Structure

Physi-Chem Properties

Molecular Weight:  345.16
Volume:  338.8
LogP:  1.803
LogD:  1.67
LogS:  -3.965
# Rotatable Bonds:  2
TPSA:  71.39
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.852
Synthetic Accessibility Score:  5.901
Fsp3:  0.579
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.876
MDCK Permeability:  1.647435055929236e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.26
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.02
30% Bioavailability (F30%):  0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.997
Plasma Protein Binding (PPB):  70.83220672607422%
Volume Distribution (VD):  2.622
Pgp-substrate:  31.097021102905273%

ADMET: Metabolism

CYP1A2-inhibitor:  0.032
CYP1A2-substrate:  0.94
CYP2C19-inhibitor:  0.036
CYP2C19-substrate:  0.947
CYP2C9-inhibitor:  0.047
CYP2C9-substrate:  0.28
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.826
CYP3A4-inhibitor:  0.238
CYP3A4-substrate:  0.951

ADMET: Excretion

Clearance (CL):  7.956
Half-life (T1/2):  0.586

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.752
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.144
Rat Oral Acute Toxicity:  0.921
Maximum Recommended Daily Dose:  0.919
Skin Sensitization:  0.513
Carcinogencity:  0.943
Eye Corrosion:  0.005
Eye Irritation:  0.063
Respiratory Toxicity:  0.946

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

  Natural Product: NPC99179

Natural Product ID:  NPC99179
Common Name*:   Prostephabyssine
IUPAC Name:   n.a.
Synonyms:   Prostephabyssine
Standard InCHIKey:  MLEYOIRGICHLGN-PZGXJPJSSA-N
Standard InCHI:  InChI=1S/C19H23NO5/c1-20-9-8-17-7-6-14(24-3)19(22)18(17,20)10-13(25-19)11-4-5-12(23-2)16(21)15(11)17/h4-6,13,21-22H,7-10H2,1-3H3/t13-,17+,18-,19-/m0/s1
SMILES:  CN1CC[C@]23CC=C([C@]4([C@@]13C[C@@H](c1ccc(c(c21)O)OC)O4)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1096482
PubChem CID:   21593990
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO11351 Stephania japonica Species Menispermaceae Eukaryota Aerial parts n.a. n.a. PMID[20426456]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9392886]
NPO14656 Stephania abyssinica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3928 Stephania longa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3928 Stephania longa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14656 Stephania abyssinica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12945 Agelas schmidti Species Agelasidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15524 Protea rubropilosa Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14656 Stephania abyssinica Species Menispermaceae 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
NPT271 Individual Protein Delta opioid receptor Homo sapiens IC50 = 5500.0 nM PMID[512479]
NPT145 Individual Protein Mu opioid receptor Homo sapiens Inhibition = 67.0 % PMID[512479]
NPT272 Individual Protein Kappa opioid receptor Homo sapiens Inhibition = 0.0 % PMID[512479]

☑ 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 NPC99179 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
0.8855 High Similarity NPC218614
0.881 High Similarity NPC252960
0.8649 High Similarity NPC11708
0.8639 High Similarity NPC124657
0.8547 High Similarity NPC470739
0.8547 High Similarity NPC225597
0.8547 High Similarity NPC477640
0.8488 Intermediate Similarity NPC474475
0.8466 Intermediate Similarity NPC305847
0.843 Intermediate Similarity NPC475686
0.843 Intermediate Similarity NPC82533
0.843 Intermediate Similarity NPC158148
0.843 Intermediate Similarity NPC58766
0.843 Intermediate Similarity NPC290759
0.843 Intermediate Similarity NPC266176
0.8418 Intermediate Similarity NPC302449
0.8402 Intermediate Similarity NPC4304
0.8382 Intermediate Similarity NPC311991
0.8371 Intermediate Similarity NPC156576
0.8352 Intermediate Similarity NPC118633
0.8352 Intermediate Similarity NPC294790
0.8352 Intermediate Similarity NPC114364
0.8352 Intermediate Similarity NPC320223
0.8352 Intermediate Similarity NPC148693
0.8343 Intermediate Similarity NPC196231
0.8315 Intermediate Similarity NPC248642
0.8314 Intermediate Similarity NPC476002
0.8305 Intermediate Similarity NPC244554
0.8295 Intermediate Similarity NPC474470
0.8266 Intermediate Similarity NPC181653
0.8266 Intermediate Similarity NPC190332
0.8249 Intermediate Similarity NPC15919
0.8239 Intermediate Similarity NPC199465
0.8239 Intermediate Similarity NPC329969
0.8239 Intermediate Similarity NPC128560
0.8239 Intermediate Similarity NPC229166
0.8225 Intermediate Similarity NPC323443
0.8225 Intermediate Similarity NPC180756
0.8222 Intermediate Similarity NPC9867
0.8202 Intermediate Similarity NPC126284
0.8192 Intermediate Similarity NPC237044
0.8187 Intermediate Similarity NPC205167
0.8187 Intermediate Similarity NPC249274
0.8182 Intermediate Similarity NPC2314
0.8162 Intermediate Similarity NPC475713
0.8162 Intermediate Similarity NPC474432
0.8161 Intermediate Similarity NPC306555
0.8161 Intermediate Similarity NPC145832
0.8161 Intermediate Similarity NPC81218
0.8161 Intermediate Similarity NPC158376
0.8161 Intermediate Similarity NPC474931
0.8161 Intermediate Similarity NPC205421
0.8161 Intermediate Similarity NPC117188
0.8161 Intermediate Similarity NPC12053
0.8161 Intermediate Similarity NPC100566
0.815 Intermediate Similarity NPC247972
0.8146 Intermediate Similarity NPC474325
0.8136 Intermediate Similarity NPC304675
0.8129 Intermediate Similarity NPC92191
0.8129 Intermediate Similarity NPC59028
0.8125 Intermediate Similarity NPC65403
0.8118 Intermediate Similarity NPC147091
0.8101 Intermediate Similarity NPC474745
0.8092 Intermediate Similarity NPC320104
0.8081 Intermediate Similarity NPC215829
0.8081 Intermediate Similarity NPC97072
0.8068 Intermediate Similarity NPC75958
0.8066 Intermediate Similarity NPC135772
0.8046 Intermediate Similarity NPC196447
0.8046 Intermediate Similarity NPC477563
0.8046 Intermediate Similarity NPC78222
0.8046 Intermediate Similarity NPC180306
0.8046 Intermediate Similarity NPC212794
0.8046 Intermediate Similarity NPC306843
0.8046 Intermediate Similarity NPC13504
0.8046 Intermediate Similarity NPC253043
0.8046 Intermediate Similarity NPC136508
0.8046 Intermediate Similarity NPC96603
0.8034 Intermediate Similarity NPC187678
0.8032 Intermediate Similarity NPC474427
0.8021 Intermediate Similarity NPC293624
0.8011 Intermediate Similarity NPC275132
0.8011 Intermediate Similarity NPC116284
0.7989 Intermediate Similarity NPC1229
0.7989 Intermediate Similarity NPC324144
0.7978 Intermediate Similarity NPC214116
0.7977 Intermediate Similarity NPC18402
0.7967 Intermediate Similarity NPC474746
0.7967 Intermediate Similarity NPC475981
0.7956 Intermediate Similarity NPC477561
0.7956 Intermediate Similarity NPC476574
0.7956 Intermediate Similarity NPC155442
0.7956 Intermediate Similarity NPC312918
0.7955 Intermediate Similarity NPC210918
0.7955 Intermediate Similarity NPC298979
0.7955 Intermediate Similarity NPC474324
0.7955 Intermediate Similarity NPC247389
0.7955 Intermediate Similarity NPC57812
0.7953 Intermediate Similarity NPC78733
0.7943 Intermediate Similarity NPC232514
0.7943 Intermediate Similarity NPC238530
0.7943 Intermediate Similarity NPC276944
0.7941 Intermediate Similarity NPC82285
0.7941 Intermediate Similarity NPC133011
0.7921 Intermediate Similarity NPC57272
0.7912 Intermediate Similarity NPC233718
0.791 Intermediate Similarity NPC475845
0.7898 Intermediate Similarity NPC24264
0.7898 Intermediate Similarity NPC219341
0.7898 Intermediate Similarity NPC476432
0.7895 Intermediate Similarity NPC151470
0.7895 Intermediate Similarity NPC64576
0.7895 Intermediate Similarity NPC254045
0.7895 Intermediate Similarity NPC201055
0.788 Intermediate Similarity NPC230098
0.7877 Intermediate Similarity NPC477020
0.7877 Intermediate Similarity NPC66341
0.7877 Intermediate Similarity NPC192135
0.7874 Intermediate Similarity NPC27410
0.7874 Intermediate Similarity NPC165797
0.7874 Intermediate Similarity NPC166014
0.7865 Intermediate Similarity NPC474708
0.7861 Intermediate Similarity NPC40389
0.7861 Intermediate Similarity NPC315707
0.7861 Intermediate Similarity NPC78359
0.7861 Intermediate Similarity NPC65490
0.7861 Intermediate Similarity NPC148014
0.7853 Intermediate Similarity NPC475747
0.7853 Intermediate Similarity NPC210140
0.7853 Intermediate Similarity NPC150879
0.7841 Intermediate Similarity NPC167546
0.7841 Intermediate Similarity NPC302527
0.7841 Intermediate Similarity NPC225774
0.7841 Intermediate Similarity NPC3375
0.7841 Intermediate Similarity NPC255607
0.7841 Intermediate Similarity NPC16805
0.7838 Intermediate Similarity NPC237579
0.7833 Intermediate Similarity NPC49353
0.7829 Intermediate Similarity NPC60186
0.7821 Intermediate Similarity NPC239775
0.7814 Intermediate Similarity NPC476575
0.7807 Intermediate Similarity NPC94499
0.7802 Intermediate Similarity NPC149285
0.7802 Intermediate Similarity NPC267408
0.7802 Intermediate Similarity NPC32154
0.7796 Intermediate Similarity NPC82763
0.7778 Intermediate Similarity NPC66909
0.7765 Intermediate Similarity NPC103379
0.7765 Intermediate Similarity NPC168753
0.7765 Intermediate Similarity NPC69712
0.7765 Intermediate Similarity NPC118274
0.7765 Intermediate Similarity NPC26240
0.7765 Intermediate Similarity NPC477565
0.7765 Intermediate Similarity NPC211296
0.7765 Intermediate Similarity NPC477562
0.7759 Intermediate Similarity NPC476572
0.7759 Intermediate Similarity NPC129603
0.7753 Intermediate Similarity NPC298186
0.7753 Intermediate Similarity NPC301189
0.7746 Intermediate Similarity NPC295691
0.7746 Intermediate Similarity NPC2413
0.7746 Intermediate Similarity NPC127674
0.7746 Intermediate Similarity NPC276588
0.7746 Intermediate Similarity NPC39701
0.7746 Intermediate Similarity NPC189266
0.7746 Intermediate Similarity NPC278799
0.7746 Intermediate Similarity NPC184026
0.7746 Intermediate Similarity NPC5238
0.7746 Intermediate Similarity NPC204828
0.7746 Intermediate Similarity NPC193949
0.7746 Intermediate Similarity NPC249797
0.7746 Intermediate Similarity NPC110416
0.7746 Intermediate Similarity NPC207757
0.7746 Intermediate Similarity NPC54379
0.7746 Intermediate Similarity NPC172765
0.7746 Intermediate Similarity NPC469817
0.7742 Intermediate Similarity NPC141440
0.7742 Intermediate Similarity NPC476576
0.7742 Intermediate Similarity NPC186546
0.774 Intermediate Similarity NPC134858
0.7735 Intermediate Similarity NPC477558
0.7733 Intermediate Similarity NPC148898
0.7725 Intermediate Similarity NPC33256
0.7719 Intermediate Similarity NPC274026
0.7714 Intermediate Similarity NPC111485
0.7713 Intermediate Similarity NPC117717
0.7709 Intermediate Similarity NPC204908
0.7709 Intermediate Similarity NPC83198
0.7709 Intermediate Similarity NPC182257
0.7706 Intermediate Similarity NPC135538
0.7706 Intermediate Similarity NPC147390
0.7706 Intermediate Similarity NPC428
0.7706 Intermediate Similarity NPC476571
0.7706 Intermediate Similarity NPC246587
0.7706 Intermediate Similarity NPC24233
0.7705 Intermediate Similarity NPC220961
0.7701 Intermediate Similarity NPC160931
0.7701 Intermediate Similarity NPC37205
0.7697 Intermediate Similarity NPC264850
0.7697 Intermediate Similarity NPC13916

  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 NPC99179 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
0.8647 High Similarity NPD2489 Approved
0.8647 High Similarity NPD27 Approved
0.8588 High Similarity NPD2969 Approved
0.8588 High Similarity NPD2970 Approved
0.8483 Intermediate Similarity NPD7906 Approved
0.8466 Intermediate Similarity NPD4577 Approved
0.8466 Intermediate Similarity NPD7311 Approved
0.8466 Intermediate Similarity NPD7312 Approved
0.8466 Intermediate Similarity NPD4578 Approved
0.8466 Intermediate Similarity NPD7313 Approved
0.8466 Intermediate Similarity NPD7310 Approved
0.8427 Intermediate Similarity NPD4663 Approved
0.8421 Intermediate Similarity NPD3051 Approved
0.8418 Intermediate Similarity NPD7309 Approved
0.8218 Intermediate Similarity NPD4481 Phase 3
0.7989 Intermediate Similarity NPD2494 Approved
0.7989 Intermediate Similarity NPD2493 Approved
0.7907 Intermediate Similarity NPD2977 Approved
0.7907 Intermediate Similarity NPD2978 Approved
0.7895 Intermediate Similarity NPD3452 Approved
0.7895 Intermediate Similarity NPD3450 Approved
0.7892 Intermediate Similarity NPD2488 Approved
0.7892 Intermediate Similarity NPD2490 Approved
0.7892 Intermediate Similarity NPD5241 Discontinued
0.7879 Intermediate Similarity NPD4236 Phase 3
0.7879 Intermediate Similarity NPD4237 Approved
0.7865 Intermediate Similarity NPD4583 Approved
0.7865 Intermediate Similarity NPD4582 Approved
0.7861 Intermediate Similarity NPD2560 Approved
0.7861 Intermediate Similarity NPD2563 Approved
0.7812 Intermediate Similarity NPD4002 Approved
0.7812 Intermediate Similarity NPD4004 Approved
0.7784 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2973 Approved
0.7778 Intermediate Similarity NPD2975 Approved
0.7778 Intermediate Similarity NPD2974 Approved
0.7751 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD7047 Phase 3
0.7697 Intermediate Similarity NPD6071 Discontinued
0.7688 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD4580 Approved
0.7616 Intermediate Similarity NPD4210 Discontinued
0.759 Intermediate Similarity NPD4040 Phase 1
0.7568 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD2968 Approved
0.7568 Intermediate Similarity NPD2971 Approved
0.753 Intermediate Similarity NPD1753 Discontinued
0.7529 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD2898 Approved
0.7512 Intermediate Similarity NPD6997 Phase 2
0.75 Intermediate Similarity NPD5773 Approved
0.75 Intermediate Similarity NPD5772 Approved
0.7472 Intermediate Similarity NPD7833 Phase 2
0.7472 Intermediate Similarity NPD7831 Phase 2
0.7472 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD2677 Approved
0.7456 Intermediate Similarity NPD3060 Approved
0.7442 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6042 Phase 2
0.7391 Intermediate Similarity NPD42 Phase 2
0.7382 Intermediate Similarity NPD7296 Approved
0.7371 Intermediate Similarity NPD4420 Approved
0.7341 Intermediate Similarity NPD4584 Approved
0.734 Intermediate Similarity NPD8053 Approved
0.734 Intermediate Similarity NPD8054 Approved
0.7337 Intermediate Similarity NPD1375 Discontinued
0.7333 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7827 Phase 1
0.731 Intermediate Similarity NPD5006 Approved
0.731 Intermediate Similarity NPD5005 Approved
0.731 Intermediate Similarity NPD2491 Approved
0.731 Intermediate Similarity NPD3057 Approved
0.7303 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD7037 Approved
0.7294 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD4666 Phase 3
0.7277 Intermediate Similarity NPD5676 Approved
0.7268 Intermediate Similarity NPD5582 Discontinued
0.7267 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD4162 Approved
0.7238 Intermediate Similarity NPD5709 Phase 3
0.7222 Intermediate Similarity NPD3448 Approved
0.7222 Intermediate Similarity NPD3533 Approved
0.7222 Intermediate Similarity NPD2972 Approved
0.7216 Intermediate Similarity NPD3687 Approved
0.7216 Intermediate Similarity NPD3686 Approved
0.7212 Intermediate Similarity NPD7907 Approved
0.72 Intermediate Similarity NPD6090 Discontinued
0.7198 Intermediate Similarity NPD4111 Phase 1
0.7198 Intermediate Similarity NPD4665 Approved
0.7193 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD4772 Phase 2
0.7191 Intermediate Similarity NPD6072 Discontinued
0.7191 Intermediate Similarity NPD4773 Phase 2
0.7186 Intermediate Similarity NPD2238 Phase 2
0.7184 Intermediate Similarity NPD2420 Approved
0.7184 Intermediate Similarity NPD2421 Approved
0.7182 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD3692 Discontinued
0.7151 Intermediate Similarity NPD5177 Phase 3
0.7143 Intermediate Similarity NPD4123 Phase 3
0.7143 Intermediate Similarity NPD7019 Approved
0.7143 Intermediate Similarity NPD7020 Approved
0.7143 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD4107 Approved
0.7118 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD5754 Discontinued
0.7108 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3109 Approved
0.7083 Intermediate Similarity NPD3110 Approved
0.7062 Intermediate Similarity NPD4727 Phase 1
0.7062 Intermediate Similarity NPD5976 Discontinued
0.7059 Intermediate Similarity NPD6895 Approved
0.7059 Intermediate Similarity NPD6896 Approved
0.7049 Intermediate Similarity NPD6234 Discontinued
0.7048 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD4721 Approved
0.7035 Intermediate Similarity NPD4726 Approved
0.7035 Intermediate Similarity NPD4725 Approved
0.7029 Intermediate Similarity NPD7124 Phase 2
0.7029 Intermediate Similarity NPD3122 Phase 3
0.7027 Intermediate Similarity NPD4010 Discontinued
0.7021 Intermediate Similarity NPD8156 Discontinued
0.7015 Intermediate Similarity NPD7497 Discontinued
0.7011 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7039 Approved
0.7 Intermediate Similarity NPD4482 Phase 3
0.7 Intermediate Similarity NPD7038 Approved
0.6983 Remote Similarity NPD4005 Discontinued
0.6982 Remote Similarity NPD3059 Approved
0.6982 Remote Similarity NPD3062 Approved
0.6982 Remote Similarity NPD3061 Approved
0.6982 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6982 Remote Similarity NPD3620 Phase 2
0.6973 Remote Similarity NPD6107 Approved
0.6968 Remote Similarity NPD8099 Discontinued
0.6968 Remote Similarity NPD8252 Approved
0.6968 Remote Similarity NPD8251 Approved
0.6949 Remote Similarity NPD3645 Discontinued
0.6947 Remote Similarity NPD7007 Discovery
0.6944 Remote Similarity NPD4678 Approved
0.6944 Remote Similarity NPD4675 Approved
0.6941 Remote Similarity NPD7048 Phase 3
0.6932 Remote Similarity NPD6666 Approved
0.6932 Remote Similarity NPD6667 Approved
0.6927 Remote Similarity NPD7281 Phase 3
0.6927 Remote Similarity NPD7280 Phase 3
0.6923 Remote Similarity NPD1130 Approved
0.6923 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1136 Approved
0.6923 Remote Similarity NPD1132 Approved
0.6919 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6331 Phase 2
0.6901 Remote Similarity NPD817 Approved
0.6901 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5314 Approved
0.6901 Remote Similarity NPD823 Approved
0.6898 Remote Similarity NPD6687 Approved
0.6898 Remote Similarity NPD6688 Approved
0.6893 Remote Similarity NPD7213 Phase 3
0.6893 Remote Similarity NPD7212 Phase 2
0.6893 Remote Similarity NPD1774 Approved
0.689 Remote Similarity NPD2232 Approved
0.689 Remote Similarity NPD2230 Approved
0.689 Remote Similarity NPD2233 Approved
0.6886 Remote Similarity NPD3637 Approved
0.6886 Remote Similarity NPD3636 Approved
0.6886 Remote Similarity NPD3635 Approved
0.6879 Remote Similarity NPD6032 Approved
0.6879 Remote Similarity NPD2161 Phase 2
0.6872 Remote Similarity NPD6031 Approved
0.6872 Remote Similarity NPD6030 Approved
0.6868 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6864 Remote Similarity NPD597 Approved
0.6864 Remote Similarity NPD5718 Phase 2
0.6864 Remote Similarity NPD598 Approved
0.6864 Remote Similarity NPD601 Approved
0.6854 Remote Similarity NPD7447 Phase 1
0.6848 Remote Similarity NPD4966 Approved
0.6848 Remote Similarity NPD4967 Phase 2
0.6848 Remote Similarity NPD4965 Approved
0.6845 Remote Similarity NPD2605 Approved
0.6845 Remote Similarity NPD2606 Approved
0.6829 Remote Similarity NPD3705 Approved
0.6826 Remote Similarity NPD6584 Phase 3
0.6824 Remote Similarity NPD2674 Phase 3
0.6824 Remote Similarity NPD554 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2154 Approved
0.6821 Remote Similarity NPD2155 Approved
0.6821 Remote Similarity NPD2156 Approved
0.6818 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7526 Approved
0.6816 Remote Similarity NPD52 Approved
0.6816 Remote Similarity NPD7527 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