Structure

Physi-Chem Properties

Molecular Weight:  736.33
Volume:  701.364
LogP:  2.281
LogD:  1.443
LogS:  -4.888
# Rotatable Bonds:  12
TPSA:  195.11
# H-Bond Aceptor:  15
# H-Bond Donor:  2
# Rings:  8
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.202
Synthetic Accessibility Score:  7.531
Fsp3:  0.892
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:  -5.329
MDCK Permeability:  0.00014731961709912866
Pgp-inhibitor:  0.981
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.29

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.077
Plasma Protein Binding (PPB):  31.692800521850586%
Volume Distribution (VD):  1.1
Pgp-substrate:  49.633087158203125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.991
CYP2C19-inhibitor:  0.007
CYP2C19-substrate:  0.652
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.001
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.071
CYP3A4-inhibitor:  0.548
CYP3A4-substrate:  0.666

ADMET: Excretion

Clearance (CL):  4.989
Half-life (T1/2):  0.124

ADMET: Toxicity

hERG Blockers:  0.508
Human Hepatotoxicity (H-HT):  0.592
Drug-inuced Liver Injury (DILI):  0.398
AMES Toxicity:  0.204
Rat Oral Acute Toxicity:  0.254
Maximum Recommended Daily Dose:  0.737
Skin Sensitization:  0.178
Carcinogencity:  0.236
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.974

Download Data

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

  Natural Product: NPC470115

Natural Product ID:  NPC470115
Common Name*:   Vepaol
IUPAC Name:   n.a.
Synonyms:   Vepaol
Standard InCHIKey:  ZMBSZFLUIUMZOK-WOPACFSYSA-N
Standard InCHI:  InChI=1S/C37H52O15/c1-9-16(2)29(40)51-20-12-21(49-17(3)38)35(31(42)46-8)15-47-24-27(35)34(20)14-48-25(30(41)45-7)26(34)32(4,28(24)39)37-23-11-19(33(37,5)52-37)36(43)13-18(44-6)10-22(36)50-23/h16,18-28,39,43H,9-15H2,1-8H3/t16?,18-,19?,20-,21+,22+,23?,24+,25-,26-,27+,28+,32-,33-,34+,35-,36-,37-/m0/s1
SMILES:  CCC(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(CC(CC8O7)OC)O)C(=O)OC)C(=O)OC)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1774408
PubChem CID:   54583360
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193038]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[1593280]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[18816111]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota fruits n.a. n.a. PMID[20669933]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota Seeds n.a. n.a. PMID[21381696]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. seed n.a. PMID[21381696]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[2607354]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[2614419]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[26339153]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota Leaves n.a. n.a. PMID[28493718]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. bark n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. fruit n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. leaf n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 20000.0 nM PMID[535855]
NPT81 Cell Line A549 Homo sapiens IC50 > 20000.0 nM PMID[535855]
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 > 20000.0 nM PMID[535855]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 20000.0 nM PMID[535855]

☑ 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 NPC470115 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 NPC470116
0.8673 High Similarity NPC475490
0.8491 Intermediate Similarity NPC253995
0.8387 Intermediate Similarity NPC219058
0.8387 Intermediate Similarity NPC256618
0.8364 Intermediate Similarity NPC166079
0.8364 Intermediate Similarity NPC306776
0.8333 Intermediate Similarity NPC298266
0.8333 Intermediate Similarity NPC97002
0.8333 Intermediate Similarity NPC259654
0.8306 Intermediate Similarity NPC475376
0.8302 Intermediate Similarity NPC116683
0.8273 Intermediate Similarity NPC100078
0.8158 Intermediate Similarity NPC473062
0.8145 Intermediate Similarity NPC42206
0.812 Intermediate Similarity NPC179429
0.8108 Intermediate Similarity NPC473526
0.8108 Intermediate Similarity NPC88469
0.8108 Intermediate Similarity NPC473701
0.8103 Intermediate Similarity NPC79193
0.8091 Intermediate Similarity NPC213528
0.8091 Intermediate Similarity NPC244969
0.8091 Intermediate Similarity NPC470172
0.8018 Intermediate Similarity NPC471253
0.8018 Intermediate Similarity NPC473406
0.7946 Intermediate Similarity NPC327093
0.7931 Intermediate Similarity NPC477489
0.7928 Intermediate Similarity NPC471254
0.789 Intermediate Similarity NPC471241
0.7874 Intermediate Similarity NPC470117
0.787 Intermediate Similarity NPC287354
0.787 Intermediate Similarity NPC17336
0.787 Intermediate Similarity NPC62407
0.785 Intermediate Similarity NPC476189
0.7838 Intermediate Similarity NPC178853
0.783 Intermediate Similarity NPC470114
0.7826 Intermediate Similarity NPC227879
0.7826 Intermediate Similarity NPC208333
0.782 Intermediate Similarity NPC194854
0.782 Intermediate Similarity NPC48813
0.7818 Intermediate Similarity NPC211087
0.7818 Intermediate Similarity NPC476294
0.781 Intermediate Similarity NPC476435
0.7807 Intermediate Similarity NPC203974
0.7787 Intermediate Similarity NPC65858
0.7778 Intermediate Similarity NPC477495
0.7778 Intermediate Similarity NPC470424
0.7761 Intermediate Similarity NPC475462
0.7761 Intermediate Similarity NPC16729
0.7757 Intermediate Similarity NPC473066
0.7757 Intermediate Similarity NPC216137
0.7744 Intermediate Similarity NPC471172
0.7724 Intermediate Similarity NPC43252
0.7724 Intermediate Similarity NPC267822
0.7724 Intermediate Similarity NPC135038
0.7706 Intermediate Similarity NPC470191
0.7706 Intermediate Similarity NPC470031
0.7699 Intermediate Similarity NPC34562
0.7692 Intermediate Similarity NPC469824
0.7685 Intermediate Similarity NPC474379
0.7672 Intermediate Similarity NPC228190
0.7672 Intermediate Similarity NPC236753
0.7664 Intermediate Similarity NPC477444
0.7664 Intermediate Similarity NPC477442
0.7664 Intermediate Similarity NPC477433
0.7661 Intermediate Similarity NPC473255
0.7661 Intermediate Similarity NPC169818
0.7642 Intermediate Similarity NPC471221
0.7642 Intermediate Similarity NPC226491
0.7642 Intermediate Similarity NPC477614
0.7636 Intermediate Similarity NPC235109
0.7636 Intermediate Similarity NPC476728
0.7632 Intermediate Similarity NPC114365
0.7632 Intermediate Similarity NPC169089
0.7632 Intermediate Similarity NPC88890
0.7632 Intermediate Similarity NPC123070
0.7632 Intermediate Similarity NPC18433
0.7632 Intermediate Similarity NPC18044
0.7632 Intermediate Similarity NPC328737
0.7632 Intermediate Similarity NPC132304
0.7632 Intermediate Similarity NPC154962
0.7632 Intermediate Similarity NPC470167
0.7632 Intermediate Similarity NPC177518
0.7627 Intermediate Similarity NPC98870
0.7627 Intermediate Similarity NPC477492
0.7615 Intermediate Similarity NPC206878
0.7594 Intermediate Similarity NPC5153
0.7594 Intermediate Similarity NPC48414
0.7593 Intermediate Similarity NPC474065
0.7586 Intermediate Similarity NPC472079
0.7586 Intermediate Similarity NPC316930
0.757 Intermediate Similarity NPC61688
0.757 Intermediate Similarity NPC200580
0.757 Intermediate Similarity NPC477443
0.757 Intermediate Similarity NPC24705
0.757 Intermediate Similarity NPC477440
0.757 Intermediate Similarity NPC56962
0.7568 Intermediate Similarity NPC266417
0.7563 Intermediate Similarity NPC94509
0.7559 Intermediate Similarity NPC470880
0.7547 Intermediate Similarity NPC5943
0.7545 Intermediate Similarity NPC82633
0.7542 Intermediate Similarity NPC472003
0.7537 Intermediate Similarity NPC471171
0.7523 Intermediate Similarity NPC182740
0.7523 Intermediate Similarity NPC472238
0.7523 Intermediate Similarity NPC122083
0.7523 Intermediate Similarity NPC472237
0.7523 Intermediate Similarity NPC211845
0.7523 Intermediate Similarity NPC256104
0.7521 Intermediate Similarity NPC321661
0.7521 Intermediate Similarity NPC320475
0.75 Intermediate Similarity NPC472144
0.75 Intermediate Similarity NPC300051
0.75 Intermediate Similarity NPC77756
0.75 Intermediate Similarity NPC292775
0.7477 Intermediate Similarity NPC156377
0.7477 Intermediate Similarity NPC163685
0.7477 Intermediate Similarity NPC193785
0.7477 Intermediate Similarity NPC56777
0.7477 Intermediate Similarity NPC477264
0.7477 Intermediate Similarity NPC201607
0.7477 Intermediate Similarity NPC475765
0.7477 Intermediate Similarity NPC476379
0.7477 Intermediate Similarity NPC475785
0.746 Intermediate Similarity NPC273962
0.7458 Intermediate Similarity NPC182185
0.7456 Intermediate Similarity NPC292803
0.7455 Intermediate Similarity NPC247877
0.7455 Intermediate Similarity NPC76136
0.7455 Intermediate Similarity NPC217567
0.7455 Intermediate Similarity NPC309127
0.7455 Intermediate Similarity NPC470423
0.7455 Intermediate Similarity NPC329713
0.7453 Intermediate Similarity NPC131365
0.7453 Intermediate Similarity NPC155531
0.7453 Intermediate Similarity NPC477283
0.7453 Intermediate Similarity NPC472272
0.7453 Intermediate Similarity NPC215968
0.7438 Intermediate Similarity NPC190185
0.7438 Intermediate Similarity NPC213084
0.7438 Intermediate Similarity NPC89929
0.7438 Intermediate Similarity NPC173686
0.7438 Intermediate Similarity NPC16081
0.7436 Intermediate Similarity NPC469826
0.7436 Intermediate Similarity NPC167044
0.7431 Intermediate Similarity NPC474699
0.7429 Intermediate Similarity NPC291310
0.7417 Intermediate Similarity NPC102619
0.7417 Intermediate Similarity NPC285086
0.7414 Intermediate Similarity NPC168890
0.7414 Intermediate Similarity NPC215408
0.7411 Intermediate Similarity NPC472145
0.7411 Intermediate Similarity NPC472273
0.7402 Intermediate Similarity NPC2757
0.7402 Intermediate Similarity NPC470882
0.7402 Intermediate Similarity NPC473253
0.7402 Intermediate Similarity NPC473265
0.7395 Intermediate Similarity NPC470281
0.7395 Intermediate Similarity NPC157476
0.7391 Intermediate Similarity NPC107385
0.7387 Intermediate Similarity NPC305808
0.7383 Intermediate Similarity NPC263802
0.7383 Intermediate Similarity NPC239938
0.7377 Intermediate Similarity NPC470778
0.7377 Intermediate Similarity NPC146432
0.7373 Intermediate Similarity NPC217041
0.7364 Intermediate Similarity NPC475307
0.7364 Intermediate Similarity NPC472232
0.7364 Intermediate Similarity NPC472231
0.7364 Intermediate Similarity NPC228700
0.7358 Intermediate Similarity NPC473350
0.7358 Intermediate Similarity NPC266651
0.7358 Intermediate Similarity NPC477445
0.7355 Intermediate Similarity NPC299849
0.7355 Intermediate Similarity NPC477465
0.7355 Intermediate Similarity NPC323821
0.7355 Intermediate Similarity NPC45218
0.7355 Intermediate Similarity NPC143268
0.7355 Intermediate Similarity NPC268238
0.735 Intermediate Similarity NPC176756
0.735 Intermediate Similarity NPC166993
0.7339 Intermediate Similarity NPC317635
0.7339 Intermediate Similarity NPC142882
0.7339 Intermediate Similarity NPC329008
0.7333 Intermediate Similarity NPC280782
0.7333 Intermediate Similarity NPC69953
0.7333 Intermediate Similarity NPC157328
0.7311 Intermediate Similarity NPC100908
0.7304 Intermediate Similarity NPC134967
0.7304 Intermediate Similarity NPC124544
0.7304 Intermediate Similarity NPC310138
0.7304 Intermediate Similarity NPC114700
0.7304 Intermediate Similarity NPC470029
0.729 Intermediate Similarity NPC475729
0.729 Intermediate Similarity NPC228593
0.729 Intermediate Similarity NPC474215
0.729 Intermediate Similarity NPC64862
0.729 Intermediate Similarity NPC477441
0.729 Intermediate Similarity NPC476727

  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 NPC470115 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
0.8679 High Similarity NPD1700 Approved
0.7632 Intermediate Similarity NPD4057 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD4056 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD7078 Approved
0.72 Intermediate Similarity NPD6319 Approved
0.7132 Intermediate Similarity NPD8293 Discontinued
0.7109 Intermediate Similarity NPD7492 Approved
0.7077 Intermediate Similarity NPD7736 Approved
0.7063 Intermediate Similarity NPD6054 Approved
0.7063 Intermediate Similarity NPD6059 Approved
0.7054 Intermediate Similarity NPD6616 Approved
0.6953 Remote Similarity NPD6370 Approved
0.6911 Remote Similarity NPD8297 Approved
0.6875 Remote Similarity NPD6016 Approved
0.6875 Remote Similarity NPD6015 Approved
0.686 Remote Similarity NPD7320 Approved
0.6825 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5988 Approved
0.6803 Remote Similarity NPD6373 Approved
0.6803 Remote Similarity NPD6372 Approved
0.6767 Remote Similarity NPD7319 Approved
0.6744 Remote Similarity NPD6921 Approved
0.6698 Remote Similarity NPD6114 Approved
0.6698 Remote Similarity NPD6697 Approved
0.6698 Remote Similarity NPD6115 Approved
0.6698 Remote Similarity NPD6118 Approved
0.6694 Remote Similarity NPD6675 Approved
0.6694 Remote Similarity NPD6649 Approved
0.6694 Remote Similarity NPD6650 Approved
0.6694 Remote Similarity NPD6402 Approved
0.6694 Remote Similarity NPD7128 Approved
0.6694 Remote Similarity NPD5739 Approved
0.6609 Remote Similarity NPD8171 Discontinued
0.6604 Remote Similarity NPD6116 Phase 1
0.6587 Remote Similarity NPD4632 Approved
0.6585 Remote Similarity NPD6881 Approved
0.6585 Remote Similarity NPD6899 Approved
0.6571 Remote Similarity NPD3702 Approved
0.6567 Remote Similarity NPD6033 Approved
0.656 Remote Similarity NPD8130 Phase 1
0.6557 Remote Similarity NPD6008 Approved
0.6541 Remote Similarity NPD7507 Approved
0.6515 Remote Similarity NPD8328 Phase 3
0.6515 Remote Similarity NPD7604 Phase 2
0.6509 Remote Similarity NPD6117 Approved
0.6508 Remote Similarity NPD6882 Approved
0.6504 Remote Similarity NPD5697 Approved
0.6504 Remote Similarity NPD5701 Approved
0.648 Remote Similarity NPD7290 Approved
0.648 Remote Similarity NPD4634 Approved
0.648 Remote Similarity NPD7102 Approved
0.648 Remote Similarity NPD6883 Approved
0.6457 Remote Similarity NPD8133 Approved
0.6434 Remote Similarity NPD6009 Approved
0.6429 Remote Similarity NPD6847 Approved
0.6429 Remote Similarity NPD6617 Approved
0.6429 Remote Similarity NPD6869 Approved
0.64 Remote Similarity NPD6013 Approved
0.64 Remote Similarity NPD6012 Approved
0.64 Remote Similarity NPD8132 Clinical (unspecified phase)
0.64 Remote Similarity NPD6014 Approved
0.64 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5983 Phase 2
0.6349 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6321 Remote Similarity NPD6113 Clinical (unspecified phase)
0.632 Remote Similarity NPD6011 Approved
0.6299 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6296 Remote Similarity NPD6336 Discontinued
0.6273 Remote Similarity NPD6928 Phase 2
0.6262 Remote Similarity NPD3703 Phase 2
0.6239 Remote Similarity NPD8035 Phase 2
0.6239 Remote Similarity NPD8034 Phase 2
0.6212 Remote Similarity NPD7516 Approved
0.6183 Remote Similarity NPD7115 Discovery
0.6136 Remote Similarity NPD7327 Approved
0.6136 Remote Similarity NPD7328 Approved
0.6119 Remote Similarity NPD8378 Approved
0.6119 Remote Similarity NPD8296 Approved
0.6119 Remote Similarity NPD8335 Approved
0.6119 Remote Similarity NPD8380 Approved
0.6119 Remote Similarity NPD8379 Approved
0.6119 Remote Similarity NPD8033 Approved
0.6116 Remote Similarity NPD6083 Phase 2
0.6116 Remote Similarity NPD6084 Phase 2
0.6116 Remote Similarity NPD4755 Approved
0.6111 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6107 Remote Similarity NPD6274 Approved
0.609 Remote Similarity NPD7100 Approved
0.609 Remote Similarity NPD7101 Approved
0.6045 Remote Similarity NPD8377 Approved
0.6045 Remote Similarity NPD8294 Approved
0.6016 Remote Similarity NPD4700 Approved
0.6016 Remote Similarity NPD4696 Approved
0.6016 Remote Similarity NPD5286 Approved
0.6016 Remote Similarity NPD5285 Approved
0.6015 Remote Similarity NPD6335 Approved
0.6 Remote Similarity NPD6908 Approved
0.6 Remote Similarity NPD6909 Approved
0.6 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5985 Remote Similarity NPD6940 Discontinued
0.5984 Remote Similarity NPD6412 Phase 2
0.5981 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5981 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5981 Remote Similarity NPD5777 Approved
0.5943 Remote Similarity NPD4267 Clinical (unspecified phase)
0.594 Remote Similarity NPD6317 Approved
0.5935 Remote Similarity NPD5696 Approved
0.592 Remote Similarity NPD5211 Phase 2
0.592 Remote Similarity NPD5225 Approved
0.592 Remote Similarity NPD5226 Approved
0.592 Remote Similarity NPD4633 Approved
0.592 Remote Similarity NPD5224 Approved
0.5906 Remote Similarity NPD4767 Approved
0.5906 Remote Similarity NPD4768 Approved
0.5896 Remote Similarity NPD6313 Approved
0.5896 Remote Similarity NPD6314 Approved
0.5888 Remote Similarity NPD4244 Approved
0.5888 Remote Similarity NPD4789 Approved
0.5888 Remote Similarity NPD4245 Approved
0.5887 Remote Similarity NPD5956 Approved
0.5878 Remote Similarity NPD6053 Discontinued
0.5873 Remote Similarity NPD5175 Approved
0.5873 Remote Similarity NPD5174 Approved
0.5862 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5859 Remote Similarity NPD7899 Clinical (unspecified phase)
0.584 Remote Similarity NPD5223 Approved
0.5827 Remote Similarity NPD5141 Approved
0.5826 Remote Similarity NPD3669 Approved
0.5826 Remote Similarity NPD3670 Clinical (unspecified phase)
0.582 Remote Similarity NPD5695 Phase 3
0.582 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5814 Remote Similarity NPD4729 Approved
0.5814 Remote Similarity NPD4730 Approved
0.5806 Remote Similarity NPD7638 Approved
0.5804 Remote Similarity NPD4802 Phase 2
0.5804 Remote Similarity NPD4238 Approved
0.5794 Remote Similarity NPD3698 Phase 2
0.5794 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5794 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5789 Remote Similarity NPD1780 Approved
0.5789 Remote Similarity NPD1779 Approved
0.5785 Remote Similarity NPD6399 Phase 3
0.5766 Remote Similarity NPD8513 Phase 3
0.5766 Remote Similarity NPD8516 Approved
0.5766 Remote Similarity NPD8517 Approved
0.5766 Remote Similarity NPD8515 Approved
0.576 Remote Similarity NPD7640 Approved
0.576 Remote Similarity NPD7639 Approved
0.576 Remote Similarity NPD8418 Phase 2
0.5748 Remote Similarity NPD4754 Approved
0.5725 Remote Similarity NPD5249 Phase 3
0.5725 Remote Similarity NPD5250 Approved
0.5725 Remote Similarity NPD5251 Approved
0.5725 Remote Similarity NPD5247 Approved
0.5725 Remote Similarity NPD5248 Approved
0.5714 Remote Similarity NPD6334 Approved
0.5714 Remote Similarity NPD6333 Approved
0.5701 Remote Similarity NPD5360 Phase 3
0.5701 Remote Similarity NPD229 Approved
0.5701 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5692 Remote Similarity NPD5128 Approved
0.5692 Remote Similarity NPD6686 Approved
0.5691 Remote Similarity NPD7991 Discontinued
0.5688 Remote Similarity NPD6081 Approved
0.5683 Remote Similarity NPD6067 Discontinued
0.5669 Remote Similarity NPD8083 Approved
0.5669 Remote Similarity NPD8085 Approved
0.5669 Remote Similarity NPD8139 Approved
0.5669 Remote Similarity NPD7632 Discontinued
0.5669 Remote Similarity NPD8138 Approved
0.5669 Remote Similarity NPD8084 Approved
0.5669 Remote Similarity NPD8082 Approved
0.5669 Remote Similarity NPD8086 Approved
0.5652 Remote Similarity NPD7503 Approved
0.5645 Remote Similarity NPD4697 Phase 3
0.563 Remote Similarity NPD6868 Approved
0.5625 Remote Similarity NPD8275 Approved
0.5625 Remote Similarity NPD8276 Approved
0.5619 Remote Similarity NPD371 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