Structure

Physi-Chem Properties

Molecular Weight:  341.16
Volume:  356.509
LogP:  3.84
LogD:  3.313
LogS:  -4.36
# Rotatable Bonds:  5
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.765
Synthetic Accessibility Score:  2.745
Fsp3:  0.3
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:  -4.809
MDCK Permeability:  2.0637800844269805e-05
Pgp-inhibitor:  0.305
Pgp-substrate:  0.927
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.097

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.992
Plasma Protein Binding (PPB):  93.5040054321289%
Volume Distribution (VD):  2.314
Pgp-substrate:  6.625446796417236%

ADMET: Metabolism

CYP1A2-inhibitor:  0.865
CYP1A2-substrate:  0.955
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.946
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.713
CYP2D6-inhibitor:  0.109
CYP2D6-substrate:  0.957
CYP3A4-inhibitor:  0.015
CYP3A4-substrate:  0.894

ADMET: Excretion

Clearance (CL):  10.187
Half-life (T1/2):  0.597

ADMET: Toxicity

hERG Blockers:  0.294
Human Hepatotoxicity (H-HT):  0.486
Drug-inuced Liver Injury (DILI):  0.864
AMES Toxicity:  0.341
Rat Oral Acute Toxicity:  0.981
Maximum Recommended Daily Dose:  0.447
Skin Sensitization:  0.949
Carcinogencity:  0.224
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.921

Download Data

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

  Natural Product: NPC475557

Natural Product ID:  NPC475557
Common Name*:   Secocularidine
IUPAC Name:   7-[2-(dimethylamino)ethyl]-2,3-dimethoxybenzo[b][1]benzoxepin-10-ol
Synonyms:   Secocularidine
Standard InCHIKey:  DBGGUODEECPLSS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H23NO4/c1-21(2)10-9-13-6-8-16(22)20-15(13)7-5-14-11-18(23-3)19(24-4)12-17(14)25-20/h5-8,11-12,22H,9-10H2,1-4H3
SMILES:  COc1cc2C=Cc3c(Oc2cc1OC)c(O)ccc3CCN(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508081
PubChem CID:   44559879
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001910] Benzoxepines
        • [CHEMONTID:0001988] Dibenzoxepines

*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
NPO33048 sarcuapnos crassfolia Species n.a. n.a. 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 = 13400.0 nM PMID[494255]
NPT2 Others Unspecified Ratio IC50 = 3.8 n.a. PMID[494255]
NPT2 Others Unspecified Ratio IC50 = 0.7 n.a. PMID[494255]

☑ 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 NPC475557 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
0.9514 High Similarity NPC473934
0.8994 High Similarity NPC232386
0.8994 High Similarity NPC190783
0.8994 High Similarity NPC152680
0.8805 High Similarity NPC204908
0.8805 High Similarity NPC83198
0.8542 High Similarity NPC214860
0.8503 High Similarity NPC472337
0.8497 Intermediate Similarity NPC178129
0.8493 Intermediate Similarity NPC37196
0.8493 Intermediate Similarity NPC94236
0.8472 Intermediate Similarity NPC10225
0.8472 Intermediate Similarity NPC45824
0.8472 Intermediate Similarity NPC58164
0.8456 Intermediate Similarity NPC245207
0.8456 Intermediate Similarity NPC319647
0.8456 Intermediate Similarity NPC25966
0.8456 Intermediate Similarity NPC127218
0.8447 Intermediate Similarity NPC264850
0.8447 Intermediate Similarity NPC13916
0.8446 Intermediate Similarity NPC472336
0.8446 Intermediate Similarity NPC472334
0.8425 Intermediate Similarity NPC161203
0.8425 Intermediate Similarity NPC6451
0.8421 Intermediate Similarity NPC50250
0.8414 Intermediate Similarity NPC126836
0.8414 Intermediate Similarity NPC311680
0.8414 Intermediate Similarity NPC299221
0.8414 Intermediate Similarity NPC51840
0.8414 Intermediate Similarity NPC234488
0.8402 Intermediate Similarity NPC116465
0.8402 Intermediate Similarity NPC212237
0.84 Intermediate Similarity NPC254759
0.84 Intermediate Similarity NPC160283
0.8389 Intermediate Similarity NPC276490
0.8389 Intermediate Similarity NPC326797
0.8389 Intermediate Similarity NPC102904
0.8389 Intermediate Similarity NPC103976
0.8389 Intermediate Similarity NPC474282
0.8389 Intermediate Similarity NPC107551
0.8389 Intermediate Similarity NPC296898
0.8389 Intermediate Similarity NPC176051
0.8385 Intermediate Similarity NPC24465
0.8378 Intermediate Similarity NPC201357
0.8378 Intermediate Similarity NPC281521
0.8378 Intermediate Similarity NPC255147
0.8367 Intermediate Similarity NPC32778
0.8367 Intermediate Similarity NPC168059
0.8367 Intermediate Similarity NPC229442
0.8365 Intermediate Similarity NPC329837
0.8356 Intermediate Similarity NPC232275
0.8356 Intermediate Similarity NPC12275
0.8356 Intermediate Similarity NPC474356
0.8356 Intermediate Similarity NPC45715
0.8355 Intermediate Similarity NPC6568
0.8344 Intermediate Similarity NPC471389
0.8333 Intermediate Similarity NPC29868
0.8333 Intermediate Similarity NPC212942
0.8333 Intermediate Similarity NPC216836
0.8333 Intermediate Similarity NPC210355
0.8333 Intermediate Similarity NPC292882
0.8333 Intermediate Similarity NPC79622
0.8322 Intermediate Similarity NPC265433
0.8322 Intermediate Similarity NPC234952
0.8322 Intermediate Similarity NPC162659
0.8322 Intermediate Similarity NPC173660
0.8322 Intermediate Similarity NPC248727
0.8322 Intermediate Similarity NPC270456
0.8312 Intermediate Similarity NPC112251
0.8311 Intermediate Similarity NPC310854
0.8311 Intermediate Similarity NPC106215
0.8299 Intermediate Similarity NPC127624
0.8299 Intermediate Similarity NPC202762
0.8299 Intermediate Similarity NPC86655
0.8289 Intermediate Similarity NPC107161
0.8288 Intermediate Similarity NPC224157
0.8288 Intermediate Similarity NPC229231
0.8288 Intermediate Similarity NPC192687
0.8278 Intermediate Similarity NPC259519
0.8276 Intermediate Similarity NPC266691
0.8274 Intermediate Similarity NPC286119
0.8264 Intermediate Similarity NPC78974
0.8264 Intermediate Similarity NPC223136
0.8264 Intermediate Similarity NPC28730
0.8264 Intermediate Similarity NPC103823
0.8264 Intermediate Similarity NPC18924
0.8264 Intermediate Similarity NPC44748
0.8264 Intermediate Similarity NPC214406
0.8255 Intermediate Similarity NPC112246
0.8255 Intermediate Similarity NPC121812
0.8255 Intermediate Similarity NPC134968
0.8255 Intermediate Similarity NPC470356
0.8255 Intermediate Similarity NPC112939
0.8255 Intermediate Similarity NPC195022
0.8255 Intermediate Similarity NPC94750
0.8255 Intermediate Similarity NPC474206
0.8243 Intermediate Similarity NPC475840
0.8243 Intermediate Similarity NPC269528
0.8235 Intermediate Similarity NPC477616
0.8231 Intermediate Similarity NPC472597
0.8225 Intermediate Similarity NPC42663
0.8225 Intermediate Similarity NPC271013
0.8225 Intermediate Similarity NPC217748
0.8225 Intermediate Similarity NPC49075
0.8225 Intermediate Similarity NPC279228
0.8225 Intermediate Similarity NPC104196
0.8225 Intermediate Similarity NPC8836
0.8225 Intermediate Similarity NPC90998
0.8225 Intermediate Similarity NPC7715
0.8225 Intermediate Similarity NPC328155
0.8225 Intermediate Similarity NPC15414
0.8225 Intermediate Similarity NPC251735
0.8225 Intermediate Similarity NPC182052
0.8225 Intermediate Similarity NPC229373
0.8225 Intermediate Similarity NPC239824
0.8225 Intermediate Similarity NPC290582
0.8225 Intermediate Similarity NPC185639
0.8225 Intermediate Similarity NPC290005
0.8225 Intermediate Similarity NPC181796
0.8225 Intermediate Similarity NPC258657
0.8225 Intermediate Similarity NPC54654
0.8225 Intermediate Similarity NPC285931
0.8225 Intermediate Similarity NPC223690
0.8225 Intermediate Similarity NPC222661
0.8225 Intermediate Similarity NPC311973
0.8225 Intermediate Similarity NPC30779
0.8224 Intermediate Similarity NPC247291
0.8224 Intermediate Similarity NPC311530
0.8219 Intermediate Similarity NPC190144
0.8217 Intermediate Similarity NPC127402
0.8212 Intermediate Similarity NPC471388
0.8212 Intermediate Similarity NPC70682
0.8212 Intermediate Similarity NPC260741
0.8212 Intermediate Similarity NPC32630
0.8207 Intermediate Similarity NPC324112
0.8207 Intermediate Similarity NPC169474
0.8207 Intermediate Similarity NPC159968
0.8207 Intermediate Similarity NPC246620
0.8207 Intermediate Similarity NPC293054
0.8207 Intermediate Similarity NPC236791
0.8207 Intermediate Similarity NPC124452
0.8207 Intermediate Similarity NPC282000
0.8207 Intermediate Similarity NPC74817
0.8207 Intermediate Similarity NPC82679
0.82 Intermediate Similarity NPC230734
0.82 Intermediate Similarity NPC306441
0.82 Intermediate Similarity NPC16435
0.82 Intermediate Similarity NPC205442
0.82 Intermediate Similarity NPC202846
0.82 Intermediate Similarity NPC227503
0.82 Intermediate Similarity NPC474639
0.82 Intermediate Similarity NPC143139
0.8199 Intermediate Similarity NPC18402
0.8194 Intermediate Similarity NPC60885
0.8194 Intermediate Similarity NPC299584
0.8194 Intermediate Similarity NPC234400
0.8194 Intermediate Similarity NPC82483
0.8194 Intermediate Similarity NPC265483
0.8188 Intermediate Similarity NPC555
0.8188 Intermediate Similarity NPC206737
0.8188 Intermediate Similarity NPC56764
0.8188 Intermediate Similarity NPC469659
0.8188 Intermediate Similarity NPC188378
0.8188 Intermediate Similarity NPC289258
0.8188 Intermediate Similarity NPC276026
0.8188 Intermediate Similarity NPC317380
0.8188 Intermediate Similarity NPC7515
0.8187 Intermediate Similarity NPC129603
0.8182 Intermediate Similarity NPC93323
0.8182 Intermediate Similarity NPC45257
0.8182 Intermediate Similarity NPC469795
0.8182 Intermediate Similarity NPC473108
0.8182 Intermediate Similarity NPC12641
0.8182 Intermediate Similarity NPC280092
0.8176 Intermediate Similarity NPC254441
0.8176 Intermediate Similarity NPC167116
0.8176 Intermediate Similarity NPC7903
0.8176 Intermediate Similarity NPC35932
0.8176 Intermediate Similarity NPC184447
0.8176 Intermediate Similarity NPC16208
0.8176 Intermediate Similarity NPC160991
0.8176 Intermediate Similarity NPC274716
0.817 Intermediate Similarity NPC175838
0.817 Intermediate Similarity NPC472332
0.817 Intermediate Similarity NPC472335
0.8163 Intermediate Similarity NPC220935
0.8163 Intermediate Similarity NPC472338
0.8163 Intermediate Similarity NPC91291
0.8158 Intermediate Similarity NPC109240
0.8158 Intermediate Similarity NPC27495
0.8158 Intermediate Similarity NPC184797
0.8158 Intermediate Similarity NPC309124
0.8153 Intermediate Similarity NPC476969
0.8151 Intermediate Similarity NPC154866
0.8151 Intermediate Similarity NPC63179
0.8146 Intermediate Similarity NPC272157
0.8146 Intermediate Similarity NPC25111
0.8146 Intermediate Similarity NPC73535
0.8146 Intermediate Similarity NPC6262
0.8146 Intermediate Similarity NPC90615

  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 NPC475557 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
0.8225 Intermediate Similarity NPD8054 Approved
0.8225 Intermediate Similarity NPD8053 Approved
0.8165 Intermediate Similarity NPD4678 Approved
0.8165 Intermediate Similarity NPD4675 Approved
0.8075 Intermediate Similarity NPD2560 Approved
0.8075 Intermediate Similarity NPD2563 Approved
0.8065 Intermediate Similarity NPD7124 Phase 2
0.8027 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8027 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD3027 Phase 3
0.7959 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD1613 Approved
0.7933 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD7906 Approved
0.7871 Intermediate Similarity NPD3060 Approved
0.7848 Intermediate Similarity NPD4123 Phase 3
0.7843 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD4663 Approved
0.7815 Intermediate Similarity NPD2238 Phase 2
0.7811 Intermediate Similarity NPD8251 Approved
0.7811 Intermediate Similarity NPD8252 Approved
0.7811 Intermediate Similarity NPD8099 Discontinued
0.7798 Intermediate Similarity NPD2489 Approved
0.7798 Intermediate Similarity NPD27 Approved
0.7791 Intermediate Similarity NPD7549 Discontinued
0.7784 Intermediate Similarity NPD6071 Discontinued
0.7771 Intermediate Similarity NPD5241 Discontinued
0.7765 Intermediate Similarity NPD8156 Discontinued
0.7764 Intermediate Similarity NPD4005 Discontinued
0.7758 Intermediate Similarity NPD4055 Discovery
0.7756 Intermediate Similarity NPD4162 Approved
0.7746 Intermediate Similarity NPD7311 Approved
0.7746 Intermediate Similarity NPD7313 Approved
0.7746 Intermediate Similarity NPD4578 Approved
0.7746 Intermediate Similarity NPD4577 Approved
0.7746 Intermediate Similarity NPD7312 Approved
0.7746 Intermediate Similarity NPD7310 Approved
0.7742 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD2969 Approved
0.7738 Intermediate Similarity NPD2970 Approved
0.7736 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD7447 Phase 1
0.7701 Intermediate Similarity NPD7309 Approved
0.7679 Intermediate Similarity NPD3051 Approved
0.7673 Intermediate Similarity NPD7213 Phase 3
0.7673 Intermediate Similarity NPD7212 Phase 2
0.7665 Intermediate Similarity NPD5677 Discontinued
0.7658 Intermediate Similarity NPD2677 Approved
0.7643 Intermediate Similarity NPD5177 Phase 3
0.76 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD3687 Approved
0.7593 Intermediate Similarity NPD3686 Approved
0.758 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD2801 Approved
0.7576 Intermediate Similarity NPD2978 Approved
0.7576 Intermediate Similarity NPD2977 Approved
0.7566 Intermediate Similarity NPD5718 Phase 2
0.7561 Intermediate Similarity NPD6072 Discontinued
0.7548 Intermediate Similarity NPD6111 Discontinued
0.7548 Intermediate Similarity NPD6895 Approved
0.7548 Intermediate Similarity NPD6896 Approved
0.7546 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7833 Phase 2
0.7545 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7831 Phase 2
0.7532 Intermediate Similarity NPD4236 Phase 3
0.7532 Intermediate Similarity NPD4237 Approved
0.7516 Intermediate Similarity NPD2674 Phase 3
0.7516 Intermediate Similarity NPD1424 Approved
0.7516 Intermediate Similarity NPD4584 Approved
0.7516 Intermediate Similarity NPD1375 Discontinued
0.75 Intermediate Similarity NPD2232 Approved
0.75 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2230 Approved
0.75 Intermediate Similarity NPD2233 Approved
0.7485 Intermediate Similarity NPD6788 Approved
0.747 Intermediate Similarity NPD4585 Approved
0.747 Intermediate Similarity NPD5773 Approved
0.747 Intermediate Similarity NPD5772 Approved
0.7469 Intermediate Similarity NPD6090 Discontinued
0.7469 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD5090 Approved
0.7455 Intermediate Similarity NPD5089 Approved
0.7438 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4908 Phase 1
0.7423 Intermediate Similarity NPD6030 Approved
0.7423 Intermediate Similarity NPD6031 Approved
0.7391 Intermediate Similarity NPD6667 Approved
0.7391 Intermediate Similarity NPD6666 Approved
0.7386 Intermediate Similarity NPD4625 Phase 3
0.7375 Intermediate Similarity NPD6331 Phase 2
0.7375 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3018 Phase 2
0.7365 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD3062 Approved
0.7355 Intermediate Similarity NPD3059 Approved
0.7355 Intermediate Similarity NPD1558 Phase 1
0.7355 Intermediate Similarity NPD3061 Approved
0.7353 Intermediate Similarity NPD4666 Phase 3
0.7351 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD3444 Approved
0.7347 Intermediate Similarity NPD3443 Approved
0.7347 Intermediate Similarity NPD3445 Approved
0.7338 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD3144 Approved
0.7338 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD3145 Approved
0.7329 Intermediate Similarity NPD2219 Phase 1
0.7329 Intermediate Similarity NPD3692 Discontinued
0.7317 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD1610 Phase 2
0.7312 Intermediate Similarity NPD2494 Approved
0.7312 Intermediate Similarity NPD2493 Approved
0.7305 Intermediate Similarity NPD1934 Approved
0.7305 Intermediate Similarity NPD3383 Approved
0.7305 Intermediate Similarity NPD3382 Approved
0.7305 Intermediate Similarity NPD3384 Approved
0.7303 Intermediate Similarity NPD6584 Phase 3
0.7301 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD2668 Approved
0.7297 Intermediate Similarity NPD2667 Approved
0.7294 Intermediate Similarity NPD5709 Phase 3
0.7283 Intermediate Similarity NPD4481 Phase 3
0.7279 Intermediate Similarity NPD1548 Phase 1
0.7278 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1653 Approved
0.7273 Intermediate Similarity NPD4210 Discontinued
0.7267 Intermediate Similarity NPD7466 Approved
0.7267 Intermediate Similarity NPD4010 Discontinued
0.7261 Intermediate Similarity NPD2653 Approved
0.7261 Intermediate Similarity NPD2568 Approved
0.7261 Intermediate Similarity NPD5314 Approved
0.7256 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD2861 Phase 2
0.7246 Intermediate Similarity NPD4773 Phase 2
0.7246 Intermediate Similarity NPD4772 Phase 2
0.7237 Intermediate Similarity NPD3053 Approved
0.7237 Intermediate Similarity NPD3055 Approved
0.7237 Intermediate Similarity NPD4098 Discontinued
0.7233 Intermediate Similarity NPD2161 Phase 2
0.7219 Intermediate Similarity NPD3450 Approved
0.7219 Intermediate Similarity NPD2983 Phase 2
0.7219 Intermediate Similarity NPD2982 Phase 2
0.7219 Intermediate Similarity NPD3452 Approved
0.7215 Intermediate Similarity NPD2200 Suspended
0.7212 Intermediate Similarity NPD2122 Discontinued
0.7198 Intermediate Similarity NPD2490 Approved
0.7198 Intermediate Similarity NPD2488 Approved
0.7196 Intermediate Similarity NPD4583 Approved
0.7196 Intermediate Similarity NPD4582 Approved
0.7184 Intermediate Similarity NPD2898 Approved
0.7182 Intermediate Similarity NPD6842 Approved
0.7182 Intermediate Similarity NPD6843 Phase 3
0.7182 Intermediate Similarity NPD6841 Approved
0.7179 Intermediate Similarity NPD4475 Approved
0.7179 Intermediate Similarity NPD4474 Approved
0.7176 Intermediate Similarity NPD3882 Suspended
0.7171 Intermediate Similarity NPD5311 Approved
0.7171 Intermediate Similarity NPD5310 Approved
0.717 Intermediate Similarity NPD2156 Approved
0.717 Intermediate Similarity NPD2154 Approved
0.717 Intermediate Similarity NPD1753 Discontinued
0.717 Intermediate Similarity NPD2155 Approved
0.716 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD42 Phase 2
0.7159 Intermediate Similarity NPD6042 Phase 2
0.7153 Intermediate Similarity NPD228 Approved
0.7152 Intermediate Similarity NPD3054 Approved
0.7152 Intermediate Similarity NPD3052 Approved
0.7152 Intermediate Similarity NPD2981 Phase 2
0.7152 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD3365 Discontinued
0.7143 Intermediate Similarity NPD4002 Approved
0.7143 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7110 Phase 1
0.7143 Intermediate Similarity NPD4004 Approved
0.7143 Intermediate Similarity NPD7037 Approved
0.7143 Intermediate Similarity NPD3489 Phase 3
0.7134 Intermediate Similarity NPD4060 Phase 1
0.7134 Intermediate Similarity NPD4357 Discontinued
0.7134 Intermediate Similarity NPD1511 Approved
0.7134 Intermediate Similarity NPD1774 Approved
0.7133 Intermediate Similarity NPD3294 Phase 2
0.7126 Intermediate Similarity NPD5242 Approved
0.7125 Intermediate Similarity NPD4476 Approved
0.7125 Intermediate Similarity NPD6032 Approved
0.7125 Intermediate Similarity NPD4477 Approved
0.7115 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD5976 Discontinued
0.7105 Intermediate Similarity NPD6582 Phase 2
0.7105 Intermediate Similarity NPD4749 Approved
0.7105 Intermediate Similarity NPD1669 Approved
0.7105 Intermediate Similarity NPD6583 Phase 3
0.7097 Intermediate Similarity NPD2973 Approved
0.7097 Intermediate Similarity NPD2974 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