Structure

Physi-Chem Properties

Molecular Weight:  339.15
Volume:  342.033
LogP:  3.135
LogD:  2.968
LogS:  -3.71
# Rotatable Bonds:  2
TPSA:  40.16
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.84
Synthetic Accessibility Score:  3.097
Fsp3:  0.4
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:  -5.002
MDCK Permeability:  3.961036418331787e-05
Pgp-inhibitor:  0.473
Pgp-substrate:  0.924
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.979
Plasma Protein Binding (PPB):  79.5480728149414%
Volume Distribution (VD):  1.939
Pgp-substrate:  9.976339340209961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.73
CYP1A2-substrate:  0.965
CYP2C19-inhibitor:  0.415
CYP2C19-substrate:  0.938
CYP2C9-inhibitor:  0.027
CYP2C9-substrate:  0.838
CYP2D6-inhibitor:  0.646
CYP2D6-substrate:  0.937
CYP3A4-inhibitor:  0.754
CYP3A4-substrate:  0.921

ADMET: Excretion

Clearance (CL):  15.227
Half-life (T1/2):  0.235

ADMET: Toxicity

hERG Blockers:  0.432
Human Hepatotoxicity (H-HT):  0.188
Drug-inuced Liver Injury (DILI):  0.577
AMES Toxicity:  0.448
Rat Oral Acute Toxicity:  0.772
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.211
Carcinogencity:  0.704
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.949

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

  Natural Product: NPC302527

Natural Product ID:  NPC302527
Common Name*:   WSVWKHTVFGTTKJ-AWEZNQCLSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  WSVWKHTVFGTTKJ-AWEZNQCLSA-N
Standard InCHI:  InChI=1S/C20H21NO4/c1-21-5-4-11-7-17(22-2)20(23-3)19-13-9-16-15(24-10-25-16)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/p+1/t14-/m0/s1
SMILES:  C[NH+]1CCc2cc(c(c3-c4cc5c(cc4C[C@H]1c23)OCO5)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL179440
PubChem CID:   197001
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
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22737858]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23194502]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. fruit n.a. PMID[24897106]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. rhizome n.a. PMID[25277281]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. tuber n.a. PMID[25670016]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[32058719]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28410 Nandina domestica Species Berberidaceae 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
NPT1788 Individual Protein Alpha-1a adrenergic receptor Homo sapiens Ki = 430.0 nM PMID[493064]
NPT290 Individual Protein Serotonin 2a (5-HT2a) receptor Homo sapiens Ke = 657.0 nM PMID[493065]
NPT1788 Individual Protein Alpha-1a adrenergic receptor Homo sapiens Ke = 196.0 nM PMID[493065]
NPT2 Others Unspecified Ratio Ke = 3.4 n.a. PMID[493065]

☑ 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 NPC302527 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 NPC167546
1.0 High Similarity NPC16805
0.9935 High Similarity NPC476432
0.9935 High Similarity NPC24264
0.987 High Similarity NPC210918
0.987 High Similarity NPC247389
0.9869 High Similarity NPC225774
0.9805 High Similarity NPC219341
0.9682 High Similarity NPC149090
0.9682 High Similarity NPC19520
0.9673 High Similarity NPC232924
0.9673 High Similarity NPC160298
0.9673 High Similarity NPC306902
0.9673 High Similarity NPC266753
0.9673 High Similarity NPC477559
0.9618 High Similarity NPC6152
0.956 High Similarity NPC199465
0.956 High Similarity NPC229166
0.956 High Similarity NPC128560
0.9539 High Similarity NPC325871
0.9539 High Similarity NPC99659
0.9441 High Similarity NPC114364
0.9441 High Similarity NPC320223
0.9416 High Similarity NPC476572
0.9367 High Similarity NPC298979
0.9308 High Similarity NPC241055
0.9304 High Similarity NPC86144
0.9304 High Similarity NPC304659
0.9268 High Similarity NPC248642
0.9268 High Similarity NPC116284
0.9264 High Similarity NPC258695
0.9264 High Similarity NPC470879
0.9264 High Similarity NPC126284
0.9241 High Similarity NPC168409
0.9216 High Similarity NPC326316
0.9216 High Similarity NPC81733
0.9212 High Similarity NPC156576
0.9207 High Similarity NPC477561
0.9207 High Similarity NPC474506
0.9207 High Similarity NPC312918
0.9207 High Similarity NPC155442
0.9207 High Similarity NPC32413
0.9207 High Similarity NPC476574
0.9202 High Similarity NPC23219
0.9177 High Similarity NPC189470
0.9146 High Similarity NPC267408
0.9141 High Similarity NPC112575
0.9119 High Similarity NPC13504
0.9119 High Similarity NPC136508
0.9119 High Similarity NPC96603
0.9119 High Similarity NPC253043
0.9119 High Similarity NPC477563
0.9119 High Similarity NPC78222
0.9119 High Similarity NPC196447
0.9119 High Similarity NPC306843
0.9119 High Similarity NPC212794
0.9096 High Similarity NPC135772
0.9085 High Similarity NPC118633
0.9085 High Similarity NPC294790
0.9085 High Similarity NPC148693
0.908 High Similarity NPC477558
0.9057 High Similarity NPC324144
0.9048 High Similarity NPC237579
0.9038 High Similarity NPC216459
0.9038 High Similarity NPC41178
0.9038 High Similarity NPC138487
0.9038 High Similarity NPC244112
0.902 High Similarity NPC475959
0.9006 High Similarity NPC145832
0.9006 High Similarity NPC474931
0.9006 High Similarity NPC81218
0.9006 High Similarity NPC12053
0.9006 High Similarity NPC158376
0.9006 High Similarity NPC306555
0.9006 High Similarity NPC117188
0.9006 High Similarity NPC205421
0.8994 High Similarity NPC82763
0.8988 High Similarity NPC57036
0.8988 High Similarity NPC214116
0.8981 High Similarity NPC146288
0.8935 High Similarity NPC476576
0.8935 High Similarity NPC312531
0.8935 High Similarity NPC186546
0.891 High Similarity NPC210148
0.891 High Similarity NPC233029
0.8896 High Similarity NPC152212
0.8889 High Similarity NPC204947
0.8868 High Similarity NPC477080
0.8861 High Similarity NPC203784
0.8861 High Similarity NPC170503
0.8861 High Similarity NPC126519
0.8861 High Similarity NPC31311
0.8861 High Similarity NPC234392
0.8841 High Similarity NPC239775
0.8839 High Similarity NPC211296
0.882 High Similarity NPC1229
0.8812 High Similarity NPC27410
0.8812 High Similarity NPC166014
0.881 High Similarity NPC476575
0.8797 High Similarity NPC76079
0.878 High Similarity NPC26240
0.878 High Similarity NPC477562
0.878 High Similarity NPC69712
0.8774 High Similarity NPC130941
0.875 High Similarity NPC179704
0.8718 High Similarity NPC219162
0.8698 High Similarity NPC275132
0.869 High Similarity NPC220961
0.8683 High Similarity NPC287588
0.8679 High Similarity NPC93593
0.8675 High Similarity NPC477020
0.8675 High Similarity NPC2314
0.8675 High Similarity NPC66341
0.8675 High Similarity NPC192135
0.8671 High Similarity NPC117717
0.8667 High Similarity NPC168753
0.8667 High Similarity NPC118274
0.865 High Similarity NPC232514
0.865 High Similarity NPC276944
0.865 High Similarity NPC238530
0.8634 High Similarity NPC111485
0.8613 High Similarity NPC475754
0.859 High Similarity NPC16107
0.859 High Similarity NPC253883
0.859 High Similarity NPC210437
0.859 High Similarity NPC95075
0.859 High Similarity NPC476144
0.859 High Similarity NPC106295
0.859 High Similarity NPC90844
0.859 High Similarity NPC51957
0.8588 High Similarity NPC249405
0.8581 High Similarity NPC145304
0.8571 High Similarity NPC128019
0.8571 High Similarity NPC476567
0.8571 High Similarity NPC136860
0.8562 High Similarity NPC188163
0.8562 High Similarity NPC470925
0.8562 High Similarity NPC328750
0.8562 High Similarity NPC474915
0.8562 High Similarity NPC213206
0.8545 High Similarity NPC474324
0.8545 High Similarity NPC57812
0.8545 High Similarity NPC150879
0.8535 High Similarity NPC7467
0.8528 High Similarity NPC60186
0.8521 High Similarity NPC190461
0.8509 High Similarity NPC323443
0.8509 High Similarity NPC180756
0.8503 High Similarity NPC65403
0.8497 Intermediate Similarity NPC474904
0.8497 Intermediate Similarity NPC314682
0.8494 Intermediate Similarity NPC475845
0.8485 Intermediate Similarity NPC81247
0.8485 Intermediate Similarity NPC35627
0.8485 Intermediate Similarity NPC476573
0.8481 Intermediate Similarity NPC92541
0.848 Intermediate Similarity NPC73492
0.848 Intermediate Similarity NPC233718
0.848 Intermediate Similarity NPC299990
0.8476 Intermediate Similarity NPC320104
0.8471 Intermediate Similarity NPC474507
0.8443 Intermediate Similarity NPC311991
0.8443 Intermediate Similarity NPC474708
0.8443 Intermediate Similarity NPC75958
0.8438 Intermediate Similarity NPC470924
0.8434 Intermediate Similarity NPC181653
0.8434 Intermediate Similarity NPC190332
0.843 Intermediate Similarity NPC302275
0.8421 Intermediate Similarity NPC7018
0.8418 Intermediate Similarity NPC37144
0.8418 Intermediate Similarity NPC59907
0.8402 Intermediate Similarity NPC187678
0.8395 Intermediate Similarity NPC186063
0.8364 Intermediate Similarity NPC233650
0.8354 Intermediate Similarity NPC144863
0.8353 Intermediate Similarity NPC173416
0.8353 Intermediate Similarity NPC476577
0.8353 Intermediate Similarity NPC148709
0.8352 Intermediate Similarity NPC302001
0.8333 Intermediate Similarity NPC47077
0.8333 Intermediate Similarity NPC123323
0.8333 Intermediate Similarity NPC14507
0.8333 Intermediate Similarity NPC78733
0.8323 Intermediate Similarity NPC148898
0.8323 Intermediate Similarity NPC100566
0.8323 Intermediate Similarity NPC26601
0.8313 Intermediate Similarity NPC180306
0.8313 Intermediate Similarity NPC134858
0.8304 Intermediate Similarity NPC477560
0.8294 Intermediate Similarity NPC304675
0.8274 Intermediate Similarity NPC266176
0.8274 Intermediate Similarity NPC290759
0.8274 Intermediate Similarity NPC82533
0.8274 Intermediate Similarity NPC158148
0.8268 Intermediate Similarity NPC193906
0.8268 Intermediate Similarity NPC23080
0.8246 Intermediate Similarity NPC237044
0.8246 Intermediate Similarity NPC241704
0.8239 Intermediate Similarity NPC476151
0.8239 Intermediate Similarity NPC281581

  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 NPC302527 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
0.859 High Similarity NPD4584 Approved
0.8562 High Similarity NPD4664 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD4481 Phase 3
0.8373 Intermediate Similarity NPD3051 Approved
0.828 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD2970 Approved
0.8214 Intermediate Similarity NPD2969 Approved
0.807 Intermediate Similarity NPD8099 Discontinued
0.807 Intermediate Similarity NPD8252 Approved
0.807 Intermediate Similarity NPD8251 Approved
0.8063 Intermediate Similarity NPD2420 Approved
0.8063 Intermediate Similarity NPD2421 Approved
0.8059 Intermediate Similarity NPD2489 Approved
0.8059 Intermediate Similarity NPD27 Approved
0.8023 Intermediate Similarity NPD8156 Discontinued
0.8 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7298 Approved
0.7964 Intermediate Similarity NPD6788 Approved
0.7927 Intermediate Similarity NPD4017 Approved
0.7921 Intermediate Similarity NPD7906 Approved
0.7898 Intermediate Similarity NPD2968 Approved
0.7898 Intermediate Similarity NPD2971 Approved
0.7824 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD3640 Phase 3
0.7805 Intermediate Similarity NPD3639 Approved
0.7805 Intermediate Similarity NPD3641 Approved
0.7797 Intermediate Similarity NPD4578 Approved
0.7797 Intermediate Similarity NPD4577 Approved
0.7797 Intermediate Similarity NPD7313 Approved
0.7797 Intermediate Similarity NPD7312 Approved
0.7797 Intermediate Similarity NPD7310 Approved
0.7797 Intermediate Similarity NPD7311 Approved
0.7772 Intermediate Similarity NPD4420 Approved
0.7765 Intermediate Similarity NPD4663 Approved
0.7756 Intermediate Similarity NPD3109 Approved
0.7756 Intermediate Similarity NPD3110 Approved
0.7753 Intermediate Similarity NPD8054 Approved
0.7753 Intermediate Similarity NPD8053 Approved
0.7753 Intermediate Similarity NPD7309 Approved
0.7738 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD5241 Discontinued
0.7697 Intermediate Similarity NPD6031 Approved
0.7697 Intermediate Similarity NPD6030 Approved
0.7697 Intermediate Similarity NPD4727 Phase 1
0.7677 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD2898 Approved
0.763 Intermediate Similarity NPD6071 Discontinued
0.7619 Intermediate Similarity NPD4772 Phase 2
0.7619 Intermediate Similarity NPD4773 Phase 2
0.7606 Intermediate Similarity NPD5005 Approved
0.7606 Intermediate Similarity NPD5006 Approved
0.7602 Intermediate Similarity NPD7831 Phase 2
0.7602 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7833 Phase 2
0.7588 Intermediate Similarity NPD2560 Approved
0.7588 Intermediate Similarity NPD2563 Approved
0.7546 Intermediate Similarity NPD5754 Discontinued
0.7541 Intermediate Similarity NPD2488 Approved
0.7541 Intermediate Similarity NPD2490 Approved
0.7529 Intermediate Similarity NPD4010 Discontinued
0.7527 Intermediate Similarity NPD2973 Approved
0.7527 Intermediate Similarity NPD2974 Approved
0.7527 Intermediate Similarity NPD2975 Approved
0.7516 Intermediate Similarity NPD5718 Phase 2
0.75 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6107 Approved
0.7471 Intermediate Similarity NPD7802 Discontinued
0.7468 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD4166 Phase 2
0.7427 Intermediate Similarity NPD2978 Approved
0.7427 Intermediate Similarity NPD2977 Approved
0.7418 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4580 Approved
0.7399 Intermediate Similarity NPD5604 Discontinued
0.7399 Intermediate Similarity NPD4055 Discovery
0.7394 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD5976 Discontinued
0.7368 Intermediate Similarity NPD2494 Approved
0.7368 Intermediate Similarity NPD2493 Approved
0.7368 Intermediate Similarity NPD3452 Approved
0.7368 Intermediate Similarity NPD3450 Approved
0.7365 Intermediate Similarity NPD1424 Approved
0.7358 Intermediate Similarity NPD4474 Approved
0.7358 Intermediate Similarity NPD4475 Approved
0.7356 Intermediate Similarity NPD7400 Phase 3
0.7349 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD3845 Phase 1
0.7348 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4859 Phase 1
0.7316 Intermediate Similarity NPD4107 Approved
0.7308 Intermediate Similarity NPD7280 Phase 3
0.7308 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7281 Phase 3
0.7305 Intermediate Similarity NPD3124 Discontinued
0.7303 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD3763 Approved
0.7284 Intermediate Similarity NPD6896 Approved
0.7284 Intermediate Similarity NPD6895 Approved
0.7278 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD8095 Phase 1
0.7254 Intermediate Similarity NPD4583 Approved
0.7254 Intermediate Similarity NPD4582 Approved
0.7246 Intermediate Similarity NPD7124 Phase 2
0.7238 Intermediate Similarity NPD6297 Approved
0.7222 Intermediate Similarity NPD2492 Phase 1
0.7222 Intermediate Similarity NPD5312 Approved
0.7222 Intermediate Similarity NPD5313 Approved
0.7202 Intermediate Similarity NPD4004 Approved
0.7202 Intermediate Similarity NPD7598 Phase 2
0.7202 Intermediate Similarity NPD4002 Approved
0.7191 Intermediate Similarity NPD6688 Approved
0.7191 Intermediate Similarity NPD6687 Approved
0.7188 Intermediate Similarity NPD4482 Phase 3
0.7184 Intermediate Similarity NPD5977 Approved
0.7184 Intermediate Similarity NPD5978 Approved
0.7172 Intermediate Similarity NPD7827 Phase 1
0.7169 Intermediate Similarity NPD4236 Phase 3
0.7169 Intermediate Similarity NPD4237 Approved
0.7161 Intermediate Similarity NPD3705 Approved
0.716 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD4108 Discontinued
0.7126 Intermediate Similarity NPD6748 Discontinued
0.7119 Intermediate Similarity NPD6037 Discontinued
0.7119 Intermediate Similarity NPD5677 Discontinued
0.7105 Intermediate Similarity NPD5582 Discontinued
0.7093 Intermediate Similarity NPD4005 Discontinued
0.7085 Intermediate Similarity NPD3815 Phase 1
0.7085 Intermediate Similarity NPD3816 Phase 1
0.7081 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6851 Approved
0.7081 Intermediate Similarity NPD6853 Approved
0.7069 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD5177 Phase 3
0.7065 Intermediate Similarity NPD7047 Phase 3
0.7062 Intermediate Similarity NPD3057 Approved
0.7059 Intermediate Similarity NPD3349 Phase 2
0.7035 Intermediate Similarity NPD4210 Discontinued
0.7029 Intermediate Similarity NPD4585 Approved
0.7024 Intermediate Similarity NPD6997 Phase 2
0.7021 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5156 Approved
0.7019 Intermediate Similarity NPD5155 Approved
0.7018 Intermediate Similarity NPD6090 Discontinued
0.7012 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7110 Phase 1
0.6995 Remote Similarity NPD3885 Approved
0.6994 Remote Similarity NPD6523 Clinical (unspecified phase)
0.699 Remote Similarity NPD4040 Phase 1
0.6977 Remote Similarity NPD1914 Approved
0.6974 Remote Similarity NPD2972 Approved
0.6974 Remote Similarity NPD3533 Approved
0.6971 Remote Similarity NPD3384 Approved
0.6971 Remote Similarity NPD3382 Approved
0.6971 Remote Similarity NPD3383 Approved
0.6968 Remote Similarity NPD7291 Discontinued
0.6964 Remote Similarity NPD3060 Approved
0.6964 Remote Similarity NPD6674 Discontinued
0.6959 Remote Similarity NPD5457 Discontinued
0.6957 Remote Similarity NPD2605 Approved
0.6957 Remote Similarity NPD2606 Approved
0.6957 Remote Similarity NPD3594 Approved
0.6957 Remote Similarity NPD3595 Approved
0.6946 Remote Similarity NPD4725 Approved
0.6946 Remote Similarity NPD1375 Discontinued
0.6946 Remote Similarity NPD4726 Approved
0.6946 Remote Similarity NPD4721 Approved
0.6944 Remote Similarity NPD6747 Phase 1
0.6941 Remote Similarity NPD6667 Approved
0.6941 Remote Similarity NPD6666 Approved
0.694 Remote Similarity NPD42 Phase 2
0.694 Remote Similarity NPD6042 Phase 2
0.6937 Remote Similarity NPD7247 Discontinued
0.6932 Remote Similarity NPD5772 Approved
0.6932 Remote Similarity NPD5773 Approved
0.6931 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1753 Discontinued
0.6923 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6386 Approved
0.6914 Remote Similarity NPD6385 Approved
0.691 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6907 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6894 Remote Similarity NPD3636 Approved
0.6894 Remote Similarity NPD3635 Approved
0.6894 Remote Similarity NPD3637 Approved
0.6888 Remote Similarity NPD2491 Approved
0.6888 Remote Similarity NPD3448 Approved
0.6886 Remote Similarity NPD1632 Clinical (unspecified phase)

  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