Structure

Physi-Chem Properties

Molecular Weight:  266.15
Volume:  272.215
LogP:  1.478
LogD:  1.344
LogS:  -2.764
# Rotatable Bonds:  0
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.647
Synthetic Accessibility Score:  5.005
Fsp3:  0.8
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:  -4.716
MDCK Permeability:  1.7632853996474296e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.221
30% Bioavailability (F30%):  0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.793
Plasma Protein Binding (PPB):  34.415443420410156%
Volume Distribution (VD):  0.783
Pgp-substrate:  47.026859283447266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.947
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.846
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.052
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.081
CYP3A4-inhibitor:  0.052
CYP3A4-substrate:  0.652

ADMET: Excretion

Clearance (CL):  6.966
Half-life (T1/2):  0.795

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.406
Drug-inuced Liver Injury (DILI):  0.086
AMES Toxicity:  0.659
Rat Oral Acute Toxicity:  0.934
Maximum Recommended Daily Dose:  0.926
Skin Sensitization:  0.359
Carcinogencity:  0.941
Eye Corrosion:  0.112
Eye Irritation:  0.511
Respiratory Toxicity:  0.939

Download Data

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

  Natural Product: NPC177232

Natural Product ID:  NPC177232
Common Name*:   8Alpha-Hydroxysambucoin
IUPAC Name:   (3aS,5aS,8S,9aR,9bR)-3a,8-dihydroxy-7,9a,9b-trimethyl-1,2,4,5a,8,9-hexahydrocyclopenta[c]chromen-3-one
Synonyms:   8Alpha-Hydroxysambucoin
Standard InCHIKey:  PYOQCUKYALILJL-RCXZEQIESA-N
Standard InCHI:  InChI=1S/C15H22O4/c1-9-6-12-13(2,7-10(9)16)14(3)5-4-11(17)15(14,18)8-19-12/h6,10,12,16,18H,4-5,7-8H2,1-3H3/t10-,12-,13-,14+,15-/m0/s1
SMILES:  CC1=C[C@H]2[C@](C)(C[C@@H]1O)[C@@]1(C)CCC(=O)[C@]1(CO2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518270
PubChem CID:   44584533
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002012] Oxanes

*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
NPO11220 Fusarium sporotrichioides Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[1800633]
NPO11220 Fusarium sporotrichioides Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[25475336]
NPO40517 Fusarium sporotrichioides MC-72083 Strain Nectriaceae Eukaryota n.a. n.a. n.a. PMID[3437285]
NPO11220 Fusarium sporotrichioides Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[8289061]
NPO10844 Lactarius pergamenus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4524 Bosistoa pentacocca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10844 Lactarius pergamenus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11220 Fusarium sporotrichioides Species Nectriaceae 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
NPT27 Others Unspecified LD50 > 10.0 ug PMID[501282]

☑ 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 NPC177232 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 NPC212465
0.8365 Intermediate Similarity NPC77089
0.8235 Intermediate Similarity NPC123505
0.8173 Intermediate Similarity NPC204884
0.8155 Intermediate Similarity NPC258532
0.8 Intermediate Similarity NPC144459
0.7961 Intermediate Similarity NPC475986
0.7944 Intermediate Similarity NPC41551
0.7944 Intermediate Similarity NPC50223
0.7885 Intermediate Similarity NPC474783
0.7885 Intermediate Similarity NPC232515
0.7885 Intermediate Similarity NPC260809
0.7857 Intermediate Similarity NPC197107
0.7843 Intermediate Similarity NPC109556
0.783 Intermediate Similarity NPC473169
0.781 Intermediate Similarity NPC75531
0.781 Intermediate Similarity NPC149124
0.7788 Intermediate Similarity NPC475956
0.7788 Intermediate Similarity NPC472004
0.7788 Intermediate Similarity NPC252242
0.7778 Intermediate Similarity NPC5103
0.7768 Intermediate Similarity NPC475130
0.7768 Intermediate Similarity NPC474286
0.7757 Intermediate Similarity NPC10150
0.7745 Intermediate Similarity NPC182811
0.7736 Intermediate Similarity NPC166607
0.7719 Intermediate Similarity NPC471999
0.7719 Intermediate Similarity NPC472001
0.7719 Intermediate Similarity NPC46570
0.7719 Intermediate Similarity NPC472000
0.7714 Intermediate Similarity NPC117185
0.7714 Intermediate Similarity NPC26478
0.7714 Intermediate Similarity NPC472755
0.7692 Intermediate Similarity NPC472753
0.7692 Intermediate Similarity NPC471401
0.7692 Intermediate Similarity NPC207885
0.7692 Intermediate Similarity NPC26557
0.7692 Intermediate Similarity NPC112613
0.7685 Intermediate Similarity NPC470257
0.7685 Intermediate Similarity NPC187876
0.767 Intermediate Similarity NPC79449
0.767 Intermediate Similarity NPC274458
0.767 Intermediate Similarity NPC474957
0.767 Intermediate Similarity NPC470541
0.7658 Intermediate Similarity NPC178289
0.7652 Intermediate Similarity NPC107493
0.7652 Intermediate Similarity NPC269642
0.7647 Intermediate Similarity NPC94337
0.7642 Intermediate Similarity NPC475676
0.7642 Intermediate Similarity NPC160843
0.7642 Intermediate Similarity NPC296950
0.7642 Intermediate Similarity NPC220964
0.7636 Intermediate Similarity NPC126691
0.7636 Intermediate Similarity NPC207251
0.7624 Intermediate Similarity NPC196227
0.7624 Intermediate Similarity NPC298919
0.7619 Intermediate Similarity NPC472754
0.7619 Intermediate Similarity NPC200672
0.7619 Intermediate Similarity NPC185530
0.7619 Intermediate Similarity NPC214714
0.76 Intermediate Similarity NPC475441
0.7573 Intermediate Similarity NPC134454
0.7573 Intermediate Similarity NPC17326
0.7573 Intermediate Similarity NPC347923
0.7573 Intermediate Similarity NPC471916
0.7573 Intermediate Similarity NPC476057
0.757 Intermediate Similarity NPC284365
0.757 Intermediate Similarity NPC85829
0.757 Intermediate Similarity NPC472749
0.757 Intermediate Similarity NPC472751
0.757 Intermediate Similarity NPC296945
0.757 Intermediate Similarity NPC476027
0.757 Intermediate Similarity NPC97202
0.757 Intermediate Similarity NPC50692
0.757 Intermediate Similarity NPC123726
0.757 Intermediate Similarity NPC260268
0.757 Intermediate Similarity NPC49958
0.757 Intermediate Similarity NPC214264
0.757 Intermediate Similarity NPC319077
0.757 Intermediate Similarity NPC202167
0.757 Intermediate Similarity NPC171137
0.757 Intermediate Similarity NPC48733
0.757 Intermediate Similarity NPC152695
0.757 Intermediate Similarity NPC150531
0.757 Intermediate Similarity NPC302607
0.7568 Intermediate Similarity NPC194100
0.7568 Intermediate Similarity NPC250109
0.7568 Intermediate Similarity NPC317210
0.7568 Intermediate Similarity NPC469454
0.7568 Intermediate Similarity NPC469496
0.7568 Intermediate Similarity NPC469463
0.7549 Intermediate Similarity NPC240838
0.7547 Intermediate Similarity NPC472747
0.7547 Intermediate Similarity NPC472750
0.7547 Intermediate Similarity NPC4620
0.7547 Intermediate Similarity NPC474775
0.7545 Intermediate Similarity NPC317107
0.7545 Intermediate Similarity NPC179798
0.7545 Intermediate Similarity NPC304180
0.7544 Intermediate Similarity NPC475041
0.7524 Intermediate Similarity NPC473174
0.7523 Intermediate Similarity NPC141350
0.7523 Intermediate Similarity NPC87335
0.7523 Intermediate Similarity NPC471400
0.7523 Intermediate Similarity NPC470615
0.7522 Intermediate Similarity NPC176513
0.7522 Intermediate Similarity NPC470775
0.7521 Intermediate Similarity NPC470922
0.7521 Intermediate Similarity NPC476729
0.75 Intermediate Similarity NPC312833
0.75 Intermediate Similarity NPC112780
0.75 Intermediate Similarity NPC220229
0.75 Intermediate Similarity NPC475060
0.75 Intermediate Similarity NPC326542
0.75 Intermediate Similarity NPC43285
0.75 Intermediate Similarity NPC83744
0.75 Intermediate Similarity NPC58370
0.7477 Intermediate Similarity NPC209502
0.7477 Intermediate Similarity NPC98038
0.7477 Intermediate Similarity NPC317687
0.7477 Intermediate Similarity NPC169843
0.7477 Intermediate Similarity NPC204833
0.7477 Intermediate Similarity NPC146731
0.7477 Intermediate Similarity NPC313921
0.7477 Intermediate Similarity NPC472748
0.7477 Intermediate Similarity NPC470104
0.7476 Intermediate Similarity NPC21302
0.7476 Intermediate Similarity NPC11396
0.7476 Intermediate Similarity NPC135576
0.7476 Intermediate Similarity NPC93271
0.7456 Intermediate Similarity NPC470776
0.7456 Intermediate Similarity NPC251310
0.7455 Intermediate Similarity NPC46407
0.7455 Intermediate Similarity NPC235077
0.7455 Intermediate Similarity NPC206595
0.7455 Intermediate Similarity NPC76084
0.7455 Intermediate Similarity NPC99760
0.7453 Intermediate Similarity NPC478176
0.7436 Intermediate Similarity NPC469789
0.7436 Intermediate Similarity NPC91693
0.7436 Intermediate Similarity NPC265557
0.7436 Intermediate Similarity NPC18945
0.7436 Intermediate Similarity NPC105926
0.7436 Intermediate Similarity NPC67251
0.7434 Intermediate Similarity NPC190286
0.7431 Intermediate Similarity NPC474664
0.7431 Intermediate Similarity NPC233379
0.7431 Intermediate Similarity NPC14862
0.7431 Intermediate Similarity NPC217201
0.7431 Intermediate Similarity NPC329417
0.7429 Intermediate Similarity NPC83709
0.7429 Intermediate Similarity NPC473176
0.7429 Intermediate Similarity NPC174314
0.7426 Intermediate Similarity NPC116726
0.7426 Intermediate Similarity NPC172101
0.7426 Intermediate Similarity NPC230623
0.7411 Intermediate Similarity NPC101965
0.7411 Intermediate Similarity NPC73300
0.7411 Intermediate Similarity NPC962
0.7411 Intermediate Similarity NPC312017
0.7411 Intermediate Similarity NPC56448
0.7411 Intermediate Similarity NPC9848
0.7411 Intermediate Similarity NPC101400
0.7411 Intermediate Similarity NPC108721
0.7407 Intermediate Similarity NPC149047
0.7407 Intermediate Similarity NPC60681
0.7404 Intermediate Similarity NPC474977
0.7404 Intermediate Similarity NPC27105
0.7404 Intermediate Similarity NPC477949
0.7404 Intermediate Similarity NPC69385
0.7395 Intermediate Similarity NPC473265
0.7395 Intermediate Similarity NPC473253
0.7395 Intermediate Similarity NPC470882
0.7391 Intermediate Similarity NPC19028
0.7391 Intermediate Similarity NPC9674
0.7391 Intermediate Similarity NPC477092
0.7387 Intermediate Similarity NPC473921
0.7387 Intermediate Similarity NPC475668
0.7387 Intermediate Similarity NPC475480
0.7387 Intermediate Similarity NPC474750
0.7383 Intermediate Similarity NPC475871
0.7383 Intermediate Similarity NPC473624
0.7383 Intermediate Similarity NPC168575
0.7383 Intermediate Similarity NPC475945
0.7383 Intermediate Similarity NPC191892
0.7383 Intermediate Similarity NPC194323
0.7379 Intermediate Similarity NPC316215
0.7374 Intermediate Similarity NPC179659
0.7373 Intermediate Similarity NPC24651
0.7368 Intermediate Similarity NPC473590
0.7368 Intermediate Similarity NPC239273
0.7368 Intermediate Similarity NPC218970
0.7364 Intermediate Similarity NPC11710
0.7364 Intermediate Similarity NPC284828
0.7364 Intermediate Similarity NPC173905
0.7364 Intermediate Similarity NPC472216
0.7364 Intermediate Similarity NPC5475
0.7364 Intermediate Similarity NPC15218
0.7364 Intermediate Similarity NPC101018
0.7358 Intermediate Similarity NPC474327

  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 NPC177232 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
0.7455 Intermediate Similarity NPD4634 Approved
0.7328 Intermediate Similarity NPD6319 Approved
0.729 Intermediate Similarity NPD5211 Phase 2
0.7257 Intermediate Similarity NPD4632 Approved
0.7238 Intermediate Similarity NPD4755 Approved
0.7179 Intermediate Similarity NPD6059 Approved
0.7179 Intermediate Similarity NPD6054 Approved
0.7156 Intermediate Similarity NPD5141 Approved
0.7119 Intermediate Similarity NPD6016 Approved
0.7119 Intermediate Similarity NPD6015 Approved
0.7117 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4700 Approved
0.7103 Intermediate Similarity NPD5286 Approved
0.7103 Intermediate Similarity NPD4696 Approved
0.7103 Intermediate Similarity NPD5285 Approved
0.7091 Intermediate Similarity NPD7128 Approved
0.7091 Intermediate Similarity NPD6402 Approved
0.7091 Intermediate Similarity NPD5739 Approved
0.7091 Intermediate Similarity NPD6675 Approved
0.7069 Intermediate Similarity NPD7115 Discovery
0.7059 Intermediate Similarity NPD6370 Approved
0.7059 Intermediate Similarity NPD5988 Approved
0.7037 Intermediate Similarity NPD5223 Approved
0.7027 Intermediate Similarity NPD5701 Approved
0.7027 Intermediate Similarity NPD5697 Approved
0.7027 Intermediate Similarity NPD6412 Phase 2
0.7018 Intermediate Similarity NPD8297 Approved
0.6992 Remote Similarity NPD7319 Approved
0.6991 Remote Similarity NPD6371 Approved
0.6972 Remote Similarity NPD4633 Approved
0.6972 Remote Similarity NPD5224 Approved
0.6972 Remote Similarity NPD5225 Approved
0.6972 Remote Similarity NPD5226 Approved
0.6964 Remote Similarity NPD6881 Approved
0.6964 Remote Similarity NPD7320 Approved
0.6964 Remote Similarity NPD6011 Approved
0.6964 Remote Similarity NPD6899 Approved
0.6952 Remote Similarity NPD5282 Discontinued
0.6942 Remote Similarity NPD7492 Approved
0.6923 Remote Similarity NPD6009 Approved
0.6909 Remote Similarity NPD4754 Approved
0.6909 Remote Similarity NPD5175 Approved
0.6909 Remote Similarity NPD5174 Approved
0.6903 Remote Similarity NPD6012 Approved
0.6903 Remote Similarity NPD6013 Approved
0.6903 Remote Similarity NPD6372 Approved
0.6903 Remote Similarity NPD6014 Approved
0.6903 Remote Similarity NPD6373 Approved
0.6893 Remote Similarity NPD4753 Phase 2
0.6885 Remote Similarity NPD6616 Approved
0.6885 Remote Similarity NPD7507 Approved
0.6875 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5778 Approved
0.6857 Remote Similarity NPD5779 Approved
0.6842 Remote Similarity NPD7290 Approved
0.6842 Remote Similarity NPD7102 Approved
0.6842 Remote Similarity NPD6883 Approved
0.6833 Remote Similarity NPD8515 Approved
0.6833 Remote Similarity NPD8516 Approved
0.6833 Remote Similarity NPD8517 Approved
0.6833 Remote Similarity NPD8513 Phase 3
0.6833 Remote Similarity NPD5983 Phase 2
0.6829 Remote Similarity NPD8293 Discontinued
0.6829 Remote Similarity NPD7078 Approved
0.6827 Remote Similarity NPD5785 Approved
0.6822 Remote Similarity NPD4697 Phase 3
0.6822 Remote Similarity NPD5221 Approved
0.6822 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5222 Approved
0.6789 Remote Similarity NPD7640 Approved
0.6789 Remote Similarity NPD7639 Approved
0.6786 Remote Similarity NPD4768 Approved
0.6786 Remote Similarity NPD4767 Approved
0.6783 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6783 Remote Similarity NPD8130 Phase 1
0.6783 Remote Similarity NPD6650 Approved
0.6783 Remote Similarity NPD6869 Approved
0.6783 Remote Similarity NPD6847 Approved
0.6783 Remote Similarity NPD6649 Approved
0.6783 Remote Similarity NPD6617 Approved
0.6774 Remote Similarity NPD6033 Approved
0.6774 Remote Similarity NPD7736 Approved
0.6765 Remote Similarity NPD5786 Approved
0.6762 Remote Similarity NPD7983 Approved
0.6759 Remote Similarity NPD6084 Phase 2
0.6759 Remote Similarity NPD6083 Phase 2
0.6759 Remote Similarity NPD5173 Approved
0.6733 Remote Similarity NPD3665 Phase 1
0.6733 Remote Similarity NPD3666 Approved
0.6733 Remote Similarity NPD3133 Approved
0.6731 Remote Similarity NPD5328 Approved
0.6729 Remote Similarity NPD5695 Phase 3
0.6729 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6724 Remote Similarity NPD6882 Approved
0.6724 Remote Similarity NPD6053 Discontinued
0.6721 Remote Similarity NPD7604 Phase 2
0.67 Remote Similarity NPD3667 Approved
0.6698 Remote Similarity NPD4202 Approved
0.6697 Remote Similarity NPD7638 Approved
0.6697 Remote Similarity NPD4225 Approved
0.6667 Remote Similarity NPD5128 Approved
0.6667 Remote Similarity NPD6698 Approved
0.6667 Remote Similarity NPD4730 Approved
0.6667 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD46 Approved
0.6667 Remote Similarity NPD4729 Approved
0.6638 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6614 Remote Similarity NPD7260 Phase 2
0.6613 Remote Similarity NPD6336 Discontinued
0.6609 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6079 Approved
0.6604 Remote Similarity NPD6411 Approved
0.6604 Remote Similarity NPD5693 Phase 1
0.6602 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6602 Remote Similarity NPD3618 Phase 1
0.6602 Remote Similarity NPD5279 Phase 3
0.6585 Remote Similarity NPD8328 Phase 3
0.6574 Remote Similarity NPD5210 Approved
0.6574 Remote Similarity NPD4629 Approved
0.6569 Remote Similarity NPD4786 Approved
0.6569 Remote Similarity NPD4197 Approved
0.656 Remote Similarity NPD8074 Phase 3
0.6555 Remote Similarity NPD6274 Approved
0.6552 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5251 Approved
0.6552 Remote Similarity NPD5135 Approved
0.6552 Remote Similarity NPD5248 Approved
0.6552 Remote Similarity NPD5249 Phase 3
0.6552 Remote Similarity NPD5169 Approved
0.6552 Remote Similarity NPD5250 Approved
0.6552 Remote Similarity NPD5247 Approved
0.6545 Remote Similarity NPD5696 Approved
0.6542 Remote Similarity NPD6399 Phase 3
0.6538 Remote Similarity NPD7524 Approved
0.6535 Remote Similarity NPD4270 Approved
0.6535 Remote Similarity NPD4269 Approved
0.6535 Remote Similarity NPD6435 Approved
0.6529 Remote Similarity NPD4522 Approved
0.6505 Remote Similarity NPD1694 Approved
0.6505 Remote Similarity NPD5329 Approved
0.65 Remote Similarity NPD6317 Approved
0.6496 Remote Similarity NPD5217 Approved
0.6496 Remote Similarity NPD5216 Approved
0.6496 Remote Similarity NPD5215 Approved
0.6496 Remote Similarity NPD5127 Approved
0.6491 Remote Similarity NPD6008 Approved
0.6471 Remote Similarity NPD6110 Phase 1
0.6465 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7637 Suspended
0.6446 Remote Similarity NPD6314 Approved
0.6446 Remote Similarity NPD6313 Approved
0.6446 Remote Similarity NPD6335 Approved
0.6442 Remote Similarity NPD4694 Approved
0.6442 Remote Similarity NPD5280 Approved
0.6442 Remote Similarity NPD5690 Phase 2
0.6436 Remote Similarity NPD5369 Approved
0.6423 Remote Similarity NPD6921 Approved
0.6415 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6415 Remote Similarity NPD6101 Approved
0.6408 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6393 Remote Similarity NPD7100 Approved
0.6393 Remote Similarity NPD7101 Approved
0.6373 Remote Similarity NPD4223 Phase 3
0.6373 Remote Similarity NPD4221 Approved
0.6364 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6346 Remote Similarity NPD1696 Phase 3
0.6346 Remote Similarity NPD5363 Approved
0.6337 Remote Similarity NPD4252 Approved
0.6337 Remote Similarity NPD5368 Approved
0.6333 Remote Similarity NPD5167 Approved
0.6321 Remote Similarity NPD5737 Approved
0.6321 Remote Similarity NPD6672 Approved
0.6311 Remote Similarity NPD7328 Approved
0.6311 Remote Similarity NPD5362 Discontinued
0.6311 Remote Similarity NPD7327 Approved
0.6311 Remote Similarity NPD6695 Phase 3
0.6308 Remote Similarity NPD6845 Suspended
0.629 Remote Similarity NPD6909 Approved
0.629 Remote Similarity NPD6908 Approved
0.629 Remote Similarity NPD6291 Clinical (unspecified phase)
0.629 Remote Similarity NPD7503 Approved
0.6286 Remote Similarity NPD6409 Approved
0.6286 Remote Similarity NPD7334 Approved
0.6286 Remote Similarity NPD6098 Approved
0.6286 Remote Similarity NPD5330 Approved
0.6286 Remote Similarity NPD7146 Approved
0.6286 Remote Similarity NPD6684 Approved
0.6286 Remote Similarity NPD7521 Approved
0.6279 Remote Similarity NPD5956 Approved
0.6271 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6673 Approved
0.6262 Remote Similarity NPD6080 Approved
0.6262 Remote Similarity NPD6904 Approved
0.626 Remote Similarity NPD7516 Approved
0.625 Remote Similarity NPD3668 Phase 3
0.6239 Remote Similarity NPD5168 Approved
0.6228 Remote Similarity NPD7632 Discontinued
0.6226 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6216 Remote Similarity NPD7839 Suspended
0.6214 Remote Similarity NPD4800 Clinical (unspecified phase)

  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