Structure

Physi-Chem Properties

Molecular Weight:  666.19
Volume:  636.707
LogP:  2.247
LogD:  0.756
LogS:  -2.713
# Rotatable Bonds:  7
TPSA:  220.26
# H-Bond Aceptor:  14
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.264
Synthetic Accessibility Score:  5.495
Fsp3:  0.471
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
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:  -5.935
MDCK Permeability:  9.974888598662801e-06
Pgp-inhibitor:  0.39
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.872
20% Bioavailability (F20%):  0.787
30% Bioavailability (F30%):  0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  85.86060333251953%
Volume Distribution (VD):  0.605
Pgp-substrate:  9.415385246276855%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.052
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.14
CYP2C9-substrate:  0.205
CYP2D6-inhibitor:  0.104
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.67
CYP3A4-substrate:  0.3

ADMET: Excretion

Clearance (CL):  2.192
Half-life (T1/2):  0.172

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.994
Drug-inuced Liver Injury (DILI):  0.979
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.971
Maximum Recommended Daily Dose:  0.041
Skin Sensitization:  0.045
Carcinogencity:  0.017
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.04

Download Data

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

  Natural Product: NPC251144

Natural Product ID:  NPC251144
Common Name*:   Dicerandrol A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LMADRJRTQXNOEP-FNCICBJWSA-N
Standard InCHI:  InChI=1S/C34H34O14/c1-13-9-19(39)25-29(43)23-21(47-33(25,11-35)31(13)45-15(3)37)7-5-17(27(23)41)18-6-8-22-24(28(18)42)30(44)26-20(40)10-14(2)32(46-16(4)38)34(26,12-36)48-22/h5-8,13-14,31-32,35-36,39-42H,9-12H2,1-4H3/t13-,14-,31-,32-,33+,34+/m1/s1
SMILES:  C[C@@H]1CC(=C2C(=O)c3c(ccc(c4ccc5c(c4O)C(=O)C4=C(C[C@@H](C)[C@H]([C@@]4(CO)O5)OC(=O)C)O)c3O)O[C@]2(CO)[C@@H]1OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460126
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones

*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
NPO15822 Stypopodium zonale Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[10395524]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO29819 Phomopsis longicolla Species Diaporthaceae Eukaryota n.a. n.a. n.a. PMID[11520215]
NPO29819 Phomopsis longicolla Species Diaporthaceae Eukaryota n.a. stem n.a. PMID[11520215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO15822 Stypopodium zonale Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[12444716]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO18853 Alstonia scholaris Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[21043460]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO24324 Halobacterium salinarum Species Halobacteriaceae Archaea n.a. n.a. n.a. PMID[24823651]
NPO7118 Manglietiastrum sinicum Species Magnoliaceae Eukaryota Mature Carpels n.a. n.a. PMID[25116183]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO18853 Alstonia scholaris Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18853 Alstonia scholaris Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18853 Alstonia scholaris Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17356 Peltigera malacea Species Peltigeraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11976 Elaeocarpus sikkimensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24324 Halobacterium salinarum Species Halobacteriaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO17903 Nepeta ruderalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14170 Streptomyces neyagawaensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18050 Stilbe ericoides Species Stilbaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27088 Oscillatoria nigro-viridis Species Oscillatoriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18853 Alstonia scholaris Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7118 Manglietiastrum sinicum Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15822 Stypopodium zonale Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2290 Clarkia exilis Species Onagraceae 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 IC100 = 7.0 ug ml-1 PMID[464537]
NPT393 Cell Line HCT-116 Homo sapiens IC100 = 7.0 ug ml-1 PMID[464537]
NPT2452 Cell Line NCI-H292 IC50 = 42500.0 nM PMID[464538]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 43300.0 nM PMID[464538]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 100000.0 nM PMID[464538]
NPT2452 Cell Line NCI-H292 IC50 = 22900.0 nM PMID[464538]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 38400.0 nM PMID[464538]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 71700.0 nM PMID[464538]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 2640.0 nM PMID[464539]
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 11.0 mm PMID[464537]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 10.8 mm PMID[464537]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 22800.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 15600.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 24600.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 28900.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 36900.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 14800.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 46600.0 nM PMID[464538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 33300.0 nM PMID[464538]

☑ 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 NPC251144 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 NPC241387
0.9812 High Similarity NPC291795
0.9812 High Similarity NPC207574
0.9812 High Similarity NPC297195
0.9755 High Similarity NPC469345
0.9693 High Similarity NPC232412
0.9693 High Similarity NPC98667
0.9693 High Similarity NPC86809
0.9341 High Similarity NPC477683
0.9341 High Similarity NPC477682
0.9325 High Similarity NPC178173
0.9222 High Similarity NPC294149
0.9157 High Similarity NPC241874
0.9102 High Similarity NPC472620
0.908 High Similarity NPC48474
0.907 High Similarity NPC197972
0.9053 High Similarity NPC312630
0.9053 High Similarity NPC324220
0.9048 High Similarity NPC154986
0.9024 High Similarity NPC473961
0.8982 High Similarity NPC472619
0.8922 High Similarity NPC472622
0.8869 High Similarity NPC102810
0.8862 High Similarity NPC469394
0.8862 High Similarity NPC472621
0.8848 High Similarity NPC3629
0.8841 High Similarity NPC186113
0.8837 High Similarity NPC245059
0.8837 High Similarity NPC84494
0.8834 High Similarity NPC164427
0.882 High Similarity NPC207346
0.882 High Similarity NPC46564
0.881 High Similarity NPC225419
0.8795 High Similarity NPC472059
0.8795 High Similarity NPC473022
0.8788 High Similarity NPC471976
0.8786 High Similarity NPC208069
0.8786 High Similarity NPC164047
0.8786 High Similarity NPC475161
0.8786 High Similarity NPC470452
0.8786 High Similarity NPC470448
0.8786 High Similarity NPC470453
0.8786 High Similarity NPC477860
0.8773 High Similarity NPC477958
0.8772 High Similarity NPC63105
0.8765 High Similarity NPC475790
0.875 High Similarity NPC191634
0.8743 High Similarity NPC472053
0.8735 High Similarity NPC97812
0.8727 High Similarity NPC474373
0.872 High Similarity NPC20530
0.872 High Similarity NPC10754
0.872 High Similarity NPC215917
0.872 High Similarity NPC146636
0.8713 High Similarity NPC213052
0.8713 High Similarity NPC476139
0.8712 High Similarity NPC112701
0.8712 High Similarity NPC326592
0.8712 High Similarity NPC109594
0.8706 High Similarity NPC313304
0.8706 High Similarity NPC103307
0.8704 High Similarity NPC474021
0.8704 High Similarity NPC474023
0.8704 High Similarity NPC471677
0.869 High Similarity NPC472051
0.869 High Similarity NPC472057
0.869 High Similarity NPC475979
0.8686 High Similarity NPC106700
0.8683 High Similarity NPC472402
0.8675 High Similarity NPC472055
0.8671 High Similarity NPC476199
0.8671 High Similarity NPC476210
0.8663 High Similarity NPC199533
0.8663 High Similarity NPC470454
0.8655 High Similarity NPC315619
0.8655 High Similarity NPC288152
0.8655 High Similarity NPC137871
0.8655 High Similarity NPC271848
0.8655 High Similarity NPC81332
0.8655 High Similarity NPC262580
0.8655 High Similarity NPC289396
0.8655 High Similarity NPC9002
0.8655 High Similarity NPC212038
0.8655 High Similarity NPC257011
0.865 High Similarity NPC161881
0.865 High Similarity NPC244583
0.865 High Similarity NPC10807
0.865 High Similarity NPC56232
0.865 High Similarity NPC150123
0.8647 High Similarity NPC246274
0.8647 High Similarity NPC217378
0.8647 High Similarity NPC177480
0.8647 High Similarity NPC326877
0.8639 High Similarity NPC120593
0.8639 High Similarity NPC251336
0.8639 High Similarity NPC207575
0.8639 High Similarity NPC13481
0.8636 High Similarity NPC473686
0.8636 High Similarity NPC229817
0.8636 High Similarity NPC475220
0.8636 High Similarity NPC241847
0.8636 High Similarity NPC87583
0.8636 High Similarity NPC475352
0.8636 High Similarity NPC221140
0.8631 High Similarity NPC63438
0.8631 High Similarity NPC124155
0.8631 High Similarity NPC257566
0.8629 High Similarity NPC293227
0.8629 High Similarity NPC475662
0.8629 High Similarity NPC473717
0.8629 High Similarity NPC473631
0.8623 High Similarity NPC92589
0.8614 High Similarity NPC51247
0.8614 High Similarity NPC470339
0.8613 High Similarity NPC475246
0.8613 High Similarity NPC46958
0.8611 High Similarity NPC470195
0.8611 High Similarity NPC316274
0.8611 High Similarity NPC282474
0.8611 High Similarity NPC470196
0.8611 High Similarity NPC470193
0.8611 High Similarity NPC470200
0.8611 High Similarity NPC470194
0.8611 High Similarity NPC470197
0.8611 High Similarity NPC470198
0.8606 High Similarity NPC471787
0.8605 High Similarity NPC476229
0.8605 High Similarity NPC476311
0.8605 High Similarity NPC469393
0.8605 High Similarity NPC476152
0.8605 High Similarity NPC168789
0.8598 High Similarity NPC135522
0.8598 High Similarity NPC472583
0.8598 High Similarity NPC100134
0.8598 High Similarity NPC469405
0.8598 High Similarity NPC223701
0.8598 High Similarity NPC209760
0.8598 High Similarity NPC7989
0.8596 High Similarity NPC210808
0.8596 High Similarity NPC193698
0.8596 High Similarity NPC74559
0.8596 High Similarity NPC314672
0.8596 High Similarity NPC199079
0.8596 High Similarity NPC298778
0.8596 High Similarity NPC76047
0.8589 High Similarity NPC471676
0.8589 High Similarity NPC209142
0.8589 High Similarity NPC263384
0.8589 High Similarity NPC473131
0.8589 High Similarity NPC472420
0.8589 High Similarity NPC472422
0.8589 High Similarity NPC328740
0.8589 High Similarity NPC244577
0.8589 High Similarity NPC470675
0.8589 High Similarity NPC289774
0.8589 High Similarity NPC209846
0.8589 High Similarity NPC312549
0.8589 High Similarity NPC477897
0.8588 High Similarity NPC249977
0.8588 High Similarity NPC105414
0.8588 High Similarity NPC474024
0.8588 High Similarity NPC6588
0.8588 High Similarity NPC117854
0.8588 High Similarity NPC473094
0.8588 High Similarity NPC477154
0.8588 High Similarity NPC234497
0.8588 High Similarity NPC282636
0.8588 High Similarity NPC472058
0.8588 High Similarity NPC63470
0.8588 High Similarity NPC470341
0.8588 High Similarity NPC294863
0.8588 High Similarity NPC324522
0.858 High Similarity NPC472628
0.858 High Similarity NPC294722
0.858 High Similarity NPC473016
0.858 High Similarity NPC473010
0.858 High Similarity NPC293319
0.8571 High Similarity NPC44947
0.8571 High Similarity NPC190450
0.8571 High Similarity NPC220912
0.8571 High Similarity NPC15374
0.8563 High Similarity NPC472618
0.8563 High Similarity NPC195136
0.8555 High Similarity NPC162248
0.8555 High Similarity NPC68381
0.8555 High Similarity NPC3718
0.8555 High Similarity NPC474345
0.8554 High Similarity NPC324358
0.8554 High Similarity NPC322459
0.8554 High Similarity NPC1796
0.8554 High Similarity NPC318527
0.8554 High Similarity NPC323627
0.8554 High Similarity NPC475184
0.8554 High Similarity NPC257166
0.8547 High Similarity NPC477529
0.8547 High Similarity NPC264302
0.8547 High Similarity NPC475669
0.8547 High Similarity NPC321046
0.8547 High Similarity NPC476159
0.8545 High Similarity NPC217706

  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 NPC251144 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
0.8554 High Similarity NPD7075 Discontinued
0.8538 High Similarity NPD7804 Clinical (unspecified phase)
0.8512 High Similarity NPD6959 Discontinued
0.8485 Intermediate Similarity NPD7819 Suspended
0.8434 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD4380 Phase 2
0.84 Intermediate Similarity NPD8313 Approved
0.84 Intermediate Similarity NPD8312 Approved
0.8373 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD7473 Discontinued
0.8313 Intermediate Similarity NPD6801 Discontinued
0.8286 Intermediate Similarity NPD6559 Discontinued
0.8278 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD7074 Phase 3
0.8274 Intermediate Similarity NPD7768 Phase 2
0.8263 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8256 Intermediate Similarity NPD6166 Phase 2
0.8256 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8256 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8256 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8218 Intermediate Similarity NPD7054 Approved
0.8218 Intermediate Similarity NPD5844 Phase 1
0.8214 Intermediate Similarity NPD5402 Approved
0.8171 Intermediate Similarity NPD7472 Approved
0.8167 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8156 Intermediate Similarity NPD8150 Discontinued
0.8144 Intermediate Similarity NPD7411 Suspended
0.814 Intermediate Similarity NPD6232 Discontinued
0.8136 Intermediate Similarity NPD7808 Phase 3
0.8129 Intermediate Similarity NPD5494 Approved
0.8095 Intermediate Similarity NPD1934 Approved
0.8079 Intermediate Similarity NPD7251 Discontinued
0.8059 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD6797 Phase 2
0.8012 Intermediate Similarity NPD5403 Approved
0.8 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD3750 Approved
0.7956 Intermediate Similarity NPD8434 Phase 2
0.7941 Intermediate Similarity NPD2801 Approved
0.7941 Intermediate Similarity NPD8455 Phase 2
0.7941 Intermediate Similarity NPD1465 Phase 2
0.7927 Intermediate Similarity NPD7783 Phase 2
0.7927 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD3749 Approved
0.7901 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD3817 Phase 2
0.7892 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD5401 Approved
0.787 Intermediate Similarity NPD6599 Discontinued
0.7853 Intermediate Similarity NPD3818 Discontinued
0.7853 Intermediate Similarity NPD1549 Phase 2
0.7853 Intermediate Similarity NPD7228 Approved
0.7831 Intermediate Similarity NPD6799 Approved
0.7824 Intermediate Similarity NPD8151 Discontinued
0.7784 Intermediate Similarity NPD2532 Approved
0.7784 Intermediate Similarity NPD2534 Approved
0.7784 Intermediate Similarity NPD2533 Approved
0.7758 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD3751 Discontinued
0.7749 Intermediate Similarity NPD7435 Discontinued
0.773 Intermediate Similarity NPD2935 Discontinued
0.7706 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD3226 Approved
0.7705 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD2346 Discontinued
0.7669 Intermediate Similarity NPD3748 Approved
0.7669 Intermediate Similarity NPD2799 Discontinued
0.7656 Intermediate Similarity NPD7696 Phase 3
0.7656 Intermediate Similarity NPD7698 Approved
0.7656 Intermediate Similarity NPD7697 Approved
0.7651 Intermediate Similarity NPD4628 Phase 3
0.7644 Intermediate Similarity NPD3882 Suspended
0.7636 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD3787 Discontinued
0.7622 Intermediate Similarity NPD1551 Phase 2
0.7622 Intermediate Similarity NPD2796 Approved
0.7619 Intermediate Similarity NPD1511 Approved
0.7604 Intermediate Similarity NPD6823 Phase 2
0.7602 Intermediate Similarity NPD7874 Approved
0.7602 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7592 Intermediate Similarity NPD6781 Approved
0.7592 Intermediate Similarity NPD6776 Approved
0.7592 Intermediate Similarity NPD6780 Approved
0.7592 Intermediate Similarity NPD6777 Approved
0.7592 Intermediate Similarity NPD6778 Approved
0.7592 Intermediate Similarity NPD6779 Approved
0.7592 Intermediate Similarity NPD6782 Approved
0.759 Intermediate Similarity NPD2800 Approved
0.759 Intermediate Similarity NPD7701 Phase 2
0.7588 Intermediate Similarity NPD920 Approved
0.7572 Intermediate Similarity NPD37 Approved
0.7561 Intermediate Similarity NPD1510 Phase 2
0.7557 Intermediate Similarity NPD6234 Discontinued
0.7543 Intermediate Similarity NPD4966 Approved
0.7543 Intermediate Similarity NPD4967 Phase 2
0.7543 Intermediate Similarity NPD4965 Approved
0.7529 Intermediate Similarity NPD1512 Approved
0.7526 Intermediate Similarity NPD7871 Phase 2
0.7526 Intermediate Similarity NPD7870 Phase 2
0.7526 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD8320 Phase 1
0.7526 Intermediate Similarity NPD8319 Approved
0.7514 Intermediate Similarity NPD7286 Phase 2
0.7514 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7699 Phase 2
0.7487 Intermediate Similarity NPD7700 Phase 2
0.7486 Intermediate Similarity NPD7240 Approved
0.7485 Intermediate Similarity NPD5124 Phase 1
0.7485 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7801 Approved
0.7471 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD6651 Approved
0.7439 Intermediate Similarity NPD1607 Approved
0.7432 Intermediate Similarity NPD5953 Discontinued
0.7423 Intermediate Similarity NPD1240 Approved
0.7412 Intermediate Similarity NPD7390 Discontinued
0.741 Intermediate Similarity NPD6099 Approved
0.741 Intermediate Similarity NPD6100 Approved
0.7407 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD2313 Discontinued
0.7399 Intermediate Similarity NPD7458 Discontinued
0.7368 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7003 Approved
0.7333 Intermediate Similarity NPD5710 Approved
0.7333 Intermediate Similarity NPD7229 Phase 3
0.7333 Intermediate Similarity NPD5711 Approved
0.733 Intermediate Similarity NPD6534 Approved
0.733 Intermediate Similarity NPD6535 Approved
0.7297 Intermediate Similarity NPD7685 Pre-registration
0.7289 Intermediate Similarity NPD7097 Phase 1
0.7284 Intermediate Similarity NPD6832 Phase 2
0.7284 Intermediate Similarity NPD4908 Phase 1
0.7278 Intermediate Similarity NPD8127 Discontinued
0.7278 Intermediate Similarity NPD1243 Approved
0.7278 Intermediate Similarity NPD7199 Phase 2
0.7273 Intermediate Similarity NPD7584 Approved
0.7273 Intermediate Similarity NPD6355 Discontinued
0.7263 Intermediate Similarity NPD919 Approved
0.7258 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD4363 Phase 3
0.724 Intermediate Similarity NPD4360 Phase 2
0.7239 Intermediate Similarity NPD4625 Phase 3
0.7233 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6273 Approved
0.7212 Intermediate Similarity NPD4060 Phase 1
0.7212 Intermediate Similarity NPD1613 Approved
0.7212 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5406 Approved
0.7202 Intermediate Similarity NPD5408 Approved
0.7202 Intermediate Similarity NPD5405 Approved
0.7202 Intermediate Similarity NPD5404 Approved
0.7195 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD1247 Approved
0.7179 Intermediate Similarity NPD8285 Discontinued
0.7168 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7033 Discontinued
0.7143 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1653 Approved
0.7135 Intermediate Similarity NPD8166 Discontinued
0.7121 Intermediate Similarity NPD7680 Approved
0.7118 Intermediate Similarity NPD2424 Discontinued
0.7108 Intermediate Similarity NPD7930 Approved
0.7104 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD3926 Phase 2
0.7101 Intermediate Similarity NPD2438 Suspended
0.7099 Intermediate Similarity NPD1203 Approved
0.7099 Intermediate Similarity NPD2797 Approved
0.7095 Intermediate Similarity NPD4288 Approved
0.7093 Intermediate Similarity NPD6190 Approved
0.7092 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD3268 Approved
0.7091 Intermediate Similarity NPD7985 Registered
0.7091 Intermediate Similarity NPD6798 Discontinued
0.7081 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD6844 Discontinued
0.7076 Intermediate Similarity NPD1652 Phase 2
0.7066 Intermediate Similarity NPD447 Suspended
0.7065 Intermediate Similarity NPD7585 Approved
0.7063 Intermediate Similarity NPD1610 Phase 2
0.7059 Intermediate Similarity NPD2344 Approved
0.7048 Intermediate Similarity NPD6233 Phase 2
0.7041 Intermediate Similarity NPD4308 Phase 3
0.7039 Intermediate Similarity NPD5760 Phase 2
0.7039 Intermediate Similarity NPD5761 Phase 2
0.7031 Intermediate Similarity NPD4287 Approved
0.7015 Intermediate Similarity NPD7583 Approved
0.701 Intermediate Similarity NPD6212 Phase 3
0.701 Intermediate Similarity NPD6214 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