Structure

Physi-Chem Properties

Molecular Weight:  222.16
Volume:  251.815
LogP:  0.992
LogD:  0.721
LogS:  -2.45
# Rotatable Bonds:  3
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.72
Synthetic Accessibility Score:  4.551
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.515
MDCK Permeability:  2.3241918825078756e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.274
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.062
30% Bioavailability (F30%):  0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.4
Plasma Protein Binding (PPB):  70.54618072509766%
Volume Distribution (VD):  0.657
Pgp-substrate:  16.35888671875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.527
CYP1A2-substrate:  0.3
CYP2C19-inhibitor:  0.125
CYP2C19-substrate:  0.886
CYP2C9-inhibitor:  0.067
CYP2C9-substrate:  0.988
CYP2D6-inhibitor:  0.553
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.382
CYP3A4-substrate:  0.347

ADMET: Excretion

Clearance (CL):  3.03
Half-life (T1/2):  0.54

ADMET: Toxicity

hERG Blockers:  0.129
Human Hepatotoxicity (H-HT):  0.734
Drug-inuced Liver Injury (DILI):  0.616
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.04
Maximum Recommended Daily Dose:  0.827
Skin Sensitization:  0.905
Carcinogencity:  0.034
Eye Corrosion:  0.948
Eye Irritation:  0.99
Respiratory Toxicity:  0.901

Download Data

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

  Natural Product: NPC476650

Natural Product ID:  NPC476650
Common Name*:   waikialide B
IUPAC Name:   (1R,3R,4R,5R)-5-[(1E,3E,5E)-hepta-1,3,5-trienyl]-4-methylcyclohexane-1,3-diol
Synonyms:   Waikialide B
Standard InCHIKey:  AOFKGHCPEZTWMZ-KXIQJYATSA-N
Standard InCHI:  InChI=1S/C14H22O2/c1-3-4-5-6-7-8-12-9-13(15)10-14(16)11(12)2/h3-8,11-16H,9-10H2,1-2H3/b4-3+,6-5+,8-7+/t11-,12+,13-,14-/m1/s1
SMILES:  C/C=C/C=C/C=C/[C@H]1C[C@H](C[C@H]([C@@H]1C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   57408411
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001661] Secondary alcohols
            • [CHEMONTID:0002647] Cyclohexanols

*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
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota rhizosphere Sonoran desert n.a. PMID[15620238]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17542490]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17564467]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19053517]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21366228]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21718031]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota healthy leaf of Ginkgo biloba campus of Nanjing University, Nanjing, China 2008-OCT PMID[22196792]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota isolated from the sponge Xestospongia testudinaria n.a. n.a. PMID[22225637]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota Isolated from a sandy-loam soil sample 50 m inland from Waikiki Beach, Honolulu, Hawaii 2010-JUL PMID[22400916]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22703109]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23527875]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24050204]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25001296]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25581396]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26273902]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31012585]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33305943]

☑ 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
NPT20 Organism Candida albicans Candida albicans MIC > 200000 nM PMID[22400916]
NPT20 Organism Candida albicans Candida albicans IC50 = 97000 nM PMID[22400916]

☑ 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 NPC476650 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
0.7917 Intermediate Similarity NPC68443
0.7895 Intermediate Similarity NPC95124
0.7895 Intermediate Similarity NPC471266
0.7857 Intermediate Similarity NPC471238
0.7838 Intermediate Similarity NPC63958
0.7808 Intermediate Similarity NPC91858
0.7794 Intermediate Similarity NPC225415
0.7792 Intermediate Similarity NPC249423
0.7792 Intermediate Similarity NPC471270
0.7778 Intermediate Similarity NPC471272
0.7778 Intermediate Similarity NPC471271
0.7778 Intermediate Similarity NPC471268
0.7733 Intermediate Similarity NPC471798
0.7671 Intermediate Similarity NPC265485
0.7671 Intermediate Similarity NPC220939
0.7662 Intermediate Similarity NPC236707
0.7639 Intermediate Similarity NPC92801
0.7632 Intermediate Similarity NPC148977
0.7606 Intermediate Similarity NPC266578
0.76 Intermediate Similarity NPC253190
0.76 Intermediate Similarity NPC106432
0.7568 Intermediate Similarity NPC243342
0.7568 Intermediate Similarity NPC477138
0.7568 Intermediate Similarity NPC306727
0.7568 Intermediate Similarity NPC476649
0.7564 Intermediate Similarity NPC242350
0.7534 Intermediate Similarity NPC242992
0.7534 Intermediate Similarity NPC477792
0.7534 Intermediate Similarity NPC164022
0.7534 Intermediate Similarity NPC23954
0.7534 Intermediate Similarity NPC167706
0.75 Intermediate Similarity NPC474493
0.75 Intermediate Similarity NPC234511
0.75 Intermediate Similarity NPC225342
0.75 Intermediate Similarity NPC31037
0.7468 Intermediate Similarity NPC259858
0.7467 Intermediate Similarity NPC291503
0.7465 Intermediate Similarity NPC253303
0.7465 Intermediate Similarity NPC269077
0.7436 Intermediate Similarity NPC287749
0.7436 Intermediate Similarity NPC96362
0.7436 Intermediate Similarity NPC324772
0.7432 Intermediate Similarity NPC182717
0.7429 Intermediate Similarity NPC471200
0.7429 Intermediate Similarity NPC300442
0.7407 Intermediate Similarity NPC470360
0.7397 Intermediate Similarity NPC283316
0.7375 Intermediate Similarity NPC82538
0.7375 Intermediate Similarity NPC113978
0.7375 Intermediate Similarity NPC185605
0.7375 Intermediate Similarity NPC237795
0.7368 Intermediate Similarity NPC265588
0.7368 Intermediate Similarity NPC250621
0.7361 Intermediate Similarity NPC96484
0.7342 Intermediate Similarity NPC470383
0.7342 Intermediate Similarity NPC476646
0.7342 Intermediate Similarity NPC320525
0.7333 Intermediate Similarity NPC471797
0.7324 Intermediate Similarity NPC149680
0.7317 Intermediate Similarity NPC6605
0.7317 Intermediate Similarity NPC299068
0.7308 Intermediate Similarity NPC472463
0.7297 Intermediate Similarity NPC242001
0.7297 Intermediate Similarity NPC110799
0.7286 Intermediate Similarity NPC144650
0.7284 Intermediate Similarity NPC136114
0.7273 Intermediate Similarity NPC477924
0.7273 Intermediate Similarity NPC130136
0.7262 Intermediate Similarity NPC128066
0.726 Intermediate Similarity NPC476431
0.7246 Intermediate Similarity NPC194208
0.7246 Intermediate Similarity NPC282694
0.7246 Intermediate Similarity NPC79576
0.7237 Intermediate Similarity NPC66566
0.7237 Intermediate Similarity NPC32832
0.7237 Intermediate Similarity NPC477923
0.7209 Intermediate Similarity NPC310013
0.72 Intermediate Similarity NPC471799
0.7195 Intermediate Similarity NPC471267
0.7183 Intermediate Similarity NPC61503
0.7179 Intermediate Similarity NPC476949
0.7179 Intermediate Similarity NPC230295
0.7179 Intermediate Similarity NPC72507
0.7179 Intermediate Similarity NPC186191
0.7179 Intermediate Similarity NPC253807
0.7179 Intermediate Similarity NPC98386
0.7179 Intermediate Similarity NPC318136
0.7179 Intermediate Similarity NPC158662
0.7179 Intermediate Similarity NPC196753
0.7179 Intermediate Similarity NPC11908
0.7179 Intermediate Similarity NPC205455
0.7176 Intermediate Similarity NPC191323
0.7162 Intermediate Similarity NPC145498
0.716 Intermediate Similarity NPC477818
0.716 Intermediate Similarity NPC471987
0.716 Intermediate Similarity NPC320548
0.716 Intermediate Similarity NPC141941
0.716 Intermediate Similarity NPC57370
0.716 Intermediate Similarity NPC193870
0.7143 Intermediate Similarity NPC1973
0.7143 Intermediate Similarity NPC4574
0.7143 Intermediate Similarity NPC212596
0.7143 Intermediate Similarity NPC473508
0.7143 Intermediate Similarity NPC167873
0.7126 Intermediate Similarity NPC209662
0.7123 Intermediate Similarity NPC208999
0.7123 Intermediate Similarity NPC245795
0.7121 Intermediate Similarity NPC67508
0.7121 Intermediate Similarity NPC84824
0.7108 Intermediate Similarity NPC269058
0.7108 Intermediate Similarity NPC472379
0.7108 Intermediate Similarity NPC71520
0.7108 Intermediate Similarity NPC201273
0.7105 Intermediate Similarity NPC27395
0.7105 Intermediate Similarity NPC100334
0.7105 Intermediate Similarity NPC201048
0.7105 Intermediate Similarity NPC329090
0.7105 Intermediate Similarity NPC476366
0.7101 Intermediate Similarity NPC240506
0.7089 Intermediate Similarity NPC53744
0.7083 Intermediate Similarity NPC202017
0.7083 Intermediate Similarity NPC267027
0.7083 Intermediate Similarity NPC326310
0.7073 Intermediate Similarity NPC231310
0.7073 Intermediate Similarity NPC475798
0.7073 Intermediate Similarity NPC127606
0.7073 Intermediate Similarity NPC302360
0.7067 Intermediate Similarity NPC469343
0.7059 Intermediate Similarity NPC101886
0.7059 Intermediate Similarity NPC109744
0.7051 Intermediate Similarity NPC214570
0.7051 Intermediate Similarity NPC40394
0.7051 Intermediate Similarity NPC472805
0.7051 Intermediate Similarity NPC470428
0.7051 Intermediate Similarity NPC157996
0.7051 Intermediate Similarity NPC91594
0.7051 Intermediate Similarity NPC85105
0.7051 Intermediate Similarity NPC90979
0.7051 Intermediate Similarity NPC470711
0.7051 Intermediate Similarity NPC149550
0.7051 Intermediate Similarity NPC34177
0.7051 Intermediate Similarity NPC470758
0.7051 Intermediate Similarity NPC101475
0.7042 Intermediate Similarity NPC101128
0.7042 Intermediate Similarity NPC219940
0.7042 Intermediate Similarity NPC290367
0.7042 Intermediate Similarity NPC300593
0.7037 Intermediate Similarity NPC224455
0.7037 Intermediate Similarity NPC201852
0.7037 Intermediate Similarity NPC202389
0.7037 Intermediate Similarity NPC248886
0.7027 Intermediate Similarity NPC210323
0.7027 Intermediate Similarity NPC9942
0.7024 Intermediate Similarity NPC304083
0.7024 Intermediate Similarity NPC474657
0.7024 Intermediate Similarity NPC186145
0.7013 Intermediate Similarity NPC171148
0.7013 Intermediate Similarity NPC313179
0.7013 Intermediate Similarity NPC69383
0.7013 Intermediate Similarity NPC328104
0.7013 Intermediate Similarity NPC319090
0.7013 Intermediate Similarity NPC103822
0.6988 Remote Similarity NPC109528
0.6988 Remote Similarity NPC280203
0.6986 Remote Similarity NPC45782
0.6986 Remote Similarity NPC139207
0.6986 Remote Similarity NPC82337
0.6986 Remote Similarity NPC185874
0.6977 Remote Similarity NPC470390
0.6977 Remote Similarity NPC14380
0.6977 Remote Similarity NPC291484
0.6977 Remote Similarity NPC329596
0.6977 Remote Similarity NPC204188
0.6977 Remote Similarity NPC192437
0.6977 Remote Similarity NPC80561
0.6977 Remote Similarity NPC473956
0.6977 Remote Similarity NPC475751
0.6977 Remote Similarity NPC270511
0.6977 Remote Similarity NPC11216
0.6977 Remote Similarity NPC245410
0.6977 Remote Similarity NPC3345
0.6974 Remote Similarity NPC95165
0.6962 Remote Similarity NPC307965
0.6962 Remote Similarity NPC275910
0.6962 Remote Similarity NPC31828
0.6962 Remote Similarity NPC470396
0.6962 Remote Similarity NPC99168
0.6962 Remote Similarity NPC244385
0.6962 Remote Similarity NPC6978
0.6962 Remote Similarity NPC300499
0.6962 Remote Similarity NPC215307
0.6962 Remote Similarity NPC474989
0.6962 Remote Similarity NPC76931
0.6962 Remote Similarity NPC52755
0.6962 Remote Similarity NPC138621
0.6962 Remote Similarity NPC22955
0.6962 Remote Similarity NPC475980
0.6962 Remote Similarity NPC285761
0.6962 Remote Similarity NPC167037
0.6962 Remote Similarity NPC87604

  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 NPC476650 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
0.7532 Intermediate Similarity NPD6929 Approved
0.75 Intermediate Similarity NPD6932 Approved
0.7436 Intermediate Similarity NPD6930 Phase 2
0.7436 Intermediate Similarity NPD6931 Approved
0.7403 Intermediate Similarity NPD7145 Approved
0.7273 Intermediate Similarity NPD5776 Phase 2
0.7273 Intermediate Similarity NPD6925 Approved
0.7215 Intermediate Similarity NPD7514 Phase 3
0.7215 Intermediate Similarity NPD7332 Phase 2
0.716 Intermediate Similarity NPD6695 Phase 3
0.7125 Intermediate Similarity NPD6902 Approved
0.7105 Intermediate Similarity NPD6926 Approved
0.7105 Intermediate Similarity NPD6924 Approved
0.7089 Intermediate Similarity NPD7645 Phase 2
0.7089 Intermediate Similarity NPD6683 Phase 2
0.7073 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD7150 Approved
0.7067 Intermediate Similarity NPD7151 Approved
0.7067 Intermediate Similarity NPD7152 Approved
0.7013 Intermediate Similarity NPD8264 Approved
0.6988 Remote Similarity NPD6893 Approved
0.6974 Remote Similarity NPD4732 Discontinued
0.6933 Remote Similarity NPD7143 Approved
0.6933 Remote Similarity NPD7144 Approved
0.6923 Remote Similarity NPD6933 Approved
0.6914 Remote Similarity NPD6898 Phase 1
0.6824 Remote Similarity NPD7750 Discontinued
0.6824 Remote Similarity NPD7524 Approved
0.68 Remote Similarity NPD6922 Approved
0.68 Remote Similarity NPD6923 Approved
0.679 Remote Similarity NPD7525 Registered
0.679 Remote Similarity NPD7509 Discontinued
0.6761 Remote Similarity NPD368 Approved
0.6709 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6618 Remote Similarity NPD342 Phase 1
0.6582 Remote Similarity NPD6942 Approved
0.6582 Remote Similarity NPD7339 Approved
0.6543 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6517 Remote Similarity NPD7087 Discontinued
0.6444 Remote Similarity NPD5778 Approved
0.6444 Remote Similarity NPD5779 Approved
0.6406 Remote Similarity NPD384 Approved
0.6406 Remote Similarity NPD385 Approved
0.6404 Remote Similarity NPD3168 Discontinued
0.6404 Remote Similarity NPD7136 Phase 2
0.6383 Remote Similarity NPD6648 Approved
0.6351 Remote Similarity NPD371 Approved
0.6333 Remote Similarity NPD7637 Suspended
0.6322 Remote Similarity NPD3618 Phase 1
0.6316 Remote Similarity NPD5344 Discontinued
0.6292 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6292 Remote Similarity NPD6101 Approved
0.625 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6235 Remote Similarity NPD3667 Approved
0.6212 Remote Similarity NPD9410 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6079 Approved
0.6154 Remote Similarity NPD6411 Approved
0.6136 Remote Similarity NPD5279 Phase 3
0.6111 Remote Similarity NPD5328 Approved
0.6092 Remote Similarity NPD4786 Approved
0.6056 Remote Similarity NPD4219 Approved
0.6 Remote Similarity NPD4748 Discontinued
0.6 Remote Similarity NPD388 Approved
0.6 Remote Similarity NPD386 Approved
0.6 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5978 Remote Similarity NPD7515 Phase 2
0.5952 Remote Similarity NPD4271 Approved
0.5952 Remote Similarity NPD4268 Approved
0.5938 Remote Similarity NPD7638 Approved
0.5914 Remote Similarity NPD4202 Approved
0.5909 Remote Similarity NPD3665 Phase 1
0.5909 Remote Similarity NPD3666 Approved
0.5909 Remote Similarity NPD3133 Approved
0.5895 Remote Similarity NPD5222 Approved
0.5895 Remote Similarity NPD5221 Approved
0.5895 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5876 Remote Similarity NPD5286 Approved
0.5876 Remote Similarity NPD4696 Approved
0.5876 Remote Similarity NPD7639 Approved
0.5876 Remote Similarity NPD5285 Approved
0.5876 Remote Similarity NPD7640 Approved
0.587 Remote Similarity NPD7838 Discovery
0.5854 Remote Similarity NPD4784 Approved
0.5854 Remote Similarity NPD4785 Approved
0.5833 Remote Similarity NPD5173 Approved
0.5833 Remote Similarity NPD4755 Approved
0.5814 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5814 Remote Similarity NPD5368 Approved
0.5814 Remote Similarity NPD4822 Approved
0.5814 Remote Similarity NPD4821 Approved
0.5814 Remote Similarity NPD4820 Approved
0.5814 Remote Similarity NPD4819 Approved
0.5802 Remote Similarity NPD4243 Approved
0.5778 Remote Similarity NPD4249 Approved
0.5773 Remote Similarity NPD5290 Discontinued
0.5773 Remote Similarity NPD4225 Approved
0.5758 Remote Similarity NPD5226 Approved
0.5758 Remote Similarity NPD5211 Phase 2
0.5758 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5758 Remote Similarity NPD4633 Approved
0.5758 Remote Similarity NPD5224 Approved
0.5758 Remote Similarity NPD5225 Approved
0.5743 Remote Similarity NPD5357 Phase 1
0.5733 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5729 Remote Similarity NPD4697 Phase 3
0.5714 Remote Similarity NPD4251 Approved
0.5714 Remote Similarity NPD4700 Approved
0.5714 Remote Similarity NPD4250 Approved
0.57 Remote Similarity NPD5175 Approved
0.57 Remote Similarity NPD5174 Approved
0.5698 Remote Similarity NPD4195 Approved
0.5684 Remote Similarity NPD7748 Approved
0.5682 Remote Similarity NPD6435 Approved
0.5679 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5673 Remote Similarity NPD4634 Approved
0.5667 Remote Similarity NPD1696 Phase 3
0.5667 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5657 Remote Similarity NPD5223 Approved
0.5644 Remote Similarity NPD5141 Approved
0.5638 Remote Similarity NPD7983 Approved

  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