Structure

Physi-Chem Properties

Molecular Weight:  225.08
Volume:  235.153
LogP:  3.105
LogD:  2.983
LogS:  -4.573
# Rotatable Bonds:  2
TPSA:  42.09
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.681
Synthetic Accessibility Score:  2.1
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.933
MDCK Permeability:  1.1359603377059102e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.783
Plasma Protein Binding (PPB):  91.96543884277344%
Volume Distribution (VD):  0.753
Pgp-substrate:  4.414909362792969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.991
CYP1A2-substrate:  0.948
CYP2C19-inhibitor:  0.603
CYP2C19-substrate:  0.274
CYP2C9-inhibitor:  0.347
CYP2C9-substrate:  0.859
CYP2D6-inhibitor:  0.493
CYP2D6-substrate:  0.726
CYP3A4-inhibitor:  0.585
CYP3A4-substrate:  0.234

ADMET: Excretion

Clearance (CL):  4.844
Half-life (T1/2):  0.579

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.107
Drug-inuced Liver Injury (DILI):  0.773
AMES Toxicity:  0.271
Rat Oral Acute Toxicity:  0.032
Maximum Recommended Daily Dose:  0.642
Skin Sensitization:  0.84
Carcinogencity:  0.325
Eye Corrosion:  0.337
Eye Irritation:  0.985
Respiratory Toxicity:  0.977

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

  Natural Product: NPC187501

Natural Product ID:  NPC187501
Common Name*:   Murrayanine
IUPAC Name:   1-methoxy-9H-carbazole-3-carbaldehyde
Synonyms:   Murrayanine
Standard InCHIKey:  FWNZQNAJETXQPP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H11NO2/c1-17-13-7-9(8-16)6-11-10-4-2-3-5-12(10)15-14(11)13/h2-8,15H,1H3
SMILES:  COc1cc(C=O)cc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1689802
PubChem CID:   96942
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. flower n.a. PMID[10757740]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10757740]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. twig n.a. PMID[10757740]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. leaf n.a. PMID[10757740]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11000023]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[12662104]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO23546 Clausena lansium Species Rutaceae Eukaryota leaves n.a. n.a. PMID[19327990]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. root n.a. PMID[21302964]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Stems n.a. n.a. PMID[22372931]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. Sri Lankan n.a. PMID[23376010]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota fruits Coimbatore, India 2010-JUN PMID[23691929]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. leaf n.a. PMID[24354205]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. twig n.a. PMID[24354205]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Roots n.a. n.a. PMID[24798144]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Leaves n.a. n.a. PMID[26523463]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[27136692]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota Root barks n.a. n.a. PMID[3236015]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17480 Murraya siamensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3364 Murraya koenigii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19266 Clausena excavata Species Rutaceae 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
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 11450.0 nM PMID[538462]
NPT91 Cell Line KB Homo sapiens IC50 = 72230.0 nM PMID[538462]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 200000.0 nM PMID[538462]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3500.0 nM PMID[538464]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3900.0 nM PMID[538464]

☑ 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 NPC187501 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
0.9639 High Similarity NPC208084
0.959 High Similarity NPC225279
0.9583 High Similarity NPC39500
0.9388 High Similarity NPC184408
0.9319 High Similarity NPC45190
0.93 High Similarity NPC179287
0.92 High Similarity NPC144452
0.9171 High Similarity NPC283117
0.9072 High Similarity NPC249583
0.904 High Similarity NPC118228
0.9034 High Similarity NPC39370
0.9029 High Similarity NPC473186
0.9021 High Similarity NPC300156
0.8985 High Similarity NPC294375
0.8981 High Similarity NPC474688
0.8976 High Similarity NPC274640
0.893 High Similarity NPC242928
0.8856 High Similarity NPC293151
0.8844 High Similarity NPC310211
0.8844 High Similarity NPC308137
0.8812 High Similarity NPC46561
0.8782 High Similarity NPC4687
0.8711 High Similarity NPC128823
0.8689 High Similarity NPC51388
0.8645 High Similarity NPC475844
0.8627 High Similarity NPC247803
0.861 High Similarity NPC474798
0.8607 High Similarity NPC87413
0.8544 High Similarity NPC150239
0.8531 High Similarity NPC474701
0.8502 High Similarity NPC198503
0.848 Intermediate Similarity NPC116238
0.8429 Intermediate Similarity NPC160381
0.8413 Intermediate Similarity NPC280799
0.8408 Intermediate Similarity NPC321428
0.8398 Intermediate Similarity NPC169402
0.8366 Intermediate Similarity NPC39679
0.8359 Intermediate Similarity NPC475190
0.8333 Intermediate Similarity NPC9894
0.8278 Intermediate Similarity NPC174760
0.823 Intermediate Similarity NPC288987
0.8195 Intermediate Similarity NPC199667
0.8186 Intermediate Similarity NPC86834
0.8186 Intermediate Similarity NPC210828
0.8165 Intermediate Similarity NPC6786
0.8155 Intermediate Similarity NPC23294
0.8146 Intermediate Similarity NPC473181
0.8116 Intermediate Similarity NPC473180
0.8116 Intermediate Similarity NPC94157
0.8107 Intermediate Similarity NPC303951
0.8095 Intermediate Similarity NPC131885
0.8086 Intermediate Similarity NPC3207
0.8084 Intermediate Similarity NPC470018
0.804 Intermediate Similarity NPC131017
0.8039 Intermediate Similarity NPC470930
0.7963 Intermediate Similarity NPC257851
0.7934 Intermediate Similarity NPC132642
0.79 Intermediate Similarity NPC49547
0.7887 Intermediate Similarity NPC473179
0.788 Intermediate Similarity NPC74575
0.7851 Intermediate Similarity NPC473188
0.7847 Intermediate Similarity NPC471304
0.7824 Intermediate Similarity NPC205372
0.7816 Intermediate Similarity NPC476138
0.7816 Intermediate Similarity NPC245816
0.7811 Intermediate Similarity NPC230403
0.781 Intermediate Similarity NPC146418
0.7806 Intermediate Similarity NPC176127
0.7798 Intermediate Similarity NPC478078
0.7798 Intermediate Similarity NPC140296
0.7793 Intermediate Similarity NPC473187
0.7783 Intermediate Similarity NPC243834
0.7783 Intermediate Similarity NPC16066
0.7783 Intermediate Similarity NPC70956
0.7778 Intermediate Similarity NPC118511
0.7778 Intermediate Similarity NPC132539
0.7762 Intermediate Similarity NPC269367
0.7757 Intermediate Similarity NPC96321
0.7754 Intermediate Similarity NPC76982
0.7745 Intermediate Similarity NPC72211
0.7729 Intermediate Similarity NPC162484
0.7717 Intermediate Similarity NPC157931
0.7714 Intermediate Similarity NPC209769
0.7703 Intermediate Similarity NPC329631
0.7653 Intermediate Similarity NPC476287
0.7653 Intermediate Similarity NPC88363
0.7647 Intermediate Similarity NPC70259
0.7639 Intermediate Similarity NPC53534
0.7636 Intermediate Similarity NPC473185
0.7634 Intermediate Similarity NPC470017
0.7632 Intermediate Similarity NPC208522
0.7619 Intermediate Similarity NPC193777
0.7613 Intermediate Similarity NPC477112
0.7613 Intermediate Similarity NPC260434
0.7606 Intermediate Similarity NPC474428
0.7604 Intermediate Similarity NPC323969
0.7602 Intermediate Similarity NPC194740
0.7598 Intermediate Similarity NPC43787
0.7598 Intermediate Similarity NPC205934
0.7594 Intermediate Similarity NPC470020
0.7593 Intermediate Similarity NPC473041
0.7588 Intermediate Similarity NPC84478
0.7581 Intermediate Similarity NPC152768
0.7581 Intermediate Similarity NPC148183
0.7577 Intermediate Similarity NPC148889
0.757 Intermediate Similarity NPC89508
0.7547 Intermediate Similarity NPC185782
0.7542 Intermediate Similarity NPC89549
0.7534 Intermediate Similarity NPC475253
0.7523 Intermediate Similarity NPC118940
0.7523 Intermediate Similarity NPC472099
0.7523 Intermediate Similarity NPC26679
0.7523 Intermediate Similarity NPC471762
0.7522 Intermediate Similarity NPC15801
0.7521 Intermediate Similarity NPC152620
0.7512 Intermediate Similarity NPC291535
0.7512 Intermediate Similarity NPC303658
0.7512 Intermediate Similarity NPC475085
0.7512 Intermediate Similarity NPC475112
0.7511 Intermediate Similarity NPC34770
0.75 Intermediate Similarity NPC122436
0.75 Intermediate Similarity NPC165964
0.7488 Intermediate Similarity NPC476106
0.7477 Intermediate Similarity NPC298436
0.7476 Intermediate Similarity NPC251090
0.7476 Intermediate Similarity NPC165599
0.7467 Intermediate Similarity NPC473182
0.7465 Intermediate Similarity NPC312645
0.7465 Intermediate Similarity NPC201697
0.7464 Intermediate Similarity NPC267423
0.7463 Intermediate Similarity NPC42591
0.7453 Intermediate Similarity NPC270918
0.7445 Intermediate Similarity NPC470022
0.7444 Intermediate Similarity NPC311906
0.744 Intermediate Similarity NPC141454
0.7438 Intermediate Similarity NPC296527
0.7438 Intermediate Similarity NPC221873
0.7437 Intermediate Similarity NPC478032
0.7435 Intermediate Similarity NPC142385
0.7429 Intermediate Similarity NPC135887
0.7429 Intermediate Similarity NPC199277
0.7427 Intermediate Similarity NPC276517
0.7426 Intermediate Similarity NPC194040
0.7422 Intermediate Similarity NPC475720
0.7422 Intermediate Similarity NPC474192
0.7418 Intermediate Similarity NPC171787
0.7416 Intermediate Similarity NPC329793
0.7416 Intermediate Similarity NPC19872
0.7402 Intermediate Similarity NPC76748
0.7395 Intermediate Similarity NPC208284
0.7393 Intermediate Similarity NPC134848
0.7393 Intermediate Similarity NPC476098
0.7393 Intermediate Similarity NPC67401
0.7393 Intermediate Similarity NPC475774
0.7393 Intermediate Similarity NPC223427
0.7387 Intermediate Similarity NPC21638
0.7385 Intermediate Similarity NPC305984
0.7381 Intermediate Similarity NPC476044
0.7379 Intermediate Similarity NPC307963
0.7374 Intermediate Similarity NPC84347
0.7373 Intermediate Similarity NPC477979
0.7368 Intermediate Similarity NPC473183
0.7368 Intermediate Similarity NPC280714
0.7366 Intermediate Similarity NPC92111
0.7366 Intermediate Similarity NPC66777
0.7363 Intermediate Similarity NPC212535
0.7361 Intermediate Similarity NPC38237
0.7361 Intermediate Similarity NPC48353
0.7361 Intermediate Similarity NPC264176
0.7357 Intermediate Similarity NPC473184
0.7353 Intermediate Similarity NPC246700
0.7352 Intermediate Similarity NPC174576
0.7345 Intermediate Similarity NPC196718
0.7345 Intermediate Similarity NPC102593
0.7339 Intermediate Similarity NPC8022
0.7339 Intermediate Similarity NPC470799
0.7339 Intermediate Similarity NPC36405
0.7333 Intermediate Similarity NPC329747
0.7333 Intermediate Similarity NPC176538
0.733 Intermediate Similarity NPC60621
0.7327 Intermediate Similarity NPC324361
0.7322 Intermediate Similarity NPC185197
0.7321 Intermediate Similarity NPC306376
0.7318 Intermediate Similarity NPC74360
0.7317 Intermediate Similarity NPC144381
0.7316 Intermediate Similarity NPC166712
0.7315 Intermediate Similarity NPC220337
0.7311 Intermediate Similarity NPC258048
0.7309 Intermediate Similarity NPC97746
0.7308 Intermediate Similarity NPC270515
0.7304 Intermediate Similarity NPC475816
0.7302 Intermediate Similarity NPC325297
0.7297 Intermediate Similarity NPC216612
0.7293 Intermediate Similarity NPC235685
0.7291 Intermediate Similarity NPC94943
0.729 Intermediate Similarity NPC244741
0.729 Intermediate Similarity NPC183777
0.7284 Intermediate Similarity NPC208364
0.7284 Intermediate Similarity NPC160100
0.7281 Intermediate Similarity NPC253675

  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 NPC187501 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
0.9104 High Similarity NPD6160 Clinical (unspecified phase)
0.8009 Intermediate Similarity NPD4429 Discontinued
0.7925 Intermediate Similarity NPD5632 Approved
0.789 Intermediate Similarity NPD5479 Discontinued
0.785 Intermediate Similarity NPD6242 Discontinued
0.7847 Intermediate Similarity NPD1166 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD3945 Discontinued
0.7727 Intermediate Similarity NPD5022 Discontinued
0.7703 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD3257 Approved
0.7634 Intermediate Similarity NPD3006 Discontinued
0.7617 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD5512 Phase 3
0.7559 Intermediate Similarity NPD5416 Discontinued
0.7558 Intermediate Similarity NPD3258 Approved
0.7536 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD5429 Discontinued
0.7524 Intermediate Similarity NPD5003 Discontinued
0.7512 Intermediate Similarity NPD7395 Discontinued
0.75 Intermediate Similarity NPD3746 Discontinued
0.75 Intermediate Similarity NPD5482 Discontinued
0.75 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD1466 Phase 3
0.7455 Intermediate Similarity NPD1467 Approved
0.7455 Intermediate Similarity NPD1867 Approved
0.7452 Intermediate Similarity NPD2778 Approved
0.7427 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD2565 Phase 2
0.7402 Intermediate Similarity NPD2564 Approved
0.7399 Intermediate Similarity NPD4328 Approved
0.7379 Intermediate Similarity NPD1038 Approved
0.7379 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD2285 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD2951 Discontinued
0.7346 Intermediate Similarity NPD2779 Approved
0.7327 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD7853 Phase 2
0.7324 Intermediate Similarity NPD3003 Approved
0.7321 Intermediate Similarity NPD7994 Phase 2
0.7309 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD5901 Discontinued
0.7269 Intermediate Similarity NPD4885 Approved
0.7265 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD4952 Phase 3
0.7256 Intermediate Similarity NPD5658 Approved
0.725 Intermediate Similarity NPD7708 Approved
0.7235 Intermediate Similarity NPD7703 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD4502 Phase 2
0.7225 Intermediate Similarity NPD1505 Phase 2
0.722 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD3825 Phase 3
0.7177 Intermediate Similarity NPD4418 Discontinued
0.7174 Intermediate Similarity NPD3250 Phase 1
0.7168 Intermediate Similarity NPD3259 Approved
0.7168 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6716 Phase 1
0.7163 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD4373 Phase 2
0.7156 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD5164 Discontinued
0.7137 Intermediate Similarity NPD5559 Phase 2
0.7136 Intermediate Similarity NPD5902 Approved
0.7136 Intermediate Similarity NPD5903 Approved
0.7136 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD5450 Discontinued
0.7131 Intermediate Similarity NPD7803 Approved
0.7131 Intermediate Similarity NPD3986 Discontinued
0.713 Intermediate Similarity NPD5850 Phase 3
0.7124 Intermediate Similarity NPD6790 Phase 1
0.7123 Intermediate Similarity NPD1768 Approved
0.7115 Intermediate Similarity NPD5913 Phase 3
0.7115 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD3392 Approved
0.7104 Intermediate Similarity NPD5612 Discontinued
0.7097 Intermediate Similarity NPD7467 Discontinued
0.7089 Intermediate Similarity NPD4558 Phase 2
0.7089 Intermediate Similarity NPD484 Approved
0.7087 Intermediate Similarity NPD5256 Discontinued
0.7085 Intermediate Similarity NPD6770 Approved
0.7069 Intermediate Similarity NPD4368 Phase 2
0.7066 Intermediate Similarity NPD7956 Approved
0.7066 Intermediate Similarity NPD7955 Approved
0.7064 Intermediate Similarity NPD4506 Discontinued
0.7062 Intermediate Similarity NPD6550 Discontinued
0.7059 Intermediate Similarity NPD5293 Phase 2
0.7051 Intermediate Similarity NPD7452 Approved
0.7051 Intermediate Similarity NPD7222 Phase 2
0.7051 Intermediate Similarity NPD7453 Approved
0.7048 Intermediate Similarity NPD7603 Discontinued
0.7046 Intermediate Similarity NPD8358 Approved
0.7045 Intermediate Similarity NPD8363 Approved
0.7045 Intermediate Similarity NPD8364 Approved
0.7045 Intermediate Similarity NPD5866 Approved
0.7037 Intermediate Similarity NPD6530 Approved
0.7037 Intermediate Similarity NPD6531 Approved
0.7026 Intermediate Similarity NPD4454 Phase 2
0.7018 Intermediate Similarity NPD6376 Discontinued
0.7009 Intermediate Similarity NPD6974 Phase 3
0.7005 Intermediate Similarity NPD2715 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5067 Phase 2
0.7 Intermediate Similarity NPD5066 Phase 2
0.7 Intermediate Similarity NPD6962 Phase 2
0.7 Intermediate Similarity NPD7688 Phase 1
0.6996 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6991 Remote Similarity NPD2920 Discontinued
0.6991 Remote Similarity NPD6176 Phase 1
0.6991 Remote Similarity NPD6995 Phase 1
0.6988 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6978 Remote Similarity NPD7180 Phase 3
0.6971 Remote Similarity NPD8463 Approved
0.6964 Remote Similarity NPD3354 Phase 2
0.6961 Remote Similarity NPD3920 Phase 2
0.6959 Remote Similarity NPD3947 Discontinued
0.6959 Remote Similarity NPD2721 Clinical (unspecified phase)
0.6959 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5924 Discontinued
0.6951 Remote Similarity NPD6456 Discontinued
0.6941 Remote Similarity NPD2509 Approved
0.6941 Remote Similarity NPD2510 Approved
0.6934 Remote Similarity NPD6590 Discontinued
0.6933 Remote Similarity NPD5488 Discontinued
0.6927 Remote Similarity NPD8403 Phase 1
0.6927 Remote Similarity NPD6245 Phase 2
0.6923 Remote Similarity NPD5939 Approved
0.6923 Remote Similarity NPD5936 Approved
0.6923 Remote Similarity NPD5805 Approved
0.692 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6915 Remote Similarity NPD1325 Approved
0.6915 Remote Similarity NPD1326 Approved
0.6913 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6911 Remote Similarity NPD5399 Discovery
0.6907 Remote Similarity NPD7417 Discontinued
0.6906 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6895 Remote Similarity NPD1392 Approved
0.6889 Remote Similarity NPD6985 Discontinued
0.6884 Remote Similarity NPD2177 Approved
0.6884 Remote Similarity NPD2176 Approved
0.6884 Remote Similarity NPD2175 Phase 3
0.6878 Remote Similarity NPD6517 Phase 3
0.6878 Remote Similarity NPD2081 Clinical (unspecified phase)
0.6877 Remote Similarity NPD8429 Approved
0.6877 Remote Similarity NPD8467 Approved
0.6877 Remote Similarity NPD8428 Approved
0.6877 Remote Similarity NPD8465 Approved
0.6877 Remote Similarity NPD8466 Approved
0.6877 Remote Similarity NPD8427 Approved
0.6875 Remote Similarity NPD8102 Discontinued
0.6869 Remote Similarity NPD6988 Phase 1
0.6867 Remote Similarity NPD6223 Clinical (unspecified phase)
0.6867 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6866 Remote Similarity NPD2681 Approved
0.6866 Remote Similarity NPD2680 Approved
0.6864 Remote Similarity NPD2187 Approved
0.6864 Remote Similarity NPD2189 Approved
0.6858 Remote Similarity NPD3875 Discontinued
0.6858 Remote Similarity NPD3402 Phase 1
0.6852 Remote Similarity NPD3289 Phase 3
0.6852 Remote Similarity NPD4501 Approved
0.6852 Remote Similarity NPD4500 Approved
0.6852 Remote Similarity NPD3290 Approved
0.6851 Remote Similarity NPD946 Discontinued
0.685 Remote Similarity NPD7872 Phase 2
0.6847 Remote Similarity NPD6220 Phase 3
0.6847 Remote Similarity NPD7470 Discontinued
0.6844 Remote Similarity NPD6961 Discontinued
0.6836 Remote Similarity NPD8459 Approved
0.6836 Remote Similarity NPD8460 Approved
0.6831 Remote Similarity NPD2311 Clinical (unspecified phase)
0.6831 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6827 Remote Similarity NPD3607 Clinical (unspecified phase)
0.6827 Remote Similarity NPD4442 Phase 2
0.682 Remote Similarity NPD4511 Phase 1
0.6816 Remote Similarity NPD7069 Discontinued
0.681 Remote Similarity NPD4948 Discontinued
0.681 Remote Similarity NPD1659 Phase 1
0.6786 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6784 Remote Similarity NPD9705 Discontinued
0.6784 Remote Similarity NPD112 Approved
0.6784 Remote Similarity NPD7194 Discontinued
0.6784 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6783 Remote Similarity NPD3925 Approved
0.6782 Remote Similarity NPD2844 Phase 3
0.6777 Remote Similarity NPD2792 Approved
0.6777 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6776 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6771 Remote Similarity NPD5475 Discontinued
0.6771 Remote Similarity NPD7468 Clinical (unspecified phase)
0.677 Remote Similarity NPD8425 Approved
0.677 Remote Similarity NPD8426 Approved
0.677 Remote Similarity NPD5443 Clinical (unspecified phase)
0.6759 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6758 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6756 Remote Similarity NPD3757 Clinical (unspecified phase)
0.6753 Remote Similarity NPD3263 Phase 3
0.6752 Remote Similarity NPD6263 Clinical (unspecified phase)
0.675 Remote Similarity NPD7206 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