Structure

Physi-Chem Properties

Molecular Weight:  385.19
Volume:  399.891
LogP:  2.634
LogD:  2.881
LogS:  -3.565
# Rotatable Bonds:  4
TPSA:  57.23
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.806
Synthetic Accessibility Score:  2.864
Fsp3:  0.409
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:  -4.866
MDCK Permeability:  1.8089507648255676e-05
Pgp-inhibitor:  0.19
Pgp-substrate:  0.724
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.99
Plasma Protein Binding (PPB):  69.9420394897461%
Volume Distribution (VD):  1.747
Pgp-substrate:  20.237947463989258%

ADMET: Metabolism

CYP1A2-inhibitor:  0.129
CYP1A2-substrate:  0.971
CYP2C19-inhibitor:  0.167
CYP2C19-substrate:  0.953
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.792
CYP2D6-inhibitor:  0.315
CYP2D6-substrate:  0.923
CYP3A4-inhibitor:  0.097
CYP3A4-substrate:  0.927

ADMET: Excretion

Clearance (CL):  10.471
Half-life (T1/2):  0.746

ADMET: Toxicity

hERG Blockers:  0.609
Human Hepatotoxicity (H-HT):  0.455
Drug-inuced Liver Injury (DILI):  0.905
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.56
Maximum Recommended Daily Dose:  0.111
Skin Sensitization:  0.186
Carcinogencity:  0.048
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.96

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  Natural Product: NPC153631

Natural Product ID:  NPC153631
Common Name*:   3,4,10,11-Tetramethoxy-6-Methyl-5,7,8,14-Tetrahydrobenzo[E][2]Benzazecin-13-One
IUPAC Name:   3,4,10,11-tetramethoxy-6-methyl-5,7,8,14-tetrahydrobenzo[e][2]benzazecin-13-one
Synonyms:  
Standard InCHIKey:  HUIJAZQRYSCNED-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H27NO5/c1-23-9-8-15-11-20(26-3)21(27-4)12-16(15)18(24)10-14-6-7-19(25-2)22(28-5)17(14)13-23/h6-7,11-12H,8-10,13H2,1-5H3
SMILES:  COc1cc2CCN(C)Cc3c(CC(=O)c2cc1OC)ccc(c3OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1971249
PubChem CID:   288122
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002743] Protopine 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
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO25921 Papaver nudicaule Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1459 Euonymus mupinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25921 Papaver nudicaule Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1459 Euonymus mupinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1459 Euonymus mupinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25921 Papaver nudicaule Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25921 Papaver nudicaule Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1459 Euonymus mupinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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

  NP Quantity Composition/Concentration

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

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

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 27669.42 nM PMID[542453]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 20511.62 nM PMID[542453]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 11885.02 nM PMID[542453]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 24490.63 nM PMID[542453]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 46344.69 nM PMID[542453]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 15595.53 nM PMID[542453]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[542453]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 32359.37 nM PMID[542453]

☑ 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 NPC153631 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
0.9554 High Similarity NPC303581
0.9554 High Similarity NPC67978
0.9434 High Similarity NPC308267
0.9198 High Similarity NPC121400
0.9182 High Similarity NPC86469
0.8718 High Similarity NPC119669
0.8563 High Similarity NPC222524
0.8353 Intermediate Similarity NPC27887
0.8344 Intermediate Similarity NPC135006
0.8274 Intermediate Similarity NPC227683
0.8218 Intermediate Similarity NPC477259
0.8218 Intermediate Similarity NPC169387
0.8199 Intermediate Similarity NPC58661
0.8171 Intermediate Similarity NPC208890
0.8133 Intermediate Similarity NPC476569
0.8113 Intermediate Similarity NPC106295
0.8113 Intermediate Similarity NPC476144
0.8113 Intermediate Similarity NPC210437
0.8113 Intermediate Similarity NPC51957
0.8113 Intermediate Similarity NPC16107
0.8103 Intermediate Similarity NPC116007
0.8095 Intermediate Similarity NPC284842
0.8077 Intermediate Similarity NPC328750
0.8077 Intermediate Similarity NPC188163
0.8077 Intermediate Similarity NPC474915
0.8077 Intermediate Similarity NPC213206
0.8063 Intermediate Similarity NPC7467
0.8025 Intermediate Similarity NPC908
0.8025 Intermediate Similarity NPC476579
0.8025 Intermediate Similarity NPC138438
0.8013 Intermediate Similarity NPC314682
0.8012 Intermediate Similarity NPC470088
0.8011 Intermediate Similarity NPC207239
0.8 Intermediate Similarity NPC172403
0.8 Intermediate Similarity NPC476151
0.7978 Intermediate Similarity NPC226708
0.7944 Intermediate Similarity NPC477258
0.7937 Intermediate Similarity NPC290404
0.7935 Intermediate Similarity NPC89504
0.7935 Intermediate Similarity NPC95485
0.7935 Intermediate Similarity NPC88065
0.7927 Intermediate Similarity NPC470708
0.7919 Intermediate Similarity NPC35680
0.7901 Intermediate Similarity NPC477565
0.7901 Intermediate Similarity NPC24228
0.7901 Intermediate Similarity NPC103379
0.7898 Intermediate Similarity NPC83511
0.7895 Intermediate Similarity NPC160193
0.7875 Intermediate Similarity NPC469978
0.7862 Intermediate Similarity NPC476567
0.7862 Intermediate Similarity NPC136860
0.7862 Intermediate Similarity NPC128019
0.7861 Intermediate Similarity NPC207721
0.7857 Intermediate Similarity NPC266425
0.7853 Intermediate Similarity NPC478189
0.7853 Intermediate Similarity NPC18306
0.7848 Intermediate Similarity NPC223336
0.7844 Intermediate Similarity NPC118804
0.7831 Intermediate Similarity NPC57512
0.78 Intermediate Similarity NPC30216
0.7791 Intermediate Similarity NPC469539
0.7791 Intermediate Similarity NPC469540
0.779 Intermediate Similarity NPC469815
0.779 Intermediate Similarity NPC469816
0.7785 Intermediate Similarity NPC470962
0.7778 Intermediate Similarity NPC63152
0.7771 Intermediate Similarity NPC295691
0.7771 Intermediate Similarity NPC110416
0.7771 Intermediate Similarity NPC41178
0.7771 Intermediate Similarity NPC276588
0.7771 Intermediate Similarity NPC54379
0.7771 Intermediate Similarity NPC172765
0.7771 Intermediate Similarity NPC207757
0.7771 Intermediate Similarity NPC2413
0.7771 Intermediate Similarity NPC469817
0.7771 Intermediate Similarity NPC127674
0.7771 Intermediate Similarity NPC39701
0.7771 Intermediate Similarity NPC184026
0.7771 Intermediate Similarity NPC216459
0.7771 Intermediate Similarity NPC189266
0.7771 Intermediate Similarity NPC278799
0.7771 Intermediate Similarity NPC5238
0.7771 Intermediate Similarity NPC204828
0.7771 Intermediate Similarity NPC138487
0.7771 Intermediate Similarity NPC193949
0.7771 Intermediate Similarity NPC249797
0.7764 Intermediate Similarity NPC185838
0.776 Intermediate Similarity NPC71124
0.776 Intermediate Similarity NPC70290
0.776 Intermediate Similarity NPC14622
0.776 Intermediate Similarity NPC46744
0.776 Intermediate Similarity NPC124302
0.776 Intermediate Similarity NPC73020
0.776 Intermediate Similarity NPC215098
0.7758 Intermediate Similarity NPC476580
0.773 Intermediate Similarity NPC476571
0.773 Intermediate Similarity NPC153644
0.773 Intermediate Similarity NPC135538
0.773 Intermediate Similarity NPC147390
0.773 Intermediate Similarity NPC428
0.773 Intermediate Similarity NPC475959
0.773 Intermediate Similarity NPC24233
0.773 Intermediate Similarity NPC246587
0.7727 Intermediate Similarity NPC99723
0.7725 Intermediate Similarity NPC146288
0.7701 Intermediate Similarity NPC268077
0.7697 Intermediate Similarity NPC81733
0.7697 Intermediate Similarity NPC326316
0.7688 Intermediate Similarity NPC119818
0.7688 Intermediate Similarity NPC328700
0.7688 Intermediate Similarity NPC2173
0.7688 Intermediate Similarity NPC202771
0.7684 Intermediate Similarity NPC298339
0.7676 Intermediate Similarity NPC72788
0.7676 Intermediate Similarity NPC120671
0.7676 Intermediate Similarity NPC226652
0.7676 Intermediate Similarity NPC314100
0.7669 Intermediate Similarity NPC179825
0.7669 Intermediate Similarity NPC191376
0.7669 Intermediate Similarity NPC321505
0.7665 Intermediate Similarity NPC93593
0.7658 Intermediate Similarity NPC471316
0.7654 Intermediate Similarity NPC130926
0.765 Intermediate Similarity NPC125924
0.7647 Intermediate Similarity NPC207971
0.7637 Intermediate Similarity NPC254957
0.7633 Intermediate Similarity NPC106786
0.7622 Intermediate Similarity NPC5374
0.7619 Intermediate Similarity NPC31311
0.7619 Intermediate Similarity NPC234392
0.7619 Intermediate Similarity NPC308943
0.7616 Intermediate Similarity NPC474691
0.7614 Intermediate Similarity NPC241704
0.7611 Intermediate Similarity NPC162694
0.7607 Intermediate Similarity NPC472836
0.7605 Intermediate Similarity NPC2295
0.7605 Intermediate Similarity NPC477564
0.7602 Intermediate Similarity NPC59567
0.7593 Intermediate Similarity NPC86455
0.7593 Intermediate Similarity NPC137920
0.7593 Intermediate Similarity NPC229218
0.7593 Intermediate Similarity NPC176030
0.7593 Intermediate Similarity NPC125134
0.7593 Intermediate Similarity NPC169214
0.7593 Intermediate Similarity NPC141817
0.7593 Intermediate Similarity NPC192597
0.759 Intermediate Similarity NPC8337
0.759 Intermediate Similarity NPC85747
0.7574 Intermediate Similarity NPC476572
0.7569 Intermediate Similarity NPC141440
0.756 Intermediate Similarity NPC325871
0.756 Intermediate Similarity NPC99659
0.7558 Intermediate Similarity NPC2770
0.7558 Intermediate Similarity NPC39103
0.7556 Intermediate Similarity NPC214629
0.7544 Intermediate Similarity NPC60186
0.7541 Intermediate Similarity NPC94499
0.7533 Intermediate Similarity NPC225245
0.7532 Intermediate Similarity NPC11147
0.753 Intermediate Similarity NPC220858
0.753 Intermediate Similarity NPC151895
0.753 Intermediate Similarity NPC88249
0.753 Intermediate Similarity NPC192768
0.753 Intermediate Similarity NPC97221
0.753 Intermediate Similarity NPC223125
0.7529 Intermediate Similarity NPC470324
0.7528 Intermediate Similarity NPC32154
0.7516 Intermediate Similarity NPC160692
0.7516 Intermediate Similarity NPC153453
0.7487 Intermediate Similarity NPC38964
0.7486 Intermediate Similarity NPC196231
0.7485 Intermediate Similarity NPC476568
0.7485 Intermediate Similarity NPC80928
0.7484 Intermediate Similarity NPC131204
0.7484 Intermediate Similarity NPC301050
0.7484 Intermediate Similarity NPC7018
0.7484 Intermediate Similarity NPC167944
0.7484 Intermediate Similarity NPC231884
0.7484 Intermediate Similarity NPC42793
0.7473 Intermediate Similarity NPC17677
0.7473 Intermediate Similarity NPC23080
0.7473 Intermediate Similarity NPC166979
0.7473 Intermediate Similarity NPC193906
0.747 Intermediate Similarity NPC60538
0.747 Intermediate Similarity NPC474999
0.747 Intermediate Similarity NPC92541
0.747 Intermediate Similarity NPC219162
0.747 Intermediate Similarity NPC207824
0.7459 Intermediate Similarity NPC33256
0.7457 Intermediate Similarity NPC238530
0.7457 Intermediate Similarity NPC255607
0.7457 Intermediate Similarity NPC306669
0.7457 Intermediate Similarity NPC3375
0.7457 Intermediate Similarity NPC231198
0.7457 Intermediate Similarity NPC232514
0.7457 Intermediate Similarity NPC276944
0.7456 Intermediate Similarity NPC244112
0.7455 Intermediate Similarity NPC160777
0.7455 Intermediate Similarity NPC73416
0.7453 Intermediate Similarity NPC44573

  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 NPC153631 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
0.8797 High Similarity NPD5977 Approved
0.8797 High Similarity NPD5978 Approved
0.8148 Intermediate Similarity NPD6386 Approved
0.8148 Intermediate Similarity NPD6385 Approved
0.8137 Intermediate Similarity NPD824 Approved
0.8125 Intermediate Similarity NPD3639 Approved
0.8125 Intermediate Similarity NPD3640 Phase 3
0.8125 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD3641 Approved
0.8113 Intermediate Similarity NPD4584 Approved
0.8086 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD5242 Approved
0.7975 Intermediate Similarity NPD6875 Approved
0.7975 Intermediate Similarity NPD6876 Approved
0.7943 Intermediate Similarity NPD6618 Phase 2
0.7927 Intermediate Similarity NPD6873 Phase 2
0.7927 Intermediate Similarity NPD7110 Phase 1
0.7927 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD4420 Approved
0.7722 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD5564 Approved
0.7688 Intermediate Similarity NPD5005 Approved
0.7688 Intermediate Similarity NPD5006 Approved
0.7684 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD7291 Discontinued
0.7581 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2898 Approved
0.7516 Intermediate Similarity NPD3142 Approved
0.7516 Intermediate Similarity NPD3140 Approved
0.75 Intermediate Similarity NPD5312 Approved
0.75 Intermediate Similarity NPD5313 Approved
0.75 Intermediate Similarity NPD4413 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD4017 Approved
0.7485 Intermediate Similarity NPD8005 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6896 Approved
0.7484 Intermediate Similarity NPD743 Approved
0.7484 Intermediate Similarity NPD6895 Approved
0.7484 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6031 Approved
0.747 Intermediate Similarity NPD6030 Approved
0.7459 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD6297 Approved
0.7401 Intermediate Similarity NPD3050 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD2968 Approved
0.7389 Intermediate Similarity NPD5718 Phase 2
0.7389 Intermediate Similarity NPD2971 Approved
0.7384 Intermediate Similarity NPD1309 Phase 2
0.7384 Intermediate Similarity NPD1307 Phase 2
0.7381 Intermediate Similarity NPD2649 Approved
0.7381 Intermediate Similarity NPD2651 Approved
0.738 Intermediate Similarity NPD5071 Phase 2
0.7378 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1670 Discontinued
0.7363 Intermediate Similarity NPD4084 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD6107 Approved
0.7353 Intermediate Similarity NPD7298 Approved
0.7325 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD4107 Approved
0.7293 Intermediate Similarity NPD7280 Phase 3
0.7293 Intermediate Similarity NPD7281 Phase 3
0.7293 Intermediate Similarity NPD6146 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD3863 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2563 Approved
0.7267 Intermediate Similarity NPD5353 Approved
0.7267 Intermediate Similarity NPD2560 Approved
0.7263 Intermediate Similarity NPD5441 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD5586 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD6853 Approved
0.7253 Intermediate Similarity NPD6851 Approved
0.7251 Intermediate Similarity NPD6844 Discontinued
0.7251 Intermediate Similarity NPD7577 Discontinued
0.7247 Intermediate Similarity NPD8252 Approved
0.7247 Intermediate Similarity NPD8099 Discontinued
0.7247 Intermediate Similarity NPD8251 Approved
0.7243 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD6894 Phase 1
0.7225 Intermediate Similarity NPD6788 Approved
0.7216 Intermediate Similarity NPD6747 Phase 1
0.7211 Intermediate Similarity NPD5457 Discontinued
0.7211 Intermediate Similarity NPD7255 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD8156 Discontinued
0.7202 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD4772 Phase 2
0.7193 Intermediate Similarity NPD4773 Phase 2
0.7184 Intermediate Similarity NPD7831 Phase 2
0.7184 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7833 Phase 2
0.7176 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD4482 Phase 3
0.7169 Intermediate Similarity NPD5241 Discontinued
0.7169 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4466 Phase 1
0.7166 Intermediate Similarity NPD6181 Discontinued
0.7159 Intermediate Similarity NPD7802 Discontinued
0.7152 Intermediate Similarity NPD2654 Approved
0.7152 Intermediate Similarity NPD5536 Phase 2
0.7151 Intermediate Similarity NPD2488 Approved
0.7151 Intermediate Similarity NPD2490 Approved
0.7151 Intermediate Similarity NPD6280 Approved
0.7151 Intermediate Similarity NPD7177 Discontinued
0.7151 Intermediate Similarity NPD6279 Approved
0.7151 Intermediate Similarity NPD2822 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2975 Approved
0.7143 Intermediate Similarity NPD2973 Approved
0.7143 Intermediate Similarity NPD2974 Approved
0.7143 Intermediate Similarity NPD1424 Approved
0.7135 Intermediate Similarity NPD3057 Approved
0.7135 Intermediate Similarity NPD6040 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD3823 Discontinued
0.7126 Intermediate Similarity NPD7124 Phase 2
0.7125 Intermediate Similarity NPD4475 Approved
0.7125 Intermediate Similarity NPD4474 Approved
0.7119 Intermediate Similarity NPD5183 Approved
0.7119 Intermediate Similarity NPD4166 Phase 2
0.7119 Intermediate Similarity NPD5186 Approved
0.7113 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD4585 Approved
0.7102 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3972 Approved
0.7095 Intermediate Similarity NPD3446 Phase 1
0.7091 Intermediate Similarity NPD3655 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD7038 Approved
0.7088 Intermediate Similarity NPD7039 Approved
0.7073 Intermediate Similarity NPD4476 Approved
0.7073 Intermediate Similarity NPD4477 Approved
0.7062 Intermediate Similarity NPD2821 Approved
0.7056 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD5914 Approved
0.7049 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD7190 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4162 Approved
0.7047 Intermediate Similarity NPD3533 Approved
0.7047 Intermediate Similarity NPD2972 Approved
0.7047 Intermediate Similarity NPD2491 Approved
0.7047 Intermediate Similarity NPD3448 Approved
0.7041 Intermediate Similarity NPD4662 Approved
0.7041 Intermediate Similarity NPD4661 Approved
0.7041 Intermediate Similarity NPD4859 Phase 1
0.7039 Intermediate Similarity NPD3451 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD4580 Approved
0.7029 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD4947 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD160 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4010 Discontinued
0.7022 Intermediate Similarity NPD6071 Discontinued
0.7006 Intermediate Similarity NPD1876 Approved
0.6995 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6995 Remote Similarity NPD3450 Approved
0.6995 Remote Similarity NPD2494 Approved
0.6995 Remote Similarity NPD3452 Approved
0.6995 Remote Similarity NPD2493 Approved
0.6994 Remote Similarity NPD2653 Approved
0.6994 Remote Similarity NPD2492 Phase 1
0.6993 Remote Similarity NPD2486 Discontinued
0.6983 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6976 Remote Similarity NPD7279 Phase 2
0.6976 Remote Similarity NPD7278 Phase 2
0.6973 Remote Similarity NPD8053 Approved
0.6973 Remote Similarity NPD8054 Approved
0.697 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6961 Remote Similarity NPD2163 Approved
0.6959 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7626 Approved
0.6959 Remote Similarity NPD7427 Discontinued
0.6959 Remote Similarity NPD956 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1914 Approved
0.6959 Remote Similarity NPD7627 Approved
0.6954 Remote Similarity NPD7248 Discontinued
0.6952 Remote Similarity NPD7693 Approved
0.6946 Remote Similarity NPD5177 Phase 3
0.6946 Remote Similarity NPD2899 Discontinued
0.6946 Remote Similarity NPD3060 Approved
0.6944 Remote Similarity NPD4481 Phase 3
0.6941 Remote Similarity NPD3146 Approved
0.6941 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6808 Phase 2
0.6923 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7905 Discontinued
0.6914 Remote Similarity NPD2674 Phase 3
0.6914 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6911 Remote Similarity NPD6834 Approved
0.691 Remote Similarity NPD5494 Approved
0.6905 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6903 Remote Similarity NPD2667 Approved
0.6903 Remote Similarity NPD2668 Approved
0.6901 Remote Similarity NPD6090 Discontinued
0.6897 Remote Similarity NPD5890 Approved
0.6897 Remote Similarity NPD5889 Approved
0.6897 Remote Similarity NPD5089 Approved
0.6897 Remote Similarity NPD5090 Approved
0.6893 Remote Similarity NPD4055 Discovery
0.689 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6888 Remote Similarity NPD4582 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