Structure

Physi-Chem Properties

Molecular Weight:  228.17
Volume:  248.582
LogP:  1.356
LogD:  0.857
LogS:  -1.633
# Rotatable Bonds:  2
TPSA:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.627
Synthetic Accessibility Score:  4.477
Fsp3:  0.846
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:  -4.782
MDCK Permeability:  8.69811192387715e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.938
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.043
30% Bioavailability (F30%):  0.611

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.966
Plasma Protein Binding (PPB):  73.0728988647461%
Volume Distribution (VD):  1.419
Pgp-substrate:  37.232460021972656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.243
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.819
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.179
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.09
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.306

ADMET: Excretion

Clearance (CL):  6.939
Half-life (T1/2):  0.422

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.289
Drug-inuced Liver Injury (DILI):  0.021
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.839
Maximum Recommended Daily Dose:  0.978
Skin Sensitization:  0.175
Carcinogencity:  0.284
Eye Corrosion:  0.005
Eye Irritation:  0.512
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC471272

Natural Product ID:  NPC471272
Common Name*:   (3S,5S,6S,9R)-3,6-Dihydroxy-5,6-Dihydro-Beta-Ionol
IUPAC Name:   (1S,4S,6S)-1-[(E,3R)-3-hydroxybut-1-enyl]-2,2,6-trimethylcyclohexane-1,4-diol
Synonyms:  
Standard InCHIKey:  OJGKTHCXUFNMIQ-RFISKLBLSA-N
Standard InCHI:  InChI=1S/C13H24O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-6,9-11,14-16H,7-8H2,1-4H3/b6-5+/t9-,10+,11-,13+/m0/s1
SMILES:  CC1CC(CC(C1(C=CC(C)O)O)(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2407704
PubChem CID:   73346008
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
NPO32875 cinnamomum wilsonii Species Lauraceae Eukaryota Leaves n.a. n.a. PMID[23822611]

☑ 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
NPT660 Cell Line SW480 Homo sapiens IC50 > 10000.0 nM PMID[575603]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[575603]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[575603]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000.0 nM PMID[575603]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[575603]

☑ 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 NPC471272 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
0.9545 High Similarity NPC471238
0.913 High Similarity NPC471271
0.913 High Similarity NPC471268
0.9028 High Similarity NPC85105
0.9028 High Similarity NPC149550
0.8919 High Similarity NPC471266
0.8919 High Similarity NPC95124
0.8857 High Similarity NPC477792
0.8857 High Similarity NPC23954
0.8857 High Similarity NPC164022
0.88 High Similarity NPC471270
0.8667 High Similarity NPC236707
0.863 High Similarity NPC265588
0.8611 High Similarity NPC201048
0.8611 High Similarity NPC476366
0.8514 High Similarity NPC470711
0.8514 High Similarity NPC470758
0.8472 Intermediate Similarity NPC265485
0.8472 Intermediate Similarity NPC220939
0.8451 Intermediate Similarity NPC92801
0.8442 Intermediate Similarity NPC259858
0.8429 Intermediate Similarity NPC96484
0.8421 Intermediate Similarity NPC96362
0.84 Intermediate Similarity NPC11908
0.8378 Intermediate Similarity NPC470749
0.8378 Intermediate Similarity NPC253190
0.8378 Intermediate Similarity NPC1973
0.8378 Intermediate Similarity NPC167873
0.8356 Intermediate Similarity NPC306727
0.8333 Intermediate Similarity NPC185605
0.8333 Intermediate Similarity NPC167706
0.8312 Intermediate Similarity NPC249423
0.8312 Intermediate Similarity NPC476646
0.831 Intermediate Similarity NPC9942
0.8286 Intermediate Similarity NPC185874
0.8286 Intermediate Similarity NPC139207
0.8267 Intermediate Similarity NPC91594
0.8243 Intermediate Similarity NPC133580
0.8243 Intermediate Similarity NPC291503
0.8243 Intermediate Similarity NPC32832
0.8219 Intermediate Similarity NPC68443
0.8205 Intermediate Similarity NPC296701
0.8205 Intermediate Similarity NPC218616
0.8205 Intermediate Similarity NPC87489
0.8194 Intermediate Similarity NPC34834
0.8125 Intermediate Similarity NPC471267
0.8116 Intermediate Similarity NPC225415
0.8116 Intermediate Similarity NPC300593
0.8108 Intermediate Similarity NPC243342
0.8108 Intermediate Similarity NPC91858
0.8108 Intermediate Similarity NPC477138
0.8101 Intermediate Similarity NPC82623
0.8056 Intermediate Similarity NPC474248
0.8056 Intermediate Similarity NPC471560
0.8028 Intermediate Similarity NPC68703
0.8028 Intermediate Similarity NPC69649
0.8025 Intermediate Similarity NPC299068
0.8 Intermediate Similarity NPC231310
0.8 Intermediate Similarity NPC258595
0.7975 Intermediate Similarity NPC155521
0.7975 Intermediate Similarity NPC49964
0.7973 Intermediate Similarity NPC182717
0.7971 Intermediate Similarity NPC81615
0.7971 Intermediate Similarity NPC83200
0.7952 Intermediate Similarity NPC115607
0.7949 Intermediate Similarity NPC281880
0.7949 Intermediate Similarity NPC206062
0.7949 Intermediate Similarity NPC295131
0.7941 Intermediate Similarity NPC240506
0.7922 Intermediate Similarity NPC167891
0.7922 Intermediate Similarity NPC476314
0.7922 Intermediate Similarity NPC83351
0.7917 Intermediate Similarity NPC276616
0.7917 Intermediate Similarity NPC245795
0.7901 Intermediate Similarity NPC470360
0.7895 Intermediate Similarity NPC106432
0.7887 Intermediate Similarity NPC476406
0.7887 Intermediate Similarity NPC202017
0.7887 Intermediate Similarity NPC267027
0.7875 Intermediate Similarity NPC134481
0.7875 Intermediate Similarity NPC79945
0.7875 Intermediate Similarity NPC470558
0.7867 Intermediate Similarity NPC309178
0.7857 Intermediate Similarity NPC96793
0.7857 Intermediate Similarity NPC101128
0.7857 Intermediate Similarity NPC68656
0.7857 Intermediate Similarity NPC144650
0.7857 Intermediate Similarity NPC323424
0.7848 Intermediate Similarity NPC159148
0.7848 Intermediate Similarity NPC264245
0.7838 Intermediate Similarity NPC242992
0.7838 Intermediate Similarity NPC110799
0.7838 Intermediate Similarity NPC242001
0.7831 Intermediate Similarity NPC133588
0.7826 Intermediate Similarity NPC207007
0.7826 Intermediate Similarity NPC321867
0.7826 Intermediate Similarity NPC68679
0.7821 Intermediate Similarity NPC273410
0.7821 Intermediate Similarity NPC30986
0.7821 Intermediate Similarity NPC80530
0.7821 Intermediate Similarity NPC209430
0.7808 Intermediate Similarity NPC473893
0.7808 Intermediate Similarity NPC210323
0.7805 Intermediate Similarity NPC139724
0.7805 Intermediate Similarity NPC261266
0.7792 Intermediate Similarity NPC474826
0.7792 Intermediate Similarity NPC477425
0.7792 Intermediate Similarity NPC477427
0.7792 Intermediate Similarity NPC477426
0.7792 Intermediate Similarity NPC471798
0.7778 Intermediate Similarity NPC269077
0.7778 Intermediate Similarity NPC114651
0.7778 Intermediate Similarity NPC476650
0.7778 Intermediate Similarity NPC253303
0.7778 Intermediate Similarity NPC238485
0.7778 Intermediate Similarity NPC171225
0.7778 Intermediate Similarity NPC205845
0.7778 Intermediate Similarity NPC470077
0.7763 Intermediate Similarity NPC171148
0.7763 Intermediate Similarity NPC66566
0.7763 Intermediate Similarity NPC477923
0.7763 Intermediate Similarity NPC313179
0.7763 Intermediate Similarity NPC313185
0.7763 Intermediate Similarity NPC69383
0.775 Intermediate Similarity NPC202389
0.775 Intermediate Similarity NPC2524
0.775 Intermediate Similarity NPC109938
0.775 Intermediate Similarity NPC471408
0.775 Intermediate Similarity NPC122945
0.7746 Intermediate Similarity NPC2728
0.7746 Intermediate Similarity NPC282619
0.7746 Intermediate Similarity NPC287339
0.7746 Intermediate Similarity NPC208198
0.7746 Intermediate Similarity NPC172613
0.7746 Intermediate Similarity NPC60837
0.7746 Intermediate Similarity NPC11555
0.7738 Intermediate Similarity NPC97103
0.7733 Intermediate Similarity NPC471799
0.7733 Intermediate Similarity NPC259049
0.7733 Intermediate Similarity NPC130665
0.7727 Intermediate Similarity NPC471269
0.7722 Intermediate Similarity NPC234193
0.7722 Intermediate Similarity NPC236237
0.7722 Intermediate Similarity NPC102253
0.7722 Intermediate Similarity NPC148685
0.7722 Intermediate Similarity NPC104120
0.7722 Intermediate Similarity NPC287749
0.7722 Intermediate Similarity NPC322313
0.7722 Intermediate Similarity NPC241290
0.7722 Intermediate Similarity NPC164840
0.7722 Intermediate Similarity NPC113024
0.7722 Intermediate Similarity NPC157895
0.7722 Intermediate Similarity NPC209944
0.7714 Intermediate Similarity NPC174956
0.7703 Intermediate Similarity NPC283316
0.7703 Intermediate Similarity NPC145498
0.7692 Intermediate Similarity NPC6978
0.7692 Intermediate Similarity NPC138621
0.7692 Intermediate Similarity NPC285761
0.7692 Intermediate Similarity NPC244385
0.7692 Intermediate Similarity NPC300499
0.7692 Intermediate Similarity NPC167037
0.7683 Intermediate Similarity NPC109528
0.7683 Intermediate Similarity NPC318390
0.7683 Intermediate Similarity NPC274448
0.7681 Intermediate Similarity NPC66020
0.7671 Intermediate Similarity NPC244790
0.7671 Intermediate Similarity NPC2648
0.7671 Intermediate Similarity NPC208999
0.7662 Intermediate Similarity NPC477925
0.7662 Intermediate Similarity NPC274079
0.7662 Intermediate Similarity NPC63958
0.7654 Intermediate Similarity NPC471987
0.7647 Intermediate Similarity NPC77796
0.7647 Intermediate Similarity NPC476226
0.7647 Intermediate Similarity NPC92885
0.7647 Intermediate Similarity NPC3345
0.7647 Intermediate Similarity NPC11216
0.7647 Intermediate Similarity NPC329596
0.7647 Intermediate Similarity NPC291484
0.7647 Intermediate Similarity NPC80561
0.7647 Intermediate Similarity NPC134321
0.7647 Intermediate Similarity NPC204188
0.7639 Intermediate Similarity NPC475897
0.7639 Intermediate Similarity NPC326310
0.7639 Intermediate Similarity NPC279434
0.7632 Intermediate Similarity NPC469593
0.7632 Intermediate Similarity NPC469534
0.7632 Intermediate Similarity NPC471797
0.7632 Intermediate Similarity NPC78527
0.7632 Intermediate Similarity NPC469533
0.7632 Intermediate Similarity NPC100334
0.7625 Intermediate Similarity NPC47761
0.7625 Intermediate Similarity NPC311891
0.7619 Intermediate Similarity NPC4574
0.7619 Intermediate Similarity NPC131453
0.7619 Intermediate Similarity NPC212596
0.7606 Intermediate Similarity NPC290367
0.7606 Intermediate Similarity NPC107540
0.7606 Intermediate Similarity NPC219940

  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 NPC471272 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
0.7826 Intermediate Similarity NPD368 Approved
0.7763 Intermediate Similarity NPD8264 Approved
0.7722 Intermediate Similarity NPD7525 Registered
0.7375 Intermediate Similarity NPD7645 Phase 2
0.725 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6924 Approved
0.7179 Intermediate Similarity NPD6926 Approved
0.7093 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6942 Approved
0.7089 Intermediate Similarity NPD7339 Approved
0.7073 Intermediate Similarity NPD7514 Phase 3
0.7073 Intermediate Similarity NPD7509 Discontinued
0.7073 Intermediate Similarity NPD7332 Phase 2
0.7073 Intermediate Similarity NPD6930 Phase 2
0.7073 Intermediate Similarity NPD6931 Approved
0.7 Intermediate Similarity NPD6933 Approved
0.6957 Remote Similarity NPD342 Phase 1
0.6951 Remote Similarity NPD6929 Approved
0.6941 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7151 Approved
0.6923 Remote Similarity NPD7150 Approved
0.6923 Remote Similarity NPD7152 Approved
0.6829 Remote Similarity NPD7145 Approved
0.6824 Remote Similarity NPD6695 Phase 3
0.6795 Remote Similarity NPD7143 Approved
0.6795 Remote Similarity NPD7144 Approved
0.6786 Remote Similarity NPD6902 Approved
0.6782 Remote Similarity NPD3618 Phase 1
0.6707 Remote Similarity NPD5776 Phase 2
0.6707 Remote Similarity NPD6932 Approved
0.6707 Remote Similarity NPD6925 Approved
0.6706 Remote Similarity NPD3667 Approved
0.6703 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD6893 Approved
0.6667 Remote Similarity NPD6922 Approved
0.6667 Remote Similarity NPD6923 Approved
0.6667 Remote Similarity NPD5211 Phase 2
0.6667 Remote Similarity NPD4748 Discontinued
0.6625 Remote Similarity NPD4732 Discontinued
0.662 Remote Similarity NPD4219 Approved
0.6593 Remote Similarity NPD6079 Approved
0.6588 Remote Similarity NPD6898 Phase 1
0.6562 Remote Similarity NPD5344 Discontinued
0.6556 Remote Similarity NPD5328 Approved
0.6552 Remote Similarity NPD4786 Approved
0.6543 Remote Similarity NPD4784 Approved
0.6543 Remote Similarity NPD4785 Approved
0.6531 Remote Similarity NPD5141 Approved
0.6526 Remote Similarity NPD4225 Approved
0.6517 Remote Similarity NPD7750 Discontinued
0.6517 Remote Similarity NPD7524 Approved
0.65 Remote Similarity NPD4243 Approved
0.6477 Remote Similarity NPD1696 Phase 3
0.6471 Remote Similarity NPD4821 Approved
0.6471 Remote Similarity NPD4819 Approved
0.6471 Remote Similarity NPD4820 Approved
0.6471 Remote Similarity NPD4822 Approved
0.6458 Remote Similarity NPD7639 Approved
0.6458 Remote Similarity NPD5286 Approved
0.6458 Remote Similarity NPD4696 Approved
0.6458 Remote Similarity NPD5285 Approved
0.6458 Remote Similarity NPD7640 Approved
0.6429 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6421 Remote Similarity NPD4755 Approved
0.6413 Remote Similarity NPD7515 Phase 2
0.6404 Remote Similarity NPD4519 Discontinued
0.6404 Remote Similarity NPD4623 Approved
0.6392 Remote Similarity NPD5223 Approved
0.6364 Remote Similarity NPD3665 Phase 1
0.6364 Remote Similarity NPD3133 Approved
0.6364 Remote Similarity NPD3666 Approved
0.6354 Remote Similarity NPD7638 Approved
0.6353 Remote Similarity NPD6683 Phase 2
0.6353 Remote Similarity NPD4195 Approved
0.6327 Remote Similarity NPD5224 Approved
0.6327 Remote Similarity NPD5226 Approved
0.6327 Remote Similarity NPD4633 Approved
0.6327 Remote Similarity NPD5225 Approved
0.6316 Remote Similarity NPD5222 Approved
0.6316 Remote Similarity NPD5221 Approved
0.6316 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6289 Remote Similarity NPD4700 Approved
0.6289 Remote Similarity NPD6648 Approved
0.6269 Remote Similarity NPD385 Approved
0.6269 Remote Similarity NPD384 Approved
0.6265 Remote Similarity NPD4190 Phase 3
0.6265 Remote Similarity NPD5275 Approved
0.6263 Remote Similarity NPD5174 Approved
0.6263 Remote Similarity NPD5175 Approved
0.625 Remote Similarity NPD5173 Approved
0.6237 Remote Similarity NPD7087 Discontinued
0.6235 Remote Similarity NPD4271 Approved
0.6235 Remote Similarity NPD4268 Approved
0.6222 Remote Similarity NPD5279 Phase 3
0.6186 Remote Similarity NPD5290 Discontinued
0.6146 Remote Similarity NPD4697 Phase 3
0.6129 Remote Similarity NPD3168 Discontinued
0.6111 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6105 Remote Similarity NPD7748 Approved
0.61 Remote Similarity NPD4754 Approved
0.6092 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6082 Remote Similarity NPD7902 Approved
0.6078 Remote Similarity NPD5697 Approved
0.6064 Remote Similarity NPD7637 Suspended
0.6049 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6022 Remote Similarity NPD4753 Phase 2
0.6019 Remote Similarity NPD4729 Approved
0.6019 Remote Similarity NPD6011 Approved
0.6019 Remote Similarity NPD6899 Approved
0.6019 Remote Similarity NPD6881 Approved
0.6019 Remote Similarity NPD4730 Approved
0.6 Remote Similarity NPD3668 Phase 3
0.6 Remote Similarity NPD5779 Approved
0.6 Remote Similarity NPD5778 Approved
0.6 Remote Similarity NPD6399 Phase 3
0.598 Remote Similarity NPD4767 Approved
0.598 Remote Similarity NPD7128 Approved
0.598 Remote Similarity NPD6402 Approved
0.598 Remote Similarity NPD5739 Approved
0.598 Remote Similarity NPD4768 Approved
0.598 Remote Similarity NPD6675 Approved
0.5962 Remote Similarity NPD6013 Approved
0.5962 Remote Similarity NPD6014 Approved
0.5962 Remote Similarity NPD6012 Approved
0.5957 Remote Similarity NPD7136 Phase 2
0.5955 Remote Similarity NPD4269 Approved
0.5955 Remote Similarity NPD4221 Approved
0.5955 Remote Similarity NPD4223 Phase 3
0.5955 Remote Similarity NPD4270 Approved
0.5934 Remote Similarity NPD1694 Approved
0.5922 Remote Similarity NPD5701 Approved
0.5909 Remote Similarity NPD4695 Discontinued
0.5909 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5905 Remote Similarity NPD5248 Approved
0.5905 Remote Similarity NPD5135 Approved
0.5905 Remote Similarity NPD5251 Approved
0.5905 Remote Similarity NPD5249 Phase 3
0.5905 Remote Similarity NPD7102 Approved
0.5905 Remote Similarity NPD5247 Approved
0.5905 Remote Similarity NPD4634 Approved
0.5905 Remote Similarity NPD6883 Approved
0.5905 Remote Similarity NPD5169 Approved
0.5905 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5905 Remote Similarity NPD5250 Approved
0.5905 Remote Similarity NPD7290 Approved
0.59 Remote Similarity NPD4159 Approved
0.5895 Remote Similarity NPD6411 Approved
0.5889 Remote Similarity NPD5332 Approved
0.5889 Remote Similarity NPD5362 Discontinued
0.5889 Remote Similarity NPD5331 Approved
0.5876 Remote Similarity NPD4629 Approved
0.5876 Remote Similarity NPD5210 Approved
0.5872 Remote Similarity NPD7115 Discovery
0.587 Remote Similarity NPD5690 Phase 2
0.587 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5865 Remote Similarity NPD7320 Approved
0.5865 Remote Similarity NPD5128 Approved
0.5857 Remote Similarity NPD9410 Clinical (unspecified phase)
0.5851 Remote Similarity NPD6051 Approved
0.5849 Remote Similarity NPD6617 Approved
0.5849 Remote Similarity NPD6847 Approved
0.5849 Remote Similarity NPD5127 Approved
0.5849 Remote Similarity NPD6649 Approved
0.5849 Remote Similarity NPD6869 Approved
0.5849 Remote Similarity NPD5216 Approved
0.5849 Remote Similarity NPD5217 Approved
0.5849 Remote Similarity NPD6650 Approved
0.5849 Remote Similarity NPD5215 Approved
0.5849 Remote Similarity NPD8130 Phase 1
0.5843 Remote Similarity NPD4790 Discontinued
0.5842 Remote Similarity NPD7632 Discontinued
0.5824 Remote Similarity NPD4197 Approved
0.5823 Remote Similarity NPD371 Approved
0.5818 Remote Similarity NPD7328 Approved
0.5818 Remote Similarity NPD7327 Approved
0.581 Remote Similarity NPD6372 Approved
0.581 Remote Similarity NPD4061 Clinical (unspecified phase)
0.581 Remote Similarity NPD6373 Approved
0.5806 Remote Similarity NPD3573 Approved
0.5794 Remote Similarity NPD6882 Approved
0.5794 Remote Similarity NPD8297 Approved
0.5789 Remote Similarity NPD5785 Approved
0.5783 Remote Similarity NPD4787 Phase 1
0.5778 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5773 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5773 Remote Similarity NPD7900 Approved
0.5769 Remote Similarity NPD4194 Approved
0.5769 Remote Similarity NPD4191 Approved
0.5769 Remote Similarity NPD4192 Approved
0.5769 Remote Similarity NPD4193 Approved
0.5766 Remote Similarity NPD7516 Approved
0.5761 Remote Similarity NPD5329 Approved
0.5761 Remote Similarity NPD5363 Approved
0.5741 Remote Similarity NPD4632 Approved
0.573 Remote Similarity NPD5368 Approved
0.573 Remote Similarity NPD4252 Approved
0.5729 Remote Similarity NPD5284 Approved
0.5729 Remote Similarity NPD8035 Phase 2
0.5729 Remote Similarity NPD5281 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