Structure

Physi-Chem Properties

Molecular Weight:  456.36
Volume:  505.751
LogP:  6.523
LogD:  5.083
LogS:  -5.734
# Rotatable Bonds:  4
TPSA:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.377
Synthetic Accessibility Score:  4.952
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.932
MDCK Permeability:  1.2131174116802868e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.978
30% Bioavailability (F30%):  0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  96.37886810302734%
Volume Distribution (VD):  1.127
Pgp-substrate:  2.030327796936035%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.476
CYP2C19-inhibitor:  0.103
CYP2C19-substrate:  0.951
CYP2C9-inhibitor:  0.241
CYP2C9-substrate:  0.149
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.14
CYP3A4-inhibitor:  0.772
CYP3A4-substrate:  0.886

ADMET: Excretion

Clearance (CL):  7.043
Half-life (T1/2):  0.101

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.303
Drug-inuced Liver Injury (DILI):  0.044
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.529
Maximum Recommended Daily Dose:  0.864
Skin Sensitization:  0.167
Carcinogencity:  0.214
Eye Corrosion:  0.022
Eye Irritation:  0.058
Respiratory Toxicity:  0.981

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

  Natural Product: NPC262870

Natural Product ID:  NPC262870
Common Name*:   Niloticin
IUPAC Name:   (5R,9R,10R,13S,14S,17S)-17-[(2R,4R)-4-[(2S)-3,3-dimethyloxiran-2-yl]-4-hydroxybutan-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:   Niloticin
Standard InCHIKey:  GKQMMZUXYRXFOH-VRUJEOEASA-N
Standard InCHI:  InChI=1S/C30H48O3/c1-18(17-22(31)25-27(4,5)33-25)19-11-15-30(8)21-9-10-23-26(2,3)24(32)13-14-28(23,6)20(21)12-16-29(19,30)7/h9,18-20,22-23,25,31H,10-17H2,1-8H3/t18-,19+,20+,22-,23+,25+,28-,29+,30-/m1/s1
SMILES:  C[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C[C@H]([C@@H]1OC1(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460656
PubChem CID:   44559946
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. xylem n.a. DOI[10.1248/cpb.24.1532]
NPO10752 Dysoxylum variabile Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[11429992]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota Roots n.a. n.a. PMID[14575431]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. root n.a. PMID[1800638]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19919052]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[22224661]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[22799262]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[23290052]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[24467387]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[25066952]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota stem barks n.a. n.a. PMID[25666824]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25905468]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22242.1 Phellodendron chinense var. glabriusculum Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24689 Turraea nilotica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242.1 Phellodendron chinense var. glabriusculum Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27463 Aglaia leucophylla Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10752 Dysoxylum variabile Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27463 Aglaia leucophylla Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24689 Turraea nilotica Species Meliaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 8.4 ug.mL-1 PMID[496429]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 72.03 % PMID[496430]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 113.71 % PMID[496430]

☑ 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 NPC262870 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
0.977 High Similarity NPC67831
0.977 High Similarity NPC174051
0.9302 High Similarity NPC90652
0.9195 High Similarity NPC470417
0.908 High Similarity NPC469322
0.8966 High Similarity NPC473168
0.8936 High Similarity NPC476897
0.8901 High Similarity NPC318332
0.8876 High Similarity NPC32830
0.883 High Similarity NPC167974
0.8764 High Similarity NPC44181
0.875 High Similarity NPC125399
0.875 High Similarity NPC89077
0.8736 High Similarity NPC221758
0.8736 High Similarity NPC85774
0.8736 High Similarity NPC59453
0.8736 High Similarity NPC82902
0.8736 High Similarity NPC214043
0.8646 High Similarity NPC473928
0.8636 High Similarity NPC471224
0.8636 High Similarity NPC474218
0.8587 High Similarity NPC274046
0.8587 High Similarity NPC198074
0.8571 High Similarity NPC171441
0.8539 High Similarity NPC145879
0.8539 High Similarity NPC51014
0.8539 High Similarity NPC31564
0.8539 High Similarity NPC474732
0.8539 High Similarity NPC474778
0.8539 High Similarity NPC469994
0.8539 High Similarity NPC474733
0.8523 High Similarity NPC473246
0.8506 High Similarity NPC151519
0.8469 Intermediate Similarity NPC149124
0.8469 Intermediate Similarity NPC75531
0.8469 Intermediate Similarity NPC100955
0.8469 Intermediate Similarity NPC121566
0.8462 Intermediate Similarity NPC476733
0.8462 Intermediate Similarity NPC215029
0.8462 Intermediate Similarity NPC76879
0.8462 Intermediate Similarity NPC1015
0.8462 Intermediate Similarity NPC31985
0.8462 Intermediate Similarity NPC2983
0.8462 Intermediate Similarity NPC474245
0.8444 Intermediate Similarity NPC475740
0.8444 Intermediate Similarity NPC474174
0.8444 Intermediate Similarity NPC251808
0.8444 Intermediate Similarity NPC58063
0.8444 Intermediate Similarity NPC317590
0.8427 Intermediate Similarity NPC474083
0.8427 Intermediate Similarity NPC469948
0.8409 Intermediate Similarity NPC86370
0.8387 Intermediate Similarity NPC474736
0.8384 Intermediate Similarity NPC63023
0.8384 Intermediate Similarity NPC95243
0.8372 Intermediate Similarity NPC215843
0.837 Intermediate Similarity NPC320026
0.8353 Intermediate Similarity NPC325946
0.8352 Intermediate Similarity NPC328313
0.8352 Intermediate Similarity NPC255176
0.8352 Intermediate Similarity NPC193360
0.8351 Intermediate Similarity NPC473174
0.8333 Intermediate Similarity NPC155011
0.8315 Intermediate Similarity NPC237712
0.8315 Intermediate Similarity NPC161423
0.8315 Intermediate Similarity NPC58841
0.8315 Intermediate Similarity NPC227064
0.8315 Intermediate Similarity NPC321187
0.8315 Intermediate Similarity NPC329043
0.83 Intermediate Similarity NPC144459
0.8298 Intermediate Similarity NPC473172
0.8295 Intermediate Similarity NPC212083
0.8283 Intermediate Similarity NPC471293
0.828 Intermediate Similarity NPC475806
0.828 Intermediate Similarity NPC154101
0.828 Intermediate Similarity NPC473166
0.828 Intermediate Similarity NPC189520
0.8276 Intermediate Similarity NPC472478
0.8265 Intermediate Similarity NPC473163
0.8261 Intermediate Similarity NPC474704
0.8261 Intermediate Similarity NPC309603
0.8261 Intermediate Similarity NPC473999
0.8261 Intermediate Similarity NPC326627
0.8261 Intermediate Similarity NPC268406
0.8261 Intermediate Similarity NPC477943
0.8261 Intermediate Similarity NPC475921
0.8261 Intermediate Similarity NPC310010
0.8261 Intermediate Similarity NPC186688
0.8261 Intermediate Similarity NPC474570
0.8261 Intermediate Similarity NPC26959
0.8256 Intermediate Similarity NPC82635
0.8247 Intermediate Similarity NPC83709
0.8242 Intermediate Similarity NPC474684
0.8242 Intermediate Similarity NPC93778
0.8242 Intermediate Similarity NPC138756
0.8242 Intermediate Similarity NPC142361
0.8242 Intermediate Similarity NPC96496
0.8242 Intermediate Similarity NPC99909
0.8222 Intermediate Similarity NPC474349
0.8222 Intermediate Similarity NPC474189
0.8222 Intermediate Similarity NPC470574
0.8222 Intermediate Similarity NPC202868
0.8211 Intermediate Similarity NPC469599
0.8211 Intermediate Similarity NPC473170
0.8202 Intermediate Similarity NPC278648
0.8202 Intermediate Similarity NPC470046
0.8202 Intermediate Similarity NPC470047
0.8202 Intermediate Similarity NPC476082
0.8191 Intermediate Similarity NPC470224
0.8182 Intermediate Similarity NPC239716
0.8182 Intermediate Similarity NPC147066
0.8173 Intermediate Similarity NPC317210
0.8172 Intermediate Similarity NPC471896
0.8172 Intermediate Similarity NPC48010
0.8161 Intermediate Similarity NPC328714
0.8152 Intermediate Similarity NPC53911
0.8152 Intermediate Similarity NPC471722
0.8152 Intermediate Similarity NPC328539
0.8132 Intermediate Similarity NPC222613
0.8132 Intermediate Similarity NPC470050
0.8132 Intermediate Similarity NPC20688
0.8132 Intermediate Similarity NPC118648
0.8132 Intermediate Similarity NPC470051
0.8132 Intermediate Similarity NPC72133
0.8132 Intermediate Similarity NPC475022
0.8132 Intermediate Similarity NPC327115
0.8132 Intermediate Similarity NPC324063
0.8132 Intermediate Similarity NPC94755
0.8125 Intermediate Similarity NPC473164
0.8125 Intermediate Similarity NPC49371
0.8125 Intermediate Similarity NPC471777
0.8111 Intermediate Similarity NPC472265
0.8111 Intermediate Similarity NPC474047
0.8111 Intermediate Similarity NPC165064
0.8111 Intermediate Similarity NPC473157
0.8105 Intermediate Similarity NPC8993
0.81 Intermediate Similarity NPC255309
0.809 Intermediate Similarity NPC145143
0.809 Intermediate Similarity NPC193347
0.809 Intermediate Similarity NPC477858
0.809 Intermediate Similarity NPC30166
0.8085 Intermediate Similarity NPC155304
0.8085 Intermediate Similarity NPC272746
0.8085 Intermediate Similarity NPC19114
0.8085 Intermediate Similarity NPC473998
0.8081 Intermediate Similarity NPC185530
0.8068 Intermediate Similarity NPC2482
0.8065 Intermediate Similarity NPC275740
0.8065 Intermediate Similarity NPC86319
0.8061 Intermediate Similarity NPC112167
0.8058 Intermediate Similarity NPC154856
0.8058 Intermediate Similarity NPC475317
0.8058 Intermediate Similarity NPC52241
0.8058 Intermediate Similarity NPC76084
0.8043 Intermediate Similarity NPC472482
0.8043 Intermediate Similarity NPC469317
0.8043 Intermediate Similarity NPC159046
0.8043 Intermediate Similarity NPC233836
0.8043 Intermediate Similarity NPC241875
0.8043 Intermediate Similarity NPC136548
0.8043 Intermediate Similarity NPC472481
0.8043 Intermediate Similarity NPC469314
0.8043 Intermediate Similarity NPC187376
0.8043 Intermediate Similarity NPC472484
0.8043 Intermediate Similarity NPC167877
0.8041 Intermediate Similarity NPC475894
0.8041 Intermediate Similarity NPC107243
0.8041 Intermediate Similarity NPC57416
0.8039 Intermediate Similarity NPC258323
0.8022 Intermediate Similarity NPC283733
0.8022 Intermediate Similarity NPC470223
0.8021 Intermediate Similarity NPC180557
0.8021 Intermediate Similarity NPC271195
0.8021 Intermediate Similarity NPC279974
0.8021 Intermediate Similarity NPC469329
0.8021 Intermediate Similarity NPC473415
0.8021 Intermediate Similarity NPC30677
0.8021 Intermediate Similarity NPC37787
0.802 Intermediate Similarity NPC162033
0.802 Intermediate Similarity NPC96377
0.8 Intermediate Similarity NPC107674
0.8 Intermediate Similarity NPC117185
0.8 Intermediate Similarity NPC141497
0.8 Intermediate Similarity NPC12722
0.8 Intermediate Similarity NPC472942
0.8 Intermediate Similarity NPC472930
0.8 Intermediate Similarity NPC475255
0.8 Intermediate Similarity NPC474807
0.8 Intermediate Similarity NPC475789
0.8 Intermediate Similarity NPC26478
0.8 Intermediate Similarity NPC109305
0.8 Intermediate Similarity NPC170220
0.8 Intermediate Similarity NPC191892
0.8 Intermediate Similarity NPC233118
0.7979 Intermediate Similarity NPC289213
0.7979 Intermediate Similarity NPC191684
0.7979 Intermediate Similarity NPC111585
0.7979 Intermediate Similarity NPC126993
0.7979 Intermediate Similarity NPC148414
0.7979 Intermediate Similarity NPC69622

  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 NPC262870 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
0.8736 High Similarity NPD4786 Approved
0.8506 High Similarity NPD3667 Approved
0.8315 Intermediate Similarity NPD3133 Approved
0.8315 Intermediate Similarity NPD3665 Phase 1
0.8315 Intermediate Similarity NPD3666 Approved
0.8261 Intermediate Similarity NPD5328 Approved
0.8261 Intermediate Similarity NPD4753 Phase 2
0.8229 Intermediate Similarity NPD6083 Phase 2
0.8229 Intermediate Similarity NPD6084 Phase 2
0.8191 Intermediate Similarity NPD6399 Phase 3
0.8132 Intermediate Similarity NPD3618 Phase 1
0.809 Intermediate Similarity NPD4221 Approved
0.809 Intermediate Similarity NPD4223 Phase 3
0.8085 Intermediate Similarity NPD6079 Approved
0.8022 Intermediate Similarity NPD5329 Approved
0.8 Intermediate Similarity NPD4202 Approved
0.7944 Intermediate Similarity NPD7115 Discovery
0.7941 Intermediate Similarity NPD6412 Phase 2
0.7935 Intermediate Similarity NPD6684 Approved
0.7935 Intermediate Similarity NPD7146 Approved
0.7935 Intermediate Similarity NPD7521 Approved
0.7935 Intermediate Similarity NPD7334 Approved
0.7935 Intermediate Similarity NPD6409 Approved
0.7935 Intermediate Similarity NPD5330 Approved
0.7935 Intermediate Similarity NPD5279 Phase 3
0.7912 Intermediate Similarity NPD4197 Approved
0.7857 Intermediate Similarity NPD4755 Approved
0.7843 Intermediate Similarity NPD7128 Approved
0.7843 Intermediate Similarity NPD5739 Approved
0.7843 Intermediate Similarity NPD6675 Approved
0.7843 Intermediate Similarity NPD6402 Approved
0.7835 Intermediate Similarity NPD5695 Phase 3
0.7835 Intermediate Similarity NPD4629 Approved
0.7835 Intermediate Similarity NPD5210 Approved
0.7802 Intermediate Similarity NPD4788 Approved
0.7778 Intermediate Similarity NPD5696 Approved
0.7766 Intermediate Similarity NPD5737 Approved
0.7766 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD6672 Approved
0.7766 Intermediate Similarity NPD6903 Approved
0.7742 Intermediate Similarity NPD6098 Approved
0.7742 Intermediate Similarity NPD4689 Approved
0.7742 Intermediate Similarity NPD4138 Approved
0.7742 Intermediate Similarity NPD5205 Approved
0.7742 Intermediate Similarity NPD4693 Phase 3
0.7742 Intermediate Similarity NPD4688 Approved
0.7742 Intermediate Similarity NPD4690 Approved
0.7736 Intermediate Similarity NPD8297 Approved
0.7717 Intermediate Similarity NPD3668 Phase 3
0.7701 Intermediate Similarity NPD6942 Approved
0.7701 Intermediate Similarity NPD7339 Approved
0.77 Intermediate Similarity NPD5286 Approved
0.77 Intermediate Similarity NPD4700 Approved
0.77 Intermediate Similarity NPD4696 Approved
0.77 Intermediate Similarity NPD5285 Approved
0.7692 Intermediate Similarity NPD6881 Approved
0.7692 Intermediate Similarity NPD6899 Approved
0.7692 Intermediate Similarity NPD7320 Approved
0.7619 Intermediate Similarity NPD6372 Approved
0.7619 Intermediate Similarity NPD6373 Approved
0.7614 Intermediate Similarity NPD6933 Approved
0.7596 Intermediate Similarity NPD5697 Approved
0.7596 Intermediate Similarity NPD5701 Approved
0.7576 Intermediate Similarity NPD5221 Approved
0.7576 Intermediate Similarity NPD5222 Approved
0.7576 Intermediate Similarity NPD4697 Phase 3
0.7576 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD5690 Phase 2
0.7553 Intermediate Similarity NPD5280 Approved
0.7553 Intermediate Similarity NPD4694 Approved
0.7549 Intermediate Similarity NPD4633 Approved
0.7549 Intermediate Similarity NPD5226 Approved
0.7549 Intermediate Similarity NPD5224 Approved
0.7549 Intermediate Similarity NPD5211 Phase 2
0.7549 Intermediate Similarity NPD5225 Approved
0.7547 Intermediate Similarity NPD7290 Approved
0.7547 Intermediate Similarity NPD6883 Approved
0.7547 Intermediate Similarity NPD7102 Approved
0.75 Intermediate Similarity NPD6904 Approved
0.75 Intermediate Similarity NPD5173 Approved
0.75 Intermediate Similarity NPD6080 Approved
0.75 Intermediate Similarity NPD6673 Approved
0.7477 Intermediate Similarity NPD6650 Approved
0.7477 Intermediate Similarity NPD6617 Approved
0.7477 Intermediate Similarity NPD6869 Approved
0.7477 Intermediate Similarity NPD6649 Approved
0.7477 Intermediate Similarity NPD6847 Approved
0.7477 Intermediate Similarity NPD8130 Phase 1
0.7476 Intermediate Similarity NPD5174 Approved
0.7476 Intermediate Similarity NPD5175 Approved
0.7475 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7524 Approved
0.7473 Intermediate Similarity NPD7525 Registered
0.7453 Intermediate Similarity NPD6012 Approved
0.7453 Intermediate Similarity NPD6013 Approved
0.7453 Intermediate Similarity NPD6014 Approved
0.7451 Intermediate Similarity NPD5223 Approved
0.7447 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD3617 Approved
0.7416 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6882 Approved
0.7404 Intermediate Similarity NPD5141 Approved
0.7396 Intermediate Similarity NPD5208 Approved
0.7391 Intermediate Similarity NPD4692 Approved
0.7391 Intermediate Similarity NPD4139 Approved
0.7386 Intermediate Similarity NPD6924 Approved
0.7386 Intermediate Similarity NPD6926 Approved
0.7383 Intermediate Similarity NPD4634 Approved
0.7374 Intermediate Similarity NPD7748 Approved
0.7368 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD4195 Approved
0.7358 Intermediate Similarity NPD6011 Approved
0.7356 Intermediate Similarity NPD4243 Approved
0.7347 Intermediate Similarity NPD7515 Phase 2
0.7339 Intermediate Similarity NPD4632 Approved
0.7333 Intermediate Similarity NPD4767 Approved
0.7333 Intermediate Similarity NPD4768 Approved
0.7315 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4754 Approved
0.7257 Intermediate Similarity NPD6054 Approved
0.7257 Intermediate Similarity NPD6059 Approved
0.7257 Intermediate Similarity NPD6319 Approved
0.7241 Intermediate Similarity NPD4747 Approved
0.7234 Intermediate Similarity NPD6695 Phase 3
0.72 Intermediate Similarity NPD6001 Approved
0.7196 Intermediate Similarity NPD5128 Approved
0.7196 Intermediate Similarity NPD4729 Approved
0.7196 Intermediate Similarity NPD4730 Approved
0.7191 Intermediate Similarity NPD4784 Approved
0.7191 Intermediate Similarity NPD4785 Approved
0.7188 Intermediate Similarity NPD4519 Discontinued
0.7188 Intermediate Similarity NPD4623 Approved
0.7174 Intermediate Similarity NPD7645 Phase 2
0.7172 Intermediate Similarity NPD8035 Phase 2
0.7172 Intermediate Similarity NPD5284 Approved
0.7172 Intermediate Similarity NPD8034 Phase 2
0.7172 Intermediate Similarity NPD6050 Approved
0.7172 Intermediate Similarity NPD5281 Approved
0.7172 Intermediate Similarity NPD5693 Phase 1
0.717 Intermediate Similarity NPD6008 Approved
0.7159 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7902 Approved
0.713 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6370 Approved
0.7126 Intermediate Similarity NPD4137 Phase 3
0.71 Intermediate Similarity NPD5133 Approved
0.7097 Intermediate Similarity NPD4695 Discontinued
0.7097 Intermediate Similarity NPD6930 Phase 2
0.7097 Intermediate Similarity NPD6931 Approved
0.7087 Intermediate Similarity NPD7638 Approved
0.7071 Intermediate Similarity NPD5207 Approved
0.7071 Intermediate Similarity NPD4096 Approved
0.7071 Intermediate Similarity NPD5692 Phase 3
0.7069 Intermediate Similarity NPD7604 Phase 2
0.7064 Intermediate Similarity NPD5249 Phase 3
0.7064 Intermediate Similarity NPD5250 Approved
0.7064 Intermediate Similarity NPD5251 Approved
0.7064 Intermediate Similarity NPD5247 Approved
0.7064 Intermediate Similarity NPD5248 Approved
0.7059 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6274 Approved
0.7045 Intermediate Similarity NPD4789 Approved
0.7045 Intermediate Similarity NPD4691 Approved
0.7045 Intermediate Similarity NPD4245 Approved
0.7045 Intermediate Similarity NPD4244 Approved
0.7043 Intermediate Similarity NPD6015 Approved
0.7043 Intermediate Similarity NPD6016 Approved
0.7037 Intermediate Similarity NPD6686 Approved
0.7019 Intermediate Similarity NPD7640 Approved
0.7019 Intermediate Similarity NPD7639 Approved
0.7018 Intermediate Similarity NPD7101 Approved
0.7018 Intermediate Similarity NPD7100 Approved
0.7011 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7492 Approved
0.7 Intermediate Similarity NPD5215 Approved
0.7 Intermediate Similarity NPD5694 Approved
0.7 Intermediate Similarity NPD5217 Approved
0.7 Intermediate Similarity NPD5216 Approved
0.7 Intermediate Similarity NPD5733 Approved
0.7 Intermediate Similarity NPD6411 Approved
0.6991 Remote Similarity NPD6009 Approved
0.6989 Remote Similarity NPD6929 Approved
0.6983 Remote Similarity NPD5988 Approved
0.697 Remote Similarity NPD6051 Approved
0.6957 Remote Similarity NPD6932 Approved
0.6949 Remote Similarity NPD6616 Approved
0.6939 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6939 Remote Similarity NPD7750 Discontinued
0.6932 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3698 Phase 2
0.6932 Remote Similarity NPD6922 Approved
0.6932 Remote Similarity NPD6923 Approved
0.693 Remote Similarity NPD6335 Approved
0.6923 Remote Similarity NPD4190 Phase 3
0.6923 Remote Similarity NPD5275 Approved
0.6909 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6909 Remote Similarity NPD5135 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