Structure

Physi-Chem Properties

Molecular Weight:  330.18
Volume:  338.945
LogP:  3.159
LogD:  2.69
LogS:  -3.549
# Rotatable Bonds:  1
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.737
Synthetic Accessibility Score:  6.254
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.489
MDCK Permeability:  1.3045619198237546e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.972
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.231
30% Bioavailability (F30%):  0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.317
Plasma Protein Binding (PPB):  95.64553833007812%
Volume Distribution (VD):  1.427
Pgp-substrate:  4.292654514312744%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.352
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.294
CYP2C9-inhibitor:  0.08
CYP2C9-substrate:  0.23
CYP2D6-inhibitor:  0.115
CYP2D6-substrate:  0.145
CYP3A4-inhibitor:  0.939
CYP3A4-substrate:  0.227

ADMET: Excretion

Clearance (CL):  12.534
Half-life (T1/2):  0.685

ADMET: Toxicity

hERG Blockers:  0.065
Human Hepatotoxicity (H-HT):  0.8
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.034
Rat Oral Acute Toxicity:  0.916
Maximum Recommended Daily Dose:  0.961
Skin Sensitization:  0.69
Carcinogencity:  0.906
Eye Corrosion:  0.005
Eye Irritation:  0.018
Respiratory Toxicity:  0.964

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

  Natural Product: NPC181147

Natural Product ID:  NPC181147
Common Name*:   OXZIAVDNDXSZFB-WOBOPYLOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  OXZIAVDNDXSZFB-WOBOPYLOSA-N
Standard InCHI:  InChI=1S/C20H26O4/c1-18-6-5-15-13(8-17(22)24-15)14(18)4-7-19-9-12(2-3-16(18)19)20(23,10-19)11-21/h5,8,12,14,16,21,23H,2-4,6-7,9-11H2,1H3/t12-,14-,16+,18-,19+,20+/m1/s1
SMILES:  OC[C@@]1(O)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)C2=CC(=O)OC2=CC1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3586295
PubChem CID:   11652840
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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 > 100000.0 nM PMID[496565]
NPT113 Cell Line RAW264.7 Mus musculus Survival > 90.0 % PMID[496565]

☑ 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 NPC181147 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
0.9479 High Similarity NPC200861
0.9479 High Similarity NPC472822
0.9053 High Similarity NPC231751
0.8866 High Similarity NPC472826
0.86 High Similarity NPC472821
0.8515 High Similarity NPC472819
0.8431 Intermediate Similarity NPC186668
0.8431 Intermediate Similarity NPC472818
0.8416 Intermediate Similarity NPC171014
0.84 Intermediate Similarity NPC222875
0.84 Intermediate Similarity NPC25177
0.84 Intermediate Similarity NPC295110
0.84 Intermediate Similarity NPC268829
0.84 Intermediate Similarity NPC247701
0.835 Intermediate Similarity NPC472820
0.835 Intermediate Similarity NPC43063
0.835 Intermediate Similarity NPC79298
0.8252 Intermediate Similarity NPC295843
0.8235 Intermediate Similarity NPC10232
0.8235 Intermediate Similarity NPC160583
0.8235 Intermediate Similarity NPC196471
0.8235 Intermediate Similarity NPC187302
0.8235 Intermediate Similarity NPC97487
0.8235 Intermediate Similarity NPC189588
0.819 Intermediate Similarity NPC75389
0.8113 Intermediate Similarity NPC103491
0.81 Intermediate Similarity NPC210337
0.8095 Intermediate Similarity NPC472825
0.8095 Intermediate Similarity NPC137462
0.8095 Intermediate Similarity NPC304276
0.8095 Intermediate Similarity NPC275060
0.8077 Intermediate Similarity NPC119855
0.8077 Intermediate Similarity NPC220217
0.8041 Intermediate Similarity NPC280149
0.8041 Intermediate Similarity NPC221111
0.8021 Intermediate Similarity NPC472302
0.802 Intermediate Similarity NPC278673
0.8 Intermediate Similarity NPC185287
0.8 Intermediate Similarity NPC88009
0.798 Intermediate Similarity NPC201725
0.7963 Intermediate Similarity NPC44537
0.7959 Intermediate Similarity NPC234335
0.7959 Intermediate Similarity NPC2882
0.7944 Intermediate Similarity NPC16270
0.7944 Intermediate Similarity NPC12795
0.7941 Intermediate Similarity NPC473510
0.7941 Intermediate Similarity NPC230546
0.7938 Intermediate Similarity NPC476733
0.7938 Intermediate Similarity NPC473647
0.7938 Intermediate Similarity NPC215029
0.7905 Intermediate Similarity NPC471206
0.789 Intermediate Similarity NPC171126
0.7885 Intermediate Similarity NPC112009
0.7879 Intermediate Similarity NPC472954
0.7872 Intermediate Similarity NPC311070
0.787 Intermediate Similarity NPC183603
0.7857 Intermediate Similarity NPC278681
0.785 Intermediate Similarity NPC475030
0.7843 Intermediate Similarity NPC92275
0.7838 Intermediate Similarity NPC203862
0.7838 Intermediate Similarity NPC157380
0.7835 Intermediate Similarity NPC471956
0.7822 Intermediate Similarity NPC16967
0.7822 Intermediate Similarity NPC190713
0.7822 Intermediate Similarity NPC473153
0.7818 Intermediate Similarity NPC471633
0.7818 Intermediate Similarity NPC84949
0.7818 Intermediate Similarity NPC69576
0.7818 Intermediate Similarity NPC31354
0.7818 Intermediate Similarity NPC106446
0.7812 Intermediate Similarity NPC471219
0.7812 Intermediate Similarity NPC131813
0.781 Intermediate Similarity NPC165969
0.78 Intermediate Similarity NPC191521
0.7788 Intermediate Similarity NPC112936
0.7778 Intermediate Similarity NPC181298
0.7778 Intermediate Similarity NPC177641
0.7768 Intermediate Similarity NPC16701
0.7767 Intermediate Similarity NPC290802
0.7767 Intermediate Similarity NPC227865
0.7767 Intermediate Similarity NPC201406
0.7757 Intermediate Similarity NPC50124
0.7755 Intermediate Similarity NPC177141
0.7755 Intermediate Similarity NPC5509
0.7755 Intermediate Similarity NPC470734
0.7748 Intermediate Similarity NPC99620
0.7748 Intermediate Similarity NPC5311
0.7748 Intermediate Similarity NPC193382
0.7748 Intermediate Similarity NPC310341
0.7748 Intermediate Similarity NPC196931
0.7748 Intermediate Similarity NPC199428
0.7745 Intermediate Similarity NPC141401
0.7745 Intermediate Similarity NPC208094
0.7745 Intermediate Similarity NPC475894
0.7736 Intermediate Similarity NPC266570
0.7736 Intermediate Similarity NPC189863
0.7736 Intermediate Similarity NPC81630
0.7727 Intermediate Similarity NPC73050
0.7727 Intermediate Similarity NPC154815
0.7727 Intermediate Similarity NPC241977
0.7723 Intermediate Similarity NPC329435
0.7723 Intermediate Similarity NPC171395
0.7723 Intermediate Similarity NPC295347
0.7714 Intermediate Similarity NPC180204
0.7714 Intermediate Similarity NPC183570
0.7708 Intermediate Similarity NPC473251
0.7708 Intermediate Similarity NPC42586
0.77 Intermediate Similarity NPC162615
0.77 Intermediate Similarity NPC214697
0.77 Intermediate Similarity NPC205034
0.77 Intermediate Similarity NPC38232
0.77 Intermediate Similarity NPC53555
0.77 Intermediate Similarity NPC152778
0.7699 Intermediate Similarity NPC35171
0.7699 Intermediate Similarity NPC213761
0.7692 Intermediate Similarity NPC475617
0.7692 Intermediate Similarity NPC99411
0.7692 Intermediate Similarity NPC11974
0.7685 Intermediate Similarity NPC475274
0.7684 Intermediate Similarity NPC23748
0.7679 Intermediate Similarity NPC471355
0.7679 Intermediate Similarity NPC84987
0.7679 Intermediate Similarity NPC196429
0.7679 Intermediate Similarity NPC290693
0.7679 Intermediate Similarity NPC471353
0.7679 Intermediate Similarity NPC27507
0.7679 Intermediate Similarity NPC87250
0.7679 Intermediate Similarity NPC99728
0.7679 Intermediate Similarity NPC474418
0.7679 Intermediate Similarity NPC50305
0.7679 Intermediate Similarity NPC471354
0.7679 Intermediate Similarity NPC158344
0.7679 Intermediate Similarity NPC93883
0.7679 Intermediate Similarity NPC243196
0.7679 Intermediate Similarity NPC142066
0.7679 Intermediate Similarity NPC152615
0.7679 Intermediate Similarity NPC473852
0.7679 Intermediate Similarity NPC471351
0.7679 Intermediate Similarity NPC309034
0.7679 Intermediate Similarity NPC244402
0.7679 Intermediate Similarity NPC34390
0.7679 Intermediate Similarity NPC77319
0.7679 Intermediate Similarity NPC157376
0.7677 Intermediate Similarity NPC182136
0.7677 Intermediate Similarity NPC310479
0.7677 Intermediate Similarity NPC78973
0.7677 Intermediate Similarity NPC302280
0.767 Intermediate Similarity NPC166745
0.767 Intermediate Similarity NPC235464
0.7664 Intermediate Similarity NPC475074
0.7653 Intermediate Similarity NPC472810
0.7653 Intermediate Similarity NPC472809
0.7642 Intermediate Similarity NPC472868
0.7642 Intermediate Similarity NPC473175
0.7642 Intermediate Similarity NPC272632
0.7636 Intermediate Similarity NPC247760
0.7636 Intermediate Similarity NPC191620
0.7632 Intermediate Similarity NPC257610
0.7629 Intermediate Similarity NPC286153
0.7629 Intermediate Similarity NPC474970
0.7624 Intermediate Similarity NPC470255
0.7624 Intermediate Similarity NPC298973
0.7624 Intermediate Similarity NPC469697
0.7624 Intermediate Similarity NPC105490
0.7624 Intermediate Similarity NPC469491
0.7624 Intermediate Similarity NPC104925
0.7624 Intermediate Similarity NPC324078
0.7619 Intermediate Similarity NPC472815
0.7619 Intermediate Similarity NPC11956
0.7611 Intermediate Similarity NPC83287
0.7611 Intermediate Similarity NPC218093
0.7609 Intermediate Similarity NPC54996
0.7607 Intermediate Similarity NPC179261
0.7604 Intermediate Similarity NPC318515
0.76 Intermediate Similarity NPC329842
0.76 Intermediate Similarity NPC212948
0.7596 Intermediate Similarity NPC251680
0.7596 Intermediate Similarity NPC38855
0.7593 Intermediate Similarity NPC220155
0.7579 Intermediate Similarity NPC16321
0.7576 Intermediate Similarity NPC82876
0.7576 Intermediate Similarity NPC472240
0.7576 Intermediate Similarity NPC174342
0.7576 Intermediate Similarity NPC146554
0.7576 Intermediate Similarity NPC262858
0.7573 Intermediate Similarity NPC57416
0.7573 Intermediate Similarity NPC107243
0.7573 Intermediate Similarity NPC475033
0.7573 Intermediate Similarity NPC99726
0.7573 Intermediate Similarity NPC202705
0.7573 Intermediate Similarity NPC475032
0.757 Intermediate Similarity NPC34768
0.7551 Intermediate Similarity NPC45957
0.7551 Intermediate Similarity NPC471657
0.7549 Intermediate Similarity NPC20546
0.7549 Intermediate Similarity NPC276110
0.7549 Intermediate Similarity NPC472441
0.7549 Intermediate Similarity NPC209355
0.7547 Intermediate Similarity NPC23584
0.7547 Intermediate Similarity NPC85742

  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 NPC181147 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
0.7938 Intermediate Similarity NPD6051 Approved
0.7876 Intermediate Similarity NPD7503 Approved
0.7745 Intermediate Similarity NPD6084 Phase 2
0.7745 Intermediate Similarity NPD6083 Phase 2
0.767 Intermediate Similarity NPD7638 Approved
0.7611 Intermediate Similarity NPD7328 Approved
0.7611 Intermediate Similarity NPD7327 Approved
0.76 Intermediate Similarity NPD5693 Phase 1
0.7596 Intermediate Similarity NPD7639 Approved
0.7596 Intermediate Similarity NPD7640 Approved
0.7549 Intermediate Similarity NPD5695 Phase 3
0.7544 Intermediate Similarity NPD7516 Approved
0.75 Intermediate Similarity NPD5696 Approved
0.7478 Intermediate Similarity NPD8294 Approved
0.7478 Intermediate Similarity NPD8377 Approved
0.7447 Intermediate Similarity NPD4195 Approved
0.7426 Intermediate Similarity NPD5284 Approved
0.7426 Intermediate Similarity NPD5281 Approved
0.7414 Intermediate Similarity NPD8379 Approved
0.7414 Intermediate Similarity NPD8296 Approved
0.7414 Intermediate Similarity NPD8378 Approved
0.7414 Intermediate Similarity NPD8033 Approved
0.7414 Intermediate Similarity NPD8380 Approved
0.7414 Intermediate Similarity NPD8335 Approved
0.74 Intermediate Similarity NPD4753 Phase 2
0.7327 Intermediate Similarity NPD5207 Approved
0.7327 Intermediate Similarity NPD5692 Phase 3
0.7321 Intermediate Similarity NPD6053 Discontinued
0.73 Intermediate Similarity NPD6903 Approved
0.7273 Intermediate Similarity NPD7146 Approved
0.7273 Intermediate Similarity NPD7334 Approved
0.7273 Intermediate Similarity NPD6409 Approved
0.7273 Intermediate Similarity NPD7320 Approved
0.7273 Intermediate Similarity NPD7521 Approved
0.7273 Intermediate Similarity NPD6684 Approved
0.7273 Intermediate Similarity NPD5330 Approved
0.7255 Intermediate Similarity NPD6050 Approved
0.7255 Intermediate Similarity NPD5694 Approved
0.7248 Intermediate Similarity NPD6675 Approved
0.7248 Intermediate Similarity NPD7128 Approved
0.7248 Intermediate Similarity NPD6402 Approved
0.7248 Intermediate Similarity NPD5739 Approved
0.7245 Intermediate Similarity NPD3133 Approved
0.7245 Intermediate Similarity NPD3665 Phase 1
0.7245 Intermediate Similarity NPD3666 Approved
0.7228 Intermediate Similarity NPD6904 Approved
0.7228 Intermediate Similarity NPD6673 Approved
0.7228 Intermediate Similarity NPD6080 Approved
0.7217 Intermediate Similarity NPD7115 Discovery
0.7216 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD4223 Phase 3
0.7216 Intermediate Similarity NPD4221 Approved
0.7212 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD5697 Approved
0.7182 Intermediate Similarity NPD5701 Approved
0.717 Intermediate Similarity NPD4225 Approved
0.7167 Intermediate Similarity NPD7507 Approved
0.7129 Intermediate Similarity NPD5737 Approved
0.7129 Intermediate Similarity NPD6672 Approved
0.7129 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5208 Approved
0.7128 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6933 Approved
0.7117 Intermediate Similarity NPD6899 Approved
0.7117 Intermediate Similarity NPD6881 Approved
0.7117 Intermediate Similarity NPD6011 Approved
0.71 Intermediate Similarity NPD5280 Approved
0.71 Intermediate Similarity NPD4694 Approved
0.7071 Intermediate Similarity NPD4197 Approved
0.7065 Intermediate Similarity NPD4243 Approved
0.7054 Intermediate Similarity NPD6014 Approved
0.7054 Intermediate Similarity NPD6012 Approved
0.7054 Intermediate Similarity NPD6373 Approved
0.7054 Intermediate Similarity NPD6372 Approved
0.7054 Intermediate Similarity NPD6013 Approved
0.7048 Intermediate Similarity NPD4629 Approved
0.7048 Intermediate Similarity NPD5210 Approved
0.703 Intermediate Similarity NPD7524 Approved
0.703 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD4202 Approved
0.7019 Intermediate Similarity NPD6399 Phase 3
0.7018 Intermediate Similarity NPD8297 Approved
0.7 Intermediate Similarity NPD5329 Approved
0.6992 Remote Similarity NPD7319 Approved
0.6991 Remote Similarity NPD7102 Approved
0.6991 Remote Similarity NPD6883 Approved
0.6991 Remote Similarity NPD7290 Approved
0.6972 Remote Similarity NPD7632 Discontinued
0.697 Remote Similarity NPD6695 Phase 3
0.6964 Remote Similarity NPD6686 Approved
0.6957 Remote Similarity NPD4632 Approved
0.6952 Remote Similarity NPD6001 Approved
0.6931 Remote Similarity NPD4138 Approved
0.6931 Remote Similarity NPD4693 Phase 3
0.6931 Remote Similarity NPD5279 Phase 3
0.6931 Remote Similarity NPD5205 Approved
0.6931 Remote Similarity NPD6098 Approved
0.6931 Remote Similarity NPD4689 Approved
0.6931 Remote Similarity NPD4688 Approved
0.6931 Remote Similarity NPD4690 Approved
0.693 Remote Similarity NPD8130 Phase 1
0.693 Remote Similarity NPD6869 Approved
0.693 Remote Similarity NPD6847 Approved
0.693 Remote Similarity NPD6617 Approved
0.693 Remote Similarity NPD6650 Approved
0.693 Remote Similarity NPD6649 Approved
0.693 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7637 Suspended
0.6916 Remote Similarity NPD4755 Approved
0.6915 Remote Similarity NPD6924 Approved
0.6915 Remote Similarity NPD4785 Approved
0.6915 Remote Similarity NPD4784 Approved
0.6915 Remote Similarity NPD6926 Approved
0.6903 Remote Similarity NPD4061 Clinical (unspecified phase)
0.69 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5654 Approved
0.6875 Remote Similarity NPD6412 Phase 2
0.687 Remote Similarity NPD6882 Approved
0.6842 Remote Similarity NPD7339 Approved
0.6842 Remote Similarity NPD5275 Approved
0.6842 Remote Similarity NPD4190 Phase 3
0.6842 Remote Similarity NPD6942 Approved
0.6837 Remote Similarity NPD7525 Registered
0.6832 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5211 Phase 2
0.68 Remote Similarity NPD4788 Approved
0.6789 Remote Similarity NPD4700 Approved
0.6789 Remote Similarity NPD4696 Approved
0.6789 Remote Similarity NPD5285 Approved
0.6789 Remote Similarity NPD5286 Approved
0.6786 Remote Similarity NPD6008 Approved
0.6765 Remote Similarity NPD3618 Phase 1
0.6765 Remote Similarity NPD5690 Phase 2
0.6759 Remote Similarity NPD5959 Approved
0.675 Remote Similarity NPD6319 Approved
0.6733 Remote Similarity NPD4786 Approved
0.6733 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5328 Approved
0.6727 Remote Similarity NPD5223 Approved
0.6727 Remote Similarity NPD4159 Approved
0.67 Remote Similarity NPD3667 Approved
0.6699 Remote Similarity NPD7750 Discontinued
0.6696 Remote Similarity NPD5141 Approved
0.6695 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD6930 Phase 2
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD6931 Approved
0.6667 Remote Similarity NPD4096 Approved
0.6639 Remote Similarity NPD6317 Approved
0.6639 Remote Similarity NPD6009 Approved
0.6636 Remote Similarity NPD5707 Approved
0.6636 Remote Similarity NPD7748 Approved
0.6607 Remote Similarity NPD5175 Approved
0.6607 Remote Similarity NPD6052 Approved
0.6607 Remote Similarity NPD5174 Approved
0.6607 Remote Similarity NPD4754 Approved
0.6604 Remote Similarity NPD6079 Approved
0.6604 Remote Similarity NPD7515 Phase 2
0.6602 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6583 Remote Similarity NPD6314 Approved
0.6583 Remote Similarity NPD6335 Approved
0.6583 Remote Similarity NPD6313 Approved
0.6571 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6929 Approved
0.6557 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6557 Remote Similarity NPD5983 Phase 2
0.6552 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6552 Remote Similarity NPD4634 Approved
0.6542 Remote Similarity NPD5133 Approved
0.6532 Remote Similarity NPD7492 Approved
0.6529 Remote Similarity NPD7101 Approved
0.6529 Remote Similarity NPD7100 Approved
0.6514 Remote Similarity NPD5221 Approved
0.6514 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6514 Remote Similarity NPD4697 Phase 3
0.6514 Remote Similarity NPD5222 Approved
0.6509 Remote Similarity NPD5785 Approved
0.65 Remote Similarity NPD4748 Discontinued
0.65 Remote Similarity NPD7514 Phase 3
0.6491 Remote Similarity NPD4768 Approved
0.6491 Remote Similarity NPD4767 Approved
0.6489 Remote Similarity NPD6922 Approved
0.6489 Remote Similarity NPD6923 Approved
0.6486 Remote Similarity NPD6404 Discontinued
0.648 Remote Similarity NPD6616 Approved
0.6476 Remote Similarity NPD4518 Approved
0.6475 Remote Similarity NPD6059 Approved
0.6475 Remote Similarity NPD6054 Approved
0.6471 Remote Similarity NPD5362 Discontinued
0.6465 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6465 Remote Similarity NPD3617 Approved
0.6455 Remote Similarity NPD7902 Approved
0.6455 Remote Similarity NPD5173 Approved
0.6452 Remote Similarity NPD7604 Phase 2
0.6449 Remote Similarity NPD7087 Discontinued
0.6442 Remote Similarity NPD4623 Approved
0.6442 Remote Similarity NPD4519 Discontinued

  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