Structure

Physi-Chem Properties

Molecular Weight:  334.21
Volume:  356.058
LogP:  3.33
LogD:  2.841
LogS:  -4.293
# Rotatable Bonds:  0
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.543
Synthetic Accessibility Score:  5.036
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.961
MDCK Permeability:  2.6471940145711415e-05
Pgp-inhibitor:  0.097
Pgp-substrate:  0.456
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.097

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.325
Plasma Protein Binding (PPB):  84.90914916992188%
Volume Distribution (VD):  1.144
Pgp-substrate:  9.266329765319824%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.125
CYP2C19-inhibitor:  0.141
CYP2C19-substrate:  0.791
CYP2C9-inhibitor:  0.202
CYP2C9-substrate:  0.243
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.085
CYP3A4-inhibitor:  0.228
CYP3A4-substrate:  0.448

ADMET: Excretion

Clearance (CL):  8.852
Half-life (T1/2):  0.784

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.114
Drug-inuced Liver Injury (DILI):  0.236
AMES Toxicity:  0.679
Rat Oral Acute Toxicity:  0.667
Maximum Recommended Daily Dose:  0.938
Skin Sensitization:  0.564
Carcinogencity:  0.096
Eye Corrosion:  0.102
Eye Irritation:  0.816
Respiratory Toxicity:  0.816

Download Data

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

  Natural Product: NPC472972

Natural Product ID:  NPC472972
Common Name*:   KFEZPUHNOOFISQ-PBGAUENZSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KFEZPUHNOOFISQ-PBGAUENZSA-N
Standard InCHI:  InChI=1S/C20H30O4/c1-12(2)13-6-9-20(16(22)10-13)19(5)8-7-15(21)18(3,4)14(19)11-17(23)24-20/h10,12,14-15,21H,6-9,11H2,1-5H3/t14-,15-,19-,20-/m1/s1
SMILES:  CC(C)C1=CC(=O)C2(CC1)C3(CCC(C(C3CC(=O)O2)(C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3594336
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans

*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
NPO32900 chloranthus sessilifolius Species Chloranthaceae Eukaryota Whole plants Fengqi Mountains, Sichuan Province, China 2012-Aug PMID[26126961]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[529871]

☑ 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 NPC472972 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
0.9278 High Similarity NPC275583
0.8911 High Similarity NPC293850
0.8835 High Similarity NPC171888
0.8835 High Similarity NPC146945
0.8812 High Similarity NPC3316
0.8812 High Similarity NPC144854
0.8762 High Similarity NPC473798
0.875 High Similarity NPC477437
0.875 High Similarity NPC477438
0.8737 High Similarity NPC477435
0.8737 High Similarity NPC477436
0.8725 High Similarity NPC277017
0.8725 High Similarity NPC192813
0.8725 High Similarity NPC154608
0.87 High Similarity NPC179208
0.8679 High Similarity NPC40632
0.8679 High Similarity NPC328374
0.8679 High Similarity NPC235539
0.8679 High Similarity NPC251236
0.8679 High Similarity NPC152199
0.8679 High Similarity NPC96312
0.8679 High Similarity NPC134869
0.8667 High Similarity NPC194100
0.8667 High Similarity NPC208998
0.8667 High Similarity NPC49451
0.8667 High Similarity NPC7921
0.8654 High Similarity NPC201992
0.8646 High Similarity NPC477439
0.8586 High Similarity NPC104861
0.8585 High Similarity NPC474906
0.8585 High Similarity NPC18547
0.8571 High Similarity NPC289312
0.8571 High Similarity NPC11252
0.8571 High Similarity NPC474516
0.8558 High Similarity NPC210005
0.8529 High Similarity NPC102352
0.8519 High Similarity NPC297179
0.8519 High Similarity NPC17772
0.8515 High Similarity NPC282233
0.8515 High Similarity NPC95585
0.8491 Intermediate Similarity NPC51978
0.8491 Intermediate Similarity NPC472926
0.8485 Intermediate Similarity NPC114274
0.8476 Intermediate Similarity NPC34315
0.8469 Intermediate Similarity NPC96859
0.8469 Intermediate Similarity NPC328162
0.8469 Intermediate Similarity NPC305483
0.8462 Intermediate Similarity NPC27814
0.8447 Intermediate Similarity NPC202524
0.8447 Intermediate Similarity NPC44063
0.8426 Intermediate Similarity NPC97908
0.8426 Intermediate Similarity NPC470854
0.8426 Intermediate Similarity NPC474654
0.8426 Intermediate Similarity NPC122033
0.8426 Intermediate Similarity NPC287343
0.8384 Intermediate Similarity NPC473456
0.8367 Intermediate Similarity NPC470016
0.8367 Intermediate Similarity NPC317586
0.8365 Intermediate Similarity NPC94529
0.8365 Intermediate Similarity NPC476479
0.835 Intermediate Similarity NPC469607
0.835 Intermediate Similarity NPC181357
0.8349 Intermediate Similarity NPC188667
0.8349 Intermediate Similarity NPC204552
0.8349 Intermediate Similarity NPC251310
0.8333 Intermediate Similarity NPC478057
0.8333 Intermediate Similarity NPC207217
0.8333 Intermediate Similarity NPC95899
0.8333 Intermediate Similarity NPC270958
0.8333 Intermediate Similarity NPC159442
0.8318 Intermediate Similarity NPC202889
0.8317 Intermediate Similarity NPC471412
0.83 Intermediate Similarity NPC475876
0.83 Intermediate Similarity NPC264378
0.83 Intermediate Similarity NPC260149
0.83 Intermediate Similarity NPC58942
0.8298 Intermediate Similarity NPC73038
0.8286 Intermediate Similarity NPC77947
0.8286 Intermediate Similarity NPC141350
0.8286 Intermediate Similarity NPC2766
0.8286 Intermediate Similarity NPC286174
0.8283 Intermediate Similarity NPC219353
0.8273 Intermediate Similarity NPC470777
0.8273 Intermediate Similarity NPC472933
0.8269 Intermediate Similarity NPC472925
0.8265 Intermediate Similarity NPC245972
0.8265 Intermediate Similarity NPC196485
0.8265 Intermediate Similarity NPC166906
0.8257 Intermediate Similarity NPC472927
0.8257 Intermediate Similarity NPC309433
0.8252 Intermediate Similarity NPC96268
0.8247 Intermediate Similarity NPC168027
0.8247 Intermediate Similarity NPC99380
0.8247 Intermediate Similarity NPC185936
0.8247 Intermediate Similarity NPC248913
0.8235 Intermediate Similarity NPC308726
0.8235 Intermediate Similarity NPC22388
0.8235 Intermediate Similarity NPC119601
0.8224 Intermediate Similarity NPC90769
0.8224 Intermediate Similarity NPC71348
0.8224 Intermediate Similarity NPC280782
0.8218 Intermediate Similarity NPC471413
0.8218 Intermediate Similarity NPC471727
0.8218 Intermediate Similarity NPC327431
0.8208 Intermediate Similarity NPC197428
0.8208 Intermediate Similarity NPC129689
0.82 Intermediate Similarity NPC43747
0.82 Intermediate Similarity NPC108078
0.82 Intermediate Similarity NPC170131
0.8198 Intermediate Similarity NPC112038
0.8198 Intermediate Similarity NPC109607
0.8198 Intermediate Similarity NPC107338
0.819 Intermediate Similarity NPC275539
0.819 Intermediate Similarity NPC322903
0.819 Intermediate Similarity NPC189075
0.8182 Intermediate Similarity NPC134067
0.8182 Intermediate Similarity NPC118638
0.8182 Intermediate Similarity NPC473240
0.8182 Intermediate Similarity NPC474727
0.8182 Intermediate Similarity NPC139570
0.8173 Intermediate Similarity NPC231530
0.8173 Intermediate Similarity NPC196528
0.8173 Intermediate Similarity NPC278628
0.8172 Intermediate Similarity NPC64600
0.8165 Intermediate Similarity NPC259306
0.8165 Intermediate Similarity NPC474734
0.8165 Intermediate Similarity NPC470628
0.8165 Intermediate Similarity NPC474046
0.8163 Intermediate Similarity NPC272075
0.8163 Intermediate Similarity NPC214756
0.8163 Intermediate Similarity NPC109414
0.8163 Intermediate Similarity NPC295643
0.8155 Intermediate Similarity NPC33973
0.8155 Intermediate Similarity NPC70967
0.8155 Intermediate Similarity NPC131366
0.8152 Intermediate Similarity NPC473420
0.8148 Intermediate Similarity NPC159333
0.8137 Intermediate Similarity NPC81530
0.8137 Intermediate Similarity NPC118964
0.8137 Intermediate Similarity NPC302537
0.8137 Intermediate Similarity NPC472643
0.8137 Intermediate Similarity NPC163372
0.8131 Intermediate Similarity NPC214797
0.8131 Intermediate Similarity NPC231589
0.8131 Intermediate Similarity NPC115303
0.8131 Intermediate Similarity NPC118860
0.8131 Intermediate Similarity NPC188738
0.8131 Intermediate Similarity NPC43775
0.8125 Intermediate Similarity NPC477046
0.8125 Intermediate Similarity NPC102822
0.8125 Intermediate Similarity NPC473229
0.8125 Intermediate Similarity NPC470921
0.8119 Intermediate Similarity NPC478056
0.8119 Intermediate Similarity NPC477854
0.8113 Intermediate Similarity NPC250018
0.8113 Intermediate Similarity NPC310546
0.8113 Intermediate Similarity NPC304495
0.8108 Intermediate Similarity NPC476529
0.8108 Intermediate Similarity NPC475775
0.8108 Intermediate Similarity NPC469488
0.8105 Intermediate Similarity NPC325594
0.8105 Intermediate Similarity NPC202394
0.81 Intermediate Similarity NPC476327
0.81 Intermediate Similarity NPC469369
0.81 Intermediate Similarity NPC202833
0.81 Intermediate Similarity NPC469528
0.81 Intermediate Similarity NPC173272
0.81 Intermediate Similarity NPC94337
0.81 Intermediate Similarity NPC62516
0.81 Intermediate Similarity NPC476318
0.81 Intermediate Similarity NPC477853
0.81 Intermediate Similarity NPC157113
0.8095 Intermediate Similarity NPC475294
0.8095 Intermediate Similarity NPC230541
0.8095 Intermediate Similarity NPC110496
0.8091 Intermediate Similarity NPC473590
0.8081 Intermediate Similarity NPC196227
0.8081 Intermediate Similarity NPC250075
0.8081 Intermediate Similarity NPC470957
0.8081 Intermediate Similarity NPC293086
0.8081 Intermediate Similarity NPC74751
0.8081 Intermediate Similarity NPC470958
0.8081 Intermediate Similarity NPC212812
0.8077 Intermediate Similarity NPC470251
0.8077 Intermediate Similarity NPC40170
0.8077 Intermediate Similarity NPC2436
0.8077 Intermediate Similarity NPC475036
0.8077 Intermediate Similarity NPC65523
0.8077 Intermediate Similarity NPC135854
0.8077 Intermediate Similarity NPC137657
0.8077 Intermediate Similarity NPC213366
0.8077 Intermediate Similarity NPC216245
0.8077 Intermediate Similarity NPC29705
0.8073 Intermediate Similarity NPC470919
0.8073 Intermediate Similarity NPC469877
0.8073 Intermediate Similarity NPC323821
0.8073 Intermediate Similarity NPC470953
0.8073 Intermediate Similarity NPC143268
0.8073 Intermediate Similarity NPC45218
0.8073 Intermediate Similarity NPC268238

  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 NPC472972 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
0.8529 High Similarity NPD5739 Approved
0.8529 High Similarity NPD7128 Approved
0.8529 High Similarity NPD6675 Approved
0.8529 High Similarity NPD6402 Approved
0.8447 Intermediate Similarity NPD5697 Approved
0.8447 Intermediate Similarity NPD5701 Approved
0.8365 Intermediate Similarity NPD6011 Approved
0.8365 Intermediate Similarity NPD6899 Approved
0.8365 Intermediate Similarity NPD6881 Approved
0.8365 Intermediate Similarity NPD7320 Approved
0.8286 Intermediate Similarity NPD6372 Approved
0.8286 Intermediate Similarity NPD6012 Approved
0.8286 Intermediate Similarity NPD6373 Approved
0.8286 Intermediate Similarity NPD6013 Approved
0.8286 Intermediate Similarity NPD6014 Approved
0.8208 Intermediate Similarity NPD7290 Approved
0.8208 Intermediate Similarity NPD7102 Approved
0.8208 Intermediate Similarity NPD6883 Approved
0.8148 Intermediate Similarity NPD4632 Approved
0.8131 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.8131 Intermediate Similarity NPD6869 Approved
0.8131 Intermediate Similarity NPD8130 Phase 1
0.8131 Intermediate Similarity NPD6649 Approved
0.8131 Intermediate Similarity NPD6847 Approved
0.8131 Intermediate Similarity NPD6617 Approved
0.8131 Intermediate Similarity NPD6650 Approved
0.8091 Intermediate Similarity NPD6009 Approved
0.8081 Intermediate Similarity NPD7748 Approved
0.8061 Intermediate Similarity NPD7515 Phase 2
0.8056 Intermediate Similarity NPD8297 Approved
0.8056 Intermediate Similarity NPD6882 Approved
0.8036 Intermediate Similarity NPD6319 Approved
0.8021 Intermediate Similarity NPD3573 Approved
0.802 Intermediate Similarity NPD4755 Approved
0.802 Intermediate Similarity NPD6083 Phase 2
0.802 Intermediate Similarity NPD6084 Phase 2
0.8 Intermediate Similarity NPD5695 Phase 3
0.8 Intermediate Similarity NPD6008 Approved
0.7965 Intermediate Similarity NPD5983 Phase 2
0.7921 Intermediate Similarity NPD4697 Phase 3
0.7921 Intermediate Similarity NPD5221 Approved
0.7921 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD5222 Approved
0.7864 Intermediate Similarity NPD5286 Approved
0.7864 Intermediate Similarity NPD4700 Approved
0.7864 Intermediate Similarity NPD4696 Approved
0.7864 Intermediate Similarity NPD5285 Approved
0.7857 Intermediate Similarity NPD5328 Approved
0.7843 Intermediate Similarity NPD7902 Approved
0.7843 Intermediate Similarity NPD5173 Approved
0.7838 Intermediate Similarity NPD6274 Approved
0.7826 Intermediate Similarity NPD7604 Phase 2
0.7826 Intermediate Similarity NPD8328 Phase 3
0.7788 Intermediate Similarity NPD5223 Approved
0.7768 Intermediate Similarity NPD6317 Approved
0.7767 Intermediate Similarity NPD7638 Approved
0.7767 Intermediate Similarity NPD5696 Approved
0.7759 Intermediate Similarity NPD7492 Approved
0.7755 Intermediate Similarity NPD6672 Approved
0.7755 Intermediate Similarity NPD5737 Approved
0.7732 Intermediate Similarity NPD3618 Phase 1
0.7719 Intermediate Similarity NPD6054 Approved
0.7719 Intermediate Similarity NPD6059 Approved
0.7714 Intermediate Similarity NPD5225 Approved
0.7714 Intermediate Similarity NPD5224 Approved
0.7714 Intermediate Similarity NPD5211 Phase 2
0.7714 Intermediate Similarity NPD5226 Approved
0.7714 Intermediate Similarity NPD4633 Approved
0.77 Intermediate Similarity NPD6079 Approved
0.77 Intermediate Similarity NPD6411 Approved
0.7699 Intermediate Similarity NPD6314 Approved
0.7699 Intermediate Similarity NPD6335 Approved
0.7699 Intermediate Similarity NPD6313 Approved
0.7692 Intermediate Similarity NPD6336 Discontinued
0.7692 Intermediate Similarity NPD7639 Approved
0.7692 Intermediate Similarity NPD6616 Approved
0.7692 Intermediate Similarity NPD7640 Approved
0.7679 Intermediate Similarity NPD6868 Approved
0.7652 Intermediate Similarity NPD6016 Approved
0.7652 Intermediate Similarity NPD6015 Approved
0.7642 Intermediate Similarity NPD5174 Approved
0.7642 Intermediate Similarity NPD4754 Approved
0.7642 Intermediate Similarity NPD5175 Approved
0.7632 Intermediate Similarity NPD7101 Approved
0.7632 Intermediate Similarity NPD7100 Approved
0.7627 Intermediate Similarity NPD8293 Discontinued
0.7627 Intermediate Similarity NPD7078 Approved
0.7624 Intermediate Similarity NPD6399 Phase 3
0.7586 Intermediate Similarity NPD5988 Approved
0.7586 Intermediate Similarity NPD6370 Approved
0.757 Intermediate Similarity NPD5141 Approved
0.7563 Intermediate Similarity NPD7736 Approved
0.7549 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD7900 Approved
0.7545 Intermediate Similarity NPD4634 Approved
0.7523 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6909 Approved
0.75 Intermediate Similarity NPD4753 Phase 2
0.75 Intermediate Similarity NPD6904 Approved
0.75 Intermediate Similarity NPD6101 Approved
0.75 Intermediate Similarity NPD6908 Approved
0.75 Intermediate Similarity NPD3667 Approved
0.75 Intermediate Similarity NPD6080 Approved
0.75 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6673 Approved
0.75 Intermediate Similarity NPD4768 Approved
0.75 Intermediate Similarity NPD4767 Approved
0.7474 Intermediate Similarity NPD4695 Discontinued
0.7456 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD4202 Approved
0.7426 Intermediate Similarity NPD5692 Phase 3
0.7374 Intermediate Similarity NPD6409 Approved
0.7374 Intermediate Similarity NPD7146 Approved
0.7374 Intermediate Similarity NPD5279 Phase 3
0.7374 Intermediate Similarity NPD6684 Approved
0.7374 Intermediate Similarity NPD7521 Approved
0.7374 Intermediate Similarity NPD7334 Approved
0.7374 Intermediate Similarity NPD5330 Approved
0.7364 Intermediate Similarity NPD5128 Approved
0.7364 Intermediate Similarity NPD4730 Approved
0.7364 Intermediate Similarity NPD4729 Approved
0.7353 Intermediate Similarity NPD5694 Approved
0.7353 Intermediate Similarity NPD5693 Phase 1
0.7353 Intermediate Similarity NPD6050 Approved
0.735 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD3133 Approved
0.7347 Intermediate Similarity NPD3666 Approved
0.7347 Intermediate Similarity NPD4786 Approved
0.7347 Intermediate Similarity NPD3665 Phase 1
0.7327 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD5778 Approved
0.7282 Intermediate Similarity NPD5779 Approved
0.7273 Intermediate Similarity NPD6412 Phase 2
0.7273 Intermediate Similarity NPD6033 Approved
0.7232 Intermediate Similarity NPD5135 Approved
0.7232 Intermediate Similarity NPD5250 Approved
0.7232 Intermediate Similarity NPD5251 Approved
0.7232 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD5169 Approved
0.7232 Intermediate Similarity NPD5247 Approved
0.7232 Intermediate Similarity NPD5249 Phase 3
0.7232 Intermediate Similarity NPD5248 Approved
0.7228 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6903 Approved
0.7212 Intermediate Similarity NPD5282 Discontinued
0.7207 Intermediate Similarity NPD5168 Approved
0.72 Intermediate Similarity NPD6098 Approved
0.7172 Intermediate Similarity NPD4197 Approved
0.7168 Intermediate Similarity NPD5215 Approved
0.7168 Intermediate Similarity NPD5127 Approved
0.7168 Intermediate Similarity NPD5216 Approved
0.7168 Intermediate Similarity NPD5217 Approved
0.7155 Intermediate Similarity NPD7115 Discovery
0.7143 Intermediate Similarity NPD5210 Approved
0.7143 Intermediate Similarity NPD4629 Approved
0.7143 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7507 Approved
0.7105 Intermediate Similarity NPD6053 Discontinued
0.71 Intermediate Similarity NPD5329 Approved
0.708 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD7632 Discontinued
0.7054 Intermediate Similarity NPD6686 Approved
0.703 Intermediate Similarity NPD5690 Phase 2
0.703 Intermediate Similarity NPD5280 Approved
0.703 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4694 Approved
0.7019 Intermediate Similarity NPD5284 Approved
0.7019 Intermediate Similarity NPD5281 Approved
0.7 Intermediate Similarity NPD3668 Phase 3
0.6983 Remote Similarity NPD5167 Approved
0.6981 Remote Similarity NPD5654 Approved
0.697 Remote Similarity NPD4221 Approved
0.697 Remote Similarity NPD4223 Phase 3
0.6944 Remote Similarity NPD4225 Approved
0.6939 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7319 Approved
0.6931 Remote Similarity NPD1694 Approved
0.6931 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6907 Remote Similarity NPD3617 Approved
0.6899 Remote Similarity NPD6333 Approved
0.6899 Remote Similarity NPD6334 Approved
0.6893 Remote Similarity NPD5208 Approved
0.6887 Remote Similarity NPD6001 Approved
0.6857 Remote Similarity NPD8035 Phase 2
0.6857 Remote Similarity NPD8034 Phase 2
0.6852 Remote Similarity NPD5959 Approved
0.6825 Remote Similarity NPD7260 Phase 2
0.6814 Remote Similarity NPD5954 Clinical (unspecified phase)
0.68 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6777 Remote Similarity NPD6921 Approved
0.6765 Remote Similarity NPD1696 Phase 3
0.6762 Remote Similarity NPD46 Approved
0.6762 Remote Similarity NPD6698 Approved
0.6762 Remote Similarity NPD5207 Approved
0.6699 Remote Similarity NPD4519 Discontinued
0.6699 Remote Similarity NPD4689 Approved
0.6699 Remote Similarity NPD4690 Approved
0.6699 Remote Similarity NPD4693 Phase 3

  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