Structure

Physi-Chem Properties

Molecular Weight:  309.14
Volume:  315.947
LogP:  3.448
LogD:  2.734
LogS:  -3.945
# Rotatable Bonds:  1
TPSA:  30.93
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.809
Synthetic Accessibility Score:  3.12
Fsp3:  0.368
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:  -4.855
MDCK Permeability:  2.7452291760710068e-05
Pgp-inhibitor:  0.331
Pgp-substrate:  0.931
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.985
Plasma Protein Binding (PPB):  93.64642333984375%
Volume Distribution (VD):  2.608
Pgp-substrate:  2.6155781745910645%

ADMET: Metabolism

CYP1A2-inhibitor:  0.827
CYP1A2-substrate:  0.857
CYP2C19-inhibitor:  0.555
CYP2C19-substrate:  0.922
CYP2C9-inhibitor:  0.023
CYP2C9-substrate:  0.753
CYP2D6-inhibitor:  0.896
CYP2D6-substrate:  0.937
CYP3A4-inhibitor:  0.764
CYP3A4-substrate:  0.905

ADMET: Excretion

Clearance (CL):  13.613
Half-life (T1/2):  0.194

ADMET: Toxicity

hERG Blockers:  0.644
Human Hepatotoxicity (H-HT):  0.191
Drug-inuced Liver Injury (DILI):  0.358
AMES Toxicity:  0.909
Rat Oral Acute Toxicity:  0.786
Maximum Recommended Daily Dose:  0.956
Skin Sensitization:  0.099
Carcinogencity:  0.833
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.889

Download Data

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

  Natural Product: NPC219341

Natural Product ID:  NPC219341
Common Name*:   SKQCMMAAFNFEPY-CYBMUJFWSA-N
IUPAC Name:   n.a.
Synonyms:   N-Methyl-Puterine
Standard InCHIKey:  SKQCMMAAFNFEPY-CYBMUJFWSA-N
Standard InCHI:  InChI=1S/C19H19NO3/c1-20-7-6-12-9-15-19(23-10-22-15)18-16(12)13(20)8-11-4-3-5-14(21-2)17(11)18/h3-5,9,13H,6-8,10H2,1-2H3/t13-/m1/s1
SMILES:  CN1CCc2cc3c(c4-c5c(cccc5OC)C[C@@H]1c24)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL486823
PubChem CID:   15748189
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
NPO32735 guatteria scbmburgkiana Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[8676127]

☑ 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
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus IC50 = 31800.0 nM PMID[453490]
NPT2 Others Unspecified Ratio IC50 > 3.1 n.a. PMID[453490]

☑ 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 NPC219341 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
0.9935 High Similarity NPC225774
0.9935 High Similarity NPC247389
0.987 High Similarity NPC476432
0.987 High Similarity NPC24264
0.9805 High Similarity NPC302527
0.9805 High Similarity NPC167546
0.9805 High Similarity NPC16805
0.9739 High Similarity NPC306902
0.9739 High Similarity NPC232924
0.9739 High Similarity NPC160298
0.9739 High Similarity NPC477559
0.9739 High Similarity NPC266753
0.9679 High Similarity NPC210918
0.9503 High Similarity NPC320223
0.9503 High Similarity NPC114364
0.9497 High Similarity NPC149090
0.9497 High Similarity NPC19520
0.9481 High Similarity NPC476572
0.9434 High Similarity NPC6152
0.943 High Similarity NPC298979
0.9379 High Similarity NPC128560
0.9379 High Similarity NPC199465
0.9379 High Similarity NPC229166
0.9371 High Similarity NPC241055
0.9367 High Similarity NPC304659
0.9367 High Similarity NPC86144
0.9351 High Similarity NPC325871
0.9351 High Similarity NPC99659
0.9329 High Similarity NPC248642
0.9325 High Similarity NPC126284
0.9304 High Similarity NPC168409
0.9281 High Similarity NPC81733
0.9281 High Similarity NPC326316
0.9273 High Similarity NPC156576
0.9268 High Similarity NPC474506
0.9268 High Similarity NPC32413
0.9241 High Similarity NPC189470
0.9207 High Similarity NPC470879
0.9207 High Similarity NPC267408
0.9207 High Similarity NPC258695
0.9202 High Similarity NPC112575
0.9157 High Similarity NPC135772
0.9146 High Similarity NPC23219
0.9141 High Similarity NPC477558
0.9096 High Similarity NPC116284
0.9068 High Similarity NPC145832
0.9068 High Similarity NPC474931
0.9068 High Similarity NPC12053
0.9068 High Similarity NPC81218
0.9068 High Similarity NPC306555
0.9068 High Similarity NPC158376
0.9068 High Similarity NPC117188
0.9068 High Similarity NPC205421
0.9036 High Similarity NPC477561
0.9036 High Similarity NPC155442
0.9036 High Similarity NPC312918
0.9036 High Similarity NPC476574
0.903 High Similarity NPC148693
0.903 High Similarity NPC294790
0.903 High Similarity NPC118633
0.9 High Similarity NPC1229
0.8994 High Similarity NPC237579
0.8981 High Similarity NPC41178
0.8981 High Similarity NPC216459
0.8981 High Similarity NPC244112
0.8981 High Similarity NPC138487
0.8961 High Similarity NPC475959
0.8957 High Similarity NPC152212
0.8944 High Similarity NPC136508
0.8944 High Similarity NPC196447
0.8944 High Similarity NPC477563
0.8944 High Similarity NPC96603
0.8944 High Similarity NPC212794
0.8944 High Similarity NPC306843
0.8944 High Similarity NPC78222
0.8944 High Similarity NPC13504
0.8944 High Similarity NPC253043
0.8935 High Similarity NPC57036
0.8935 High Similarity NPC214116
0.8924 High Similarity NPC170503
0.8924 High Similarity NPC146288
0.8924 High Similarity NPC126519
0.8924 High Similarity NPC203784
0.8882 High Similarity NPC324144
0.8875 High Similarity NPC27410
0.8875 High Similarity NPC166014
0.8869 High Similarity NPC476575
0.8861 High Similarity NPC76079
0.883 High Similarity NPC82763
0.8812 High Similarity NPC477080
0.8805 High Similarity NPC31311
0.8805 High Similarity NPC234392
0.8782 High Similarity NPC219162
0.8782 High Similarity NPC211296
0.8772 High Similarity NPC312531
0.8772 High Similarity NPC476576
0.8772 High Similarity NPC186546
0.8735 High Similarity NPC2314
0.8735 High Similarity NPC477020
0.8735 High Similarity NPC66341
0.8735 High Similarity NPC192135
0.8734 High Similarity NPC210148
0.8734 High Similarity NPC233029
0.8727 High Similarity NPC168753
0.8727 High Similarity NPC118274
0.872 High Similarity NPC204947
0.8698 High Similarity NPC179704
0.8675 High Similarity NPC239775
0.8671 High Similarity NPC475754
0.8654 High Similarity NPC90844
0.8654 High Similarity NPC95075
0.8654 High Similarity NPC253883
0.8647 High Similarity NPC275132
0.8647 High Similarity NPC249405
0.8645 High Similarity NPC145304
0.8639 High Similarity NPC220961
0.8631 High Similarity NPC287588
0.8627 High Similarity NPC470925
0.8625 High Similarity NPC93593
0.8621 High Similarity NPC117717
0.8614 High Similarity NPC477562
0.8614 High Similarity NPC69712
0.8614 High Similarity NPC26240
0.8599 High Similarity NPC130941
0.8598 High Similarity NPC232514
0.8598 High Similarity NPC276944
0.8598 High Similarity NPC238530
0.8571 High Similarity NPC323443
0.8571 High Similarity NPC180756
0.8562 High Similarity NPC314682
0.8555 High Similarity NPC474904
0.8545 High Similarity NPC81247
0.8545 High Similarity NPC35627
0.8545 High Similarity NPC476573
0.8544 High Similarity NPC92541
0.8535 High Similarity NPC106295
0.8535 High Similarity NPC210437
0.8535 High Similarity NPC51957
0.8535 High Similarity NPC476144
0.8535 High Similarity NPC16107
0.8506 High Similarity NPC188163
0.8506 High Similarity NPC328750
0.8506 High Similarity NPC213206
0.8506 High Similarity NPC474915
0.85 High Similarity NPC470924
0.8494 Intermediate Similarity NPC150879
0.8481 Intermediate Similarity NPC7467
0.8476 Intermediate Similarity NPC60186
0.8466 Intermediate Similarity NPC111485
0.843 Intermediate Similarity NPC73492
0.843 Intermediate Similarity NPC233718
0.843 Intermediate Similarity NPC299990
0.8424 Intermediate Similarity NPC320104
0.8421 Intermediate Similarity NPC474507
0.8418 Intermediate Similarity NPC144863
0.8412 Intermediate Similarity NPC148709
0.8412 Intermediate Similarity NPC173416
0.8412 Intermediate Similarity NPC476577
0.8409 Intermediate Similarity NPC302001
0.8397 Intermediate Similarity NPC128019
0.8397 Intermediate Similarity NPC476567
0.8397 Intermediate Similarity NPC136860
0.8395 Intermediate Similarity NPC78733
0.8393 Intermediate Similarity NPC75958
0.8385 Intermediate Similarity NPC148898
0.8385 Intermediate Similarity NPC26601
0.8383 Intermediate Similarity NPC474324
0.8383 Intermediate Similarity NPC57812
0.8382 Intermediate Similarity NPC302275
0.8366 Intermediate Similarity NPC7018
0.8365 Intermediate Similarity NPC37144
0.8365 Intermediate Similarity NPC59907
0.8363 Intermediate Similarity NPC190461
0.8343 Intermediate Similarity NPC65403
0.8333 Intermediate Similarity NPC475845
0.8313 Intermediate Similarity NPC233650
0.8302 Intermediate Similarity NPC476151
0.8294 Intermediate Similarity NPC285941
0.8291 Intermediate Similarity NPC185838
0.8286 Intermediate Similarity NPC14507
0.8286 Intermediate Similarity NPC47077
0.8284 Intermediate Similarity NPC474708
0.8284 Intermediate Similarity NPC311991
0.8282 Intermediate Similarity NPC123323
0.8274 Intermediate Similarity NPC190332
0.8274 Intermediate Similarity NPC181653
0.8263 Intermediate Similarity NPC134858
0.8263 Intermediate Similarity NPC180306
0.8263 Intermediate Similarity NPC247972
0.8256 Intermediate Similarity NPC477560
0.8253 Intermediate Similarity NPC24954
0.8246 Intermediate Similarity NPC187678
0.8235 Intermediate Similarity NPC477640
0.8235 Intermediate Similarity NPC225597
0.8235 Intermediate Similarity NPC470739
0.8232 Intermediate Similarity NPC186063
0.8225 Intermediate Similarity NPC158148
0.8225 Intermediate Similarity NPC266176
0.8225 Intermediate Similarity NPC290759
0.8225 Intermediate Similarity NPC82533

  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 NPC219341 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
0.8535 High Similarity NPD4584 Approved
0.8506 High Similarity NPD4664 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD3051 Approved
0.8344 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD4481 Phase 3
0.8274 Intermediate Similarity NPD2970 Approved
0.8274 Intermediate Similarity NPD2969 Approved
0.8125 Intermediate Similarity NPD2420 Approved
0.8125 Intermediate Similarity NPD2421 Approved
0.8118 Intermediate Similarity NPD2489 Approved
0.8118 Intermediate Similarity NPD27 Approved
0.8063 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD6788 Approved
0.8023 Intermediate Similarity NPD8099 Discontinued
0.8023 Intermediate Similarity NPD8252 Approved
0.8023 Intermediate Similarity NPD8251 Approved
0.7988 Intermediate Similarity NPD4017 Approved
0.7978 Intermediate Similarity NPD7906 Approved
0.7977 Intermediate Similarity NPD8156 Discontinued
0.7955 Intermediate Similarity NPD4577 Approved
0.7955 Intermediate Similarity NPD2968 Approved
0.7955 Intermediate Similarity NPD2971 Approved
0.7955 Intermediate Similarity NPD4578 Approved
0.7904 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD7310 Approved
0.7853 Intermediate Similarity NPD7313 Approved
0.7853 Intermediate Similarity NPD7312 Approved
0.7853 Intermediate Similarity NPD7311 Approved
0.7844 Intermediate Similarity NPD7298 Approved
0.7826 Intermediate Similarity NPD4420 Approved
0.7821 Intermediate Similarity NPD3109 Approved
0.7821 Intermediate Similarity NPD3110 Approved
0.7821 Intermediate Similarity NPD4663 Approved
0.7809 Intermediate Similarity NPD7309 Approved
0.7778 Intermediate Similarity NPD5241 Discontinued
0.7758 Intermediate Similarity NPD3640 Phase 3
0.7758 Intermediate Similarity NPD3641 Approved
0.7758 Intermediate Similarity NPD3639 Approved
0.7736 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD8053 Approved
0.7709 Intermediate Similarity NPD8054 Approved
0.7701 Intermediate Similarity NPD2898 Approved
0.7688 Intermediate Similarity NPD6071 Discontinued
0.7661 Intermediate Similarity NPD7831 Phase 2
0.7661 Intermediate Similarity NPD7833 Phase 2
0.7661 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD5006 Approved
0.766 Intermediate Similarity NPD5005 Approved
0.7651 Intermediate Similarity NPD6031 Approved
0.7651 Intermediate Similarity NPD6030 Approved
0.7651 Intermediate Similarity NPD4727 Phase 1
0.7647 Intermediate Similarity NPD2563 Approved
0.7647 Intermediate Similarity NPD2560 Approved
0.7628 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD5754 Discontinued
0.7596 Intermediate Similarity NPD2490 Approved
0.7596 Intermediate Similarity NPD2488 Approved
0.7581 Intermediate Similarity NPD2975 Approved
0.7581 Intermediate Similarity NPD2974 Approved
0.7581 Intermediate Similarity NPD2973 Approved
0.758 Intermediate Similarity NPD5718 Phase 2
0.7574 Intermediate Similarity NPD4772 Phase 2
0.7574 Intermediate Similarity NPD4773 Phase 2
0.756 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD5604 Discontinued
0.7532 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2978 Approved
0.7485 Intermediate Similarity NPD2977 Approved
0.746 Intermediate Similarity NPD4580 Approved
0.7455 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD5976 Discontinued
0.7433 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD7802 Discontinued
0.7425 Intermediate Similarity NPD1424 Approved
0.7421 Intermediate Similarity NPD3450 Approved
0.7421 Intermediate Similarity NPD4475 Approved
0.7421 Intermediate Similarity NPD2494 Approved
0.7421 Intermediate Similarity NPD4474 Approved
0.7421 Intermediate Similarity NPD2493 Approved
0.7421 Intermediate Similarity NPD3452 Approved
0.7414 Intermediate Similarity NPD7400 Phase 3
0.741 Intermediate Similarity NPD3845 Phase 1
0.741 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4166 Phase 2
0.7386 Intermediate Similarity NPD4010 Discontinued
0.7365 Intermediate Similarity NPD3124 Discontinued
0.736 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD4055 Discovery
0.7342 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD6107 Approved
0.7308 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD4583 Approved
0.7306 Intermediate Similarity NPD4582 Approved
0.7299 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD2492 Phase 1
0.7283 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD4859 Phase 1
0.7278 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD4107 Approved
0.7268 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7280 Phase 3
0.7268 Intermediate Similarity NPD7281 Phase 3
0.7268 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD3763 Approved
0.7262 Intermediate Similarity NPD7598 Phase 2
0.7254 Intermediate Similarity NPD4004 Approved
0.7254 Intermediate Similarity NPD4002 Approved
0.7241 Intermediate Similarity NPD5978 Approved
0.7241 Intermediate Similarity NPD5977 Approved
0.7239 Intermediate Similarity NPD6895 Approved
0.7239 Intermediate Similarity NPD6896 Approved
0.7229 Intermediate Similarity NPD5177 Phase 3
0.7225 Intermediate Similarity NPD8095 Phase 1
0.7219 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7124 Phase 2
0.7198 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD6297 Approved
0.7186 Intermediate Similarity NPD6748 Discontinued
0.7175 Intermediate Similarity NPD5677 Discontinued
0.7175 Intermediate Similarity NPD6037 Discontinued
0.7158 Intermediate Similarity NPD5582 Discontinued
0.715 Intermediate Similarity NPD4482 Phase 3
0.7143 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4236 Phase 3
0.7126 Intermediate Similarity NPD4237 Approved
0.7126 Intermediate Similarity NPD3383 Approved
0.7126 Intermediate Similarity NPD3384 Approved
0.7126 Intermediate Similarity NPD3382 Approved
0.7115 Intermediate Similarity NPD3705 Approved
0.7114 Intermediate Similarity NPD7047 Phase 3
0.7113 Intermediate Similarity NPD3057 Approved
0.7112 Intermediate Similarity NPD3349 Phase 2
0.7091 Intermediate Similarity NPD1753 Discontinued
0.7091 Intermediate Similarity NPD4108 Discontinued
0.7088 Intermediate Similarity NPD5313 Approved
0.7088 Intermediate Similarity NPD5312 Approved
0.7083 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5156 Approved
0.7081 Intermediate Similarity NPD5155 Approved
0.7073 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6997 Phase 2
0.7056 Intermediate Similarity NPD6688 Approved
0.7056 Intermediate Similarity NPD6687 Approved
0.7052 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD7827 Phase 1
0.705 Intermediate Similarity NPD3815 Phase 1
0.705 Intermediate Similarity NPD3816 Phase 1
0.7043 Intermediate Similarity NPD6851 Approved
0.7043 Intermediate Similarity NPD6853 Approved
0.7041 Intermediate Similarity NPD4040 Phase 1
0.7035 Intermediate Similarity NPD1914 Approved
0.7029 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD2972 Approved
0.7026 Intermediate Similarity NPD3533 Approved
0.7021 Intermediate Similarity NPD7291 Discontinued
0.7019 Intermediate Similarity NPD3594 Approved
0.7019 Intermediate Similarity NPD3595 Approved
0.7019 Intermediate Similarity NPD2606 Approved
0.7019 Intermediate Similarity NPD2605 Approved
0.7006 Intermediate Similarity NPD4726 Approved
0.7006 Intermediate Similarity NPD4721 Approved
0.7006 Intermediate Similarity NPD1375 Discontinued
0.7006 Intermediate Similarity NPD4725 Approved
0.7 Intermediate Similarity NPD7247 Discontinued
0.7 Intermediate Similarity NPD6666 Approved
0.7 Intermediate Similarity NPD6667 Approved
0.6995 Remote Similarity NPD42 Phase 2
0.6995 Remote Similarity NPD6042 Phase 2
0.6994 Remote Similarity NPD4210 Discontinued
0.6989 Remote Similarity NPD5772 Approved
0.6989 Remote Similarity NPD5773 Approved
0.6984 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6984 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6090 Discontinued
0.6971 Remote Similarity NPD6386 Approved
0.6971 Remote Similarity NPD7110 Phase 1
0.6971 Remote Similarity NPD6385 Approved
0.6971 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6966 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3636 Approved
0.6957 Remote Similarity NPD3637 Approved
0.6957 Remote Similarity NPD3885 Approved
0.6957 Remote Similarity NPD3635 Approved
0.6954 Remote Similarity NPD4005 Discontinued
0.6941 Remote Similarity NPD5160 Discontinued
0.6939 Remote Similarity NPD3448 Approved
0.6939 Remote Similarity NPD2491 Approved
0.6923 Remote Similarity NPD3060 Approved
0.6923 Remote Similarity NPD6674 Discontinued
0.6923 Remote Similarity NPD5457 Discontinued
0.6919 Remote Similarity NPD4123 Phase 3
0.6918 Remote Similarity NPD1669 Approved
0.6906 Remote Similarity NPD6747 Phase 1
0.6893 Remote Similarity NPD4585 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