Structure

Physi-Chem Properties

Molecular Weight:  353.13
Volume:  348.187
LogP:  2.589
LogD:  2.746
LogS:  -3.982
# Rotatable Bonds:  1
TPSA:  68.23
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.848
Synthetic Accessibility Score:  3.958
Fsp3:  0.35
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:  -4.827
MDCK Permeability:  2.3883108951849863e-05
Pgp-inhibitor:  0.027
Pgp-substrate:  0.052
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.994
Plasma Protein Binding (PPB):  82.10395050048828%
Volume Distribution (VD):  2.009
Pgp-substrate:  11.526853561401367%

ADMET: Metabolism

CYP1A2-inhibitor:  0.899
CYP1A2-substrate:  0.878
CYP2C19-inhibitor:  0.88
CYP2C19-substrate:  0.911
CYP2C9-inhibitor:  0.587
CYP2C9-substrate:  0.821
CYP2D6-inhibitor:  0.957
CYP2D6-substrate:  0.883
CYP3A4-inhibitor:  0.959
CYP3A4-substrate:  0.927

ADMET: Excretion

Clearance (CL):  17.697
Half-life (T1/2):  0.221

ADMET: Toxicity

hERG Blockers:  0.081
Human Hepatotoxicity (H-HT):  0.328
Drug-inuced Liver Injury (DILI):  0.257
AMES Toxicity:  0.508
Rat Oral Acute Toxicity:  0.33
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.058
Carcinogencity:  0.883
Eye Corrosion:  0.003
Eye Irritation:  0.018
Respiratory Toxicity:  0.401

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

  Natural Product: NPC207239

Natural Product ID:  NPC207239
Common Name*:   (1S)-7-Hydroxy-6-Methoxy-2-Methylspiro[3,4-Dihydroisoquinoline-1,7'-6H-Cyclopenta[G][1,3]Benzodioxole]-8'-One
IUPAC Name:   (1S)-7-hydroxy-6-methoxy-2-methylspiro[3,4-dihydroisoquinoline-1,7'-6H-cyclopenta[g][1,3]benzodioxole]-8'-one
Synonyms:  
Standard InCHIKey:  AHNUBWYOIHCGFN-FQEVSTJZSA-N
Standard InCHI:  InChI=1S/C20H19NO5/c1-21-6-5-11-7-16(24-2)14(22)8-13(11)20(21)9-12-3-4-15-18(26-10-25-15)17(12)19(20)23/h3-4,7-8,22H,5-6,9-10H2,1-2H3/t20-/m0/s1
SMILES:  COc1cc2CCN([C@]3(c2cc1O)Cc1c(C3=O)c2OCOc2cc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2374322
PubChem CID:   185623
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000027] Indanes
        • [CHEMONTID:0001151] Indanones

*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
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. root n.a. PMID[22029392]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. seed n.a. PMID[22029392]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. aerial part n.a. PMID[22029392]
NPO14103 Fumaria parviflora Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO14103 Fumaria parviflora Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14103 Fumaria parviflora Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14103 Fumaria parviflora Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8675 Fumaria vaillantii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14103 Fumaria parviflora Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 73451.39 nM PMID[467974]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[467974]

☑ 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 NPC207239 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
0.8919 High Similarity NPC24228
0.8907 High Similarity NPC226708
0.8778 High Similarity NPC27887
0.861 High Similarity NPC469816
0.861 High Similarity NPC469815
0.8564 High Similarity NPC125924
0.8541 High Similarity NPC477259
0.8541 High Similarity NPC169387
0.8407 Intermediate Similarity NPC308267
0.8398 Intermediate Similarity NPC303581
0.8398 Intermediate Similarity NPC67978
0.8287 Intermediate Similarity NPC86469
0.8281 Intermediate Similarity NPC46744
0.8281 Intermediate Similarity NPC70290
0.8281 Intermediate Similarity NPC124302
0.8281 Intermediate Similarity NPC215098
0.8281 Intermediate Similarity NPC73020
0.8281 Intermediate Similarity NPC14622
0.8272 Intermediate Similarity NPC477258
0.8235 Intermediate Similarity NPC116007
0.8196 Intermediate Similarity NPC72788
0.8196 Intermediate Similarity NPC314100
0.8196 Intermediate Similarity NPC120671
0.8196 Intermediate Similarity NPC226652
0.8162 Intermediate Similarity NPC222524
0.8138 Intermediate Similarity NPC83511
0.8122 Intermediate Similarity NPC276944
0.8122 Intermediate Similarity NPC238530
0.8122 Intermediate Similarity NPC232514
0.8118 Intermediate Similarity NPC121400
0.8112 Intermediate Similarity NPC2173
0.8112 Intermediate Similarity NPC328700
0.8112 Intermediate Similarity NPC202771
0.8112 Intermediate Similarity NPC119818
0.8011 Intermediate Similarity NPC153631
0.8 Intermediate Similarity NPC111485
0.8 Intermediate Similarity NPC18306
0.799 Intermediate Similarity NPC80472
0.7989 Intermediate Similarity NPC470324
0.796 Intermediate Similarity NPC46990
0.7956 Intermediate Similarity NPC135006
0.7917 Intermediate Similarity NPC166979
0.7897 Intermediate Similarity NPC33256
0.7853 Intermediate Similarity NPC470088
0.7835 Intermediate Similarity NPC63152
0.7824 Intermediate Similarity NPC208890
0.7821 Intermediate Similarity NPC223124
0.7817 Intermediate Similarity NPC71124
0.7797 Intermediate Similarity NPC246587
0.7797 Intermediate Similarity NPC147390
0.7797 Intermediate Similarity NPC24233
0.7797 Intermediate Similarity NPC428
0.7797 Intermediate Similarity NPC135538
0.7797 Intermediate Similarity NPC476571
0.7797 Intermediate Similarity NPC475959
0.7772 Intermediate Similarity NPC162694
0.7772 Intermediate Similarity NPC59567
0.7753 Intermediate Similarity NPC477565
0.7753 Intermediate Similarity NPC103379
0.7749 Intermediate Similarity NPC298339
0.7742 Intermediate Similarity NPC298979
0.774 Intermediate Similarity NPC191376
0.774 Intermediate Similarity NPC321505
0.774 Intermediate Similarity NPC179825
0.7737 Intermediate Similarity NPC320223
0.7737 Intermediate Similarity NPC114364
0.7735 Intermediate Similarity NPC110416
0.7735 Intermediate Similarity NPC184026
0.7735 Intermediate Similarity NPC193949
0.7735 Intermediate Similarity NPC276588
0.7735 Intermediate Similarity NPC54379
0.7735 Intermediate Similarity NPC41178
0.7735 Intermediate Similarity NPC216459
0.7735 Intermediate Similarity NPC172765
0.7735 Intermediate Similarity NPC295691
0.7735 Intermediate Similarity NPC469817
0.7735 Intermediate Similarity NPC127674
0.7735 Intermediate Similarity NPC2413
0.7735 Intermediate Similarity NPC39701
0.7735 Intermediate Similarity NPC278799
0.7735 Intermediate Similarity NPC207757
0.7735 Intermediate Similarity NPC189266
0.7735 Intermediate Similarity NPC5238
0.7735 Intermediate Similarity NPC249797
0.7735 Intermediate Similarity NPC204828
0.7735 Intermediate Similarity NPC138487
0.7725 Intermediate Similarity NPC199465
0.7725 Intermediate Similarity NPC128560
0.7725 Intermediate Similarity NPC229166
0.7711 Intermediate Similarity NPC207971
0.7709 Intermediate Similarity NPC223125
0.7704 Intermediate Similarity NPC254957
0.7692 Intermediate Similarity NPC31311
0.7692 Intermediate Similarity NPC234392
0.7692 Intermediate Similarity NPC146288
0.7688 Intermediate Similarity NPC5374
0.7673 Intermediate Similarity NPC268077
0.7653 Intermediate Similarity NPC196231
0.7644 Intermediate Similarity NPC21885
0.764 Intermediate Similarity NPC476151
0.7634 Intermediate Similarity NPC231198
0.7627 Intermediate Similarity NPC185838
0.7624 Intermediate Similarity NPC233029
0.7624 Intermediate Similarity NPC210148
0.7617 Intermediate Similarity NPC116284
0.7611 Intermediate Similarity NPC88249
0.7611 Intermediate Similarity NPC97221
0.7611 Intermediate Similarity NPC151895
0.7611 Intermediate Similarity NPC192768
0.7611 Intermediate Similarity NPC220858
0.7609 Intermediate Similarity NPC118804
0.7609 Intermediate Similarity NPC106786
0.76 Intermediate Similarity NPC267414
0.7596 Intermediate Similarity NPC55470
0.759 Intermediate Similarity NPC230098
0.7581 Intermediate Similarity NPC315914
0.7579 Intermediate Similarity NPC2314
0.7577 Intermediate Similarity NPC474746
0.7577 Intermediate Similarity NPC475981
0.7574 Intermediate Similarity NPC286135
0.7569 Intermediate Similarity NPC119669
0.7569 Intermediate Similarity NPC37220
0.7556 Intermediate Similarity NPC469540
0.7556 Intermediate Similarity NPC469539
0.7551 Intermediate Similarity NPC141440
0.7541 Intermediate Similarity NPC93593
0.7539 Intermediate Similarity NPC207721
0.7528 Intermediate Similarity NPC469978
0.7528 Intermediate Similarity NPC46880
0.7527 Intermediate Similarity NPC133011
0.7527 Intermediate Similarity NPC148898
0.7527 Intermediate Similarity NPC82285
0.7526 Intermediate Similarity NPC102760
0.7513 Intermediate Similarity NPC474745
0.7513 Intermediate Similarity NPC32154
0.7487 Intermediate Similarity NPC135772
0.7487 Intermediate Similarity NPC476569
0.7486 Intermediate Similarity NPC477564
0.7486 Intermediate Similarity NPC2295
0.7476 Intermediate Similarity NPC478048
0.7474 Intermediate Similarity NPC476574
0.7474 Intermediate Similarity NPC155442
0.7474 Intermediate Similarity NPC312918
0.7474 Intermediate Similarity NPC477561
0.7473 Intermediate Similarity NPC76213
0.7473 Intermediate Similarity NPC97072
0.7473 Intermediate Similarity NPC166014
0.7473 Intermediate Similarity NPC160298
0.7473 Intermediate Similarity NPC266753
0.7473 Intermediate Similarity NPC477559
0.7473 Intermediate Similarity NPC232924
0.7473 Intermediate Similarity NPC27410
0.7473 Intermediate Similarity NPC215829
0.7473 Intermediate Similarity NPC306902
0.7473 Intermediate Similarity NPC277669
0.7463 Intermediate Similarity NPC193906
0.7463 Intermediate Similarity NPC17677
0.7463 Intermediate Similarity NPC23080
0.7461 Intermediate Similarity NPC118633
0.7461 Intermediate Similarity NPC327005
0.7461 Intermediate Similarity NPC294790
0.7461 Intermediate Similarity NPC148693
0.7461 Intermediate Similarity NPC474325
0.746 Intermediate Similarity NPC100566
0.7458 Intermediate Similarity NPC138438
0.7458 Intermediate Similarity NPC908
0.7448 Intermediate Similarity NPC187678
0.7447 Intermediate Similarity NPC3375
0.7447 Intermediate Similarity NPC255607
0.7441 Intermediate Similarity NPC321226
0.7441 Intermediate Similarity NPC478047
0.7441 Intermediate Similarity NPC180210
0.7441 Intermediate Similarity NPC478046
0.7441 Intermediate Similarity NPC328856
0.7441 Intermediate Similarity NPC314914
0.7437 Intermediate Similarity NPC94499
0.7424 Intermediate Similarity NPC82763
0.7423 Intermediate Similarity NPC149285
0.7421 Intermediate Similarity NPC241055
0.7409 Intermediate Similarity NPC237044
0.7409 Intermediate Similarity NPC241704
0.7409 Intermediate Similarity NPC35680
0.7407 Intermediate Similarity NPC264850
0.7407 Intermediate Similarity NPC13916
0.7407 Intermediate Similarity NPC476432
0.7407 Intermediate Similarity NPC24264
0.7406 Intermediate Similarity NPC316368
0.7406 Intermediate Similarity NPC284236
0.7405 Intermediate Similarity NPC147091
0.7402 Intermediate Similarity NPC97086
0.7401 Intermediate Similarity NPC213206
0.7401 Intermediate Similarity NPC474915
0.7401 Intermediate Similarity NPC188163
0.7401 Intermediate Similarity NPC328750
0.7394 Intermediate Similarity NPC324144
0.7391 Intermediate Similarity NPC470708
0.7382 Intermediate Similarity NPC152212
0.7382 Intermediate Similarity NPC311991
0.7376 Intermediate Similarity NPC293624
0.7376 Intermediate Similarity NPC83019

  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 NPC207239 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
0.8281 Intermediate Similarity NPD4420 Approved
0.8146 Intermediate Similarity NPD5978 Approved
0.8146 Intermediate Similarity NPD5977 Approved
0.8112 Intermediate Similarity NPD5006 Approved
0.8112 Intermediate Similarity NPD5005 Approved
0.7989 Intermediate Similarity NPD2898 Approved
0.7749 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD824 Approved
0.7565 Intermediate Similarity NPD7281 Phase 3
0.7565 Intermediate Similarity NPD7280 Phase 3
0.7513 Intermediate Similarity NPD2488 Approved
0.7513 Intermediate Similarity NPD2490 Approved
0.7475 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD3641 Approved
0.7459 Intermediate Similarity NPD3640 Phase 3
0.7459 Intermediate Similarity NPD3639 Approved
0.745 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD6297 Approved
0.7401 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5457 Discontinued
0.7379 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD3450 Approved
0.7353 Intermediate Similarity NPD3452 Approved
0.7353 Intermediate Similarity NPD2494 Approved
0.7353 Intermediate Similarity NPD2493 Approved
0.7348 Intermediate Similarity NPD4584 Approved
0.7337 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3448 Approved
0.7317 Intermediate Similarity NPD2491 Approved
0.7265 Intermediate Similarity NPD7048 Phase 3
0.7259 Intermediate Similarity NPD6853 Approved
0.7259 Intermediate Similarity NPD6851 Approved
0.7259 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD4582 Approved
0.7246 Intermediate Similarity NPD4583 Approved
0.7233 Intermediate Similarity NPD956 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD3057 Approved
0.7222 Intermediate Similarity NPD7907 Approved
0.7216 Intermediate Similarity NPD5312 Approved
0.7216 Intermediate Similarity NPD5313 Approved
0.7198 Intermediate Similarity NPD4004 Approved
0.7198 Intermediate Similarity NPD4002 Approved
0.7182 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD2973 Approved
0.7157 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD2975 Approved
0.7157 Intermediate Similarity NPD2974 Approved
0.7151 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD3533 Approved
0.715 Intermediate Similarity NPD2972 Approved
0.7135 Intermediate Similarity NPD4010 Discontinued
0.713 Intermediate Similarity NPD2899 Discontinued
0.713 Intermediate Similarity NPD4111 Phase 1
0.713 Intermediate Similarity NPD4665 Approved
0.7129 Intermediate Similarity NPD7296 Approved
0.7128 Intermediate Similarity NPD3050 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD2968 Approved
0.7121 Intermediate Similarity NPD2971 Approved
0.7114 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD6385 Approved
0.7112 Intermediate Similarity NPD6386 Approved
0.7112 Intermediate Similarity NPD7110 Phase 1
0.7105 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD7833 Phase 2
0.7105 Intermediate Similarity NPD7831 Phase 2
0.7098 Intermediate Similarity NPD5242 Approved
0.7095 Intermediate Similarity NPD7584 Approved
0.7085 Intermediate Similarity NPD6618 Phase 2
0.7081 Intermediate Similarity NPD4040 Phase 1
0.7077 Intermediate Similarity NPD3818 Discontinued
0.7062 Intermediate Similarity NPD4859 Phase 1
0.7056 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD4580 Approved
0.7053 Intermediate Similarity NPD4107 Approved
0.7032 Intermediate Similarity NPD6997 Phase 2
0.7 Intermediate Similarity NPD8053 Approved
0.7 Intermediate Similarity NPD8054 Approved
0.699 Remote Similarity NPD5564 Approved
0.6989 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7701 Phase 2
0.698 Remote Similarity NPD7291 Discontinued
0.6978 Remote Similarity NPD6625 Approved
0.6976 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6974 Remote Similarity NPD2489 Approved
0.6974 Remote Similarity NPD27 Approved
0.6967 Remote Similarity NPD8161 Suspended
0.6963 Remote Similarity NPD5676 Approved
0.6947 Remote Similarity NPD2977 Approved
0.6947 Remote Similarity NPD2978 Approved
0.6946 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7930 Approved
0.6939 Remote Similarity NPD3446 Phase 1
0.6938 Remote Similarity NPD4482 Phase 3
0.6927 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7074 Phase 3
0.6915 Remote Similarity NPD4017 Approved
0.6912 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6909 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6907 Remote Similarity NPD6107 Approved
0.6898 Remote Similarity NPD1670 Discontinued
0.6895 Remote Similarity NPD1934 Approved
0.6895 Remote Similarity NPD6844 Discontinued
0.6882 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6878 Remote Similarity NPD6875 Approved
0.6878 Remote Similarity NPD6876 Approved
0.6875 Remote Similarity NPD3882 Suspended
0.6872 Remote Similarity NPD7497 Discontinued
0.6872 Remote Similarity NPD6071 Discontinued
0.6869 Remote Similarity NPD7054 Approved
0.6869 Remote Similarity NPD6020 Phase 2
0.6865 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6859 Remote Similarity NPD2801 Approved
0.6856 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7827 Phase 1
0.6847 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6212 Phase 3
0.6845 Remote Similarity NPD6213 Phase 3
0.6845 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6873 Phase 2
0.6842 Remote Similarity NPD4773 Phase 2
0.6842 Remote Similarity NPD4772 Phase 2
0.6837 Remote Similarity NPD2970 Approved
0.6837 Remote Similarity NPD2969 Approved
0.6836 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7047 Phase 3
0.6834 Remote Similarity NPD7472 Approved
0.6828 Remote Similarity NPD2421 Approved
0.6828 Remote Similarity NPD2420 Approved
0.6825 Remote Similarity NPD3455 Phase 2
0.6823 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6823 Remote Similarity NPD2560 Approved
0.6823 Remote Similarity NPD5967 Approved
0.6823 Remote Similarity NPD2563 Approved
0.6821 Remote Similarity NPD7199 Phase 2
0.6811 Remote Similarity NPD5241 Discontinued
0.6809 Remote Similarity NPD6030 Approved
0.6809 Remote Similarity NPD6031 Approved
0.6806 Remote Similarity NPD7298 Approved
0.6806 Remote Similarity NPD683 Approved
0.68 Remote Similarity NPD3823 Discontinued
0.6796 Remote Similarity NPD5968 Phase 3
0.6794 Remote Similarity NPD5071 Phase 2
0.6789 Remote Similarity NPD7028 Phase 2
0.6786 Remote Similarity NPD6232 Discontinued
0.6786 Remote Similarity NPD3051 Approved
0.6786 Remote Similarity NPD5711 Approved
0.6786 Remote Similarity NPD4166 Phase 2
0.6786 Remote Similarity NPD5710 Approved
0.6782 Remote Similarity NPD6146 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4078 Clinical (unspecified phase)
0.6779 Remote Similarity NPD4361 Phase 2
0.6779 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6771 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7473 Discontinued
0.6766 Remote Similarity NPD7039 Approved
0.6766 Remote Similarity NPD7038 Approved
0.6762 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6751 Remote Similarity NPD7184 Clinical (unspecified phase)
0.675 Remote Similarity NPD5441 Clinical (unspecified phase)
0.674 Remote Similarity NPD2492 Phase 1
0.6739 Remote Similarity NPD4846 Phase 2
0.6737 Remote Similarity NPD8153 Approved
0.6737 Remote Similarity NPD8152 Approved
0.6733 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7906 Approved
0.673 Remote Similarity NPD6779 Approved
0.673 Remote Similarity NPD6780 Approved
0.673 Remote Similarity NPD6777 Approved
0.673 Remote Similarity NPD6782 Approved
0.673 Remote Similarity NPD6781 Approved
0.673 Remote Similarity NPD6778 Approved
0.673 Remote Similarity NPD6776 Approved
0.6721 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7577 Discontinued
0.6717 Remote Similarity NPD4481 Phase 3
0.6716 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6716 Remote Similarity NPD6797 Phase 2
0.6701 Remote Similarity NPD6747 Phase 1
0.6701 Remote Similarity NPD7315 Approved
0.67 Remote Similarity NPD7313 Approved
0.67 Remote Similarity NPD7310 Approved
0.67 Remote Similarity NPD7311 Approved
0.67 Remote Similarity NPD7312 Approved
0.6699 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7278 Phase 2
0.6696 Remote Similarity NPD7279 Phase 2
0.6684 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6683 Remote Similarity NPD4466 Phase 1
0.6683 Remote Similarity NPD7251 Discontinued
0.6683 Remote Similarity NPD7685 Pre-registration
0.6681 Remote Similarity NPD7922 Phase 1
0.6667 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7309 Approved
0.6667 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7585 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