Structure

Physi-Chem Properties

Molecular Weight:  294.26
Volume:  346.851
LogP:  6.234
LogD:  4.316
LogS:  -5.887
# Rotatable Bonds:  15
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.224
Synthetic Accessibility Score:  2.319
Fsp3:  0.737
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.586
MDCK Permeability:  2.331721771042794e-05
Pgp-inhibitor:  0.044
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.65
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.352
Plasma Protein Binding (PPB):  97.30188751220703%
Volume Distribution (VD):  1.066
Pgp-substrate:  1.7196998596191406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.901
CYP1A2-substrate:  0.351
CYP2C19-inhibitor:  0.707
CYP2C19-substrate:  0.502
CYP2C9-inhibitor:  0.439
CYP2C9-substrate:  0.941
CYP2D6-inhibitor:  0.789
CYP2D6-substrate:  0.267
CYP3A4-inhibitor:  0.931
CYP3A4-substrate:  0.145

ADMET: Excretion

Clearance (CL):  5.968
Half-life (T1/2):  0.416

ADMET: Toxicity

hERG Blockers:  0.418
Human Hepatotoxicity (H-HT):  0.521
Drug-inuced Liver Injury (DILI):  0.337
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.518
Skin Sensitization:  0.961
Carcinogencity:  0.112
Eye Corrosion:  0.607
Eye Irritation:  0.878
Respiratory Toxicity:  0.944

Download Data

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

  Natural Product: NPC228473

Natural Product ID:  NPC228473
Common Name*:   Methyl (10E,12Z)-Octadeca-10,12-Dienoate
IUPAC Name:   methyl (10E,12Z)-octadeca-10,12-dienoate
Synonyms:  
Standard InCHIKey:  KMXSXYSNZMSDFK-UQGDGPGGSA-N
Standard InCHI:  InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-10H,3-6,11-18H2,1-2H3/b8-7-,10-9+
SMILES:  CCCCC/C=CC=CCCCCCCCCC(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2004275
PubChem CID:   5471014
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO23320 Marsdenia tenacissima Species Apocynaceae Eukaryota stems Simao County, Yunnan Province, China 2005-MAR PMID[25215856]
NPO23320 Marsdenia tenacissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23320 Marsdenia tenacissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]

☑ 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 13867.56 nM PMID[529015]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 24043.63 nM PMID[529015]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 29785.16 nM PMID[529015]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[529015]

☑ 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 NPC228473 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
0.9608 High Similarity NPC309606
0.9608 High Similarity NPC39633
0.9608 High Similarity NPC139545
0.9245 High Similarity NPC128061
0.9245 High Similarity NPC200845
0.9245 High Similarity NPC10316
0.9245 High Similarity NPC223677
0.9245 High Similarity NPC28779
0.9216 High Similarity NPC262968
0.9074 High Similarity NPC18951
0.902 High Similarity NPC224227
0.8868 High Similarity NPC71761
0.8704 High Similarity NPC32467
0.8704 High Similarity NPC154245
0.8704 High Similarity NPC88966
0.8704 High Similarity NPC85813
0.8704 High Similarity NPC87564
0.8704 High Similarity NPC261831
0.8704 High Similarity NPC6095
0.8704 High Similarity NPC281972
0.8704 High Similarity NPC25417
0.8704 High Similarity NPC290563
0.8704 High Similarity NPC424
0.8627 High Similarity NPC216130
0.8571 High Similarity NPC225929
0.8519 High Similarity NPC70387
0.8519 High Similarity NPC294548
0.8519 High Similarity NPC139029
0.8519 High Similarity NPC36061
0.8519 High Similarity NPC321062
0.8519 High Similarity NPC1813
0.8448 Intermediate Similarity NPC143857
0.8448 Intermediate Similarity NPC229252
0.8393 Intermediate Similarity NPC477201
0.8333 Intermediate Similarity NPC281245
0.8333 Intermediate Similarity NPC92114
0.8333 Intermediate Similarity NPC161366
0.8305 Intermediate Similarity NPC201939
0.8197 Intermediate Similarity NPC245947
0.8197 Intermediate Similarity NPC136164
0.8197 Intermediate Similarity NPC326268
0.8197 Intermediate Similarity NPC255863
0.8197 Intermediate Similarity NPC318420
0.8167 Intermediate Similarity NPC54925
0.8136 Intermediate Similarity NPC251042
0.8136 Intermediate Similarity NPC174447
0.8136 Intermediate Similarity NPC122521
0.8136 Intermediate Similarity NPC243532
0.8113 Intermediate Similarity NPC207815
0.807 Intermediate Similarity NPC187777
0.807 Intermediate Similarity NPC179764
0.8033 Intermediate Similarity NPC328089
0.8033 Intermediate Similarity NPC68343
0.8 Intermediate Similarity NPC40082
0.7969 Intermediate Similarity NPC473772
0.7966 Intermediate Similarity NPC274927
0.7966 Intermediate Similarity NPC106851
0.7963 Intermediate Similarity NPC59051
0.7895 Intermediate Similarity NPC54766
0.7895 Intermediate Similarity NPC274290
0.7895 Intermediate Similarity NPC473863
0.7846 Intermediate Similarity NPC476660
0.7778 Intermediate Similarity NPC5413
0.7778 Intermediate Similarity NPC149821
0.7778 Intermediate Similarity NPC163345
0.7705 Intermediate Similarity NPC320305
0.7705 Intermediate Similarity NPC328776
0.7679 Intermediate Similarity NPC310746
0.7656 Intermediate Similarity NPC473829
0.7656 Intermediate Similarity NPC22101
0.7656 Intermediate Similarity NPC475443
0.7656 Intermediate Similarity NPC127091
0.7656 Intermediate Similarity NPC104537
0.7656 Intermediate Similarity NPC148192
0.7656 Intermediate Similarity NPC271921
0.7656 Intermediate Similarity NPC330426
0.7593 Intermediate Similarity NPC180534
0.7593 Intermediate Similarity NPC91495
0.7593 Intermediate Similarity NPC207292
0.7586 Intermediate Similarity NPC52264
0.7586 Intermediate Similarity NPC474672
0.7576 Intermediate Similarity NPC475310
0.7541 Intermediate Similarity NPC235242
0.7541 Intermediate Similarity NPC45097
0.7541 Intermediate Similarity NPC299730
0.7541 Intermediate Similarity NPC328311
0.7541 Intermediate Similarity NPC327112
0.7538 Intermediate Similarity NPC473559
0.7538 Intermediate Similarity NPC324981
0.7538 Intermediate Similarity NPC141481
0.7538 Intermediate Similarity NPC48218
0.75 Intermediate Similarity NPC469373
0.75 Intermediate Similarity NPC474321
0.746 Intermediate Similarity NPC470320
0.7458 Intermediate Similarity NPC325977
0.7424 Intermediate Similarity NPC317583
0.7424 Intermediate Similarity NPC143396
0.7419 Intermediate Similarity NPC174560
0.7419 Intermediate Similarity NPC321838
0.7419 Intermediate Similarity NPC125312
0.7414 Intermediate Similarity NPC87394
0.7414 Intermediate Similarity NPC137538
0.7407 Intermediate Similarity NPC110234
0.7407 Intermediate Similarity NPC44363
0.7407 Intermediate Similarity NPC163751
0.7391 Intermediate Similarity NPC228978
0.7385 Intermediate Similarity NPC26500
0.7385 Intermediate Similarity NPC99619
0.7368 Intermediate Similarity NPC216407
0.7368 Intermediate Similarity NPC18357
0.7344 Intermediate Similarity NPC476657
0.7344 Intermediate Similarity NPC476654
0.7344 Intermediate Similarity NPC476655
0.7313 Intermediate Similarity NPC42526
0.7286 Intermediate Similarity NPC239127
0.7273 Intermediate Similarity NPC218477
0.7255 Intermediate Similarity NPC28598
0.7255 Intermediate Similarity NPC161097
0.7246 Intermediate Similarity NPC227396
0.7246 Intermediate Similarity NPC306928
0.7231 Intermediate Similarity NPC304665
0.7231 Intermediate Similarity NPC126899
0.7231 Intermediate Similarity NPC154728
0.7231 Intermediate Similarity NPC476656
0.7231 Intermediate Similarity NPC476659
0.7222 Intermediate Similarity NPC239754
0.7222 Intermediate Similarity NPC117572
0.7213 Intermediate Similarity NPC267817
0.7213 Intermediate Similarity NPC34416
0.7206 Intermediate Similarity NPC320119
0.7193 Intermediate Similarity NPC470412
0.7193 Intermediate Similarity NPC284212
0.7193 Intermediate Similarity NPC28205
0.7193 Intermediate Similarity NPC470410
0.7188 Intermediate Similarity NPC226592
0.7183 Intermediate Similarity NPC145898
0.7143 Intermediate Similarity NPC98284
0.7143 Intermediate Similarity NPC255060
0.7143 Intermediate Similarity NPC469414
0.7143 Intermediate Similarity NPC250919
0.7143 Intermediate Similarity NPC329826
0.7119 Intermediate Similarity NPC322461
0.7101 Intermediate Similarity NPC325627
0.7101 Intermediate Similarity NPC167145
0.7101 Intermediate Similarity NPC470237
0.7101 Intermediate Similarity NPC326024
0.7101 Intermediate Similarity NPC474705
0.7097 Intermediate Similarity NPC329550
0.7097 Intermediate Similarity NPC329249
0.7077 Intermediate Similarity NPC317881
0.7077 Intermediate Similarity NPC320642
0.7077 Intermediate Similarity NPC323045
0.7049 Intermediate Similarity NPC211752
0.7049 Intermediate Similarity NPC323498
0.7049 Intermediate Similarity NPC323597
0.7042 Intermediate Similarity NPC899
0.7031 Intermediate Similarity NPC155849
0.7015 Intermediate Similarity NPC53302
0.7 Intermediate Similarity NPC330016
0.7 Intermediate Similarity NPC477984
0.7 Intermediate Similarity NPC166797
0.7 Intermediate Similarity NPC92558
0.6986 Remote Similarity NPC263574
0.6986 Remote Similarity NPC469747
0.6986 Remote Similarity NPC158565
0.6981 Remote Similarity NPC203531
0.6981 Remote Similarity NPC236579
0.697 Remote Similarity NPC16119
0.697 Remote Similarity NPC142423
0.697 Remote Similarity NPC308294
0.697 Remote Similarity NPC284447
0.6957 Remote Similarity NPC84038
0.6923 Remote Similarity NPC12156
0.6923 Remote Similarity NPC34883
0.6923 Remote Similarity NPC476658
0.6912 Remote Similarity NPC199557
0.6901 Remote Similarity NPC476844
0.6897 Remote Similarity NPC477458
0.6897 Remote Similarity NPC48162
0.6892 Remote Similarity NPC469920
0.6885 Remote Similarity NPC327388
0.6875 Remote Similarity NPC477829
0.6866 Remote Similarity NPC49863
0.6866 Remote Similarity NPC474619
0.6863 Remote Similarity NPC305660
0.6863 Remote Similarity NPC54980
0.6863 Remote Similarity NPC22903
0.6863 Remote Similarity NPC201622
0.6852 Remote Similarity NPC270796
0.6849 Remote Similarity NPC4827
0.6833 Remote Similarity NPC269615
0.6825 Remote Similarity NPC474267
0.6825 Remote Similarity NPC322002
0.6818 Remote Similarity NPC98897
0.6818 Remote Similarity NPC133904
0.6806 Remote Similarity NPC472967
0.6806 Remote Similarity NPC266159
0.6806 Remote Similarity NPC474447
0.678 Remote Similarity NPC170167
0.678 Remote Similarity NPC106531

  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 NPC228473 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
0.9216 High Similarity NPD29 Approved
0.9216 High Similarity NPD28 Approved
0.8704 High Similarity NPD3195 Phase 2
0.8704 High Similarity NPD4266 Approved
0.8704 High Similarity NPD3196 Approved
0.8704 High Similarity NPD3194 Approved
0.8519 High Similarity NPD3172 Approved
0.8235 Intermediate Similarity NPD3174 Discontinued
0.7925 Intermediate Similarity NPD5343 Approved
0.7778 Intermediate Similarity NPD3173 Approved
0.7742 Intermediate Similarity NPD3197 Phase 1
0.7593 Intermediate Similarity NPD622 Approved
0.7541 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD8039 Approved
0.7358 Intermediate Similarity NPD6096 Approved
0.7358 Intermediate Similarity NPD6097 Approved
0.7222 Intermediate Similarity NPD39 Approved
0.7222 Intermediate Similarity NPD4222 Approved
0.697 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6866 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6863 Remote Similarity NPD3206 Approved
0.6852 Remote Similarity NPD5326 Phase 3
0.6727 Remote Similarity NPD2699 Approved
0.6712 Remote Similarity NPD4756 Discovery
0.661 Remote Similarity NPD6927 Phase 3
0.6481 Remote Similarity NPD2270 Approved
0.6406 Remote Similarity NPD6109 Phase 1
0.64 Remote Similarity NPD3732 Approved
0.6364 Remote Similarity NPD5369 Approved
0.6282 Remote Similarity NPD6435 Approved
0.6234 Remote Similarity NPD5368 Approved
0.6232 Remote Similarity NPD7331 Phase 2
0.6203 Remote Similarity NPD7154 Phase 3
0.6203 Remote Similarity NPD5362 Discontinued
0.6184 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6176 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6145 Remote Similarity NPD6101 Approved
0.6145 Remote Similarity NPD5764 Clinical (unspecified phase)
0.614 Remote Similarity NPD3199 Clinical (unspecified phase)
0.6111 Remote Similarity NPD9448 Phase 2
0.6111 Remote Similarity NPD633 Phase 3
0.6102 Remote Similarity NPD6125 Clinical (unspecified phase)
0.6076 Remote Similarity NPD4270 Approved
0.6076 Remote Similarity NPD4269 Approved
0.6029 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6026 Remote Similarity NPD4252 Approved
0.6026 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6 Remote Similarity NPD4220 Pre-registration
0.6 Remote Similarity NPD7983 Approved
0.6 Remote Similarity NPD6411 Approved
0.5976 Remote Similarity NPD5786 Approved
0.5974 Remote Similarity NPD4268 Approved
0.5974 Remote Similarity NPD4271 Approved
0.593 Remote Similarity NPD5779 Approved
0.593 Remote Similarity NPD5778 Approved
0.5882 Remote Similarity NPD3672 Approved
0.5882 Remote Similarity NPD3673 Approved
0.5875 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5875 Remote Similarity NPD5209 Approved
0.5857 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5854 Remote Similarity NPD5363 Approved
0.5823 Remote Similarity NPD4819 Approved
0.5823 Remote Similarity NPD4821 Approved
0.5823 Remote Similarity NPD4820 Approved
0.5823 Remote Similarity NPD4822 Approved
0.5818 Remote Similarity NPD5783 Phase 3
0.5818 Remote Similarity NPD9655 Approved
0.5789 Remote Similarity NPD387 Clinical (unspecified phase)
0.5783 Remote Similarity NPD7146 Approved
0.5783 Remote Similarity NPD6684 Approved
0.5783 Remote Similarity NPD5330 Approved
0.5783 Remote Similarity NPD7521 Approved
0.5783 Remote Similarity NPD6409 Approved
0.5783 Remote Similarity NPD6422 Discontinued
0.5783 Remote Similarity NPD7334 Approved
0.5781 Remote Similarity NPD3730 Approved
0.5781 Remote Similarity NPD3728 Approved
0.5775 Remote Similarity NPD3704 Approved
0.5769 Remote Similarity NPD225 Approved
0.5769 Remote Similarity NPD227 Approved
0.5765 Remote Similarity NPD5346 Phase 2
0.5765 Remote Similarity NPD5347 Phase 2
0.573 Remote Similarity NPD7839 Suspended
0.5714 Remote Similarity NPD4793 Discontinued
0.5698 Remote Similarity NPD5785 Approved
0.5698 Remote Similarity NPD5207 Approved
0.5652 Remote Similarity NPD4194 Approved
0.5652 Remote Similarity NPD4191 Approved
0.5652 Remote Similarity NPD4193 Approved
0.5652 Remote Similarity NPD4192 Approved
0.5647 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5647 Remote Similarity NPD6903 Approved
0.5647 Remote Similarity NPD5737 Approved
0.5647 Remote Similarity NPD6672 Approved
0.5634 Remote Similarity NPD7341 Phase 2
0.5632 Remote Similarity NPD5694 Approved
0.5632 Remote Similarity NPD6050 Approved
0.561 Remote Similarity NPD5332 Approved
0.561 Remote Similarity NPD5331 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