Structure

Physi-Chem Properties

Molecular Weight:  234.16
Volume:  254.634
LogP:  2.88
LogD:  2.519
LogS:  -4.363
# Rotatable Bonds:  0
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.654
Synthetic Accessibility Score:  4.746
Fsp3:  0.8
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:  -4.722
MDCK Permeability:  2.7843454518006183e-05
Pgp-inhibitor:  0.011
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.317
Plasma Protein Binding (PPB):  65.82764434814453%
Volume Distribution (VD):  0.746
Pgp-substrate:  53.005184173583984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.817
CYP2C19-inhibitor:  0.207
CYP2C19-substrate:  0.794
CYP2C9-inhibitor:  0.209
CYP2C9-substrate:  0.128
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.22
CYP3A4-inhibitor:  0.123
CYP3A4-substrate:  0.225

ADMET: Excretion

Clearance (CL):  5.887
Half-life (T1/2):  0.123

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.378
Drug-inuced Liver Injury (DILI):  0.23
AMES Toxicity:  0.08
Rat Oral Acute Toxicity:  0.855
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.796
Carcinogencity:  0.842
Eye Corrosion:  0.861
Eye Irritation:  0.913
Respiratory Toxicity:  0.973

Download Data

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

  Natural Product: NPC201263

Natural Product ID:  NPC201263
Common Name*:   Delta (9(12))-Capnellene-10Alpha-Ol-8-One
IUPAC Name:   (3aS,3bR,6aR,7aS)-3b-hydroxy-3,3,7a-trimethyl-4-methylidene-1,2,3a,6,6a,7-hexahydrocyclopenta[a]pentalen-5-one
Synonyms:  
Standard InCHIKey:  HNSDLIGSLVJPQF-HQRZJTNHSA-N
Standard InCHI:  InChI=1S/C15H22O2/c1-9-11(16)7-10-8-14(4)6-5-13(2,3)12(14)15(9,10)17/h10,12,17H,1,5-8H2,2-4H3/t10-,12-,14-,15+/m0/s1
SMILES:  O=C1C[C@@H]2[C@@](C1=C)(O)[C@@H]1[C@@](C2)(C)CCC1(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL457465
PubChem CID:   44567558
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002004] Triquinane sesquiterpenoids
            • [CHEMONTID:0003583] Linear triquinanes
              • [CHEMONTID:0003581] Capnellane and isocapnellane 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
NPO2368 Capnella imbricata Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[18302334]

☑ 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
NPT113 Cell Line RAW264.7 Mus musculus Activity = 34.8 n.a. PMID[556248]

☑ 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 NPC201263 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
0.7922 Intermediate Similarity NPC251435
0.7922 Intermediate Similarity NPC77501
0.7805 Intermediate Similarity NPC473629
0.775 Intermediate Similarity NPC32758
0.775 Intermediate Similarity NPC301769
0.7683 Intermediate Similarity NPC256750
0.7683 Intermediate Similarity NPC20262
0.7654 Intermediate Similarity NPC164218
0.7632 Intermediate Similarity NPC18543
0.7614 Intermediate Similarity NPC475488
0.7471 Intermediate Similarity NPC41217
0.7471 Intermediate Similarity NPC170775
0.7386 Intermediate Similarity NPC2946
0.7381 Intermediate Similarity NPC65350
0.7375 Intermediate Similarity NPC182848
0.7342 Intermediate Similarity NPC7382
0.7326 Intermediate Similarity NPC472479
0.7326 Intermediate Similarity NPC472488
0.7317 Intermediate Similarity NPC7232
0.7308 Intermediate Similarity NPC469737
0.7284 Intermediate Similarity NPC74685
0.726 Intermediate Similarity NPC15152
0.7241 Intermediate Similarity NPC201658
0.7229 Intermediate Similarity NPC45495
0.7215 Intermediate Similarity NPC300940
0.7179 Intermediate Similarity NPC133873
0.716 Intermediate Similarity NPC141346
0.716 Intermediate Similarity NPC25908
0.716 Intermediate Similarity NPC124289
0.716 Intermediate Similarity NPC142759
0.716 Intermediate Similarity NPC115719
0.716 Intermediate Similarity NPC473437
0.7125 Intermediate Similarity NPC206875
0.7108 Intermediate Similarity NPC472013
0.7108 Intermediate Similarity NPC476624
0.7108 Intermediate Similarity NPC84185
0.7108 Intermediate Similarity NPC471890
0.7108 Intermediate Similarity NPC66677
0.7093 Intermediate Similarity NPC472480
0.7079 Intermediate Similarity NPC472489
0.7079 Intermediate Similarity NPC232747
0.7079 Intermediate Similarity NPC472477
0.7079 Intermediate Similarity NPC472475
0.7073 Intermediate Similarity NPC276769
0.7059 Intermediate Similarity NPC477271
0.7059 Intermediate Similarity NPC477269
0.7059 Intermediate Similarity NPC46881
0.7059 Intermediate Similarity NPC477270
0.7059 Intermediate Similarity NPC129080
0.7053 Intermediate Similarity NPC195192
0.7053 Intermediate Similarity NPC304738
0.7037 Intermediate Similarity NPC89374
0.7033 Intermediate Similarity NPC37816
0.7024 Intermediate Similarity NPC476625
0.7024 Intermediate Similarity NPC279667
0.7013 Intermediate Similarity NPC263161
0.7 Intermediate Similarity NPC472476
0.6988 Remote Similarity NPC476627
0.6977 Remote Similarity NPC474748
0.6977 Remote Similarity NPC245665
0.6977 Remote Similarity NPC472492
0.6977 Remote Similarity NPC62214
0.6966 Remote Similarity NPC58532
0.6966 Remote Similarity NPC472677
0.6957 Remote Similarity NPC298919
0.6951 Remote Similarity NPC215481
0.6951 Remote Similarity NPC469646
0.6941 Remote Similarity NPC171665
0.6897 Remote Similarity NPC230527
0.6897 Remote Similarity NPC7927
0.6892 Remote Similarity NPC270042
0.6892 Remote Similarity NPC162109
0.6882 Remote Similarity NPC471624
0.6882 Remote Similarity NPC197158
0.6875 Remote Similarity NPC144627
0.6875 Remote Similarity NPC29328
0.6867 Remote Similarity NPC472014
0.686 Remote Similarity NPC193347
0.686 Remote Similarity NPC133844
0.6854 Remote Similarity NPC472482
0.6854 Remote Similarity NPC472484
0.6854 Remote Similarity NPC472481
0.6848 Remote Similarity NPC125180
0.6848 Remote Similarity NPC473234
0.6848 Remote Similarity NPC200237
0.6848 Remote Similarity NPC153590
0.6848 Remote Similarity NPC473263
0.6848 Remote Similarity NPC60386
0.6848 Remote Similarity NPC308656
0.6848 Remote Similarity NPC473273
0.6824 Remote Similarity NPC233352
0.6824 Remote Similarity NPC6823
0.6824 Remote Similarity NPC824
0.6824 Remote Similarity NPC30675
0.6824 Remote Similarity NPC80622
0.6824 Remote Similarity NPC138492
0.6818 Remote Similarity NPC204105
0.6818 Remote Similarity NPC245434
0.6818 Remote Similarity NPC476628
0.6818 Remote Similarity NPC102292
0.6818 Remote Similarity NPC300082
0.6818 Remote Similarity NPC284534
0.6804 Remote Similarity NPC25639
0.679 Remote Similarity NPC275098
0.6782 Remote Similarity NPC472740
0.6782 Remote Similarity NPC472498
0.6778 Remote Similarity NPC472483
0.6774 Remote Similarity NPC90453
0.6744 Remote Similarity NPC78677
0.6744 Remote Similarity NPC47031
0.6744 Remote Similarity NPC59994
0.6742 Remote Similarity NPC472491
0.6742 Remote Similarity NPC56593
0.6742 Remote Similarity NPC472494
0.6737 Remote Similarity NPC311904
0.6711 Remote Similarity NPC474480
0.6709 Remote Similarity NPC476629
0.6705 Remote Similarity NPC90446
0.6705 Remote Similarity NPC475796
0.6705 Remote Similarity NPC144258
0.6703 Remote Similarity NPC168679
0.6703 Remote Similarity NPC12872
0.6703 Remote Similarity NPC97032
0.6667 Remote Similarity NPC103734
0.6667 Remote Similarity NPC212661
0.6667 Remote Similarity NPC7414
0.6667 Remote Similarity NPC40206
0.6667 Remote Similarity NPC145143
0.6667 Remote Similarity NPC106078
0.6667 Remote Similarity NPC165895
0.6667 Remote Similarity NPC471035
0.6667 Remote Similarity NPC475932
0.6667 Remote Similarity NPC197089
0.6667 Remote Similarity NPC472493
0.6634 Remote Similarity NPC9013
0.6632 Remote Similarity NPC91771
0.6632 Remote Similarity NPC142529
0.6629 Remote Similarity NPC179006
0.6629 Remote Similarity NPC474853
0.6628 Remote Similarity NPC287817
0.6628 Remote Similarity NPC258965
0.6628 Remote Similarity NPC156658
0.6628 Remote Similarity NPC74445
0.6627 Remote Similarity NPC39362
0.6627 Remote Similarity NPC474011
0.6625 Remote Similarity NPC475952
0.6625 Remote Similarity NPC67608
0.6623 Remote Similarity NPC128608
0.6623 Remote Similarity NPC53642
0.6623 Remote Similarity NPC470325
0.6596 Remote Similarity NPC473331
0.6593 Remote Similarity NPC477710
0.6593 Remote Similarity NPC183374
0.6593 Remote Similarity NPC79549
0.6593 Remote Similarity NPC471941
0.6593 Remote Similarity NPC211162
0.6591 Remote Similarity NPC477373
0.6591 Remote Similarity NPC291320
0.6591 Remote Similarity NPC471036
0.6588 Remote Similarity NPC19443
0.6585 Remote Similarity NPC472813
0.6585 Remote Similarity NPC52667
0.6569 Remote Similarity NPC474901
0.6569 Remote Similarity NPC475941
0.6566 Remote Similarity NPC168575
0.6562 Remote Similarity NPC170143
0.6562 Remote Similarity NPC108475
0.6562 Remote Similarity NPC213947
0.6562 Remote Similarity NPC477949
0.6559 Remote Similarity NPC184063
0.6556 Remote Similarity NPC469994
0.6556 Remote Similarity NPC476043
0.6552 Remote Similarity NPC150506
0.6552 Remote Similarity NPC164210
0.6552 Remote Similarity NPC103754
0.6552 Remote Similarity NPC474484
0.6552 Remote Similarity NPC232625
0.6548 Remote Similarity NPC472472
0.6543 Remote Similarity NPC235586
0.6543 Remote Similarity NPC254845
0.6533 Remote Similarity NPC184049
0.6533 Remote Similarity NPC99480
0.6531 Remote Similarity NPC206079
0.6531 Remote Similarity NPC477950
0.6531 Remote Similarity NPC475099
0.6526 Remote Similarity NPC469873
0.6522 Remote Similarity NPC155935
0.6522 Remote Similarity NPC215556
0.6522 Remote Similarity NPC24772
0.6522 Remote Similarity NPC262043
0.6522 Remote Similarity NPC205548
0.6522 Remote Similarity NPC472970
0.6522 Remote Similarity NPC155479
0.6522 Remote Similarity NPC2983
0.6522 Remote Similarity NPC116146
0.6522 Remote Similarity NPC472971
0.6517 Remote Similarity NPC156485
0.6517 Remote Similarity NPC238197
0.6512 Remote Similarity NPC181195
0.6512 Remote Similarity NPC472490

  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 NPC201263 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
0.6977 Remote Similarity NPD4788 Approved
0.6932 Remote Similarity NPD3574 Clinical (unspecified phase)
0.686 Remote Similarity NPD4223 Phase 3
0.686 Remote Similarity NPD4221 Approved
0.6818 Remote Similarity NPD5363 Approved
0.6813 Remote Similarity NPD5785 Approved
0.6742 Remote Similarity NPD5690 Phase 2
0.6705 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD4270 Approved
0.6667 Remote Similarity NPD4269 Approved
0.6629 Remote Similarity NPD5329 Approved
0.6556 Remote Similarity NPD4138 Approved
0.6556 Remote Similarity NPD4693 Phase 3
0.6556 Remote Similarity NPD4689 Approved
0.6556 Remote Similarity NPD4690 Approved
0.6556 Remote Similarity NPD5280 Approved
0.6556 Remote Similarity NPD5205 Approved
0.6556 Remote Similarity NPD4688 Approved
0.6556 Remote Similarity NPD4694 Approved
0.6552 Remote Similarity NPD4790 Discontinued
0.6552 Remote Similarity NPD4692 Approved
0.6552 Remote Similarity NPD4139 Approved
0.6552 Remote Similarity NPD5369 Approved
0.6437 Remote Similarity NPD4252 Approved
0.6413 Remote Similarity NPD4518 Approved
0.6404 Remote Similarity NPD5362 Discontinued
0.6395 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6383 Remote Similarity NPD5284 Approved
0.6383 Remote Similarity NPD5281 Approved
0.6374 Remote Similarity NPD5786 Approved
0.6354 Remote Similarity NPD5210 Approved
0.6354 Remote Similarity NPD4629 Approved
0.6344 Remote Similarity NPD4753 Phase 2
0.6333 Remote Similarity NPD3666 Approved
0.6333 Remote Similarity NPD3665 Phase 1
0.6333 Remote Similarity NPD3133 Approved
0.6322 Remote Similarity NPD4195 Approved
0.6292 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6277 Remote Similarity NPD4096 Approved
0.6222 Remote Similarity NPD5332 Approved
0.6222 Remote Similarity NPD5331 Approved
0.6207 Remote Similarity NPD3617 Approved
0.6146 Remote Similarity NPD4202 Approved
0.6146 Remote Similarity NPD5133 Approved
0.6139 Remote Similarity NPD5211 Phase 2
0.6125 Remote Similarity NPD7341 Phase 2
0.6105 Remote Similarity NPD5207 Approved
0.6049 Remote Similarity NPD7331 Phase 2
0.6022 Remote Similarity NPD4519 Discontinued
0.6022 Remote Similarity NPD4623 Approved
0.6022 Remote Similarity NPD3618 Phase 1
0.6022 Remote Similarity NPD5279 Phase 3
0.602 Remote Similarity NPD1698 Clinical (unspecified phase)
0.602 Remote Similarity NPD5695 Phase 3
0.6019 Remote Similarity NPD5141 Approved
0.6 Remote Similarity NPD5696 Approved
0.6 Remote Similarity NPD345 Approved
0.6 Remote Similarity NPD344 Approved
0.6 Remote Similarity NPD343 Approved
0.598 Remote Similarity NPD5091 Approved
0.5978 Remote Similarity NPD4786 Approved
0.5941 Remote Similarity NPD5285 Approved
0.5941 Remote Similarity NPD5286 Approved
0.5941 Remote Similarity NPD4696 Approved
0.5934 Remote Similarity NPD3667 Approved
0.5926 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5918 Remote Similarity NPD5282 Discontinued
0.5918 Remote Similarity NPD6001 Approved
0.5914 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5904 Remote Similarity NPD5360 Phase 3
0.5904 Remote Similarity NPD5361 Clinical (unspecified phase)
0.59 Remote Similarity NPD6084 Phase 2
0.59 Remote Similarity NPD4755 Approved
0.59 Remote Similarity NPD6083 Phase 2
0.5897 Remote Similarity NPD3198 Approved
0.5895 Remote Similarity NPD5208 Approved
0.5895 Remote Similarity NPD6903 Approved
0.5889 Remote Similarity NPD4822 Approved
0.5889 Remote Similarity NPD4695 Discontinued
0.5889 Remote Similarity NPD5368 Approved
0.5889 Remote Similarity NPD4820 Approved
0.5889 Remote Similarity NPD4821 Approved
0.5889 Remote Similarity NPD4819 Approved
0.5888 Remote Similarity NPD6371 Approved
0.5882 Remote Similarity NPD5223 Approved
0.5876 Remote Similarity NPD6079 Approved
0.5876 Remote Similarity NPD5693 Phase 1
0.5859 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5851 Remote Similarity NPD6098 Approved
0.5833 Remote Similarity NPD5328 Approved
0.5833 Remote Similarity NPD6080 Approved
0.5833 Remote Similarity NPD6673 Approved
0.5833 Remote Similarity NPD6904 Approved
0.5833 Remote Similarity NPD3698 Phase 2
0.5825 Remote Similarity NPD5225 Approved
0.5825 Remote Similarity NPD4633 Approved
0.5825 Remote Similarity NPD5226 Approved
0.5825 Remote Similarity NPD5224 Approved
0.5784 Remote Similarity NPD4700 Approved
0.5773 Remote Similarity NPD5692 Phase 3
0.5769 Remote Similarity NPD5175 Approved
0.5769 Remote Similarity NPD5174 Approved
0.5765 Remote Similarity NPD4245 Approved
0.5765 Remote Similarity NPD4691 Approved
0.5765 Remote Similarity NPD4244 Approved
0.5765 Remote Similarity NPD4747 Approved
0.5761 Remote Similarity NPD6435 Approved
0.5745 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5745 Remote Similarity NPD1696 Phase 3
0.5741 Remote Similarity NPD4634 Approved
0.5714 Remote Similarity NPD6050 Approved
0.5714 Remote Similarity NPD5694 Approved
0.5701 Remote Similarity NPD7320 Approved
0.5698 Remote Similarity NPD4758 Discontinued
0.5698 Remote Similarity NPD4243 Approved
0.5698 Remote Similarity NPD5276 Approved
0.5684 Remote Similarity NPD5330 Approved
0.5684 Remote Similarity NPD6684 Approved
0.5684 Remote Similarity NPD7146 Approved
0.5684 Remote Similarity NPD7521 Approved
0.5684 Remote Similarity NPD6409 Approved
0.5684 Remote Similarity NPD7334 Approved
0.5682 Remote Similarity NPD3702 Approved
0.567 Remote Similarity NPD1695 Approved
0.5667 Remote Similarity NPD4271 Approved
0.5667 Remote Similarity NPD4268 Approved
0.5663 Remote Similarity NPD4224 Phase 2
0.5657 Remote Similarity NPD6399 Phase 3
0.5647 Remote Similarity NPD4137 Phase 3
0.5644 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5644 Remote Similarity NPD4697 Phase 3
0.5644 Remote Similarity NPD5221 Approved
0.5644 Remote Similarity NPD5222 Approved
0.5619 Remote Similarity NPD4754 Approved
0.5607 Remote Similarity NPD5697 Approved
0.5607 Remote Similarity NPD7899 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data