Structure

Physi-Chem Properties

Molecular Weight:  250.16
Volume:  263.425
LogP:  1.685
LogD:  1.251
LogS:  -3.803
# Rotatable Bonds:  1
TPSA:  52.99
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.551
Synthetic Accessibility Score:  5.214
Fsp3:  0.733
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:  -4.638
MDCK Permeability:  1.577333932800684e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.432
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.919
30% Bioavailability (F30%):  0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.96
Plasma Protein Binding (PPB):  43.572410583496094%
Volume Distribution (VD):  1.178
Pgp-substrate:  63.61193084716797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.889
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.843
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.089
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.49
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.283

ADMET: Excretion

Clearance (CL):  4.707
Half-life (T1/2):  0.788

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.513
Drug-inuced Liver Injury (DILI):  0.064
AMES Toxicity:  0.329
Rat Oral Acute Toxicity:  0.962
Maximum Recommended Daily Dose:  0.903
Skin Sensitization:  0.169
Carcinogencity:  0.444
Eye Corrosion:  0.047
Eye Irritation:  0.225
Respiratory Toxicity:  0.974

Download Data

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

  Natural Product: NPC255143

Natural Product ID:  NPC255143
Common Name*:   CHWPMFMUQATVNK-IUCIJCHOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CHWPMFMUQATVNK-IUCIJCHOSA-N
Standard InCHI:  InChI=1S/C15H22O3/c1-8(2)15-12(17)7-10-5-6-11(16)9(3)14(10,4)13(15)18-15/h7,9,11-13,16-17H,1,5-6H2,2-4H3/t9-,11+,12-,13+,14+,15-/m0/s1
SMILES:  O[C@@H]1CCC2=C[C@@H]([C@]3([C@@H]([C@@]2([C@H]1C)C)O3)C(=C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3581339
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32481 Penicillium copticola Under-species n.a. n.a. n.a. n.a. n.a. PMID[25734623]

☑ 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 24050.0 nM PMID[489680]

☑ 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 NPC255143 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
0.9176 High Similarity NPC49783
0.9048 High Similarity NPC281316
0.881 High Similarity NPC83702
0.8571 High Similarity NPC57664
0.8571 High Similarity NPC259858
0.8506 High Similarity NPC476948
0.8478 Intermediate Similarity NPC261807
0.8462 Intermediate Similarity NPC8774
0.8444 Intermediate Similarity NPC119379
0.837 Intermediate Similarity NPC288970
0.837 Intermediate Similarity NPC98457
0.837 Intermediate Similarity NPC210717
0.837 Intermediate Similarity NPC227583
0.837 Intermediate Similarity NPC72204
0.837 Intermediate Similarity NPC103165
0.837 Intermediate Similarity NPC12103
0.8353 Intermediate Similarity NPC471408
0.8352 Intermediate Similarity NPC65402
0.8352 Intermediate Similarity NPC127718
0.8315 Intermediate Similarity NPC115607
0.8313 Intermediate Similarity NPC68119
0.8313 Intermediate Similarity NPC13823
0.828 Intermediate Similarity NPC205143
0.8242 Intermediate Similarity NPC137461
0.8222 Intermediate Similarity NPC191323
0.8222 Intermediate Similarity NPC197107
0.8148 Intermediate Similarity NPC220939
0.8148 Intermediate Similarity NPC265485
0.814 Intermediate Similarity NPC155521
0.8132 Intermediate Similarity NPC114389
0.8111 Intermediate Similarity NPC470361
0.8111 Intermediate Similarity NPC246028
0.8111 Intermediate Similarity NPC97103
0.8105 Intermediate Similarity NPC38855
0.8095 Intermediate Similarity NPC477089
0.8085 Intermediate Similarity NPC473244
0.8072 Intermediate Similarity NPC170148
0.8068 Intermediate Similarity NPC290731
0.8049 Intermediate Similarity NPC190859
0.8025 Intermediate Similarity NPC23954
0.8023 Intermediate Similarity NPC476646
0.8023 Intermediate Similarity NPC471270
0.8022 Intermediate Similarity NPC204188
0.8022 Intermediate Similarity NPC329596
0.8022 Intermediate Similarity NPC3345
0.8022 Intermediate Similarity NPC291484
0.8022 Intermediate Similarity NPC11216
0.8022 Intermediate Similarity NPC80561
0.8021 Intermediate Similarity NPC476896
0.8 Intermediate Similarity NPC233295
0.7979 Intermediate Similarity NPC284194
0.7979 Intermediate Similarity NPC471765
0.7979 Intermediate Similarity NPC211810
0.7979 Intermediate Similarity NPC221801
0.7978 Intermediate Similarity NPC125399
0.7978 Intermediate Similarity NPC476217
0.7957 Intermediate Similarity NPC472360
0.7957 Intermediate Similarity NPC472416
0.7955 Intermediate Similarity NPC46320
0.7935 Intermediate Similarity NPC41554
0.7935 Intermediate Similarity NPC97404
0.7917 Intermediate Similarity NPC79303
0.7912 Intermediate Similarity NPC20946
0.7912 Intermediate Similarity NPC128066
0.7907 Intermediate Similarity NPC95124
0.7907 Intermediate Similarity NPC474592
0.7907 Intermediate Similarity NPC471266
0.7907 Intermediate Similarity NPC236707
0.7907 Intermediate Similarity NPC96362
0.7901 Intermediate Similarity NPC92801
0.7889 Intermediate Similarity NPC189777
0.7882 Intermediate Similarity NPC476314
0.7882 Intermediate Similarity NPC52755
0.7875 Intermediate Similarity NPC96484
0.7865 Intermediate Similarity NPC119001
0.7865 Intermediate Similarity NPC35933
0.7857 Intermediate Similarity NPC265588
0.7849 Intermediate Similarity NPC307776
0.7849 Intermediate Similarity NPC310013
0.7841 Intermediate Similarity NPC477978
0.7841 Intermediate Similarity NPC185605
0.7835 Intermediate Similarity NPC475617
0.7835 Intermediate Similarity NPC207885
0.7835 Intermediate Similarity NPC112613
0.7835 Intermediate Similarity NPC472554
0.7826 Intermediate Similarity NPC295668
0.7826 Intermediate Similarity NPC220216
0.7826 Intermediate Similarity NPC470817
0.7816 Intermediate Similarity NPC249423
0.7812 Intermediate Similarity NPC476895
0.7812 Intermediate Similarity NPC312325
0.7805 Intermediate Similarity NPC164022
0.7805 Intermediate Similarity NPC242992
0.7802 Intermediate Similarity NPC133588
0.7802 Intermediate Similarity NPC474668
0.7789 Intermediate Similarity NPC90583
0.7789 Intermediate Similarity NPC129569
0.7789 Intermediate Similarity NPC94337
0.7778 Intermediate Similarity NPC6391
0.7778 Intermediate Similarity NPC473543
0.7766 Intermediate Similarity NPC144202
0.7765 Intermediate Similarity NPC476703
0.7765 Intermediate Similarity NPC130136
0.7755 Intermediate Similarity NPC472552
0.7753 Intermediate Similarity NPC474047
0.775 Intermediate Similarity NPC82337
0.7742 Intermediate Similarity NPC302584
0.7742 Intermediate Similarity NPC210268
0.7742 Intermediate Similarity NPC124374
0.7738 Intermediate Similarity NPC32832
0.7732 Intermediate Similarity NPC473510
0.7732 Intermediate Similarity NPC64348
0.7732 Intermediate Similarity NPC271295
0.7717 Intermediate Similarity NPC470819
0.7717 Intermediate Similarity NPC187785
0.7717 Intermediate Similarity NPC259875
0.7717 Intermediate Similarity NPC261320
0.7717 Intermediate Similarity NPC477917
0.7717 Intermediate Similarity NPC299527
0.7711 Intermediate Similarity NPC95165
0.7708 Intermediate Similarity NPC182811
0.7708 Intermediate Similarity NPC476893
0.7708 Intermediate Similarity NPC210337
0.7708 Intermediate Similarity NPC26307
0.7701 Intermediate Similarity NPC287749
0.7692 Intermediate Similarity NPC131329
0.7692 Intermediate Similarity NPC233744
0.7692 Intermediate Similarity NPC245004
0.7692 Intermediate Similarity NPC149224
0.7684 Intermediate Similarity NPC276110
0.7677 Intermediate Similarity NPC474124
0.7677 Intermediate Similarity NPC473624
0.7677 Intermediate Similarity NPC473523
0.7674 Intermediate Similarity NPC167891
0.7674 Intermediate Similarity NPC83351
0.767 Intermediate Similarity NPC317107
0.7667 Intermediate Similarity NPC274448
0.7667 Intermediate Similarity NPC298595
0.7667 Intermediate Similarity NPC266511
0.766 Intermediate Similarity NPC99653
0.766 Intermediate Similarity NPC91654
0.766 Intermediate Similarity NPC53555
0.766 Intermediate Similarity NPC474792
0.766 Intermediate Similarity NPC27531
0.766 Intermediate Similarity NPC67398
0.7647 Intermediate Similarity NPC253190
0.7647 Intermediate Similarity NPC472901
0.7647 Intermediate Similarity NPC87335
0.764 Intermediate Similarity NPC475789
0.7634 Intermediate Similarity NPC473099
0.7629 Intermediate Similarity NPC274458
0.7625 Intermediate Similarity NPC326310
0.7624 Intermediate Similarity NPC67321
0.7624 Intermediate Similarity NPC187435
0.7619 Intermediate Similarity NPC201048
0.7619 Intermediate Similarity NPC476366
0.7619 Intermediate Similarity NPC471525
0.7619 Intermediate Similarity NPC24590
0.7619 Intermediate Similarity NPC306727
0.7609 Intermediate Similarity NPC67872
0.7609 Intermediate Similarity NPC471952
0.7604 Intermediate Similarity NPC88009
0.7604 Intermediate Similarity NPC165632
0.76 Intermediate Similarity NPC258532
0.7596 Intermediate Similarity NPC317687
0.759 Intermediate Similarity NPC471272
0.759 Intermediate Similarity NPC471271
0.759 Intermediate Similarity NPC471268
0.759 Intermediate Similarity NPC477792
0.7586 Intermediate Similarity NPC476701
0.7586 Intermediate Similarity NPC476367
0.7586 Intermediate Similarity NPC72755
0.7582 Intermediate Similarity NPC94462
0.7582 Intermediate Similarity NPC299068
0.7582 Intermediate Similarity NPC237344
0.7582 Intermediate Similarity NPC261266
0.7579 Intermediate Similarity NPC105375
0.7579 Intermediate Similarity NPC189513
0.7579 Intermediate Similarity NPC196227
0.7579 Intermediate Similarity NPC182826
0.7576 Intermediate Similarity NPC475344
0.7576 Intermediate Similarity NPC11956
0.7576 Intermediate Similarity NPC476471
0.7576 Intermediate Similarity NPC109195
0.7576 Intermediate Similarity NPC478176
0.7576 Intermediate Similarity NPC475038
0.7576 Intermediate Similarity NPC472815
0.7561 Intermediate Similarity NPC473893
0.7558 Intermediate Similarity NPC477924
0.7558 Intermediate Similarity NPC471798
0.7558 Intermediate Similarity NPC91594
0.7558 Intermediate Similarity NPC470758
0.7558 Intermediate Similarity NPC470711
0.7556 Intermediate Similarity NPC470077
0.7556 Intermediate Similarity NPC185568
0.7553 Intermediate Similarity NPC471453
0.7553 Intermediate Similarity NPC116726
0.7551 Intermediate Similarity NPC471242
0.7551 Intermediate Similarity NPC188968
0.7551 Intermediate Similarity NPC230546

  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 NPC255143 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
0.7653 Intermediate Similarity NPD5344 Discontinued
0.75 Intermediate Similarity NPD7524 Approved
0.7363 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD4159 Approved
0.7273 Intermediate Similarity NPD4225 Approved
0.7253 Intermediate Similarity NPD6695 Phase 3
0.72 Intermediate Similarity NPD6648 Approved
0.7191 Intermediate Similarity NPD7645 Phase 2
0.7143 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD368 Approved
0.7111 Intermediate Similarity NPD6930 Phase 2
0.7111 Intermediate Similarity NPD6931 Approved
0.7 Intermediate Similarity NPD7115 Discovery
0.7 Intermediate Similarity NPD6929 Approved
0.6947 Remote Similarity NPD7750 Discontinued
0.6932 Remote Similarity NPD8264 Approved
0.6923 Remote Similarity NPD7525 Registered
0.6923 Remote Similarity NPD7332 Phase 2
0.6923 Remote Similarity NPD7514 Phase 3
0.6907 Remote Similarity NPD3168 Discontinued
0.6863 Remote Similarity NPD7639 Approved
0.6863 Remote Similarity NPD7640 Approved
0.6854 Remote Similarity NPD6933 Approved
0.6854 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6848 Remote Similarity NPD6902 Approved
0.6778 Remote Similarity NPD5776 Phase 2
0.6778 Remote Similarity NPD6925 Approved
0.6765 Remote Similarity NPD7638 Approved
0.6759 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6747 Remote Similarity NPD371 Approved
0.6742 Remote Similarity NPD6942 Approved
0.6742 Remote Similarity NPD7339 Approved
0.6737 Remote Similarity NPD6893 Approved
0.6735 Remote Similarity NPD7838 Discovery
0.6735 Remote Similarity NPD46 Approved
0.6735 Remote Similarity NPD6698 Approved
0.6703 Remote Similarity NPD7145 Approved
0.6667 Remote Similarity NPD7087 Discontinued
0.6667 Remote Similarity NPD6898 Phase 1
0.6637 Remote Similarity NPD7327 Approved
0.6637 Remote Similarity NPD7328 Approved
0.6629 Remote Similarity NPD6924 Approved
0.6629 Remote Similarity NPD6926 Approved
0.6609 Remote Similarity NPD8033 Approved
0.6593 Remote Similarity NPD6932 Approved
0.6579 Remote Similarity NPD7516 Approved
0.6559 Remote Similarity NPD7509 Discontinued
0.6542 Remote Similarity NPD6640 Phase 3
0.6522 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6522 Remote Similarity NPD8377 Approved
0.6522 Remote Similarity NPD8294 Approved
0.6481 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6466 Remote Similarity NPD8380 Approved
0.6466 Remote Similarity NPD8379 Approved
0.6466 Remote Similarity NPD7503 Approved
0.6466 Remote Similarity NPD8296 Approved
0.6466 Remote Similarity NPD8378 Approved
0.6466 Remote Similarity NPD8335 Approved
0.6452 Remote Similarity NPD6683 Phase 2
0.6436 Remote Similarity NPD5778 Approved
0.6436 Remote Similarity NPD5779 Approved
0.6422 Remote Similarity NPD6686 Approved
0.6421 Remote Similarity NPD3667 Approved
0.6383 Remote Similarity NPD4748 Discontinued
0.6375 Remote Similarity NPD342 Phase 1
0.6337 Remote Similarity NPD7637 Suspended
0.6333 Remote Similarity NPD4732 Discontinued
0.6327 Remote Similarity NPD3618 Phase 1
0.6306 Remote Similarity NPD6371 Approved
0.6289 Remote Similarity NPD4786 Approved
0.6289 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6275 Remote Similarity NPD4202 Approved
0.6273 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6262 Remote Similarity NPD5211 Phase 2
0.6262 Remote Similarity NPD7632 Discontinued
0.6262 Remote Similarity NPD3653 Clinical (unspecified phase)
0.625 Remote Similarity NPD7507 Approved
0.6239 Remote Similarity NPD5357 Phase 1
0.6224 Remote Similarity NPD1696 Phase 3
0.6224 Remote Similarity NPD1694 Approved
0.6222 Remote Similarity NPD7151 Approved
0.6222 Remote Similarity NPD7152 Approved
0.6222 Remote Similarity NPD7150 Approved
0.619 Remote Similarity NPD4755 Approved
0.6186 Remote Similarity NPD8513 Phase 3
0.6186 Remote Similarity NPD8515 Approved
0.6186 Remote Similarity NPD8516 Approved
0.6186 Remote Similarity NPD8517 Approved
0.6182 Remote Similarity NPD6412 Phase 2
0.618 Remote Similarity NPD6922 Approved
0.618 Remote Similarity NPD6923 Approved
0.6161 Remote Similarity NPD4634 Approved
0.6147 Remote Similarity NPD5141 Approved
0.614 Remote Similarity NPD4632 Approved
0.6139 Remote Similarity NPD5328 Approved
0.6139 Remote Similarity NPD6051 Approved
0.6132 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6117 Remote Similarity NPD6399 Phase 3
0.6111 Remote Similarity NPD7143 Approved
0.6111 Remote Similarity NPD7144 Approved
0.6102 Remote Similarity NPD6319 Approved
0.6098 Remote Similarity NPD7319 Approved
0.6091 Remote Similarity NPD5739 Approved
0.6091 Remote Similarity NPD6675 Approved
0.6091 Remote Similarity NPD6008 Approved
0.6091 Remote Similarity NPD7128 Approved
0.6091 Remote Similarity NPD6402 Approved
0.6087 Remote Similarity NPD4784 Approved
0.6087 Remote Similarity NPD4785 Approved
0.6075 Remote Similarity NPD4700 Approved
0.6075 Remote Similarity NPD4696 Approved
0.6075 Remote Similarity NPD5286 Approved
0.6075 Remote Similarity NPD5285 Approved
0.6071 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6058 Remote Similarity NPD7748 Approved
0.6053 Remote Similarity NPD8297 Approved
0.6044 Remote Similarity NPD4243 Approved
0.6038 Remote Similarity NPD7902 Approved
0.6036 Remote Similarity NPD5701 Approved
0.6036 Remote Similarity NPD5697 Approved
0.6019 Remote Similarity NPD7983 Approved
0.6019 Remote Similarity NPD6079 Approved
0.6019 Remote Similarity NPD6411 Approved
0.6019 Remote Similarity NPD7515 Phase 2
0.6 Remote Similarity NPD8133 Approved
0.5982 Remote Similarity NPD6881 Approved
0.5982 Remote Similarity NPD6899 Approved
0.5982 Remote Similarity NPD7320 Approved
0.5966 Remote Similarity NPD6054 Approved
0.5966 Remote Similarity NPD6059 Approved
0.5965 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5963 Remote Similarity NPD5225 Approved
0.5963 Remote Similarity NPD4633 Approved
0.5963 Remote Similarity NPD5224 Approved
0.5963 Remote Similarity NPD5226 Approved
0.596 Remote Similarity NPD3665 Phase 1
0.596 Remote Similarity NPD3666 Approved
0.596 Remote Similarity NPD3133 Approved
0.5952 Remote Similarity NPD585 Clinical (unspecified phase)
0.5935 Remote Similarity NPD8074 Phase 3
0.5929 Remote Similarity NPD6013 Approved
0.5929 Remote Similarity NPD6372 Approved
0.5929 Remote Similarity NPD6012 Approved
0.5929 Remote Similarity NPD6373 Approved
0.5929 Remote Similarity NPD6014 Approved
0.5922 Remote Similarity NPD7136 Phase 2
0.5917 Remote Similarity NPD6015 Approved
0.5917 Remote Similarity NPD6016 Approved
0.5913 Remote Similarity NPD6053 Discontinued
0.5909 Remote Similarity NPD5174 Approved
0.5909 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5175 Approved
0.59 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5877 Remote Similarity NPD6883 Approved
0.5877 Remote Similarity NPD7290 Approved
0.5877 Remote Similarity NPD7102 Approved
0.5872 Remote Similarity NPD5223 Approved
0.5868 Remote Similarity NPD5988 Approved
0.5868 Remote Similarity NPD6370 Approved
0.5851 Remote Similarity NPD5275 Approved
0.5851 Remote Similarity NPD4190 Phase 3
0.5847 Remote Similarity NPD6009 Approved
0.5847 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5842 Remote Similarity NPD4623 Approved
0.5842 Remote Similarity NPD4519 Discontinued
0.5841 Remote Similarity NPD6011 Approved
0.5826 Remote Similarity NPD6650 Approved
0.5826 Remote Similarity NPD6617 Approved
0.5826 Remote Similarity NPD6847 Approved
0.5826 Remote Similarity NPD8130 Phase 1
0.5826 Remote Similarity NPD6649 Approved
0.5826 Remote Similarity NPD6869 Approved
0.5825 Remote Similarity NPD1695 Approved
0.5825 Remote Similarity NPD6101 Approved
0.5825 Remote Similarity NPD4753 Phase 2
0.5825 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5824 Remote Similarity NPD4267 Clinical (unspecified phase)
0.582 Remote Similarity NPD7604 Phase 2
0.582 Remote Similarity NPD8328 Phase 3
0.5814 Remote Similarity NPD1145 Discontinued
0.5804 Remote Similarity NPD4768 Approved
0.5804 Remote Similarity NPD4767 Approved
0.58 Remote Similarity NPD3668 Phase 3
0.5794 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5794 Remote Similarity NPD5222 Approved
0.5794 Remote Similarity NPD4697 Phase 3
0.5794 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5794 Remote Similarity NPD5221 Approved
0.5785 Remote Similarity NPD5983 Phase 2
0.5776 Remote Similarity NPD6882 Approved
0.5773 Remote Similarity NPD4195 Approved
0.5772 Remote Similarity NPD7492 Approved
0.5766 Remote Similarity NPD4754 Approved
0.5758 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5755 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5755 Remote Similarity NPD5282 Discontinued
0.5755 Remote Similarity NPD7900 Approved
0.5752 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5741 Remote Similarity NPD6084 Phase 2

  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