Structure

Physi-Chem Properties

Molecular Weight:  309.14
Volume:  327.787
LogP:  5.324
LogD:  3.559
LogS:  -3.952
# Rotatable Bonds:  4
TPSA:  62.32
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.556
Synthetic Accessibility Score:  2.755
Fsp3:  0.211
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.043
MDCK Permeability:  1.0012370694312267e-05
Pgp-inhibitor:  0.068
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.877
30% Bioavailability (F30%):  0.48

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.097
Plasma Protein Binding (PPB):  90.87906646728516%
Volume Distribution (VD):  0.875
Pgp-substrate:  5.5246992111206055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.769
CYP2C19-inhibitor:  0.922
CYP2C19-substrate:  0.153
CYP2C9-inhibitor:  0.821
CYP2C9-substrate:  0.903
CYP2D6-inhibitor:  0.76
CYP2D6-substrate:  0.853
CYP3A4-inhibitor:  0.447
CYP3A4-substrate:  0.128

ADMET: Excretion

Clearance (CL):  5.536
Half-life (T1/2):  0.187

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.735
Drug-inuced Liver Injury (DILI):  0.417
AMES Toxicity:  0.334
Rat Oral Acute Toxicity:  0.248
Maximum Recommended Daily Dose:  0.937
Skin Sensitization:  0.878
Carcinogencity:  0.381
Eye Corrosion:  0.01
Eye Irritation:  0.677
Respiratory Toxicity:  0.973

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

  Natural Product: NPC150239

Natural Product ID:  NPC150239
Common Name*:   7-Methoxyheptaphylline
IUPAC Name:   2-hydroxy-7-methoxy-1-(3-methylbut-2-enyl)-9H-carbazole-3-carbaldehyde
Synonyms:   7-Methoxyheptaphylline
Standard InCHIKey:  RJWKVZMWLOWCMX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H19NO3/c1-11(2)4-6-15-18-16(8-12(10-21)19(15)22)14-7-5-13(23-3)9-17(14)20-18/h4-5,7-10,20,22H,6H2,1-3H3
SMILES:  O=Cc1cc2c(c(c1O)CC=C(C)C)[nH]c1c2ccc(c1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464275
PubChem CID:   189688
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
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]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. root n.a. PMID[21302964]
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]
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]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota Root barks n.a. n.a. PMID[3236015]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29180 Monachosorum maximowiczii Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29070 Bulbine asphodeloides Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28961 Croton hutchinsonianus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28544 Podocalyx loranthoides Species Picrodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4806 Clausena wallichii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23710 Otholobium pubescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29161 Hyptis urticoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29321 Octopus octopodia Species Octopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29028 Cicer cuneatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28943 Daldinia vernicosa Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27603 Populus candicans Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28735 Helicia erratica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25073 Saccharina latissima Species Laminariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29461 Sarcophyton infundibuliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29497 Delphinium speciosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29387 Eudendrium racemosum Species Eudendriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28427 Gutenbergia marginata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28639 Trixis grisebachii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27349 Rhododendron edgeworthii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29035 Pseudomonas cichorii Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25248 Gloydius blomhoffii Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28500 Griselinia scandens Species Griseliniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29073 Ipomoea carnea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29095 Yucca elata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29518 Nardia scalaris Species Solenostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21978 Clausena harmandiana 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
NPT81 Cell Line A549 Homo sapiens ED50 = 2.16 ug ml-1 PMID[572579]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 1.36 ug ml-1 PMID[572579]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 1680.0 nM PMID[572580]
NPT91 Cell Line KB Homo sapiens IC50 = 2750.0 nM PMID[572580]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 200000.0 nM PMID[572580]
NPT91 Cell Line KB Homo sapiens IC50 = 2750.0 nM PMID[572581]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 1680.0 nM PMID[572581]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 53900.0 nM PMID[572582]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 42300.0 nM PMID[572582]
NPT4715 Cell Line NG108-15 Murinae Activity = 65.53 % PMID[572583]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 100000.0 nM PMID[572583]
NPT140 Organism Artemia Artemia LC50 > 500.0 ppm PMID[572579]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 3.01 ug ml-1 PMID[572579]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.87 ug ml-1 PMID[572579]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 10.0 ug ml-1 PMID[572579]
NPT19 Organism Escherichia coli Escherichia coli MIC = 128.0 ug.mL-1 PMID[572582]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 128.0 ug.mL-1 PMID[572582]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[572583]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 10780.0 nM PMID[572583]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC90 = 20600.0 nM PMID[572584]

☑ 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 NPC150239 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
0.9897 High Similarity NPC247803
0.9641 High Similarity NPC308137
0.9641 High Similarity NPC310211
0.959 High Similarity NPC23294
0.9538 High Similarity NPC303951
0.9453 High Similarity NPC198503
0.9436 High Similarity NPC86834
0.9436 High Similarity NPC210828
0.9403 High Similarity NPC174760
0.94 High Similarity NPC46561
0.9385 High Similarity NPC249583
0.93 High Similarity NPC3207
0.9293 High Similarity NPC87413
0.9254 High Similarity NPC169402
0.925 High Similarity NPC116238
0.9238 High Similarity NPC6786
0.9141 High Similarity NPC39679
0.9126 High Similarity NPC179287
0.91 High Similarity NPC473187
0.9091 High Similarity NPC4687
0.8923 High Similarity NPC70956
0.8923 High Similarity NPC243834
0.8883 High Similarity NPC208084
0.885 High Similarity NPC45190
0.8725 High Similarity NPC9894
0.8607 High Similarity NPC291535
0.8607 High Similarity NPC475085
0.8607 High Similarity NPC475112
0.859 High Similarity NPC89549
0.8571 High Similarity NPC300156
0.8571 High Similarity NPC225279
0.8544 High Similarity NPC187501
0.8529 High Similarity NPC193777
0.848 Intermediate Similarity NPC476106
0.8476 Intermediate Similarity NPC184408
0.8429 Intermediate Similarity NPC293151
0.841 Intermediate Similarity NPC94943
0.8408 Intermediate Similarity NPC72211
0.838 Intermediate Similarity NPC274640
0.8364 Intermediate Similarity NPC51388
0.8359 Intermediate Similarity NPC190007
0.8357 Intermediate Similarity NPC280799
0.835 Intermediate Similarity NPC283117
0.835 Intermediate Similarity NPC131017
0.8333 Intermediate Similarity NPC118228
0.8318 Intermediate Similarity NPC144452
0.8308 Intermediate Similarity NPC70259
0.8308 Intermediate Similarity NPC212535
0.8286 Intermediate Similarity NPC39500
0.8282 Intermediate Similarity NPC473188
0.8278 Intermediate Similarity NPC294375
0.8259 Intermediate Similarity NPC43787
0.8259 Intermediate Similarity NPC205934
0.8238 Intermediate Similarity NPC48353
0.8204 Intermediate Similarity NPC162484
0.8182 Intermediate Similarity NPC160381
0.8157 Intermediate Similarity NPC97746
0.8136 Intermediate Similarity NPC474688
0.8136 Intermediate Similarity NPC474701
0.8128 Intermediate Similarity NPC194740
0.8116 Intermediate Similarity NPC134848
0.8093 Intermediate Similarity NPC473179
0.8089 Intermediate Similarity NPC475844
0.8088 Intermediate Similarity NPC153042
0.8086 Intermediate Similarity NPC321428
0.8047 Intermediate Similarity NPC473041
0.8047 Intermediate Similarity NPC303658
0.8037 Intermediate Similarity NPC152768
0.8037 Intermediate Similarity NPC148183
0.8027 Intermediate Similarity NPC39370
0.8019 Intermediate Similarity NPC267423
0.8019 Intermediate Similarity NPC476044
0.8018 Intermediate Similarity NPC473186
0.8018 Intermediate Similarity NPC477532
0.8009 Intermediate Similarity NPC209769
0.8 Intermediate Similarity NPC183777
0.7981 Intermediate Similarity NPC135887
0.7981 Intermediate Similarity NPC199277
0.7961 Intermediate Similarity NPC306376
0.7953 Intermediate Similarity NPC330009
0.7926 Intermediate Similarity NPC298436
0.7925 Intermediate Similarity NPC201697
0.7923 Intermediate Similarity NPC128823
0.79 Intermediate Similarity NPC84478
0.7887 Intermediate Similarity NPC11464
0.7883 Intermediate Similarity NPC471762
0.7879 Intermediate Similarity NPC91868
0.7879 Intermediate Similarity NPC63971
0.7877 Intermediate Similarity NPC475910
0.7857 Intermediate Similarity NPC474409
0.7854 Intermediate Similarity NPC60621
0.785 Intermediate Similarity NPC146418
0.7838 Intermediate Similarity NPC473185
0.7834 Intermediate Similarity NPC305984
0.7828 Intermediate Similarity NPC21638
0.7822 Intermediate Similarity NPC473105
0.782 Intermediate Similarity NPC470930
0.7814 Intermediate Similarity NPC12344
0.7814 Intermediate Similarity NPC264176
0.7804 Intermediate Similarity NPC269367
0.7803 Intermediate Similarity NPC252251
0.7799 Intermediate Similarity NPC329747
0.7793 Intermediate Similarity NPC470931
0.7783 Intermediate Similarity NPC122436
0.7778 Intermediate Similarity NPC132329
0.7773 Intermediate Similarity NPC223427
0.7763 Intermediate Similarity NPC470784
0.7749 Intermediate Similarity NPC78609
0.7745 Intermediate Similarity NPC246700
0.7733 Intermediate Similarity NPC477531
0.7723 Intermediate Similarity NPC66777
0.7719 Intermediate Similarity NPC184680
0.7717 Intermediate Similarity NPC264285
0.77 Intermediate Similarity NPC88363
0.77 Intermediate Similarity NPC72980
0.7689 Intermediate Similarity NPC209174
0.7686 Intermediate Similarity NPC470785
0.7686 Intermediate Similarity NPC101350
0.7685 Intermediate Similarity NPC220337
0.7665 Intermediate Similarity NPC473182
0.7661 Intermediate Similarity NPC16066
0.7659 Intermediate Similarity NPC242928
0.7647 Intermediate Similarity NPC323969
0.7642 Intermediate Similarity NPC235685
0.7639 Intermediate Similarity NPC471304
0.7639 Intermediate Similarity NPC475666
0.7636 Intermediate Similarity NPC96321
0.7626 Intermediate Similarity NPC170114
0.7615 Intermediate Similarity NPC469592
0.7615 Intermediate Similarity NPC471080
0.76 Intermediate Similarity NPC478078
0.7597 Intermediate Similarity NPC81939
0.7593 Intermediate Similarity NPC325297
0.7585 Intermediate Similarity NPC67401
0.758 Intermediate Similarity NPC470549
0.7577 Intermediate Similarity NPC260434
0.7573 Intermediate Similarity NPC128751
0.757 Intermediate Similarity NPC285558
0.7568 Intermediate Similarity NPC477533
0.7565 Intermediate Similarity NPC473183
0.7564 Intermediate Similarity NPC469734
0.7556 Intermediate Similarity NPC202503
0.7555 Intermediate Similarity NPC473184
0.7554 Intermediate Similarity NPC188400
0.7545 Intermediate Similarity NPC469928
0.7545 Intermediate Similarity NPC205372
0.7545 Intermediate Similarity NPC74969
0.7544 Intermediate Similarity NPC475720
0.7544 Intermediate Similarity NPC474192
0.7536 Intermediate Similarity NPC469497
0.7536 Intermediate Similarity NPC106833
0.7531 Intermediate Similarity NPC315634
0.7531 Intermediate Similarity NPC88923
0.7531 Intermediate Similarity NPC100734
0.7531 Intermediate Similarity NPC472589
0.7523 Intermediate Similarity NPC213530
0.7523 Intermediate Similarity NPC193267
0.7521 Intermediate Similarity NPC472588
0.7511 Intermediate Similarity NPC312645
0.75 Intermediate Similarity NPC16352
0.75 Intermediate Similarity NPC217176
0.75 Intermediate Similarity NPC220851
0.75 Intermediate Similarity NPC270918
0.7479 Intermediate Similarity NPC189079
0.7478 Intermediate Similarity NPC470018
0.7477 Intermediate Similarity NPC469594
0.7476 Intermediate Similarity NPC276517
0.7476 Intermediate Similarity NPC194040
0.7469 Intermediate Similarity NPC284685
0.7466 Intermediate Similarity NPC322064
0.7465 Intermediate Similarity NPC171787
0.7465 Intermediate Similarity NPC11017
0.7463 Intermediate Similarity NPC62069
0.7457 Intermediate Similarity NPC131486
0.7455 Intermediate Similarity NPC89508
0.7454 Intermediate Similarity NPC472286
0.7454 Intermediate Similarity NPC472287
0.7448 Intermediate Similarity NPC244543
0.7447 Intermediate Similarity NPC208522
0.7447 Intermediate Similarity NPC160898
0.7445 Intermediate Similarity NPC157931
0.7444 Intermediate Similarity NPC74360
0.7442 Intermediate Similarity NPC165599
0.7437 Intermediate Similarity NPC133609
0.7436 Intermediate Similarity NPC76982
0.743 Intermediate Similarity NPC232727
0.7425 Intermediate Similarity NPC475816
0.7419 Intermediate Similarity NPC53344
0.7418 Intermediate Similarity NPC132385
0.7415 Intermediate Similarity NPC176127
0.7414 Intermediate Similarity NPC15801
0.7411 Intermediate Similarity NPC472099
0.7411 Intermediate Similarity NPC132642
0.7411 Intermediate Similarity NPC469439
0.7409 Intermediate Similarity NPC316981
0.74 Intermediate Similarity NPC237901
0.74 Intermediate Similarity NPC195788
0.7397 Intermediate Similarity NPC199667
0.7397 Intermediate Similarity NPC470020
0.7395 Intermediate Similarity NPC165964

  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 NPC150239 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
0.8148 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.8131 Intermediate Similarity NPD5632 Approved
0.793 Intermediate Similarity NPD6790 Phase 1
0.7907 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7783 Intermediate Similarity NPD3003 Approved
0.7729 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD5488 Discontinued
0.7665 Intermediate Similarity NPD4373 Phase 2
0.7655 Intermediate Similarity NPD6962 Phase 2
0.7647 Intermediate Similarity NPD6242 Discontinued
0.7611 Intermediate Similarity NPD4952 Phase 3
0.7611 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD3258 Approved
0.76 Intermediate Similarity NPD3259 Approved
0.7571 Intermediate Similarity NPD5003 Discontinued
0.757 Intermediate Similarity NPD5901 Discontinued
0.7546 Intermediate Similarity NPD2916 Discontinued
0.7546 Intermediate Similarity NPD5658 Approved
0.7542 Intermediate Similarity NPD5482 Discontinued
0.7542 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD5479 Discontinued
0.7531 Intermediate Similarity NPD7803 Approved
0.7524 Intermediate Similarity NPD5512 Phase 3
0.7523 Intermediate Similarity NPD5416 Discontinued
0.75 Intermediate Similarity NPD5902 Approved
0.75 Intermediate Similarity NPD5903 Approved
0.75 Intermediate Similarity NPD1768 Approved
0.7469 Intermediate Similarity NPD7956 Approved
0.7469 Intermediate Similarity NPD7955 Approved
0.7452 Intermediate Similarity NPD2564 Approved
0.7452 Intermediate Similarity NPD2565 Phase 2
0.7445 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD3925 Approved
0.7421 Intermediate Similarity NPD3257 Approved
0.7407 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD8465 Approved
0.74 Intermediate Similarity NPD8429 Approved
0.74 Intermediate Similarity NPD8466 Approved
0.74 Intermediate Similarity NPD8467 Approved
0.74 Intermediate Similarity NPD8428 Approved
0.74 Intermediate Similarity NPD8427 Approved
0.7399 Intermediate Similarity NPD7395 Discontinued
0.7395 Intermediate Similarity NPD3986 Discontinued
0.7393 Intermediate Similarity NPD7417 Discontinued
0.7381 Intermediate Similarity NPD5937 Approved
0.7368 Intermediate Similarity NPD4328 Approved
0.7368 Intermediate Similarity NPD8363 Approved
0.7368 Intermediate Similarity NPD8364 Approved
0.7366 Intermediate Similarity NPD6531 Approved
0.7366 Intermediate Similarity NPD6530 Approved
0.7366 Intermediate Similarity NPD7708 Approved
0.7352 Intermediate Similarity NPD8460 Approved
0.7352 Intermediate Similarity NPD8459 Approved
0.7345 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD5429 Discontinued
0.7336 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7309 Intermediate Similarity NPD5612 Discontinued
0.7309 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD7558 Phase 2
0.7283 Intermediate Similarity NPD8426 Approved
0.7283 Intermediate Similarity NPD8425 Approved
0.7269 Intermediate Similarity NPD6995 Phase 1
0.7265 Intermediate Similarity NPD5293 Phase 2
0.7264 Intermediate Similarity NPD1038 Approved
0.726 Intermediate Similarity NPD1392 Approved
0.7252 Intermediate Similarity NPD7069 Discontinued
0.7244 Intermediate Similarity NPD6985 Discontinued
0.7241 Intermediate Similarity NPD4885 Approved
0.724 Intermediate Similarity NPD648 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6716 Phase 1
0.7213 Intermediate Similarity NPD8091 Phase 3
0.7212 Intermediate Similarity NPD7194 Discontinued
0.72 Intermediate Similarity NPD5164 Discontinued
0.7198 Intermediate Similarity NPD1505 Phase 2
0.7191 Intermediate Similarity NPD5805 Approved
0.719 Intermediate Similarity NPD4948 Discontinued
0.7183 Intermediate Similarity NPD4539 Phase 1
0.7182 Intermediate Similarity NPD7453 Approved
0.7182 Intermediate Similarity NPD7222 Phase 2
0.7182 Intermediate Similarity NPD7452 Approved
0.7177 Intermediate Similarity NPD5450 Discontinued
0.715 Intermediate Similarity NPD4418 Discontinued
0.7149 Intermediate Similarity NPD7853 Phase 2
0.7149 Intermediate Similarity NPD6376 Discontinued
0.7143 Intermediate Similarity NPD7994 Phase 2
0.7143 Intermediate Similarity NPD1325 Approved
0.7143 Intermediate Similarity NPD1326 Approved
0.7136 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD5066 Phase 2
0.713 Intermediate Similarity NPD5067 Phase 2
0.713 Intermediate Similarity NPD7703 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD1867 Approved
0.7117 Intermediate Similarity NPD4506 Discontinued
0.711 Intermediate Similarity NPD4511 Phase 1
0.7103 Intermediate Similarity NPD7689 Approved
0.7103 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD5866 Approved
0.7095 Intermediate Similarity NPD8358 Approved
0.7094 Intermediate Similarity NPD2844 Phase 3
0.7093 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD4429 Discontinued
0.7087 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7948 Phase 1
0.7082 Intermediate Similarity NPD4981 Phase 2
0.7075 Intermediate Similarity NPD2792 Approved
0.707 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD484 Approved
0.7064 Intermediate Similarity NPD4600 Approved
0.7064 Intermediate Similarity NPD4601 Approved
0.7064 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD8403 Phase 1
0.7048 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD2920 Discontinued
0.7035 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD2951 Discontinued
0.7021 Intermediate Similarity NPD3746 Discontinued
0.702 Intermediate Similarity NPD5532 Phase 2
0.702 Intermediate Similarity NPD6252 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3354 Phase 2
0.7018 Intermediate Similarity NPD1926 Approved
0.7014 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5022 Discontinued
0.7005 Intermediate Similarity NPD7238 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6517 Phase 3
0.6992 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6991 Remote Similarity NPD3945 Discontinued
0.6991 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6991 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6987 Remote Similarity NPD6974 Phase 3
0.6983 Remote Similarity NPD6247 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5530 Phase 1
0.6981 Remote Similarity NPD8489 Phase 1
0.6978 Remote Similarity NPD6220 Phase 3
0.6978 Remote Similarity NPD4502 Phase 2
0.6976 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6176 Phase 1
0.6966 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6953 Remote Similarity NPD3263 Phase 3
0.6953 Remote Similarity NPD7426 Phase 1
0.6952 Remote Similarity NPD4204 Approved
0.6952 Remote Similarity NPD4203 Approved
0.6951 Remote Similarity NPD8463 Approved
0.6949 Remote Similarity NPD5151 Clinical (unspecified phase)
0.6944 Remote Similarity NPD802 Phase 2
0.6944 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3825 Phase 3
0.6938 Remote Similarity NPD7181 Phase 3
0.6938 Remote Similarity NPD3920 Phase 2
0.6937 Remote Similarity NPD3947 Discontinued
0.6933 Remote Similarity NPD1166 Clinical (unspecified phase)
0.6926 Remote Similarity NPD8102 Discontinued
0.6926 Remote Similarity NPD4558 Phase 2
0.692 Remote Similarity NPD2509 Approved
0.692 Remote Similarity NPD2510 Approved
0.6917 Remote Similarity NPD4561 Discontinued
0.6913 Remote Similarity NPD4312 Approved
0.6913 Remote Similarity NPD6770 Approved
0.6912 Remote Similarity NPD6590 Discontinued
0.6909 Remote Similarity NPD4500 Approved
0.6909 Remote Similarity NPD4501 Approved
0.6906 Remote Similarity NPD2715 Clinical (unspecified phase)
0.6904 Remote Similarity NPD4368 Phase 2
0.6903 Remote Similarity NPD7470 Discontinued
0.69 Remote Similarity NPD3949 Clinical (unspecified phase)
0.6892 Remote Similarity NPD5513 Phase 2
0.6892 Remote Similarity NPD2121 Clinical (unspecified phase)
0.687 Remote Similarity NPD7878 Phase 2
0.6863 Remote Similarity NPD955 Approved
0.6862 Remote Similarity NPD3006 Discontinued
0.6861 Remote Similarity NPD2721 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5913 Phase 3
0.6851 Remote Similarity NPD4845 Discontinued
0.6849 Remote Similarity NPD6494 Phase 2
0.6848 Remote Similarity NPD6709 Phase 3
0.6847 Remote Similarity NPD2779 Approved
0.6846 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3243 Approved
0.6835 Remote Similarity NPD7688 Phase 1
0.6833 Remote Similarity NPD3289 Phase 3
0.6833 Remote Similarity NPD3290 Approved
0.683 Remote Similarity NPD6245 Phase 2
0.683 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6826 Remote Similarity NPD1976 Approved
0.6825 Remote Similarity NPD5445 Approved
0.6824 Remote Similarity NPD7219 Approved
0.6824 Remote Similarity NPD7221 Approved
0.6818 Remote Similarity NPD7946 Pre-registration
0.6818 Remote Similarity NPD4668 Phase 2
0.6818 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6228 Discontinued
0.681 Remote Similarity NPD7180 Phase 3

  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