Structure

Physi-Chem Properties

Molecular Weight:  416.26
Volume:  434.216
LogP:  3.999
LogD:  3.881
LogS:  -4.652
# Rotatable Bonds:  4
TPSA:  76.13
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.328
Synthetic Accessibility Score:  5.537
Fsp3:  0.84
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.799
MDCK Permeability:  3.6853660276392475e-05
Pgp-inhibitor:  0.14
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.035
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.696

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.528
Plasma Protein Binding (PPB):  91.18124389648438%
Volume Distribution (VD):  1.735
Pgp-substrate:  6.715060710906982%

ADMET: Metabolism

CYP1A2-inhibitor:  0.212
CYP1A2-substrate:  0.362
CYP2C19-inhibitor:  0.065
CYP2C19-substrate:  0.702
CYP2C9-inhibitor:  0.106
CYP2C9-substrate:  0.013
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.104
CYP3A4-inhibitor:  0.738
CYP3A4-substrate:  0.372

ADMET: Excretion

Clearance (CL):  8.172
Half-life (T1/2):  0.404

ADMET: Toxicity

hERG Blockers:  0.307
Human Hepatotoxicity (H-HT):  0.968
Drug-inuced Liver Injury (DILI):  0.533
AMES Toxicity:  0.269
Rat Oral Acute Toxicity:  0.321
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.822
Carcinogencity:  0.53
Eye Corrosion:  0.966
Eye Irritation:  0.571
Respiratory Toxicity:  0.984

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  Natural Product: NPC298278

Natural Product ID:  NPC298278
Common Name*:   CQIQFZVEWSZZEF-ODZCDXGJSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CQIQFZVEWSZZEF-ODZCDXGJSA-N
Standard InCHI:  InChI=1S/C25H36O5/c1-5-15(13-26)20-21(29-14(2)27)22-25(30-22)19-7-6-16-12-17(28)8-10-23(16,3)18(19)9-11-24(20,25)4/h5,13,16-22,28H,6-12H2,1-4H3/b15-5+/t16-,17+,18+,19-,20+,21-,22-,23+,24-,25-/m1/s1
SMILES:  C/C=C(C=O)/[C@H]1[C@H]([C@@H]2[C@@]3([C@@H]4CC[C@@H]5C[C@H](CC[C@]5(C)[C@H]4CC[C@]13C)O)O2)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2431148
PubChem CID:   72702443
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001194] Oxosteroids
          • [CHEMONTID:0003060] 16-oxosteroids

*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
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)99818-1]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota roots n.a. n.a. PMID[10346940]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11421725]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15165135]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. aerial part n.a. PMID[15635246]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15730237]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[17504571]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[21185919]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. twig n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota twigs and leaves Yunnan Province, China 2008-OCT PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. leaf n.a. PMID[21954912]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[22708620]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota venom n.a. n.a. PMID[24050254]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[26722868]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[28256122]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[32223924]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26231 Vicia villosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2917 Artemisia oranensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7543 Haplopappus venetus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12250 Strychnos fendleri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4797 Gavia immer Species Gaviidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12952 Cabucala madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10043 Phebalium ozothamnoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5177 Lecanora conizaeoides Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6887 Lytanthus salicinus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12735 Halimeda macroloba Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2498 Kochia trichophylla Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9398 Cortinarius rubellus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6011 Pleurotus citrinopileatus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21463 Aruncus dioicus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7884 Centaurea amara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11515 Streptomyces plumbeus Species Streptomycetaceae Bacteria 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 IC50 = 45600.0 nM PMID[571528]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 26800.0 nM PMID[571528]
NPT27 Others Unspecified IC50 > 100000.0 nM PMID[571528]

☑ 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 NPC298278 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
0.8729 High Similarity NPC159499
0.8534 High Similarity NPC473203
0.8435 Intermediate Similarity NPC196931
0.8421 Intermediate Similarity NPC317210
0.8403 Intermediate Similarity NPC6193
0.8376 Intermediate Similarity NPC61520
0.8349 Intermediate Similarity NPC22388
0.8333 Intermediate Similarity NPC71348
0.8319 Intermediate Similarity NPC197428
0.8305 Intermediate Similarity NPC79579
0.8291 Intermediate Similarity NPC118638
0.8291 Intermediate Similarity NPC329736
0.8288 Intermediate Similarity NPC231530
0.8288 Intermediate Similarity NPC278628
0.8276 Intermediate Similarity NPC72772
0.8276 Intermediate Similarity NPC469794
0.8276 Intermediate Similarity NPC270958
0.8261 Intermediate Similarity NPC194100
0.8261 Intermediate Similarity NPC962
0.8261 Intermediate Similarity NPC202889
0.8261 Intermediate Similarity NPC250109
0.8257 Intermediate Similarity NPC469327
0.825 Intermediate Similarity NPC469789
0.8235 Intermediate Similarity NPC312481
0.8235 Intermediate Similarity NPC310511
0.8224 Intermediate Similarity NPC471039
0.822 Intermediate Similarity NPC475041
0.822 Intermediate Similarity NPC472667
0.8214 Intermediate Similarity NPC44063
0.8214 Intermediate Similarity NPC59530
0.8211 Intermediate Similarity NPC470880
0.8205 Intermediate Similarity NPC157380
0.8198 Intermediate Similarity NPC29705
0.8198 Intermediate Similarity NPC471293
0.8197 Intermediate Similarity NPC287423
0.8197 Intermediate Similarity NPC473253
0.819 Intermediate Similarity NPC326542
0.8182 Intermediate Similarity NPC473255
0.8174 Intermediate Similarity NPC280782
0.8174 Intermediate Similarity NPC476163
0.8174 Intermediate Similarity NPC234042
0.8174 Intermediate Similarity NPC152117
0.816 Intermediate Similarity NPC298783
0.816 Intermediate Similarity NPC157817
0.816 Intermediate Similarity NPC225385
0.816 Intermediate Similarity NPC104585
0.8158 Intermediate Similarity NPC76084
0.8151 Intermediate Similarity NPC474370
0.8142 Intermediate Similarity NPC94529
0.8136 Intermediate Similarity NPC153440
0.8136 Intermediate Similarity NPC16701
0.8125 Intermediate Similarity NPC470587
0.812 Intermediate Similarity NPC270929
0.812 Intermediate Similarity NPC49492
0.812 Intermediate Similarity NPC266728
0.8115 Intermediate Similarity NPC469750
0.8115 Intermediate Similarity NPC293112
0.8115 Intermediate Similarity NPC250556
0.8108 Intermediate Similarity NPC470310
0.8108 Intermediate Similarity NPC87927
0.8108 Intermediate Similarity NPC282233
0.8108 Intermediate Similarity NPC95585
0.8108 Intermediate Similarity NPC140723
0.8103 Intermediate Similarity NPC52634
0.8099 Intermediate Similarity NPC11895
0.8091 Intermediate Similarity NPC163963
0.8091 Intermediate Similarity NPC237190
0.8091 Intermediate Similarity NPC52899
0.8091 Intermediate Similarity NPC252614
0.8091 Intermediate Similarity NPC289148
0.8087 Intermediate Similarity NPC469656
0.8087 Intermediate Similarity NPC214797
0.8087 Intermediate Similarity NPC474846
0.8087 Intermediate Similarity NPC469655
0.8087 Intermediate Similarity NPC231589
0.8087 Intermediate Similarity NPC118860
0.8083 Intermediate Similarity NPC67569
0.808 Intermediate Similarity NPC42670
0.808 Intermediate Similarity NPC19124
0.8073 Intermediate Similarity NPC20479
0.8073 Intermediate Similarity NPC28864
0.8073 Intermediate Similarity NPC38296
0.8073 Intermediate Similarity NPC194196
0.8073 Intermediate Similarity NPC119036
0.8073 Intermediate Similarity NPC477854
0.8073 Intermediate Similarity NPC38471
0.8073 Intermediate Similarity NPC162459
0.8073 Intermediate Similarity NPC98837
0.807 Intermediate Similarity NPC475941
0.807 Intermediate Similarity NPC258543
0.807 Intermediate Similarity NPC241927
0.807 Intermediate Similarity NPC41405
0.807 Intermediate Similarity NPC474901
0.807 Intermediate Similarity NPC2766
0.8067 Intermediate Similarity NPC476960
0.8067 Intermediate Similarity NPC264954
0.8067 Intermediate Similarity NPC278681
0.8067 Intermediate Similarity NPC161065
0.8067 Intermediate Similarity NPC35171
0.8067 Intermediate Similarity NPC5292
0.8067 Intermediate Similarity NPC213761
0.8065 Intermediate Similarity NPC231529
0.8056 Intermediate Similarity NPC200054
0.8056 Intermediate Similarity NPC29410
0.8051 Intermediate Similarity NPC185287
0.8051 Intermediate Similarity NPC471854
0.8049 Intermediate Similarity NPC471356
0.8049 Intermediate Similarity NPC473265
0.8049 Intermediate Similarity NPC179412
0.8037 Intermediate Similarity NPC471040
0.8036 Intermediate Similarity NPC96268
0.8036 Intermediate Similarity NPC477812
0.8036 Intermediate Similarity NPC235889
0.8036 Intermediate Similarity NPC301787
0.8034 Intermediate Similarity NPC238667
0.8034 Intermediate Similarity NPC243354
0.8033 Intermediate Similarity NPC8369
0.8033 Intermediate Similarity NPC469790
0.8033 Intermediate Similarity NPC8374
0.8033 Intermediate Similarity NPC81736
0.8033 Intermediate Similarity NPC172154
0.8018 Intermediate Similarity NPC148628
0.8018 Intermediate Similarity NPC136289
0.8018 Intermediate Similarity NPC88203
0.8018 Intermediate Similarity NPC286519
0.8018 Intermediate Similarity NPC473928
0.8018 Intermediate Similarity NPC246736
0.8018 Intermediate Similarity NPC193934
0.8018 Intermediate Similarity NPC214946
0.8018 Intermediate Similarity NPC76866
0.8018 Intermediate Similarity NPC304832
0.8018 Intermediate Similarity NPC271980
0.8017 Intermediate Similarity NPC153700
0.8017 Intermediate Similarity NPC107493
0.8017 Intermediate Similarity NPC65858
0.8017 Intermediate Similarity NPC470063
0.8017 Intermediate Similarity NPC88326
0.8017 Intermediate Similarity NPC470265
0.8017 Intermediate Similarity NPC170538
0.8017 Intermediate Similarity NPC269642
0.8017 Intermediate Similarity NPC170487
0.8017 Intermediate Similarity NPC207251
0.8017 Intermediate Similarity NPC23786
0.8017 Intermediate Similarity NPC222688
0.8016 Intermediate Similarity NPC142756
0.8 Intermediate Similarity NPC6206
0.8 Intermediate Similarity NPC253456
0.8 Intermediate Similarity NPC159338
0.8 Intermediate Similarity NPC5284
0.8 Intermediate Similarity NPC474585
0.8 Intermediate Similarity NPC268530
0.8 Intermediate Similarity NPC287676
0.8 Intermediate Similarity NPC16569
0.8 Intermediate Similarity NPC251226
0.8 Intermediate Similarity NPC112936
0.8 Intermediate Similarity NPC154491
0.8 Intermediate Similarity NPC143755
0.8 Intermediate Similarity NPC241192
0.8 Intermediate Similarity NPC293866
0.7983 Intermediate Similarity NPC709
0.7983 Intermediate Similarity NPC311554
0.7983 Intermediate Similarity NPC257457
0.7983 Intermediate Similarity NPC50774
0.7982 Intermediate Similarity NPC273155
0.7982 Intermediate Similarity NPC112895
0.7982 Intermediate Similarity NPC218123
0.7982 Intermediate Similarity NPC211224
0.7982 Intermediate Similarity NPC275539
0.7982 Intermediate Similarity NPC189075
0.7982 Intermediate Similarity NPC177064
0.7982 Intermediate Similarity NPC329417
0.7982 Intermediate Similarity NPC231278
0.7967 Intermediate Similarity NPC473635
0.7966 Intermediate Similarity NPC190286
0.7966 Intermediate Similarity NPC302471
0.7965 Intermediate Similarity NPC472655
0.7965 Intermediate Similarity NPC196528
0.7965 Intermediate Similarity NPC220217
0.7965 Intermediate Similarity NPC102352
0.7965 Intermediate Similarity NPC265127
0.7965 Intermediate Similarity NPC96377
0.7965 Intermediate Similarity NPC200957
0.7965 Intermediate Similarity NPC119855
0.7965 Intermediate Similarity NPC181265
0.7965 Intermediate Similarity NPC37600
0.7965 Intermediate Similarity NPC138908
0.7965 Intermediate Similarity NPC222833
0.7963 Intermediate Similarity NPC98639
0.7963 Intermediate Similarity NPC469599
0.7963 Intermediate Similarity NPC279974
0.7951 Intermediate Similarity NPC55602
0.7951 Intermediate Similarity NPC473979
0.7951 Intermediate Similarity NPC27363
0.7951 Intermediate Similarity NPC43252
0.7951 Intermediate Similarity NPC135038
0.7951 Intermediate Similarity NPC204812
0.7949 Intermediate Similarity NPC471627
0.7949 Intermediate Similarity NPC178981
0.7949 Intermediate Similarity NPC255017
0.7949 Intermediate Similarity NPC471173

  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 NPC298278 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
0.8333 Intermediate Similarity NPD8297 Approved
0.8304 Intermediate Similarity NPD6899 Approved
0.8304 Intermediate Similarity NPD6881 Approved
0.8288 Intermediate Similarity NPD6675 Approved
0.8288 Intermediate Similarity NPD7128 Approved
0.8288 Intermediate Similarity NPD6402 Approved
0.8288 Intermediate Similarity NPD5739 Approved
0.8288 Intermediate Similarity NPD6008 Approved
0.8246 Intermediate Similarity NPD6649 Approved
0.8246 Intermediate Similarity NPD6650 Approved
0.823 Intermediate Similarity NPD6373 Approved
0.823 Intermediate Similarity NPD6372 Approved
0.8214 Intermediate Similarity NPD5697 Approved
0.8158 Intermediate Similarity NPD7102 Approved
0.8158 Intermediate Similarity NPD7290 Approved
0.8158 Intermediate Similarity NPD6883 Approved
0.8151 Intermediate Similarity NPD6319 Approved
0.8142 Intermediate Similarity NPD7320 Approved
0.8115 Intermediate Similarity NPD7507 Approved
0.8103 Intermediate Similarity NPD4632 Approved
0.8087 Intermediate Similarity NPD6869 Approved
0.8087 Intermediate Similarity NPD6617 Approved
0.8087 Intermediate Similarity NPD8130 Phase 1
0.8087 Intermediate Similarity NPD6847 Approved
0.807 Intermediate Similarity NPD6013 Approved
0.807 Intermediate Similarity NPD6012 Approved
0.807 Intermediate Similarity NPD6014 Approved
0.8053 Intermediate Similarity NPD5701 Approved
0.8033 Intermediate Similarity NPD7492 Approved
0.8017 Intermediate Similarity NPD6882 Approved
0.8 Intermediate Similarity NPD6054 Approved
0.7984 Intermediate Similarity NPD7736 Approved
0.7982 Intermediate Similarity NPD6011 Approved
0.7967 Intermediate Similarity NPD6616 Approved
0.7951 Intermediate Similarity NPD7604 Phase 2
0.792 Intermediate Similarity NPD7319 Approved
0.7903 Intermediate Similarity NPD7078 Approved
0.7899 Intermediate Similarity NPD7115 Discovery
0.7899 Intermediate Similarity NPD6009 Approved
0.7869 Intermediate Similarity NPD6370 Approved
0.7851 Intermediate Similarity NPD6059 Approved
0.7838 Intermediate Similarity NPD4696 Approved
0.7838 Intermediate Similarity NPD5286 Approved
0.7838 Intermediate Similarity NPD5285 Approved
0.7818 Intermediate Similarity NPD4755 Approved
0.7787 Intermediate Similarity NPD5983 Phase 2
0.7787 Intermediate Similarity NPD6016 Approved
0.7787 Intermediate Similarity NPD6015 Approved
0.7778 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD8293 Discontinued
0.7748 Intermediate Similarity NPD7638 Approved
0.7724 Intermediate Similarity NPD5988 Approved
0.7699 Intermediate Similarity NPD5224 Approved
0.7699 Intermediate Similarity NPD5225 Approved
0.7699 Intermediate Similarity NPD4633 Approved
0.7699 Intermediate Similarity NPD5211 Phase 2
0.7699 Intermediate Similarity NPD5226 Approved
0.7692 Intermediate Similarity NPD4634 Approved
0.768 Intermediate Similarity NPD6336 Discontinued
0.7679 Intermediate Similarity NPD7640 Approved
0.7679 Intermediate Similarity NPD7639 Approved
0.7679 Intermediate Similarity NPD4700 Approved
0.7667 Intermediate Similarity NPD6274 Approved
0.7658 Intermediate Similarity NPD6083 Phase 2
0.7658 Intermediate Similarity NPD6084 Phase 2
0.7632 Intermediate Similarity NPD5174 Approved
0.7632 Intermediate Similarity NPD5175 Approved
0.7623 Intermediate Similarity NPD7100 Approved
0.7623 Intermediate Similarity NPD7101 Approved
0.7615 Intermediate Similarity NPD6399 Phase 3
0.7611 Intermediate Similarity NPD5223 Approved
0.7568 Intermediate Similarity NPD4697 Phase 3
0.7565 Intermediate Similarity NPD5141 Approved
0.7541 Intermediate Similarity NPD6335 Approved
0.7523 Intermediate Similarity NPD6079 Approved
0.75 Intermediate Similarity NPD5328 Approved
0.7477 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD6317 Approved
0.7455 Intermediate Similarity NPD4202 Approved
0.7436 Intermediate Similarity NPD6412 Phase 2
0.7434 Intermediate Similarity NPD5696 Approved
0.7417 Intermediate Similarity NPD6053 Discontinued
0.7398 Intermediate Similarity NPD6313 Approved
0.7398 Intermediate Similarity NPD6314 Approved
0.7373 Intermediate Similarity NPD4729 Approved
0.7373 Intermediate Similarity NPD5128 Approved
0.7373 Intermediate Similarity NPD4730 Approved
0.7364 Intermediate Similarity NPD8034 Phase 2
0.7364 Intermediate Similarity NPD8035 Phase 2
0.736 Intermediate Similarity NPD6908 Approved
0.736 Intermediate Similarity NPD8033 Approved
0.736 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6909 Approved
0.735 Intermediate Similarity NPD4767 Approved
0.735 Intermediate Similarity NPD4768 Approved
0.7345 Intermediate Similarity NPD7902 Approved
0.7328 Intermediate Similarity NPD4754 Approved
0.7321 Intermediate Similarity NPD5695 Phase 3
0.7311 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD6033 Approved
0.7258 Intermediate Similarity NPD7327 Approved
0.7258 Intermediate Similarity NPD7328 Approved
0.7257 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD5221 Approved
0.7257 Intermediate Similarity NPD5222 Approved
0.725 Intermediate Similarity NPD5251 Approved
0.725 Intermediate Similarity NPD5250 Approved
0.725 Intermediate Similarity NPD5249 Phase 3
0.725 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD5248 Approved
0.725 Intermediate Similarity NPD5247 Approved
0.7248 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7748 Approved
0.7222 Intermediate Similarity NPD3618 Phase 1
0.7222 Intermediate Similarity NPD5330 Approved
0.7222 Intermediate Similarity NPD6684 Approved
0.7222 Intermediate Similarity NPD7334 Approved
0.7222 Intermediate Similarity NPD7521 Approved
0.7222 Intermediate Similarity NPD7146 Approved
0.7222 Intermediate Similarity NPD6409 Approved
0.7207 Intermediate Similarity NPD7515 Phase 2
0.72 Intermediate Similarity NPD7516 Approved
0.7193 Intermediate Similarity NPD5173 Approved
0.719 Intermediate Similarity NPD5217 Approved
0.719 Intermediate Similarity NPD5216 Approved
0.719 Intermediate Similarity NPD5215 Approved
0.7182 Intermediate Similarity NPD4753 Phase 2
0.7168 Intermediate Similarity NPD4629 Approved
0.7168 Intermediate Similarity NPD5210 Approved
0.7143 Intermediate Similarity NPD8377 Approved
0.7143 Intermediate Similarity NPD8294 Approved
0.713 Intermediate Similarity NPD4225 Approved
0.713 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD8328 Phase 3
0.7107 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5135 Approved
0.7107 Intermediate Similarity NPD5169 Approved
0.7097 Intermediate Similarity NPD6868 Approved
0.7094 Intermediate Similarity NPD7632 Discontinued
0.7091 Intermediate Similarity NPD6903 Approved
0.7087 Intermediate Similarity NPD8378 Approved
0.7087 Intermediate Similarity NPD8335 Approved
0.7087 Intermediate Similarity NPD8380 Approved
0.7087 Intermediate Similarity NPD8296 Approved
0.7087 Intermediate Similarity NPD8379 Approved
0.7083 Intermediate Similarity NPD6686 Approved
0.708 Intermediate Similarity NPD7900 Approved
0.708 Intermediate Similarity NPD6001 Approved
0.708 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD5284 Approved
0.7054 Intermediate Similarity NPD5281 Approved
0.7049 Intermediate Similarity NPD5127 Approved
0.7037 Intermediate Similarity NPD3665 Phase 1
0.7037 Intermediate Similarity NPD3666 Approved
0.7037 Intermediate Similarity NPD3133 Approved
0.7037 Intermediate Similarity NPD4786 Approved
0.7027 Intermediate Similarity NPD6673 Approved
0.7027 Intermediate Similarity NPD6080 Approved
0.7027 Intermediate Similarity NPD6904 Approved
0.7 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7525 Registered
0.6977 Remote Similarity NPD6067 Discontinued
0.6967 Remote Similarity NPD6371 Approved
0.6953 Remote Similarity NPD7503 Approved
0.6944 Remote Similarity NPD4788 Approved
0.6942 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6672 Approved
0.6937 Remote Similarity NPD5737 Approved
0.6935 Remote Similarity NPD8133 Approved
0.6909 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6905 Remote Similarity NPD8295 Clinical (unspecified phase)
0.688 Remote Similarity NPD5167 Approved
0.6852 Remote Similarity NPD3667 Approved
0.6852 Remote Similarity NPD4223 Phase 3
0.6852 Remote Similarity NPD6435 Approved
0.6852 Remote Similarity NPD4221 Approved
0.6847 Remote Similarity NPD3573 Approved
0.6818 Remote Similarity NPD5329 Approved
0.6786 Remote Similarity NPD5208 Approved
0.6757 Remote Similarity NPD6098 Approved
0.6754 Remote Similarity NPD6050 Approved
0.6754 Remote Similarity NPD6411 Approved
0.6754 Remote Similarity NPD5693 Phase 1
0.6748 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6727 Remote Similarity NPD4197 Approved
0.6723 Remote Similarity NPD1700 Approved
0.6723 Remote Similarity NPD5344 Discontinued
0.6698 Remote Similarity NPD6116 Phase 1
0.6667 Remote Similarity NPD6698 Approved
0.6667 Remote Similarity NPD46 Approved
0.6667 Remote Similarity NPD5207 Approved
0.6667 Remote Similarity NPD5956 Approved
0.6667 Remote Similarity NPD5692 Phase 3
0.6667 Remote Similarity NPD5168 Approved
0.6667 Remote Similarity NPD5368 Approved
0.6636 Remote Similarity NPD6114 Approved
0.6636 Remote Similarity NPD6115 Approved
0.6636 Remote Similarity NPD6697 Approved
0.6636 Remote Similarity NPD6118 Approved
0.6609 Remote Similarity NPD5694 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