Structure

Physi-Chem Properties

Molecular Weight:  248.14
Volume:  266.708
LogP:  1.302
LogD:  0.498
LogS:  -1.358
# Rotatable Bonds:  3
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.614
Synthetic Accessibility Score:  4.521
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.483
MDCK Permeability:  5.1565693865995854e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.371
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.885
Plasma Protein Binding (PPB):  48.036033630371094%
Volume Distribution (VD):  0.642
Pgp-substrate:  66.37906646728516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.164
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.392
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.055
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.132
CYP3A4-inhibitor:  0.095
CYP3A4-substrate:  0.259

ADMET: Excretion

Clearance (CL):  7.124
Half-life (T1/2):  0.799

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.11
Drug-inuced Liver Injury (DILI):  0.396
AMES Toxicity:  0.664
Rat Oral Acute Toxicity:  0.78
Maximum Recommended Daily Dose:  0.142
Skin Sensitization:  0.928
Carcinogencity:  0.822
Eye Corrosion:  0.962
Eye Irritation:  0.967
Respiratory Toxicity:  0.983

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

  Natural Product: NPC45495

Natural Product ID:  NPC45495
Common Name*:   12-Hydroxychiloscypha-2,7-Dione
IUPAC Name:   (1S,7S,7aS)-1-[2-(hydroxymethyl)prop-2-enoyl]-7,7a-dimethyl-2,3,6,7-tetrahydro-1H-inden-5-one
Synonyms:  
Standard InCHIKey:  HSEYGUUBMYCCIJ-PSOPSSQASA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-9(8-16)14(18)13-5-4-11-7-12(17)6-10(2)15(11,13)3/h7,10,13,16H,1,4-6,8H2,2-3H3/t10-,13+,15+/m0/s1
SMILES:  C=C(CO)C(=O)[C@H]1CCC2=CC(=O)C[C@H](C)[C@@]12C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462819
PubChem CID:   10586644
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO8475 Chiloscyphus rivularis Species Lophocoleaceae Eukaryota n.a. n.a. n.a. PMID[9463110]
NPO8475 Chiloscyphus rivularis Species Lophocoleaceae 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
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 > 500.0 ug ml-1 PMID[487819]

☑ 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 NPC45495 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
0.9865 High Similarity NPC7232
0.8961 High Similarity NPC62336
0.8947 High Similarity NPC263582
0.878 High Similarity NPC194417
0.8718 High Similarity NPC475994
0.8701 High Similarity NPC470525
0.8659 High Similarity NPC474853
0.8659 High Similarity NPC179006
0.8625 High Similarity NPC136150
0.8608 High Similarity NPC308038
0.8571 High Similarity NPC114236
0.85 High Similarity NPC157895
0.85 High Similarity NPC148685
0.85 High Similarity NPC104120
0.8471 Intermediate Similarity NPC123912
0.8462 Intermediate Similarity NPC469646
0.8415 Intermediate Similarity NPC62214
0.8395 Intermediate Similarity NPC116797
0.8354 Intermediate Similarity NPC97377
0.8354 Intermediate Similarity NPC74995
0.8353 Intermediate Similarity NPC474854
0.8313 Intermediate Similarity NPC85774
0.8313 Intermediate Similarity NPC214043
0.8313 Intermediate Similarity NPC473246
0.8313 Intermediate Similarity NPC329043
0.8313 Intermediate Similarity NPC237712
0.8313 Intermediate Similarity NPC161423
0.8313 Intermediate Similarity NPC58841
0.8313 Intermediate Similarity NPC227064
0.8313 Intermediate Similarity NPC476412
0.8313 Intermediate Similarity NPC230527
0.8313 Intermediate Similarity NPC7927
0.8313 Intermediate Similarity NPC321187
0.8312 Intermediate Similarity NPC186042
0.8293 Intermediate Similarity NPC93590
0.8272 Intermediate Similarity NPC172013
0.8272 Intermediate Similarity NPC472478
0.8256 Intermediate Similarity NPC472475
0.8256 Intermediate Similarity NPC309603
0.8256 Intermediate Similarity NPC473999
0.8256 Intermediate Similarity NPC472477
0.8235 Intermediate Similarity NPC287079
0.8235 Intermediate Similarity NPC93778
0.8214 Intermediate Similarity NPC469948
0.8214 Intermediate Similarity NPC471224
0.8214 Intermediate Similarity NPC474083
0.8214 Intermediate Similarity NPC470574
0.8205 Intermediate Similarity NPC215050
0.8193 Intermediate Similarity NPC474748
0.8182 Intermediate Similarity NPC474736
0.8182 Intermediate Similarity NPC474807
0.8182 Intermediate Similarity NPC109305
0.8161 Intermediate Similarity NPC48010
0.8161 Intermediate Similarity NPC230332
0.8148 Intermediate Similarity NPC229204
0.8148 Intermediate Similarity NPC472490
0.8148 Intermediate Similarity NPC19900
0.8148 Intermediate Similarity NPC152061
0.814 Intermediate Similarity NPC471724
0.8125 Intermediate Similarity NPC266193
0.8125 Intermediate Similarity NPC197659
0.8125 Intermediate Similarity NPC257666
0.8118 Intermediate Similarity NPC474733
0.8118 Intermediate Similarity NPC145879
0.8118 Intermediate Similarity NPC474778
0.8118 Intermediate Similarity NPC474732
0.8118 Intermediate Similarity NPC472974
0.8118 Intermediate Similarity NPC476043
0.8118 Intermediate Similarity NPC31564
0.8118 Intermediate Similarity NPC327115
0.8118 Intermediate Similarity NPC469994
0.8111 Intermediate Similarity NPC29152
0.8101 Intermediate Similarity NPC474011
0.8095 Intermediate Similarity NPC165064
0.8077 Intermediate Similarity NPC275098
0.8072 Intermediate Similarity NPC103486
0.8072 Intermediate Similarity NPC151519
0.8072 Intermediate Similarity NPC38796
0.8072 Intermediate Similarity NPC158411
0.8068 Intermediate Similarity NPC475806
0.8068 Intermediate Similarity NPC473998
0.8049 Intermediate Similarity NPC233352
0.8049 Intermediate Similarity NPC2482
0.8049 Intermediate Similarity NPC824
0.8049 Intermediate Similarity NPC138492
0.8049 Intermediate Similarity NPC271104
0.8046 Intermediate Similarity NPC472970
0.8046 Intermediate Similarity NPC472971
0.8046 Intermediate Similarity NPC170775
0.8046 Intermediate Similarity NPC472489
0.8046 Intermediate Similarity NPC214387
0.8025 Intermediate Similarity NPC275494
0.8025 Intermediate Similarity NPC471409
0.8025 Intermediate Similarity NPC178852
0.8025 Intermediate Similarity NPC297996
0.8023 Intermediate Similarity NPC475740
0.8023 Intermediate Similarity NPC136548
0.8023 Intermediate Similarity NPC96496
0.8023 Intermediate Similarity NPC58063
0.8022 Intermediate Similarity NPC156546
0.8 Intermediate Similarity NPC476426
0.8 Intermediate Similarity NPC36350
0.8 Intermediate Similarity NPC70685
0.8 Intermediate Similarity NPC215481
0.7978 Intermediate Similarity NPC115021
0.7978 Intermediate Similarity NPC472930
0.7978 Intermediate Similarity NPC69454
0.7976 Intermediate Similarity NPC470165
0.7976 Intermediate Similarity NPC97913
0.7973 Intermediate Similarity NPC212210
0.7957 Intermediate Similarity NPC472924
0.7955 Intermediate Similarity NPC191684
0.7955 Intermediate Similarity NPC477147
0.7955 Intermediate Similarity NPC51486
0.7955 Intermediate Similarity NPC472476
0.7955 Intermediate Similarity NPC477149
0.7952 Intermediate Similarity NPC477372
0.7952 Intermediate Similarity NPC121984
0.7952 Intermediate Similarity NPC14151
0.7931 Intermediate Similarity NPC471793
0.7931 Intermediate Similarity NPC193843
0.7931 Intermediate Similarity NPC471722
0.7931 Intermediate Similarity NPC328539
0.7931 Intermediate Similarity NPC471791
0.7931 Intermediate Similarity NPC249889
0.7931 Intermediate Similarity NPC328313
0.7927 Intermediate Similarity NPC281138
0.7927 Intermediate Similarity NPC261125
0.7927 Intermediate Similarity NPC181195
0.7912 Intermediate Similarity NPC472941
0.7912 Intermediate Similarity NPC456
0.7907 Intermediate Similarity NPC118648
0.7907 Intermediate Similarity NPC222613
0.7907 Intermediate Similarity NPC472479
0.7907 Intermediate Similarity NPC475022
0.7907 Intermediate Similarity NPC472985
0.7907 Intermediate Similarity NPC472986
0.7907 Intermediate Similarity NPC198761
0.7907 Intermediate Similarity NPC470955
0.7907 Intermediate Similarity NPC72133
0.7901 Intermediate Similarity NPC203403
0.7889 Intermediate Similarity NPC8993
0.7889 Intermediate Similarity NPC299100
0.7889 Intermediate Similarity NPC53685
0.7882 Intermediate Similarity NPC221758
0.7882 Intermediate Similarity NPC59453
0.7882 Intermediate Similarity NPC82902
0.7882 Intermediate Similarity NPC472265
0.7882 Intermediate Similarity NPC164577
0.7875 Intermediate Similarity NPC77501
0.7875 Intermediate Similarity NPC476795
0.7865 Intermediate Similarity NPC272746
0.7865 Intermediate Similarity NPC472814
0.7865 Intermediate Similarity NPC233116
0.7865 Intermediate Similarity NPC63748
0.7865 Intermediate Similarity NPC177037
0.7857 Intermediate Similarity NPC129080
0.7857 Intermediate Similarity NPC20262
0.7857 Intermediate Similarity NPC256750
0.7857 Intermediate Similarity NPC477269
0.7857 Intermediate Similarity NPC477271
0.7857 Intermediate Similarity NPC477270
0.7857 Intermediate Similarity NPC193347
0.7848 Intermediate Similarity NPC247586
0.7841 Intermediate Similarity NPC5509
0.7841 Intermediate Similarity NPC268406
0.7841 Intermediate Similarity NPC472973
0.7841 Intermediate Similarity NPC326627
0.7841 Intermediate Similarity NPC119416
0.7841 Intermediate Similarity NPC472983
0.7841 Intermediate Similarity NPC2983
0.7841 Intermediate Similarity NPC1015
0.7841 Intermediate Similarity NPC262043
0.7841 Intermediate Similarity NPC86319
0.7841 Intermediate Similarity NPC31985
0.7841 Intermediate Similarity NPC186688
0.7841 Intermediate Similarity NPC477943
0.7841 Intermediate Similarity NPC275740
0.7841 Intermediate Similarity NPC26959
0.7841 Intermediate Similarity NPC310010
0.7841 Intermediate Similarity NPC310236
0.7831 Intermediate Similarity NPC471514
0.7831 Intermediate Similarity NPC306095
0.7831 Intermediate Similarity NPC472301
0.7826 Intermediate Similarity NPC253826
0.7816 Intermediate Similarity NPC312561
0.7816 Intermediate Similarity NPC141292
0.7816 Intermediate Similarity NPC317590
0.7816 Intermediate Similarity NPC472484
0.7816 Intermediate Similarity NPC472481
0.7816 Intermediate Similarity NPC472482
0.7816 Intermediate Similarity NPC136948
0.7805 Intermediate Similarity NPC74410
0.7805 Intermediate Similarity NPC207772
0.7802 Intermediate Similarity NPC472932
0.7802 Intermediate Similarity NPC476174
0.7802 Intermediate Similarity NPC259286
0.7802 Intermediate Similarity NPC271195
0.7802 Intermediate Similarity NPC180950
0.7792 Intermediate Similarity NPC117804

  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 NPC45495 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
0.8313 Intermediate Similarity NPD3665 Phase 1
0.8313 Intermediate Similarity NPD3133 Approved
0.8313 Intermediate Similarity NPD3666 Approved
0.8118 Intermediate Similarity NPD5279 Phase 3
0.8118 Intermediate Similarity NPD3618 Phase 1
0.8072 Intermediate Similarity NPD3667 Approved
0.7907 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD4786 Approved
0.7865 Intermediate Similarity NPD6079 Approved
0.7857 Intermediate Similarity NPD4223 Phase 3
0.7857 Intermediate Similarity NPD4221 Approved
0.7841 Intermediate Similarity NPD5328 Approved
0.7841 Intermediate Similarity NPD4753 Phase 2
0.7701 Intermediate Similarity NPD5690 Phase 2
0.7674 Intermediate Similarity NPD4197 Approved
0.7619 Intermediate Similarity NPD4695 Discontinued
0.7609 Intermediate Similarity NPD4629 Approved
0.7609 Intermediate Similarity NPD5210 Approved
0.759 Intermediate Similarity NPD3617 Approved
0.7586 Intermediate Similarity NPD5329 Approved
0.7586 Intermediate Similarity NPD5363 Approved
0.7582 Intermediate Similarity NPD4202 Approved
0.7556 Intermediate Similarity NPD5785 Approved
0.7527 Intermediate Similarity NPD5221 Approved
0.7527 Intermediate Similarity NPD5222 Approved
0.7527 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5211 Phase 2
0.75 Intermediate Similarity NPD4693 Phase 3
0.75 Intermediate Similarity NPD4623 Approved
0.75 Intermediate Similarity NPD4690 Approved
0.75 Intermediate Similarity NPD4138 Approved
0.75 Intermediate Similarity NPD5205 Approved
0.75 Intermediate Similarity NPD4689 Approved
0.75 Intermediate Similarity NPD4688 Approved
0.75 Intermediate Similarity NPD4519 Discontinued
0.75 Intermediate Similarity NPD5280 Approved
0.75 Intermediate Similarity NPD4694 Approved
0.7447 Intermediate Similarity NPD5173 Approved
0.7386 Intermediate Similarity NPD1696 Phase 3
0.7381 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD4691 Approved
0.7356 Intermediate Similarity NPD4788 Approved
0.7347 Intermediate Similarity NPD5141 Approved
0.734 Intermediate Similarity NPD4697 Phase 3
0.7303 Intermediate Similarity NPD5330 Approved
0.7303 Intermediate Similarity NPD7521 Approved
0.7303 Intermediate Similarity NPD7334 Approved
0.7303 Intermediate Similarity NPD6409 Approved
0.7303 Intermediate Similarity NPD6684 Approved
0.7303 Intermediate Similarity NPD7146 Approved
0.7294 Intermediate Similarity NPD4195 Approved
0.7292 Intermediate Similarity NPD5285 Approved
0.7292 Intermediate Similarity NPD4696 Approved
0.7292 Intermediate Similarity NPD5286 Approved
0.7273 Intermediate Similarity NPD3668 Phase 3
0.7263 Intermediate Similarity NPD6083 Phase 2
0.7263 Intermediate Similarity NPD4755 Approved
0.7263 Intermediate Similarity NPD6084 Phase 2
0.725 Intermediate Similarity NPD4137 Phase 3
0.7241 Intermediate Similarity NPD4269 Approved
0.7241 Intermediate Similarity NPD4270 Approved
0.7234 Intermediate Similarity NPD5695 Phase 3
0.7216 Intermediate Similarity NPD5223 Approved
0.7174 Intermediate Similarity NPD4096 Approved
0.716 Intermediate Similarity NPD4747 Approved
0.7143 Intermediate Similarity NPD5224 Approved
0.7143 Intermediate Similarity NPD6903 Approved
0.7143 Intermediate Similarity NPD5225 Approved
0.7143 Intermediate Similarity NPD6672 Approved
0.7143 Intermediate Similarity NPD5226 Approved
0.7143 Intermediate Similarity NPD5737 Approved
0.7143 Intermediate Similarity NPD4518 Approved
0.7143 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4633 Approved
0.7113 Intermediate Similarity NPD4700 Approved
0.7108 Intermediate Similarity NPD4058 Approved
0.7097 Intermediate Similarity NPD7515 Phase 2
0.7097 Intermediate Similarity NPD5281 Approved
0.7097 Intermediate Similarity NPD5284 Approved
0.7089 Intermediate Similarity NPD7331 Phase 2
0.7073 Intermediate Similarity NPD5276 Approved
0.7071 Intermediate Similarity NPD5174 Approved
0.7071 Intermediate Similarity NPD5175 Approved
0.7053 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6399 Phase 3
0.7011 Intermediate Similarity NPD4252 Approved
0.701 Intermediate Similarity NPD5696 Approved
0.699 Remote Similarity NPD4634 Approved
0.6962 Remote Similarity NPD7341 Phase 2
0.6941 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6932 Remote Similarity NPD5369 Approved
0.6932 Remote Similarity NPD4692 Approved
0.6932 Remote Similarity NPD4139 Approved
0.6923 Remote Similarity NPD5786 Approved
0.6916 Remote Similarity NPD7115 Discovery
0.6905 Remote Similarity NPD5733 Approved
0.6905 Remote Similarity NPD4687 Approved
0.69 Remote Similarity NPD4754 Approved
0.6863 Remote Similarity NPD5697 Approved
0.6842 Remote Similarity NPD5133 Approved
0.6837 Remote Similarity NPD4225 Approved
0.6824 Remote Similarity NPD6942 Approved
0.6824 Remote Similarity NPD7339 Approved
0.6813 Remote Similarity NPD1694 Approved
0.6796 Remote Similarity NPD6899 Approved
0.6796 Remote Similarity NPD6881 Approved
0.6796 Remote Similarity NPD6011 Approved
0.6796 Remote Similarity NPD4730 Approved
0.6796 Remote Similarity NPD4729 Approved
0.6796 Remote Similarity NPD5128 Approved
0.6796 Remote Similarity NPD5168 Approved
0.6778 Remote Similarity NPD5362 Discontinued
0.6774 Remote Similarity NPD5208 Approved
0.6771 Remote Similarity NPD7748 Approved
0.6771 Remote Similarity NPD5282 Discontinued
0.6768 Remote Similarity NPD7640 Approved
0.6768 Remote Similarity NPD7639 Approved
0.6768 Remote Similarity NPD6404 Discontinued
0.6765 Remote Similarity NPD6402 Approved
0.6765 Remote Similarity NPD7128 Approved
0.6765 Remote Similarity NPD4767 Approved
0.6765 Remote Similarity NPD5739 Approved
0.6765 Remote Similarity NPD6675 Approved
0.6765 Remote Similarity NPD4768 Approved
0.675 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6411 Approved
0.6737 Remote Similarity NPD5693 Phase 1
0.6731 Remote Similarity NPD6013 Approved
0.6731 Remote Similarity NPD6012 Approved
0.6731 Remote Similarity NPD6014 Approved
0.6707 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6706 Remote Similarity NPD6926 Approved
0.6706 Remote Similarity NPD6924 Approved
0.6705 Remote Similarity NPD6929 Approved
0.6702 Remote Similarity NPD6080 Approved
0.6702 Remote Similarity NPD6904 Approved
0.6702 Remote Similarity NPD6673 Approved
0.6699 Remote Similarity NPD6412 Phase 2
0.6699 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD5169 Approved
0.6667 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD5248 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6667 Remote Similarity NPD5247 Approved
0.6667 Remote Similarity NPD5135 Approved
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD5251 Approved
0.6667 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5250 Approved
0.6667 Remote Similarity NPD5249 Phase 3
0.6667 Remote Similarity NPD5779 Approved
0.6635 Remote Similarity NPD7320 Approved
0.6634 Remote Similarity NPD5091 Approved
0.6632 Remote Similarity NPD5207 Approved
0.6632 Remote Similarity NPD5692 Phase 3
0.663 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6629 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6931 Approved
0.6629 Remote Similarity NPD5368 Approved
0.6629 Remote Similarity NPD6930 Phase 2
0.6623 Remote Similarity NPD287 Approved
0.6604 Remote Similarity NPD6847 Approved
0.6604 Remote Similarity NPD8130 Phase 1
0.6604 Remote Similarity NPD6650 Approved
0.6604 Remote Similarity NPD6617 Approved
0.6604 Remote Similarity NPD5215 Approved
0.6604 Remote Similarity NPD5127 Approved
0.6604 Remote Similarity NPD5217 Approved
0.6604 Remote Similarity NPD6869 Approved
0.6604 Remote Similarity NPD5216 Approved
0.6604 Remote Similarity NPD6649 Approved
0.6571 Remote Similarity NPD6373 Approved
0.6571 Remote Similarity NPD6372 Approved
0.6566 Remote Similarity NPD7902 Approved
0.6562 Remote Similarity NPD7637 Suspended
0.6562 Remote Similarity NPD5694 Approved
0.6562 Remote Similarity NPD6050 Approved
0.6559 Remote Similarity NPD6098 Approved
0.6552 Remote Similarity NPD6933 Approved
0.6542 Remote Similarity NPD6882 Approved
0.6542 Remote Similarity NPD8297 Approved
0.6531 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6526 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6526 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6526 Remote Similarity NPD6101 Approved
0.65 Remote Similarity NPD2664 Clinical (unspecified phase)
0.65 Remote Similarity NPD5290 Discontinued
0.6489 Remote Similarity NPD3573 Approved
0.6489 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4522 Approved
0.6484 Remote Similarity NPD6435 Approved
0.6481 Remote Similarity NPD4632 Approved
0.6477 Remote Similarity NPD5776 Phase 2
0.6477 Remote Similarity NPD6925 Approved
0.6471 Remote Similarity NPD4243 Approved
0.6449 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6447 Remote Similarity NPD342 Phase 1

  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