Structure

Physi-Chem Properties

Molecular Weight:  313.17
Volume:  333.059
LogP:  2.483
LogD:  2.942
LogS:  -1.964
# Rotatable Bonds:  4
TPSA:  41.93
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.941
Synthetic Accessibility Score:  2.581
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.559
MDCK Permeability:  1.7639922589296475e-05
Pgp-inhibitor:  0.051
Pgp-substrate:  0.481
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.1
30% Bioavailability (F30%):  0.467

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.991
Plasma Protein Binding (PPB):  67.57552337646484%
Volume Distribution (VD):  2.296
Pgp-substrate:  18.003358840942383%

ADMET: Metabolism

CYP1A2-inhibitor:  0.194
CYP1A2-substrate:  0.959
CYP2C19-inhibitor:  0.22
CYP2C19-substrate:  0.948
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.73
CYP2D6-inhibitor:  0.758
CYP2D6-substrate:  0.938
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.92

ADMET: Excretion

Clearance (CL):  13.196
Half-life (T1/2):  0.863

ADMET: Toxicity

hERG Blockers:  0.648
Human Hepatotoxicity (H-HT):  0.223
Drug-inuced Liver Injury (DILI):  0.117
AMES Toxicity:  0.13
Rat Oral Acute Toxicity:  0.644
Maximum Recommended Daily Dose:  0.903
Skin Sensitization:  0.617
Carcinogencity:  0.079
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.89

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

  Natural Product: NPC185838

Natural Product ID:  NPC185838
Common Name*:   4-[(6,7-Dimethoxy-2-Methyl-3,4-Dihydro-1H-Isoquinolin-1-Yl)Methyl]Phenol
IUPAC Name:   4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]phenol
Synonyms:   D,L-Armepavine
Standard InCHIKey:  ZBKFZIUKXTWQTP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3
SMILES:  COc1cc2c(cc1OC)CCN(C2Cc1ccc(cc1)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451722
PubChem CID:   98348
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota flower buds and leaves Khon Kaen province, Thailand 2010 PMID[23270663]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Leaves n.a. n.a. PMID[23642481]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO30631 Rhamnus frangula Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2957 Papaver caucasicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2957 Papaver caucasicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30631 Rhamnus frangula Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30157 Euonymus europaeua Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2957 Papaver caucasicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5536 Papaver persicum 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PMID[470646]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[470646]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 50118.7 nM PMID[470646]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 5623.4 nM PMID[470646]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 19952.6 nM PMID[470646]
NPT968 Protein Family Adrenergic receptor alpha-1 Rattus norvegicus Ki = 7244.36 nM PMID[470645]
NPT2685 Protein Family Voltage-gated L-type calcium channel Rattus norvegicus Ki = 9549.93 nM PMID[470645]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 208929.61 nM PMID[470645]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 114815.36 nM PMID[470645]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 44668.4 nM PMID[470646]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 25118.9 nM PMID[470646]
NPT2 Others Unspecified Potency n.a. 2909.3 nM PMID[470646]
NPT2 Others Unspecified Inhibition = 18.2 % PMID[470647]
NPT2 Others Unspecified Inhibition = 7.5 % PMID[470647]
NPT27 Others Unspecified Inhibition = 82.0 % PMID[470647]
NPT27 Others Unspecified Inhibition = 86.0 % PMID[470647]
NPT2 Others Unspecified IC50 = 25600.0 nM PMID[470647]
NPT2 Others Unspecified Inhibition = 80.3 % PMID[470647]
NPT2 Others Unspecified Inhibition = 50.4 % PMID[470647]
NPT2 Others Unspecified Inhibition = 34.0 % PMID[470647]

☑ 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 NPC185838 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
0.9855 High Similarity NPC191376
0.9855 High Similarity NPC321505
0.9855 High Similarity NPC179825
0.9784 High Similarity NPC476571
0.9784 High Similarity NPC428
0.9784 High Similarity NPC24233
0.9784 High Similarity NPC135538
0.9784 High Similarity NPC147390
0.9784 High Similarity NPC246587
0.9712 High Similarity NPC476151
0.9632 High Similarity NPC314682
0.9574 High Similarity NPC103379
0.9574 High Similarity NPC477565
0.9574 High Similarity NPC60538
0.9574 High Similarity NPC207824
0.9562 High Similarity NPC188163
0.9562 High Similarity NPC474915
0.9562 High Similarity NPC213206
0.9562 High Similarity NPC328750
0.9507 High Similarity NPC151895
0.9507 High Similarity NPC192768
0.9507 High Similarity NPC97221
0.9507 High Similarity NPC88249
0.9507 High Similarity NPC220858
0.9441 High Similarity NPC277669
0.9441 High Similarity NPC76213
0.9379 High Similarity NPC2413
0.9379 High Similarity NPC204828
0.9379 High Similarity NPC110416
0.9379 High Similarity NPC39701
0.9379 High Similarity NPC276588
0.9379 High Similarity NPC207757
0.9379 High Similarity NPC189266
0.9379 High Similarity NPC193949
0.9379 High Similarity NPC127674
0.9379 High Similarity NPC249797
0.9379 High Similarity NPC172765
0.9379 High Similarity NPC184026
0.9379 High Similarity NPC278799
0.9379 High Similarity NPC5238
0.9379 High Similarity NPC54379
0.9379 High Similarity NPC295691
0.9379 High Similarity NPC469817
0.9286 High Similarity NPC476567
0.9286 High Similarity NPC136860
0.9286 High Similarity NPC128019
0.9178 High Similarity NPC477564
0.9178 High Similarity NPC2295
0.9161 High Similarity NPC476144
0.9161 High Similarity NPC210437
0.9161 High Similarity NPC51957
0.9161 High Similarity NPC106295
0.9161 High Similarity NPC16107
0.913 High Similarity NPC301050
0.913 High Similarity NPC131204
0.9128 High Similarity NPC166014
0.9128 High Similarity NPC27410
0.911 High Similarity NPC82285
0.911 High Similarity NPC133011
0.9103 High Similarity NPC274026
0.9097 High Similarity NPC475959
0.9097 High Similarity NPC7467
0.906 High Similarity NPC111485
0.9054 High Similarity NPC147091
0.898 High Similarity NPC26601
0.8971 High Similarity NPC160193
0.8951 High Similarity NPC294249
0.8947 High Similarity NPC238530
0.8947 High Similarity NPC276944
0.8947 High Similarity NPC232514
0.8912 High Similarity NPC326316
0.8912 High Similarity NPC81733
0.8889 High Similarity NPC317272
0.8889 High Similarity NPC13916
0.8889 High Similarity NPC268503
0.8889 High Similarity NPC130926
0.8889 High Similarity NPC42549
0.8889 High Similarity NPC250846
0.8889 High Similarity NPC240841
0.8889 High Similarity NPC256012
0.8889 High Similarity NPC264850
0.8882 High Similarity NPC324144
0.8851 High Similarity NPC37272
0.8831 High Similarity NPC117188
0.8831 High Similarity NPC205421
0.8831 High Similarity NPC12053
0.8831 High Similarity NPC474931
0.8831 High Similarity NPC306555
0.8831 High Similarity NPC298979
0.8831 High Similarity NPC145832
0.8831 High Similarity NPC81218
0.8831 High Similarity NPC158376
0.8824 High Similarity NPC136508
0.8824 High Similarity NPC134858
0.8824 High Similarity NPC253043
0.8824 High Similarity NPC196447
0.8824 High Similarity NPC121275
0.8824 High Similarity NPC78222
0.8824 High Similarity NPC24465
0.8824 High Similarity NPC4138
0.8824 High Similarity NPC477563
0.8824 High Similarity NPC306843
0.8824 High Similarity NPC212794
0.8824 High Similarity NPC96603
0.8824 High Similarity NPC13504
0.8824 High Similarity NPC172403
0.8824 High Similarity NPC284183
0.88 High Similarity NPC186063
0.8794 High Similarity NPC253429
0.8794 High Similarity NPC193528
0.8784 High Similarity NPC476568
0.8776 High Similarity NPC92541
0.8776 High Similarity NPC219162
0.8774 High Similarity NPC204908
0.8774 High Similarity NPC83198
0.8766 High Similarity NPC35627
0.8766 High Similarity NPC476573
0.8766 High Similarity NPC81247
0.8758 High Similarity NPC233650
0.8758 High Similarity NPC1229
0.875 High Similarity NPC205167
0.875 High Similarity NPC249274
0.8733 High Similarity NPC41178
0.8733 High Similarity NPC216459
0.8733 High Similarity NPC138487
0.8725 High Similarity NPC233029
0.8725 High Similarity NPC210148
0.871 High Similarity NPC210140
0.8693 High Similarity NPC60186
0.8684 High Similarity NPC92191
0.8684 High Similarity NPC59028
0.8675 High Similarity NPC146288
0.8675 High Similarity NPC247639
0.8675 High Similarity NPC25084
0.8654 High Similarity NPC66573
0.8639 High Similarity NPC144863
0.8639 High Similarity NPC90844
0.8639 High Similarity NPC95075
0.8639 High Similarity NPC253883
0.8627 High Similarity NPC97072
0.8627 High Similarity NPC215829
0.8618 High Similarity NPC476572
0.8618 High Similarity NPC475326
0.8609 High Similarity NPC325871
0.8609 High Similarity NPC99659
0.8609 High Similarity NPC80129
0.8609 High Similarity NPC187022
0.8608 High Similarity NPC152680
0.8608 High Similarity NPC190783
0.8608 High Similarity NPC232386
0.8601 High Similarity NPC170170
0.8601 High Similarity NPC219233
0.8601 High Similarity NPC211468
0.8599 High Similarity NPC168753
0.8599 High Similarity NPC118274
0.8599 High Similarity NPC109925
0.859 High Similarity NPC150879
0.8581 High Similarity NPC130941
0.8553 High Similarity NPC126519
0.8553 High Similarity NPC31311
0.8553 High Similarity NPC234392
0.8553 High Similarity NPC170503
0.8553 High Similarity NPC203784
0.8544 High Similarity NPC239775
0.8544 High Similarity NPC108434
0.8544 High Similarity NPC475215
0.8542 High Similarity NPC323123
0.8535 High Similarity NPC470324
0.8533 High Similarity NPC476579
0.8521 High Similarity NPC11147
0.8511 High Similarity NPC160692
0.8506 High Similarity NPC477559
0.8506 High Similarity NPC160298
0.8506 High Similarity NPC306902
0.8506 High Similarity NPC266753
0.8506 High Similarity NPC232924
0.85 High Similarity NPC241704
0.8491 Intermediate Similarity NPC477020
0.8491 Intermediate Similarity NPC66341
0.8491 Intermediate Similarity NPC192135
0.8491 Intermediate Similarity NPC2314
0.8487 Intermediate Similarity NPC78733
0.8483 Intermediate Similarity NPC470925
0.8481 Intermediate Similarity NPC26240
0.8481 Intermediate Similarity NPC69712
0.8481 Intermediate Similarity NPC477562
0.8477 Intermediate Similarity NPC148898
0.8462 Intermediate Similarity NPC169743
0.8462 Intermediate Similarity NPC7018
0.8447 Intermediate Similarity NPC320223
0.8447 Intermediate Similarity NPC114364
0.8442 Intermediate Similarity NPC216816
0.8442 Intermediate Similarity NPC477080
0.844 Intermediate Similarity NPC118419
0.8438 Intermediate Similarity NPC229166
0.8438 Intermediate Similarity NPC128560
0.8438 Intermediate Similarity NPC199465
0.8408 Intermediate Similarity NPC124657
0.8397 Intermediate Similarity NPC475393
0.8395 Intermediate Similarity NPC32154

  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 NPC185838 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
0.9562 High Similarity NPD4664 Clinical (unspecified phase)
0.9161 High Similarity NPD4584 Approved
0.8912 High Similarity NPD4017 Approved
0.8819 High Similarity NPD5241 Discontinued
0.8792 High Similarity NPD4772 Phase 2
0.8792 High Similarity NPD4773 Phase 2
0.8766 High Similarity NPD4010 Discontinued
0.8758 High Similarity NPD7201 Clinical (unspecified phase)
0.8649 High Similarity NPD3640 Phase 3
0.8649 High Similarity NPD3641 Approved
0.8649 High Similarity NPD3639 Approved
0.8609 High Similarity NPD7298 Approved
0.8553 High Similarity NPD6818 Clinical (unspecified phase)
0.8535 High Similarity NPD2898 Approved
0.8523 High Similarity NPD6030 Approved
0.8523 High Similarity NPD6031 Approved
0.8506 High Similarity NPD7832 Clinical (unspecified phase)
0.8506 High Similarity NPD7833 Phase 2
0.8506 High Similarity NPD7831 Phase 2
0.85 High Similarity NPD5718 Phase 2
0.8429 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD2421 Approved
0.8322 Intermediate Similarity NPD2420 Approved
0.8293 Intermediate Similarity NPD8053 Approved
0.8293 Intermediate Similarity NPD8054 Approved
0.8276 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD3845 Phase 1
0.8227 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD27 Approved
0.8187 Intermediate Similarity NPD2489 Approved
0.8182 Intermediate Similarity NPD2674 Phase 3
0.8176 Intermediate Similarity NPD6071 Discontinued
0.8176 Intermediate Similarity NPD5177 Phase 3
0.816 Intermediate Similarity NPD6297 Approved
0.8141 Intermediate Similarity NPD2563 Approved
0.8141 Intermediate Similarity NPD2560 Approved
0.8137 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD2969 Approved
0.8125 Intermediate Similarity NPD2970 Approved
0.8089 Intermediate Similarity NPD6788 Approved
0.8086 Intermediate Similarity NPD8099 Discontinued
0.8086 Intermediate Similarity NPD8252 Approved
0.8086 Intermediate Similarity NPD8251 Approved
0.8082 Intermediate Similarity NPD6895 Approved
0.8082 Intermediate Similarity NPD6896 Approved
0.8079 Intermediate Similarity NPD3124 Discontinued
0.8063 Intermediate Similarity NPD3051 Approved
0.8054 Intermediate Similarity NPD3060 Approved
0.8037 Intermediate Similarity NPD8156 Discontinued
0.8027 Intermediate Similarity NPD1753 Discontinued
0.8 Intermediate Similarity NPD7802 Discontinued
0.8 Intermediate Similarity NPD6107 Approved
0.7986 Intermediate Similarity NPD3145 Approved
0.7986 Intermediate Similarity NPD3144 Approved
0.7973 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD6851 Approved
0.7964 Intermediate Similarity NPD6853 Approved
0.795 Intermediate Similarity NPD4166 Phase 2
0.7947 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD5978 Approved
0.7911 Intermediate Similarity NPD5977 Approved
0.7895 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD3109 Approved
0.7877 Intermediate Similarity NPD3110 Approved
0.7842 Intermediate Similarity NPD2667 Approved
0.7842 Intermediate Similarity NPD2668 Approved
0.7829 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD4475 Approved
0.7808 Intermediate Similarity NPD4474 Approved
0.7801 Intermediate Similarity NPD2232 Approved
0.7801 Intermediate Similarity NPD2230 Approved
0.7801 Intermediate Similarity NPD2233 Approved
0.7778 Intermediate Similarity NPD3635 Approved
0.7778 Intermediate Similarity NPD3636 Approved
0.7778 Intermediate Similarity NPD3637 Approved
0.777 Intermediate Similarity NPD4093 Discontinued
0.7762 Intermediate Similarity NPD3055 Approved
0.7762 Intermediate Similarity NPD3053 Approved
0.7736 Intermediate Similarity NPD2978 Approved
0.7736 Intermediate Similarity NPD2977 Approved
0.7722 Intermediate Similarity NPD7110 Phase 1
0.7722 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7906 Approved
0.7712 Intermediate Similarity NPD3692 Discontinued
0.7711 Intermediate Similarity NPD5313 Approved
0.7711 Intermediate Similarity NPD5312 Approved
0.7707 Intermediate Similarity NPD4005 Discontinued
0.7702 Intermediate Similarity NPD4055 Discovery
0.7697 Intermediate Similarity NPD4236 Phase 3
0.7697 Intermediate Similarity NPD4237 Approved
0.7697 Intermediate Similarity NPD4162 Approved
0.7692 Intermediate Similarity NPD7310 Approved
0.7692 Intermediate Similarity NPD4577 Approved
0.7692 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7312 Approved
0.7692 Intermediate Similarity NPD4578 Approved
0.7692 Intermediate Similarity NPD7311 Approved
0.7692 Intermediate Similarity NPD7313 Approved
0.7677 Intermediate Similarity NPD1424 Approved
0.7677 Intermediate Similarity NPD4123 Phase 3
0.7671 Intermediate Similarity NPD5155 Approved
0.7671 Intermediate Similarity NPD5156 Approved
0.7662 Intermediate Similarity NPD7124 Phase 2
0.7657 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6331 Phase 2
0.7647 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD7309 Approved
0.764 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD4481 Phase 3
0.7635 Intermediate Similarity NPD2238 Phase 2
0.7628 Intermediate Similarity NPD6090 Discontinued
0.7622 Intermediate Similarity NPD1669 Approved
0.7619 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD3595 Approved
0.7603 Intermediate Similarity NPD3594 Approved
0.7603 Intermediate Similarity NPD2606 Approved
0.7603 Intermediate Similarity NPD2605 Approved
0.7595 Intermediate Similarity NPD824 Approved
0.7593 Intermediate Similarity NPD5604 Discontinued
0.7588 Intermediate Similarity NPD7280 Phase 3
0.7588 Intermediate Similarity NPD7281 Phase 3
0.7586 Intermediate Similarity NPD6584 Phase 3
0.7586 Intermediate Similarity NPD7905 Discontinued
0.758 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD6687 Approved
0.7576 Intermediate Similarity NPD6688 Approved
0.7571 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD4663 Approved
0.7532 Intermediate Similarity NPD6748 Discontinued
0.7532 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2488 Approved
0.7529 Intermediate Similarity NPD2490 Approved
0.7517 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD4103 Phase 2
0.7517 Intermediate Similarity NPD4098 Discontinued
0.7516 Intermediate Similarity NPD5773 Approved
0.7516 Intermediate Similarity NPD7153 Discontinued
0.7516 Intermediate Similarity NPD7037 Approved
0.7516 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD5772 Approved
0.7514 Intermediate Similarity NPD7291 Discontinued
0.75 Intermediate Similarity NPD2161 Phase 2
0.75 Intermediate Similarity NPD4659 Approved
0.7485 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD4083 Discontinued
0.7468 Intermediate Similarity NPD44 Approved
0.7468 Intermediate Similarity NPD6364 Approved
0.7468 Intermediate Similarity NPD2122 Discontinued
0.7464 Intermediate Similarity NPD5283 Phase 1
0.7456 Intermediate Similarity NPD3920 Phase 2
0.7456 Intermediate Similarity NPD7479 Phase 2
0.7453 Intermediate Similarity NPD5720 Discontinued
0.7453 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD5311 Approved
0.7448 Intermediate Similarity NPD5310 Approved
0.7447 Intermediate Similarity NPD5304 Approved
0.7447 Intermediate Similarity NPD5303 Approved
0.7438 Intermediate Similarity NPD6875 Approved
0.7438 Intermediate Similarity NPD4678 Approved
0.7438 Intermediate Similarity NPD4675 Approved
0.7438 Intermediate Similarity NPD6876 Approved
0.7429 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD823 Approved
0.7417 Intermediate Similarity NPD817 Approved
0.7394 Intermediate Similarity NPD5677 Discontinued
0.7389 Intermediate Similarity NPD7598 Phase 2
0.7383 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD6582 Phase 2
0.7379 Intermediate Similarity NPD6583 Phase 3
0.7379 Intermediate Similarity NPD1420 Approved
0.7379 Intermediate Similarity NPD1421 Approved
0.7375 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD5160 Discontinued
0.7361 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD1914 Approved
0.7355 Intermediate Similarity NPD2460 Phase 3
0.7355 Intermediate Similarity NPD2458 Approved
0.7355 Intermediate Similarity NPD2459 Approved
0.7343 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD2874 Phase 2
0.7341 Intermediate Similarity NPD6618 Phase 2
0.7338 Intermediate Similarity NPD2228 Approved
0.7338 Intermediate Similarity NPD3656 Approved
0.7338 Intermediate Similarity NPD2229 Approved
0.7338 Intermediate Similarity NPD2234 Approved
0.7337 Intermediate Similarity NPD5708 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3531 Approved
0.7333 Intermediate Similarity NPD3532 Approved
0.7333 Intermediate Similarity NPD3530 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