Structure

Physi-Chem Properties

Molecular Weight:  385.3
Volume:  421.478
LogP:  2.862
LogD:  2.774
LogS:  -4.383
# Rotatable Bonds:  2
TPSA:  40.54
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.714
Synthetic Accessibility Score:  5.812
Fsp3:  0.88
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.297
MDCK Permeability:  5.214969405642478e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.043
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.025
30% Bioavailability (F30%):  0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.876
Plasma Protein Binding (PPB):  49.33363342285156%
Volume Distribution (VD):  2.411
Pgp-substrate:  59.04763412475586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.722
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.947
CYP2C9-inhibitor:  0.069
CYP2C9-substrate:  0.127
CYP2D6-inhibitor:  0.112
CYP2D6-substrate:  0.884
CYP3A4-inhibitor:  0.951
CYP3A4-substrate:  0.769

ADMET: Excretion

Clearance (CL):  13.235
Half-life (T1/2):  0.173

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.355
Drug-inuced Liver Injury (DILI):  0.559
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.898
Maximum Recommended Daily Dose:  0.914
Skin Sensitization:  0.512
Carcinogencity:  0.688
Eye Corrosion:  0.027
Eye Irritation:  0.02
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC476755

Natural Product ID:  NPC476755
Common Name*:   buxippine K
IUPAC Name:   1-[(1S,3R,6S,11S,12S,14R,15R,16R)-6-(dimethylamino)-14-hydroxy-12,16-dimethyl-7-methylidene-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]ethanone
Synonyms:   Buxippine K
Standard InCHIKey:  GNRVDDAXIDKEFJ-VOKDCXLQSA-N
Standard InCHI:  InChI=1S/C25H39NO2/c1-15-17-7-8-20-23(4)13-19(28)21(16(2)27)22(23,3)11-12-25(20)14-24(17,25)10-9-18(15)26(5)6/h17-21,28H,1,7-14H2,2-6H3/t17?,18-,19+,20-,21-,22+,23-,24+,25-/m0/s1
SMILES:  CC(=O)[C@H]1[C@@H](C[C@@]2([C@@]1(CC[C@]34[C@H]2CCC5[C@]3(C4)CC[C@@H](C5=C)N(C)C)C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   45271308
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
NPO24301 Buxus microphylla Species Buxaceae Eukaryota leaves and stems Kunming, Yunnan, China 2007-AUG PMID[19133780]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24301 Buxus microphylla Species Buxaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 = 57130 nM PMID[19133780]
NPT111 Cell Line K562 Homo sapiens IC50 = 35290 nM PMID[19133780]

☑ 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 NPC476755 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
0.9394 High Similarity NPC244982
0.9394 High Similarity NPC476756
0.783 Intermediate Similarity NPC98765
0.7748 Intermediate Similarity NPC124358
0.7708 Intermediate Similarity NPC46881
0.7708 Intermediate Similarity NPC477858
0.7624 Intermediate Similarity NPC312637
0.7593 Intermediate Similarity NPC475239
0.757 Intermediate Similarity NPC470592
0.7526 Intermediate Similarity NPC110780
0.75 Intermediate Similarity NPC241879
0.75 Intermediate Similarity NPC134197
0.7475 Intermediate Similarity NPC76518
0.7449 Intermediate Similarity NPC245866
0.7426 Intermediate Similarity NPC146937
0.7426 Intermediate Similarity NPC328313
0.7426 Intermediate Similarity NPC183374
0.7426 Intermediate Similarity NPC211162
0.74 Intermediate Similarity NPC70661
0.7396 Intermediate Similarity NPC201459
0.7383 Intermediate Similarity NPC135799
0.7374 Intermediate Similarity NPC82902
0.7353 Intermediate Similarity NPC116146
0.7353 Intermediate Similarity NPC24772
0.7347 Intermediate Similarity NPC145143
0.7327 Intermediate Similarity NPC57469
0.73 Intermediate Similarity NPC201655
0.73 Intermediate Similarity NPC474218
0.73 Intermediate Similarity NPC102292
0.7273 Intermediate Similarity NPC475726
0.7273 Intermediate Similarity NPC471036
0.7273 Intermediate Similarity NPC472498
0.7273 Intermediate Similarity NPC472743
0.7273 Intermediate Similarity NPC291320
0.7264 Intermediate Similarity NPC234564
0.7264 Intermediate Similarity NPC476903
0.7255 Intermediate Similarity NPC259252
0.7245 Intermediate Similarity NPC474484
0.7245 Intermediate Similarity NPC103754
0.7228 Intermediate Similarity NPC469994
0.7228 Intermediate Similarity NPC80590
0.72 Intermediate Similarity NPC474233
0.72 Intermediate Similarity NPC475745
0.72 Intermediate Similarity NPC474482
0.72 Intermediate Similarity NPC263974
0.7188 Intermediate Similarity NPC106078
0.7172 Intermediate Similarity NPC170985
0.717 Intermediate Similarity NPC266431
0.717 Intermediate Similarity NPC311164
0.717 Intermediate Similarity NPC174117
0.717 Intermediate Similarity NPC272732
0.7157 Intermediate Similarity NPC317590
0.7157 Intermediate Similarity NPC21035
0.7157 Intermediate Similarity NPC165895
0.7143 Intermediate Similarity NPC164999
0.713 Intermediate Similarity NPC220111
0.7129 Intermediate Similarity NPC182106
0.7129 Intermediate Similarity NPC190704
0.7129 Intermediate Similarity NPC292553
0.7129 Intermediate Similarity NPC311769
0.7129 Intermediate Similarity NPC471034
0.7119 Intermediate Similarity NPC474006
0.7117 Intermediate Similarity NPC119329
0.71 Intermediate Similarity NPC175410
0.7087 Intermediate Similarity NPC471900
0.7083 Intermediate Similarity NPC238323
0.708 Intermediate Similarity NPC470595
0.7075 Intermediate Similarity NPC476754
0.7059 Intermediate Similarity NPC472738
0.7054 Intermediate Similarity NPC55462
0.7054 Intermediate Similarity NPC195841
0.7054 Intermediate Similarity NPC233256
0.7037 Intermediate Similarity NPC140300
0.703 Intermediate Similarity NPC264665
0.703 Intermediate Similarity NPC321187
0.703 Intermediate Similarity NPC59453
0.703 Intermediate Similarity NPC227064
0.703 Intermediate Similarity NPC58841
0.703 Intermediate Similarity NPC85774
0.703 Intermediate Similarity NPC161423
0.703 Intermediate Similarity NPC214043
0.703 Intermediate Similarity NPC329043
0.703 Intermediate Similarity NPC74595
0.703 Intermediate Similarity NPC221758
0.7027 Intermediate Similarity NPC470310
0.7021 Intermediate Similarity NPC473267
0.7019 Intermediate Similarity NPC57954
0.7019 Intermediate Similarity NPC135005
0.7019 Intermediate Similarity NPC477943
0.7019 Intermediate Similarity NPC76879
0.7019 Intermediate Similarity NPC213832
0.7019 Intermediate Similarity NPC2983
0.7018 Intermediate Similarity NPC473994
0.7009 Intermediate Similarity NPC263135
0.7009 Intermediate Similarity NPC205173
0.7009 Intermediate Similarity NPC288906
0.699 Remote Similarity NPC472495
0.699 Remote Similarity NPC472481
0.699 Remote Similarity NPC472484
0.699 Remote Similarity NPC259009
0.699 Remote Similarity NPC472497
0.699 Remote Similarity NPC472482
0.699 Remote Similarity NPC96496
0.699 Remote Similarity NPC4643
0.6981 Remote Similarity NPC12722
0.6964 Remote Similarity NPC470596
0.6961 Remote Similarity NPC294438
0.6961 Remote Similarity NPC471224
0.6961 Remote Similarity NPC264317
0.6961 Remote Similarity NPC75810
0.6952 Remote Similarity NPC261994
0.6952 Remote Similarity NPC180849
0.6952 Remote Similarity NPC149761
0.6952 Remote Similarity NPC320026
0.6952 Remote Similarity NPC169933
0.6952 Remote Similarity NPC470378
0.6952 Remote Similarity NPC171441
0.6947 Remote Similarity NPC310766
0.6944 Remote Similarity NPC29152
0.6937 Remote Similarity NPC271980
0.6937 Remote Similarity NPC471083
0.6937 Remote Similarity NPC193934
0.6937 Remote Similarity NPC176012
0.6937 Remote Similarity NPC50815
0.6931 Remote Similarity NPC118800
0.6923 Remote Similarity NPC471724
0.6923 Remote Similarity NPC472739
0.6923 Remote Similarity NPC474719
0.6923 Remote Similarity NPC53911
0.6923 Remote Similarity NPC193360
0.6917 Remote Similarity NPC35037
0.6907 Remote Similarity NPC20466
0.6903 Remote Similarity NPC265127
0.69 Remote Similarity NPC109533
0.6893 Remote Similarity NPC269396
0.6893 Remote Similarity NPC474778
0.6893 Remote Similarity NPC474733
0.6893 Remote Similarity NPC145879
0.6893 Remote Similarity NPC2783
0.6893 Remote Similarity NPC475007
0.6893 Remote Similarity NPC474732
0.6893 Remote Similarity NPC31564
0.6893 Remote Similarity NPC12774
0.6893 Remote Similarity NPC98236
0.6893 Remote Similarity NPC472505
0.6893 Remote Similarity NPC51014
0.6887 Remote Similarity NPC299185
0.6887 Remote Similarity NPC278106
0.6887 Remote Similarity NPC154101
0.6887 Remote Similarity NPC476168
0.6887 Remote Similarity NPC475416
0.6881 Remote Similarity NPC156546
0.6881 Remote Similarity NPC292819
0.6869 Remote Similarity NPC215843
0.6869 Remote Similarity NPC192744
0.6863 Remote Similarity NPC473246
0.6863 Remote Similarity NPC146683
0.6857 Remote Similarity NPC122116
0.6857 Remote Similarity NPC54689
0.6857 Remote Similarity NPC472971
0.6857 Remote Similarity NPC472970
0.6852 Remote Similarity NPC263347
0.6852 Remote Similarity NPC476174
0.6852 Remote Similarity NPC210214
0.6847 Remote Similarity NPC71706
0.6847 Remote Similarity NPC118275
0.6837 Remote Similarity NPC149249
0.6837 Remote Similarity NPC66105
0.6832 Remote Similarity NPC151519
0.6827 Remote Similarity NPC93778
0.6827 Remote Similarity NPC269360
0.6827 Remote Similarity NPC90652
0.6827 Remote Similarity NPC264005
0.6827 Remote Similarity NPC475740
0.6827 Remote Similarity NPC33768
0.6827 Remote Similarity NPC58063
0.6822 Remote Similarity NPC93027
0.6822 Remote Similarity NPC476752
0.6822 Remote Similarity NPC144739
0.6822 Remote Similarity NPC476753
0.6822 Remote Similarity NPC59350
0.6822 Remote Similarity NPC82138
0.6822 Remote Similarity NPC471902
0.6822 Remote Similarity NPC287118
0.6822 Remote Similarity NPC59170
0.6822 Remote Similarity NPC473690
0.6822 Remote Similarity NPC181594
0.6818 Remote Similarity NPC91604
0.6814 Remote Similarity NPC212874
0.681 Remote Similarity NPC63511
0.6809 Remote Similarity NPC321732
0.6809 Remote Similarity NPC324607
0.6804 Remote Similarity NPC70982
0.6804 Remote Similarity NPC230704
0.6804 Remote Similarity NPC273366
0.6796 Remote Similarity NPC202868
0.6796 Remote Similarity NPC474083
0.6796 Remote Similarity NPC469948
0.6792 Remote Similarity NPC69622
0.6792 Remote Similarity NPC126993

  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 NPC476755 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
0.7449 Intermediate Similarity NPD4788 Approved
0.7054 Intermediate Similarity NPD6920 Discontinued
0.703 Intermediate Similarity NPD3666 Approved
0.703 Intermediate Similarity NPD3665 Phase 1
0.703 Intermediate Similarity NPD4786 Approved
0.703 Intermediate Similarity NPD3133 Approved
0.6961 Remote Similarity NPD7520 Clinical (unspecified phase)
0.693 Remote Similarity NPD6415 Discontinued
0.6915 Remote Similarity NPD4244 Approved
0.6915 Remote Similarity NPD4245 Approved
0.6832 Remote Similarity NPD3667 Approved
0.6809 Remote Similarity NPD3698 Phase 2
0.6789 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6757 Remote Similarity NPD8418 Phase 2
0.6754 Remote Similarity NPD7333 Discontinued
0.6698 Remote Similarity NPD4753 Phase 2
0.6698 Remote Similarity NPD5328 Approved
0.6667 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5329 Approved
0.6574 Remote Similarity NPD6079 Approved
0.6571 Remote Similarity NPD3618 Phase 1
0.6562 Remote Similarity NPD4789 Approved
0.6538 Remote Similarity NPD4197 Approved
0.6532 Remote Similarity NPD6909 Approved
0.6532 Remote Similarity NPD6908 Approved
0.6529 Remote Similarity NPD7754 Approved
0.6529 Remote Similarity NPD7755 Approved
0.65 Remote Similarity NPD8298 Phase 2
0.6458 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6458 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5769 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4755 Approved
0.6429 Remote Similarity NPD6083 Phase 2
0.6429 Remote Similarity NPD6084 Phase 2
0.6422 Remote Similarity NPD8035 Phase 2
0.6422 Remote Similarity NPD8034 Phase 2
0.6415 Remote Similarity NPD6684 Approved
0.6415 Remote Similarity NPD5205 Approved
0.6415 Remote Similarity NPD4689 Approved
0.6415 Remote Similarity NPD4138 Approved
0.6415 Remote Similarity NPD4690 Approved
0.6415 Remote Similarity NPD4693 Phase 3
0.6415 Remote Similarity NPD5279 Phase 3
0.6415 Remote Similarity NPD7146 Approved
0.6415 Remote Similarity NPD7334 Approved
0.6415 Remote Similarity NPD7521 Approved
0.6415 Remote Similarity NPD6409 Approved
0.6415 Remote Similarity NPD4688 Approved
0.6415 Remote Similarity NPD5330 Approved
0.6396 Remote Similarity NPD5210 Approved
0.6396 Remote Similarity NPD4629 Approved
0.6383 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6371 Remote Similarity NPD7517 Approved
0.6371 Remote Similarity NPD7519 Approved
0.6371 Remote Similarity NPD7518 Approved
0.6364 Remote Similarity NPD6399 Phase 3
0.6364 Remote Similarity NPD6113 Clinical (unspecified phase)
0.633 Remote Similarity NPD4096 Approved
0.6316 Remote Similarity NPD4700 Approved
0.6316 Remote Similarity NPD4696 Approved
0.6316 Remote Similarity NPD5285 Approved
0.6316 Remote Similarity NPD5286 Approved
0.6296 Remote Similarity NPD6903 Approved
0.6281 Remote Similarity NPD8078 Approved
0.6281 Remote Similarity NPD8077 Approved
0.6271 Remote Similarity NPD7646 Clinical (unspecified phase)
0.6262 Remote Similarity NPD4694 Approved
0.6262 Remote Similarity NPD5280 Approved
0.6262 Remote Similarity NPD5690 Phase 2
0.6262 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6261 Remote Similarity NPD5223 Approved
0.625 Remote Similarity NPD4692 Approved
0.625 Remote Similarity NPD4139 Approved
0.6238 Remote Similarity NPD6117 Approved
0.6238 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6226 Remote Similarity NPD3668 Phase 3
0.6207 Remote Similarity NPD4633 Approved
0.6207 Remote Similarity NPD5225 Approved
0.6207 Remote Similarity NPD5226 Approved
0.6207 Remote Similarity NPD5211 Phase 2
0.6207 Remote Similarity NPD5224 Approved
0.6195 Remote Similarity NPD4697 Phase 3
0.6195 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5222 Approved
0.6195 Remote Similarity NPD5221 Approved
0.6186 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6675 Approved
0.6186 Remote Similarity NPD7128 Approved
0.6186 Remote Similarity NPD6402 Approved
0.6186 Remote Similarity NPD5360 Phase 3
0.6186 Remote Similarity NPD5739 Approved
0.6176 Remote Similarity NPD6116 Phase 1
0.6162 Remote Similarity NPD5777 Approved
0.6154 Remote Similarity NPD7525 Registered
0.6154 Remote Similarity NPD4754 Approved
0.6154 Remote Similarity NPD5174 Approved
0.6154 Remote Similarity NPD5175 Approved
0.614 Remote Similarity NPD7920 Phase 3
0.614 Remote Similarity NPD5173 Approved
0.614 Remote Similarity NPD7919 Phase 3
0.6139 Remote Similarity NPD6942 Approved
0.6139 Remote Similarity NPD3703 Phase 2
0.6139 Remote Similarity NPD7339 Approved
0.6126 Remote Similarity NPD7515 Phase 2
0.6117 Remote Similarity NPD6114 Approved
0.6117 Remote Similarity NPD6697 Approved
0.6117 Remote Similarity NPD6115 Approved
0.6117 Remote Similarity NPD3617 Approved
0.6117 Remote Similarity NPD6118 Approved
0.6116 Remote Similarity NPD4634 Approved
0.6111 Remote Similarity NPD6098 Approved
0.6106 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6106 Remote Similarity NPD5695 Phase 3
0.6102 Remote Similarity NPD5141 Approved
0.6087 Remote Similarity NPD5696 Approved
0.6087 Remote Similarity NPD8088 Phase 1
0.6083 Remote Similarity NPD6881 Approved
0.6083 Remote Similarity NPD7320 Approved
0.6083 Remote Similarity NPD6899 Approved
0.6071 Remote Similarity NPD5133 Approved
0.6058 Remote Similarity NPD4195 Approved
0.6058 Remote Similarity NPD7155 Clinical (unspecified phase)
0.605 Remote Similarity NPD8040 Discontinued
0.605 Remote Similarity NPD4767 Approved
0.605 Remote Similarity NPD4768 Approved
0.6047 Remote Similarity NPD7604 Phase 2
0.6033 Remote Similarity NPD6372 Approved
0.6033 Remote Similarity NPD6373 Approved
0.6018 Remote Similarity NPD5771 Approved
0.6 Remote Similarity NPD6412 Phase 2
0.6 Remote Similarity NPD5737 Approved
0.6 Remote Similarity NPD6672 Approved
0.6 Remote Similarity NPD5697 Approved
0.6 Remote Similarity NPD6081 Approved
0.6 Remote Similarity NPD5701 Approved
0.6 Remote Similarity NPD4243 Approved
0.5984 Remote Similarity NPD7290 Approved
0.5984 Remote Similarity NPD6883 Approved
0.5984 Remote Similarity NPD6420 Discontinued
0.5984 Remote Similarity NPD7102 Approved
0.5982 Remote Similarity NPD5284 Approved
0.5982 Remote Similarity NPD5281 Approved
0.598 Remote Similarity NPD3702 Approved
0.5979 Remote Similarity NPD4224 Phase 2
0.5962 Remote Similarity NPD3671 Phase 1
0.595 Remote Similarity NPD4729 Approved
0.595 Remote Similarity NPD6011 Approved
0.595 Remote Similarity NPD5128 Approved
0.595 Remote Similarity NPD4730 Approved
0.5948 Remote Similarity NPD7638 Approved
0.5946 Remote Similarity NPD6904 Approved
0.5946 Remote Similarity NPD6080 Approved
0.5946 Remote Similarity NPD6673 Approved
0.5938 Remote Similarity NPD7148 Clinical (unspecified phase)
0.5938 Remote Similarity NPD7147 Phase 3
0.5935 Remote Similarity NPD8130 Phase 1
0.5935 Remote Similarity NPD6869 Approved
0.5935 Remote Similarity NPD6847 Approved
0.5935 Remote Similarity NPD6649 Approved
0.5935 Remote Similarity NPD6617 Approved
0.5935 Remote Similarity NPD6650 Approved
0.5935 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5923 Remote Similarity NPD7122 Discontinued
0.5903 Remote Similarity NPD7295 Approved
0.5902 Remote Similarity NPD6013 Approved
0.5902 Remote Similarity NPD6014 Approved
0.5902 Remote Similarity NPD6012 Approved
0.5897 Remote Similarity NPD7640 Approved
0.5897 Remote Similarity NPD6404 Discontinued
0.5897 Remote Similarity NPD7639 Approved
0.5896 Remote Similarity NPD7751 Phase 1
0.5893 Remote Similarity NPD6934 Discontinued
0.5891 Remote Similarity NPD6921 Approved
0.5887 Remote Similarity NPD6882 Approved
0.5887 Remote Similarity NPD8297 Approved
0.5882 Remote Similarity NPD4785 Approved
0.5882 Remote Similarity NPD6926 Approved
0.5882 Remote Similarity NPD7912 Approved
0.5882 Remote Similarity NPD7911 Approved
0.5882 Remote Similarity NPD7987 Approved
0.5882 Remote Similarity NPD6924 Approved
0.5882 Remote Similarity NPD7986 Approved
0.5882 Remote Similarity NPD4784 Approved
0.5877 Remote Similarity NPD7748 Approved
0.5877 Remote Similarity NPD6001 Approved
0.5865 Remote Similarity NPD8336 Approved
0.5865 Remote Similarity NPD8337 Approved
0.5856 Remote Similarity NPD5208 Approved
0.5854 Remote Similarity NPD5135 Approved
0.5854 Remote Similarity NPD5247 Approved
0.5854 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5854 Remote Similarity NPD5250 Approved
0.5854 Remote Similarity NPD5249 Phase 3
0.5854 Remote Similarity NPD5251 Approved
0.5854 Remote Similarity NPD5248 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