Structure

Physi-Chem Properties

Molecular Weight:  611.22
Volume:  598.873
LogP:  3.332
LogD:  2.294
LogS:  -3.991
# Rotatable Bonds:  10
TPSA:  202.84
# H-Bond Aceptor:  13
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.273
Synthetic Accessibility Score:  4.71
Fsp3:  0.387
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.347
MDCK Permeability:  7.581880709039979e-06
Pgp-inhibitor:  0.369
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.24
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  83.38263702392578%
Volume Distribution (VD):  0.951
Pgp-substrate:  8.14411449432373%

ADMET: Metabolism

CYP1A2-inhibitor:  0.04
CYP1A2-substrate:  0.077
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.117
CYP2C9-substrate:  0.111
CYP2D6-inhibitor:  0.119
CYP2D6-substrate:  0.135
CYP3A4-inhibitor:  0.08
CYP3A4-substrate:  0.063

ADMET: Excretion

Clearance (CL):  1.992
Half-life (T1/2):  0.177

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.963
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.159
Rat Oral Acute Toxicity:  0.927
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.11
Carcinogencity:  0.747
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.003

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

  Natural Product: NPC257266

Natural Product ID:  NPC257266
Common Name*:   Sodium;4-[[7-(4-Carbamoyloxy-3-Hydroxy-5-Methoxy-6,6-Dimethyloxan-2-Yl)Oxy-4-Hydroxy-8-Methyl-2-Oxochromen-3-Yl]Carbamoyl]-2-(3-Methylbut-2-Enyl)Phenolate
IUPAC Name:   sodium;4-[[7-(4-carbamoyloxy-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl)oxy-4-hydroxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-2-(3-methylbut-2-enyl)phenolate
Synonyms:  
Standard InCHIKey:  WWPRGAYLRGSOSU-UHFFFAOYSA-M
Standard InCHI:  InChI=1S/C31H36N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q;+1/p-1
SMILES:  CC(=CCc1cc(ccc1[O-])C(=O)Nc1c(c2ccc(c(C)c2oc1=O)OC1C(C(C(C(C)(C)O1)OC)OC(=N)O)O)O)C.[Na+]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2079809
PubChem CID:   54730021
23710502
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0001743] Coumarin glycosides

*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
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. DOI[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[16317898]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[17449162]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[19235686]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19666019]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[22707864]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[23088673]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[2393954]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[25594733]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28245 Strychnos nux-vomica Species Loganiaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 47973.34 nM PMID[548936]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 99540.54 nM PMID[548936]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 18407.72 nM PMID[548936]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 10000.0 nM PMID[548936]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 62950.62 nM PMID[548936]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 28379.19 nM PMID[548936]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 47533.52 nM PMID[548936]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 60534.09 nM PMID[548936]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 62230.03 nM PMID[548936]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 69183.1 nM PMID[548936]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 71779.43 nM PMID[548936]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 77803.66 nM PMID[548936]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 73790.42 nM PMID[548936]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[548936]

☑ 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 NPC257266 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
0.9946 High Similarity NPC257728
0.9892 High Similarity NPC153365
0.8201 Intermediate Similarity NPC314025
0.8158 Intermediate Similarity NPC314656
0.8158 Intermediate Similarity NPC314213
0.8115 Intermediate Similarity NPC315913
0.7812 Intermediate Similarity NPC76047
0.7807 Intermediate Similarity NPC43761
0.7737 Intermediate Similarity NPC183672
0.7737 Intermediate Similarity NPC257566
0.7737 Intermediate Similarity NPC124155
0.7725 Intermediate Similarity NPC478048
0.7713 Intermediate Similarity NPC73511
0.7703 Intermediate Similarity NPC92235
0.7701 Intermediate Similarity NPC45165
0.7689 Intermediate Similarity NPC328856
0.7689 Intermediate Similarity NPC321226
0.7689 Intermediate Similarity NPC180210
0.7689 Intermediate Similarity NPC478046
0.7689 Intermediate Similarity NPC314914
0.7689 Intermediate Similarity NPC478047
0.7684 Intermediate Similarity NPC44947
0.7684 Intermediate Similarity NPC131745
0.7672 Intermediate Similarity NPC472320
0.7663 Intermediate Similarity NPC107197
0.766 Intermediate Similarity NPC313163
0.766 Intermediate Similarity NPC161749
0.766 Intermediate Similarity NPC258035
0.766 Intermediate Similarity NPC197896
0.766 Intermediate Similarity NPC156457
0.766 Intermediate Similarity NPC43638
0.766 Intermediate Similarity NPC23817
0.7653 Intermediate Similarity NPC316368
0.7653 Intermediate Similarity NPC284236
0.7644 Intermediate Similarity NPC179198
0.7644 Intermediate Similarity NPC66087
0.7644 Intermediate Similarity NPC278419
0.7638 Intermediate Similarity NPC469437
0.7635 Intermediate Similarity NPC83019
0.7632 Intermediate Similarity NPC47923
0.7632 Intermediate Similarity NPC303913
0.7632 Intermediate Similarity NPC101636
0.7606 Intermediate Similarity NPC127406
0.7604 Intermediate Similarity NPC294722
0.7593 Intermediate Similarity NPC172355
0.7592 Intermediate Similarity NPC190450
0.7592 Intermediate Similarity NPC298171
0.7592 Intermediate Similarity NPC259834
0.7586 Intermediate Similarity NPC204580
0.7581 Intermediate Similarity NPC170101
0.7577 Intermediate Similarity NPC5319
0.7568 Intermediate Similarity NPC103116
0.7568 Intermediate Similarity NPC100818
0.7563 Intermediate Similarity NPC325176
0.7563 Intermediate Similarity NPC67629
0.7563 Intermediate Similarity NPC79736
0.7553 Intermediate Similarity NPC95090
0.7553 Intermediate Similarity NPC470604
0.7553 Intermediate Similarity NPC99233
0.7553 Intermediate Similarity NPC27408
0.7553 Intermediate Similarity NPC470603
0.7553 Intermediate Similarity NPC470605
0.7552 Intermediate Similarity NPC121703
0.7551 Intermediate Similarity NPC309692
0.7539 Intermediate Similarity NPC477628
0.7539 Intermediate Similarity NPC259957
0.7539 Intermediate Similarity NPC195685
0.7539 Intermediate Similarity NPC129217
0.7539 Intermediate Similarity NPC477629
0.7539 Intermediate Similarity NPC216496
0.7539 Intermediate Similarity NPC224530
0.7539 Intermediate Similarity NPC270675
0.7539 Intermediate Similarity NPC48093
0.7539 Intermediate Similarity NPC159579
0.7539 Intermediate Similarity NPC85707
0.7539 Intermediate Similarity NPC472994
0.7539 Intermediate Similarity NPC210961
0.7526 Intermediate Similarity NPC473634
0.7526 Intermediate Similarity NPC249977
0.7526 Intermediate Similarity NPC470607
0.7526 Intermediate Similarity NPC138811
0.7526 Intermediate Similarity NPC22062
0.7525 Intermediate Similarity NPC267549
0.7513 Intermediate Similarity NPC7752
0.7513 Intermediate Similarity NPC63105
0.7513 Intermediate Similarity NPC206378
0.7513 Intermediate Similarity NPC475979
0.7513 Intermediate Similarity NPC169645
0.7513 Intermediate Similarity NPC295613
0.7513 Intermediate Similarity NPC17521
0.7513 Intermediate Similarity NPC139060
0.7513 Intermediate Similarity NPC72016
0.7513 Intermediate Similarity NPC473657
0.7513 Intermediate Similarity NPC84482
0.7513 Intermediate Similarity NPC170475
0.75 Intermediate Similarity NPC106625
0.75 Intermediate Similarity NPC83283
0.75 Intermediate Similarity NPC472876
0.75 Intermediate Similarity NPC27942
0.75 Intermediate Similarity NPC87950
0.75 Intermediate Similarity NPC78021
0.75 Intermediate Similarity NPC472583
0.75 Intermediate Similarity NPC223701
0.75 Intermediate Similarity NPC108706
0.75 Intermediate Similarity NPC39360
0.75 Intermediate Similarity NPC211158
0.75 Intermediate Similarity NPC471764
0.75 Intermediate Similarity NPC210003
0.75 Intermediate Similarity NPC315914
0.75 Intermediate Similarity NPC7989
0.75 Intermediate Similarity NPC29763
0.75 Intermediate Similarity NPC87304
0.75 Intermediate Similarity NPC143851
0.75 Intermediate Similarity NPC268950
0.7487 Intermediate Similarity NPC200708
0.7487 Intermediate Similarity NPC97285
0.7487 Intermediate Similarity NPC473623
0.7487 Intermediate Similarity NPC246469
0.7487 Intermediate Similarity NPC271479
0.7487 Intermediate Similarity NPC142860
0.7487 Intermediate Similarity NPC271270
0.7486 Intermediate Similarity NPC85624
0.7474 Intermediate Similarity NPC298666
0.7474 Intermediate Similarity NPC260504
0.7474 Intermediate Similarity NPC473512
0.7474 Intermediate Similarity NPC89809
0.7474 Intermediate Similarity NPC470606
0.7474 Intermediate Similarity NPC129827
0.7474 Intermediate Similarity NPC65003
0.7474 Intermediate Similarity NPC64425
0.7474 Intermediate Similarity NPC44931
0.7474 Intermediate Similarity NPC262222
0.7474 Intermediate Similarity NPC182634
0.7474 Intermediate Similarity NPC122809
0.7474 Intermediate Similarity NPC473278
0.7474 Intermediate Similarity NPC60966
0.7474 Intermediate Similarity NPC108831
0.7474 Intermediate Similarity NPC68592
0.7473 Intermediate Similarity NPC104172
0.7473 Intermediate Similarity NPC88886
0.7463 Intermediate Similarity NPC106700
0.7462 Intermediate Similarity NPC163165
0.7462 Intermediate Similarity NPC208668
0.7461 Intermediate Similarity NPC80068
0.746 Intermediate Similarity NPC72649
0.746 Intermediate Similarity NPC97052
0.746 Intermediate Similarity NPC470681
0.746 Intermediate Similarity NPC26195
0.746 Intermediate Similarity NPC39351
0.746 Intermediate Similarity NPC477958
0.746 Intermediate Similarity NPC169248
0.7459 Intermediate Similarity NPC169510
0.745 Intermediate Similarity NPC477860
0.745 Intermediate Similarity NPC475161
0.7449 Intermediate Similarity NPC298778
0.7449 Intermediate Similarity NPC199079
0.7449 Intermediate Similarity NPC138990
0.7449 Intermediate Similarity NPC277532
0.7449 Intermediate Similarity NPC175429
0.7449 Intermediate Similarity NPC150767
0.7449 Intermediate Similarity NPC78734
0.7449 Intermediate Similarity NPC188815
0.7449 Intermediate Similarity NPC210808
0.7449 Intermediate Similarity NPC209550
0.7448 Intermediate Similarity NPC282169
0.7447 Intermediate Similarity NPC88484
0.7447 Intermediate Similarity NPC161881
0.7447 Intermediate Similarity NPC150123
0.7447 Intermediate Similarity NPC121001
0.7447 Intermediate Similarity NPC244583
0.7447 Intermediate Similarity NPC10807
0.7447 Intermediate Similarity NPC256141
0.7447 Intermediate Similarity NPC259182
0.7447 Intermediate Similarity NPC259767
0.7447 Intermediate Similarity NPC56232
0.7446 Intermediate Similarity NPC474044
0.7436 Intermediate Similarity NPC229729
0.7435 Intermediate Similarity NPC41121
0.7435 Intermediate Similarity NPC308265
0.7435 Intermediate Similarity NPC111929
0.7435 Intermediate Similarity NPC320283
0.7435 Intermediate Similarity NPC472459
0.7435 Intermediate Similarity NPC104677
0.7424 Intermediate Similarity NPC199533
0.7424 Intermediate Similarity NPC470454
0.7424 Intermediate Similarity NPC68381
0.7423 Intermediate Similarity NPC205824
0.7423 Intermediate Similarity NPC85751
0.7423 Intermediate Similarity NPC19240
0.7423 Intermediate Similarity NPC129264
0.7421 Intermediate Similarity NPC261866
0.7421 Intermediate Similarity NPC203500
0.7421 Intermediate Similarity NPC265480
0.7421 Intermediate Similarity NPC471787
0.7421 Intermediate Similarity NPC149368
0.7421 Intermediate Similarity NPC307938
0.7421 Intermediate Similarity NPC323593
0.7411 Intermediate Similarity NPC101399
0.7411 Intermediate Similarity NPC11847
0.7411 Intermediate Similarity NPC474522

  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 NPC257266 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
1.0 High Similarity NPD7583 Approved
0.9946 High Similarity NPD7585 Approved
0.9365 High Similarity NPD7584 Approved
0.7716 Intermediate Similarity NPD3863 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7577 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD3451 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD5192 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD7783 Phase 2
0.7453 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD7597 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7811 Phase 3
0.7427 Intermediate Similarity NPD7810 Phase 3
0.7391 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD7075 Discontinued
0.734 Intermediate Similarity NPD4380 Phase 2
0.7337 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7054 Approved
0.7286 Intermediate Similarity NPD7039 Approved
0.7286 Intermediate Similarity NPD7038 Approved
0.7282 Intermediate Similarity NPD5242 Approved
0.7273 Intermediate Similarity NPD7472 Approved
0.7273 Intermediate Similarity NPD7074 Phase 3
0.7269 Intermediate Similarity NPD7930 Approved
0.7263 Intermediate Similarity NPD6801 Discontinued
0.7236 Intermediate Similarity NPD3823 Discontinued
0.723 Intermediate Similarity NPD7701 Phase 2
0.722 Intermediate Similarity NPD8059 Phase 3
0.722 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD7999 Approved
0.7206 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7251 Discontinued
0.72 Intermediate Similarity NPD6559 Discontinued
0.7196 Intermediate Similarity NPD8151 Discontinued
0.7183 Intermediate Similarity NPD6973 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD3818 Discontinued
0.7164 Intermediate Similarity NPD7808 Phase 3
0.7164 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5005 Approved
0.7156 Intermediate Similarity NPD5006 Approved
0.7156 Intermediate Similarity NPD6823 Phase 2
0.715 Intermediate Similarity NPD4360 Phase 2
0.715 Intermediate Similarity NPD6797 Phase 2
0.715 Intermediate Similarity NPD4363 Phase 3
0.715 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6781 Approved
0.7143 Intermediate Similarity NPD6777 Approved
0.7143 Intermediate Similarity NPD6776 Approved
0.7143 Intermediate Similarity NPD6779 Approved
0.7143 Intermediate Similarity NPD6780 Approved
0.7143 Intermediate Similarity NPD6782 Approved
0.7143 Intermediate Similarity NPD6778 Approved
0.7136 Intermediate Similarity NPD5844 Phase 1
0.713 Intermediate Similarity NPD7801 Approved
0.7123 Intermediate Similarity NPD7696 Phase 3
0.7123 Intermediate Similarity NPD7697 Approved
0.7123 Intermediate Similarity NPD7698 Approved
0.712 Intermediate Similarity NPD7411 Suspended
0.7115 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7106 Intermediate Similarity NPD8152 Approved
0.7106 Intermediate Similarity NPD8153 Approved
0.7089 Intermediate Similarity NPD7871 Phase 2
0.7089 Intermediate Similarity NPD8319 Approved
0.7089 Intermediate Similarity NPD8320 Phase 1
0.7089 Intermediate Similarity NPD7870 Phase 2
0.7087 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7874 Approved
0.7083 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7061 Intermediate Similarity NPD6625 Approved
0.7048 Intermediate Similarity NPD4420 Approved
0.7047 Intermediate Similarity NPD7819 Suspended
0.7047 Intermediate Similarity NPD8455 Phase 2
0.7045 Intermediate Similarity NPD3949 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7064 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7435 Discontinued
0.702 Intermediate Similarity NPD2388 Discontinued
0.7014 Intermediate Similarity NPD8285 Discontinued
0.7 Intermediate Similarity NPD7177 Discontinued
0.6986 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5457 Discontinued
0.6971 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6968 Remote Similarity NPD8404 Phase 2
0.6959 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7880 Clinical (unspecified phase)
0.6952 Remote Similarity NPD4361 Phase 2
0.6952 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6104 Discontinued
0.6943 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6793 Clinical (unspecified phase)
0.6939 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6938 Remote Similarity NPD4466 Phase 1
0.6934 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6851 Approved
0.6927 Remote Similarity NPD6853 Approved
0.6923 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6916 Remote Similarity NPD8469 Approved
0.6911 Remote Similarity NPD5403 Approved
0.6908 Remote Similarity NPD1898 Discontinued
0.6905 Remote Similarity NPD6535 Approved
0.6905 Remote Similarity NPD6534 Approved
0.69 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6895 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6895 Remote Similarity NPD4378 Clinical (unspecified phase)
0.689 Remote Similarity NPD3819 Phase 2
0.6889 Remote Similarity NPD6997 Phase 2
0.6887 Remote Similarity NPD7700 Phase 2
0.6887 Remote Similarity NPD7699 Phase 2
0.6884 Remote Similarity NPD7608 Discontinued
0.6869 Remote Similarity NPD7476 Discontinued
0.6869 Remote Similarity NPD2904 Discontinued
0.6862 Remote Similarity NPD4628 Phase 3
0.6857 Remote Similarity NPD6213 Phase 3
0.6857 Remote Similarity NPD6212 Phase 3
0.6857 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6856 Remote Similarity NPD5890 Approved
0.6856 Remote Similarity NPD5889 Approved
0.6854 Remote Similarity NPD7565 Approved
0.6842 Remote Similarity NPD6799 Approved
0.684 Remote Similarity NPD6621 Clinical (unspecified phase)
0.684 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6839 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6837 Remote Similarity NPD5402 Approved
0.6837 Remote Similarity NPD3817 Phase 2
0.6827 Remote Similarity NPD7693 Approved
0.6824 Remote Similarity NPD7048 Phase 3
0.6821 Remote Similarity NPD1934 Approved
0.6816 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6166 Phase 2
0.6814 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6809 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6806 Remote Similarity NPD5401 Approved
0.6804 Remote Similarity NPD6585 Discontinued
0.6802 Remote Similarity NPD7768 Phase 2
0.6796 Remote Similarity NPD8312 Approved
0.6796 Remote Similarity NPD8313 Approved
0.679 Remote Similarity NPD8461 Discontinued
0.6789 Remote Similarity NPD6666 Approved
0.6789 Remote Similarity NPD6667 Approved
0.6788 Remote Similarity NPD1653 Approved
0.6787 Remote Similarity NPD7827 Phase 1
0.6784 Remote Similarity NPD5677 Discontinued
0.6784 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6784 Remote Similarity NPD2041 Clinical (unspecified phase)
0.678 Remote Similarity NPD7685 Pre-registration
0.6777 Remote Similarity NPD6181 Discontinued
0.6776 Remote Similarity NPD6874 Approved
0.6772 Remote Similarity NPD3750 Approved
0.6771 Remote Similarity NPD7047 Phase 3
0.677 Remote Similarity NPD8366 Approved
0.6769 Remote Similarity NPD6072 Discontinued
0.6769 Remote Similarity NPD6677 Suspended
0.6755 Remote Similarity NPD1549 Phase 2
0.6753 Remote Similarity NPD8067 Phase 3
0.6753 Remote Similarity NPD7458 Discontinued
0.6751 Remote Similarity NPD5353 Approved
0.6751 Remote Similarity NPD7318 Phase 3
0.6745 Remote Similarity NPD7256 Discontinued
0.6745 Remote Similarity NPD3473 Clinical (unspecified phase)
0.6738 Remote Similarity NPD2796 Approved
0.6735 Remote Similarity NPD4433 Discontinued
0.6732 Remote Similarity NPD6297 Approved
0.6725 Remote Similarity NPD8491 Approved
0.6721 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7447 Phase 1
0.6718 Remote Similarity NPD6599 Discontinued
0.6716 Remote Similarity NPD42 Phase 2
0.6716 Remote Similarity NPD6042 Phase 2
0.6713 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6703 Remote Similarity NPD5124 Phase 1
0.6703 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6702 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6702 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6701 Remote Similarity NPD1465 Phase 2
0.67 Remote Similarity NPD4666 Phase 3
0.67 Remote Similarity NPD3366 Approved
0.6699 Remote Similarity NPD8150 Discontinued
0.6684 Remote Similarity NPD6385 Approved
0.6684 Remote Similarity NPD6386 Approved
0.6683 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6683 Remote Similarity NPD1309 Phase 2
0.6683 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6683 Remote Similarity NPD8031 Discontinued
0.6683 Remote Similarity NPD1307 Phase 2
0.6682 Remote Similarity NPD8162 Phase 2
0.6682 Remote Similarity NPD6863 Phase 2
0.6682 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7190 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7212 Phase 2
0.6667 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7549 Discontinued
0.6667 Remote Similarity NPD7199 Phase 2
0.6667 Remote Similarity NPD7228 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