Structure

Physi-Chem Properties

Molecular Weight:  274.15
Volume:  309.776
LogP:  4.383
LogD:  3.983
LogS:  -4.663
# Rotatable Bonds:  3
TPSA:  16.13
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.7
Synthetic Accessibility Score:  2.007
Fsp3:  0.105
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.682
MDCK Permeability:  1.6894562577363104e-05
Pgp-inhibitor:  0.335
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.872
Plasma Protein Binding (PPB):  96.8379135131836%
Volume Distribution (VD):  1.281
Pgp-substrate:  2.236081123352051%

ADMET: Metabolism

CYP1A2-inhibitor:  0.985
CYP1A2-substrate:  0.578
CYP2C19-inhibitor:  0.838
CYP2C19-substrate:  0.275
CYP2C9-inhibitor:  0.664
CYP2C9-substrate:  0.878
CYP2D6-inhibitor:  0.737
CYP2D6-substrate:  0.904
CYP3A4-inhibitor:  0.81
CYP3A4-substrate:  0.286

ADMET: Excretion

Clearance (CL):  5.335
Half-life (T1/2):  0.196

ADMET: Toxicity

hERG Blockers:  0.623
Human Hepatotoxicity (H-HT):  0.265
Drug-inuced Liver Injury (DILI):  0.926
AMES Toxicity:  0.921
Rat Oral Acute Toxicity:  0.131
Maximum Recommended Daily Dose:  0.082
Skin Sensitization:  0.837
Carcinogencity:  0.807
Eye Corrosion:  0.024
Eye Irritation:  0.99
Respiratory Toxicity:  0.989

Download Data

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

  Natural Product: NPC251722

Natural Product ID:  NPC251722
Common Name*:   N,N-Dimethyl-4-[(E)-2-Quinolin-4-Ylethenyl]Aniline;Hydrochloride
IUPAC Name:   N,N-dimethyl-4-[(E)-2-quinolin-4-ylethenyl]aniline;hydrochloride
Synonyms:  
Standard InCHIKey:  RMENITNYNPMFHY-HCUGZAAXSA-N
Standard InCHI:  InChI=1S/C19H18N2.ClH/c1-21(2)17-11-8-15(9-12-17)7-10-16-13-14-20-19-6-4-3-5-18(16)19;/h3-14H,1-2H3;1H/b10-7+;
SMILES:  CN(C)c1ccc(/C=C/c2ccnc3ccccc23)cc1.Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1979913
PubChem CID:   6538066
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference

☑ 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. 64863.44 nM PMID[536474]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 17701.09 nM PMID[536474]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 39355.01 nM PMID[536474]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 43853.07 nM PMID[536474]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 40271.7 nM PMID[536474]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 31550.05 nM PMID[536474]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 93325.43 nM PMID[536474]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 47863.01 nM PMID[536474]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 75857.76 nM PMID[536474]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 53210.83 nM PMID[536474]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 33496.54 nM PMID[536474]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 84722.74 nM PMID[536474]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 64268.77 nM PMID[536474]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 23334.58 nM PMID[536474]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 30478.95 nM PMID[536474]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 39445.73 nM PMID[536474]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 65765.78 nM PMID[536474]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 55847.02 nM PMID[536474]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 65765.78 nM PMID[536474]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 51050.5 nM PMID[536474]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 55590.43 nM PMID[536474]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 53333.49 nM PMID[536474]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 18155.16 nM PMID[536474]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 58210.32 nM PMID[536474]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 61376.2 nM PMID[536474]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 28840.32 nM PMID[536474]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 61094.2 nM PMID[536474]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 39810.72 nM PMID[536474]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 48977.88 nM PMID[536474]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 90157.11 nM PMID[536474]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 96827.79 nM PMID[536474]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 54450.27 nM PMID[536474]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 47863.01 nM PMID[536474]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 43052.66 nM PMID[536474]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 23067.47 nM PMID[536474]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 54701.6 nM PMID[536474]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 14487.72 nM PMID[536474]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[536474]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 89742.88 nM PMID[536474]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 49545.02 nM PMID[536474]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 72610.6 nM PMID[536474]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 25292.98 nM PMID[536474]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 28773.98 nM PMID[536474]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 54325.03 nM PMID[536474]

☑ 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 NPC251722 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
1.0 High Similarity NPC314102
0.9185 High Similarity NPC169433
0.8992 High Similarity NPC46358
0.8832 High Similarity NPC150259
0.8811 High Similarity NPC40070
0.8779 High Similarity NPC122718
0.8605 High Similarity NPC162689
0.8605 High Similarity NPC54102
0.8605 High Similarity NPC91958
0.8581 High Similarity NPC56765
0.8571 High Similarity NPC73767
0.8542 High Similarity NPC470111
0.8529 High Similarity NPC282398
0.8527 High Similarity NPC81561
0.8523 High Similarity NPC215584
0.8523 High Similarity NPC44773
0.8511 High Similarity NPC469768
0.8511 High Similarity NPC469779
0.8511 High Similarity NPC469783
0.8511 High Similarity NPC469780
0.8511 High Similarity NPC469784
0.8511 High Similarity NPC469761
0.8511 High Similarity NPC469767
0.8493 Intermediate Similarity NPC470233
0.8473 Intermediate Similarity NPC215519
0.8451 Intermediate Similarity NPC469766
0.845 Intermediate Similarity NPC148140
0.8446 Intermediate Similarity NPC51054
0.844 Intermediate Similarity NPC315348
0.844 Intermediate Similarity NPC32002
0.844 Intermediate Similarity NPC110126
0.844 Intermediate Similarity NPC316811
0.8435 Intermediate Similarity NPC325903
0.8429 Intermediate Similarity NPC84911
0.8425 Intermediate Similarity NPC53947
0.8414 Intermediate Similarity NPC179787
0.8414 Intermediate Similarity NPC201380
0.8392 Intermediate Similarity NPC20144
0.8385 Intermediate Similarity NPC297486
0.8385 Intermediate Similarity NPC471402
0.8385 Intermediate Similarity NPC240136
0.8357 Intermediate Similarity NPC96102
0.8357 Intermediate Similarity NPC261195
0.8357 Intermediate Similarity NPC29886
0.8356 Intermediate Similarity NPC321911
0.8345 Intermediate Similarity NPC63545
0.8345 Intermediate Similarity NPC288838
0.8333 Intermediate Similarity NPC206819
0.8333 Intermediate Similarity NPC318065
0.8321 Intermediate Similarity NPC143603
0.831 Intermediate Similarity NPC104483
0.8298 Intermediate Similarity NPC105127
0.8289 Intermediate Similarity NPC478182
0.8289 Intermediate Similarity NPC90723
0.8288 Intermediate Similarity NPC469811
0.8276 Intermediate Similarity NPC86288
0.8261 Intermediate Similarity NPC69914
0.8222 Intermediate Similarity NPC476322
0.8188 Intermediate Similarity NPC476131
0.8156 Intermediate Similarity NPC198988
0.8151 Intermediate Similarity NPC314372
0.8148 Intermediate Similarity NPC290094
0.8146 Intermediate Similarity NPC129721
0.8146 Intermediate Similarity NPC216643
0.8146 Intermediate Similarity NPC286427
0.8138 Intermediate Similarity NPC190296
0.8134 Intermediate Similarity NPC265605
0.8134 Intermediate Similarity NPC48564
0.8134 Intermediate Similarity NPC182570
0.8125 Intermediate Similarity NPC279081
0.8125 Intermediate Similarity NPC59084
0.8125 Intermediate Similarity NPC2949
0.8092 Intermediate Similarity NPC293487
0.8092 Intermediate Similarity NPC477591
0.8092 Intermediate Similarity NPC41257
0.8079 Intermediate Similarity NPC476464
0.8074 Intermediate Similarity NPC329825
0.8071 Intermediate Similarity NPC256893
0.8071 Intermediate Similarity NPC82295
0.8069 Intermediate Similarity NPC473868
0.8069 Intermediate Similarity NPC63157
0.8056 Intermediate Similarity NPC88097
0.8054 Intermediate Similarity NPC24678
0.8054 Intermediate Similarity NPC33421
0.8054 Intermediate Similarity NPC105818
0.8052 Intermediate Similarity NPC317105
0.8041 Intermediate Similarity NPC21605
0.8027 Intermediate Similarity NPC285731
0.8026 Intermediate Similarity NPC236711
0.8 Intermediate Similarity NPC230002
0.7987 Intermediate Similarity NPC280852
0.7987 Intermediate Similarity NPC470203
0.7984 Intermediate Similarity NPC27802
0.7974 Intermediate Similarity NPC135141
0.7974 Intermediate Similarity NPC92796
0.7973 Intermediate Similarity NPC143872
0.7972 Intermediate Similarity NPC325252
0.7971 Intermediate Similarity NPC169625
0.7971 Intermediate Similarity NPC202957
0.7962 Intermediate Similarity NPC194411
0.7949 Intermediate Similarity NPC478183
0.7947 Intermediate Similarity NPC469765
0.7947 Intermediate Similarity NPC200214
0.7947 Intermediate Similarity NPC469763
0.7947 Intermediate Similarity NPC469786
0.7947 Intermediate Similarity NPC138842
0.7947 Intermediate Similarity NPC25008
0.7947 Intermediate Similarity NPC73952
0.7947 Intermediate Similarity NPC469760
0.7947 Intermediate Similarity NPC259644
0.7943 Intermediate Similarity NPC179365
0.7943 Intermediate Similarity NPC475450
0.7943 Intermediate Similarity NPC101165
0.7935 Intermediate Similarity NPC478184
0.7922 Intermediate Similarity NPC470204
0.7922 Intermediate Similarity NPC122141
0.7919 Intermediate Similarity NPC471957
0.7911 Intermediate Similarity NPC201634
0.7905 Intermediate Similarity NPC159856
0.7899 Intermediate Similarity NPC166424
0.7899 Intermediate Similarity NPC245244
0.7899 Intermediate Similarity NPC146373
0.7895 Intermediate Similarity NPC70922
0.7895 Intermediate Similarity NPC80597
0.7895 Intermediate Similarity NPC476219
0.7895 Intermediate Similarity NPC75540
0.7895 Intermediate Similarity NPC212376
0.7895 Intermediate Similarity NPC211572
0.7872 Intermediate Similarity NPC22079
0.7871 Intermediate Similarity NPC225018
0.7871 Intermediate Similarity NPC478185
0.7857 Intermediate Similarity NPC89490
0.7848 Intermediate Similarity NPC91895
0.7842 Intermediate Similarity NPC250361
0.7834 Intermediate Similarity NPC56233
0.7812 Intermediate Similarity NPC275305
0.7812 Intermediate Similarity NPC37423
0.7801 Intermediate Similarity NPC329896
0.7801 Intermediate Similarity NPC475090
0.7801 Intermediate Similarity NPC475105
0.7801 Intermediate Similarity NPC473587
0.7799 Intermediate Similarity NPC82331
0.7785 Intermediate Similarity NPC469525
0.7785 Intermediate Similarity NPC63751
0.7778 Intermediate Similarity NPC476297
0.7778 Intermediate Similarity NPC34844
0.7763 Intermediate Similarity NPC470823
0.7762 Intermediate Similarity NPC473930
0.7761 Intermediate Similarity NPC476566
0.7755 Intermediate Similarity NPC115611
0.7752 Intermediate Similarity NPC76540
0.7752 Intermediate Similarity NPC231655
0.7746 Intermediate Similarity NPC475428
0.7742 Intermediate Similarity NPC475990
0.7742 Intermediate Similarity NPC221786
0.7742 Intermediate Similarity NPC6436
0.7742 Intermediate Similarity NPC474880
0.7736 Intermediate Similarity NPC32534
0.773 Intermediate Similarity NPC473762
0.7727 Intermediate Similarity NPC469785
0.7716 Intermediate Similarity NPC68354
0.7716 Intermediate Similarity NPC157583
0.7714 Intermediate Similarity NPC476140
0.7712 Intermediate Similarity NPC141926
0.7702 Intermediate Similarity NPC297034
0.7698 Intermediate Similarity NPC27740
0.7692 Intermediate Similarity NPC229173
0.7677 Intermediate Similarity NPC469762
0.7669 Intermediate Similarity NPC215795
0.7669 Intermediate Similarity NPC176199
0.7667 Intermediate Similarity NPC470440
0.766 Intermediate Similarity NPC471311
0.766 Intermediate Similarity NPC471313
0.7658 Intermediate Similarity NPC2165
0.7658 Intermediate Similarity NPC274229
0.7658 Intermediate Similarity NPC195507
0.7654 Intermediate Similarity NPC150048
0.7654 Intermediate Similarity NPC203754
0.7654 Intermediate Similarity NPC474958
0.7647 Intermediate Similarity NPC216713
0.761 Intermediate Similarity NPC474561
0.761 Intermediate Similarity NPC49954
0.7603 Intermediate Similarity NPC218268
0.7595 Intermediate Similarity NPC311276
0.7593 Intermediate Similarity NPC471579
0.758 Intermediate Similarity NPC255229
0.758 Intermediate Similarity NPC81229
0.7566 Intermediate Similarity NPC477974
0.7564 Intermediate Similarity NPC193740
0.7564 Intermediate Similarity NPC167635
0.7562 Intermediate Similarity NPC201700
0.7561 Intermediate Similarity NPC12649
0.7554 Intermediate Similarity NPC41174
0.755 Intermediate Similarity NPC204141
0.7532 Intermediate Similarity NPC282231
0.7531 Intermediate Similarity NPC477611
0.7517 Intermediate Similarity NPC284635
0.7516 Intermediate Similarity NPC97343
0.7515 Intermediate Similarity NPC314919
0.75 Intermediate Similarity NPC237188

  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 NPC251722 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
0.9209 High Similarity NPD4547 Phase 3
0.9154 High Similarity NPD2118 Approved
0.9154 High Similarity NPD2119 Approved
0.903 High Similarity NPD3385 Approved
0.8889 High Similarity NPD3944 Approved
0.8889 High Similarity NPD3942 Approved
0.8857 High Similarity NPD1918 Clinical (unspecified phase)
0.8806 High Similarity NPD3476 Approved
0.8806 High Similarity NPD3475 Approved
0.875 High Similarity NPD4030 Approved
0.875 High Similarity NPD4028 Approved
0.875 High Similarity NPD4029 Approved
0.8652 High Similarity NPD2006 Phase 2
0.8623 High Similarity NPD1256 Approved
0.8623 High Similarity NPD1255 Approved
0.8623 High Similarity NPD1253 Approved
0.8623 High Similarity NPD1254 Approved
0.8611 High Similarity NPD2430 Phase 2
0.8611 High Similarity NPD3100 Discontinued
0.8582 High Similarity NPD1722 Approved
0.8562 High Similarity NPD2837 Discontinued
0.8533 High Similarity NPD3323 Discontinued
0.8521 High Similarity NPD4637 Clinical (unspecified phase)
0.8483 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD5315 Discontinued
0.8456 Intermediate Similarity NPD3654 Approved
0.8444 Intermediate Similarity NPD991 Phase 2
0.8444 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD2072 Approved
0.844 Intermediate Similarity NPD2075 Approved
0.844 Intermediate Similarity NPD2068 Approved
0.844 Intermediate Similarity NPD786 Approved
0.844 Intermediate Similarity NPD2074 Approved
0.844 Intermediate Similarity NPD2073 Approved
0.844 Intermediate Similarity NPD2070 Approved
0.844 Intermediate Similarity NPD2069 Approved
0.844 Intermediate Similarity NPD2071 Approved
0.8429 Intermediate Similarity NPD6554 Approved
0.8429 Intermediate Similarity NPD45 Approved
0.8394 Intermediate Similarity NPD715 Phase 3
0.8357 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.8345 Intermediate Similarity NPD1683 Approved
0.8345 Intermediate Similarity NPD7469 Discontinued
0.8333 Intermediate Similarity NPD3401 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD947 Approved
0.8299 Intermediate Similarity NPD2172 Phase 1
0.8247 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD9583 Approved
0.8207 Intermediate Similarity NPD4509 Discontinued
0.8188 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.8143 Intermediate Similarity NPD1994 Approved
0.8143 Intermediate Similarity NPD1993 Approved
0.8143 Intermediate Similarity NPD1995 Approved
0.8141 Intermediate Similarity NPD3610 Approved
0.8141 Intermediate Similarity NPD3609 Approved
0.8134 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.8134 Intermediate Similarity NPD268 Approved
0.8134 Intermediate Similarity NPD271 Approved
0.8133 Intermediate Similarity NPD2165 Phase 1
0.8129 Intermediate Similarity NPD2640 Approved
0.8129 Intermediate Similarity NPD2641 Approved
0.8125 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD2720 Phase 1
0.8117 Intermediate Similarity NPD2719 Clinical (unspecified phase)
0.8088 Intermediate Similarity NPD9357 Approved
0.8079 Intermediate Similarity NPD3112 Approved
0.8079 Intermediate Similarity NPD3113 Approved
0.8079 Intermediate Similarity NPD3114 Approved
0.8079 Intermediate Similarity NPD3115 Approved
0.8077 Intermediate Similarity NPD5436 Phase 1
0.805 Intermediate Similarity NPD7111 Discontinued
0.8041 Intermediate Similarity NPD4703 Approved
0.8041 Intermediate Similarity NPD4702 Approved
0.8041 Intermediate Similarity NPD1661 Suspended
0.8026 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD4640 Approved
0.8013 Intermediate Similarity NPD4639 Approved
0.8013 Intermediate Similarity NPD4638 Approved
0.8013 Intermediate Similarity NPD5862 Discovery
0.7987 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD5254 Discontinued
0.7943 Intermediate Similarity NPD1251 Discontinued
0.7937 Intermediate Similarity NPD4181 Approved
0.7925 Intermediate Similarity NPD5065 Approved
0.7922 Intermediate Similarity NPD1403 Approved
0.7922 Intermediate Similarity NPD1404 Approved
0.7922 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD6497 Approved
0.7908 Intermediate Similarity NPD4326 Phase 2
0.7898 Intermediate Similarity NPD2390 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD976 Approved
0.7895 Intermediate Similarity NPD977 Approved
0.7895 Intermediate Similarity NPD975 Approved
0.7891 Intermediate Similarity NPD4510 Discontinued
0.7881 Intermediate Similarity NPD2882 Phase 1
0.7866 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7863 Intermediate Similarity NPD4824 Approved
0.7863 Intermediate Similarity NPD4823 Approved
0.7843 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD3813 Approved
0.7834 Intermediate Similarity NPD2639 Approved
0.7834 Intermediate Similarity NPD2642 Approved
0.7812 Intermediate Similarity NPD4128 Approved
0.7786 Intermediate Similarity NPD1598 Discontinued
0.7785 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2142 Approved
0.7778 Intermediate Similarity NPD2141 Approved
0.7778 Intermediate Similarity NPD2140 Approved
0.7771 Intermediate Similarity NPD7394 Phase 2
0.777 Intermediate Similarity NPD4047 Discontinued
0.7764 Intermediate Similarity NPD4075 Phase 2
0.7763 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD6158 Phase 2
0.7756 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6771 Discontinued
0.7752 Intermediate Similarity NPD9098 Phase 3
0.7752 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD7216 Approved
0.775 Intermediate Similarity NPD7217 Approved
0.7748 Intermediate Similarity NPD1183 Approved
0.7748 Intermediate Similarity NPD5538 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD5418 Discontinued
0.7742 Intermediate Similarity NPD5255 Approved
0.7733 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD2580 Discontinued
0.7716 Intermediate Similarity NPD3506 Approved
0.7716 Intermediate Similarity NPD3505 Approved
0.7712 Intermediate Similarity NPD3339 Approved
0.7707 Intermediate Similarity NPD3583 Phase 2
0.7704 Intermediate Similarity NPD9392 Approved
0.7704 Intermediate Similarity NPD9396 Approved
0.7702 Intermediate Similarity NPD3859 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7564 Discontinued
0.7697 Intermediate Similarity NPD4957 Phase 2
0.7697 Intermediate Similarity NPD2466 Phase 3
0.7697 Intermediate Similarity NPD2462 Phase 3
0.7697 Intermediate Similarity NPD2465 Approved
0.7687 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD2581 Approved
0.7677 Intermediate Similarity NPD2582 Approved
0.7677 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD4076 Approved
0.7669 Intermediate Similarity NPD4079 Approved
0.7662 Intermediate Similarity NPD6285 Phase 2
0.7658 Intermediate Similarity NPD4550 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3262 Approved
0.7643 Intermediate Similarity NPD5400 Approved
0.7643 Intermediate Similarity NPD4384 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD5105 Approved
0.7636 Intermediate Similarity NPD5106 Approved
0.7607 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD4902 Discontinued
0.7605 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD792 Discontinued
0.759 Intermediate Similarity NPD5892 Approved
0.7582 Intermediate Similarity NPD4463 Approved
0.7582 Intermediate Similarity NPD4462 Approved
0.7578 Intermediate Similarity NPD3117 Approved
0.7578 Intermediate Similarity NPD3116 Approved
0.7574 Intermediate Similarity NPD6281 Approved
0.7562 Intermediate Similarity NPD5021 Discontinued
0.756 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD5995 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD3348 Phase 2
0.7545 Intermediate Similarity NPD4298 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD6299 Approved
0.7538 Intermediate Similarity NPD6300 Approved
0.7533 Intermediate Similarity NPD3717 Discontinued
0.7532 Intermediate Similarity NPD4641 Discontinued
0.7516 Intermediate Similarity NPD3433 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2150 Discontinued
0.75 Intermediate Similarity NPD2144 Approved
0.75 Intermediate Similarity NPD8122 Approved
0.75 Intermediate Similarity NPD8123 Approved
0.75 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2896 Discontinued
0.75 Intermediate Similarity NPD3929 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3799 Suspended
0.7485 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD5671 Approved
0.7471 Intermediate Similarity NPD5145 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD7287 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD2333 Discontinued
0.7439 Intermediate Similarity NPD2406 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD2771 Approved
0.7432 Intermediate Similarity NPD1262 Discovery
0.7429 Intermediate Similarity NPD5787 Discontinued
0.7424 Intermediate Similarity NPD4116 Approved
0.741 Intermediate Similarity NPD6595 Phase 3
0.7407 Intermediate Similarity NPD4973 Approved
0.7407 Intermediate Similarity NPD4184 Clinical (unspecified phase)

  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