Structure

Physi-Chem Properties

Molecular Weight:  301.13
Volume:  289.498
LogP:  1.832
LogD:  1.478
LogS:  -3.588
# Rotatable Bonds:  1
TPSA:  43.46
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.734
Synthetic Accessibility Score:  5.122
Fsp3:  0.647
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.097
MDCK Permeability:  2.7688556656357832e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.994
Plasma Protein Binding (PPB):  40.60633850097656%
Volume Distribution (VD):  2.446
Pgp-substrate:  40.01472854614258%

ADMET: Metabolism

CYP1A2-inhibitor:  0.179
CYP1A2-substrate:  0.575
CYP2C19-inhibitor:  0.077
CYP2C19-substrate:  0.843
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.196
CYP2D6-inhibitor:  0.957
CYP2D6-substrate:  0.849
CYP3A4-inhibitor:  0.794
CYP3A4-substrate:  0.67

ADMET: Excretion

Clearance (CL):  17.496
Half-life (T1/2):  0.456

ADMET: Toxicity

hERG Blockers:  0.691
Human Hepatotoxicity (H-HT):  0.697
Drug-inuced Liver Injury (DILI):  0.257
AMES Toxicity:  0.1
Rat Oral Acute Toxicity:  0.556
Maximum Recommended Daily Dose:  0.898
Skin Sensitization:  0.139
Carcinogencity:  0.747
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.94

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Structure MOL file  
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  Natural Product: NPC65403

Natural Product ID:  NPC65403
Common Name*:   QLRRUWXMMVXORS-NRKLIOEPSA-N
IUPAC Name:   n.a.
Synonyms:   (-)-Augustine
Standard InCHIKey:  QLRRUWXMMVXORS-NRKLIOEPSA-N
Standard InCHI:  InChI=1S/C17H19NO4/c1-19-13-6-14-17(16-15(13)22-16)2-3-18(14)7-9-4-11-12(5-10(9)17)21-8-20-11/h4-5,13-16H,2-3,6-8H2,1H3/t13-,14-,15+,16+,17+/m1/s1
SMILES:  CO[C@@H]1C[C@H]2N3CC[C@]2([C@@H]2[C@H]1O2)c1c(C3)cc2c(c1)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462743
PubChem CID:   157561
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001775] Amaryllidaceae alkaloids
        • [CHEMONTID:0004123] Crinine- and Haemanthamine-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
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16562843]
NPO22317 Crinum amabile Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[8229016]
NPO22317 Crinum amabile Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22317 Crinum amabile Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22317 Crinum amabile Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23091 Halocarpus bidwillii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9457 Machaerium opacum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21398 Jasminum laurifolium f. nitidum Species Oleaceae 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
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 3.2 ug ml-1 PMID[537138]
NPT91 Cell Line KB Homo sapiens ED50 = 0.6 ug ml-1 PMID[537138]
NPT168 Cell Line P388 Mus musculus ED50 = 0.6 ug ml-1 PMID[537138]
NPT762 Cell Line A-431 Homo sapiens ED50 = 4.9 ug ml-1 PMID[537138]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 1.7 ug ml-1 PMID[537138]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 1.8 ug ml-1 PMID[537138]
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 1.2 ug ml-1 PMID[537138]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 602.56 nM PMID[537139]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 157.4 nM PMID[537139]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 1342.76 nM PMID[537139]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 851.14 nM PMID[537139]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[537139]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 3.7 ug ml-1 PMID[537138]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.4 ug ml-1 PMID[537138]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[537138]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.6 ug ml-1 PMID[537138]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 140.0 ug ml-1 PMID[537138]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 180.0 ug ml-1 PMID[537138]
NPT2 Others Unspecified Ratio ED50 = 4.0 n.a. PMID[537138]
NPT2 Others Unspecified Ratio ED50 = 3.0 n.a. PMID[537138]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.8 ug ml-1 PMID[537138]

☑ 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 NPC65403 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
0.963 High Similarity NPC15919
0.9341 High Similarity NPC9867
0.9321 High Similarity NPC311991
0.9202 High Similarity NPC75958
0.9036 High Similarity NPC187678
0.8994 High Similarity NPC78733
0.8963 High Similarity NPC474324
0.8963 High Similarity NPC57812
0.8909 High Similarity NPC82533
0.8909 High Similarity NPC158148
0.8909 High Similarity NPC475845
0.8909 High Similarity NPC290759
0.8909 High Similarity NPC266176
0.8876 High Similarity NPC244554
0.8855 High Similarity NPC474708
0.8848 High Similarity NPC100566
0.8841 High Similarity NPC247972
0.8802 High Similarity NPC470739
0.8802 High Similarity NPC225597
0.8802 High Similarity NPC477640
0.8795 High Similarity NPC475686
0.8795 High Similarity NPC58766
0.878 High Similarity NPC320104
0.8757 High Similarity NPC474470
0.8743 High Similarity NPC474475
0.8735 High Similarity NPC190332
0.8735 High Similarity NPC181653
0.8706 High Similarity NPC294790
0.8706 High Similarity NPC118633
0.8706 High Similarity NPC148693
0.8698 High Similarity NPC304675
0.8659 High Similarity NPC215829
0.8659 High Similarity NPC97072
0.8647 High Similarity NPC237044
0.8634 High Similarity NPC210148
0.8634 High Similarity NPC233029
0.8623 High Similarity NPC210918
0.8616 High Similarity NPC475959
0.8614 High Similarity NPC180306
0.8596 High Similarity NPC474325
0.8589 High Similarity NPC31311
0.8589 High Similarity NPC234392
0.8554 High Similarity NPC218614
0.8547 High Similarity NPC474745
0.8528 High Similarity NPC216459
0.8528 High Similarity NPC41178
0.8528 High Similarity NPC138487
0.8519 High Similarity NPC148898
0.8506 High Similarity NPC475981
0.8506 High Similarity NPC474746
0.8503 High Similarity NPC16805
0.8503 High Similarity NPC167546
0.8503 High Similarity NPC302527
0.8485 Intermediate Similarity NPC477080
0.8476 Intermediate Similarity NPC146288
0.8471 Intermediate Similarity NPC149090
0.8471 Intermediate Similarity NPC19520
0.8452 Intermediate Similarity NPC476432
0.8452 Intermediate Similarity NPC476002
0.8452 Intermediate Similarity NPC24264
0.8421 Intermediate Similarity NPC2314
0.8402 Intermediate Similarity NPC252960
0.8402 Intermediate Similarity NPC247389
0.8393 Intermediate Similarity NPC225774
0.8385 Intermediate Similarity NPC37144
0.8385 Intermediate Similarity NPC59907
0.8371 Intermediate Similarity NPC63152
0.8343 Intermediate Similarity NPC219341
0.8343 Intermediate Similarity NPC275132
0.8323 Intermediate Similarity NPC4304
0.8305 Intermediate Similarity NPC230098
0.8282 Intermediate Similarity NPC223125
0.8253 Intermediate Similarity NPC323443
0.8253 Intermediate Similarity NPC180756
0.8239 Intermediate Similarity NPC73492
0.8239 Intermediate Similarity NPC299990
0.8214 Intermediate Similarity NPC232924
0.8214 Intermediate Similarity NPC266753
0.8214 Intermediate Similarity NPC205167
0.8214 Intermediate Similarity NPC477559
0.8214 Intermediate Similarity NPC160298
0.8214 Intermediate Similarity NPC249274
0.8214 Intermediate Similarity NPC306902
0.8198 Intermediate Similarity NPC6152
0.8193 Intermediate Similarity NPC93593
0.8182 Intermediate Similarity NPC223124
0.8176 Intermediate Similarity NPC328750
0.8176 Intermediate Similarity NPC238530
0.8176 Intermediate Similarity NPC474915
0.8176 Intermediate Similarity NPC232514
0.8176 Intermediate Similarity NPC188163
0.8176 Intermediate Similarity NPC231198
0.8176 Intermediate Similarity NPC213206
0.8176 Intermediate Similarity NPC276944
0.8161 Intermediate Similarity NPC199465
0.8161 Intermediate Similarity NPC229166
0.8161 Intermediate Similarity NPC49353
0.8161 Intermediate Similarity NPC128560
0.8155 Intermediate Similarity NPC111485
0.8153 Intermediate Similarity NPC7018
0.8144 Intermediate Similarity NPC147091
0.8136 Intermediate Similarity NPC248642
0.8136 Intermediate Similarity NPC102760
0.8125 Intermediate Similarity NPC99179
0.8125 Intermediate Similarity NPC126284
0.8125 Intermediate Similarity NPC470879
0.8125 Intermediate Similarity NPC258695
0.8113 Intermediate Similarity NPC314682
0.8101 Intermediate Similarity NPC214116
0.8098 Intermediate Similarity NPC476144
0.8098 Intermediate Similarity NPC51957
0.8098 Intermediate Similarity NPC210437
0.8098 Intermediate Similarity NPC106295
0.8098 Intermediate Similarity NPC16107
0.8095 Intermediate Similarity NPC129603
0.809 Intermediate Similarity NPC156576
0.8086 Intermediate Similarity NPC130926
0.8084 Intermediate Similarity NPC325871
0.8084 Intermediate Similarity NPC76079
0.8084 Intermediate Similarity NPC99659
0.8079 Intermediate Similarity NPC32413
0.8079 Intermediate Similarity NPC474506
0.8075 Intermediate Similarity NPC136860
0.8075 Intermediate Similarity NPC476567
0.8075 Intermediate Similarity NPC128019
0.8068 Intermediate Similarity NPC320223
0.8068 Intermediate Similarity NPC23219
0.8068 Intermediate Similarity NPC114364
0.8056 Intermediate Similarity NPC237579
0.8049 Intermediate Similarity NPC7467
0.8023 Intermediate Similarity NPC267408
0.8011 Intermediate Similarity NPC281581
0.8011 Intermediate Similarity NPC112575
0.7988 Intermediate Similarity NPC476572
0.7977 Intermediate Similarity NPC298979
0.7976 Intermediate Similarity NPC244112
0.7968 Intermediate Similarity NPC2173
0.7968 Intermediate Similarity NPC202771
0.7968 Intermediate Similarity NPC119818
0.7968 Intermediate Similarity NPC328700
0.7967 Intermediate Similarity NPC475597
0.7967 Intermediate Similarity NPC473716
0.7965 Intermediate Similarity NPC24465
0.7946 Intermediate Similarity NPC14622
0.7946 Intermediate Similarity NPC70290
0.7946 Intermediate Similarity NPC46744
0.7946 Intermediate Similarity NPC124302
0.7946 Intermediate Similarity NPC73020
0.7946 Intermediate Similarity NPC215098
0.7941 Intermediate Similarity NPC92191
0.7941 Intermediate Similarity NPC59028
0.7933 Intermediate Similarity NPC116284
0.7931 Intermediate Similarity NPC83198
0.7931 Intermediate Similarity NPC204908
0.7931 Intermediate Similarity NPC241055
0.7923 Intermediate Similarity NPC24260
0.7919 Intermediate Similarity NPC13916
0.7919 Intermediate Similarity NPC124657
0.7919 Intermediate Similarity NPC264850
0.7919 Intermediate Similarity NPC304659
0.7919 Intermediate Similarity NPC86144
0.7912 Intermediate Similarity NPC82763
0.791 Intermediate Similarity NPC283999
0.7901 Intermediate Similarity NPC57036
0.7882 Intermediate Similarity NPC315707
0.7882 Intermediate Similarity NPC148014
0.7882 Intermediate Similarity NPC40389
0.7882 Intermediate Similarity NPC78359
0.7882 Intermediate Similarity NPC65490
0.7879 Intermediate Similarity NPC476151
0.7877 Intermediate Similarity NPC155442
0.7877 Intermediate Similarity NPC477561
0.7877 Intermediate Similarity NPC476574
0.7877 Intermediate Similarity NPC312918
0.7874 Intermediate Similarity NPC150879
0.7866 Intermediate Similarity NPC185838
0.7861 Intermediate Similarity NPC226652
0.7861 Intermediate Similarity NPC72788
0.7861 Intermediate Similarity NPC168409
0.7861 Intermediate Similarity NPC314100
0.7861 Intermediate Similarity NPC120671
0.7857 Intermediate Similarity NPC186546
0.7857 Intermediate Similarity NPC476576
0.7844 Intermediate Similarity NPC274026
0.7841 Intermediate Similarity NPC276890
0.7841 Intermediate Similarity NPC76682
0.7841 Intermediate Similarity NPC227060
0.7841 Intermediate Similarity NPC198498
0.7841 Intermediate Similarity NPC10908
0.7841 Intermediate Similarity NPC317145
0.7841 Intermediate Similarity NPC115284
0.7841 Intermediate Similarity NPC317439
0.7841 Intermediate Similarity NPC63646
0.7836 Intermediate Similarity NPC106786
0.7831 Intermediate Similarity NPC428
0.7831 Intermediate Similarity NPC246587
0.7831 Intermediate Similarity NPC476571
0.7831 Intermediate Similarity NPC135538
0.7831 Intermediate Similarity NPC24233
0.7831 Intermediate Similarity NPC130941

  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 NPC65403 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
0.8176 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD4584 Approved
0.8035 Intermediate Similarity NPD4481 Phase 3
0.7968 Intermediate Similarity NPD5005 Approved
0.7968 Intermediate Similarity NPD5006 Approved
0.7946 Intermediate Similarity NPD4420 Approved
0.7919 Intermediate Similarity NPD3051 Approved
0.7919 Intermediate Similarity NPD6071 Discontinued
0.7914 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD8156 Discontinued
0.7882 Intermediate Similarity NPD2563 Approved
0.7882 Intermediate Similarity NPD2560 Approved
0.7874 Intermediate Similarity NPD2969 Approved
0.7874 Intermediate Similarity NPD2970 Approved
0.7841 Intermediate Similarity NPD8251 Approved
0.7841 Intermediate Similarity NPD8099 Discontinued
0.7841 Intermediate Similarity NPD8252 Approved
0.7811 Intermediate Similarity NPD4773 Phase 2
0.7811 Intermediate Similarity NPD4772 Phase 2
0.7758 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD27 Approved
0.7727 Intermediate Similarity NPD2489 Approved
0.7705 Intermediate Similarity NPD7906 Approved
0.768 Intermediate Similarity NPD7310 Approved
0.768 Intermediate Similarity NPD7313 Approved
0.768 Intermediate Similarity NPD7311 Approved
0.768 Intermediate Similarity NPD4577 Approved
0.768 Intermediate Similarity NPD4578 Approved
0.768 Intermediate Similarity NPD7312 Approved
0.7657 Intermediate Similarity NPD6107 Approved
0.7637 Intermediate Similarity NPD7309 Approved
0.763 Intermediate Similarity NPD6788 Approved
0.7588 Intermediate Similarity NPD4017 Approved
0.7574 Intermediate Similarity NPD3640 Phase 3
0.7574 Intermediate Similarity NPD6031 Approved
0.7574 Intermediate Similarity NPD3639 Approved
0.7574 Intermediate Similarity NPD3641 Approved
0.7574 Intermediate Similarity NPD6030 Approved
0.7558 Intermediate Similarity NPD7298 Approved
0.7554 Intermediate Similarity NPD4663 Approved
0.7541 Intermediate Similarity NPD8053 Approved
0.7541 Intermediate Similarity NPD8054 Approved
0.7486 Intermediate Similarity NPD2971 Approved
0.7486 Intermediate Similarity NPD2968 Approved
0.7485 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD4236 Phase 3
0.747 Intermediate Similarity NPD4237 Approved
0.746 Intermediate Similarity NPD5582 Discontinued
0.7438 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD4210 Discontinued
0.7414 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD5313 Approved
0.7403 Intermediate Similarity NPD5312 Approved
0.7394 Intermediate Similarity NPD7296 Approved
0.7391 Intermediate Similarity NPD7280 Phase 3
0.7391 Intermediate Similarity NPD7281 Phase 3
0.7353 Intermediate Similarity NPD1424 Approved
0.7337 Intermediate Similarity NPD7124 Phase 2
0.7333 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2898 Approved
0.7333 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD2973 Approved
0.733 Intermediate Similarity NPD2975 Approved
0.733 Intermediate Similarity NPD2974 Approved
0.7318 Intermediate Similarity NPD4166 Phase 2
0.7314 Intermediate Similarity NPD2977 Approved
0.7314 Intermediate Similarity NPD2978 Approved
0.7306 Intermediate Similarity NPD4580 Approved
0.7288 Intermediate Similarity NPD7833 Phase 2
0.7288 Intermediate Similarity NPD7831 Phase 2
0.7288 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5241 Discontinued
0.7267 Intermediate Similarity NPD4727 Phase 1
0.7258 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6365 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4010 Discontinued
0.7216 Intermediate Similarity NPD5773 Approved
0.7216 Intermediate Similarity NPD5772 Approved
0.7207 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD6625 Approved
0.7184 Intermediate Similarity NPD6997 Phase 2
0.7182 Intermediate Similarity NPD6688 Approved
0.7182 Intermediate Similarity NPD6687 Approved
0.7179 Intermediate Similarity NPD2494 Approved
0.7179 Intermediate Similarity NPD2493 Approved
0.7179 Intermediate Similarity NPD3452 Approved
0.7179 Intermediate Similarity NPD3450 Approved
0.7178 Intermediate Similarity NPD5718 Phase 2
0.7169 Intermediate Similarity NPD6895 Approved
0.7169 Intermediate Similarity NPD6896 Approved
0.716 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD3383 Approved
0.7159 Intermediate Similarity NPD3382 Approved
0.7159 Intermediate Similarity NPD3384 Approved
0.7158 Intermediate Similarity NPD2490 Approved
0.7158 Intermediate Similarity NPD2488 Approved
0.7157 Intermediate Similarity NPD4582 Approved
0.7157 Intermediate Similarity NPD4583 Approved
0.7152 Intermediate Similarity NPD3705 Approved
0.7143 Intermediate Similarity NPD7047 Phase 3
0.7111 Intermediate Similarity NPD5677 Discontinued
0.7107 Intermediate Similarity NPD4004 Approved
0.7107 Intermediate Similarity NPD4002 Approved
0.7098 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4055 Discovery
0.7095 Intermediate Similarity NPD5604 Discontinued
0.7091 Intermediate Similarity NPD3109 Approved
0.7091 Intermediate Similarity NPD3110 Approved
0.7086 Intermediate Similarity NPD4005 Discontinued
0.7079 Intermediate Similarity NPD7827 Phase 1
0.7077 Intermediate Similarity NPD8095 Phase 1
0.7069 Intermediate Similarity NPD5976 Discontinued
0.7066 Intermediate Similarity NPD6111 Discontinued
0.7052 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4474 Approved
0.703 Intermediate Similarity NPD4475 Approved
0.7006 Intermediate Similarity NPD2492 Phase 1
0.6994 Remote Similarity NPD3124 Discontinued
0.699 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2238 Phase 2
0.6984 Remote Similarity NPD6853 Approved
0.6984 Remote Similarity NPD6851 Approved
0.6979 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6978 Remote Similarity NPD7802 Discontinued
0.6966 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5177 Phase 3
0.6954 Remote Similarity NPD4107 Approved
0.6952 Remote Similarity NPD6297 Approved
0.6947 Remote Similarity NPD5087 Clinical (unspecified phase)
0.6941 Remote Similarity NPD1375 Discontinued
0.6927 Remote Similarity NPD4585 Approved
0.6927 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5754 Discontinued
0.6915 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6914 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1372 Clinical (unspecified phase)
0.69 Remote Similarity NPD4040 Phase 1
0.6898 Remote Similarity NPD3885 Approved
0.6889 Remote Similarity NPD5977 Approved
0.6889 Remote Similarity NPD5978 Approved
0.6866 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6864 Remote Similarity NPD2200 Suspended
0.6862 Remote Similarity NPD7007 Discovery
0.686 Remote Similarity NPD4162 Approved
0.686 Remote Similarity NPD3060 Approved
0.6845 Remote Similarity NPD5600 Discontinued
0.6834 Remote Similarity NPD4482 Phase 3
0.6828 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6824 Remote Similarity NPD4108 Discontinued
0.6824 Remote Similarity NPD1753 Discontinued
0.6821 Remote Similarity NPD6748 Discontinued
0.6816 Remote Similarity NPD6385 Approved
0.6816 Remote Similarity NPD6386 Approved
0.6811 Remote Similarity NPD5242 Approved
0.68 Remote Similarity NPD2421 Approved
0.68 Remote Similarity NPD2420 Approved
0.68 Remote Similarity NPD5297 Approved
0.6798 Remote Similarity NPD4859 Phase 1
0.6793 Remote Similarity NPD3983 Phase 3
0.6793 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6841 Approved
0.6788 Remote Similarity NPD6843 Phase 3
0.6788 Remote Similarity NPD6842 Approved
0.6778 Remote Similarity NPD5720 Discontinued
0.6776 Remote Similarity NPD7400 Phase 3
0.6772 Remote Similarity NPD6996 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7497 Discontinued
0.6761 Remote Similarity NPD4123 Phase 3
0.6761 Remote Similarity NPD7019 Approved
0.6761 Remote Similarity NPD7020 Approved
0.676 Remote Similarity NPD4675 Approved
0.676 Remote Similarity NPD4678 Approved
0.6758 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6758 Remote Similarity NPD4967 Phase 2
0.6758 Remote Similarity NPD4966 Approved
0.6758 Remote Similarity NPD4965 Approved
0.6754 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6724 Remote Similarity NPD7466 Approved
0.6723 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6722 Remote Similarity NPD5089 Approved
0.6722 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6722 Remote Similarity NPD5090 Approved
0.6722 Remote Similarity NPD7110 Phase 1
0.6718 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6716 Remote Similarity NPD3057 Approved
0.6707 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7549 Discontinued
0.6702 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6701 Remote Similarity NPD3349 Phase 2
0.6701 Remote Similarity NPD7291 Discontinued
0.6686 Remote Similarity NPD5160 Discontinued
0.6686 Remote Similarity NPD2677 Approved
0.6686 Remote Similarity NPD2161 Phase 2
0.6685 Remote Similarity NPD6234 Discontinued
0.6685 Remote Similarity NPD4796 Discontinued

  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