Structure

Physi-Chem Properties

Molecular Weight:  378.17
Volume:  365.316
LogP:  1.43
LogD:  0.93
LogS:  -4.192
# Rotatable Bonds:  0
TPSA:  110.13
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.465
Synthetic Accessibility Score:  6.514
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:  -5.285
MDCK Permeability:  3.444275716901757e-05
Pgp-inhibitor:  0.838
Pgp-substrate:  0.214
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.524

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.913
Plasma Protein Binding (PPB):  44.624847412109375%
Volume Distribution (VD):  0.644
Pgp-substrate:  58.989845275878906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.937
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.652
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.132
CYP3A4-inhibitor:  0.103
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  2.921
Half-life (T1/2):  0.515

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.34
Drug-inuced Liver Injury (DILI):  0.543
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.782
Maximum Recommended Daily Dose:  0.311
Skin Sensitization:  0.29
Carcinogencity:  0.488
Eye Corrosion:  0.006
Eye Irritation:  0.022
Respiratory Toxicity:  0.949

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

  Natural Product: NPC201992

Natural Product ID:  NPC201992
Common Name*:   Chaparrinone
IUPAC Name:   n.a.
Synonyms:   NSC-288754; TCMDC-142261
Standard InCHIKey:  VLYMLZRDCSQUQF-RZUZYEBMSA-N
Standard InCHI:  InChI=1S/C20H26O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,9-11,13,15-17,23-25H,5-7H2,1-3H3/t9-,10+,11+,13-,15-,16-,17-,18-,19-,20+/m1/s1
SMILES:  O=C1O[C@@H]2C[C@H]3C(=CC(=O)[C@H]([C@@]3([C@@H]3[C@@]42[C@@H](C1)[C@@H](C)[C@H]([C@@]3(OC4)O)O)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL472016
PubChem CID:   73154
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
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. xylem n.a. DOI[10.1016/S0040-4039(00)86970-1]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. xylem n.a. DOI[10.1248/cpb.24.1532]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[17340534]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[22224661]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[22799262]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[23290052]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota stem barks n.a. n.a. PMID[25666824]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota Fruits n.a. n.a. PMID[3760884]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6736970]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6875576]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6875577]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. xylem n.a. PMID[6875577]
NPO22346 Simaba cedron Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[9644063]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22346 Simaba cedron Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 = 1200.0 nM PMID[494783]
NPT116 Cell Line HL-60 Homo sapiens EC50 = 2400.0 nM PMID[494783]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 5000.0 nM PMID[494783]
NPT116 Cell Line HL-60 Homo sapiens Ratio IC50 = 4.3 n.a. PMID[494783]
NPT168 Cell Line P388 Mus musculus IC50 = 0.92 ug.mL-1 PMID[494784]
NPT91 Cell Line KB Homo sapiens ED50 = 0.025 ug ml-1 PMID[494785]
NPT111 Cell Line K562 Homo sapiens IC50 = 1.8 ug.mL-1 PMID[494786]
NPT91 Cell Line KB Homo sapiens IC50 = 1.2 ug.mL-1 PMID[494786]
NPT457 Cell Line BT-549 Homo sapiens IC50 = 0.8 ug.mL-1 PMID[494786]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 0.5 ug.mL-1 PMID[494786]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 1.5 ug.mL-1 PMID[494786]
NPT65 Cell Line HepG2 Homo sapiens Inhibition = 38.0 % PMID[494787]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 50000.0 nM PMID[494788]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 1200.0 nM PMID[494788]
NPT2 Others Unspecified Inhibition = 25.0 % PMID[494783]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.25 ug.mL-1 PMID[494786]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.2 ug.mL-1 PMID[494786]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum XC50 = 346.53 nM PMID[494787]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition = 98.0 % PMID[494787]
NPT2 Others Unspecified IFI = 7.19 % PMID[494787]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition = 99.0 % PMID[494787]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition = 4.0 % PMID[494787]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2170.0 nM PMID[494788]
NPT942 Individual Protein Glucose transporter Homo sapiens Inhibition = 7.27 % PMID[494789]
NPT943 Individual Protein Hexose transporter 1 Plasmodium falciparum Inhibition = 2.51 % PMID[494789]
NPT944 Individual Protein Glucose transporter Leishmania mexicana Inhibition = 0.79 % PMID[494789]

☑ 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 NPC201992 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
0.9903 High Similarity NPC289312
0.9903 High Similarity NPC11252
0.9808 High Similarity NPC51978
0.9714 High Similarity NPC474906
0.9714 High Similarity NPC18547
0.9623 High Similarity NPC152199
0.9623 High Similarity NPC235539
0.9623 High Similarity NPC134869
0.9515 High Similarity NPC293850
0.9444 High Similarity NPC188667
0.9444 High Similarity NPC297179
0.9444 High Similarity NPC204552
0.9434 High Similarity NPC49451
0.9417 High Similarity NPC144854
0.9417 High Similarity NPC3316
0.9358 High Similarity NPC476529
0.9358 High Similarity NPC475775
0.934 High Similarity NPC302146
0.9327 High Similarity NPC277017
0.9327 High Similarity NPC192813
0.9327 High Similarity NPC154608
0.9273 High Similarity NPC112038
0.9273 High Similarity NPC109607
0.9273 High Similarity NPC107338
0.9259 High Similarity NPC96312
0.9259 High Similarity NPC328374
0.9259 High Similarity NPC40632
0.9259 High Similarity NPC251236
0.9238 High Similarity NPC472534
0.9238 High Similarity NPC143706
0.9189 High Similarity NPC477046
0.9189 High Similarity NPC102822
0.9182 High Similarity NPC469488
0.9174 High Similarity NPC97908
0.9174 High Similarity NPC122033
0.9174 High Similarity NPC474654
0.9174 High Similarity NPC309433
0.9174 High Similarity NPC470854
0.9174 High Similarity NPC287343
0.9167 High Similarity NPC469877
0.9167 High Similarity NPC470919
0.9167 High Similarity NPC473798
0.9159 High Similarity NPC474516
0.9135 High Similarity NPC102352
0.9091 High Similarity NPC17772
0.9083 High Similarity NPC470628
0.9083 High Similarity NPC259306
0.9083 High Similarity NPC474046
0.9074 High Similarity NPC208998
0.9074 High Similarity NPC7921
0.9065 High Similarity NPC171888
0.9065 High Similarity NPC146945
0.9 High Similarity NPC473968
0.8991 High Similarity NPC243354
0.8972 High Similarity NPC210005
0.8952 High Similarity NPC181357
0.8947 High Similarity NPC470922
0.8909 High Similarity NPC207217
0.8899 High Similarity NPC194273
0.8899 High Similarity NPC194100
0.8889 High Similarity NPC471243
0.8879 High Similarity NPC141350
0.8839 High Similarity NPC470777
0.8762 High Similarity NPC275583
0.875 High Similarity NPC251310
0.8739 High Similarity NPC474734
0.8727 High Similarity NPC255017
0.8704 High Similarity NPC27814
0.8692 High Similarity NPC230541
0.8661 High Similarity NPC176513
0.8661 High Similarity NPC470775
0.8661 High Similarity NPC473590
0.8654 High Similarity NPC472972
0.8649 High Similarity NPC323821
0.8649 High Similarity NPC143268
0.8649 High Similarity NPC102088
0.8649 High Similarity NPC268238
0.8649 High Similarity NPC45218
0.8636 High Similarity NPC472002
0.8624 High Similarity NPC474567
0.8621 High Similarity NPC24651
0.8609 High Similarity NPC312833
0.8584 High Similarity NPC470776
0.8571 High Similarity NPC179626
0.8571 High Similarity NPC16081
0.8571 High Similarity NPC173686
0.8559 High Similarity NPC320118
0.8559 High Similarity NPC62696
0.8559 High Similarity NPC293038
0.8547 High Similarity NPC285091
0.8545 High Similarity NPC188738
0.8534 High Similarity NPC227397
0.8534 High Similarity NPC265557
0.8534 High Similarity NPC105926
0.8534 High Similarity NPC67251
0.8534 High Similarity NPC91693
0.8534 High Similarity NPC18945
0.8532 High Similarity NPC310546
0.8519 High Similarity NPC293512
0.8509 High Similarity NPC473401
0.8509 High Similarity NPC473920
0.8509 High Similarity NPC127530
0.8509 High Similarity NPC122971
0.8482 Intermediate Similarity NPC475633
0.8468 Intermediate Similarity NPC471967
0.8468 Intermediate Similarity NPC205534
0.8462 Intermediate Similarity NPC476729
0.8455 Intermediate Similarity NPC471093
0.8448 Intermediate Similarity NPC471965
0.844 Intermediate Similarity NPC272576
0.844 Intermediate Similarity NPC471094
0.844 Intermediate Similarity NPC63841
0.844 Intermediate Similarity NPC473410
0.844 Intermediate Similarity NPC469984
0.8435 Intermediate Similarity NPC471406
0.8403 Intermediate Similarity NPC188291
0.8393 Intermediate Similarity NPC178981
0.839 Intermediate Similarity NPC47113
0.839 Intermediate Similarity NPC174367
0.8378 Intermediate Similarity NPC213320
0.8378 Intermediate Similarity NPC263827
0.8378 Intermediate Similarity NPC29505
0.8378 Intermediate Similarity NPC250481
0.8378 Intermediate Similarity NPC285410
0.8376 Intermediate Similarity NPC478066
0.8376 Intermediate Similarity NPC14617
0.8376 Intermediate Similarity NPC262199
0.8376 Intermediate Similarity NPC471964
0.8376 Intermediate Similarity NPC202666
0.8376 Intermediate Similarity NPC471961
0.8365 Intermediate Similarity NPC256227
0.8364 Intermediate Similarity NPC102741
0.8364 Intermediate Similarity NPC246205
0.8364 Intermediate Similarity NPC41405
0.8362 Intermediate Similarity NPC470779
0.8362 Intermediate Similarity NPC275675
0.8362 Intermediate Similarity NPC202051
0.8349 Intermediate Similarity NPC186054
0.8349 Intermediate Similarity NPC202524
0.8349 Intermediate Similarity NPC471474
0.8348 Intermediate Similarity NPC9674
0.8348 Intermediate Similarity NPC268958
0.8348 Intermediate Similarity NPC319570
0.8348 Intermediate Similarity NPC19028
0.8347 Intermediate Similarity NPC471855
0.8347 Intermediate Similarity NPC100390
0.8347 Intermediate Similarity NPC254614
0.8333 Intermediate Similarity NPC65523
0.8333 Intermediate Similarity NPC477252
0.8333 Intermediate Similarity NPC13713
0.8333 Intermediate Similarity NPC218970
0.8333 Intermediate Similarity NPC27999
0.8333 Intermediate Similarity NPC477116
0.8333 Intermediate Similarity NPC475036
0.8333 Intermediate Similarity NPC470171
0.8319 Intermediate Similarity NPC472274
0.8319 Intermediate Similarity NPC471398
0.8319 Intermediate Similarity NPC117712
0.8319 Intermediate Similarity NPC470780
0.8305 Intermediate Similarity NPC30188
0.8305 Intermediate Similarity NPC247315
0.8305 Intermediate Similarity NPC471963
0.8305 Intermediate Similarity NPC470477
0.8305 Intermediate Similarity NPC471962
0.8305 Intermediate Similarity NPC473255
0.8305 Intermediate Similarity NPC177820
0.8304 Intermediate Similarity NPC234042
0.8304 Intermediate Similarity NPC152117
0.8304 Intermediate Similarity NPC12046
0.8304 Intermediate Similarity NPC130427
0.8304 Intermediate Similarity NPC116794
0.8304 Intermediate Similarity NPC90769
0.8304 Intermediate Similarity NPC280782
0.8304 Intermediate Similarity NPC477253
0.8304 Intermediate Similarity NPC473352
0.8304 Intermediate Similarity NPC194951
0.8304 Intermediate Similarity NPC474927
0.8304 Intermediate Similarity NPC473397
0.8291 Intermediate Similarity NPC222688
0.8291 Intermediate Similarity NPC40775
0.8291 Intermediate Similarity NPC107966
0.8291 Intermediate Similarity NPC249848
0.8291 Intermediate Similarity NPC235438
0.8288 Intermediate Similarity NPC75747
0.8288 Intermediate Similarity NPC102914
0.8288 Intermediate Similarity NPC85391
0.8288 Intermediate Similarity NPC68419
0.8288 Intermediate Similarity NPC474786
0.8288 Intermediate Similarity NPC5103
0.8288 Intermediate Similarity NPC5284
0.8288 Intermediate Similarity NPC7870
0.8288 Intermediate Similarity NPC320383
0.8288 Intermediate Similarity NPC274507
0.8288 Intermediate Similarity NPC220984
0.8288 Intermediate Similarity NPC199457
0.8288 Intermediate Similarity NPC108709
0.8288 Intermediate Similarity NPC163314
0.8288 Intermediate Similarity NPC137104
0.8288 Intermediate Similarity NPC110139
0.8273 Intermediate Similarity NPC275539

  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 NPC201992 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
0.8376 Intermediate Similarity NPD8328 Phase 3
0.823 Intermediate Similarity NPD4632 Approved
0.8182 Intermediate Similarity NPD6412 Phase 2
0.8174 Intermediate Similarity NPD6009 Approved
0.8151 Intermediate Similarity NPD7492 Approved
0.812 Intermediate Similarity NPD6059 Approved
0.812 Intermediate Similarity NPD6054 Approved
0.812 Intermediate Similarity NPD6319 Approved
0.8099 Intermediate Similarity NPD7736 Approved
0.8091 Intermediate Similarity NPD6675 Approved
0.8091 Intermediate Similarity NPD6402 Approved
0.8091 Intermediate Similarity NPD5739 Approved
0.8091 Intermediate Similarity NPD7128 Approved
0.8083 Intermediate Similarity NPD6616 Approved
0.8051 Intermediate Similarity NPD6015 Approved
0.8051 Intermediate Similarity NPD6016 Approved
0.8036 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD5701 Approved
0.8018 Intermediate Similarity NPD5697 Approved
0.8017 Intermediate Similarity NPD8293 Discontinued
0.8017 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8017 Intermediate Similarity NPD7078 Approved
0.7983 Intermediate Similarity NPD6370 Approved
0.7983 Intermediate Similarity NPD5988 Approved
0.7982 Intermediate Similarity NPD8297 Approved
0.7982 Intermediate Similarity NPD6882 Approved
0.7946 Intermediate Similarity NPD6899 Approved
0.7946 Intermediate Similarity NPD6881 Approved
0.7946 Intermediate Similarity NPD7320 Approved
0.7876 Intermediate Similarity NPD6012 Approved
0.7876 Intermediate Similarity NPD6014 Approved
0.7876 Intermediate Similarity NPD6373 Approved
0.7876 Intermediate Similarity NPD6013 Approved
0.7876 Intermediate Similarity NPD6372 Approved
0.7807 Intermediate Similarity NPD7290 Approved
0.7807 Intermediate Similarity NPD7102 Approved
0.7807 Intermediate Similarity NPD6883 Approved
0.7788 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD6011 Approved
0.7788 Intermediate Similarity NPD6686 Approved
0.7787 Intermediate Similarity NPD7507 Approved
0.7778 Intermediate Similarity NPD4755 Approved
0.7768 Intermediate Similarity NPD6008 Approved
0.775 Intermediate Similarity NPD5983 Phase 2
0.7739 Intermediate Similarity NPD6649 Approved
0.7739 Intermediate Similarity NPD6847 Approved
0.7739 Intermediate Similarity NPD6650 Approved
0.7739 Intermediate Similarity NPD8130 Phase 1
0.7739 Intermediate Similarity NPD6617 Approved
0.7739 Intermediate Similarity NPD6869 Approved
0.7719 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD7748 Approved
0.7652 Intermediate Similarity NPD4634 Approved
0.7642 Intermediate Similarity NPD7515 Phase 2
0.7636 Intermediate Similarity NPD4700 Approved
0.7636 Intermediate Similarity NPD5286 Approved
0.7636 Intermediate Similarity NPD4696 Approved
0.7636 Intermediate Similarity NPD5285 Approved
0.7623 Intermediate Similarity NPD7604 Phase 2
0.7615 Intermediate Similarity NPD7902 Approved
0.76 Intermediate Similarity NPD7319 Approved
0.7586 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7523 Intermediate Similarity NPD4697 Phase 3
0.7523 Intermediate Similarity NPD5221 Approved
0.7523 Intermediate Similarity NPD5222 Approved
0.7523 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD6033 Approved
0.75 Intermediate Similarity NPD5225 Approved
0.75 Intermediate Similarity NPD5211 Phase 2
0.75 Intermediate Similarity NPD4633 Approved
0.75 Intermediate Similarity NPD6336 Discontinued
0.75 Intermediate Similarity NPD5226 Approved
0.75 Intermediate Similarity NPD5224 Approved
0.7479 Intermediate Similarity NPD6274 Approved
0.7455 Intermediate Similarity NPD6083 Phase 2
0.7455 Intermediate Similarity NPD6084 Phase 2
0.7455 Intermediate Similarity NPD5173 Approved
0.7453 Intermediate Similarity NPD5328 Approved
0.7434 Intermediate Similarity NPD5175 Approved
0.7434 Intermediate Similarity NPD5174 Approved
0.7429 Intermediate Similarity NPD3573 Approved
0.7417 Intermediate Similarity NPD7115 Discovery
0.7411 Intermediate Similarity NPD5223 Approved
0.7407 Intermediate Similarity NPD6399 Phase 3
0.7387 Intermediate Similarity NPD4225 Approved
0.7387 Intermediate Similarity NPD7638 Approved
0.7368 Intermediate Similarity NPD5141 Approved
0.735 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD7900 Approved
0.7339 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3618 Phase 1
0.7321 Intermediate Similarity NPD7639 Approved
0.7321 Intermediate Similarity NPD7640 Approved
0.7315 Intermediate Similarity NPD6079 Approved
0.7304 Intermediate Similarity NPD4767 Approved
0.7304 Intermediate Similarity NPD4768 Approved
0.7295 Intermediate Similarity NPD7100 Approved
0.7295 Intermediate Similarity NPD7101 Approved
0.7295 Intermediate Similarity NPD7516 Approved
0.7281 Intermediate Similarity NPD4754 Approved
0.7273 Intermediate Similarity NPD6317 Approved
0.7273 Intermediate Similarity NPD5695 Phase 3
0.7232 Intermediate Similarity NPD5696 Approved
0.7213 Intermediate Similarity NPD6314 Approved
0.7213 Intermediate Similarity NPD7327 Approved
0.7213 Intermediate Similarity NPD6335 Approved
0.7213 Intermediate Similarity NPD6313 Approved
0.7213 Intermediate Similarity NPD7328 Approved
0.72 Intermediate Similarity NPD6067 Discontinued
0.7196 Intermediate Similarity NPD6672 Approved
0.7196 Intermediate Similarity NPD5737 Approved
0.719 Intermediate Similarity NPD6868 Approved
0.7179 Intermediate Similarity NPD5128 Approved
0.7179 Intermediate Similarity NPD4730 Approved
0.7179 Intermediate Similarity NPD4729 Approved
0.7177 Intermediate Similarity NPD8513 Phase 3
0.7177 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD6908 Approved
0.7177 Intermediate Similarity NPD6909 Approved
0.7177 Intermediate Similarity NPD8516 Approved
0.7177 Intermediate Similarity NPD8515 Approved
0.7177 Intermediate Similarity NPD8517 Approved
0.7177 Intermediate Similarity NPD8033 Approved
0.7167 Intermediate Similarity NPD8133 Approved
0.7156 Intermediate Similarity NPD6411 Approved
0.713 Intermediate Similarity NPD4753 Phase 2
0.7115 Intermediate Similarity NPD3667 Approved
0.7097 Intermediate Similarity NPD8377 Approved
0.7097 Intermediate Similarity NPD8294 Approved
0.7094 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD4202 Approved
0.7059 Intermediate Similarity NPD5249 Phase 3
0.7059 Intermediate Similarity NPD5248 Approved
0.7059 Intermediate Similarity NPD5250 Approved
0.7059 Intermediate Similarity NPD5251 Approved
0.7059 Intermediate Similarity NPD5247 Approved
0.704 Intermediate Similarity NPD8296 Approved
0.704 Intermediate Similarity NPD6921 Approved
0.704 Intermediate Similarity NPD7503 Approved
0.704 Intermediate Similarity NPD8380 Approved
0.704 Intermediate Similarity NPD8378 Approved
0.704 Intermediate Similarity NPD8379 Approved
0.704 Intermediate Similarity NPD8335 Approved
0.7037 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5282 Discontinued
0.7009 Intermediate Similarity NPD7146 Approved
0.7009 Intermediate Similarity NPD5330 Approved
0.7009 Intermediate Similarity NPD7521 Approved
0.7009 Intermediate Similarity NPD7334 Approved
0.7009 Intermediate Similarity NPD6684 Approved
0.7009 Intermediate Similarity NPD6409 Approved
0.7 Intermediate Similarity NPD5215 Approved
0.7 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5217 Approved
0.7 Intermediate Similarity NPD5216 Approved
0.6981 Remote Similarity NPD3133 Approved
0.6981 Remote Similarity NPD3665 Phase 1
0.6981 Remote Similarity NPD3666 Approved
0.6981 Remote Similarity NPD4786 Approved
0.6972 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6972 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6101 Approved
0.6923 Remote Similarity NPD4695 Discontinued
0.6917 Remote Similarity NPD5169 Approved
0.6917 Remote Similarity NPD5135 Approved
0.6917 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6909 Remote Similarity NPD46 Approved
0.6909 Remote Similarity NPD6698 Approved
0.6891 Remote Similarity NPD5168 Approved
0.6881 Remote Similarity NPD6903 Approved
0.687 Remote Similarity NPD5956 Approved
0.686 Remote Similarity NPD5127 Approved
0.6852 Remote Similarity NPD5279 Phase 3
0.6847 Remote Similarity NPD8035 Phase 2
0.6847 Remote Similarity NPD8034 Phase 2
0.6818 Remote Similarity NPD6904 Approved
0.6818 Remote Similarity NPD6673 Approved
0.6818 Remote Similarity NPD7260 Phase 2
0.6818 Remote Similarity NPD6080 Approved
0.6814 Remote Similarity NPD5210 Approved
0.6814 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6814 Remote Similarity NPD4629 Approved
0.6803 Remote Similarity NPD6053 Discontinued
0.6786 Remote Similarity NPD5779 Approved
0.6786 Remote Similarity NPD5778 Approved
0.678 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6769 Remote Similarity NPD8074 Phase 3
0.6759 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7632 Discontinued
0.6696 Remote Similarity NPD5693 Phase 1
0.6694 Remote Similarity NPD5167 Approved
0.6667 Remote Similarity NPD5344 Discontinued
0.6667 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3668 Phase 3
0.6642 Remote Similarity NPD6845 Suspended
0.6642 Remote Similarity NPD6333 Approved
0.6642 Remote Similarity NPD6334 Approved
0.6607 Remote Similarity NPD5692 Phase 3
0.6606 Remote Similarity NPD5329 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