Structure

Physi-Chem Properties

Molecular Weight:  514.29
Volume:  521.163
LogP:  4.146
LogD:  3.78
LogS:  -4.744
# Rotatable Bonds:  4
TPSA:  93.82
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  7
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.33
Synthetic Accessibility Score:  6.372
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
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:  -5.23
MDCK Permeability:  1.5273313692887314e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.03
30% Bioavailability (F30%):  0.523

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  97.10071563720703%
Volume Distribution (VD):  1.4
Pgp-substrate:  3.0164127349853516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.983
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.815
CYP2C9-inhibitor:  0.215
CYP2C9-substrate:  0.034
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.299
CYP3A4-inhibitor:  0.696
CYP3A4-substrate:  0.893

ADMET: Excretion

Clearance (CL):  10.49
Half-life (T1/2):  0.286

ADMET: Toxicity

hERG Blockers:  0.667
Human Hepatotoxicity (H-HT):  0.799
Drug-inuced Liver Injury (DILI):  0.033
AMES Toxicity:  0.03
Rat Oral Acute Toxicity:  0.908
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.083
Carcinogencity:  0.187
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.957

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  Natural Product: NPC268326

Natural Product ID:  NPC268326
Common Name*:   QXQSONDGTHTLKY-MKFWVJGXSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QXQSONDGTHTLKY-MKFWVJGXSA-N
Standard InCHI:  InChI=1S/C30H42O7/c1-17-26(32)22(33-4)15-25(35-17)36-20-6-9-27(2)19(14-20)5-11-29-23(27)8-10-28(3)21(7-12-30(28,29)37-29)18-13-24(31)34-16-18/h7,13,17,19-20,22-23,25-26,32H,5-6,8-12,14-16H2,1-4H3/t17-,19-,20+,22-,23-,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)CC=C3C2=CC(=O)OC2)C)C)O[C@@H]([C@@H]1O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL229373
PubChem CID:   44425147
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002207] O-glycosyl compounds

*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 Niigata City, Niigata Province, Japan 2001-NOV PMID[17595134]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs n.a. n.a. 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]
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]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae 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[HerDing]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14048 Cryptotaenia japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14048 Cryptotaenia japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2518 Crinum kirkii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14048 Cryptotaenia japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1607 Croton rhamnifolius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20132 Scutellaria seleriana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO715 Teucrium pestalozzae Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5980 Eria subsessilis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15583 Tripodanthus acutifolius Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3146 Ammodendron conollyi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8472 Knightia deplanchei Species Proteaceae 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]
NPO2518 Crinum kirkii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO351 Cirsium dipsacolepis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4253 Viguiera annua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5197 Streptomyces eurythermus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6776 Trifolium apertum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1308 Veronica pectinata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2361 Aconitum brevicalcaratum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8585 Verpa digitaliformis Species Morchellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14048 Cryptotaenia japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6377 Cocculus diversifolius Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4082 Ophiarthrum elegans Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7097 Rhynchosporium orthosporum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12987 Rhododendron farrerae Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8840 Ptilidium ciliare Species Ptilidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18054 Curvularia coicis Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6974 Solanum racemigerum Species Solanaceae 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]
NPO13325 Plantago lanceolata Species Plantaginaceae 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 = 161000000.0 nM PMID[505294]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 151000000.0 nM PMID[505294]
NPT81 Cell Line A549 Homo sapiens IC50 = 133000.0 nM PMID[505294]
NPT81 Cell Line A549 Homo sapiens IC50 > 316000.0 nM PMID[505294]
NPT27 Others Unspecified IC50 = 102000000.0 nM PMID[505294]
NPT2 Others Unspecified Activity = 88.0 % PMID[505294]
NPT2 Others Unspecified Activity = 89.0 % PMID[505294]
NPT2 Others Unspecified Activity = 99.0 % PMID[505294]

☑ 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 NPC268326 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 NPC153085
0.9459 High Similarity NPC290693
0.9279 High Similarity NPC471633
0.9279 High Similarity NPC84949
0.9279 High Similarity NPC31354
0.9279 High Similarity NPC69576
0.9217 High Similarity NPC115349
0.9196 High Similarity NPC5311
0.9196 High Similarity NPC310341
0.9196 High Similarity NPC199428
0.9196 High Similarity NPC193382
0.9196 High Similarity NPC99620
0.9123 High Similarity NPC29639
0.9123 High Similarity NPC5883
0.9123 High Similarity NPC44899
0.9123 High Similarity NPC304260
0.9115 High Similarity NPC157376
0.9115 High Similarity NPC99728
0.9115 High Similarity NPC243196
0.9115 High Similarity NPC87250
0.9115 High Similarity NPC50305
0.9115 High Similarity NPC473852
0.9115 High Similarity NPC84987
0.9115 High Similarity NPC93883
0.9115 High Similarity NPC471353
0.9115 High Similarity NPC158344
0.9115 High Similarity NPC309034
0.9115 High Similarity NPC34390
0.9115 High Similarity NPC474418
0.9115 High Similarity NPC471355
0.9115 High Similarity NPC152615
0.9115 High Similarity NPC244402
0.9115 High Similarity NPC471351
0.9115 High Similarity NPC203862
0.9115 High Similarity NPC196429
0.9115 High Similarity NPC77319
0.9115 High Similarity NPC471354
0.9115 High Similarity NPC142066
0.9115 High Similarity NPC27507
0.9035 High Similarity NPC83287
0.8966 High Similarity NPC231518
0.8966 High Similarity NPC475219
0.8957 High Similarity NPC30483
0.8957 High Similarity NPC469756
0.8957 High Similarity NPC236973
0.8957 High Similarity NPC329905
0.8957 High Similarity NPC32177
0.8957 High Similarity NPC470897
0.8957 High Similarity NPC292467
0.8957 High Similarity NPC55532
0.8889 High Similarity NPC193893
0.8879 High Similarity NPC72260
0.8879 High Similarity NPC475629
0.8879 High Similarity NPC474466
0.8879 High Similarity NPC475556
0.8879 High Similarity NPC475136
0.887 High Similarity NPC218093
0.8803 High Similarity NPC120390
0.8803 High Similarity NPC475590
0.8803 High Similarity NPC475419
0.8803 High Similarity NPC314535
0.8803 High Similarity NPC474908
0.8803 High Similarity NPC173555
0.8803 High Similarity NPC40749
0.8793 High Similarity NPC291820
0.8793 High Similarity NPC81222
0.875 High Similarity NPC177047
0.8729 High Similarity NPC264336
0.8729 High Similarity NPC74259
0.8729 High Similarity NPC474423
0.8718 High Similarity NPC107607
0.8661 High Similarity NPC475030
0.8661 High Similarity NPC472901
0.8661 High Similarity NPC206618
0.8655 High Similarity NPC308262
0.8655 High Similarity NPC208193
0.8655 High Similarity NPC117445
0.8655 High Similarity NPC27363
0.8571 High Similarity NPC38948
0.8559 High Similarity NPC470312
0.8545 High Similarity NPC45897
0.8534 High Similarity NPC113425
0.8534 High Similarity NPC232564
0.8512 High Similarity NPC469750
0.8512 High Similarity NPC250556
0.8509 High Similarity NPC473021
0.8509 High Similarity NPC472987
0.8475 Intermediate Similarity NPC278681
0.8468 Intermediate Similarity NPC470060
0.8468 Intermediate Similarity NPC470043
0.8468 Intermediate Similarity NPC470057
0.8468 Intermediate Similarity NPC470062
0.8468 Intermediate Similarity NPC470061
0.8468 Intermediate Similarity NPC470064
0.8468 Intermediate Similarity NPC470058
0.8468 Intermediate Similarity NPC470059
0.8443 Intermediate Similarity NPC471357
0.8443 Intermediate Similarity NPC117702
0.8443 Intermediate Similarity NPC146456
0.8443 Intermediate Similarity NPC469757
0.8443 Intermediate Similarity NPC240070
0.8443 Intermediate Similarity NPC471356
0.8443 Intermediate Similarity NPC329784
0.8443 Intermediate Similarity NPC179412
0.8417 Intermediate Similarity NPC471082
0.8403 Intermediate Similarity NPC135369
0.8403 Intermediate Similarity NPC112936
0.8393 Intermediate Similarity NPC473199
0.8393 Intermediate Similarity NPC470056
0.8393 Intermediate Similarity NPC220217
0.8393 Intermediate Similarity NPC119855
0.8393 Intermediate Similarity NPC470055
0.839 Intermediate Similarity NPC16701
0.8378 Intermediate Similarity NPC281378
0.8378 Intermediate Similarity NPC120009
0.8378 Intermediate Similarity NPC472821
0.8376 Intermediate Similarity NPC207637
0.8374 Intermediate Similarity NPC311534
0.8364 Intermediate Similarity NPC470054
0.8348 Intermediate Similarity NPC65034
0.8348 Intermediate Similarity NPC208189
0.8333 Intermediate Similarity NPC233500
0.8333 Intermediate Similarity NPC257853
0.8319 Intermediate Similarity NPC213761
0.8319 Intermediate Similarity NPC475074
0.8319 Intermediate Similarity NPC472820
0.8319 Intermediate Similarity NPC219656
0.8319 Intermediate Similarity NPC35171
0.8306 Intermediate Similarity NPC469755
0.8306 Intermediate Similarity NPC6108
0.8306 Intermediate Similarity NPC471360
0.8306 Intermediate Similarity NPC276838
0.8306 Intermediate Similarity NPC140092
0.8306 Intermediate Similarity NPC197707
0.8306 Intermediate Similarity NPC471359
0.8306 Intermediate Similarity NPC219085
0.8306 Intermediate Similarity NPC17896
0.8306 Intermediate Similarity NPC469752
0.8306 Intermediate Similarity NPC9499
0.8306 Intermediate Similarity NPC471352
0.8306 Intermediate Similarity NPC469751
0.8306 Intermediate Similarity NPC86159
0.8306 Intermediate Similarity NPC284406
0.8306 Intermediate Similarity NPC232785
0.8306 Intermediate Similarity NPC471358
0.8306 Intermediate Similarity NPC180079
0.8306 Intermediate Similarity NPC89514
0.8306 Intermediate Similarity NPC125077
0.8306 Intermediate Similarity NPC329986
0.8306 Intermediate Similarity NPC471361
0.8306 Intermediate Similarity NPC251866
0.8306 Intermediate Similarity NPC469754
0.8306 Intermediate Similarity NPC70542
0.8306 Intermediate Similarity NPC469753
0.8306 Intermediate Similarity NPC10823
0.8306 Intermediate Similarity NPC188234
0.8305 Intermediate Similarity NPC157380
0.8305 Intermediate Similarity NPC185287
0.8293 Intermediate Similarity NPC298841
0.8291 Intermediate Similarity NPC477580
0.8291 Intermediate Similarity NPC106446
0.8288 Intermediate Similarity NPC472815
0.8288 Intermediate Similarity NPC470053
0.8288 Intermediate Similarity NPC470571
0.8288 Intermediate Similarity NPC121423
0.8276 Intermediate Similarity NPC231797
0.8276 Intermediate Similarity NPC470063
0.8273 Intermediate Similarity NPC477716
0.8273 Intermediate Similarity NPC477721
0.8264 Intermediate Similarity NPC196130
0.8254 Intermediate Similarity NPC225385
0.8254 Intermediate Similarity NPC104585
0.8254 Intermediate Similarity NPC157817
0.8254 Intermediate Similarity NPC298783
0.825 Intermediate Similarity NPC257610
0.8246 Intermediate Similarity NPC38217
0.8246 Intermediate Similarity NPC472988
0.824 Intermediate Similarity NPC253456
0.824 Intermediate Similarity NPC159338
0.824 Intermediate Similarity NPC16569
0.8235 Intermediate Similarity NPC473828
0.8235 Intermediate Similarity NPC472080
0.8235 Intermediate Similarity NPC473617
0.823 Intermediate Similarity NPC51719
0.823 Intermediate Similarity NPC472818
0.823 Intermediate Similarity NPC472899
0.823 Intermediate Similarity NPC186668
0.823 Intermediate Similarity NPC472898
0.823 Intermediate Similarity NPC239961
0.823 Intermediate Similarity NPC472900
0.823 Intermediate Similarity NPC82251
0.823 Intermediate Similarity NPC85670
0.8214 Intermediate Similarity NPC10232
0.8214 Intermediate Similarity NPC196471
0.8214 Intermediate Similarity NPC160583
0.8214 Intermediate Similarity NPC189588
0.8214 Intermediate Similarity NPC187302
0.8214 Intermediate Similarity NPC97487
0.8211 Intermediate Similarity NPC179261
0.8205 Intermediate Similarity NPC171126

  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 NPC268326 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
0.9035 High Similarity NPD7328 Approved
0.9035 High Similarity NPD7327 Approved
0.8966 High Similarity NPD8033 Approved
0.8957 High Similarity NPD7516 Approved
0.8879 High Similarity NPD8377 Approved
0.8879 High Similarity NPD8294 Approved
0.8803 High Similarity NPD8335 Approved
0.8803 High Similarity NPD8378 Approved
0.8803 High Similarity NPD8296 Approved
0.8803 High Similarity NPD8380 Approved
0.8803 High Similarity NPD8379 Approved
0.8512 High Similarity NPD7507 Approved
0.8487 Intermediate Similarity NPD7503 Approved
0.8306 Intermediate Similarity NPD7319 Approved
0.7931 Intermediate Similarity NPD6686 Approved
0.7699 Intermediate Similarity NPD7638 Approved
0.7632 Intermediate Similarity NPD7639 Approved
0.7632 Intermediate Similarity NPD7640 Approved
0.7603 Intermediate Similarity NPD8133 Approved
0.7542 Intermediate Similarity NPD6412 Phase 2
0.7419 Intermediate Similarity NPD7115 Discovery
0.7417 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7736 Approved
0.7265 Intermediate Similarity NPD5344 Discontinued
0.7234 Intermediate Similarity NPD7625 Phase 1
0.7179 Intermediate Similarity NPD6648 Approved
0.7176 Intermediate Similarity NPD8293 Discontinued
0.7132 Intermediate Similarity NPD6370 Approved
0.7094 Intermediate Similarity NPD4225 Approved
0.7077 Intermediate Similarity NPD8328 Phase 3
0.7073 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7632 Discontinued
0.7054 Intermediate Similarity NPD8517 Approved
0.7054 Intermediate Similarity NPD8513 Phase 3
0.7054 Intermediate Similarity NPD8516 Approved
0.7054 Intermediate Similarity NPD8515 Approved
0.7023 Intermediate Similarity NPD7492 Approved
0.6992 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6059 Approved
0.6977 Remote Similarity NPD6054 Approved
0.697 Remote Similarity NPD6616 Approved
0.693 Remote Similarity NPD7838 Discovery
0.6917 Remote Similarity NPD7078 Approved
0.6885 Remote Similarity NPD6008 Approved
0.6875 Remote Similarity NPD6009 Approved
0.6875 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6882 Approved
0.6814 Remote Similarity NPD7524 Approved
0.6807 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6794 Remote Similarity NPD6015 Approved
0.6794 Remote Similarity NPD6016 Approved
0.6783 Remote Similarity NPD6698 Approved
0.6783 Remote Similarity NPD46 Approved
0.6774 Remote Similarity NPD7320 Approved
0.6772 Remote Similarity NPD4632 Approved
0.6748 Remote Similarity NPD6675 Approved
0.6748 Remote Similarity NPD6402 Approved
0.6748 Remote Similarity NPD7128 Approved
0.6748 Remote Similarity NPD5739 Approved
0.6742 Remote Similarity NPD5988 Approved
0.6718 Remote Similarity NPD6319 Approved
0.6696 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6693 Remote Similarity NPD6053 Discontinued
0.6693 Remote Similarity NPD8297 Approved
0.6692 Remote Similarity NPD6067 Discontinued
0.6667 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD8171 Discontinued
0.664 Remote Similarity NPD6899 Approved
0.664 Remote Similarity NPD6881 Approved
0.6636 Remote Similarity NPD7525 Registered
0.6607 Remote Similarity NPD6695 Phase 3
0.6587 Remote Similarity NPD6372 Approved
0.6587 Remote Similarity NPD6373 Approved
0.6581 Remote Similarity NPD7637 Suspended
0.6567 Remote Similarity NPD7604 Phase 2
0.656 Remote Similarity NPD5701 Approved
0.656 Remote Similarity NPD5697 Approved
0.6552 Remote Similarity NPD6051 Approved
0.6535 Remote Similarity NPD7102 Approved
0.6535 Remote Similarity NPD6883 Approved
0.6535 Remote Similarity NPD7290 Approved
0.6508 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6496 Remote Similarity NPD6033 Approved
0.6484 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6484 Remote Similarity NPD6617 Approved
0.6484 Remote Similarity NPD8130 Phase 1
0.6484 Remote Similarity NPD6649 Approved
0.6484 Remote Similarity NPD6847 Approved
0.6484 Remote Similarity NPD6869 Approved
0.6484 Remote Similarity NPD6650 Approved
0.6471 Remote Similarity NPD7748 Approved
0.6457 Remote Similarity NPD6013 Approved
0.6457 Remote Similarity NPD6014 Approved
0.6457 Remote Similarity NPD6012 Approved
0.6446 Remote Similarity NPD7902 Approved
0.6446 Remote Similarity NPD6084 Phase 2
0.6446 Remote Similarity NPD6083 Phase 2
0.6441 Remote Similarity NPD7515 Phase 2
0.6429 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6423 Remote Similarity NPD4159 Approved
0.6423 Remote Similarity NPD8074 Phase 3
0.6418 Remote Similarity NPD5983 Phase 2
0.64 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6387 Remote Similarity NPD6399 Phase 3
0.6379 Remote Similarity NPD7750 Discontinued
0.6378 Remote Similarity NPD6011 Approved
0.6357 Remote Similarity NPD6401 Clinical (unspecified phase)
0.635 Remote Similarity NPD6336 Discontinued
0.6339 Remote Similarity NPD7332 Phase 2
0.6339 Remote Similarity NPD6931 Approved
0.6339 Remote Similarity NPD6930 Phase 2
0.6339 Remote Similarity NPD6928 Phase 2
0.6319 Remote Similarity NPD7799 Discontinued
0.6312 Remote Similarity NPD8449 Approved
0.6311 Remote Similarity NPD4755 Approved
0.6303 Remote Similarity NPD8035 Phase 2
0.6303 Remote Similarity NPD8034 Phase 2
0.6281 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6279 Remote Similarity NPD4634 Approved
0.6273 Remote Similarity NPD6933 Approved
0.6268 Remote Similarity NPD8450 Suspended
0.625 Remote Similarity NPD4202 Approved
0.625 Remote Similarity NPD6929 Approved
0.625 Remote Similarity NPD7645 Phase 2
0.624 Remote Similarity NPD5211 Phase 2
0.6239 Remote Similarity NPD4751 Clinical (unspecified phase)
0.622 Remote Similarity NPD6640 Phase 3
0.621 Remote Similarity NPD4700 Approved
0.621 Remote Similarity NPD4696 Approved
0.621 Remote Similarity NPD5286 Approved
0.621 Remote Similarity NPD5285 Approved
0.6207 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6204 Remote Similarity NPD7830 Approved
0.6204 Remote Similarity NPD7829 Approved
0.6198 Remote Similarity NPD7900 Approved
0.6198 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6195 Remote Similarity NPD7509 Discontinued
0.6195 Remote Similarity NPD7514 Phase 3
0.6186 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7087 Discontinued
0.6165 Remote Similarity NPD6274 Approved
0.6148 Remote Similarity NPD5695 Phase 3
0.6148 Remote Similarity NPD7100 Approved
0.6148 Remote Similarity NPD7101 Approved
0.6142 Remote Similarity NPD5141 Approved
0.614 Remote Similarity NPD6898 Phase 1
0.614 Remote Similarity NPD6902 Approved
0.6134 Remote Similarity NPD1695 Approved
0.6134 Remote Similarity NPD5328 Approved
0.6129 Remote Similarity NPD5696 Approved
0.6127 Remote Similarity NPD7260 Phase 2
0.6111 Remote Similarity NPD5224 Approved
0.6111 Remote Similarity NPD5225 Approved
0.6111 Remote Similarity NPD5226 Approved
0.6111 Remote Similarity NPD4633 Approved
0.6091 Remote Similarity NPD6924 Approved
0.6091 Remote Similarity NPD6926 Approved
0.6087 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6083 Remote Similarity NPD3168 Discontinued
0.6074 Remote Similarity NPD6335 Approved
0.6071 Remote Similarity NPD5776 Phase 2
0.6071 Remote Similarity NPD6932 Approved
0.6071 Remote Similarity NPD6925 Approved
0.6068 Remote Similarity NPD6893 Approved
0.6063 Remote Similarity NPD5174 Approved
0.6063 Remote Similarity NPD5175 Approved
0.6058 Remote Similarity NPD6909 Approved
0.6058 Remote Similarity NPD6908 Approved
0.6056 Remote Similarity NPD5956 Approved
0.605 Remote Similarity NPD6903 Approved
0.6036 Remote Similarity NPD6942 Approved
0.6036 Remote Similarity NPD7339 Approved
0.6033 Remote Similarity NPD5284 Approved
0.6033 Remote Similarity NPD6079 Approved
0.6033 Remote Similarity NPD6411 Approved
0.6033 Remote Similarity NPD5693 Phase 1
0.6033 Remote Similarity NPD5281 Approved
0.6032 Remote Similarity NPD5223 Approved
0.6018 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6018 Remote Similarity NPD7145 Approved
0.6017 Remote Similarity NPD7521 Approved
0.6017 Remote Similarity NPD6409 Approved
0.6017 Remote Similarity NPD7334 Approved
0.6017 Remote Similarity NPD6684 Approved
0.6017 Remote Similarity NPD3618 Phase 1
0.6017 Remote Similarity NPD7146 Approved
0.6017 Remote Similarity NPD5330 Approved
0.6014 Remote Similarity NPD5126 Approved
0.6014 Remote Similarity NPD5125 Phase 3
0.6013 Remote Similarity NPD7236 Approved
0.6 Remote Similarity NPD4753 Phase 2
0.6 Remote Similarity NPD6317 Approved
0.5984 Remote Similarity NPD5779 Approved
0.5984 Remote Similarity NPD5778 Approved
0.5983 Remote Similarity NPD4786 Approved
0.5982 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5972 Remote Similarity NPD6845 Suspended
0.5969 Remote Similarity NPD4767 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