC55529
0.6316 Remote Similarity NPC27833
0.6316 Remote Similarity NPC114808
0.6307 Remote Similarity NPC279527
0.6307 Remote Similarity NPC214960
0.6304 Remote Similarity NPC133003
0.6294 Remote Similarity NPC143516
0.6294 Remote Similarity NPC285381
0.6291 Remote Similarity NPC220698
0.6287 Remote Similarity NPC470579
0.6287 Remote Similarity NPC478039
0.6286 Remote Similarity NPC328270
0.6282 Remote Similarity NPC250476
0.628 Remote Similarity NPC301760
0.6276 Remote Similarity NPC473676
0.627 Remote Similarity NPC17273
0.627 Remote Similarity NPC135601
0.627 Remote Similarity NPC141612
0.6269 Remote Similarity NPC471944
0.6265 Remote Similarity NPC130797
0.6264 Remote Similarity NPC143457
0.6264 Remote Similarity NPC39822
0.6258 Remote Similarity NPC181527
0.6257 Remote Similarity NPC281094
0.625 Remote Similarity NPC130898
0.625 Remote Similarity NPC477003
0.625 Remote Similarity NPC52059
0.625 Remote Similarity NPC474973
0.625 Remote Similarity NPC474804
0.625 Remote Similarity NPC470069
0.6243 Remote Similarity NPC113946
0.6243 Remote Similarity NPC153694
0.6243 Remote Similarity NPC211525
0.6242 Remote Similarity NPC476950
0.6232 Remote Similarity NPC256452
0.6229 Remote Similarity NPC472121
0.622 Remote Similarity NPC472243
0.6218 Remote Similarity NPC470343
0.6218 Remote Similarity NPC472244
0.6215 Remote Similarity NPC300631
0.6209 Remote Similarity NPC130931

  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 NPC324445 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
0.8456 Intermediate Similarity NPD478 Approved
0.8026 Intermediate Similarity NPD4939 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD1919 Approved
0.7986 Intermediate Similarity NPD1920 Approved
0.7792 Intermediate Similarity NPD4942 Approved
0.7778 Intermediate Similarity NPD1524 Phase 1
0.761 Intermediate Similarity NPD951 Approved
0.7597 Intermediate Similarity NPD6017 Discontinued
0.7564 Intermediate Similarity NPD979 Approved
0.7365 Intermediate Similarity NPD1165 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD477 Phase 1
0.7284 Intermediate Similarity NPD6395 Phase 2
0.7284 Intermediate Similarity NPD6396 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD5042 Phase 1
0.7208 Intermediate Similarity NPD6655 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3248 Phase 1
0.7183 Intermediate Similarity NPD1344 Phase 2
0.7181 Intermediate Similarity NPD1781 Discontinued
0.7162 Intermediate Similarity NPD797 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7443 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7072 Phase 2
0.7105 Intermediate Similarity NPD1541 Approved
0.7073 Intermediate Similarity NPD1663 Discontinued
0.7073 Intermediate Similarity NPD6855 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD4077 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5715 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5681 Clinical (unspecified phase)
0.6993 Remote Similarity NPD1527 Phase 2
0.6993 Remote Similarity NPD2950 Approved
0.6993 Remote Similarity NPD2949 Approved
0.6989 Remote Similarity NPD3802 Phase 3
0.6966 Remote Similarity NPD4988 Discontinued
0.6954 Remote Similarity NPD7428 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6557 Phase 2
0.6939 Remote Similarity NPD1079 Discontinued
0.6933 Remote Similarity NPD6575 Clinical (unspecified phase)
0.6933 Remote Similarity NPD9540 Approved
0.6918 Remote Similarity NPD4464 Clinical (unspecified phase)
0.6899 Remote Similarity NPD2093 Discontinued
0.6893 Remote Similarity NPD5923 Phase 1
0.6883 Remote Similarity NPD941 Approved
0.6879 Remote Similarity NPD4167 Phase 3
0.6872 Remote Similarity NPD4515 Suspended
0.6871 Remote Similarity NPD2356 Phase 1
0.6863 Remote Similarity NPD486 Clinical (unspecified phase)
0.6853 Remote Similarity NPD1175 Approved
0.68 Remote Similarity NPD7065 Clinical (unspecified phase)
0.68 Remote Similarity NPD9539 Approved
0.68 Remote Similarity NPD9541 Approved
0.6786 Remote Similarity NPD4393 Approved
0.6786 Remote Similarity NPD33 Approved
0.6782 Remote Similarity NPD6613 Clinical (unspecified phase)
0.6781 Remote Similarity NPD2638 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6740 Clinical (unspecified phase)
0.6771 Remote Similarity NPD6204 Clinical (unspecified phase)
0.6757 Remote Similarity NPD5515 Phase 2
0.6755 Remote Similarity NPD6792 Phase 3
0.6747 Remote Similarity NPD2603 Clinical (unspecified phase)
0.6733 Remote Similarity NPD519 Approved
0.6723 Remote Similarity NPD3989 Phase 3
0.672 Remote Similarity NPD1990 Phase 2
0.672 Remote Similarity NPD1991 Phase 2
0.672 Remote Similarity NPD1992 Phase 2
0.6719 Remote Similarity NPD5593 Approved
0.6719 Remote Similarity NPD5594 Approved
0.6711 Remote Similarity NPD1124 Approved
0.6711 Remote Similarity NPD1123 Approved
0.6702 Remote Similarity NPD7817 Phase 1
0.6687 Remote Similarity NPD3434 Clinical (unspecified phase)
0.6685 Remote Similarity NPD3990 Phase 3
0.6667 Remote Similarity NPD480 Approved
0.6667 Remote Similarity NPD5748 Phase 2
0.6667 Remote Similarity NPD441 Approved
0.6646 Remote Similarity NPD2365 Approved
0.6646 Remote Similarity NPD7088 Discontinued
0.6646 Remote Similarity NPD7441 Clinical (unspecified phase)
0.6645 Remote Similarity NPD1619 Phase 3
0.6645 Remote Similarity NPD2634 Clinical (unspecified phase)
0.6628 Remote Similarity NPD7591 Clinical (unspecified phase)
0.6626 Remote Similarity NPD4711 Clinical (unspecified phase)
0.6623 Remote Similarity NPD4549 Discontinued
0.661 Remote Similarity NPD3996 Approved
0.661 Remote Similarity NPD3992 Approved
0.661 Remote Similarity NPD7587 Clinical (unspecified phase)
0.661 Remote Similarity NPD3994 Approved
0.661 Remote Similarity NPD3991 Approved
0.661 Remote Similarity NPD3993 Approved
0.661 Remote Similarity NPD3995 Approved
0.6609 Remote Similarity NPD7795 Phase 2
0.6606 Remote Similarity NPD5423 Phase 2
0.6605 Remote Similarity NPD2820 Phase 3
0.6601 Remote Similarity NPD1593 Approved
0.6596 Remote Similarity NPD1065 Approved
0.6596 Remote Similarity NPD8050 Clinical (unspecified phase)
0.6596 Remote Similarity NPD1064 Approved
0.6593 Remote Similarity NPD3246 Discontinued
0.6591 Remote Similarity NPD7662 Clinical (unspecified phase)
0.6582 Remote Similarity NPD2791 Discontinued
0.6573 Remote Similarity NPD3997 Approved
0.6573 Remote Similarity NPD3999 Approved
0.6573 Remote Similarity NPD3998 Approved
0.657 Remote Similarity NPD2288 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4158 Clinical (unspecified phase)
0.6561 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6558 Remote Similarity NPD3588 Discontinued
0.6554 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6554 Remote Similarity NPD4091 Approved
0.6548 Remote Similarity NPD2360 Approved
0.6543 Remote Similarity NPD6566 Discontinued
0.6538 Remote Similarity NPD1001 Discontinued
0.6529 Remote Similarity NPD7011 Discontinued
0.6529 Remote Similarity NPD4517 Clinical (unspecified phase)
0.6517 Remote Similarity NPD5840 Discontinued
0.6517 Remote Similarity NPD4092 Approved
0.6516 Remote Similarity NPD3626 Phase 3
0.6506 Remote Similarity NPD4432 Discontinued
0.6503 Remote Similarity NPD2129 Approved
0.65 Remote Similarity NPD4214 Discontinued
0.6497 Remote Similarity NPD3632 Clinical (unspecified phase)
0.6497 Remote Similarity NPD3522 Approved
0.6488 Remote Similarity NPD2501 Discontinued
0.6486 Remote Similarity NPD5076 Approved
0.6486 Remote Similarity NPD5077 Approved
0.6471 Remote Similarity NPD2527 Approved
0.6467 Remote Similarity NPD6144 Discontinued
0.6467 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6458 Remote Similarity NPD1107 Approved
0.6458 Remote Similarity NPD1108 Approved
0.645 Remote Similarity NPD2790 Discontinued
0.645 Remote Similarity NPD737 Phase 2
0.6447 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6444 Remote Similarity NPD1618 Phase 2
0.6444 Remote Similarity NPD7014 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3513 Phase 3
0.6442 Remote Similarity NPD6768 Approved
0.6433 Remote Similarity NPD4300 Clinical (unspecified phase)
0.6424 Remote Similarity NPD6485 Discontinued
0.6412 Remote Similarity NPD7267 Clinical (unspecified phase)
0.6405 Remote Similarity NPD3622 Clinical (unspecified phase)
0.6405 Remote Similarity NPD2584 Suspended
0.6405 Remote Similarity NPD3623 Clinical (unspecified phase)
0.6402 Remote Similarity NPD4430 Phase 2
0.6402 Remote Similarity NPD1952 Discontinued
0.6395 Remote Similarity NPD7599 Phase 2
0.6392 Remote Similarity NPD6260 Discontinued
0.6389 Remote Similarity NPD2678 Approved
0.6389 Remote Similarity NPD2679 Approved
0.6386 Remote Similarity NPD3519 Discontinued
0.638 Remote Similarity NPD569 Clinical (unspecified phase)
0.6374 Remote Similarity NPD3067 Approved
0.6374 Remote Similarity NPD7105 Phase 1
0.637 Remote Similarity NPD753 Approved
0.6369 Remote Similarity NPD1271 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5918 Discontinued
0.6364 Remote Similarity NPD1640 Clinical (unspecified phase)
0.6359 Remote Similarity NPD5809 Phase 3
0.6359 Remote Similarity NPD4940 Approved
0.6358 Remote Similarity NPD7142 Discontinued
0.6358 Remote Similarity NPD7600 Phase 2
0.6358 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6347 Remote Similarity NPD6631 Clinical (unspecified phase)
0.6346 Remote Similarity NPD3604 Clinical (unspecified phase)
0.634 Remote Similarity NPD3624 Phase 2
0.6339 Remote Similarity NPD4412 Phase 2
0.6339 Remote Similarity NPD721 Approved
0.6335 Remote Similarity NPD5227 Clinical (unspecified phase)
0.6332 Remote Similarity NPD3780 Phase 2
0.6328 Remote Similarity NPD2369 Discontinued
0.6327 Remote Similarity NPD1764 Approved
0.6327 Remote Similarity NPD1762 Approved
0.6325 Remote Similarity NPD5060 Phase 1
0.6323 Remote Similarity NPD1324 Clinical (unspecified phase)
0.6323 Remote Similarity NPD1036 Approved
0.6322 Remote Similarity NPD5551 Clinical (unspecified phase)
0.6318 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7572 Phase 2
0.6313 Remote Similarity NPD2461 Phase 1
0.6312 Remote Similarity NPD1419 Approved
0.6312 Remote Similarity NPD3034 Discontinued
0.6312 Remote Similarity NPD1417 Approved
0.6312 Remote Similarity NPD813 Approved
0.6312 Remote Similarity NPD708 Approved
0.631 Remote Similarity NPD1658 Discontinued
0.6309 Remote Similarity NPD2622 Approved
0.6309 Remote Similarity NPD1323 Discontinued
0.6298 Remote Similarity NPD7771 Discontinued
0.6291 Remote Similarity NPD18 Approved
0.6291 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6284 Remote Similarity NPD2658 Approved
0.6284 Remote Similarity NPD2659 Approved
0.6284 Remote Similarity NPD3147 Approved
0.6284 Remote Similarity NPD3149 Approved
0.6284 Remote Similarity NPD3148 Approved
0.6284 Remote Similarity NPD3150 Approved
0.6283 Remote Similarity NPD5856 Discontinued
0.6282 Remote Similarity NPD2113 Approved
0.6279 Remote Similarity NPD2351 Discontinued
0.6273 Remote Similarity NPD2331 Discontinued
0.6269 Remote Similarity NPD7439 Clinical (unspecified phase)
0.6268 Remote Similarity NPD2244 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