Structure

Physi-Chem Properties

Molecular Weight:  334.21
Volume:  356.058
LogP:  2.393
LogD:  2.397
LogS:  -3.762
# Rotatable Bonds:  3
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.615
Synthetic Accessibility Score:  4.798
Fsp3:  0.75
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:  -4.623
MDCK Permeability:  2.36135001614457e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.079
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.021
30% Bioavailability (F30%):  0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.913
Plasma Protein Binding (PPB):  34.020965576171875%
Volume Distribution (VD):  0.787
Pgp-substrate:  67.89456176757812%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.308
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.63
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.053
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.283
CYP3A4-inhibitor:  0.842
CYP3A4-substrate:  0.237

ADMET: Excretion

Clearance (CL):  10.034
Half-life (T1/2):  0.318

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.037
Drug-inuced Liver Injury (DILI):  0.084
AMES Toxicity:  0.054
Rat Oral Acute Toxicity:  0.899
Maximum Recommended Daily Dose:  0.952
Skin Sensitization:  0.289
Carcinogencity:  0.128
Eye Corrosion:  0.008
Eye Irritation:  0.061
Respiratory Toxicity:  0.95

Download Data

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

  Natural Product: NPC72845

Natural Product ID:  NPC72845
Common Name*:   (12E)-3Beta,18-Dihydroxylabda-8(17),12-Dien-16,15-Olide
IUPAC Name:   (3E)-3-[2-[(1S,4aR,5R,6S,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one
Synonyms:  
Standard InCHIKey:  VFAUHRWHZPEKBY-IFBPREHGSA-N
Standard InCHI:  InChI=1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5,15-17,21-22H,1,4,6-12H2,2-3H3/b14-5+/t15-,16+,17-,19+,20-/m0/s1
SMILES:  OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CCC(=C)[C@@H]2C/C=C/1CCOC1=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2333386
PubChem CID:   71578897
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
NPO31457 Amomum kravanh Species Zingiberaceae Eukaryota fruits n.a. n.a. PMID[23394284]
NPO31457 Amomum kravanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31457 Amomum kravanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT113 Cell Line RAW264.7 Mus musculus Inhibition < 10.0 % PMID[486147]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 90.0 % PMID[486147]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 200000.0 nM PMID[486147]

☑ 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 NPC72845 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
0.9545 High Similarity NPC57117
0.9535 High Similarity NPC474396
0.9535 High Similarity NPC50488
0.9444 High Similarity NPC73911
0.9341 High Similarity NPC124512
0.9341 High Similarity NPC278386
0.9341 High Similarity NPC159763
0.9213 High Similarity NPC152778
0.9213 High Similarity NPC162615
0.9213 High Similarity NPC139692
0.9213 High Similarity NPC205034
0.9186 High Similarity NPC329692
0.9186 High Similarity NPC131813
0.913 High Similarity NPC473154
0.907 High Similarity NPC476602
0.9022 High Similarity NPC474343
0.9011 High Similarity NPC183012
0.8989 High Similarity NPC78973
0.8989 High Similarity NPC310479
0.8913 High Similarity NPC134072
0.8913 High Similarity NPC16967
0.8913 High Similarity NPC242848
0.8913 High Similarity NPC234993
0.8901 High Similarity NPC191521
0.883 High Similarity NPC47024
0.8791 High Similarity NPC472812
0.8778 High Similarity NPC182136
0.8778 High Similarity NPC221111
0.8778 High Similarity NPC280149
0.8723 High Similarity NPC474440
0.871 High Similarity NPC473153
0.8681 High Similarity NPC233345
0.8681 High Similarity NPC186363
0.8681 High Similarity NPC472811
0.8652 High Similarity NPC166857
0.8646 High Similarity NPC476081
0.8632 High Similarity NPC476299
0.8632 High Similarity NPC474012
0.8621 High Similarity NPC311070
0.8621 High Similarity NPC79945
0.8602 High Similarity NPC276110
0.8587 High Similarity NPC53555
0.8557 High Similarity NPC476237
0.8557 High Similarity NPC120321
0.8556 High Similarity NPC104560
0.8542 High Similarity NPC303559
0.8526 High Similarity NPC216478
0.8523 High Similarity NPC96055
0.8478 Intermediate Similarity NPC177037
0.8478 Intermediate Similarity NPC472814
0.8462 Intermediate Similarity NPC79027
0.8462 Intermediate Similarity NPC168131
0.8462 Intermediate Similarity NPC174342
0.8454 Intermediate Similarity NPC114540
0.8454 Intermediate Similarity NPC32577
0.8454 Intermediate Similarity NPC155332
0.8444 Intermediate Similarity NPC473891
0.8444 Intermediate Similarity NPC305029
0.8444 Intermediate Similarity NPC181103
0.8438 Intermediate Similarity NPC476303
0.8427 Intermediate Similarity NPC30984
0.8427 Intermediate Similarity NPC65661
0.8427 Intermediate Similarity NPC86316
0.8427 Intermediate Similarity NPC106416
0.8421 Intermediate Similarity NPC253826
0.8404 Intermediate Similarity NPC259042
0.8404 Intermediate Similarity NPC157686
0.84 Intermediate Similarity NPC189075
0.84 Intermediate Similarity NPC275539
0.8391 Intermediate Similarity NPC170303
0.8391 Intermediate Similarity NPC159148
0.837 Intermediate Similarity NPC158488
0.837 Intermediate Similarity NPC51486
0.8367 Intermediate Similarity NPC297617
0.8367 Intermediate Similarity NPC176883
0.8367 Intermediate Similarity NPC112009
0.8352 Intermediate Similarity NPC477302
0.8352 Intermediate Similarity NPC277771
0.8352 Intermediate Similarity NPC472809
0.8352 Intermediate Similarity NPC472810
0.8351 Intermediate Similarity NPC471412
0.8333 Intermediate Similarity NPC108368
0.8333 Intermediate Similarity NPC57079
0.8333 Intermediate Similarity NPC316598
0.8333 Intermediate Similarity NPC218107
0.8333 Intermediate Similarity NPC85698
0.8333 Intermediate Similarity NPC478056
0.8333 Intermediate Similarity NPC185638
0.8333 Intermediate Similarity NPC9231
0.8316 Intermediate Similarity NPC202833
0.8316 Intermediate Similarity NPC165632
0.83 Intermediate Similarity NPC187435
0.83 Intermediate Similarity NPC110496
0.83 Intermediate Similarity NPC67321
0.8298 Intermediate Similarity NPC24861
0.8298 Intermediate Similarity NPC225474
0.8298 Intermediate Similarity NPC470255
0.8298 Intermediate Similarity NPC477129
0.8298 Intermediate Similarity NPC477130
0.8298 Intermediate Similarity NPC469596
0.8298 Intermediate Similarity NPC470697
0.8298 Intermediate Similarity NPC148000
0.8298 Intermediate Similarity NPC105490
0.828 Intermediate Similarity NPC329842
0.8276 Intermediate Similarity NPC281880
0.8265 Intermediate Similarity NPC475038
0.8265 Intermediate Similarity NPC109195
0.8265 Intermediate Similarity NPC469606
0.8265 Intermediate Similarity NPC273668
0.8265 Intermediate Similarity NPC273005
0.8265 Intermediate Similarity NPC58329
0.8265 Intermediate Similarity NPC31058
0.8261 Intermediate Similarity NPC116620
0.8261 Intermediate Similarity NPC218927
0.8261 Intermediate Similarity NPC314727
0.8261 Intermediate Similarity NPC82876
0.8261 Intermediate Similarity NPC206001
0.8261 Intermediate Similarity NPC288699
0.8261 Intermediate Similarity NPC5509
0.8261 Intermediate Similarity NPC73995
0.8247 Intermediate Similarity NPC251680
0.8247 Intermediate Similarity NPC117685
0.8247 Intermediate Similarity NPC471413
0.8247 Intermediate Similarity NPC38855
0.8247 Intermediate Similarity NPC201406
0.8242 Intermediate Similarity NPC470012
0.8229 Intermediate Similarity NPC132753
0.8229 Intermediate Similarity NPC473963
0.8229 Intermediate Similarity NPC475709
0.8229 Intermediate Similarity NPC121402
0.8229 Intermediate Similarity NPC224356
0.8229 Intermediate Similarity NPC151681
0.8229 Intermediate Similarity NPC287668
0.8229 Intermediate Similarity NPC51499
0.8229 Intermediate Similarity NPC175351
0.8222 Intermediate Similarity NPC329738
0.8222 Intermediate Similarity NPC474013
0.8222 Intermediate Similarity NPC217394
0.8222 Intermediate Similarity NPC52628
0.8218 Intermediate Similarity NPC306265
0.8211 Intermediate Similarity NPC476519
0.8211 Intermediate Similarity NPC209355
0.8211 Intermediate Similarity NPC472441
0.8202 Intermediate Similarity NPC42476
0.8202 Intermediate Similarity NPC470948
0.8202 Intermediate Similarity NPC476927
0.82 Intermediate Similarity NPC469607
0.82 Intermediate Similarity NPC478208
0.82 Intermediate Similarity NPC477125
0.82 Intermediate Similarity NPC218158
0.82 Intermediate Similarity NPC34768
0.82 Intermediate Similarity NPC266570
0.8191 Intermediate Similarity NPC38232
0.8191 Intermediate Similarity NPC115021
0.8191 Intermediate Similarity NPC472640
0.8191 Intermediate Similarity NPC7349
0.8191 Intermediate Similarity NPC472641
0.8182 Intermediate Similarity NPC471938
0.8182 Intermediate Similarity NPC180204
0.8173 Intermediate Similarity NPC264153
0.8172 Intermediate Similarity NPC152467
0.8172 Intermediate Similarity NPC253186
0.8172 Intermediate Similarity NPC38952
0.8172 Intermediate Similarity NPC472642
0.8163 Intermediate Similarity NPC115899
0.8163 Intermediate Similarity NPC473160
0.8163 Intermediate Similarity NPC81530
0.8163 Intermediate Similarity NPC235142
0.8152 Intermediate Similarity NPC136879
0.8152 Intermediate Similarity NPC93411
0.8152 Intermediate Similarity NPC473229
0.8152 Intermediate Similarity NPC477128
0.8152 Intermediate Similarity NPC226863
0.8152 Intermediate Similarity NPC215831
0.8144 Intermediate Similarity NPC278673
0.8144 Intermediate Similarity NPC325229
0.8144 Intermediate Similarity NPC275086
0.8144 Intermediate Similarity NPC252295
0.8144 Intermediate Similarity NPC23364
0.8144 Intermediate Similarity NPC92275
0.814 Intermediate Similarity NPC189206
0.8137 Intermediate Similarity NPC474243
0.8132 Intermediate Similarity NPC250981
0.8132 Intermediate Similarity NPC477920
0.8132 Intermediate Similarity NPC6979
0.8125 Intermediate Similarity NPC472363
0.8125 Intermediate Similarity NPC473964
0.8125 Intermediate Similarity NPC284518
0.8125 Intermediate Similarity NPC190713
0.8125 Intermediate Similarity NPC154526
0.8125 Intermediate Similarity NPC93245
0.8125 Intermediate Similarity NPC472362
0.8125 Intermediate Similarity NPC307164
0.8119 Intermediate Similarity NPC302788
0.8119 Intermediate Similarity NPC179380
0.8111 Intermediate Similarity NPC32223
0.8105 Intermediate Similarity NPC469697
0.8105 Intermediate Similarity NPC250075
0.8105 Intermediate Similarity NPC279410
0.8105 Intermediate Similarity NPC476186

  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 NPC72845 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
0.9341 High Similarity NPD4225 Approved
0.8333 Intermediate Similarity NPD7638 Approved
0.8247 Intermediate Similarity NPD7640 Approved
0.8247 Intermediate Similarity NPD7639 Approved
0.809 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD1694 Approved
0.7778 Intermediate Similarity NPD7115 Discovery
0.7553 Intermediate Similarity NPD3618 Phase 1
0.7551 Intermediate Similarity NPD7748 Approved
0.7549 Intermediate Similarity NPD7632 Discontinued
0.7526 Intermediate Similarity NPD7515 Phase 2
0.7524 Intermediate Similarity NPD6686 Approved
0.75 Intermediate Similarity NPD7902 Approved
0.7475 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD6399 Phase 3
0.7429 Intermediate Similarity NPD5697 Approved
0.7358 Intermediate Similarity NPD6899 Approved
0.7358 Intermediate Similarity NPD6881 Approved
0.7347 Intermediate Similarity NPD7637 Suspended
0.734 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7128 Approved
0.7333 Intermediate Similarity NPD5739 Approved
0.7333 Intermediate Similarity NPD6675 Approved
0.7333 Intermediate Similarity NPD6402 Approved
0.7315 Intermediate Similarity NPD6649 Approved
0.7315 Intermediate Similarity NPD6650 Approved
0.729 Intermediate Similarity NPD6014 Approved
0.729 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6372 Approved
0.729 Intermediate Similarity NPD6013 Approved
0.729 Intermediate Similarity NPD6012 Approved
0.729 Intermediate Similarity NPD6373 Approved
0.7282 Intermediate Similarity NPD5344 Discontinued
0.7264 Intermediate Similarity NPD5701 Approved
0.7245 Intermediate Similarity NPD5785 Approved
0.7222 Intermediate Similarity NPD6883 Approved
0.7222 Intermediate Similarity NPD7102 Approved
0.7222 Intermediate Similarity NPD7290 Approved
0.7222 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7900 Approved
0.7196 Intermediate Similarity NPD6011 Approved
0.7196 Intermediate Similarity NPD7320 Approved
0.7172 Intermediate Similarity NPD6079 Approved
0.7157 Intermediate Similarity NPD6083 Phase 2
0.7157 Intermediate Similarity NPD6084 Phase 2
0.7156 Intermediate Similarity NPD8130 Phase 1
0.7156 Intermediate Similarity NPD6617 Approved
0.7156 Intermediate Similarity NPD6869 Approved
0.7156 Intermediate Similarity NPD6847 Approved
0.7143 Intermediate Similarity NPD5328 Approved
0.7128 Intermediate Similarity NPD3667 Approved
0.7091 Intermediate Similarity NPD8297 Approved
0.7091 Intermediate Similarity NPD6882 Approved
0.7087 Intermediate Similarity NPD5696 Approved
0.7059 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD5222 Approved
0.7059 Intermediate Similarity NPD5221 Approved
0.7059 Intermediate Similarity NPD4697 Phase 3
0.7048 Intermediate Similarity NPD5211 Phase 2
0.7019 Intermediate Similarity NPD5286 Approved
0.7019 Intermediate Similarity NPD5285 Approved
0.7019 Intermediate Similarity NPD4696 Approved
0.7019 Intermediate Similarity NPD6648 Approved
0.701 Intermediate Similarity NPD7521 Approved
0.701 Intermediate Similarity NPD7146 Approved
0.701 Intermediate Similarity NPD7334 Approved
0.701 Intermediate Similarity NPD5330 Approved
0.701 Intermediate Similarity NPD6684 Approved
0.701 Intermediate Similarity NPD6409 Approved
0.7009 Intermediate Similarity NPD6008 Approved
0.7 Intermediate Similarity NPD8034 Phase 2
0.7 Intermediate Similarity NPD8035 Phase 2
0.7 Intermediate Similarity NPD6411 Approved
0.699 Remote Similarity NPD5173 Approved
0.699 Remote Similarity NPD4755 Approved
0.6989 Remote Similarity NPD7645 Phase 2
0.6979 Remote Similarity NPD3666 Approved
0.6979 Remote Similarity NPD4786 Approved
0.6979 Remote Similarity NPD3665 Phase 1
0.6979 Remote Similarity NPD3133 Approved
0.697 Remote Similarity NPD6051 Approved
0.6961 Remote Similarity NPD5695 Phase 3
0.6961 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6939 Remote Similarity NPD3573 Approved
0.6931 Remote Similarity NPD4202 Approved
0.6931 Remote Similarity NPD5779 Approved
0.6931 Remote Similarity NPD5778 Approved
0.693 Remote Similarity NPD7328 Approved
0.693 Remote Similarity NPD7327 Approved
0.6916 Remote Similarity NPD5141 Approved
0.6915 Remote Similarity NPD7525 Registered
0.6915 Remote Similarity NPD4695 Discontinued
0.6907 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6907 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6274 Approved
0.69 Remote Similarity NPD6698 Approved
0.69 Remote Similarity NPD46 Approved
0.69 Remote Similarity NPD7838 Discovery
0.6897 Remote Similarity NPD8033 Approved
0.6887 Remote Similarity NPD5226 Approved
0.6887 Remote Similarity NPD5224 Approved
0.6887 Remote Similarity NPD5225 Approved
0.6887 Remote Similarity NPD4633 Approved
0.6875 Remote Similarity NPD6695 Phase 3
0.687 Remote Similarity NPD7516 Approved
0.6869 Remote Similarity NPD5737 Approved
0.6869 Remote Similarity NPD6903 Approved
0.6869 Remote Similarity NPD6672 Approved
0.6869 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6857 Remote Similarity NPD4700 Approved
0.6848 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6847 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5693 Phase 1
0.6822 Remote Similarity NPD5174 Approved
0.6822 Remote Similarity NPD5175 Approved
0.681 Remote Similarity NPD8377 Approved
0.681 Remote Similarity NPD8294 Approved
0.6807 Remote Similarity NPD7507 Approved
0.6804 Remote Similarity NPD7338 Clinical (unspecified phase)
0.68 Remote Similarity NPD5764 Clinical (unspecified phase)
0.68 Remote Similarity NPD6101 Approved
0.68 Remote Similarity NPD4753 Phase 2
0.6796 Remote Similarity NPD5210 Approved
0.6796 Remote Similarity NPD4629 Approved
0.6792 Remote Similarity NPD5223 Approved
0.6771 Remote Similarity NPD5209 Approved
0.6762 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6371 Approved
0.6754 Remote Similarity NPD6868 Approved
0.6752 Remote Similarity NPD8379 Approved
0.6752 Remote Similarity NPD8378 Approved
0.6752 Remote Similarity NPD8335 Approved
0.6752 Remote Similarity NPD8296 Approved
0.6752 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6752 Remote Similarity NPD8380 Approved
0.6752 Remote Similarity NPD7503 Approved
0.6739 Remote Similarity NPD6942 Approved
0.6739 Remote Similarity NPD7339 Approved
0.6737 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6735 Remote Similarity NPD5363 Approved
0.6726 Remote Similarity NPD4632 Approved
0.6724 Remote Similarity NPD7100 Approved
0.6724 Remote Similarity NPD7101 Approved
0.6701 Remote Similarity NPD7154 Phase 3
0.6699 Remote Similarity NPD6001 Approved
0.6696 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD5279 Phase 3
0.6639 Remote Similarity NPD7319 Approved
0.6638 Remote Similarity NPD6314 Approved
0.6638 Remote Similarity NPD6335 Approved
0.6638 Remote Similarity NPD6313 Approved
0.6637 Remote Similarity NPD6053 Discontinued
0.6636 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6633 Remote Similarity NPD3668 Phase 3
0.6632 Remote Similarity NPD6929 Approved
0.663 Remote Similarity NPD6926 Approved
0.663 Remote Similarity NPD6924 Approved
0.66 Remote Similarity NPD7750 Discontinued
0.66 Remote Similarity NPD7524 Approved
0.6583 Remote Similarity NPD7492 Approved
0.6577 Remote Similarity NPD5128 Approved
0.6577 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6577 Remote Similarity NPD4730 Approved
0.6577 Remote Similarity NPD4729 Approved
0.6566 Remote Similarity NPD1696 Phase 3
0.6562 Remote Similarity NPD4821 Approved
0.6562 Remote Similarity NPD4822 Approved
0.6562 Remote Similarity NPD4819 Approved
0.6562 Remote Similarity NPD4820 Approved
0.6562 Remote Similarity NPD6931 Approved
0.6562 Remote Similarity NPD6930 Phase 2
0.6559 Remote Similarity NPD8264 Approved
0.6552 Remote Similarity NPD6009 Approved
0.6545 Remote Similarity NPD4767 Approved
0.6545 Remote Similarity NPD4768 Approved
0.6538 Remote Similarity NPD5282 Discontinued
0.6531 Remote Similarity NPD5362 Discontinued
0.6529 Remote Similarity NPD6616 Approved
0.6526 Remote Similarity NPD4268 Approved
0.6526 Remote Similarity NPD4271 Approved
0.6526 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6054 Approved
0.6514 Remote Similarity NPD4754 Approved
0.6505 Remote Similarity NPD5284 Approved
0.6505 Remote Similarity NPD5281 Approved
0.65 Remote Similarity NPD4519 Discontinued
0.65 Remote Similarity NPD4249 Approved
0.65 Remote Similarity NPD4623 Approved
0.6489 Remote Similarity NPD6933 Approved
0.6486 Remote Similarity NPD6412 Phase 2
0.6477 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6475 Remote Similarity NPD7078 Approved
0.6471 Remote Similarity NPD6909 Approved
0.6471 Remote Similarity NPD6673 Approved
0.6471 Remote Similarity NPD6015 Approved
0.6471 Remote Similarity NPD6016 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data