Structure

Physi-Chem Properties

Molecular Weight:  295.12
Volume:  298.651
LogP:  2.815
LogD:  2.367
LogS:  -2.156
# Rotatable Bonds:  1
TPSA:  39.72
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.878
Synthetic Accessibility Score:  3.258
Fsp3:  0.333
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:  -4.953
MDCK Permeability:  1.9219725800212473e-05
Pgp-inhibitor:  0.084
Pgp-substrate:  0.496
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.974
Plasma Protein Binding (PPB):  88.38823699951172%
Volume Distribution (VD):  1.699
Pgp-substrate:  3.3659894466400146%

ADMET: Metabolism

CYP1A2-inhibitor:  0.877
CYP1A2-substrate:  0.348
CYP2C19-inhibitor:  0.527
CYP2C19-substrate:  0.826
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.745
CYP2D6-inhibitor:  0.858
CYP2D6-substrate:  0.912
CYP3A4-inhibitor:  0.689
CYP3A4-substrate:  0.817

ADMET: Excretion

Clearance (CL):  5.664
Half-life (T1/2):  0.143

ADMET: Toxicity

hERG Blockers:  0.235
Human Hepatotoxicity (H-HT):  0.393
Drug-inuced Liver Injury (DILI):  0.236
AMES Toxicity:  0.874
Rat Oral Acute Toxicity:  0.563
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.134
Carcinogencity:  0.275
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.922

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

  Natural Product: NPC112575

Natural Product ID:  NPC112575
Common Name*:   Norstephalagine
IUPAC Name:   n.a.
Synonyms:   Norstephalagine
Standard InCHIKey:  TYZKUSBTFHNPMV-CYBMUJFWSA-N
Standard InCHI:  InChI=1S/C18H17NO3/c1-20-16-12-6-7-19-13-8-10-4-2-3-5-11(10)15(14(12)13)17-18(16)22-9-21-17/h2-5,13,19H,6-9H2,1H3/t13-/m1/s1
SMILES:  COc1c2CCN[C@@H]3Cc4ccccc4-c(c23)c2c1OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL257745
PubChem CID:   133381
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
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota flowers n.a. n.a. PMID[10075775]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[10479331]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[15387664]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18524603]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. stem n.a. PMID[21443171]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches San Antonio, Texas 2004-JUN PMID[25685941]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches n.a. n.a. PMID[25685941]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota Fruits n.a. n.a. PMID[26110443]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[26238319]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota Roots n.a. n.a. PMID[29924604]
NPO32838 artabottys maingayi Species n.a. n.a. n.a. n.a. n.a. PMID[8676127]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. Suriname rainforest n.a. PMID[9428162]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17230 Psidium acutangulum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19709 Pseudocyphellaria australiensis Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11373 0nomuraea spiralis Species Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12223 Stellaria media Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19371 Costasiella ocellifera Species Costasiellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15887 Absidia orchidis Species Cunninghamellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4679 Hedysarum gmelini Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18348 Crotalaria stolzii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9906 Zephyranthes flava Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12992 Shigella boydii Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17630 Helenium integrifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8172 Emericellopsis minima Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17114 Streptomyces melanogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO968 Artemisia pectinata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18533 Delisea elegans Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16135 Pestalotiopsis oenotherae Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25370 Botrychium ternatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5455 Euploca racemosa Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15802 Papaver pseudocanescens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13646 Phlebia strigosozonata Species Meruliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18169 Creosphaeria sassafras Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16325 Sideritis dasygnaphala Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17499 Bursera kerberi Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12870 Curcuma aeruginosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11081 Baccharis grandicapitulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16981 Gutierrezia dracunculoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15127 Senecio congestus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19572 Pellacalyx axillaris Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11646 Morella pensylvanica Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17964 Aspergillus subolivaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18262 Aspergillus microcysticus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12914 Sarcophyton flexuosum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19170 Lasianthaea podocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18424 Selinum libanotis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29531 Lupinus cosentinii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18927 Clinacanthus nutans Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17354 Micromonospora echinospora Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17612 Xanthium sibiricum Species Asteraceae 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
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus IC50 = 4800.0 nM PMID[541684]
NPT1858 Individual Protein Dopamine D2 receptor Rattus norvegicus IC50 = 27000.0 nM PMID[541684]
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus IC50 = 1400.0 nM PMID[541684]
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus IC50 = 1400.0 nM PMID[541685]
NPT2 Others Unspecified Ratio IC50 = 3.4 n.a. PMID[541685]
NPT2 Others Unspecified Ratio IC50 = 19.6 n.a. PMID[541685]

☑ 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 NPC112575 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
0.9816 High Similarity NPC32413
0.9816 High Similarity NPC474506
0.9815 High Similarity NPC23219
0.9755 High Similarity NPC258695
0.9755 High Similarity NPC470879
0.9506 High Similarity NPC6152
0.9464 High Similarity NPC57036
0.9448 High Similarity NPC19520
0.9448 High Similarity NPC149090
0.9441 High Similarity NPC304659
0.9441 High Similarity NPC86144
0.9408 High Similarity NPC476576
0.9408 High Similarity NPC186546
0.9383 High Similarity NPC204947
0.9357 High Similarity NPC117717
0.9317 High Similarity NPC189470
0.9281 High Similarity NPC267408
0.9259 High Similarity NPC225774
0.9217 High Similarity NPC477558
0.9202 High Similarity NPC219341
0.9202 High Similarity NPC476432
0.9202 High Similarity NPC24264
0.9162 High Similarity NPC476577
0.9162 High Similarity NPC148709
0.9162 High Similarity NPC173416
0.9146 High Similarity NPC247389
0.9141 High Similarity NPC16805
0.9141 High Similarity NPC302527
0.9141 High Similarity NPC167546
0.9118 High Similarity NPC135772
0.9112 High Similarity NPC155442
0.9112 High Similarity NPC477561
0.9112 High Similarity NPC312918
0.9112 High Similarity NPC476574
0.9074 High Similarity NPC232924
0.9074 High Similarity NPC477559
0.9074 High Similarity NPC160298
0.9074 High Similarity NPC266753
0.9074 High Similarity NPC306902
0.9053 High Similarity NPC474507
0.9036 High Similarity NPC152212
0.903 High Similarity NPC210918
0.9012 High Similarity NPC214116
0.9006 High Similarity NPC203784
0.9006 High Similarity NPC170503
0.9006 High Similarity NPC126519
0.8947 High Similarity NPC476575
0.881 High Similarity NPC118274
0.881 High Similarity NPC168753
0.8802 High Similarity NPC298979
0.88 High Similarity NPC82763
0.8772 High Similarity NPC320223
0.8772 High Similarity NPC114364
0.8765 High Similarity NPC128560
0.8765 High Similarity NPC199465
0.8765 High Similarity NPC229166
0.875 High Similarity NPC475754
0.875 High Similarity NPC241055
0.8728 High Similarity NPC275132
0.8721 High Similarity NPC126284
0.872 High Similarity NPC476572
0.8712 High Similarity NPC325871
0.8712 High Similarity NPC99659
0.8706 High Similarity NPC192135
0.8706 High Similarity NPC66341
0.8706 High Similarity NPC477020
0.8698 High Similarity NPC69712
0.8698 High Similarity NPC477562
0.8698 High Similarity NPC26240
0.8693 High Similarity NPC281581
0.8683 High Similarity NPC168409
0.8667 High Similarity NPC7393
0.8649 High Similarity NPC46990
0.8647 High Similarity NPC239775
0.8642 High Similarity NPC326316
0.8642 High Similarity NPC81733
0.8631 High Similarity NPC476573
0.8631 High Similarity NPC35627
0.8631 High Similarity NPC81247
0.8621 High Similarity NPC248642
0.8571 High Similarity NPC156576
0.8514 High Similarity NPC116284
0.8476 Intermediate Similarity NPC114124
0.8448 Intermediate Similarity NPC148693
0.8448 Intermediate Similarity NPC118633
0.8448 Intermediate Similarity NPC294790
0.8427 Intermediate Similarity NPC237579
0.8412 Intermediate Similarity NPC193853
0.8412 Intermediate Similarity NPC223077
0.8412 Intermediate Similarity NPC56887
0.8409 Intermediate Similarity NPC73492
0.8409 Intermediate Similarity NPC299990
0.8373 Intermediate Similarity NPC138487
0.8373 Intermediate Similarity NPC244112
0.8373 Intermediate Similarity NPC216459
0.8373 Intermediate Similarity NPC41178
0.8372 Intermediate Similarity NPC75958
0.8363 Intermediate Similarity NPC81218
0.8363 Intermediate Similarity NPC158376
0.8363 Intermediate Similarity NPC12053
0.8363 Intermediate Similarity NPC117188
0.8363 Intermediate Similarity NPC205421
0.8363 Intermediate Similarity NPC306555
0.8363 Intermediate Similarity NPC145832
0.8363 Intermediate Similarity NPC474931
0.8362 Intermediate Similarity NPC302275
0.8353 Intermediate Similarity NPC306843
0.8353 Intermediate Similarity NPC196447
0.8353 Intermediate Similarity NPC96603
0.8353 Intermediate Similarity NPC253043
0.8353 Intermediate Similarity NPC477563
0.8353 Intermediate Similarity NPC209377
0.8353 Intermediate Similarity NPC212794
0.8353 Intermediate Similarity NPC78222
0.8353 Intermediate Similarity NPC136508
0.8353 Intermediate Similarity NPC13504
0.8344 Intermediate Similarity NPC37144
0.8344 Intermediate Similarity NPC475959
0.8344 Intermediate Similarity NPC59907
0.8323 Intermediate Similarity NPC146288
0.8295 Intermediate Similarity NPC243454
0.8295 Intermediate Similarity NPC475479
0.8294 Intermediate Similarity NPC1229
0.8294 Intermediate Similarity NPC324144
0.8284 Intermediate Similarity NPC27410
0.8284 Intermediate Similarity NPC166014
0.8263 Intermediate Similarity NPC123323
0.8263 Intermediate Similarity NPC76079
0.8249 Intermediate Similarity NPC239584
0.8235 Intermediate Similarity NPC156728
0.8235 Intermediate Similarity NPC244606
0.8225 Intermediate Similarity NPC477080
0.8222 Intermediate Similarity NPC312531
0.8214 Intermediate Similarity NPC234392
0.8214 Intermediate Similarity NPC31311
0.8198 Intermediate Similarity NPC68328
0.8182 Intermediate Similarity NPC211296
0.8182 Intermediate Similarity NPC219162
0.8167 Intermediate Similarity NPC14507
0.8167 Intermediate Similarity NPC47077
0.8166 Intermediate Similarity NPC79328
0.8162 Intermediate Similarity NPC212163
0.8146 Intermediate Similarity NPC179704
0.8144 Intermediate Similarity NPC210148
0.8144 Intermediate Similarity NPC233029
0.8142 Intermediate Similarity NPC256124
0.814 Intermediate Similarity NPC180306
0.8132 Intermediate Similarity NPC473716
0.8132 Intermediate Similarity NPC475597
0.8125 Intermediate Similarity NPC329969
0.8101 Intermediate Similarity NPC249405
0.8092 Intermediate Similarity NPC13916
0.8092 Intermediate Similarity NPC264850
0.8092 Intermediate Similarity NPC195392
0.809 Intermediate Similarity NPC220961
0.809 Intermediate Similarity NPC244554
0.8087 Intermediate Similarity NPC24260
0.8087 Intermediate Similarity NPC478093
0.8079 Intermediate Similarity NPC287588
0.8075 Intermediate Similarity NPC295676
0.8072 Intermediate Similarity NPC60538
0.8072 Intermediate Similarity NPC207824
0.807 Intermediate Similarity NPC119649
0.807 Intermediate Similarity NPC235143
0.807 Intermediate Similarity NPC230956
0.807 Intermediate Similarity NPC271388
0.807 Intermediate Similarity NPC205255
0.8068 Intermediate Similarity NPC2314
0.8061 Intermediate Similarity NPC253883
0.8061 Intermediate Similarity NPC90844
0.8061 Intermediate Similarity NPC95075
0.8049 Intermediate Similarity NPC145304
0.8047 Intermediate Similarity NPC93593
0.8043 Intermediate Similarity NPC30182
0.8043 Intermediate Similarity NPC473589
0.8043 Intermediate Similarity NPC478092
0.8043 Intermediate Similarity NPC478091
0.8035 Intermediate Similarity NPC238530
0.8035 Intermediate Similarity NPC276944
0.8035 Intermediate Similarity NPC232514
0.8035 Intermediate Similarity NPC24465
0.8025 Intermediate Similarity NPC470925
0.8023 Intermediate Similarity NPC80759
0.8023 Intermediate Similarity NPC79402
0.8022 Intermediate Similarity NPC474904
0.8012 Intermediate Similarity NPC130941
0.8012 Intermediate Similarity NPC221864
0.8011 Intermediate Similarity NPC76682
0.8011 Intermediate Similarity NPC317439
0.8011 Intermediate Similarity NPC317145
0.8011 Intermediate Similarity NPC115284
0.8011 Intermediate Similarity NPC198498
0.8011 Intermediate Similarity NPC276890
0.8011 Intermediate Similarity NPC227060
0.8011 Intermediate Similarity NPC10908
0.8011 Intermediate Similarity NPC63646
0.8011 Intermediate Similarity NPC65403
0.8011 Intermediate Similarity NPC231371
0.8 Intermediate Similarity NPC180756
0.8 Intermediate Similarity NPC29647

  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 NPC112575 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
0.8012 Intermediate Similarity NPD6788 Approved
0.8011 Intermediate Similarity NPD8251 Approved
0.8011 Intermediate Similarity NPD8252 Approved
0.8011 Intermediate Similarity NPD8099 Discontinued
0.7966 Intermediate Similarity NPD8156 Discontinued
0.7952 Intermediate Similarity NPD4584 Approved
0.7952 Intermediate Similarity NPD1424 Approved
0.7914 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD3051 Approved
0.7836 Intermediate Similarity NPD7298 Approved
0.7797 Intermediate Similarity NPD4481 Phase 3
0.779 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD4727 Phase 1
0.7751 Intermediate Similarity NPD6031 Approved
0.7751 Intermediate Similarity NPD6030 Approved
0.774 Intermediate Similarity NPD2969 Approved
0.774 Intermediate Similarity NPD2970 Approved
0.7705 Intermediate Similarity NPD8053 Approved
0.7705 Intermediate Similarity NPD8054 Approved
0.764 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD3384 Approved
0.763 Intermediate Similarity NPD3383 Approved
0.763 Intermediate Similarity NPD3382 Approved
0.76 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD2489 Approved
0.7598 Intermediate Similarity NPD27 Approved
0.7581 Intermediate Similarity NPD7906 Approved
0.7576 Intermediate Similarity NPD7827 Phase 1
0.7574 Intermediate Similarity NPD2421 Approved
0.7574 Intermediate Similarity NPD2420 Approved
0.7565 Intermediate Similarity NPD5005 Approved
0.7565 Intermediate Similarity NPD5006 Approved
0.7558 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD4578 Approved
0.7554 Intermediate Similarity NPD4577 Approved
0.7544 Intermediate Similarity NPD5976 Discontinued
0.7515 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD3845 Phase 1
0.7515 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD2978 Approved
0.7486 Intermediate Similarity NPD2977 Approved
0.7486 Intermediate Similarity NPD4585 Approved
0.7459 Intermediate Similarity NPD2971 Approved
0.7459 Intermediate Similarity NPD2968 Approved
0.7458 Intermediate Similarity NPD4055 Discovery
0.7457 Intermediate Similarity NPD4017 Approved
0.7448 Intermediate Similarity NPD4420 Approved
0.7433 Intermediate Similarity NPD4663 Approved
0.7384 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.738 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD7311 Approved
0.7366 Intermediate Similarity NPD7312 Approved
0.7366 Intermediate Similarity NPD7310 Approved
0.7366 Intermediate Similarity NPD7313 Approved
0.7353 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7309 Approved
0.7293 Intermediate Similarity NPD4166 Phase 2
0.7293 Intermediate Similarity NPD6071 Discontinued
0.7288 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD4859 Phase 1
0.7273 Intermediate Similarity NPD3110 Approved
0.7273 Intermediate Similarity NPD3109 Approved
0.7267 Intermediate Similarity NPD7598 Phase 2
0.7264 Intermediate Similarity NPD6723 Discontinued
0.7251 Intermediate Similarity NPD5241 Discontinued
0.7247 Intermediate Similarity NPD2563 Approved
0.7247 Intermediate Similarity NPD2560 Approved
0.7241 Intermediate Similarity NPD3641 Approved
0.7241 Intermediate Similarity NPD3639 Approved
0.7241 Intermediate Similarity NPD3640 Phase 3
0.7238 Intermediate Similarity NPD6107 Approved
0.7231 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD8095 Phase 1
0.7216 Intermediate Similarity NPD2975 Approved
0.7216 Intermediate Similarity NPD2974 Approved
0.7216 Intermediate Similarity NPD2973 Approved
0.7213 Intermediate Similarity NPD2898 Approved
0.7209 Intermediate Similarity NPD7124 Phase 2
0.7204 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD6297 Approved
0.7202 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7833 Phase 2
0.7167 Intermediate Similarity NPD7831 Phase 2
0.7143 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2490 Approved
0.7135 Intermediate Similarity NPD2488 Approved
0.7107 Intermediate Similarity NPD4580 Approved
0.7093 Intermediate Similarity NPD5754 Discontinued
0.7093 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD5677 Discontinued
0.7079 Intermediate Similarity NPD4772 Phase 2
0.7079 Intermediate Similarity NPD4773 Phase 2
0.7071 Intermediate Similarity NPD2493 Approved
0.7071 Intermediate Similarity NPD3450 Approved
0.7071 Intermediate Similarity NPD3452 Approved
0.7071 Intermediate Similarity NPD2494 Approved
0.7062 Intermediate Similarity NPD4005 Discontinued
0.7053 Intermediate Similarity NPD6851 Approved
0.7053 Intermediate Similarity NPD6853 Approved
0.7052 Intermediate Similarity NPD5160 Discontinued
0.7048 Intermediate Similarity NPD5718 Phase 2
0.7035 Intermediate Similarity NPD3060 Approved
0.7035 Intermediate Similarity NPD3515 Approved
0.7035 Intermediate Similarity NPD3516 Approved
0.7031 Intermediate Similarity NPD3349 Phase 2
0.6995 Remote Similarity NPD6037 Discontinued
0.699 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6978 Remote Similarity NPD5604 Discontinued
0.6978 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6965 Remote Similarity NPD4582 Approved
0.6965 Remote Similarity NPD4583 Approved
0.6959 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7802 Discontinued
0.694 Remote Similarity NPD7400 Phase 3
0.694 Remote Similarity NPD5709 Phase 3
0.6935 Remote Similarity NPD5457 Discontinued
0.692 Remote Similarity NPD8152 Approved
0.692 Remote Similarity NPD8153 Approved
0.6919 Remote Similarity NPD4010 Discontinued
0.6915 Remote Similarity NPD42 Phase 2
0.6915 Remote Similarity NPD6042 Phase 2
0.6915 Remote Similarity NPD4004 Approved
0.6915 Remote Similarity NPD4002 Approved
0.6907 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6907 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4475 Approved
0.6905 Remote Similarity NPD4474 Approved
0.6902 Remote Similarity NPD4666 Phase 3
0.6898 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7466 Approved
0.6893 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6881 Remote Similarity NPD4040 Phase 1
0.6875 Remote Similarity NPD3124 Discontinued
0.6866 Remote Similarity NPD6625 Approved
0.6857 Remote Similarity NPD3763 Approved
0.6851 Remote Similarity NPD5720 Discontinued
0.685 Remote Similarity NPD4107 Approved
0.6842 Remote Similarity NPD2200 Suspended
0.6842 Remote Similarity NPD6111 Discontinued
0.6839 Remote Similarity NPD5177 Phase 3
0.6839 Remote Similarity NPD4162 Approved
0.6826 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6823 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6823 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6823 Remote Similarity NPD7281 Phase 3
0.6823 Remote Similarity NPD7280 Phase 3
0.6802 Remote Similarity NPD4108 Discontinued
0.6796 Remote Similarity NPD5089 Approved
0.6796 Remote Similarity NPD5090 Approved
0.6794 Remote Similarity NPD7047 Phase 3
0.6789 Remote Similarity NPD7479 Phase 2
0.6788 Remote Similarity NPD6618 Phase 2
0.6784 Remote Similarity NPD2492 Phase 1
0.6782 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6778 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6777 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6776 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6776 Remote Similarity NPD5977 Approved
0.6776 Remote Similarity NPD5978 Approved
0.6772 Remote Similarity NPD5708 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7549 Discontinued
0.6766 Remote Similarity NPD6612 Phase 2
0.6761 Remote Similarity NPD6997 Phase 2
0.6758 Remote Similarity NPD37 Approved
0.6744 Remote Similarity NPD6896 Approved
0.6744 Remote Similarity NPD6895 Approved
0.6742 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6737 Remote Similarity NPD4873 Discontinued
0.6733 Remote Similarity NPD4482 Phase 3
0.6724 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6723 Remote Similarity NPD2120 Phase 2
0.672 Remote Similarity NPD3489 Phase 3
0.6706 Remote Similarity NPD3532 Approved
0.6706 Remote Similarity NPD3530 Approved
0.6706 Remote Similarity NPD3531 Approved
0.6705 Remote Similarity NPD2154 Approved
0.6705 Remote Similarity NPD2155 Approved
0.6705 Remote Similarity NPD6748 Discontinued
0.6705 Remote Similarity NPD2156 Approved
0.6702 Remote Similarity NPD5242 Approved
0.67 Remote Similarity NPD3057 Approved
0.6686 Remote Similarity NPD4257 Approved
0.6686 Remote Similarity NPD2989 Phase 2
0.6686 Remote Similarity NPD4256 Phase 2
0.6686 Remote Similarity NPD2986 Phase 2
0.6686 Remote Similarity NPD2653 Approved
0.6685 Remote Similarity NPD5297 Approved
0.6684 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3454 Phase 3
0.6667 Remote Similarity NPD2677 Approved
0.6651 Remote Similarity NPD3816 Phase 1
0.6651 Remote Similarity NPD3815 Phase 1
0.665 Remote Similarity NPD5582 Discontinued
0.665 Remote Similarity NPD2845 Phase 2

  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