Structure

Physi-Chem Properties

Molecular Weight:  380.85
Volume:  249.23
LogP:  4.466
LogD:  2.223
LogS:  -6.439
# Rotatable Bonds:  2
TPSA:  38.85
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.625
Synthetic Accessibility Score:  4.349
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.837
MDCK Permeability:  2.112870970449876e-05
Pgp-inhibitor:  0.037
Pgp-substrate:  0.116
Human Intestinal Absorption (HIA):  0.951
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.337
Plasma Protein Binding (PPB):  98.4771499633789%
Volume Distribution (VD):  3.119
Pgp-substrate:  2.8145194053649902%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.719
CYP2C19-inhibitor:  0.315
CYP2C19-substrate:  0.653
CYP2C9-inhibitor:  0.341
CYP2C9-substrate:  0.85
CYP2D6-inhibitor:  0.388
CYP2D6-substrate:  0.579
CYP3A4-inhibitor:  0.33
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  1.592
Half-life (T1/2):  0.469

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.17
Drug-inuced Liver Injury (DILI):  0.952
AMES Toxicity:  0.433
Rat Oral Acute Toxicity:  0.893
Maximum Recommended Daily Dose:  0.931
Skin Sensitization:  0.825
Carcinogencity:  0.966
Eye Corrosion:  0.924
Eye Irritation:  0.953
Respiratory Toxicity:  0.968

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

  Natural Product: NPC474168

Natural Product ID:  NPC474168
Common Name*:   Sid492474
IUPAC Name:   4,6-dibromo-3-methylsulfanyl-2-methylsulfinyl-1H-indole
Synonyms:  
Standard InCHIKey:  RPUHYZCTFRSRAR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H9Br2NOS2/c1-15-9-8-6(12)3-5(11)4-7(8)13-10(9)16(2)14/h3-4,13H,1-2H3
SMILES:  CSc1c([nH]c2c1c(Br)cc(c2)Br)S(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463143
PubChem CID:   362040
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles

*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
NPO4291 Laurencia brongniartii Species Rhodomelaceae Eukaryota n.a. Formosan red alga n.a. PMID[15921441]
NPO4291 Laurencia brongniartii Species Rhodomelaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 16672.47 nM PMID[543810]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 19275.25 nM PMID[543810]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 23442.29 nM PMID[543810]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 24490.63 nM PMID[543810]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 21281.39 nM PMID[543810]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10889.3 nM PMID[543810]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 22387.21 nM PMID[543810]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 18281.0 nM PMID[543810]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 24945.95 nM PMID[543810]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 24154.61 nM PMID[543810]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 20558.91 nM PMID[543810]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 22130.95 nM PMID[543810]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 18113.4 nM PMID[543810]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 37.58 nM PMID[543810]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 22029.26 nM PMID[543810]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 16405.9 nM PMID[543810]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 29174.27 nM PMID[543810]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 32809.53 nM PMID[543810]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 27797.13 nM PMID[543810]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 23280.91 nM PMID[543810]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 25585.86 nM PMID[543810]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 24603.68 nM PMID[543810]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 18793.17 nM PMID[543810]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 27164.39 nM PMID[543810]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 16218.1 nM PMID[543810]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 23988.33 nM PMID[543810]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 18281.0 nM PMID[543810]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 17298.16 nM PMID[543810]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 22803.42 nM PMID[543810]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 17579.24 nM PMID[543810]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 14256.08 nM PMID[543810]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 21086.28 nM PMID[543810]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 20370.42 nM PMID[543810]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 27861.21 nM PMID[543810]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 16749.43 nM PMID[543810]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 17947.34 nM PMID[543810]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 25118.86 nM PMID[543810]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 17060.82 nM PMID[543810]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 20653.8 nM PMID[543810]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 37068.07 nM PMID[543810]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 19319.68 nM PMID[543810]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 15995.58 nM PMID[543810]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 33265.96 nM PMID[543810]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 16519.62 nM PMID[543810]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 22233.1 nM PMID[543810]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 27415.74 nM PMID[543810]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 20701.41 nM PMID[543810]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 26853.44 nM PMID[543810]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 13963.68 nM PMID[543810]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 17988.71 nM PMID[543810]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 39536.66 nM PMID[543810]

☑ 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 NPC474168 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
0.7758 Intermediate Similarity NPC148592
0.759 Intermediate Similarity NPC2272
0.7485 Intermediate Similarity NPC474791
0.7456 Intermediate Similarity NPC141926
0.729 Intermediate Similarity NPC41174
0.7257 Intermediate Similarity NPC149265
0.7093 Intermediate Similarity NPC470823
0.7062 Intermediate Similarity NPC247987
0.7059 Intermediate Similarity NPC316069
0.7022 Intermediate Similarity NPC17751
0.7022 Intermediate Similarity NPC274229
0.7017 Intermediate Similarity NPC64055
0.7011 Intermediate Similarity NPC34844
0.7 Intermediate Similarity NPC250361
0.7 Intermediate Similarity NPC476140
0.6994 Remote Similarity NPC216713
0.6975 Remote Similarity NPC473587
0.6961 Remote Similarity NPC82331
0.6954 Remote Similarity NPC232798
0.6954 Remote Similarity NPC161108
0.6933 Remote Similarity NPC22079
0.6933 Remote Similarity NPC475428
0.6923 Remote Similarity NPC477611
0.6919 Remote Similarity NPC471957
0.6914 Remote Similarity NPC473762
0.689 Remote Similarity NPC475450
0.689 Remote Similarity NPC179365
0.6889 Remote Similarity NPC109447
0.6879 Remote Similarity NPC161550
0.6865 Remote Similarity NPC233050
0.6865 Remote Similarity NPC276540
0.6848 Remote Similarity NPC474958
0.6828 Remote Similarity NPC164228
0.6793 Remote Similarity NPC280297
0.6791 Remote Similarity NPC275292
0.6791 Remote Similarity NPC243381
0.6766 Remote Similarity NPC198988
0.6761 Remote Similarity NPC200214
0.6747 Remote Similarity NPC473930
0.6739 Remote Similarity NPC288074
0.6726 Remote Similarity NPC29886
0.6726 Remote Similarity NPC261195
0.6726 Remote Similarity NPC325252
0.6687 Remote Similarity NPC82295
0.6686 Remote Similarity NPC84911
0.6648 Remote Similarity NPC280864
0.6627 Remote Similarity NPC96102
0.6627 Remote Similarity NPC218268
0.6614 Remote Similarity NPC307191
0.6608 Remote Similarity NPC110126
0.6608 Remote Similarity NPC73767
0.659 Remote Similarity NPC190296
0.6588 Remote Similarity NPC125746
0.6588 Remote Similarity NPC105127
0.657 Remote Similarity NPC469784
0.657 Remote Similarity NPC469780
0.657 Remote Similarity NPC115611
0.657 Remote Similarity NPC469783
0.657 Remote Similarity NPC2949
0.657 Remote Similarity NPC59084
0.657 Remote Similarity NPC469768
0.657 Remote Similarity NPC469761
0.657 Remote Similarity NPC469767
0.657 Remote Similarity NPC469779
0.6552 Remote Similarity NPC242556
0.6546 Remote Similarity NPC231536
0.6545 Remote Similarity NPC110158
0.6543 Remote Similarity NPC248454
0.6541 Remote Similarity NPC97343
0.6532 Remote Similarity NPC88121
0.6532 Remote Similarity NPC63157
0.6532 Remote Similarity NPC469766
0.6532 Remote Similarity NPC473868
0.6514 Remote Similarity NPC314372
0.6514 Remote Similarity NPC470440
0.6512 Remote Similarity NPC312092
0.6512 Remote Similarity NPC88097
0.6478 Remote Similarity NPC148140
0.6474 Remote Similarity NPC279081
0.6474 Remote Similarity NPC284635
0.6467 Remote Similarity NPC2165
0.6447 Remote Similarity NPC188821
0.6447 Remote Similarity NPC474180
0.6447 Remote Similarity NPC88315
0.6438 Remote Similarity NPC81561
0.6424 Remote Similarity NPC273714
0.642 Remote Similarity NPC285731
0.642 Remote Similarity NPC159856
0.6406 Remote Similarity NPC163055
0.6404 Remote Similarity NPC37548
0.6404 Remote Similarity NPC124005
0.6396 Remote Similarity NPC477167
0.6396 Remote Similarity NPC304187
0.6396 Remote Similarity NPC473342
0.6396 Remote Similarity NPC477166
0.6379 Remote Similarity NPC230002
0.6373 Remote Similarity NPC108011
0.6369 Remote Similarity NPC105818
0.6369 Remote Similarity NPC24678
0.6348 Remote Similarity NPC477134
0.6348 Remote Similarity NPC21605
0.6348 Remote Similarity NPC179787
0.6348 Remote Similarity NPC201380
0.6328 Remote Similarity NPC204141
0.6319 Remote Similarity NPC215519
0.6318 Remote Similarity NPC474389
0.6316 Remote Similarity NPC121903
0.6313 Remote Similarity NPC321911
0.6298 Remote Similarity NPC469765
0.6298 Remote Similarity NPC469760
0.6298 Remote Similarity NPC469763
0.6298 Remote Similarity NPC469786
0.6298 Remote Similarity NPC259644
0.6298 Remote Similarity NPC73952
0.6298 Remote Similarity NPC25008
0.6296 Remote Similarity NPC54102
0.6296 Remote Similarity NPC162689
0.6292 Remote Similarity NPC143872
0.6292 Remote Similarity NPC63545
0.6292 Remote Similarity NPC288838
0.6287 Remote Similarity NPC237414
0.6278 Remote Similarity NPC53947
0.6278 Remote Similarity NPC33421
0.6264 Remote Similarity NPC38736
0.6264 Remote Similarity NPC211572
0.6264 Remote Similarity NPC212376
0.6264 Remote Similarity NPC471458
0.6264 Remote Similarity NPC75540
0.6264 Remote Similarity NPC80597
0.6264 Remote Similarity NPC470507
0.6264 Remote Similarity NPC70922
0.6257 Remote Similarity NPC469811
0.6256 Remote Similarity NPC269203
0.6256 Remote Similarity NPC77241
0.6256 Remote Similarity NPC13456
0.6256 Remote Similarity NPC166209
0.625 Remote Similarity NPC6436
0.623 Remote Similarity NPC285469
0.623 Remote Similarity NPC184476
0.6229 Remote Similarity NPC316811
0.6228 Remote Similarity NPC69277
0.6225 Remote Similarity NPC52909
0.6225 Remote Similarity NPC475935
0.6225 Remote Similarity NPC94211
0.6222 Remote Similarity NPC187951
0.6219 Remote Similarity NPC222018
0.6211 Remote Similarity NPC247980
0.6207 Remote Similarity NPC268744
0.6207 Remote Similarity NPC477004
0.6207 Remote Similarity NPC201266
0.6207 Remote Similarity NPC220797
0.6207 Remote Similarity NPC474318
0.6207 Remote Similarity NPC153123
0.6207 Remote Similarity NPC475914
0.6201 Remote Similarity NPC129042
0.6196 Remote Similarity NPC236711
0.6196 Remote Similarity NPC316910
0.6196 Remote Similarity NPC299594
0.6195 Remote Similarity NPC473761
0.619 Remote Similarity NPC151779
0.6188 Remote Similarity NPC272483
0.6176 Remote Similarity NPC106771
0.6176 Remote Similarity NPC23420
0.6176 Remote Similarity NPC303820
0.6176 Remote Similarity NPC205254
0.6168 Remote Similarity NPC122718
0.6141 Remote Similarity NPC469785
0.6141 Remote Similarity NPC141353
0.614 Remote Similarity NPC255110
0.6129 Remote Similarity NPC473320
0.612 Remote Similarity NPC325903
0.6118 Remote Similarity NPC287895
0.6117 Remote Similarity NPC195507
0.6108 Remote Similarity NPC76982
0.6108 Remote Similarity NPC286427
0.6108 Remote Similarity NPC469762
0.6106 Remote Similarity NPC82053
0.61 Remote Similarity NPC243716
0.6096 Remote Similarity NPC16667
0.6096 Remote Similarity NPC282231
0.6096 Remote Similarity NPC214106
0.6089 Remote Similarity NPC294693
0.6075 Remote Similarity NPC56765
0.6075 Remote Similarity NPC474880
0.6075 Remote Similarity NPC221786
0.6075 Remote Similarity NPC475990
0.6075 Remote Similarity NPC318065
0.6075 Remote Similarity NPC41257
0.6075 Remote Similarity NPC92796
0.6075 Remote Similarity NPC135141
0.6075 Remote Similarity NPC206819
0.6075 Remote Similarity NPC230869
0.6073 Remote Similarity NPC245348
0.6066 Remote Similarity NPC470233
0.6064 Remote Similarity NPC21174
0.6064 Remote Similarity NPC271797
0.6064 Remote Similarity NPC271734
0.6064 Remote Similarity NPC40779
0.6064 Remote Similarity NPC311276
0.6064 Remote Similarity NPC8104

  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 NPC474168 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
0.7365 Intermediate Similarity NPD1528 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1597 Phase 1
0.676 Remote Similarity NPD1403 Approved
0.676 Remote Similarity NPD1404 Approved
0.6755 Remote Similarity NPD5105 Approved
0.6755 Remote Similarity NPD5106 Approved
0.6744 Remote Similarity NPD3401 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4509 Discontinued
0.6667 Remote Similarity NPD3512 Clinical (unspecified phase)
0.6627 Remote Similarity NPD198 Clinical (unspecified phase)
0.6615 Remote Similarity NPD5590 Clinical (unspecified phase)
0.6612 Remote Similarity NPD2639 Approved
0.6612 Remote Similarity NPD2642 Approved
0.6608 Remote Similarity NPD786 Approved
0.6588 Remote Similarity NPD1262 Discovery
0.6576 Remote Similarity NPD2641 Approved
0.6576 Remote Similarity NPD2640 Approved
0.6576 Remote Similarity NPD2185 Clinical (unspecified phase)
0.657 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6519 Remote Similarity NPD2308 Clinical (unspecified phase)
0.6517 Remote Similarity NPD3015 Discontinued
0.651 Remote Similarity NPD5439 Approved
0.651 Remote Similarity NPD5438 Approved
0.6457 Remote Similarity NPD5254 Discontinued
0.6437 Remote Similarity NPD1592 Phase 3
0.6437 Remote Similarity NPD1722 Approved
0.6417 Remote Similarity NPD3610 Approved
0.6417 Remote Similarity NPD3609 Approved
0.6369 Remote Similarity NPD3833 Phase 3
0.6369 Remote Similarity NPD3835 Phase 3
0.6369 Remote Similarity NPD4463 Approved
0.6369 Remote Similarity NPD4462 Approved
0.6359 Remote Similarity NPD2385 Clinical (unspecified phase)
0.6313 Remote Similarity NPD3100 Discontinued
0.6298 Remote Similarity NPD3843 Clinical (unspecified phase)
0.6284 Remote Similarity NPD1647 Phase 1
0.6284 Remote Similarity NPD1648 Phase 1
0.6278 Remote Similarity NPD2172 Phase 1
0.6272 Remote Similarity NPD3654 Approved
0.623 Remote Similarity NPD3348 Phase 2
0.6229 Remote Similarity NPD2069 Approved
0.6229 Remote Similarity NPD2070 Approved
0.6229 Remote Similarity NPD2071 Approved
0.6229 Remote Similarity NPD2068 Approved
0.6222 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6215 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6196 Remote Similarity NPD2330 Approved
0.619 Remote Similarity NPD5412 Discontinued
0.618 Remote Similarity NPD649 Clinical (unspecified phase)
0.6176 Remote Similarity NPD947 Approved
0.6173 Remote Similarity NPD1227 Phase 2
0.6127 Remote Similarity NPD6264 Discontinued
0.6127 Remote Similarity NPD3385 Approved
0.612 Remote Similarity NPD2837 Discontinued
0.6111 Remote Similarity NPD2310 Clinical (unspecified phase)
0.6111 Remote Similarity NPD1683 Approved
0.6092 Remote Similarity NPD4880 Discontinued
0.608 Remote Similarity NPD8110 Clinical (unspecified phase)
0.608 Remote Similarity NPD2323 Clinical (unspecified phase)
0.6069 Remote Similarity NPD1995 Approved
0.6069 Remote Similarity NPD1993 Approved
0.6069 Remote Similarity NPD1994 Approved
0.6067 Remote Similarity NPD3834 Clinical (unspecified phase)
0.6057 Remote Similarity NPD1255 Approved
0.6057 Remote Similarity NPD1253 Approved
0.6057 Remote Similarity NPD1256 Approved
0.6057 Remote Similarity NPD1254 Approved
0.6045 Remote Similarity NPD680 Discontinued
0.6044 Remote Similarity NPD1183 Approved
0.6032 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6031 Remote Similarity NPD4398 Clinical (unspecified phase)
0.6023 Remote Similarity NPD6554 Approved
0.6023 Remote Similarity NPD45 Approved
0.6012 Remote Similarity NPD1251 Discontinued
0.6011 Remote Similarity NPD972 Clinical (unspecified phase)
0.6011 Remote Similarity NPD5315 Discontinued
0.601 Remote Similarity NPD3859 Clinical (unspecified phase)
0.6 Remote Similarity NPD7884 Discontinued
0.6 Remote Similarity NPD5502 Approved
0.6 Remote Similarity NPD5503 Approved
0.6 Remote Similarity NPD9583 Approved
0.599 Remote Similarity NPD647 Approved
0.599 Remote Similarity NPD4318 Clinical (unspecified phase)
0.5989 Remote Similarity NPD1554 Clinical (unspecified phase)
0.5979 Remote Similarity NPD3323 Discontinued
0.5976 Remote Similarity NPD9357 Approved
0.5972 Remote Similarity NPD5409 Clinical (unspecified phase)
0.5966 Remote Similarity NPD792 Discontinued
0.5952 Remote Similarity NPD1561 Phase 2
0.5946 Remote Similarity NPD5189 Clinical (unspecified phase)
0.5939 Remote Similarity NPD4399 Phase 2
0.5938 Remote Similarity NPD4184 Clinical (unspecified phase)
0.5938 Remote Similarity NPD1326 Approved
0.5938 Remote Similarity NPD1325 Approved
0.593 Remote Similarity NPD3279 Phase 2
0.5926 Remote Similarity NPD1853 Clinical (unspecified phase)
0.5918 Remote Similarity NPD676 Discontinued
0.5897 Remote Similarity NPD2771 Approved
0.5895 Remote Similarity NPD5140 Approved
0.5895 Remote Similarity NPD5138 Approved
0.5885 Remote Similarity NPD1857 Discontinued
0.5885 Remote Similarity NPD5069 Clinical (unspecified phase)
0.5882 Remote Similarity NPD5634 Approved
0.5882 Remote Similarity NPD2150 Discontinued
0.5882 Remote Similarity NPD6265 Discontinued
0.5876 Remote Similarity NPD4112 Clinical (unspecified phase)
0.5874 Remote Similarity NPD1219 Approved
0.5874 Remote Similarity NPD1218 Approved
0.5856 Remote Similarity NPD4047 Discontinued
0.5856 Remote Similarity NPD2006 Phase 2
0.5856 Remote Similarity NPD4510 Discontinued
0.5846 Remote Similarity NPD4128 Approved
0.5846 Remote Similarity NPD1569 Phase 2
0.5826 Remote Similarity NPD5818 Discontinued
0.5825 Remote Similarity NPD3127 Clinical (unspecified phase)
0.5825 Remote Similarity NPD754 Clinical (unspecified phase)
0.5816 Remote Similarity NPD4075 Phase 2
0.5816 Remote Similarity NPD749 Clinical (unspecified phase)
0.5815 Remote Similarity NPD1661 Suspended
0.5813 Remote Similarity NPD2818 Discontinued
0.5806 Remote Similarity NPD4641 Discontinued
0.5805 Remote Similarity NPD2717 Phase 2
0.5803 Remote Similarity NPD773 Approved
0.5803 Remote Similarity NPD2844 Phase 3
0.5802 Remote Similarity NPD2849 Clinical (unspecified phase)
0.5798 Remote Similarity NPD473 Clinical (unspecified phase)
0.5787 Remote Similarity NPD5755 Clinical (unspecified phase)
0.5787 Remote Similarity NPD4181 Approved
0.5787 Remote Similarity NPD3506 Approved
0.5787 Remote Similarity NPD3505 Approved
0.5787 Remote Similarity NPD2144 Approved
0.5784 Remote Similarity NPD4918 Discontinued
0.578 Remote Similarity NPD1556 Clinical (unspecified phase)
0.578 Remote Similarity NPD992 Clinical (unspecified phase)
0.578 Remote Similarity NPD991 Phase 2
0.5779 Remote Similarity NPD412 Approved
0.5771 Remote Similarity NPD3475 Approved
0.5771 Remote Similarity NPD3476 Approved
0.5765 Remote Similarity NPD5065 Approved
0.5765 Remote Similarity NPD482 Approved
0.5758 Remote Similarity NPD4079 Approved
0.5758 Remote Similarity NPD4076 Approved
0.5756 Remote Similarity NPD7127 Clinical (unspecified phase)
0.5751 Remote Similarity NPD1248 Discontinued
0.5743 Remote Similarity NPD2409 Clinical (unspecified phase)
0.5742 Remote Similarity NPD1315 Clinical (unspecified phase)
0.5735 Remote Similarity NPD8073 Approved
0.573 Remote Similarity NPD4547 Phase 3
0.5729 Remote Similarity NPD8464 Clinical (unspecified phase)
0.5729 Remote Similarity NPD6277 Clinical (unspecified phase)
0.5729 Remote Similarity NPD4050 Phase 1
0.5729 Remote Similarity NPD6595 Phase 3
0.5728 Remote Similarity NPD2320 Discontinued
0.5722 Remote Similarity NPD2059 Approved
0.5722 Remote Similarity NPD5021 Discontinued
0.5722 Remote Similarity NPD4779 Clinical (unspecified phase)
0.5722 Remote Similarity NPD2058 Phase 2
0.5722 Remote Similarity NPD2057 Approved
0.5708 Remote Similarity NPD8072 Approved
0.5707 Remote Similarity NPD6203 Clinical (unspecified phase)
0.5701 Remote Similarity NPD4865 Approved
0.57 Remote Similarity NPD3038 Discontinued
0.5699 Remote Similarity NPD2430 Phase 2
0.5699 Remote Similarity NPD2719 Clinical (unspecified phase)
0.5699 Remote Similarity NPD2720 Phase 1
0.5684 Remote Similarity NPD2865 Clinical (unspecified phase)
0.5681 Remote Similarity NPD8272 Phase 2
0.5672 Remote Similarity NPD3319 Phase 1
0.5672 Remote Similarity NPD3318 Approved
0.5672 Remote Similarity NPD3320 Approved
0.5663 Remote Similarity NPD3883 Clinical (unspecified phase)
0.5663 Remote Similarity NPD6827 Clinical (unspecified phase)
0.5663 Remote Similarity NPD6828 Phase 2
0.5661 Remote Similarity NPD2165 Phase 1
0.5661 Remote Similarity NPD4436 Clinical (unspecified phase)
0.5661 Remote Similarity NPD1328 Approved
0.5659 Remote Similarity NPD7135 Phase 2
0.565 Remote Similarity NPD5473 Discontinued
0.565 Remote Similarity NPD702 Clinical (unspecified phase)
0.5645 Remote Similarity NPD2089 Clinical (unspecified phase)
0.5645 Remote Similarity NPD1005 Phase 2
0.5645 Remote Similarity NPD1004 Phase 2
0.5644 Remote Similarity NPD3607 Clinical (unspecified phase)
0.5644 Remote Similarity NPD2306 Approved
0.5641 Remote Similarity NPD7287 Clinical (unspecified phase)
0.5641 Remote Similarity NPD4320 Clinical (unspecified phase)
0.5634 Remote Similarity NPD6888 Discontinued
0.5634 Remote Similarity NPD6139 Clinical (unspecified phase)
0.5632 Remote Similarity NPD3112 Approved
0.5632 Remote Similarity NPD3114 Approved
0.5632 Remote Similarity NPD3113 Approved
0.5632 Remote Similarity NPD2580 Discontinued
0.5632 Remote Similarity NPD3115 Approved
0.5628 Remote Similarity NPD2815 Clinical (unspecified phase)
0.5622 Remote Similarity NPD1708 Approved
0.5622 Remote Similarity NPD1707 Approved
0.5619 Remote Similarity NPD509 Phase 3
0.5619 Remote Similarity NPD4470 Phase 2
0.5619 Remote Similarity NPD6846 Clinical (unspecified phase)
0.5616 Remote Similarity NPD6610 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data