Structure

Physi-Chem Properties

Molecular Weight:  530.29
Volume:  524.033
LogP:  3.547
LogD:  3.36
LogS:  -4.624
# Rotatable Bonds:  4
TPSA:  106.35
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  8
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.436
Synthetic Accessibility Score:  6.545
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.428
MDCK Permeability:  1.78300488187233e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.102
30% Bioavailability (F30%):  0.632

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.031
Plasma Protein Binding (PPB):  89.7620620727539%
Volume Distribution (VD):  0.935
Pgp-substrate:  4.2359819412231445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.984
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.85
CYP2C9-inhibitor:  0.135
CYP2C9-substrate:  0.018
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.177
CYP3A4-inhibitor:  0.625
CYP3A4-substrate:  0.907

ADMET: Excretion

Clearance (CL):  10.373
Half-life (T1/2):  0.598

ADMET: Toxicity

hERG Blockers:  0.876
Human Hepatotoxicity (H-HT):  0.747
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.041
Rat Oral Acute Toxicity:  0.924
Maximum Recommended Daily Dose:  0.97
Skin Sensitization:  0.644
Carcinogencity:  0.195
Eye Corrosion:  0.003
Eye Irritation:  0.031
Respiratory Toxicity:  0.962

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Similar NPs/Drugs  

  Natural Product: NPC115349

Natural Product ID:  NPC115349
Common Name*:   SEHQMXOXGIZASS-KMNGBJDXSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SEHQMXOXGIZASS-KMNGBJDXSA-N
Standard InCHI:  InChI=1S/C30H42O8/c1-16-25(32)20(33-4)13-24(35-16)36-19-6-8-26(2)17(11-19)5-10-28-21(26)7-9-27(3)29(28,38-28)14-22-30(27,37-22)18-12-23(31)34-15-18/h12,16-17,19-22,24-25,32H,5-11,13-15H2,1-4H3/t16-,17-,19+,20-,21-,22-,24+,25+,26+,27+,28+,29-,30-/m1/s1
SMILES:  CO[C@@H]1C[C@H](O[C@H]2CC[C@]3([C@@H](C2)CC[C@@]24[C@@H]3CC[C@]3([C@]4(O2)C[C@@H]2[C@]3(O2)C2=CC(=O)OC2)C)C)O[C@@H]([C@@H]1O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL229203
PubChem CID:   16756312
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001555] Cardenolides and derivatives
            • [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/C39730000707]
NPO1071 Parerythropodium fulvum Species n.a. n.a. n.a. n.a. n.a. PMID[11277760]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota leaves Niigata City, Niigata Province, Japan 2000-Nov PMID[15730243]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota leaves n.a. n.a. PMID[16933868]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[17253842]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs n.a. n.a. PMID[17595134]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs Niigata City, Niigata Province, Japan 2001-NOV PMID[17595134]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18491868]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[19731587]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[29693393]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota Leaves; Stems n.a. n.a. PMID[9214727]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2518 Crinum kirkii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5980 Eria subsessilis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20132 Scutellaria seleriana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3146 Ammodendron conollyi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2518 Crinum kirkii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO715 Teucrium pestalozzae Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4253 Viguiera annua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8472 Knightia deplanchei Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1308 Veronica pectinata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15583 Tripodanthus acutifolius Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1071 Parerythropodium fulvum Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO351 Cirsium dipsacolepis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8585 Verpa digitaliformis Species Morchellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5197 Streptomyces eurythermus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6377 Cocculus diversifolius Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6776 Trifolium apertum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7097 Rhynchosporium orthosporum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2361 Aconitum brevicalcaratum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6974 Solanum racemigerum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4082 Ophiarthrum elegans Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1607 Croton rhamnifolius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8840 Ptilidium ciliare Species Ptilidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5591 Fucus spiralis Species Fucaceae 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
NPT1475 Cell Line WI-38 VA13 Homo sapiens IC50 = 178000000.0 nM PMID[533262]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 74100000.0 nM PMID[533262]
NPT81 Cell Line A549 Homo sapiens IC50 = 45600.0 nM PMID[533262]
NPT81 Cell Line A549 Homo sapiens IC50 = 62100.0 nM PMID[533262]
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[533262]
NPT27 Others Unspecified IC50 = 40900000.0 nM PMID[533262]
NPT2 Others Unspecified Activity = 104.0 % PMID[533262]
NPT2 Others Unspecified Activity = 96.0 % PMID[533262]
NPT2 Others Unspecified Activity = 97.0 % PMID[533262]

☑ 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 NPC115349 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
0.9558 High Similarity NPC304260
0.9558 High Similarity NPC5883
0.9558 High Similarity NPC29639
0.9558 High Similarity NPC44899
0.9554 High Similarity NPC290693
0.9464 High Similarity NPC310341
0.9464 High Similarity NPC99620
0.9464 High Similarity NPC199428
0.9464 High Similarity NPC193382
0.9464 High Similarity NPC5311
0.9391 High Similarity NPC475219
0.9391 High Similarity NPC231518
0.9381 High Similarity NPC77319
0.9381 High Similarity NPC471353
0.9381 High Similarity NPC474418
0.9381 High Similarity NPC152615
0.9381 High Similarity NPC244402
0.9381 High Similarity NPC87250
0.9381 High Similarity NPC158344
0.9381 High Similarity NPC157376
0.9381 High Similarity NPC471355
0.9381 High Similarity NPC471351
0.9381 High Similarity NPC473852
0.9381 High Similarity NPC309034
0.9381 High Similarity NPC243196
0.9381 High Similarity NPC93883
0.9381 High Similarity NPC84987
0.9381 High Similarity NPC196429
0.9381 High Similarity NPC142066
0.9381 High Similarity NPC27507
0.9381 High Similarity NPC203862
0.9381 High Similarity NPC471354
0.9381 High Similarity NPC99728
0.9381 High Similarity NPC50305
0.9381 High Similarity NPC34390
0.9375 High Similarity NPC471633
0.9375 High Similarity NPC84949
0.9375 High Similarity NPC69576
0.9375 High Similarity NPC31354
0.931 High Similarity NPC193893
0.9298 High Similarity NPC83287
0.9224 High Similarity NPC40749
0.9217 High Similarity NPC30483
0.9217 High Similarity NPC32177
0.9217 High Similarity NPC292467
0.9217 High Similarity NPC268326
0.9217 High Similarity NPC81222
0.9217 High Similarity NPC153085
0.9217 High Similarity NPC469756
0.9217 High Similarity NPC329905
0.9217 High Similarity NPC236973
0.9217 High Similarity NPC291820
0.9217 High Similarity NPC55532
0.9217 High Similarity NPC470897
0.9138 High Similarity NPC475136
0.9138 High Similarity NPC475629
0.9138 High Similarity NPC475556
0.9138 High Similarity NPC72260
0.9138 High Similarity NPC474466
0.9138 High Similarity NPC107607
0.913 High Similarity NPC218093
0.906 High Similarity NPC173555
0.906 High Similarity NPC120390
0.906 High Similarity NPC475590
0.906 High Similarity NPC314535
0.906 High Similarity NPC474908
0.906 High Similarity NPC475419
0.8983 High Similarity NPC264336
0.8983 High Similarity NPC74259
0.8983 High Similarity NPC474423
0.8957 High Similarity NPC113425
0.8957 High Similarity NPC232564
0.8908 High Similarity NPC27363
0.8908 High Similarity NPC308262
0.8908 High Similarity NPC208193
0.8908 High Similarity NPC117445
0.8761 High Similarity NPC475030
0.8761 High Similarity NPC472901
0.876 High Similarity NPC250556
0.876 High Similarity NPC469750
0.8689 High Similarity NPC471357
0.8689 High Similarity NPC329784
0.8689 High Similarity NPC469757
0.8689 High Similarity NPC471356
0.8689 High Similarity NPC240070
0.8689 High Similarity NPC146456
0.8689 High Similarity NPC117702
0.8689 High Similarity NPC179412
0.8661 High Similarity NPC119855
0.8661 High Similarity NPC220217
0.8655 High Similarity NPC470312
0.864 High Similarity NPC225385
0.864 High Similarity NPC298783
0.864 High Similarity NPC157817
0.864 High Similarity NPC104585
0.8618 High Similarity NPC311534
0.8609 High Similarity NPC472987
0.8609 High Similarity NPC473021
0.8548 High Similarity NPC219085
0.8548 High Similarity NPC232785
0.8548 High Similarity NPC140092
0.8548 High Similarity NPC17896
0.8548 High Similarity NPC469752
0.8548 High Similarity NPC188234
0.8548 High Similarity NPC469755
0.8548 High Similarity NPC471352
0.8548 High Similarity NPC6108
0.8548 High Similarity NPC180079
0.8548 High Similarity NPC471358
0.8548 High Similarity NPC89514
0.8548 High Similarity NPC469753
0.8548 High Similarity NPC197707
0.8548 High Similarity NPC471361
0.8548 High Similarity NPC276838
0.8548 High Similarity NPC471360
0.8548 High Similarity NPC469751
0.8548 High Similarity NPC10823
0.8548 High Similarity NPC284406
0.8548 High Similarity NPC469754
0.8548 High Similarity NPC125077
0.8548 High Similarity NPC471359
0.8548 High Similarity NPC329986
0.8548 High Similarity NPC9499
0.8548 High Similarity NPC251866
0.8548 High Similarity NPC86159
0.8548 High Similarity NPC70542
0.8534 High Similarity NPC150228
0.8534 High Similarity NPC214005
0.8512 High Similarity NPC471082
0.85 High Similarity NPC135369
0.8496 Intermediate Similarity NPC473199
0.8492 Intermediate Similarity NPC142756
0.8487 Intermediate Similarity NPC472080
0.8482 Intermediate Similarity NPC472821
0.848 Intermediate Similarity NPC253456
0.848 Intermediate Similarity NPC159338
0.848 Intermediate Similarity NPC16569
0.8475 Intermediate Similarity NPC212660
0.8475 Intermediate Similarity NPC207637
0.8462 Intermediate Similarity NPC144068
0.8448 Intermediate Similarity NPC114188
0.8435 Intermediate Similarity NPC206618
0.8435 Intermediate Similarity NPC257853
0.843 Intermediate Similarity NPC233500
0.8421 Intermediate Similarity NPC472820
0.8417 Intermediate Similarity NPC219656
0.8417 Intermediate Similarity NPC278681
0.8413 Intermediate Similarity NPC19124
0.8413 Intermediate Similarity NPC93416
0.8413 Intermediate Similarity NPC42670
0.84 Intermediate Similarity NPC91
0.8362 Intermediate Similarity NPC177047
0.8361 Intermediate Similarity NPC196130
0.8348 Intermediate Similarity NPC38948
0.8348 Intermediate Similarity NPC38217
0.8348 Intermediate Similarity NPC472988
0.8347 Intermediate Similarity NPC112936
0.8346 Intermediate Similarity NPC116075
0.8346 Intermediate Similarity NPC247190
0.8346 Intermediate Similarity NPC146857
0.8346 Intermediate Similarity NPC32793
0.8346 Intermediate Similarity NPC476221
0.8346 Intermediate Similarity NPC477709
0.8346 Intermediate Similarity NPC469749
0.8333 Intermediate Similarity NPC16701
0.8333 Intermediate Similarity NPC472899
0.8333 Intermediate Similarity NPC475403
0.8333 Intermediate Similarity NPC472898
0.8333 Intermediate Similarity NPC472818
0.8333 Intermediate Similarity NPC186668
0.8333 Intermediate Similarity NPC173347
0.8333 Intermediate Similarity NPC472900
0.8333 Intermediate Similarity NPC160888
0.8333 Intermediate Similarity NPC85670
0.8319 Intermediate Similarity NPC281378
0.8319 Intermediate Similarity NPC187302
0.8319 Intermediate Similarity NPC160583
0.8319 Intermediate Similarity NPC189588
0.8319 Intermediate Similarity NPC97487
0.8319 Intermediate Similarity NPC10232
0.8319 Intermediate Similarity NPC196471
0.8304 Intermediate Similarity NPC247701
0.8304 Intermediate Similarity NPC25177
0.8304 Intermediate Similarity NPC222875
0.8304 Intermediate Similarity NPC268829
0.8304 Intermediate Similarity NPC295110
0.8293 Intermediate Similarity NPC219804
0.8281 Intermediate Similarity NPC329636
0.8276 Intermediate Similarity NPC128133
0.8276 Intermediate Similarity NPC296761
0.8276 Intermediate Similarity NPC125361
0.8276 Intermediate Similarity NPC51925
0.8276 Intermediate Similarity NPC43976
0.8276 Intermediate Similarity NPC473570
0.8276 Intermediate Similarity NPC154085
0.8264 Intermediate Similarity NPC195560
0.8264 Intermediate Similarity NPC473633
0.8264 Intermediate Similarity NPC477071
0.8264 Intermediate Similarity NPC35171
0.8264 Intermediate Similarity NPC229962

  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 NPC115349 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
0.9391 High Similarity NPD8033 Approved
0.9298 High Similarity NPD7327 Approved
0.9298 High Similarity NPD7328 Approved
0.9217 High Similarity NPD7516 Approved
0.9138 High Similarity NPD8377 Approved
0.9138 High Similarity NPD8294 Approved
0.906 High Similarity NPD8296 Approved
0.906 High Similarity NPD8378 Approved
0.906 High Similarity NPD8379 Approved
0.906 High Similarity NPD8335 Approved
0.906 High Similarity NPD8380 Approved
0.876 High Similarity NPD7507 Approved
0.8548 High Similarity NPD7319 Approved
0.843 Intermediate Similarity NPD7503 Approved
0.7881 Intermediate Similarity NPD6686 Approved
0.7705 Intermediate Similarity NPD8133 Approved
0.7652 Intermediate Similarity NPD7638 Approved
0.7647 Intermediate Similarity NPD6412 Phase 2
0.7586 Intermediate Similarity NPD7640 Approved
0.7586 Intermediate Similarity NPD7639 Approved
0.7521 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD7736 Approved
0.7447 Intermediate Similarity NPD7625 Phase 1
0.7381 Intermediate Similarity NPD7115 Discovery
0.7373 Intermediate Similarity NPD5344 Discontinued
0.7317 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD8293 Discontinued
0.7231 Intermediate Similarity NPD6370 Approved
0.7121 Intermediate Similarity NPD7492 Approved
0.7077 Intermediate Similarity NPD6059 Approved
0.7077 Intermediate Similarity NPD6054 Approved
0.7073 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD6616 Approved
0.7063 Intermediate Similarity NPD6882 Approved
0.7045 Intermediate Similarity NPD8328 Phase 3
0.7025 Intermediate Similarity NPD7632 Discontinued
0.7015 Intermediate Similarity NPD7078 Approved
0.7 Intermediate Similarity NPD6648 Approved
0.6992 Remote Similarity NPD6008 Approved
0.6977 Remote Similarity NPD6009 Approved
0.696 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6947 Remote Similarity NPD6319 Approved
0.6929 Remote Similarity NPD8297 Approved
0.6929 Remote Similarity NPD6053 Discontinued
0.6923 Remote Similarity NPD8171 Discontinued
0.6917 Remote Similarity NPD4225 Approved
0.6894 Remote Similarity NPD6016 Approved
0.6894 Remote Similarity NPD6015 Approved
0.688 Remote Similarity NPD7320 Approved
0.6875 Remote Similarity NPD4632 Approved
0.6855 Remote Similarity NPD7128 Approved
0.6855 Remote Similarity NPD6675 Approved
0.6855 Remote Similarity NPD6402 Approved
0.6855 Remote Similarity NPD5739 Approved
0.6846 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5988 Approved
0.6825 Remote Similarity NPD6373 Approved
0.6825 Remote Similarity NPD6372 Approved
0.6791 Remote Similarity NPD6067 Discontinued
0.6767 Remote Similarity NPD8515 Approved
0.6767 Remote Similarity NPD8517 Approved
0.6767 Remote Similarity NPD8516 Approved
0.6767 Remote Similarity NPD8513 Phase 3
0.6752 Remote Similarity NPD46 Approved
0.6752 Remote Similarity NPD6698 Approved
0.6746 Remote Similarity NPD6899 Approved
0.6746 Remote Similarity NPD6881 Approved
0.6719 Remote Similarity NPD6650 Approved
0.6719 Remote Similarity NPD6649 Approved
0.6667 Remote Similarity NPD7604 Phase 2
0.6667 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD6051 Approved
0.6641 Remote Similarity NPD7102 Approved
0.6641 Remote Similarity NPD6883 Approved
0.6641 Remote Similarity NPD7290 Approved
0.664 Remote Similarity NPD8170 Clinical (unspecified phase)
0.661 Remote Similarity NPD7838 Discovery
0.6607 Remote Similarity NPD7525 Registered
0.6594 Remote Similarity NPD6033 Approved
0.6589 Remote Similarity NPD6869 Approved
0.6589 Remote Similarity NPD6847 Approved
0.6589 Remote Similarity NPD6617 Approved
0.6589 Remote Similarity NPD8130 Phase 1
0.6562 Remote Similarity NPD6012 Approved
0.6562 Remote Similarity NPD6014 Approved
0.6562 Remote Similarity NPD6013 Approved
0.6557 Remote Similarity NPD6084 Phase 2
0.6557 Remote Similarity NPD6083 Phase 2
0.6532 Remote Similarity NPD4159 Approved
0.6525 Remote Similarity NPD8449 Approved
0.6522 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6519 Remote Similarity NPD5983 Phase 2
0.6512 Remote Similarity NPD6371 Approved
0.6504 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6496 Remote Similarity NPD7524 Approved
0.6484 Remote Similarity NPD6011 Approved
0.6479 Remote Similarity NPD8450 Suspended
0.6462 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6462 Remote Similarity NPD8413 Clinical (unspecified phase)
0.646 Remote Similarity NPD6928 Phase 2
0.6449 Remote Similarity NPD6336 Discontinued
0.6423 Remote Similarity NPD4755 Approved
0.6406 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6385 Remote Similarity NPD4634 Approved
0.6379 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6399 Phase 3
0.6364 Remote Similarity NPD4202 Approved
0.6357 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6356 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6349 Remote Similarity NPD5211 Phase 2
0.632 Remote Similarity NPD5286 Approved
0.632 Remote Similarity NPD5285 Approved
0.632 Remote Similarity NPD4696 Approved
0.632 Remote Similarity NPD4700 Approved
0.6311 Remote Similarity NPD7748 Approved
0.6303 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7799 Discontinued
0.6293 Remote Similarity NPD6695 Phase 3
0.629 Remote Similarity NPD7902 Approved
0.6281 Remote Similarity NPD7515 Phase 2
0.6281 Remote Similarity NPD8034 Phase 2
0.6281 Remote Similarity NPD8035 Phase 2
0.6281 Remote Similarity NPD7637 Suspended
0.6269 Remote Similarity NPD6274 Approved
0.626 Remote Similarity NPD5695 Phase 3
0.625 Remote Similarity NPD7100 Approved
0.625 Remote Similarity NPD5141 Approved
0.625 Remote Similarity NPD7101 Approved
0.624 Remote Similarity NPD5696 Approved
0.622 Remote Similarity NPD5225 Approved
0.622 Remote Similarity NPD5224 Approved
0.622 Remote Similarity NPD4633 Approved
0.622 Remote Similarity NPD5226 Approved
0.6202 Remote Similarity NPD4767 Approved
0.6202 Remote Similarity NPD4768 Approved
0.6198 Remote Similarity NPD3168 Discontinued
0.6186 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6179 Remote Similarity NPD6001 Approved
0.6176 Remote Similarity NPD6335 Approved
0.6172 Remote Similarity NPD5175 Approved
0.6172 Remote Similarity NPD5174 Approved
0.617 Remote Similarity NPD8074 Phase 3
0.6167 Remote Similarity NPD6903 Approved
0.6159 Remote Similarity NPD6909 Approved
0.6159 Remote Similarity NPD6908 Approved
0.6154 Remote Similarity NPD5956 Approved
0.6148 Remote Similarity NPD5693 Phase 1
0.6142 Remote Similarity NPD5223 Approved
0.6134 Remote Similarity NPD6684 Approved
0.6134 Remote Similarity NPD7521 Approved
0.6134 Remote Similarity NPD5330 Approved
0.6134 Remote Similarity NPD7334 Approved
0.6134 Remote Similarity NPD6409 Approved
0.6134 Remote Similarity NPD7146 Approved
0.6116 Remote Similarity NPD4753 Phase 2
0.6116 Remote Similarity NPD5328 Approved
0.6107 Remote Similarity NPD4729 Approved
0.6107 Remote Similarity NPD4730 Approved
0.6106 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6103 Remote Similarity NPD6317 Approved
0.6087 Remote Similarity NPD7645 Phase 2
0.6083 Remote Similarity NPD7750 Discontinued
0.6083 Remote Similarity NPD4250 Approved
0.6083 Remote Similarity NPD4251 Approved
0.6058 Remote Similarity NPD6313 Approved
0.6058 Remote Similarity NPD6314 Approved
0.605 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6048 Remote Similarity NPD7900 Approved
0.6048 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6047 Remote Similarity NPD4754 Approved
0.6043 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6034 Remote Similarity NPD6930 Phase 2
0.6034 Remote Similarity NPD6931 Approved
0.6018 Remote Similarity NPD6942 Approved
0.6018 Remote Similarity NPD7339 Approved
0.6016 Remote Similarity NPD6079 Approved
0.6015 Remote Similarity NPD5250 Approved
0.6015 Remote Similarity NPD5249 Phase 3
0.6015 Remote Similarity NPD5248 Approved
0.6015 Remote Similarity NPD5251 Approved
0.6015 Remote Similarity NPD5247 Approved
0.6 Remote Similarity NPD4249 Approved
0.6 Remote Similarity NPD7260 Phase 2
0.6 Remote Similarity NPD3618 Phase 1
0.5985 Remote Similarity NPD5128 Approved
0.5984 Remote Similarity NPD6080 Approved
0.5984 Remote Similarity NPD6904 Approved
0.5984 Remote Similarity NPD6673 Approved
0.5966 Remote Similarity NPD4786 Approved
0.5966 Remote Similarity NPD3666 Approved
0.5966 Remote Similarity NPD3133 Approved
0.5966 Remote Similarity NPD3665 Phase 1
0.5965 Remote Similarity NPD6933 Approved
0.5957 Remote Similarity NPD7829 Approved
0.5957 Remote Similarity NPD7830 Approved
0.5948 Remote Similarity NPD6929 Approved
0.5948 Remote Similarity NPD4195 Approved
0.5932 Remote Similarity NPD4752 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