Structure

Physi-Chem Properties

Molecular Weight:  255.09
Volume:  261.239
LogP:  3.38
LogD:  3.188
LogS:  -5.38
# Rotatable Bonds:  3
TPSA:  51.32
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.731
Synthetic Accessibility Score:  2.187
Fsp3:  0.133
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:  -4.941
MDCK Permeability:  8.792198968876619e-06
Pgp-inhibitor:  0.004
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.708
Plasma Protein Binding (PPB):  91.28186798095703%
Volume Distribution (VD):  0.889
Pgp-substrate:  6.594790458679199%

ADMET: Metabolism

CYP1A2-inhibitor:  0.983
CYP1A2-substrate:  0.97
CYP2C19-inhibitor:  0.576
CYP2C19-substrate:  0.65
CYP2C9-inhibitor:  0.176
CYP2C9-substrate:  0.927
CYP2D6-inhibitor:  0.381
CYP2D6-substrate:  0.925
CYP3A4-inhibitor:  0.536
CYP3A4-substrate:  0.209

ADMET: Excretion

Clearance (CL):  5.055
Half-life (T1/2):  0.332

ADMET: Toxicity

hERG Blockers:  0.041
Human Hepatotoxicity (H-HT):  0.219
Drug-inuced Liver Injury (DILI):  0.818
AMES Toxicity:  0.886
Rat Oral Acute Toxicity:  0.213
Maximum Recommended Daily Dose:  0.935
Skin Sensitization:  0.803
Carcinogencity:  0.498
Eye Corrosion:  0.149
Eye Irritation:  0.986
Respiratory Toxicity:  0.963

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

  Natural Product: NPC310211

Natural Product ID:  NPC310211
Common Name*:   Lansine
IUPAC Name:   2,7-dimethoxy-9H-carbazole-3-carbaldehyde
Synonyms:   Lansine
Standard InCHIKey:  KSAHTWWUVLYPSK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H13NO3/c1-18-10-3-4-11-12-5-9(8-17)15(19-2)7-14(12)16-13(11)6-10/h3-8,16H,1-2H3
SMILES:  COc1ccc2c3cc(C=O)c(cc3[nH]c2c1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1689805
PubChem CID:   5317755
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
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11000023]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11720530]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724858]
NPO29161 Hyptis urticoides Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19265396]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. Guam Island, Pacific Ocean n.a. PMID[21774474]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22050382]
NPO18135 Clausena vestita Species Rutaceae Eukaryota whole plants Yunnan Province, China 2008-JAN PMID[22093759]
NPO4806 Clausena wallichii Species Rutaceae Eukaryota Roots n.a. n.a. PMID[22482432]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. Guam Island, Pacific Ocean n.a. PMID[23164710]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26203536]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota Seeds n.a. n.a. PMID[28951079]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12271 Micromelum hirsutum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12271 Micromelum hirsutum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28500 Griselinia scandens Species Griseliniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28961 Croton hutchinsonianus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29095 Yucca elata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18135 Clausena vestita Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12271 Micromelum hirsutum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28544 Podocalyx loranthoides Species Picrodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28943 Daldinia vernicosa Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29161 Hyptis urticoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29070 Bulbine asphodeloides Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29321 Octopus octopodia Species Octopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25073 Saccharina latissima Species Laminariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4806 Clausena wallichii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29028 Cicer cuneatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29497 Delphinium speciosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23710 Otholobium pubescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28427 Gutenbergia marginata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27603 Populus candicans Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28735 Helicia erratica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27349 Rhododendron edgeworthii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25248 Gloydius blomhoffii Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29461 Sarcophyton infundibuliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29073 Ipomoea carnea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29387 Eudendrium racemosum Species Eudendriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29518 Nardia scalaris Species Solenostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28639 Trixis grisebachii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29180 Monachosorum maximowiczii Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29035 Pseudomonas cichorii Species Pseudomonadaceae Bacteria 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 = 102010.0 nM PMID[551719]
NPT91 Cell Line KB Homo sapiens IC50 > 200000.0 nM PMID[551719]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 200000.0 nM PMID[551719]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 102200.0 nM PMID[551720]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 96000.0 nM PMID[551722]
NPT19 Organism Escherichia coli Escherichia coli MIC = 128.0 ug.mL-1 PMID[551721]
NPT2 Others Unspecified Selectivity Index < 0.8 n.a. PMID[551722]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC90 > 128000.0 nM PMID[551722]

☑ 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 NPC310211 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
1.0 High Similarity NPC308137
0.9741 High Similarity NPC46561
0.9741 High Similarity NPC247803
0.9734 High Similarity NPC249583
0.9641 High Similarity NPC150239
0.9592 High Similarity NPC198503
0.9585 High Similarity NPC116238
0.9487 High Similarity NPC169402
0.9424 High Similarity NPC4687
0.9343 High Similarity NPC174760
0.9275 High Similarity NPC86834
0.9275 High Similarity NPC210828
0.9231 High Similarity NPC23294
0.9231 High Similarity NPC87413
0.9196 High Similarity NPC208084
0.9179 High Similarity NPC303951
0.9171 High Similarity NPC45190
0.9141 High Similarity NPC3207
0.8995 High Similarity NPC6786
0.898 High Similarity NPC39679
0.8971 High Similarity NPC179287
0.8878 High Similarity NPC300156
0.8844 High Similarity NPC187501
0.8768 High Similarity NPC473187
0.8683 High Similarity NPC225279
0.8653 High Similarity NPC131017
0.8571 High Similarity NPC39500
0.8564 High Similarity NPC243834
0.8564 High Similarity NPC70956
0.852 High Similarity NPC72211
0.8482 Intermediate Similarity NPC160381
0.8462 Intermediate Similarity NPC280799
0.8421 Intermediate Similarity NPC144452
0.8418 Intermediate Similarity NPC70259
0.8406 Intermediate Similarity NPC184408
0.8382 Intermediate Similarity NPC9894
0.8367 Intermediate Similarity NPC43787
0.8367 Intermediate Similarity NPC205934
0.8308 Intermediate Similarity NPC162484
0.8282 Intermediate Similarity NPC89549
0.8259 Intermediate Similarity NPC475112
0.8259 Intermediate Similarity NPC291535
0.8259 Intermediate Similarity NPC475085
0.8233 Intermediate Similarity NPC474688
0.8227 Intermediate Similarity NPC476106
0.8224 Intermediate Similarity NPC274640
0.819 Intermediate Similarity NPC298436
0.8187 Intermediate Similarity NPC84478
0.8186 Intermediate Similarity NPC283117
0.8186 Intermediate Similarity NPC193777
0.8173 Intermediate Similarity NPC118228
0.8143 Intermediate Similarity NPC473041
0.8135 Intermediate Similarity NPC212535
0.8134 Intermediate Similarity NPC152768
0.8134 Intermediate Similarity NPC148183
0.8119 Intermediate Similarity NPC39370
0.8119 Intermediate Similarity NPC476044
0.8119 Intermediate Similarity NPC267423
0.8116 Intermediate Similarity NPC294375
0.8116 Intermediate Similarity NPC146418
0.8111 Intermediate Similarity NPC473186
0.8095 Intermediate Similarity NPC293151
0.8068 Intermediate Similarity NPC269367
0.8056 Intermediate Similarity NPC471762
0.8051 Intermediate Similarity NPC94943
0.8037 Intermediate Similarity NPC122436
0.8037 Intermediate Similarity NPC51388
0.8019 Intermediate Similarity NPC201697
0.801 Intermediate Similarity NPC321428
0.8 Intermediate Similarity NPC190007
0.8 Intermediate Similarity NPC97746
0.7974 Intermediate Similarity NPC473188
0.7972 Intermediate Similarity NPC194740
0.7951 Intermediate Similarity NPC134848
0.7937 Intermediate Similarity NPC475844
0.7929 Intermediate Similarity NPC242928
0.7925 Intermediate Similarity NPC305984
0.7917 Intermediate Similarity NPC21638
0.7915 Intermediate Similarity NPC16066
0.7913 Intermediate Similarity NPC470930
0.7905 Intermediate Similarity NPC48353
0.7905 Intermediate Similarity NPC264176
0.79 Intermediate Similarity NPC474701
0.7892 Intermediate Similarity NPC329747
0.789 Intermediate Similarity NPC66777
0.7887 Intermediate Similarity NPC303658
0.786 Intermediate Similarity NPC60621
0.7843 Intermediate Similarity NPC128823
0.7837 Intermediate Similarity NPC183777
0.7818 Intermediate Similarity NPC260434
0.7816 Intermediate Similarity NPC199277
0.7816 Intermediate Similarity NPC135887
0.7803 Intermediate Similarity NPC235685
0.7794 Intermediate Similarity NPC306376
0.7768 Intermediate Similarity NPC101350
0.7767 Intermediate Similarity NPC473179
0.7745 Intermediate Similarity NPC153042
0.7738 Intermediate Similarity NPC217176
0.7731 Intermediate Similarity NPC323969
0.7725 Intermediate Similarity NPC471304
0.7721 Intermediate Similarity NPC96321
0.7719 Intermediate Similarity NPC475666
0.7714 Intermediate Similarity NPC475910
0.7713 Intermediate Similarity NPC76982
0.771 Intermediate Similarity NPC170114
0.7696 Intermediate Similarity NPC477532
0.7682 Intermediate Similarity NPC478078
0.7681 Intermediate Similarity NPC232727
0.768 Intermediate Similarity NPC474409
0.7678 Intermediate Similarity NPC209769
0.7677 Intermediate Similarity NPC176127
0.7675 Intermediate Similarity NPC81939
0.7668 Intermediate Similarity NPC473105
0.7664 Intermediate Similarity NPC470549
0.7656 Intermediate Similarity NPC285558
0.7653 Intermediate Similarity NPC12344
0.7652 Intermediate Similarity NPC63971
0.7652 Intermediate Similarity NPC91868
0.765 Intermediate Similarity NPC477533
0.7636 Intermediate Similarity NPC470018
0.7628 Intermediate Similarity NPC330009
0.7626 Intermediate Similarity NPC474798
0.761 Intermediate Similarity NPC13880
0.7605 Intermediate Similarity NPC100734
0.7605 Intermediate Similarity NPC315634
0.7605 Intermediate Similarity NPC88923
0.7602 Intermediate Similarity NPC157931
0.7566 Intermediate Similarity NPC184680
0.7559 Intermediate Similarity NPC11464
0.7559 Intermediate Similarity NPC470020
0.7558 Intermediate Similarity NPC131885
0.7548 Intermediate Similarity NPC11017
0.7545 Intermediate Similarity NPC132329
0.7542 Intermediate Similarity NPC284685
0.7533 Intermediate Similarity NPC470785
0.7533 Intermediate Similarity NPC470784
0.7525 Intermediate Similarity NPC72980
0.7525 Intermediate Similarity NPC88363
0.7523 Intermediate Similarity NPC473185
0.7523 Intermediate Similarity NPC220337
0.7522 Intermediate Similarity NPC78609
0.75 Intermediate Similarity NPC168922
0.7489 Intermediate Similarity NPC472099
0.7489 Intermediate Similarity NPC252251
0.7488 Intermediate Similarity NPC132539
0.7477 Intermediate Similarity NPC123976
0.7477 Intermediate Similarity NPC264285
0.7477 Intermediate Similarity NPC167860
0.7477 Intermediate Similarity NPC199667
0.7476 Intermediate Similarity NPC295898
0.7465 Intermediate Similarity NPC470931
0.7457 Intermediate Similarity NPC1608
0.7444 Intermediate Similarity NPC74575
0.7441 Intermediate Similarity NPC223427
0.7437 Intermediate Similarity NPC191489
0.743 Intermediate Similarity NPC325297
0.743 Intermediate Similarity NPC473181
0.7427 Intermediate Similarity NPC475190
0.7424 Intermediate Similarity NPC84347
0.7422 Intermediate Similarity NPC475253
0.7422 Intermediate Similarity NPC477531
0.7411 Intermediate Similarity NPC311906
0.7409 Intermediate Similarity NPC86078
0.7407 Intermediate Similarity NPC473180
0.7403 Intermediate Similarity NPC188400
0.7402 Intermediate Similarity NPC246700
0.7401 Intermediate Similarity NPC34770
0.7389 Intermediate Similarity NPC474192
0.7389 Intermediate Similarity NPC475720
0.7389 Intermediate Similarity NPC49547
0.7387 Intermediate Similarity NPC205372
0.7378 Intermediate Similarity NPC209174
0.7373 Intermediate Similarity NPC471080
0.7373 Intermediate Similarity NPC469592
0.7373 Intermediate Similarity NPC89508
0.7364 Intermediate Similarity NPC288987
0.7358 Intermediate Similarity NPC165599
0.7357 Intermediate Similarity NPC473182
0.7356 Intermediate Similarity NPC251090
0.735 Intermediate Similarity NPC270515
0.7349 Intermediate Similarity NPC174758
0.7344 Intermediate Similarity NPC26850
0.7342 Intermediate Similarity NPC303374
0.7342 Intermediate Similarity NPC16352
0.7336 Intermediate Similarity NPC270918
0.7327 Intermediate Similarity NPC94157
0.7317 Intermediate Similarity NPC296527
0.7311 Intermediate Similarity NPC478083
0.7309 Intermediate Similarity NPC322482
0.7308 Intermediate Similarity NPC276517
0.7304 Intermediate Similarity NPC194040
0.7304 Intermediate Similarity NPC131486
0.7302 Intermediate Similarity NPC171787
0.73 Intermediate Similarity NPC244543
0.7299 Intermediate Similarity NPC329793
0.7299 Intermediate Similarity NPC121772
0.7291 Intermediate Similarity NPC62069
0.7289 Intermediate Similarity NPC257851
0.7289 Intermediate Similarity NPC140296
0.7288 Intermediate Similarity NPC67401

  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 NPC310211 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
0.8246 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.823 Intermediate Similarity NPD5632 Approved
0.8018 Intermediate Similarity NPD6790 Phase 1
0.7812 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7731 Intermediate Similarity NPD6242 Discontinued
0.7703 Intermediate Similarity NPD3003 Approved
0.7692 Intermediate Similarity NPD4952 Phase 3
0.7664 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD5658 Approved
0.7619 Intermediate Similarity NPD5482 Discontinued
0.7613 Intermediate Similarity NPD5479 Discontinued
0.7605 Intermediate Similarity NPD7803 Approved
0.7589 Intermediate Similarity NPD4373 Phase 2
0.7581 Intermediate Similarity NPD3257 Approved
0.7542 Intermediate Similarity NPD7955 Approved
0.7542 Intermediate Similarity NPD7956 Approved
0.7523 Intermediate Similarity NPD3259 Approved
0.7523 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1768 Approved
0.75 Intermediate Similarity NPD6962 Phase 2
0.7489 Intermediate Similarity NPD5488 Discontinued
0.7455 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD3258 Approved
0.7437 Intermediate Similarity NPD7708 Approved
0.7419 Intermediate Similarity NPD5903 Approved
0.7419 Intermediate Similarity NPD5902 Approved
0.7416 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD5003 Discontinued
0.7371 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD5512 Phase 3
0.7339 Intermediate Similarity NPD5293 Phase 2
0.7324 Intermediate Similarity NPD5901 Discontinued
0.7319 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD4885 Approved
0.7308 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD4328 Approved
0.7282 Intermediate Similarity NPD2564 Approved
0.7282 Intermediate Similarity NPD2565 Phase 2
0.7281 Intermediate Similarity NPD5416 Discontinued
0.726 Intermediate Similarity NPD1038 Approved
0.726 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD8427 Approved
0.7258 Intermediate Similarity NPD8428 Approved
0.7258 Intermediate Similarity NPD8467 Approved
0.7258 Intermediate Similarity NPD8429 Approved
0.7258 Intermediate Similarity NPD8466 Approved
0.7258 Intermediate Similarity NPD8465 Approved
0.7256 Intermediate Similarity NPD1392 Approved
0.7243 Intermediate Similarity NPD5450 Discontinued
0.7225 Intermediate Similarity NPD4418 Discontinued
0.7224 Intermediate Similarity NPD8363 Approved
0.7224 Intermediate Similarity NPD8364 Approved
0.7222 Intermediate Similarity NPD2916 Discontinued
0.7212 Intermediate Similarity NPD7994 Phase 2
0.7212 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD8459 Approved
0.7211 Intermediate Similarity NPD8460 Approved
0.7189 Intermediate Similarity NPD4506 Discontinued
0.7188 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD5429 Discontinued
0.7167 Intermediate Similarity NPD7417 Discontinued
0.7166 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6985 Discontinued
0.7162 Intermediate Similarity NPD7395 Discontinued
0.7162 Intermediate Similarity NPD4429 Discontinued
0.7161 Intermediate Similarity NPD8358 Approved
0.7156 Intermediate Similarity NPD1166 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD6531 Approved
0.7149 Intermediate Similarity NPD6530 Approved
0.7143 Intermediate Similarity NPD8425 Approved
0.7143 Intermediate Similarity NPD8426 Approved
0.713 Intermediate Similarity NPD7194 Discontinued
0.713 Intermediate Similarity NPD8403 Phase 1
0.7124 Intermediate Similarity NPD3925 Approved
0.7111 Intermediate Similarity NPD6995 Phase 1
0.7101 Intermediate Similarity NPD3986 Discontinued
0.7091 Intermediate Similarity NPD7069 Discontinued
0.7083 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD648 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3945 Discontinued
0.7056 Intermediate Similarity NPD7558 Phase 2
0.7056 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD4724 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5937 Approved
0.7045 Intermediate Similarity NPD5067 Phase 2
0.7045 Intermediate Similarity NPD5066 Phase 2
0.7043 Intermediate Similarity NPD1867 Approved
0.7043 Intermediate Similarity NPD1505 Phase 2
0.7037 Intermediate Similarity NPD6176 Phase 1
0.7014 Intermediate Similarity NPD802 Phase 2
0.701 Intermediate Similarity NPD3920 Phase 2
0.7009 Intermediate Similarity NPD3825 Phase 3
0.7005 Intermediate Similarity NPD3947 Discontinued
0.7 Intermediate Similarity NPD4981 Phase 2
0.6996 Remote Similarity NPD7853 Phase 2
0.6996 Remote Similarity NPD8091 Phase 3
0.6996 Remote Similarity NPD5612 Discontinued
0.6992 Remote Similarity NPD6716 Phase 1
0.6987 Remote Similarity NPD4558 Phase 2
0.6986 Remote Similarity NPD2510 Approved
0.6986 Remote Similarity NPD2509 Approved
0.6978 Remote Similarity NPD6770 Approved
0.6977 Remote Similarity NPD4500 Approved
0.6977 Remote Similarity NPD4501 Approved
0.6966 Remote Similarity NPD5805 Approved
0.6965 Remote Similarity NPD1325 Approved
0.6965 Remote Similarity NPD1326 Approved
0.6964 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5513 Phase 2
0.6959 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6252 Clinical (unspecified phase)
0.6942 Remote Similarity NPD5532 Phase 2
0.6938 Remote Similarity NPD4948 Discontinued
0.6937 Remote Similarity NPD5866 Approved
0.6934 Remote Similarity NPD4539 Phase 1
0.693 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6926 Remote Similarity NPD5022 Discontinued
0.6923 Remote Similarity NPD3006 Discontinued
0.692 Remote Similarity NPD2433 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5913 Phase 3
0.69 Remote Similarity NPD6247 Clinical (unspecified phase)
0.6898 Remote Similarity NPD484 Approved
0.6898 Remote Similarity NPD3289 Phase 3
0.6898 Remote Similarity NPD4600 Approved
0.6898 Remote Similarity NPD4601 Approved
0.6898 Remote Similarity NPD3290 Approved
0.6897 Remote Similarity NPD7688 Phase 1
0.6895 Remote Similarity NPD6245 Phase 2
0.6892 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6892 Remote Similarity NPD7689 Approved
0.6889 Remote Similarity NPD5164 Discontinued
0.6884 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6881 Remote Similarity NPD2920 Discontinued
0.687 Remote Similarity NPD7426 Phase 1
0.687 Remote Similarity NPD6228 Discontinued
0.6869 Remote Similarity NPD6550 Discontinued
0.6864 Remote Similarity NPD7452 Approved
0.6864 Remote Similarity NPD7453 Approved
0.6864 Remote Similarity NPD7222 Phase 2
0.6861 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6858 Remote Similarity NPD1926 Approved
0.6858 Remote Similarity NPD3354 Phase 2
0.6852 Remote Similarity NPD2778 Approved
0.6849 Remote Similarity NPD4795 Phase 2
0.6849 Remote Similarity NPD6517 Phase 3
0.6846 Remote Similarity NPD8102 Discontinued
0.6844 Remote Similarity NPD8489 Phase 1
0.6833 Remote Similarity NPD6376 Discontinued
0.6832 Remote Similarity NPD2844 Phase 3
0.683 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6828 Remote Similarity NPD6974 Phase 3
0.6825 Remote Similarity NPD2792 Approved
0.6822 Remote Similarity NPD4368 Phase 2
0.6822 Remote Similarity NPD6491 Clinical (unspecified phase)
0.682 Remote Similarity NPD1740 Approved
0.682 Remote Similarity NPD1739 Approved
0.6816 Remote Similarity NPD6220 Phase 3
0.6814 Remote Similarity NPD3949 Clinical (unspecified phase)
0.681 Remote Similarity NPD5559 Phase 2
0.68 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6798 Remote Similarity NPD5930 Phase 3
0.6795 Remote Similarity NPD3746 Discontinued
0.6794 Remote Similarity NPD3607 Clinical (unspecified phase)
0.6794 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4499 Approved
0.6789 Remote Similarity NPD4511 Phase 1
0.6784 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6778 Remote Similarity NPD3914 Clinical (unspecified phase)
0.677 Remote Similarity NPD3389 Approved
0.677 Remote Similarity NPD3393 Approved
0.677 Remote Similarity NPD3394 Approved
0.6766 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6763 Remote Similarity NPD6460 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7948 Phase 1
0.6759 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6758 Remote Similarity NPD2779 Approved
0.6757 Remote Similarity NPD2189 Approved
0.6757 Remote Similarity NPD2187 Approved
0.6745 Remote Similarity NPD1534 Approved
0.6744 Remote Similarity NPD6590 Discontinued
0.6742 Remote Similarity NPD2715 Clinical (unspecified phase)
0.6742 Remote Similarity NPD5530 Phase 1
0.6741 Remote Similarity NPD7470 Discontinued
0.6739 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6738 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6737 Remote Similarity NPD2951 Discontinued
0.6735 Remote Similarity NPD8463 Approved
0.673 Remote Similarity NPD5256 Discontinued
0.6725 Remote Similarity NPD7180 Phase 3
0.6716 Remote Similarity NPD5186 Approved
0.6716 Remote Similarity NPD5183 Approved
0.6711 Remote Similarity NPD3815 Phase 1
0.6711 Remote Similarity NPD3816 Phase 1
0.6709 Remote Similarity NPD5924 Discontinued
0.6706 Remote Similarity NPD7393 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