Structure

Physi-Chem Properties

Molecular Weight:  278.12
Volume:  281.652
LogP:  0.694
LogD:  0.211
LogS:  -1.783
# Rotatable Bonds:  4
TPSA:  77.51
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.439
Synthetic Accessibility Score:  4.346
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.682
MDCK Permeability:  3.776088124141097e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.251
20% Bioavailability (F20%):  0.038
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.106
Plasma Protein Binding (PPB):  59.46825408935547%
Volume Distribution (VD):  0.361
Pgp-substrate:  57.25764083862305%

ADMET: Metabolism

CYP1A2-inhibitor:  0.042
CYP1A2-substrate:  0.268
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.185
CYP2C9-inhibitor:  0.058
CYP2C9-substrate:  0.157
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.218
CYP3A4-inhibitor:  0.067
CYP3A4-substrate:  0.235

ADMET: Excretion

Clearance (CL):  11.618
Half-life (T1/2):  0.89

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.408
Drug-inuced Liver Injury (DILI):  0.809
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.771
Maximum Recommended Daily Dose:  0.172
Skin Sensitization:  0.718
Carcinogencity:  0.147
Eye Corrosion:  0.941
Eye Irritation:  0.414
Respiratory Toxicity:  0.903

Download Data

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

  Natural Product: NPC71533

Natural Product ID:  NPC71533
Common Name*:   3-Beta-Oxy-Iso-Secotanapartholide
IUPAC Name:   (4R,5S)-5-[(3S)-3-hydroxy-2-methyl-5-oxocyclopenten-1-yl]-3-methylidene-4-(3-oxobutyl)oxolan-2-one
Synonyms:  
Standard InCHIKey:  XXYRTFCLQHKIDU-SUNKGSAMSA-N
Standard InCHI:  InChI=1S/C15H18O5/c1-7(16)4-5-10-8(2)15(19)20-14(10)13-9(3)11(17)6-12(13)18/h10-11,14,17H,2,4-6H2,1,3H3/t10-,11+,14+/m1/s1
SMILES:  CC(=O)CC[C@@H]1C(=C)C(=O)O[C@@H]1C1=C(C)[C@H](CC1=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1085174
PubChem CID:   45111066
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO28039 Alstonia vitiensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18647 Achillea falcata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27802 Candida albicaus Species Debaryomycetaceae 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
NPT941 Cell Line HaCaT Homo sapiens Activity = 2.0 % PMID[474245]
NPT941 Cell Line HaCaT Homo sapiens Activity = 0.0 % PMID[474245]
NPT941 Cell Line HaCaT Homo sapiens Activity = 11.0 % PMID[474245]
NPT941 Cell Line HaCaT Homo sapiens Activity = 18.0 % PMID[474245]
NPT941 Cell Line HaCaT Homo sapiens Activity = 4.0 % PMID[474245]
NPT941 Cell Line HaCaT Homo sapiens IC50 = 13.0 ug.mL-1 PMID[474245]

☑ 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 NPC71533 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 NPC106510
0.8977 High Similarity NPC295312
0.881 High Similarity NPC223904
0.8778 High Similarity NPC261607
0.8778 High Similarity NPC300312
0.8778 High Similarity NPC111114
0.875 High Similarity NPC100487
0.8681 High Similarity NPC135776
0.8556 High Similarity NPC474032
0.8556 High Similarity NPC268298
0.8462 Intermediate Similarity NPC129419
0.8427 Intermediate Similarity NPC284902
0.8421 Intermediate Similarity NPC141191
0.8409 Intermediate Similarity NPC472957
0.8409 Intermediate Similarity NPC472958
0.8367 Intermediate Similarity NPC203659
0.8352 Intermediate Similarity NPC32922
0.8333 Intermediate Similarity NPC160138
0.8333 Intermediate Similarity NPC72513
0.8333 Intermediate Similarity NPC288876
0.8316 Intermediate Similarity NPC169205
0.8315 Intermediate Similarity NPC21469
0.8298 Intermediate Similarity NPC48803
0.8298 Intermediate Similarity NPC90121
0.8298 Intermediate Similarity NPC275960
0.8298 Intermediate Similarity NPC193645
0.8298 Intermediate Similarity NPC477922
0.8298 Intermediate Similarity NPC304886
0.8298 Intermediate Similarity NPC471142
0.8295 Intermediate Similarity NPC318468
0.828 Intermediate Similarity NPC295204
0.828 Intermediate Similarity NPC288240
0.828 Intermediate Similarity NPC475912
0.828 Intermediate Similarity NPC273579
0.828 Intermediate Similarity NPC200237
0.828 Intermediate Similarity NPC162205
0.828 Intermediate Similarity NPC81419
0.828 Intermediate Similarity NPC179746
0.8265 Intermediate Similarity NPC110989
0.8261 Intermediate Similarity NPC476004
0.8261 Intermediate Similarity NPC474761
0.8261 Intermediate Similarity NPC77337
0.8247 Intermediate Similarity NPC171759
0.8242 Intermediate Similarity NPC202672
0.8242 Intermediate Similarity NPC473715
0.8211 Intermediate Similarity NPC477921
0.8211 Intermediate Similarity NPC185553
0.8211 Intermediate Similarity NPC473859
0.8211 Intermediate Similarity NPC230800
0.8202 Intermediate Similarity NPC96259
0.8202 Intermediate Similarity NPC141193
0.8191 Intermediate Similarity NPC469632
0.8191 Intermediate Similarity NPC167219
0.8191 Intermediate Similarity NPC474035
0.8191 Intermediate Similarity NPC303942
0.8191 Intermediate Similarity NPC81386
0.8191 Intermediate Similarity NPC57405
0.8172 Intermediate Similarity NPC473321
0.8172 Intermediate Similarity NPC12172
0.8172 Intermediate Similarity NPC208886
0.8172 Intermediate Similarity NPC30515
0.8163 Intermediate Similarity NPC225353
0.814 Intermediate Similarity NPC108816
0.814 Intermediate Similarity NPC93763
0.8132 Intermediate Similarity NPC475703
0.8132 Intermediate Similarity NPC237540
0.8125 Intermediate Similarity NPC108475
0.8125 Intermediate Similarity NPC170143
0.8125 Intermediate Similarity NPC213947
0.8111 Intermediate Similarity NPC165162
0.8111 Intermediate Similarity NPC125290
0.8111 Intermediate Similarity NPC470755
0.8105 Intermediate Similarity NPC170120
0.8105 Intermediate Similarity NPC475659
0.8105 Intermediate Similarity NPC270013
0.8105 Intermediate Similarity NPC36954
0.8105 Intermediate Similarity NPC14961
0.81 Intermediate Similarity NPC243998
0.809 Intermediate Similarity NPC250315
0.8085 Intermediate Similarity NPC153590
0.8085 Intermediate Similarity NPC475838
0.8085 Intermediate Similarity NPC469645
0.8085 Intermediate Similarity NPC469692
0.8085 Intermediate Similarity NPC228451
0.8085 Intermediate Similarity NPC125674
0.8081 Intermediate Similarity NPC475945
0.8081 Intermediate Similarity NPC475871
0.8068 Intermediate Similarity NPC35089
0.8068 Intermediate Similarity NPC10276
0.8065 Intermediate Similarity NPC473455
0.8065 Intermediate Similarity NPC473619
0.8065 Intermediate Similarity NPC144133
0.8065 Intermediate Similarity NPC475855
0.8065 Intermediate Similarity NPC51004
0.8065 Intermediate Similarity NPC179394
0.8061 Intermediate Similarity NPC474742
0.8061 Intermediate Similarity NPC185141
0.8061 Intermediate Similarity NPC133907
0.8061 Intermediate Similarity NPC46998
0.8061 Intermediate Similarity NPC128733
0.8061 Intermediate Similarity NPC110443
0.8043 Intermediate Similarity NPC476805
0.8043 Intermediate Similarity NPC475819
0.8041 Intermediate Similarity NPC23364
0.8041 Intermediate Similarity NPC473326
0.8023 Intermediate Similarity NPC116177
0.8023 Intermediate Similarity NPC320630
0.8023 Intermediate Similarity NPC7563
0.8022 Intermediate Similarity NPC261721
0.8022 Intermediate Similarity NPC67493
0.8022 Intermediate Similarity NPC305475
0.8022 Intermediate Similarity NPC475461
0.8022 Intermediate Similarity NPC122502
0.8021 Intermediate Similarity NPC91771
0.8021 Intermediate Similarity NPC476315
0.8021 Intermediate Similarity NPC142529
0.8 Intermediate Similarity NPC474338
0.8 Intermediate Similarity NPC121825
0.8 Intermediate Similarity NPC158756
0.8 Intermediate Similarity NPC114979
0.8 Intermediate Similarity NPC470013
0.8 Intermediate Similarity NPC477131
0.8 Intermediate Similarity NPC191476
0.8 Intermediate Similarity NPC470010
0.8 Intermediate Similarity NPC474247
0.8 Intermediate Similarity NPC323008
0.8 Intermediate Similarity NPC262133
0.8 Intermediate Similarity NPC140543
0.798 Intermediate Similarity NPC149371
0.798 Intermediate Similarity NPC474747
0.7979 Intermediate Similarity NPC20713
0.7979 Intermediate Similarity NPC184463
0.7979 Intermediate Similarity NPC131209
0.7978 Intermediate Similarity NPC173609
0.7957 Intermediate Similarity NPC307411
0.7957 Intermediate Similarity NPC87306
0.7941 Intermediate Similarity NPC475960
0.7938 Intermediate Similarity NPC471462
0.7935 Intermediate Similarity NPC118601
0.7935 Intermediate Similarity NPC186148
0.7931 Intermediate Similarity NPC196653
0.7931 Intermediate Similarity NPC471465
0.7921 Intermediate Similarity NPC223450
0.7917 Intermediate Similarity NPC214694
0.7917 Intermediate Similarity NPC52044
0.7917 Intermediate Similarity NPC213698
0.7912 Intermediate Similarity NPC137033
0.7912 Intermediate Similarity NPC215364
0.7912 Intermediate Similarity NPC255307
0.7912 Intermediate Similarity NPC261380
0.79 Intermediate Similarity NPC472755
0.7895 Intermediate Similarity NPC473234
0.7895 Intermediate Similarity NPC60386
0.7895 Intermediate Similarity NPC473273
0.7895 Intermediate Similarity NPC212486
0.7895 Intermediate Similarity NPC308656
0.7895 Intermediate Similarity NPC473263
0.7895 Intermediate Similarity NPC475302
0.7895 Intermediate Similarity NPC476300
0.7889 Intermediate Similarity NPC40746
0.7889 Intermediate Similarity NPC39588
0.7889 Intermediate Similarity NPC169575
0.7879 Intermediate Similarity NPC47880
0.7879 Intermediate Similarity NPC201718
0.7879 Intermediate Similarity NPC150923
0.7872 Intermediate Similarity NPC301969
0.7872 Intermediate Similarity NPC19087
0.7872 Intermediate Similarity NPC37607
0.7872 Intermediate Similarity NPC62815
0.7865 Intermediate Similarity NPC24417
0.7864 Intermediate Similarity NPC38154
0.7857 Intermediate Similarity NPC187268
0.7857 Intermediate Similarity NPC471144
0.7849 Intermediate Similarity NPC227379
0.7849 Intermediate Similarity NPC58219
0.7849 Intermediate Similarity NPC177629
0.7849 Intermediate Similarity NPC178875
0.7849 Intermediate Similarity NPC474471
0.7849 Intermediate Similarity NPC153805
0.7849 Intermediate Similarity NPC91248
0.7849 Intermediate Similarity NPC476803
0.7841 Intermediate Similarity NPC470239
0.7841 Intermediate Similarity NPC470244
0.7835 Intermediate Similarity NPC279621
0.7835 Intermediate Similarity NPC126156
0.7826 Intermediate Similarity NPC477010
0.7826 Intermediate Similarity NPC112685
0.7826 Intermediate Similarity NPC164393
0.7826 Intermediate Similarity NPC469910
0.7826 Intermediate Similarity NPC470242
0.7822 Intermediate Similarity NPC474741
0.7812 Intermediate Similarity NPC473331
0.7812 Intermediate Similarity NPC476267
0.7812 Intermediate Similarity NPC127019
0.7812 Intermediate Similarity NPC53685
0.7812 Intermediate Similarity NPC90453
0.7812 Intermediate Similarity NPC198853
0.7802 Intermediate Similarity NPC476804
0.7802 Intermediate Similarity NPC212363
0.7802 Intermediate Similarity NPC474780

  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 NPC71533 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
0.8298 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD5785 Approved
0.7717 Intermediate Similarity NPD5363 Approved
0.767 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD5786 Approved
0.7619 Intermediate Similarity NPD6371 Approved
0.7527 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7983 Approved
0.7391 Intermediate Similarity NPD4269 Approved
0.7391 Intermediate Similarity NPD4270 Approved
0.732 Intermediate Similarity NPD46 Approved
0.732 Intermediate Similarity NPD6698 Approved
0.7312 Intermediate Similarity NPD5362 Discontinued
0.7216 Intermediate Similarity NPD1695 Approved
0.7174 Intermediate Similarity NPD4252 Approved
0.7172 Intermediate Similarity NPD5778 Approved
0.7172 Intermediate Similarity NPD5779 Approved
0.7128 Intermediate Similarity NPD7154 Phase 3
0.71 Intermediate Similarity NPD5282 Discontinued
0.7097 Intermediate Similarity NPD5369 Approved
0.7083 Intermediate Similarity NPD4249 Approved
0.7021 Intermediate Similarity NPD5209 Approved
0.701 Intermediate Similarity NPD4250 Approved
0.701 Intermediate Similarity NPD4251 Approved
0.699 Remote Similarity NPD4225 Approved
0.6961 Remote Similarity NPD7839 Suspended
0.6847 Remote Similarity NPD6053 Discontinued
0.6842 Remote Similarity NPD6435 Approved
0.6827 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6804 Remote Similarity NPD1694 Approved
0.6804 Remote Similarity NPD6082 Clinical (unspecified phase)
0.68 Remote Similarity NPD7838 Discovery
0.67 Remote Similarity NPD5370 Suspended
0.6632 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5368 Approved
0.6604 Remote Similarity NPD7640 Approved
0.6604 Remote Similarity NPD7639 Approved
0.6598 Remote Similarity NPD5332 Approved
0.6598 Remote Similarity NPD5331 Approved
0.6596 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6569 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4790 Discontinued
0.6535 Remote Similarity NPD6101 Approved
0.6535 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6525 Remote Similarity NPD8516 Approved
0.6525 Remote Similarity NPD8513 Phase 3
0.6525 Remote Similarity NPD8517 Approved
0.6525 Remote Similarity NPD8515 Approved
0.6509 Remote Similarity NPD7638 Approved
0.6495 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6686 Approved
0.6466 Remote Similarity NPD7115 Discovery
0.646 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4819 Approved
0.6458 Remote Similarity NPD4822 Approved
0.6458 Remote Similarity NPD4821 Approved
0.6458 Remote Similarity NPD4820 Approved
0.6455 Remote Similarity NPD6008 Approved
0.6421 Remote Similarity NPD4268 Approved
0.6421 Remote Similarity NPD4271 Approved
0.6408 Remote Similarity NPD7637 Suspended
0.6408 Remote Similarity NPD6411 Approved
0.6327 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4756 Discovery
0.6281 Remote Similarity NPD7642 Approved
0.6263 Remote Similarity NPD6110 Phase 1
0.626 Remote Similarity NPD8074 Phase 3
0.6239 Remote Similarity NPD5344 Discontinued
0.623 Remote Similarity NPD7492 Approved
0.6222 Remote Similarity NPD4247 Clinical (unspecified phase)
0.62 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6182 Remote Similarity NPD7632 Discontinued
0.618 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6179 Remote Similarity NPD6616 Approved
0.6167 Remote Similarity NPD6054 Approved
0.6167 Remote Similarity NPD6319 Approved
0.616 Remote Similarity NPD7319 Approved
0.6148 Remote Similarity NPD7829 Approved
0.6148 Remote Similarity NPD7830 Approved
0.6129 Remote Similarity NPD7078 Approved
0.6116 Remote Similarity NPD6015 Approved
0.6116 Remote Similarity NPD6016 Approved
0.6111 Remote Similarity NPD7331 Phase 2
0.6106 Remote Similarity NPD5697 Approved
0.608 Remote Similarity NPD7736 Approved
0.6068 Remote Similarity NPD4632 Approved
0.6066 Remote Similarity NPD5988 Approved
0.6066 Remote Similarity NPD6370 Approved
0.6053 Remote Similarity NPD6899 Approved
0.6053 Remote Similarity NPD6881 Approved
0.6053 Remote Similarity NPD7320 Approved
0.6053 Remote Similarity NPD6011 Approved
0.605 Remote Similarity NPD7500 Approved
0.6048 Remote Similarity NPD7507 Approved
0.6038 Remote Similarity NPD6399 Phase 3
0.6034 Remote Similarity NPD6650 Approved
0.6034 Remote Similarity NPD6649 Approved
0.6033 Remote Similarity NPD6059 Approved
0.6018 Remote Similarity NPD5739 Approved
0.6018 Remote Similarity NPD6675 Approved
0.6018 Remote Similarity NPD7128 Approved
0.6018 Remote Similarity NPD6402 Approved
0.6016 Remote Similarity NPD6845 Suspended
0.6 Remote Similarity NPD7341 Phase 2
0.6 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6 Remote Similarity NPD6014 Approved
0.6 Remote Similarity NPD6648 Approved
0.6 Remote Similarity NPD7641 Discontinued
0.6 Remote Similarity NPD6372 Approved
0.6 Remote Similarity NPD8293 Discontinued
0.6 Remote Similarity NPD6013 Approved
0.6 Remote Similarity NPD6012 Approved
0.6 Remote Similarity NPD6373 Approved
0.5984 Remote Similarity NPD8444 Approved
0.5982 Remote Similarity NPD6647 Phase 2
0.598 Remote Similarity NPD1696 Phase 3
0.5965 Remote Similarity NPD5701 Approved
0.5963 Remote Similarity NPD6083 Phase 2
0.5963 Remote Similarity NPD6084 Phase 2
0.5962 Remote Similarity NPD6903 Approved
0.5954 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5948 Remote Similarity NPD7290 Approved
0.5948 Remote Similarity NPD7102 Approved
0.5948 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5948 Remote Similarity NPD6883 Approved
0.5938 Remote Similarity NPD8039 Approved
0.5938 Remote Similarity NPD7260 Phase 2
0.5926 Remote Similarity NPD5695 Phase 3
0.5922 Remote Similarity NPD7146 Approved
0.5922 Remote Similarity NPD6409 Approved
0.5922 Remote Similarity NPD7521 Approved
0.5922 Remote Similarity NPD5330 Approved
0.5922 Remote Similarity NPD6422 Discontinued
0.5922 Remote Similarity NPD6684 Approved
0.5922 Remote Similarity NPD7334 Approved
0.5917 Remote Similarity NPD6009 Approved
0.5913 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5696 Approved
0.5897 Remote Similarity NPD6847 Approved
0.5897 Remote Similarity NPD8130 Phase 1
0.5897 Remote Similarity NPD6869 Approved
0.5897 Remote Similarity NPD6617 Approved
0.5893 Remote Similarity NPD5211 Phase 2
0.5882 Remote Similarity NPD3666 Approved
0.5882 Remote Similarity NPD3133 Approved
0.5882 Remote Similarity NPD3665 Phase 1
0.5877 Remote Similarity NPD5048 Discontinued
0.5854 Remote Similarity NPD8268 Approved
0.5854 Remote Similarity NPD8269 Approved
0.5854 Remote Similarity NPD8266 Approved
0.5854 Remote Similarity NPD8267 Approved
0.5854 Remote Similarity NPD5983 Phase 2
0.5854 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5847 Remote Similarity NPD8297 Approved
0.5847 Remote Similarity NPD6882 Approved
0.5833 Remote Similarity NPD7748 Approved
0.5826 Remote Similarity NPD6412 Phase 2
0.5818 Remote Similarity NPD7902 Approved
0.5812 Remote Similarity NPD4634 Approved
0.581 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5794 Remote Similarity NPD8451 Approved
0.5794 Remote Similarity NPD6079 Approved
0.5794 Remote Similarity NPD5693 Phase 1
0.5794 Remote Similarity NPD7515 Phase 2
0.5789 Remote Similarity NPD5141 Approved
0.578 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5769 Remote Similarity NPD3618 Phase 1
0.5769 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5763 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5763 Remote Similarity NPD2204 Approved
0.5763 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5761 Remote Similarity NPD3704 Approved
0.576 Remote Similarity NPD7604 Phase 2
0.576 Remote Similarity NPD8328 Phase 3
0.5758 Remote Similarity NPD4802 Phase 2
0.5758 Remote Similarity NPD4238 Approved
0.5755 Remote Similarity NPD5328 Approved
0.5748 Remote Similarity NPD8448 Approved
0.5736 Remote Similarity NPD6007 Clinical (unspecified phase)
0.5727 Remote Similarity NPD4697 Phase 3
0.5727 Remote Similarity NPD5221 Approved
0.5727 Remote Similarity NPD5222 Approved
0.5727 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8340 Approved
0.5714 Remote Similarity NPD8341 Approved
0.5714 Remote Similarity NPD8299 Approved
0.5714 Remote Similarity NPD5286 Approved
0.5714 Remote Similarity NPD4696 Approved
0.5714 Remote Similarity NPD5285 Approved
0.5714 Remote Similarity NPD8342 Approved
0.5703 Remote Similarity NPD6033 Approved
0.5702 Remote Similarity NPD6274 Approved
0.5701 Remote Similarity NPD5207 Approved
0.569 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5686 Remote Similarity NPD3667 Approved
0.568 Remote Similarity NPD8080 Discontinued
0.5676 Remote Similarity NPD5173 Approved
0.5676 Remote Similarity NPD4755 Approved
0.5669 Remote Similarity NPD6336 Discontinued
0.5669 Remote Similarity NPD8273 Phase 1

  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