Structure

Physi-Chem Properties

Molecular Weight:  235.1
Volume:  249.962
LogP:  2.72
LogD:  3.589
LogS:  -3.553
# Rotatable Bonds:  6
TPSA:  20.31
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.731
Synthetic Accessibility Score:  2.373
Fsp3:  0.308
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.429
MDCK Permeability:  2.198699803557247e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.817
Plasma Protein Binding (PPB):  77.89218139648438%
Volume Distribution (VD):  0.51
Pgp-substrate:  19.153350830078125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.87
CYP1A2-substrate:  0.918
CYP2C19-inhibitor:  0.871
CYP2C19-substrate:  0.799
CYP2C9-inhibitor:  0.303
CYP2C9-substrate:  0.895
CYP2D6-inhibitor:  0.798
CYP2D6-substrate:  0.791
CYP3A4-inhibitor:  0.175
CYP3A4-substrate:  0.47

ADMET: Excretion

Clearance (CL):  9.523
Half-life (T1/2):  0.806

ADMET: Toxicity

hERG Blockers:  0.101
Human Hepatotoxicity (H-HT):  0.193
Drug-inuced Liver Injury (DILI):  0.196
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.081
Maximum Recommended Daily Dose:  0.038
Skin Sensitization:  0.93
Carcinogencity:  0.307
Eye Corrosion:  0.161
Eye Irritation:  0.912
Respiratory Toxicity:  0.355

Download Data

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

  Natural Product: NPC473661

Natural Product ID:  NPC473661
Common Name*:   N-Methylsinharin
IUPAC Name:   (E)-N-methyl-3-methylsulfanyl-N-(2-phenylethyl)prop-2-enamide
Synonyms:   N-Methylsinharin
Standard InCHIKey:  MJMYEUZTXGLJEX-PKNBQFBNSA-N
Standard InCHI:  InChI=1S/C13H17NOS/c1-14(13(15)9-11-16-2)10-8-12-6-4-3-5-7-12/h3-7,9,11H,8,10H2,1-2H3/b11-9+
SMILES:  CS/C=C/C(=O)N(CCc1ccccc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448347
PubChem CID:   10879097
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted 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
NPO33498 glycosmis sp. Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[9036182]

☑ 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
NPT776 Organism Spodoptera littoralis Spodoptera littoralis EC50 = 0.47 umol/g PMID[529656]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis LC50 = 4.24 umol/g PMID[529656]
NPT1780 Organism Davidiella tassiana Davidiella tassiana ED50 = 17.6 ug ml-1 PMID[529656]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis LC50 = 0.03 umol/dm'2 PMID[529656]

☑ 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 NPC473661 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
0.8764 High Similarity NPC53492
0.8736 High Similarity NPC474088
0.8556 High Similarity NPC305602
0.8556 High Similarity NPC17497
0.8211 Intermediate Similarity NPC71140
0.8021 Intermediate Similarity NPC474974
0.7938 Intermediate Similarity NPC256452
0.783 Intermediate Similarity NPC475013
0.7778 Intermediate Similarity NPC475573
0.7778 Intermediate Similarity NPC475289
0.7685 Intermediate Similarity NPC476048
0.7528 Intermediate Similarity NPC271642
0.7426 Intermediate Similarity NPC472258
0.7416 Intermediate Similarity NPC98976
0.7264 Intermediate Similarity NPC143516
0.7264 Intermediate Similarity NPC473418
0.7196 Intermediate Similarity NPC471447
0.7196 Intermediate Similarity NPC130898
0.7196 Intermediate Similarity NPC474804
0.7196 Intermediate Similarity NPC474973
0.7191 Intermediate Similarity NPC244738
0.7158 Intermediate Similarity NPC104070
0.7143 Intermediate Similarity NPC329375
0.7143 Intermediate Similarity NPC139658
0.713 Intermediate Similarity NPC55529
0.7128 Intermediate Similarity NPC231986
0.7064 Intermediate Similarity NPC473676
0.7037 Intermediate Similarity NPC45033
0.7019 Intermediate Similarity NPC120203
0.6991 Remote Similarity NPC246904
0.6989 Remote Similarity NPC12857
0.6923 Remote Similarity NPC299134
0.6923 Remote Similarity NPC302169
0.6907 Remote Similarity NPC169016
0.6869 Remote Similarity NPC473031
0.6857 Remote Similarity NPC322598
0.6852 Remote Similarity NPC275467
0.6789 Remote Similarity NPC167336
0.6778 Remote Similarity NPC229235
0.6765 Remote Similarity NPC470926
0.6754 Remote Similarity NPC276949
0.6754 Remote Similarity NPC35850
0.6742 Remote Similarity NPC311343
0.6739 Remote Similarity NPC122327
0.6739 Remote Similarity NPC112609
0.6739 Remote Similarity NPC113000
0.6733 Remote Similarity NPC470877
0.6729 Remote Similarity NPC11466
0.6726 Remote Similarity NPC181390
0.6724 Remote Similarity NPC239357
0.6719 Remote Similarity NPC307682
0.6702 Remote Similarity NPC325662
0.6702 Remote Similarity NPC98269
0.6697 Remote Similarity NPC469974
0.6696 Remote Similarity NPC33742
0.6694 Remote Similarity NPC300315
0.6667 Remote Similarity NPC141139
0.6667 Remote Similarity NPC121872
0.6667 Remote Similarity NPC276699
0.6667 Remote Similarity NPC159178
0.6667 Remote Similarity NPC98880
0.6667 Remote Similarity NPC78041
0.6667 Remote Similarity NPC471307
0.6667 Remote Similarity NPC209764
0.6667 Remote Similarity NPC74936
0.6639 Remote Similarity NPC27833
0.6635 Remote Similarity NPC291070
0.6635 Remote Similarity NPC246757
0.6634 Remote Similarity NPC12429
0.6629 Remote Similarity NPC52330
0.6606 Remote Similarity NPC202613
0.66 Remote Similarity NPC203076
0.66 Remote Similarity NPC258046
0.6593 Remote Similarity NPC219246
0.6593 Remote Similarity NPC95289
0.6581 Remote Similarity NPC470544
0.6557 Remote Similarity NPC22746
0.6535 Remote Similarity NPC471638
0.6531 Remote Similarity NPC14326
0.6526 Remote Similarity NPC290638
0.6525 Remote Similarity NPC470545
0.6522 Remote Similarity NPC326200
0.6509 Remote Similarity NPC471320
0.6509 Remote Similarity NPC471319
0.6505 Remote Similarity NPC185501
0.6504 Remote Similarity NPC79698
0.65 Remote Similarity NPC316582
0.6496 Remote Similarity NPC473573
0.6486 Remote Similarity NPC476198
0.6484 Remote Similarity NPC16190
0.6484 Remote Similarity NPC235059
0.6484 Remote Similarity NPC169222
0.6476 Remote Similarity NPC471309
0.6471 Remote Similarity NPC220698
0.6471 Remote Similarity NPC228515
0.6471 Remote Similarity NPC470546
0.6458 Remote Similarity NPC76455
0.6458 Remote Similarity NPC137847
0.6457 Remote Similarity NPC194857
0.6457 Remote Similarity NPC32858
0.6442 Remote Similarity NPC245259
0.6441 Remote Similarity NPC14672
0.6441 Remote Similarity NPC315276
0.6441 Remote Similarity NPC285926
0.6437 Remote Similarity NPC45255
0.6429 Remote Similarity NPC473498
0.6422 Remote Similarity NPC228400
0.6422 Remote Similarity NPC214200
0.64 Remote Similarity NPC218323
0.6364 Remote Similarity NPC476990
0.6364 Remote Similarity NPC200964
0.6354 Remote Similarity NPC329318
0.6349 Remote Similarity NPC213969
0.6349 Remote Similarity NPC165726
0.6344 Remote Similarity NPC74458
0.6337 Remote Similarity NPC3210
0.6336 Remote Similarity NPC89489
0.6333 Remote Similarity NPC36440
0.633 Remote Similarity NPC75496
0.6321 Remote Similarity NPC322040
0.6316 Remote Similarity NPC468984
0.6311 Remote Similarity NPC202521
0.6311 Remote Similarity NPC71684
0.6306 Remote Similarity NPC471317
0.6304 Remote Similarity NPC5324
0.63 Remote Similarity NPC119677
0.6299 Remote Similarity NPC187231
0.6293 Remote Similarity NPC269340
0.6289 Remote Similarity NPC2785
0.6289 Remote Similarity NPC285470
0.6289 Remote Similarity NPC36342
0.6279 Remote Similarity NPC120441
0.6279 Remote Similarity NPC65873
0.6279 Remote Similarity NPC300345
0.6279 Remote Similarity NPC212114
0.6277 Remote Similarity NPC285679
0.6273 Remote Similarity NPC155847
0.6273 Remote Similarity NPC289381
0.6271 Remote Similarity NPC113099
0.6262 Remote Similarity NPC108339
0.6262 Remote Similarity NPC303045
0.6262 Remote Similarity NPC329430
0.6262 Remote Similarity NPC161972
0.6262 Remote Similarity NPC58674
0.6261 Remote Similarity NPC158854
0.626 Remote Similarity NPC252878
0.625 Remote Similarity NPC126458
0.625 Remote Similarity NPC210849
0.6238 Remote Similarity NPC133162
0.6224 Remote Similarity NPC300205
0.6224 Remote Similarity NPC139901
0.6224 Remote Similarity NPC151405
0.6216 Remote Similarity NPC239854
0.621 Remote Similarity NPC46427
0.621 Remote Similarity NPC6975
0.6204 Remote Similarity NPC25565
0.6202 Remote Similarity NPC473962
0.6195 Remote Similarity NPC67043
0.619 Remote Similarity NPC316108
0.6186 Remote Similarity NPC3672
0.6186 Remote Similarity NPC245966
0.6186 Remote Similarity NPC287790
0.6186 Remote Similarity NPC179726
0.6182 Remote Similarity NPC12730
0.6168 Remote Similarity NPC469330
0.6163 Remote Similarity NPC269586
0.6163 Remote Similarity NPC198841
0.6162 Remote Similarity NPC190567
0.6162 Remote Similarity NPC164086
0.6162 Remote Similarity NPC17408
0.6162 Remote Similarity NPC285716
0.616 Remote Similarity NPC222466
0.6159 Remote Similarity NPC13470
0.6154 Remote Similarity NPC325441
0.6148 Remote Similarity NPC177684
0.6148 Remote Similarity NPC291962
0.6147 Remote Similarity NPC473501
0.6147 Remote Similarity NPC475439
0.6146 Remote Similarity NPC32203
0.6146 Remote Similarity NPC206800
0.6132 Remote Similarity NPC226438
0.6131 Remote Similarity NPC313850
0.6122 Remote Similarity NPC103488
0.6122 Remote Similarity NPC50192
0.6116 Remote Similarity NPC254088
0.6111 Remote Similarity NPC101719
0.6111 Remote Similarity NPC171372
0.6111 Remote Similarity NPC50266
0.6107 Remote Similarity NPC266425
0.6105 Remote Similarity NPC271437
0.6103 Remote Similarity NPC471680
0.6103 Remote Similarity NPC322878
0.61 Remote Similarity NPC303245
0.61 Remote Similarity NPC145053
0.6098 Remote Similarity NPC112373
0.6098 Remote Similarity NPC161956
0.6098 Remote Similarity NPC258531
0.6094 Remote Similarity NPC17374
0.608 Remote Similarity NPC474082
0.608 Remote Similarity NPC175726

  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 NPC473661 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
0.7822 Intermediate Similarity NPD813 Approved
0.764 Intermediate Similarity NPD603 Approved
0.7582 Intermediate Similarity NPD5372 Approved
0.7582 Intermediate Similarity NPD5371 Approved
0.7524 Intermediate Similarity NPD1065 Approved
0.7524 Intermediate Similarity NPD1064 Approved
0.7476 Intermediate Similarity NPD4803 Discontinued
0.7473 Intermediate Similarity NPD1053 Approved
0.7473 Intermediate Similarity NPD1052 Approved
0.7473 Intermediate Similarity NPD1051 Approved
0.7451 Intermediate Similarity NPD787 Suspended
0.7444 Intermediate Similarity NPD4147 Approved
0.7444 Intermediate Similarity NPD4144 Approved
0.7429 Intermediate Similarity NPD1576 Approved
0.7426 Intermediate Similarity NPD1100 Approved
0.7426 Intermediate Similarity NPD1099 Approved
0.7353 Intermediate Similarity NPD466 Approved
0.7327 Intermediate Similarity NPD157 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD507 Approved
0.7283 Intermediate Similarity NPD508 Approved
0.7282 Intermediate Similarity NPD742 Approved
0.7264 Intermediate Similarity NPD959 Discontinued
0.7264 Intermediate Similarity NPD1766 Approved
0.7264 Intermediate Similarity NPD1765 Approved
0.7264 Intermediate Similarity NPD1763 Approved
0.7264 Intermediate Similarity NPD1767 Approved
0.7264 Intermediate Similarity NPD1761 Approved
0.7263 Intermediate Similarity NPD2539 Approved
0.7263 Intermediate Similarity NPD2538 Approved
0.7241 Intermediate Similarity NPD4478 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5630 Phase 1
0.7196 Intermediate Similarity NPD7130 Phase 3
0.7193 Intermediate Similarity NPD474 Approved
0.7191 Intermediate Similarity NPD9728 Phase 1
0.7156 Intermediate Similarity NPD4063 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6588 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4026 Approved
0.7128 Intermediate Similarity NPD4027 Approved
0.7083 Intermediate Similarity NPD5178 Approved
0.7054 Intermediate Similarity NPD5064 Approved
0.7054 Intermediate Similarity NPD5063 Approved
0.7053 Intermediate Similarity NPD4170 Approved
0.7053 Intermediate Similarity NPD4169 Approved
0.7053 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD1795 Discontinued
0.6989 Remote Similarity NPD296 Approved
0.6989 Remote Similarity NPD293 Approved
0.6989 Remote Similarity NPD295 Approved
0.6981 Remote Similarity NPD2193 Phase 2
0.6981 Remote Similarity NPD2171 Approved
0.6981 Remote Similarity NPD2196 Discontinued
0.6981 Remote Similarity NPD2648 Phase 3
0.6979 Remote Similarity NPD831 Approved
0.6979 Remote Similarity NPD830 Approved
0.697 Remote Similarity NPD3345 Approved
0.6952 Remote Similarity NPD1796 Phase 3
0.6947 Remote Similarity NPD3035 Approved
0.6944 Remote Similarity NPD2192 Approved
0.6944 Remote Similarity NPD2197 Approved
0.6939 Remote Similarity NPD5252 Clinical (unspecified phase)
0.693 Remote Similarity NPD1323 Discontinued
0.6915 Remote Similarity NPD589 Approved
0.6915 Remote Similarity NPD590 Approved
0.6907 Remote Similarity NPD785 Approved
0.6903 Remote Similarity NPD5181 Approved
0.6903 Remote Similarity NPD5180 Approved
0.6903 Remote Similarity NPD5179 Approved
0.69 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6893 Remote Similarity NPD4094 Approved
0.6864 Remote Similarity NPD5187 Clinical (unspecified phase)
0.6847 Remote Similarity NPD3581 Discontinued
0.6842 Remote Similarity NPD851 Approved
0.6842 Remote Similarity NPD853 Approved
0.6837 Remote Similarity NPD5916 Discontinued
0.6832 Remote Similarity NPD4728 Approved
0.6822 Remote Similarity NPD708 Approved
0.6814 Remote Similarity NPD480 Approved
0.6804 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6804 Remote Similarity NPD4635 Approved
0.68 Remote Similarity NPD587 Approved
0.68 Remote Similarity NPD5675 Discontinued
0.68 Remote Similarity NPD588 Approved
0.6789 Remote Similarity NPD1677 Discontinued
0.6783 Remote Similarity NPD1025 Discontinued
0.6768 Remote Similarity NPD4636 Approved
0.6768 Remote Similarity NPD4409 Approved
0.6768 Remote Similarity NPD4406 Approved
0.6765 Remote Similarity NPD3000 Approved
0.6765 Remote Similarity NPD2998 Approved
0.6765 Remote Similarity NPD2997 Approved
0.6762 Remote Similarity NPD4657 Approved
0.6762 Remote Similarity NPD4655 Approved
0.6759 Remote Similarity NPD1387 Phase 1
0.6759 Remote Similarity NPD3357 Discontinued
0.675 Remote Similarity NPD6408 Phase 1
0.6739 Remote Similarity NPD9591 Approved
0.6739 Remote Similarity NPD9593 Approved
0.6739 Remote Similarity NPD9594 Approved
0.6739 Remote Similarity NPD9588 Approved
0.6739 Remote Similarity NPD9589 Approved
0.6739 Remote Similarity NPD9590 Approved
0.6739 Remote Similarity NPD9592 Approved
0.6739 Remote Similarity NPD80 Approved
0.67 Remote Similarity NPD781 Approved
0.67 Remote Similarity NPD780 Approved
0.67 Remote Similarity NPD782 Approved
0.67 Remote Similarity NPD783 Approved
0.6699 Remote Similarity NPD4407 Approved
0.6699 Remote Similarity NPD4408 Approved
0.6699 Remote Similarity NPD4405 Approved
0.6697 Remote Similarity NPD488 Approved
0.6697 Remote Similarity NPD489 Approved
0.6697 Remote Similarity NPD2577 Clinical (unspecified phase)
0.6696 Remote Similarity NPD2508 Discontinued
0.6696 Remote Similarity NPD3551 Approved
0.6695 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6694 Remote Similarity NPD6729 Phase 2
0.6694 Remote Similarity NPD4125 Approved
0.6667 Remote Similarity NPD3457 Approved
0.6667 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1386 Phase 1
0.6667 Remote Similarity NPD3903 Approved
0.6667 Remote Similarity NPD6024 Approved
0.6667 Remote Similarity NPD3346 Approved
0.6667 Remote Similarity NPD2205 Approved
0.6667 Remote Similarity NPD3979 Approved
0.6667 Remote Similarity NPD6027 Approved
0.6667 Remote Similarity NPD3981 Approved
0.6667 Remote Similarity NPD3904 Approved
0.6667 Remote Similarity NPD3458 Approved
0.6667 Remote Similarity NPD3344 Approved
0.6667 Remote Similarity NPD2208 Approved
0.6667 Remote Similarity NPD3456 Approved
0.6636 Remote Similarity NPD4007 Approved
0.6636 Remote Similarity NPD4008 Approved
0.6635 Remote Similarity NPD4545 Approved
0.6635 Remote Similarity NPD4542 Approved
0.66 Remote Similarity NPD3099 Discontinued
0.6589 Remote Similarity NPD4705 Clinical (unspecified phase)
0.6585 Remote Similarity NPD2585 Clinical (unspecified phase)
0.6583 Remote Similarity NPD1124 Approved
0.6583 Remote Similarity NPD1123 Approved
0.6581 Remote Similarity NPD1344 Phase 2
0.6581 Remote Similarity NPD7679 Phase 2
0.6579 Remote Similarity NPD2124 Approved
0.6577 Remote Similarity NPD3459 Approved
0.6559 Remote Similarity NPD505 Clinical (unspecified phase)
0.6542 Remote Similarity NPD4813 Approved
0.6542 Remote Similarity NPD4263 Approved
0.6542 Remote Similarity NPD1724 Approved
0.6542 Remote Similarity NPD4117 Approved
0.6538 Remote Similarity NPD6690 Approved
0.6535 Remote Similarity NPD4145 Approved
0.6535 Remote Similarity NPD4146 Approved
0.6535 Remote Similarity NPD4680 Discontinued
0.6532 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5990 Approved
0.6525 Remote Similarity NPD5991 Approved
0.6522 Remote Similarity NPD292 Approved
0.6522 Remote Similarity NPD294 Approved
0.6518 Remote Similarity NPD3420 Clinical (unspecified phase)
0.6514 Remote Similarity NPD855 Approved
0.6514 Remote Similarity NPD854 Approved
0.6505 Remote Similarity NPD5915 Approved
0.65 Remote Similarity NPD6806 Phase 1
0.6484 Remote Similarity NPD5272 Discontinued
0.6481 Remote Similarity NPD1067 Discontinued
0.6476 Remote Similarity NPD6549 Approved
0.6476 Remote Similarity NPD6548 Approved
0.6475 Remote Similarity NPD3356 Approved
0.6475 Remote Similarity NPD3355 Approved
0.6471 Remote Similarity NPD6345 Approved
0.6471 Remote Similarity NPD6343 Approved
0.6466 Remote Similarity NPD3598 Phase 3
0.6457 Remote Similarity NPD6076 Approved
0.6457 Remote Similarity NPD6075 Approved
0.6455 Remote Similarity NPD5103 Approved
0.6452 Remote Similarity NPD5653 Discontinued
0.6449 Remote Similarity NPD5598 Approved
0.6449 Remote Similarity NPD1672 Phase 2
0.6449 Remote Similarity NPD5597 Approved
0.6442 Remote Similarity NPD7160 Approved
0.6442 Remote Similarity NPD4543 Discontinued
0.6435 Remote Similarity NPD753 Approved
0.6434 Remote Similarity NPD7733 Phase 2
0.6429 Remote Similarity NPD472 Approved
0.6423 Remote Similarity NPD3549 Approved
0.6423 Remote Similarity NPD3550 Clinical (unspecified phase)
0.6423 Remote Similarity NPD3547 Approved
0.6417 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6415 Remote Similarity NPD5554 Approved
0.641 Remote Similarity NPD2543 Discontinued
0.641 Remote Similarity NPD3867 Phase 2
0.6408 Remote Similarity NPD771 Phase 3
0.64 Remote Similarity NPD4544 Approved
0.6396 Remote Similarity NPD3407 Phase 3
0.6393 Remote Similarity NPD3624 Phase 2
0.6393 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6387 Remote Similarity NPD3806 Clinical (unspecified phase)
0.6385 Remote Similarity NPD5004 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