Structure

Physi-Chem Properties

Molecular Weight:  562.24
Volume:  548.231
LogP:  2.003
LogD:  1.104
LogS:  -4.357
# Rotatable Bonds:  8
TPSA:  148.57
# H-Bond Aceptor:  11
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.275
Synthetic Accessibility Score:  6.587
Fsp3:  0.793
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.148
MDCK Permeability:  0.00012475984112825245
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.027
30% Bioavailability (F30%):  0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.832
Plasma Protein Binding (PPB):  53.352806091308594%
Volume Distribution (VD):  0.991
Pgp-substrate:  51.614559173583984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.069
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.196
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.012
CYP2D6-inhibitor:  0.037
CYP2D6-substrate:  0.069
CYP3A4-inhibitor:  0.561
CYP3A4-substrate:  0.266

ADMET: Excretion

Clearance (CL):  3.778
Half-life (T1/2):  0.167

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.927
Drug-inuced Liver Injury (DILI):  0.928
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.286
Maximum Recommended Daily Dose:  0.074
Skin Sensitization:  0.186
Carcinogencity:  0.104
Eye Corrosion:  0.004
Eye Irritation:  0.027
Respiratory Toxicity:  0.313

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

  Natural Product: NPC473798

Natural Product ID:  NPC473798
Common Name*:   APYOGAWRWBDYOS-RUEGVPMCSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  APYOGAWRWBDYOS-RUEGVPMCSA-N
Standard InCHI:  InChI=1S/C29H38O11/c1-8-12(2)25(34)40-20-22-28(7)24(38-15(5)31)19(37-14(4)30)21-27(6)16(13(3)9-17(32)23(27)33)10-18(39-26(20)35)29(21,22)11-36-28/h9,12,16,18-24,33H,8,10-11H2,1-7H3/t12-,16+,18-,19-,20-,21-,22+,23-,24+,27+,28-,29-/m1/s1
SMILES:  CC[C@H](C(=O)O[C@H]1C(=O)O[C@H]2[C@]34[C@@H]1[C@@](C)(OC3)[C@@H](OC(=O)C)[C@@H]([C@@H]4[C@@]1([C@@H](C2)C(=CC(=O)[C@H]1O)C)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL452089
PubChem CID:   44559537
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
NPO33291 simaba orinocensis Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[15165136]

☑ 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 23.8 ug.mL-1 PMID[497623]
NPT916 Cell Line SK-MEL Homo sapiens IC50 > 10.0 ug.mL-1 PMID[497623]
NPT91 Cell Line KB Homo sapiens IC50 > 10.0 ug.mL-1 PMID[497623]
NPT457 Cell Line BT-549 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[497623]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[497623]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 40.0 ug.mL-1 PMID[497623]
NPT1161 Cell Line CHO Cricetulus griseus IC50 = 39.0 ug.mL-1 PMID[497623]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 23.0 ug.mL-1 PMID[497623]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 24.0 ug.mL-1 PMID[497623]
NPT165 Cell Line HeLa Homo sapiens Activity = 100.0 % PMID[497623]
NPT165 Cell Line HeLa Homo sapiens Inhibition = 0.0 % PMID[497623]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3.2 ug.mL-1 PMID[497623]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1.7 ug.mL-1 PMID[497623]
NPT2 Others Unspecified Ratio IC50 > 7.4 n.a. PMID[497623]
NPT2 Others Unspecified Ratio IC50 > 14.0 n.a. PMID[497623]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 > 50.0 ug.mL-1 PMID[497623]
NPT3964 Protein Complex Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 Homo sapiens MIC = 20.8 ug.mL-1 PMID[497623]
NPT2 Others Unspecified Ratio = 1.9 n.a. PMID[497623]
NPT3964 Protein Complex Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 Homo sapiens IC50 > 25.0 ug.mL-1 PMID[497623]
NPT2 Others Unspecified Ratio = 1.0 n.a. PMID[497623]
NPT2 Others Unspecified Activity = 0.42 n.a. PMID[497623]
NPT2 Others Unspecified Activity = 1.34 n.a. PMID[497623]
NPT2 Others Unspecified Activity = 0.52 n.a. PMID[497623]
NPT2 Others Unspecified Activity = 0.87 n.a. PMID[497623]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 > 50.0 ug.mL-1 PMID[497623]

☑ 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 NPC473798 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
0.9906 High Similarity NPC328374
0.9906 High Similarity NPC96312
0.9906 High Similarity NPC251236
0.9906 High Similarity NPC40632
0.9717 High Similarity NPC49451
0.9541 High Similarity NPC17772
0.9537 High Similarity NPC235539
0.9537 High Similarity NPC134869
0.9537 High Similarity NPC152199
0.945 High Similarity NPC97908
0.945 High Similarity NPC122033
0.945 High Similarity NPC470854
0.945 High Similarity NPC287343
0.945 High Similarity NPC474654
0.9444 High Similarity NPC18547
0.9444 High Similarity NPC474906
0.9364 High Similarity NPC297179
0.9358 High Similarity NPC474734
0.9279 High Similarity NPC470777
0.9273 High Similarity NPC473590
0.9259 High Similarity NPC289312
0.9259 High Similarity NPC474516
0.9259 High Similarity NPC11252
0.9245 High Similarity NPC293850
0.9189 High Similarity NPC188667
0.9189 High Similarity NPC204552
0.9182 High Similarity NPC16081
0.9182 High Similarity NPC173686
0.9174 High Similarity NPC7921
0.9174 High Similarity NPC208998
0.9167 High Similarity NPC201992
0.9151 High Similarity NPC3316
0.9151 High Similarity NPC144854
0.9123 High Similarity NPC91693
0.9123 High Similarity NPC105926
0.9123 High Similarity NPC265557
0.9123 High Similarity NPC67251
0.9123 High Similarity NPC18945
0.9115 High Similarity NPC477046
0.9115 High Similarity NPC102822
0.9091 High Similarity NPC45218
0.9091 High Similarity NPC323821
0.9091 High Similarity NPC268238
0.9091 High Similarity NPC143268
0.9065 High Similarity NPC277017
0.9065 High Similarity NPC154608
0.9065 High Similarity NPC192813
0.9043 High Similarity NPC24651
0.9043 High Similarity NPC476729
0.9035 High Similarity NPC312833
0.9027 High Similarity NPC112038
0.9027 High Similarity NPC107338
0.9027 High Similarity NPC109607
0.9018 High Similarity NPC470776
0.9018 High Similarity NPC251310
0.9009 High Similarity NPC470628
0.9009 High Similarity NPC259306
0.9009 High Similarity NPC474046
0.9009 High Similarity NPC207217
0.9 High Similarity NPC51978
0.8991 High Similarity NPC146945
0.8991 High Similarity NPC171888
0.8947 High Similarity NPC470779
0.8938 High Similarity NPC469488
0.8938 High Similarity NPC475775
0.8938 High Similarity NPC476529
0.8929 High Similarity NPC176513
0.8929 High Similarity NPC470775
0.8919 High Similarity NPC469877
0.8919 High Similarity NPC470919
0.8879 High Similarity NPC470922
0.8879 High Similarity NPC102352
0.8807 High Similarity NPC27814
0.8793 High Similarity NPC227397
0.8785 High Similarity NPC65523
0.8762 High Similarity NPC472972
0.8761 High Similarity NPC309433
0.8739 High Similarity NPC472002
0.8739 High Similarity NPC90769
0.8739 High Similarity NPC302146
0.8727 High Similarity NPC210005
0.8707 High Similarity NPC222688
0.8704 High Similarity NPC181357
0.8692 High Similarity NPC275583
0.8673 High Similarity NPC179626
0.8661 High Similarity NPC194100
0.8661 High Similarity NPC198539
0.8655 High Similarity NPC188291
0.8636 High Similarity NPC141350
0.8636 High Similarity NPC310546
0.8621 High Similarity NPC275675
0.8596 High Similarity NPC470778
0.8596 High Similarity NPC473968
0.8596 High Similarity NPC146432
0.8595 High Similarity NPC100390
0.8595 High Similarity NPC254614
0.8571 High Similarity NPC476008
0.8571 High Similarity NPC280782
0.8559 High Similarity NPC473255
0.8545 High Similarity NPC94942
0.8509 High Similarity NPC213084
0.8509 High Similarity NPC190185
0.8509 High Similarity NPC89929
0.85 High Similarity NPC295220
0.85 High Similarity NPC475636
0.8496 Intermediate Similarity NPC25909
0.8496 Intermediate Similarity NPC94509
0.8487 Intermediate Similarity NPC477745
0.8487 Intermediate Similarity NPC285091
0.8487 Intermediate Similarity NPC87662
0.8482 Intermediate Similarity NPC469656
0.8482 Intermediate Similarity NPC469655
0.8482 Intermediate Similarity NPC157476
0.8482 Intermediate Similarity NPC34315
0.8482 Intermediate Similarity NPC474846
0.8468 Intermediate Similarity NPC474242
0.8468 Intermediate Similarity NPC472534
0.8468 Intermediate Similarity NPC143706
0.8455 Intermediate Similarity NPC59530
0.8455 Intermediate Similarity NPC230541
0.8448 Intermediate Similarity NPC473920
0.8448 Intermediate Similarity NPC279143
0.8448 Intermediate Similarity NPC127530
0.8443 Intermediate Similarity NPC102316
0.844 Intermediate Similarity NPC475036
0.843 Intermediate Similarity NPC54614
0.843 Intermediate Similarity NPC309096
0.8421 Intermediate Similarity NPC299849
0.8421 Intermediate Similarity NPC117712
0.8421 Intermediate Similarity NPC247069
0.8421 Intermediate Similarity NPC243354
0.8417 Intermediate Similarity NPC470882
0.8417 Intermediate Similarity NPC470780
0.8407 Intermediate Similarity NPC193948
0.84 Intermediate Similarity NPC596
0.8393 Intermediate Similarity NPC253906
0.8393 Intermediate Similarity NPC100908
0.8393 Intermediate Similarity NPC474567
0.839 Intermediate Similarity NPC471965
0.839 Intermediate Similarity NPC65858
0.8387 Intermediate Similarity NPC262813
0.8381 Intermediate Similarity NPC477438
0.8381 Intermediate Similarity NPC477437
0.8378 Intermediate Similarity NPC476479
0.8378 Intermediate Similarity NPC189075
0.8378 Intermediate Similarity NPC275539
0.8376 Intermediate Similarity NPC109973
0.8376 Intermediate Similarity NPC478051
0.8376 Intermediate Similarity NPC471406
0.8364 Intermediate Similarity NPC477877
0.8362 Intermediate Similarity NPC21326
0.8348 Intermediate Similarity NPC270958
0.8348 Intermediate Similarity NPC266728
0.8348 Intermediate Similarity NPC49492
0.8333 Intermediate Similarity NPC225049
0.8333 Intermediate Similarity NPC202889
0.8333 Intermediate Similarity NPC181999
0.8333 Intermediate Similarity NPC255017
0.8333 Intermediate Similarity NPC477266
0.8333 Intermediate Similarity NPC471204
0.8333 Intermediate Similarity NPC250109
0.8333 Intermediate Similarity NPC194273
0.8333 Intermediate Similarity NPC118964
0.8333 Intermediate Similarity NPC962
0.832 Intermediate Similarity NPC251998
0.832 Intermediate Similarity NPC190065
0.832 Intermediate Similarity NPC141215
0.832 Intermediate Similarity NPC471089
0.8319 Intermediate Similarity NPC478066
0.8319 Intermediate Similarity NPC135038
0.8319 Intermediate Similarity NPC14617
0.8319 Intermediate Similarity NPC43252
0.8319 Intermediate Similarity NPC188738
0.8319 Intermediate Similarity NPC471964
0.8319 Intermediate Similarity NPC262199
0.8319 Intermediate Similarity NPC471961
0.8319 Intermediate Similarity NPC267822
0.8319 Intermediate Similarity NPC471243
0.8319 Intermediate Similarity NPC202666
0.8305 Intermediate Similarity NPC75417
0.8304 Intermediate Similarity NPC41405
0.8293 Intermediate Similarity NPC471855
0.8293 Intermediate Similarity NPC33378
0.8293 Intermediate Similarity NPC6274
0.8293 Intermediate Similarity NPC254146
0.8291 Intermediate Similarity NPC475041
0.8291 Intermediate Similarity NPC319570
0.8288 Intermediate Similarity NPC293512
0.8288 Intermediate Similarity NPC202524
0.8288 Intermediate Similarity NPC110496
0.8286 Intermediate Similarity NPC477439
0.8279 Intermediate Similarity NPC264192
0.8276 Intermediate Similarity NPC469684
0.8276 Intermediate Similarity NPC27999
0.8276 Intermediate Similarity NPC477116
0.8273 Intermediate Similarity NPC301787
0.8273 Intermediate Similarity NPC471293
0.8264 Intermediate Similarity NPC473265
0.8261 Intermediate Similarity NPC475633
0.8261 Intermediate Similarity NPC102088

  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 NPC473798 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
0.8468 Intermediate Similarity NPD6372 Approved
0.8468 Intermediate Similarity NPD6373 Approved
0.8407 Intermediate Similarity NPD8297 Approved
0.8364 Intermediate Similarity NPD5739 Approved
0.8364 Intermediate Similarity NPD6402 Approved
0.8364 Intermediate Similarity NPD7128 Approved
0.8364 Intermediate Similarity NPD6675 Approved
0.8319 Intermediate Similarity NPD6650 Approved
0.8319 Intermediate Similarity NPD6649 Approved
0.8319 Intermediate Similarity NPD8328 Phase 3
0.822 Intermediate Similarity NPD6319 Approved
0.8214 Intermediate Similarity NPD6899 Approved
0.8214 Intermediate Similarity NPD6881 Approved
0.8214 Intermediate Similarity NPD7320 Approved
0.8125 Intermediate Similarity NPD5701 Approved
0.8125 Intermediate Similarity NPD5697 Approved
0.8099 Intermediate Similarity NPD7492 Approved
0.8087 Intermediate Similarity NPD6882 Approved
0.807 Intermediate Similarity NPD7102 Approved
0.807 Intermediate Similarity NPD7290 Approved
0.807 Intermediate Similarity NPD6883 Approved
0.8067 Intermediate Similarity NPD6054 Approved
0.8067 Intermediate Similarity NPD6059 Approved
0.8053 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD7736 Approved
0.8033 Intermediate Similarity NPD6616 Approved
0.8017 Intermediate Similarity NPD4632 Approved
0.8 Intermediate Similarity NPD6869 Approved
0.8 Intermediate Similarity NPD8130 Phase 1
0.8 Intermediate Similarity NPD6617 Approved
0.8 Intermediate Similarity NPD6847 Approved
0.7982 Intermediate Similarity NPD6013 Approved
0.7982 Intermediate Similarity NPD6014 Approved
0.7982 Intermediate Similarity NPD6012 Approved
0.7967 Intermediate Similarity NPD7078 Approved
0.7967 Intermediate Similarity NPD8293 Discontinued
0.7966 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD6009 Approved
0.7934 Intermediate Similarity NPD6370 Approved
0.7895 Intermediate Similarity NPD6011 Approved
0.7876 Intermediate Similarity NPD6008 Approved
0.7869 Intermediate Similarity NPD7604 Phase 2
0.7851 Intermediate Similarity NPD6016 Approved
0.7851 Intermediate Similarity NPD6015 Approved
0.7851 Intermediate Similarity NPD5983 Phase 2
0.7845 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7787 Intermediate Similarity NPD5988 Approved
0.7759 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD6336 Discontinued
0.7727 Intermediate Similarity NPD6083 Phase 2
0.7727 Intermediate Similarity NPD7902 Approved
0.7727 Intermediate Similarity NPD4755 Approved
0.7727 Intermediate Similarity NPD6084 Phase 2
0.7672 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7652 Intermediate Similarity NPD6412 Phase 2
0.7615 Intermediate Similarity NPD7748 Approved
0.76 Intermediate Similarity NPD7507 Approved
0.7593 Intermediate Similarity NPD7515 Phase 2
0.7589 Intermediate Similarity NPD5286 Approved
0.7589 Intermediate Similarity NPD4700 Approved
0.7589 Intermediate Similarity NPD4696 Approved
0.7589 Intermediate Similarity NPD5285 Approved
0.7583 Intermediate Similarity NPD6274 Approved
0.7559 Intermediate Similarity NPD7319 Approved
0.7541 Intermediate Similarity NPD7100 Approved
0.7541 Intermediate Similarity NPD7101 Approved
0.7523 Intermediate Similarity NPD6399 Phase 3
0.7521 Intermediate Similarity NPD7115 Discovery
0.75 Intermediate Similarity NPD5696 Approved
0.75 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD6033 Approved
0.7477 Intermediate Similarity NPD4697 Phase 3
0.7459 Intermediate Similarity NPD6335 Approved
0.7458 Intermediate Similarity NPD4634 Approved
0.7456 Intermediate Similarity NPD5224 Approved
0.7456 Intermediate Similarity NPD5211 Phase 2
0.7456 Intermediate Similarity NPD5225 Approved
0.7456 Intermediate Similarity NPD5226 Approved
0.7456 Intermediate Similarity NPD4633 Approved
0.7455 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD7900 Approved
0.7436 Intermediate Similarity NPD6686 Approved
0.7419 Intermediate Similarity NPD6909 Approved
0.7419 Intermediate Similarity NPD6908 Approved
0.7419 Intermediate Similarity NPD6921 Approved
0.7414 Intermediate Similarity NPD4768 Approved
0.7414 Intermediate Similarity NPD4767 Approved
0.7407 Intermediate Similarity NPD5328 Approved
0.7391 Intermediate Similarity NPD5175 Approved
0.7391 Intermediate Similarity NPD5174 Approved
0.7387 Intermediate Similarity NPD5695 Phase 3
0.7383 Intermediate Similarity NPD3573 Approved
0.7377 Intermediate Similarity NPD6317 Approved
0.7368 Intermediate Similarity NPD5223 Approved
0.7345 Intermediate Similarity NPD7638 Approved
0.7328 Intermediate Similarity NPD5141 Approved
0.7321 Intermediate Similarity NPD5222 Approved
0.7321 Intermediate Similarity NPD5221 Approved
0.7321 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6314 Approved
0.7317 Intermediate Similarity NPD6313 Approved
0.7315 Intermediate Similarity NPD6672 Approved
0.7315 Intermediate Similarity NPD5737 Approved
0.7295 Intermediate Similarity NPD6868 Approved
0.729 Intermediate Similarity NPD3618 Phase 1
0.7288 Intermediate Similarity NPD4730 Approved
0.7288 Intermediate Similarity NPD4729 Approved
0.7281 Intermediate Similarity NPD7639 Approved
0.7281 Intermediate Similarity NPD7640 Approved
0.728 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6079 Approved
0.7258 Intermediate Similarity NPD7516 Approved
0.7257 Intermediate Similarity NPD5173 Approved
0.7241 Intermediate Similarity NPD4754 Approved
0.7193 Intermediate Similarity NPD4225 Approved
0.7177 Intermediate Similarity NPD7327 Approved
0.7177 Intermediate Similarity NPD7328 Approved
0.7167 Intermediate Similarity NPD5248 Approved
0.7167 Intermediate Similarity NPD5250 Approved
0.7167 Intermediate Similarity NPD5247 Approved
0.7167 Intermediate Similarity NPD5251 Approved
0.7167 Intermediate Similarity NPD5249 Phase 3
0.7143 Intermediate Similarity NPD8515 Approved
0.7143 Intermediate Similarity NPD5128 Approved
0.7143 Intermediate Similarity NPD8513 Phase 3
0.7143 Intermediate Similarity NPD8517 Approved
0.7143 Intermediate Similarity NPD8516 Approved
0.7143 Intermediate Similarity NPD5282 Discontinued
0.7117 Intermediate Similarity NPD6411 Approved
0.7091 Intermediate Similarity NPD6904 Approved
0.7091 Intermediate Similarity NPD4753 Phase 2
0.7091 Intermediate Similarity NPD6080 Approved
0.7091 Intermediate Similarity NPD6673 Approved
0.708 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD4202 Approved
0.7045 Intermediate Similarity NPD7260 Phase 2
0.7008 Intermediate Similarity NPD8379 Approved
0.7008 Intermediate Similarity NPD8033 Approved
0.7008 Intermediate Similarity NPD8296 Approved
0.7008 Intermediate Similarity NPD8335 Approved
0.7008 Intermediate Similarity NPD8380 Approved
0.7008 Intermediate Similarity NPD8378 Approved
0.7 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8133 Approved
0.6972 Remote Similarity NPD7334 Approved
0.6972 Remote Similarity NPD6409 Approved
0.6972 Remote Similarity NPD7146 Approved
0.6972 Remote Similarity NPD5330 Approved
0.6972 Remote Similarity NPD6684 Approved
0.6972 Remote Similarity NPD7521 Approved
0.6967 Remote Similarity NPD5215 Approved
0.6967 Remote Similarity NPD5217 Approved
0.6967 Remote Similarity NPD5216 Approved
0.6967 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6964 Remote Similarity NPD8034 Phase 2
0.6964 Remote Similarity NPD8035 Phase 2
0.6944 Remote Similarity NPD4786 Approved
0.6937 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6101 Approved
0.693 Remote Similarity NPD4629 Approved
0.693 Remote Similarity NPD5210 Approved
0.6929 Remote Similarity NPD8377 Approved
0.6929 Remote Similarity NPD8294 Approved
0.6916 Remote Similarity NPD3667 Approved
0.6911 Remote Similarity NPD6053 Discontinued
0.6899 Remote Similarity NPD6067 Discontinued
0.6885 Remote Similarity NPD5135 Approved
0.6885 Remote Similarity NPD5169 Approved
0.6885 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6875 Remote Similarity NPD46 Approved
0.6875 Remote Similarity NPD7503 Approved
0.6875 Remote Similarity NPD6698 Approved
0.6866 Remote Similarity NPD6845 Suspended
0.6847 Remote Similarity NPD6903 Approved
0.6829 Remote Similarity NPD5127 Approved
0.6818 Remote Similarity NPD6098 Approved
0.6814 Remote Similarity NPD5693 Phase 1
0.6814 Remote Similarity NPD6050 Approved
0.6789 Remote Similarity NPD3666 Approved
0.6789 Remote Similarity NPD3133 Approved
0.6789 Remote Similarity NPD3665 Phase 1
0.678 Remote Similarity NPD5344 Discontinued
0.6777 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5779 Approved
0.6754 Remote Similarity NPD5778 Approved
0.6742 Remote Similarity NPD8074 Phase 3
0.6729 Remote Similarity NPD4695 Discontinued
0.6727 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5329 Approved
0.6726 Remote Similarity NPD5692 Phase 3
0.6723 Remote Similarity NPD7632 Discontinued
0.6721 Remote Similarity NPD5168 Approved
0.6716 Remote Similarity NPD5956 Approved
0.6696 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD5281 Approved
0.6667 Remote Similarity NPD5167 Approved
0.6667 Remote Similarity NPD5694 Approved
0.6667 Remote Similarity NPD5284 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