Structure

Physi-Chem Properties

Molecular Weight:  520.3
Volume:  529.77
LogP:  1.784
LogD:  0.41
LogS:  -3.526
# Rotatable Bonds:  4
TPSA:  144.52
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.28
Synthetic Accessibility Score:  5.719
Fsp3:  0.862
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.025
MDCK Permeability:  3.5341658076504245e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.045
20% Bioavailability (F20%):  0.248
30% Bioavailability (F30%):  0.23

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.162
Plasma Protein Binding (PPB):  61.461769104003906%
Volume Distribution (VD):  1.033
Pgp-substrate:  22.958370208740234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.479
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.78
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.073
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.036
CYP3A4-inhibitor:  0.652
CYP3A4-substrate:  0.765

ADMET: Excretion

Clearance (CL):  2.73
Half-life (T1/2):  0.303

ADMET: Toxicity

hERG Blockers:  0.087
Human Hepatotoxicity (H-HT):  0.337
Drug-inuced Liver Injury (DILI):  0.106
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.473
Maximum Recommended Daily Dose:  0.938
Skin Sensitization:  0.163
Carcinogencity:  0.073
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.915

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

  Natural Product: NPC266728

Natural Product ID:  NPC266728
Common Name*:   (3S,4S,5R)-4-[(2R,3R)-2,3-Dihydroxy-3-[(2S,3R,5R,10R,13R,14S)-2,3,14-Trihydroxy-10,13-Dimethyl-6-Oxo-2,3,4,5,9,11,12,15,16,17-Decahydro-1H-Cyclopenta[A]Phenanthren-17-Yl]Butyl]-3,5-Dimethyloxolan-2-One
IUPAC Name:   (3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5R,10R,13R,14S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one
Synonyms:  
Standard InCHIKey:  NEFYSBQJYCICOG-VHVOLZJXSA-N
Standard InCHI:  InChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17?,19-,21+,22-,23?,24+,26+,27+,28+,29+/m0/s1
SMILES:  C[C@H]1[C@H](C[C@H]([C@@](C)(C2CC[C@]3(C4=CC(=O)[C@@H]5C[C@H]([C@H](C[C@]5(C)C4CC[C@]23C)O)O)O)O)O)[C@@H](C)OC1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1736717
PubChem CID:   44201988
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota flowering whole plant n.a. n.a. PMID[10425119]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15043410]
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[21682262]
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota whole plants Zhejiang Province, China 2008-AUG PMID[21682262]
NPO16818 Trillium tschonoskii Species Melanthiaceae Eukaryota n.a. n.a. n.a. PMID[32870000]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[9748375]
NPO2775 Cyathula officinalis Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16818 Trillium tschonoskii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3975 Cyathula capitata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11283 Ajuga chamaepitys Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7849 Ajuga taiwanensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6471 Trillium camtschaticum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6471 Trillium camtschaticum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2775 Cyathula officinalis Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16818 Trillium tschonoskii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7849 Ajuga taiwanensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11283 Ajuga chamaepitys Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3975 Cyathula capitata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3975 Cyathula capitata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11283 Ajuga chamaepitys Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16818 Trillium tschonoskii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2775 Cyathula officinalis Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6471 Trillium camtschaticum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2775 Cyathula officinalis Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6471 Trillium camtschaticum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7849 Ajuga taiwanensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2775 Cyathula officinalis Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16818 Trillium tschonoskii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11283 Ajuga chamaepitys Species Lamiaceae 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
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 16353.5 nM PMID[565993]

☑ 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 NPC266728 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 NPC49492
0.9811 High Similarity NPC962
0.9636 High Similarity NPC109973
0.9626 High Similarity NPC250109
0.9464 High Similarity NPC222688
0.9358 High Similarity NPC326542
0.9352 High Similarity NPC207251
0.9196 High Similarity NPC475041
0.9167 High Similarity NPC76084
0.9151 High Similarity NPC152695
0.9151 High Similarity NPC50692
0.9151 High Similarity NPC202167
0.9151 High Similarity NPC85829
0.9151 High Similarity NPC48733
0.9151 High Similarity NPC260268
0.9151 High Similarity NPC150531
0.9151 High Similarity NPC97202
0.9151 High Similarity NPC476027
0.9151 High Similarity NPC319077
0.9151 High Similarity NPC214264
0.9151 High Similarity NPC296945
0.9151 High Similarity NPC49958
0.9151 High Similarity NPC302607
0.9151 High Similarity NPC171137
0.9123 High Similarity NPC269642
0.9091 High Similarity NPC317210
0.9074 High Similarity NPC11710
0.9065 High Similarity NPC220229
0.9065 High Similarity NPC475060
0.9065 High Similarity NPC83744
0.9057 High Similarity NPC209502
0.9057 High Similarity NPC204833
0.8981 High Similarity NPC329417
0.8981 High Similarity NPC217201
0.8972 High Similarity NPC149047
0.8962 High Similarity NPC140723
0.8929 High Similarity NPC196931
0.8919 High Similarity NPC52634
0.8889 High Similarity NPC477916
0.8868 High Similarity NPC477915
0.885 High Similarity NPC471854
0.8829 High Similarity NPC280782
0.8814 High Similarity NPC470882
0.8796 High Similarity NPC323834
0.8793 High Similarity NPC28532
0.875 High Similarity NPC73300
0.875 High Similarity NPC108721
0.8739 High Similarity NPC473888
0.8716 High Similarity NPC230541
0.8716 High Similarity NPC59530
0.8704 High Similarity NPC471293
0.8692 High Similarity NPC22388
0.8679 High Similarity NPC218383
0.8679 High Similarity NPC154072
0.8667 High Similarity NPC231529
0.8661 High Similarity NPC472002
0.8655 High Similarity NPC473265
0.8624 High Similarity NPC102352
0.8624 High Similarity NPC96377
0.8609 High Similarity NPC311554
0.8609 High Similarity NPC257457
0.8571 High Similarity NPC188738
0.8559 High Similarity NPC141350
0.8559 High Similarity NPC473979
0.8545 High Similarity NPC144854
0.8545 High Similarity NPC3316
0.8545 High Similarity NPC473037
0.8532 High Similarity NPC28656
0.8532 High Similarity NPC255309
0.8522 High Similarity NPC284068
0.8519 High Similarity NPC136289
0.8512 High Similarity NPC470880
0.8509 High Similarity NPC117712
0.8509 High Similarity NPC471398
0.8509 High Similarity NPC178289
0.8505 High Similarity NPC476274
0.85 High Similarity NPC473253
0.8496 Intermediate Similarity NPC126691
0.8491 Intermediate Similarity NPC475894
0.8487 Intermediate Similarity NPC473255
0.8487 Intermediate Similarity NPC8369
0.8482 Intermediate Similarity NPC473036
0.8482 Intermediate Similarity NPC197428
0.8482 Intermediate Similarity NPC272898
0.8468 Intermediate Similarity NPC88701
0.8468 Intermediate Similarity NPC258323
0.8468 Intermediate Similarity NPC192813
0.8468 Intermediate Similarity NPC472218
0.8468 Intermediate Similarity NPC19412
0.8468 Intermediate Similarity NPC277017
0.8468 Intermediate Similarity NPC472219
0.8468 Intermediate Similarity NPC154608
0.8468 Intermediate Similarity NPC65941
0.8468 Intermediate Similarity NPC472217
0.8462 Intermediate Similarity NPC474585
0.8455 Intermediate Similarity NPC196528
0.8455 Intermediate Similarity NPC231530
0.8455 Intermediate Similarity NPC278628
0.844 Intermediate Similarity NPC36688
0.844 Intermediate Similarity NPC236390
0.844 Intermediate Similarity NPC474775
0.844 Intermediate Similarity NPC55872
0.8435 Intermediate Similarity NPC474734
0.8435 Intermediate Similarity NPC96312
0.8435 Intermediate Similarity NPC251236
0.8435 Intermediate Similarity NPC138372
0.8435 Intermediate Similarity NPC40632
0.8435 Intermediate Similarity NPC148458
0.8435 Intermediate Similarity NPC106228
0.8435 Intermediate Similarity NPC270958
0.8435 Intermediate Similarity NPC328374
0.8435 Intermediate Similarity NPC190286
0.843 Intermediate Similarity NPC311534
0.8426 Intermediate Similarity NPC81530
0.8426 Intermediate Similarity NPC476240
0.8426 Intermediate Similarity NPC476223
0.8426 Intermediate Similarity NPC224720
0.8421 Intermediate Similarity NPC49451
0.8421 Intermediate Similarity NPC202889
0.8421 Intermediate Similarity NPC194100
0.8421 Intermediate Similarity NPC25909
0.8421 Intermediate Similarity NPC178981
0.8417 Intermediate Similarity NPC293112
0.8417 Intermediate Similarity NPC47113
0.8417 Intermediate Similarity NPC174367
0.8411 Intermediate Similarity NPC153792
0.8411 Intermediate Similarity NPC271387
0.8403 Intermediate Similarity NPC469789
0.8403 Intermediate Similarity NPC27363
0.8393 Intermediate Similarity NPC214644
0.8393 Intermediate Similarity NPC475941
0.8393 Intermediate Similarity NPC474901
0.839 Intermediate Similarity NPC46570
0.8378 Intermediate Similarity NPC220974
0.8376 Intermediate Similarity NPC61520
0.8376 Intermediate Similarity NPC230513
0.8376 Intermediate Similarity NPC19028
0.8376 Intermediate Similarity NPC5292
0.8376 Intermediate Similarity NPC9674
0.8376 Intermediate Similarity NPC473203
0.8374 Intermediate Similarity NPC471855
0.8364 Intermediate Similarity NPC29705
0.8362 Intermediate Similarity NPC473968
0.8362 Intermediate Similarity NPC55296
0.8349 Intermediate Similarity NPC473928
0.8349 Intermediate Similarity NPC204450
0.8349 Intermediate Similarity NPC195290
0.8349 Intermediate Similarity NPC473424
0.8348 Intermediate Similarity NPC473798
0.8348 Intermediate Similarity NPC474181
0.8333 Intermediate Similarity NPC316964
0.8333 Intermediate Similarity NPC71348
0.8333 Intermediate Similarity NPC172154
0.8333 Intermediate Similarity NPC81736
0.8333 Intermediate Similarity NPC474516
0.8333 Intermediate Similarity NPC269530
0.8333 Intermediate Similarity NPC476729
0.8319 Intermediate Similarity NPC5284
0.8319 Intermediate Similarity NPC65858
0.8319 Intermediate Similarity NPC107493
0.8319 Intermediate Similarity NPC23786
0.8319 Intermediate Similarity NPC470265
0.8319 Intermediate Similarity NPC6206
0.8318 Intermediate Similarity NPC107243
0.8306 Intermediate Similarity NPC88668
0.8305 Intermediate Similarity NPC79579
0.8305 Intermediate Similarity NPC472004
0.8305 Intermediate Similarity NPC476961
0.8304 Intermediate Similarity NPC472825
0.8304 Intermediate Similarity NPC275539
0.8304 Intermediate Similarity NPC189075
0.8304 Intermediate Similarity NPC94529
0.8302 Intermediate Similarity NPC271195
0.8293 Intermediate Similarity NPC253456
0.8293 Intermediate Similarity NPC159338
0.8293 Intermediate Similarity NPC16569
0.8291 Intermediate Similarity NPC118638
0.8291 Intermediate Similarity NPC329736
0.8291 Intermediate Similarity NPC153440
0.8291 Intermediate Similarity NPC251310
0.8288 Intermediate Similarity NPC186668
0.8276 Intermediate Similarity NPC235539
0.8276 Intermediate Similarity NPC179626
0.8276 Intermediate Similarity NPC207217
0.8276 Intermediate Similarity NPC134869
0.8276 Intermediate Similarity NPC469794
0.8276 Intermediate Similarity NPC176840
0.8276 Intermediate Similarity NPC474046
0.8276 Intermediate Similarity NPC72772
0.8276 Intermediate Similarity NPC259306
0.8276 Intermediate Similarity NPC470628
0.8276 Intermediate Similarity NPC152199
0.8273 Intermediate Similarity NPC472821
0.8273 Intermediate Similarity NPC478057
0.8273 Intermediate Similarity NPC191892
0.8264 Intermediate Similarity NPC473635
0.8264 Intermediate Similarity NPC469750
0.8264 Intermediate Similarity NPC250556
0.8264 Intermediate Similarity NPC15095
0.8261 Intermediate Similarity NPC51978

  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 NPC266728 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
0.8624 High Similarity NPD6008 Approved
0.8559 High Similarity NPD6373 Approved
0.8559 High Similarity NPD6372 Approved
0.8468 Intermediate Similarity NPD7320 Approved
0.8455 Intermediate Similarity NPD7128 Approved
0.8455 Intermediate Similarity NPD6675 Approved
0.8455 Intermediate Similarity NPD6402 Approved
0.8455 Intermediate Similarity NPD5739 Approved
0.8421 Intermediate Similarity NPD4632 Approved
0.8407 Intermediate Similarity NPD6650 Approved
0.8407 Intermediate Similarity NPD6649 Approved
0.8333 Intermediate Similarity NPD8297 Approved
0.8305 Intermediate Similarity NPD6319 Approved
0.8304 Intermediate Similarity NPD6899 Approved
0.8304 Intermediate Similarity NPD6881 Approved
0.8264 Intermediate Similarity NPD7507 Approved
0.8214 Intermediate Similarity NPD5697 Approved
0.8214 Intermediate Similarity NPD5701 Approved
0.8182 Intermediate Similarity NPD7492 Approved
0.8174 Intermediate Similarity NPD6882 Approved
0.8165 Intermediate Similarity NPD7639 Approved
0.8165 Intermediate Similarity NPD7640 Approved
0.8158 Intermediate Similarity NPD7102 Approved
0.8158 Intermediate Similarity NPD7290 Approved
0.8158 Intermediate Similarity NPD6883 Approved
0.8151 Intermediate Similarity NPD6054 Approved
0.8151 Intermediate Similarity NPD6059 Approved
0.8142 Intermediate Similarity NPD6011 Approved
0.8115 Intermediate Similarity NPD6616 Approved
0.8087 Intermediate Similarity NPD6869 Approved
0.8087 Intermediate Similarity NPD6617 Approved
0.8087 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.8087 Intermediate Similarity NPD8130 Phase 1
0.8087 Intermediate Similarity NPD6847 Approved
0.8073 Intermediate Similarity NPD7638 Approved
0.807 Intermediate Similarity NPD6013 Approved
0.807 Intermediate Similarity NPD6012 Approved
0.807 Intermediate Similarity NPD6014 Approved
0.8065 Intermediate Similarity NPD7319 Approved
0.8051 Intermediate Similarity NPD6009 Approved
0.8049 Intermediate Similarity NPD7078 Approved
0.8049 Intermediate Similarity NPD8293 Discontinued
0.8018 Intermediate Similarity NPD5211 Phase 2
0.8017 Intermediate Similarity NPD6370 Approved
0.7984 Intermediate Similarity NPD7736 Approved
0.7982 Intermediate Similarity NPD4755 Approved
0.7963 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7951 Intermediate Similarity NPD7604 Phase 2
0.7934 Intermediate Similarity NPD6015 Approved
0.7934 Intermediate Similarity NPD6016 Approved
0.7934 Intermediate Similarity NPD5983 Phase 2
0.7899 Intermediate Similarity NPD7115 Discovery
0.7876 Intermediate Similarity NPD5141 Approved
0.7869 Intermediate Similarity NPD5988 Approved
0.7845 Intermediate Similarity NPD4634 Approved
0.7838 Intermediate Similarity NPD4700 Approved
0.7838 Intermediate Similarity NPD4696 Approved
0.7838 Intermediate Similarity NPD5286 Approved
0.7838 Intermediate Similarity NPD5285 Approved
0.783 Intermediate Similarity NPD5328 Approved
0.7823 Intermediate Similarity NPD6336 Discontinued
0.7818 Intermediate Similarity NPD6084 Phase 2
0.7818 Intermediate Similarity NPD6083 Phase 2
0.7787 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6399 Phase 3
0.7778 Intermediate Similarity NPD4202 Approved
0.7769 Intermediate Similarity NPD7516 Approved
0.7768 Intermediate Similarity NPD5223 Approved
0.7739 Intermediate Similarity NPD6412 Phase 2
0.7712 Intermediate Similarity NPD6053 Discontinued
0.7699 Intermediate Similarity NPD5224 Approved
0.7699 Intermediate Similarity NPD5225 Approved
0.7699 Intermediate Similarity NPD4633 Approved
0.7699 Intermediate Similarity NPD5226 Approved
0.7698 Intermediate Similarity NPD6033 Approved
0.7686 Intermediate Similarity NPD7328 Approved
0.7686 Intermediate Similarity NPD6335 Approved
0.7686 Intermediate Similarity NPD7327 Approved
0.7685 Intermediate Similarity NPD6079 Approved
0.7667 Intermediate Similarity NPD6274 Approved
0.7652 Intermediate Similarity NPD4768 Approved
0.7652 Intermediate Similarity NPD4767 Approved
0.7632 Intermediate Similarity NPD4754 Approved
0.7632 Intermediate Similarity NPD5174 Approved
0.7632 Intermediate Similarity NPD5175 Approved
0.7623 Intermediate Similarity NPD7100 Approved
0.7623 Intermediate Similarity NPD7101 Approved
0.7607 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD6317 Approved
0.7589 Intermediate Similarity NPD5696 Approved
0.757 Intermediate Similarity NPD6903 Approved
0.7568 Intermediate Similarity NPD4697 Phase 3
0.7561 Intermediate Similarity NPD8377 Approved
0.7561 Intermediate Similarity NPD8294 Approved
0.7547 Intermediate Similarity NPD7521 Approved
0.7547 Intermediate Similarity NPD7334 Approved
0.7547 Intermediate Similarity NPD5330 Approved
0.7547 Intermediate Similarity NPD3618 Phase 1
0.7547 Intermediate Similarity NPD6684 Approved
0.7547 Intermediate Similarity NPD6409 Approved
0.7547 Intermediate Similarity NPD7146 Approved
0.7545 Intermediate Similarity NPD6001 Approved
0.7544 Intermediate Similarity NPD7632 Discontinued
0.7542 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD6314 Approved
0.7541 Intermediate Similarity NPD6313 Approved
0.7521 Intermediate Similarity NPD4730 Approved
0.7521 Intermediate Similarity NPD4729 Approved
0.75 Intermediate Similarity NPD6909 Approved
0.75 Intermediate Similarity NPD8033 Approved
0.75 Intermediate Similarity NPD8335 Approved
0.75 Intermediate Similarity NPD7902 Approved
0.75 Intermediate Similarity NPD8380 Approved
0.75 Intermediate Similarity NPD8379 Approved
0.75 Intermediate Similarity NPD6908 Approved
0.75 Intermediate Similarity NPD8378 Approved
0.75 Intermediate Similarity NPD8296 Approved
0.7477 Intermediate Similarity NPD5695 Phase 3
0.7411 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD5222 Approved
0.7411 Intermediate Similarity NPD5221 Approved
0.7407 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5250 Approved
0.7395 Intermediate Similarity NPD5247 Approved
0.7395 Intermediate Similarity NPD5251 Approved
0.7395 Intermediate Similarity NPD5249 Phase 3
0.7395 Intermediate Similarity NPD5248 Approved
0.7387 Intermediate Similarity NPD7748 Approved
0.7381 Intermediate Similarity NPD8328 Phase 3
0.7381 Intermediate Similarity NPD6067 Discontinued
0.7373 Intermediate Similarity NPD6686 Approved
0.7373 Intermediate Similarity NPD5128 Approved
0.7373 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD5284 Approved
0.7364 Intermediate Similarity NPD5281 Approved
0.7364 Intermediate Similarity NPD7515 Phase 2
0.736 Intermediate Similarity NPD7503 Approved
0.7358 Intermediate Similarity NPD3666 Approved
0.7358 Intermediate Similarity NPD3665 Phase 1
0.7358 Intermediate Similarity NPD3133 Approved
0.7345 Intermediate Similarity NPD5173 Approved
0.7339 Intermediate Similarity NPD6673 Approved
0.7339 Intermediate Similarity NPD4753 Phase 2
0.7339 Intermediate Similarity NPD6904 Approved
0.7339 Intermediate Similarity NPD6080 Approved
0.7311 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7281 Intermediate Similarity NPD4225 Approved
0.7273 Intermediate Similarity NPD5207 Approved
0.725 Intermediate Similarity NPD5169 Approved
0.725 Intermediate Similarity NPD5135 Approved
0.725 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6672 Approved
0.7248 Intermediate Similarity NPD5737 Approved
0.7236 Intermediate Similarity NPD6868 Approved
0.7232 Intermediate Similarity NPD7900 Approved
0.7232 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD5693 Phase 1
0.7207 Intermediate Similarity NPD8035 Phase 2
0.7207 Intermediate Similarity NPD8034 Phase 2
0.7196 Intermediate Similarity NPD4786 Approved
0.719 Intermediate Similarity NPD5217 Approved
0.719 Intermediate Similarity NPD5216 Approved
0.719 Intermediate Similarity NPD5127 Approved
0.719 Intermediate Similarity NPD5215 Approved
0.717 Intermediate Similarity NPD4223 Phase 3
0.717 Intermediate Similarity NPD4221 Approved
0.7168 Intermediate Similarity NPD4629 Approved
0.7168 Intermediate Similarity NPD5210 Approved
0.713 Intermediate Similarity NPD5329 Approved
0.7107 Intermediate Similarity NPD6371 Approved
0.7091 Intermediate Similarity NPD5208 Approved
0.7073 Intermediate Similarity NPD8133 Approved
0.7064 Intermediate Similarity NPD6098 Approved
0.7064 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6050 Approved
0.7037 Intermediate Similarity NPD4197 Approved
0.7034 Intermediate Similarity NPD6052 Approved
0.7016 Intermediate Similarity NPD5167 Approved
0.7009 Intermediate Similarity NPD3667 Approved
0.7 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3573 Approved
0.6972 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6964 Remote Similarity NPD5692 Phase 3
0.6953 Remote Similarity NPD8516 Approved
0.6953 Remote Similarity NPD8513 Phase 3
0.6953 Remote Similarity NPD8515 Approved
0.6953 Remote Similarity NPD8517 Approved
0.6934 Remote Similarity NPD6334 Approved
0.6934 Remote Similarity NPD6333 Approved
0.6909 Remote Similarity NPD4138 Approved
0.6909 Remote Similarity NPD4689 Approved
0.6909 Remote Similarity NPD4693 Phase 3
0.6909 Remote Similarity NPD4690 Approved
0.6909 Remote Similarity NPD5205 Approved
0.6909 Remote Similarity NPD4688 Approved
0.6905 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5694 Approved
0.6875 Remote Similarity NPD6051 Approved
0.6866 Remote Similarity NPD7260 Phase 2

  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