Structure

Physi-Chem Properties

Molecular Weight:  1060.55
Volume:  1019.052
LogP:  0.969
LogD:  0.383
LogS:  -3.265
# Rotatable Bonds:  13
TPSA:  342.9
# H-Bond Aceptor:  22
# H-Bond Donor:  12
# Rings:  9
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.094
Synthetic Accessibility Score:  7.404
Fsp3:  0.942
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
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:  -6.304
MDCK Permeability:  0.00011185779294464737
Pgp-inhibitor:  0.088
Pgp-substrate:  0.995
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  0.079
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.21
Plasma Protein Binding (PPB):  65.27811431884766%
Volume Distribution (VD):  -0.054
Pgp-substrate:  11.469573020935059%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.993
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.52
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.001
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.014
CYP3A4-inhibitor:  0.068
CYP3A4-substrate:  0.027

ADMET: Excretion

Clearance (CL):  0.187
Half-life (T1/2):  0.847

ADMET: Toxicity

hERG Blockers:  0.286
Human Hepatotoxicity (H-HT):  0.185
Drug-inuced Liver Injury (DILI):  0.015
AMES Toxicity:  0.084
Rat Oral Acute Toxicity:  0.169
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.204
Carcinogencity:  0.213
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.95

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

  Natural Product: NPC131824

Natural Product ID:  NPC131824
Common Name*:   (23S)-17Alpha,23-Epoxy-29-Hydroxy-3Beta-[(O-Alpha-L-Rhamnopyranosyl-(1->2)-O-Beta-D-Glucopyranosyl-(1->2)-O-Alpha-L-Arabinopyranosyl-(1->6)-Beta-D-Glucopyranosyl)Oxy]-27-Norlanost-8-En-24-One
IUPAC Name:   1-[(2'S,3S,4S,4'R,5R,10S,13S,14S,17S)-3-[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(hydroxymethyl)-4,4',10,13,14-pentamethylspiro[1,2,3,5,6,7,11,12,15,16-decahydrocyclopenta[a]phenanthrene-17,5'-oxolane]-2'-yl]propan-1-one
Synonyms:  
Standard InCHIKey:  HSEIJEWAYARWCQ-QWCYNRMUSA-N
Standard InCHI:  InChI=1S/C52H84O22/c1-8-26(55)28-17-22(2)52(74-28)16-15-50(6)25-9-10-31-48(4,24(25)11-14-51(50,52)7)13-12-32(49(31,5)21-54)71-45-41(65)38(62)36(60)30(70-45)20-67-46-42(34(58)27(56)19-66-46)73-47-43(39(63)35(59)29(18-53)69-47)72-44-40(64)37(61)33(57)23(3)68-44/h22-23,27-47,53-54,56-65H,8-21H2,1-7H3/t22-,23+,27+,28+,29-,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40-,41-,42-,43-,44+,45+,46+,47+,48-,49-,50+,51+,52+/m1/s1
SMILES:  CCC(=O)[C@@H]1C[C@@H](C)[C@]2(CC[C@@]3(C)C4=C(CC[C@]23C)[C@@]2(C)CC[C@@H]([C@](C)(CO)[C@@H]2CC4)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)O)O)O)O1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL486617
PubChem CID:   21632991
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
NPO9383 Scilla scilloides Species Hyacinthaceae Eukaryota n.a. bulb n.a. PMID[12237544]
NPO9251 Muscari paradoxum Species Hyacinthaceae Eukaryota bulbs n.a. n.a. PMID[15620262]
NPO28718 Penicillium terrestre Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18163588]
NPO29396 Bidens bipinnata Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[25282892]
NPO29250 Coprinus comatus Species Agaricaceae Eukaryota n.a. n.a. n.a. PMID[26338495]
NPO9383 Scilla scilloides Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29396 Bidens bipinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29125 Ulex europaeus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29125 Ulex europaeus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9251 Muscari paradoxum Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9383 Scilla scilloides Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29396 Bidens bipinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29213 Bulbine narcissifolia Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29278 Sicyos angulatus Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28718 Penicillium terrestre Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29534 Sarcomelicope leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9251 Muscari paradoxum Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29396 Bidens bipinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29250 Coprinus comatus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29481 Streptomyces reticuli Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29499 Chionodoxa luciliae n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29125 Ulex europaeus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11162 Aplidium glabrum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18245 Coprinellus micaceus Species Psathyrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9383 Scilla scilloides Species Hyacinthaceae 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
NPT924 Cell Line HSC-2 Homo sapiens IC50 = 32000.0 nM PMID[548470]

☑ 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 NPC131824 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
0.9912 High Similarity NPC228701
0.9739 High Similarity NPC104427
0.9655 High Similarity NPC292290
0.9487 High Similarity NPC2757
0.906 High Similarity NPC476543
0.906 High Similarity NPC476544
0.906 High Similarity NPC476545
0.8898 High Similarity NPC182900
0.8898 High Similarity NPC249553
0.8833 High Similarity NPC190846
0.8833 High Similarity NPC473505
0.8833 High Similarity NPC277191
0.8824 High Similarity NPC94072
0.8824 High Similarity NPC15918
0.8824 High Similarity NPC169816
0.8824 High Similarity NPC305771
0.8783 High Similarity NPC477074
0.878 High Similarity NPC241008
0.875 High Similarity NPC476542
0.8729 High Similarity NPC161738
0.872 High Similarity NPC478069
0.871 High Similarity NPC473805
0.871 High Similarity NPC473519
0.8678 High Similarity NPC130229
0.864 High Similarity NPC102015
0.864 High Similarity NPC475487
0.8632 High Similarity NPC279638
0.8618 High Similarity NPC69273
0.8618 High Similarity NPC293623
0.8618 High Similarity NPC168899
0.8609 High Similarity NPC477073
0.8583 High Similarity NPC476672
0.8547 High Similarity NPC474557
0.8525 High Similarity NPC476674
0.85 High Similarity NPC108072
0.8455 Intermediate Similarity NPC273962
0.8455 Intermediate Similarity NPC476673
0.845 Intermediate Similarity NPC477233
0.845 Intermediate Similarity NPC477232
0.8443 Intermediate Similarity NPC256983
0.8435 Intermediate Similarity NPC477070
0.8435 Intermediate Similarity NPC477069
0.843 Intermediate Similarity NPC475182
0.843 Intermediate Similarity NPC187950
0.843 Intermediate Similarity NPC278163
0.843 Intermediate Similarity NPC42675
0.8376 Intermediate Similarity NPC210420
0.8376 Intermediate Similarity NPC474265
0.8376 Intermediate Similarity NPC130427
0.8376 Intermediate Similarity NPC233003
0.8374 Intermediate Similarity NPC475194
0.8374 Intermediate Similarity NPC248202
0.8348 Intermediate Similarity NPC475319
0.8348 Intermediate Similarity NPC92890
0.8348 Intermediate Similarity NPC202898
0.8347 Intermediate Similarity NPC475187
0.8347 Intermediate Similarity NPC129393
0.8347 Intermediate Similarity NPC476849
0.8347 Intermediate Similarity NPC471406
0.8308 Intermediate Similarity NPC290746
0.8308 Intermediate Similarity NPC79250
0.8306 Intermediate Similarity NPC93368
0.8306 Intermediate Similarity NPC469947
0.8306 Intermediate Similarity NPC181066
0.8306 Intermediate Similarity NPC470218
0.8305 Intermediate Similarity NPC251309
0.8305 Intermediate Similarity NPC260665
0.8295 Intermediate Similarity NPC477236
0.8293 Intermediate Similarity NPC30735
0.8293 Intermediate Similarity NPC235405
0.8293 Intermediate Similarity NPC160084
0.8293 Intermediate Similarity NPC281148
0.8293 Intermediate Similarity NPC141196
0.8293 Intermediate Similarity NPC1980
0.8293 Intermediate Similarity NPC238005
0.8279 Intermediate Similarity NPC470478
0.8279 Intermediate Similarity NPC476675
0.8276 Intermediate Similarity NPC220836
0.8276 Intermediate Similarity NPC273002
0.8276 Intermediate Similarity NPC92297
0.8276 Intermediate Similarity NPC233433
0.8276 Intermediate Similarity NPC473817
0.8276 Intermediate Similarity NPC94086
0.8264 Intermediate Similarity NPC190939
0.8264 Intermediate Similarity NPC197003
0.8264 Intermediate Similarity NPC192791
0.825 Intermediate Similarity NPC179429
0.8235 Intermediate Similarity NPC477810
0.8235 Intermediate Similarity NPC473882
0.8226 Intermediate Similarity NPC6615
0.8226 Intermediate Similarity NPC470477
0.8226 Intermediate Similarity NPC473474
0.8226 Intermediate Similarity NPC7850
0.8211 Intermediate Similarity NPC10607
0.8211 Intermediate Similarity NPC80986
0.8211 Intermediate Similarity NPC40775
0.8211 Intermediate Similarity NPC4749
0.8211 Intermediate Similarity NPC21691
0.8211 Intermediate Similarity NPC156789
0.8211 Intermediate Similarity NPC187290
0.8211 Intermediate Similarity NPC28532
0.8211 Intermediate Similarity NPC162574
0.8211 Intermediate Similarity NPC249848
0.8211 Intermediate Similarity NPC475591
0.8211 Intermediate Similarity NPC235438
0.8211 Intermediate Similarity NPC107966
0.8211 Intermediate Similarity NPC236870
0.8205 Intermediate Similarity NPC154856
0.8205 Intermediate Similarity NPC52241
0.8205 Intermediate Similarity NPC114961
0.8205 Intermediate Similarity NPC27551
0.8205 Intermediate Similarity NPC129340
0.8205 Intermediate Similarity NPC475317
0.8197 Intermediate Similarity NPC476670
0.819 Intermediate Similarity NPC195708
0.8182 Intermediate Similarity NPC475632
0.8182 Intermediate Similarity NPC86020
0.8182 Intermediate Similarity NPC109588
0.8182 Intermediate Similarity NPC475899
0.8182 Intermediate Similarity NPC176005
0.8174 Intermediate Similarity NPC215408
0.8167 Intermediate Similarity NPC63609
0.8167 Intermediate Similarity NPC477031
0.8167 Intermediate Similarity NPC472718
0.816 Intermediate Similarity NPC285091
0.816 Intermediate Similarity NPC198714
0.816 Intermediate Similarity NPC47113
0.816 Intermediate Similarity NPC174367
0.816 Intermediate Similarity NPC87662
0.8151 Intermediate Similarity NPC178981
0.8151 Intermediate Similarity NPC477944
0.8145 Intermediate Similarity NPC283417
0.8145 Intermediate Similarity NPC200049
0.8145 Intermediate Similarity NPC258617
0.8145 Intermediate Similarity NPC302543
0.8145 Intermediate Similarity NPC257211
0.814 Intermediate Similarity NPC477234
0.8136 Intermediate Similarity NPC477032
0.8136 Intermediate Similarity NPC475247
0.8136 Intermediate Similarity NPC294129
0.8136 Intermediate Similarity NPC476547
0.8136 Intermediate Similarity NPC477028
0.8136 Intermediate Similarity NPC124677
0.8136 Intermediate Similarity NPC197231
0.813 Intermediate Similarity NPC169727
0.813 Intermediate Similarity NPC301449
0.813 Intermediate Similarity NPC64715
0.813 Intermediate Similarity NPC222580
0.813 Intermediate Similarity NPC194310
0.813 Intermediate Similarity NPC159309
0.813 Intermediate Similarity NPC62725
0.813 Intermediate Similarity NPC412
0.813 Intermediate Similarity NPC297263
0.813 Intermediate Similarity NPC171544
0.813 Intermediate Similarity NPC131841
0.813 Intermediate Similarity NPC31838
0.813 Intermediate Similarity NPC302887
0.813 Intermediate Similarity NPC223301
0.813 Intermediate Similarity NPC104372
0.813 Intermediate Similarity NPC241310
0.813 Intermediate Similarity NPC47567
0.813 Intermediate Similarity NPC86222
0.813 Intermediate Similarity NPC11242
0.813 Intermediate Similarity NPC258815
0.813 Intermediate Similarity NPC114484
0.813 Intermediate Similarity NPC187618
0.813 Intermediate Similarity NPC258789
0.813 Intermediate Similarity NPC477463
0.813 Intermediate Similarity NPC22956
0.812 Intermediate Similarity NPC224098
0.812 Intermediate Similarity NPC265655
0.812 Intermediate Similarity NPC475333
0.812 Intermediate Similarity NPC249265
0.812 Intermediate Similarity NPC248746
0.812 Intermediate Similarity NPC475550
0.812 Intermediate Similarity NPC244086
0.812 Intermediate Similarity NPC150372
0.812 Intermediate Similarity NPC171073
0.812 Intermediate Similarity NPC309278
0.812 Intermediate Similarity NPC84956
0.812 Intermediate Similarity NPC476835
0.812 Intermediate Similarity NPC232054
0.812 Intermediate Similarity NPC218571
0.812 Intermediate Similarity NPC102016
0.812 Intermediate Similarity NPC477809
0.812 Intermediate Similarity NPC194207
0.812 Intermediate Similarity NPC300557
0.812 Intermediate Similarity NPC6806
0.812 Intermediate Similarity NPC95051
0.812 Intermediate Similarity NPC208383
0.812 Intermediate Similarity NPC470433
0.812 Intermediate Similarity NPC228190
0.812 Intermediate Similarity NPC22779
0.812 Intermediate Similarity NPC46190
0.812 Intermediate Similarity NPC73243
0.812 Intermediate Similarity NPC236753
0.8115 Intermediate Similarity NPC477464
0.8115 Intermediate Similarity NPC473920
0.811 Intermediate Similarity NPC477235
0.8099 Intermediate Similarity NPC477252

  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 NPC131824 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
0.8246 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.8211 Intermediate Similarity NPD6370 Approved
0.8175 Intermediate Similarity NPD7736 Approved
0.8099 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD8293 Discontinued
0.8049 Intermediate Similarity NPD6054 Approved
0.8049 Intermediate Similarity NPD6059 Approved
0.8 Intermediate Similarity NPD8328 Phase 3
0.7966 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7851 Intermediate Similarity NPD8133 Approved
0.784 Intermediate Similarity NPD6015 Approved
0.784 Intermediate Similarity NPD6016 Approved
0.7797 Intermediate Similarity NPD6412 Phase 2
0.7795 Intermediate Similarity NPD7492 Approved
0.7778 Intermediate Similarity NPD5988 Approved
0.7734 Intermediate Similarity NPD7507 Approved
0.7734 Intermediate Similarity NPD6616 Approved
0.7674 Intermediate Similarity NPD7078 Approved
0.7623 Intermediate Similarity NPD8297 Approved
0.7623 Intermediate Similarity NPD6882 Approved
0.7619 Intermediate Similarity NPD8377 Approved
0.7619 Intermediate Similarity NPD8294 Approved
0.7559 Intermediate Similarity NPD8335 Approved
0.7559 Intermediate Similarity NPD8380 Approved
0.7559 Intermediate Similarity NPD8378 Approved
0.7559 Intermediate Similarity NPD8296 Approved
0.7559 Intermediate Similarity NPD8379 Approved
0.7557 Intermediate Similarity NPD7319 Approved
0.752 Intermediate Similarity NPD6009 Approved
0.7481 Intermediate Similarity NPD6033 Approved
0.748 Intermediate Similarity NPD6319 Approved
0.7438 Intermediate Similarity NPD7320 Approved
0.7422 Intermediate Similarity NPD8033 Approved
0.7417 Intermediate Similarity NPD7128 Approved
0.7417 Intermediate Similarity NPD6675 Approved
0.7417 Intermediate Similarity NPD5739 Approved
0.7417 Intermediate Similarity NPD6402 Approved
0.7377 Intermediate Similarity NPD6373 Approved
0.7377 Intermediate Similarity NPD6372 Approved
0.7368 Intermediate Similarity NPD8171 Discontinued
0.7295 Intermediate Similarity NPD6899 Approved
0.7295 Intermediate Similarity NPD6881 Approved
0.7287 Intermediate Similarity NPD8516 Approved
0.7287 Intermediate Similarity NPD8517 Approved
0.7287 Intermediate Similarity NPD8515 Approved
0.728 Intermediate Similarity NPD4632 Approved
0.7258 Intermediate Similarity NPD6650 Approved
0.7258 Intermediate Similarity NPD8130 Phase 1
0.7258 Intermediate Similarity NPD6649 Approved
0.7213 Intermediate Similarity NPD5697 Approved
0.7213 Intermediate Similarity NPD5701 Approved
0.7188 Intermediate Similarity NPD7328 Approved
0.7188 Intermediate Similarity NPD7327 Approved
0.7177 Intermediate Similarity NPD7102 Approved
0.7177 Intermediate Similarity NPD7290 Approved
0.7177 Intermediate Similarity NPD6883 Approved
0.7154 Intermediate Similarity NPD8513 Phase 3
0.7132 Intermediate Similarity NPD7516 Approved
0.712 Intermediate Similarity NPD6617 Approved
0.712 Intermediate Similarity NPD6869 Approved
0.712 Intermediate Similarity NPD6847 Approved
0.7119 Intermediate Similarity NPD4755 Approved
0.7097 Intermediate Similarity NPD6012 Approved
0.7097 Intermediate Similarity NPD6014 Approved
0.7097 Intermediate Similarity NPD6013 Approved
0.7045 Intermediate Similarity NPD6067 Discontinued
0.7045 Intermediate Similarity NPD7604 Phase 2
0.704 Intermediate Similarity NPD4634 Approved
0.7023 Intermediate Similarity NPD5983 Phase 2
0.7023 Intermediate Similarity NPD7503 Approved
0.7016 Intermediate Similarity NPD6011 Approved
0.7 Intermediate Similarity NPD4700 Approved
0.7 Intermediate Similarity NPD5286 Approved
0.7 Intermediate Similarity NPD4696 Approved
0.7 Intermediate Similarity NPD5285 Approved
0.6984 Remote Similarity NPD6401 Clinical (unspecified phase)
0.694 Remote Similarity NPD6336 Discontinued
0.6885 Remote Similarity NPD5226 Approved
0.6885 Remote Similarity NPD5211 Phase 2
0.6885 Remote Similarity NPD5224 Approved
0.6885 Remote Similarity NPD5225 Approved
0.6885 Remote Similarity NPD4633 Approved
0.6855 Remote Similarity NPD4767 Approved
0.6855 Remote Similarity NPD6008 Approved
0.6855 Remote Similarity NPD4768 Approved
0.685 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6835 Remote Similarity NPD8450 Suspended
0.6833 Remote Similarity NPD6084 Phase 2
0.6833 Remote Similarity NPD6083 Phase 2
0.6829 Remote Similarity NPD5174 Approved
0.6829 Remote Similarity NPD5175 Approved
0.6807 Remote Similarity NPD5695 Phase 3
0.6803 Remote Similarity NPD5223 Approved
0.6774 Remote Similarity NPD5141 Approved
0.6769 Remote Similarity NPD6274 Approved
0.6763 Remote Similarity NPD8449 Approved
0.6746 Remote Similarity NPD4730 Approved
0.6746 Remote Similarity NPD4729 Approved
0.6746 Remote Similarity NPD6686 Approved
0.6742 Remote Similarity NPD7100 Approved
0.6742 Remote Similarity NPD7101 Approved
0.6739 Remote Similarity NPD5956 Approved
0.6694 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD6335 Approved
0.6642 Remote Similarity NPD6908 Approved
0.6642 Remote Similarity NPD6909 Approved
0.6641 Remote Similarity NPD5250 Approved
0.6641 Remote Similarity NPD5248 Approved
0.6641 Remote Similarity NPD5247 Approved
0.6641 Remote Similarity NPD5249 Phase 3
0.6641 Remote Similarity NPD5251 Approved
0.6614 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6614 Remote Similarity NPD5128 Approved
0.6591 Remote Similarity NPD6317 Approved
0.6541 Remote Similarity NPD6314 Approved
0.6541 Remote Similarity NPD6313 Approved
0.6525 Remote Similarity NPD5328 Approved
0.6525 Remote Similarity NPD4753 Phase 2
0.6519 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6504 Remote Similarity NPD5696 Approved
0.65 Remote Similarity NPD4202 Approved
0.6475 Remote Similarity NPD4697 Phase 3
0.6475 Remote Similarity NPD5222 Approved
0.6475 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6475 Remote Similarity NPD5221 Approved
0.6462 Remote Similarity NPD5217 Approved
0.6462 Remote Similarity NPD5215 Approved
0.6462 Remote Similarity NPD5216 Approved
0.6434 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6423 Remote Similarity NPD5173 Approved
0.6417 Remote Similarity NPD6079 Approved
0.64 Remote Similarity NPD1700 Approved
0.6397 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6385 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6385 Remote Similarity NPD5135 Approved
0.6385 Remote Similarity NPD5169 Approved
0.6378 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6378 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6399 Phase 3
0.635 Remote Similarity NPD8080 Discontinued
0.6343 Remote Similarity NPD7115 Discovery
0.6336 Remote Similarity NPD5127 Approved
0.6316 Remote Similarity NPD6928 Phase 2
0.6311 Remote Similarity NPD7748 Approved
0.6303 Remote Similarity NPD7799 Discontinued
0.629 Remote Similarity NPD7902 Approved
0.6288 Remote Similarity NPD6053 Discontinued
0.6286 Remote Similarity NPD8074 Phase 3
0.6281 Remote Similarity NPD8035 Phase 2
0.6281 Remote Similarity NPD6050 Approved
0.6281 Remote Similarity NPD8034 Phase 2
0.6271 Remote Similarity NPD6098 Approved
0.6269 Remote Similarity NPD6868 Approved
0.626 Remote Similarity NPD5955 Clinical (unspecified phase)
0.626 Remote Similarity NPD5210 Approved
0.626 Remote Similarity NPD6356 Clinical (unspecified phase)
0.626 Remote Similarity NPD4629 Approved
0.625 Remote Similarity NPD6673 Approved
0.625 Remote Similarity NPD6904 Approved
0.625 Remote Similarity NPD6080 Approved
0.6241 Remote Similarity NPD8337 Approved
0.6241 Remote Similarity NPD8336 Approved
0.624 Remote Similarity NPD7638 Approved
0.6239 Remote Similarity NPD4786 Approved
0.6198 Remote Similarity NPD5692 Phase 3
0.6194 Remote Similarity NPD5167 Approved
0.619 Remote Similarity NPD7640 Approved
0.619 Remote Similarity NPD7639 Approved
0.6186 Remote Similarity NPD5329 Approved
0.6181 Remote Similarity NPD6845 Suspended
0.6167 Remote Similarity NPD6672 Approved
0.6167 Remote Similarity NPD5737 Approved
0.6159 Remote Similarity NPD6921 Approved
0.6148 Remote Similarity NPD7515 Phase 2
0.6148 Remote Similarity NPD5694 Approved
0.6134 Remote Similarity NPD5280 Approved
0.6134 Remote Similarity NPD4694 Approved
0.6134 Remote Similarity NPD5690 Phase 2
0.6134 Remote Similarity NPD5279 Phase 3
0.6134 Remote Similarity NPD3618 Phase 1
0.6121 Remote Similarity NPD4692 Approved
0.6121 Remote Similarity NPD4139 Approved
0.6103 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6102 Remote Similarity NPD3133 Approved
0.6102 Remote Similarity NPD3666 Approved
0.6102 Remote Similarity NPD4197 Approved
0.6102 Remote Similarity NPD3665 Phase 1
0.6094 Remote Similarity NPD7632 Discontinued
0.6081 Remote Similarity NPD6333 Approved
0.6081 Remote Similarity NPD6334 Approved
0.6078 Remote Similarity NPD7625 Phase 1
0.6069 Remote Similarity NPD8338 Approved
0.6068 Remote Similarity NPD3667 Approved
0.605 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6048 Remote Similarity NPD7900 Approved
0.6048 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6033 Remote Similarity NPD6903 Approved
0.6033 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6031 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6031 Remote Similarity NPD5954 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