Structure

Physi-Chem Properties

Molecular Weight:  426.36
Volume:  493.333
LogP:  8.841
LogD:  5.007
LogS:  -3.318
# Rotatable Bonds:  20
TPSA:  44.89
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.219
Synthetic Accessibility Score:  2.118
Fsp3:  0.679
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.181
MDCK Permeability:  8.233447260863613e-06
Pgp-inhibitor:  0.003
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.175
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.092
Plasma Protein Binding (PPB):  98.42798614501953%
Volume Distribution (VD):  3.019
Pgp-substrate:  0.7997453212738037%

ADMET: Metabolism

CYP1A2-inhibitor:  0.145
CYP1A2-substrate:  0.197
CYP2C19-inhibitor:  0.516
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.166
CYP2C9-substrate:  0.968
CYP2D6-inhibitor:  0.83
CYP2D6-substrate:  0.291
CYP3A4-inhibitor:  0.75
CYP3A4-substrate:  0.087

ADMET: Excretion

Clearance (CL):  4.73
Half-life (T1/2):  0.253

ADMET: Toxicity

hERG Blockers:  0.751
Human Hepatotoxicity (H-HT):  0.33
Drug-inuced Liver Injury (DILI):  0.194
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.058
Maximum Recommended Daily Dose:  0.408
Skin Sensitization:  0.965
Carcinogencity:  0.038
Eye Corrosion:  0.004
Eye Irritation:  0.143
Respiratory Toxicity:  0.767

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

  Natural Product: NPC25008

Natural Product ID:  NPC25008
Common Name*:   N-Stearoyltryptamine
IUPAC Name:   N-[2-(1H-indol-3-yl)ethyl]octadecanamide
Synonyms:   N-Stearoyltryptamine
Standard InCHIKey:  AIIVCXFBTONHDU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C28H46N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21-28(31)29-23-22-25-24-30-27-20-18-17-19-26(25)27/h17-20,24,30H,2-16,21-23H2,1H3,(H,29,31)
SMILES:  CCCCCCCCCCCCCCCCCC(=NCCc1c[nH]c2c1cccc2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL491707
PubChem CID:   11796710
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles
          • [CHEMONTID:0004196] 3-alkylindoles

*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
NPO32731 rollinia mucosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[10479316]
NPO31161 Annonaceae Genus Annonaceae Eukaryota n.a. n.a. n.a. PMID[20579892]
NPO31161 Annonaceae Genus Annonaceae Eukaryota n.a. leaf n.a. PMID[23513739]
NPO31161 Annonaceae Genus Annonaceae Eukaryota n.a. fruit n.a. PMID[26920282]

☑ 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
NPT81 Cell Line A549 Homo sapiens ED50 > 10.0 ug ml-1 PMID[524039]
NPT83 Cell Line MCF7 Homo sapiens ED50 > 10.0 ug ml-1 PMID[524039]
NPT139 Cell Line HT-29 Homo sapiens ED50 > 10.0 ug ml-1 PMID[524039]
NPT306 Cell Line PC-3 Homo sapiens ED50 > 10.0 ug ml-1 PMID[524039]
NPT783 Cell Line MIA PaCa-2 Homo sapiens ED50 > 10.0 ug ml-1 PMID[524039]
NPT4564 Cell Line Neurons Activity = 110.0 % PMID[524040]
NPT4564 Cell Line Neurons Activity = 149.9 % PMID[524040]
NPT176 Organism Artemia salina Artemia salina LC50 > 500.0 ug.mL-1 PMID[524039]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 10.0 ug ml-1 PMID[524039]

☑ 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 NPC25008 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 NPC469760
1.0 High Similarity NPC73952
1.0 High Similarity NPC469786
1.0 High Similarity NPC469765
1.0 High Similarity NPC259644
1.0 High Similarity NPC469763
0.993 High Similarity NPC75540
0.993 High Similarity NPC211572
0.993 High Similarity NPC212376
0.993 High Similarity NPC70922
0.993 High Similarity NPC80597
0.9724 High Similarity NPC469785
0.9658 High Similarity NPC469762
0.9577 High Similarity NPC314372
0.953 High Similarity NPC311276
0.9448 High Similarity NPC105818
0.9448 High Similarity NPC24678
0.9437 High Similarity NPC190296
0.9404 High Similarity NPC160105
0.9296 High Similarity NPC469761
0.9296 High Similarity NPC469767
0.9296 High Similarity NPC469783
0.9296 High Similarity NPC469780
0.9296 High Similarity NPC469768
0.9296 High Similarity NPC469784
0.9296 High Similarity NPC469779
0.9276 High Similarity NPC474561
0.9276 High Similarity NPC49954
0.9272 High Similarity NPC40779
0.9231 High Similarity NPC469766
0.9216 High Similarity NPC201700
0.9205 High Similarity NPC282231
0.9172 High Similarity NPC159856
0.9161 High Similarity NPC314603
0.9139 High Similarity NPC279918
0.9139 High Similarity NPC131718
0.9091 High Similarity NPC73767
0.9091 High Similarity NPC63751
0.9085 High Similarity NPC84911
0.9073 High Similarity NPC230869
0.9048 High Similarity NPC471957
0.902 High Similarity NPC194640
0.9014 High Similarity NPC261195
0.9014 High Similarity NPC96102
0.9014 High Similarity NPC29886
0.8958 High Similarity NPC110126
0.8951 High Similarity NPC105127
0.8903 High Similarity NPC54988
0.8896 High Similarity NPC102423
0.8868 High Similarity NPC248454
0.8824 High Similarity NPC92796
0.8824 High Similarity NPC135141
0.8797 High Similarity NPC313791
0.8767 High Similarity NPC279081
0.8758 High Similarity NPC300688
0.875 High Similarity NPC151939
0.875 High Similarity NPC59269
0.8742 High Similarity NPC216713
0.8732 High Similarity NPC82295
0.8726 High Similarity NPC78020
0.8704 High Similarity NPC233936
0.8696 High Similarity NPC213468
0.8688 High Similarity NPC267885
0.8684 High Similarity NPC200214
0.8675 High Similarity NPC53947
0.8671 High Similarity NPC194411
0.865 High Similarity NPC163055
0.8639 High Similarity NPC230002
0.8625 High Similarity NPC110500
0.8625 High Similarity NPC149155
0.8625 High Similarity NPC203468
0.8606 High Similarity NPC94752
0.86 High Similarity NPC288838
0.858 High Similarity NPC248041
0.858 High Similarity NPC126709
0.8571 High Similarity NPC285469
0.8516 High Similarity NPC129721
0.8509 High Similarity NPC37423
0.8509 High Similarity NPC275305
0.8503 High Similarity NPC213629
0.8494 Intermediate Similarity NPC235684
0.8494 Intermediate Similarity NPC474707
0.8487 Intermediate Similarity NPC321911
0.8477 Intermediate Similarity NPC143872
0.8466 Intermediate Similarity NPC283219
0.8443 Intermediate Similarity NPC317030
0.8434 Intermediate Similarity NPC280290
0.8434 Intermediate Similarity NPC15102
0.8428 Intermediate Similarity NPC49217
0.8421 Intermediate Similarity NPC469811
0.8421 Intermediate Similarity NPC201380
0.8421 Intermediate Similarity NPC179787
0.8405 Intermediate Similarity NPC145885
0.8405 Intermediate Similarity NPC14113
0.8405 Intermediate Similarity NPC84827
0.8405 Intermediate Similarity NPC111275
0.8405 Intermediate Similarity NPC68354
0.8397 Intermediate Similarity NPC286427
0.8393 Intermediate Similarity NPC65215
0.8393 Intermediate Similarity NPC173028
0.8385 Intermediate Similarity NPC470498
0.8383 Intermediate Similarity NPC171171
0.8377 Intermediate Similarity NPC470823
0.8373 Intermediate Similarity NPC204717
0.8373 Intermediate Similarity NPC228835
0.8366 Intermediate Similarity NPC37548
0.8364 Intermediate Similarity NPC71037
0.8355 Intermediate Similarity NPC63545
0.8354 Intermediate Similarity NPC55772
0.8354 Intermediate Similarity NPC16667
0.8354 Intermediate Similarity NPC215795
0.8354 Intermediate Similarity NPC176199
0.8344 Intermediate Similarity NPC56765
0.8344 Intermediate Similarity NPC206819
0.8344 Intermediate Similarity NPC41257
0.8344 Intermediate Similarity NPC318065
0.8343 Intermediate Similarity NPC95783
0.8333 Intermediate Similarity NPC204565
0.8323 Intermediate Similarity NPC188387
0.8323 Intermediate Similarity NPC141926
0.8323 Intermediate Similarity NPC314002
0.8323 Intermediate Similarity NPC325903
0.8323 Intermediate Similarity NPC163421
0.8313 Intermediate Similarity NPC220765
0.8311 Intermediate Similarity NPC150259
0.8284 Intermediate Similarity NPC321708
0.828 Intermediate Similarity NPC216643
0.8276 Intermediate Similarity NPC22079
0.8269 Intermediate Similarity NPC34844
0.8269 Intermediate Similarity NPC207726
0.8263 Intermediate Similarity NPC165495
0.8258 Intermediate Similarity NPC470233
0.8256 Intermediate Similarity NPC195239
0.8256 Intermediate Similarity NPC157828
0.8243 Intermediate Similarity NPC218268
0.8243 Intermediate Similarity NPC325252
0.8242 Intermediate Similarity NPC11126
0.8228 Intermediate Similarity NPC67056
0.8224 Intermediate Similarity NPC242556
0.8217 Intermediate Similarity NPC141353
0.821 Intermediate Similarity NPC280548
0.8208 Intermediate Similarity NPC11445
0.8204 Intermediate Similarity NPC48938
0.8204 Intermediate Similarity NPC469358
0.8199 Intermediate Similarity NPC109447
0.8198 Intermediate Similarity NPC474177
0.8187 Intermediate Similarity NPC90723
0.8176 Intermediate Similarity NPC198988
0.8165 Intermediate Similarity NPC236711
0.8153 Intermediate Similarity NPC38736
0.8153 Intermediate Similarity NPC470507
0.815 Intermediate Similarity NPC133366
0.8148 Intermediate Similarity NPC317430
0.8146 Intermediate Similarity NPC59084
0.8146 Intermediate Similarity NPC2949
0.814 Intermediate Similarity NPC477167
0.814 Intermediate Similarity NPC99666
0.814 Intermediate Similarity NPC473342
0.8129 Intermediate Similarity NPC187951
0.8125 Intermediate Similarity NPC470203
0.8118 Intermediate Similarity NPC46580
0.8118 Intermediate Similarity NPC17059
0.8114 Intermediate Similarity NPC473640
0.8114 Intermediate Similarity NPC171317
0.811 Intermediate Similarity NPC472123
0.8099 Intermediate Similarity NPC41174
0.8095 Intermediate Similarity NPC475450
0.8092 Intermediate Similarity NPC473868
0.8092 Intermediate Similarity NPC63157
0.8072 Intermediate Similarity NPC184964
0.8069 Intermediate Similarity NPC471311
0.8069 Intermediate Similarity NPC471313
0.8068 Intermediate Similarity NPC100321
0.8068 Intermediate Similarity NPC293917
0.8063 Intermediate Similarity NPC215584
0.8063 Intermediate Similarity NPC44773
0.8063 Intermediate Similarity NPC470204
0.8061 Intermediate Similarity NPC189812
0.8061 Intermediate Similarity NPC329688
0.8059 Intermediate Similarity NPC315555
0.8059 Intermediate Similarity NPC62749
0.8057 Intermediate Similarity NPC227582
0.8052 Intermediate Similarity NPC470440
0.8035 Intermediate Similarity NPC324149
0.8025 Intermediate Similarity NPC470508
0.8013 Intermediate Similarity NPC124005
0.8011 Intermediate Similarity NPC470499
0.8011 Intermediate Similarity NPC265576
0.8 Intermediate Similarity NPC34508
0.8 Intermediate Similarity NPC316069
0.8 Intermediate Similarity NPC250361
0.7989 Intermediate Similarity NPC307963
0.7978 Intermediate Similarity NPC300183
0.7978 Intermediate Similarity NPC475506
0.7976 Intermediate Similarity NPC16659
0.7964 Intermediate Similarity NPC96890
0.7963 Intermediate Similarity NPC476118
0.7963 Intermediate Similarity NPC317105
0.7961 Intermediate Similarity NPC88097
0.7959 Intermediate Similarity NPC473587

  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 NPC25008 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
0.9156 High Similarity NPD4184 Clinical (unspecified phase)
0.9091 High Similarity NPD786 Approved
0.9014 High Similarity NPD198 Clinical (unspecified phase)
0.8861 High Similarity NPD5065 Approved
0.8836 High Similarity NPD1722 Approved
0.8758 High Similarity NPD6595 Phase 3
0.875 High Similarity NPD2144 Approved
0.8733 High Similarity NPD3100 Discontinued
0.8688 High Similarity NPD749 Clinical (unspecified phase)
0.8675 High Similarity NPD2172 Phase 1
0.865 High Similarity NPD5728 Clinical (unspecified phase)
0.8625 High Similarity NPD482 Approved
0.8609 High Similarity NPD4374 Clinical (unspecified phase)
0.8589 High Similarity NPD3038 Discontinued
0.8554 High Similarity NPD8431 Approved
0.8545 High Similarity NPD6610 Clinical (unspecified phase)
0.8537 High Similarity NPD2094 Phase 2
0.8537 High Similarity NPD2095 Phase 2
0.8537 High Similarity NPD2092 Phase 2
0.8519 High Similarity NPD6203 Clinical (unspecified phase)
0.8503 High Similarity NPD8110 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD2091 Phase 2
0.8485 Intermediate Similarity NPD2096 Phase 2
0.8466 Intermediate Similarity NPD4076 Approved
0.8466 Intermediate Similarity NPD4079 Approved
0.8431 Intermediate Similarity NPD4462 Approved
0.8431 Intermediate Similarity NPD4463 Approved
0.8405 Intermediate Similarity NPD3506 Approved
0.8405 Intermediate Similarity NPD3505 Approved
0.8333 Intermediate Similarity NPD750 Phase 2
0.8323 Intermediate Similarity NPD2837 Discontinued
0.8301 Intermediate Similarity NPD4703 Approved
0.8301 Intermediate Similarity NPD4702 Approved
0.8291 Intermediate Similarity NPD1404 Approved
0.8291 Intermediate Similarity NPD1403 Approved
0.8282 Intermediate Similarity NPD4128 Approved
0.8212 Intermediate Similarity NPD1592 Phase 3
0.821 Intermediate Similarity NPD1325 Approved
0.821 Intermediate Similarity NPD1326 Approved
0.8199 Intermediate Similarity NPD2639 Approved
0.8199 Intermediate Similarity NPD2642 Approved
0.8187 Intermediate Similarity NPD3323 Discontinued
0.8182 Intermediate Similarity NPD4181 Approved
0.8148 Intermediate Similarity NPD2640 Approved
0.8148 Intermediate Similarity NPD2641 Approved
0.8148 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.8146 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD4075 Phase 2
0.8121 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.8057 Intermediate Similarity NPD7948 Phase 1
0.8049 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD3717 Discontinued
0.7989 Intermediate Similarity NPD1038 Approved
0.7987 Intermediate Similarity NPD5254 Discontinued
0.7976 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD5138 Approved
0.7963 Intermediate Similarity NPD5140 Approved
0.7959 Intermediate Similarity NPD3654 Approved
0.7939 Intermediate Similarity NPD3609 Approved
0.7939 Intermediate Similarity NPD3610 Approved
0.7933 Intermediate Similarity NPD8073 Approved
0.7927 Intermediate Similarity NPD4640 Approved
0.7927 Intermediate Similarity NPD4639 Approved
0.7927 Intermediate Similarity NPD4638 Approved
0.7922 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD8386 Phase 2
0.7907 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD3961 Discontinued
0.7905 Intermediate Similarity NPD3476 Approved
0.7905 Intermediate Similarity NPD3475 Approved
0.7901 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD8072 Approved
0.7886 Intermediate Similarity NPD802 Phase 2
0.7845 Intermediate Similarity NPD8272 Phase 2
0.7841 Intermediate Similarity NPD7618 Phase 3
0.7841 Intermediate Similarity NPD7619 Phase 3
0.7836 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD1661 Suspended
0.7834 Intermediate Similarity NPD4547 Phase 3
0.7829 Intermediate Similarity NPD3404 Approved
0.7823 Intermediate Similarity NPD991 Phase 2
0.7823 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD2119 Approved
0.7823 Intermediate Similarity NPD2118 Approved
0.7818 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD2006 Phase 2
0.7802 Intermediate Similarity NPD7957 Phase 1
0.7802 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD2430 Phase 2
0.7784 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD2580 Discontinued
0.776 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD3385 Approved
0.7746 Intermediate Similarity NPD6217 Discontinued
0.7746 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD5021 Discontinued
0.7701 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD8026 Phase 1
0.7679 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD5106 Approved
0.7674 Intermediate Similarity NPD5105 Approved
0.7669 Intermediate Similarity NPD5255 Approved
0.7663 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1683 Approved
0.7654 Intermediate Similarity NPD6664 Approved
0.765 Intermediate Similarity NPD5426 Phase 3
0.765 Intermediate Similarity NPD5901 Discontinued
0.7634 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD4030 Approved
0.7632 Intermediate Similarity NPD4029 Approved
0.7632 Intermediate Similarity NPD4028 Approved
0.7624 Intermediate Similarity NPD484 Approved
0.7619 Intermediate Similarity NPD3116 Approved
0.7619 Intermediate Similarity NPD3117 Approved
0.7609 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD1262 Discovery
0.7594 Intermediate Similarity NPD7470 Discontinued
0.7594 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD2165 Phase 1
0.7578 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6158 Phase 2
0.7578 Intermediate Similarity NPD2882 Phase 1
0.7576 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD2391 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD1554 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD8093 Discontinued
0.7553 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD2896 Discontinued
0.7547 Intermediate Similarity NPD7469 Discontinued
0.7546 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD3113 Approved
0.7546 Intermediate Similarity NPD3112 Approved
0.7546 Intermediate Similarity NPD3114 Approved
0.7546 Intermediate Similarity NPD3115 Approved
0.7545 Intermediate Similarity NPD1248 Discontinued
0.754 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD8129 Discovery
0.7529 Intermediate Similarity NPD2928 Phase 2
0.7529 Intermediate Similarity NPD6178 Phase 3
0.7528 Intermediate Similarity NPD4615 Phase 2
0.7517 Intermediate Similarity NPD9583 Approved
0.7516 Intermediate Similarity NPD3833 Phase 3
0.7516 Intermediate Similarity NPD3944 Approved
0.7516 Intermediate Similarity NPD3835 Phase 3
0.7516 Intermediate Similarity NPD3942 Approved
0.7514 Intermediate Similarity NPD1707 Approved
0.7514 Intermediate Similarity NPD1708 Approved
0.7513 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD8094 Discontinued
0.75 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5862 Discovery
0.75 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2390 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2844 Phase 3
0.7486 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD5100 Phase 3
0.7474 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD3825 Phase 3
0.7472 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD1332 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD5315 Discontinued
0.7469 Intermediate Similarity NPD3262 Approved
0.7456 Intermediate Similarity NPD5436 Phase 1
0.7444 Intermediate Similarity NPD7944 Discontinued
0.7443 Intermediate Similarity NPD706 Phase 1
0.7442 Intermediate Similarity NPD8123 Approved
0.7442 Intermediate Similarity NPD8122 Approved
0.744 Intermediate Similarity NPD5611 Phase 2
0.7439 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD3813 Approved
0.7417 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD6281 Approved
0.7415 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD271 Approved
0.7415 Intermediate Similarity NPD268 Approved
0.7414 Intermediate Similarity NPD3178 Discontinued
0.7414 Intermediate Similarity NPD1895 Discontinued
0.7407 Intermediate Similarity NPD5066 Phase 2
0.7407 Intermediate Similarity NPD5067 Phase 2
0.7405 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2581 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