Structure

Physi-Chem Properties

Molecular Weight:  644.43
Volume:  688.718
LogP:  7.699
LogD:  4.406
LogS:  -4.841
# Rotatable Bonds:  19
TPSA:  130.36
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.093
Synthetic Accessibility Score:  4.987
Fsp3:  0.816
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.85
MDCK Permeability:  1.9525094103300944e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.052
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.514
Plasma Protein Binding (PPB):  96.96172332763672%
Volume Distribution (VD):  1.973
Pgp-substrate:  2.9068334102630615%

ADMET: Metabolism

CYP1A2-inhibitor:  0.05
CYP1A2-substrate:  0.106
CYP2C19-inhibitor:  0.516
CYP2C19-substrate:  0.092
CYP2C9-inhibitor:  0.58
CYP2C9-substrate:  0.236
CYP2D6-inhibitor:  0.094
CYP2D6-substrate:  0.016
CYP3A4-inhibitor:  0.894
CYP3A4-substrate:  0.115

ADMET: Excretion

Clearance (CL):  3.302
Half-life (T1/2):  0.04

ADMET: Toxicity

hERG Blockers:  0.889
Human Hepatotoxicity (H-HT):  0.945
Drug-inuced Liver Injury (DILI):  0.384
AMES Toxicity:  0.022
Rat Oral Acute Toxicity:  0.873
Maximum Recommended Daily Dose:  0.902
Skin Sensitization:  0.925
Carcinogencity:  0.058
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.978

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

  Natural Product: NPC59907

Natural Product ID:  NPC59907
Common Name*:   Hydrocotarnine
IUPAC Name:   4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
Synonyms:  
Standard InCHIKey:  XXANNZJIZQTCBP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H15NO3/c1-13-4-3-8-5-10-12(16-7-15-10)11(14-2)9(8)6-13/h5H,3-4,6-7H2,1-2H3/p+1
SMILES:  C[NH+]1CCc2cc3c(c(c2C1)OC)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1606295
PubChem CID:   3646
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[15019787]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23517479]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12265 Aquilaria agallochum Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31048 Papaver sommiferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12265 Aquilaria agallochum Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7312 Aplidium multiplicatum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2466 Aloe microstigma Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10176 Chrozophora prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12265 Aquilaria agallochum Species Thymelaeaceae 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
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 3981.1 nM PMID[568181]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 3981.07 nM PMID[568181]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 1995.26 nM PMID[568181]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 98.91 % PMID[568182]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 77.76 % PMID[568182]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[568183]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[568183]

☑ 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 NPC59907 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 NPC37144
0.9209 High Similarity NPC7018
0.891 High Similarity NPC75958
0.8734 High Similarity NPC19520
0.8734 High Similarity NPC149090
0.8643 High Similarity NPC160193
0.858 High Similarity NPC244554
0.8562 High Similarity NPC93593
0.8562 High Similarity NPC216459
0.8562 High Similarity NPC41178
0.8562 High Similarity NPC138487
0.8535 High Similarity NPC180306
0.8533 High Similarity NPC475959
0.8506 High Similarity NPC146288
0.8476 Intermediate Similarity NPC299990
0.8476 Intermediate Similarity NPC73492
0.8431 Intermediate Similarity NPC148898
0.8418 Intermediate Similarity NPC302527
0.8418 Intermediate Similarity NPC16805
0.8418 Intermediate Similarity NPC167546
0.8418 Intermediate Similarity NPC225774
0.8414 Intermediate Similarity NPC416184
0.8387 Intermediate Similarity NPC234392
0.8387 Intermediate Similarity NPC31311
0.8385 Intermediate Similarity NPC65403
0.8365 Intermediate Similarity NPC24264
0.8365 Intermediate Similarity NPC219341
0.8365 Intermediate Similarity NPC476432
0.8354 Intermediate Similarity NPC470879
0.8354 Intermediate Similarity NPC258695
0.8344 Intermediate Similarity NPC112575
0.8333 Intermediate Similarity NPC160692
0.8323 Intermediate Similarity NPC78733
0.8313 Intermediate Similarity NPC247389
0.8313 Intermediate Similarity NPC210918
0.8312 Intermediate Similarity NPC210148
0.8312 Intermediate Similarity NPC233029
0.8303 Intermediate Similarity NPC32413
0.8303 Intermediate Similarity NPC474506
0.8302 Intermediate Similarity NPC24465
0.8301 Intermediate Similarity NPC223125
0.8293 Intermediate Similarity NPC23219
0.8288 Intermediate Similarity NPC131204
0.8288 Intermediate Similarity NPC301050
0.8282 Intermediate Similarity NPC187678
0.8263 Intermediate Similarity NPC9867
0.825 Intermediate Similarity NPC264850
0.825 Intermediate Similarity NPC13916
0.8239 Intermediate Similarity NPC320104
0.8228 Intermediate Similarity NPC477559
0.8228 Intermediate Similarity NPC160298
0.8228 Intermediate Similarity NPC306902
0.8228 Intermediate Similarity NPC266753
0.8228 Intermediate Similarity NPC232924
0.8225 Intermediate Similarity NPC281581
0.8221 Intermediate Similarity NPC228040
0.8221 Intermediate Similarity NPC2314
0.8212 Intermediate Similarity NPC110337
0.8199 Intermediate Similarity NPC474324
0.8199 Intermediate Similarity NPC100566
0.8199 Intermediate Similarity NPC57812
0.8194 Intermediate Similarity NPC223124
0.8187 Intermediate Similarity NPC232514
0.8187 Intermediate Similarity NPC247972
0.8187 Intermediate Similarity NPC276944
0.8187 Intermediate Similarity NPC238530
0.8176 Intermediate Similarity NPC473716
0.8176 Intermediate Similarity NPC63152
0.8176 Intermediate Similarity NPC475597
0.8148 Intermediate Similarity NPC158148
0.8148 Intermediate Similarity NPC475845
0.8148 Intermediate Similarity NPC83198
0.8148 Intermediate Similarity NPC204908
0.8148 Intermediate Similarity NPC266176
0.8148 Intermediate Similarity NPC290759
0.8148 Intermediate Similarity NPC82533
0.8129 Intermediate Similarity NPC24260
0.8121 Intermediate Similarity NPC314682
0.8118 Intermediate Similarity NPC82763
0.8117 Intermediate Similarity NPC211296
0.8108 Intermediate Similarity NPC253429
0.8107 Intermediate Similarity NPC57036
0.8107 Intermediate Similarity NPC214116
0.8105 Intermediate Similarity NPC51957
0.8105 Intermediate Similarity NPC106295
0.8105 Intermediate Similarity NPC16107
0.8105 Intermediate Similarity NPC476144
0.8105 Intermediate Similarity NPC210437
0.8105 Intermediate Similarity NPC476151
0.8101 Intermediate Similarity NPC129603
0.8098 Intermediate Similarity NPC6152
0.8098 Intermediate Similarity NPC474708
0.8098 Intermediate Similarity NPC311991
0.8092 Intermediate Similarity NPC130926
0.8086 Intermediate Similarity NPC181653
0.8086 Intermediate Similarity NPC190332
0.8072 Intermediate Similarity NPC15919
0.8072 Intermediate Similarity NPC294790
0.8072 Intermediate Similarity NPC118633
0.8072 Intermediate Similarity NPC148693
0.8067 Intermediate Similarity NPC188163
0.8067 Intermediate Similarity NPC474915
0.8067 Intermediate Similarity NPC213206
0.8067 Intermediate Similarity NPC328750
0.8061 Intermediate Similarity NPC128560
0.8061 Intermediate Similarity NPC199465
0.8061 Intermediate Similarity NPC229166
0.8059 Intermediate Similarity NPC476576
0.8059 Intermediate Similarity NPC186546
0.8052 Intermediate Similarity NPC7467
0.805 Intermediate Similarity NPC106786
0.805 Intermediate Similarity NPC111485
0.805 Intermediate Similarity NPC477080
0.8049 Intermediate Similarity NPC317145
0.8049 Intermediate Similarity NPC63646
0.8049 Intermediate Similarity NPC470739
0.8049 Intermediate Similarity NPC10908
0.8049 Intermediate Similarity NPC227060
0.8049 Intermediate Similarity NPC317439
0.8049 Intermediate Similarity NPC225597
0.8049 Intermediate Similarity NPC76682
0.8049 Intermediate Similarity NPC477640
0.8049 Intermediate Similarity NPC115284
0.8049 Intermediate Similarity NPC198498
0.8049 Intermediate Similarity NPC276890
0.8039 Intermediate Similarity NPC473934
0.8037 Intermediate Similarity NPC58766
0.8037 Intermediate Similarity NPC475686
0.8025 Intermediate Similarity NPC476002
0.8 Intermediate Similarity NPC97072
0.8 Intermediate Similarity NPC152680
0.8 Intermediate Similarity NPC232386
0.8 Intermediate Similarity NPC477565
0.8 Intermediate Similarity NPC129518
0.8 Intermediate Similarity NPC215829
0.8 Intermediate Similarity NPC103379
0.8 Intermediate Similarity NPC251580
0.8 Intermediate Similarity NPC12424
0.8 Intermediate Similarity NPC41376
0.8 Intermediate Similarity NPC262641
0.8 Intermediate Similarity NPC190783
0.7988 Intermediate Similarity NPC474475
0.7987 Intermediate Similarity NPC315707
0.7987 Intermediate Similarity NPC40389
0.7987 Intermediate Similarity NPC148014
0.7987 Intermediate Similarity NPC65490
0.7987 Intermediate Similarity NPC78359
0.7986 Intermediate Similarity NPC172403
0.7975 Intermediate Similarity NPC298979
0.7975 Intermediate Similarity NPC204947
0.7975 Intermediate Similarity NPC99659
0.7975 Intermediate Similarity NPC244112
0.7975 Intermediate Similarity NPC325871
0.7974 Intermediate Similarity NPC145304
0.7964 Intermediate Similarity NPC114364
0.7964 Intermediate Similarity NPC320223
0.7963 Intermediate Similarity NPC231198
0.7963 Intermediate Similarity NPC168409
0.7961 Intermediate Similarity NPC476567
0.7961 Intermediate Similarity NPC136860
0.7961 Intermediate Similarity NPC128019
0.7952 Intermediate Similarity NPC304675
0.7952 Intermediate Similarity NPC49353
0.795 Intermediate Similarity NPC24954
0.7939 Intermediate Similarity NPC239775
0.7927 Intermediate Similarity NPC241055
0.7917 Intermediate Similarity NPC126284
0.7914 Intermediate Similarity NPC304659
0.7914 Intermediate Similarity NPC86144
0.7904 Intermediate Similarity NPC237044
0.7904 Intermediate Similarity NPC293093
0.7904 Intermediate Similarity NPC474470
0.7901 Intermediate Similarity NPC189470
0.7901 Intermediate Similarity NPC59567
0.7888 Intermediate Similarity NPC249274
0.7879 Intermediate Similarity NPC118274
0.7879 Intermediate Similarity NPC168753
0.7875 Intermediate Similarity NPC476572
0.7862 Intermediate Similarity NPC76079
0.7862 Intermediate Similarity NPC123323
0.7857 Intermediate Similarity NPC119949
0.7857 Intermediate Similarity NPC474325
0.7857 Intermediate Similarity NPC185838
0.7853 Intermediate Similarity NPC306669
0.7853 Intermediate Similarity NPC475654
0.7844 Intermediate Similarity NPC477558
0.784 Intermediate Similarity NPC60186
0.7834 Intermediate Similarity NPC274026
0.7831 Intermediate Similarity NPC10871
0.7826 Intermediate Similarity NPC59028
0.7826 Intermediate Similarity NPC92191
0.7824 Intermediate Similarity NPC248642
0.7824 Intermediate Similarity NPC116284
0.7816 Intermediate Similarity NPC117717
0.7812 Intermediate Similarity NPC180756
0.7812 Intermediate Similarity NPC323443
0.7811 Intermediate Similarity NPC267408
0.7811 Intermediate Similarity NPC475479
0.7811 Intermediate Similarity NPC243454
0.7811 Intermediate Similarity NPC474745

  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 NPC59907 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
0.8591 High Similarity NPD1424 Approved
0.8165 Intermediate Similarity NPD6788 Approved
0.8105 Intermediate Similarity NPD4584 Approved
0.8067 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD8252 Approved
0.8049 Intermediate Similarity NPD8099 Discontinued
0.8049 Intermediate Similarity NPD8251 Approved
0.8026 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8156 Discontinued
0.7987 Intermediate Similarity NPD2560 Approved
0.7987 Intermediate Similarity NPD2563 Approved
0.7914 Intermediate Similarity NPD6071 Discontinued
0.7898 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD5005 Approved
0.7765 Intermediate Similarity NPD5006 Approved
0.7755 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7124 Phase 2
0.7742 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD8054 Approved
0.7719 Intermediate Similarity NPD8053 Approved
0.7682 Intermediate Similarity NPD6111 Discontinued
0.7658 Intermediate Similarity NPD3641 Approved
0.7658 Intermediate Similarity NPD3639 Approved
0.7658 Intermediate Similarity NPD3640 Phase 3
0.7616 Intermediate Similarity NPD2492 Phase 1
0.7584 Intermediate Similarity NPD5718 Phase 2
0.7578 Intermediate Similarity NPD4772 Phase 2
0.7578 Intermediate Similarity NPD4773 Phase 2
0.7576 Intermediate Similarity NPD5677 Discontinued
0.7562 Intermediate Similarity NPD4017 Approved
0.7547 Intermediate Similarity NPD6031 Approved
0.7547 Intermediate Similarity NPD6030 Approved
0.7542 Intermediate Similarity NPD4420 Approved
0.7531 Intermediate Similarity NPD3383 Approved
0.7531 Intermediate Similarity NPD3382 Approved
0.7531 Intermediate Similarity NPD3384 Approved
0.7516 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD5297 Approved
0.7455 Intermediate Similarity NPD5604 Discontinued
0.7455 Intermediate Similarity NPD4055 Discovery
0.745 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD3705 Approved
0.7423 Intermediate Similarity NPD7298 Approved
0.7396 Intermediate Similarity NPD4481 Phase 3
0.7381 Intermediate Similarity NPD3051 Approved
0.7378 Intermediate Similarity NPD4585 Approved
0.7337 Intermediate Similarity NPD2969 Approved
0.7337 Intermediate Similarity NPD2970 Approved
0.7321 Intermediate Similarity NPD6107 Approved
0.7314 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD2898 Approved
0.7284 Intermediate Similarity NPD4210 Discontinued
0.7278 Intermediate Similarity NPD4166 Phase 2
0.7273 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6896 Approved
0.7226 Intermediate Similarity NPD6895 Approved
0.7226 Intermediate Similarity NPD2200 Suspended
0.7222 Intermediate Similarity NPD5976 Discontinued
0.7215 Intermediate Similarity NPD4237 Approved
0.7215 Intermediate Similarity NPD4236 Phase 3
0.7215 Intermediate Similarity NPD5177 Phase 3
0.7213 Intermediate Similarity NPD8095 Phase 1
0.7197 Intermediate Similarity NPD1375 Discontinued
0.7195 Intermediate Similarity NPD4678 Approved
0.7195 Intermediate Similarity NPD4675 Approved
0.7193 Intermediate Similarity NPD2489 Approved
0.7193 Intermediate Similarity NPD27 Approved
0.7184 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD2978 Approved
0.7169 Intermediate Similarity NPD2977 Approved
0.716 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5090 Approved
0.7152 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5089 Approved
0.7143 Intermediate Similarity NPD7833 Phase 2
0.7143 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2238 Phase 2
0.7143 Intermediate Similarity NPD7831 Phase 2
0.7134 Intermediate Similarity NPD4005 Discontinued
0.7126 Intermediate Similarity NPD5977 Approved
0.7126 Intermediate Similarity NPD5978 Approved
0.7125 Intermediate Similarity NPD5241 Discontinued
0.7118 Intermediate Similarity NPD7802 Discontinued
0.7099 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7906 Approved
0.7078 Intermediate Similarity NPD4475 Approved
0.7078 Intermediate Similarity NPD2674 Phase 3
0.7078 Intermediate Similarity NPD4474 Approved
0.7076 Intermediate Similarity NPD4010 Discontinued
0.7069 Intermediate Similarity NPD5312 Approved
0.7069 Intermediate Similarity NPD5313 Approved
0.7063 Intermediate Similarity NPD7466 Approved
0.7062 Intermediate Similarity NPD7280 Phase 3
0.7062 Intermediate Similarity NPD7281 Phase 3
0.7062 Intermediate Similarity NPD4577 Approved
0.7062 Intermediate Similarity NPD4578 Approved
0.7055 Intermediate Similarity NPD1350 Approved
0.7055 Intermediate Similarity NPD1349 Approved
0.7055 Intermediate Similarity NPD1351 Approved
0.7041 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3124 Discontinued
0.7035 Intermediate Similarity NPD5242 Approved
0.7025 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7549 Discontinued
0.7 Intermediate Similarity NPD3060 Approved
0.6978 Remote Similarity NPD7296 Approved
0.6966 Remote Similarity NPD2971 Approved
0.6966 Remote Similarity NPD7313 Approved
0.6966 Remote Similarity NPD2968 Approved
0.6966 Remote Similarity NPD7311 Approved
0.6966 Remote Similarity NPD7312 Approved
0.6966 Remote Similarity NPD7310 Approved
0.6964 Remote Similarity NPD5773 Approved
0.6964 Remote Similarity NPD5772 Approved
0.6957 Remote Similarity NPD5582 Discontinued
0.6951 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7110 Phase 1
0.6946 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4663 Approved
0.6943 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6936 Remote Similarity NPD6687 Approved
0.6936 Remote Similarity NPD6688 Approved
0.6933 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3885 Approved
0.6927 Remote Similarity NPD7309 Approved
0.6923 Remote Similarity NPD5353 Approved
0.691 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6906 Remote Similarity NPD6842 Approved
0.6906 Remote Similarity NPD6841 Approved
0.6906 Remote Similarity NPD6843 Phase 3
0.6903 Remote Similarity NPD1336 Approved
0.6903 Remote Similarity NPD3144 Approved
0.6903 Remote Similarity NPD3145 Approved
0.6894 Remote Similarity NPD4162 Approved
0.6893 Remote Similarity NPD6297 Approved
0.689 Remote Similarity NPD4123 Phase 3
0.6887 Remote Similarity NPD1420 Approved
0.6887 Remote Similarity NPD1421 Approved
0.6886 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3656 Approved
0.6865 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6857 Remote Similarity NPD3489 Phase 3
0.6846 Remote Similarity NPD2668 Approved
0.6846 Remote Similarity NPD2667 Approved
0.6835 Remote Similarity NPD2653 Approved
0.6828 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2230 Approved
0.6821 Remote Similarity NPD2233 Approved
0.6821 Remote Similarity NPD2232 Approved
0.6818 Remote Similarity NPD3018 Phase 2
0.6815 Remote Similarity NPD3109 Approved
0.6815 Remote Similarity NPD3110 Approved
0.681 Remote Similarity NPD2219 Phase 1
0.6807 Remote Similarity NPD1914 Approved
0.6805 Remote Similarity NPD37 Approved
0.6805 Remote Similarity NPD7945 Clinical (unspecified phase)
0.679 Remote Similarity NPD2654 Approved
0.6788 Remote Similarity NPD7447 Phase 1
0.6786 Remote Similarity NPD6875 Approved
0.6786 Remote Similarity NPD6876 Approved
0.6776 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6769 Remote Similarity NPD7827 Phase 1
0.6768 Remote Similarity NPD2120 Phase 2
0.6761 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6757 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6753 Remote Similarity NPD7905 Discontinued
0.675 Remote Similarity NPD4108 Discontinued
0.6748 Remote Similarity NPD6625 Approved
0.6748 Remote Similarity NPD6748 Discontinued
0.6748 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6748 Remote Similarity NPD5754 Discontinued
0.6747 Remote Similarity NPD6090 Discontinued
0.6746 Remote Similarity NPD6386 Approved
0.6746 Remote Similarity NPD6385 Approved
0.674 Remote Similarity NPD6853 Approved
0.674 Remote Similarity NPD6851 Approved
0.6738 Remote Similarity NPD2973 Approved
0.6738 Remote Similarity NPD2974 Approved
0.6738 Remote Similarity NPD2975 Approved
0.6735 Remote Similarity NPD709 Approved
0.6728 Remote Similarity NPD7153 Discontinued
0.6727 Remote Similarity NPD2420 Approved
0.6727 Remote Similarity NPD7212 Phase 2
0.6727 Remote Similarity NPD2421 Approved
0.6727 Remote Similarity NPD7213 Phase 3
0.6726 Remote Similarity NPD824 Approved
0.6725 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6721 Remote Similarity NPD3349 Phase 2
0.6711 Remote Similarity NPD2981 Phase 2
0.671 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6708 Remote Similarity NPD2161 Phase 2
0.6707 Remote Similarity NPD3692 Discontinued
0.6707 Remote Similarity NPD4727 Phase 1
0.6707 Remote Similarity NPD2677 Approved
0.6706 Remote Similarity NPD5720 Discontinued
0.6688 Remote Similarity NPD4098 Discontinued

  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