Structure

Physi-Chem Properties

Molecular Weight:  512.35
Volume:  564.491
LogP:  6.754
LogD:  5.42
LogS:  -5.166
# Rotatable Bonds:  9
TPSA:  80.67
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.275
Synthetic Accessibility Score:  6.037
Fsp3:  0.719
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.981
MDCK Permeability:  1.4800150893279351e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.015
Human Intestinal Absorption (HIA):  0.085
20% Bioavailability (F20%):  0.932
30% Bioavailability (F30%):  0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.473
Plasma Protein Binding (PPB):  93.17169952392578%
Volume Distribution (VD):  1.805
Pgp-substrate:  4.435008525848389%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.533
CYP2C19-inhibitor:  0.15
CYP2C19-substrate:  0.938
CYP2C9-inhibitor:  0.277
CYP2C9-substrate:  0.208
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.033
CYP3A4-inhibitor:  0.885
CYP3A4-substrate:  0.929

ADMET: Excretion

Clearance (CL):  11.114
Half-life (T1/2):  0.043

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.751
Drug-inuced Liver Injury (DILI):  0.907
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.893
Maximum Recommended Daily Dose:  0.026
Skin Sensitization:  0.02
Carcinogencity:  0.72
Eye Corrosion:  0.003
Eye Irritation:  0.022
Respiratory Toxicity:  0.805

Download Data

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

  Natural Product: NPC472728

Natural Product ID:  NPC472728
Common Name*:   IDXNDMRSSYBBIJ-WGCTUJHDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  IDXNDMRSSYBBIJ-WGCTUJHDSA-N
Standard InCHI:  InChI=1S/C32H48O5/c1-11-21(6)25(33)32-27-23(17-24(37-27)29(7,8)36)26(34)30(9,28(32)35)18-22(15-14-20(4)5)31(32,10)16-12-13-19(2)3/h13-14,21-22,24,36H,11-12,15-18H2,1-10H3/t21-,22-,24-,30+,31+,32-/m0/s1
SMILES:  CCC(C)C(=O)C12C3=C(CC(O3)C(C)(C)O)C(=O)C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3581912
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids

*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
NPO32997 Hypericum monogynum Species Hypericaceae Eukaryota Flowers n.a. n.a. PMID[25924023]
NPO32997 Hypericum monogynum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[27525351]

☑ 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 IC50 = 23700.0 nM PMID[469517]
NPT65 Cell Line HepG2 Homo sapiens Inhibition = 15.03 % PMID[469518]

☑ 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 NPC472728 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 NPC472727
0.9891 High Similarity NPC177680
0.9891 High Similarity NPC153776
0.9891 High Similarity NPC472729
0.9891 High Similarity NPC472730
0.9783 High Similarity NPC472732
0.9783 High Similarity NPC472731
0.9674 High Similarity NPC472734
0.9674 High Similarity NPC472733
0.9263 High Similarity NPC203388
0.9263 High Similarity NPC471331
0.9263 High Similarity NPC472687
0.9263 High Similarity NPC99657
0.9263 High Similarity NPC471330
0.9255 High Similarity NPC21681
0.9255 High Similarity NPC472675
0.9158 High Similarity NPC27105
0.89 High Similarity NPC471332
0.89 High Similarity NPC471333
0.8842 High Similarity NPC469819
0.8842 High Similarity NPC114162
0.8602 High Similarity NPC38885
0.8571 High Similarity NPC239895
0.8265 Intermediate Similarity NPC477241
0.8218 Intermediate Similarity NPC46761
0.8152 Intermediate Similarity NPC189237
0.8152 Intermediate Similarity NPC472684
0.8152 Intermediate Similarity NPC44963
0.81 Intermediate Similarity NPC93271
0.81 Intermediate Similarity NPC135576
0.8077 Intermediate Similarity NPC13385
0.8058 Intermediate Similarity NPC163249
0.7963 Intermediate Similarity NPC324683
0.7961 Intermediate Similarity NPC477870
0.7961 Intermediate Similarity NPC476213
0.7961 Intermediate Similarity NPC476134
0.7961 Intermediate Similarity NPC477871
0.7961 Intermediate Similarity NPC476246
0.7961 Intermediate Similarity NPC101067
0.7921 Intermediate Similarity NPC473164
0.7909 Intermediate Similarity NPC247069
0.7885 Intermediate Similarity NPC476126
0.7885 Intermediate Similarity NPC473163
0.7885 Intermediate Similarity NPC476235
0.787 Intermediate Similarity NPC239097
0.7864 Intermediate Similarity NPC54705
0.7843 Intermediate Similarity NPC477267
0.7843 Intermediate Similarity NPC473161
0.7843 Intermediate Similarity NPC472690
0.7843 Intermediate Similarity NPC124246
0.7843 Intermediate Similarity NPC472689
0.7843 Intermediate Similarity NPC477268
0.783 Intermediate Similarity NPC478052
0.783 Intermediate Similarity NPC32006
0.783 Intermediate Similarity NPC85529
0.783 Intermediate Similarity NPC292588
0.7822 Intermediate Similarity NPC473170
0.781 Intermediate Similarity NPC474330
0.781 Intermediate Similarity NPC474207
0.7788 Intermediate Similarity NPC475867
0.7788 Intermediate Similarity NPC270155
0.7778 Intermediate Similarity NPC472325
0.7778 Intermediate Similarity NPC470257
0.7767 Intermediate Similarity NPC147954
0.7745 Intermediate Similarity NPC471775
0.7736 Intermediate Similarity NPC40170
0.7723 Intermediate Similarity NPC473172
0.7723 Intermediate Similarity NPC318332
0.7706 Intermediate Similarity NPC473627
0.7692 Intermediate Similarity NPC110149
0.7684 Intermediate Similarity NPC212083
0.767 Intermediate Similarity NPC273269
0.7667 Intermediate Similarity NPC316553
0.7658 Intermediate Similarity NPC326264
0.7653 Intermediate Similarity NPC99909
0.7642 Intermediate Similarity NPC320294
0.7642 Intermediate Similarity NPC264048
0.7642 Intermediate Similarity NPC239716
0.7642 Intermediate Similarity NPC475321
0.7636 Intermediate Similarity NPC474229
0.7636 Intermediate Similarity NPC43775
0.7634 Intermediate Similarity NPC478246
0.7634 Intermediate Similarity NPC478247
0.7629 Intermediate Similarity NPC79573
0.7624 Intermediate Similarity NPC61275
0.7624 Intermediate Similarity NPC474807
0.76 Intermediate Similarity NPC469464
0.7593 Intermediate Similarity NPC43285
0.7593 Intermediate Similarity NPC58370
0.7579 Intermediate Similarity NPC327002
0.7576 Intermediate Similarity NPC143025
0.7576 Intermediate Similarity NPC474854
0.7573 Intermediate Similarity NPC8803
0.7573 Intermediate Similarity NPC269492
0.757 Intermediate Similarity NPC255309
0.757 Intermediate Similarity NPC470104
0.7568 Intermediate Similarity NPC205534
0.7568 Intermediate Similarity NPC193948
0.7551 Intermediate Similarity NPC477479
0.7551 Intermediate Similarity NPC477478
0.7551 Intermediate Similarity NPC203795
0.7551 Intermediate Similarity NPC470345
0.7551 Intermediate Similarity NPC229717
0.7549 Intermediate Similarity NPC196227
0.7549 Intermediate Similarity NPC472977
0.7549 Intermediate Similarity NPC67831
0.7549 Intermediate Similarity NPC472976
0.7549 Intermediate Similarity NPC174051
0.7549 Intermediate Similarity NPC473162
0.7547 Intermediate Similarity NPC473928
0.7547 Intermediate Similarity NPC80781
0.7545 Intermediate Similarity NPC37116
0.7527 Intermediate Similarity NPC325946
0.7525 Intermediate Similarity NPC471329
0.7525 Intermediate Similarity NPC262870
0.7525 Intermediate Similarity NPC146852
0.7525 Intermediate Similarity NPC116726
0.7525 Intermediate Similarity NPC475441
0.7525 Intermediate Similarity NPC296114
0.7525 Intermediate Similarity NPC19114
0.7524 Intermediate Similarity NPC316964
0.7524 Intermediate Similarity NPC198880
0.7524 Intermediate Similarity NPC112167
0.7523 Intermediate Similarity NPC318363
0.7523 Intermediate Similarity NPC473482
0.7523 Intermediate Similarity NPC475418
0.75 Intermediate Similarity NPC471999
0.75 Intermediate Similarity NPC472929
0.75 Intermediate Similarity NPC474570
0.75 Intermediate Similarity NPC96377
0.75 Intermediate Similarity NPC472074
0.75 Intermediate Similarity NPC472688
0.75 Intermediate Similarity NPC102352
0.75 Intermediate Similarity NPC477943
0.75 Intermediate Similarity NPC53844
0.75 Intermediate Similarity NPC294050
0.75 Intermediate Similarity NPC472676
0.75 Intermediate Similarity NPC32830
0.75 Intermediate Similarity NPC472073
0.75 Intermediate Similarity NPC472000
0.75 Intermediate Similarity NPC328997
0.7477 Intermediate Similarity NPC34315
0.7476 Intermediate Similarity NPC31021
0.7475 Intermediate Similarity NPC472324
0.7475 Intermediate Similarity NPC90652
0.7474 Intermediate Similarity NPC2482
0.7456 Intermediate Similarity NPC472934
0.7455 Intermediate Similarity NPC250018
0.7455 Intermediate Similarity NPC153239
0.7455 Intermediate Similarity NPC87335
0.7455 Intermediate Similarity NPC475065
0.7455 Intermediate Similarity NPC41405
0.7453 Intermediate Similarity NPC9878
0.7453 Intermediate Similarity NPC472702
0.7453 Intermediate Similarity NPC472685
0.7453 Intermediate Similarity NPC181645
0.7453 Intermediate Similarity NPC115862
0.7453 Intermediate Similarity NPC473514
0.7449 Intermediate Similarity NPC6185
0.7449 Intermediate Similarity NPC132228
0.7449 Intermediate Similarity NPC263997
0.7449 Intermediate Similarity NPC469948
0.7449 Intermediate Similarity NPC8518
0.7449 Intermediate Similarity NPC241512
0.7434 Intermediate Similarity NPC473898
0.7431 Intermediate Similarity NPC144854
0.7431 Intermediate Similarity NPC473169
0.7431 Intermediate Similarity NPC220974
0.7431 Intermediate Similarity NPC473284
0.7431 Intermediate Similarity NPC3316
0.7429 Intermediate Similarity NPC471582
0.7426 Intermediate Similarity NPC280592
0.7426 Intermediate Similarity NPC113393
0.7426 Intermediate Similarity NPC166554
0.7426 Intermediate Similarity NPC253177
0.7426 Intermediate Similarity NPC15059
0.7426 Intermediate Similarity NPC213636
0.7423 Intermediate Similarity NPC278648
0.7423 Intermediate Similarity NPC476082
0.7423 Intermediate Similarity NPC64600
0.7414 Intermediate Similarity NPC478051
0.7411 Intermediate Similarity NPC269530
0.7407 Intermediate Similarity NPC146731
0.7407 Intermediate Similarity NPC75531
0.7407 Intermediate Similarity NPC149124
0.7404 Intermediate Similarity NPC125622
0.7404 Intermediate Similarity NPC471463
0.74 Intermediate Similarity NPC470417
0.74 Intermediate Similarity NPC476708
0.74 Intermediate Similarity NPC53911
0.7396 Intermediate Similarity NPC116797
0.7391 Intermediate Similarity NPC106644
0.7391 Intermediate Similarity NPC17772
0.7387 Intermediate Similarity NPC5284
0.7387 Intermediate Similarity NPC286880
0.7387 Intermediate Similarity NPC29133
0.7383 Intermediate Similarity NPC283567
0.7383 Intermediate Similarity NPC70369
0.7383 Intermediate Similarity NPC53222
0.7383 Intermediate Similarity NPC473424

  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 NPC472728 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
0.7327 Intermediate Similarity NPD5328 Approved
0.7282 Intermediate Similarity NPD6399 Phase 3
0.7264 Intermediate Similarity NPD5696 Approved
0.7212 Intermediate Similarity NPD5282 Discontinued
0.7212 Intermediate Similarity NPD7748 Approved
0.72 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD3618 Phase 1
0.7184 Intermediate Similarity NPD6079 Approved
0.7172 Intermediate Similarity NPD4786 Approved
0.7172 Intermediate Similarity NPD3665 Phase 1
0.7172 Intermediate Similarity NPD3666 Approved
0.7172 Intermediate Similarity NPD3133 Approved
0.717 Intermediate Similarity NPD7902 Approved
0.7155 Intermediate Similarity NPD7115 Discovery
0.7143 Intermediate Similarity NPD3667 Approved
0.7143 Intermediate Similarity NPD5210 Approved
0.7143 Intermediate Similarity NPD4629 Approved
0.7113 Intermediate Similarity NPD4695 Discontinued
0.7105 Intermediate Similarity NPD8297 Approved
0.7075 Intermediate Similarity NPD4697 Phase 3
0.703 Intermediate Similarity NPD7146 Approved
0.703 Intermediate Similarity NPD7521 Approved
0.703 Intermediate Similarity NPD7334 Approved
0.703 Intermediate Similarity NPD5330 Approved
0.703 Intermediate Similarity NPD6684 Approved
0.703 Intermediate Similarity NPD6409 Approved
0.7027 Intermediate Similarity NPD7128 Approved
0.7027 Intermediate Similarity NPD5739 Approved
0.7027 Intermediate Similarity NPD6675 Approved
0.7027 Intermediate Similarity NPD6402 Approved
0.7019 Intermediate Similarity NPD6411 Approved
0.7009 Intermediate Similarity NPD4755 Approved
0.7009 Intermediate Similarity NPD6084 Phase 2
0.7009 Intermediate Similarity NPD6083 Phase 2
0.6991 Remote Similarity NPD6372 Approved
0.6991 Remote Similarity NPD6373 Approved
0.699 Remote Similarity NPD4753 Phase 2
0.6981 Remote Similarity NPD5695 Phase 3
0.697 Remote Similarity NPD4221 Approved
0.697 Remote Similarity NPD4223 Phase 3
0.6964 Remote Similarity NPD6412 Phase 2
0.6944 Remote Similarity NPD4225 Approved
0.6931 Remote Similarity NPD5329 Approved
0.693 Remote Similarity NPD4634 Approved
0.6916 Remote Similarity NPD5221 Approved
0.6916 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6916 Remote Similarity NPD5222 Approved
0.6903 Remote Similarity NPD6881 Approved
0.6903 Remote Similarity NPD6899 Approved
0.6903 Remote Similarity NPD7320 Approved
0.6893 Remote Similarity NPD6903 Approved
0.6893 Remote Similarity NPD6672 Approved
0.6893 Remote Similarity NPD5737 Approved
0.6893 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7900 Approved
0.6887 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6881 Remote Similarity NPD4700 Approved
0.6881 Remote Similarity NPD4696 Approved
0.6881 Remote Similarity NPD5286 Approved
0.6881 Remote Similarity NPD5285 Approved
0.687 Remote Similarity NPD6650 Approved
0.687 Remote Similarity NPD8130 Phase 1
0.687 Remote Similarity NPD6649 Approved
0.6863 Remote Similarity NPD5279 Phase 3
0.6857 Remote Similarity NPD7515 Phase 2
0.6852 Remote Similarity NPD5173 Approved
0.6833 Remote Similarity NPD6319 Approved
0.6833 Remote Similarity NPD6059 Approved
0.6833 Remote Similarity NPD6054 Approved
0.6832 Remote Similarity NPD3668 Phase 3
0.6832 Remote Similarity NPD4197 Approved
0.6827 Remote Similarity NPD6101 Approved
0.6827 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5223 Approved
0.6814 Remote Similarity NPD5701 Approved
0.6814 Remote Similarity NPD5697 Approved
0.6803 Remote Similarity NPD8328 Phase 3
0.68 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4202 Approved
0.6783 Remote Similarity NPD7102 Approved
0.6783 Remote Similarity NPD7290 Approved
0.6783 Remote Similarity NPD6883 Approved
0.6757 Remote Similarity NPD5224 Approved
0.6757 Remote Similarity NPD5211 Phase 2
0.6757 Remote Similarity NPD5226 Approved
0.6757 Remote Similarity NPD5225 Approved
0.6757 Remote Similarity NPD4633 Approved
0.6754 Remote Similarity NPD6011 Approved
0.6752 Remote Similarity NPD4632 Approved
0.6735 Remote Similarity NPD3617 Approved
0.6726 Remote Similarity NPD6008 Approved
0.6724 Remote Similarity NPD6869 Approved
0.6724 Remote Similarity NPD6847 Approved
0.6724 Remote Similarity NPD6617 Approved
0.6724 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6721 Remote Similarity NPD6370 Approved
0.6699 Remote Similarity NPD4519 Discontinued
0.6699 Remote Similarity NPD4689 Approved
0.6699 Remote Similarity NPD4690 Approved
0.6699 Remote Similarity NPD5280 Approved
0.6699 Remote Similarity NPD4693 Phase 3
0.6699 Remote Similarity NPD5205 Approved
0.6699 Remote Similarity NPD4688 Approved
0.6699 Remote Similarity NPD4694 Approved
0.6699 Remote Similarity NPD5690 Phase 2
0.6699 Remote Similarity NPD4623 Approved
0.6699 Remote Similarity NPD4138 Approved
0.6698 Remote Similarity NPD5281 Approved
0.6698 Remote Similarity NPD5284 Approved
0.6696 Remote Similarity NPD5174 Approved
0.6696 Remote Similarity NPD4754 Approved
0.6696 Remote Similarity NPD5175 Approved
0.6696 Remote Similarity NPD6013 Approved
0.6696 Remote Similarity NPD6014 Approved
0.6696 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6904 Approved
0.6667 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD6080 Approved
0.6667 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6673 Approved
0.664 Remote Similarity NPD8293 Discontinued
0.6639 Remote Similarity NPD6015 Approved
0.6639 Remote Similarity NPD6016 Approved
0.6637 Remote Similarity NPD5141 Approved
0.6636 Remote Similarity NPD5779 Approved
0.6636 Remote Similarity NPD5778 Approved
0.6635 Remote Similarity NPD3573 Approved
0.6634 Remote Similarity NPD4752 Clinical (unspecified phase)
0.663 Remote Similarity NPD7331 Phase 2
0.6613 Remote Similarity NPD7492 Approved
0.6609 Remote Similarity NPD6686 Approved
0.6587 Remote Similarity NPD7736 Approved
0.6585 Remote Similarity NPD5988 Approved
0.6579 Remote Similarity NPD4767 Approved
0.6579 Remote Similarity NPD4768 Approved
0.6569 Remote Similarity NPD4788 Approved
0.656 Remote Similarity NPD6616 Approved
0.6542 Remote Similarity NPD6050 Approved
0.6535 Remote Similarity NPD5369 Approved
0.6525 Remote Similarity NPD6053 Discontinued
0.6522 Remote Similarity NPD7341 Phase 2
0.6508 Remote Similarity NPD7078 Approved
0.6496 Remote Similarity NPD6371 Approved
0.6466 Remote Similarity NPD5128 Approved
0.6466 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6466 Remote Similarity NPD4729 Approved
0.6466 Remote Similarity NPD4730 Approved
0.646 Remote Similarity NPD5091 Approved
0.6457 Remote Similarity NPD6033 Approved
0.6455 Remote Similarity NPD7732 Phase 3
0.6455 Remote Similarity NPD7614 Phase 1
0.6449 Remote Similarity NPD5785 Approved
0.6449 Remote Similarity NPD5207 Approved
0.6449 Remote Similarity NPD5692 Phase 3
0.6446 Remote Similarity NPD6009 Approved
0.6446 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6442 Remote Similarity NPD1694 Approved
0.6436 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6434 Remote Similarity NPD7260 Phase 2
0.6415 Remote Similarity NPD5208 Approved
0.641 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6408 Remote Similarity NPD6110 Phase 1
0.6406 Remote Similarity NPD7319 Approved
0.64 Remote Similarity NPD7604 Phase 2
0.6393 Remote Similarity NPD6335 Approved
0.6389 Remote Similarity NPD5693 Phase 1
0.6389 Remote Similarity NPD8035 Phase 2
0.6389 Remote Similarity NPD7983 Approved
0.6389 Remote Similarity NPD5694 Approved
0.6389 Remote Similarity NPD8034 Phase 2
0.6381 Remote Similarity NPD6098 Approved
0.6381 Remote Similarity NPD5786 Approved
0.6379 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6371 Remote Similarity NPD5983 Phase 2
0.6364 Remote Similarity NPD6933 Approved
0.6364 Remote Similarity NPD6868 Approved
0.6364 Remote Similarity NPD6274 Approved
0.6356 Remote Similarity NPD5247 Approved
0.6356 Remote Similarity NPD5251 Approved
0.6356 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6356 Remote Similarity NPD5169 Approved
0.6356 Remote Similarity NPD5135 Approved
0.6356 Remote Similarity NPD5248 Approved
0.6356 Remote Similarity NPD5249 Phase 3
0.6356 Remote Similarity NPD5250 Approved
0.6356 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6341 Remote Similarity NPD7100 Approved
0.6341 Remote Similarity NPD7101 Approved
0.6339 Remote Similarity NPD7638 Approved
0.6337 Remote Similarity NPD4195 Approved
0.6325 Remote Similarity NPD5168 Approved
0.6321 Remote Similarity NPD7524 Approved
0.6311 Remote Similarity NPD6317 Approved
0.6303 Remote Similarity NPD5215 Approved
0.6303 Remote Similarity NPD5216 Approved
0.6303 Remote Similarity NPD5127 Approved
0.6303 Remote Similarity NPD5217 Approved
0.6299 Remote Similarity NPD7507 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