Structure

Physi-Chem Properties

Molecular Weight:  540.28
Volume:  591.276
LogP:  8.853
LogD:  5.828
LogS:  -7.656
# Rotatable Bonds:  6
TPSA:  39.18
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  7
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.214
Synthetic Accessibility Score:  3.583
Fsp3:  0.243
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.537
MDCK Permeability:  8.389518370677251e-06
Pgp-inhibitor:  1.0
Pgp-substrate:  0.415
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.771
30% Bioavailability (F30%):  0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  96.90233612060547%
Volume Distribution (VD):  2.098
Pgp-substrate:  1.0088993310928345%

ADMET: Metabolism

CYP1A2-inhibitor:  0.75
CYP1A2-substrate:  0.31
CYP2C19-inhibitor:  0.944
CYP2C19-substrate:  0.175
CYP2C9-inhibitor:  0.915
CYP2C9-substrate:  0.951
CYP2D6-inhibitor:  0.953
CYP2D6-substrate:  0.891
CYP3A4-inhibitor:  0.927
CYP3A4-substrate:  0.514

ADMET: Excretion

Clearance (CL):  7.53
Half-life (T1/2):  0.026

ADMET: Toxicity

hERG Blockers:  0.754
Human Hepatotoxicity (H-HT):  0.948
Drug-inuced Liver Injury (DILI):  0.494
AMES Toxicity:  0.917
Rat Oral Acute Toxicity:  0.096
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.934
Carcinogencity:  0.908
Eye Corrosion:  0.003
Eye Irritation:  0.134
Respiratory Toxicity:  0.823

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

  Natural Product: NPC475253

Natural Product ID:  NPC475253
Common Name*:   Chrestfoline C
IUPAC Name:   11-[(1-methoxy-9H-carbazol-3-yl)methyl]-3,5-dimethyl-3-(4-methylpent-3-enyl)pyrano[3,2-a]carbazole
Synonyms:   Chrestfoline C
Standard InCHIKey:  WZDZCOAWFXDCTD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C37H36N2O2/c1-23(2)11-10-17-37(4)18-16-28-35-30(19-24(3)36(28)41-37)27-13-7-9-15-32(27)39(35)22-25-20-29-26-12-6-8-14-31(26)38-34(29)33(21-25)40-5/h6-9,11-16,18-21,38H,10,17,22H2,1-5H3
SMILES:  CC1=CC2=C(C3=C1OC(C=C3)(C)CCC=C(C)C)N(C4=CC=CC=C42)CC5=CC6=C(C(=C5)OC)NC7=CC=CC=C76
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL502119
PubChem CID:   375157
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
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota stem bark;fruit n.a. n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota root bark Kuantaochi, Nantou Hsien, Taiwan n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3118 Murraya euchrestifolia 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 88511.56 nM PMID[495140]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[495140]

☑ 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 NPC475253 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
0.9378 High Similarity NPC473185
0.9275 High Similarity NPC477533
0.9216 High Similarity NPC94157
0.9043 High Similarity NPC473179
0.9032 High Similarity NPC473183
0.894 High Similarity NPC473184
0.891 High Similarity NPC132642
0.8873 High Similarity NPC470930
0.8868 High Similarity NPC477532
0.875 High Similarity NPC199667
0.8716 High Similarity NPC477531
0.871 High Similarity NPC252251
0.8702 High Similarity NPC473181
0.867 High Similarity NPC209174
0.8667 High Similarity NPC473180
0.8641 High Similarity NPC162484
0.8578 High Similarity NPC72211
0.8552 High Similarity NPC473182
0.8532 High Similarity NPC202503
0.8524 High Similarity NPC209769
0.848 Intermediate Similarity NPC70259
0.8436 Intermediate Similarity NPC201697
0.8431 Intermediate Similarity NPC43787
0.8431 Intermediate Similarity NPC205934
0.843 Intermediate Similarity NPC39370
0.8423 Intermediate Similarity NPC473186
0.8365 Intermediate Similarity NPC267423
0.8325 Intermediate Similarity NPC475112
0.8325 Intermediate Similarity NPC291535
0.8325 Intermediate Similarity NPC475085
0.8267 Intermediate Similarity NPC277351
0.8252 Intermediate Similarity NPC131017
0.8233 Intermediate Similarity NPC48353
0.8208 Intermediate Similarity NPC476106
0.8203 Intermediate Similarity NPC170114
0.819 Intermediate Similarity NPC476044
0.8186 Intermediate Similarity NPC242928
0.8157 Intermediate Similarity NPC470549
0.8086 Intermediate Similarity NPC70956
0.8086 Intermediate Similarity NPC243834
0.8075 Intermediate Similarity NPC285558
0.8057 Intermediate Similarity NPC11017
0.8036 Intermediate Similarity NPC227908
0.8028 Intermediate Similarity NPC475774
0.8018 Intermediate Similarity NPC469554
0.8009 Intermediate Similarity NPC128823
0.8 Intermediate Similarity NPC193777
0.7972 Intermediate Similarity NPC329747
0.7965 Intermediate Similarity NPC314954
0.7963 Intermediate Similarity NPC470931
0.7939 Intermediate Similarity NPC101543
0.7902 Intermediate Similarity NPC84478
0.7892 Intermediate Similarity NPC474798
0.7872 Intermediate Similarity NPC475666
0.7864 Intermediate Similarity NPC471080
0.7864 Intermediate Similarity NPC469592
0.7857 Intermediate Similarity NPC475190
0.7848 Intermediate Similarity NPC208084
0.783 Intermediate Similarity NPC81939
0.7826 Intermediate Similarity NPC180504
0.7815 Intermediate Similarity NPC473188
0.7812 Intermediate Similarity NPC86078
0.7803 Intermediate Similarity NPC469594
0.7778 Intermediate Similarity NPC198503
0.7773 Intermediate Similarity NPC208284
0.7759 Intermediate Similarity NPC473187
0.7738 Intermediate Similarity NPC26679
0.7735 Intermediate Similarity NPC477861
0.7727 Intermediate Similarity NPC167860
0.7727 Intermediate Similarity NPC123976
0.7717 Intermediate Similarity NPC475910
0.7702 Intermediate Similarity NPC477066
0.7699 Intermediate Similarity NPC26543
0.7696 Intermediate Similarity NPC245816
0.7696 Intermediate Similarity NPC476138
0.7692 Intermediate Similarity NPC473189
0.7682 Intermediate Similarity NPC185782
0.7682 Intermediate Similarity NPC469589
0.7681 Intermediate Similarity NPC176127
0.7669 Intermediate Similarity NPC478081
0.7667 Intermediate Similarity NPC133609
0.7647 Intermediate Similarity NPC11464
0.7644 Intermediate Similarity NPC303658
0.7639 Intermediate Similarity NPC329793
0.7623 Intermediate Similarity NPC476287
0.7623 Intermediate Similarity NPC478074
0.7617 Intermediate Similarity NPC131486
0.7615 Intermediate Similarity NPC223427
0.7611 Intermediate Similarity NPC193267
0.7611 Intermediate Similarity NPC213530
0.7608 Intermediate Similarity NPC94943
0.7606 Intermediate Similarity NPC473178
0.7604 Intermediate Similarity NPC232727
0.7598 Intermediate Similarity NPC179287
0.7595 Intermediate Similarity NPC477067
0.7595 Intermediate Similarity NPC478082
0.7588 Intermediate Similarity NPC144452
0.7581 Intermediate Similarity NPC153042
0.7577 Intermediate Similarity NPC225279
0.7562 Intermediate Similarity NPC189079
0.756 Intermediate Similarity NPC190007
0.7558 Intermediate Similarity NPC19872
0.7556 Intermediate Similarity NPC183407
0.7549 Intermediate Similarity NPC195788
0.7549 Intermediate Similarity NPC237901
0.7545 Intermediate Similarity NPC39500
0.7544 Intermediate Similarity NPC280799
0.754 Intermediate Similarity NPC471303
0.7535 Intermediate Similarity NPC13880
0.7534 Intermediate Similarity NPC187501
0.7522 Intermediate Similarity NPC305984
0.7521 Intermediate Similarity NPC329631
0.7512 Intermediate Similarity NPC212535
0.7512 Intermediate Similarity NPC18487
0.7512 Intermediate Similarity NPC92111
0.7511 Intermediate Similarity NPC474688
0.7511 Intermediate Similarity NPC162748
0.75 Intermediate Similarity NPC274640
0.75 Intermediate Similarity NPC6786
0.7489 Intermediate Similarity NPC290689
0.7489 Intermediate Similarity NPC135887
0.7489 Intermediate Similarity NPC199277
0.7489 Intermediate Similarity NPC46561
0.7489 Intermediate Similarity NPC471304
0.7489 Intermediate Similarity NPC473041
0.7478 Intermediate Similarity NPC8022
0.7478 Intermediate Similarity NPC470799
0.7469 Intermediate Similarity NPC17437
0.7468 Intermediate Similarity NPC11408
0.7467 Intermediate Similarity NPC310118
0.7465 Intermediate Similarity NPC76748
0.7448 Intermediate Similarity NPC473540
0.7442 Intermediate Similarity NPC307963
0.7435 Intermediate Similarity NPC280272
0.7432 Intermediate Similarity NPC249583
0.7432 Intermediate Similarity NPC4687
0.7432 Intermediate Similarity NPC260909
0.7422 Intermediate Similarity NPC310211
0.7422 Intermediate Similarity NPC294620
0.7422 Intermediate Similarity NPC308137
0.7418 Intermediate Similarity NPC296527
0.7412 Intermediate Similarity NPC184408
0.7406 Intermediate Similarity NPC217554
0.7397 Intermediate Similarity NPC471891
0.7397 Intermediate Similarity NPC176538
0.7382 Intermediate Similarity NPC470126
0.7368 Intermediate Similarity NPC314552
0.7368 Intermediate Similarity NPC169402
0.7362 Intermediate Similarity NPC476999
0.7358 Intermediate Similarity NPC478080
0.7357 Intermediate Similarity NPC116238
0.7356 Intermediate Similarity NPC56618
0.735 Intermediate Similarity NPC253580
0.735 Intermediate Similarity NPC194740
0.7348 Intermediate Similarity NPC150239
0.7345 Intermediate Similarity NPC316981
0.7336 Intermediate Similarity NPC96321
0.7333 Intermediate Similarity NPC475844
0.7328 Intermediate Similarity NPC53534
0.7325 Intermediate Similarity NPC148183
0.7325 Intermediate Similarity NPC152768
0.7322 Intermediate Similarity NPC470785
0.7314 Intermediate Similarity NPC284141
0.7313 Intermediate Similarity NPC162530
0.7313 Intermediate Similarity NPC266931
0.7311 Intermediate Similarity NPC295228
0.7309 Intermediate Similarity NPC89549
0.7308 Intermediate Similarity NPC110151
0.7304 Intermediate Similarity NPC46451
0.7301 Intermediate Similarity NPC87413
0.7294 Intermediate Similarity NPC251090
0.7291 Intermediate Similarity NPC132385
0.729 Intermediate Similarity NPC473177
0.7288 Intermediate Similarity NPC476451
0.7286 Intermediate Similarity NPC72980
0.7284 Intermediate Similarity NPC469734
0.728 Intermediate Similarity NPC184680
0.7277 Intermediate Similarity NPC476997
0.7269 Intermediate Similarity NPC264176
0.7265 Intermediate Similarity NPC36229
0.7265 Intermediate Similarity NPC16452
0.7265 Intermediate Similarity NPC476581
0.7265 Intermediate Similarity NPC200888
0.7261 Intermediate Similarity NPC100079
0.7261 Intermediate Similarity NPC247803
0.7261 Intermediate Similarity NPC23614
0.7257 Intermediate Similarity NPC49547
0.7256 Intermediate Similarity NPC246700
0.7252 Intermediate Similarity NPC295898
0.725 Intermediate Similarity NPC470784
0.725 Intermediate Similarity NPC101350
0.7247 Intermediate Similarity NPC244543
0.7246 Intermediate Similarity NPC476998
0.7246 Intermediate Similarity NPC476996
0.7243 Intermediate Similarity NPC208522
0.7243 Intermediate Similarity NPC78609
0.724 Intermediate Similarity NPC121772
0.7232 Intermediate Similarity NPC472111
0.7232 Intermediate Similarity NPC45190
0.7232 Intermediate Similarity NPC300156

  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 NPC475253 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
0.8084 Intermediate Similarity NPD7222 Phase 2
0.8073 Intermediate Similarity NPD5903 Approved
0.8073 Intermediate Similarity NPD5902 Approved
0.8037 Intermediate Similarity NPD3003 Approved
0.8 Intermediate Similarity NPD7452 Approved
0.8 Intermediate Similarity NPD7453 Approved
0.7963 Intermediate Similarity NPD5658 Approved
0.7904 Intermediate Similarity NPD7558 Phase 2
0.7892 Intermediate Similarity NPD7678 Clinical (unspecified phase)
0.7883 Intermediate Similarity NPD6985 Discontinued
0.787 Intermediate Similarity NPD8403 Phase 1
0.7848 Intermediate Similarity NPD7194 Discontinued
0.782 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7757 Intermediate Similarity NPD1768 Approved
0.7757 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD8363 Approved
0.7733 Intermediate Similarity NPD8364 Approved
0.7671 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7653 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7653 Intermediate Similarity NPD4418 Discontinued
0.7594 Intermediate Similarity NPD5913 Phase 3
0.7594 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD1392 Approved
0.7566 Intermediate Similarity NPD5632 Approved
0.7556 Intermediate Similarity NPD5612 Discontinued
0.7549 Intermediate Similarity NPD8467 Approved
0.7549 Intermediate Similarity NPD8466 Approved
0.7549 Intermediate Similarity NPD8465 Approved
0.7549 Intermediate Similarity NPD8429 Approved
0.7549 Intermediate Similarity NPD8427 Approved
0.7549 Intermediate Similarity NPD8428 Approved
0.7533 Intermediate Similarity NPD3875 Discontinued
0.7523 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD8244 Phase 2
0.7469 Intermediate Similarity NPD8358 Approved
0.7447 Intermediate Similarity NPD6494 Phase 2
0.7442 Intermediate Similarity NPD1038 Approved
0.7441 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD8460 Approved
0.7432 Intermediate Similarity NPD8426 Approved
0.7432 Intermediate Similarity NPD8425 Approved
0.7432 Intermediate Similarity NPD8459 Approved
0.7431 Intermediate Similarity NPD3825 Phase 3
0.7425 Intermediate Similarity NPD5559 Phase 2
0.7406 Intermediate Similarity NPD5256 Discontinued
0.738 Intermediate Similarity NPD3402 Phase 1
0.7378 Intermediate Similarity NPD5067 Phase 2
0.7378 Intermediate Similarity NPD5066 Phase 2
0.7378 Intermediate Similarity NPD4502 Phase 2
0.7368 Intermediate Similarity NPD5164 Discontinued
0.7368 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD5482 Discontinued
0.7336 Intermediate Similarity NPD6243 Phase 3
0.7336 Intermediate Similarity NPD6244 Phase 3
0.7319 Intermediate Similarity NPD5479 Discontinued
0.7309 Intermediate Similarity NPD5530 Phase 1
0.7308 Intermediate Similarity NPD7994 Phase 2
0.7304 Intermediate Similarity NPD3763 Approved
0.7281 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5930 Phase 3
0.7265 Intermediate Similarity NPD4795 Phase 2
0.7261 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD7948 Phase 1
0.7243 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6220 Phase 3
0.7222 Intermediate Similarity NPD7719 Discontinued
0.7206 Intermediate Similarity NPD7659 Discontinued
0.7203 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7956 Approved
0.72 Intermediate Similarity NPD7955 Approved
0.7198 Intermediate Similarity NPD6242 Discontinued
0.7195 Intermediate Similarity NPD8396 Approved
0.7195 Intermediate Similarity NPD8395 Approved
0.7193 Intermediate Similarity NPD3816 Phase 1
0.7193 Intermediate Similarity NPD3815 Phase 1
0.7189 Intermediate Similarity NPD6961 Discontinued
0.7185 Intermediate Similarity NPD4885 Approved
0.7156 Intermediate Similarity NPD6569 Phase 2
0.7155 Intermediate Similarity NPD3514 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD6743 Phase 2
0.7137 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD6742 Phase 2
0.7137 Intermediate Similarity NPD7859 Phase 2
0.7131 Intermediate Similarity NPD7067 Approved
0.7131 Intermediate Similarity NPD7068 Approved
0.7131 Intermediate Similarity NPD7555 Discontinued
0.713 Intermediate Similarity NPD4511 Phase 1
0.713 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD8489 Phase 1
0.7124 Intermediate Similarity NPD5429 Discontinued
0.7123 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD802 Phase 2
0.7119 Intermediate Similarity NPD7417 Discontinued
0.7119 Intermediate Similarity NPD7675 Phase 3
0.7119 Intermediate Similarity NPD7674 Phase 3
0.7119 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD6202 Discontinued
0.7112 Intermediate Similarity NPD7395 Discontinued
0.7107 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD6643 Discontinued
0.7095 Intermediate Similarity NPD3006 Discontinued
0.7093 Intermediate Similarity NPD7672 Approved
0.7093 Intermediate Similarity NPD7671 Approved
0.709 Intermediate Similarity NPD6473 Phase 1
0.7089 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD8279 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5936 Approved
0.7074 Intermediate Similarity NPD5939 Approved
0.7064 Intermediate Similarity NPD7219 Approved
0.7064 Intermediate Similarity NPD7221 Approved
0.7061 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7061 Intermediate Similarity NPD7592 Phase 2
0.7059 Intermediate Similarity NPD3477 Phase 2
0.7059 Intermediate Similarity NPD8284 Discontinued
0.7059 Intermediate Similarity NPD7803 Approved
0.7059 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6550 Discontinued
0.7054 Intermediate Similarity NPD6964 Approved
0.7054 Intermediate Similarity NPD6963 Approved
0.7046 Intermediate Similarity NPD7050 Clinical (unspecified phase)
0.7046 Intermediate Similarity NPD7426 Phase 1
0.7046 Intermediate Similarity NPD7051 Phase 3
0.7035 Intermediate Similarity NPD3397 Phase 2
0.7033 Intermediate Similarity NPD5044 Phase 2
0.7029 Intermediate Similarity NPD4952 Phase 3
0.7025 Intermediate Similarity NPD7853 Phase 2
0.7025 Intermediate Similarity NPD4454 Phase 2
0.7018 Intermediate Similarity NPD2189 Approved
0.7018 Intermediate Similarity NPD5863 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2187 Approved
0.7014 Intermediate Similarity NPD6590 Discontinued
0.7014 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD8442 Discontinued
0.7009 Intermediate Similarity NPD1739 Approved
0.7009 Intermediate Similarity NPD1740 Approved
0.7004 Intermediate Similarity NPD8100 Phase 3
0.7004 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8525 Approved
0.6992 Remote Similarity NPD5450 Discontinued
0.6992 Remote Similarity NPD7413 Phase 3
0.6979 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4204 Approved
0.6977 Remote Similarity NPD4203 Approved
0.6976 Remote Similarity NPD7868 Clinical (unspecified phase)
0.6975 Remote Similarity NPD7603 Discontinued
0.6974 Remote Similarity NPD8524 Approved
0.6974 Remote Similarity NPD6290 Phase 2
0.697 Remote Similarity NPD7069 Discontinued
0.697 Remote Similarity NPD3330 Phase 1
0.6967 Remote Similarity NPD6750 Phase 2
0.6966 Remote Similarity NPD4429 Discontinued
0.6964 Remote Similarity NPD6230 Discontinued
0.6964 Remote Similarity NPD2177 Approved
0.6964 Remote Similarity NPD2176 Approved
0.6964 Remote Similarity NPD2175 Phase 3
0.6963 Remote Similarity NPD3920 Phase 2
0.6957 Remote Similarity NPD8091 Phase 3
0.6951 Remote Similarity NPD6716 Phase 1
0.6951 Remote Similarity NPD6988 Phase 1
0.6942 Remote Similarity NPD4373 Phase 2
0.6939 Remote Similarity NPD8016 Phase 3
0.6939 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6976 Clinical (unspecified phase)
0.693 Remote Similarity NPD6150 Discontinued
0.6926 Remote Similarity NPD3343 Phase 3
0.6923 Remote Similarity NPD3923 Approved
0.6923 Remote Similarity NPD3921 Approved
0.6923 Remote Similarity NPD3924 Approved
0.6923 Remote Similarity NPD3922 Approved
0.6923 Remote Similarity NPD4440 Clinical (unspecified phase)
0.692 Remote Similarity NPD6525 Clinical (unspecified phase)
0.692 Remote Similarity NPD8101 Phase 3
0.6914 Remote Similarity NPD6760 Discontinued
0.6911 Remote Similarity NPD6790 Phase 1
0.6906 Remote Similarity NPD5512 Phase 3
0.6902 Remote Similarity NPD6531 Approved
0.6902 Remote Similarity NPD6530 Approved
0.6902 Remote Similarity NPD7708 Approved
0.6897 Remote Similarity NPD4927 Discontinued
0.6895 Remote Similarity NPD4349 Approved
0.6895 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6895 Remote Similarity NPD4350 Approved
0.6895 Remote Similarity NPD1034 Phase 3
0.6894 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5999 Phase 2
0.6889 Remote Similarity NPD4548 Discontinued
0.6889 Remote Similarity NPD5547 Clinical (unspecified phase)
0.6888 Remote Similarity NPD5022 Discontinued
0.6888 Remote Similarity NPD8512 Phase 3
0.6886 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6884 Remote Similarity NPD7479 Phase 2
0.6883 Remote Similarity NPD7392 Phase 2
0.688 Remote Similarity NPD6147 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