Structure

Physi-Chem Properties

Molecular Weight:  310.2
Volume:  331.932
LogP:  3.973
LogD:  3.329
LogS:  -2.339
# Rotatable Bonds:  2
TPSA:  17.4
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.824
Synthetic Accessibility Score:  3.927
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.715
MDCK Permeability:  1.554764821776189e-05
Pgp-inhibitor:  0.067
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.186
30% Bioavailability (F30%):  0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.986
Plasma Protein Binding (PPB):  85.6679916381836%
Volume Distribution (VD):  3.036
Pgp-substrate:  8.893941879272461%

ADMET: Metabolism

CYP1A2-inhibitor:  0.119
CYP1A2-substrate:  0.919
CYP2C19-inhibitor:  0.064
CYP2C19-substrate:  0.944
CYP2C9-inhibitor:  0.023
CYP2C9-substrate:  0.1
CYP2D6-inhibitor:  0.969
CYP2D6-substrate:  0.874
CYP3A4-inhibitor:  0.598
CYP3A4-substrate:  0.902

ADMET: Excretion

Clearance (CL):  12.744
Half-life (T1/2):  0.072

ADMET: Toxicity

hERG Blockers:  0.65
Human Hepatotoxicity (H-HT):  0.672
Drug-inuced Liver Injury (DILI):  0.305
AMES Toxicity:  0.388
Rat Oral Acute Toxicity:  0.392
Maximum Recommended Daily Dose:  0.975
Skin Sensitization:  0.168
Carcinogencity:  0.716
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.819

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

  Natural Product: NPC81229

Natural Product ID:  NPC81229
Common Name*:   BVWWUWXMEWKEMC-SXLOBPIMSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BVWWUWXMEWKEMC-SXLOBPIMSA-N
Standard InCHI:  InChI=1S/C20H26N2O/c1-3-20-10-6-11-21-12-9-15-14-7-4-5-8-16(14)22(17(13-20)23-2)18(15)19(20)21/h4-5,7-8,17,19H,3,6,9-13H2,1-2H3/t17-,19+,20-/m0/s1
SMILES:  CC[C@]12CCCN3CCc4c5ccccc5n([C@H](C1)OC)c4[C@H]23
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1164562
PubChem CID:   46906969
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002671] Eburnan-type alkaloids

*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
NPO3298 Melodinus tenuicaudatus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[20462230]
NPO17129 Melodinus hemsleyanus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[32683864]
NPO17129 Melodinus hemsleyanus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3298 Melodinus tenuicaudatus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17129 Melodinus hemsleyanus Species Apocynaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 15900.0 nM PMID[554358]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 22100.0 nM PMID[554358]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 29300.0 nM PMID[554358]
NPT660 Cell Line SW480 Homo sapiens IC50 = 32200.0 nM PMID[554358]
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[554358]
NPT26252 TISSUE Aortic artery Rattus norvegicus EC50 > 10000.0 nM PMID[554359]

☑ 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 NPC81229 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 NPC255229
0.9125 High Similarity NPC133261
0.8882 High Similarity NPC472122
0.8882 High Similarity NPC24594
0.8854 High Similarity NPC469541
0.8834 High Similarity NPC187827
0.8834 High Similarity NPC472105
0.8758 High Similarity NPC472123
0.8733 High Similarity NPC20144
0.8727 High Similarity NPC472104
0.8614 High Similarity NPC472110
0.8614 High Similarity NPC143533
0.8614 High Similarity NPC472109
0.8598 High Similarity NPC326575
0.8571 High Similarity NPC317430
0.8533 High Similarity NPC104483
0.8512 High Similarity NPC472107
0.8512 High Similarity NPC79062
0.8452 Intermediate Similarity NPC258480
0.8452 Intermediate Similarity NPC472119
0.8438 Intermediate Similarity NPC194881
0.8393 Intermediate Similarity NPC472108
0.8393 Intermediate Similarity NPC139291
0.8383 Intermediate Similarity NPC15840
0.8365 Intermediate Similarity NPC129721
0.8353 Intermediate Similarity NPC66210
0.8333 Intermediate Similarity NPC57994
0.8333 Intermediate Similarity NPC289299
0.8266 Intermediate Similarity NPC472097
0.8263 Intermediate Similarity NPC234987
0.8246 Intermediate Similarity NPC478077
0.8208 Intermediate Similarity NPC469501
0.8208 Intermediate Similarity NPC469470
0.8204 Intermediate Similarity NPC121903
0.8133 Intermediate Similarity NPC158129
0.8095 Intermediate Similarity NPC134586
0.8092 Intermediate Similarity NPC472323
0.809 Intermediate Similarity NPC52557
0.8079 Intermediate Similarity NPC245916
0.8079 Intermediate Similarity NPC472116
0.8052 Intermediate Similarity NPC88097
0.805 Intermediate Similarity NPC40070
0.8047 Intermediate Similarity NPC211997
0.8012 Intermediate Similarity NPC113626
0.8 Intermediate Similarity NPC472112
0.7963 Intermediate Similarity NPC285469
0.7943 Intermediate Similarity NPC63199
0.7943 Intermediate Similarity NPC111602
0.7943 Intermediate Similarity NPC102338
0.7943 Intermediate Similarity NPC175474
0.7943 Intermediate Similarity NPC196251
0.7929 Intermediate Similarity NPC329688
0.7929 Intermediate Similarity NPC189812
0.7919 Intermediate Similarity NPC472294
0.791 Intermediate Similarity NPC472113
0.7882 Intermediate Similarity NPC150048
0.7882 Intermediate Similarity NPC203754
0.7866 Intermediate Similarity NPC221786
0.7866 Intermediate Similarity NPC474880
0.7861 Intermediate Similarity NPC19679
0.7818 Intermediate Similarity NPC229173
0.7802 Intermediate Similarity NPC249040
0.7799 Intermediate Similarity NPC469525
0.7792 Intermediate Similarity NPC198988
0.7791 Intermediate Similarity NPC207726
0.7791 Intermediate Similarity NPC476219
0.7784 Intermediate Similarity NPC472111
0.7771 Intermediate Similarity NPC2949
0.7771 Intermediate Similarity NPC16667
0.7759 Intermediate Similarity NPC159125
0.7742 Intermediate Similarity NPC325252
0.7725 Intermediate Similarity NPC21174
0.7725 Intermediate Similarity NPC271797
0.7702 Intermediate Similarity NPC21605
0.7688 Intermediate Similarity NPC248462
0.7688 Intermediate Similarity NPC470440
0.7679 Intermediate Similarity NPC2165
0.7679 Intermediate Similarity NPC195507
0.7679 Intermediate Similarity NPC470508
0.7651 Intermediate Similarity NPC67056
0.7651 Intermediate Similarity NPC475990
0.7644 Intermediate Similarity NPC469896
0.7619 Intermediate Similarity NPC126066
0.7619 Intermediate Similarity NPC478182
0.761 Intermediate Similarity NPC63157
0.761 Intermediate Similarity NPC473868
0.7609 Intermediate Similarity NPC294909
0.7609 Intermediate Similarity NPC49196
0.7609 Intermediate Similarity NPC79129
0.7609 Intermediate Similarity NPC195461
0.7609 Intermediate Similarity NPC313985
0.7609 Intermediate Similarity NPC128265
0.7609 Intermediate Similarity NPC254240
0.7609 Intermediate Similarity NPC81654
0.7609 Intermediate Similarity NPC249150
0.7609 Intermediate Similarity NPC312870
0.7609 Intermediate Similarity NPC199851
0.7607 Intermediate Similarity NPC33421
0.7606 Intermediate Similarity NPC87755
0.758 Intermediate Similarity NPC314102
0.758 Intermediate Similarity NPC251722
0.758 Intermediate Similarity NPC150259
0.7571 Intermediate Similarity NPC62510
0.7547 Intermediate Similarity NPC59084
0.7545 Intermediate Similarity NPC230869
0.7544 Intermediate Similarity NPC280548
0.7544 Intermediate Similarity NPC474897
0.7531 Intermediate Similarity NPC478186
0.753 Intermediate Similarity NPC469785
0.7529 Intermediate Similarity NPC49954
0.7529 Intermediate Similarity NPC474561
0.7527 Intermediate Similarity NPC220151
0.7527 Intermediate Similarity NPC19692
0.7526 Intermediate Similarity NPC475422
0.7515 Intermediate Similarity NPC469763
0.7515 Intermediate Similarity NPC73952
0.7515 Intermediate Similarity NPC78375
0.7515 Intermediate Similarity NPC469786
0.7515 Intermediate Similarity NPC259644
0.7515 Intermediate Similarity NPC469765
0.7515 Intermediate Similarity NPC469760
0.7515 Intermediate Similarity NPC25008
0.7515 Intermediate Similarity NPC311276
0.7515 Intermediate Similarity NPC469813
0.7515 Intermediate Similarity NPC476446
0.7514 Intermediate Similarity NPC472586
0.75 Intermediate Similarity NPC95783
0.75 Intermediate Similarity NPC50503
0.75 Intermediate Similarity NPC475841
0.75 Intermediate Similarity NPC314333
0.75 Intermediate Similarity NPC238457
0.75 Intermediate Similarity NPC329858
0.75 Intermediate Similarity NPC474145
0.7486 Intermediate Similarity NPC472443
0.7485 Intermediate Similarity NPC201700
0.7485 Intermediate Similarity NPC470111
0.7485 Intermediate Similarity NPC469762
0.7485 Intermediate Similarity NPC63751
0.7483 Intermediate Similarity NPC81561
0.7474 Intermediate Similarity NPC469589
0.7471 Intermediate Similarity NPC280852
0.747 Intermediate Similarity NPC80597
0.747 Intermediate Similarity NPC212376
0.747 Intermediate Similarity NPC211572
0.747 Intermediate Similarity NPC70922
0.747 Intermediate Similarity NPC476297
0.747 Intermediate Similarity NPC470507
0.747 Intermediate Similarity NPC75540
0.7458 Intermediate Similarity NPC472444
0.7457 Intermediate Similarity NPC161861
0.7456 Intermediate Similarity NPC282231
0.7446 Intermediate Similarity NPC469736
0.744 Intermediate Similarity NPC6436
0.744 Intermediate Similarity NPC293487
0.7439 Intermediate Similarity NPC37548
0.7429 Intermediate Similarity NPC64436
0.7429 Intermediate Similarity NPC28848
0.7429 Intermediate Similarity NPC14325
0.7427 Intermediate Similarity NPC56233
0.7427 Intermediate Similarity NPC54988
0.7427 Intermediate Similarity NPC160105
0.7425 Intermediate Similarity NPC51054
0.7415 Intermediate Similarity NPC148140
0.7412 Intermediate Similarity NPC194640
0.741 Intermediate Similarity NPC281094
0.7405 Intermediate Similarity NPC265576
0.7405 Intermediate Similarity NPC218268
0.7399 Intermediate Similarity NPC126492
0.7396 Intermediate Similarity NPC279918
0.7386 Intermediate Similarity NPC219336
0.7384 Intermediate Similarity NPC154293
0.7377 Intermediate Similarity NPC473178
0.7374 Intermediate Similarity NPC15102
0.7371 Intermediate Similarity NPC56618
0.7368 Intermediate Similarity NPC166492
0.7368 Intermediate Similarity NPC473362
0.7363 Intermediate Similarity NPC473763
0.7363 Intermediate Similarity NPC117244
0.7362 Intermediate Similarity NPC204141
0.7358 Intermediate Similarity NPC264176
0.7358 Intermediate Similarity NPC472098
0.7356 Intermediate Similarity NPC34508
0.7349 Intermediate Similarity NPC470233
0.734 Intermediate Similarity NPC162730
0.7333 Intermediate Similarity NPC187951
0.7333 Intermediate Similarity NPC251936
0.7333 Intermediate Similarity NPC472027
0.733 Intermediate Similarity NPC15573
0.733 Intermediate Similarity NPC183662
0.733 Intermediate Similarity NPC217372
0.733 Intermediate Similarity NPC151939
0.7329 Intermediate Similarity NPC115611
0.7329 Intermediate Similarity NPC238499
0.7326 Intermediate Similarity NPC329793
0.7326 Intermediate Similarity NPC478183
0.7322 Intermediate Similarity NPC55493
0.7315 Intermediate Similarity NPC162689
0.7315 Intermediate Similarity NPC54102
0.7314 Intermediate Similarity NPC469938
0.731 Intermediate Similarity NPC478184

  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 NPC81229 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
0.8333 Intermediate Similarity NPD4602 Approved
0.82 Intermediate Similarity NPD3385 Approved
0.8129 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD5104 Approved
0.7988 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD3654 Approved
0.7917 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD1683 Approved
0.7812 Intermediate Similarity NPD4547 Phase 3
0.7784 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD2915 Discontinued
0.7784 Intermediate Similarity NPD4550 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6158 Phase 2
0.7778 Intermediate Similarity NPD2882 Phase 1
0.7771 Intermediate Similarity NPD5075 Discontinued
0.7754 Intermediate Similarity NPD4520 Approved
0.7702 Intermediate Similarity NPD4702 Approved
0.7702 Intermediate Similarity NPD4703 Approved
0.7692 Intermediate Similarity NPD6554 Approved
0.7692 Intermediate Similarity NPD45 Approved
0.7673 Intermediate Similarity NPD4047 Discontinued
0.7609 Intermediate Similarity NPD4600 Approved
0.7609 Intermediate Similarity NPD4601 Approved
0.7609 Intermediate Similarity NPD4500 Approved
0.7609 Intermediate Similarity NPD4501 Approved
0.759 Intermediate Similarity NPD4326 Phase 2
0.7571 Intermediate Similarity NPD6227 Discontinued
0.7542 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD7469 Discontinued
0.75 Intermediate Similarity NPD4204 Approved
0.75 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4499 Approved
0.75 Intermediate Similarity NPD4203 Approved
0.75 Intermediate Similarity NPD6281 Approved
0.7485 Intermediate Similarity NPD4639 Approved
0.7485 Intermediate Similarity NPD4638 Approved
0.7485 Intermediate Similarity NPD5862 Discovery
0.7485 Intermediate Similarity NPD4640 Approved
0.7472 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6285 Phase 2
0.7459 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD5255 Approved
0.7429 Intermediate Similarity NPD7111 Discontinued
0.7419 Intermediate Similarity NPD3475 Approved
0.7419 Intermediate Similarity NPD3476 Approved
0.7414 Intermediate Similarity NPD5065 Approved
0.741 Intermediate Similarity NPD2837 Discontinued
0.7405 Intermediate Similarity NPD4397 Phase 1
0.7396 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD2383 Phase 1
0.7389 Intermediate Similarity NPD3942 Approved
0.7389 Intermediate Similarity NPD3944 Approved
0.7384 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD2380 Approved
0.7371 Intermediate Similarity NPD2382 Approved
0.7371 Intermediate Similarity NPD2381 Approved
0.7363 Intermediate Similarity NPD5913 Phase 3
0.7363 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD1326 Approved
0.7341 Intermediate Similarity NPD1325 Approved
0.7338 Intermediate Similarity NPD2119 Approved
0.7338 Intermediate Similarity NPD2118 Approved
0.7337 Intermediate Similarity NPD7944 Discontinued
0.7333 Intermediate Similarity NPD5538 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7666 Phase 3
0.733 Intermediate Similarity NPD7665 Phase 2
0.733 Intermediate Similarity NPD2144 Approved
0.7329 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD4957 Phase 2
0.7314 Intermediate Similarity NPD6492 Phase 2
0.7296 Intermediate Similarity NPD1256 Approved
0.7296 Intermediate Similarity NPD1253 Approved
0.7296 Intermediate Similarity NPD1254 Approved
0.7296 Intermediate Similarity NPD1255 Approved
0.7284 Intermediate Similarity NPD1722 Approved
0.7283 Intermediate Similarity NPD5021 Discontinued
0.7278 Intermediate Similarity NPD2581 Approved
0.7278 Intermediate Similarity NPD2582 Approved
0.7278 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1661 Suspended
0.7267 Intermediate Similarity NPD786 Approved
0.7263 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD750 Phase 2
0.7251 Intermediate Similarity NPD5315 Discontinued
0.7249 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD6595 Phase 3
0.7247 Intermediate Similarity NPD6452 Discontinued
0.7247 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD7112 Discontinued
0.7243 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD3717 Discontinued
0.7239 Intermediate Similarity NPD2006 Phase 2
0.7235 Intermediate Similarity NPD5418 Discontinued
0.7232 Intermediate Similarity NPD8123 Approved
0.7232 Intermediate Similarity NPD8122 Approved
0.7229 Intermediate Similarity NPD2430 Phase 2
0.7219 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2580 Discontinued
0.7219 Intermediate Similarity NPD2150 Discontinued
0.7209 Intermediate Similarity NPD3323 Discontinued
0.7207 Intermediate Similarity NPD3038 Discontinued
0.7207 Intermediate Similarity NPD4383 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7935 Phase 2
0.7202 Intermediate Similarity NPD4121 Phase 3
0.7202 Intermediate Similarity NPD4120 Approved
0.7198 Intermediate Similarity NPD7394 Phase 2
0.7197 Intermediate Similarity NPD715 Phase 3
0.7195 Intermediate Similarity NPD3401 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5254 Discontinued
0.7191 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD8386 Phase 2
0.7191 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7222 Phase 2
0.7186 Intermediate Similarity NPD4462 Approved
0.7186 Intermediate Similarity NPD4463 Approved
0.7184 Intermediate Similarity NPD2390 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD5555 Phase 1
0.7181 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD5020 Approved
0.7176 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD5100 Phase 3
0.7174 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD4030 Approved
0.717 Intermediate Similarity NPD4029 Approved
0.717 Intermediate Similarity NPD4028 Approved
0.716 Intermediate Similarity NPD5741 Approved
0.716 Intermediate Similarity NPD5743 Approved
0.716 Intermediate Similarity NPD5742 Approved
0.7151 Intermediate Similarity NPD5897 Approved
0.7151 Intermediate Similarity NPD5899 Approved
0.7151 Intermediate Similarity NPD5898 Approved
0.7143 Intermediate Similarity NPD5444 Phase 1
0.7135 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD4181 Approved
0.7126 Intermediate Similarity NPD3100 Discontinued
0.7112 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD8408 Discontinued
0.711 Intermediate Similarity NPD5140 Approved
0.711 Intermediate Similarity NPD5138 Approved
0.7105 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD8431 Approved
0.7095 Intermediate Similarity NPD4076 Approved
0.7095 Intermediate Similarity NPD4079 Approved
0.7091 Intermediate Similarity NPD5671 Approved
0.7091 Intermediate Similarity NPD4509 Discontinued
0.709 Intermediate Similarity NPD6999 Discontinued
0.709 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7287 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD4037 Approved
0.7083 Intermediate Similarity NPD4035 Approved
0.7083 Intermediate Similarity NPD4034 Approved
0.7083 Intermediate Similarity NPD4038 Approved
0.7083 Intermediate Similarity NPD32 Approved
0.7083 Intermediate Similarity NPD4122 Approved
0.7083 Intermediate Similarity NPD31 Approved
0.7083 Intermediate Similarity NPD4036 Approved
0.7083 Intermediate Similarity NPD4039 Approved
0.7083 Intermediate Similarity NPD2172 Phase 1
0.7083 Intermediate Similarity NPD4033 Approved
0.7081 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD4334 Discontinued
0.7056 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD6771 Discontinued
0.7039 Intermediate Similarity NPD6159 Phase 2
0.7039 Intermediate Similarity NPD3506 Approved
0.7039 Intermediate Similarity NPD3505 Approved
0.7033 Intermediate Similarity NPD7483 Phase 2
0.7033 Intermediate Similarity NPD7482 Phase 2
0.7031 Intermediate Similarity NPD4886 Phase 2
0.7029 Intermediate Similarity NPD6794 Approved
0.7024 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4128 Approved
0.7021 Intermediate Similarity NPD3477 Phase 2
0.7021 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6026 Approved
0.7016 Intermediate Similarity NPD6307 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD8021 Approved
0.7011 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD8020 Approved
0.7005 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.699 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6989 Remote Similarity NPD3785 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6272 Phase 1
0.6989 Remote Similarity NPD5069 Clinical (unspecified phase)
0.6988 Remote Similarity NPD3813 Approved
0.6988 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6978 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6978 Remote Similarity NPD2095 Phase 2
0.6978 Remote Similarity NPD2094 Phase 2
0.6978 Remote Similarity NPD2092 Phase 2
0.6978 Remote Similarity NPD5596 Phase 2
0.6978 Remote Similarity NPD4345 Clinical (unspecified phase)
0.6974 Remote Similarity NPD5658 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