Structure

Physi-Chem Properties

Molecular Weight:  306.27
Volume:  351.498
LogP:  5.105
LogD:  3.714
LogS:  -2.885
# Rotatable Bonds:  14
TPSA:  34.15
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.391
Synthetic Accessibility Score:  2.799
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:  -4.521
MDCK Permeability:  1.9991730368928984e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.331
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.891
Plasma Protein Binding (PPB):  91.12625885009766%
Volume Distribution (VD):  1.372
Pgp-substrate:  4.035679817199707%

ADMET: Metabolism

CYP1A2-inhibitor:  0.932
CYP1A2-substrate:  0.602
CYP2C19-inhibitor:  0.87
CYP2C19-substrate:  0.827
CYP2C9-inhibitor:  0.635
CYP2C9-substrate:  0.842
CYP2D6-inhibitor:  0.933
CYP2D6-substrate:  0.427
CYP3A4-inhibitor:  0.955
CYP3A4-substrate:  0.294

ADMET: Excretion

Clearance (CL):  9.243
Half-life (T1/2):  0.298

ADMET: Toxicity

hERG Blockers:  0.7
Human Hepatotoxicity (H-HT):  0.487
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.639
Maximum Recommended Daily Dose:  0.398
Skin Sensitization:  0.962
Carcinogencity:  0.041
Eye Corrosion:  0.624
Eye Irritation:  0.43
Respiratory Toxicity:  0.98

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

  Natural Product: NPC475105

Natural Product ID:  NPC475105
Common Name*:   Hachijodine C
IUPAC Name:   N-methoxy-2-methyl-12-pyridin-3-yldodecan-1-amine
Synonyms:   Hachijodine C
Standard InCHIKey:  BBEGJVYEJJDIJI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H34N2O/c1-18(16-21-22-2)12-9-7-5-3-4-6-8-10-13-19-14-11-15-20-17-19/h11,14-15,17-18,21H,3-10,12-13,16H2,1-2H3
SMILES:  CC(CCCCCCCCCCC1=CN=CC=C1)CNOC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL498080
PubChem CID:   9995340
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines 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
NPO32714 xestospongia Genus Petrosiidae Eukaryota n.a. n.a. n.a. PMID[10843588]
NPO32954 amphimedon Genus Niphatidae Eukaryota n.a. n.a. n.a. PMID[10843588]
NPO32714 xestospongia Genus Petrosiidae Eukaryota n.a. South Pacific n.a. PMID[20634081]

☑ 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
NPT168 Cell Line P388 Mus musculus Activity = 2.2 ug ml-1 PMID[524153]

☑ 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 NPC475105 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 NPC329896
1.0 High Similarity NPC475090
0.9918 High Similarity NPC89490
0.935 High Similarity NPC290094
0.9127 High Similarity NPC202957
0.9127 High Similarity NPC169625
0.871 High Similarity NPC471402
0.871 High Similarity NPC240136
0.871 High Similarity NPC297486
0.8636 High Similarity NPC471322
0.8605 High Similarity NPC166424
0.8605 High Similarity NPC146373
0.8605 High Similarity NPC245244
0.8527 High Similarity NPC27740
0.8473 Intermediate Similarity NPC471311
0.8473 Intermediate Similarity NPC471313
0.8443 Intermediate Similarity NPC27802
0.8385 Intermediate Similarity NPC476322
0.8372 Intermediate Similarity NPC329825
0.8346 Intermediate Similarity NPC91958
0.8295 Intermediate Similarity NPC182570
0.8295 Intermediate Similarity NPC265605
0.8295 Intermediate Similarity NPC48564
0.8197 Intermediate Similarity NPC76540
0.8148 Intermediate Similarity NPC69914
0.8088 Intermediate Similarity NPC101165
0.8074 Intermediate Similarity NPC476131
0.8062 Intermediate Similarity NPC143603
0.8015 Intermediate Similarity NPC282398
0.8014 Intermediate Similarity NPC469779
0.8014 Intermediate Similarity NPC469761
0.8014 Intermediate Similarity NPC469780
0.8014 Intermediate Similarity NPC469767
0.8014 Intermediate Similarity NPC469783
0.8014 Intermediate Similarity NPC469784
0.8014 Intermediate Similarity NPC469768
0.7958 Intermediate Similarity NPC469766
0.7956 Intermediate Similarity NPC256893
0.7929 Intermediate Similarity NPC471312
0.7874 Intermediate Similarity NPC235843
0.7832 Intermediate Similarity NPC476454
0.7826 Intermediate Similarity NPC324611
0.7823 Intermediate Similarity NPC105818
0.7823 Intermediate Similarity NPC24678
0.7817 Intermediate Similarity NPC73767
0.7817 Intermediate Similarity NPC315348
0.7817 Intermediate Similarity NPC316811
0.7817 Intermediate Similarity NPC32002
0.7808 Intermediate Similarity NPC470111
0.7801 Intermediate Similarity NPC251722
0.7801 Intermediate Similarity NPC84911
0.7801 Intermediate Similarity NPC314102
0.7793 Intermediate Similarity NPC314372
0.7778 Intermediate Similarity NPC190296
0.7761 Intermediate Similarity NPC46358
0.773 Intermediate Similarity NPC96102
0.773 Intermediate Similarity NPC29886
0.773 Intermediate Similarity NPC261195
0.7724 Intermediate Similarity NPC471323
0.7718 Intermediate Similarity NPC73952
0.7718 Intermediate Similarity NPC469765
0.7718 Intermediate Similarity NPC259644
0.7718 Intermediate Similarity NPC469760
0.7718 Intermediate Similarity NPC469763
0.7718 Intermediate Similarity NPC469786
0.7718 Intermediate Similarity NPC25008
0.7712 Intermediate Similarity NPC474217
0.7705 Intermediate Similarity NPC83987
0.7692 Intermediate Similarity NPC110126
0.7687 Intermediate Similarity NPC477974
0.7676 Intermediate Similarity NPC65408
0.7676 Intermediate Similarity NPC105127
0.7671 Intermediate Similarity NPC285731
0.7667 Intermediate Similarity NPC212376
0.7667 Intermediate Similarity NPC75540
0.7667 Intermediate Similarity NPC211572
0.7667 Intermediate Similarity NPC70922
0.7667 Intermediate Similarity NPC80597
0.7651 Intermediate Similarity NPC470233
0.7647 Intermediate Similarity NPC71079
0.7619 Intermediate Similarity NPC231655
0.7616 Intermediate Similarity NPC469785
0.7616 Intermediate Similarity NPC51054
0.7584 Intermediate Similarity NPC53947
0.7571 Intermediate Similarity NPC82295
0.7568 Intermediate Similarity NPC471957
0.7566 Intermediate Similarity NPC469762
0.7552 Intermediate Similarity NPC150259
0.7551 Intermediate Similarity NPC159856
0.7536 Intermediate Similarity NPC212125
0.7536 Intermediate Similarity NPC306397
0.7517 Intermediate Similarity NPC279081
0.7517 Intermediate Similarity NPC321911
0.7516 Intermediate Similarity NPC56765
0.75 Intermediate Similarity NPC127730
0.75 Intermediate Similarity NPC278366
0.75 Intermediate Similarity NPC476566
0.7484 Intermediate Similarity NPC311276
0.7483 Intermediate Similarity NPC200214
0.7451 Intermediate Similarity NPC236711
0.745 Intermediate Similarity NPC201380
0.745 Intermediate Similarity NPC179787
0.745 Intermediate Similarity NPC469811
0.7436 Intermediate Similarity NPC85918
0.7434 Intermediate Similarity NPC477815
0.7424 Intermediate Similarity NPC84268
0.7397 Intermediate Similarity NPC230002
0.7389 Intermediate Similarity NPC160105
0.7386 Intermediate Similarity NPC476464
0.7383 Intermediate Similarity NPC288838
0.7383 Intermediate Similarity NPC63545
0.7376 Intermediate Similarity NPC315320
0.7372 Intermediate Similarity NPC476446
0.7372 Intermediate Similarity NPC78375
0.7372 Intermediate Similarity NPC40779
0.7372 Intermediate Similarity NPC469813
0.7372 Intermediate Similarity NPC90723
0.7368 Intermediate Similarity NPC325903
0.7342 Intermediate Similarity NPC201700
0.7338 Intermediate Similarity NPC193740
0.7338 Intermediate Similarity NPC469897
0.7338 Intermediate Similarity NPC167635
0.7338 Intermediate Similarity NPC286427
0.7329 Intermediate Similarity NPC104483
0.7315 Intermediate Similarity NPC467188
0.7313 Intermediate Similarity NPC81561
0.7308 Intermediate Similarity NPC225018
0.7303 Intermediate Similarity NPC216713
0.7297 Intermediate Similarity NPC477977
0.729 Intermediate Similarity NPC92796
0.729 Intermediate Similarity NPC41257
0.729 Intermediate Similarity NPC135141
0.729 Intermediate Similarity NPC318065
0.729 Intermediate Similarity NPC206819
0.7286 Intermediate Similarity NPC165370
0.7279 Intermediate Similarity NPC59084
0.7278 Intermediate Similarity NPC49954
0.7278 Intermediate Similarity NPC474561
0.7273 Intermediate Similarity NPC330326
0.7267 Intermediate Similarity NPC143872
0.726 Intermediate Similarity NPC104049
0.726 Intermediate Similarity NPC169433
0.725 Intermediate Similarity NPC201634
0.7241 Intermediate Similarity NPC325252
0.7239 Intermediate Similarity NPC148140
0.7237 Intermediate Similarity NPC40070
0.7234 Intermediate Similarity NPC471589
0.723 Intermediate Similarity NPC63157
0.723 Intermediate Similarity NPC473868
0.7226 Intermediate Similarity NPC216643
0.7226 Intermediate Similarity NPC129721
0.7219 Intermediate Similarity NPC105811
0.7215 Intermediate Similarity NPC477975
0.7206 Intermediate Similarity NPC11863
0.7205 Intermediate Similarity NPC314603
0.7197 Intermediate Similarity NPC470203
0.719 Intermediate Similarity NPC470823
0.7188 Intermediate Similarity NPC194411
0.7174 Intermediate Similarity NPC56856
0.7172 Intermediate Similarity NPC198988
0.717 Intermediate Similarity NPC98187
0.7163 Intermediate Similarity NPC278451
0.7162 Intermediate Similarity NPC2949
0.716 Intermediate Similarity NPC275305
0.716 Intermediate Similarity NPC37423
0.7153 Intermediate Similarity NPC322488
0.7143 Intermediate Similarity NPC141926
0.7143 Intermediate Similarity NPC473901
0.7143 Intermediate Similarity NPC138842
0.7134 Intermediate Similarity NPC215584
0.7134 Intermediate Similarity NPC470204
0.7134 Intermediate Similarity NPC44773
0.7123 Intermediate Similarity NPC29702
0.7097 Intermediate Similarity NPC34844
0.7097 Intermediate Similarity NPC209362
0.7092 Intermediate Similarity NPC135488
0.7089 Intermediate Similarity NPC282231
0.7086 Intermediate Similarity NPC86288
0.7078 Intermediate Similarity NPC70406
0.7073 Intermediate Similarity NPC68354
0.707 Intermediate Similarity NPC230869
0.7044 Intermediate Similarity NPC317105
0.7044 Intermediate Similarity NPC478182
0.7032 Intermediate Similarity NPC251391
0.703 Intermediate Similarity NPC215795
0.703 Intermediate Similarity NPC176199
0.7029 Intermediate Similarity NPC215519
0.7025 Intermediate Similarity NPC131718
0.7025 Intermediate Similarity NPC279918
0.7025 Intermediate Similarity NPC122141
0.7019 Intermediate Similarity NPC63751
0.7014 Intermediate Similarity NPC22079
0.7012 Intermediate Similarity NPC474958
0.7007 Intermediate Similarity NPC162689
0.7007 Intermediate Similarity NPC54102
0.7007 Intermediate Similarity NPC218268
0.7006 Intermediate Similarity NPC213914
0.6993 Remote Similarity NPC21605
0.6988 Remote Similarity NPC300688
0.6984 Remote Similarity NPC213774

  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 NPC475105 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
0.8699 High Similarity NPD269 Clinical (unspecified phase)
0.8473 Intermediate Similarity NPD991 Phase 2
0.8473 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.8473 Intermediate Similarity NPD2119 Approved
0.8473 Intermediate Similarity NPD2118 Approved
0.8397 Intermediate Similarity NPD9583 Approved
0.8306 Intermediate Similarity NPD4824 Approved
0.8306 Intermediate Similarity NPD4823 Approved
0.8295 Intermediate Similarity NPD271 Approved
0.8295 Intermediate Similarity NPD268 Approved
0.8295 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.8244 Intermediate Similarity NPD9357 Approved
0.8148 Intermediate Similarity NPD3476 Approved
0.8148 Intermediate Similarity NPD3475 Approved
0.8125 Intermediate Similarity NPD9396 Approved
0.8125 Intermediate Similarity NPD9392 Approved
0.8102 Intermediate Similarity NPD4029 Approved
0.8102 Intermediate Similarity NPD4030 Approved
0.8102 Intermediate Similarity NPD4028 Approved
0.806 Intermediate Similarity NPD1598 Discontinued
0.8029 Intermediate Similarity NPD1993 Approved
0.8029 Intermediate Similarity NPD1995 Approved
0.8029 Intermediate Similarity NPD1994 Approved
0.8028 Intermediate Similarity NPD3717 Discontinued
0.8028 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.7971 Intermediate Similarity NPD3944 Approved
0.7971 Intermediate Similarity NPD3942 Approved
0.7958 Intermediate Similarity NPD1722 Approved
0.7943 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD4641 Discontinued
0.7857 Intermediate Similarity NPD792 Discontinued
0.7826 Intermediate Similarity NPD9726 Discontinued
0.782 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD2072 Approved
0.7817 Intermediate Similarity NPD2071 Approved
0.7817 Intermediate Similarity NPD2075 Approved
0.7817 Intermediate Similarity NPD2070 Approved
0.7817 Intermediate Similarity NPD2073 Approved
0.7817 Intermediate Similarity NPD2074 Approved
0.7817 Intermediate Similarity NPD786 Approved
0.7817 Intermediate Similarity NPD2069 Approved
0.7817 Intermediate Similarity NPD2068 Approved
0.7808 Intermediate Similarity NPD4703 Approved
0.7808 Intermediate Similarity NPD4702 Approved
0.7762 Intermediate Similarity NPD1395 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD715 Phase 3
0.7746 Intermediate Similarity NPD2896 Discontinued
0.774 Intermediate Similarity NPD7469 Discontinued
0.773 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD803 Phase 1
0.7676 Intermediate Similarity NPD201 Phase 2
0.7676 Intermediate Similarity NPD200 Phase 2
0.7667 Intermediate Similarity NPD5358 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD2142 Approved
0.766 Intermediate Similarity NPD2140 Approved
0.766 Intermediate Similarity NPD2141 Approved
0.7655 Intermediate Similarity NPD1427 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD9098 Phase 3
0.7619 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD3813 Approved
0.755 Intermediate Similarity NPD2809 Approved
0.7536 Intermediate Similarity NPD9080 Approved
0.7536 Intermediate Similarity NPD9284 Approved
0.7534 Intermediate Similarity NPD4510 Discontinued
0.7532 Intermediate Similarity NPD8026 Phase 1
0.7517 Intermediate Similarity NPD3100 Discontinued
0.7517 Intermediate Similarity NPD9599 Approved
0.75 Intermediate Similarity NPD1380 Discovery
0.75 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3583 Phase 2
0.7483 Intermediate Similarity NPD3339 Approved
0.7481 Intermediate Similarity NPD9598 Discontinued
0.7467 Intermediate Similarity NPD2172 Phase 1
0.7452 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD7287 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD2061 Approved
0.7434 Intermediate Similarity NPD2165 Phase 1
0.7426 Intermediate Similarity NPD5787 Discontinued
0.7419 Intermediate Similarity NPD6771 Discontinued
0.7415 Intermediate Similarity NPD2006 Phase 2
0.7405 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3112 Approved
0.7386 Intermediate Similarity NPD3115 Approved
0.7386 Intermediate Similarity NPD6026 Approved
0.7386 Intermediate Similarity NPD3114 Approved
0.7386 Intermediate Similarity NPD3113 Approved
0.7376 Intermediate Similarity NPD9206 Approved
0.7376 Intermediate Similarity NPD9207 Approved
0.7372 Intermediate Similarity NPD3323 Discontinued
0.7368 Intermediate Similarity NPD2837 Discontinued
0.7365 Intermediate Similarity NPD1352 Discontinued
0.7355 Intermediate Similarity NPD2511 Approved
0.7347 Intermediate Similarity NPD1382 Phase 2
0.7347 Intermediate Similarity NPD1383 Phase 3
0.7342 Intermediate Similarity NPD2641 Approved
0.7342 Intermediate Similarity NPD2640 Approved
0.7342 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD2581 Approved
0.7338 Intermediate Similarity NPD2582 Approved
0.7333 Intermediate Similarity NPD1270 Approved
0.7333 Intermediate Similarity NPD4547 Phase 3
0.7333 Intermediate Similarity NPD2089 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4804 Approved
0.7324 Intermediate Similarity NPD809 Discontinued
0.732 Intermediate Similarity NPD977 Approved
0.732 Intermediate Similarity NPD975 Approved
0.732 Intermediate Similarity NPD1328 Approved
0.732 Intermediate Similarity NPD976 Approved
0.731 Intermediate Similarity NPD9506 Approved
0.7308 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD3262 Approved
0.7297 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD60 Approved
0.7292 Intermediate Similarity NPD272 Approved
0.7285 Intermediate Similarity NPD2430 Phase 2
0.7279 Intermediate Similarity NPD4811 Discontinued
0.7278 Intermediate Similarity NPD5611 Phase 2
0.7273 Intermediate Similarity NPD9100 Approved
0.7273 Intermediate Similarity NPD2580 Discontinued
0.7273 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD6635 Approved
0.725 Intermediate Similarity NPD3117 Approved
0.725 Intermediate Similarity NPD3116 Approved
0.7248 Intermediate Similarity NPD1918 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD206 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD490 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD2462 Phase 3
0.7237 Intermediate Similarity NPD2466 Phase 3
0.7237 Intermediate Similarity NPD2465 Approved
0.723 Intermediate Similarity NPD4805 Approved
0.7226 Intermediate Similarity NPD2145 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5541 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6044 Discontinued
0.7222 Intermediate Similarity NPD3385 Approved
0.7219 Intermediate Similarity NPD1661 Suspended
0.719 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD2619 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD2620 Phase 2
0.7185 Intermediate Similarity NPD8840 Approved
0.7183 Intermediate Similarity NPD3654 Approved
0.7179 Intermediate Similarity NPD5255 Approved
0.7178 Intermediate Similarity NPD4181 Approved
0.7171 Intermediate Similarity NPD1183 Approved
0.7162 Intermediate Similarity NPD1649 Discontinued
0.7143 Intermediate Similarity NPD1917 Discontinued
0.7143 Intermediate Similarity NPD3609 Approved
0.7143 Intermediate Similarity NPD3610 Approved
0.7134 Intermediate Similarity NPD1403 Approved
0.7134 Intermediate Similarity NPD1404 Approved
0.7125 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD4463 Approved
0.7124 Intermediate Similarity NPD4462 Approved
0.7123 Intermediate Similarity NPD1254 Approved
0.7123 Intermediate Similarity NPD1256 Approved
0.7123 Intermediate Similarity NPD1253 Approved
0.7123 Intermediate Similarity NPD1255 Approved
0.7105 Intermediate Similarity NPD2110 Approved
0.7089 Intermediate Similarity NPD4239 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD4384 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5315 Discontinued
0.7081 Intermediate Similarity NPD5436 Phase 1
0.7081 Intermediate Similarity NPD4024 Phase 3
0.7073 Intermediate Similarity NPD3505 Approved
0.7073 Intermediate Similarity NPD3506 Approved
0.7063 Intermediate Similarity NPD2642 Approved
0.7063 Intermediate Similarity NPD2639 Approved
0.7055 Intermediate Similarity NPD5065 Approved
0.7055 Intermediate Similarity NPD5322 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4891 Phase 2
0.7044 Intermediate Similarity NPD5088 Discontinued
0.7044 Intermediate Similarity NPD8129 Discovery
0.7039 Intermediate Similarity NPD1683 Approved
0.703 Intermediate Similarity NPD4076 Approved
0.703 Intermediate Similarity NPD4079 Approved
0.7027 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD1988 Phase 1
0.7019 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4075 Phase 2
0.7006 Intermediate Similarity NPD5300 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6497 Approved
0.7006 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5020 Approved
0.6981 Remote Similarity NPD1853 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4973 Approved
0.697 Remote Similarity NPD4071 Approved
0.697 Remote Similarity NPD2144 Approved
0.697 Remote Similarity NPD4072 Approved
0.6964 Remote Similarity NPD7564 Discontinued
0.6962 Remote Similarity NPD3433 Clinical (unspecified phase)
0.6962 Remote Similarity NPD1679 Approved
0.6957 Remote Similarity NPD5636 Discontinued
0.6957 Remote Similarity NPD3929 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