Structure

Physi-Chem Properties

Molecular Weight:  396.18
Volume:  382.663
LogP:  0.648
LogD:  0.177
LogS:  -3.425
# Rotatable Bonds:  0
TPSA:  141.36
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.308
Synthetic Accessibility Score:  5.409
Fsp3:  0.85
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.416
MDCK Permeability:  5.7823963288683444e-05
Pgp-inhibitor:  0.829
Pgp-substrate:  0.921
Human Intestinal Absorption (HIA):  0.296
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.425

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.379
Plasma Protein Binding (PPB):  29.758670806884766%
Volume Distribution (VD):  0.466
Pgp-substrate:  62.86097717285156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.328
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.66
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.085
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.122
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.106

ADMET: Excretion

Clearance (CL):  2.293
Half-life (T1/2):  0.352

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.299
Drug-inuced Liver Injury (DILI):  0.267
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.516
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.289
Carcinogencity:  0.045
Eye Corrosion:  0.015
Eye Irritation:  0.029
Respiratory Toxicity:  0.84

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  Natural Product: NPC208998

Natural Product ID:  NPC208998
Common Name*:   NWNMAVFXIRDAPM-RELKVJPISA-N
IUPAC Name:   n.a.
Synonyms:   14,15Beta-Dihydroxyklaineanone
Standard InCHIKey:  NWNMAVFXIRDAPM-RELKVJPISA-N
Standard InCHI:  InChI=1S/C20H28O8/c1-7-5-10(21)15(24)18(3)9(7)6-11-19(4)14(18)13(23)12(22)8(2)20(19,27)16(25)17(26)28-11/h5,8-9,11-16,22-25,27H,6H2,1-4H3/t8-,9-,11+,12+,13-,14+,15+,16-,18-,19+,20-/m0/s1
SMILES:  CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@H]1OC(=O)[C@@H]([C@@]3([C@]1([C@@H]2[C@@H](O)[C@@H]([C@@H]3C)O)C)O)O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1080347
PubChem CID:   10883790
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
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 1100.0 nM PMID[470821]
NPT81 Cell Line A549 Homo sapiens Activity = 99.47 % PMID[470823]
NPT81 Cell Line A549 Homo sapiens Activity = 86.42 % PMID[470823]
NPT81 Cell Line A549 Homo sapiens Activity = 43.3 % PMID[470823]
NPT165 Cell Line HeLa Homo sapiens Activity = 100.6 % PMID[470823]
NPT165 Cell Line HeLa Homo sapiens Activity = 71.58 % PMID[470823]
NPT165 Cell Line HeLa Homo sapiens Activity = 21.01 % PMID[470823]
NPT165 Cell Line HeLa Homo sapiens IC50 = 48180.0 nM PMID[470823]
NPT140 Organism Artemia Artemia LD50 = 323.5 ug ml-1 PMID[470822]
NPT2 Others Unspecified IC50 = 1000.0 nM PMID[470822]
NPT2 Others Unspecified Inhibition > 50.0 % PMID[470822]

☑ 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 NPC208998 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 NPC7921
0.9808 High Similarity NPC171888
0.9808 High Similarity NPC146945
0.972 High Similarity NPC97908
0.972 High Similarity NPC122033
0.972 High Similarity NPC470854
0.972 High Similarity NPC287343
0.972 High Similarity NPC474654
0.963 High Similarity NPC188667
0.963 High Similarity NPC204552
0.963 High Similarity NPC251310
0.9519 High Similarity NPC293850
0.9455 High Similarity NPC112038
0.945 High Similarity NPC17772
0.9439 High Similarity NPC49451
0.9369 High Similarity NPC102822
0.9369 High Similarity NPC477046
0.9364 High Similarity NPC469488
0.9273 High Similarity NPC297179
0.9266 High Similarity NPC96312
0.9266 High Similarity NPC40632
0.9266 High Similarity NPC251236
0.9266 High Similarity NPC328374
0.9189 High Similarity NPC470777
0.9182 High Similarity NPC176513
0.9182 High Similarity NPC470775
0.9174 High Similarity NPC473798
0.9167 High Similarity NPC11252
0.9167 High Similarity NPC474516
0.9167 High Similarity NPC289312
0.9091 High Similarity NPC134869
0.9091 High Similarity NPC207217
0.9091 High Similarity NPC152199
0.9091 High Similarity NPC235539
0.9074 High Similarity NPC201992
0.9 High Similarity NPC474906
0.9 High Similarity NPC143268
0.9 High Similarity NPC18547
0.9 High Similarity NPC268238
0.9 High Similarity NPC45218
0.9 High Similarity NPC323821
0.8957 High Similarity NPC24651
0.8947 High Similarity NPC312833
0.8929 High Similarity NPC470776
0.8919 High Similarity NPC173686
0.8919 High Similarity NPC16081
0.8909 High Similarity NPC51978
0.8879 High Similarity NPC3316
0.8879 High Similarity NPC144854
0.887 High Similarity NPC91693
0.887 High Similarity NPC105926
0.887 High Similarity NPC18945
0.887 High Similarity NPC265557
0.887 High Similarity NPC67251
0.8868 High Similarity NPC475036
0.8839 High Similarity NPC309433
0.8818 High Similarity NPC90769
0.8796 High Similarity NPC154608
0.8796 High Similarity NPC192813
0.8796 High Similarity NPC277017
0.8793 High Similarity NPC470922
0.8793 High Similarity NPC476729
0.875 High Similarity NPC474734
0.8739 High Similarity NPC477266
0.8739 High Similarity NPC194100
0.8739 High Similarity NPC198539
0.8696 High Similarity NPC470779
0.8692 High Similarity NPC65523
0.8684 High Similarity NPC475775
0.8684 High Similarity NPC476529
0.8673 High Similarity NPC473590
0.8667 High Similarity NPC472972
0.8661 High Similarity NPC243354
0.8649 High Similarity NPC472002
0.8649 High Similarity NPC302146
0.8632 High Similarity NPC473255
0.8611 High Similarity NPC102352
0.8609 High Similarity NPC107338
0.8609 High Similarity NPC109607
0.8598 High Similarity NPC275583
0.8584 High Similarity NPC259306
0.8584 High Similarity NPC179626
0.8584 High Similarity NPC470628
0.8584 High Similarity NPC474046
0.8571 High Similarity NPC194273
0.8559 High Similarity NPC471243
0.8545 High Similarity NPC310546
0.8545 High Similarity NPC27814
0.8532 High Similarity NPC202524
0.8522 High Similarity NPC473636
0.8522 High Similarity NPC77689
0.8509 High Similarity NPC134430
0.8496 Intermediate Similarity NPC117712
0.8496 Intermediate Similarity NPC470919
0.8496 Intermediate Similarity NPC469877
0.8496 Intermediate Similarity NPC247069
0.8487 Intermediate Similarity NPC476008
0.8487 Intermediate Similarity NPC470780
0.8487 Intermediate Similarity NPC470882
0.8482 Intermediate Similarity NPC193948
0.8468 Intermediate Similarity NPC474567
0.8468 Intermediate Similarity NPC100908
0.8468 Intermediate Similarity NPC210005
0.8462 Intermediate Similarity NPC222688
0.8462 Intermediate Similarity NPC471965
0.8455 Intermediate Similarity NPC94942
0.8455 Intermediate Similarity NPC289702
0.8455 Intermediate Similarity NPC208461
0.8448 Intermediate Similarity NPC472004
0.844 Intermediate Similarity NPC477877
0.844 Intermediate Similarity NPC181357
0.8417 Intermediate Similarity NPC188291
0.8407 Intermediate Similarity NPC320118
0.8403 Intermediate Similarity NPC225049
0.8403 Intermediate Similarity NPC477745
0.8393 Intermediate Similarity NPC34315
0.839 Intermediate Similarity NPC471964
0.839 Intermediate Similarity NPC471961
0.839 Intermediate Similarity NPC202666
0.839 Intermediate Similarity NPC262199
0.839 Intermediate Similarity NPC14617
0.8381 Intermediate Similarity NPC469369
0.8381 Intermediate Similarity NPC469528
0.8378 Intermediate Similarity NPC143706
0.8378 Intermediate Similarity NPC472534
0.8378 Intermediate Similarity NPC141350
0.8376 Intermediate Similarity NPC75417
0.8376 Intermediate Similarity NPC275675
0.8376 Intermediate Similarity NPC470921
0.8362 Intermediate Similarity NPC211093
0.8362 Intermediate Similarity NPC473839
0.8361 Intermediate Similarity NPC100390
0.8361 Intermediate Similarity NPC254614
0.8349 Intermediate Similarity NPC284865
0.8348 Intermediate Similarity NPC27999
0.8348 Intermediate Similarity NPC146432
0.8348 Intermediate Similarity NPC477116
0.8348 Intermediate Similarity NPC473968
0.8348 Intermediate Similarity NPC475809
0.8348 Intermediate Similarity NPC470778
0.8347 Intermediate Similarity NPC231529
0.8333 Intermediate Similarity NPC473265
0.8333 Intermediate Similarity NPC102088
0.8333 Intermediate Similarity NPC299849
0.8319 Intermediate Similarity NPC471962
0.8319 Intermediate Similarity NPC473397
0.8319 Intermediate Similarity NPC280782
0.8319 Intermediate Similarity NPC247315
0.8319 Intermediate Similarity NPC471963
0.8305 Intermediate Similarity NPC269642
0.8304 Intermediate Similarity NPC85391
0.8291 Intermediate Similarity NPC476961
0.8288 Intermediate Similarity NPC273155
0.8276 Intermediate Similarity NPC286347
0.8264 Intermediate Similarity NPC475636
0.8264 Intermediate Similarity NPC295220
0.8261 Intermediate Similarity NPC89929
0.8261 Intermediate Similarity NPC213084
0.8261 Intermediate Similarity NPC190185
0.825 Intermediate Similarity NPC293112
0.825 Intermediate Similarity NPC181066
0.825 Intermediate Similarity NPC473635
0.825 Intermediate Similarity NPC285091
0.825 Intermediate Similarity NPC87662
0.825 Intermediate Similarity NPC469947
0.825 Intermediate Similarity NPC181999
0.8246 Intermediate Similarity NPC94509
0.8246 Intermediate Similarity NPC471204
0.8246 Intermediate Similarity NPC255017
0.8246 Intermediate Similarity NPC471252
0.8246 Intermediate Similarity NPC62696
0.8246 Intermediate Similarity NPC293038
0.8235 Intermediate Similarity NPC11895
0.8235 Intermediate Similarity NPC227397
0.823 Intermediate Similarity NPC472003
0.823 Intermediate Similarity NPC213320
0.823 Intermediate Similarity NPC29505
0.823 Intermediate Similarity NPC474229
0.823 Intermediate Similarity NPC157476
0.822 Intermediate Similarity NPC472401
0.8214 Intermediate Similarity NPC87335
0.8214 Intermediate Similarity NPC41405
0.8214 Intermediate Similarity NPC218853
0.8214 Intermediate Similarity NPC474242
0.8211 Intermediate Similarity NPC6274
0.8211 Intermediate Similarity NPC254146
0.8211 Intermediate Similarity NPC102316
0.8211 Intermediate Similarity NPC33378
0.8205 Intermediate Similarity NPC6377
0.8205 Intermediate Similarity NPC309780
0.8205 Intermediate Similarity NPC114441
0.8205 Intermediate Similarity NPC473203
0.8205 Intermediate Similarity NPC279143
0.8205 Intermediate Similarity NPC472949
0.8205 Intermediate Similarity NPC475171
0.8205 Intermediate Similarity NPC319570
0.8205 Intermediate Similarity NPC208381
0.8205 Intermediate Similarity NPC180550
0.8205 Intermediate Similarity NPC157868
0.8205 Intermediate Similarity NPC268958

  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 NPC208998 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
0.8455 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.8448 Intermediate Similarity NPD6319 Approved
0.839 Intermediate Similarity NPD8328 Phase 3
0.8087 Intermediate Similarity NPD4632 Approved
0.8034 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8297 Approved
0.7946 Intermediate Similarity NPD6675 Approved
0.7946 Intermediate Similarity NPD6402 Approved
0.7946 Intermediate Similarity NPD7128 Approved
0.7946 Intermediate Similarity NPD5739 Approved
0.7895 Intermediate Similarity NPD6373 Approved
0.7895 Intermediate Similarity NPD6372 Approved
0.7895 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7876 Intermediate Similarity NPD5701 Approved
0.7876 Intermediate Similarity NPD5697 Approved
0.7869 Intermediate Similarity NPD7492 Approved
0.7833 Intermediate Similarity NPD6059 Approved
0.7833 Intermediate Similarity NPD6054 Approved
0.7826 Intermediate Similarity NPD4634 Approved
0.7823 Intermediate Similarity NPD7736 Approved
0.7807 Intermediate Similarity NPD7320 Approved
0.7807 Intermediate Similarity NPD6899 Approved
0.7807 Intermediate Similarity NPD6881 Approved
0.7805 Intermediate Similarity NPD6616 Approved
0.7769 Intermediate Similarity NPD6016 Approved
0.7769 Intermediate Similarity NPD6921 Approved
0.7769 Intermediate Similarity NPD6015 Approved
0.776 Intermediate Similarity NPD7319 Approved
0.7759 Intermediate Similarity NPD6649 Approved
0.7759 Intermediate Similarity NPD6650 Approved
0.7742 Intermediate Similarity NPD7078 Approved
0.7742 Intermediate Similarity NPD8293 Discontinued
0.7739 Intermediate Similarity NPD6012 Approved
0.7739 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD6014 Approved
0.7739 Intermediate Similarity NPD6013 Approved
0.7731 Intermediate Similarity NPD6009 Approved
0.7705 Intermediate Similarity NPD6370 Approved
0.7705 Intermediate Similarity NPD5988 Approved
0.7692 Intermediate Similarity NPD6882 Approved
0.7672 Intermediate Similarity NPD7102 Approved
0.7672 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD6883 Approved
0.7672 Intermediate Similarity NPD7290 Approved
0.7652 Intermediate Similarity NPD6011 Approved
0.7636 Intermediate Similarity NPD4755 Approved
0.7623 Intermediate Similarity NPD5983 Phase 2
0.7607 Intermediate Similarity NPD8130 Phase 1
0.7607 Intermediate Similarity NPD6617 Approved
0.7607 Intermediate Similarity NPD6869 Approved
0.7607 Intermediate Similarity NPD6847 Approved
0.7583 Intermediate Similarity NPD7115 Discovery
0.7565 Intermediate Similarity NPD6412 Phase 2
0.7523 Intermediate Similarity NPD7748 Approved
0.752 Intermediate Similarity NPD7507 Approved
0.75 Intermediate Similarity NPD5286 Approved
0.75 Intermediate Similarity NPD4700 Approved
0.75 Intermediate Similarity NPD7515 Phase 2
0.75 Intermediate Similarity NPD4696 Approved
0.75 Intermediate Similarity NPD7604 Phase 2
0.75 Intermediate Similarity NPD5285 Approved
0.7478 Intermediate Similarity NPD6008 Approved
0.7477 Intermediate Similarity NPD7902 Approved
0.7458 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD3573 Approved
0.7414 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD6336 Discontinued
0.7368 Intermediate Similarity NPD5224 Approved
0.7368 Intermediate Similarity NPD5211 Phase 2
0.7368 Intermediate Similarity NPD5225 Approved
0.7368 Intermediate Similarity NPD4633 Approved
0.7368 Intermediate Similarity NPD5226 Approved
0.7355 Intermediate Similarity NPD6274 Approved
0.735 Intermediate Similarity NPD6686 Approved
0.7339 Intermediate Similarity NPD6411 Approved
0.7328 Intermediate Similarity NPD4768 Approved
0.7328 Intermediate Similarity NPD4767 Approved
0.7321 Intermediate Similarity NPD6084 Phase 2
0.7321 Intermediate Similarity NPD6083 Phase 2
0.7317 Intermediate Similarity NPD7516 Approved
0.7304 Intermediate Similarity NPD5175 Approved
0.7304 Intermediate Similarity NPD5174 Approved
0.7281 Intermediate Similarity NPD5223 Approved
0.7266 Intermediate Similarity NPD6033 Approved
0.7257 Intermediate Similarity NPD4225 Approved
0.7241 Intermediate Similarity NPD5141 Approved
0.7236 Intermediate Similarity NPD7327 Approved
0.7236 Intermediate Similarity NPD7328 Approved
0.7232 Intermediate Similarity NPD4697 Phase 3
0.7232 Intermediate Similarity NPD5221 Approved
0.7232 Intermediate Similarity NPD5222 Approved
0.7232 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD7900 Approved
0.7207 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD4730 Approved
0.7203 Intermediate Similarity NPD4729 Approved
0.7177 Intermediate Similarity NPD7101 Approved
0.7177 Intermediate Similarity NPD7100 Approved
0.7168 Intermediate Similarity NPD5173 Approved
0.7156 Intermediate Similarity NPD5328 Approved
0.7156 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD6101 Approved
0.7155 Intermediate Similarity NPD4754 Approved
0.7154 Intermediate Similarity NPD6317 Approved
0.7143 Intermediate Similarity NPD5695 Phase 3
0.7117 Intermediate Similarity NPD6399 Phase 3
0.7105 Intermediate Similarity NPD5696 Approved
0.7105 Intermediate Similarity NPD7638 Approved
0.7097 Intermediate Similarity NPD6335 Approved
0.7097 Intermediate Similarity NPD6314 Approved
0.7097 Intermediate Similarity NPD6313 Approved
0.7083 Intermediate Similarity NPD5247 Approved
0.7083 Intermediate Similarity NPD5250 Approved
0.7083 Intermediate Similarity NPD5249 Phase 3
0.7083 Intermediate Similarity NPD5248 Approved
0.7083 Intermediate Similarity NPD5251 Approved
0.7063 Intermediate Similarity NPD8515 Approved
0.7063 Intermediate Similarity NPD8517 Approved
0.7063 Intermediate Similarity NPD6909 Approved
0.7063 Intermediate Similarity NPD8516 Approved
0.7063 Intermediate Similarity NPD6908 Approved
0.7063 Intermediate Similarity NPD8513 Phase 3
0.7059 Intermediate Similarity NPD5128 Approved
0.7054 Intermediate Similarity NPD5282 Discontinued
0.7043 Intermediate Similarity NPD7639 Approved
0.7043 Intermediate Similarity NPD7640 Approved
0.7037 Intermediate Similarity NPD3618 Phase 1
0.7027 Intermediate Similarity NPD6079 Approved
0.7 Intermediate Similarity NPD4753 Phase 2
0.6983 Remote Similarity NPD5344 Discontinued
0.6964 Remote Similarity NPD5778 Approved
0.6964 Remote Similarity NPD5779 Approved
0.6964 Remote Similarity NPD4202 Approved
0.6937 Remote Similarity NPD46 Approved
0.6937 Remote Similarity NPD6698 Approved
0.6935 Remote Similarity NPD6868 Approved
0.6929 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6929 Remote Similarity NPD8379 Approved
0.6929 Remote Similarity NPD8296 Approved
0.6929 Remote Similarity NPD8033 Approved
0.6929 Remote Similarity NPD8378 Approved
0.6929 Remote Similarity NPD8335 Approved
0.6929 Remote Similarity NPD8380 Approved
0.6911 Remote Similarity NPD8133 Approved
0.6909 Remote Similarity NPD5737 Approved
0.6909 Remote Similarity NPD6672 Approved
0.6885 Remote Similarity NPD5215 Approved
0.6885 Remote Similarity NPD5217 Approved
0.6885 Remote Similarity NPD5216 Approved
0.6875 Remote Similarity NPD7983 Approved
0.685 Remote Similarity NPD8377 Approved
0.685 Remote Similarity NPD8294 Approved
0.6847 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6822 Remote Similarity NPD3667 Approved
0.6803 Remote Similarity NPD5135 Approved
0.6803 Remote Similarity NPD5169 Approved
0.6803 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6797 Remote Similarity NPD7503 Approved
0.6792 Remote Similarity NPD4695 Discontinued
0.6757 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6748 Remote Similarity NPD5127 Approved
0.6727 Remote Similarity NPD7334 Approved
0.6727 Remote Similarity NPD6409 Approved
0.6727 Remote Similarity NPD7521 Approved
0.6727 Remote Similarity NPD5330 Approved
0.6727 Remote Similarity NPD7146 Approved
0.6727 Remote Similarity NPD6684 Approved
0.6727 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7260 Phase 2
0.6697 Remote Similarity NPD3665 Phase 1
0.6697 Remote Similarity NPD3133 Approved
0.6697 Remote Similarity NPD4786 Approved
0.6697 Remote Similarity NPD3666 Approved
0.6696 Remote Similarity NPD6080 Approved
0.6696 Remote Similarity NPD5210 Approved
0.6696 Remote Similarity NPD6673 Approved
0.6696 Remote Similarity NPD6904 Approved
0.6696 Remote Similarity NPD4629 Approved
0.6694 Remote Similarity NPD6053 Discontinued
0.6694 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6334 Approved
0.6667 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD6333 Approved
0.6667 Remote Similarity NPD6371 Approved
0.6642 Remote Similarity NPD5956 Approved
0.6641 Remote Similarity NPD4522 Approved
0.6639 Remote Similarity NPD5168 Approved
0.6613 Remote Similarity NPD8413 Clinical (unspecified phase)
0.661 Remote Similarity NPD6648 Approved
0.6607 Remote Similarity NPD6903 Approved
0.6587 Remote Similarity NPD5167 Approved
0.6579 Remote Similarity NPD5693 Phase 1
0.6579 Remote Similarity NPD8034 Phase 2
0.6579 Remote Similarity NPD8035 Phase 2
0.6577 Remote Similarity NPD5279 Phase 3
0.6565 Remote Similarity NPD6067 Discontinued
0.6555 Remote Similarity NPD1700 Approved
0.6552 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6552 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6545 Remote Similarity NPD4197 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