Structure

Physi-Chem Properties

Molecular Weight:  271.05
Volume:  252.967
LogP:  2.612
LogD:  2.093
LogS:  -4.083
# Rotatable Bonds:  0
TPSA:  91.78
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.542
Synthetic Accessibility Score:  2.624
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.082
MDCK Permeability:  1.1849653674289584e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.15

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.021
Plasma Protein Binding (PPB):  95.33858489990234%
Volume Distribution (VD):  0.459
Pgp-substrate:  4.474422931671143%

ADMET: Metabolism

CYP1A2-inhibitor:  0.981
CYP1A2-substrate:  0.281
CYP2C19-inhibitor:  0.36
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.736
CYP2C9-substrate:  0.639
CYP2D6-inhibitor:  0.802
CYP2D6-substrate:  0.208
CYP3A4-inhibitor:  0.67
CYP3A4-substrate:  0.081

ADMET: Excretion

Clearance (CL):  13.343
Half-life (T1/2):  0.489

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.15
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.602
Rat Oral Acute Toxicity:  0.266
Maximum Recommended Daily Dose:  0.054
Skin Sensitization:  0.883
Carcinogencity:  0.867
Eye Corrosion:  0.015
Eye Irritation:  0.937
Respiratory Toxicity:  0.879

Download Data

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

  Natural Product: NPC148409

Natural Product ID:  NPC148409
Common Name*:   Narciprimine
IUPAC Name:   4,7-dihydroxy-5H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:   Narciprimine
Standard InCHIKey:  PEOASDPEDCJOME-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H9NO5/c16-8-3-1-2-6-7-4-9-13(20-5-19-9)12(17)10(7)14(18)15-11(6)8/h1-4,16-17H,5H2,(H,15,18)
SMILES:  Oc1nc2c(O)cccc2c2c1c(O)c1OCOc1c2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1980408
PubChem CID:   5387508
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001775] Amaryllidaceae alkaloids
        • [CHEMONTID:0004129] Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids

*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
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[21314165]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[21314165]
NPO33437 amaryllidaceae Family Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[22921081]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9927 Crinum asiaticum Species Amaryllidaceae 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. 20749.14 nM PMID[498370]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 17100.15 nM PMID[498370]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 15812.48 nM PMID[498370]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 6441.69 nM PMID[498370]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 13427.65 nM PMID[498370]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 17988.71 nM PMID[498370]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 17100.15 nM PMID[498370]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 22803.42 nM PMID[498370]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 21232.44 nM PMID[498370]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 17498.47 nM PMID[498370]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 21478.3 nM PMID[498370]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 16826.74 nM PMID[498370]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 19230.92 nM PMID[498370]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 15958.79 nM PMID[498370]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 23550.49 nM PMID[498370]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 18663.8 nM PMID[498370]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 13583.13 nM PMID[498370]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 26607.25 nM PMID[498370]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 20276.83 nM PMID[498370]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 42657.95 nM PMID[498370]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 19319.68 nM PMID[498370]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 16672.47 nM PMID[498370]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 15631.48 nM PMID[498370]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 20370.42 nM PMID[498370]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 18836.49 nM PMID[498370]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 25003.45 nM PMID[498370]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 11885.02 nM PMID[498370]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 10990.06 nM PMID[498370]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 25527.01 nM PMID[498370]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 12793.81 nM PMID[498370]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 19543.39 nM PMID[498370]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 20844.91 nM PMID[498370]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 22542.39 nM PMID[498370]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 23173.95 nM PMID[498370]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 13772.09 nM PMID[498370]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 25822.6 nM PMID[498370]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 19054.61 nM PMID[498370]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 18323.14 nM PMID[498370]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 23604.78 nM PMID[498370]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 14621.77 nM PMID[498370]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 18323.14 nM PMID[498370]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 20892.96 nM PMID[498370]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 26121.61 nM PMID[498370]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 20137.24 nM PMID[498370]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 19724.23 nM PMID[498370]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 25468.3 nM PMID[498370]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 21281.39 nM PMID[498370]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 10000.0 nM PMID[498370]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 14621.77 nM PMID[498370]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 17418.07 nM PMID[498370]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 21232.44 nM PMID[498370]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 13122.0 nM PMID[498370]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 52.36 nM PMID[498370]
NPT404 Cell Line CCRF-CEM Homo sapiens FC = 1.8 n.a. PMID[498371]
NPT1160 Cell Line BJ Homo sapiens IC50 = 7900.0 nM PMID[498371]
NPT2468 Cell Line G-361 Homo sapiens IC50 > 50000.0 nM PMID[498371]
NPT165 Cell Line HeLa Homo sapiens IC50 > 50000.0 nM PMID[498371]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 50000.0 nM PMID[498371]
NPT111 Cell Line K562 Homo sapiens IC50 > 50000.0 nM PMID[498371]
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 = 13300.0 nM PMID[498371]

☑ 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 NPC148409 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
0.915 High Similarity NPC474594
0.885 High Similarity NPC474595
0.865 High Similarity NPC66815
0.8522 High Similarity NPC304183
0.8498 Intermediate Similarity NPC200888
0.8365 Intermediate Similarity NPC203168
0.8357 Intermediate Similarity NPC219664
0.8249 Intermediate Similarity NPC476997
0.8211 Intermediate Similarity NPC476996
0.8211 Intermediate Similarity NPC476998
0.8186 Intermediate Similarity NPC118121
0.8165 Intermediate Similarity NPC476994
0.8084 Intermediate Similarity NPC473822
0.8025 Intermediate Similarity NPC101312
0.8 Intermediate Similarity NPC204446
0.7991 Intermediate Similarity NPC476995
0.799 Intermediate Similarity NPC42591
0.795 Intermediate Similarity NPC204385
0.7943 Intermediate Similarity NPC137929
0.7943 Intermediate Similarity NPC164374
0.7929 Intermediate Similarity NPC206201
0.7926 Intermediate Similarity NPC174049
0.7923 Intermediate Similarity NPC234197
0.786 Intermediate Similarity NPC235076
0.7854 Intermediate Similarity NPC122463
0.7794 Intermediate Similarity NPC469390
0.7772 Intermediate Similarity NPC61350
0.7767 Intermediate Similarity NPC171409
0.7767 Intermediate Similarity NPC53069
0.7767 Intermediate Similarity NPC112206
0.7767 Intermediate Similarity NPC202768
0.7767 Intermediate Similarity NPC202605
0.7767 Intermediate Similarity NPC296482
0.7767 Intermediate Similarity NPC96405
0.7762 Intermediate Similarity NPC135887
0.7762 Intermediate Similarity NPC199277
0.7761 Intermediate Similarity NPC62069
0.7752 Intermediate Similarity NPC100079
0.7752 Intermediate Similarity NPC23614
0.7717 Intermediate Similarity NPC46451
0.7699 Intermediate Similarity NPC473182
0.7689 Intermediate Similarity NPC476999
0.7689 Intermediate Similarity NPC201508
0.7674 Intermediate Similarity NPC188420
0.7671 Intermediate Similarity NPC173080
0.7662 Intermediate Similarity NPC160100
0.7633 Intermediate Similarity NPC79293
0.7633 Intermediate Similarity NPC279401
0.7628 Intermediate Similarity NPC209769
0.7585 Intermediate Similarity NPC114335
0.7585 Intermediate Similarity NPC280964
0.7585 Intermediate Similarity NPC141915
0.7583 Intermediate Similarity NPC477019
0.7569 Intermediate Similarity NPC149471
0.7569 Intermediate Similarity NPC271215
0.7561 Intermediate Similarity NPC66083
0.7559 Intermediate Similarity NPC469440
0.7547 Intermediate Similarity NPC31930
0.7545 Intermediate Similarity NPC314552
0.7544 Intermediate Similarity NPC255800
0.7544 Intermediate Similarity NPC96584
0.7542 Intermediate Similarity NPC183537
0.7542 Intermediate Similarity NPC77878
0.7535 Intermediate Similarity NPC135549
0.7535 Intermediate Similarity NPC313189
0.7532 Intermediate Similarity NPC173250
0.7524 Intermediate Similarity NPC224928
0.7522 Intermediate Similarity NPC473183
0.7511 Intermediate Similarity NPC202503
0.7511 Intermediate Similarity NPC208364
0.75 Intermediate Similarity NPC217554
0.75 Intermediate Similarity NPC294244
0.75 Intermediate Similarity NPC312872
0.749 Intermediate Similarity NPC120513
0.7479 Intermediate Similarity NPC284141
0.7443 Intermediate Similarity NPC251160
0.7442 Intermediate Similarity NPC476581
0.7442 Intermediate Similarity NPC16452
0.7442 Intermediate Similarity NPC36229
0.7438 Intermediate Similarity NPC478032
0.7435 Intermediate Similarity NPC473184
0.7435 Intermediate Similarity NPC277351
0.7429 Intermediate Similarity NPC29472
0.7427 Intermediate Similarity NPC129897
0.7421 Intermediate Similarity NPC470799
0.7421 Intermediate Similarity NPC8022
0.7414 Intermediate Similarity NPC11408
0.7373 Intermediate Similarity NPC58209
0.7371 Intermediate Similarity NPC128823
0.7361 Intermediate Similarity NPC470930
0.7359 Intermediate Similarity NPC34770
0.735 Intermediate Similarity NPC210296
0.7333 Intermediate Similarity NPC133140
0.7333 Intermediate Similarity NPC195268
0.7331 Intermediate Similarity NPC124313
0.7327 Intermediate Similarity NPC471736
0.7321 Intermediate Similarity NPC112676
0.7321 Intermediate Similarity NPC473179
0.7317 Intermediate Similarity NPC474798
0.7311 Intermediate Similarity NPC162653
0.7299 Intermediate Similarity NPC78284
0.7294 Intermediate Similarity NPC193777
0.7291 Intermediate Similarity NPC288943
0.7288 Intermediate Similarity NPC15406
0.728 Intermediate Similarity NPC134637
0.728 Intermediate Similarity NPC203373
0.7273 Intermediate Similarity NPC22928
0.7269 Intermediate Similarity NPC472068
0.7261 Intermediate Similarity NPC469792
0.7255 Intermediate Similarity NPC283152
0.7252 Intermediate Similarity NPC266931
0.725 Intermediate Similarity NPC302807
0.7246 Intermediate Similarity NPC207283
0.7246 Intermediate Similarity NPC84164
0.7238 Intermediate Similarity NPC296742
0.7236 Intermediate Similarity NPC118511
0.7234 Intermediate Similarity NPC41501
0.7225 Intermediate Similarity NPC280272
0.7225 Intermediate Similarity NPC180253
0.7225 Intermediate Similarity NPC69213
0.7225 Intermediate Similarity NPC219170
0.7209 Intermediate Similarity NPC476582
0.7209 Intermediate Similarity NPC476578
0.7209 Intermediate Similarity NPC4071
0.7206 Intermediate Similarity NPC194724
0.7197 Intermediate Similarity NPC1608
0.7196 Intermediate Similarity NPC243834
0.7196 Intermediate Similarity NPC70956
0.7193 Intermediate Similarity NPC205372
0.7192 Intermediate Similarity NPC182257
0.719 Intermediate Similarity NPC224293
0.7182 Intermediate Similarity NPC470931
0.7178 Intermediate Similarity NPC473188
0.7175 Intermediate Similarity NPC162530
0.7174 Intermediate Similarity NPC473185
0.7173 Intermediate Similarity NPC166712
0.7171 Intermediate Similarity NPC289743
0.7171 Intermediate Similarity NPC110374
0.7156 Intermediate Similarity NPC474904
0.7156 Intermediate Similarity NPC223427
0.7156 Intermediate Similarity NPC473513
0.7149 Intermediate Similarity NPC185782
0.7137 Intermediate Similarity NPC472066
0.7137 Intermediate Similarity NPC472031
0.7137 Intermediate Similarity NPC472067
0.7131 Intermediate Similarity NPC49672
0.713 Intermediate Similarity NPC48353
0.713 Intermediate Similarity NPC316981
0.7129 Intermediate Similarity NPC28425
0.7129 Intermediate Similarity NPC276060
0.7118 Intermediate Similarity NPC94842
0.7114 Intermediate Similarity NPC24954
0.7111 Intermediate Similarity NPC288349
0.7109 Intermediate Similarity NPC242928
0.7106 Intermediate Similarity NPC108342
0.7104 Intermediate Similarity NPC18348
0.7103 Intermediate Similarity NPC131017
0.7101 Intermediate Similarity NPC115343
0.7101 Intermediate Similarity NPC1291
0.71 Intermediate Similarity NPC140296
0.7089 Intermediate Similarity NPC168922
0.7087 Intermediate Similarity NPC228040
0.7081 Intermediate Similarity NPC119579
0.7081 Intermediate Similarity NPC179704
0.7078 Intermediate Similarity NPC159101
0.7076 Intermediate Similarity NPC182907
0.7076 Intermediate Similarity NPC189903
0.7072 Intermediate Similarity NPC469589
0.7061 Intermediate Similarity NPC318068
0.7061 Intermediate Similarity NPC469439
0.7059 Intermediate Similarity NPC252590
0.7056 Intermediate Similarity NPC302001
0.7056 Intermediate Similarity NPC475190
0.7054 Intermediate Similarity NPC26679
0.7053 Intermediate Similarity NPC472168
0.705 Intermediate Similarity NPC235628
0.7048 Intermediate Similarity NPC469594
0.7046 Intermediate Similarity NPC166722
0.7035 Intermediate Similarity NPC26850
0.7033 Intermediate Similarity NPC192939
0.7033 Intermediate Similarity NPC311936
0.7033 Intermediate Similarity NPC215747
0.7032 Intermediate Similarity NPC291535
0.7032 Intermediate Similarity NPC475112
0.7032 Intermediate Similarity NPC475085
0.7028 Intermediate Similarity NPC214116
0.7013 Intermediate Similarity NPC179287
0.7005 Intermediate Similarity NPC474051
0.7 Intermediate Similarity NPC475774
0.7 Intermediate Similarity NPC188400
0.6995 Remote Similarity NPC312531
0.6995 Remote Similarity NPC186546
0.6995 Remote Similarity NPC476576
0.6991 Remote Similarity NPC2905
0.6988 Remote Similarity NPC209981
0.6987 Remote Similarity NPC119134
0.6987 Remote Similarity NPC475844
0.6986 Remote Similarity NPC320223
0.6986 Remote Similarity NPC114364
0.6986 Remote Similarity NPC260118

  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 NPC148409 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
0.7767 Intermediate Similarity NPD3816 Phase 1
0.7767 Intermediate Similarity NPD3815 Phase 1
0.7721 Intermediate Similarity NPD4502 Phase 2
0.7717 Intermediate Similarity NPD3763 Approved
0.765 Intermediate Similarity NPD3920 Phase 2
0.7545 Intermediate Similarity NPD5164 Discontinued
0.7542 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3923 Approved
0.7333 Intermediate Similarity NPD3921 Approved
0.7333 Intermediate Similarity NPD3922 Approved
0.7333 Intermediate Similarity NPD3924 Approved
0.7327 Intermediate Similarity NPD4305 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD6494 Phase 2
0.7294 Intermediate Similarity NPD6290 Phase 2
0.726 Intermediate Similarity NPD5658 Approved
0.7246 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD7222 Phase 2
0.7209 Intermediate Similarity NPD2177 Approved
0.7209 Intermediate Similarity NPD2176 Approved
0.7209 Intermediate Similarity NPD2175 Phase 3
0.7177 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD7169 Suspended
0.7162 Intermediate Similarity NPD5939 Approved
0.7162 Intermediate Similarity NPD5936 Approved
0.7143 Intermediate Similarity NPD5902 Approved
0.7143 Intermediate Similarity NPD5903 Approved
0.7131 Intermediate Similarity NPD8244 Phase 2
0.7059 Intermediate Similarity NPD7452 Approved
0.7059 Intermediate Similarity NPD7453 Approved
0.7026 Intermediate Similarity NPD6553 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD5530 Phase 1
0.7005 Intermediate Similarity NPD6159 Phase 2
0.6991 Remote Similarity NPD5512 Phase 3
0.6987 Remote Similarity NPD5930 Phase 3
0.6987 Remote Similarity NPD7417 Discontinued
0.696 Remote Similarity NPD5612 Discontinued
0.6949 Remote Similarity NPD7558 Phase 2
0.6944 Remote Similarity NPD6590 Discontinued
0.6937 Remote Similarity NPD3003 Approved
0.6935 Remote Similarity NPD7956 Approved
0.6935 Remote Similarity NPD7955 Approved
0.6933 Remote Similarity NPD5805 Approved
0.6926 Remote Similarity NPD1856 Discontinued
0.6912 Remote Similarity NPD6550 Discontinued
0.6907 Remote Similarity NPD4885 Approved
0.6906 Remote Similarity NPD5429 Discontinued
0.688 Remote Similarity NPD7862 Clinical (unspecified phase)
0.687 Remote Similarity NPD2899 Discontinued
0.687 Remote Similarity NPD3875 Discontinued
0.6866 Remote Similarity NPD4418 Discontinued
0.6861 Remote Similarity NPD3842 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5256 Discontinued
0.684 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7069 Discontinued
0.6818 Remote Similarity NPD1483 Discontinued
0.681 Remote Similarity NPD1503 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7803 Approved
0.6793 Remote Similarity NPD1505 Phase 2
0.6789 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6789 Remote Similarity NPD6491 Clinical (unspecified phase)
0.6781 Remote Similarity NPD1954 Phase 1
0.6773 Remote Similarity NPD7708 Approved
0.6766 Remote Similarity NPD3263 Phase 3
0.6753 Remote Similarity NPD7395 Discontinued
0.6749 Remote Similarity NPD6517 Phase 3
0.6745 Remote Similarity NPD4203 Approved
0.6745 Remote Similarity NPD4204 Approved
0.6742 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6742 Remote Similarity NPD1768 Approved
0.6741 Remote Similarity NPD4036 Approved
0.6741 Remote Similarity NPD4033 Approved
0.6741 Remote Similarity NPD4035 Approved
0.6741 Remote Similarity NPD4122 Approved
0.6741 Remote Similarity NPD4034 Approved
0.6741 Remote Similarity NPD4038 Approved
0.6741 Remote Similarity NPD4037 Approved
0.6741 Remote Similarity NPD31 Approved
0.6741 Remote Similarity NPD4039 Approved
0.6741 Remote Similarity NPD32 Approved
0.6729 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6727 Remote Similarity NPD1229 Phase 2
0.6727 Remote Similarity NPD6988 Phase 1
0.6724 Remote Similarity NPD7194 Discontinued
0.6713 Remote Similarity NPD9714 Clinical (unspecified phase)
0.6709 Remote Similarity NPD6736 Discontinued
0.6697 Remote Similarity NPD2727 Phase 2
0.6683 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6682 Remote Similarity NPD5582 Discontinued
0.6681 Remote Similarity NPD6985 Discontinued
0.6681 Remote Similarity NPD4927 Discontinued
0.668 Remote Similarity NPD6716 Phase 1
0.668 Remote Similarity NPD4876 Phase 3
0.668 Remote Similarity NPD4875 Phase 3
0.6667 Remote Similarity NPD3386 Phase 2
0.6667 Remote Similarity NPD6361 Phase 2
0.6667 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6653 Remote Similarity NPD3925 Approved
0.6651 Remote Similarity NPD8054 Approved
0.6651 Remote Similarity NPD8053 Approved
0.6639 Remote Similarity NPD6963 Approved
0.6639 Remote Similarity NPD6964 Approved
0.6639 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6220 Phase 3
0.6621 Remote Similarity NPD6569 Phase 2
0.6619 Remote Similarity NPD677 Clinical (unspecified phase)
0.6608 Remote Similarity NPD7263 Phase 2
0.66 Remote Similarity NPD7859 Phase 2
0.6595 Remote Similarity NPD2433 Clinical (unspecified phase)
0.6592 Remote Similarity NPD4118 Clinical (unspecified phase)
0.659 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6589 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6588 Remote Similarity NPD9690 Approved
0.6579 Remote Similarity NPD5863 Clinical (unspecified phase)
0.6579 Remote Similarity NPD7671 Approved
0.6579 Remote Similarity NPD7672 Approved
0.6574 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6565 Remote Similarity NPD4131 Phase 3
0.6559 Remote Similarity NPD6230 Discontinued
0.6555 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7675 Phase 3
0.6555 Remote Similarity NPD7674 Phase 3
0.6552 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6991 Approved
0.6545 Remote Similarity NPD3963 Phase 1
0.6543 Remote Similarity NPD4454 Phase 2
0.6535 Remote Similarity NPD1392 Approved
0.6529 Remote Similarity NPD4080 Discontinued
0.6529 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5506 Approved
0.6525 Remote Similarity NPD5507 Approved
0.6516 Remote Similarity NPD1038 Approved
0.6515 Remote Similarity NPD6814 Phase 3
0.6513 Remote Similarity NPD7719 Discontinued
0.6504 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6498 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6498 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6495 Remote Similarity NPD1620 Clinical (unspecified phase)
0.6493 Remote Similarity NPD4083 Discontinued
0.6478 Remote Similarity NPD5833 Phase 1
0.6473 Remote Similarity NPD9705 Discontinued
0.6473 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6473 Remote Similarity NPD112 Approved
0.6473 Remote Similarity NPD7567 Approved
0.6471 Remote Similarity NPD4005 Discontinued
0.6468 Remote Similarity NPD4375 Approved
0.6466 Remote Similarity NPD5488 Discontinued
0.6462 Remote Similarity NPD8363 Approved
0.6462 Remote Similarity NPD8364 Approved
0.6461 Remote Similarity NPD6625 Approved
0.6461 Remote Similarity NPD6723 Discontinued
0.6455 Remote Similarity NPD2845 Phase 2
0.6455 Remote Similarity NPD2843 Phase 2
0.645 Remote Similarity NPD7682 Approved
0.645 Remote Similarity NPD7684 Approved
0.6448 Remote Similarity NPD7673 Phase 3
0.6446 Remote Similarity NPD6962 Phase 2
0.6444 Remote Similarity NPD6246 Approved
0.6444 Remote Similarity NPD4052 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6974 Phase 3
0.6441 Remote Similarity NPD4551 Phase 2
0.6438 Remote Similarity NPD2383 Phase 1
0.6438 Remote Similarity NPD5945 Phase 1
0.6438 Remote Similarity NPD5944 Phase 1
0.6436 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6432 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6431 Remote Similarity NPD8461 Discontinued
0.6431 Remote Similarity NPD8091 Phase 3
0.6429 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6429 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6422 Remote Similarity NPD9706 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5416 Discontinued
0.6422 Remote Similarity NPD5067 Phase 2
0.6422 Remote Similarity NPD5066 Phase 2
0.6422 Remote Similarity NPD2762 Phase 2
0.6417 Remote Similarity NPD7426 Phase 1
0.6413 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6412 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6411 Remote Similarity NPD5604 Discontinued
0.641 Remote Similarity NPD4897 Phase 2
0.6409 Remote Similarity NPD7906 Approved
0.6408 Remote Similarity NPD3778 Approved
0.6407 Remote Similarity NPD4437 Phase 3
0.6406 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6405 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6405 Remote Similarity NPD5022 Discontinued
0.6404 Remote Similarity NPD6669 Phase 2
0.6397 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6397 Remote Similarity NPD8016 Phase 3
0.6397 Remote Similarity NPD5905 Phase 1
0.6389 Remote Similarity NPD6244 Phase 3
0.6389 Remote Similarity NPD6243 Phase 3
0.6388 Remote Similarity NPD7134 Clinical (unspecified phase)
0.6387 Remote Similarity NPD6298 Discontinued
0.6385 Remote Similarity NPD6607 Clinical (unspecified phase)
0.638 Remote Similarity NPD1213 Phase 3
0.638 Remote Similarity NPD3342 Phase 2
0.6376 Remote Similarity NPD4577 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