Structure

Physi-Chem Properties

Molecular Weight:  412.17
Volume:  391.453
LogP:  0.111
LogD:  -0.309
LogS:  -3.348
# Rotatable Bonds:  0
TPSA:  161.59
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.293
Synthetic Accessibility Score:  5.718
Fsp3:  0.85
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.817
MDCK Permeability:  3.758941966225393e-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.967
Human Intestinal Absorption (HIA):  0.744
20% Bioavailability (F20%):  0.654
30% Bioavailability (F30%):  0.285

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.18
Plasma Protein Binding (PPB):  27.76143455505371%
Volume Distribution (VD):  0.5
Pgp-substrate:  67.43827819824219%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.772
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.761
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.079
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.084
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.09

ADMET: Excretion

Clearance (CL):  1.883
Half-life (T1/2):  0.721

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.236
Drug-inuced Liver Injury (DILI):  0.197
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.498
Maximum Recommended Daily Dose:  0.075
Skin Sensitization:  0.168
Carcinogencity:  0.106
Eye Corrosion:  0.004
Eye Irritation:  0.039
Respiratory Toxicity:  0.582

Download Data

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

  Natural Product: NPC251310

Natural Product ID:  NPC251310
Common Name*:   UJAVIKYBXBAYED-KGDUUCQMSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UJAVIKYBXBAYED-KGDUUCQMSA-N
Standard InCHI:  InChI=1S/C20H28O9/c1-7-5-9(21)14(24)18(4)13-12(23)11(22)8(2)20(28)15(25)16(26)29-10(17(13,20)3)6-19(7,18)27/h5,8,10-15,22-25,27-28H,6H2,1-4H3/t8-,10+,11+,12-,13-,14+,15-,17+,18-,19+,20-/m0/s1
SMILES:  CC1=CC(=O)[C@H]([C@]2(C)[C@H]3[C@H]([C@@H]([C@H](C)[C@@]4([C@H](C(=O)O[C@H](C[C@@]12O)[C@]34C)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3317746
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota Roots n.a. n.a. PMID[14575431]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. root n.a. PMID[1800638]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[19299148]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. PMID[19659728]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19919052]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[24467387]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[25066952]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25905468]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[28368118]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[29667820]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13494 Prosopis kuntzei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3924 Penicillium alutaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13798 Cheilanthes marantae Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22888 Lophiostoma vaginatispora Species Lophiostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12890 Ophryosporus charua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9024 Aralidium pinnatifidum Species Torricelliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8640 Nemuaron humboldtii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8820 Lophocereus marginatus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13604 Dermocybe cardinalis Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8220 Russula sardonia Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1418 Boletinus paluster Species Gyrodontaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12577 Pinus glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13692 Leontice kiangnanensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2084 Acinetobacter calcoaceticus Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12988 Blainvillea latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6626 Pteris spinulosa Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20318 Acinetobacter baumannii Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12026 Papaver radicatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2505 Pachycereus pringlei Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11072 Geigeria schinzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20383 Stenocereus thurberi Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9375 Medium grandiflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6014 Goniothalamus undulatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14280 Helichrysum angustifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3576 Bersama swinnyi Species Melianthaceae 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
NPT81 Cell Line A549 Homo sapiens Activity = 99.8 % PMID[452126]
NPT81 Cell Line A549 Homo sapiens Activity = 101.0 % PMID[452126]
NPT81 Cell Line A549 Homo sapiens Activity = 99.32 % PMID[452126]
NPT165 Cell Line HeLa Homo sapiens Activity = 101.0 % PMID[452126]
NPT165 Cell Line HeLa Homo sapiens Activity = 103.0 % PMID[452126]
NPT165 Cell Line HeLa Homo sapiens Activity = 100.0 % PMID[452126]

☑ 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 NPC251310 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
0.963 High Similarity NPC208998
0.963 High Similarity NPC7921
0.9545 High Similarity NPC176513
0.9545 High Similarity NPC474654
0.9545 High Similarity NPC470775
0.9545 High Similarity NPC470854
0.9545 High Similarity NPC97908
0.9545 High Similarity NPC122033
0.9545 High Similarity NPC287343
0.9464 High Similarity NPC112038
0.9444 High Similarity NPC146945
0.9444 High Similarity NPC171888
0.9286 High Similarity NPC470776
0.9286 High Similarity NPC17772
0.9286 High Similarity NPC188667
0.9286 High Similarity NPC204552
0.9273 High Similarity NPC49451
0.9217 High Similarity NPC67251
0.9211 High Similarity NPC477046
0.9211 High Similarity NPC102822
0.9167 High Similarity NPC293850
0.9138 High Similarity NPC476729
0.9138 High Similarity NPC24651
0.913 High Similarity NPC312833
0.9107 High Similarity NPC474734
0.9107 High Similarity NPC40632
0.9107 High Similarity NPC328374
0.9107 High Similarity NPC251236
0.9107 High Similarity NPC96312
0.9052 High Similarity NPC91693
0.9052 High Similarity NPC18945
0.9052 High Similarity NPC105926
0.9052 High Similarity NPC265557
0.9035 High Similarity NPC470777
0.9035 High Similarity NPC469488
0.9018 High Similarity NPC473798
0.9009 High Similarity NPC472002
0.8974 High Similarity NPC470922
0.8947 High Similarity NPC297179
0.8938 High Similarity NPC179626
0.8938 High Similarity NPC207217
0.8929 High Similarity NPC51978
0.8879 High Similarity NPC470779
0.886 High Similarity NPC473590
0.885 High Similarity NPC143268
0.885 High Similarity NPC117712
0.885 High Similarity NPC268238
0.885 High Similarity NPC323821
0.885 High Similarity NPC45218
0.8839 High Similarity NPC289312
0.8839 High Similarity NPC11252
0.8839 High Similarity NPC474516
0.8839 High Similarity NPC302146
0.8824 High Similarity NPC470882
0.8803 High Similarity NPC222688
0.8772 High Similarity NPC235539
0.8772 High Similarity NPC152199
0.8772 High Similarity NPC474046
0.8772 High Similarity NPC16081
0.8772 High Similarity NPC470628
0.8772 High Similarity NPC134869
0.8772 High Similarity NPC173686
0.8772 High Similarity NPC259306
0.875 High Similarity NPC201992
0.8739 High Similarity NPC225049
0.8739 High Similarity NPC141350
0.8727 High Similarity NPC3316
0.8727 High Similarity NPC144854
0.8707 High Similarity NPC476529
0.8707 High Similarity NPC475775
0.8696 High Similarity NPC27999
0.8696 High Similarity NPC477116
0.8684 High Similarity NPC470919
0.8684 High Similarity NPC474906
0.8684 High Similarity NPC469877
0.8684 High Similarity NPC18547
0.8667 High Similarity NPC476008
0.8667 High Similarity NPC473265
0.8667 High Similarity NPC470780
0.8649 High Similarity NPC277017
0.8649 High Similarity NPC154608
0.8649 High Similarity NPC192813
0.8644 High Similarity NPC269642
0.8632 High Similarity NPC107338
0.8632 High Similarity NPC109607
0.8596 High Similarity NPC198539
0.8596 High Similarity NPC477266
0.8583 High Similarity NPC293112
0.8583 High Similarity NPC477745
0.8571 High Similarity NPC472534
0.8571 High Similarity NPC143706
0.8571 High Similarity NPC87335
0.8559 High Similarity NPC230541
0.8559 High Similarity NPC472401
0.8547 High Similarity NPC473636
0.8547 High Similarity NPC268958
0.8547 High Similarity NPC77689
0.8545 High Similarity NPC65523
0.8545 High Similarity NPC475036
0.8537 High Similarity NPC102316
0.8534 High Similarity NPC473968
0.8534 High Similarity NPC470778
0.8534 High Similarity NPC469684
0.8534 High Similarity NPC134430
0.8534 High Similarity NPC146432
0.8534 High Similarity NPC309433
0.8525 High Similarity NPC470880
0.8525 High Similarity NPC231529
0.8522 High Similarity NPC243354
0.8522 High Similarity NPC299849
0.8512 High Similarity NPC473253
0.8509 High Similarity NPC317687
0.8509 High Similarity NPC269530
0.8509 High Similarity NPC90769
0.85 High Similarity NPC172154
0.85 High Similarity NPC473255
0.85 High Similarity NPC81736
0.8487 Intermediate Similarity NPC19464
0.8482 Intermediate Similarity NPC208461
0.8482 Intermediate Similarity NPC289702
0.8475 Intermediate Similarity NPC472004
0.8468 Intermediate Similarity NPC168879
0.8468 Intermediate Similarity NPC102352
0.8462 Intermediate Similarity NPC240509
0.8455 Intermediate Similarity NPC275583
0.8448 Intermediate Similarity NPC89929
0.8448 Intermediate Similarity NPC190185
0.8448 Intermediate Similarity NPC213084
0.8435 Intermediate Similarity NPC194100
0.8435 Intermediate Similarity NPC962
0.8435 Intermediate Similarity NPC73300
0.8435 Intermediate Similarity NPC94509
0.8435 Intermediate Similarity NPC250109
0.8435 Intermediate Similarity NPC194273
0.8435 Intermediate Similarity NPC108721
0.8435 Intermediate Similarity NPC471204
0.843 Intermediate Similarity NPC473635
0.843 Intermediate Similarity NPC181999
0.8421 Intermediate Similarity NPC317107
0.8421 Intermediate Similarity NPC157476
0.8421 Intermediate Similarity NPC188738
0.8421 Intermediate Similarity NPC471243
0.8417 Intermediate Similarity NPC11895
0.8417 Intermediate Similarity NPC472399
0.8417 Intermediate Similarity NPC469789
0.8413 Intermediate Similarity NPC243014
0.8413 Intermediate Similarity NPC251998
0.8407 Intermediate Similarity NPC27814
0.8407 Intermediate Similarity NPC310546
0.8403 Intermediate Similarity NPC159456
0.8403 Intermediate Similarity NPC4021
0.8393 Intermediate Similarity NPC202524
0.839 Intermediate Similarity NPC475041
0.839 Intermediate Similarity NPC473839
0.839 Intermediate Similarity NPC211093
0.8387 Intermediate Similarity NPC476193
0.8376 Intermediate Similarity NPC55296
0.8376 Intermediate Similarity NPC53396
0.8376 Intermediate Similarity NPC58662
0.8376 Intermediate Similarity NPC475809
0.8376 Intermediate Similarity NPC156252
0.8376 Intermediate Similarity NPC98249
0.8376 Intermediate Similarity NPC470171
0.8362 Intermediate Similarity NPC247069
0.8349 Intermediate Similarity NPC472972
0.8348 Intermediate Similarity NPC174836
0.8348 Intermediate Similarity NPC193948
0.8346 Intermediate Similarity NPC140045
0.8346 Intermediate Similarity NPC596
0.8346 Intermediate Similarity NPC295885
0.8333 Intermediate Similarity NPC471965
0.8333 Intermediate Similarity NPC23786
0.8333 Intermediate Similarity NPC470265
0.8333 Intermediate Similarity NPC210005
0.8333 Intermediate Similarity NPC170538
0.8333 Intermediate Similarity NPC262813
0.8333 Intermediate Similarity NPC5103
0.8333 Intermediate Similarity NPC100908
0.8319 Intermediate Similarity NPC154491
0.8319 Intermediate Similarity NPC109973
0.8319 Intermediate Similarity NPC94942
0.8319 Intermediate Similarity NPC251226
0.8319 Intermediate Similarity NPC476961
0.8319 Intermediate Similarity NPC151393
0.8319 Intermediate Similarity NPC478051
0.8319 Intermediate Similarity NPC268530
0.8319 Intermediate Similarity NPC48692
0.8319 Intermediate Similarity NPC476479
0.8306 Intermediate Similarity NPC477197
0.8305 Intermediate Similarity NPC472397
0.8305 Intermediate Similarity NPC21326
0.8305 Intermediate Similarity NPC284707
0.8305 Intermediate Similarity NPC171905
0.8305 Intermediate Similarity NPC471125
0.8305 Intermediate Similarity NPC472758
0.8304 Intermediate Similarity NPC181357
0.8293 Intermediate Similarity NPC475281
0.8293 Intermediate Similarity NPC477078
0.8293 Intermediate Similarity NPC477075
0.8293 Intermediate Similarity NPC329923

  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 NPC251310 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
0.8482 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.8264 Intermediate Similarity NPD8328 Phase 3
0.8167 Intermediate Similarity NPD6319 Approved
0.7931 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD7115 Discovery
0.7917 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7863 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD4632 Approved
0.7805 Intermediate Similarity NPD6921 Approved
0.7795 Intermediate Similarity NPD7319 Approved
0.7778 Intermediate Similarity NPD6373 Approved
0.7778 Intermediate Similarity NPD6372 Approved
0.7731 Intermediate Similarity NPD8297 Approved
0.7672 Intermediate Similarity NPD6675 Approved
0.7672 Intermediate Similarity NPD6402 Approved
0.7672 Intermediate Similarity NPD5739 Approved
0.7672 Intermediate Similarity NPD7128 Approved
0.7647 Intermediate Similarity NPD6650 Approved
0.7647 Intermediate Similarity NPD6649 Approved
0.7627 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7492 Approved
0.7611 Intermediate Similarity NPD4225 Approved
0.7607 Intermediate Similarity NPD5697 Approved
0.7607 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD5701 Approved
0.7581 Intermediate Similarity NPD6059 Approved
0.7581 Intermediate Similarity NPD6054 Approved
0.7578 Intermediate Similarity NPD7736 Approved
0.7563 Intermediate Similarity NPD4634 Approved
0.7559 Intermediate Similarity NPD6616 Approved
0.7559 Intermediate Similarity NPD7507 Approved
0.7542 Intermediate Similarity NPD6899 Approved
0.7542 Intermediate Similarity NPD6881 Approved
0.7542 Intermediate Similarity NPD7320 Approved
0.752 Intermediate Similarity NPD6016 Approved
0.752 Intermediate Similarity NPD6015 Approved
0.75 Intermediate Similarity NPD7078 Approved
0.75 Intermediate Similarity NPD8293 Discontinued
0.748 Intermediate Similarity NPD6009 Approved
0.7479 Intermediate Similarity NPD6012 Approved
0.7479 Intermediate Similarity NPD6014 Approved
0.7479 Intermediate Similarity NPD6013 Approved
0.746 Intermediate Similarity NPD6370 Approved
0.746 Intermediate Similarity NPD5988 Approved
0.7438 Intermediate Similarity NPD6882 Approved
0.7417 Intermediate Similarity NPD7102 Approved
0.7417 Intermediate Similarity NPD6883 Approved
0.7417 Intermediate Similarity NPD7290 Approved
0.7414 Intermediate Similarity NPD5211 Phase 2
0.7395 Intermediate Similarity NPD6011 Approved
0.7395 Intermediate Similarity NPD6686 Approved
0.7381 Intermediate Similarity NPD5983 Phase 2
0.7381 Intermediate Similarity NPD8513 Phase 3
0.7381 Intermediate Similarity NPD8517 Approved
0.7381 Intermediate Similarity NPD8515 Approved
0.7381 Intermediate Similarity NPD8516 Approved
0.7373 Intermediate Similarity NPD6008 Approved
0.7368 Intermediate Similarity NPD7902 Approved
0.7368 Intermediate Similarity NPD4755 Approved
0.736 Intermediate Similarity NPD7516 Approved
0.7355 Intermediate Similarity NPD8130 Phase 1
0.7355 Intermediate Similarity NPD6869 Approved
0.7355 Intermediate Similarity NPD6617 Approved
0.7355 Intermediate Similarity NPD6847 Approved
0.7311 Intermediate Similarity NPD6412 Phase 2
0.7288 Intermediate Similarity NPD5141 Approved
0.728 Intermediate Similarity NPD7327 Approved
0.728 Intermediate Similarity NPD7328 Approved
0.7266 Intermediate Similarity NPD7604 Phase 2
0.7257 Intermediate Similarity NPD7748 Approved
0.7241 Intermediate Similarity NPD7640 Approved
0.7241 Intermediate Similarity NPD5285 Approved
0.7241 Intermediate Similarity NPD7639 Approved
0.7241 Intermediate Similarity NPD5286 Approved
0.7241 Intermediate Similarity NPD4700 Approved
0.7241 Intermediate Similarity NPD4696 Approved
0.7232 Intermediate Similarity NPD7515 Phase 2
0.7213 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD3573 Approved
0.7179 Intermediate Similarity NPD5344 Discontinued
0.7168 Intermediate Similarity NPD5778 Approved
0.7168 Intermediate Similarity NPD5779 Approved
0.7155 Intermediate Similarity NPD7638 Approved
0.7154 Intermediate Similarity NPD6336 Discontinued
0.713 Intermediate Similarity NPD4697 Phase 3
0.712 Intermediate Similarity NPD6274 Approved
0.7119 Intermediate Similarity NPD5225 Approved
0.7119 Intermediate Similarity NPD4633 Approved
0.7119 Intermediate Similarity NPD5224 Approved
0.7119 Intermediate Similarity NPD5226 Approved
0.7105 Intermediate Similarity NPD7900 Approved
0.7105 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD4768 Approved
0.7083 Intermediate Similarity NPD4767 Approved
0.708 Intermediate Similarity NPD7983 Approved
0.708 Intermediate Similarity NPD6411 Approved
0.7069 Intermediate Similarity NPD6083 Phase 2
0.7069 Intermediate Similarity NPD6084 Phase 2
0.7059 Intermediate Similarity NPD5174 Approved
0.7059 Intermediate Similarity NPD5175 Approved
0.7045 Intermediate Similarity NPD6033 Approved
0.7034 Intermediate Similarity NPD5223 Approved
0.7018 Intermediate Similarity NPD6399 Phase 3
0.7009 Intermediate Similarity NPD5696 Approved
0.6992 Remote Similarity NPD6371 Approved
0.6991 Remote Similarity NPD6698 Approved
0.6991 Remote Similarity NPD46 Approved
0.6983 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6983 Remote Similarity NPD5221 Approved
0.6983 Remote Similarity NPD5222 Approved
0.6977 Remote Similarity NPD8379 Approved
0.6977 Remote Similarity NPD8296 Approved
0.6977 Remote Similarity NPD8378 Approved
0.6977 Remote Similarity NPD8335 Approved
0.6977 Remote Similarity NPD8380 Approved
0.6977 Remote Similarity NPD8033 Approved
0.697 Remote Similarity NPD8074 Phase 3
0.6967 Remote Similarity NPD4729 Approved
0.6967 Remote Similarity NPD4730 Approved
0.6957 Remote Similarity NPD5282 Discontinued
0.6953 Remote Similarity NPD7100 Approved
0.6953 Remote Similarity NPD7101 Approved
0.6937 Remote Similarity NPD3618 Phase 1
0.6935 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6317 Approved
0.6923 Remote Similarity NPD5173 Approved
0.6917 Remote Similarity NPD4754 Approved
0.6903 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5328 Approved
0.6903 Remote Similarity NPD6101 Approved
0.6899 Remote Similarity NPD8377 Approved
0.6899 Remote Similarity NPD8294 Approved
0.6897 Remote Similarity NPD5695 Phase 3
0.6889 Remote Similarity NPD7260 Phase 2
0.6885 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6314 Approved
0.6875 Remote Similarity NPD6335 Approved
0.6875 Remote Similarity NPD6313 Approved
0.6855 Remote Similarity NPD5247 Approved
0.6855 Remote Similarity NPD5249 Phase 3
0.6855 Remote Similarity NPD5251 Approved
0.6855 Remote Similarity NPD5250 Approved
0.6855 Remote Similarity NPD5248 Approved
0.6846 Remote Similarity NPD6909 Approved
0.6846 Remote Similarity NPD6908 Approved
0.6846 Remote Similarity NPD7503 Approved
0.6846 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5128 Approved
0.6825 Remote Similarity NPD8133 Approved
0.6807 Remote Similarity NPD6648 Approved
0.6783 Remote Similarity NPD6079 Approved
0.6754 Remote Similarity NPD4753 Phase 2
0.6746 Remote Similarity NPD6053 Discontinued
0.6724 Remote Similarity NPD4202 Approved
0.6719 Remote Similarity NPD6868 Approved
0.6694 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD5215 Approved
0.6667 Remote Similarity NPD5216 Approved
0.6667 Remote Similarity NPD6672 Approved
0.6667 Remote Similarity NPD5737 Approved
0.6667 Remote Similarity NPD5217 Approved
0.6638 Remote Similarity NPD7637 Suspended
0.6637 Remote Similarity NPD3574 Clinical (unspecified phase)
0.661 Remote Similarity NPD4629 Approved
0.661 Remote Similarity NPD1698 Clinical (unspecified phase)
0.661 Remote Similarity NPD5210 Approved
0.6609 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6594 Remote Similarity NPD6845 Suspended
0.6587 Remote Similarity NPD5135 Approved
0.6587 Remote Similarity NPD5169 Approved
0.6587 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6577 Remote Similarity NPD3667 Approved
0.6545 Remote Similarity NPD4695 Discontinued
0.6535 Remote Similarity NPD5127 Approved
0.6522 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6518 Remote Similarity NPD6110 Phase 1
0.6496 Remote Similarity NPD8034 Phase 2
0.6496 Remote Similarity NPD5693 Phase 1
0.6496 Remote Similarity NPD8035 Phase 2
0.6491 Remote Similarity NPD6409 Approved
0.6491 Remote Similarity NPD7334 Approved
0.6491 Remote Similarity NPD5330 Approved
0.6491 Remote Similarity NPD6684 Approved
0.6491 Remote Similarity NPD7521 Approved
0.6491 Remote Similarity NPD7146 Approved
0.6479 Remote Similarity NPD6334 Approved
0.6479 Remote Similarity NPD6333 Approved
0.6475 Remote Similarity NPD1700 Approved
0.6471 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6466 Remote Similarity NPD6904 Approved
0.6466 Remote Similarity NPD6673 Approved
0.6466 Remote Similarity NPD6080 Approved
0.646 Remote Similarity NPD3665 Phase 1
0.646 Remote Similarity NPD3666 Approved
0.646 Remote Similarity NPD4786 Approved
0.646 Remote Similarity NPD3133 Approved
0.6454 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5956 Approved
0.6446 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6439 Remote Similarity NPD4522 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