Structure

Physi-Chem Properties

Molecular Weight:  456.36
Volume:  505.751
LogP:  6.08
LogD:  4.322
LogS:  -3.872
# Rotatable Bonds:  1
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.444
Synthetic Accessibility Score:  4.867
Fsp3:  0.933
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.445
MDCK Permeability:  1.1365379577910062e-05
Pgp-inhibitor:  0.699
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.097
20% Bioavailability (F20%):  0.029
30% Bioavailability (F30%):  0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.386
Plasma Protein Binding (PPB):  90.34587860107422%
Volume Distribution (VD):  0.724
Pgp-substrate:  3.636211633682251%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.629
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.904
CYP2C9-inhibitor:  0.048
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.063
CYP3A4-inhibitor:  0.583
CYP3A4-substrate:  0.499

ADMET: Excretion

Clearance (CL):  8.358
Half-life (T1/2):  0.142

ADMET: Toxicity

hERG Blockers:  0.041
Human Hepatotoxicity (H-HT):  0.481
Drug-inuced Liver Injury (DILI):  0.031
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.716
Maximum Recommended Daily Dose:  0.57
Skin Sensitization:  0.484
Carcinogencity:  0.592
Eye Corrosion:  0.087
Eye Irritation:  0.02
Respiratory Toxicity:  0.973

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Similar NPs/Drugs  

  Natural Product: NPC281203

Natural Product ID:  NPC281203
Common Name*:   (2S,4As,6Ar,6Bs,8As,9R,12As,12Bs,14As,14Br)-2,4A,6A,8A,9,12B,14A-Heptamethyl-10-Oxodocosahydropicene-2-Carboxylic Acid
IUPAC Name:   (2S,4aS,6aS,6aR,6bS,8aS,9R,12aS,14aS,14bR)-2,4a,6a,6a,8a,9,14a-heptamethyl-10-oxo-3,4,5,6,6b,7,8,9,11,12,12a,13,14,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms:  
Standard InCHIKey:  WHWHDGKOSUKYOV-VYTNREEISA-N
Standard InCHI:  InChI=1S/C30H48O3/c1-19-20(31)8-9-21-27(19,4)11-10-22-28(21,5)15-17-30(7)23-18-26(3,24(32)33)13-12-25(23,2)14-16-29(22,30)6/h19,21-23H,8-18H2,1-7H3,(H,32,33)/t19-,21+,22-,23+,25+,26-,27+,28-,29+,30-/m0/s1
SMILES:  C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]12C)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL483029
PubChem CID:   14108946
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO24927 Calyx podatypa Species Phloeodictyidae Eukaryota n.a. n.a. n.a. PMID[10843583]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO25232 Peperomia heyneana Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[17291043]
NPO24927 Calyx podatypa Species Phloeodictyidae Eukaryota n.a. n.a. n.a. PMID[1791477]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO8412 Monanchora arbuscula Species Crambeidae Eukaryota n.a. Caribbean n.a. PMID[19743809]
NPO631 Osyris lanceolata Species Santalaceae Eukaryota n.a. n.a. n.a. PMID[20499922]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO4016 Ligularia fischeri Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24892518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO8412 Monanchora arbuscula Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[25924111]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4016 Ligularia fischeri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4016 Ligularia fischeri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8117 Aureolaria virginica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8412 Monanchora arbuscula Species Crambeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26578 Astragalus pamirensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27107 Coleus coerulescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24927 Calyx podatypa Species Phloeodictyidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8818 Rohdea wattii Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2871 Canistrocarpus cervicornis Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26370 Iryanthera juruensis Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27395 Mandragora officinarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24417 Centaurea hololeuca Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25232 Peperomia heyneana Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16903 Chisocheton siamensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO631 Osyris lanceolata Species Santalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25293 Beaumontia brevituba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4016 Ligularia fischeri Species Asteraceae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 44000.0 nM PMID[487789]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 ED50 = 59.0 uM PMID[487789]

☑ 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 NPC281203 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 NPC100917
1.0 High Similarity NPC31187
1.0 High Similarity NPC469724
0.9104 High Similarity NPC108131
0.9091 High Similarity NPC2568
0.9091 High Similarity NPC260319
0.9091 High Similarity NPC180777
0.9091 High Similarity NPC103647
0.8873 High Similarity NPC112463
0.875 High Similarity NPC26029
0.8696 High Similarity NPC290058
0.8696 High Similarity NPC247195
0.8571 High Similarity NPC282905
0.8571 High Similarity NPC68426
0.8571 High Similarity NPC475230
0.8571 High Similarity NPC477229
0.8529 High Similarity NPC470956
0.8529 High Similarity NPC473225
0.8529 High Similarity NPC475977
0.8507 High Similarity NPC42060
0.8493 Intermediate Similarity NPC31031
0.8493 Intermediate Similarity NPC243594
0.8493 Intermediate Similarity NPC472608
0.8451 Intermediate Similarity NPC168511
0.8451 Intermediate Similarity NPC159325
0.8451 Intermediate Similarity NPC130011
0.8406 Intermediate Similarity NPC474962
0.8358 Intermediate Similarity NPC19311
0.8358 Intermediate Similarity NPC230047
0.8358 Intermediate Similarity NPC469791
0.8333 Intermediate Similarity NPC267753
0.831 Intermediate Similarity NPC36310
0.8235 Intermediate Similarity NPC268736
0.8235 Intermediate Similarity NPC477931
0.8219 Intermediate Similarity NPC108840
0.8194 Intermediate Similarity NPC255168
0.8169 Intermediate Similarity NPC472309
0.8158 Intermediate Similarity NPC474870
0.8158 Intermediate Similarity NPC271572
0.8158 Intermediate Similarity NPC162632
0.8158 Intermediate Similarity NPC476071
0.8158 Intermediate Similarity NPC274050
0.8158 Intermediate Similarity NPC263272
0.8158 Intermediate Similarity NPC267691
0.8158 Intermediate Similarity NPC280781
0.8158 Intermediate Similarity NPC48756
0.8143 Intermediate Similarity NPC196197
0.8143 Intermediate Similarity NPC469941
0.8143 Intermediate Similarity NPC252032
0.8143 Intermediate Similarity NPC476734
0.8143 Intermediate Similarity NPC178541
0.8143 Intermediate Similarity NPC319671
0.8133 Intermediate Similarity NPC192744
0.8116 Intermediate Similarity NPC41542
0.8116 Intermediate Similarity NPC478180
0.8116 Intermediate Similarity NPC474221
0.8116 Intermediate Similarity NPC130459
0.8108 Intermediate Similarity NPC298168
0.8108 Intermediate Similarity NPC143133
0.8095 Intermediate Similarity NPC307063
0.8082 Intermediate Similarity NPC179858
0.8056 Intermediate Similarity NPC81759
0.8052 Intermediate Similarity NPC69101
0.8052 Intermediate Similarity NPC251779
0.8028 Intermediate Similarity NPC477929
0.8 Intermediate Similarity NPC127798
0.8 Intermediate Similarity NPC474954
0.7975 Intermediate Similarity NPC62572
0.7949 Intermediate Similarity NPC70834
0.7945 Intermediate Similarity NPC280026
0.7945 Intermediate Similarity NPC167702
0.7917 Intermediate Similarity NPC469940
0.7917 Intermediate Similarity NPC478227
0.7895 Intermediate Similarity NPC16394
0.7887 Intermediate Similarity NPC64466
0.7867 Intermediate Similarity NPC477918
0.7867 Intermediate Similarity NPC68828
0.7848 Intermediate Similarity NPC96095
0.7838 Intermediate Similarity NPC174964
0.7838 Intermediate Similarity NPC472311
0.7838 Intermediate Similarity NPC195155
0.7838 Intermediate Similarity NPC97534
0.7838 Intermediate Similarity NPC212733
0.7821 Intermediate Similarity NPC61107
0.7821 Intermediate Similarity NPC289486
0.7821 Intermediate Similarity NPC30583
0.7792 Intermediate Similarity NPC261616
0.7778 Intermediate Similarity NPC477850
0.7763 Intermediate Similarity NPC185465
0.7733 Intermediate Similarity NPC475742
0.7733 Intermediate Similarity NPC89294
0.7733 Intermediate Similarity NPC4209
0.7733 Intermediate Similarity NPC104806
0.7733 Intermediate Similarity NPC5767
0.7722 Intermediate Similarity NPC472740
0.7703 Intermediate Similarity NPC477930
0.7692 Intermediate Similarity NPC50658
0.7692 Intermediate Similarity NPC471898
0.7671 Intermediate Similarity NPC58057
0.7671 Intermediate Similarity NPC151018
0.7671 Intermediate Similarity NPC197701
0.7671 Intermediate Similarity NPC320549
0.7671 Intermediate Similarity NPC156277
0.7662 Intermediate Similarity NPC231431
0.7662 Intermediate Similarity NPC320144
0.7662 Intermediate Similarity NPC73013
0.7654 Intermediate Similarity NPC187545
0.7639 Intermediate Similarity NPC213178
0.7639 Intermediate Similarity NPC6120
0.7639 Intermediate Similarity NPC321732
0.7639 Intermediate Similarity NPC324607
0.7639 Intermediate Similarity NPC327728
0.7639 Intermediate Similarity NPC131892
0.7632 Intermediate Similarity NPC207010
0.7632 Intermediate Similarity NPC317913
0.7632 Intermediate Similarity NPC23884
0.7632 Intermediate Similarity NPC212661
0.7632 Intermediate Similarity NPC477919
0.7632 Intermediate Similarity NPC221420
0.7632 Intermediate Similarity NPC66105
0.7632 Intermediate Similarity NPC107039
0.7632 Intermediate Similarity NPC471897
0.7632 Intermediate Similarity NPC471899
0.7632 Intermediate Similarity NPC180199
0.7632 Intermediate Similarity NPC471035
0.7625 Intermediate Similarity NPC237938
0.7625 Intermediate Similarity NPC219535
0.76 Intermediate Similarity NPC477934
0.7568 Intermediate Similarity NPC232112
0.7568 Intermediate Similarity NPC161187
0.7568 Intermediate Similarity NPC310766
0.7568 Intermediate Similarity NPC244708
0.7568 Intermediate Similarity NPC177826
0.7568 Intermediate Similarity NPC330659
0.7564 Intermediate Similarity NPC37038
0.7564 Intermediate Similarity NPC472853
0.7564 Intermediate Similarity NPC267517
0.7564 Intermediate Similarity NPC18955
0.7561 Intermediate Similarity NPC173089
0.7561 Intermediate Similarity NPC158141
0.7534 Intermediate Similarity NPC476731
0.7532 Intermediate Similarity NPC476810
0.7532 Intermediate Similarity NPC280654
0.7532 Intermediate Similarity NPC324700
0.7532 Intermediate Similarity NPC34046
0.7532 Intermediate Similarity NPC476732
0.7532 Intermediate Similarity NPC171426
0.7532 Intermediate Similarity NPC110094
0.7532 Intermediate Similarity NPC80089
0.7532 Intermediate Similarity NPC224802
0.7532 Intermediate Similarity NPC329117
0.7532 Intermediate Similarity NPC260385
0.7532 Intermediate Similarity NPC63020
0.7532 Intermediate Similarity NPC199965
0.7531 Intermediate Similarity NPC474537
0.7531 Intermediate Similarity NPC201655
0.75 Intermediate Similarity NPC477933
0.75 Intermediate Similarity NPC477932
0.75 Intermediate Similarity NPC246445
0.75 Intermediate Similarity NPC290445
0.75 Intermediate Similarity NPC20466
0.75 Intermediate Similarity NPC36616
0.75 Intermediate Similarity NPC200752
0.747 Intermediate Similarity NPC474474
0.747 Intermediate Similarity NPC474511
0.747 Intermediate Similarity NPC1753
0.7468 Intermediate Similarity NPC3915
0.7468 Intermediate Similarity NPC142244
0.7467 Intermediate Similarity NPC162164
0.7467 Intermediate Similarity NPC254340
0.7467 Intermediate Similarity NPC472854
0.7439 Intermediate Similarity NPC83242
0.7439 Intermediate Similarity NPC72638
0.7439 Intermediate Similarity NPC56588
0.7436 Intermediate Similarity NPC80891
0.7436 Intermediate Similarity NPC199595
0.7436 Intermediate Similarity NPC201276
0.7436 Intermediate Similarity NPC201459
0.7436 Intermediate Similarity NPC472310
0.7432 Intermediate Similarity NPC89310
0.7432 Intermediate Similarity NPC473267
0.7407 Intermediate Similarity NPC25037
0.7407 Intermediate Similarity NPC473299
0.7407 Intermediate Similarity NPC34984
0.7407 Intermediate Similarity NPC105895
0.7407 Intermediate Similarity NPC171789
0.7403 Intermediate Similarity NPC474404
0.7381 Intermediate Similarity NPC474700
0.7381 Intermediate Similarity NPC281524
0.7375 Intermediate Similarity NPC310989
0.7368 Intermediate Similarity NPC201027
0.7368 Intermediate Similarity NPC21220
0.7368 Intermediate Similarity NPC273366
0.7368 Intermediate Similarity NPC125767
0.7361 Intermediate Similarity NPC472984
0.7349 Intermediate Similarity NPC88716
0.7349 Intermediate Similarity NPC242468
0.7349 Intermediate Similarity NPC98442
0.7349 Intermediate Similarity NPC51700
0.7349 Intermediate Similarity NPC142415

  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 NPC281203 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
0.8788 High Similarity NPD4224 Phase 2
0.8429 Intermediate Similarity NPD6081 Approved
0.8 Intermediate Similarity NPD5360 Phase 3
0.8 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD4244 Approved
0.7778 Intermediate Similarity NPD4245 Approved
0.7778 Intermediate Similarity NPD4789 Approved
0.7733 Intermediate Similarity NPD6117 Approved
0.7671 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD5777 Approved
0.7671 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD3698 Phase 2
0.7632 Intermediate Similarity NPD6116 Phase 1
0.7571 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6697 Approved
0.7532 Intermediate Similarity NPD6118 Approved
0.7532 Intermediate Similarity NPD6115 Approved
0.7532 Intermediate Similarity NPD6114 Approved
0.7432 Intermediate Similarity NPD4758 Discontinued
0.7385 Intermediate Similarity NPD615 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3702 Approved
0.7317 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD7515 Phase 2
0.7176 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3703 Phase 2
0.7089 Intermediate Similarity NPD5364 Discontinued
0.7045 Intermediate Similarity NPD7748 Approved
0.6875 Remote Similarity NPD3671 Phase 1
0.6818 Remote Similarity NPD8034 Phase 2
0.6818 Remote Similarity NPD8035 Phase 2
0.6813 Remote Similarity NPD7902 Approved
0.6703 Remote Similarity NPD7614 Phase 1
0.6667 Remote Similarity NPD3617 Approved
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD634 Phase 3
0.6618 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6567 Remote Similarity NPD3186 Phase 1
0.6484 Remote Similarity NPD7900 Approved
0.6484 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6477 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6395 Remote Similarity NPD4786 Approved
0.6389 Remote Similarity NPD3198 Approved
0.6374 Remote Similarity NPD6399 Phase 3
0.6353 Remote Similarity NPD3667 Approved
0.6353 Remote Similarity NPD4223 Phase 3
0.6353 Remote Similarity NPD4221 Approved
0.6322 Remote Similarity NPD5329 Approved
0.631 Remote Similarity NPD4695 Discontinued
0.625 Remote Similarity NPD6409 Approved
0.625 Remote Similarity NPD5330 Approved
0.625 Remote Similarity NPD7521 Approved
0.625 Remote Similarity NPD6098 Approved
0.625 Remote Similarity NPD6684 Approved
0.625 Remote Similarity NPD7334 Approved
0.625 Remote Similarity NPD7146 Approved
0.6235 Remote Similarity NPD4692 Approved
0.6235 Remote Similarity NPD4139 Approved
0.6207 Remote Similarity NPD4197 Approved
0.6207 Remote Similarity NPD3133 Approved
0.6207 Remote Similarity NPD3665 Phase 1
0.6207 Remote Similarity NPD3666 Approved
0.619 Remote Similarity NPD387 Clinical (unspecified phase)
0.618 Remote Similarity NPD3573 Approved
0.617 Remote Similarity NPD7732 Phase 3
0.6111 Remote Similarity NPD6672 Approved
0.6111 Remote Similarity NPD6903 Approved
0.6111 Remote Similarity NPD5737 Approved
0.6105 Remote Similarity NPD6084 Phase 2
0.6105 Remote Similarity NPD6083 Phase 2
0.6087 Remote Similarity NPD5284 Approved
0.6087 Remote Similarity NPD5281 Approved
0.6076 Remote Similarity NPD3725 Approved
0.6076 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6076 Remote Similarity NPD3726 Approved
0.6067 Remote Similarity NPD4689 Approved
0.6067 Remote Similarity NPD4690 Approved
0.6067 Remote Similarity NPD4138 Approved
0.6067 Remote Similarity NPD5205 Approved
0.6067 Remote Similarity NPD4688 Approved
0.6067 Remote Similarity NPD4623 Approved
0.6067 Remote Similarity NPD3618 Phase 1
0.6067 Remote Similarity NPD4519 Discontinued
0.6067 Remote Similarity NPD4693 Phase 3
0.6067 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6053 Remote Similarity NPD7909 Approved
0.6044 Remote Similarity NPD6673 Approved
0.6044 Remote Similarity NPD6080 Approved
0.6044 Remote Similarity NPD6904 Approved
0.6044 Remote Similarity NPD5328 Approved
0.6032 Remote Similarity NPD2270 Approved
0.6 Remote Similarity NPD4787 Phase 1
0.6 Remote Similarity NPD7645 Phase 2
0.5979 Remote Similarity NPD8418 Phase 2
0.5934 Remote Similarity NPD5208 Approved
0.5914 Remote Similarity NPD6079 Approved
0.59 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5895 Remote Similarity NPD5695 Phase 3
0.5889 Remote Similarity NPD5690 Phase 2
0.5889 Remote Similarity NPD5280 Approved
0.5889 Remote Similarity NPD4694 Approved
0.5876 Remote Similarity NPD5696 Approved
0.587 Remote Similarity NPD4753 Phase 2
0.5867 Remote Similarity NPD9656 Approved
0.5843 Remote Similarity NPD3668 Phase 3
0.5825 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5769 Remote Similarity NPD7341 Phase 2
0.5758 Remote Similarity NPD3199 Clinical (unspecified phase)
0.5747 Remote Similarity NPD6928 Phase 2
0.5745 Remote Similarity NPD5693 Phase 1
0.5745 Remote Similarity NPD6050 Approved
0.5735 Remote Similarity NPD2266 Phase 2
0.5729 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7638 Approved
0.5714 Remote Similarity NPD9638 Phase 2
0.5714 Remote Similarity NPD633 Phase 3
0.5714 Remote Similarity NPD77 Approved
0.5714 Remote Similarity NPD9448 Phase 2
0.5714 Remote Similarity NPD9450 Approved
0.5714 Remote Similarity NPD5279 Phase 3
0.5698 Remote Similarity NPD4238 Approved
0.5698 Remote Similarity NPD4802 Phase 2
0.5696 Remote Similarity NPD375 Phase 2
0.5686 Remote Similarity NPD5739 Approved
0.5686 Remote Similarity NPD6402 Approved
0.5686 Remote Similarity NPD6675 Approved
0.5686 Remote Similarity NPD7128 Approved
0.5684 Remote Similarity NPD4202 Approved
0.5682 Remote Similarity NPD8028 Phase 2
0.5679 Remote Similarity NPD4137 Phase 3
0.5676 Remote Similarity NPD9438 Approved
0.5676 Remote Similarity NPD9439 Approved
0.5672 Remote Similarity NPD386 Approved
0.5672 Remote Similarity NPD388 Approved
0.5657 Remote Similarity NPD7640 Approved
0.5657 Remote Similarity NPD7639 Approved
0.5638 Remote Similarity NPD5207 Approved
0.5638 Remote Similarity NPD5692 Phase 3
0.5632 Remote Similarity NPD4195 Approved
0.5625 Remote Similarity NPD6001 Approved
0.5618 Remote Similarity NPD4752 Clinical (unspecified phase)
0.561 Remote Similarity NPD4747 Approved
0.561 Remote Similarity NPD4691 Approved
0.5607 Remote Similarity NPD8133 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