Structure

Physi-Chem Properties

Molecular Weight:  208.11
Volume:  217.457
LogP:  2.522
LogD:  1.804
LogS:  -2.257
# Rotatable Bonds:  1
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.487
Synthetic Accessibility Score:  4.269
Fsp3:  0.667
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:  -4.601
MDCK Permeability:  4.9148275138577446e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.084
20% Bioavailability (F20%):  0.866
30% Bioavailability (F30%):  0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.937
Plasma Protein Binding (PPB):  51.56251525878906%
Volume Distribution (VD):  1.248
Pgp-substrate:  55.095970153808594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.124
CYP1A2-substrate:  0.1
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.739
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.102
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.097
CYP3A4-inhibitor:  0.241
CYP3A4-substrate:  0.371

ADMET: Excretion

Clearance (CL):  7.548
Half-life (T1/2):  0.648

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.855
Drug-inuced Liver Injury (DILI):  0.259
AMES Toxicity:  0.436
Rat Oral Acute Toxicity:  0.425
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.944
Carcinogencity:  0.922
Eye Corrosion:  0.936
Eye Irritation:  0.949
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: NPC472959

Natural Product ID:  NPC472959
Common Name*:   AACLWACKHXOGDA-URPMGSGRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  AACLWACKHXOGDA-URPMGSGRSA-N
Standard InCHI:  InChI=1S/C12H16O3/c1-7-5-11-10(4-3-9(7)6-13)8(2)12(14)15-11/h3,6-8,10-11H,4-5H2,1-2H3/t7-,8+,10+,11-/m0/s1
SMILES:  O=CC1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)[C@@H]2C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3594191
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota Fruits n.a. n.a. PMID[26110443]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17612 Xanthium sibiricum Species Asteraceae 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
NPT3119 Organism Human coxsackievirus B3 Human coxsackievirus B3 IC50 > 35000.0 nM PMID[497846]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[497846]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 35000.0 nM PMID[497846]

☑ 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 NPC472959 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
0.9189 High Similarity NPC472960
0.8919 High Similarity NPC472967
0.8919 High Similarity NPC266159
0.8873 High Similarity NPC296522
0.8873 High Similarity NPC144511
0.8767 High Similarity NPC472956
0.875 High Similarity NPC472955
0.8553 High Similarity NPC195785
0.8553 High Similarity NPC15975
0.8533 High Similarity NPC226669
0.8533 High Similarity NPC138408
0.8533 High Similarity NPC193351
0.85 High Similarity NPC472958
0.85 High Similarity NPC472957
0.84 Intermediate Similarity NPC472966
0.8375 Intermediate Similarity NPC39588
0.8354 Intermediate Similarity NPC35089
0.8354 Intermediate Similarity NPC10276
0.8333 Intermediate Similarity NPC63649
0.8333 Intermediate Similarity NPC264227
0.8333 Intermediate Similarity NPC472965
0.8333 Intermediate Similarity NPC182550
0.8312 Intermediate Similarity NPC65603
0.8312 Intermediate Similarity NPC476794
0.8312 Intermediate Similarity NPC470240
0.8228 Intermediate Similarity NPC302426
0.8171 Intermediate Similarity NPC161957
0.8158 Intermediate Similarity NPC469643
0.8158 Intermediate Similarity NPC469641
0.8148 Intermediate Similarity NPC52609
0.8148 Intermediate Similarity NPC1761
0.8125 Intermediate Similarity NPC39411
0.8125 Intermediate Similarity NPC255580
0.8108 Intermediate Similarity NPC261398
0.8108 Intermediate Similarity NPC199557
0.8101 Intermediate Similarity NPC470244
0.8101 Intermediate Similarity NPC470239
0.8077 Intermediate Similarity NPC187568
0.8077 Intermediate Similarity NPC41780
0.8052 Intermediate Similarity NPC155587
0.8 Intermediate Similarity NPC276356
0.8 Intermediate Similarity NPC69271
0.8 Intermediate Similarity NPC74673
0.8 Intermediate Similarity NPC223904
0.7975 Intermediate Similarity NPC128276
0.7949 Intermediate Similarity NPC235906
0.7922 Intermediate Similarity NPC476355
0.7901 Intermediate Similarity NPC281949
0.7901 Intermediate Similarity NPC301477
0.7901 Intermediate Similarity NPC25684
0.7895 Intermediate Similarity NPC129665
0.7895 Intermediate Similarity NPC163003
0.7875 Intermediate Similarity NPC261125
0.7875 Intermediate Similarity NPC469690
0.7875 Intermediate Similarity NPC181195
0.7857 Intermediate Similarity NPC70422
0.7857 Intermediate Similarity NPC107787
0.7857 Intermediate Similarity NPC70555
0.7857 Intermediate Similarity NPC104961
0.7848 Intermediate Similarity NPC57744
0.7831 Intermediate Similarity NPC165287
0.7831 Intermediate Similarity NPC115786
0.7821 Intermediate Similarity NPC324762
0.7805 Intermediate Similarity NPC173609
0.7792 Intermediate Similarity NPC58956
0.7792 Intermediate Similarity NPC295633
0.7792 Intermediate Similarity NPC269206
0.7778 Intermediate Similarity NPC281132
0.7765 Intermediate Similarity NPC237540
0.775 Intermediate Similarity NPC207186
0.775 Intermediate Similarity NPC299235
0.7738 Intermediate Similarity NPC21471
0.7738 Intermediate Similarity NPC33570
0.7738 Intermediate Similarity NPC78089
0.7722 Intermediate Similarity NPC123360
0.7711 Intermediate Similarity NPC272814
0.7711 Intermediate Similarity NPC318468
0.7701 Intermediate Similarity NPC62815
0.7701 Intermediate Similarity NPC253144
0.7692 Intermediate Similarity NPC140287
0.7683 Intermediate Similarity NPC475665
0.7683 Intermediate Similarity NPC470241
0.7683 Intermediate Similarity NPC207188
0.7683 Intermediate Similarity NPC471325
0.7654 Intermediate Similarity NPC469620
0.7654 Intermediate Similarity NPC178277
0.7654 Intermediate Similarity NPC617
0.7647 Intermediate Similarity NPC150755
0.7647 Intermediate Similarity NPC284902
0.7632 Intermediate Similarity NPC5714
0.7625 Intermediate Similarity NPC208223
0.7619 Intermediate Similarity NPC156485
0.7614 Intermediate Similarity NPC70595
0.7614 Intermediate Similarity NPC150978
0.7614 Intermediate Similarity NPC284185
0.7614 Intermediate Similarity NPC74103
0.7614 Intermediate Similarity NPC123177
0.7595 Intermediate Similarity NPC471491
0.7595 Intermediate Similarity NPC472256
0.759 Intermediate Similarity NPC89555
0.7586 Intermediate Similarity NPC52198
0.7586 Intermediate Similarity NPC268298
0.7586 Intermediate Similarity NPC117405
0.7561 Intermediate Similarity NPC293418
0.7561 Intermediate Similarity NPC290508
0.7561 Intermediate Similarity NPC73052
0.7558 Intermediate Similarity NPC475703
0.7531 Intermediate Similarity NPC108816
0.7531 Intermediate Similarity NPC93763
0.7531 Intermediate Similarity NPC35574
0.7529 Intermediate Similarity NPC50362
0.7529 Intermediate Similarity NPC110405
0.7529 Intermediate Similarity NPC38468
0.7529 Intermediate Similarity NPC319795
0.7529 Intermediate Similarity NPC165162
0.7529 Intermediate Similarity NPC235792
0.75 Intermediate Similarity NPC312042
0.75 Intermediate Similarity NPC152467
0.75 Intermediate Similarity NPC59097
0.75 Intermediate Similarity NPC215481
0.75 Intermediate Similarity NPC129419
0.75 Intermediate Similarity NPC215294
0.75 Intermediate Similarity NPC475947
0.7471 Intermediate Similarity NPC190718
0.747 Intermediate Similarity NPC286229
0.747 Intermediate Similarity NPC141810
0.747 Intermediate Similarity NPC42470
0.7468 Intermediate Similarity NPC15499
0.7468 Intermediate Similarity NPC117746
0.7468 Intermediate Similarity NPC143979
0.7468 Intermediate Similarity NPC320537
0.7468 Intermediate Similarity NPC294434
0.7468 Intermediate Similarity NPC259599
0.7442 Intermediate Similarity NPC67493
0.7439 Intermediate Similarity NPC270126
0.7439 Intermediate Similarity NPC89128
0.7416 Intermediate Similarity NPC111114
0.7416 Intermediate Similarity NPC300312
0.7416 Intermediate Similarity NPC261607
0.7407 Intermediate Similarity NPC141789
0.7407 Intermediate Similarity NPC7563
0.7407 Intermediate Similarity NPC320630
0.7407 Intermediate Similarity NPC97516
0.7407 Intermediate Similarity NPC171204
0.7407 Intermediate Similarity NPC474760
0.7407 Intermediate Similarity NPC116177
0.7407 Intermediate Similarity NPC476028
0.7403 Intermediate Similarity NPC477449
0.7403 Intermediate Similarity NPC477448
0.7386 Intermediate Similarity NPC166919
0.7386 Intermediate Similarity NPC295312
0.7381 Intermediate Similarity NPC178676
0.7381 Intermediate Similarity NPC470813
0.7375 Intermediate Similarity NPC244166
0.7375 Intermediate Similarity NPC475861
0.7363 Intermediate Similarity NPC90121
0.7363 Intermediate Similarity NPC48803
0.7363 Intermediate Similarity NPC193645
0.7363 Intermediate Similarity NPC275960
0.7356 Intermediate Similarity NPC231889
0.7349 Intermediate Similarity NPC474510
0.7349 Intermediate Similarity NPC304795
0.7349 Intermediate Similarity NPC233377
0.7333 Intermediate Similarity NPC477615
0.7333 Intermediate Similarity NPC135776
0.7326 Intermediate Similarity NPC197903
0.7326 Intermediate Similarity NPC177932
0.7326 Intermediate Similarity NPC125290
0.7326 Intermediate Similarity NPC474547
0.7326 Intermediate Similarity NPC99395
0.7317 Intermediate Similarity NPC471465
0.7317 Intermediate Similarity NPC267231
0.7317 Intermediate Similarity NPC474056
0.7317 Intermediate Similarity NPC196653
0.7317 Intermediate Similarity NPC471220
0.7308 Intermediate Similarity NPC475310
0.7303 Intermediate Similarity NPC49342
0.7303 Intermediate Similarity NPC328141
0.7303 Intermediate Similarity NPC37607
0.7303 Intermediate Similarity NPC301969
0.7303 Intermediate Similarity NPC251385
0.7294 Intermediate Similarity NPC54468
0.7294 Intermediate Similarity NPC22611
0.7294 Intermediate Similarity NPC53867
0.7294 Intermediate Similarity NPC170377
0.7284 Intermediate Similarity NPC226242
0.7284 Intermediate Similarity NPC474527
0.7284 Intermediate Similarity NPC471726
0.7284 Intermediate Similarity NPC473223
0.7283 Intermediate Similarity NPC476275
0.7283 Intermediate Similarity NPC185553
0.7273 Intermediate Similarity NPC476614
0.7273 Intermediate Similarity NPC224652
0.7273 Intermediate Similarity NPC91248
0.7273 Intermediate Similarity NPC475906
0.7273 Intermediate Similarity NPC471047
0.7273 Intermediate Similarity NPC218477
0.7273 Intermediate Similarity NPC470256
0.7273 Intermediate Similarity NPC202672
0.7273 Intermediate Similarity NPC469628

  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 NPC472959 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
0.7529 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD1694 Approved
0.7191 Intermediate Similarity NPD1695 Approved
0.6977 Remote Similarity NPD6435 Approved
0.6977 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6854 Remote Similarity NPD6409 Approved
0.6854 Remote Similarity NPD7334 Approved
0.6854 Remote Similarity NPD5330 Approved
0.6854 Remote Similarity NPD6684 Approved
0.6854 Remote Similarity NPD7146 Approved
0.6854 Remote Similarity NPD7521 Approved
0.6744 Remote Similarity NPD5368 Approved
0.6742 Remote Similarity NPD5363 Approved
0.6703 Remote Similarity NPD6903 Approved
0.6703 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD5369 Approved
0.6593 Remote Similarity NPD3573 Approved
0.6591 Remote Similarity NPD5209 Approved
0.6582 Remote Similarity NPD7331 Phase 2
0.6559 Remote Similarity NPD5785 Approved
0.6522 Remote Similarity NPD6672 Approved
0.6522 Remote Similarity NPD5737 Approved
0.6517 Remote Similarity NPD5362 Discontinued
0.6517 Remote Similarity NPD7154 Phase 3
0.6452 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6101 Approved
0.6404 Remote Similarity NPD4270 Approved
0.6404 Remote Similarity NPD4269 Approved
0.6383 Remote Similarity NPD5207 Approved
0.6373 Remote Similarity NPD6008 Approved
0.6354 Remote Similarity NPD7900 Approved
0.6354 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6353 Remote Similarity NPD8039 Approved
0.6322 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6411 Approved
0.6311 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6422 Discontinued
0.6289 Remote Similarity NPD6356 Clinical (unspecified phase)
0.625 Remote Similarity NPD6399 Phase 3
0.625 Remote Similarity NPD7341 Phase 2
0.625 Remote Similarity NPD5779 Approved
0.625 Remote Similarity NPD5778 Approved
0.6224 Remote Similarity NPD4697 Phase 3
0.6211 Remote Similarity NPD6698 Approved
0.6211 Remote Similarity NPD46 Approved
0.6196 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6186 Remote Similarity NPD5282 Discontinued
0.6186 Remote Similarity NPD7748 Approved
0.6186 Remote Similarity NPD6001 Approved
0.618 Remote Similarity NPD5790 Clinical (unspecified phase)
0.618 Remote Similarity NPD4252 Approved
0.617 Remote Similarity NPD5208 Approved
0.6162 Remote Similarity NPD7902 Approved
0.6154 Remote Similarity NPD5697 Approved
0.6146 Remote Similarity NPD6079 Approved
0.6146 Remote Similarity NPD7983 Approved
0.6132 Remote Similarity NPD6371 Approved
0.6129 Remote Similarity NPD3618 Phase 1
0.6122 Remote Similarity NPD5695 Phase 3
0.6105 Remote Similarity NPD6904 Approved
0.6105 Remote Similarity NPD6080 Approved
0.6105 Remote Similarity NPD5328 Approved
0.6105 Remote Similarity NPD6673 Approved
0.61 Remote Similarity NPD5696 Approved
0.61 Remote Similarity NPD4225 Approved
0.6095 Remote Similarity NPD6011 Approved
0.6095 Remote Similarity NPD6899 Approved
0.6095 Remote Similarity NPD6881 Approved
0.6087 Remote Similarity NPD3133 Approved
0.6087 Remote Similarity NPD3665 Phase 1
0.6087 Remote Similarity NPD3666 Approved
0.6075 Remote Similarity NPD6650 Approved
0.6075 Remote Similarity NPD6649 Approved
0.6061 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6058 Remote Similarity NPD6675 Approved
0.6058 Remote Similarity NPD7128 Approved
0.6058 Remote Similarity NPD5739 Approved
0.6058 Remote Similarity NPD6402 Approved
0.6042 Remote Similarity NPD5692 Phase 3
0.6038 Remote Similarity NPD6012 Approved
0.6038 Remote Similarity NPD6014 Approved
0.6038 Remote Similarity NPD6013 Approved
0.6038 Remote Similarity NPD6372 Approved
0.6038 Remote Similarity NPD6373 Approved
0.6027 Remote Similarity NPD29 Approved
0.6027 Remote Similarity NPD28 Approved
0.6 Remote Similarity NPD4821 Approved
0.6 Remote Similarity NPD6083 Phase 2
0.6 Remote Similarity NPD6084 Phase 2
0.6 Remote Similarity NPD5701 Approved
0.6 Remote Similarity NPD4822 Approved
0.6 Remote Similarity NPD4819 Approved
0.6 Remote Similarity NPD4820 Approved
0.5981 Remote Similarity NPD7290 Approved
0.5981 Remote Similarity NPD6883 Approved
0.5981 Remote Similarity NPD7102 Approved
0.5979 Remote Similarity NPD5694 Approved
0.5979 Remote Similarity NPD6050 Approved
0.5979 Remote Similarity NPD5693 Phase 1
0.5979 Remote Similarity NPD7515 Phase 2
0.5978 Remote Similarity NPD5331 Approved
0.5978 Remote Similarity NPD5332 Approved
0.5976 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5957 Remote Similarity NPD4249 Approved
0.5957 Remote Similarity NPD6098 Approved
0.5957 Remote Similarity NPD5279 Phase 3
0.5955 Remote Similarity NPD4271 Approved
0.5955 Remote Similarity NPD4268 Approved
0.5943 Remote Similarity NPD7320 Approved
0.5934 Remote Similarity NPD4790 Discontinued
0.5926 Remote Similarity NPD6847 Approved
0.5926 Remote Similarity NPD6869 Approved
0.5926 Remote Similarity NPD3197 Phase 1
0.5926 Remote Similarity NPD6617 Approved
0.5926 Remote Similarity NPD8130 Phase 1
0.59 Remote Similarity NPD5221 Approved
0.59 Remote Similarity NPD5220 Clinical (unspecified phase)
0.59 Remote Similarity NPD5222 Approved
0.59 Remote Similarity NPD7839 Suspended
0.5895 Remote Similarity NPD4250 Approved
0.5895 Remote Similarity NPD4251 Approved
0.5882 Remote Similarity NPD4691 Approved
0.5872 Remote Similarity NPD6053 Discontinued
0.5872 Remote Similarity NPD8297 Approved
0.5872 Remote Similarity NPD6882 Approved
0.587 Remote Similarity NPD3667 Approved
0.5867 Remote Similarity NPD3172 Approved
0.5843 Remote Similarity NPD4756 Discovery
0.5842 Remote Similarity NPD5173 Approved
0.5824 Remote Similarity NPD4695 Discontinued
0.5816 Remote Similarity NPD5284 Approved
0.5816 Remote Similarity NPD5281 Approved
0.5794 Remote Similarity NPD6686 Approved
0.5789 Remote Similarity NPD4266 Approved
0.5789 Remote Similarity NPD3195 Phase 2
0.5789 Remote Similarity NPD9298 Approved
0.5789 Remote Similarity NPD3196 Approved
0.5789 Remote Similarity NPD3194 Approved
0.5784 Remote Similarity NPD7638 Approved
0.578 Remote Similarity NPD6401 Clinical (unspecified phase)
0.578 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5765 Remote Similarity NPD4137 Phase 3
0.5761 Remote Similarity NPD857 Phase 3
0.5752 Remote Similarity NPD7641 Discontinued
0.5745 Remote Similarity NPD3668 Phase 3
0.5745 Remote Similarity NPD4786 Approved
0.5743 Remote Similarity NPD7732 Phase 3
0.5739 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5728 Remote Similarity NPD7639 Approved
0.5728 Remote Similarity NPD7640 Approved
0.5728 Remote Similarity NPD5285 Approved
0.5728 Remote Similarity NPD5286 Approved
0.5728 Remote Similarity NPD4696 Approved
0.5714 Remote Similarity NPD6274 Approved
0.5714 Remote Similarity NPD3673 Approved
0.5714 Remote Similarity NPD6868 Approved
0.5714 Remote Similarity NPD6052 Approved
0.5714 Remote Similarity NPD7838 Discovery
0.5714 Remote Similarity NPD3672 Approved
0.5699 Remote Similarity NPD4221 Approved
0.5699 Remote Similarity NPD4223 Phase 3
0.5699 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5698 Remote Similarity NPD4747 Approved
0.5686 Remote Similarity NPD4755 Approved
0.5682 Remote Similarity NPD4058 Approved
0.5676 Remote Similarity NPD4632 Approved
0.5673 Remote Similarity NPD5223 Approved
0.5664 Remote Similarity NPD6317 Approved
0.5657 Remote Similarity NPD8034 Phase 2
0.5657 Remote Similarity NPD8035 Phase 2
0.5644 Remote Similarity NPD5210 Approved
0.5644 Remote Similarity NPD4629 Approved
0.5644 Remote Similarity NPD5654 Approved
0.5632 Remote Similarity NPD5276 Approved
0.5631 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5625 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5690 Phase 2
0.5625 Remote Similarity NPD3198 Approved
0.5619 Remote Similarity NPD5211 Phase 2
0.5619 Remote Similarity NPD5226 Approved
0.5619 Remote Similarity NPD4633 Approved
0.5619 Remote Similarity NPD5225 Approved
0.5619 Remote Similarity NPD5224 Approved
0.5616 Remote Similarity NPD5343 Approved
0.5614 Remote Similarity NPD6335 Approved
0.5614 Remote Similarity NPD6313 Approved
0.5614 Remote Similarity NPD6314 Approved
0.5612 Remote Similarity NPD5370 Suspended
0.5612 Remote Similarity NPD4753 Phase 2
0.561 Remote Similarity NPD2664 Clinical (unspecified phase)
0.56 Remote Similarity NPD4202 Approved
0.56 Remote Similarity NPD5781 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