Structure

Physi-Chem Properties

Molecular Weight:  334.21
Volume:  356.058
LogP:  2.559
LogD:  2.776
LogS:  -3.686
# Rotatable Bonds:  2
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.602
Synthetic Accessibility Score:  4.914
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:  -4.779
MDCK Permeability:  5.1110477215843275e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.977
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.034
30% Bioavailability (F30%):  0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.774
Plasma Protein Binding (PPB):  25.854537963867188%
Volume Distribution (VD):  0.787
Pgp-substrate:  71.428955078125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.153
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.628
CYP2C9-inhibitor:  0.037
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.33
CYP3A4-inhibitor:  0.421
CYP3A4-substrate:  0.237

ADMET: Excretion

Clearance (CL):  10.649
Half-life (T1/2):  0.172

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.031
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.719
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.124
Carcinogencity:  0.042
Eye Corrosion:  0.052
Eye Irritation:  0.101
Respiratory Toxicity:  0.962

Download Data

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

  Natural Product: NPC57117

Natural Product ID:  NPC57117
Common Name*:   Pacovatinin B
IUPAC Name:   (3E)-3-[2-[(1R,3S,4aR,6S,8aS)-3,6-dihydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one
Synonyms:  
Standard InCHIKey:  HIWGZSDNWGIXOJ-TVDCSIBBSA-N
Standard InCHI:  InChI=1S/C20H30O4/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/h5,14-17,21-22H,1,6-11H2,2-4H3/b13-5+/t14-,15-,16-,17-,20+/m0/s1
SMILES:  C=C1[C@H](C/C=C/2CCOC2=O)[C@@]2(C)CC[C@@H](C(C)(C)[C@@H]2C[C@@H]1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL517955
PubChem CID:   10065491
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 > 10.0 ug.mL-1 PMID[536571]
NPT91 Cell Line KB Homo sapiens IC50 > 10.0 ug.mL-1 PMID[536571]

☑ 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 NPC57117 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 NPC72845
0.954 High Similarity NPC50488
0.954 High Similarity NPC474396
0.9195 High Similarity NPC329692
0.914 High Similarity NPC124512
0.914 High Similarity NPC159763
0.914 High Similarity NPC278386
0.913 High Similarity NPC234993
0.913 High Similarity NPC134072
0.9032 High Similarity NPC73911
0.9032 High Similarity NPC474343
0.8936 High Similarity NPC473154
0.8842 High Similarity NPC47024
0.8817 High Similarity NPC183012
0.8804 High Similarity NPC162615
0.8804 High Similarity NPC205034
0.8804 High Similarity NPC139692
0.8804 High Similarity NPC152778
0.8791 High Similarity NPC182136
0.8791 High Similarity NPC310479
0.8791 High Similarity NPC78973
0.8764 High Similarity NPC131813
0.8737 High Similarity NPC218107
0.8723 High Similarity NPC473153
0.8723 High Similarity NPC242848
0.8696 High Similarity NPC472811
0.866 High Similarity NPC476081
0.8652 High Similarity NPC476602
0.8646 High Similarity NPC251680
0.8617 High Similarity NPC276110
0.8602 High Similarity NPC472812
0.8602 High Similarity NPC53555
0.86 High Similarity NPC275539
0.86 High Similarity NPC189075
0.8587 High Similarity NPC280149
0.8587 High Similarity NPC221111
0.8587 High Similarity NPC158488
0.8571 High Similarity NPC476237
0.8571 High Similarity NPC120321
0.8557 High Similarity NPC303559
0.8557 High Similarity NPC471412
0.8542 High Similarity NPC216478
0.8542 High Similarity NPC23364
0.8526 High Similarity NPC202833
0.8526 High Similarity NPC165632
0.8526 High Similarity NPC16967
0.8511 High Similarity NPC105490
0.8511 High Similarity NPC191521
0.8511 High Similarity NPC119562
0.8511 High Similarity NPC279410
0.8511 High Similarity NPC24861
0.85 High Similarity NPC187435
0.85 High Similarity NPC110496
0.85 High Similarity NPC67321
0.8495 Intermediate Similarity NPC473675
0.8495 Intermediate Similarity NPC186363
0.8495 Intermediate Similarity NPC233345
0.8478 Intermediate Similarity NPC116620
0.8478 Intermediate Similarity NPC314727
0.8469 Intermediate Similarity NPC58329
0.8469 Intermediate Similarity NPC109195
0.8469 Intermediate Similarity NPC469606
0.8469 Intermediate Similarity NPC273005
0.8469 Intermediate Similarity NPC31058
0.8469 Intermediate Similarity NPC475038
0.8462 Intermediate Similarity NPC166857
0.8462 Intermediate Similarity NPC181103
0.8454 Intermediate Similarity NPC471413
0.8454 Intermediate Similarity NPC38855
0.8438 Intermediate Similarity NPC287668
0.8438 Intermediate Similarity NPC253826
0.8427 Intermediate Similarity NPC79945
0.8427 Intermediate Similarity NPC311070
0.8421 Intermediate Similarity NPC157686
0.8421 Intermediate Similarity NPC259042
0.8416 Intermediate Similarity NPC306265
0.8409 Intermediate Similarity NPC170303
0.8409 Intermediate Similarity NPC159148
0.8404 Intermediate Similarity NPC472640
0.8404 Intermediate Similarity NPC7349
0.8404 Intermediate Similarity NPC472641
0.84 Intermediate Similarity NPC469607
0.84 Intermediate Similarity NPC478208
0.8387 Intermediate Similarity NPC232202
0.8387 Intermediate Similarity NPC472642
0.8384 Intermediate Similarity NPC471938
0.837 Intermediate Similarity NPC104560
0.837 Intermediate Similarity NPC291665
0.8365 Intermediate Similarity NPC264153
0.8351 Intermediate Similarity NPC474440
0.8351 Intermediate Similarity NPC275086
0.8351 Intermediate Similarity NPC325229
0.8351 Intermediate Similarity NPC316598
0.8351 Intermediate Similarity NPC478056
0.8333 Intermediate Similarity NPC474243
0.8333 Intermediate Similarity NPC284518
0.8333 Intermediate Similarity NPC102048
0.8333 Intermediate Similarity NPC32223
0.8333 Intermediate Similarity NPC96055
0.8316 Intermediate Similarity NPC225474
0.8316 Intermediate Similarity NPC250075
0.8316 Intermediate Similarity NPC469596
0.8316 Intermediate Similarity NPC148000
0.8316 Intermediate Similarity NPC470255
0.83 Intermediate Similarity NPC471937
0.8298 Intermediate Similarity NPC177037
0.8298 Intermediate Similarity NPC472814
0.8298 Intermediate Similarity NPC78594
0.8298 Intermediate Similarity NPC329842
0.8298 Intermediate Similarity NPC477574
0.8295 Intermediate Similarity NPC281880
0.8283 Intermediate Similarity NPC162973
0.8283 Intermediate Similarity NPC472815
0.8283 Intermediate Similarity NPC471914
0.828 Intermediate Similarity NPC246028
0.828 Intermediate Similarity NPC168131
0.828 Intermediate Similarity NPC170633
0.828 Intermediate Similarity NPC79027
0.8269 Intermediate Similarity NPC12046
0.8269 Intermediate Similarity NPC194951
0.8265 Intermediate Similarity NPC476299
0.8265 Intermediate Similarity NPC476767
0.8265 Intermediate Similarity NPC474012
0.8265 Intermediate Similarity NPC476303
0.8265 Intermediate Similarity NPC16601
0.8265 Intermediate Similarity NPC324841
0.8261 Intermediate Similarity NPC175293
0.8261 Intermediate Similarity NPC305029
0.8261 Intermediate Similarity NPC473891
0.8252 Intermediate Similarity NPC478211
0.8247 Intermediate Similarity NPC473963
0.8247 Intermediate Similarity NPC51499
0.8247 Intermediate Similarity NPC99726
0.8242 Intermediate Similarity NPC30984
0.8242 Intermediate Similarity NPC65661
0.8242 Intermediate Similarity NPC86316
0.8242 Intermediate Similarity NPC52628
0.8242 Intermediate Similarity NPC106416
0.8229 Intermediate Similarity NPC472441
0.8222 Intermediate Similarity NPC476927
0.8218 Intermediate Similarity NPC218158
0.8218 Intermediate Similarity NPC34768
0.8211 Intermediate Similarity NPC99653
0.8211 Intermediate Similarity NPC475657
0.8211 Intermediate Similarity NPC38232
0.82 Intermediate Similarity NPC471208
0.82 Intermediate Similarity NPC254202
0.82 Intermediate Similarity NPC478057
0.82 Intermediate Similarity NPC95899
0.82 Intermediate Similarity NPC36688
0.82 Intermediate Similarity NPC176883
0.8191 Intermediate Similarity NPC51486
0.819 Intermediate Similarity NPC157441
0.819 Intermediate Similarity NPC25909
0.8182 Intermediate Similarity NPC81530
0.8173 Intermediate Similarity NPC132790
0.8173 Intermediate Similarity NPC100329
0.8173 Intermediate Similarity NPC247031
0.8173 Intermediate Similarity NPC97939
0.8172 Intermediate Similarity NPC472810
0.8172 Intermediate Similarity NPC106332
0.8172 Intermediate Similarity NPC472809
0.8172 Intermediate Similarity NPC277771
0.8163 Intermediate Similarity NPC278673
0.8163 Intermediate Similarity NPC57079
0.8163 Intermediate Similarity NPC108368
0.8155 Intermediate Similarity NPC478210
0.8152 Intermediate Similarity NPC85698
0.8152 Intermediate Similarity NPC471219
0.8152 Intermediate Similarity NPC185638
0.8144 Intermediate Similarity NPC473964
0.8144 Intermediate Similarity NPC190713
0.8144 Intermediate Similarity NPC29952
0.8144 Intermediate Similarity NPC93245
0.8137 Intermediate Similarity NPC302788
0.8137 Intermediate Similarity NPC179380
0.8125 Intermediate Similarity NPC477130
0.8125 Intermediate Similarity NPC476186
0.8125 Intermediate Similarity NPC477129
0.8119 Intermediate Similarity NPC118911
0.8119 Intermediate Similarity NPC296950
0.8119 Intermediate Similarity NPC146731
0.8111 Intermediate Similarity NPC256112
0.8111 Intermediate Similarity NPC2524
0.8105 Intermediate Similarity NPC477783
0.8105 Intermediate Similarity NPC124374
0.8105 Intermediate Similarity NPC234335
0.81 Intermediate Similarity NPC32577
0.81 Intermediate Similarity NPC471363
0.81 Intermediate Similarity NPC155332
0.81 Intermediate Similarity NPC164551
0.81 Intermediate Similarity NPC114540
0.81 Intermediate Similarity NPC137430
0.81 Intermediate Similarity NPC238397
0.81 Intermediate Similarity NPC136289
0.81 Intermediate Similarity NPC165250
0.8095 Intermediate Similarity NPC269530
0.809 Intermediate Similarity NPC469802
0.8085 Intermediate Similarity NPC288699
0.8085 Intermediate Similarity NPC174342

  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 NPC57117 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
0.914 High Similarity NPD4225 Approved
0.8646 High Similarity NPD7640 Approved
0.8646 High Similarity NPD7639 Approved
0.8542 High Similarity NPD7638 Approved
0.7921 Intermediate Similarity NPD7632 Discontinued
0.7912 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD1694 Approved
0.7636 Intermediate Similarity NPD7115 Discovery
0.7551 Intermediate Similarity NPD7637 Suspended
0.7547 Intermediate Similarity NPD6686 Approved
0.7476 Intermediate Similarity NPD5344 Discontinued
0.74 Intermediate Similarity NPD7748 Approved
0.7396 Intermediate Similarity NPD3618 Phase 1
0.7374 Intermediate Similarity NPD7515 Phase 2
0.7353 Intermediate Similarity NPD7902 Approved
0.7315 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD6399 Phase 3
0.7273 Intermediate Similarity NPD5785 Approved
0.7248 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6648 Approved
0.7196 Intermediate Similarity NPD6008 Approved
0.7188 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD5697 Approved
0.7129 Intermediate Similarity NPD5779 Approved
0.7129 Intermediate Similarity NPD5778 Approved
0.7115 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6695 Phase 3
0.7064 Intermediate Similarity NPD6881 Approved
0.7064 Intermediate Similarity NPD6011 Approved
0.7064 Intermediate Similarity NPD6899 Approved
0.7059 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7900 Approved
0.7037 Intermediate Similarity NPD6402 Approved
0.7037 Intermediate Similarity NPD7128 Approved
0.7037 Intermediate Similarity NPD5739 Approved
0.7037 Intermediate Similarity NPD6675 Approved
0.703 Intermediate Similarity NPD6079 Approved
0.7027 Intermediate Similarity NPD6650 Approved
0.7027 Intermediate Similarity NPD6649 Approved
0.701 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6014 Approved
0.7 Intermediate Similarity NPD6013 Approved
0.7 Intermediate Similarity NPD5328 Approved
0.7 Intermediate Similarity NPD6372 Approved
0.7 Intermediate Similarity NPD6012 Approved
0.7 Intermediate Similarity NPD6373 Approved
0.6979 Remote Similarity NPD3667 Approved
0.6972 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5701 Approved
0.6957 Remote Similarity NPD7327 Approved
0.6957 Remote Similarity NPD7328 Approved
0.6937 Remote Similarity NPD7290 Approved
0.6937 Remote Similarity NPD6371 Approved
0.6937 Remote Similarity NPD7102 Approved
0.6937 Remote Similarity NPD6883 Approved
0.6931 Remote Similarity NPD46 Approved
0.6931 Remote Similarity NPD6698 Approved
0.6931 Remote Similarity NPD7838 Discovery
0.6923 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4697 Phase 3
0.6923 Remote Similarity NPD5222 Approved
0.6923 Remote Similarity NPD5221 Approved
0.6923 Remote Similarity NPD8033 Approved
0.6916 Remote Similarity NPD5211 Phase 2
0.6909 Remote Similarity NPD7320 Approved
0.6903 Remote Similarity NPD4632 Approved
0.6897 Remote Similarity NPD7516 Approved
0.6875 Remote Similarity NPD8130 Phase 1
0.6875 Remote Similarity NPD6617 Approved
0.6875 Remote Similarity NPD6869 Approved
0.6875 Remote Similarity NPD6847 Approved
0.6869 Remote Similarity NPD7146 Approved
0.6869 Remote Similarity NPD6684 Approved
0.6869 Remote Similarity NPD7334 Approved
0.6869 Remote Similarity NPD6409 Approved
0.6869 Remote Similarity NPD5330 Approved
0.6869 Remote Similarity NPD7521 Approved
0.6863 Remote Similarity NPD8034 Phase 2
0.6863 Remote Similarity NPD8035 Phase 2
0.6857 Remote Similarity NPD6083 Phase 2
0.6857 Remote Similarity NPD5173 Approved
0.6857 Remote Similarity NPD6084 Phase 2
0.6842 Remote Similarity NPD6929 Approved
0.6838 Remote Similarity NPD8294 Approved
0.6838 Remote Similarity NPD8377 Approved
0.6837 Remote Similarity NPD3133 Approved
0.6837 Remote Similarity NPD4786 Approved
0.6837 Remote Similarity NPD3666 Approved
0.6837 Remote Similarity NPD3665 Phase 1
0.6833 Remote Similarity NPD7507 Approved
0.6832 Remote Similarity NPD6051 Approved
0.6827 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6814 Remote Similarity NPD8297 Approved
0.6814 Remote Similarity NPD6882 Approved
0.68 Remote Similarity NPD4751 Clinical (unspecified phase)
0.68 Remote Similarity NPD7750 Discontinued
0.68 Remote Similarity NPD7524 Approved
0.68 Remote Similarity NPD3573 Approved
0.6796 Remote Similarity NPD4202 Approved
0.6792 Remote Similarity NPD5696 Approved
0.6789 Remote Similarity NPD5141 Approved
0.678 Remote Similarity NPD8335 Approved
0.678 Remote Similarity NPD8296 Approved
0.678 Remote Similarity NPD7503 Approved
0.678 Remote Similarity NPD8378 Approved
0.678 Remote Similarity NPD8380 Approved
0.678 Remote Similarity NPD8379 Approved
0.6771 Remote Similarity NPD6931 Approved
0.6771 Remote Similarity NPD6930 Phase 2
0.6771 Remote Similarity NPD7525 Registered
0.6771 Remote Similarity NPD4695 Discontinued
0.6768 Remote Similarity NPD5363 Approved
0.6768 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5737 Approved
0.6733 Remote Similarity NPD6903 Approved
0.6733 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6672 Approved
0.6729 Remote Similarity NPD5286 Approved
0.6729 Remote Similarity NPD4696 Approved
0.6729 Remote Similarity NPD5285 Approved
0.6726 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6724 Remote Similarity NPD6009 Approved
0.6702 Remote Similarity NPD3701 Clinical (unspecified phase)
0.67 Remote Similarity NPD3574 Clinical (unspecified phase)
0.67 Remote Similarity NPD4249 Approved
0.6699 Remote Similarity NPD6411 Approved
0.6699 Remote Similarity NPD5693 Phase 1
0.6698 Remote Similarity NPD4755 Approved
0.6695 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD5695 Phase 3
0.6667 Remote Similarity NPD7645 Phase 2
0.6667 Remote Similarity NPD7319 Approved
0.6667 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6639 Remote Similarity NPD5983 Phase 2
0.6639 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6868 Approved
0.6638 Remote Similarity NPD6274 Approved
0.6634 Remote Similarity NPD4250 Approved
0.6634 Remote Similarity NPD4251 Approved
0.6633 Remote Similarity NPD5209 Approved
0.6632 Remote Similarity NPD6925 Approved
0.6632 Remote Similarity NPD5776 Phase 2
0.6612 Remote Similarity NPD7492 Approved
0.6607 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6606 Remote Similarity NPD5225 Approved
0.6606 Remote Similarity NPD5224 Approved
0.6606 Remote Similarity NPD5226 Approved
0.6606 Remote Similarity NPD4633 Approved
0.66 Remote Similarity NPD1696 Phase 3
0.6598 Remote Similarity NPD7514 Phase 3
0.6598 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6598 Remote Similarity NPD7332 Phase 2
0.6596 Remote Similarity NPD7339 Approved
0.6596 Remote Similarity NPD6942 Approved
0.6596 Remote Similarity NPD8264 Approved
0.6581 Remote Similarity NPD6317 Approved
0.6574 Remote Similarity NPD4700 Approved
0.6571 Remote Similarity NPD5282 Discontinued
0.6571 Remote Similarity NPD6001 Approved
0.6566 Remote Similarity NPD5362 Discontinued
0.6566 Remote Similarity NPD7154 Phase 3
0.6562 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7145 Approved
0.6557 Remote Similarity NPD6616 Approved
0.6555 Remote Similarity NPD6054 Approved
0.6545 Remote Similarity NPD5174 Approved
0.6545 Remote Similarity NPD5175 Approved
0.6538 Remote Similarity NPD7087 Discontinued
0.6535 Remote Similarity NPD4519 Discontinued
0.6535 Remote Similarity NPD4623 Approved
0.6535 Remote Similarity NPD5279 Phase 3
0.6531 Remote Similarity NPD6902 Approved
0.6529 Remote Similarity NPD7604 Phase 2
0.6525 Remote Similarity NPD6314 Approved
0.6525 Remote Similarity NPD6335 Approved
0.6525 Remote Similarity NPD6313 Approved
0.6518 Remote Similarity NPD6412 Phase 2
0.6509 Remote Similarity NPD4629 Approved
0.6509 Remote Similarity NPD5210 Approved
0.6505 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6101 Approved
0.6505 Remote Similarity NPD4753 Phase 2
0.6505 Remote Similarity NPD1695 Approved
0.6504 Remote Similarity NPD7078 Approved
0.65 Remote Similarity NPD6015 Approved
0.65 Remote Similarity NPD6016 Approved
0.65 Remote Similarity NPD3668 Phase 3
0.6491 Remote Similarity NPD4634 Approved
0.6489 Remote Similarity NPD6924 Approved
0.6489 Remote Similarity NPD6926 Approved
0.6471 Remote Similarity NPD7100 Approved
0.6471 Remote Similarity NPD7101 Approved
0.6465 Remote Similarity NPD4270 Approved
0.6465 Remote Similarity NPD4269 Approved
0.6452 Remote Similarity NPD7736 Approved
0.6446 Remote Similarity NPD5988 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