Structure

Physi-Chem Properties

Molecular Weight:  323.12
Volume:  322.1
LogP:  3.128
LogD:  2.673
LogS:  -4.908
# Rotatable Bonds:  1
TPSA:  63.99
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.552
Synthetic Accessibility Score:  3.633
Fsp3:  0.316
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.735
MDCK Permeability:  1.4967127754061949e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.529

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.261
Plasma Protein Binding (PPB):  96.0323715209961%
Volume Distribution (VD):  0.461
Pgp-substrate:  1.9740263223648071%

ADMET: Metabolism

CYP1A2-inhibitor:  0.953
CYP1A2-substrate:  0.92
CYP2C19-inhibitor:  0.682
CYP2C19-substrate:  0.419
CYP2C9-inhibitor:  0.648
CYP2C9-substrate:  0.88
CYP2D6-inhibitor:  0.672
CYP2D6-substrate:  0.835
CYP3A4-inhibitor:  0.422
CYP3A4-substrate:  0.26

ADMET: Excretion

Clearance (CL):  3.318
Half-life (T1/2):  0.197

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.172
Drug-inuced Liver Injury (DILI):  0.44
AMES Toxicity:  0.916
Rat Oral Acute Toxicity:  0.631
Maximum Recommended Daily Dose:  0.868
Skin Sensitization:  0.897
Carcinogencity:  0.954
Eye Corrosion:  0.003
Eye Irritation:  0.801
Respiratory Toxicity:  0.557

Download Data

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

  Natural Product: NPC321166

Natural Product ID:  NPC321166
Common Name*:   5-Hydroxy-11-Methyl-2-(2-Methyloxiran-2-Yl)-1,2-Dihydrofuro[2,3-C]Acridin-6-One
IUPAC Name:   5-hydroxy-11-methyl-2-(2-methyloxiran-2-yl)-1,2-dihydrofuro[2,3-c]acridin-6-one
Synonyms:  
Standard InCHIKey:  YXQGLAPCZDYVLL-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H17NO4/c1-19(9-23-19)15-7-11-14(24-15)8-13(21)16-17(11)20(2)12-6-4-3-5-10(12)18(16)22/h3-6,8,15,21H,7,9H2,1-2H3
SMILES:  Oc1cc2OC(Cc2c2c1c(=O)c1c(n2C)cccc1)C1(C)CO1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1968498
PubChem CID:   5281850
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0001908] Benzoquinolines
          • [CHEMONTID:0000274] Acridines
            • [CHEMONTID:0001811] Acridones

*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
NPO3854 Ruta graveolens Species Rutaceae Eukaryota leaves n.a. n.a. PMID[12568545]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19191562]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota Whole Plants n.a. n.a. PMID[28093914]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1415.79 nM PMID[448592]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1383.57 nM PMID[448592]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2004.47 nM PMID[448592]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2018.37 nM PMID[448592]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1422.33 nM PMID[448592]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 9078.21 nM PMID[448592]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 10715.19 nM PMID[448592]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 49.55 nM PMID[448592]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 3198.9 nM PMID[448592]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1794.73 nM PMID[448592]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 10519.62 nM PMID[448592]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 11246.05 nM PMID[448592]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 260.02 nM PMID[448592]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 3614.1 nM PMID[448592]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 66.53 nM PMID[448592]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 3147.75 nM PMID[448592]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1315.22 nM PMID[448592]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 3162.28 nM PMID[448592]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 966.05 nM PMID[448592]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 6531.31 nM PMID[448592]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 2032.36 nM PMID[448592]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 21877.62 nM PMID[448592]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 10399.2 nM PMID[448592]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 11428.78 nM PMID[448592]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 110.92 nM PMID[448592]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 1166.81 nM PMID[448592]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 324.34 nM PMID[448592]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2409.91 nM PMID[448592]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 2930.89 nM PMID[448592]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 1883.65 nM PMID[448592]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1506.61 nM PMID[448592]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 11481.54 nM PMID[448592]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 2818.38 nM PMID[448592]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 8830.8 nM PMID[448592]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 11.09 nM PMID[448592]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 1667.25 nM PMID[448592]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 4655.86 nM PMID[448592]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 887.16 nM PMID[448592]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 5164.16 nM PMID[448592]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1794.73 nM PMID[448592]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 7277.8 nM PMID[448592]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 4688.13 nM PMID[448592]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 935.41 nM PMID[448592]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 941.89 nM PMID[448592]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 3076.1 nM PMID[448592]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 3372.87 nM PMID[448592]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 462.38 nM PMID[448592]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 228.56 nM PMID[448592]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 2133.04 nM PMID[448592]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 5533.5 nM PMID[448592]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 11455.13 nM PMID[448592]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 3288.52 nM PMID[448592]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2992.26 nM PMID[448592]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 2157.74 nM PMID[448592]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1640.59 nM PMID[448592]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 9440.61 nM PMID[448592]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 5874.89 nM PMID[448592]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 3605.79 nM PMID[448592]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2004.47 nM PMID[448592]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1713.96 nM PMID[448592]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 3926.45 nM PMID[448592]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 55.98 nM PMID[448592]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 3639.15 nM PMID[448592]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 13335.21 nM PMID[448592]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 4405.55 nM PMID[448592]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 2786.12 nM PMID[448592]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1174.9 nM PMID[448592]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 6095.37 nM PMID[448592]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 32284.94 nM PMID[448592]

☑ 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 NPC321166 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
0.9842 High Similarity NPC116178
0.9791 High Similarity NPC217903
0.9683 High Similarity NPC198160
0.9444 High Similarity NPC329830
0.9267 High Similarity NPC15987
0.9058 High Similarity NPC234933
0.8995 High Similarity NPC206109
0.8995 High Similarity NPC114039
0.89 High Similarity NPC30749
0.8872 High Similarity NPC288759
0.885 High Similarity NPC305542
0.88 High Similarity NPC295479
0.88 High Similarity NPC220241
0.8788 High Similarity NPC212123
0.8782 High Similarity NPC313112
0.8782 High Similarity NPC301292
0.8718 High Similarity NPC241263
0.8571 High Similarity NPC13249
0.8549 High Similarity NPC1820
0.8544 High Similarity NPC182853
0.8522 High Similarity NPC218303
0.8488 Intermediate Similarity NPC176113
0.8466 Intermediate Similarity NPC298320
0.8454 Intermediate Similarity NPC134702
0.8421 Intermediate Similarity NPC118189
0.8398 Intermediate Similarity NPC148391
0.8382 Intermediate Similarity NPC474366
0.8333 Intermediate Similarity NPC7560
0.8333 Intermediate Similarity NPC76478
0.8283 Intermediate Similarity NPC170333
0.8278 Intermediate Similarity NPC195120
0.8278 Intermediate Similarity NPC87560
0.8261 Intermediate Similarity NPC268223
0.8261 Intermediate Similarity NPC114468
0.8221 Intermediate Similarity NPC2905
0.8113 Intermediate Similarity NPC118154
0.8113 Intermediate Similarity NPC157983
0.8093 Intermediate Similarity NPC285254
0.8049 Intermediate Similarity NPC133156
0.7949 Intermediate Similarity NPC327005
0.7943 Intermediate Similarity NPC25961
0.7913 Intermediate Similarity NPC41216
0.7884 Intermediate Similarity NPC204867
0.7749 Intermediate Similarity NPC299582
0.7647 Intermediate Similarity NPC471825
0.7563 Intermediate Similarity NPC129578
0.7545 Intermediate Similarity NPC251071
0.7526 Intermediate Similarity NPC472580
0.7525 Intermediate Similarity NPC9475
0.75 Intermediate Similarity NPC309692
0.75 Intermediate Similarity NPC469437
0.7487 Intermediate Similarity NPC477957
0.7487 Intermediate Similarity NPC473996
0.7455 Intermediate Similarity NPC469439
0.7435 Intermediate Similarity NPC472636
0.7416 Intermediate Similarity NPC83019
0.7415 Intermediate Similarity NPC45389
0.7396 Intermediate Similarity NPC327269
0.7396 Intermediate Similarity NPC285623
0.7396 Intermediate Similarity NPC476238
0.7396 Intermediate Similarity NPC31627
0.7382 Intermediate Similarity NPC472421
0.7368 Intermediate Similarity NPC204580
0.7357 Intermediate Similarity NPC476429
0.7348 Intermediate Similarity NPC151171
0.7344 Intermediate Similarity NPC474744
0.7344 Intermediate Similarity NPC472420
0.7344 Intermediate Similarity NPC472423
0.7344 Intermediate Similarity NPC244577
0.7344 Intermediate Similarity NPC263384
0.7344 Intermediate Similarity NPC471676
0.7344 Intermediate Similarity NPC474772
0.7344 Intermediate Similarity NPC472422
0.7344 Intermediate Similarity NPC471675
0.7333 Intermediate Similarity NPC17677
0.7309 Intermediate Similarity NPC148124
0.7302 Intermediate Similarity NPC209040
0.729 Intermediate Similarity NPC268077
0.7286 Intermediate Similarity NPC108433
0.7277 Intermediate Similarity NPC168085
0.7277 Intermediate Similarity NPC5167
0.7277 Intermediate Similarity NPC85613
0.7273 Intermediate Similarity NPC264938
0.7269 Intermediate Similarity NPC207873
0.7269 Intermediate Similarity NPC100573
0.7268 Intermediate Similarity NPC223701
0.7268 Intermediate Similarity NPC7989
0.7268 Intermediate Similarity NPC472583
0.7265 Intermediate Similarity NPC99724
0.7264 Intermediate Similarity NPC127082
0.7254 Intermediate Similarity NPC471677
0.7249 Intermediate Similarity NPC316816
0.7249 Intermediate Similarity NPC478086
0.7249 Intermediate Similarity NPC106985
0.7249 Intermediate Similarity NPC310130
0.7249 Intermediate Similarity NPC68104
0.7249 Intermediate Similarity NPC164980
0.7249 Intermediate Similarity NPC257097
0.7249 Intermediate Similarity NPC150408
0.7249 Intermediate Similarity NPC149026
0.7249 Intermediate Similarity NPC175504
0.7249 Intermediate Similarity NPC18585
0.7249 Intermediate Similarity NPC91560
0.7249 Intermediate Similarity NPC221432
0.7249 Intermediate Similarity NPC39329
0.7249 Intermediate Similarity NPC75049
0.7249 Intermediate Similarity NPC214166
0.7249 Intermediate Similarity NPC143896
0.7249 Intermediate Similarity NPC166138
0.7249 Intermediate Similarity NPC169591
0.7246 Intermediate Similarity NPC474059
0.7244 Intermediate Similarity NPC97746
0.7244 Intermediate Similarity NPC122886
0.7244 Intermediate Similarity NPC19175
0.724 Intermediate Similarity NPC317492
0.724 Intermediate Similarity NPC472628
0.7235 Intermediate Similarity NPC477160
0.7231 Intermediate Similarity NPC477958
0.7225 Intermediate Similarity NPC23728
0.7225 Intermediate Similarity NPC472627
0.7225 Intermediate Similarity NPC14875
0.7225 Intermediate Similarity NPC296998
0.7225 Intermediate Similarity NPC110303
0.7225 Intermediate Similarity NPC473077
0.7222 Intermediate Similarity NPC478075
0.7216 Intermediate Similarity NPC171651
0.7216 Intermediate Similarity NPC35567
0.7216 Intermediate Similarity NPC243171
0.7216 Intermediate Similarity NPC475790
0.7215 Intermediate Similarity NPC127996
0.7212 Intermediate Similarity NPC476436
0.7211 Intermediate Similarity NPC131579
0.7211 Intermediate Similarity NPC197252
0.7211 Intermediate Similarity NPC473015
0.7211 Intermediate Similarity NPC470857
0.7211 Intermediate Similarity NPC236766
0.7211 Intermediate Similarity NPC473013
0.7211 Intermediate Similarity NPC131568
0.7209 Intermediate Similarity NPC87714
0.7207 Intermediate Similarity NPC77777
0.7196 Intermediate Similarity NPC227579
0.7196 Intermediate Similarity NPC182852
0.7196 Intermediate Similarity NPC76372
0.7196 Intermediate Similarity NPC228504
0.7196 Intermediate Similarity NPC324134
0.7196 Intermediate Similarity NPC78
0.7196 Intermediate Similarity NPC220998
0.7196 Intermediate Similarity NPC194432
0.7196 Intermediate Similarity NPC177354
0.7196 Intermediate Similarity NPC66515
0.7196 Intermediate Similarity NPC265040
0.7196 Intermediate Similarity NPC167624
0.7196 Intermediate Similarity NPC296917
0.7196 Intermediate Similarity NPC64915
0.7196 Intermediate Similarity NPC161506
0.7196 Intermediate Similarity NPC40833
0.7196 Intermediate Similarity NPC1089
0.7196 Intermediate Similarity NPC328164
0.7196 Intermediate Similarity NPC37496
0.7196 Intermediate Similarity NPC166482
0.7196 Intermediate Similarity NPC166934
0.7196 Intermediate Similarity NPC148757
0.7196 Intermediate Similarity NPC147145
0.7196 Intermediate Similarity NPC76338
0.7196 Intermediate Similarity NPC125855
0.7196 Intermediate Similarity NPC223500
0.7196 Intermediate Similarity NPC324436
0.7196 Intermediate Similarity NPC32739
0.7196 Intermediate Similarity NPC144499
0.7196 Intermediate Similarity NPC107572
0.7196 Intermediate Similarity NPC306829
0.7196 Intermediate Similarity NPC10937
0.7195 Intermediate Similarity NPC470002
0.7195 Intermediate Similarity NPC470001
0.7188 Intermediate Similarity NPC132592
0.7188 Intermediate Similarity NPC160821
0.7188 Intermediate Similarity NPC128476
0.7181 Intermediate Similarity NPC248903
0.7179 Intermediate Similarity NPC293286
0.7179 Intermediate Similarity NPC236756
0.7179 Intermediate Similarity NPC311579
0.7179 Intermediate Similarity NPC469722
0.7179 Intermediate Similarity NPC122365
0.7179 Intermediate Similarity NPC469405
0.7177 Intermediate Similarity NPC473004
0.7173 Intermediate Similarity NPC83357
0.7173 Intermediate Similarity NPC285630
0.7173 Intermediate Similarity NPC312973
0.7173 Intermediate Similarity NPC142405
0.7173 Intermediate Similarity NPC301276
0.7173 Intermediate Similarity NPC246948
0.7173 Intermediate Similarity NPC54577
0.7173 Intermediate Similarity NPC475052
0.7173 Intermediate Similarity NPC67805
0.7173 Intermediate Similarity NPC176229
0.7173 Intermediate Similarity NPC470647
0.7173 Intermediate Similarity NPC88964
0.7173 Intermediate Similarity NPC195621
0.7173 Intermediate Similarity NPC267375
0.7173 Intermediate Similarity NPC144691

  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 NPC321166 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
0.8325 Intermediate Similarity NPD2899 Discontinued
0.7887 Intermediate Similarity NPD3949 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD7064 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD6874 Approved
0.7619 Intermediate Similarity NPD3298 Approved
0.7586 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD7584 Approved
0.7536 Intermediate Similarity NPD7238 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD8461 Discontinued
0.7464 Intermediate Similarity NPD3297 Approved
0.7409 Intermediate Similarity NPD5496 Approved
0.7364 Intermediate Similarity NPD6198 Phase 1
0.7361 Intermediate Similarity NPD5726 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD956 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD4981 Phase 2
0.7325 Intermediate Similarity NPD6625 Approved
0.7321 Intermediate Similarity NPD4361 Phase 2
0.7321 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD7566 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD6608 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4363 Phase 3
0.7273 Intermediate Similarity NPD4360 Phase 2
0.7212 Intermediate Similarity NPD7186 Phase 3
0.7186 Intermediate Similarity NPD5186 Approved
0.7186 Intermediate Similarity NPD5183 Approved
0.7183 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD5937 Approved
0.7162 Intermediate Similarity NPD8067 Phase 3
0.7162 Intermediate Similarity NPD6962 Phase 2
0.7157 Intermediate Similarity NPD6104 Discontinued
0.711 Intermediate Similarity NPD7585 Approved
0.7093 Intermediate Similarity NPD3925 Approved
0.7082 Intermediate Similarity NPD4846 Phase 2
0.7079 Intermediate Similarity NPD3446 Phase 1
0.7071 Intermediate Similarity NPD7075 Discontinued
0.7064 Intermediate Similarity NPD7417 Discontinued
0.7064 Intermediate Similarity NPD7583 Approved
0.7037 Intermediate Similarity NPD5005 Approved
0.7037 Intermediate Similarity NPD5006 Approved
0.7034 Intermediate Similarity NPD1483 Discontinued
0.7026 Intermediate Similarity NPD4380 Phase 2
0.701 Intermediate Similarity NPD3793 Phase 3
0.701 Intermediate Similarity NPD6020 Phase 2
0.7009 Intermediate Similarity NPD4668 Phase 2
0.7005 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8367 Approved
0.6986 Remote Similarity NPD6296 Discontinued
0.6984 Remote Similarity NPD1549 Phase 2
0.6972 Remote Similarity NPD4465 Phase 2
0.6972 Remote Similarity NPD4467 Phase 2
0.6961 Remote Similarity NPD5940 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7626 Approved
0.6959 Remote Similarity NPD7627 Approved
0.6955 Remote Similarity NPD8492 Approved
0.6953 Remote Similarity NPD4373 Phase 2
0.6949 Remote Similarity NPD7560 Approved
0.6943 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6937 Remote Similarity NPD683 Approved
0.6935 Remote Similarity NPD7803 Approved
0.6931 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6931 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6927 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6926 Remote Similarity NPD7654 Discontinued
0.6905 Remote Similarity NPD3863 Clinical (unspecified phase)
0.69 Remote Similarity NPD955 Approved
0.6897 Remote Similarity NPD4952 Phase 3
0.6895 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6893 Remote Similarity NPD5900 Clinical (unspecified phase)
0.689 Remote Similarity NPD6021 Clinical (unspecified phase)
0.6884 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6884 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6883 Remote Similarity NPD3899 Clinical (unspecified phase)
0.6878 Remote Similarity NPD4613 Phase 2
0.6872 Remote Similarity NPD1898 Discontinued
0.6869 Remote Similarity NPD1934 Approved
0.6863 Remote Similarity NPD2246 Approved
0.6863 Remote Similarity NPD2248 Approved
0.6861 Remote Similarity NPD1945 Phase 1
0.686 Remote Similarity NPD3823 Discontinued
0.6856 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4420 Approved
0.6849 Remote Similarity NPD6790 Phase 1
0.6844 Remote Similarity NPD7559 Phase 2
0.6842 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7880 Clinical (unspecified phase)
0.6826 Remote Similarity NPD7278 Phase 2
0.6826 Remote Similarity NPD7279 Phase 2
0.6822 Remote Similarity NPD4539 Phase 1
0.6818 Remote Similarity NPD7411 Suspended
0.6816 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6816 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6816 Remote Similarity NPD5860 Discontinued
0.6812 Remote Similarity NPD7907 Approved
0.6809 Remote Similarity NPD7922 Phase 1
0.6808 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6806 Remote Similarity NPD4979 Clinical (unspecified phase)
0.6804 Remote Similarity NPD7071 Clinical (unspecified phase)
0.6798 Remote Similarity NPD2821 Approved
0.6798 Remote Similarity NPD4111 Phase 1
0.6789 Remote Similarity NPD2796 Approved
0.6784 Remote Similarity NPD6801 Discontinued
0.6783 Remote Similarity NPD6997 Phase 2
0.6779 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6777 Remote Similarity NPD3153 Approved
0.6777 Remote Similarity NPD3154 Approved
0.6774 Remote Similarity NPD5071 Phase 2
0.6774 Remote Similarity NPD7708 Approved
0.6771 Remote Similarity NPD2654 Approved
0.677 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6769 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6766 Remote Similarity NPD3882 Suspended
0.6762 Remote Similarity NPD7546 Discontinued
0.6761 Remote Similarity NPD5928 Phase 1
0.6758 Remote Similarity NPD2494 Approved
0.6758 Remote Similarity NPD3450 Approved
0.6758 Remote Similarity NPD2493 Approved
0.6758 Remote Similarity NPD3452 Approved
0.6758 Remote Similarity NPD6321 Discontinued
0.6757 Remote Similarity NPD7263 Phase 2
0.6754 Remote Similarity NPD1926 Approved
0.6753 Remote Similarity NPD3912 Discontinued
0.675 Remote Similarity NPD7819 Suspended
0.6749 Remote Similarity NPD5494 Approved
0.6744 Remote Similarity NPD4466 Phase 1
0.6743 Remote Similarity NPD8285 Discontinued
0.6742 Remote Similarity NPD4582 Approved
0.6742 Remote Similarity NPD4583 Approved
0.6741 Remote Similarity NPD5914 Approved
0.6737 Remote Similarity NPD1510 Phase 2
0.6734 Remote Similarity NPD7956 Approved
0.6734 Remote Similarity NPD7955 Approved
0.6734 Remote Similarity NPD2366 Approved
0.6732 Remote Similarity NPD5242 Approved
0.6728 Remote Similarity NPD2974 Approved
0.6728 Remote Similarity NPD2975 Approved
0.6728 Remote Similarity NPD2973 Approved
0.6727 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6725 Remote Similarity NPD4665 Approved
0.6723 Remote Similarity NPD7048 Phase 3
0.6716 Remote Similarity NPD6457 Approved
0.6715 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6712 Remote Similarity NPD7255 Clinical (unspecified phase)
0.6712 Remote Similarity NPD4580 Approved
0.6712 Remote Similarity NPD7174 Clinical (unspecified phase)
0.67 Remote Similarity NPD7577 Discontinued
0.67 Remote Similarity NPD6844 Discontinued
0.6699 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6699 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6697 Remote Similarity NPD4004 Approved
0.6697 Remote Similarity NPD4002 Approved
0.6696 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6696 Remote Similarity NPD3437 Discontinued
0.6695 Remote Similarity NPD7224 Discontinued
0.6695 Remote Similarity NPD7223 Discontinued
0.6683 Remote Similarity NPD5711 Approved
0.6683 Remote Similarity NPD5710 Approved
0.6683 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6683 Remote Similarity NPD3965 Phase 1
0.6682 Remote Similarity NPD4258 Approved
0.6682 Remote Similarity NPD4259 Approved
0.6681 Remote Similarity NPD6199 Discontinued
0.6681 Remote Similarity NPD5632 Approved
0.668 Remote Similarity NPD6716 Phase 1
0.6667 Remote Similarity NPD7556 Discontinued
0.6667 Remote Similarity NPD7811 Phase 3
0.6667 Remote Similarity NPD5025 Approved
0.6667 Remote Similarity NPD7810 Phase 3
0.6667 Remote Similarity NPD1880 Phase 3
0.6667 Remote Similarity NPD6559 Discontinued
0.6667 Remote Similarity NPD5637 Discontinued
0.6667 Remote Similarity NPD5488 Discontinued
0.6653 Remote Similarity NPD2300 Clinical (unspecified phase)
0.6652 Remote Similarity NPD4377 Discontinued
0.6652 Remote Similarity NPD7701 Phase 2
0.6652 Remote Similarity NPD2906 Approved
0.6652 Remote Similarity NPD2907 Approved
0.6652 Remote Similarity NPD4082 Approved
0.6652 Remote Similarity NPD3057 Approved
0.6651 Remote Similarity NPD2488 Approved
0.6651 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6651 Remote Similarity NPD7479 Phase 2
0.6651 Remote Similarity NPD2490 Approved
0.665 Remote Similarity NPD5889 Approved
0.665 Remote Similarity NPD8005 Clinical (unspecified phase)
0.665 Remote Similarity NPD6533 Clinical (unspecified phase)
0.665 Remote Similarity NPD5890 Approved
0.6636 Remote Similarity NPD5620 Clinical (unspecified phase)
0.6635 Remote Similarity NPD3818 Discontinued
0.6634 Remote Similarity NPD4986 Clinical (unspecified phase)
0.6633 Remote Similarity NPD6799 Approved
0.6624 Remote Similarity NPD7031 Phase 1
0.6622 Remote Similarity NPD7497 Discontinued
0.6621 Remote Similarity NPD5197 Approved
0.6621 Remote Similarity NPD5194 Approved
0.6621 Remote Similarity NPD5196 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