Structure

Physi-Chem Properties

Molecular Weight:  327.15
Volume:  333.293
LogP:  2.156
LogD:  2.826
LogS:  -1.724
# 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:  0.888
Synthetic Accessibility Score:  3.053
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:  -5.062
MDCK Permeability:  1.978200816665776e-05
Pgp-inhibitor:  0.075
Pgp-substrate:  0.146
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.034
30% Bioavailability (F30%):  0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.972
Plasma Protein Binding (PPB):  92.62212371826172%
Volume Distribution (VD):  1.03
Pgp-substrate:  8.635332107543945%

ADMET: Metabolism

CYP1A2-inhibitor:  0.763
CYP1A2-substrate:  0.957
CYP2C19-inhibitor:  0.182
CYP2C19-substrate:  0.726
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.601
CYP2D6-inhibitor:  0.785
CYP2D6-substrate:  0.911
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.878

ADMET: Excretion

Clearance (CL):  17.463
Half-life (T1/2):  0.845

ADMET: Toxicity

hERG Blockers:  0.296
Human Hepatotoxicity (H-HT):  0.108
Drug-inuced Liver Injury (DILI):  0.168
AMES Toxicity:  0.348
Rat Oral Acute Toxicity:  0.445
Maximum Recommended Daily Dose:  0.925
Skin Sensitization:  0.803
Carcinogencity:  0.156
Eye Corrosion:  0.003
Eye Irritation:  0.051
Respiratory Toxicity:  0.87

Download Data

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

  Natural Product: NPC110416

Natural Product ID:  NPC110416
Common Name*:   3,9-Dimethoxy-5,8,13,13A-Tetrahydro-6H-Isoquino[3,2-A]Isoquinoline-2,10-Diol
IUPAC Name:   3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
Synonyms:  
Standard InCHIKey:  JKPISQIIWUONPB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3
SMILES:  COc1cc2CCN3C(c2cc1O)Cc1c(C3)c(OC)c(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL595489
PubChem CID:   5290
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
NPO2341 Fibraurea recisa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2341 Fibraurea recisa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2341 Fibraurea recisa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]

☑ 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
NPT296 Individual Protein Sigma opioid receptor Homo sapiens Ki = 269.0 nM PMID[479866]
NPT244 Individual Protein Dopamine D3 receptor Homo sapiens Ki = 101.0 nM PMID[479866]
NPT243 Individual Protein Dopamine D2 receptor Homo sapiens Ki = 115.5 nM PMID[479866]
NPT242 Individual Protein Dopamine D1 receptor Homo sapiens Ki = 5.6 nM PMID[479866]
NPT2 Others Unspecified Ki = 9.0 nM PMID[479866]
NPT2 Others Unspecified Ratio Ki = 20.6 n.a. PMID[479866]
NPT2 Others Unspecified Ratio Ki = 18.0 n.a. PMID[479866]
NPT2 Others Unspecified Ratio Ki = 1.1 n.a. PMID[479866]
NPT2 Others Unspecified Ratio Ki = 30.0 n.a. PMID[479866]

☑ 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 NPC110416 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 NPC189266
1.0 High Similarity NPC184026
1.0 High Similarity NPC204828
1.0 High Similarity NPC295691
1.0 High Similarity NPC54379
1.0 High Similarity NPC207757
1.0 High Similarity NPC276588
1.0 High Similarity NPC39701
1.0 High Similarity NPC5238
1.0 High Similarity NPC172765
1.0 High Similarity NPC127674
1.0 High Similarity NPC249797
1.0 High Similarity NPC2413
1.0 High Similarity NPC469817
1.0 High Similarity NPC278799
1.0 High Similarity NPC193949
0.9724 High Similarity NPC220858
0.9724 High Similarity NPC192768
0.9724 High Similarity NPC151895
0.9724 High Similarity NPC97221
0.9724 High Similarity NPC88249
0.9655 High Similarity NPC477565
0.9655 High Similarity NPC103379
0.9586 High Similarity NPC135538
0.9586 High Similarity NPC476571
0.9586 High Similarity NPC24233
0.9586 High Similarity NPC147390
0.9586 High Similarity NPC246587
0.9586 High Similarity NPC428
0.9539 High Similarity NPC238530
0.9539 High Similarity NPC276944
0.9539 High Similarity NPC232514
0.9517 High Similarity NPC179825
0.9517 High Similarity NPC476144
0.9517 High Similarity NPC476151
0.9517 High Similarity NPC106295
0.9517 High Similarity NPC191376
0.9517 High Similarity NPC210437
0.9517 High Similarity NPC16107
0.9517 High Similarity NPC51957
0.9517 High Similarity NPC321505
0.9477 High Similarity NPC264850
0.9477 High Similarity NPC13916
0.9452 High Similarity NPC7467
0.9412 High Similarity NPC24465
0.9379 High Similarity NPC185838
0.9276 High Similarity NPC111485
0.9267 High Similarity NPC2295
0.9267 High Similarity NPC477564
0.9241 High Similarity NPC136860
0.9241 High Similarity NPC128019
0.9241 High Similarity NPC476567
0.9216 High Similarity NPC166014
0.9216 High Similarity NPC27410
0.9133 High Similarity NPC76213
0.9133 High Similarity NPC277669
0.9103 High Similarity NPC317272
0.9103 High Similarity NPC42549
0.9103 High Similarity NPC240841
0.9103 High Similarity NPC256012
0.9103 High Similarity NPC474915
0.9103 High Similarity NPC250846
0.9103 High Similarity NPC328750
0.9103 High Similarity NPC268503
0.9103 High Similarity NPC188163
0.9103 High Similarity NPC213206
0.9097 High Similarity NPC324144
0.9079 High Similarity NPC216459
0.9079 High Similarity NPC41178
0.9079 High Similarity NPC138487
0.9073 High Similarity NPC37272
0.9045 High Similarity NPC145832
0.9045 High Similarity NPC205421
0.9045 High Similarity NPC474931
0.9045 High Similarity NPC12053
0.9045 High Similarity NPC81218
0.9045 High Similarity NPC158376
0.9045 High Similarity NPC306555
0.9045 High Similarity NPC117188
0.9038 High Similarity NPC96603
0.9038 High Similarity NPC13504
0.9038 High Similarity NPC284183
0.9038 High Similarity NPC136508
0.9038 High Similarity NPC477563
0.9038 High Similarity NPC253043
0.9038 High Similarity NPC306843
0.9038 High Similarity NPC78222
0.9038 High Similarity NPC121275
0.9038 High Similarity NPC196447
0.9038 High Similarity NPC4138
0.9038 High Similarity NPC212794
0.9034 High Similarity NPC314682
0.9032 High Similarity NPC60186
0.902 High Similarity NPC146288
0.9 High Similarity NPC207824
0.9 High Similarity NPC60538
0.8987 High Similarity NPC204908
0.8987 High Similarity NPC83198
0.8951 High Similarity NPC32154
0.8947 High Similarity NPC82285
0.8947 High Similarity NPC133011
0.8896 High Similarity NPC147091
0.8896 High Similarity NPC31311
0.8896 High Similarity NPC234392
0.8868 High Similarity NPC66573
0.8861 High Similarity NPC476573
0.8861 High Similarity NPC35627
0.8861 High Similarity NPC81247
0.8854 High Similarity NPC1229
0.8841 High Similarity NPC290005
0.8841 High Similarity NPC8836
0.8841 High Similarity NPC239824
0.8841 High Similarity NPC217748
0.8841 High Similarity NPC328155
0.8841 High Similarity NPC42663
0.8841 High Similarity NPC182052
0.8841 High Similarity NPC104196
0.8841 High Similarity NPC54654
0.8841 High Similarity NPC222661
0.8841 High Similarity NPC90998
0.8841 High Similarity NPC290582
0.8841 High Similarity NPC285931
0.8841 High Similarity NPC271013
0.8841 High Similarity NPC223690
0.8841 High Similarity NPC251735
0.8841 High Similarity NPC49075
0.8841 High Similarity NPC15414
0.8841 High Similarity NPC279228
0.8841 High Similarity NPC258657
0.8841 High Similarity NPC181796
0.8841 High Similarity NPC311973
0.8841 High Similarity NPC185639
0.8841 High Similarity NPC229373
0.8841 High Similarity NPC7715
0.8828 High Similarity NPC301050
0.8828 High Similarity NPC131204
0.8827 High Similarity NPC241704
0.882 High Similarity NPC190783
0.882 High Similarity NPC232386
0.882 High Similarity NPC2314
0.882 High Similarity NPC152680
0.8812 High Similarity NPC109925
0.8788 High Similarity NPC274716
0.8788 High Similarity NPC254441
0.8788 High Similarity NPC167116
0.878 High Similarity NPC286119
0.8774 High Similarity NPC186063
0.8758 High Similarity NPC81733
0.8758 High Similarity NPC239775
0.8758 High Similarity NPC326316
0.8758 High Similarity NPC108434
0.8758 High Similarity NPC475215
0.8727 High Similarity NPC30779
0.8726 High Similarity NPC205167
0.8704 High Similarity NPC192135
0.8704 High Similarity NPC66341
0.8704 High Similarity NPC477020
0.8701 High Similarity NPC233029
0.8701 High Similarity NPC210148
0.8696 High Similarity NPC69712
0.8696 High Similarity NPC477562
0.8696 High Similarity NPC26240
0.8696 High Similarity NPC118274
0.8696 High Similarity NPC168753
0.8693 High Similarity NPC274026
0.8688 High Similarity NPC210140
0.8688 High Similarity NPC298979
0.8684 High Similarity NPC475959
0.8683 High Similarity NPC212237
0.8683 High Similarity NPC116465
0.8667 High Similarity NPC294249
0.8659 High Similarity NPC320223
0.8659 High Similarity NPC114364
0.8654 High Similarity NPC247639
0.8654 High Similarity NPC25084
0.865 High Similarity NPC128560
0.865 High Similarity NPC199465
0.865 High Similarity NPC229166
0.8631 High Similarity NPC22115
0.8631 High Similarity NPC275680
0.8627 High Similarity NPC92541
0.8608 High Similarity NPC249274
0.8599 High Similarity NPC475326
0.8599 High Similarity NPC476572
0.859 High Similarity NPC187022
0.859 High Similarity NPC99659
0.859 High Similarity NPC80129
0.859 High Similarity NPC325871
0.8581 High Similarity NPC26601
0.858 High Similarity NPC274661
0.858 High Similarity NPC48490
0.858 High Similarity NPC175890
0.858 High Similarity NPC206900
0.858 High Similarity NPC11296
0.858 High Similarity NPC82457
0.8562 High Similarity NPC3375
0.8562 High Similarity NPC255607
0.8562 High Similarity NPC134858
0.8529 High Similarity NPC191132
0.8529 High Similarity NPC60295

  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 NPC110416 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
0.9517 High Similarity NPD4584 Approved
0.9103 High Similarity NPD4664 Clinical (unspecified phase)
0.8841 High Similarity NPD8054 Approved
0.8841 High Similarity NPD8053 Approved
0.8645 High Similarity NPD4773 Phase 2
0.8645 High Similarity NPD4772 Phase 2
0.8625 High Similarity NPD4010 Discontinued
0.859 High Similarity NPD7298 Approved
0.8519 High Similarity NPD2898 Approved
0.8497 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD2420 Approved
0.8431 Intermediate Similarity NPD2421 Approved
0.8415 Intermediate Similarity NPD8252 Approved
0.8415 Intermediate Similarity NPD8251 Approved
0.8415 Intermediate Similarity NPD8099 Discontinued
0.8397 Intermediate Similarity NPD4017 Approved
0.8387 Intermediate Similarity NPD3641 Approved
0.8387 Intermediate Similarity NPD3639 Approved
0.8387 Intermediate Similarity NPD3640 Phase 3
0.8385 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD8156 Discontinued
0.8301 Intermediate Similarity NPD5241 Discontinued
0.8293 Intermediate Similarity NPD27 Approved
0.8293 Intermediate Similarity NPD2489 Approved
0.8267 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8267 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD6031 Approved
0.8153 Intermediate Similarity NPD6030 Approved
0.8148 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD7833 Phase 2
0.8148 Intermediate Similarity NPD7831 Phase 2
0.8129 Intermediate Similarity NPD3845 Phase 1
0.8121 Intermediate Similarity NPD2969 Approved
0.8121 Intermediate Similarity NPD2970 Approved
0.8086 Intermediate Similarity NPD6788 Approved
0.8061 Intermediate Similarity NPD3051 Approved
0.8013 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6107 Approved
0.7987 Intermediate Similarity NPD5718 Phase 2
0.7962 Intermediate Similarity NPD3124 Discontinued
0.7952 Intermediate Similarity NPD6071 Discontinued
0.7935 Intermediate Similarity NPD5177 Phase 3
0.7933 Intermediate Similarity NPD2674 Phase 3
0.7931 Intermediate Similarity NPD7906 Approved
0.7919 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD2563 Approved
0.7914 Intermediate Similarity NPD2560 Approved
0.7907 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD7313 Approved
0.7907 Intermediate Similarity NPD7312 Approved
0.7907 Intermediate Similarity NPD7310 Approved
0.7907 Intermediate Similarity NPD7311 Approved
0.7861 Intermediate Similarity NPD7309 Approved
0.7836 Intermediate Similarity NPD6297 Approved
0.7811 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD4577 Approved
0.7803 Intermediate Similarity NPD4578 Approved
0.7784 Intermediate Similarity NPD7802 Discontinued
0.7771 Intermediate Similarity NPD4663 Approved
0.7748 Intermediate Similarity NPD3145 Approved
0.7748 Intermediate Similarity NPD3144 Approved
0.7746 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD4166 Phase 2
0.7733 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6896 Approved
0.7727 Intermediate Similarity NPD6895 Approved
0.7722 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD5313 Approved
0.7719 Intermediate Similarity NPD5312 Approved
0.7707 Intermediate Similarity NPD3060 Approved
0.7697 Intermediate Similarity NPD4474 Approved
0.7697 Intermediate Similarity NPD4475 Approved
0.7677 Intermediate Similarity NPD1753 Discontinued
0.7667 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD6853 Approved
0.7657 Intermediate Similarity NPD6851 Approved
0.7651 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD4481 Phase 3
0.764 Intermediate Similarity NPD6090 Discontinued
0.764 Intermediate Similarity NPD2488 Approved
0.764 Intermediate Similarity NPD2490 Approved
0.7636 Intermediate Similarity NPD2978 Approved
0.7636 Intermediate Similarity NPD2977 Approved
0.7625 Intermediate Similarity NPD7598 Phase 2
0.7605 Intermediate Similarity NPD4055 Discovery
0.7595 Intermediate Similarity NPD4162 Approved
0.7578 Intermediate Similarity NPD1424 Approved
0.7568 Intermediate Similarity NPD2232 Approved
0.7568 Intermediate Similarity NPD2230 Approved
0.7568 Intermediate Similarity NPD2233 Approved
0.7562 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD6748 Discontinued
0.7541 Intermediate Similarity NPD8095 Phase 1
0.7533 Intermediate Similarity NPD3055 Approved
0.7533 Intermediate Similarity NPD3053 Approved
0.7532 Intermediate Similarity NPD3110 Approved
0.7532 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD3109 Approved
0.75 Intermediate Similarity NPD3692 Discontinued
0.75 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD5978 Approved
0.7485 Intermediate Similarity NPD5977 Approved
0.7484 Intermediate Similarity NPD4237 Approved
0.7484 Intermediate Similarity NPD4236 Phase 3
0.7483 Intermediate Similarity NPD2668 Approved
0.7483 Intermediate Similarity NPD2667 Approved
0.7468 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2238 Phase 2
0.741 Intermediate Similarity NPD7110 Phase 1
0.741 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD7280 Phase 3
0.7401 Intermediate Similarity NPD7281 Phase 3
0.7394 Intermediate Similarity NPD824 Approved
0.7394 Intermediate Similarity NPD4005 Discontinued
0.7391 Intermediate Similarity NPD5160 Discontinued
0.7378 Intermediate Similarity NPD2122 Discontinued
0.7366 Intermediate Similarity NPD3450 Approved
0.7366 Intermediate Similarity NPD3452 Approved
0.7366 Intermediate Similarity NPD2493 Approved
0.7366 Intermediate Similarity NPD2494 Approved
0.7365 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4123 Phase 3
0.736 Intermediate Similarity NPD6618 Phase 2
0.7347 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD7124 Phase 2
0.7345 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD5156 Approved
0.7338 Intermediate Similarity NPD5155 Approved
0.7329 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD5772 Approved
0.7321 Intermediate Similarity NPD5773 Approved
0.732 Intermediate Similarity NPD3635 Approved
0.732 Intermediate Similarity NPD3636 Approved
0.732 Intermediate Similarity NPD3637 Approved
0.7314 Intermediate Similarity NPD4873 Discontinued
0.7297 Intermediate Similarity NPD4093 Discontinued
0.7283 Intermediate Similarity NPD6688 Approved
0.7283 Intermediate Similarity NPD6687 Approved
0.7278 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2606 Approved
0.7273 Intermediate Similarity NPD3595 Approved
0.7273 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3594 Approved
0.7273 Intermediate Similarity NPD2605 Approved
0.7273 Intermediate Similarity NPD7479 Phase 2
0.7253 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD3656 Approved
0.7249 Intermediate Similarity NPD4582 Approved
0.7249 Intermediate Similarity NPD4583 Approved
0.7238 Intermediate Similarity NPD7291 Discontinued
0.7237 Intermediate Similarity NPD5310 Approved
0.7237 Intermediate Similarity NPD5311 Approved
0.7237 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD2156 Approved
0.7233 Intermediate Similarity NPD2154 Approved
0.7233 Intermediate Similarity NPD2155 Approved
0.723 Intermediate Similarity NPD5303 Approved
0.723 Intermediate Similarity NPD5304 Approved
0.7222 Intermediate Similarity NPD6331 Phase 2
0.7215 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD823 Approved
0.7215 Intermediate Similarity NPD817 Approved
0.7209 Intermediate Similarity NPD2904 Discontinued
0.7209 Intermediate Similarity NPD4666 Phase 3
0.7207 Intermediate Similarity NPD2971 Approved
0.7207 Intermediate Similarity NPD2968 Approved
0.7207 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD7037 Approved
0.7204 Intermediate Similarity NPD4420 Approved
0.72 Intermediate Similarity NPD5938 Phase 3
0.7196 Intermediate Similarity NPD4002 Approved
0.7196 Intermediate Similarity NPD4004 Approved
0.7193 Intermediate Similarity NPD5604 Discontinued
0.719 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD4103 Phase 2
0.719 Intermediate Similarity NPD4098 Discontinued
0.7184 Intermediate Similarity NPD4083 Discontinued
0.7178 Intermediate Similarity NPD2677 Approved
0.7171 Intermediate Similarity NPD1669 Approved
0.7169 Intermediate Similarity NPD1914 Approved
0.716 Intermediate Similarity NPD5061 Approved
0.716 Intermediate Similarity NPD5062 Approved
0.7158 Intermediate Similarity NPD4040 Phase 1
0.7152 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7447 Phase 1
0.7151 Intermediate Similarity NPD2975 Approved
0.7151 Intermediate Similarity NPD2974 Approved
0.7151 Intermediate Similarity NPD2973 Approved
0.7151 Intermediate Similarity NPD7549 Discontinued
0.7151 Intermediate Similarity NPD5709 Phase 3
0.7143 Intermediate Similarity NPD6875 Approved
0.7143 Intermediate Similarity NPD4675 Approved
0.7143 Intermediate Similarity NPD3296 Phase 1

  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