Structure

Physi-Chem Properties

Molecular Weight:  236.07
Volume:  229.764
LogP:  0.681
LogD:  0.785
LogS:  -1.913
# Rotatable Bonds:  1
TPSA:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.494
Synthetic Accessibility Score:  4.772
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.632
MDCK Permeability:  2.190274062741082e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.205
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.849
Plasma Protein Binding (PPB):  71.96512603759766%
Volume Distribution (VD):  1.868
Pgp-substrate:  26.0091609954834%

ADMET: Metabolism

CYP1A2-inhibitor:  0.803
CYP1A2-substrate:  0.222
CYP2C19-inhibitor:  0.098
CYP2C19-substrate:  0.519
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.064
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.052
CYP3A4-substrate:  0.197

ADMET: Excretion

Clearance (CL):  1.755
Half-life (T1/2):  0.697

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.472
Drug-inuced Liver Injury (DILI):  0.748
AMES Toxicity:  0.953
Rat Oral Acute Toxicity:  0.987
Maximum Recommended Daily Dose:  0.951
Skin Sensitization:  0.902
Carcinogencity:  0.932
Eye Corrosion:  0.009
Eye Irritation:  0.427
Respiratory Toxicity:  0.982

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

  Natural Product: NPC131864

Natural Product ID:  NPC131864
Common Name*:   Sid436559
IUPAC Name:   (7R,8S)-7,8-dihydroxy-3,7-dimethyl-6-oxo-8H-isochromene-5-carbaldehyde
Synonyms:  
Standard InCHIKey:  QVMUHZHZYCDMAI-RYUDHWBXSA-N
Standard InCHI:  InChI=1S/C12H12O5/c1-6-3-7-8(4-13)10(14)12(2,16)11(15)9(7)5-17-6/h3-5,11,15-16H,1-2H3/t11-,12-/m0/s1
SMILES:  O=CC1=C2C=C(C)OC=C2[C@@H]([C@@](C1=O)(C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1976714
PubChem CID:   40604
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0003477] Azaphilones

*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
NPO501 Mycoleptodiscus indicus Species Magnaporthaceae Eukaryota n.a. n.a. n.a. PMID[24387625]
NPO501 Mycoleptodiscus indicus Species Magnaporthaceae 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. 28575.91 nM PMID[508939]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 37239.17 nM PMID[508939]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 16788.04 nM PMID[508939]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 65463.62 nM PMID[508939]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 29444.22 nM PMID[508939]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 24603.68 nM PMID[508939]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 26424.09 nM PMID[508939]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 24266.1 nM PMID[508939]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 27861.21 nM PMID[508939]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1555.97 nM PMID[508939]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 15595.53 nM PMID[508939]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 24266.1 nM PMID[508939]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 25234.81 nM PMID[508939]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 53826.98 nM PMID[508939]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 64714.26 nM PMID[508939]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 50815.94 nM PMID[508939]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 981.75 nM PMID[508939]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 28906.8 nM PMID[508939]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 29376.5 nM PMID[508939]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 22438.82 nM PMID[508939]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 17218.69 nM PMID[508939]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 33265.96 nM PMID[508939]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 54325.03 nM PMID[508939]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 41879.36 nM PMID[508939]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 15885.47 nM PMID[508939]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 39084.09 nM PMID[508939]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 27669.42 nM PMID[508939]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 14962.36 nM PMID[508939]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 24210.29 nM PMID[508939]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 1207.81 nM PMID[508939]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 27989.81 nM PMID[508939]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 19098.53 nM PMID[508939]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 13772.09 nM PMID[508939]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 22335.72 nM PMID[508939]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 28773.98 nM PMID[508939]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 24888.57 nM PMID[508939]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 39355.01 nM PMID[508939]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 46881.34 nM PMID[508939]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 29922.65 nM PMID[508939]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 19453.6 nM PMID[508939]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 23496.33 nM PMID[508939]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 14454.4 nM PMID[508939]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 33496.54 nM PMID[508939]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 32136.61 nM PMID[508939]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 35727.28 nM PMID[508939]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 33189.45 nM PMID[508939]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 38547.84 nM PMID[508939]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 28906.8 nM PMID[508939]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 21478.3 nM PMID[508939]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 25763.21 nM PMID[508939]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 25234.81 nM PMID[508939]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 37670.38 nM PMID[508939]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 28054.34 nM PMID[508939]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 16749.43 nM PMID[508939]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 54450.27 nM PMID[508939]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 30408.85 nM PMID[508939]
NPT399 Cell Line SF-295 Homo sapiens IC50 = 28000.0 nM PMID[508940]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 38800.0 nM PMID[508940]
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 34300.0 nM PMID[508940]
NPT27 Others Unspecified IC50 > 113000.0 nM PMID[508940]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 12900.0 nM PMID[508940]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 80500.0 nM PMID[508940]
NPT841 Organism Leishmania major Leishmania major LD50 = 20.5 uM PMID[508940]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 8.5 % PMID[508941]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 3.32 % PMID[508941]
NPT20 Organism Candida albicans Candida albicans Inhibition = 4.9 % PMID[508941]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -12.05 % PMID[508941]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = -0.76 % PMID[508941]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 11.76 % PMID[508941]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 9.69 % PMID[508941]

☑ 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 NPC131864 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
0.8298 Intermediate Similarity NPC471698
0.8125 Intermediate Similarity NPC471694
0.7912 Intermediate Similarity NPC187529
0.7684 Intermediate Similarity NPC469464
0.7549 Intermediate Similarity NPC320294
0.75 Intermediate Similarity NPC35717
0.7473 Intermediate Similarity NPC275766
0.7447 Intermediate Similarity NPC203795
0.7423 Intermediate Similarity NPC32552
0.7416 Intermediate Similarity NPC97173
0.7404 Intermediate Similarity NPC469852
0.74 Intermediate Similarity NPC20066
0.7353 Intermediate Similarity NPC224172
0.7347 Intermediate Similarity NPC282644
0.7347 Intermediate Similarity NPC29798
0.7333 Intermediate Similarity NPC469853
0.7327 Intermediate Similarity NPC306908
0.732 Intermediate Similarity NPC477684
0.732 Intermediate Similarity NPC265856
0.7292 Intermediate Similarity NPC472008
0.7263 Intermediate Similarity NPC196381
0.7245 Intermediate Similarity NPC142838
0.7238 Intermediate Similarity NPC85529
0.7238 Intermediate Similarity NPC32006
0.7228 Intermediate Similarity NPC239895
0.7222 Intermediate Similarity NPC82666
0.7212 Intermediate Similarity NPC473144
0.7212 Intermediate Similarity NPC297281
0.7188 Intermediate Similarity NPC472007
0.7188 Intermediate Similarity NPC23622
0.7184 Intermediate Similarity NPC469851
0.7143 Intermediate Similarity NPC248624
0.7143 Intermediate Similarity NPC478122
0.7129 Intermediate Similarity NPC93271
0.7129 Intermediate Similarity NPC472734
0.7129 Intermediate Similarity NPC472733
0.7129 Intermediate Similarity NPC135576
0.7128 Intermediate Similarity NPC477786
0.7128 Intermediate Similarity NPC477784
0.7128 Intermediate Similarity NPC477785
0.71 Intermediate Similarity NPC196227
0.7091 Intermediate Similarity NPC326264
0.7087 Intermediate Similarity NPC215253
0.7087 Intermediate Similarity NPC185253
0.7083 Intermediate Similarity NPC472009
0.7079 Intermediate Similarity NPC122244
0.7071 Intermediate Similarity NPC172101
0.7071 Intermediate Similarity NPC146852
0.7071 Intermediate Similarity NPC116726
0.7059 Intermediate Similarity NPC472731
0.7059 Intermediate Similarity NPC472732
0.7048 Intermediate Similarity NPC118902
0.7048 Intermediate Similarity NPC104161
0.7048 Intermediate Similarity NPC469980
0.7041 Intermediate Similarity NPC95364
0.7041 Intermediate Similarity NPC142159
0.7033 Intermediate Similarity NPC473536
0.703 Intermediate Similarity NPC279313
0.703 Intermediate Similarity NPC91408
0.703 Intermediate Similarity NPC31021
0.7 Intermediate Similarity NPC61275
0.699 Remote Similarity NPC153776
0.699 Remote Similarity NPC166770
0.699 Remote Similarity NPC472729
0.699 Remote Similarity NPC177680
0.699 Remote Similarity NPC472730
0.699 Remote Similarity NPC300584
0.6979 Remote Similarity NPC281172
0.6979 Remote Similarity NPC15807
0.6979 Remote Similarity NPC307112
0.697 Remote Similarity NPC274075
0.697 Remote Similarity NPC166554
0.6966 Remote Similarity NPC261316
0.6966 Remote Similarity NPC49737
0.6952 Remote Similarity NPC39996
0.6947 Remote Similarity NPC110150
0.6947 Remote Similarity NPC66764
0.6944 Remote Similarity NPC327106
0.6939 Remote Similarity NPC53454
0.6937 Remote Similarity NPC321496
0.6931 Remote Similarity NPC78159
0.6931 Remote Similarity NPC477241
0.6923 Remote Similarity NPC472728
0.6923 Remote Similarity NPC472727
0.6923 Remote Similarity NPC46761
0.6915 Remote Similarity NPC67254
0.6915 Remote Similarity NPC470298
0.6907 Remote Similarity NPC262026
0.69 Remote Similarity NPC166110
0.69 Remote Similarity NPC32944
0.69 Remote Similarity NPC193396
0.6893 Remote Similarity NPC471916
0.6893 Remote Similarity NPC134083
0.6893 Remote Similarity NPC27105
0.6887 Remote Similarity NPC271059
0.6887 Remote Similarity NPC25666
0.6887 Remote Similarity NPC473624
0.6881 Remote Similarity NPC23497
0.6875 Remote Similarity NPC247069
0.6863 Remote Similarity NPC227494
0.6857 Remote Similarity NPC471699
0.6852 Remote Similarity NPC199107
0.6852 Remote Similarity NPC232969
0.6852 Remote Similarity NPC266514
0.6837 Remote Similarity NPC476079
0.6837 Remote Similarity NPC103743
0.6837 Remote Similarity NPC113370
0.6832 Remote Similarity NPC248193
0.6827 Remote Similarity NPC471331
0.6827 Remote Similarity NPC471330
0.6827 Remote Similarity NPC99657
0.6827 Remote Similarity NPC203388
0.6827 Remote Similarity NPC472687
0.6822 Remote Similarity NPC213366
0.6809 Remote Similarity NPC470946
0.6809 Remote Similarity NPC470947
0.6809 Remote Similarity NPC74086
0.6809 Remote Similarity NPC470945
0.6804 Remote Similarity NPC79573
0.6804 Remote Similarity NPC32037
0.68 Remote Similarity NPC471399
0.68 Remote Similarity NPC134321
0.6796 Remote Similarity NPC279722
0.6774 Remote Similarity NPC264391
0.6771 Remote Similarity NPC185256
0.6771 Remote Similarity NPC251475
0.6771 Remote Similarity NPC169941
0.6765 Remote Similarity NPC472976
0.6765 Remote Similarity NPC469819
0.6765 Remote Similarity NPC472977
0.6765 Remote Similarity NPC114162
0.6765 Remote Similarity NPC473162
0.6759 Remote Similarity NPC471333
0.6759 Remote Similarity NPC478052
0.6759 Remote Similarity NPC1679
0.6759 Remote Similarity NPC471332
0.6757 Remote Similarity NPC476023
0.6739 Remote Similarity NPC477708
0.6737 Remote Similarity NPC119229
0.6733 Remote Similarity NPC99380
0.6733 Remote Similarity NPC475441
0.6731 Remote Similarity NPC20078
0.6731 Remote Similarity NPC473574
0.6727 Remote Similarity NPC471400
0.6727 Remote Similarity NPC87335
0.6724 Remote Similarity NPC478051
0.6701 Remote Similarity NPC136114
0.6701 Remote Similarity NPC469809
0.6701 Remote Similarity NPC40687
0.67 Remote Similarity NPC472676
0.67 Remote Similarity NPC472688
0.6699 Remote Similarity NPC476245
0.6699 Remote Similarity NPC280725
0.6698 Remote Similarity NPC470184
0.6698 Remote Similarity NPC207885
0.6698 Remote Similarity NPC112613
0.6698 Remote Similarity NPC472637
0.6696 Remote Similarity NPC66108
0.6667 Remote Similarity NPC472072
0.6667 Remote Similarity NPC47450
0.6667 Remote Similarity NPC40170
0.6667 Remote Similarity NPC99760
0.6667 Remote Similarity NPC272267
0.6667 Remote Similarity NPC471738
0.6636 Remote Similarity NPC168883
0.6636 Remote Similarity NPC478176
0.6636 Remote Similarity NPC264819
0.6635 Remote Similarity NPC318082
0.6635 Remote Similarity NPC472675
0.6635 Remote Similarity NPC21681
0.6635 Remote Similarity NPC192428
0.6634 Remote Similarity NPC472325
0.6634 Remote Similarity NPC316228
0.6634 Remote Similarity NPC128672
0.6633 Remote Similarity NPC70685
0.6633 Remote Similarity NPC255174
0.6629 Remote Similarity NPC474060
0.6604 Remote Similarity NPC198880
0.6604 Remote Similarity NPC174314
0.6602 Remote Similarity NPC181393
0.6602 Remote Similarity NPC217624
0.6598 Remote Similarity NPC475083
0.6598 Remote Similarity NPC64600
0.6596 Remote Similarity NPC178852
0.6596 Remote Similarity NPC231739
0.6591 Remote Similarity NPC269985
0.6581 Remote Similarity NPC473145
0.6581 Remote Similarity NPC31641
0.6581 Remote Similarity NPC476815
0.6579 Remote Similarity NPC80650
0.6577 Remote Similarity NPC300026
0.6577 Remote Similarity NPC214644
0.6577 Remote Similarity NPC20192
0.6574 Remote Similarity NPC131366
0.6574 Remote Similarity NPC475050
0.6571 Remote Similarity NPC474785
0.6571 Remote Similarity NPC472073
0.6571 Remote Similarity NPC472074
0.6571 Remote Similarity NPC474938
0.6571 Remote Similarity NPC161147

  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 NPC131864 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
0.6809 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6635 Remote Similarity NPD4697 Phase 3
0.6633 Remote Similarity NPD1696 Phase 3
0.6598 Remote Similarity NPD6110 Phase 1
0.6489 Remote Similarity NPD4756 Discovery
0.6346 Remote Similarity NPD5778 Approved
0.6346 Remote Similarity NPD5779 Approved
0.633 Remote Similarity NPD5211 Phase 2
0.6292 Remote Similarity NPD3704 Approved
0.6262 Remote Similarity NPD4755 Approved
0.6228 Remote Similarity NPD4634 Approved
0.6216 Remote Similarity NPD5141 Approved
0.6214 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6214 Remote Similarity NPD6101 Approved
0.6186 Remote Similarity NPD7115 Discovery
0.6168 Remote Similarity NPD5221 Approved
0.6168 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5222 Approved
0.6162 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6147 Remote Similarity NPD5286 Approved
0.6147 Remote Similarity NPD5285 Approved
0.6147 Remote Similarity NPD4696 Approved
0.6147 Remote Similarity NPD4700 Approved
0.6132 Remote Similarity NPD5282 Discontinued
0.6111 Remote Similarity NPD5173 Approved
0.6111 Remote Similarity NPD7331 Phase 2
0.6095 Remote Similarity NPD7983 Approved
0.6095 Remote Similarity NPD6411 Approved
0.6091 Remote Similarity NPD5223 Approved
0.6078 Remote Similarity NPD5279 Phase 3
0.6078 Remote Similarity NPD3618 Phase 1
0.6058 Remote Similarity NPD5328 Approved
0.6036 Remote Similarity NPD5224 Approved
0.6036 Remote Similarity NPD5226 Approved
0.6036 Remote Similarity NPD4633 Approved
0.6036 Remote Similarity NPD5225 Approved
0.6018 Remote Similarity NPD5739 Approved
0.6018 Remote Similarity NPD6675 Approved
0.6018 Remote Similarity NPD7128 Approved
0.6018 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD6372 Approved
0.6 Remote Similarity NPD6373 Approved
0.5984 Remote Similarity NPD8513 Phase 3
0.5982 Remote Similarity NPD5175 Approved
0.5982 Remote Similarity NPD5174 Approved
0.5982 Remote Similarity NPD4754 Approved
0.5965 Remote Similarity NPD5701 Approved
0.5965 Remote Similarity NPD5697 Approved
0.596 Remote Similarity NPD4695 Discontinued
0.5955 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5943 Remote Similarity NPD6079 Approved
0.5932 Remote Similarity NPD4632 Approved
0.5922 Remote Similarity NPD5786 Approved
0.5913 Remote Similarity NPD6899 Approved
0.5913 Remote Similarity NPD6881 Approved
0.5913 Remote Similarity NPD7320 Approved
0.5913 Remote Similarity NPD6011 Approved
0.5909 Remote Similarity NPD4225 Approved
0.5905 Remote Similarity NPD4753 Phase 2
0.5902 Remote Similarity NPD6319 Approved
0.5897 Remote Similarity NPD6649 Approved
0.5897 Remote Similarity NPD6650 Approved
0.5877 Remote Similarity NPD4767 Approved
0.5877 Remote Similarity NPD4768 Approved
0.5862 Remote Similarity NPD6012 Approved
0.5862 Remote Similarity NPD6014 Approved
0.5862 Remote Similarity NPD6013 Approved
0.5854 Remote Similarity NPD8516 Approved
0.5854 Remote Similarity NPD8517 Approved
0.5854 Remote Similarity NPD8515 Approved
0.5847 Remote Similarity NPD8297 Approved
0.5842 Remote Similarity NPD3667 Approved
0.5825 Remote Similarity NPD5363 Approved
0.5812 Remote Similarity NPD7102 Approved
0.5812 Remote Similarity NPD6883 Approved
0.5812 Remote Similarity NPD7290 Approved
0.58 Remote Similarity NPD4252 Approved
0.5794 Remote Similarity NPD7515 Phase 2
0.578 Remote Similarity NPD4629 Approved
0.578 Remote Similarity NPD1698 Clinical (unspecified phase)
0.578 Remote Similarity NPD5210 Approved
0.5776 Remote Similarity NPD4729 Approved
0.5776 Remote Similarity NPD4730 Approved
0.5776 Remote Similarity NPD5128 Approved
0.5772 Remote Similarity NPD6054 Approved
0.5772 Remote Similarity NPD6059 Approved
0.5769 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5769 Remote Similarity NPD4694 Approved
0.5769 Remote Similarity NPD5280 Approved
0.5763 Remote Similarity NPD6869 Approved
0.5763 Remote Similarity NPD6847 Approved
0.5763 Remote Similarity NPD6617 Approved
0.5763 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5763 Remote Similarity NPD8130 Phase 1
0.5761 Remote Similarity NPD6108 Clinical (unspecified phase)
0.576 Remote Similarity NPD8328 Phase 3
0.5755 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5743 Remote Similarity NPD5369 Approved
0.5741 Remote Similarity NPD4202 Approved
0.5728 Remote Similarity NPD3666 Approved
0.5728 Remote Similarity NPD4786 Approved
0.5728 Remote Similarity NPD3665 Phase 1
0.5728 Remote Similarity NPD3133 Approved
0.5727 Remote Similarity NPD7839 Suspended
0.5726 Remote Similarity NPD6016 Approved
0.5726 Remote Similarity NPD6015 Approved
0.5714 Remote Similarity NPD6053 Discontinued
0.5714 Remote Similarity NPD6882 Approved
0.5701 Remote Similarity NPD5785 Approved
0.5688 Remote Similarity NPD7748 Approved
0.5686 Remote Similarity NPD4269 Approved
0.5686 Remote Similarity NPD4270 Approved
0.568 Remote Similarity NPD5988 Approved
0.568 Remote Similarity NPD6370 Approved
0.5678 Remote Similarity NPD5251 Approved
0.5678 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5678 Remote Similarity NPD5169 Approved
0.5678 Remote Similarity NPD5249 Phase 3
0.5678 Remote Similarity NPD5248 Approved
0.5678 Remote Similarity NPD5247 Approved
0.5678 Remote Similarity NPD5135 Approved
0.5678 Remote Similarity NPD5250 Approved
0.5676 Remote Similarity NPD6084 Phase 2
0.5676 Remote Similarity NPD6083 Phase 2
0.5676 Remote Similarity NPD7902 Approved
0.5656 Remote Similarity NPD6009 Approved
0.5652 Remote Similarity NPD7341 Phase 2
0.5641 Remote Similarity NPD5168 Approved
0.5641 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5636 Remote Similarity NPD5695 Phase 3
0.5631 Remote Similarity NPD7154 Phase 3
0.563 Remote Similarity NPD5216 Approved
0.563 Remote Similarity NPD5217 Approved
0.563 Remote Similarity NPD5215 Approved
0.563 Remote Similarity NPD5127 Approved
0.5625 Remote Similarity NPD5696 Approved
0.5625 Remote Similarity NPD8074 Phase 3
0.5612 Remote Similarity NPD8264 Approved

  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