Structure

Physi-Chem Properties

Molecular Weight:  682.41
Volume:  712.35
LogP:  6.408
LogD:  4.317
LogS:  -5.668
# Rotatable Bonds:  12
TPSA:  117.73
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.083
Synthetic Accessibility Score:  5.656
Fsp3:  0.8
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.074
MDCK Permeability:  3.76554271497298e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.832
30% Bioavailability (F30%):  0.685

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.035
Plasma Protein Binding (PPB):  89.28594207763672%
Volume Distribution (VD):  2.611
Pgp-substrate:  4.733465671539307%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.087
CYP2C19-inhibitor:  0.133
CYP2C19-substrate:  0.628
CYP2C9-inhibitor:  0.466
CYP2C9-substrate:  0.025
CYP2D6-inhibitor:  0.087
CYP2D6-substrate:  0.014
CYP3A4-inhibitor:  0.842
CYP3A4-substrate:  0.673

ADMET: Excretion

Clearance (CL):  3.136
Half-life (T1/2):  0.113

ADMET: Toxicity

hERG Blockers:  0.739
Human Hepatotoxicity (H-HT):  0.271
Drug-inuced Liver Injury (DILI):  0.835
AMES Toxicity:  0.033
Rat Oral Acute Toxicity:  0.418
Maximum Recommended Daily Dose:  0.903
Skin Sensitization:  0.932
Carcinogencity:  0.112
Eye Corrosion:  0.004
Eye Irritation:  0.008
Respiratory Toxicity:  0.976

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

  Natural Product: NPC243981

Natural Product ID:  NPC243981
Common Name*:   Bruceajavanone A 7-Acetate
IUPAC Name:   [(5R,7R,8R,9R,10S,11R,13S,17S)-7-acetyloxy-17-[(2R,3S,5S)-2-acetyloxy-5-[(2S)-3,3-dimethyloxiran-2-yl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-11-yl] hexanoate
Synonyms:   Bruceajavanone A 7-Acetate
Standard InCHIKey:  GTRFQPHJLLOEKM-XRSRLCKASA-N
Standard InCHI:  InChI=1S/C40H58O9/c1-11-12-13-14-32(44)47-27-21-39(9)25(24-19-26(34-37(6,7)49-34)48-35(24)46-23(3)42)15-16-28(39)40(10)31(45-22(2)41)20-29-36(4,5)30(43)17-18-38(29,8)33(27)40/h16-18,24-27,29,31,33-35H,11-15,19-21H2,1-10H3/t24-,25-,26-,27+,29-,31+,33+,34-,35-,38-,39-,40+/m0/s1
SMILES:  CCCCCC(=O)O[C@@H]1C[C@@]2(C)[C@@H](CC=C2[C@]2([C@H]1[C@@]1(C)C=CC(=O)C([C@@H]1C[C@H]2OC(=O)C)(C)C)C)[C@@H]1C[C@H](O[C@@H]1OC(=O)C)[C@@H]1OC1(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504211
PubChem CID:   44582339
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids
          • [CHEMONTID:0002380] Limonoids

*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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. seed n.a. DOI[10.1016/0031-9422(96)00258-0]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S1383-5769(99)00023-9]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[10086989]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[1512598]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[15165151]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[15949825]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia n.a. PMID[17896817]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[18723353]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. Vietnam n.a. PMID[19026551]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota seeds n.a. n.a. PMID[20050684]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[22506620]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26522747]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6481366]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7561896]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[8350091]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1641 Amycolatopsis azurea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11873 Oecophylla smaragdina Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11432 Centrolobium tomentosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12717 Parmelia metastrigosa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9203 Cephalonomia gallicola Species Bethylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26718 Chelidonura fulvipunctata Species Aglajidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11084 Asplenium normale Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14749 Lippia carviodora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14150 Solanum jamaicense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11637 Psilostrophe cooperi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5303 Castanea crenata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12944 Sideritis tragoriganum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14528 Pneumatospora obcoronata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3164 Yponomeuta malinellus Species Yponomeutidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14845 Ceratophyllum submersum Species Ceratophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10818 Carpobrotus edulis Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14948 Brucea javanica Species Simaroubaceae 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
NPT83 Cell Line MCF7 Homo sapiens ED50 > 10.0 uM PMID[466180]
NPT858 Cell Line LNCaP Homo sapiens ED50 > 10.0 uM PMID[466180]
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 10.0 uM PMID[466180]

☑ 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 NPC243981 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
0.9636 High Similarity NPC241192
0.955 High Similarity NPC204731
0.9545 High Similarity NPC161065
0.9273 High Similarity NPC302471
0.8919 High Similarity NPC471627
0.8919 High Similarity NPC471173
0.8814 High Similarity NPC298841
0.8814 High Similarity NPC42399
0.8649 High Similarity NPC5284
0.8584 High Similarity NPC255017
0.8496 Intermediate Similarity NPC152117
0.8496 Intermediate Similarity NPC234042
0.8482 Intermediate Similarity NPC470065
0.8468 Intermediate Similarity NPC469844
0.843 Intermediate Similarity NPC473620
0.8376 Intermediate Similarity NPC475520
0.8333 Intermediate Similarity NPC222834
0.8319 Intermediate Similarity NPC101450
0.8318 Intermediate Similarity NPC292133
0.8305 Intermediate Similarity NPC151616
0.8304 Intermediate Similarity NPC258323
0.8291 Intermediate Similarity NPC473720
0.8264 Intermediate Similarity NPC174367
0.8264 Intermediate Similarity NPC47113
0.8235 Intermediate Similarity NPC202051
0.823 Intermediate Similarity NPC474242
0.823 Intermediate Similarity NPC41405
0.8211 Intermediate Similarity NPC473593
0.8197 Intermediate Similarity NPC305496
0.8158 Intermediate Similarity NPC253906
0.8145 Intermediate Similarity NPC471170
0.8142 Intermediate Similarity NPC469845
0.8142 Intermediate Similarity NPC94942
0.8113 Intermediate Similarity NPC79117
0.8091 Intermediate Similarity NPC119467
0.8091 Intermediate Similarity NPC475767
0.808 Intermediate Similarity NPC231240
0.808 Intermediate Similarity NPC471855
0.8073 Intermediate Similarity NPC471582
0.807 Intermediate Similarity NPC118225
0.807 Intermediate Similarity NPC112457
0.8067 Intermediate Similarity NPC477071
0.8065 Intermediate Similarity NPC175186
0.8049 Intermediate Similarity NPC287423
0.8036 Intermediate Similarity NPC470060
0.8036 Intermediate Similarity NPC470064
0.8036 Intermediate Similarity NPC470062
0.8036 Intermediate Similarity NPC470061
0.8036 Intermediate Similarity NPC470043
0.8036 Intermediate Similarity NPC470059
0.8036 Intermediate Similarity NPC470057
0.8036 Intermediate Similarity NPC470058
0.8034 Intermediate Similarity NPC473882
0.8034 Intermediate Similarity NPC74727
0.8034 Intermediate Similarity NPC165439
0.8033 Intermediate Similarity NPC86346
0.8033 Intermediate Similarity NPC75856
0.8033 Intermediate Similarity NPC469379
0.8016 Intermediate Similarity NPC316915
0.8 Intermediate Similarity NPC48692
0.8 Intermediate Similarity NPC154856
0.8 Intermediate Similarity NPC474567
0.8 Intermediate Similarity NPC475317
0.8 Intermediate Similarity NPC52241
0.7984 Intermediate Similarity NPC245094
0.7984 Intermediate Similarity NPC311534
0.7983 Intermediate Similarity NPC239293
0.7982 Intermediate Similarity NPC272576
0.7967 Intermediate Similarity NPC473635
0.7966 Intermediate Similarity NPC152199
0.7966 Intermediate Similarity NPC235539
0.7966 Intermediate Similarity NPC134869
0.7966 Intermediate Similarity NPC268213
0.7965 Intermediate Similarity NPC95243
0.7965 Intermediate Similarity NPC63023
0.7951 Intermediate Similarity NPC469382
0.7949 Intermediate Similarity NPC260665
0.7949 Intermediate Similarity NPC62696
0.7949 Intermediate Similarity NPC293038
0.7946 Intermediate Similarity NPC471364
0.7946 Intermediate Similarity NPC132395
0.7946 Intermediate Similarity NPC471365
0.7944 Intermediate Similarity NPC469315
0.7931 Intermediate Similarity NPC263827
0.7931 Intermediate Similarity NPC474229
0.7931 Intermediate Similarity NPC285410
0.7931 Intermediate Similarity NPC250481
0.7928 Intermediate Similarity NPC469327
0.792 Intermediate Similarity NPC104382
0.792 Intermediate Similarity NPC471407
0.792 Intermediate Similarity NPC476966
0.7917 Intermediate Similarity NPC473203
0.7913 Intermediate Similarity NPC477070
0.7913 Intermediate Similarity NPC477069
0.7913 Intermediate Similarity NPC469370
0.7913 Intermediate Similarity NPC246205
0.7913 Intermediate Similarity NPC218853
0.7899 Intermediate Similarity NPC477252
0.7899 Intermediate Similarity NPC13713
0.7899 Intermediate Similarity NPC309433
0.7895 Intermediate Similarity NPC180744
0.7895 Intermediate Similarity NPC293512
0.7886 Intermediate Similarity NPC8369
0.7886 Intermediate Similarity NPC30188
0.7886 Intermediate Similarity NPC177820
0.7881 Intermediate Similarity NPC102088
0.7881 Intermediate Similarity NPC471398
0.7881 Intermediate Similarity NPC472274
0.7881 Intermediate Similarity NPC474906
0.7881 Intermediate Similarity NPC18547
0.7881 Intermediate Similarity NPC90472
0.7881 Intermediate Similarity NPC477580
0.7876 Intermediate Similarity NPC121566
0.7876 Intermediate Similarity NPC85593
0.7876 Intermediate Similarity NPC164835
0.7876 Intermediate Similarity NPC31430
0.7876 Intermediate Similarity NPC100955
0.7876 Intermediate Similarity NPC228669
0.7869 Intermediate Similarity NPC28532
0.7863 Intermediate Similarity NPC477253
0.7863 Intermediate Similarity NPC174836
0.7863 Intermediate Similarity NPC289312
0.7863 Intermediate Similarity NPC210420
0.7863 Intermediate Similarity NPC130427
0.7863 Intermediate Similarity NPC471967
0.7863 Intermediate Similarity NPC11252
0.7863 Intermediate Similarity NPC474265
0.7857 Intermediate Similarity NPC173347
0.7851 Intermediate Similarity NPC308459
0.7851 Intermediate Similarity NPC470312
0.7851 Intermediate Similarity NPC471406
0.785 Intermediate Similarity NPC474631
0.7845 Intermediate Similarity NPC129340
0.7845 Intermediate Similarity NPC250956
0.7845 Intermediate Similarity NPC475501
0.7845 Intermediate Similarity NPC197428
0.784 Intermediate Similarity NPC473888
0.7833 Intermediate Similarity NPC297179
0.7833 Intermediate Similarity NPC473617
0.7833 Intermediate Similarity NPC118638
0.7833 Intermediate Similarity NPC473828
0.7833 Intermediate Similarity NPC234522
0.7826 Intermediate Similarity NPC470269
0.7826 Intermediate Similarity NPC295389
0.7826 Intermediate Similarity NPC473288
0.7815 Intermediate Similarity NPC270958
0.7812 Intermediate Similarity NPC198361
0.7807 Intermediate Similarity NPC210178
0.7807 Intermediate Similarity NPC469874
0.7807 Intermediate Similarity NPC96377
0.7805 Intermediate Similarity NPC469789
0.7805 Intermediate Similarity NPC227397
0.7805 Intermediate Similarity NPC27363
0.7805 Intermediate Similarity NPC41129
0.7797 Intermediate Similarity NPC75167
0.7797 Intermediate Similarity NPC311592
0.7797 Intermediate Similarity NPC157441
0.7797 Intermediate Similarity NPC52634
0.7797 Intermediate Similarity NPC470120
0.7797 Intermediate Similarity NPC251309
0.7797 Intermediate Similarity NPC25909
0.7797 Intermediate Similarity NPC178981
0.7797 Intermediate Similarity NPC477944
0.7788 Intermediate Similarity NPC264048
0.7788 Intermediate Similarity NPC474575
0.7787 Intermediate Similarity NPC477046
0.7787 Intermediate Similarity NPC310511
0.7787 Intermediate Similarity NPC102822
0.7778 Intermediate Similarity NPC201992
0.7778 Intermediate Similarity NPC470851
0.7778 Intermediate Similarity NPC477073
0.7769 Intermediate Similarity NPC469488
0.7769 Intermediate Similarity NPC473401
0.7769 Intermediate Similarity NPC474179
0.7769 Intermediate Similarity NPC178548
0.7769 Intermediate Similarity NPC161738
0.7769 Intermediate Similarity NPC475775
0.7769 Intermediate Similarity NPC258592
0.7769 Intermediate Similarity NPC476529
0.7769 Intermediate Similarity NPC475834
0.776 Intermediate Similarity NPC240070
0.776 Intermediate Similarity NPC329784
0.7759 Intermediate Similarity NPC265655
0.775 Intermediate Similarity NPC473968
0.775 Intermediate Similarity NPC284068
0.7742 Intermediate Similarity NPC6615
0.7742 Intermediate Similarity NPC241456
0.7742 Intermediate Similarity NPC475194
0.7742 Intermediate Similarity NPC318135
0.7742 Intermediate Similarity NPC3381
0.7742 Intermediate Similarity NPC7850
0.7742 Intermediate Similarity NPC469842
0.7742 Intermediate Similarity NPC32868
0.7742 Intermediate Similarity NPC469841
0.7742 Intermediate Similarity NPC473505
0.7739 Intermediate Similarity NPC59530
0.7739 Intermediate Similarity NPC471601
0.7731 Intermediate Similarity NPC473798
0.7731 Intermediate Similarity NPC474557
0.7731 Intermediate Similarity NPC475633

  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 NPC243981 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
0.8288 Intermediate Similarity NPD6008 Approved
0.8279 Intermediate Similarity NPD7736 Approved
0.8167 Intermediate Similarity NPD6370 Approved
0.8049 Intermediate Similarity NPD8293 Discontinued
0.8033 Intermediate Similarity NPD7492 Approved
0.8 Intermediate Similarity NPD6054 Approved
0.7967 Intermediate Similarity NPD6616 Approved
0.7903 Intermediate Similarity NPD7078 Approved
0.7863 Intermediate Similarity NPD8297 Approved
0.7863 Intermediate Similarity NPD6882 Approved
0.7787 Intermediate Similarity NPD6016 Approved
0.7787 Intermediate Similarity NPD6015 Approved
0.775 Intermediate Similarity NPD6009 Approved
0.7724 Intermediate Similarity NPD5988 Approved
0.7705 Intermediate Similarity NPD6059 Approved
0.768 Intermediate Similarity NPD7507 Approved
0.7561 Intermediate Similarity NPD6319 Approved
0.7521 Intermediate Similarity NPD6881 Approved
0.7521 Intermediate Similarity NPD6899 Approved
0.752 Intermediate Similarity NPD8328 Phase 3
0.75 Intermediate Similarity NPD7319 Approved
0.75 Intermediate Similarity NPD4632 Approved
0.7479 Intermediate Similarity NPD6650 Approved
0.7479 Intermediate Similarity NPD6649 Approved
0.7479 Intermediate Similarity NPD8130 Phase 1
0.7458 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5697 Approved
0.7436 Intermediate Similarity NPD6412 Phase 2
0.7395 Intermediate Similarity NPD6883 Approved
0.7395 Intermediate Similarity NPD7102 Approved
0.7395 Intermediate Similarity NPD7290 Approved
0.7381 Intermediate Similarity NPD7604 Phase 2
0.7373 Intermediate Similarity NPD7320 Approved
0.7373 Intermediate Similarity NPD6686 Approved
0.735 Intermediate Similarity NPD5739 Approved
0.735 Intermediate Similarity NPD6402 Approved
0.735 Intermediate Similarity NPD7128 Approved
0.735 Intermediate Similarity NPD6675 Approved
0.7333 Intermediate Similarity NPD6869 Approved
0.7333 Intermediate Similarity NPD6617 Approved
0.7333 Intermediate Similarity NPD6847 Approved
0.7321 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7115 Discovery
0.7311 Intermediate Similarity NPD6012 Approved
0.7311 Intermediate Similarity NPD6373 Approved
0.7311 Intermediate Similarity NPD6013 Approved
0.7311 Intermediate Similarity NPD6372 Approved
0.7311 Intermediate Similarity NPD6014 Approved
0.7288 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD6011 Approved
0.7222 Intermediate Similarity NPD8033 Approved
0.7222 Intermediate Similarity NPD5983 Phase 2
0.7156 Intermediate Similarity NPD3573 Approved
0.7154 Intermediate Similarity NPD6033 Approved
0.7143 Intermediate Similarity NPD8294 Approved
0.7143 Intermediate Similarity NPD5701 Approved
0.7143 Intermediate Similarity NPD8377 Approved
0.7132 Intermediate Similarity NPD6336 Discontinued
0.712 Intermediate Similarity NPD7328 Approved
0.712 Intermediate Similarity NPD7327 Approved
0.7109 Intermediate Similarity NPD6067 Discontinued
0.7107 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD8335 Approved
0.7087 Intermediate Similarity NPD8380 Approved
0.7087 Intermediate Similarity NPD8296 Approved
0.7087 Intermediate Similarity NPD8378 Approved
0.7087 Intermediate Similarity NPD7503 Approved
0.7087 Intermediate Similarity NPD8379 Approved
0.708 Intermediate Similarity NPD7900 Approved
0.708 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5286 Approved
0.7069 Intermediate Similarity NPD4696 Approved
0.7069 Intermediate Similarity NPD5285 Approved
0.7068 Intermediate Similarity NPD8338 Approved
0.7063 Intermediate Similarity NPD7516 Approved
0.7054 Intermediate Similarity NPD6079 Approved
0.7025 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD8336 Approved
0.7023 Intermediate Similarity NPD8337 Approved
0.6991 Remote Similarity NPD6399 Phase 3
0.6967 Remote Similarity NPD4634 Approved
0.6953 Remote Similarity NPD8516 Approved
0.6953 Remote Similarity NPD8513 Phase 3
0.6953 Remote Similarity NPD8515 Approved
0.6953 Remote Similarity NPD8517 Approved
0.6949 Remote Similarity NPD5225 Approved
0.6949 Remote Similarity NPD5211 Phase 2
0.6949 Remote Similarity NPD5224 Approved
0.6949 Remote Similarity NPD5226 Approved
0.6949 Remote Similarity NPD4633 Approved
0.6937 Remote Similarity NPD6672 Approved
0.6937 Remote Similarity NPD6903 Approved
0.6937 Remote Similarity NPD5737 Approved
0.6935 Remote Similarity NPD8133 Approved
0.693 Remote Similarity NPD7748 Approved
0.693 Remote Similarity NPD6001 Approved
0.6929 Remote Similarity NPD7100 Approved
0.6929 Remote Similarity NPD7101 Approved
0.6911 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7521 Approved
0.6909 Remote Similarity NPD7146 Approved
0.6909 Remote Similarity NPD5330 Approved
0.6909 Remote Similarity NPD7334 Approved
0.6909 Remote Similarity NPD6684 Approved
0.6909 Remote Similarity NPD6409 Approved
0.6897 Remote Similarity NPD4755 Approved
0.6897 Remote Similarity NPD7902 Approved
0.6891 Remote Similarity NPD5174 Approved
0.6891 Remote Similarity NPD5175 Approved
0.6875 Remote Similarity NPD5328 Approved
0.6864 Remote Similarity NPD5223 Approved
0.685 Remote Similarity NPD6335 Approved
0.6833 Remote Similarity NPD5141 Approved
0.6833 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6274 Approved
0.6822 Remote Similarity NPD6291 Clinical (unspecified phase)
0.681 Remote Similarity NPD5220 Clinical (unspecified phase)
0.681 Remote Similarity NPD5222 Approved
0.681 Remote Similarity NPD5221 Approved
0.6803 Remote Similarity NPD4729 Approved
0.6803 Remote Similarity NPD4730 Approved
0.6786 Remote Similarity NPD7513 Clinical (unspecified phase)
0.678 Remote Similarity NPD4700 Approved
0.6772 Remote Similarity NPD6317 Approved
0.6752 Remote Similarity NPD5173 Approved
0.6752 Remote Similarity NPD6084 Phase 2
0.6752 Remote Similarity NPD6083 Phase 2
0.6726 Remote Similarity NPD6673 Approved
0.6726 Remote Similarity NPD6080 Approved
0.6726 Remote Similarity NPD6904 Approved
0.6719 Remote Similarity NPD6313 Approved
0.6719 Remote Similarity NPD6314 Approved
0.6695 Remote Similarity NPD7638 Approved
0.6694 Remote Similarity NPD5248 Approved
0.6694 Remote Similarity NPD5249 Phase 3
0.6694 Remote Similarity NPD5247 Approved
0.6694 Remote Similarity NPD5250 Approved
0.6694 Remote Similarity NPD5251 Approved
0.6693 Remote Similarity NPD6868 Approved
0.6667 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD5207 Approved
0.6667 Remote Similarity NPD5956 Approved
0.6639 Remote Similarity NPD4768 Approved
0.6639 Remote Similarity NPD7640 Approved
0.6639 Remote Similarity NPD7639 Approved
0.6639 Remote Similarity NPD4767 Approved
0.6609 Remote Similarity NPD7515 Phase 2
0.6587 Remote Similarity NPD6053 Discontinued
0.6581 Remote Similarity NPD5695 Phase 3
0.6579 Remote Similarity NPD1695 Approved
0.6565 Remote Similarity NPD6908 Approved
0.6565 Remote Similarity NPD6909 Approved
0.6555 Remote Similarity NPD5696 Approved
0.6552 Remote Similarity NPD4202 Approved
0.6532 Remote Similarity NPD5128 Approved
0.6525 Remote Similarity NPD4697 Phase 3
0.6508 Remote Similarity NPD5215 Approved
0.6508 Remote Similarity NPD5217 Approved
0.6508 Remote Similarity NPD5216 Approved
0.6491 Remote Similarity NPD5208 Approved
0.6475 Remote Similarity NPD4754 Approved
0.6466 Remote Similarity NPD5694 Approved
0.6466 Remote Similarity NPD8034 Phase 2
0.6466 Remote Similarity NPD6050 Approved
0.6466 Remote Similarity NPD8035 Phase 2
0.6466 Remote Similarity NPD5693 Phase 1
0.646 Remote Similarity NPD3618 Phase 1
0.646 Remote Similarity NPD6098 Approved
0.6452 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6444 Remote Similarity NPD8074 Phase 3
0.6438 Remote Similarity NPD7799 Discontinued
0.6429 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5135 Approved
0.6429 Remote Similarity NPD4786 Approved
0.6429 Remote Similarity NPD5169 Approved
0.6417 Remote Similarity NPD4225 Approved
0.6379 Remote Similarity NPD5692 Phase 3
0.6378 Remote Similarity NPD5127 Approved
0.6377 Remote Similarity NPD7260 Phase 2
0.6372 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6648 Approved
0.6356 Remote Similarity NPD5282 Discontinued
0.6341 Remote Similarity NPD6052 Approved
0.6331 Remote Similarity NPD6845 Suspended
0.6325 Remote Similarity NPD5284 Approved
0.6325 Remote Similarity NPD5281 Approved
0.6325 Remote Similarity NPD6411 Approved
0.6316 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5344 Discontinued
0.6303 Remote Similarity NPD4629 Approved
0.6303 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6303 Remote Similarity NPD5210 Approved
0.6299 Remote Similarity NPD6371 Approved
0.6293 Remote Similarity NPD4753 Phase 2
0.6283 Remote Similarity NPD3668 Phase 3
0.627 Remote Similarity NPD5168 Approved
0.626 Remote Similarity NPD7632 Discontinued
0.625 Remote Similarity NPD3667 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