Structure

Physi-Chem Properties

Molecular Weight:  332.2
Volume:  353.422
LogP:  1.973
LogD:  2.373
LogS:  -3.791
# Rotatable Bonds:  2
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.623
Synthetic Accessibility Score:  4.859
Fsp3:  0.7
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:  -4.898
MDCK Permeability:  2.301593303855043e-05
Pgp-inhibitor:  0.013
Pgp-substrate:  0.507
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.135
30% Bioavailability (F30%):  0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.893
Plasma Protein Binding (PPB):  45.49333572387695%
Volume Distribution (VD):  0.782
Pgp-substrate:  59.626651763916016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.557
CYP2C19-inhibitor:  0.146
CYP2C19-substrate:  0.724
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.172
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.46
CYP3A4-inhibitor:  0.519
CYP3A4-substrate:  0.286

ADMET: Excretion

Clearance (CL):  9.109
Half-life (T1/2):  0.654

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.055
Drug-inuced Liver Injury (DILI):  0.109
AMES Toxicity:  0.034
Rat Oral Acute Toxicity:  0.57
Maximum Recommended Daily Dose:  0.964
Skin Sensitization:  0.104
Carcinogencity:  0.103
Eye Corrosion:  0.044
Eye Irritation:  0.128
Respiratory Toxicity:  0.966

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

  Natural Product: NPC474343

Natural Product ID:  NPC474343
Common Name*:   Pacovatinin C
IUPAC Name:   (3Z)-3-[2-[(1R,3S,4aR,8aR)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]ethylidene]oxolan-2-one
Synonyms:   Pacovatinin C
Standard InCHIKey:  XDMURUTWTFRCDW-HQQVEHBJSA-N
Standard InCHI:  InChI=1S/C20H28O4/c1-12-14(6-5-13-8-10-24-18(13)23)20(4)9-7-17(22)19(2,3)16(20)11-15(12)21/h5,14-16,21H,1,6-11H2,2-4H3/b13-5-/t14-,15-,16-,20+/m0/s1
SMILES:  CC1(C2CC(C(=C)C(C2(CCC1=O)C)CC=C3CCOC3=O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465486
PubChem CID:   10088154
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
NPO10066 Renealmia exaltata Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11520240]
NPO10066 Renealmia exaltata Species Zingiberaceae 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
NPT137 Cell Line L1210 Mus musculus IC50 = 4.7 ug.mL-1 PMID[463467]
NPT91 Cell Line KB Homo sapiens IC50 = 7.3 ug.mL-1 PMID[463467]

☑ 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 NPC474343 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
0.9222 High Similarity NPC50488
0.9222 High Similarity NPC474396
0.9032 High Similarity NPC57117
0.9022 High Similarity NPC72845
0.8936 High Similarity NPC183012
0.8925 High Similarity NPC139692
0.8889 High Similarity NPC329692
0.8866 High Similarity NPC81530
0.8854 High Similarity NPC23364
0.8842 High Similarity NPC242848
0.8842 High Similarity NPC134072
0.8842 High Similarity NPC234993
0.8788 High Similarity NPC118911
0.8776 High Similarity NPC136289
0.8763 High Similarity NPC476274
0.8763 High Similarity NPC472644
0.8763 High Similarity NPC117685
0.875 High Similarity NPC253826
0.8713 High Similarity NPC189075
0.8713 High Similarity NPC275539
0.871 High Similarity NPC51486
0.871 High Similarity NPC152467
0.8687 High Similarity NPC476237
0.8673 High Similarity NPC224720
0.8673 High Similarity NPC303559
0.8673 High Similarity NPC476223
0.8673 High Similarity NPC472643
0.8673 High Similarity NPC476240
0.8673 High Similarity NPC471412
0.866 High Similarity NPC124512
0.866 High Similarity NPC316598
0.866 High Similarity NPC478056
0.866 High Similarity NPC278386
0.866 High Similarity NPC159763
0.8632 High Similarity NPC250075
0.8617 High Similarity NPC233345
0.8617 High Similarity NPC177037
0.8617 High Similarity NPC186363
0.8617 High Similarity NPC472814
0.8614 High Similarity NPC110496
0.8602 High Similarity NPC168131
0.8602 High Similarity NPC5509
0.8587 High Similarity NPC181103
0.8571 High Similarity NPC471413
0.8571 High Similarity NPC86316
0.8571 High Similarity NPC106416
0.8571 High Similarity NPC110405
0.8571 High Similarity NPC65661
0.8571 High Similarity NPC47024
0.8557 High Similarity NPC254496
0.8557 High Similarity NPC170131
0.8557 High Similarity NPC73911
0.8542 High Similarity NPC209355
0.8515 High Similarity NPC469607
0.8515 High Similarity NPC478208
0.8511 High Similarity NPC182136
0.8511 High Similarity NPC158488
0.8511 High Similarity NPC232202
0.8495 Intermediate Similarity NPC104560
0.8476 Intermediate Similarity NPC25909
0.8469 Intermediate Similarity NPC222011
0.8469 Intermediate Similarity NPC108368
0.8469 Intermediate Similarity NPC473154
0.8469 Intermediate Similarity NPC57079
0.8454 Intermediate Similarity NPC202833
0.8447 Intermediate Similarity NPC474243
0.8438 Intermediate Similarity NPC476415
0.8431 Intermediate Similarity NPC475294
0.8421 Intermediate Similarity NPC477783
0.8421 Intermediate Similarity NPC472975
0.8404 Intermediate Similarity NPC174342
0.8404 Intermediate Similarity NPC73995
0.84 Intermediate Similarity NPC32577
0.84 Intermediate Similarity NPC162973
0.84 Intermediate Similarity NPC273005
0.84 Intermediate Similarity NPC155332
0.84 Intermediate Similarity NPC469606
0.84 Intermediate Similarity NPC114540
0.84 Intermediate Similarity NPC476081
0.84 Intermediate Similarity NPC31058
0.8387 Intermediate Similarity NPC305029
0.8387 Intermediate Similarity NPC312561
0.8384 Intermediate Similarity NPC474012
0.8384 Intermediate Similarity NPC476767
0.8384 Intermediate Similarity NPC306856
0.8384 Intermediate Similarity NPC476299
0.8384 Intermediate Similarity NPC476303
0.8384 Intermediate Similarity NPC266955
0.8381 Intermediate Similarity NPC12046
0.8381 Intermediate Similarity NPC194951
0.837 Intermediate Similarity NPC52628
0.8367 Intermediate Similarity NPC285513
0.8367 Intermediate Similarity NPC69385
0.8367 Intermediate Similarity NPC84335
0.8367 Intermediate Similarity NPC38530
0.8367 Intermediate Similarity NPC475709
0.8365 Intermediate Similarity NPC478211
0.8351 Intermediate Similarity NPC134067
0.8351 Intermediate Similarity NPC316215
0.8333 Intermediate Similarity NPC152778
0.8333 Intermediate Similarity NPC472645
0.8333 Intermediate Similarity NPC476416
0.8333 Intermediate Similarity NPC472303
0.8333 Intermediate Similarity NPC162615
0.8333 Intermediate Similarity NPC115021
0.8333 Intermediate Similarity NPC127609
0.8333 Intermediate Similarity NPC205034
0.8317 Intermediate Similarity NPC120321
0.8317 Intermediate Similarity NPC254202
0.8317 Intermediate Similarity NPC176883
0.8316 Intermediate Similarity NPC281942
0.8316 Intermediate Similarity NPC78973
0.8316 Intermediate Similarity NPC310479
0.8316 Intermediate Similarity NPC477782
0.8316 Intermediate Similarity NPC232426
0.8302 Intermediate Similarity NPC157441
0.83 Intermediate Similarity NPC472637
0.83 Intermediate Similarity NPC115899
0.83 Intermediate Similarity NPC115862
0.8298 Intermediate Similarity NPC226863
0.8298 Intermediate Similarity NPC277771
0.8298 Intermediate Similarity NPC215831
0.8286 Intermediate Similarity NPC247031
0.8286 Intermediate Similarity NPC100329
0.8286 Intermediate Similarity NPC97939
0.8286 Intermediate Similarity NPC474315
0.8286 Intermediate Similarity NPC132790
0.8283 Intermediate Similarity NPC141191
0.8283 Intermediate Similarity NPC216478
0.8283 Intermediate Similarity NPC252295
0.828 Intermediate Similarity NPC185638
0.828 Intermediate Similarity NPC131813
0.828 Intermediate Similarity NPC85698
0.828 Intermediate Similarity NPC220478
0.828 Intermediate Similarity NPC202394
0.8269 Intermediate Similarity NPC474901
0.8269 Intermediate Similarity NPC478210
0.8269 Intermediate Similarity NPC475941
0.8265 Intermediate Similarity NPC473153
0.8265 Intermediate Similarity NPC250757
0.8265 Intermediate Similarity NPC184065
0.8265 Intermediate Similarity NPC301534
0.8265 Intermediate Similarity NPC29952
0.8252 Intermediate Similarity NPC67321
0.8252 Intermediate Similarity NPC230541
0.8252 Intermediate Similarity NPC187435
0.8247 Intermediate Similarity NPC472976
0.8247 Intermediate Similarity NPC53685
0.8247 Intermediate Similarity NPC470697
0.8247 Intermediate Similarity NPC477129
0.8247 Intermediate Similarity NPC24861
0.8247 Intermediate Similarity NPC472977
0.8247 Intermediate Similarity NPC477130
0.8242 Intermediate Similarity NPC200513
0.8242 Intermediate Similarity NPC178676
0.8241 Intermediate Similarity NPC284068
0.8235 Intermediate Similarity NPC189616
0.8229 Intermediate Similarity NPC252433
0.8229 Intermediate Similarity NPC472811
0.8229 Intermediate Similarity NPC141831
0.8229 Intermediate Similarity NPC289479
0.8229 Intermediate Similarity NPC472978
0.8218 Intermediate Similarity NPC58329
0.8218 Intermediate Similarity NPC137430
0.8211 Intermediate Similarity NPC295312
0.8211 Intermediate Similarity NPC251528
0.8211 Intermediate Similarity NPC288699
0.8211 Intermediate Similarity NPC218927
0.8211 Intermediate Similarity NPC472973
0.8211 Intermediate Similarity NPC116620
0.8211 Intermediate Similarity NPC206001
0.8208 Intermediate Similarity NPC475524
0.8208 Intermediate Similarity NPC269530
0.8208 Intermediate Similarity NPC264634
0.8208 Intermediate Similarity NPC100267
0.82 Intermediate Similarity NPC201406
0.82 Intermediate Similarity NPC471041
0.8191 Intermediate Similarity NPC470012
0.819 Intermediate Similarity NPC478209
0.819 Intermediate Similarity NPC286880
0.819 Intermediate Similarity NPC5103
0.819 Intermediate Similarity NPC37116
0.8182 Intermediate Similarity NPC208094
0.8182 Intermediate Similarity NPC169205
0.8182 Intermediate Similarity NPC224356
0.8182 Intermediate Similarity NPC121402
0.8182 Intermediate Similarity NPC132753
0.8182 Intermediate Similarity NPC175351
0.8182 Intermediate Similarity NPC151681
0.8173 Intermediate Similarity NPC476802
0.8173 Intermediate Similarity NPC89171
0.8173 Intermediate Similarity NPC306265
0.8172 Intermediate Similarity NPC189311
0.8172 Intermediate Similarity NPC476602
0.8163 Intermediate Similarity NPC259042
0.8163 Intermediate Similarity NPC139459
0.8163 Intermediate Similarity NPC157686
0.8163 Intermediate Similarity NPC90014
0.8155 Intermediate Similarity NPC1679
0.8155 Intermediate Similarity NPC266570

  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 NPC474343 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
0.866 High Similarity NPD4225 Approved
0.8242 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.802 Intermediate Similarity NPD7639 Approved
0.802 Intermediate Similarity NPD7640 Approved
0.798 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7979 Intermediate Similarity NPD1694 Approved
0.7921 Intermediate Similarity NPD7638 Approved
0.7909 Intermediate Similarity NPD7115 Discovery
0.7778 Intermediate Similarity NPD6399 Phase 3
0.7755 Intermediate Similarity NPD5785 Approved
0.7736 Intermediate Similarity NPD5697 Approved
0.7708 Intermediate Similarity NPD3618 Phase 1
0.77 Intermediate Similarity NPD7748 Approved
0.7677 Intermediate Similarity NPD6079 Approved
0.7677 Intermediate Similarity NPD7515 Phase 2
0.7664 Intermediate Similarity NPD6881 Approved
0.7664 Intermediate Similarity NPD6011 Approved
0.7664 Intermediate Similarity NPD6899 Approved
0.7653 Intermediate Similarity NPD5328 Approved
0.7647 Intermediate Similarity NPD7902 Approved
0.7642 Intermediate Similarity NPD6675 Approved
0.7642 Intermediate Similarity NPD5739 Approved
0.7642 Intermediate Similarity NPD6402 Approved
0.7642 Intermediate Similarity NPD7128 Approved
0.7615 Intermediate Similarity NPD6649 Approved
0.7615 Intermediate Similarity NPD6650 Approved
0.7593 Intermediate Similarity NPD6373 Approved
0.7593 Intermediate Similarity NPD6372 Approved
0.7593 Intermediate Similarity NPD6013 Approved
0.7593 Intermediate Similarity NPD6012 Approved
0.7593 Intermediate Similarity NPD6014 Approved
0.757 Intermediate Similarity NPD5701 Approved
0.7549 Intermediate Similarity NPD5222 Approved
0.7549 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD4697 Phase 3
0.7549 Intermediate Similarity NPD5221 Approved
0.7524 Intermediate Similarity NPD5211 Phase 2
0.7523 Intermediate Similarity NPD7102 Approved
0.7523 Intermediate Similarity NPD7290 Approved
0.7523 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD6686 Approved
0.7477 Intermediate Similarity NPD6008 Approved
0.7476 Intermediate Similarity NPD5173 Approved
0.7474 Intermediate Similarity NPD3667 Approved
0.7455 Intermediate Similarity NPD8130 Phase 1
0.7455 Intermediate Similarity NPD6617 Approved
0.7455 Intermediate Similarity NPD6869 Approved
0.7455 Intermediate Similarity NPD6847 Approved
0.7449 Intermediate Similarity NPD3573 Approved
0.7426 Intermediate Similarity NPD5778 Approved
0.7426 Intermediate Similarity NPD5779 Approved
0.7387 Intermediate Similarity NPD6882 Approved
0.7387 Intermediate Similarity NPD8297 Approved
0.7383 Intermediate Similarity NPD5141 Approved
0.7358 Intermediate Similarity NPD7632 Discontinued
0.7353 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7900 Approved
0.7347 Intermediate Similarity NPD5330 Approved
0.7347 Intermediate Similarity NPD7146 Approved
0.7347 Intermediate Similarity NPD7521 Approved
0.7347 Intermediate Similarity NPD7334 Approved
0.7347 Intermediate Similarity NPD6409 Approved
0.7347 Intermediate Similarity NPD6684 Approved
0.7333 Intermediate Similarity NPD5285 Approved
0.7333 Intermediate Similarity NPD5286 Approved
0.7333 Intermediate Similarity NPD4696 Approved
0.7327 Intermediate Similarity NPD6411 Approved
0.732 Intermediate Similarity NPD3665 Phase 1
0.732 Intermediate Similarity NPD4786 Approved
0.732 Intermediate Similarity NPD3133 Approved
0.732 Intermediate Similarity NPD3666 Approved
0.7308 Intermediate Similarity NPD4755 Approved
0.7308 Intermediate Similarity NPD6084 Phase 2
0.7308 Intermediate Similarity NPD6083 Phase 2
0.7297 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD5223 Approved
0.7263 Intermediate Similarity NPD4695 Discontinued
0.7245 Intermediate Similarity NPD5363 Approved
0.7238 Intermediate Similarity NPD5696 Approved
0.72 Intermediate Similarity NPD6903 Approved
0.72 Intermediate Similarity NPD6672 Approved
0.72 Intermediate Similarity NPD5737 Approved
0.72 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD4633 Approved
0.7196 Intermediate Similarity NPD5224 Approved
0.7196 Intermediate Similarity NPD5225 Approved
0.7196 Intermediate Similarity NPD5226 Approved
0.7193 Intermediate Similarity NPD6868 Approved
0.7193 Intermediate Similarity NPD6274 Approved
0.7179 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5786 Approved
0.717 Intermediate Similarity NPD4700 Approved
0.7168 Intermediate Similarity NPD4632 Approved
0.7157 Intermediate Similarity NPD5693 Phase 1
0.713 Intermediate Similarity NPD6317 Approved
0.713 Intermediate Similarity NPD5174 Approved
0.713 Intermediate Similarity NPD5175 Approved
0.7129 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD6101 Approved
0.7117 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5695 Phase 3
0.7087 Intermediate Similarity NPD4202 Approved
0.7069 Intermediate Similarity NPD6335 Approved
0.7069 Intermediate Similarity NPD6313 Approved
0.7069 Intermediate Similarity NPD6314 Approved
0.7054 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6371 Approved
0.7053 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7101 Approved
0.7009 Intermediate Similarity NPD7100 Approved
0.7 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4519 Discontinued
0.7 Intermediate Similarity NPD4623 Approved
0.7 Intermediate Similarity NPD5279 Phase 3
0.699 Remote Similarity NPD8034 Phase 2
0.699 Remote Similarity NPD8035 Phase 2
0.699 Remote Similarity NPD7637 Suspended
0.6983 Remote Similarity NPD6009 Approved
0.6972 Remote Similarity NPD4754 Approved
0.697 Remote Similarity NPD3668 Phase 3
0.697 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6961 Remote Similarity NPD4753 Phase 2
0.6952 Remote Similarity NPD5210 Approved
0.6952 Remote Similarity NPD4629 Approved
0.6949 Remote Similarity NPD6319 Approved
0.6942 Remote Similarity NPD7507 Approved
0.6939 Remote Similarity NPD4269 Approved
0.6939 Remote Similarity NPD4270 Approved
0.693 Remote Similarity NPD6053 Discontinued
0.69 Remote Similarity NPD7520 Clinical (unspecified phase)
0.69 Remote Similarity NPD1696 Phase 3
0.6893 Remote Similarity NPD6698 Approved
0.6893 Remote Similarity NPD46 Approved
0.6891 Remote Similarity NPD5983 Phase 2
0.6875 Remote Similarity NPD5168 Approved
0.6875 Remote Similarity NPD4730 Approved
0.6875 Remote Similarity NPD4729 Approved
0.6875 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5128 Approved
0.6869 Remote Similarity NPD7154 Phase 3
0.6869 Remote Similarity NPD5362 Discontinued
0.686 Remote Similarity NPD7492 Approved
0.6857 Remote Similarity NPD6001 Approved
0.6847 Remote Similarity NPD4768 Approved
0.6847 Remote Similarity NPD4767 Approved
0.6827 Remote Similarity NPD5281 Approved
0.6827 Remote Similarity NPD5284 Approved
0.6807 Remote Similarity NPD6054 Approved
0.6803 Remote Similarity NPD6616 Approved
0.6796 Remote Similarity NPD6080 Approved
0.6796 Remote Similarity NPD6673 Approved
0.6796 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6904 Approved
0.6789 Remote Similarity NPD5344 Discontinued
0.6786 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6777 Remote Similarity NPD7604 Phase 2
0.6774 Remote Similarity NPD7319 Approved
0.6768 Remote Similarity NPD4223 Phase 3
0.6768 Remote Similarity NPD4221 Approved
0.6768 Remote Similarity NPD6435 Approved
0.6768 Remote Similarity NPD5209 Approved
0.6754 Remote Similarity NPD5249 Phase 3
0.6754 Remote Similarity NPD4634 Approved
0.6754 Remote Similarity NPD5247 Approved
0.6754 Remote Similarity NPD5169 Approved
0.6754 Remote Similarity NPD5135 Approved
0.6754 Remote Similarity NPD5250 Approved
0.6754 Remote Similarity NPD5251 Approved
0.6754 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5248 Approved
0.675 Remote Similarity NPD6015 Approved
0.675 Remote Similarity NPD6909 Approved
0.675 Remote Similarity NPD6016 Approved
0.675 Remote Similarity NPD6908 Approved
0.6748 Remote Similarity NPD7078 Approved
0.6735 Remote Similarity NPD4252 Approved
0.6733 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5207 Approved
0.6699 Remote Similarity NPD5208 Approved
0.6698 Remote Similarity NPD5282 Discontinued
0.6696 Remote Similarity NPD5217 Approved
0.6696 Remote Similarity NPD5215 Approved
0.6696 Remote Similarity NPD5216 Approved
0.6696 Remote Similarity NPD5127 Approved
0.6694 Remote Similarity NPD6370 Approved
0.6694 Remote Similarity NPD5988 Approved
0.6694 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD6336 Discontinued
0.6667 Remote Similarity NPD5369 Approved
0.6667 Remote Similarity NPD6059 Approved
0.6639 Remote Similarity NPD8328 Phase 3
0.6637 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6412 Phase 2
0.6635 Remote Similarity NPD6051 Approved
0.6634 Remote Similarity NPD4197 Approved
0.6613 Remote Similarity NPD8293 Discontinued
0.6606 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6574 Remote Similarity NPD7614 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