Structure

Physi-Chem Properties

Molecular Weight:  165.12
Volume:  184.837
LogP:  1.765
LogD:  1.338
LogS:  -2.7
# Rotatable Bonds:  3
TPSA:  35.25
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.738
Synthetic Accessibility Score:  1.927
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.747
MDCK Permeability:  5.489146496984176e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.272
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.825
Plasma Protein Binding (PPB):  34.4121208190918%
Volume Distribution (VD):  5.23
Pgp-substrate:  67.42475891113281%

ADMET: Metabolism

CYP1A2-inhibitor:  0.711
CYP1A2-substrate:  0.893
CYP2C19-inhibitor:  0.142
CYP2C19-substrate:  0.923
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.375
CYP2D6-inhibitor:  0.954
CYP2D6-substrate:  0.922
CYP3A4-inhibitor:  0.076
CYP3A4-substrate:  0.465

ADMET: Excretion

Clearance (CL):  11.121
Half-life (T1/2):  0.358

ADMET: Toxicity

hERG Blockers:  0.415
Human Hepatotoxicity (H-HT):  0.342
Drug-inuced Liver Injury (DILI):  0.079
AMES Toxicity:  0.116
Rat Oral Acute Toxicity:  0.943
Maximum Recommended Daily Dose:  0.671
Skin Sensitization:  0.276
Carcinogencity:  0.136
Eye Corrosion:  0.008
Eye Irritation:  0.027
Respiratory Toxicity:  0.945

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

  Natural Product: NPC97811

Natural Product ID:  NPC97811
Common Name*:   Para-Methoxyamphetamine
IUPAC Name:   1-(4-methoxyphenyl)propan-2-amine
Synonyms:   beta-methoxyamphetamine; para-Methoxyamphetamine
Standard InCHIKey:  NEGYEDYHPHMHGK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
SMILES:  CC(Cc1ccc(cc1)OC)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL278663
PubChem CID:   31721
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000186] Phenethylamines
          • [CHEMONTID:0000188] Amphetamines 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
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19472 Thymus vulgaris Species Lamiaceae 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
NPT1779 Individual Protein Serotonin 2b (5-HT2b) receptor Rattus norvegicus Kd = 6918.31 nM PMID[550715]
NPT1488 Individual Protein Monoamine oxidase A Rattus norvegicus IC50 = 300.0 nM PMID[550717]
NPT1488 Individual Protein Monoamine oxidase A Rattus norvegicus Ki = 250.0 nM PMID[550718]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus IC50 = 173.0 nM PMID[550719]
NPT71 Cell Line HEK293 Homo sapiens EC50 = 457088.19 nM PMID[550719]
NPT295 Individual Protein Serotonin transporter Homo sapiens EC50 = 1071519.31 nM PMID[550719]
NPT295 Individual Protein Serotonin transporter Homo sapiens EC50 = 32359.37 nM PMID[550719]
NPT519 Cell Line SH-SY5Y Homo sapiens EC50 > 10000000.0 nM PMID[550719]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[550720]
NPT1530 Protein Family Serotonin (5-HT) receptor Rattus norvegicus Kd = 7079.46 nM PMID[550711]
NPT29 Organism Rattus norvegicus Rattus norvegicus DOM = 13.0 % PMID[550712]
NPT29 Organism Rattus norvegicus Rattus norvegicus DOM = 15.0 % PMID[550712]
NPT1530 Protein Family Serotonin (5-HT) receptor Rattus norvegicus Kd = 7079.46 nM PMID[550712]
NPT29 Organism Rattus norvegicus Rattus norvegicus No. of animals = 5.0 n.a. PMID[550712]
NPT29 Organism Rattus norvegicus Rattus norvegicus No. of animals = 4.0 n.a. PMID[550712]
NPT29 Organism Rattus norvegicus Rattus norvegicus No. of animals = 2.0 n.a. PMID[550712]
NPT1776 Protein Family Serotonin 1 (5-HT1) receptor Rattus norvegicus Ki = 79400.0 nM PMID[550713]
NPT1777 Protein Family Serotonin 2 (5-HT2) receptor Rattus norvegicus Ki = 33600.0 nM PMID[550713]
NPT605 Organism Homo sapiens Homo sapiens Activity = 5.0 MU PMID[550714]
NPT605 Organism Homo sapiens Homo sapiens Log activity = 0.699 n.a. PMID[550714]
NPT35 Others n.a. LogP = 1.77 n.a. PMID[550715]
NPT605 Organism Homo sapiens Homo sapiens Relative activity = 4.0 n.a. PMID[550715]
NPT2 Others Unspecified KDNB = 1.02 n.a. PMID[550715]
NPT605 Organism Homo sapiens Homo sapiens Activity = 5.0 n.a. PMID[550716]
NPT20913 TISSUE Whole blood Homo sapiens Retention_time = 2.91 min PMID[550721]
NPT2 Others Unspecified IC50 = 2691534.8 nM PMID[550723]
NPT605 Organism Homo sapiens Homo sapiens log(activity) = 0.59 n.a. PMID[550724]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[550725]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[550725]

☑ 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 NPC97811 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
0.97 High Similarity NPC42383
0.9524 High Similarity NPC26524
0.9333 High Similarity NPC21890
0.932 High Similarity NPC186469
0.8829 High Similarity NPC120075
0.86 High Similarity NPC321956
0.85 High Similarity NPC71853
0.8448 Intermediate Similarity NPC211992
0.84 Intermediate Similarity NPC177844
0.84 Intermediate Similarity NPC259134
0.84 Intermediate Similarity NPC8002
0.84 Intermediate Similarity NPC99886
0.8376 Intermediate Similarity NPC298486
0.8305 Intermediate Similarity NPC13020
0.8305 Intermediate Similarity NPC140359
0.8286 Intermediate Similarity NPC125732
0.8182 Intermediate Similarity NPC291847
0.8151 Intermediate Similarity NPC217277
0.8151 Intermediate Similarity NPC328267
0.8113 Intermediate Similarity NPC100870
0.8083 Intermediate Similarity NPC105513
0.8077 Intermediate Similarity NPC471581
0.8051 Intermediate Similarity NPC318357
0.8034 Intermediate Similarity NPC43275
0.8018 Intermediate Similarity NPC146530
0.8018 Intermediate Similarity NPC309982
0.8017 Intermediate Similarity NPC320242
0.7966 Intermediate Similarity NPC321133
0.7965 Intermediate Similarity NPC166837
0.7963 Intermediate Similarity NPC300166
0.7946 Intermediate Similarity NPC290566
0.7946 Intermediate Similarity NPC145638
0.789 Intermediate Similarity NPC298224
0.789 Intermediate Similarity NPC68055
0.785 Intermediate Similarity NPC470161
0.785 Intermediate Similarity NPC175298
0.784 Intermediate Similarity NPC329595
0.784 Intermediate Similarity NPC326599
0.7818 Intermediate Similarity NPC38209
0.7818 Intermediate Similarity NPC292792
0.7818 Intermediate Similarity NPC38079
0.7818 Intermediate Similarity NPC241224
0.7818 Intermediate Similarity NPC108875
0.7815 Intermediate Similarity NPC263835
0.7778 Intermediate Similarity NPC471576
0.776 Intermediate Similarity NPC262641
0.7748 Intermediate Similarity NPC470393
0.7748 Intermediate Similarity NPC473855
0.7727 Intermediate Similarity NPC305205
0.7724 Intermediate Similarity NPC136112
0.7724 Intermediate Similarity NPC141739
0.7706 Intermediate Similarity NPC29601
0.7706 Intermediate Similarity NPC13755
0.7706 Intermediate Similarity NPC155847
0.7706 Intermediate Similarity NPC289381
0.7705 Intermediate Similarity NPC211218
0.7692 Intermediate Similarity NPC213
0.7692 Intermediate Similarity NPC10286
0.7685 Intermediate Similarity NPC290515
0.7685 Intermediate Similarity NPC95755
0.7685 Intermediate Similarity NPC303611
0.7685 Intermediate Similarity NPC226096
0.7685 Intermediate Similarity NPC108606
0.7685 Intermediate Similarity NPC164514
0.7679 Intermediate Similarity NPC1065
0.7679 Intermediate Similarity NPC113457
0.7667 Intermediate Similarity NPC289330
0.7667 Intermediate Similarity NPC53596
0.7667 Intermediate Similarity NPC160120
0.7667 Intermediate Similarity NPC471308
0.7667 Intermediate Similarity NPC17388
0.7642 Intermediate Similarity NPC62101
0.7642 Intermediate Similarity NPC272463
0.7642 Intermediate Similarity NPC95733
0.7638 Intermediate Similarity NPC247018
0.7638 Intermediate Similarity NPC97870
0.7638 Intermediate Similarity NPC307123
0.7636 Intermediate Similarity NPC51633
0.7636 Intermediate Similarity NPC12714
0.7636 Intermediate Similarity NPC307425
0.7636 Intermediate Similarity NPC310905
0.7632 Intermediate Similarity NPC24777
0.7627 Intermediate Similarity NPC106551
0.7627 Intermediate Similarity NPC281686
0.7627 Intermediate Similarity NPC188867
0.7615 Intermediate Similarity NPC253429
0.7611 Intermediate Similarity NPC251306
0.7589 Intermediate Similarity NPC238115
0.7586 Intermediate Similarity NPC146422
0.7583 Intermediate Similarity NPC283760
0.7581 Intermediate Similarity NPC29477
0.7581 Intermediate Similarity NPC124776
0.7578 Intermediate Similarity NPC160692
0.7576 Intermediate Similarity NPC204546
0.7576 Intermediate Similarity NPC66518
0.7568 Intermediate Similarity NPC192596
0.7568 Intermediate Similarity NPC12870
0.7568 Intermediate Similarity NPC179686
0.7568 Intermediate Similarity NPC178902
0.7568 Intermediate Similarity NPC24327
0.7545 Intermediate Similarity NPC107101
0.7544 Intermediate Similarity NPC75440
0.7542 Intermediate Similarity NPC303370
0.752 Intermediate Similarity NPC301713
0.75 Intermediate Similarity NPC2518
0.75 Intermediate Similarity NPC474603
0.75 Intermediate Similarity NPC283546
0.75 Intermediate Similarity NPC118419
0.75 Intermediate Similarity NPC12987
0.75 Intermediate Similarity NPC109637
0.75 Intermediate Similarity NPC470392
0.748 Intermediate Similarity NPC471314
0.748 Intermediate Similarity NPC471315
0.7478 Intermediate Similarity NPC234639
0.7478 Intermediate Similarity NPC474272
0.7477 Intermediate Similarity NPC84325
0.746 Intermediate Similarity NPC153990
0.7442 Intermediate Similarity NPC325568
0.7438 Intermediate Similarity NPC239697
0.7434 Intermediate Similarity NPC8302
0.7434 Intermediate Similarity NPC128730
0.7424 Intermediate Similarity NPC318984
0.7424 Intermediate Similarity NPC317741
0.7424 Intermediate Similarity NPC328137
0.7424 Intermediate Similarity NPC318028
0.7424 Intermediate Similarity NPC241086
0.7424 Intermediate Similarity NPC282087
0.7424 Intermediate Similarity NPC259800
0.7417 Intermediate Similarity NPC323948
0.7414 Intermediate Similarity NPC88868
0.7414 Intermediate Similarity NPC25067
0.7414 Intermediate Similarity NPC137685
0.7414 Intermediate Similarity NPC473809
0.7414 Intermediate Similarity NPC231251
0.7414 Intermediate Similarity NPC475852
0.7407 Intermediate Similarity NPC20142
0.7407 Intermediate Similarity NPC215351
0.7402 Intermediate Similarity NPC471321
0.7402 Intermediate Similarity NPC471306
0.74 Intermediate Similarity NPC124576
0.7391 Intermediate Similarity NPC201959
0.7391 Intermediate Similarity NPC291837
0.7381 Intermediate Similarity NPC218323
0.7373 Intermediate Similarity NPC59387
0.7368 Intermediate Similarity NPC231705
0.7368 Intermediate Similarity NPC176971
0.7368 Intermediate Similarity NPC326447
0.7364 Intermediate Similarity NPC107619
0.7355 Intermediate Similarity NPC85276
0.735 Intermediate Similarity NPC257124
0.735 Intermediate Similarity NPC173746
0.735 Intermediate Similarity NPC156840
0.735 Intermediate Similarity NPC8547
0.735 Intermediate Similarity NPC23332
0.7345 Intermediate Similarity NPC150254
0.7345 Intermediate Similarity NPC147000
0.7345 Intermediate Similarity NPC226778
0.7345 Intermediate Similarity NPC304761
0.7333 Intermediate Similarity NPC258992
0.7333 Intermediate Similarity NPC23167
0.7328 Intermediate Similarity NPC237227
0.7328 Intermediate Similarity NPC11147
0.7328 Intermediate Similarity NPC258056
0.7328 Intermediate Similarity NPC259554
0.7323 Intermediate Similarity NPC251571
0.7323 Intermediate Similarity NPC172403
0.7317 Intermediate Similarity NPC183262
0.7317 Intermediate Similarity NPC326079
0.7313 Intermediate Similarity NPC323204
0.7311 Intermediate Similarity NPC118202
0.7304 Intermediate Similarity NPC157473
0.7304 Intermediate Similarity NPC151530
0.7304 Intermediate Similarity NPC258171
0.7304 Intermediate Similarity NPC142297
0.7304 Intermediate Similarity NPC233320
0.7304 Intermediate Similarity NPC227894
0.7295 Intermediate Similarity NPC256369
0.7293 Intermediate Similarity NPC326860
0.7293 Intermediate Similarity NPC197239
0.7288 Intermediate Similarity NPC199462
0.7287 Intermediate Similarity NPC114102
0.7281 Intermediate Similarity NPC227255
0.7281 Intermediate Similarity NPC473393
0.728 Intermediate Similarity NPC255253
0.7279 Intermediate Similarity NPC294249
0.7273 Intermediate Similarity NPC137096
0.7266 Intermediate Similarity NPC283079
0.7266 Intermediate Similarity NPC155838
0.7265 Intermediate Similarity NPC106141
0.7265 Intermediate Similarity NPC474149
0.7265 Intermediate Similarity NPC31279
0.7265 Intermediate Similarity NPC183648
0.7264 Intermediate Similarity NPC25493
0.7264 Intermediate Similarity NPC113460
0.725 Intermediate Similarity NPC317254
0.7241 Intermediate Similarity NPC153690
0.7239 Intermediate Similarity NPC59661
0.7238 Intermediate Similarity NPC197783
0.7236 Intermediate Similarity NPC41801
0.7236 Intermediate Similarity NPC118522

  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 NPC97811 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
0.9074 High Similarity NPD595 Approved
0.9074 High Similarity NPD593 Approved
0.8667 High Similarity NPD9608 Approved
0.8667 High Similarity NPD9610 Approved
0.839 Intermediate Similarity NPD196 Phase 1
0.8304 Intermediate Similarity NPD594 Approved
0.8304 Intermediate Similarity NPD592 Approved
0.8151 Intermediate Similarity NPD2428 Approved
0.8151 Intermediate Similarity NPD2429 Approved
0.812 Intermediate Similarity NPD2554 Approved
0.812 Intermediate Similarity NPD2556 Approved
0.8065 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD3049 Approved
0.8017 Intermediate Similarity NPD1818 Approved
0.8017 Intermediate Similarity NPD1819 Approved
0.8017 Intermediate Similarity NPD1820 Approved
0.8017 Intermediate Similarity NPD1817 Approved
0.8 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7967 Intermediate Similarity NPD600 Approved
0.7967 Intermediate Similarity NPD596 Approved
0.7966 Intermediate Similarity NPD2667 Approved
0.7966 Intermediate Similarity NPD2668 Approved
0.7946 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD3052 Approved
0.7874 Intermediate Similarity NPD3054 Approved
0.7863 Intermediate Similarity NPD318 Approved
0.7863 Intermediate Similarity NPD317 Approved
0.784 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3596 Phase 2
0.7769 Intermediate Similarity NPD2231 Phase 2
0.7769 Intermediate Similarity NPD2235 Phase 2
0.776 Intermediate Similarity NPD3165 Approved
0.776 Intermediate Similarity NPD3167 Approved
0.776 Intermediate Similarity NPD3164 Approved
0.776 Intermediate Similarity NPD3166 Approved
0.7759 Intermediate Similarity NPD9618 Approved
0.7759 Intermediate Similarity NPD9614 Approved
0.7739 Intermediate Similarity NPD821 Approved
0.7724 Intermediate Similarity NPD1794 Approved
0.7724 Intermediate Similarity NPD1770 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD1669 Approved
0.7685 Intermediate Similarity NPD9612 Approved
0.7685 Intermediate Similarity NPD9611 Approved
0.7685 Intermediate Similarity NPD9609 Approved
0.7661 Intermediate Similarity NPD3690 Phase 2
0.7661 Intermediate Similarity NPD3691 Phase 2
0.7661 Intermediate Similarity NPD558 Phase 2
0.7647 Intermediate Similarity NPD2486 Discontinued
0.7647 Intermediate Similarity NPD6581 Approved
0.7647 Intermediate Similarity NPD6580 Approved
0.7638 Intermediate Similarity NPD1423 Approved
0.7632 Intermediate Similarity NPD550 Approved
0.7632 Intermediate Similarity NPD551 Approved
0.7627 Intermediate Similarity NPD9568 Approved
0.7619 Intermediate Similarity NPD3179 Approved
0.7619 Intermediate Similarity NPD3180 Approved
0.7619 Intermediate Similarity NPD5746 Approved
0.7611 Intermediate Similarity NPD9624 Approved
0.7597 Intermediate Similarity NPD2986 Phase 2
0.7597 Intermediate Similarity NPD2989 Phase 2
0.7586 Intermediate Similarity NPD9377 Approved
0.7586 Intermediate Similarity NPD9379 Approved
0.7583 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7563 Intermediate Similarity NPD856 Approved
0.7563 Intermediate Similarity NPD16 Approved
0.7561 Intermediate Similarity NPD1421 Approved
0.7561 Intermediate Similarity NPD1420 Approved
0.7557 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD2684 Approved
0.7542 Intermediate Similarity NPD2557 Approved
0.754 Intermediate Similarity NPD2614 Approved
0.7538 Intermediate Similarity NPD1536 Approved
0.75 Intermediate Similarity NPD2245 Discovery
0.75 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5745 Approved
0.748 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD5163 Phase 2
0.748 Intermediate Similarity NPD2561 Approved
0.748 Intermediate Similarity NPD2562 Approved
0.7478 Intermediate Similarity NPD5451 Approved
0.7462 Intermediate Similarity NPD2653 Approved
0.7459 Intermediate Similarity NPD3294 Phase 2
0.7442 Intermediate Similarity NPD3110 Approved
0.7442 Intermediate Similarity NPD3109 Approved
0.7438 Intermediate Similarity NPD2595 Approved
0.7438 Intermediate Similarity NPD2594 Approved
0.7424 Intermediate Similarity NPD1537 Approved
0.7424 Intermediate Similarity NPD1519 Approved
0.7424 Intermediate Similarity NPD1538 Phase 1
0.7422 Intermediate Similarity NPD1039 Discontinued
0.7419 Intermediate Similarity NPD9622 Approved
0.7405 Intermediate Similarity NPD1521 Approved
0.7405 Intermediate Similarity NPD1520 Approved
0.7402 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD2460 Phase 3
0.7388 Intermediate Similarity NPD2459 Approved
0.7388 Intermediate Similarity NPD2458 Approved
0.7368 Intermediate Similarity NPD3134 Approved
0.7364 Intermediate Similarity NPD3530 Approved
0.7364 Intermediate Similarity NPD839 Approved
0.7364 Intermediate Similarity NPD3532 Approved
0.7364 Intermediate Similarity NPD3531 Approved
0.7364 Intermediate Similarity NPD840 Approved
0.735 Intermediate Similarity NPD228 Approved
0.7348 Intermediate Similarity NPD7425 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD311 Approved
0.7345 Intermediate Similarity NPD310 Approved
0.7345 Intermediate Similarity NPD314 Approved
0.7345 Intermediate Similarity NPD315 Approved
0.7345 Intermediate Similarity NPD309 Approved
0.7345 Intermediate Similarity NPD10 Approved
0.7344 Intermediate Similarity NPD6179 Discontinued
0.7344 Intermediate Similarity NPD1024 Discontinued
0.7339 Intermediate Similarity NPD2232 Approved
0.7339 Intermediate Similarity NPD2233 Approved
0.7339 Intermediate Similarity NPD2230 Approved
0.7313 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD7153 Discontinued
0.7304 Intermediate Similarity NPD5373 Approved
0.7304 Intermediate Similarity NPD5374 Approved
0.7304 Intermediate Similarity NPD1358 Approved
0.7299 Intermediate Similarity NPD7598 Phase 2
0.7295 Intermediate Similarity NPD3445 Approved
0.7295 Intermediate Similarity NPD6382 Discontinued
0.7295 Intermediate Similarity NPD3443 Approved
0.7295 Intermediate Similarity NPD3444 Approved
0.7293 Intermediate Similarity NPD2239 Approved
0.7293 Intermediate Similarity NPD2240 Approved
0.7293 Intermediate Similarity NPD1523 Approved
0.7293 Intermediate Similarity NPD1522 Approved
0.7288 Intermediate Similarity NPD7843 Approved
0.7287 Intermediate Similarity NPD5718 Phase 2
0.728 Intermediate Similarity NPD6539 Approved
0.728 Intermediate Similarity NPD6543 Approved
0.728 Intermediate Similarity NPD6583 Phase 3
0.728 Intermediate Similarity NPD4129 Approved
0.728 Intermediate Similarity NPD6582 Phase 2
0.728 Intermediate Similarity NPD3685 Discontinued
0.728 Intermediate Similarity NPD6540 Phase 3
0.728 Intermediate Similarity NPD6542 Approved
0.7273 Intermediate Similarity NPD9615 Approved
0.7273 Intermediate Similarity NPD9613 Approved
0.7273 Intermediate Similarity NPD9616 Approved
0.7259 Intermediate Similarity NPD4162 Approved
0.7259 Intermediate Similarity NPD3060 Approved
0.725 Intermediate Similarity NPD256 Approved
0.725 Intermediate Similarity NPD255 Approved
0.7246 Intermediate Similarity NPD3536 Discontinued
0.7246 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2987 Approved
0.7244 Intermediate Similarity NPD7905 Discontinued
0.7244 Intermediate Similarity NPD2990 Approved
0.7244 Intermediate Similarity NPD7018 Phase 2
0.7236 Intermediate Similarity NPD9381 Approved
0.7236 Intermediate Similarity NPD9384 Approved
0.7231 Intermediate Similarity NPD7477 Discontinued
0.7231 Intermediate Similarity NPD3163 Approved
0.7231 Intermediate Similarity NPD4475 Approved
0.7231 Intermediate Similarity NPD2674 Phase 3
0.7231 Intermediate Similarity NPD3162 Approved
0.7231 Intermediate Similarity NPD4474 Approved
0.7227 Intermediate Similarity NPD5283 Phase 1
0.7227 Intermediate Similarity NPD1241 Discontinued
0.7226 Intermediate Similarity NPD2120 Phase 2
0.7222 Intermediate Similarity NPD6538 Approved
0.7222 Intermediate Similarity NPD6541 Approved
0.7217 Intermediate Similarity NPD810 Approved
0.7217 Intermediate Similarity NPD812 Approved
0.7217 Intermediate Similarity NPD811 Approved
0.7213 Intermediate Similarity NPD316 Approved
0.7206 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD3847 Discontinued
0.7176 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2203 Discontinued
0.7165 Intermediate Similarity NPD3055 Approved
0.7165 Intermediate Similarity NPD1134 Approved
0.7165 Intermediate Similarity NPD1131 Approved
0.7165 Intermediate Similarity NPD1129 Approved
0.7165 Intermediate Similarity NPD1135 Approved
0.7165 Intermediate Similarity NPD3567 Approved
0.7165 Intermediate Similarity NPD4098 Discontinued
0.7165 Intermediate Similarity NPD3053 Approved
0.7165 Intermediate Similarity NPD3568 Approved
0.7165 Intermediate Similarity NPD1133 Approved
0.7155 Intermediate Similarity NPD290 Approved
0.7154 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4727 Phase 1
0.7143 Intermediate Similarity NPD5535 Approved
0.7132 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD2874 Phase 2
0.7109 Intermediate Similarity NPD2194 Approved
0.7109 Intermediate Similarity NPD7451 Discontinued
0.7109 Intermediate Similarity NPD6584 Phase 3
0.7109 Intermediate Similarity NPD2195 Approved
0.7107 Intermediate Similarity NPD7157 Approved
0.7107 Intermediate Similarity NPD709 Approved
0.7099 Intermediate Similarity NPD259 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