Structure

Physi-Chem Properties

Molecular Weight:  325.13
Volume:  324.737
LogP:  2.636
LogD:  2.926
LogS:  -1.86
# Rotatable Bonds:  1
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.874
Synthetic Accessibility Score:  3.119
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:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.013
MDCK Permeability:  2.8542219297378324e-05
Pgp-inhibitor:  0.072
Pgp-substrate:  0.201
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.983
Plasma Protein Binding (PPB):  95.27322387695312%
Volume Distribution (VD):  1.189
Pgp-substrate:  4.139463424682617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.925
CYP1A2-substrate:  0.852
CYP2C19-inhibitor:  0.747
CYP2C19-substrate:  0.775
CYP2C9-inhibitor:  0.031
CYP2C9-substrate:  0.539
CYP2D6-inhibitor:  0.98
CYP2D6-substrate:  0.925
CYP3A4-inhibitor:  0.835
CYP3A4-substrate:  0.872

ADMET: Excretion

Clearance (CL):  20.025
Half-life (T1/2):  0.516

ADMET: Toxicity

hERG Blockers:  0.201
Human Hepatotoxicity (H-HT):  0.126
Drug-inuced Liver Injury (DILI):  0.21
AMES Toxicity:  0.566
Rat Oral Acute Toxicity:  0.603
Maximum Recommended Daily Dose:  0.931
Skin Sensitization:  0.617
Carcinogencity:  0.886
Eye Corrosion:  0.003
Eye Irritation:  0.019
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: NPC232514

Natural Product ID:  NPC232514
Common Name*:   Cheilanthifoline
IUPAC Name:   n.a.
Synonyms:   Cheilanthifoline
Standard InCHIKey:  FVXCQULKSPVRPK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H19NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3
SMILES:  COc1cc2CCN3Cc4c(ccc5c4OCO5)CC3c2cc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1209678
PubChem CID:   5117621
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO20526 Menispermum dauricum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[11473438]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. PMID[11754604]
NPO6328 Corydalis incisa Species Papaveraceae Eukaryota n.a. aerial part n.a. PMID[17366734]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota Roots Simao city, Yunnan Province, China 2007-MAY PMID[19374435]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO20526 Menispermum dauricum Species Menispermaceae Eukaryota n.a. rhizome n.a. PMID[8281582]
NPO29868 Dicentra spectabilis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6328 Corydalis incisa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20526 Menispermum dauricum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17796 Lamprocapnos spectabilis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19361 Herba meconpsis integrifoliae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6328 Corydalis incisa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20526 Menispermum dauricum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20526 Menispermum dauricum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6328 Corydalis incisa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29868 Dicentra spectabilis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17796 Lamprocapnos spectabilis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20526 Menispermum dauricum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6328 Corydalis incisa Species Papaveraceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 20630.0 nM PMID[465816]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 27410.0 nM PMID[465816]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 22240.0 nM PMID[465816]
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 29840.0 nM PMID[465816]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1880.0 nM PMID[465817]

☑ 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 NPC232514 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 NPC276944
1.0 High Similarity NPC238530
0.9737 High Similarity NPC111485
0.9539 High Similarity NPC469817
0.9539 High Similarity NPC193949
0.9539 High Similarity NPC276588
0.9539 High Similarity NPC2413
0.9539 High Similarity NPC39701
0.9539 High Similarity NPC216459
0.9539 High Similarity NPC5238
0.9539 High Similarity NPC138487
0.9539 High Similarity NPC189266
0.9539 High Similarity NPC110416
0.9539 High Similarity NPC295691
0.9539 High Similarity NPC249797
0.9539 High Similarity NPC41178
0.9539 High Similarity NPC184026
0.9539 High Similarity NPC54379
0.9539 High Similarity NPC204828
0.9539 High Similarity NPC172765
0.9539 High Similarity NPC278799
0.9539 High Similarity NPC207757
0.9539 High Similarity NPC127674
0.9477 High Similarity NPC146288
0.9351 High Similarity NPC234392
0.9351 High Similarity NPC31311
0.9276 High Similarity NPC97221
0.9276 High Similarity NPC220858
0.9276 High Similarity NPC88249
0.9276 High Similarity NPC192768
0.9276 High Similarity NPC151895
0.9255 High Similarity NPC2314
0.9211 High Similarity NPC103379
0.9211 High Similarity NPC477565
0.9156 High Similarity NPC210148
0.9156 High Similarity NPC233029
0.9145 High Similarity NPC147390
0.9145 High Similarity NPC246587
0.9145 High Similarity NPC428
0.9145 High Similarity NPC475959
0.9145 High Similarity NPC135538
0.9145 High Similarity NPC24233
0.9145 High Similarity NPC476571
0.9125 High Similarity NPC298979
0.9085 High Similarity NPC320223
0.9085 High Similarity NPC114364
0.908 High Similarity NPC199465
0.908 High Similarity NPC128560
0.908 High Similarity NPC229166
0.9079 High Similarity NPC210437
0.9079 High Similarity NPC476151
0.9079 High Similarity NPC191376
0.9079 High Similarity NPC476144
0.9079 High Similarity NPC106295
0.9079 High Similarity NPC179825
0.9079 High Similarity NPC51957
0.9079 High Similarity NPC321505
0.9079 High Similarity NPC16107
0.9062 High Similarity NPC13916
0.9062 High Similarity NPC264850
0.902 High Similarity NPC7467
0.9 High Similarity NPC24465
0.8947 High Similarity NPC185838
0.8917 High Similarity NPC93593
0.8889 High Similarity NPC24260
0.8854 High Similarity NPC477564
0.8854 High Similarity NPC2295
0.8816 High Similarity NPC128019
0.8816 High Similarity NPC476567
0.8816 High Similarity NPC136860
0.8812 High Similarity NPC160298
0.8812 High Similarity NPC232924
0.8812 High Similarity NPC266753
0.8812 High Similarity NPC477559
0.8812 High Similarity NPC166014
0.8812 High Similarity NPC306902
0.8812 High Similarity NPC27410
0.881 High Similarity NPC116284
0.8757 High Similarity NPC135772
0.875 High Similarity NPC476574
0.875 High Similarity NPC155442
0.875 High Similarity NPC312918
0.875 High Similarity NPC477080
0.875 High Similarity NPC477561
0.8743 High Similarity NPC294790
0.8743 High Similarity NPC148693
0.8743 High Similarity NPC118633
0.8742 High Similarity NPC147091
0.8736 High Similarity NPC24228
0.8726 High Similarity NPC277669
0.8726 High Similarity NPC76213
0.8712 High Similarity NPC24264
0.8712 High Similarity NPC250846
0.8712 High Similarity NPC317272
0.8712 High Similarity NPC42549
0.8712 High Similarity NPC256012
0.8712 High Similarity NPC476432
0.8712 High Similarity NPC240841
0.8712 High Similarity NPC268503
0.8704 High Similarity NPC59567
0.8704 High Similarity NPC324144
0.8696 High Similarity NPC215829
0.8696 High Similarity NPC97072
0.869 High Similarity NPC32154
0.8684 High Similarity NPC328750
0.8684 High Similarity NPC188163
0.8684 High Similarity NPC213206
0.8684 High Similarity NPC474915
0.8671 High Similarity NPC37272
0.8671 High Similarity NPC82285
0.8671 High Similarity NPC133011
0.8667 High Similarity NPC152212
0.8659 High Similarity NPC474931
0.8659 High Similarity NPC12053
0.8659 High Similarity NPC81218
0.8659 High Similarity NPC158376
0.8659 High Similarity NPC306555
0.8659 High Similarity NPC145832
0.8659 High Similarity NPC117188
0.8659 High Similarity NPC205421
0.8659 High Similarity NPC100566
0.8659 High Similarity NPC247389
0.865 High Similarity NPC16805
0.865 High Similarity NPC121275
0.865 High Similarity NPC284183
0.865 High Similarity NPC306843
0.865 High Similarity NPC302527
0.865 High Similarity NPC78222
0.865 High Similarity NPC4138
0.865 High Similarity NPC212794
0.865 High Similarity NPC96603
0.865 High Similarity NPC225774
0.865 High Similarity NPC196447
0.865 High Similarity NPC167546
0.865 High Similarity NPC136508
0.865 High Similarity NPC253043
0.865 High Similarity NPC13504
0.865 High Similarity NPC477563
0.8642 High Similarity NPC60186
0.8625 High Similarity NPC186063
0.8623 High Similarity NPC187678
0.8618 High Similarity NPC314682
0.8606 High Similarity NPC83198
0.8606 High Similarity NPC204908
0.8599 High Similarity NPC207824
0.8599 High Similarity NPC60538
0.8598 High Similarity NPC219341
0.8588 High Similarity NPC475654
0.8588 High Similarity NPC248642
0.858 High Similarity NPC126284
0.858 High Similarity NPC205167
0.8571 High Similarity NPC241704
0.8562 High Similarity NPC78733
0.8555 High Similarity NPC82763
0.8554 High Similarity NPC311991
0.8553 High Similarity NPC148898
0.8545 High Similarity NPC210918
0.8545 High Similarity NPC210140
0.8545 High Similarity NPC181653
0.8545 High Similarity NPC190332
0.8538 High Similarity NPC156576
0.8519 High Similarity NPC106786
0.8512 High Similarity NPC477558
0.8503 High Similarity NPC477640
0.8503 High Similarity NPC470739
0.8503 High Similarity NPC225597
0.8497 Intermediate Similarity NPC186546
0.8497 Intermediate Similarity NPC476576
0.8494 Intermediate Similarity NPC241055
0.8494 Intermediate Similarity NPC266176
0.8494 Intermediate Similarity NPC82533
0.8494 Intermediate Similarity NPC158148
0.8494 Intermediate Similarity NPC475686
0.8494 Intermediate Similarity NPC58766
0.8494 Intermediate Similarity NPC66573
0.8494 Intermediate Similarity NPC290759
0.8485 Intermediate Similarity NPC81247
0.8485 Intermediate Similarity NPC35627
0.8485 Intermediate Similarity NPC304659
0.8485 Intermediate Similarity NPC476573
0.8485 Intermediate Similarity NPC86144
0.848 Intermediate Similarity NPC49075
0.848 Intermediate Similarity NPC311973
0.848 Intermediate Similarity NPC54654
0.848 Intermediate Similarity NPC15414
0.848 Intermediate Similarity NPC185639
0.848 Intermediate Similarity NPC182052
0.848 Intermediate Similarity NPC285931
0.848 Intermediate Similarity NPC181796
0.848 Intermediate Similarity NPC73492
0.848 Intermediate Similarity NPC42663
0.848 Intermediate Similarity NPC290582
0.848 Intermediate Similarity NPC222661
0.848 Intermediate Similarity NPC217748
0.848 Intermediate Similarity NPC251735
0.848 Intermediate Similarity NPC258657
0.848 Intermediate Similarity NPC7715
0.848 Intermediate Similarity NPC299990
0.848 Intermediate Similarity NPC223690
0.848 Intermediate Similarity NPC239824

  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 NPC232514 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
0.9079 High Similarity NPD4584 Approved
0.8684 High Similarity NPD4664 Clinical (unspecified phase)
0.848 Intermediate Similarity NPD8053 Approved
0.848 Intermediate Similarity NPD8054 Approved
0.8274 Intermediate Similarity NPD2898 Approved
0.8272 Intermediate Similarity NPD4773 Phase 2
0.8272 Intermediate Similarity NPD4772 Phase 2
0.8263 Intermediate Similarity NPD4010 Discontinued
0.8221 Intermediate Similarity NPD7298 Approved
0.8166 Intermediate Similarity NPD2489 Approved
0.8166 Intermediate Similarity NPD27 Approved
0.8165 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD8252 Approved
0.807 Intermediate Similarity NPD8251 Approved
0.807 Intermediate Similarity NPD8099 Discontinued
0.8063 Intermediate Similarity NPD2421 Approved
0.8063 Intermediate Similarity NPD2420 Approved
0.8061 Intermediate Similarity NPD2978 Approved
0.8061 Intermediate Similarity NPD2977 Approved
0.8037 Intermediate Similarity NPD4017 Approved
0.8036 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD3639 Approved
0.8025 Intermediate Similarity NPD3640 Phase 3
0.8025 Intermediate Similarity NPD3641 Approved
0.8023 Intermediate Similarity NPD8156 Discontinued
0.8 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2970 Approved
0.8 Intermediate Similarity NPD2969 Approved
0.7941 Intermediate Similarity NPD3051 Approved
0.7937 Intermediate Similarity NPD5241 Discontinued
0.7917 Intermediate Similarity NPD7833 Phase 2
0.7917 Intermediate Similarity NPD7831 Phase 2
0.7917 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD6071 Discontinued
0.7821 Intermediate Similarity NPD7906 Approved
0.7805 Intermediate Similarity NPD6031 Approved
0.7805 Intermediate Similarity NPD6030 Approved
0.7798 Intermediate Similarity NPD2560 Approved
0.7798 Intermediate Similarity NPD2563 Approved
0.7797 Intermediate Similarity NPD7310 Approved
0.7797 Intermediate Similarity NPD7313 Approved
0.7797 Intermediate Similarity NPD7312 Approved
0.7797 Intermediate Similarity NPD7281 Phase 3
0.7797 Intermediate Similarity NPD7280 Phase 3
0.7797 Intermediate Similarity NPD7311 Approved
0.7778 Intermediate Similarity NPD6107 Approved
0.7778 Intermediate Similarity NPD3845 Phase 1
0.7753 Intermediate Similarity NPD7309 Approved
0.7751 Intermediate Similarity NPD6788 Approved
0.7697 Intermediate Similarity NPD4577 Approved
0.7697 Intermediate Similarity NPD4578 Approved
0.7677 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD4663 Approved
0.7644 Intermediate Similarity NPD4481 Phase 3
0.763 Intermediate Similarity NPD4166 Phase 2
0.7628 Intermediate Similarity NPD5718 Phase 2
0.7627 Intermediate Similarity NPD6297 Approved
0.7622 Intermediate Similarity NPD3124 Discontinued
0.7602 Intermediate Similarity NPD5604 Discontinued
0.7598 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD5177 Phase 3
0.7581 Intermediate Similarity NPD4420 Approved
0.758 Intermediate Similarity NPD2674 Phase 3
0.758 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD2488 Approved
0.7541 Intermediate Similarity NPD2490 Approved
0.7514 Intermediate Similarity NPD5312 Approved
0.7514 Intermediate Similarity NPD5313 Approved
0.7513 Intermediate Similarity NPD5005 Approved
0.7513 Intermediate Similarity NPD5006 Approved
0.75 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7802 Discontinued
0.7459 Intermediate Similarity NPD6851 Approved
0.7459 Intermediate Similarity NPD6853 Approved
0.7444 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD3145 Approved
0.7405 Intermediate Similarity NPD3144 Approved
0.7391 Intermediate Similarity NPD6895 Approved
0.7391 Intermediate Similarity NPD6896 Approved
0.7389 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.738 Intermediate Similarity NPD5582 Discontinued
0.7378 Intermediate Similarity NPD3060 Approved
0.7378 Intermediate Similarity NPD4236 Phase 3
0.7378 Intermediate Similarity NPD4237 Approved
0.7363 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4474 Approved
0.7358 Intermediate Similarity NPD4475 Approved
0.7347 Intermediate Similarity NPD3815 Phase 1
0.7347 Intermediate Similarity NPD3816 Phase 1
0.7346 Intermediate Similarity NPD1753 Discontinued
0.7341 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD2492 Phase 1
0.7321 Intermediate Similarity NPD6090 Discontinued
0.7305 Intermediate Similarity NPD7598 Phase 2
0.7299 Intermediate Similarity NPD4055 Discovery
0.7283 Intermediate Similarity NPD5978 Approved
0.7283 Intermediate Similarity NPD5977 Approved
0.7277 Intermediate Similarity NPD2494 Approved
0.7277 Intermediate Similarity NPD3452 Approved
0.7277 Intermediate Similarity NPD3450 Approved
0.7277 Intermediate Similarity NPD2493 Approved
0.7273 Intermediate Similarity NPD4162 Approved
0.7263 Intermediate Similarity NPD8095 Phase 1
0.7262 Intermediate Similarity NPD1424 Approved
0.7229 Intermediate Similarity NPD6748 Discontinued
0.7226 Intermediate Similarity NPD2233 Approved
0.7226 Intermediate Similarity NPD2230 Approved
0.7226 Intermediate Similarity NPD2232 Approved
0.7225 Intermediate Similarity NPD5773 Approved
0.7225 Intermediate Similarity NPD5772 Approved
0.7222 Intermediate Similarity NPD4873 Discontinued
0.7219 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3109 Approved
0.7205 Intermediate Similarity NPD3110 Approved
0.7197 Intermediate Similarity NPD3055 Approved
0.7197 Intermediate Similarity NPD3053 Approved
0.7193 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD3692 Discontinued
0.7176 Intermediate Similarity NPD4727 Phase 1
0.7173 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD4582 Approved
0.7165 Intermediate Similarity NPD4583 Approved
0.7152 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2668 Approved
0.7143 Intermediate Similarity NPD2667 Approved
0.7134 Intermediate Similarity NPD4108 Discontinued
0.7126 Intermediate Similarity NPD5754 Discontinued
0.7126 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD2971 Approved
0.712 Intermediate Similarity NPD2968 Approved
0.7113 Intermediate Similarity NPD4002 Approved
0.7113 Intermediate Similarity NPD4004 Approved
0.7112 Intermediate Similarity NPD3408 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7110 Phase 1
0.7108 Intermediate Similarity NPD7037 Approved
0.7099 Intermediate Similarity NPD2238 Phase 2
0.7093 Intermediate Similarity NPD824 Approved
0.7093 Intermediate Similarity NPD4005 Discontinued
0.7088 Intermediate Similarity NPD3885 Approved
0.7085 Intermediate Similarity NPD7827 Phase 1
0.7083 Intermediate Similarity NPD5160 Discontinued
0.7081 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6618 Phase 2
0.7077 Intermediate Similarity NPD4040 Phase 1
0.7076 Intermediate Similarity NPD2122 Discontinued
0.7074 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD2973 Approved
0.7068 Intermediate Similarity NPD2974 Approved
0.7068 Intermediate Similarity NPD2975 Approved
0.7065 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3349 Phase 2
0.7059 Intermediate Similarity NPD4123 Phase 3
0.7048 Intermediate Similarity NPD3656 Approved
0.7047 Intermediate Similarity NPD5457 Discontinued
0.7044 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7124 Phase 2
0.7041 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7296 Approved
0.7024 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6331 Phase 2
0.7022 Intermediate Similarity NPD4666 Phase 3
0.7019 Intermediate Similarity NPD5155 Approved
0.7019 Intermediate Similarity NPD5156 Approved
0.7013 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3635 Approved
0.7 Intermediate Similarity NPD3637 Approved
0.7 Intermediate Similarity NPD6688 Approved
0.7 Intermediate Similarity NPD3636 Approved
0.7 Intermediate Similarity NPD6687 Approved
0.6995 Remote Similarity NPD7479 Phase 2
0.698 Remote Similarity NPD7047 Phase 3
0.6977 Remote Similarity NPD1914 Approved
0.6977 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6977 Remote Similarity NPD5976 Discontinued
0.6973 Remote Similarity NPD7549 Discontinued
0.697 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4093 Discontinued
0.6968 Remote Similarity NPD7291 Discontinued
0.6966 Remote Similarity NPD5709 Phase 3
0.6966 Remote Similarity NPD7400 Phase 3
0.6959 Remote Similarity NPD4580 Approved
0.6957 Remote Similarity NPD3594 Approved
0.6957 Remote Similarity NPD2605 Approved
0.6957 Remote Similarity NPD3595 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data