Structure

Physi-Chem Properties

Molecular Weight:  303.18
Volume:  326.956
LogP:  2.135
LogD:  2.736
LogS:  -2.579
# Rotatable Bonds:  7
TPSA:  66.4
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.81
Synthetic Accessibility Score:  3.632
Fsp3:  0.556
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.801
MDCK Permeability:  0.00012104943016311154
Pgp-inhibitor:  0.003
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.362
Plasma Protein Binding (PPB):  35.730377197265625%
Volume Distribution (VD):  1.099
Pgp-substrate:  50.51551055908203%

ADMET: Metabolism

CYP1A2-inhibitor:  0.05
CYP1A2-substrate:  0.132
CYP2C19-inhibitor:  0.289
CYP2C19-substrate:  0.335
CYP2C9-inhibitor:  0.345
CYP2C9-substrate:  0.902
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.362
CYP3A4-inhibitor:  0.26
CYP3A4-substrate:  0.346

ADMET: Excretion

Clearance (CL):  10.391
Half-life (T1/2):  0.866

ADMET: Toxicity

hERG Blockers:  0.046
Human Hepatotoxicity (H-HT):  0.191
Drug-inuced Liver Injury (DILI):  0.487
AMES Toxicity:  0.282
Rat Oral Acute Toxicity:  0.724
Maximum Recommended Daily Dose:  0.269
Skin Sensitization:  0.398
Carcinogencity:  0.323
Eye Corrosion:  0.004
Eye Irritation:  0.034
Respiratory Toxicity:  0.232

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

  Natural Product: NPC188010

Natural Product ID:  NPC188010
Common Name*:   Berkeleyamide A
IUPAC Name:   (3R,5S)-3-[(1S)-1-hydroxy-3-oxo-4-phenylbutyl]-5-(2-methylpropyl)pyrrolidin-2-one
Synonyms:  
Standard InCHIKey:  KACACYYTPVUKSL-UAGQMJEPSA-N
Standard InCHI:  InChI=1S/C18H25NO3/c1-12(2)8-14-10-16(18(22)19-14)17(21)11-15(20)9-13-6-4-3-5-7-13/h3-7,12,14,16-17,21H,8-11H2,1-2H3,(H,19,22)/t14-,16+,17-/m0/s1
SMILES:  O[C@H]([C@H]1C[C@@H](N=C1O)CC(C)C)CC(=O)Cc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL466565
PubChem CID:   44577362
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO10881 Gyrophyllum sibogae Species Pennatulidae Eukaryota n.a. n.a. n.a. PMID[15270580]
NPO3909 Leucas aspera Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16872130]
NPO29761 Penicillium rubrum Species Trichocomaceae Eukaryota n.a. Berkeley Pit Lake, Butte, Montana n.a. PMID[18330993]
NPO29761 Penicillium rubrum Species Trichocomaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO29761 Penicillium rubrum Species Trichocomaceae Eukaryota n.a. n.a. n.a. PMID[22295871]
NPO15056 Helianthus pumilus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15056 Helianthus pumilus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3909 Leucas aspera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15056 Helianthus pumilus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15056 Helianthus pumilus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10881 Gyrophyllum sibogae Species Pennatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3221 Schkuhria anthemoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3909 Leucas aspera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO263 Clibadium microcephalum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17828 Talaromyces ruber Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9306 Globularia nudicaulis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15438 Stemona parviflora Species Stemonaceae 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
NPT277 Individual Protein Caspase-1 Homo sapiens IC50 = 330.0 nM PMID[469438]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens IC50 = 330.0 nM PMID[469438]

☑ 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 NPC188010 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
0.8403 Intermediate Similarity NPC478016
0.8403 Intermediate Similarity NPC478014
0.8403 Intermediate Similarity NPC478015
0.8306 Intermediate Similarity NPC116057
0.8036 Intermediate Similarity NPC471317
0.8031 Intermediate Similarity NPC183722
0.8016 Intermediate Similarity NPC472413
0.7951 Intermediate Similarity NPC80150
0.7934 Intermediate Similarity NPC310467
0.7903 Intermediate Similarity NPC472415
0.7863 Intermediate Similarity NPC208725
0.7851 Intermediate Similarity NPC169328
0.7778 Intermediate Similarity NPC472414
0.7769 Intermediate Similarity NPC328070
0.771 Intermediate Similarity NPC477680
0.7685 Intermediate Similarity NPC316108
0.768 Intermediate Similarity NPC213126
0.768 Intermediate Similarity NPC84281
0.768 Intermediate Similarity NPC169485
0.768 Intermediate Similarity NPC317474
0.768 Intermediate Similarity NPC291027
0.7669 Intermediate Similarity NPC473055
0.7669 Intermediate Similarity NPC473052
0.7661 Intermediate Similarity NPC190663
0.7652 Intermediate Similarity NPC224610
0.7652 Intermediate Similarity NPC113326
0.7652 Intermediate Similarity NPC194390
0.7652 Intermediate Similarity NPC88267
0.7642 Intermediate Similarity NPC314992
0.7619 Intermediate Similarity NPC35996
0.7612 Intermediate Similarity NPC322526
0.7611 Intermediate Similarity NPC12730
0.7597 Intermediate Similarity NPC71271
0.7568 Intermediate Similarity NPC58674
0.7565 Intermediate Similarity NPC202613
0.7557 Intermediate Similarity NPC42423
0.754 Intermediate Similarity NPC160493
0.752 Intermediate Similarity NPC477061
0.752 Intermediate Similarity NPC45777
0.7519 Intermediate Similarity NPC113325
0.7519 Intermediate Similarity NPC279045
0.75 Intermediate Similarity NPC47667
0.7481 Intermediate Similarity NPC471201
0.748 Intermediate Similarity NPC2265
0.7455 Intermediate Similarity NPC187725
0.7455 Intermediate Similarity NPC141607
0.7444 Intermediate Similarity NPC228511
0.7438 Intermediate Similarity NPC474584
0.7373 Intermediate Similarity NPC327481
0.736 Intermediate Similarity NPC237420
0.7345 Intermediate Similarity NPC25565
0.7333 Intermediate Similarity NPC175870
0.7317 Intermediate Similarity NPC471318
0.7281 Intermediate Similarity NPC473501
0.7281 Intermediate Similarity NPC475439
0.7273 Intermediate Similarity NPC69496
0.7273 Intermediate Similarity NPC319579
0.7265 Intermediate Similarity NPC164859
0.7257 Intermediate Similarity NPC206764
0.7257 Intermediate Similarity NPC161972
0.7257 Intermediate Similarity NPC303045
0.7252 Intermediate Similarity NPC319766
0.7236 Intermediate Similarity NPC35850
0.7236 Intermediate Similarity NPC276949
0.7227 Intermediate Similarity NPC25385
0.7227 Intermediate Similarity NPC193640
0.7227 Intermediate Similarity NPC475905
0.7209 Intermediate Similarity NPC6975
0.7203 Intermediate Similarity NPC19136
0.7185 Intermediate Similarity NPC248283
0.7183 Intermediate Similarity NPC339338
0.7183 Intermediate Similarity NPC227905
0.7183 Intermediate Similarity NPC146097
0.7177 Intermediate Similarity NPC33742
0.7176 Intermediate Similarity NPC278097
0.7174 Intermediate Similarity NPC239770
0.7154 Intermediate Similarity NPC273814
0.7132 Intermediate Similarity NPC252878
0.712 Intermediate Similarity NPC197470
0.7117 Intermediate Similarity NPC470877
0.7117 Intermediate Similarity NPC231591
0.7111 Intermediate Similarity NPC245836
0.7111 Intermediate Similarity NPC233910
0.7083 Intermediate Similarity NPC185404
0.7077 Intermediate Similarity NPC46427
0.7073 Intermediate Similarity NPC329011
0.7068 Intermediate Similarity NPC295478
0.7059 Intermediate Similarity NPC64897
0.7059 Intermediate Similarity NPC90693
0.7054 Intermediate Similarity NPC121872
0.7054 Intermediate Similarity NPC141139
0.7054 Intermediate Similarity NPC471307
0.7054 Intermediate Similarity NPC209764
0.7054 Intermediate Similarity NPC78041
0.7054 Intermediate Similarity NPC74936
0.7054 Intermediate Similarity NPC202521
0.7054 Intermediate Similarity NPC159178
0.7037 Intermediate Similarity NPC246913
0.7034 Intermediate Similarity NPC474820
0.7034 Intermediate Similarity NPC475978
0.7023 Intermediate Similarity NPC285394
0.7015 Intermediate Similarity NPC478147
0.7008 Intermediate Similarity NPC254088
0.7 Intermediate Similarity NPC474307
0.6991 Remote Similarity NPC226438
0.6991 Remote Similarity NPC245259
0.6985 Remote Similarity NPC287401
0.6983 Remote Similarity NPC311242
0.6983 Remote Similarity NPC324569
0.6978 Remote Similarity NPC476259
0.6977 Remote Similarity NPC476990
0.6972 Remote Similarity NPC49565
0.697 Remote Similarity NPC477248
0.697 Remote Similarity NPC477249
0.695 Remote Similarity NPC476978
0.6949 Remote Similarity NPC94487
0.6949 Remote Similarity NPC469457
0.6947 Remote Similarity NPC474082
0.6947 Remote Similarity NPC175726
0.6942 Remote Similarity NPC191215
0.6942 Remote Similarity NPC274089
0.693 Remote Similarity NPC323164
0.6923 Remote Similarity NPC317280
0.6923 Remote Similarity NPC271475
0.6923 Remote Similarity NPC329387
0.6903 Remote Similarity NPC172128
0.6879 Remote Similarity NPC161069
0.6875 Remote Similarity NPC470545
0.6875 Remote Similarity NPC325441
0.687 Remote Similarity NPC474862
0.687 Remote Similarity NPC471309
0.686 Remote Similarity NPC321670
0.686 Remote Similarity NPC211551
0.6857 Remote Similarity NPC239762
0.6857 Remote Similarity NPC268841
0.6857 Remote Similarity NPC163392
0.6857 Remote Similarity NPC307357
0.6857 Remote Similarity NPC46098
0.6853 Remote Similarity NPC262216
0.6849 Remote Similarity NPC162104
0.6846 Remote Similarity NPC200964
0.6842 Remote Similarity NPC474847
0.6842 Remote Similarity NPC101719
0.6842 Remote Similarity NPC4974
0.6838 Remote Similarity NPC477767
0.6838 Remote Similarity NPC130309
0.6838 Remote Similarity NPC122493
0.6838 Remote Similarity NPC10781
0.6838 Remote Similarity NPC293628
0.6829 Remote Similarity NPC475282
0.6828 Remote Similarity NPC2501
0.6822 Remote Similarity NPC470546
0.6815 Remote Similarity NPC296712
0.6809 Remote Similarity NPC263493
0.6809 Remote Similarity NPC269398
0.6807 Remote Similarity NPC158623
0.6806 Remote Similarity NPC145113
0.6797 Remote Similarity NPC470544
0.6791 Remote Similarity NPC65310
0.6786 Remote Similarity NPC471638
0.6783 Remote Similarity NPC5620
0.678 Remote Similarity NPC322598
0.6772 Remote Similarity NPC215419
0.6767 Remote Similarity NPC222466
0.6763 Remote Similarity NPC260045
0.6763 Remote Similarity NPC293377
0.6763 Remote Similarity NPC79465
0.6763 Remote Similarity NPC475598
0.6763 Remote Similarity NPC76785
0.6763 Remote Similarity NPC474811
0.6763 Remote Similarity NPC273907
0.6763 Remote Similarity NPC9687
0.6763 Remote Similarity NPC118099
0.6763 Remote Similarity NPC151706
0.6763 Remote Similarity NPC90194
0.6763 Remote Similarity NPC474787
0.6763 Remote Similarity NPC475318
0.6763 Remote Similarity NPC474855
0.6763 Remote Similarity NPC476102
0.6763 Remote Similarity NPC49577
0.6761 Remote Similarity NPC111586
0.6761 Remote Similarity NPC91953
0.6761 Remote Similarity NPC108852
0.6761 Remote Similarity NPC176226
0.6761 Remote Similarity NPC261709
0.6755 Remote Similarity NPC476194
0.6754 Remote Similarity NPC258627
0.675 Remote Similarity NPC474112
0.6744 Remote Similarity NPC471553
0.6727 Remote Similarity NPC44830
0.6726 Remote Similarity NPC477693
0.6726 Remote Similarity NPC12429
0.6726 Remote Similarity NPC477704
0.6723 Remote Similarity NPC476042
0.6723 Remote Similarity NPC54647
0.6721 Remote Similarity NPC67043
0.6721 Remote Similarity NPC471186
0.672 Remote Similarity NPC265513
0.6719 Remote Similarity NPC235421
0.6718 Remote Similarity NPC476183

  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 NPC188010 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
0.7863 Intermediate Similarity NPD3644 Approved
0.7863 Intermediate Similarity NPD3643 Approved
0.7863 Intermediate Similarity NPD3642 Approved
0.7826 Intermediate Similarity NPD467 Phase 1
0.768 Intermediate Similarity NPD3131 Approved
0.768 Intermediate Similarity NPD2610 Approved
0.768 Intermediate Similarity NPD4217 Approved
0.768 Intermediate Similarity NPD2612 Approved
0.768 Intermediate Similarity NPD4218 Approved
0.768 Intermediate Similarity NPD4216 Approved
0.768 Intermediate Similarity NPD2609 Approved
0.768 Intermediate Similarity NPD2611 Approved
0.768 Intermediate Similarity NPD3132 Approved
0.768 Intermediate Similarity NPD4215 Approved
0.768 Intermediate Similarity NPD2608 Approved
0.7642 Intermediate Similarity NPD2218 Phase 2
0.7642 Intermediate Similarity NPD2217 Approved
0.7615 Intermediate Similarity NPD4738 Phase 2
0.7603 Intermediate Similarity NPD1711 Phase 2
0.7581 Intermediate Similarity NPD5981 Approved
0.75 Intermediate Similarity NPD6325 Discontinued
0.7463 Intermediate Similarity NPD8172 Phase 2
0.7463 Intermediate Similarity NPD8173 Phase 2
0.7436 Intermediate Similarity NPD1018 Approved
0.7419 Intermediate Similarity NPD7522 Discontinued
0.7411 Intermediate Similarity NPD4814 Discontinued
0.7391 Intermediate Similarity NPD4760 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD2652 Approved
0.7377 Intermediate Similarity NPD2650 Approved
0.7288 Intermediate Similarity NPD999 Phase 2
0.7273 Intermediate Similarity NPD2613 Approved
0.7232 Intermediate Similarity NPD6690 Approved
0.7185 Intermediate Similarity NPD8265 Approved
0.7167 Intermediate Similarity NPD6406 Approved
0.7143 Intermediate Similarity NPD1040 Phase 2
0.7132 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD1348 Approved
0.7111 Intermediate Similarity NPD2574 Discontinued
0.7111 Intermediate Similarity NPD3615 Approved
0.7111 Intermediate Similarity NPD2573 Approved
0.7111 Intermediate Similarity NPD2566 Approved
0.7111 Intermediate Similarity NPD2570 Approved
0.7111 Intermediate Similarity NPD3614 Approved
0.7111 Intermediate Similarity NPD4746 Phase 3
0.7111 Intermediate Similarity NPD3090 Approved
0.7111 Intermediate Similarity NPD3616 Approved
0.7111 Intermediate Similarity NPD4745 Approved
0.7111 Intermediate Similarity NPD2571 Approved
0.7111 Intermediate Similarity NPD2572 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD3088 Approved
0.7111 Intermediate Similarity NPD3089 Approved
0.7111 Intermediate Similarity NPD3087 Approved
0.7077 Intermediate Similarity NPD5108 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD3123 Discovery
0.7034 Intermediate Similarity NPD4719 Phase 2
0.7023 Intermediate Similarity NPD5157 Phase 1
0.7023 Intermediate Similarity NPD5159 Phase 2
0.7023 Intermediate Similarity NPD5158 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD1066 Discontinued
0.7007 Intermediate Similarity NPD4686 Approved
0.7007 Intermediate Similarity NPD4684 Phase 3
0.7007 Intermediate Similarity NPD4685 Phase 3
0.6953 Remote Similarity NPD4479 Discontinued
0.6953 Remote Similarity NPD2617 Discontinued
0.6947 Remote Similarity NPD2584 Suspended
0.694 Remote Similarity NPD3626 Phase 3
0.6934 Remote Similarity NPD8416 Discontinued
0.693 Remote Similarity NPD1814 Approved
0.693 Remote Similarity NPD1812 Approved
0.6923 Remote Similarity NPD253 Approved
0.6899 Remote Similarity NPD4209 Clinical (unspecified phase)
0.687 Remote Similarity NPD1080 Approved
0.687 Remote Similarity NPD3719 Approved
0.687 Remote Similarity NPD3718 Approved
0.6864 Remote Similarity NPD1067 Discontinued
0.6842 Remote Similarity NPD5577 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5578 Approved
0.6838 Remote Similarity NPD4657 Approved
0.6838 Remote Similarity NPD4655 Approved
0.6838 Remote Similarity NPD9566 Approved
0.6838 Remote Similarity NPD3136 Phase 2
0.681 Remote Similarity NPD1693 Approved
0.6797 Remote Similarity NPD4574 Approved
0.6797 Remote Similarity NPD4576 Approved
0.6794 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6791 Remote Similarity NPD2160 Approved
0.6791 Remote Similarity NPD2628 Approved
0.6791 Remote Similarity NPD2159 Approved
0.6791 Remote Similarity NPD2625 Approved
0.6791 Remote Similarity NPD2626 Approved
0.6791 Remote Similarity NPD2627 Approved
0.6786 Remote Similarity NPD6852 Discontinued
0.6769 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2607 Approved
0.6742 Remote Similarity NPD5618 Discontinued
0.6742 Remote Similarity NPD3603 Phase 3
0.6733 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6724 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6721 Remote Similarity NPD5048 Discontinued
0.672 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6718 Remote Similarity NPD7342 Discontinued
0.6694 Remote Similarity NPD5765 Approved
0.6693 Remote Similarity NPD1680 Approved
0.6693 Remote Similarity NPD3598 Phase 3
0.6693 Remote Similarity NPD1681 Approved
0.6693 Remote Similarity NPD1682 Approved
0.6692 Remote Similarity NPD998 Approved
0.669 Remote Similarity NPD8323 Discontinued
0.6667 Remote Similarity NPD5704 Approved
0.6667 Remote Similarity NPD800 Approved
0.6667 Remote Similarity NPD5705 Approved
0.6667 Remote Similarity NPD5706 Approved
0.6667 Remote Similarity NPD6685 Approved
0.6667 Remote Similarity NPD4094 Approved
0.6667 Remote Similarity NPD5347 Phase 2
0.6667 Remote Similarity NPD5346 Phase 2
0.6643 Remote Similarity NPD8643 Discontinued
0.6642 Remote Similarity NPD4125 Approved
0.664 Remote Similarity NPD1756 Approved
0.664 Remote Similarity NPD1752 Approved
0.662 Remote Similarity NPD3648 Clinical (unspecified phase)
0.662 Remote Similarity NPD6865 Phase 2
0.662 Remote Similarity NPD6864 Phase 2
0.6619 Remote Similarity NPD7714 Approved
0.6619 Remote Similarity NPD7715 Approved
0.6618 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6615 Remote Similarity NPD1758 Phase 1
0.6614 Remote Similarity NPD181 Approved
0.6612 Remote Similarity NPD6027 Approved
0.6612 Remote Similarity NPD2196 Discontinued
0.6612 Remote Similarity NPD6024 Approved
0.6612 Remote Similarity NPD854 Approved
0.6612 Remote Similarity NPD855 Approved
0.6609 Remote Similarity NPD1089 Approved
0.6609 Remote Similarity NPD1090 Approved
0.6609 Remote Similarity NPD1086 Approved
0.6593 Remote Similarity NPD6330 Clinical (unspecified phase)
0.6593 Remote Similarity NPD6792 Phase 3
0.6593 Remote Similarity NPD1036 Approved
0.6585 Remote Similarity NPD5717 Approved
0.6585 Remote Similarity NPD2197 Approved
0.6585 Remote Similarity NPD2192 Approved
0.6583 Remote Similarity NPD2066 Phase 3
0.6579 Remote Similarity NPD1101 Approved
0.6575 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6565 Remote Similarity NPD6093 Discontinued
0.6565 Remote Similarity NPD1759 Phase 1
0.6562 Remote Similarity NPD1370 Approved
0.6562 Remote Similarity NPD1371 Approved
0.6562 Remote Similarity NPD1373 Approved
0.6562 Remote Similarity NPD1374 Approved
0.6557 Remote Similarity NPD6647 Phase 2
0.6555 Remote Similarity NPD2487 Clinical (unspecified phase)
0.6555 Remote Similarity NPD1100 Approved
0.6555 Remote Similarity NPD1099 Approved
0.6552 Remote Similarity NPD530 Approved
0.6545 Remote Similarity NPD226 Approved
0.6544 Remote Similarity NPD6302 Clinical (unspecified phase)
0.6528 Remote Similarity NPD7978 Discontinued
0.6528 Remote Similarity NPD4152 Approved
0.6512 Remote Similarity NPD747 Discontinued
0.6512 Remote Similarity NPD4766 Approved
0.6508 Remote Similarity NPD4234 Approved
0.6508 Remote Similarity NPD4233 Approved
0.6507 Remote Similarity NPD3400 Discontinued
0.6507 Remote Similarity NPD2575 Approved
0.65 Remote Similarity NPD9612 Approved
0.65 Remote Similarity NPD9609 Approved
0.65 Remote Similarity NPD9611 Approved
0.6496 Remote Similarity NPD5339 Clinical (unspecified phase)
0.6496 Remote Similarity NPD1088 Approved
0.6496 Remote Similarity NPD752 Approved
0.6491 Remote Similarity NPD4793 Discontinued
0.6489 Remote Similarity NPD2117 Pre-registration
0.6489 Remote Similarity NPD2115 Approved
0.6489 Remote Similarity NPD6065 Approved
0.6489 Remote Similarity NPD2116 Approved
0.6484 Remote Similarity NPD4165 Phase 2
0.6484 Remote Similarity NPD3066 Phase 2
0.6484 Remote Similarity NPD480 Approved
0.6483 Remote Similarity NPD2437 Approved
0.6483 Remote Similarity NPD2436 Approved
0.648 Remote Similarity NPD4095 Clinical (unspecified phase)
0.6479 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6475 Remote Similarity NPD2193 Phase 2
0.6475 Remote Similarity NPD4119 Approved
0.6475 Remote Similarity NPD2648 Phase 3
0.6471 Remote Similarity NPD2895 Discontinued
0.6466 Remote Similarity NPD5306 Approved
0.6466 Remote Similarity NPD3672 Approved
0.6466 Remote Similarity NPD4733 Approved
0.6466 Remote Similarity NPD5305 Approved
0.6466 Remote Similarity NPD3673 Approved
0.6462 Remote Similarity NPD7508 Discontinued
0.6449 Remote Similarity NPD3663 Approved
0.6449 Remote Similarity NPD7828 Discontinued
0.6449 Remote Similarity NPD3661 Approved
0.6449 Remote Similarity NPD3664 Approved
0.6449 Remote Similarity NPD3662 Phase 3

  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