Structure

Physi-Chem Properties

Molecular Weight:  323.12
Volume:  316.18
LogP:  3.27
LogD:  2.925
LogS:  -3.024
# Rotatable Bonds:  0
TPSA:  40.16
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.745
Synthetic Accessibility Score:  4.16
Fsp3:  0.368
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:  -4.822
MDCK Permeability:  3.5053788451477885e-05
Pgp-inhibitor:  0.076
Pgp-substrate:  0.299
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.933
Plasma Protein Binding (PPB):  95.80319213867188%
Volume Distribution (VD):  1.278
Pgp-substrate:  4.321482181549072%

ADMET: Metabolism

CYP1A2-inhibitor:  0.928
CYP1A2-substrate:  0.549
CYP2C19-inhibitor:  0.96
CYP2C19-substrate:  0.857
CYP2C9-inhibitor:  0.11
CYP2C9-substrate:  0.775
CYP2D6-inhibitor:  0.97
CYP2D6-substrate:  0.932
CYP3A4-inhibitor:  0.946
CYP3A4-substrate:  0.924

ADMET: Excretion

Clearance (CL):  20.094
Half-life (T1/2):  0.188

ADMET: Toxicity

hERG Blockers:  0.104
Human Hepatotoxicity (H-HT):  0.075
Drug-inuced Liver Injury (DILI):  0.33
AMES Toxicity:  0.635
Rat Oral Acute Toxicity:  0.351
Maximum Recommended Daily Dose:  0.966
Skin Sensitization:  0.174
Carcinogencity:  0.952
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.868

Download Data

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

  Natural Product: NPC233029

Natural Product ID:  NPC233029
Common Name*:   PGINMPJZCWDQNT-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  PGINMPJZCWDQNT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H17NO4/c1-20-14-2-10-4-16-18(23-8-21-16)6-12(10)15(20)3-11-5-17-19(7-13(11)14)24-9-22-17/h4-7,14-15H,2-3,8-9H2,1H3
SMILES:  CN1C2Cc3cc4c(cc3C1Cc1cc3c(cc21)OCO3)OCO4
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL165903
PubChem CID:   421259
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002793] Pavine alkaloids

*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
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota leaves Lai-I, Pingtung County, Taiwan 2005-May PMID[20704331]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15311 Cryptocarya chinensis Species Lauraceae 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
NPT32 Organism Mus musculus Mus musculus IC50 = 19000.0 nM PMID[542316]

☑ 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 NPC233029 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
1.0 High Similarity NPC210148
0.966 High Similarity NPC31311
0.966 High Similarity NPC234392
0.9592 High Similarity NPC138487
0.9592 High Similarity NPC216459
0.9592 High Similarity NPC41178
0.9583 High Similarity NPC475959
0.953 High Similarity NPC477080
0.9527 High Similarity NPC146288
0.94 High Similarity NPC111485
0.9371 High Similarity NPC128019
0.9371 High Similarity NPC476567
0.9371 High Similarity NPC136860
0.9156 High Similarity NPC276944
0.9156 High Similarity NPC238530
0.9156 High Similarity NPC232514
0.9116 High Similarity NPC210437
0.9116 High Similarity NPC51957
0.9116 High Similarity NPC16107
0.9116 High Similarity NPC106295
0.9116 High Similarity NPC476144
0.9097 High Similarity NPC474915
0.9097 High Similarity NPC188163
0.9097 High Similarity NPC213206
0.9097 High Similarity NPC328750
0.9073 High Similarity NPC78733
0.9054 High Similarity NPC7467
0.9038 High Similarity NPC210918
0.9028 High Similarity NPC314682
0.8961 High Similarity NPC306902
0.8961 High Similarity NPC160298
0.8961 High Similarity NPC232924
0.8961 High Similarity NPC477559
0.8961 High Similarity NPC266753
0.8951 High Similarity NPC7018
0.8947 High Similarity NPC93593
0.8947 High Similarity NPC76079
0.894 High Similarity NPC148898
0.8933 High Similarity NPC151895
0.8933 High Similarity NPC97221
0.8933 High Similarity NPC220858
0.8933 High Similarity NPC223125
0.8933 High Similarity NPC88249
0.8933 High Similarity NPC192768
0.891 High Similarity NPC167546
0.891 High Similarity NPC16805
0.891 High Similarity NPC302527
0.8896 High Similarity NPC106786
0.8854 High Similarity NPC476432
0.8854 High Similarity NPC24264
0.8846 High Similarity NPC59567
0.8816 High Similarity NPC223124
0.8812 High Similarity NPC2314
0.8797 High Similarity NPC247389
0.879 High Similarity NPC225774
0.8734 High Similarity NPC219341
0.8725 High Similarity NPC185838
0.8718 High Similarity NPC215829
0.8718 High Similarity NPC97072
0.8701 High Similarity NPC276588
0.8701 High Similarity NPC2413
0.8701 High Similarity NPC39701
0.8701 High Similarity NPC204828
0.8701 High Similarity NPC295691
0.8701 High Similarity NPC127674
0.8701 High Similarity NPC189266
0.8701 High Similarity NPC80129
0.8701 High Similarity NPC469817
0.8701 High Similarity NPC249797
0.8701 High Similarity NPC187022
0.8701 High Similarity NPC207757
0.8701 High Similarity NPC278799
0.8701 High Similarity NPC54379
0.8701 High Similarity NPC184026
0.8701 High Similarity NPC172765
0.8701 High Similarity NPC193949
0.8701 High Similarity NPC5238
0.8701 High Similarity NPC110416
0.8679 High Similarity NPC298979
0.8679 High Similarity NPC474324
0.8679 High Similarity NPC57812
0.8679 High Similarity NPC100566
0.8675 High Similarity NPC135538
0.8675 High Similarity NPC24233
0.8675 High Similarity NPC428
0.8675 High Similarity NPC130941
0.8675 High Similarity NPC147390
0.8675 High Similarity NPC476571
0.8675 High Similarity NPC246587
0.865 High Similarity NPC118633
0.865 High Similarity NPC294790
0.865 High Similarity NPC148693
0.8645 High Similarity NPC25084
0.8645 High Similarity NPC247639
0.8634 High Similarity NPC19520
0.8634 High Similarity NPC149090
0.8634 High Similarity NPC65403
0.8627 High Similarity NPC476568
0.8625 High Similarity NPC266176
0.8625 High Similarity NPC82533
0.8625 High Similarity NPC290759
0.8625 High Similarity NPC475845
0.8625 High Similarity NPC158148
0.8625 High Similarity NPC241055
0.8618 High Similarity NPC92541
0.8618 High Similarity NPC219162
0.8616 High Similarity NPC86144
0.8616 High Similarity NPC304659
0.8609 High Similarity NPC191376
0.8609 High Similarity NPC321505
0.8609 High Similarity NPC179825
0.8608 High Similarity NPC320104
0.8571 High Similarity NPC474708
0.8571 High Similarity NPC75958
0.8571 High Similarity NPC6152
0.8571 High Similarity NPC311991
0.8562 High Similarity NPC181653
0.8562 High Similarity NPC190332
0.8553 High Similarity NPC231198
0.8553 High Similarity NPC247972
0.8553 High Similarity NPC168409
0.8535 High Similarity NPC216816
0.8531 High Similarity NPC160193
0.8528 High Similarity NPC128560
0.8528 High Similarity NPC199465
0.8528 High Similarity NPC229166
0.8519 High Similarity NPC225597
0.8519 High Similarity NPC477640
0.8519 High Similarity NPC470739
0.8509 High Similarity NPC58766
0.8509 High Similarity NPC475686
0.8506 High Similarity NPC81733
0.8506 High Similarity NPC326316
0.8506 High Similarity NPC476579
0.8494 Intermediate Similarity NPC299990
0.8494 Intermediate Similarity NPC73492
0.8491 Intermediate Similarity NPC189470
0.8487 Intermediate Similarity NPC95075
0.8487 Intermediate Similarity NPC144863
0.8487 Intermediate Similarity NPC253883
0.8487 Intermediate Similarity NPC476151
0.8487 Intermediate Similarity NPC90844
0.8477 Intermediate Similarity NPC130926
0.8462 Intermediate Similarity NPC325871
0.8462 Intermediate Similarity NPC99659
0.8457 Intermediate Similarity NPC474475
0.8428 Intermediate Similarity NPC24954
0.8424 Intermediate Similarity NPC114364
0.8424 Intermediate Similarity NPC320223
0.8415 Intermediate Similarity NPC187678
0.8415 Intermediate Similarity NPC304675
0.8378 Intermediate Similarity NPC253429
0.8377 Intermediate Similarity NPC207824
0.8377 Intermediate Similarity NPC477565
0.8377 Intermediate Similarity NPC60538
0.8377 Intermediate Similarity NPC103379
0.8375 Intermediate Similarity NPC475393
0.8367 Intermediate Similarity NPC11147
0.8364 Intermediate Similarity NPC287588
0.8364 Intermediate Similarity NPC237044
0.8364 Intermediate Similarity NPC474470
0.8354 Intermediate Similarity NPC476572
0.8344 Intermediate Similarity NPC244112
0.8343 Intermediate Similarity NPC477259
0.8343 Intermediate Similarity NPC169387
0.8333 Intermediate Similarity NPC37272
0.8323 Intermediate Similarity NPC284183
0.8323 Intermediate Similarity NPC24465
0.8323 Intermediate Similarity NPC4138
0.8323 Intermediate Similarity NPC121275
0.8313 Intermediate Similarity NPC15919
0.8313 Intermediate Similarity NPC474325
0.8312 Intermediate Similarity NPC59907
0.8312 Intermediate Similarity NPC37144
0.8291 Intermediate Similarity NPC186063
0.8274 Intermediate Similarity NPC116284
0.8274 Intermediate Similarity NPC275132
0.8274 Intermediate Similarity NPC248642
0.8272 Intermediate Similarity NPC264850
0.8272 Intermediate Similarity NPC250846
0.8272 Intermediate Similarity NPC240841
0.8272 Intermediate Similarity NPC476002
0.8272 Intermediate Similarity NPC268503
0.8272 Intermediate Similarity NPC317272
0.8272 Intermediate Similarity NPC42549
0.8272 Intermediate Similarity NPC13916
0.8272 Intermediate Similarity NPC256012
0.8269 Intermediate Similarity NPC277669
0.8269 Intermediate Similarity NPC76213
0.8264 Intermediate Similarity NPC172403
0.8263 Intermediate Similarity NPC258695
0.8263 Intermediate Similarity NPC474745
0.8263 Intermediate Similarity NPC126284
0.8263 Intermediate Similarity NPC27887
0.8263 Intermediate Similarity NPC244554
0.8263 Intermediate Similarity NPC470879
0.8261 Intermediate Similarity NPC233650
0.8246 Intermediate Similarity NPC281581
0.8235 Intermediate Similarity NPC145304
0.8232 Intermediate Similarity NPC152212

  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 NPC233029 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
0.9116 High Similarity NPD4584 Approved
0.9097 High Similarity NPD4664 Clinical (unspecified phase)
0.8701 High Similarity NPD7298 Approved
0.8533 High Similarity NPD5084 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD3641 Approved
0.8497 Intermediate Similarity NPD3640 Phase 3
0.8497 Intermediate Similarity NPD3639 Approved
0.8387 Intermediate Similarity NPD4017 Approved
0.8355 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD4773 Phase 2
0.828 Intermediate Similarity NPD4772 Phase 2
0.8151 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD6030 Approved
0.8141 Intermediate Similarity NPD6031 Approved
0.8098 Intermediate Similarity NPD6107 Approved
0.8072 Intermediate Similarity NPD8252 Approved
0.8072 Intermediate Similarity NPD8251 Approved
0.8072 Intermediate Similarity NPD8099 Discontinued
0.8049 Intermediate Similarity NPD4166 Phase 2
0.8037 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD8156 Discontinued
0.8013 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD5718 Phase 2
0.7949 Intermediate Similarity NPD3124 Discontinued
0.7939 Intermediate Similarity NPD4010 Discontinued
0.7919 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD7281 Phase 3
0.7895 Intermediate Similarity NPD7280 Phase 3
0.7865 Intermediate Similarity NPD4420 Approved
0.7821 Intermediate Similarity NPD5241 Discontinued
0.7811 Intermediate Similarity NPD5313 Approved
0.7811 Intermediate Similarity NPD5312 Approved
0.7771 Intermediate Similarity NPD7802 Discontinued
0.7746 Intermediate Similarity NPD8053 Approved
0.7746 Intermediate Similarity NPD8054 Approved
0.7744 Intermediate Similarity NPD6788 Approved
0.7738 Intermediate Similarity NPD4481 Phase 3
0.773 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD6895 Approved
0.7712 Intermediate Similarity NPD6896 Approved
0.7697 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7831 Phase 2
0.7697 Intermediate Similarity NPD7833 Phase 2
0.7692 Intermediate Similarity NPD5006 Approved
0.7692 Intermediate Similarity NPD5005 Approved
0.7647 Intermediate Similarity NPD2492 Phase 1
0.7633 Intermediate Similarity NPD2898 Approved
0.7622 Intermediate Similarity NPD2978 Approved
0.7622 Intermediate Similarity NPD2977 Approved
0.7619 Intermediate Similarity NPD3051 Approved
0.7616 Intermediate Similarity NPD6297 Approved
0.7588 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD5977 Approved
0.7576 Intermediate Similarity NPD5978 Approved
0.7574 Intermediate Similarity NPD2970 Approved
0.7574 Intermediate Similarity NPD2969 Approved
0.7529 Intermediate Similarity NPD27 Approved
0.7529 Intermediate Similarity NPD2489 Approved
0.7516 Intermediate Similarity NPD3110 Approved
0.7516 Intermediate Similarity NPD3109 Approved
0.7515 Intermediate Similarity NPD6071 Discontinued
0.7485 Intermediate Similarity NPD5604 Discontinued
0.7485 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD2563 Approved
0.747 Intermediate Similarity NPD2560 Approved
0.7469 Intermediate Similarity NPD4727 Phase 1
0.7453 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD6851 Approved
0.7443 Intermediate Similarity NPD6853 Approved
0.7401 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7110 Phase 1
0.7394 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD2420 Approved
0.7391 Intermediate Similarity NPD2421 Approved
0.7368 Intermediate Similarity NPD6687 Approved
0.7368 Intermediate Similarity NPD6688 Approved
0.7363 Intermediate Similarity NPD5582 Discontinued
0.7356 Intermediate Similarity NPD3885 Approved
0.7349 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD6618 Phase 2
0.7338 Intermediate Similarity NPD4474 Approved
0.7338 Intermediate Similarity NPD4475 Approved
0.733 Intermediate Similarity NPD3816 Phase 1
0.733 Intermediate Similarity NPD3815 Phase 1
0.7329 Intermediate Similarity NPD3845 Phase 1
0.7329 Intermediate Similarity NPD7124 Phase 2
0.7318 Intermediate Similarity NPD3349 Phase 2
0.7312 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD4859 Phase 1
0.7301 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD7598 Phase 2
0.7268 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD5177 Phase 3
0.725 Intermediate Similarity NPD4236 Phase 3
0.725 Intermediate Similarity NPD4237 Approved
0.7248 Intermediate Similarity NPD3705 Approved
0.7247 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD8095 Phase 1
0.7239 Intermediate Similarity NPD1424 Approved
0.7237 Intermediate Similarity NPD7247 Discontinued
0.7229 Intermediate Similarity NPD6875 Approved
0.7229 Intermediate Similarity NPD6876 Approved
0.7225 Intermediate Similarity NPD6365 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7906 Approved
0.7222 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7291 Discontinued
0.7219 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD4108 Discontinued
0.7212 Intermediate Similarity NPD4210 Discontinued
0.7205 Intermediate Similarity NPD6748 Discontinued
0.7205 Intermediate Similarity NPD5754 Discontinued
0.7193 Intermediate Similarity NPD5677 Discontinued
0.7191 Intermediate Similarity NPD2971 Approved
0.7191 Intermediate Similarity NPD7311 Approved
0.7191 Intermediate Similarity NPD7312 Approved
0.7191 Intermediate Similarity NPD7310 Approved
0.7191 Intermediate Similarity NPD2968 Approved
0.7191 Intermediate Similarity NPD7313 Approved
0.7188 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD3408 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4055 Discovery
0.7169 Intermediate Similarity NPD4005 Discontinued
0.7152 Intermediate Similarity NPD5976 Discontinued
0.7151 Intermediate Similarity NPD7309 Approved
0.7143 Intermediate Similarity NPD4162 Approved
0.7143 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3060 Approved
0.7124 Intermediate Similarity NPD7905 Discontinued
0.712 Intermediate Similarity NPD6493 Phase 3
0.7115 Intermediate Similarity NPD2674 Phase 3
0.7112 Intermediate Similarity NPD5457 Discontinued
0.7104 Intermediate Similarity NPD7296 Approved
0.7103 Intermediate Similarity NPD5283 Phase 1
0.7099 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4578 Approved
0.7095 Intermediate Similarity NPD4577 Approved
0.7089 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD4663 Approved
0.7063 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD3920 Phase 2
0.7059 Intermediate Similarity NPD2358 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4098 Discontinued
0.7051 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5708 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4498 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD3384 Approved
0.7041 Intermediate Similarity NPD3383 Approved
0.7041 Intermediate Similarity NPD3382 Approved
0.7041 Intermediate Similarity NPD5720 Discontinued
0.7039 Intermediate Similarity NPD1421 Approved
0.7039 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD1420 Approved
0.7039 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7400 Phase 3
0.7033 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD3763 Approved
0.7019 Intermediate Similarity NPD1375 Discontinued
0.7018 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD2120 Phase 2
0.7011 Intermediate Similarity NPD3922 Approved
0.7011 Intermediate Similarity NPD3921 Approved
0.7011 Intermediate Similarity NPD3923 Approved
0.7011 Intermediate Similarity NPD3924 Approved
0.7006 Intermediate Similarity NPD5600 Discontinued
0.7 Intermediate Similarity NPD2667 Approved
0.7 Intermediate Similarity NPD1753 Discontinued
0.7 Intermediate Similarity NPD5773 Approved
0.7 Intermediate Similarity NPD2668 Approved
0.7 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5772 Approved
0.6994 Remote Similarity NPD6331 Phase 2
0.6982 Remote Similarity NPD6386 Approved
0.6982 Remote Similarity NPD6385 Approved
0.6981 Remote Similarity NPD2653 Approved
0.6957 Remote Similarity NPD2161 Phase 2
0.6957 Remote Similarity NPD2490 Approved
0.6957 Remote Similarity NPD2488 Approved
0.6954 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6954 Remote Similarity NPD3983 Phase 3
0.6952 Remote Similarity NPD7034 Discontinued
0.6952 Remote Similarity NPD5564 Approved
0.6946 Remote Similarity NPD2122 Discontinued
0.6943 Remote Similarity NPD5110 Phase 2
0.6943 Remote Similarity NPD3145 Approved
0.6943 Remote Similarity NPD5111 Phase 2
0.6943 Remote Similarity NPD5109 Approved
0.6943 Remote Similarity NPD3144 Approved
0.6937 Remote Similarity NPD6111 Discontinued
0.6937 Remote Similarity NPD7119 Phase 2
0.6935 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1669 Approved
0.6928 Remote Similarity NPD4123 Phase 3

  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