Structure

Physi-Chem Properties

Molecular Weight:  726.35
Volume:  744.561
LogP:  4.954
LogD:  3.931
LogS:  -3.657
# Rotatable Bonds:  12
TPSA:  89.55
# H-Bond Aceptor:  11
# H-Bond Donor:  0
# Rings:  7
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.15
Synthetic Accessibility Score:  4.09
Fsp3:  0.429
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.87
MDCK Permeability:  2.942132778116502e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.142
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.68

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.073
Plasma Protein Binding (PPB):  46.8538703918457%
Volume Distribution (VD):  1.14
Pgp-substrate:  53.10497283935547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.993
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.982
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.826
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.968
CYP3A4-inhibitor:  0.086
CYP3A4-substrate:  0.967

ADMET: Excretion

Clearance (CL):  7.838
Half-life (T1/2):  0.209

ADMET: Toxicity

hERG Blockers:  0.972
Human Hepatotoxicity (H-HT):  0.032
Drug-inuced Liver Injury (DILI):  0.879
AMES Toxicity:  0.046
Rat Oral Acute Toxicity:  0.223
Maximum Recommended Daily Dose:  0.933
Skin Sensitization:  0.227
Carcinogencity:  0.008
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.686

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

  Natural Product: NPC47077

Natural Product ID:  NPC47077
Common Name*:   9-[2-[(6,7-Dimethoxy-2-Methyl-3,4-Dihydro-1H-Isoquinolin-1-Yl)Methyl]-4,5-Dimethoxyphenoxy]-1,2,3,10-Tetramethoxy-6-Methyl-5,6,6A,7-Tetrahydro-4H-Dibenzo[De,G]Quinoline
IUPAC Name:   9-[2-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-4,5-dimethoxyphenoxy]-1,2,3,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:  
Standard InCHIKey:  UEKRHVIBSZVFQN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C42H50N2O9/c1-43-13-11-23-17-32(45-3)34(47-5)20-27(23)29(43)16-25-19-33(46-4)36(49-7)22-31(25)53-37-18-24-15-30-38-26(12-14-44(30)2)40(50-8)42(52-10)41(51-9)39(38)28(24)21-35(37)48-6/h17-22,29-30H,11-16H2,1-10H3
SMILES:  CN1CCc2cc(c(cc2C1Cc1cc(c(cc1Oc1cc2CC3c4c(CCN3C)c(c(c(c4-c2cc1OC)OC)OC)OC)OC)OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2002665
PubChem CID:   422708
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO13508 Thalictrum honanenae Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11635.1 Thalictrum minus var. adiantifolium Varieties Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13508 Thalictrum honanenae Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11635.1 Thalictrum minus var. adiantifolium Varieties Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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. 13995.87 nM PMID[526685]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 17139.57 nM PMID[526685]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 7925.01 nM PMID[526685]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 15848.93 nM PMID[526685]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 9289.66 nM PMID[526685]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 6531.31 nM PMID[526685]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 13001.7 nM PMID[526685]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 4325.14 nM PMID[526685]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2494.59 nM PMID[526685]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 2630.27 nM PMID[526685]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 15275.66 nM PMID[526685]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 12302.69 nM PMID[526685]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 4518.56 nM PMID[526685]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 17338.04 nM PMID[526685]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 12589.25 nM PMID[526685]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 16218.1 nM PMID[526685]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 14927.94 nM PMID[526685]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 12502.59 nM PMID[526685]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 19408.86 nM PMID[526685]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 15417.0 nM PMID[526685]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 15559.66 nM PMID[526685]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 14962.36 nM PMID[526685]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 11668.1 nM PMID[526685]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 12735.03 nM PMID[526685]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 13001.7 nM PMID[526685]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 2404.36 nM PMID[526685]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 39355.01 nM PMID[526685]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 13995.87 nM PMID[526685]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 15958.79 nM PMID[526685]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 6729.77 nM PMID[526685]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 14588.14 nM PMID[526685]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 15885.47 nM PMID[526685]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 5929.25 nM PMID[526685]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 11376.27 nM PMID[526685]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 5321.08 nM PMID[526685]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 10115.79 nM PMID[526685]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 14962.36 nM PMID[526685]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 11668.1 nM PMID[526685]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 16557.7 nM PMID[526685]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 12133.89 nM PMID[526685]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 13677.29 nM PMID[526685]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 19678.86 nM PMID[526685]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 15595.53 nM PMID[526685]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 15240.53 nM PMID[526685]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 14757.07 nM PMID[526685]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 14588.14 nM PMID[526685]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 14288.94 nM PMID[526685]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 12246.16 nM PMID[526685]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 6309.57 nM PMID[526685]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 17418.07 nM PMID[526685]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 8394.6 nM PMID[526685]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 15452.54 nM PMID[526685]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 16405.9 nM PMID[526685]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 17218.69 nM PMID[526685]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 8770.01 nM PMID[526685]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 9638.29 nM PMID[526685]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 2897.34 nM PMID[526685]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 7227.7 nM PMID[526685]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 16368.17 nM PMID[526685]

☑ 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 NPC47077 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 NPC14507
0.9762 High Similarity NPC302275
0.9371 High Similarity NPC30182
0.9371 High Similarity NPC473589
0.9371 High Similarity NPC478091
0.9371 High Similarity NPC478092
0.9349 High Similarity NPC293093
0.9314 High Similarity NPC478093
0.9172 High Similarity NPC198498
0.9172 High Similarity NPC317145
0.9172 High Similarity NPC317439
0.9172 High Similarity NPC63646
0.9172 High Similarity NPC115284
0.9172 High Similarity NPC276890
0.9172 High Similarity NPC10908
0.9172 High Similarity NPC227060
0.9172 High Similarity NPC76682
0.9138 High Similarity NPC16357
0.9138 High Similarity NPC302245
0.9138 High Similarity NPC95426
0.9118 High Similarity NPC41376
0.9118 High Similarity NPC12424
0.9118 High Similarity NPC251580
0.9118 High Similarity NPC129518
0.9086 High Similarity NPC139783
0.9086 High Similarity NPC65312
0.9034 High Similarity NPC275680
0.9034 High Similarity NPC22115
0.8977 High Similarity NPC212237
0.8977 High Similarity NPC116465
0.8914 High Similarity NPC30779
0.8908 High Similarity NPC243454
0.8908 High Similarity NPC475479
0.8857 High Similarity NPC239584
0.8857 High Similarity NPC286119
0.8833 High Similarity NPC256124
0.8807 High Similarity NPC239824
0.8807 High Similarity NPC217748
0.8807 High Similarity NPC290005
0.8807 High Similarity NPC299990
0.8807 High Similarity NPC8836
0.8807 High Similarity NPC42663
0.8807 High Similarity NPC328155
0.8807 High Similarity NPC182052
0.8807 High Similarity NPC290582
0.8807 High Similarity NPC223690
0.8807 High Similarity NPC104196
0.8807 High Similarity NPC279228
0.8807 High Similarity NPC54654
0.8807 High Similarity NPC49075
0.8807 High Similarity NPC285931
0.8807 High Similarity NPC271013
0.8807 High Similarity NPC73492
0.8807 High Similarity NPC251735
0.8807 High Similarity NPC15414
0.8807 High Similarity NPC222661
0.8807 High Similarity NPC311973
0.8807 High Similarity NPC185639
0.8807 High Similarity NPC258657
0.8807 High Similarity NPC181796
0.8807 High Similarity NPC7715
0.8807 High Similarity NPC90998
0.8807 High Similarity NPC229373
0.8771 High Similarity NPC206900
0.8757 High Similarity NPC254441
0.8757 High Similarity NPC167116
0.8757 High Similarity NPC274716
0.869 High Similarity NPC476572
0.8683 High Similarity NPC99659
0.8683 High Similarity NPC325871
0.8663 High Similarity NPC204947
0.8644 High Similarity NPC195538
0.8631 High Similarity NPC247639
0.8631 High Similarity NPC25084
0.8621 High Similarity NPC149090
0.8621 High Similarity NPC239775
0.8621 High Similarity NPC19520
0.8603 High Similarity NPC249996
0.8596 High Similarity NPC476202
0.8564 High Similarity NPC281581
0.8564 High Similarity NPC175890
0.8564 High Similarity NPC48490
0.8564 High Similarity NPC82457
0.8564 High Similarity NPC11296
0.8564 High Similarity NPC274661
0.8516 High Similarity NPC473716
0.8516 High Similarity NPC475597
0.8516 High Similarity NPC191132
0.8516 High Similarity NPC60295
0.847 Intermediate Similarity NPC24260
0.8457 Intermediate Similarity NPC168753
0.8457 Intermediate Similarity NPC254581
0.8457 Intermediate Similarity NPC118274
0.8436 Intermediate Similarity NPC230276
0.8436 Intermediate Similarity NPC257269
0.8393 Intermediate Similarity NPC326316
0.8393 Intermediate Similarity NPC81733
0.8382 Intermediate Similarity NPC475393
0.838 Intermediate Similarity NPC119068
0.838 Intermediate Similarity NPC258695
0.838 Intermediate Similarity NPC470879
0.838 Intermediate Similarity NPC40496
0.8353 Intermediate Similarity NPC123323
0.8343 Intermediate Similarity NPC81218
0.8343 Intermediate Similarity NPC158376
0.8343 Intermediate Similarity NPC12053
0.8343 Intermediate Similarity NPC117188
0.8343 Intermediate Similarity NPC205421
0.8343 Intermediate Similarity NPC247389
0.8343 Intermediate Similarity NPC306555
0.8343 Intermediate Similarity NPC145832
0.8343 Intermediate Similarity NPC474931
0.8333 Intermediate Similarity NPC306843
0.8333 Intermediate Similarity NPC253043
0.8333 Intermediate Similarity NPC302527
0.8333 Intermediate Similarity NPC16805
0.8333 Intermediate Similarity NPC196447
0.8333 Intermediate Similarity NPC96603
0.8333 Intermediate Similarity NPC477563
0.8333 Intermediate Similarity NPC212794
0.8333 Intermediate Similarity NPC167546
0.8333 Intermediate Similarity NPC13504
0.8333 Intermediate Similarity NPC32413
0.8333 Intermediate Similarity NPC78222
0.8333 Intermediate Similarity NPC136508
0.8333 Intermediate Similarity NPC474506
0.8315 Intermediate Similarity NPC318805
0.8315 Intermediate Similarity NPC41122
0.8305 Intermediate Similarity NPC10871
0.8286 Intermediate Similarity NPC476432
0.8286 Intermediate Similarity NPC317272
0.8286 Intermediate Similarity NPC240841
0.8286 Intermediate Similarity NPC250846
0.8286 Intermediate Similarity NPC256012
0.8286 Intermediate Similarity NPC24264
0.8286 Intermediate Similarity NPC42549
0.8286 Intermediate Similarity NPC219341
0.8286 Intermediate Similarity NPC268503
0.8278 Intermediate Similarity NPC474507
0.8276 Intermediate Similarity NPC324144
0.8258 Intermediate Similarity NPC232386
0.8258 Intermediate Similarity NPC190783
0.8258 Intermediate Similarity NPC152680
0.8239 Intermediate Similarity NPC210918
0.8235 Intermediate Similarity NPC234318
0.8229 Intermediate Similarity NPC225774
0.8229 Intermediate Similarity NPC24465
0.8226 Intermediate Similarity NPC85381
0.8222 Intermediate Similarity NPC23219
0.8201 Intermediate Similarity NPC475654
0.8182 Intermediate Similarity NPC264850
0.8182 Intermediate Similarity NPC13916
0.8171 Intermediate Similarity NPC1229
0.8167 Intermediate Similarity NPC476577
0.8167 Intermediate Similarity NPC112575
0.8167 Intermediate Similarity NPC173416
0.8167 Intermediate Similarity NPC148709
0.8166 Intermediate Similarity NPC92541
0.8152 Intermediate Similarity NPC57036
0.814 Intermediate Similarity NPC244112
0.8118 Intermediate Similarity NPC475754
0.8115 Intermediate Similarity NPC473660
0.8114 Intermediate Similarity NPC80759
0.8114 Intermediate Similarity NPC79402
0.8092 Intermediate Similarity NPC126519
0.8092 Intermediate Similarity NPC203784
0.8092 Intermediate Similarity NPC170503
0.809 Intermediate Similarity NPC204908
0.809 Intermediate Similarity NPC83198
0.8065 Intermediate Similarity NPC82763
0.8057 Intermediate Similarity NPC205255
0.8057 Intermediate Similarity NPC235143
0.8057 Intermediate Similarity NPC477559
0.8057 Intermediate Similarity NPC271388
0.8057 Intermediate Similarity NPC119649
0.8057 Intermediate Similarity NPC306902
0.8057 Intermediate Similarity NPC166014
0.8057 Intermediate Similarity NPC232924
0.8057 Intermediate Similarity NPC27410
0.8057 Intermediate Similarity NPC266753
0.8057 Intermediate Similarity NPC230956
0.8057 Intermediate Similarity NPC160298
0.8056 Intermediate Similarity NPC477020
0.8056 Intermediate Similarity NPC192135
0.8056 Intermediate Similarity NPC66341
0.8054 Intermediate Similarity NPC214116
0.8047 Intermediate Similarity NPC16107
0.8047 Intermediate Similarity NPC210437
0.8047 Intermediate Similarity NPC144863
0.8047 Intermediate Similarity NPC476144
0.8047 Intermediate Similarity NPC106295
0.8047 Intermediate Similarity NPC51957
0.8045 Intermediate Similarity NPC69712
0.8045 Intermediate Similarity NPC477562
0.8045 Intermediate Similarity NPC26240
0.8045 Intermediate Similarity NPC6152
0.8024 Intermediate Similarity NPC128019
0.8024 Intermediate Similarity NPC136860
0.8024 Intermediate Similarity NPC476567
0.8022 Intermediate Similarity NPC114364

  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 NPC47077 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
0.9172 High Similarity NPD8099 Discontinued
0.9172 High Similarity NPD8252 Approved
0.9172 High Similarity NPD8251 Approved
0.9118 High Similarity NPD8156 Discontinued
0.8807 High Similarity NPD8054 Approved
0.8807 High Similarity NPD8053 Approved
0.838 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.8245 Intermediate Similarity NPD8095 Phase 1
0.8054 Intermediate Similarity NPD7906 Approved
0.8047 Intermediate Similarity NPD4584 Approved
0.8 Intermediate Similarity NPD6788 Approved
0.7829 Intermediate Similarity NPD7298 Approved
0.7798 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3051 Approved
0.7692 Intermediate Similarity NPD4481 Phase 3
0.7657 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD7313 Approved
0.7647 Intermediate Similarity NPD7311 Approved
0.7647 Intermediate Similarity NPD7312 Approved
0.7647 Intermediate Similarity NPD7310 Approved
0.7637 Intermediate Similarity NPD2970 Approved
0.7637 Intermediate Similarity NPD2969 Approved
0.7619 Intermediate Similarity NPD4663 Approved
0.7606 Intermediate Similarity NPD7309 Approved
0.7571 Intermediate Similarity NPD4772 Phase 2
0.7571 Intermediate Similarity NPD4773 Phase 2
0.7569 Intermediate Similarity NPD5677 Discontinued
0.7553 Intermediate Similarity NPD4578 Approved
0.7553 Intermediate Similarity NPD4577 Approved
0.7526 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2489 Approved
0.75 Intermediate Similarity NPD27 Approved
0.7486 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD7833 Phase 2
0.7459 Intermediate Similarity NPD7831 Phase 2
0.7459 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6071 Discontinued
0.7377 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD2420 Approved
0.7371 Intermediate Similarity NPD2421 Approved
0.7368 Intermediate Similarity NPD2971 Approved
0.7368 Intermediate Similarity NPD2968 Approved
0.7363 Intermediate Similarity NPD4055 Discovery
0.7345 Intermediate Similarity NPD6031 Approved
0.7345 Intermediate Similarity NPD3640 Phase 3
0.7345 Intermediate Similarity NPD6030 Approved
0.7345 Intermediate Similarity NPD3639 Approved
0.7345 Intermediate Similarity NPD3641 Approved
0.733 Intermediate Similarity NPD1424 Approved
0.7316 Intermediate Similarity NPD7549 Discontinued
0.7314 Intermediate Similarity NPD7124 Phase 2
0.731 Intermediate Similarity NPD2973 Approved
0.731 Intermediate Similarity NPD2974 Approved
0.731 Intermediate Similarity NPD2975 Approved
0.7263 Intermediate Similarity NPD4017 Approved
0.7243 Intermediate Similarity NPD6107 Approved
0.7243 Intermediate Similarity NPD7802 Discontinued
0.7213 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4580 Approved
0.7175 Intermediate Similarity NPD7598 Phase 2
0.7164 Intermediate Similarity NPD3452 Approved
0.7164 Intermediate Similarity NPD3450 Approved
0.7164 Intermediate Similarity NPD2493 Approved
0.7164 Intermediate Similarity NPD2494 Approved
0.7158 Intermediate Similarity NPD2563 Approved
0.7158 Intermediate Similarity NPD2560 Approved
0.7135 Intermediate Similarity NPD7447 Phase 1
0.712 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD4474 Approved
0.7118 Intermediate Similarity NPD4475 Approved
0.7095 Intermediate Similarity NPD6090 Discontinued
0.7089 Intermediate Similarity NPD6997 Phase 2
0.708 Intermediate Similarity NPD8152 Approved
0.708 Intermediate Similarity NPD8153 Approved
0.7076 Intermediate Similarity NPD3110 Approved
0.7076 Intermediate Similarity NPD3109 Approved
0.7062 Intermediate Similarity NPD5241 Discontinued
0.7059 Intermediate Similarity NPD5718 Phase 2
0.7059 Intermediate Similarity NPD4582 Approved
0.7059 Intermediate Similarity NPD4583 Approved
0.7056 Intermediate Similarity NPD2490 Approved
0.7056 Intermediate Similarity NPD2488 Approved
0.7052 Intermediate Similarity NPD2200 Suspended
0.705 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7047 Phase 3
0.7044 Intermediate Similarity NPD5006 Approved
0.7044 Intermediate Similarity NPD5005 Approved
0.7041 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD4675 Approved
0.7033 Intermediate Similarity NPD4678 Approved
0.7016 Intermediate Similarity NPD5313 Approved
0.7016 Intermediate Similarity NPD5312 Approved
0.701 Intermediate Similarity NPD4004 Approved
0.701 Intermediate Similarity NPD4002 Approved
0.7006 Intermediate Similarity NPD7466 Approved
0.7006 Intermediate Similarity NPD6748 Discontinued
0.6989 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7213 Phase 3
0.6983 Remote Similarity NPD7212 Phase 2
0.6983 Remote Similarity NPD3124 Discontinued
0.6978 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6978 Remote Similarity NPD4005 Discontinued
0.6959 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6111 Discontinued
0.6947 Remote Similarity NPD2898 Approved
0.6944 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6931 Remote Similarity NPD4166 Phase 2
0.6931 Remote Similarity NPD4420 Approved
0.6931 Remote Similarity NPD4010 Discontinued
0.6927 Remote Similarity NPD42 Phase 2
0.6927 Remote Similarity NPD6042 Phase 2
0.6919 Remote Similarity NPD4585 Approved
0.6906 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7827 Phase 1
0.6901 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6884 Remote Similarity NPD7907 Approved
0.6872 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7291 Discontinued
0.6868 Remote Similarity NPD5976 Discontinued
0.6863 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6896 Approved
0.6857 Remote Similarity NPD6895 Approved
0.6853 Remote Similarity NPD5087 Clinical (unspecified phase)
0.6837 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6833 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6833 Remote Similarity NPD3845 Phase 1
0.6825 Remote Similarity NPD6037 Discontinued
0.6823 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6816 Remote Similarity NPD5754 Discontinued
0.6811 Remote Similarity NPD6072 Discontinued
0.6806 Remote Similarity NPD6687 Approved
0.6806 Remote Similarity NPD6688 Approved
0.6802 Remote Similarity NPD7090 Clinical (unspecified phase)
0.678 Remote Similarity NPD4107 Approved
0.6776 Remote Similarity NPD2122 Discontinued
0.6774 Remote Similarity NPD3382 Approved
0.6774 Remote Similarity NPD3383 Approved
0.6774 Remote Similarity NPD3384 Approved
0.676 Remote Similarity NPD5177 Phase 3
0.6758 Remote Similarity NPD4123 Phase 3
0.6751 Remote Similarity NPD3534 Clinical (unspecified phase)
0.674 Remote Similarity NPD2422 Clinical (unspecified phase)
0.6738 Remote Similarity NPD5772 Approved
0.6738 Remote Similarity NPD5773 Approved
0.6733 Remote Similarity NPD7125 Discontinued
0.6733 Remote Similarity NPD7262 Phase 1
0.6732 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6625 Approved
0.6722 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6722 Remote Similarity NPD6658 Clinical (unspecified phase)
0.672 Remote Similarity NPD5090 Approved
0.672 Remote Similarity NPD5089 Approved
0.6719 Remote Similarity NPD5242 Approved
0.6717 Remote Similarity NPD6853 Approved
0.6717 Remote Similarity NPD6851 Approved
0.6715 Remote Similarity NPD7590 Clinical (unspecified phase)
0.6703 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6703 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6698 Remote Similarity NPD5676 Approved
0.6684 Remote Similarity NPD6297 Approved
0.6684 Remote Similarity NPD5720 Discontinued
0.6667 Remote Similarity NPD4482 Phase 3
0.6667 Remote Similarity NPD4098 Discontinued
0.6667 Remote Similarity NPD5844 Phase 1
0.6651 Remote Similarity NPD4040 Phase 1
0.6648 Remote Similarity NPD6666 Approved
0.6648 Remote Similarity NPD6667 Approved
0.6635 Remote Similarity NPD3057 Approved
0.6634 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6633 Remote Similarity NPD6618 Phase 2
0.6632 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6631 Remote Similarity NPD7110 Phase 1
0.6631 Remote Similarity NPD7109 Clinical (unspecified phase)
0.663 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6617 Remote Similarity NPD6842 Approved
0.6617 Remote Similarity NPD6843 Phase 3
0.6617 Remote Similarity NPD6841 Approved
0.6608 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6606 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6603 Remote Similarity NPD7497 Discontinued
0.6597 Remote Similarity NPD7400 Phase 3
0.6596 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6595 Remote Similarity NPD4727 Phase 1
0.6593 Remote Similarity NPD3692 Discontinued
0.6593 Remote Similarity NPD5160 Discontinued
0.6578 Remote Similarity NPD6723 Discontinued
0.6575 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6571 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7294 Phase 1
0.657 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6564 Remote Similarity NPD7048 Phase 3
0.6564 Remote Similarity NPD5938 Phase 3
0.6561 Remote Similarity NPD7046 Clinical (unspecified phase)
0.656 Remote Similarity NPD4665 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