Structure

Physi-Chem Properties

Molecular Weight:  287.26
Volume:  340.451
LogP:  6.533
LogD:  4.425
LogS:  -5.828
# Rotatable Bonds:  10
TPSA:  3.24
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.518
Synthetic Accessibility Score:  2.305
Fsp3:  0.7
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:  -4.688
MDCK Permeability:  9.247298294212669e-06
Pgp-inhibitor:  0.639
Pgp-substrate:  0.255
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.044
30% Bioavailability (F30%):  0.553

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.874
Plasma Protein Binding (PPB):  94.90167999267578%
Volume Distribution (VD):  1.797
Pgp-substrate:  2.9154090881347656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.253
CYP1A2-substrate:  0.738
CYP2C19-inhibitor:  0.357
CYP2C19-substrate:  0.934
CYP2C9-inhibitor:  0.039
CYP2C9-substrate:  0.082
CYP2D6-inhibitor:  0.992
CYP2D6-substrate:  0.897
CYP3A4-inhibitor:  0.224
CYP3A4-substrate:  0.472

ADMET: Excretion

Clearance (CL):  5.748
Half-life (T1/2):  0.132

ADMET: Toxicity

hERG Blockers:  0.981
Human Hepatotoxicity (H-HT):  0.457
Drug-inuced Liver Injury (DILI):  0.054
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.073
Maximum Recommended Daily Dose:  0.555
Skin Sensitization:  0.961
Carcinogencity:  0.072
Eye Corrosion:  0.902
Eye Irritation:  0.545
Respiratory Toxicity:  0.909

Download Data

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

  Natural Product: NPC231986

Natural Product ID:  NPC231986
Common Name*:   N-Methyl-2-(9'-Phenylnonyl)-Pyrrolidine
IUPAC Name:   (2R)-1-methyl-2-(9-phenylnonyl)pyrrolidine
Synonyms:  
Standard InCHIKey:  MNVHQKNDNJJRIX-HXUWFJFHSA-N
Standard InCHI:  InChI=1S/C20H33N/c1-21-18-12-17-20(21)16-11-6-4-2-3-5-8-13-19-14-9-7-10-15-19/h7,9-10,14-15,20H,2-6,8,11-13,16-18H2,1H3/t20-/m1/s1
SMILES:  CN1CCC[C@H]1CCCCCCCCCc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL490575
PubChem CID:   461558
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004707] Organic nitrogen compounds
      • [CHEMONTID:0000278] Organonitrogen compounds
        • [CHEMONTID:0002449] Amines
          • [CHEMONTID:0003899] Aralkylamines

*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
NPO7837 Crassostrea rivularis Species Ostreidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11569 Hypsizygus ulmarius Species Lyophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7837 Crassostrea rivularis Species Ostreidae 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
NPT140 Organism Artemia Artemia LC50 = 1.0 ug.mL-1 PMID[504048]

☑ 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 NPC231986 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
0.8125 Intermediate Similarity NPC271642
0.8 Intermediate Similarity NPC98976
0.7978 Intermediate Similarity NPC470926
0.7901 Intermediate Similarity NPC139658
0.7875 Intermediate Similarity NPC112609
0.7875 Intermediate Similarity NPC113000
0.7875 Intermediate Similarity NPC122327
0.7805 Intermediate Similarity NPC290638
0.7684 Intermediate Similarity NPC474582
0.7674 Intermediate Similarity NPC104070
0.76 Intermediate Similarity NPC210849
0.759 Intermediate Similarity NPC325662
0.759 Intermediate Similarity NPC98269
0.7561 Intermediate Similarity NPC276699
0.7531 Intermediate Similarity NPC244738
0.75 Intermediate Similarity NPC12857
0.75 Intermediate Similarity NPC229235
0.7471 Intermediate Similarity NPC474088
0.7386 Intermediate Similarity NPC169016
0.7386 Intermediate Similarity NPC133162
0.7374 Intermediate Similarity NPC474695
0.7368 Intermediate Similarity NPC472258
0.734 Intermediate Similarity NPC329430
0.7273 Intermediate Similarity NPC119677
0.7245 Intermediate Similarity NPC239854
0.7234 Intermediate Similarity NPC474974
0.72 Intermediate Similarity NPC300345
0.72 Intermediate Similarity NPC120441
0.72 Intermediate Similarity NPC212114
0.72 Intermediate Similarity NPC65873
0.7143 Intermediate Similarity NPC17497
0.7143 Intermediate Similarity NPC54368
0.7143 Intermediate Similarity NPC248705
0.7143 Intermediate Similarity NPC150196
0.7143 Intermediate Similarity NPC305602
0.7143 Intermediate Similarity NPC135924
0.7128 Intermediate Similarity NPC473661
0.7089 Intermediate Similarity NPC155172
0.7089 Intermediate Similarity NPC32312
0.7089 Intermediate Similarity NPC198023
0.7073 Intermediate Similarity NPC219246
0.7067 Intermediate Similarity NPC269586
0.7067 Intermediate Similarity NPC198841
0.7051 Intermediate Similarity NPC22786
0.7051 Intermediate Similarity NPC29680
0.7033 Intermediate Similarity NPC258046
0.703 Intermediate Similarity NPC167336
0.7024 Intermediate Similarity NPC299134
0.7013 Intermediate Similarity NPC147062
0.7 Intermediate Similarity NPC178527
0.6966 Remote Similarity NPC14326
0.6962 Remote Similarity NPC50266
0.6962 Remote Similarity NPC88566
0.6962 Remote Similarity NPC45756
0.6957 Remote Similarity NPC60408
0.6957 Remote Similarity NPC473031
0.6939 Remote Similarity NPC322598
0.6933 Remote Similarity NPC277704
0.6933 Remote Similarity NPC149436
0.6932 Remote Similarity NPC475573
0.6932 Remote Similarity NPC475289
0.6931 Remote Similarity NPC469974
0.6923 Remote Similarity NPC310758
0.6923 Remote Similarity NPC238023
0.6923 Remote Similarity NPC246588
0.6915 Remote Similarity NPC141139
0.6915 Remote Similarity NPC74936
0.6915 Remote Similarity NPC78041
0.6915 Remote Similarity NPC159178
0.6915 Remote Similarity NPC121872
0.6915 Remote Similarity NPC209764
0.6915 Remote Similarity NPC471307
0.6915 Remote Similarity NPC316108
0.6907 Remote Similarity NPC471320
0.6907 Remote Similarity NPC471319
0.6907 Remote Similarity NPC25565
0.69 Remote Similarity NPC291610
0.6883 Remote Similarity NPC8235
0.6883 Remote Similarity NPC64270
0.6882 Remote Similarity NPC12429
0.6863 Remote Similarity NPC473418
0.6848 Remote Similarity NPC203076
0.6837 Remote Similarity NPC473501
0.6837 Remote Similarity NPC475439
0.6835 Remote Similarity NPC66517
0.6809 Remote Similarity NPC470877
0.68 Remote Similarity NPC228400
0.68 Remote Similarity NPC214200
0.6795 Remote Similarity NPC169110
0.6762 Remote Similarity NPC292758
0.6762 Remote Similarity NPC65855
0.6759 Remote Similarity NPC246904
0.675 Remote Similarity NPC113670
0.675 Remote Similarity NPC21211
0.6747 Remote Similarity NPC473206
0.6747 Remote Similarity NPC200936
0.6739 Remote Similarity NPC3210
0.6707 Remote Similarity NPC267443
0.6707 Remote Similarity NPC6107
0.6706 Remote Similarity NPC54269
0.6701 Remote Similarity NPC7067
0.6701 Remote Similarity NPC469330
0.6701 Remote Similarity NPC322040
0.6701 Remote Similarity NPC471309
0.6699 Remote Similarity NPC143516
0.6697 Remote Similarity NPC473573
0.6667 Remote Similarity NPC36357
0.6667 Remote Similarity NPC114327
0.6667 Remote Similarity NPC110264
0.6667 Remote Similarity NPC264580
0.6635 Remote Similarity NPC474804
0.6635 Remote Similarity NPC474973
0.6635 Remote Similarity NPC130898
0.6633 Remote Similarity NPC256452
0.6633 Remote Similarity NPC161972
0.6633 Remote Similarity NPC303045
0.6633 Remote Similarity NPC58674
0.6627 Remote Similarity NPC22760
0.6625 Remote Similarity NPC71009
0.6596 Remote Similarity NPC471638
0.6585 Remote Similarity NPC113837
0.6585 Remote Similarity NPC289915
0.6549 Remote Similarity NPC476990
0.6549 Remote Similarity NPC200964
0.6548 Remote Similarity NPC139416
0.6548 Remote Similarity NPC246822
0.6548 Remote Similarity NPC297358
0.6548 Remote Similarity NPC213570
0.6531 Remote Similarity NPC71140
0.6514 Remote Similarity NPC35850
0.6514 Remote Similarity NPC276949
0.6509 Remote Similarity NPC473676
0.6509 Remote Similarity NPC77294
0.65 Remote Similarity NPC311242
0.6495 Remote Similarity NPC245259
0.6495 Remote Similarity NPC226438
0.6491 Remote Similarity NPC202521
0.6486 Remote Similarity NPC313673
0.6481 Remote Similarity NPC269340
0.6476 Remote Similarity NPC45033
0.6471 Remote Similarity NPC469457
0.6471 Remote Similarity NPC251490
0.6471 Remote Similarity NPC263385
0.6463 Remote Similarity NPC291066
0.6463 Remote Similarity NPC264470
0.6455 Remote Similarity NPC33742
0.6442 Remote Similarity NPC113326
0.6442 Remote Similarity NPC194390
0.6442 Remote Similarity NPC224610
0.6442 Remote Similarity NPC88267
0.6435 Remote Similarity NPC291027
0.6435 Remote Similarity NPC213126
0.6435 Remote Similarity NPC84281
0.6435 Remote Similarity NPC169485
0.6435 Remote Similarity NPC317474
0.6435 Remote Similarity NPC252878
0.6421 Remote Similarity NPC53492
0.642 Remote Similarity NPC200745
0.6408 Remote Similarity NPC329375
0.6404 Remote Similarity NPC249018
0.6404 Remote Similarity NPC3190
0.6395 Remote Similarity NPC193578
0.6395 Remote Similarity NPC39799
0.6395 Remote Similarity NPC158028
0.6395 Remote Similarity NPC87099
0.6395 Remote Similarity NPC121708
0.6395 Remote Similarity NPC125144
0.6395 Remote Similarity NPC135433
0.6395 Remote Similarity NPC280135
0.6395 Remote Similarity NPC226999
0.6395 Remote Similarity NPC1008
0.6392 Remote Similarity NPC172128
0.6381 Remote Similarity NPC476198
0.6379 Remote Similarity NPC46427
0.6379 Remote Similarity NPC6975
0.6364 Remote Similarity NPC291070
0.6364 Remote Similarity NPC246757
0.6355 Remote Similarity NPC164802
0.6354 Remote Similarity NPC30445
0.6348 Remote Similarity NPC475915
0.6339 Remote Similarity NPC285926
0.6339 Remote Similarity NPC14672
0.6339 Remote Similarity NPC315276
0.6339 Remote Similarity NPC470544
0.633 Remote Similarity NPC475013
0.6322 Remote Similarity NPC1901
0.6322 Remote Similarity NPC212463
0.6321 Remote Similarity NPC471447
0.6311 Remote Similarity NPC316797
0.6311 Remote Similarity NPC155847
0.6311 Remote Similarity NPC289381
0.631 Remote Similarity NPC52330
0.63 Remote Similarity NPC108339
0.6296 Remote Similarity NPC45255
0.6296 Remote Similarity NPC158854
0.6286 Remote Similarity NPC304761
0.6286 Remote Similarity NPC150254
0.6286 Remote Similarity NPC275467
0.6286 Remote Similarity NPC226778
0.6286 Remote Similarity NPC147000

  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 NPC231986 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
0.9367 High Similarity NPD5178 Approved
0.8875 High Similarity NPD4701 Clinical (unspecified phase)
0.8875 High Similarity NPD4169 Approved
0.8875 High Similarity NPD4170 Approved
0.875 High Similarity NPD3035 Approved
0.8734 High Similarity NPD1051 Approved
0.8734 High Similarity NPD1053 Approved
0.8734 High Similarity NPD1052 Approved
0.8718 High Similarity NPD4144 Approved
0.8718 High Similarity NPD4147 Approved
0.8625 High Similarity NPD5372 Approved
0.8625 High Similarity NPD5371 Approved
0.8519 High Similarity NPD4026 Approved
0.8519 High Similarity NPD4027 Approved
0.8452 Intermediate Similarity NPD3099 Discontinued
0.8434 Intermediate Similarity NPD2538 Approved
0.8434 Intermediate Similarity NPD2539 Approved
0.8333 Intermediate Similarity NPD2208 Approved
0.8333 Intermediate Similarity NPD2205 Approved
0.825 Intermediate Similarity NPD603 Approved
0.8235 Intermediate Similarity NPD4636 Approved
0.8235 Intermediate Similarity NPD5252 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD5964 Phase 2
0.8222 Intermediate Similarity NPD5963 Phase 2
0.8148 Intermediate Similarity NPD296 Approved
0.8148 Intermediate Similarity NPD293 Approved
0.8148 Intermediate Similarity NPD295 Approved
0.814 Intermediate Similarity NPD4146 Approved
0.814 Intermediate Similarity NPD4145 Approved
0.8095 Intermediate Similarity NPD831 Approved
0.8095 Intermediate Similarity NPD4635 Approved
0.8095 Intermediate Similarity NPD830 Approved
0.8049 Intermediate Similarity NPD589 Approved
0.8049 Intermediate Similarity NPD590 Approved
0.8023 Intermediate Similarity NPD4406 Approved
0.8023 Intermediate Similarity NPD4409 Approved
0.8 Intermediate Similarity NPD785 Approved
0.7978 Intermediate Similarity NPD2997 Approved
0.7978 Intermediate Similarity NPD2998 Approved
0.7978 Intermediate Similarity NPD3000 Approved
0.7978 Intermediate Similarity NPD4543 Discontinued
0.7955 Intermediate Similarity NPD5656 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD3979 Approved
0.7952 Intermediate Similarity NPD3904 Approved
0.7952 Intermediate Similarity NPD3981 Approved
0.7952 Intermediate Similarity NPD3903 Approved
0.7931 Intermediate Similarity NPD782 Approved
0.7931 Intermediate Similarity NPD781 Approved
0.7931 Intermediate Similarity NPD783 Approved
0.7931 Intermediate Similarity NPD780 Approved
0.7907 Intermediate Similarity NPD5916 Discontinued
0.7875 Intermediate Similarity NPD9589 Approved
0.7875 Intermediate Similarity NPD9590 Approved
0.7875 Intermediate Similarity NPD80 Approved
0.7875 Intermediate Similarity NPD9588 Approved
0.7875 Intermediate Similarity NPD9591 Approved
0.7875 Intermediate Similarity NPD9592 Approved
0.7875 Intermediate Similarity NPD9594 Approved
0.7875 Intermediate Similarity NPD9593 Approved
0.7865 Intermediate Similarity NPD3346 Approved
0.7865 Intermediate Similarity NPD5915 Approved
0.7865 Intermediate Similarity NPD3344 Approved
0.7841 Intermediate Similarity NPD3345 Approved
0.7841 Intermediate Similarity NPD5675 Discontinued
0.7831 Intermediate Similarity NPD507 Approved
0.7831 Intermediate Similarity NPD508 Approved
0.7753 Intermediate Similarity NPD771 Phase 3
0.7701 Intermediate Similarity NPD9505 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD1800 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD294 Approved
0.7625 Intermediate Similarity NPD292 Approved
0.7609 Intermediate Similarity NPD6548 Approved
0.7609 Intermediate Similarity NPD6549 Approved
0.7586 Intermediate Similarity NPD4544 Approved
0.7579 Intermediate Similarity NPD1946 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD2197 Approved
0.7551 Intermediate Similarity NPD2192 Approved
0.7531 Intermediate Similarity NPD9728 Phase 1
0.7528 Intermediate Similarity NPD3428 Approved
0.7528 Intermediate Similarity NPD3426 Approved
0.7528 Intermediate Similarity NPD2002 Discontinued
0.7527 Intermediate Similarity NPD2655 Approved
0.7527 Intermediate Similarity NPD2656 Approved
0.7527 Intermediate Similarity NPD5554 Approved
0.75 Intermediate Similarity NPD79 Approved
0.75 Intermediate Similarity NPD4408 Approved
0.75 Intermediate Similarity NPD4405 Approved
0.75 Intermediate Similarity NPD9564 Approved
0.75 Intermediate Similarity NPD9563 Approved
0.75 Intermediate Similarity NPD4407 Approved
0.7447 Intermediate Similarity NPD1738 Approved
0.7442 Intermediate Similarity NPD472 Approved
0.7423 Intermediate Similarity NPD5716 Approved
0.7423 Intermediate Similarity NPD2196 Discontinued
0.7423 Intermediate Similarity NPD5753 Discontinued
0.7419 Intermediate Similarity NPD4542 Approved
0.7419 Intermediate Similarity NPD4545 Approved
0.7386 Intermediate Similarity NPD3427 Approved
0.7386 Intermediate Similarity NPD3429 Approved
0.7368 Intermediate Similarity NPD4655 Approved
0.7368 Intermediate Similarity NPD4657 Approved
0.7292 Intermediate Similarity NPD4813 Approved
0.7292 Intermediate Similarity NPD6499 Approved
0.7292 Intermediate Similarity NPD6498 Approved
0.7292 Intermediate Similarity NPD4263 Approved
0.7273 Intermediate Similarity NPD2001 Discontinued
0.7273 Intermediate Similarity NPD4000 Phase 3
0.7263 Intermediate Similarity NPD2005 Discontinued
0.7253 Intermediate Similarity NPD587 Approved
0.7253 Intermediate Similarity NPD588 Approved
0.7245 Intermediate Similarity NPD6588 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD6027 Approved
0.7245 Intermediate Similarity NPD6024 Approved
0.7229 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7160 Approved
0.72 Intermediate Similarity NPD5717 Approved
0.7188 Intermediate Similarity NPD5597 Approved
0.7188 Intermediate Similarity NPD1099 Approved
0.7188 Intermediate Similarity NPD5598 Approved
0.7188 Intermediate Similarity NPD1100 Approved
0.7172 Intermediate Similarity NPD3680 Approved
0.7172 Intermediate Similarity NPD3682 Approved
0.7158 Intermediate Similarity NPD4094 Approved
0.7157 Intermediate Similarity NPD8009 Approved
0.7157 Intermediate Similarity NPD8010 Approved
0.7128 Intermediate Similarity NPD6690 Approved
0.7126 Intermediate Similarity NPD260 Discontinued
0.7115 Intermediate Similarity NPD4571 Approved
0.7115 Intermediate Similarity NPD4573 Approved
0.7115 Intermediate Similarity NPD4572 Approved
0.7113 Intermediate Similarity NPD4117 Approved
0.7113 Intermediate Similarity NPD466 Approved
0.71 Intermediate Similarity NPD2939 Approved
0.71 Intermediate Similarity NPD2937 Phase 1
0.7089 Intermediate Similarity NPD173 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD3581 Discontinued
0.7083 Intermediate Similarity NPD6472 Discontinued
0.7071 Intermediate Similarity NPD4719 Phase 2
0.7071 Intermediate Similarity NPD4803 Discontinued
0.7071 Intermediate Similarity NPD4817 Approved
0.7071 Intermediate Similarity NPD4818 Approved
0.7059 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD2878 Approved
0.7053 Intermediate Similarity NPD3982 Approved
0.7053 Intermediate Similarity NPD3980 Approved
0.7053 Intermediate Similarity NPD736 Approved
0.7053 Intermediate Similarity NPD735 Approved
0.7041 Intermediate Similarity NPD4008 Approved
0.7041 Intermediate Similarity NPD4007 Approved
0.7041 Intermediate Similarity NPD742 Approved
0.703 Intermediate Similarity NPD1677 Discontinued
0.7009 Intermediate Similarity NPD4801 Phase 1
0.7 Intermediate Similarity NPD9395 Approved
0.699 Remote Similarity NPD1721 Clinical (unspecified phase)
0.6961 Remote Similarity NPD3459 Approved
0.6961 Remote Similarity NPD7130 Phase 3
0.6939 Remote Similarity NPD5832 Phase 3
0.6932 Remote Similarity NPD1617 Discontinued
0.6931 Remote Similarity NPD4936 Approved
0.6931 Remote Similarity NPD488 Approved
0.6931 Remote Similarity NPD489 Approved
0.6931 Remote Similarity NPD4937 Approved
0.6923 Remote Similarity NPD7633 Discontinued
0.6915 Remote Similarity NPD4728 Approved
0.6907 Remote Similarity NPD157 Clinical (unspecified phase)
0.6907 Remote Similarity NPD2895 Discontinued
0.69 Remote Similarity NPD2648 Phase 3
0.69 Remote Similarity NPD2193 Phase 2
0.69 Remote Similarity NPD855 Approved
0.69 Remote Similarity NPD4119 Approved
0.69 Remote Similarity NPD854 Approved
0.6897 Remote Similarity NPD9393 Approved
0.6897 Remote Similarity NPD9397 Approved
0.6893 Remote Similarity NPD5253 Approved
0.6869 Remote Similarity NPD1796 Phase 3
0.6869 Remote Similarity NPD787 Suspended
0.6848 Remote Similarity NPD304 Approved
0.6848 Remote Similarity NPD305 Approved
0.6837 Remote Similarity NPD528 Clinical (unspecified phase)
0.6832 Remote Similarity NPD3681 Approved
0.6832 Remote Similarity NPD3357 Discontinued
0.6832 Remote Similarity NPD3683 Approved
0.6832 Remote Similarity NPD5655 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6343 Approved
0.6818 Remote Similarity NPD6345 Approved
0.6804 Remote Similarity NPD7343 Discovery
0.6804 Remote Similarity NPD7344 Phase 1
0.68 Remote Similarity NPD1916 Discontinued
0.68 Remote Similarity NPD1795 Discontinued
0.68 Remote Similarity NPD5630 Phase 1
0.6796 Remote Similarity NPD5705 Approved
0.6796 Remote Similarity NPD5706 Approved
0.6796 Remote Similarity NPD5704 Approved
0.6796 Remote Similarity NPD3546 Approved
0.6796 Remote Similarity NPD3545 Approved
0.6771 Remote Similarity NPD1812 Approved
0.6771 Remote Similarity NPD1814 Approved
0.6768 Remote Similarity NPD1724 Approved
0.6762 Remote Similarity NPD6236 Approved
0.6762 Remote Similarity NPD6235 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