Structure

Physi-Chem Properties

Molecular Weight:  323.12
Volume:  316.18
LogP:  3.634
LogD:  2.771
LogS:  -4.548
# Rotatable Bonds:  0
TPSA:  40.16
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.745
Synthetic Accessibility Score:  3.292
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:  -5.086
MDCK Permeability:  3.5611476050689816e-05
Pgp-inhibitor:  0.034
Pgp-substrate:  0.082
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.963
Plasma Protein Binding (PPB):  92.08832550048828%
Volume Distribution (VD):  2.637
Pgp-substrate:  4.9876885414123535%

ADMET: Metabolism

CYP1A2-inhibitor:  0.937
CYP1A2-substrate:  0.441
CYP2C19-inhibitor:  0.89
CYP2C19-substrate:  0.843
CYP2C9-inhibitor:  0.049
CYP2C9-substrate:  0.814
CYP2D6-inhibitor:  0.882
CYP2D6-substrate:  0.936
CYP3A4-inhibitor:  0.897
CYP3A4-substrate:  0.81

ADMET: Excretion

Clearance (CL):  18.753
Half-life (T1/2):  0.172

ADMET: Toxicity

hERG Blockers:  0.409
Human Hepatotoxicity (H-HT):  0.151
Drug-inuced Liver Injury (DILI):  0.458
AMES Toxicity:  0.767
Rat Oral Acute Toxicity:  0.605
Maximum Recommended Daily Dose:  0.965
Skin Sensitization:  0.184
Carcinogencity:  0.932
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.948

Download Data

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

  Natural Product: NPC210918

Natural Product ID:  NPC210918
Common Name*:   Neolitsine
IUPAC Name:   n.a.
Synonyms:   Neolitsine
Standard InCHIKey:  GKEOKAJRKHTDOS-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C19H17NO4/c1-20-3-2-10-5-16-19(24-9-23-16)18-12-7-15-14(21-8-22-15)6-11(12)4-13(20)17(10)18/h5-7,13H,2-4,8-9H2,1H3/p+1/t13-/m0/s1
SMILES:  C[NH+]1CCc2cc3c(c4-c5cc6c(cc5C[C@H]1c24)OCO6)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL404684
PubChem CID:   10064778
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
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. leaf n.a. DOI[10.1080/10412905.2001.9699624]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[11912066]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. leaf n.a. PMID[12419922]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[18217715]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. leaf n.a. PMID[21188975]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO628 Schisandra nigra Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO189 Pachypodium lealii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2058 Sideritis discolor Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20755 Ballota hirsuta Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2256 Pseudaxinyssa cantharella n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO628 Schisandra nigra Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3183 Phalaenopsis equestris Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO413 Astragalus prusianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8841 Shorea leprosula Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4921 Brickellia diffusa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23324 Porphyridium purpureum Species Porphyridiaceae 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
NPT177 Tissue Aorta Rattus norvegicus IC50 = 290.0 nM PMID[570938]

☑ 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 NPC210918 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
0.987 High Similarity NPC16805
0.987 High Similarity NPC167546
0.987 High Similarity NPC302527
0.9806 High Similarity NPC476432
0.9806 High Similarity NPC24264
0.9744 High Similarity NPC247389
0.9742 High Similarity NPC225774
0.9679 High Similarity NPC219341
0.956 High Similarity NPC149090
0.956 High Similarity NPC19520
0.9548 High Similarity NPC306902
0.9548 High Similarity NPC232924
0.9548 High Similarity NPC477559
0.9548 High Similarity NPC266753
0.9548 High Similarity NPC160298
0.9497 High Similarity NPC6152
0.9441 High Similarity NPC128560
0.9441 High Similarity NPC199465
0.9441 High Similarity NPC229166
0.9416 High Similarity NPC325871
0.9416 High Similarity NPC99659
0.9325 High Similarity NPC320223
0.9325 High Similarity NPC114364
0.9295 High Similarity NPC476572
0.925 High Similarity NPC298979
0.9207 High Similarity NPC148693
0.9207 High Similarity NPC118633
0.9207 High Similarity NPC294790
0.9193 High Similarity NPC241055
0.9187 High Similarity NPC304659
0.9187 High Similarity NPC86144
0.9157 High Similarity NPC248642
0.9157 High Similarity NPC116284
0.9152 High Similarity NPC258695
0.9152 High Similarity NPC126284
0.9152 High Similarity NPC470879
0.9125 High Similarity NPC168409
0.9102 High Similarity NPC156576
0.9097 High Similarity NPC81733
0.9097 High Similarity NPC326316
0.9096 High Similarity NPC476574
0.9096 High Similarity NPC32413
0.9096 High Similarity NPC474506
0.9096 High Similarity NPC155442
0.9096 High Similarity NPC477561
0.9096 High Similarity NPC312918
0.9091 High Similarity NPC23219
0.9062 High Similarity NPC189470
0.9038 High Similarity NPC210148
0.9038 High Similarity NPC233029
0.9036 High Similarity NPC267408
0.903 High Similarity NPC112575
0.9006 High Similarity NPC253043
0.9006 High Similarity NPC306843
0.9006 High Similarity NPC78222
0.9006 High Similarity NPC196447
0.9006 High Similarity NPC96603
0.9006 High Similarity NPC212794
0.9006 High Similarity NPC477563
0.9006 High Similarity NPC13504
0.9006 High Similarity NPC136508
0.8994 High Similarity NPC477080
0.8988 High Similarity NPC135772
0.8987 High Similarity NPC31311
0.8987 High Similarity NPC234392
0.897 High Similarity NPC477558
0.8944 High Similarity NPC324144
0.8941 High Similarity NPC237579
0.8924 High Similarity NPC41178
0.8924 High Similarity NPC244112
0.8924 High Similarity NPC138487
0.8924 High Similarity NPC76079
0.8924 High Similarity NPC216459
0.8903 High Similarity NPC475959
0.8896 High Similarity NPC12053
0.8896 High Similarity NPC117188
0.8896 High Similarity NPC205421
0.8896 High Similarity NPC474931
0.8896 High Similarity NPC145832
0.8896 High Similarity NPC81218
0.8896 High Similarity NPC306555
0.8896 High Similarity NPC158376
0.8889 High Similarity NPC82763
0.8882 High Similarity NPC57036
0.8882 High Similarity NPC214116
0.8868 High Similarity NPC146288
0.883 High Similarity NPC186546
0.883 High Similarity NPC312531
0.883 High Similarity NPC476576
0.8817 High Similarity NPC275132
0.8788 High Similarity NPC152212
0.878 High Similarity NPC204947
0.875 High Similarity NPC126519
0.875 High Similarity NPC170503
0.875 High Similarity NPC203784
0.8735 High Similarity NPC239775
0.8726 High Similarity NPC211296
0.8712 High Similarity NPC1229
0.8706 High Similarity NPC476575
0.8704 High Similarity NPC27410
0.8704 High Similarity NPC166014
0.8675 High Similarity NPC26240
0.8675 High Similarity NPC69712
0.8675 High Similarity NPC477562
0.8667 High Similarity NPC474324
0.8667 High Similarity NPC57812
0.8662 High Similarity NPC130941
0.8647 High Similarity NPC179704
0.8623 High Similarity NPC65403
0.8614 High Similarity NPC475845
0.8608 High Similarity NPC219162
0.8598 High Similarity NPC320104
0.8588 High Similarity NPC220961
0.858 High Similarity NPC287588
0.8571 High Similarity NPC66341
0.8571 High Similarity NPC117717
0.8571 High Similarity NPC2314
0.8571 High Similarity NPC93593
0.8571 High Similarity NPC477020
0.8571 High Similarity NPC192135
0.8563 High Similarity NPC311991
0.8563 High Similarity NPC168753
0.8563 High Similarity NPC474708
0.8563 High Similarity NPC118274
0.8563 High Similarity NPC75958
0.8554 High Similarity NPC181653
0.8554 High Similarity NPC190332
0.8545 High Similarity NPC238530
0.8545 High Similarity NPC232514
0.8545 High Similarity NPC276944
0.8528 High Similarity NPC111485
0.8514 High Similarity NPC475754
0.8488 Intermediate Similarity NPC249405
0.8481 Intermediate Similarity NPC95075
0.8481 Intermediate Similarity NPC476144
0.8481 Intermediate Similarity NPC253883
0.8481 Intermediate Similarity NPC106295
0.8481 Intermediate Similarity NPC51957
0.8481 Intermediate Similarity NPC210437
0.8481 Intermediate Similarity NPC90844
0.8481 Intermediate Similarity NPC16107
0.8471 Intermediate Similarity NPC145304
0.8466 Intermediate Similarity NPC302001
0.8462 Intermediate Similarity NPC128019
0.8462 Intermediate Similarity NPC476567
0.8462 Intermediate Similarity NPC136860
0.8457 Intermediate Similarity NPC78733
0.8452 Intermediate Similarity NPC474915
0.8452 Intermediate Similarity NPC213206
0.8452 Intermediate Similarity NPC188163
0.8452 Intermediate Similarity NPC470925
0.8452 Intermediate Similarity NPC328750
0.8443 Intermediate Similarity NPC150879
0.8443 Intermediate Similarity NPC100566
0.8428 Intermediate Similarity NPC7467
0.8424 Intermediate Similarity NPC60186
0.8421 Intermediate Similarity NPC190461
0.8412 Intermediate Similarity NPC187678
0.8412 Intermediate Similarity NPC304675
0.8405 Intermediate Similarity NPC323443
0.8405 Intermediate Similarity NPC180756
0.84 Intermediate Similarity NPC474904
0.8393 Intermediate Similarity NPC158148
0.8393 Intermediate Similarity NPC290759
0.8393 Intermediate Similarity NPC266176
0.8393 Intermediate Similarity NPC82533
0.8387 Intermediate Similarity NPC314682
0.8383 Intermediate Similarity NPC35627
0.8383 Intermediate Similarity NPC81247
0.8383 Intermediate Similarity NPC476573
0.8382 Intermediate Similarity NPC299990
0.8382 Intermediate Similarity NPC233718
0.8382 Intermediate Similarity NPC73492
0.8375 Intermediate Similarity NPC92541
0.8372 Intermediate Similarity NPC474507
0.8363 Intermediate Similarity NPC237044
0.8333 Intermediate Similarity NPC148898
0.8333 Intermediate Similarity NPC302275
0.8333 Intermediate Similarity NPC470924
0.8323 Intermediate Similarity NPC223125
0.8323 Intermediate Similarity NPC247972
0.8314 Intermediate Similarity NPC15919
0.8314 Intermediate Similarity NPC474325
0.8313 Intermediate Similarity NPC37144
0.8313 Intermediate Similarity NPC59907
0.8312 Intermediate Similarity NPC7018
0.8306 Intermediate Similarity NPC156728
0.8306 Intermediate Similarity NPC244606
0.8294 Intermediate Similarity NPC477640
0.8294 Intermediate Similarity NPC225597
0.8294 Intermediate Similarity NPC470739
0.8293 Intermediate Similarity NPC186063
0.8284 Intermediate Similarity NPC475686
0.8284 Intermediate Similarity NPC58766
0.8268 Intermediate Similarity NPC162653
0.8266 Intermediate Similarity NPC474745
0.8266 Intermediate Similarity NPC244554
0.8263 Intermediate Similarity NPC233650
0.8256 Intermediate Similarity NPC476577
0.8256 Intermediate Similarity NPC148709

  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 NPC210918 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
0.8481 Intermediate Similarity NPD4584 Approved
0.8452 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8408 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD4481 Phase 3
0.8274 Intermediate Similarity NPD3051 Approved
0.8118 Intermediate Similarity NPD2969 Approved
0.8118 Intermediate Similarity NPD2970 Approved
0.7977 Intermediate Similarity NPD8252 Approved
0.7977 Intermediate Similarity NPD8251 Approved
0.7977 Intermediate Similarity NPD8099 Discontinued
0.7965 Intermediate Similarity NPD27 Approved
0.7965 Intermediate Similarity NPD2489 Approved
0.7963 Intermediate Similarity NPD2421 Approved
0.7963 Intermediate Similarity NPD2420 Approved
0.7931 Intermediate Similarity NPD8156 Discontinued
0.7904 Intermediate Similarity NPD7298 Approved
0.7901 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.788 Intermediate Similarity NPD4420 Approved
0.787 Intermediate Similarity NPD6788 Approved
0.7833 Intermediate Similarity NPD7906 Approved
0.7831 Intermediate Similarity NPD4017 Approved
0.7809 Intermediate Similarity NPD2971 Approved
0.7809 Intermediate Similarity NPD2968 Approved
0.7733 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD5006 Approved
0.7713 Intermediate Similarity NPD5005 Approved
0.7711 Intermediate Similarity NPD3639 Approved
0.7711 Intermediate Similarity NPD3641 Approved
0.7711 Intermediate Similarity NPD3640 Phase 3
0.7709 Intermediate Similarity NPD4578 Approved
0.7709 Intermediate Similarity NPD7312 Approved
0.7709 Intermediate Similarity NPD7310 Approved
0.7709 Intermediate Similarity NPD4577 Approved
0.7709 Intermediate Similarity NPD7313 Approved
0.7709 Intermediate Similarity NPD7311 Approved
0.768 Intermediate Similarity NPD4663 Approved
0.7667 Intermediate Similarity NPD8053 Approved
0.7667 Intermediate Similarity NPD8054 Approved
0.7667 Intermediate Similarity NPD7309 Approved
0.7658 Intermediate Similarity NPD3110 Approved
0.7658 Intermediate Similarity NPD3109 Approved
0.7647 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD5241 Discontinued
0.7605 Intermediate Similarity NPD4727 Phase 1
0.7605 Intermediate Similarity NPD6030 Approved
0.7605 Intermediate Similarity NPD6031 Approved
0.758 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD2898 Approved
0.7543 Intermediate Similarity NPD6071 Discontinued
0.7529 Intermediate Similarity NPD4772 Phase 2
0.7529 Intermediate Similarity NPD4773 Phase 2
0.7514 Intermediate Similarity NPD7833 Phase 2
0.7514 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7831 Phase 2
0.75 Intermediate Similarity NPD2563 Approved
0.75 Intermediate Similarity NPD2560 Approved
0.7459 Intermediate Similarity NPD2490 Approved
0.7459 Intermediate Similarity NPD2488 Approved
0.7455 Intermediate Similarity NPD5754 Discontinued
0.7447 Intermediate Similarity NPD2975 Approved
0.7447 Intermediate Similarity NPD2973 Approved
0.7447 Intermediate Similarity NPD2974 Approved
0.7443 Intermediate Similarity NPD4010 Discontinued
0.7423 Intermediate Similarity NPD4859 Phase 1
0.7421 Intermediate Similarity NPD5718 Phase 2
0.7418 Intermediate Similarity NPD7281 Phase 3
0.7418 Intermediate Similarity NPD7280 Phase 3
0.7412 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD3763 Approved
0.7396 Intermediate Similarity NPD5976 Discontinued
0.7394 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7802 Discontinued
0.7386 Intermediate Similarity NPD6107 Approved
0.7377 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD4166 Phase 2
0.7341 Intermediate Similarity NPD2978 Approved
0.7341 Intermediate Similarity NPD2977 Approved
0.7337 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD4580 Approved
0.7314 Intermediate Similarity NPD5604 Discontinued
0.7314 Intermediate Similarity NPD4055 Discovery
0.7305 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD3450 Approved
0.7292 Intermediate Similarity NPD3452 Approved
0.7292 Intermediate Similarity NPD2493 Approved
0.7292 Intermediate Similarity NPD2494 Approved
0.7278 Intermediate Similarity NPD1424 Approved
0.7273 Intermediate Similarity NPD7827 Phase 1
0.7273 Intermediate Similarity NPD7400 Phase 3
0.7268 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4475 Approved
0.7267 Intermediate Similarity NPD4474 Approved
0.7262 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD3845 Phase 1
0.7258 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD4107 Approved
0.7235 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD3124 Discontinued
0.7211 Intermediate Similarity NPD5582 Discontinued
0.7195 Intermediate Similarity NPD6895 Approved
0.7195 Intermediate Similarity NPD6896 Approved
0.7188 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8095 Phase 1
0.7179 Intermediate Similarity NPD4583 Approved
0.7179 Intermediate Similarity NPD4582 Approved
0.7164 Intermediate Similarity NPD7047 Phase 3
0.716 Intermediate Similarity NPD7124 Phase 2
0.7158 Intermediate Similarity NPD6297 Approved
0.7143 Intermediate Similarity NPD5312 Approved
0.7143 Intermediate Similarity NPD5313 Approved
0.7134 Intermediate Similarity NPD2492 Phase 1
0.7128 Intermediate Similarity NPD4002 Approved
0.7128 Intermediate Similarity NPD4004 Approved
0.7122 Intermediate Similarity NPD6997 Phase 2
0.7118 Intermediate Similarity NPD7598 Phase 2
0.7113 Intermediate Similarity NPD4482 Phase 3
0.7111 Intermediate Similarity NPD6688 Approved
0.7111 Intermediate Similarity NPD6687 Approved
0.7102 Intermediate Similarity NPD5978 Approved
0.7102 Intermediate Similarity NPD5977 Approved
0.7083 Intermediate Similarity NPD4237 Approved
0.7083 Intermediate Similarity NPD4236 Phase 3
0.7076 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3705 Approved
0.7065 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD4210 Discontinued
0.7048 Intermediate Similarity NPD4108 Discontinued
0.7041 Intermediate Similarity NPD6748 Discontinued
0.7039 Intermediate Similarity NPD6037 Discontinued
0.7039 Intermediate Similarity NPD5677 Discontinued
0.7015 Intermediate Similarity NPD3816 Phase 1
0.7015 Intermediate Similarity NPD3815 Phase 1
0.7011 Intermediate Similarity NPD4005 Discontinued
0.701 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD6851 Approved
0.7005 Intermediate Similarity NPD6853 Approved
0.6994 Remote Similarity NPD6812 Clinical (unspecified phase)
0.699 Remote Similarity NPD3057 Approved
0.6989 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6984 Remote Similarity NPD3349 Phase 2
0.6982 Remote Similarity NPD5177 Phase 3
0.6963 Remote Similarity NPD7296 Approved
0.6949 Remote Similarity NPD4585 Approved
0.6947 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6936 Remote Similarity NPD6090 Discontinued
0.6933 Remote Similarity NPD5155 Approved
0.6933 Remote Similarity NPD5156 Approved
0.6932 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7110 Phase 1
0.6928 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6919 Remote Similarity NPD4040 Phase 1
0.6919 Remote Similarity NPD3885 Approved
0.6914 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6904 Remote Similarity NPD2972 Approved
0.6904 Remote Similarity NPD3533 Approved
0.6901 Remote Similarity NPD6625 Approved
0.6901 Remote Similarity NPD6723 Discontinued
0.6897 Remote Similarity NPD1914 Approved
0.6895 Remote Similarity NPD7291 Discontinued
0.6893 Remote Similarity NPD3384 Approved
0.6893 Remote Similarity NPD3383 Approved
0.6893 Remote Similarity NPD3382 Approved
0.6888 Remote Similarity NPD5457 Discontinued
0.6882 Remote Similarity NPD3060 Approved
0.6882 Remote Similarity NPD6674 Discontinued
0.6879 Remote Similarity NPD7019 Approved
0.6879 Remote Similarity NPD7020 Approved
0.6871 Remote Similarity NPD3595 Approved
0.6871 Remote Similarity NPD2606 Approved
0.6871 Remote Similarity NPD2605 Approved
0.6871 Remote Similarity NPD3594 Approved
0.6868 Remote Similarity NPD6747 Phase 1
0.6865 Remote Similarity NPD42 Phase 2
0.6865 Remote Similarity NPD6042 Phase 2
0.6864 Remote Similarity NPD1375 Discontinued
0.6864 Remote Similarity NPD4725 Approved
0.6864 Remote Similarity NPD4726 Approved
0.6864 Remote Similarity NPD4721 Approved
0.686 Remote Similarity NPD6666 Approved
0.686 Remote Similarity NPD6667 Approved
0.6859 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5772 Approved
0.6854 Remote Similarity NPD5773 Approved
0.6852 Remote Similarity NPD7247 Discontinued
0.6845 Remote Similarity NPD1753 Discontinued
0.6842 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6836 Remote Similarity NPD6385 Approved
0.6836 Remote Similarity NPD6386 Approved
0.6833 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6818 Remote Similarity NPD3448 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