Structure

Physi-Chem Properties

Molecular Weight:  266.15
Volume:  272.215
LogP:  2.336
LogD:  1.363
LogS:  -3.972
# 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:  0.678
Synthetic Accessibility Score:  4.498
Fsp3:  0.867
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:  -4.794
MDCK Permeability:  3.081958129769191e-05
Pgp-inhibitor:  0.019
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.968
Plasma Protein Binding (PPB):  42.160972595214844%
Volume Distribution (VD):  0.801
Pgp-substrate:  77.21150970458984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.602
CYP2C19-inhibitor:  0.161
CYP2C19-substrate:  0.779
CYP2C9-inhibitor:  0.106
CYP2C9-substrate:  0.124
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.152
CYP3A4-inhibitor:  0.186
CYP3A4-substrate:  0.213

ADMET: Excretion

Clearance (CL):  5.932
Half-life (T1/2):  0.197

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.174
Drug-inuced Liver Injury (DILI):  0.145
AMES Toxicity:  0.145
Rat Oral Acute Toxicity:  0.246
Maximum Recommended Daily Dose:  0.161
Skin Sensitization:  0.13
Carcinogencity:  0.086
Eye Corrosion:  0.02
Eye Irritation:  0.047
Respiratory Toxicity:  0.631

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

  Natural Product: NPC296950

Natural Product ID:  NPC296950
Common Name*:   Pereniporin B
IUPAC Name:   (5R,5aS,9aS,9bS)-5,9b-dihydroxy-6,6,9a-trimethyl-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-3-one
Synonyms:  
Standard InCHIKey:  HLEGAPKZEJEXHT-FDRIWYBQSA-N
Standard InCHI:  InChI=1S/C15H22O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-12(17)19-8-15(9,14)18/h7,10-11,16,18H,4-6,8H2,1-3H3/t10-,11+,14+,15-/m1/s1
SMILES:  O[C@@H]1C=C2C(=O)OC[C@@]2([C@@]2([C@@H]1C(C)(C)CCC2)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL256709
PubChem CID:   161192
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. PMID[18179176]
NPO16566 Cinnamosma madagascariensis Species Canellaceae 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
NPT2 Others Unspecified Inhibition = 7.2 % PMID[451383]

☑ 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 NPC296950 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
0.9794 High Similarity NPC146731
0.9505 High Similarity NPC235014
0.9135 High Similarity NPC269530
0.9126 High Similarity NPC5103
0.91 High Similarity NPC159533
0.901 High Similarity NPC258532
0.8868 High Similarity NPC469496
0.8868 High Similarity NPC469454
0.8868 High Similarity NPC469463
0.8857 High Similarity NPC304180
0.8857 High Similarity NPC179798
0.8725 High Similarity NPC72842
0.87 High Similarity NPC23364
0.87 High Similarity NPC216478
0.8692 High Similarity NPC56448
0.8654 High Similarity NPC187435
0.8654 High Similarity NPC67321
0.8627 High Similarity NPC295791
0.8624 High Similarity NPC469684
0.86 High Similarity NPC91695
0.86 High Similarity NPC70145
0.8571 High Similarity NPC151393
0.8558 High Similarity NPC477125
0.8544 High Similarity NPC69171
0.8544 High Similarity NPC474165
0.8544 High Similarity NPC99510
0.8529 High Similarity NPC308824
0.8515 High Similarity NPC222303
0.8515 High Similarity NPC278386
0.8515 High Similarity NPC159763
0.8515 High Similarity NPC124512
0.8505 High Similarity NPC317107
0.8482 Intermediate Similarity NPC67569
0.8476 Intermediate Similarity NPC112780
0.8462 Intermediate Similarity NPC283850
0.8455 Intermediate Similarity NPC58662
0.8455 Intermediate Similarity NPC473656
0.8455 Intermediate Similarity NPC475323
0.8455 Intermediate Similarity NPC53396
0.8455 Intermediate Similarity NPC98249
0.8455 Intermediate Similarity NPC23046
0.8447 Intermediate Similarity NPC183571
0.8447 Intermediate Similarity NPC58329
0.8431 Intermediate Similarity NPC47024
0.8426 Intermediate Similarity NPC236217
0.8426 Intermediate Similarity NPC472002
0.8426 Intermediate Similarity NPC317687
0.8407 Intermediate Similarity NPC470265
0.8407 Intermediate Similarity NPC23786
0.84 Intermediate Similarity NPC183012
0.8396 Intermediate Similarity NPC306265
0.8384 Intermediate Similarity NPC115021
0.8378 Intermediate Similarity NPC284707
0.8367 Intermediate Similarity NPC15059
0.8365 Intermediate Similarity NPC99266
0.8365 Intermediate Similarity NPC156681
0.8349 Intermediate Similarity NPC25909
0.8349 Intermediate Similarity NPC477126
0.8333 Intermediate Similarity NPC469656
0.8333 Intermediate Similarity NPC67251
0.8333 Intermediate Similarity NPC316598
0.8333 Intermediate Similarity NPC324683
0.8333 Intermediate Similarity NPC469789
0.8333 Intermediate Similarity NPC469655
0.8333 Intermediate Similarity NPC474846
0.8319 Intermediate Similarity NPC46570
0.8318 Intermediate Similarity NPC474243
0.8318 Intermediate Similarity NPC42662
0.8302 Intermediate Similarity NPC143609
0.8288 Intermediate Similarity NPC473968
0.8286 Intermediate Similarity NPC475676
0.8286 Intermediate Similarity NPC220964
0.8283 Intermediate Similarity NPC186363
0.8283 Intermediate Similarity NPC233345
0.8283 Intermediate Similarity NPC252433
0.8273 Intermediate Similarity NPC117712
0.8269 Intermediate Similarity NPC469606
0.8269 Intermediate Similarity NPC273005
0.8269 Intermediate Similarity NPC164551
0.8269 Intermediate Similarity NPC476081
0.8269 Intermediate Similarity NPC31058
0.8269 Intermediate Similarity NPC137430
0.8265 Intermediate Similarity NPC168131
0.8261 Intermediate Similarity NPC8369
0.8261 Intermediate Similarity NPC470922
0.8261 Intermediate Similarity NPC24651
0.8257 Intermediate Similarity NPC42658
0.8257 Intermediate Similarity NPC126691
0.8257 Intermediate Similarity NPC476801
0.8252 Intermediate Similarity NPC474012
0.8252 Intermediate Similarity NPC476299
0.8246 Intermediate Similarity NPC107493
0.8241 Intermediate Similarity NPC161816
0.8241 Intermediate Similarity NPC29133
0.8241 Intermediate Similarity NPC115257
0.8241 Intermediate Similarity NPC478211
0.8235 Intermediate Similarity NPC474395
0.8235 Intermediate Similarity NPC73911
0.8224 Intermediate Similarity NPC37628
0.8224 Intermediate Similarity NPC94377
0.8224 Intermediate Similarity NPC469916
0.8224 Intermediate Similarity NPC275539
0.8224 Intermediate Similarity NPC189075
0.8224 Intermediate Similarity NPC322903
0.8224 Intermediate Similarity NPC472439
0.8214 Intermediate Similarity NPC108581
0.8214 Intermediate Similarity NPC186525
0.8214 Intermediate Similarity NPC50774
0.8214 Intermediate Similarity NPC475372
0.8214 Intermediate Similarity NPC478206
0.8214 Intermediate Similarity NPC709
0.8214 Intermediate Similarity NPC478205
0.8208 Intermediate Similarity NPC469607
0.8208 Intermediate Similarity NPC111952
0.82 Intermediate Similarity NPC475912
0.82 Intermediate Similarity NPC475657
0.8198 Intermediate Similarity NPC64318
0.8198 Intermediate Similarity NPC270478
0.819 Intermediate Similarity NPC293112
0.819 Intermediate Similarity NPC4620
0.819 Intermediate Similarity NPC8196
0.819 Intermediate Similarity NPC61442
0.8182 Intermediate Similarity NPC158488
0.8182 Intermediate Similarity NPC264153
0.8182 Intermediate Similarity NPC472307
0.8182 Intermediate Similarity NPC478212
0.8173 Intermediate Similarity NPC244456
0.8173 Intermediate Similarity NPC242666
0.8173 Intermediate Similarity NPC97435
0.8173 Intermediate Similarity NPC469657
0.8165 Intermediate Similarity NPC470961
0.8165 Intermediate Similarity NPC247031
0.8165 Intermediate Similarity NPC188738
0.8165 Intermediate Similarity NPC97939
0.8165 Intermediate Similarity NPC132790
0.8165 Intermediate Similarity NPC100329
0.8148 Intermediate Similarity NPC475922
0.8142 Intermediate Similarity NPC312536
0.8142 Intermediate Similarity NPC77689
0.8142 Intermediate Similarity NPC473636
0.8142 Intermediate Similarity NPC268958
0.8137 Intermediate Similarity NPC93245
0.8137 Intermediate Similarity NPC234993
0.8137 Intermediate Similarity NPC134072
0.8137 Intermediate Similarity NPC284518
0.8137 Intermediate Similarity NPC202833
0.8137 Intermediate Similarity NPC242848
0.8136 Intermediate Similarity NPC473593
0.8131 Intermediate Similarity NPC78966
0.8131 Intermediate Similarity NPC284732
0.8131 Intermediate Similarity NPC230541
0.8131 Intermediate Similarity NPC110496
0.8125 Intermediate Similarity NPC286528
0.8125 Intermediate Similarity NPC20302
0.8125 Intermediate Similarity NPC312824
0.8125 Intermediate Similarity NPC478204
0.8125 Intermediate Similarity NPC140055
0.8125 Intermediate Similarity NPC470492
0.8125 Intermediate Similarity NPC470493
0.8125 Intermediate Similarity NPC13713
0.8125 Intermediate Similarity NPC176513
0.8125 Intermediate Similarity NPC470775
0.8125 Intermediate Similarity NPC134430
0.8125 Intermediate Similarity NPC167606
0.8125 Intermediate Similarity NPC183580
0.812 Intermediate Similarity NPC204556
0.8119 Intermediate Similarity NPC474555
0.8119 Intermediate Similarity NPC469596
0.8119 Intermediate Similarity NPC24861
0.8119 Intermediate Similarity NPC225474
0.8119 Intermediate Similarity NPC57117
0.8119 Intermediate Similarity NPC148000
0.8119 Intermediate Similarity NPC250075
0.8113 Intermediate Similarity NPC203659
0.8108 Intermediate Similarity NPC474181
0.8108 Intermediate Similarity NPC147912
0.8108 Intermediate Similarity NPC67259
0.8103 Intermediate Similarity NPC172154
0.8103 Intermediate Similarity NPC476729
0.8103 Intermediate Similarity NPC81736
0.8103 Intermediate Similarity NPC8374
0.81 Intermediate Similarity NPC303697
0.81 Intermediate Similarity NPC472814
0.81 Intermediate Similarity NPC177037
0.8095 Intermediate Similarity NPC472552
0.8095 Intermediate Similarity NPC165250
0.8091 Intermediate Similarity NPC470063
0.8091 Intermediate Similarity NPC277769
0.8091 Intermediate Similarity NPC191620
0.8091 Intermediate Similarity NPC90952
0.8091 Intermediate Similarity NPC473877
0.8087 Intermediate Similarity NPC312833
0.8087 Intermediate Similarity NPC287236
0.8087 Intermediate Similarity NPC269642
0.8081 Intermediate Similarity NPC79027
0.8077 Intermediate Similarity NPC38855
0.8077 Intermediate Similarity NPC54705
0.8077 Intermediate Similarity NPC288876
0.8073 Intermediate Similarity NPC478209
0.8073 Intermediate Similarity NPC474567

  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 NPC296950 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
0.8515 High Similarity NPD4225 Approved
0.8125 Intermediate Similarity NPD7115 Discovery
0.7982 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7909 Intermediate Similarity NPD6371 Approved
0.789 Intermediate Similarity NPD6686 Approved
0.7748 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD1694 Approved
0.7636 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.757 Intermediate Similarity NPD7639 Approved
0.757 Intermediate Similarity NPD7640 Approved
0.7524 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD7638 Approved
0.7476 Intermediate Similarity NPD46 Approved
0.7476 Intermediate Similarity NPD6698 Approved
0.7458 Intermediate Similarity NPD6319 Approved
0.7411 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD5344 Discontinued
0.7258 Intermediate Similarity NPD7319 Approved
0.725 Intermediate Similarity NPD8517 Approved
0.725 Intermediate Similarity NPD8516 Approved
0.725 Intermediate Similarity NPD8513 Phase 3
0.725 Intermediate Similarity NPD8515 Approved
0.7241 Intermediate Similarity NPD4632 Approved
0.7213 Intermediate Similarity NPD7492 Approved
0.72 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5779 Approved
0.717 Intermediate Similarity NPD5778 Approved
0.7168 Intermediate Similarity NPD6412 Phase 2
0.7167 Intermediate Similarity NPD6054 Approved
0.7155 Intermediate Similarity NPD6053 Discontinued
0.7154 Intermediate Similarity NPD7507 Approved
0.7154 Intermediate Similarity NPD6616 Approved
0.7143 Intermediate Similarity NPD5785 Approved
0.7117 Intermediate Similarity NPD7632 Discontinued
0.7107 Intermediate Similarity NPD6016 Approved
0.7107 Intermediate Similarity NPD6015 Approved
0.7103 Intermediate Similarity NPD5282 Discontinued
0.7097 Intermediate Similarity NPD7078 Approved
0.708 Intermediate Similarity NPD6008 Approved
0.7075 Intermediate Similarity NPD7983 Approved
0.7069 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD5988 Approved
0.7049 Intermediate Similarity NPD6370 Approved
0.704 Intermediate Similarity NPD7736 Approved
0.7025 Intermediate Similarity NPD6059 Approved
0.7018 Intermediate Similarity NPD5697 Approved
0.7009 Intermediate Similarity NPD6399 Phase 3
0.7009 Intermediate Similarity NPD8297 Approved
0.7 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8328 Phase 3
0.699 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6983 Remote Similarity NPD4634 Approved
0.6981 Remote Similarity NPD7838 Discovery
0.6967 Remote Similarity NPD7503 Approved
0.696 Remote Similarity NPD8293 Discontinued
0.696 Remote Similarity NPD8074 Phase 3
0.6957 Remote Similarity NPD6881 Approved
0.6957 Remote Similarity NPD6899 Approved
0.6937 Remote Similarity NPD6648 Approved
0.693 Remote Similarity NPD6402 Approved
0.693 Remote Similarity NPD5739 Approved
0.693 Remote Similarity NPD7128 Approved
0.693 Remote Similarity NPD6675 Approved
0.6923 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6649 Approved
0.6923 Remote Similarity NPD6650 Approved
0.6917 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6009 Approved
0.6916 Remote Similarity NPD7637 Suspended
0.6909 Remote Similarity NPD7902 Approved
0.6909 Remote Similarity NPD6083 Phase 2
0.6909 Remote Similarity NPD6084 Phase 2
0.6897 Remote Similarity NPD6014 Approved
0.6897 Remote Similarity NPD6013 Approved
0.6897 Remote Similarity NPD6373 Approved
0.6897 Remote Similarity NPD6012 Approved
0.6897 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6372 Approved
0.6887 Remote Similarity NPD1695 Approved
0.6881 Remote Similarity NPD5695 Phase 3
0.687 Remote Similarity NPD5701 Approved
0.686 Remote Similarity NPD7328 Approved
0.686 Remote Similarity NPD7327 Approved
0.6847 Remote Similarity NPD5696 Approved
0.6838 Remote Similarity NPD7290 Approved
0.6838 Remote Similarity NPD7102 Approved
0.6838 Remote Similarity NPD6883 Approved
0.6829 Remote Similarity NPD8033 Approved
0.6829 Remote Similarity NPD5983 Phase 2
0.6814 Remote Similarity NPD5211 Phase 2
0.681 Remote Similarity NPD7320 Approved
0.681 Remote Similarity NPD6011 Approved
0.6803 Remote Similarity NPD7516 Approved
0.6789 Remote Similarity NPD7748 Approved
0.678 Remote Similarity NPD6847 Approved
0.678 Remote Similarity NPD6617 Approved
0.678 Remote Similarity NPD6869 Approved
0.678 Remote Similarity NPD8130 Phase 1
0.6762 Remote Similarity NPD3618 Phase 1
0.6759 Remote Similarity NPD7515 Phase 2
0.6759 Remote Similarity NPD6411 Approved
0.6748 Remote Similarity NPD8377 Approved
0.6748 Remote Similarity NPD8294 Approved
0.6744 Remote Similarity NPD7260 Phase 2
0.6723 Remote Similarity NPD6882 Approved
0.672 Remote Similarity NPD7604 Phase 2
0.6696 Remote Similarity NPD5141 Approved
0.6694 Remote Similarity NPD8335 Approved
0.6694 Remote Similarity NPD8380 Approved
0.6694 Remote Similarity NPD8296 Approved
0.6694 Remote Similarity NPD6921 Approved
0.6694 Remote Similarity NPD8379 Approved
0.6694 Remote Similarity NPD8378 Approved
0.6692 Remote Similarity NPD6845 Suspended
0.6667 Remote Similarity NPD5363 Approved
0.6667 Remote Similarity NPD8133 Approved
0.6637 Remote Similarity NPD4696 Approved
0.6637 Remote Similarity NPD5285 Approved
0.6637 Remote Similarity NPD5286 Approved
0.6636 Remote Similarity NPD7900 Approved
0.6636 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6614 Remote Similarity NPD6336 Discontinued
0.6607 Remote Similarity NPD4755 Approved
0.6606 Remote Similarity NPD5693 Phase 1
0.6606 Remote Similarity NPD5281 Approved
0.6606 Remote Similarity NPD5284 Approved
0.6604 Remote Similarity NPD7334 Approved
0.6604 Remote Similarity NPD6684 Approved
0.6604 Remote Similarity NPD6409 Approved
0.6604 Remote Similarity NPD7521 Approved
0.6604 Remote Similarity NPD5330 Approved
0.6604 Remote Similarity NPD7146 Approved
0.6577 Remote Similarity NPD5210 Approved
0.6577 Remote Similarity NPD4629 Approved
0.6577 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6574 Remote Similarity NPD6101 Approved
0.6574 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6574 Remote Similarity NPD4753 Phase 2
0.6571 Remote Similarity NPD3666 Approved
0.6571 Remote Similarity NPD3133 Approved
0.6571 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6571 Remote Similarity NPD3665 Phase 1
0.6557 Remote Similarity NPD6274 Approved
0.6545 Remote Similarity NPD4202 Approved
0.6542 Remote Similarity NPD7524 Approved
0.6538 Remote Similarity NPD3667 Approved
0.6538 Remote Similarity NPD5956 Approved
0.6522 Remote Similarity NPD5225 Approved
0.6522 Remote Similarity NPD4633 Approved
0.6522 Remote Similarity NPD5224 Approved
0.6522 Remote Similarity NPD5226 Approved
0.6512 Remote Similarity NPD6033 Approved
0.65 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6493 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4700 Approved
0.6481 Remote Similarity NPD6672 Approved
0.6481 Remote Similarity NPD6903 Approved
0.6481 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5737 Approved
0.6466 Remote Similarity NPD5175 Approved
0.6466 Remote Similarity NPD5174 Approved
0.6455 Remote Similarity NPD6079 Approved
0.6449 Remote Similarity NPD4623 Approved
0.6449 Remote Similarity NPD4519 Discontinued
0.6449 Remote Similarity NPD4249 Approved
0.6435 Remote Similarity NPD5223 Approved
0.6429 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5328 Approved
0.6415 Remote Similarity NPD4786 Approved
0.6415 Remote Similarity NPD7338 Clinical (unspecified phase)
0.64 Remote Similarity NPD7101 Approved
0.64 Remote Similarity NPD7100 Approved
0.64 Remote Similarity NPD4522 Approved
0.6389 Remote Similarity NPD4251 Approved
0.6389 Remote Similarity NPD4250 Approved
0.6389 Remote Similarity NPD3573 Approved
0.6381 Remote Similarity NPD4269 Approved
0.6381 Remote Similarity NPD4270 Approved
0.6372 Remote Similarity NPD5222 Approved
0.6372 Remote Similarity NPD4697 Phase 3
0.6372 Remote Similarity NPD5221 Approved
0.6372 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6371 Remote Similarity NPD6317 Approved
0.6364 Remote Similarity NPD5207 Approved
0.6355 Remote Similarity NPD1696 Phase 3
0.6346 Remote Similarity NPD4695 Discontinued
0.6339 Remote Similarity NPD6001 Approved
0.6328 Remote Similarity NPD7642 Approved
0.6328 Remote Similarity NPD6067 Discontinued
0.6321 Remote Similarity NPD7154 Phase 3
0.6321 Remote Similarity NPD6695 Phase 3
0.632 Remote Similarity NPD6314 Approved
0.632 Remote Similarity NPD6335 Approved
0.632 Remote Similarity NPD6313 Approved
0.6316 Remote Similarity NPD5173 Approved
0.6306 Remote Similarity NPD8034 Phase 2
0.6306 Remote Similarity NPD8035 Phase 2
0.6296 Remote Similarity NPD5786 Approved
0.6296 Remote Similarity NPD5279 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