Structure

Physi-Chem Properties

Molecular Weight:  327.15
Volume:  333.293
LogP:  1.852
LogD:  2.123
LogS:  -1.096
# Rotatable Bonds:  2
TPSA:  62.16
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.831
Synthetic Accessibility Score:  3.15
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.868
MDCK Permeability:  1.5031388102215715e-05
Pgp-inhibitor:  0.02
Pgp-substrate:  0.812
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.981
Plasma Protein Binding (PPB):  94.10027313232422%
Volume Distribution (VD):  1.316
Pgp-substrate:  7.575519561767578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.299
CYP1A2-substrate:  0.955
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.769
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.587
CYP2D6-inhibitor:  0.083
CYP2D6-substrate:  0.9
CYP3A4-inhibitor:  0.064
CYP3A4-substrate:  0.885

ADMET: Excretion

Clearance (CL):  9.82
Half-life (T1/2):  0.646

ADMET: Toxicity

hERG Blockers:  0.306
Human Hepatotoxicity (H-HT):  0.121
Drug-inuced Liver Injury (DILI):  0.382
AMES Toxicity:  0.596
Rat Oral Acute Toxicity:  0.713
Maximum Recommended Daily Dose:  0.94
Skin Sensitization:  0.519
Carcinogencity:  0.096
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.862

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

  Natural Product: NPC474931

Natural Product ID:  NPC474931
Common Name*:   Sauveoline
IUPAC Name:   (6aR)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
Synonyms:   Sauveoline
Standard InCHIKey:  FNHRMNVLZGCBIE-GFCCVEGCSA-N
Standard InCHI:  InChI=1S/C19H21NO4/c1-20-7-6-11-9-14(23-2)19(24-3)17-15(11)12(20)8-10-4-5-13(21)18(22)16(10)17/h4-5,9,12,21-22H,6-8H2,1-3H3/t12-/m1/s1
SMILES:  CN1CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)O)O)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL488204
PubChem CID:   44559867
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO32838 artabottys maingayi Species n.a. n.a. n.a. n.a. n.a. PMID[8676127]

☑ 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
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus IC50 > 100000.0 nM PMID[492377]
NPT2 Others Unspecified Ratio IC50 < 0.63 n.a. PMID[492377]
NPT2 Others Unspecified Ratio IC50 < 0.005 n.a. PMID[492377]

☑ 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 NPC474931 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 NPC158376
1.0 High Similarity NPC145832
1.0 High Similarity NPC205421
1.0 High Similarity NPC81218
1.0 High Similarity NPC12053
1.0 High Similarity NPC117188
1.0 High Similarity NPC306555
0.987 High Similarity NPC212794
0.987 High Similarity NPC13504
0.987 High Similarity NPC306843
0.987 High Similarity NPC78222
0.987 High Similarity NPC96603
0.987 High Similarity NPC253043
0.987 High Similarity NPC196447
0.987 High Similarity NPC136508
0.987 High Similarity NPC477563
0.9805 High Similarity NPC324144
0.9805 High Similarity NPC1229
0.9675 High Similarity NPC166014
0.9675 High Similarity NPC27410
0.9623 High Similarity NPC192135
0.9623 High Similarity NPC477020
0.9623 High Similarity NPC66341
0.9565 High Similarity NPC320223
0.9565 High Similarity NPC114364
0.956 High Similarity NPC239775
0.9545 High Similarity NPC476572
0.9497 High Similarity NPC26240
0.9497 High Similarity NPC477562
0.9497 High Similarity NPC69712
0.9497 High Similarity NPC168753
0.9497 High Similarity NPC118274
0.9441 High Similarity NPC128560
0.9441 High Similarity NPC199465
0.9441 High Similarity NPC229166
0.9416 High Similarity NPC325871
0.9416 High Similarity NPC99659
0.9363 High Similarity NPC60186
0.9308 High Similarity NPC81247
0.9308 High Similarity NPC35627
0.9308 High Similarity NPC476573
0.9268 High Similarity NPC474507
0.9221 High Similarity NPC326316
0.9221 High Similarity NPC81733
0.9217 High Similarity NPC135772
0.9157 High Similarity NPC116284
0.9146 High Similarity NPC476577
0.9146 High Similarity NPC148709
0.9146 High Similarity NPC173416
0.913 High Similarity NPC247389
0.913 High Similarity NPC298979
0.9096 High Similarity NPC476574
0.9096 High Similarity NPC155442
0.9096 High Similarity NPC312918
0.9096 High Similarity NPC477561
0.9068 High Similarity NPC24264
0.9068 High Similarity NPC219341
0.9068 High Similarity NPC476432
0.9045 High Similarity NPC189266
0.9045 High Similarity NPC2413
0.9045 High Similarity NPC184026
0.9045 High Similarity NPC207757
0.9045 High Similarity NPC5238
0.9045 High Similarity NPC469817
0.9045 High Similarity NPC193949
0.9045 High Similarity NPC276588
0.9045 High Similarity NPC110416
0.9045 High Similarity NPC204828
0.9045 High Similarity NPC249797
0.9045 High Similarity NPC295691
0.9045 High Similarity NPC39701
0.9045 High Similarity NPC127674
0.9045 High Similarity NPC172765
0.9045 High Similarity NPC278799
0.9045 High Similarity NPC54379
0.9042 High Similarity NPC248642
0.9026 High Similarity NPC147390
0.9026 High Similarity NPC246587
0.9026 High Similarity NPC428
0.9026 High Similarity NPC476571
0.9026 High Similarity NPC24233
0.9026 High Similarity NPC135538
0.9006 High Similarity NPC302527
0.9006 High Similarity NPC16805
0.9006 High Similarity NPC167546
0.9006 High Similarity NPC225774
0.8988 High Similarity NPC156576
0.8968 High Similarity NPC477565
0.8968 High Similarity NPC103379
0.8961 High Similarity NPC321505
0.8961 High Similarity NPC179825
0.8961 High Similarity NPC191376
0.8951 High Similarity NPC13916
0.8951 High Similarity NPC264850
0.8922 High Similarity NPC126284
0.891 High Similarity NPC220858
0.891 High Similarity NPC97221
0.891 High Similarity NPC88249
0.891 High Similarity NPC151895
0.891 High Similarity NPC192768
0.8896 High Similarity NPC210918
0.8895 High Similarity NPC478093
0.8889 High Similarity NPC82763
0.8889 High Similarity NPC24465
0.8868 High Similarity NPC203784
0.8868 High Similarity NPC186063
0.8868 High Similarity NPC170503
0.8868 High Similarity NPC126519
0.8855 High Similarity NPC477558
0.8844 High Similarity NPC478092
0.8844 High Similarity NPC478091
0.8844 High Similarity NPC473589
0.8844 High Similarity NPC30182
0.8839 High Similarity NPC476151
0.8831 High Similarity NPC185838
0.883 High Similarity NPC186546
0.883 High Similarity NPC476576
0.882 High Similarity NPC160298
0.882 High Similarity NPC306902
0.882 High Similarity NPC232924
0.882 High Similarity NPC266753
0.882 High Similarity NPC477559
0.881 High Similarity NPC32154
0.8805 High Similarity NPC244112
0.878 High Similarity NPC204947
0.878 High Similarity NPC210140
0.878 High Similarity NPC150879
0.8772 High Similarity NPC320088
0.8772 High Similarity NPC57036
0.8765 High Similarity NPC80759
0.8765 High Similarity NPC79402
0.8735 High Similarity NPC149090
0.8735 High Similarity NPC19520
0.8735 High Similarity NPC231371
0.8727 High Similarity NPC204908
0.8727 High Similarity NPC83198
0.8721 High Similarity NPC275680
0.8721 High Similarity NPC22115
0.872 High Similarity NPC124657
0.8704 High Similarity NPC119649
0.8704 High Similarity NPC271388
0.8704 High Similarity NPC235143
0.8704 High Similarity NPC230956
0.8704 High Similarity NPC205255
0.869 High Similarity NPC241704
0.8683 High Similarity NPC152680
0.8683 High Similarity NPC190783
0.8683 High Similarity NPC232386
0.8679 High Similarity NPC26601
0.8675 High Similarity NPC6152
0.8675 High Similarity NPC152212
0.8663 High Similarity NPC214116
0.8659 High Similarity NPC276944
0.8659 High Similarity NPC134858
0.8659 High Similarity NPC169743
0.8659 High Similarity NPC238530
0.8659 High Similarity NPC232514
0.8655 High Similarity NPC33902
0.8655 High Similarity NPC276674
0.8642 High Similarity NPC221864
0.8639 High Similarity NPC118633
0.8639 High Similarity NPC148693
0.8639 High Similarity NPC294790
0.8631 High Similarity NPC329969
0.8625 High Similarity NPC477564
0.8625 High Similarity NPC2295
0.8621 High Similarity NPC475754
0.8616 High Similarity NPC277669
0.8616 High Similarity NPC76213
0.8605 High Similarity NPC16357
0.8605 High Similarity NPC95426
0.8605 High Similarity NPC302245
0.8599 High Similarity NPC210437
0.8599 High Similarity NPC106295
0.8599 High Similarity NPC476144
0.8599 High Similarity NPC16107
0.8599 High Similarity NPC51957
0.8598 High Similarity NPC233650
0.8589 High Similarity NPC205167
0.8589 High Similarity NPC249274
0.8588 High Similarity NPC220961
0.8571 High Similarity NPC470925
0.8571 High Similarity NPC328750
0.8571 High Similarity NPC474915
0.8571 High Similarity NPC213206
0.8571 High Similarity NPC78284
0.8571 High Similarity NPC188163
0.8555 High Similarity NPC65312
0.8555 High Similarity NPC139783
0.8544 High Similarity NPC7467
0.8538 High Similarity NPC286119
0.8538 High Similarity NPC474506
0.8538 High Similarity NPC32413
0.8528 High Similarity NPC111485
0.8506 High Similarity NPC314682
0.8503 High Similarity NPC241055
0.8494 Intermediate Similarity NPC268503
0.8494 Intermediate Similarity NPC256012
0.8494 Intermediate Similarity NPC304659
0.8494 Intermediate Similarity NPC86144

  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 NPC474931 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
0.8896 High Similarity NPD2420 Approved
0.8896 High Similarity NPD2421 Approved
0.8614 High Similarity NPD27 Approved
0.8614 High Similarity NPD2489 Approved
0.8606 High Similarity NPD3051 Approved
0.8599 High Similarity NPD4584 Approved
0.8571 High Similarity NPD4664 Clinical (unspecified phase)
0.8555 High Similarity NPD7906 Approved
0.8554 High Similarity NPD2969 Approved
0.8554 High Similarity NPD2970 Approved
0.8488 Intermediate Similarity NPD8053 Approved
0.8488 Intermediate Similarity NPD8054 Approved
0.843 Intermediate Similarity NPD4577 Approved
0.843 Intermediate Similarity NPD4578 Approved
0.843 Intermediate Similarity NPD7313 Approved
0.843 Intermediate Similarity NPD7312 Approved
0.843 Intermediate Similarity NPD7311 Approved
0.843 Intermediate Similarity NPD7310 Approved
0.8391 Intermediate Similarity NPD4663 Approved
0.8382 Intermediate Similarity NPD7309 Approved
0.8293 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD2898 Approved
0.8176 Intermediate Similarity NPD5241 Discontinued
0.8166 Intermediate Similarity NPD4010 Discontinued
0.8155 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD3845 Phase 1
0.8081 Intermediate Similarity NPD8099 Discontinued
0.8081 Intermediate Similarity NPD8252 Approved
0.8081 Intermediate Similarity NPD8251 Approved
0.807 Intermediate Similarity NPD4481 Phase 3
0.8045 Intermediate Similarity NPD2488 Approved
0.8045 Intermediate Similarity NPD2490 Approved
0.8036 Intermediate Similarity NPD7831 Phase 2
0.8036 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD7833 Phase 2
0.8035 Intermediate Similarity NPD8156 Discontinued
0.8011 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD6788 Approved
0.7946 Intermediate Similarity NPD3450 Approved
0.7946 Intermediate Similarity NPD2493 Approved
0.7946 Intermediate Similarity NPD2494 Approved
0.7946 Intermediate Similarity NPD3452 Approved
0.7939 Intermediate Similarity NPD4017 Approved
0.7914 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7298 Approved
0.7853 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD6071 Discontinued
0.7844 Intermediate Similarity NPD4773 Phase 2
0.7844 Intermediate Similarity NPD4772 Phase 2
0.7819 Intermediate Similarity NPD4583 Approved
0.7819 Intermediate Similarity NPD4582 Approved
0.7811 Intermediate Similarity NPD2560 Approved
0.7811 Intermediate Similarity NPD2563 Approved
0.7771 Intermediate Similarity NPD3110 Approved
0.7771 Intermediate Similarity NPD3109 Approved
0.7766 Intermediate Similarity NPD4002 Approved
0.7766 Intermediate Similarity NPD4004 Approved
0.7765 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD2975 Approved
0.773 Intermediate Similarity NPD2974 Approved
0.773 Intermediate Similarity NPD2973 Approved
0.7711 Intermediate Similarity NPD3639 Approved
0.7711 Intermediate Similarity NPD6031 Approved
0.7711 Intermediate Similarity NPD6030 Approved
0.7711 Intermediate Similarity NPD3641 Approved
0.7711 Intermediate Similarity NPD3640 Phase 3
0.7709 Intermediate Similarity NPD2968 Approved
0.7709 Intermediate Similarity NPD2971 Approved
0.7688 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD4055 Discovery
0.7607 Intermediate Similarity NPD5177 Phase 3
0.7606 Intermediate Similarity NPD4580 Approved
0.7602 Intermediate Similarity NPD7047 Phase 3
0.758 Intermediate Similarity NPD5156 Approved
0.758 Intermediate Similarity NPD5155 Approved
0.7578 Intermediate Similarity NPD1753 Discontinued
0.755 Intermediate Similarity NPD6997 Phase 2
0.7545 Intermediate Similarity NPD6090 Discontinued
0.7544 Intermediate Similarity NPD2978 Approved
0.7544 Intermediate Similarity NPD2977 Approved
0.7532 Intermediate Similarity NPD5718 Phase 2
0.7528 Intermediate Similarity NPD6042 Phase 2
0.7528 Intermediate Similarity NPD42 Phase 2
0.7516 Intermediate Similarity NPD2606 Approved
0.7516 Intermediate Similarity NPD2605 Approved
0.7516 Intermediate Similarity NPD3595 Approved
0.7516 Intermediate Similarity NPD3594 Approved
0.7515 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3060 Approved
0.7486 Intermediate Similarity NPD7802 Discontinued
0.7485 Intermediate Similarity NPD4726 Approved
0.7485 Intermediate Similarity NPD4721 Approved
0.7485 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD4725 Approved
0.7484 Intermediate Similarity NPD2674 Phase 3
0.7468 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD3636 Approved
0.7452 Intermediate Similarity NPD3637 Approved
0.7452 Intermediate Similarity NPD3635 Approved
0.7448 Intermediate Similarity NPD4040 Phase 1
0.7444 Intermediate Similarity NPD6297 Approved
0.7381 Intermediate Similarity NPD4123 Phase 3
0.7381 Intermediate Similarity NPD1424 Approved
0.7381 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD4475 Approved
0.7375 Intermediate Similarity NPD4474 Approved
0.7344 Intermediate Similarity NPD3448 Approved
0.7344 Intermediate Similarity NPD2491 Approved
0.7344 Intermediate Similarity NPD3057 Approved
0.733 Intermediate Similarity NPD4666 Phase 3
0.7321 Intermediate Similarity NPD3124 Discontinued
0.7312 Intermediate Similarity NPD3145 Approved
0.7312 Intermediate Similarity NPD3144 Approved
0.731 Intermediate Similarity NPD4005 Discontinued
0.7301 Intermediate Similarity NPD6895 Approved
0.7301 Intermediate Similarity NPD6896 Approved
0.7296 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD4237 Approved
0.7289 Intermediate Similarity NPD4236 Phase 3
0.7288 Intermediate Similarity NPD6107 Approved
0.7283 Intermediate Similarity NPD6853 Approved
0.7283 Intermediate Similarity NPD6851 Approved
0.7277 Intermediate Similarity NPD8095 Phase 1
0.7273 Intermediate Similarity NPD5709 Phase 3
0.7262 Intermediate Similarity NPD7124 Phase 2
0.7262 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6666 Approved
0.7262 Intermediate Similarity NPD6667 Approved
0.7254 Intermediate Similarity NPD3533 Approved
0.7254 Intermediate Similarity NPD2972 Approved
0.7246 Intermediate Similarity NPD5754 Discontinued
0.7241 Intermediate Similarity NPD5772 Approved
0.7241 Intermediate Similarity NPD5773 Approved
0.7235 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD4257 Approved
0.7229 Intermediate Similarity NPD4256 Phase 2
0.7228 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD4420 Approved
0.7225 Intermediate Similarity NPD6072 Discontinued
0.7222 Intermediate Similarity NPD2238 Phase 2
0.7219 Intermediate Similarity NPD7598 Phase 2
0.7216 Intermediate Similarity NPD5604 Discontinued
0.7209 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5160 Discontinued
0.7202 Intermediate Similarity NPD3692 Discontinued
0.7198 Intermediate Similarity NPD7479 Phase 2
0.7195 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD2122 Discontinued
0.7193 Intermediate Similarity NPD5976 Discontinued
0.7193 Intermediate Similarity NPD4727 Phase 1
0.7189 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7447 Phase 1
0.7174 Intermediate Similarity NPD7549 Discontinued
0.7168 Intermediate Similarity NPD4678 Approved
0.7168 Intermediate Similarity NPD4675 Approved
0.7157 Intermediate Similarity NPD7907 Approved
0.7151 Intermediate Similarity NPD6747 Phase 1
0.7151 Intermediate Similarity NPD4166 Phase 2
0.7143 Intermediate Similarity NPD4873 Discontinued
0.7143 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6748 Discontinued
0.7135 Intermediate Similarity NPD5677 Discontinued
0.7135 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2230 Approved
0.7134 Intermediate Similarity NPD823 Approved
0.7134 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2232 Approved
0.7134 Intermediate Similarity NPD2233 Approved
0.7134 Intermediate Similarity NPD817 Approved
0.7126 Intermediate Similarity NPD7037 Approved
0.7118 Intermediate Similarity NPD7213 Phase 3
0.7118 Intermediate Similarity NPD7212 Phase 2
0.7111 Intermediate Similarity NPD6687 Approved
0.7111 Intermediate Similarity NPD6688 Approved
0.7107 Intermediate Similarity NPD3053 Approved
0.7107 Intermediate Similarity NPD3055 Approved
0.7102 Intermediate Similarity NPD5978 Approved
0.7102 Intermediate Similarity NPD5977 Approved
0.7101 Intermediate Similarity NPD2677 Approved
0.71 Intermediate Similarity NPD7827 Phase 1
0.7099 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4093 Discontinued
0.7093 Intermediate Similarity NPD1914 Approved
0.709 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1669 Approved
0.7083 Intermediate Similarity NPD4162 Approved
0.7079 Intermediate Similarity NPD7400 Phase 3
0.7077 Intermediate Similarity NPD5005 Approved
0.7077 Intermediate Similarity NPD5006 Approved
0.7065 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4107 Approved
0.7059 Intermediate Similarity NPD4111 Phase 1
0.7059 Intermediate Similarity NPD5087 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