Structure

Physi-Chem Properties

Molecular Weight:  215.13
Volume:  240.192
LogP:  3.004
LogD:  2.993
LogS:  -3.04
# Rotatable Bonds:  3
TPSA:  20.31
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.695
Synthetic Accessibility Score:  1.7
Fsp3:  0.357
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.608
MDCK Permeability:  2.2197640646481887e-05
Pgp-inhibitor:  0.086
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.041
30% Bioavailability (F30%):  0.358

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.521
Plasma Protein Binding (PPB):  93.95771026611328%
Volume Distribution (VD):  0.691
Pgp-substrate:  5.305591583251953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.929
CYP1A2-substrate:  0.818
CYP2C19-inhibitor:  0.636
CYP2C19-substrate:  0.594
CYP2C9-inhibitor:  0.271
CYP2C9-substrate:  0.45
CYP2D6-inhibitor:  0.038
CYP2D6-substrate:  0.74
CYP3A4-inhibitor:  0.079
CYP3A4-substrate:  0.255

ADMET: Excretion

Clearance (CL):  4.105
Half-life (T1/2):  0.752

ADMET: Toxicity

hERG Blockers:  0.275
Human Hepatotoxicity (H-HT):  0.087
Drug-inuced Liver Injury (DILI):  0.06
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.237
Maximum Recommended Daily Dose:  0.1
Skin Sensitization:  0.955
Carcinogencity:  0.278
Eye Corrosion:  0.293
Eye Irritation:  0.945
Respiratory Toxicity:  0.935

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

  Natural Product: NPC305602

Natural Product ID:  NPC305602
Common Name*:   3-Phenyl-1-Piperidin-1-Ylprop-2-En-1-One
IUPAC Name:   3-phenyl-1-piperidin-1-ylprop-2-en-1-one
Synonyms:  
Standard InCHIKey:  KNOXUMZPTHELAO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H17NO/c16-14(15-11-5-2-6-12-15)10-9-13-7-3-1-4-8-13/h1,3-4,7-10H,2,5-6,11-12H2
SMILES:  c1ccc(cc1)C=CC(=O)N1CCCCC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1703375
PubChem CID:   223147
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives

*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
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4039(01)00209-X]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[10575373]
NPO10274 Pothomorphe peltata n.a. n.a. n.a. n.a. Dominican Republic n.a. PMID[11430019]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[14695795]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. leaf n.a. PMID[15467205]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. whole plant n.a. PMID[16808005]
NPO3968 Dracontium loretense Species Araceae Eukaryota corms Iquitos, Peru 2005-MAY PMID[19341262]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. PMID[19341262]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19485332]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. PMID[22909174]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23102654]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[23149469]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota Fruits n.a. n.a. PMID[23506561]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota leaves n.a. n.a. PMID[25127165]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. PMID[25988621]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31103896]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27487 Silene banksia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2393 Matsumurella chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13059 Abies webbiana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6428 Euphorbia wangii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27487 Silene banksia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8639 Agaricus xanthodermus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7536 Mycoplasma mycoides Species Mycoplasmataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2840 Podocarpus minor Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10459 Brickellia longifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11137 Dichotomanthes tristaniicarpa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO964 Homalium laurifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9950 Coelogyne nitida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10274 Pothomorphe peltata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9166 Monascus rubropunctatus Species Fellodistomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO230 Palisota barteri Species Commelinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO876 Didymosphaeria enalia Species Didymosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11511 Cochlearia officinalis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO43 Leifsonia aquatica Species Microbacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12488 Bupleurum rigidum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6880 Crocus corsicus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23642 Penicillium tardum Species Aspergillaceae 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 7307.8 nM PMID[495040]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 7943.3 nM PMID[495040]
NPT1043 Individual Protein Glycoprotein hormones alpha chain Homo sapiens Potency n.a. 2238.7 nM PMID[495040]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[495040]
NPT2 Others Unspecified Potency n.a. 1778.3 nM PMID[495040]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Potency n.a. 7519.3 nM PMID[495040]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[495040]

☑ 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 NPC305602 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 NPC17497
0.8571 High Similarity NPC256452
0.8556 High Similarity NPC473661
0.8462 Intermediate Similarity NPC474974
0.7812 Intermediate Similarity NPC472258
0.7802 Intermediate Similarity NPC53492
0.7753 Intermediate Similarity NPC474088
0.7624 Intermediate Similarity NPC143516
0.7624 Intermediate Similarity NPC473418
0.7558 Intermediate Similarity NPC271642
0.7556 Intermediate Similarity NPC104070
0.7549 Intermediate Similarity NPC474804
0.7549 Intermediate Similarity NPC474973
0.7549 Intermediate Similarity NPC130898
0.7549 Intermediate Similarity NPC471447
0.7451 Intermediate Similarity NPC167336
0.7442 Intermediate Similarity NPC98976
0.7404 Intermediate Similarity NPC473676
0.732 Intermediate Similarity NPC71140
0.7315 Intermediate Similarity NPC246904
0.7222 Intermediate Similarity NPC475573
0.7222 Intermediate Similarity NPC475289
0.7212 Intermediate Similarity NPC45033
0.7196 Intermediate Similarity NPC475013
0.7157 Intermediate Similarity NPC329375
0.7143 Intermediate Similarity NPC55529
0.7143 Intermediate Similarity NPC231986
0.7143 Intermediate Similarity NPC311343
0.7128 Intermediate Similarity NPC258046
0.7113 Intermediate Similarity NPC470926
0.7097 Intermediate Similarity NPC169016
0.708 Intermediate Similarity NPC27833
0.7064 Intermediate Similarity NPC476048
0.7059 Intermediate Similarity NPC235059
0.7059 Intermediate Similarity NPC98880
0.7059 Intermediate Similarity NPC16190
0.7059 Intermediate Similarity NPC169222
0.7027 Intermediate Similarity NPC239357
0.7 Intermediate Similarity NPC12857
0.6977 Remote Similarity NPC95289
0.6966 Remote Similarity NPC139658
0.6897 Remote Similarity NPC326200
0.6889 Remote Similarity NPC179726
0.6863 Remote Similarity NPC120203
0.6857 Remote Similarity NPC275467
0.6818 Remote Similarity NPC244738
0.68 Remote Similarity NPC322040
0.6782 Remote Similarity NPC229235
0.6782 Remote Similarity NPC219246
0.6771 Remote Similarity NPC203076
0.6742 Remote Similarity NPC299134
0.6739 Remote Similarity NPC139901
0.6739 Remote Similarity NPC151405
0.6733 Remote Similarity NPC329430
0.6703 Remote Similarity NPC329318
0.6701 Remote Similarity NPC473031
0.6699 Remote Similarity NPC322598
0.6697 Remote Similarity NPC158854
0.6696 Remote Similarity NPC33742
0.6667 Remote Similarity NPC32203
0.6667 Remote Similarity NPC206800
0.6639 Remote Similarity NPC79698
0.6637 Remote Similarity NPC473573
0.6634 Remote Similarity NPC246757
0.6634 Remote Similarity NPC291070
0.663 Remote Similarity NPC76455
0.663 Remote Similarity NPC137847
0.6607 Remote Similarity NPC35850
0.6607 Remote Similarity NPC276949
0.6604 Remote Similarity NPC202613
0.6579 Remote Similarity NPC285926
0.6579 Remote Similarity NPC14672
0.6579 Remote Similarity NPC315276
0.6579 Remote Similarity NPC470544
0.6569 Remote Similarity NPC108339
0.6566 Remote Similarity NPC470877
0.6556 Remote Similarity NPC122327
0.6556 Remote Similarity NPC113000
0.6556 Remote Similarity NPC112609
0.6555 Remote Similarity NPC22746
0.6531 Remote Similarity NPC471638
0.6529 Remote Similarity NPC218323
0.6526 Remote Similarity NPC14326
0.6522 Remote Similarity NPC245966
0.6522 Remote Similarity NPC470545
0.6522 Remote Similarity NPC287790
0.6522 Remote Similarity NPC98269
0.6522 Remote Similarity NPC3672
0.6522 Remote Similarity NPC325662
0.6509 Remote Similarity NPC291610
0.6509 Remote Similarity NPC239854
0.6506 Remote Similarity NPC42477
0.65 Remote Similarity NPC159178
0.65 Remote Similarity NPC141139
0.65 Remote Similarity NPC121872
0.65 Remote Similarity NPC471307
0.65 Remote Similarity NPC78041
0.65 Remote Similarity NPC209764
0.65 Remote Similarity NPC74936
0.6496 Remote Similarity NPC302169
0.6489 Remote Similarity NPC71664
0.6484 Remote Similarity NPC276699
0.6476 Remote Similarity NPC75496
0.6471 Remote Similarity NPC206660
0.6466 Remote Similarity NPC470546
0.6466 Remote Similarity NPC220698
0.6465 Remote Similarity NPC12429
0.6458 Remote Similarity NPC243289
0.6458 Remote Similarity NPC208183
0.6458 Remote Similarity NPC119677
0.6452 Remote Similarity NPC176228
0.6452 Remote Similarity NPC2785
0.6452 Remote Similarity NPC285470
0.6452 Remote Similarity NPC50192
0.6452 Remote Similarity NPC36342
0.6441 Remote Similarity NPC314192
0.6429 Remote Similarity NPC167096
0.6429 Remote Similarity NPC181390
0.6422 Remote Similarity NPC473498
0.6421 Remote Similarity NPC12936
0.6421 Remote Similarity NPC303245
0.6421 Remote Similarity NPC273033
0.6421 Remote Similarity NPC71795
0.642 Remote Similarity NPC149436
0.6396 Remote Similarity NPC65855
0.6396 Remote Similarity NPC292758
0.6392 Remote Similarity NPC133162
0.6387 Remote Similarity NPC26285
0.6386 Remote Similarity NPC36357
0.6386 Remote Similarity NPC114327
0.6383 Remote Similarity NPC167577
0.6383 Remote Similarity NPC78517
0.6383 Remote Similarity NPC300205
0.6378 Remote Similarity NPC73883
0.6378 Remote Similarity NPC251454
0.6378 Remote Similarity NPC230698
0.6378 Remote Similarity NPC136330
0.6378 Remote Similarity NPC255817
0.6378 Remote Similarity NPC196609
0.6378 Remote Similarity NPC277042
0.6378 Remote Similarity NPC205178
0.6371 Remote Similarity NPC126458
0.6356 Remote Similarity NPC316582
0.6353 Remote Similarity NPC22786
0.6346 Remote Similarity NPC471320
0.6346 Remote Similarity NPC471319
0.6344 Remote Similarity NPC290638
0.6344 Remote Similarity NPC9796
0.6341 Remote Similarity NPC165726
0.6341 Remote Similarity NPC213969
0.6341 Remote Similarity NPC198841
0.6341 Remote Similarity NPC269586
0.6337 Remote Similarity NPC172128
0.6333 Remote Similarity NPC155429
0.6333 Remote Similarity NPC74458
0.633 Remote Similarity NPC476198
0.6328 Remote Similarity NPC99078
0.6327 Remote Similarity NPC3210
0.6325 Remote Similarity NPC228515
0.632 Remote Similarity NPC473962
0.6316 Remote Similarity NPC285716
0.6316 Remote Similarity NPC164086
0.6316 Remote Similarity NPC190567
0.6316 Remote Similarity NPC95868
0.6316 Remote Similarity NPC17408
0.6311 Remote Similarity NPC471309
0.6303 Remote Similarity NPC71684
0.63 Remote Similarity NPC325441
0.6289 Remote Similarity NPC127491
0.6289 Remote Similarity NPC324835
0.6289 Remote Similarity NPC273758
0.6289 Remote Similarity NPC308619
0.6286 Remote Similarity NPC472788
0.6283 Remote Similarity NPC275410
0.6281 Remote Similarity NPC285394
0.6279 Remote Similarity NPC220923
0.6279 Remote Similarity NPC252107
0.6279 Remote Similarity NPC470707
0.6279 Remote Similarity NPC50266
0.6275 Remote Similarity NPC226438
0.6275 Remote Similarity NPC245259
0.6271 Remote Similarity NPC177684
0.6271 Remote Similarity NPC291962
0.6265 Remote Similarity NPC65873
0.6265 Remote Similarity NPC300345
0.6265 Remote Similarity NPC120441
0.6265 Remote Similarity NPC212114
0.6264 Remote Similarity NPC271437
0.6264 Remote Similarity NPC285679
0.6262 Remote Similarity NPC228400
0.6262 Remote Similarity NPC11466
0.6262 Remote Similarity NPC214200
0.6261 Remote Similarity NPC113099
0.625 Remote Similarity NPC100039
0.625 Remote Similarity NPC145053
0.625 Remote Similarity NPC303045
0.625 Remote Similarity NPC161972
0.625 Remote Similarity NPC89950
0.624 Remote Similarity NPC120251
0.6237 Remote Similarity NPC78500

  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 NPC305602 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
0.8041 Intermediate Similarity NPD813 Approved
0.7857 Intermediate Similarity NPD6588 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD4803 Discontinued
0.7843 Intermediate Similarity NPD4063 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD4027 Approved
0.7727 Intermediate Similarity NPD4026 Approved
0.7723 Intermediate Similarity NPD1064 Approved
0.7723 Intermediate Similarity NPD1065 Approved
0.7677 Intermediate Similarity NPD2171 Approved
0.7677 Intermediate Similarity NPD2648 Phase 3
0.7677 Intermediate Similarity NPD2193 Phase 2
0.7674 Intermediate Similarity NPD4147 Approved
0.7674 Intermediate Similarity NPD603 Approved
0.7674 Intermediate Similarity NPD4144 Approved
0.7653 Intermediate Similarity NPD787 Suspended
0.757 Intermediate Similarity NPD1323 Discontinued
0.7556 Intermediate Similarity NPD1800 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD2577 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD1100 Approved
0.7449 Intermediate Similarity NPD1099 Approved
0.7426 Intermediate Similarity NPD3357 Discontinued
0.7416 Intermediate Similarity NPD5372 Approved
0.7416 Intermediate Similarity NPD5371 Approved
0.7407 Intermediate Similarity NPD1025 Discontinued
0.74 Intermediate Similarity NPD5630 Phase 1
0.7333 Intermediate Similarity NPD3581 Discontinued
0.7312 Intermediate Similarity NPD5252 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD4636 Approved
0.7312 Intermediate Similarity NPD4406 Approved
0.7312 Intermediate Similarity NPD4409 Approved
0.7303 Intermediate Similarity NPD1053 Approved
0.7303 Intermediate Similarity NPD507 Approved
0.7303 Intermediate Similarity NPD1051 Approved
0.7303 Intermediate Similarity NPD508 Approved
0.7303 Intermediate Similarity NPD1052 Approved
0.7283 Intermediate Similarity NPD2539 Approved
0.7283 Intermediate Similarity NPD2538 Approved
0.7283 Intermediate Similarity NPD5178 Approved
0.7253 Intermediate Similarity NPD4169 Approved
0.7253 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD4170 Approved
0.7222 Intermediate Similarity NPD5181 Approved
0.7222 Intermediate Similarity NPD5179 Approved
0.7222 Intermediate Similarity NPD5180 Approved
0.7212 Intermediate Similarity NPD7130 Phase 3
0.7204 Intermediate Similarity NPD5916 Discontinued
0.72 Intermediate Similarity NPD466 Approved
0.7157 Intermediate Similarity NPD2196 Discontinued
0.7157 Intermediate Similarity NPD708 Approved
0.7157 Intermediate Similarity NPD6024 Approved
0.7157 Intermediate Similarity NPD6027 Approved
0.7156 Intermediate Similarity NPD3551 Approved
0.7143 Intermediate Similarity NPD1306 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3035 Approved
0.7129 Intermediate Similarity NPD742 Approved
0.7115 Intermediate Similarity NPD1765 Approved
0.7115 Intermediate Similarity NPD1767 Approved
0.7115 Intermediate Similarity NPD1761 Approved
0.7115 Intermediate Similarity NPD1576 Approved
0.7115 Intermediate Similarity NPD1763 Approved
0.7115 Intermediate Similarity NPD1766 Approved
0.7115 Intermediate Similarity NPD959 Discontinued
0.7113 Intermediate Similarity NPD2997 Approved
0.7113 Intermediate Similarity NPD2998 Approved
0.7113 Intermediate Similarity NPD3000 Approved
0.7105 Intermediate Similarity NPD3624 Phase 2
0.7071 Intermediate Similarity NPD4094 Approved
0.703 Intermediate Similarity NPD4813 Approved
0.703 Intermediate Similarity NPD4263 Approved
0.703 Intermediate Similarity NPD1724 Approved
0.7027 Intermediate Similarity NPD7679 Phase 2
0.7 Intermediate Similarity NPD851 Approved
0.7 Intermediate Similarity NPD2508 Discontinued
0.7 Intermediate Similarity NPD157 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD853 Approved
0.6989 Remote Similarity NPD4635 Approved
0.6983 Remote Similarity NPD3549 Approved
0.6983 Remote Similarity NPD3550 Clinical (unspecified phase)
0.6983 Remote Similarity NPD3547 Approved
0.6979 Remote Similarity NPD3345 Approved
0.697 Remote Similarity NPD6549 Approved
0.697 Remote Similarity NPD6548 Approved
0.6952 Remote Similarity NPD1677 Discontinued
0.6952 Remote Similarity NPD2197 Approved
0.6952 Remote Similarity NPD2192 Approved
0.6931 Remote Similarity NPD4657 Approved
0.6931 Remote Similarity NPD4655 Approved
0.6923 Remote Similarity NPD5103 Approved
0.6907 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6893 Remote Similarity NPD2657 Approved
0.6881 Remote Similarity NPD2124 Approved
0.6864 Remote Similarity NPD1321 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3979 Approved
0.6848 Remote Similarity NPD3904 Approved
0.6848 Remote Similarity NPD3981 Approved
0.6848 Remote Similarity NPD3903 Approved
0.6842 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3346 Approved
0.6837 Remote Similarity NPD3344 Approved
0.6822 Remote Similarity NPD3420 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5979 Clinical (unspecified phase)
0.6818 Remote Similarity NPD9728 Phase 1
0.6814 Remote Similarity NPD5991 Approved
0.6814 Remote Similarity NPD5990 Approved
0.6813 Remote Similarity NPD295 Approved
0.6813 Remote Similarity NPD293 Approved
0.6813 Remote Similarity NPD296 Approved
0.6809 Remote Similarity NPD831 Approved
0.6809 Remote Similarity NPD830 Approved
0.6804 Remote Similarity NPD5675 Discontinued
0.6804 Remote Similarity NPD588 Approved
0.6804 Remote Similarity NPD587 Approved
0.68 Remote Similarity NPD8 Approved
0.68 Remote Similarity NPD243 Approved
0.6783 Remote Similarity NPD6806 Phase 1
0.678 Remote Similarity NPD1482 Clinical (unspecified phase)
0.6771 Remote Similarity NPD3099 Discontinued
0.6762 Remote Similarity NPD4658 Approved
0.6762 Remote Similarity NPD3683 Approved
0.6762 Remote Similarity NPD4229 Approved
0.6762 Remote Similarity NPD4656 Approved
0.6762 Remote Similarity NPD4231 Approved
0.6762 Remote Similarity NPD3681 Approved
0.6757 Remote Similarity NPD3598 Phase 3
0.6754 Remote Similarity NPD5859 Discontinued
0.6754 Remote Similarity NPD6345 Approved
0.6754 Remote Similarity NPD6343 Approved
0.6754 Remote Similarity NPD474 Approved
0.675 Remote Similarity NPD1050 Approved
0.675 Remote Similarity NPD4549 Discontinued
0.6742 Remote Similarity NPD505 Clinical (unspecified phase)
0.6739 Remote Similarity NPD590 Approved
0.6739 Remote Similarity NPD589 Approved
0.6737 Remote Similarity NPD785 Approved
0.6724 Remote Similarity NPD1124 Approved
0.6724 Remote Similarity NPD1123 Approved
0.6701 Remote Similarity NPD4146 Approved
0.6701 Remote Similarity NPD4145 Approved
0.67 Remote Similarity NPD4408 Approved
0.67 Remote Similarity NPD4407 Approved
0.67 Remote Similarity NPD4405 Approved
0.6699 Remote Similarity NPD6498 Approved
0.6699 Remote Similarity NPD4117 Approved
0.6699 Remote Similarity NPD6499 Approved
0.6697 Remote Similarity NPD1752 Approved
0.6697 Remote Similarity NPD1756 Approved
0.6696 Remote Similarity NPD3867 Phase 2
0.6667 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2205 Approved
0.6667 Remote Similarity NPD5964 Phase 2
0.6667 Remote Similarity NPD480 Approved
0.6667 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5963 Phase 2
0.6667 Remote Similarity NPD4478 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2208 Approved
0.6667 Remote Similarity NPD260 Discontinued
0.6667 Remote Similarity NPD2005 Discontinued
0.6667 Remote Similarity NPD9716 Approved
0.6639 Remote Similarity NPD2962 Approved
0.6639 Remote Similarity NPD2961 Approved
0.6638 Remote Similarity NPD4164 Clinical (unspecified phase)
0.6638 Remote Similarity NPD3064 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5927 Discontinued
0.6636 Remote Similarity NPD2201 Approved
0.6635 Remote Similarity NPD1796 Phase 3
0.6634 Remote Similarity NPD4545 Approved
0.6634 Remote Similarity NPD4542 Approved
0.6609 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6604 Remote Similarity NPD5655 Clinical (unspecified phase)
0.66 Remote Similarity NPD4543 Discontinued
0.66 Remote Similarity NPD7160 Approved
0.6585 Remote Similarity NPD2846 Clinical (unspecified phase)
0.6583 Remote Similarity NPD5653 Discontinued
0.6581 Remote Similarity NPD1302 Clinical (unspecified phase)
0.6579 Remote Similarity NPD1344 Phase 2
0.6574 Remote Similarity NPD811 Approved
0.6574 Remote Similarity NPD3526 Approved
0.6574 Remote Similarity NPD812 Approved
0.6574 Remote Similarity NPD810 Approved
0.6574 Remote Similarity NPD3524 Approved
0.6571 Remote Similarity NPD1795 Discontinued
0.6562 Remote Similarity NPD4544 Approved
0.6556 Remote Similarity NPD9589 Approved
0.6556 Remote Similarity NPD9592 Approved
0.6556 Remote Similarity NPD80 Approved
0.6556 Remote Similarity NPD9590 Approved
0.6556 Remote Similarity NPD9593 Approved
0.6556 Remote Similarity NPD9591 Approved
0.6556 Remote Similarity NPD9594 Approved
0.6556 Remote Similarity NPD9588 Approved
0.6555 Remote Similarity NPD7464 Phase 3
0.6532 Remote Similarity NPD6740 Clinical (unspecified phase)
0.6531 Remote Similarity NPD3428 Approved
0.6531 Remote Similarity NPD783 Approved
0.6531 Remote Similarity NPD3426 Approved
0.6531 Remote Similarity NPD781 Approved
0.6531 Remote Similarity NPD187 Approved
0.6531 Remote Similarity NPD780 Approved
0.6531 Remote Similarity NPD2002 Discontinued
0.6531 Remote Similarity NPD782 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