Structure

Physi-Chem Properties

Molecular Weight:  306.18
Volume:  315.546
LogP:  0.818
LogD:  1.16
LogS:  -2.641
# Rotatable Bonds:  1
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.687
Synthetic Accessibility Score:  6.146
Fsp3:  0.833
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:  -5.661
MDCK Permeability:  1.2234518180775922e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.86
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.062
30% Bioavailability (F30%):  0.572

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.647
Plasma Protein Binding (PPB):  78.86173248291016%
Volume Distribution (VD):  0.456
Pgp-substrate:  20.88237190246582%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.916
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.448
CYP2C9-inhibitor:  0.03
CYP2C9-substrate:  0.065
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.034
CYP3A4-inhibitor:  0.879
CYP3A4-substrate:  0.512

ADMET: Excretion

Clearance (CL):  3.766
Half-life (T1/2):  0.527

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.795
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.173
Maximum Recommended Daily Dose:  0.963
Skin Sensitization:  0.914
Carcinogencity:  0.98
Eye Corrosion:  0.028
Eye Irritation:  0.094
Respiratory Toxicity:  0.983

Download Data

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

  Natural Product: NPC472824

Natural Product ID:  NPC472824
Common Name*:   XWOCMLGYYIIDPY-WLZXLALPSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  XWOCMLGYYIIDPY-WLZXLALPSA-N
Standard InCHI:  InChI=1S/C18H26O4/c1-15-5-3-13(20)8-12(15)2-6-16-9-17(21,7-4-14(15)16)18(22,10-16)11-19/h3,5,12,14,19,21-22H,2,4,6-11H2,1H3/t12-,14+,15-,16+,17-,18+/m1/s1
SMILES:  CC12C=CC(=O)CC1CCC34C2CCC(C3)(C(C4)(CO)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3586291
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0004325] Cyclohexenones

*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
NPO32576 tricalysia fruticosa Species Rubiaceae Eukaryota Twigs n.a. n.a. PMID[26052978]

☑ 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 IC50 > 27100.0 nM PMID[489390]
NPT113 Cell Line RAW264.7 Mus musculus Survival > 90.0 % PMID[489390]

☑ 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 NPC472824 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
0.8889 High Similarity NPC472825
0.8713 High Similarity NPC235077
0.8617 High Similarity NPC111015
0.8587 High Similarity NPC310010
0.8587 High Similarity NPC326627
0.8557 High Similarity NPC144956
0.8416 Intermediate Similarity NPC83744
0.8416 Intermediate Similarity NPC477916
0.84 Intermediate Similarity NPC209502
0.84 Intermediate Similarity NPC204833
0.837 Intermediate Similarity NPC90652
0.8367 Intermediate Similarity NPC154072
0.8351 Intermediate Similarity NPC108078
0.8351 Intermediate Similarity NPC18509
0.8333 Intermediate Similarity NPC472485
0.8333 Intermediate Similarity NPC329417
0.8333 Intermediate Similarity NPC65941
0.8317 Intermediate Similarity NPC97202
0.8317 Intermediate Similarity NPC214264
0.8317 Intermediate Similarity NPC302607
0.8317 Intermediate Similarity NPC48733
0.8317 Intermediate Similarity NPC150531
0.8317 Intermediate Similarity NPC319077
0.8317 Intermediate Similarity NPC296945
0.8317 Intermediate Similarity NPC257353
0.8317 Intermediate Similarity NPC50692
0.8317 Intermediate Similarity NPC152695
0.8317 Intermediate Similarity NPC49958
0.8317 Intermediate Similarity NPC171137
0.8317 Intermediate Similarity NPC85829
0.8317 Intermediate Similarity NPC149047
0.8317 Intermediate Similarity NPC260268
0.8317 Intermediate Similarity NPC476027
0.8317 Intermediate Similarity NPC202167
0.8316 Intermediate Similarity NPC233118
0.83 Intermediate Similarity NPC191892
0.828 Intermediate Similarity NPC470417
0.8265 Intermediate Similarity NPC114274
0.8252 Intermediate Similarity NPC214644
0.8247 Intermediate Similarity NPC477853
0.8247 Intermediate Similarity NPC49371
0.8242 Intermediate Similarity NPC161423
0.8242 Intermediate Similarity NPC58841
0.8242 Intermediate Similarity NPC227064
0.8242 Intermediate Similarity NPC321187
0.8242 Intermediate Similarity NPC329043
0.8235 Intermediate Similarity NPC220229
0.8235 Intermediate Similarity NPC475060
0.8229 Intermediate Similarity NPC245972
0.8229 Intermediate Similarity NPC8993
0.8229 Intermediate Similarity NPC196485
0.8222 Intermediate Similarity NPC193347
0.8211 Intermediate Similarity NPC475806
0.8211 Intermediate Similarity NPC131872
0.8211 Intermediate Similarity NPC272746
0.82 Intermediate Similarity NPC473424
0.82 Intermediate Similarity NPC22388
0.82 Intermediate Similarity NPC477915
0.8191 Intermediate Similarity NPC186688
0.8191 Intermediate Similarity NPC1015
0.8191 Intermediate Similarity NPC32830
0.8191 Intermediate Similarity NPC215029
0.8191 Intermediate Similarity NPC31985
0.8191 Intermediate Similarity NPC476733
0.8191 Intermediate Similarity NPC477943
0.8182 Intermediate Similarity NPC474720
0.8172 Intermediate Similarity NPC58063
0.8172 Intermediate Similarity NPC93778
0.8172 Intermediate Similarity NPC472482
0.8172 Intermediate Similarity NPC472484
0.8172 Intermediate Similarity NPC472481
0.8155 Intermediate Similarity NPC217201
0.8144 Intermediate Similarity NPC473170
0.8144 Intermediate Similarity NPC200702
0.8144 Intermediate Similarity NPC271195
0.8125 Intermediate Similarity NPC474736
0.8125 Intermediate Similarity NPC109305
0.8125 Intermediate Similarity NPC474807
0.8119 Intermediate Similarity NPC117185
0.8119 Intermediate Similarity NPC311612
0.8119 Intermediate Similarity NPC249187
0.8119 Intermediate Similarity NPC247957
0.8113 Intermediate Similarity NPC178981
0.8105 Intermediate Similarity NPC171441
0.8105 Intermediate Similarity NPC136801
0.8105 Intermediate Similarity NPC320026
0.8085 Intermediate Similarity NPC44181
0.8085 Intermediate Similarity NPC328539
0.8085 Intermediate Similarity NPC193360
0.8081 Intermediate Similarity NPC103051
0.8081 Intermediate Similarity NPC477854
0.8077 Intermediate Similarity NPC11710
0.8077 Intermediate Similarity NPC10064
0.8077 Intermediate Similarity NPC170221
0.8065 Intermediate Similarity NPC474733
0.8065 Intermediate Similarity NPC474778
0.8065 Intermediate Similarity NPC145879
0.8065 Intermediate Similarity NPC474732
0.8065 Intermediate Similarity NPC31564
0.8061 Intermediate Similarity NPC471463
0.8058 Intermediate Similarity NPC58370
0.8058 Intermediate Similarity NPC43285
0.8058 Intermediate Similarity NPC165873
0.8058 Intermediate Similarity NPC44063
0.8043 Intermediate Similarity NPC237712
0.8043 Intermediate Similarity NPC144258
0.8043 Intermediate Similarity NPC214043
0.8043 Intermediate Similarity NPC85774
0.8043 Intermediate Similarity NPC82902
0.8041 Intermediate Similarity NPC473172
0.8021 Intermediate Similarity NPC168027
0.8021 Intermediate Similarity NPC155304
0.8021 Intermediate Similarity NPC185936
0.8021 Intermediate Similarity NPC19114
0.8021 Intermediate Similarity NPC473998
0.802 Intermediate Similarity NPC87351
0.8019 Intermediate Similarity NPC207251
0.8 Intermediate Similarity NPC6206
0.8 Intermediate Similarity NPC119416
0.8 Intermediate Similarity NPC469637
0.8 Intermediate Similarity NPC5284
0.8 Intermediate Similarity NPC2983
0.8 Intermediate Similarity NPC473999
0.8 Intermediate Similarity NPC472478
0.8 Intermediate Similarity NPC83709
0.8 Intermediate Similarity NPC77263
0.8 Intermediate Similarity NPC472477
0.8 Intermediate Similarity NPC250592
0.8 Intermediate Similarity NPC472475
0.8 Intermediate Similarity NPC76879
0.8 Intermediate Similarity NPC76084
0.8 Intermediate Similarity NPC309603
0.8 Intermediate Similarity NPC476809
0.798 Intermediate Similarity NPC474938
0.798 Intermediate Similarity NPC190554
0.798 Intermediate Similarity NPC474785
0.7979 Intermediate Similarity NPC317590
0.7979 Intermediate Similarity NPC99909
0.7979 Intermediate Similarity NPC138756
0.7979 Intermediate Similarity NPC475740
0.7959 Intermediate Similarity NPC180950
0.7957 Intermediate Similarity NPC470574
0.7957 Intermediate Similarity NPC474218
0.7957 Intermediate Similarity NPC469948
0.7944 Intermediate Similarity NPC73300
0.7944 Intermediate Similarity NPC317210
0.7944 Intermediate Similarity NPC108721
0.7941 Intermediate Similarity NPC239716
0.7938 Intermediate Similarity NPC475255
0.7917 Intermediate Similarity NPC191684
0.7917 Intermediate Similarity NPC126993
0.7917 Intermediate Similarity NPC85173
0.7912 Intermediate Similarity NPC6434
0.7905 Intermediate Similarity NPC470257
0.7905 Intermediate Similarity NPC2766
0.79 Intermediate Similarity NPC191565
0.7895 Intermediate Similarity NPC310752
0.7895 Intermediate Similarity NPC158778
0.7895 Intermediate Similarity NPC472483
0.7895 Intermediate Similarity NPC292491
0.7895 Intermediate Similarity NPC471722
0.7895 Intermediate Similarity NPC474677
0.7895 Intermediate Similarity NPC328313
0.7885 Intermediate Similarity NPC185
0.7879 Intermediate Similarity NPC117133
0.7879 Intermediate Similarity NPC249954
0.7879 Intermediate Similarity NPC473158
0.7879 Intermediate Similarity NPC473164
0.7872 Intermediate Similarity NPC472491
0.7872 Intermediate Similarity NPC472494
0.7872 Intermediate Similarity NPC72133
0.7872 Intermediate Similarity NPC118648
0.7872 Intermediate Similarity NPC473168
0.7872 Intermediate Similarity NPC222613
0.7872 Intermediate Similarity NPC475022
0.7872 Intermediate Similarity NPC327115
0.7872 Intermediate Similarity NPC89077
0.7872 Intermediate Similarity NPC469994
0.787 Intermediate Similarity NPC326542
0.7864 Intermediate Similarity NPC72255
0.7864 Intermediate Similarity NPC255309
0.7864 Intermediate Similarity NPC160843
0.7857 Intermediate Similarity NPC471207
0.7857 Intermediate Similarity NPC67831
0.7857 Intermediate Similarity NPC299100
0.7857 Intermediate Similarity NPC209662
0.7857 Intermediate Similarity NPC174051
0.785 Intermediate Similarity NPC234042
0.785 Intermediate Similarity NPC152117
0.7849 Intermediate Similarity NPC33913
0.7849 Intermediate Similarity NPC472480
0.7849 Intermediate Similarity NPC473246
0.7849 Intermediate Similarity NPC59453
0.7849 Intermediate Similarity NPC472265
0.7849 Intermediate Similarity NPC221758
0.7835 Intermediate Similarity NPC262870
0.7835 Intermediate Similarity NPC473167
0.7835 Intermediate Similarity NPC233116
0.7835 Intermediate Similarity NPC189520
0.783 Intermediate Similarity NPC197428

  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 NPC472824 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
0.8713 High Similarity NPD4634 Approved
0.8587 High Similarity NPD4753 Phase 2
0.8557 High Similarity NPD4696 Approved
0.8557 High Similarity NPD5286 Approved
0.8557 High Similarity NPD5285 Approved
0.8526 High Similarity NPD4629 Approved
0.8526 High Similarity NPD5210 Approved
0.8384 Intermediate Similarity NPD5226 Approved
0.8384 Intermediate Similarity NPD4633 Approved
0.8384 Intermediate Similarity NPD5225 Approved
0.8384 Intermediate Similarity NPD5224 Approved
0.8384 Intermediate Similarity NPD5211 Phase 2
0.8351 Intermediate Similarity NPD4755 Approved
0.8316 Intermediate Similarity NPD4202 Approved
0.83 Intermediate Similarity NPD5175 Approved
0.83 Intermediate Similarity NPD5174 Approved
0.8283 Intermediate Similarity NPD5223 Approved
0.8242 Intermediate Similarity NPD3133 Approved
0.8242 Intermediate Similarity NPD3666 Approved
0.8242 Intermediate Similarity NPD3665 Phase 1
0.8222 Intermediate Similarity NPD4223 Phase 3
0.8222 Intermediate Similarity NPD4221 Approved
0.8218 Intermediate Similarity NPD5141 Approved
0.8211 Intermediate Similarity NPD6079 Approved
0.8182 Intermediate Similarity NPD4700 Approved
0.8113 Intermediate Similarity NPD4632 Approved
0.8065 Intermediate Similarity NPD3618 Phase 1
0.8065 Intermediate Similarity NPD5690 Phase 2
0.8065 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD5222 Approved
0.8061 Intermediate Similarity NPD5221 Approved
0.8061 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.8058 Intermediate Similarity NPD5697 Approved
0.8043 Intermediate Similarity NPD4197 Approved
0.8 Intermediate Similarity NPD6319 Approved
0.8 Intermediate Similarity NPD5328 Approved
0.7981 Intermediate Similarity NPD6881 Approved
0.7981 Intermediate Similarity NPD4729 Approved
0.7981 Intermediate Similarity NPD6899 Approved
0.7981 Intermediate Similarity NPD4730 Approved
0.798 Intermediate Similarity NPD6083 Phase 2
0.798 Intermediate Similarity NPD6084 Phase 2
0.798 Intermediate Similarity NPD5173 Approved
0.7957 Intermediate Similarity NPD5329 Approved
0.7905 Intermediate Similarity NPD6012 Approved
0.7905 Intermediate Similarity NPD6014 Approved
0.7905 Intermediate Similarity NPD6013 Approved
0.7889 Intermediate Similarity NPD4195 Approved
0.7872 Intermediate Similarity NPD4689 Approved
0.7872 Intermediate Similarity NPD5205 Approved
0.7872 Intermediate Similarity NPD4138 Approved
0.7872 Intermediate Similarity NPD4690 Approved
0.7872 Intermediate Similarity NPD4688 Approved
0.7872 Intermediate Similarity NPD4693 Phase 3
0.785 Intermediate Similarity NPD8297 Approved
0.7849 Intermediate Similarity NPD4786 Approved
0.7838 Intermediate Similarity NPD6054 Approved
0.783 Intermediate Similarity NPD5249 Phase 3
0.783 Intermediate Similarity NPD5247 Approved
0.783 Intermediate Similarity NPD7102 Approved
0.783 Intermediate Similarity NPD5248 Approved
0.783 Intermediate Similarity NPD5251 Approved
0.783 Intermediate Similarity NPD6883 Approved
0.783 Intermediate Similarity NPD5250 Approved
0.783 Intermediate Similarity NPD7290 Approved
0.7826 Intermediate Similarity NPD3667 Approved
0.781 Intermediate Similarity NPD6011 Approved
0.781 Intermediate Similarity NPD5128 Approved
0.7788 Intermediate Similarity NPD7128 Approved
0.7788 Intermediate Similarity NPD4767 Approved
0.7788 Intermediate Similarity NPD5739 Approved
0.7788 Intermediate Similarity NPD6675 Approved
0.7788 Intermediate Similarity NPD4768 Approved
0.7788 Intermediate Similarity NPD6402 Approved
0.7778 Intermediate Similarity NPD5695 Phase 3
0.7768 Intermediate Similarity NPD6016 Approved
0.7768 Intermediate Similarity NPD6015 Approved
0.7767 Intermediate Similarity NPD4754 Approved
0.7757 Intermediate Similarity NPD5217 Approved
0.7757 Intermediate Similarity NPD5215 Approved
0.7757 Intermediate Similarity NPD6869 Approved
0.7757 Intermediate Similarity NPD6617 Approved
0.7757 Intermediate Similarity NPD6847 Approved
0.7757 Intermediate Similarity NPD6649 Approved
0.7757 Intermediate Similarity NPD5216 Approved
0.7757 Intermediate Similarity NPD6650 Approved
0.7757 Intermediate Similarity NPD8130 Phase 1
0.7748 Intermediate Similarity NPD4522 Approved
0.7742 Intermediate Similarity NPD4788 Approved
0.7727 Intermediate Similarity NPD6009 Approved
0.7723 Intermediate Similarity NPD5696 Approved
0.7714 Intermediate Similarity NPD6412 Phase 2
0.7714 Intermediate Similarity NPD5701 Approved
0.77 Intermediate Similarity NPD4697 Phase 3
0.7699 Intermediate Similarity NPD6370 Approved
0.7699 Intermediate Similarity NPD5988 Approved
0.7685 Intermediate Similarity NPD6882 Approved
0.7684 Intermediate Similarity NPD5280 Approved
0.7684 Intermediate Similarity NPD4694 Approved
0.7664 Intermediate Similarity NPD5169 Approved
0.7664 Intermediate Similarity NPD5135 Approved
0.7664 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7653 Intermediate Similarity NPD5281 Approved
0.7653 Intermediate Similarity NPD5284 Approved
0.7642 Intermediate Similarity NPD7320 Approved
0.7593 Intermediate Similarity NPD5127 Approved
0.757 Intermediate Similarity NPD6372 Approved
0.757 Intermediate Similarity NPD6373 Approved
0.7565 Intermediate Similarity NPD7492 Approved
0.7522 Intermediate Similarity NPD6059 Approved
0.75 Intermediate Similarity NPD6616 Approved
0.75 Intermediate Similarity NPD5279 Phase 3
0.7456 Intermediate Similarity NPD5983 Phase 2
0.7436 Intermediate Similarity NPD7078 Approved
0.7411 Intermediate Similarity NPD7115 Discovery
0.7391 Intermediate Similarity NPD3617 Approved
0.7387 Intermediate Similarity NPD5167 Approved
0.7373 Intermediate Similarity NPD7736 Approved
0.734 Intermediate Similarity NPD4139 Approved
0.734 Intermediate Similarity NPD4692 Approved
0.7333 Intermediate Similarity NPD5091 Approved
0.7328 Intermediate Similarity NPD7604 Phase 2
0.7321 Intermediate Similarity NPD6274 Approved
0.732 Intermediate Similarity NPD6409 Approved
0.732 Intermediate Similarity NPD7334 Approved
0.732 Intermediate Similarity NPD6684 Approved
0.732 Intermediate Similarity NPD7521 Approved
0.732 Intermediate Similarity NPD5330 Approved
0.732 Intermediate Similarity NPD7146 Approved
0.7315 Intermediate Similarity NPD5168 Approved
0.73 Intermediate Similarity NPD7515 Phase 2
0.7292 Intermediate Similarity NPD3668 Phase 3
0.729 Intermediate Similarity NPD6008 Approved
0.7281 Intermediate Similarity NPD7101 Approved
0.7281 Intermediate Similarity NPD7100 Approved
0.7273 Intermediate Similarity NPD6080 Approved
0.7273 Intermediate Similarity NPD6673 Approved
0.7273 Intermediate Similarity NPD6904 Approved
0.7273 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD6317 Approved
0.7255 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD4695 Discontinued
0.7228 Intermediate Similarity NPD6399 Phase 3
0.7228 Intermediate Similarity NPD5133 Approved
0.7212 Intermediate Similarity NPD7638 Approved
0.7203 Intermediate Similarity NPD6336 Discontinued
0.72 Intermediate Similarity NPD4096 Approved
0.7193 Intermediate Similarity NPD6313 Approved
0.7193 Intermediate Similarity NPD6314 Approved
0.7193 Intermediate Similarity NPD6335 Approved
0.7174 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5208 Approved
0.7172 Intermediate Similarity NPD6903 Approved
0.7172 Intermediate Similarity NPD6672 Approved
0.7172 Intermediate Similarity NPD5737 Approved
0.7172 Intermediate Similarity NPD4518 Approved
0.7172 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4519 Discontinued
0.7143 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD7639 Approved
0.7143 Intermediate Similarity NPD8293 Discontinued
0.7143 Intermediate Similarity NPD4623 Approved
0.7129 Intermediate Similarity NPD5693 Phase 1
0.7129 Intermediate Similarity NPD5694 Approved
0.7071 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD7525 Registered
0.703 Intermediate Similarity NPD5207 Approved
0.703 Intermediate Similarity NPD5692 Phase 3
0.7009 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4747 Approved
0.7 Intermediate Similarity NPD4691 Approved
0.699 Remote Similarity NPD7748 Approved
0.699 Remote Similarity NPD6001 Approved
0.697 Remote Similarity NPD6098 Approved
0.6967 Remote Similarity NPD5956 Approved
0.6961 Remote Similarity NPD6050 Approved
0.6957 Remote Similarity NPD4058 Approved
0.6957 Remote Similarity NPD4785 Approved
0.6957 Remote Similarity NPD4784 Approved
0.6942 Remote Similarity NPD6033 Approved
0.6937 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4243 Approved
0.6923 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6917 Remote Similarity NPD7507 Approved
0.69 Remote Similarity NPD3573 Approved
0.6891 Remote Similarity NPD6067 Discontinued
0.6889 Remote Similarity NPD3698 Phase 2
0.6889 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6889 Remote Similarity NPD4137 Phase 3
0.6882 Remote Similarity NPD3703 Phase 2
0.6882 Remote Similarity NPD7339 Approved
0.6882 Remote Similarity NPD6942 Approved
0.6875 Remote Similarity NPD4748 Discontinued
0.687 Remote Similarity NPD6868 Approved
0.6869 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6909 Approved
0.6864 Remote Similarity NPD6908 Approved
0.6842 Remote Similarity NPD6118 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