Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  269.578
LogP:  1.159
LogD:  1.21
LogS:  -2.555
# Rotatable Bonds:  0
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.393
Synthetic Accessibility Score:  4.891
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.678
MDCK Permeability:  1.9585340851335786e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.027
20% Bioavailability (F20%):  0.135
30% Bioavailability (F30%):  0.156

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.535
Plasma Protein Binding (PPB):  60.1273078918457%
Volume Distribution (VD):  1.017
Pgp-substrate:  36.7330207824707%

ADMET: Metabolism

CYP1A2-inhibitor:  0.057
CYP1A2-substrate:  0.273
CYP2C19-inhibitor:  0.054
CYP2C19-substrate:  0.606
CYP2C9-inhibitor:  0.06
CYP2C9-substrate:  0.147
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.08
CYP3A4-inhibitor:  0.337
CYP3A4-substrate:  0.272

ADMET: Excretion

Clearance (CL):  5.245
Half-life (T1/2):  0.435

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.195
Drug-inuced Liver Injury (DILI):  0.461
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.93
Maximum Recommended Daily Dose:  0.949
Skin Sensitization:  0.231
Carcinogencity:  0.903
Eye Corrosion:  0.164
Eye Irritation:  0.78
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC470013

Natural Product ID:  NPC470013
Common Name*:   4Alpha,10Beta-Dihydroxy-5Alpha(H)-1,11(13)-Guaidien-8B,12-Olide
IUPAC Name:   (3aR,5S,8R,8aR,9aR)-5,8-dihydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one
Synonyms:  
Standard InCHIKey:  SKXYOUKPVUIPFP-SYZWTGEBSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h4,9,11-12,17-18H,1,5-7H2,2-3H3/t9-,11-,12-,14-,15+/m1/s1
SMILES:  CC1(CC=C2C1CC3C(CC2(C)O)OC(=O)C3=C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1644104
PubChem CID:   53317933
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
NPO23499 Carpesium faberi Species Asteraceae Eukaryota whole plant Changshou County, Chongqing, China 2008-Aug PMID[21109433]
NPO33441 leucophyta brownii Species Asteraceae Eukaryota Resinous Exudates n.a. n.a. PMID[26218649]
NPO23499 Carpesium faberi Species Asteraceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 26.5 ug.mL-1 PMID[464297]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 37500.0 nM PMID[464298]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 21200.0 nM PMID[464298]

☑ 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 NPC470013 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 NPC323008
1.0 High Similarity NPC470010
1.0 High Similarity NPC262133
0.9773 High Similarity NPC198853
0.9551 High Similarity NPC477131
0.9545 High Similarity NPC133698
0.9545 High Similarity NPC131209
0.9425 High Similarity NPC91248
0.9231 High Similarity NPC52044
0.9231 High Similarity NPC67584
0.9231 High Similarity NPC304886
0.914 High Similarity NPC221615
0.913 High Similarity NPC213078
0.9101 High Similarity NPC4986
0.9053 High Similarity NPC86077
0.9032 High Similarity NPC161493
0.9022 High Similarity NPC170120
0.9011 High Similarity NPC135776
0.9 High Similarity NPC301969
0.9 High Similarity NPC37607
0.8989 High Similarity NPC79549
0.8913 High Similarity NPC127019
0.8901 High Similarity NPC475925
0.8889 High Similarity NPC215556
0.8817 High Similarity NPC213698
0.8804 High Similarity NPC258216
0.8791 High Similarity NPC216284
0.8778 High Similarity NPC217983
0.8778 High Similarity NPC207114
0.8776 High Similarity NPC166115
0.8776 High Similarity NPC223450
0.8776 High Similarity NPC243998
0.8764 High Similarity NPC187661
0.8763 High Similarity NPC124881
0.875 High Similarity NPC150923
0.8696 High Similarity NPC155215
0.8696 High Similarity NPC184063
0.8681 High Similarity NPC32922
0.8652 High Similarity NPC284534
0.8652 High Similarity NPC300082
0.8652 High Similarity NPC204105
0.8587 High Similarity NPC129419
0.8587 High Similarity NPC19087
0.8571 High Similarity NPC178875
0.8556 High Similarity NPC67493
0.8556 High Similarity NPC64153
0.8539 High Similarity NPC224386
0.8539 High Similarity NPC194859
0.8526 High Similarity NPC24956
0.8526 High Similarity NPC18019
0.8511 High Similarity NPC167219
0.8511 High Similarity NPC474338
0.8506 High Similarity NPC276356
0.85 High Similarity NPC26617
0.8478 Intermediate Similarity NPC155935
0.8478 Intermediate Similarity NPC268298
0.8478 Intermediate Similarity NPC38392
0.8462 Intermediate Similarity NPC118601
0.8462 Intermediate Similarity NPC160138
0.8454 Intermediate Similarity NPC70865
0.8444 Intermediate Similarity NPC165162
0.8438 Intermediate Similarity NPC181151
0.8427 Intermediate Similarity NPC128246
0.8427 Intermediate Similarity NPC245665
0.8427 Intermediate Similarity NPC250315
0.8421 Intermediate Similarity NPC220221
0.8421 Intermediate Similarity NPC476053
0.8421 Intermediate Similarity NPC163228
0.8421 Intermediate Similarity NPC472873
0.8404 Intermediate Similarity NPC125674
0.8404 Intermediate Similarity NPC228451
0.8404 Intermediate Similarity NPC475838
0.8404 Intermediate Similarity NPC475912
0.8387 Intermediate Similarity NPC475855
0.8387 Intermediate Similarity NPC54065
0.8387 Intermediate Similarity NPC179394
0.8387 Intermediate Similarity NPC35809
0.8387 Intermediate Similarity NPC297474
0.8387 Intermediate Similarity NPC144133
0.837 Intermediate Similarity NPC224652
0.8352 Intermediate Similarity NPC107787
0.8333 Intermediate Similarity NPC156485
0.8333 Intermediate Similarity NPC114979
0.8333 Intermediate Similarity NPC191476
0.8316 Intermediate Similarity NPC474247
0.8315 Intermediate Similarity NPC246076
0.8315 Intermediate Similarity NPC89555
0.83 Intermediate Similarity NPC100487
0.8298 Intermediate Similarity NPC293001
0.8298 Intermediate Similarity NPC63193
0.8298 Intermediate Similarity NPC261607
0.8298 Intermediate Similarity NPC57304
0.8298 Intermediate Similarity NPC29821
0.8298 Intermediate Similarity NPC171360
0.8298 Intermediate Similarity NPC133888
0.8298 Intermediate Similarity NPC300312
0.8298 Intermediate Similarity NPC35959
0.8298 Intermediate Similarity NPC111114
0.828 Intermediate Similarity NPC472872
0.828 Intermediate Similarity NPC295312
0.8269 Intermediate Similarity NPC35069
0.8269 Intermediate Similarity NPC189338
0.8269 Intermediate Similarity NPC258711
0.8269 Intermediate Similarity NPC95290
0.8261 Intermediate Similarity NPC237540
0.8247 Intermediate Similarity NPC213947
0.8247 Intermediate Similarity NPC170143
0.8247 Intermediate Similarity NPC108475
0.8247 Intermediate Similarity NPC474313
0.8242 Intermediate Similarity NPC255307
0.8242 Intermediate Similarity NPC235792
0.8242 Intermediate Similarity NPC78089
0.8229 Intermediate Similarity NPC36954
0.8229 Intermediate Similarity NPC270013
0.8229 Intermediate Similarity NPC224689
0.8229 Intermediate Similarity NPC14961
0.8222 Intermediate Similarity NPC111409
0.8218 Intermediate Similarity NPC54737
0.8211 Intermediate Similarity NPC476300
0.8211 Intermediate Similarity NPC81419
0.8211 Intermediate Similarity NPC179746
0.8202 Intermediate Similarity NPC126248
0.8191 Intermediate Similarity NPC51004
0.8191 Intermediate Similarity NPC62815
0.8182 Intermediate Similarity NPC171759
0.8172 Intermediate Similarity NPC202672
0.8163 Intermediate Similarity NPC187268
0.8163 Intermediate Similarity NPC45125
0.8163 Intermediate Similarity NPC141191
0.8152 Intermediate Similarity NPC50637
0.8152 Intermediate Similarity NPC304558
0.8152 Intermediate Similarity NPC475461
0.8152 Intermediate Similarity NPC56593
0.8152 Intermediate Similarity NPC236692
0.8152 Intermediate Similarity NPC305475
0.8152 Intermediate Similarity NPC470242
0.8152 Intermediate Similarity NPC309757
0.8144 Intermediate Similarity NPC279621
0.8144 Intermediate Similarity NPC476315
0.8144 Intermediate Similarity NPC230800
0.8132 Intermediate Similarity NPC154893
0.8132 Intermediate Similarity NPC16887
0.8132 Intermediate Similarity NPC53011
0.8132 Intermediate Similarity NPC37005
0.8132 Intermediate Similarity NPC476804
0.8132 Intermediate Similarity NPC165287
0.8132 Intermediate Similarity NPC472958
0.8132 Intermediate Similarity NPC141193
0.8132 Intermediate Similarity NPC96259
0.8132 Intermediate Similarity NPC115786
0.8132 Intermediate Similarity NPC472957
0.8132 Intermediate Similarity NPC212363
0.8125 Intermediate Similarity NPC81386
0.8125 Intermediate Similarity NPC57405
0.8125 Intermediate Similarity NPC474035
0.8125 Intermediate Similarity NPC303942
0.8119 Intermediate Similarity NPC203659
0.8113 Intermediate Similarity NPC471380
0.8111 Intermediate Similarity NPC229825
0.8105 Intermediate Similarity NPC208886
0.8105 Intermediate Similarity NPC30515
0.8105 Intermediate Similarity NPC184463
0.8105 Intermediate Similarity NPC12172
0.809 Intermediate Similarity NPC74673
0.809 Intermediate Similarity NPC258965
0.809 Intermediate Similarity NPC156658
0.809 Intermediate Similarity NPC69271
0.8085 Intermediate Similarity NPC212664
0.8085 Intermediate Similarity NPC473564
0.8085 Intermediate Similarity NPC307411
0.8081 Intermediate Similarity NPC471381
0.8081 Intermediate Similarity NPC186861
0.8077 Intermediate Similarity NPC471884
0.8077 Intermediate Similarity NPC257240
0.8065 Intermediate Similarity NPC24728
0.8065 Intermediate Similarity NPC270270
0.8065 Intermediate Similarity NPC190753
0.8061 Intermediate Similarity NPC471462
0.8061 Intermediate Similarity NPC477949
0.8061 Intermediate Similarity NPC471150
0.8061 Intermediate Similarity NPC169205
0.8061 Intermediate Similarity NPC311904
0.8043 Intermediate Similarity NPC215364
0.8041 Intermediate Similarity NPC193645
0.8041 Intermediate Similarity NPC48803
0.8041 Intermediate Similarity NPC90121
0.8041 Intermediate Similarity NPC469873
0.8041 Intermediate Similarity NPC275960
0.8039 Intermediate Similarity NPC475217
0.8039 Intermediate Similarity NPC179891
0.8022 Intermediate Similarity NPC131669
0.8022 Intermediate Similarity NPC473390
0.8021 Intermediate Similarity NPC212486
0.8021 Intermediate Similarity NPC153590
0.8021 Intermediate Similarity NPC60386
0.8021 Intermediate Similarity NPC473234
0.8021 Intermediate Similarity NPC473263
0.8021 Intermediate Similarity NPC472874
0.8021 Intermediate Similarity NPC473273
0.8021 Intermediate Similarity NPC308656

  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 NPC470013 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
0.9101 High Similarity NPD1695 Approved
0.85 High Similarity NPD7899 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD6371 Approved
0.8041 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD5362 Discontinued
0.7579 Intermediate Similarity NPD4249 Approved
0.75 Intermediate Similarity NPD4250 Approved
0.75 Intermediate Similarity NPD4251 Approved
0.7474 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD7154 Phase 3
0.7431 Intermediate Similarity NPD6053 Discontinued
0.7292 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5785 Approved
0.7273 Intermediate Similarity NPD46 Approved
0.7273 Intermediate Similarity NPD6698 Approved
0.7228 Intermediate Similarity NPD5282 Discontinued
0.7128 Intermediate Similarity NPD4820 Approved
0.7128 Intermediate Similarity NPD4819 Approved
0.7128 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4821 Approved
0.7128 Intermediate Similarity NPD4822 Approved
0.7113 Intermediate Similarity NPD5363 Approved
0.6979 Remote Similarity NPD4270 Approved
0.6979 Remote Similarity NPD4269 Approved
0.6931 Remote Similarity NPD7838 Discovery
0.6915 Remote Similarity NPD4271 Approved
0.6915 Remote Similarity NPD4268 Approved
0.6907 Remote Similarity NPD5332 Approved
0.6907 Remote Similarity NPD5331 Approved
0.6887 Remote Similarity NPD7640 Approved
0.6887 Remote Similarity NPD7639 Approved
0.6875 Remote Similarity NPD4790 Discontinued
0.6875 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5369 Approved
0.6869 Remote Similarity NPD5786 Approved
0.6863 Remote Similarity NPD7983 Approved
0.6804 Remote Similarity NPD6435 Approved
0.6796 Remote Similarity NPD5779 Approved
0.6796 Remote Similarity NPD5778 Approved
0.6792 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4225 Approved
0.6792 Remote Similarity NPD7638 Approved
0.6771 Remote Similarity NPD4252 Approved
0.6768 Remote Similarity NPD1694 Approved
0.6757 Remote Similarity NPD6686 Approved
0.6737 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD5344 Discontinued
0.6635 Remote Similarity NPD6399 Phase 3
0.6633 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5368 Approved
0.6581 Remote Similarity NPD7115 Discovery
0.6574 Remote Similarity NPD6648 Approved
0.6538 Remote Similarity NPD7637 Suspended
0.6509 Remote Similarity NPD5695 Phase 3
0.6481 Remote Similarity NPD5696 Approved
0.6423 Remote Similarity NPD7507 Approved
0.6389 Remote Similarity NPD6084 Phase 2
0.6389 Remote Similarity NPD6083 Phase 2
0.6372 Remote Similarity NPD5697 Approved
0.6364 Remote Similarity NPD8513 Phase 3
0.6364 Remote Similarity NPD8516 Approved
0.6364 Remote Similarity NPD8517 Approved
0.6364 Remote Similarity NPD8515 Approved
0.6348 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6337 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6899 Approved
0.6316 Remote Similarity NPD6881 Approved
0.6316 Remote Similarity NPD7320 Approved
0.6306 Remote Similarity NPD7632 Discontinued
0.63 Remote Similarity NPD5209 Approved
0.6296 Remote Similarity NPD7839 Suspended
0.6293 Remote Similarity NPD6649 Approved
0.6293 Remote Similarity NPD6650 Approved
0.6283 Remote Similarity NPD5739 Approved
0.6283 Remote Similarity NPD6675 Approved
0.6283 Remote Similarity NPD7128 Approved
0.6283 Remote Similarity NPD6402 Approved
0.627 Remote Similarity NPD7319 Approved
0.6261 Remote Similarity NPD6013 Approved
0.6261 Remote Similarity NPD6372 Approved
0.6261 Remote Similarity NPD6014 Approved
0.6261 Remote Similarity NPD6012 Approved
0.6261 Remote Similarity NPD6373 Approved
0.6261 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6695 Phase 3
0.6228 Remote Similarity NPD5701 Approved
0.6226 Remote Similarity NPD5693 Phase 1
0.6226 Remote Similarity NPD5281 Approved
0.6226 Remote Similarity NPD5284 Approved
0.621 Remote Similarity NPD7492 Approved
0.6207 Remote Similarity NPD6883 Approved
0.6207 Remote Similarity NPD7290 Approved
0.6207 Remote Similarity NPD7102 Approved
0.6204 Remote Similarity NPD6356 Clinical (unspecified phase)
0.619 Remote Similarity NPD5764 Clinical (unspecified phase)
0.619 Remote Similarity NPD6101 Approved
0.6186 Remote Similarity NPD4632 Approved
0.6174 Remote Similarity NPD6011 Approved
0.6161 Remote Similarity NPD5211 Phase 2
0.616 Remote Similarity NPD6616 Approved
0.6154 Remote Similarity NPD6617 Approved
0.6154 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6869 Approved
0.6154 Remote Similarity NPD8130 Phase 1
0.6154 Remote Similarity NPD6847 Approved
0.6148 Remote Similarity NPD6054 Approved
0.6148 Remote Similarity NPD6319 Approved
0.6132 Remote Similarity NPD5207 Approved
0.6116 Remote Similarity NPD7328 Approved
0.6116 Remote Similarity NPD7327 Approved
0.6111 Remote Similarity NPD8074 Phase 3
0.6111 Remote Similarity NPD7078 Approved
0.6102 Remote Similarity NPD8297 Approved
0.6102 Remote Similarity NPD6882 Approved
0.6098 Remote Similarity NPD6016 Approved
0.6098 Remote Similarity NPD8033 Approved
0.6098 Remote Similarity NPD6015 Approved
0.6095 Remote Similarity NPD6903 Approved
0.6087 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6412 Phase 2
0.6075 Remote Similarity NPD6411 Approved
0.6066 Remote Similarity NPD7516 Approved
0.6063 Remote Similarity NPD7736 Approved
0.6058 Remote Similarity NPD7334 Approved
0.6058 Remote Similarity NPD5330 Approved
0.6058 Remote Similarity NPD7521 Approved
0.6058 Remote Similarity NPD6409 Approved
0.6058 Remote Similarity NPD6684 Approved
0.6058 Remote Similarity NPD7146 Approved
0.6055 Remote Similarity NPD5210 Approved
0.6055 Remote Similarity NPD4629 Approved
0.6053 Remote Similarity NPD5141 Approved
0.6048 Remote Similarity NPD6370 Approved
0.6048 Remote Similarity NPD5988 Approved
0.6038 Remote Similarity NPD6051 Approved
0.6038 Remote Similarity NPD4753 Phase 2
0.6033 Remote Similarity NPD6009 Approved
0.6032 Remote Similarity NPD8273 Phase 1
0.6019 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6016 Remote Similarity NPD8294 Approved
0.6016 Remote Similarity NPD8377 Approved
0.6016 Remote Similarity NPD6059 Approved
0.6 Remote Similarity NPD7750 Discontinued
0.6 Remote Similarity NPD7524 Approved
0.5984 Remote Similarity NPD8293 Discontinued
0.5982 Remote Similarity NPD5285 Approved
0.5982 Remote Similarity NPD5286 Approved
0.5982 Remote Similarity NPD4696 Approved
0.5969 Remote Similarity NPD6007 Clinical (unspecified phase)
0.5968 Remote Similarity NPD8379 Approved
0.5968 Remote Similarity NPD8296 Approved
0.5968 Remote Similarity NPD8335 Approved
0.5968 Remote Similarity NPD5983 Phase 2
0.5968 Remote Similarity NPD7503 Approved
0.5968 Remote Similarity NPD8380 Approved
0.5968 Remote Similarity NPD8378 Approved
0.5968 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5963 Remote Similarity NPD6001 Approved
0.596 Remote Similarity NPD4756 Discovery
0.595 Remote Similarity NPD6274 Approved
0.5946 Remote Similarity NPD7902 Approved
0.5946 Remote Similarity NPD4755 Approved
0.5943 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5943 Remote Similarity NPD6672 Approved
0.5943 Remote Similarity NPD5737 Approved
0.5941 Remote Similarity NPD6931 Approved
0.5941 Remote Similarity NPD6930 Phase 2
0.5941 Remote Similarity NPD7332 Phase 2
0.5926 Remote Similarity NPD8034 Phase 2
0.5926 Remote Similarity NPD8035 Phase 2
0.5923 Remote Similarity NPD7260 Phase 2
0.5918 Remote Similarity NPD8039 Approved
0.5917 Remote Similarity NPD8133 Approved
0.5888 Remote Similarity NPD6673 Approved
0.5888 Remote Similarity NPD5370 Suspended
0.5888 Remote Similarity NPD6904 Approved
0.5888 Remote Similarity NPD6080 Approved
0.5882 Remote Similarity NPD2204 Approved
0.5882 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5878 Remote Similarity NPD6845 Suspended
0.5877 Remote Similarity NPD5225 Approved
0.5877 Remote Similarity NPD4633 Approved
0.5877 Remote Similarity NPD5226 Approved
0.5877 Remote Similarity NPD5224 Approved
0.5873 Remote Similarity NPD7604 Phase 2
0.5872 Remote Similarity NPD4202 Approved
0.5865 Remote Similarity NPD3133 Approved
0.5865 Remote Similarity NPD3666 Approved
0.5865 Remote Similarity NPD3665 Phase 1
0.5865 Remote Similarity NPD4786 Approved
0.5842 Remote Similarity NPD6929 Approved
0.5841 Remote Similarity NPD4700 Approved
0.5833 Remote Similarity NPD5692 Phase 3
0.5826 Remote Similarity NPD5174 Approved
0.5826 Remote Similarity NPD5175 Approved
0.5825 Remote Similarity NPD3667 Approved
0.5825 Remote Similarity NPD4221 Approved
0.5825 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5825 Remote Similarity NPD4223 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