Structure

Physi-Chem Properties

Molecular Weight:  430.31
Volume:  456.734
LogP:  4.618
LogD:  3.831
LogS:  -5.105
# Rotatable Bonds:  0
TPSA:  58.92
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.548
Synthetic Accessibility Score:  5.453
Fsp3:  0.926
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.74
MDCK Permeability:  7.202312190202065e-06
Pgp-inhibitor:  0.917
Pgp-substrate:  0.978
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.472
Plasma Protein Binding (PPB):  75.3691177368164%
Volume Distribution (VD):  1.735
Pgp-substrate:  8.694767951965332%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.376
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.747
CYP2C9-inhibitor:  0.095
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.305
CYP3A4-inhibitor:  0.573
CYP3A4-substrate:  0.383

ADMET: Excretion

Clearance (CL):  12.616
Half-life (T1/2):  0.146

ADMET: Toxicity

hERG Blockers:  0.973
Human Hepatotoxicity (H-HT):  0.456
Drug-inuced Liver Injury (DILI):  0.735
AMES Toxicity:  0.101
Rat Oral Acute Toxicity:  0.788
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.96
Carcinogencity:  0.65
Eye Corrosion:  0.029
Eye Irritation:  0.278
Respiratory Toxicity:  0.968

Download Data

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

  Natural Product: NPC177818

Natural Product ID:  NPC177818
Common Name*:   Ruscogenin
IUPAC Name:   n.a.
Synonyms:   Ruscogenin
Standard InCHIKey:  QMQIQBOGXYYATH-IDABPMKMSA-N
Standard InCHI:  InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
SMILES:  C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)[C@H](O)C[C@@H](C3)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1169820
PubChem CID:   441893
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO25265 Sophora secundiflora Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(00)78784-3]
NPO26956 Crambe crambe Species Esperiopsidae Eukaryota n.a. n.a. n.a. DOI[10.1021/jo00019a049]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[11325235]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[14575439]
NPO26173 Anomospermum grandifolium Species Menispermaceae Eukaryota Stems n.a. n.a. PMID[14695805]
NPO26683 Dichomitus squalens Species Polyporaceae Eukaryota n.a. n.a. n.a. PMID[15620268]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO24757 Meryta denhamii Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[18442289]
NPO9613 Anisomeles indica Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18547115]
NPO24883 Angiopteris caudatiformis Species Marattiaceae Eukaryota n.a. n.a. n.a. PMID[19371069]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota roots n.a. n.a. PMID[20346658]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. PMID[20581114]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[23439553]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. PMID[25515814]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO26550 Ruscus aculeatus Species Asparagaceae Eukaryota Underground parts n.a. n.a. PMID[9784168]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. tuber n.a. Database[Article]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25843 Solanum chacoense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9613 Anisomeles indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26550 Ruscus aculeatus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5275 Liriope muscari Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26915 Erinus alpinus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9613 Anisomeles indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26550 Ruscus aculeatus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25843 Solanum chacoense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26550 Ruscus aculeatus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25808 Fritillaria taipaiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5275 Liriope muscari Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2096 Stenostomum acutatum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27053 Maclura aurantiaca Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26173 Anomospermum grandifolium Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25729 Centaurea aemulans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5275 Liriope muscari Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25025 Gypothamnium pinifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23570 Hypolaena fastigiata Species Restionaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26427 Heterocapsa triquetra Species Heterocapsaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26550 Ruscus aculeatus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25210 Fulmarus glacialis Species Procellariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26683 Dichomitus squalens Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18404 Clarkia unguiculata Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24883 Angiopteris caudatiformis Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26862 Pentaceraster alveolatus Species Oreasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24509 Randia longispina Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24757 Meryta denhamii Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26693 Daphne papyracea Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26300 Penianthus zenkeri Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26467 Nipaecoccus aurilanatus Species Pseudococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12552 Aloe indica Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26444 Mimosa invisa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26489 Arthrobacter viscosus Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26793 Trichia carnea Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29139 Agave huachucensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26222 Gonepteryx rhamni Species Pieridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25265 Sophora secundiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26956 Crambe crambe Species Esperiopsidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23068 Guettarda eximia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27000 Geranium macrorrhizum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24150 Baptisia lecontii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25843 Solanum chacoense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23463 Basanacantha spinosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24594 Polypodium hastatum Species Polypodiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26915 Erinus alpinus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26843 Heliconius cydno Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9613 Anisomeles indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25783 Tulipa silvestris Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26577 Clinostemon mahuba n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24375 Micrococcus luteus Species Micrococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25438 Xiphophora gladiata Species Fucaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20000 Adina rubescens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25808 Fritillaria taipaiensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27027 Renilla muelleri Species Renillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26020 Dahlstedtia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27038 Senecio macrophyllus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25592 Pedicularis densispica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26106 Lactarius pubescens Species Russulaceae 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
NPT1970 Cell Line THP-1 Homo sapiens IC50 = 2270.0 nM PMID[503743]

☑ 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 NPC177818 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
0.9677 High Similarity NPC176406
0.9677 High Similarity NPC474022
0.9556 High Similarity NPC235126
0.9556 High Similarity NPC242419
0.9278 High Similarity NPC474015
0.9271 High Similarity NPC475701
0.9184 High Similarity NPC226642
0.9175 High Similarity NPC474464
0.9091 High Similarity NPC476539
0.9091 High Similarity NPC476540
0.9091 High Similarity NPC476541
0.9091 High Similarity NPC476538
0.9 High Similarity NPC128133
0.9 High Similarity NPC477027
0.9 High Similarity NPC475670
0.9 High Similarity NPC70204
0.9 High Similarity NPC306131
0.9 High Similarity NPC477026
0.898 High Similarity NPC471111
0.8889 High Similarity NPC473476
0.8889 High Similarity NPC473923
0.8889 High Similarity NPC181845
0.8854 High Similarity NPC275865
0.8854 High Similarity NPC309493
0.8824 High Similarity NPC475247
0.8824 High Similarity NPC294129
0.8824 High Similarity NPC13190
0.88 High Similarity NPC113044
0.88 High Similarity NPC305423
0.88 High Similarity NPC14704
0.88 High Similarity NPC230507
0.88 High Similarity NPC161676
0.88 High Similarity NPC283829
0.88 High Similarity NPC470432
0.8776 High Similarity NPC22634
0.875 High Similarity NPC473890
0.875 High Similarity NPC243728
0.8738 High Similarity NPC112274
0.8713 High Similarity NPC98696
0.87 High Similarity NPC242748
0.87 High Similarity NPC26798
0.866 High Similarity NPC158088
0.866 High Similarity NPC216260
0.866 High Similarity NPC5358
0.8654 High Similarity NPC51154
0.8646 High Similarity NPC207617
0.8641 High Similarity NPC197231
0.8627 High Similarity NPC95051
0.8627 High Similarity NPC475550
0.8627 High Similarity NPC42482
0.8627 High Similarity NPC194207
0.8627 High Similarity NPC244086
0.8627 High Similarity NPC171073
0.8627 High Similarity NPC309278
0.8627 High Similarity NPC300557
0.8627 High Similarity NPC248746
0.8627 High Similarity NPC46190
0.8627 High Similarity NPC6806
0.8627 High Similarity NPC208383
0.8627 High Similarity NPC470433
0.8627 High Similarity NPC150372
0.8627 High Similarity NPC475333
0.8627 High Similarity NPC218571
0.8627 High Similarity NPC84956
0.8627 High Similarity NPC22779
0.8627 High Similarity NPC73243
0.8627 High Similarity NPC102016
0.8627 High Similarity NPC40440
0.8627 High Similarity NPC224098
0.8627 High Similarity NPC249265
0.8627 High Similarity NPC477809
0.8627 High Similarity NPC232054
0.8614 High Similarity NPC473469
0.86 High Similarity NPC475365
0.8571 High Similarity NPC11548
0.8571 High Similarity NPC324598
0.8571 High Similarity NPC282669
0.8558 High Similarity NPC19888
0.8544 High Similarity NPC222202
0.8544 High Similarity NPC224314
0.8544 High Similarity NPC269297
0.8544 High Similarity NPC87998
0.8544 High Similarity NPC23808
0.8544 High Similarity NPC247037
0.8544 High Similarity NPC141433
0.8544 High Similarity NPC477811
0.8515 High Similarity NPC474569
0.85 High Similarity NPC471886
0.85 High Similarity NPC471887
0.85 High Similarity NPC213190
0.85 High Similarity NPC471885
0.85 High Similarity NPC471888
0.8491 Intermediate Similarity NPC63609
0.8491 Intermediate Similarity NPC477030
0.8491 Intermediate Similarity NPC477029
0.8485 Intermediate Similarity NPC470434
0.8485 Intermediate Similarity NPC267510
0.8478 Intermediate Similarity NPC24277
0.8476 Intermediate Similarity NPC144068
0.8469 Intermediate Similarity NPC234287
0.8469 Intermediate Similarity NPC280825
0.8462 Intermediate Similarity NPC476547
0.8462 Intermediate Similarity NPC477032
0.8462 Intermediate Similarity NPC13193
0.8462 Intermediate Similarity NPC477028
0.8462 Intermediate Similarity NPC124677
0.8462 Intermediate Similarity NPC124172
0.8454 Intermediate Similarity NPC304899
0.8454 Intermediate Similarity NPC253115
0.8447 Intermediate Similarity NPC476835
0.8444 Intermediate Similarity NPC470614
0.8444 Intermediate Similarity NPC1272
0.8431 Intermediate Similarity NPC94272
0.8416 Intermediate Similarity NPC93352
0.8416 Intermediate Similarity NPC470885
0.8416 Intermediate Similarity NPC221562
0.8416 Intermediate Similarity NPC187400
0.8416 Intermediate Similarity NPC75608
0.8411 Intermediate Similarity NPC477807
0.84 Intermediate Similarity NPC136816
0.84 Intermediate Similarity NPC272015
0.84 Intermediate Similarity NPC37207
0.84 Intermediate Similarity NPC228049
0.84 Intermediate Similarity NPC471482
0.84 Intermediate Similarity NPC300399
0.84 Intermediate Similarity NPC68630
0.84 Intermediate Similarity NPC154452
0.84 Intermediate Similarity NPC52585
0.8396 Intermediate Similarity NPC477810
0.8384 Intermediate Similarity NPC469942
0.8384 Intermediate Similarity NPC7341
0.8384 Intermediate Similarity NPC473790
0.8384 Intermediate Similarity NPC473200
0.8384 Intermediate Similarity NPC471242
0.8381 Intermediate Similarity NPC32361
0.8381 Intermediate Similarity NPC42171
0.8381 Intermediate Similarity NPC31896
0.8381 Intermediate Similarity NPC244431
0.8381 Intermediate Similarity NPC263359
0.8381 Intermediate Similarity NPC477050
0.8381 Intermediate Similarity NPC254255
0.8381 Intermediate Similarity NPC210569
0.8367 Intermediate Similarity NPC476893
0.8367 Intermediate Similarity NPC76486
0.8365 Intermediate Similarity NPC191439
0.8365 Intermediate Similarity NPC170974
0.8365 Intermediate Similarity NPC163314
0.8365 Intermediate Similarity NPC103627
0.8351 Intermediate Similarity NPC476894
0.835 Intermediate Similarity NPC295980
0.835 Intermediate Similarity NPC7213
0.8333 Intermediate Similarity NPC309448
0.8333 Intermediate Similarity NPC470383
0.8333 Intermediate Similarity NPC475403
0.8333 Intermediate Similarity NPC98193
0.8333 Intermediate Similarity NPC160888
0.8318 Intermediate Similarity NPC148965
0.8317 Intermediate Similarity NPC473198
0.8317 Intermediate Similarity NPC471450
0.8302 Intermediate Similarity NPC476693
0.8302 Intermediate Similarity NPC79900
0.8302 Intermediate Similarity NPC178981
0.83 Intermediate Similarity NPC129372
0.83 Intermediate Similarity NPC160734
0.83 Intermediate Similarity NPC21064
0.83 Intermediate Similarity NPC88000
0.83 Intermediate Similarity NPC121072
0.83 Intermediate Similarity NPC309425
0.83 Intermediate Similarity NPC4831
0.83 Intermediate Similarity NPC47566
0.83 Intermediate Similarity NPC472023
0.8298 Intermediate Similarity NPC470542
0.8286 Intermediate Similarity NPC65034
0.8286 Intermediate Similarity NPC114188
0.8286 Intermediate Similarity NPC208189
0.8283 Intermediate Similarity NPC476895
0.828 Intermediate Similarity NPC201273
0.8269 Intermediate Similarity NPC473328
0.8269 Intermediate Similarity NPC473318
0.8269 Intermediate Similarity NPC157530
0.8269 Intermediate Similarity NPC14630
0.8269 Intermediate Similarity NPC250089
0.8269 Intermediate Similarity NPC28844
0.8269 Intermediate Similarity NPC475030
0.8261 Intermediate Similarity NPC209802
0.8257 Intermediate Similarity NPC476085
0.8257 Intermediate Similarity NPC195560
0.8257 Intermediate Similarity NPC473633
0.8257 Intermediate Similarity NPC229962
0.8252 Intermediate Similarity NPC33053
0.8252 Intermediate Similarity NPC190395
0.8247 Intermediate Similarity NPC305160
0.8247 Intermediate Similarity NPC477927
0.8247 Intermediate Similarity NPC72817
0.8235 Intermediate Similarity NPC85593
0.8235 Intermediate Similarity NPC312774
0.8235 Intermediate Similarity NPC31430
0.8224 Intermediate Similarity NPC477808
0.8224 Intermediate Similarity NPC167183
0.8224 Intermediate Similarity NPC32707

  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 NPC177818 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
0.7905 Intermediate Similarity NPD6412 Phase 2
0.7838 Intermediate Similarity NPD7327 Approved
0.7838 Intermediate Similarity NPD7328 Approved
0.7826 Intermediate Similarity NPD6928 Phase 2
0.7778 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7768 Intermediate Similarity NPD7516 Approved
0.7684 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD7339 Approved
0.7667 Intermediate Similarity NPD6942 Approved
0.7634 Intermediate Similarity NPD7525 Registered
0.7632 Intermediate Similarity NPD8379 Approved
0.7632 Intermediate Similarity NPD8378 Approved
0.7632 Intermediate Similarity NPD8380 Approved
0.7632 Intermediate Similarity NPD8033 Approved
0.7632 Intermediate Similarity NPD8335 Approved
0.7632 Intermediate Similarity NPD8296 Approved
0.7579 Intermediate Similarity NPD6695 Phase 3
0.7544 Intermediate Similarity NPD6054 Approved
0.7544 Intermediate Similarity NPD8377 Approved
0.7544 Intermediate Similarity NPD8294 Approved
0.7544 Intermediate Similarity NPD6059 Approved
0.7449 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD6370 Approved
0.734 Intermediate Similarity NPD6929 Approved
0.734 Intermediate Similarity NPD7645 Phase 2
0.7328 Intermediate Similarity NPD7503 Approved
0.7328 Intermediate Similarity NPD6015 Approved
0.7328 Intermediate Similarity NPD6016 Approved
0.7288 Intermediate Similarity NPD7492 Approved
0.7273 Intermediate Similarity NPD7524 Approved
0.7273 Intermediate Similarity NPD7750 Discontinued
0.7265 Intermediate Similarity NPD5988 Approved
0.7263 Intermediate Similarity NPD6931 Approved
0.7263 Intermediate Similarity NPD6930 Phase 2
0.7255 Intermediate Similarity NPD6399 Phase 3
0.7255 Intermediate Similarity NPD8171 Discontinued
0.725 Intermediate Similarity NPD7736 Approved
0.7238 Intermediate Similarity NPD7638 Approved
0.7232 Intermediate Similarity NPD6882 Approved
0.7227 Intermediate Similarity NPD6616 Approved
0.7227 Intermediate Similarity NPD7507 Approved
0.719 Intermediate Similarity NPD7319 Approved
0.7182 Intermediate Similarity NPD7320 Approved
0.7174 Intermediate Similarity NPD4785 Approved
0.7174 Intermediate Similarity NPD4784 Approved
0.717 Intermediate Similarity NPD7640 Approved
0.717 Intermediate Similarity NPD7639 Approved
0.7167 Intermediate Similarity NPD8293 Discontinued
0.7167 Intermediate Similarity NPD7078 Approved
0.7156 Intermediate Similarity NPD7128 Approved
0.7156 Intermediate Similarity NPD6402 Approved
0.7156 Intermediate Similarity NPD5739 Approved
0.7156 Intermediate Similarity NPD6675 Approved
0.7156 Intermediate Similarity NPD6008 Approved
0.7154 Intermediate Similarity NPD8449 Approved
0.7143 Intermediate Similarity NPD4786 Approved
0.7143 Intermediate Similarity NPD4243 Approved
0.7128 Intermediate Similarity NPD6932 Approved
0.7128 Intermediate Similarity NPD6925 Approved
0.7128 Intermediate Similarity NPD5776 Phase 2
0.7097 Intermediate Similarity NPD8450 Suspended
0.7059 Intermediate Similarity NPD6067 Discontinued
0.7053 Intermediate Similarity NPD7145 Approved
0.7027 Intermediate Similarity NPD6881 Approved
0.7027 Intermediate Similarity NPD6899 Approved
0.699 Remote Similarity NPD7087 Discontinued
0.6989 Remote Similarity NPD6924 Approved
0.6989 Remote Similarity NPD6926 Approved
0.6983 Remote Similarity NPD6009 Approved
0.6981 Remote Similarity NPD4755 Approved
0.6981 Remote Similarity NPD6083 Phase 2
0.6981 Remote Similarity NPD6084 Phase 2
0.6979 Remote Similarity NPD6683 Phase 2
0.6967 Remote Similarity NPD6033 Approved
0.6964 Remote Similarity NPD6373 Approved
0.6964 Remote Similarity NPD6372 Approved
0.6939 Remote Similarity NPD3667 Approved
0.6937 Remote Similarity NPD5701 Approved
0.6937 Remote Similarity NPD5697 Approved
0.6923 Remote Similarity NPD4202 Approved
0.6907 Remote Similarity NPD4748 Discontinued
0.6907 Remote Similarity NPD7514 Phase 3
0.6903 Remote Similarity NPD6883 Approved
0.6903 Remote Similarity NPD7290 Approved
0.6903 Remote Similarity NPD7102 Approved
0.69 Remote Similarity NPD6893 Approved
0.6852 Remote Similarity NPD5286 Approved
0.6852 Remote Similarity NPD4700 Approved
0.6852 Remote Similarity NPD5285 Approved
0.6852 Remote Similarity NPD4696 Approved
0.6842 Remote Similarity NPD6649 Approved
0.6842 Remote Similarity NPD6847 Approved
0.6842 Remote Similarity NPD6650 Approved
0.6842 Remote Similarity NPD6617 Approved
0.6842 Remote Similarity NPD6869 Approved
0.6842 Remote Similarity NPD6933 Approved
0.6842 Remote Similarity NPD8130 Phase 1
0.6837 Remote Similarity NPD6902 Approved
0.6827 Remote Similarity NPD7637 Suspended
0.6814 Remote Similarity NPD6012 Approved
0.6814 Remote Similarity NPD6014 Approved
0.6814 Remote Similarity NPD6013 Approved
0.6814 Remote Similarity NPD8132 Clinical (unspecified phase)
0.68 Remote Similarity NPD3666 Approved
0.68 Remote Similarity NPD3133 Approved
0.68 Remote Similarity NPD3665 Phase 1
0.6796 Remote Similarity NPD5328 Approved
0.6796 Remote Similarity NPD4753 Phase 2
0.6796 Remote Similarity NPD6051 Approved
0.6792 Remote Similarity NPD7991 Discontinued
0.6783 Remote Similarity NPD8297 Approved
0.6774 Remote Similarity NPD7151 Approved
0.6774 Remote Similarity NPD7152 Approved
0.6774 Remote Similarity NPD7150 Approved
0.6739 Remote Similarity NPD6923 Approved
0.6739 Remote Similarity NPD6922 Approved
0.6737 Remote Similarity NPD5275 Approved
0.6737 Remote Similarity NPD4190 Phase 3
0.6735 Remote Similarity NPD7332 Phase 2
0.6727 Remote Similarity NPD5211 Phase 2
0.6727 Remote Similarity NPD5226 Approved
0.6727 Remote Similarity NPD5225 Approved
0.6727 Remote Similarity NPD5224 Approved
0.6727 Remote Similarity NPD4633 Approved
0.6726 Remote Similarity NPD6686 Approved
0.6726 Remote Similarity NPD6011 Approved
0.6724 Remote Similarity NPD8133 Approved
0.6724 Remote Similarity NPD4632 Approved
0.6699 Remote Similarity NPD6903 Approved
0.6699 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8034 Phase 2
0.6667 Remote Similarity NPD5175 Approved
0.6667 Remote Similarity NPD5330 Approved
0.6667 Remote Similarity NPD8035 Phase 2
0.6667 Remote Similarity NPD5174 Approved
0.6667 Remote Similarity NPD6409 Approved
0.6667 Remote Similarity NPD7146 Approved
0.6667 Remote Similarity NPD7521 Approved
0.6667 Remote Similarity NPD3618 Phase 1
0.6667 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD7334 Approved
0.6667 Remote Similarity NPD7144 Approved
0.6667 Remote Similarity NPD6898 Phase 1
0.6667 Remote Similarity NPD6684 Approved
0.6667 Remote Similarity NPD7143 Approved
0.6667 Remote Similarity NPD6079 Approved
0.6638 Remote Similarity NPD6053 Discontinued
0.6636 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5223 Approved
0.6636 Remote Similarity NPD5695 Phase 3
0.6633 Remote Similarity NPD4195 Approved
0.6609 Remote Similarity NPD4634 Approved
0.6607 Remote Similarity NPD5141 Approved
0.6607 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6606 Remote Similarity NPD5696 Approved
0.6587 Remote Similarity NPD5956 Approved
0.6577 Remote Similarity NPD7632 Discontinued
0.6569 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7509 Discontinued
0.6555 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6549 Remote Similarity NPD4767 Approved
0.6549 Remote Similarity NPD4768 Approved
0.6542 Remote Similarity NPD7748 Approved
0.6518 Remote Similarity NPD4754 Approved
0.6514 Remote Similarity NPD7902 Approved
0.6509 Remote Similarity NPD7515 Phase 2
0.6504 Remote Similarity NPD8328 Phase 3
0.6504 Remote Similarity NPD7604 Phase 2
0.6486 Remote Similarity NPD4159 Approved
0.6481 Remote Similarity NPD4629 Approved
0.6481 Remote Similarity NPD5210 Approved
0.6475 Remote Similarity NPD5983 Phase 2
0.6471 Remote Similarity NPD6274 Approved
0.6471 Remote Similarity NPD3668 Phase 3
0.6446 Remote Similarity NPD7101 Approved
0.6446 Remote Similarity NPD7100 Approved
0.6442 Remote Similarity NPD4251 Approved
0.6442 Remote Similarity NPD4250 Approved
0.6436 Remote Similarity NPD4221 Approved
0.6436 Remote Similarity NPD4223 Phase 3
0.6435 Remote Similarity NPD4729 Approved
0.6435 Remote Similarity NPD5128 Approved
0.6435 Remote Similarity NPD4730 Approved
0.6422 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5222 Approved
0.6422 Remote Similarity NPD5221 Approved
0.6422 Remote Similarity NPD4697 Phase 3
0.6417 Remote Similarity NPD7115 Discovery
0.6415 Remote Similarity NPD3168 Discontinued
0.6408 Remote Similarity NPD5329 Approved
0.64 Remote Similarity NPD6336 Discontinued
0.6381 Remote Similarity NPD5737 Approved
0.6381 Remote Similarity NPD6672 Approved
0.6364 Remote Similarity NPD6335 Approved
0.6364 Remote Similarity NPD5173 Approved
0.6346 Remote Similarity NPD6098 Approved
0.6346 Remote Similarity NPD4249 Approved
0.6341 Remote Similarity NPD6909 Approved
0.6341 Remote Similarity NPD6908 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