Structure

Physi-Chem Properties

Molecular Weight:  480.27
Volume:  486.439
LogP:  2.184
LogD:  2.6
LogS:  -3.46
# Rotatable Bonds:  7
TPSA:  132.75
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.376
Synthetic Accessibility Score:  4.963
Fsp3:  0.769
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.689
MDCK Permeability:  4.5710557969869114e-06
Pgp-inhibitor:  0.003
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.84
20% Bioavailability (F20%):  0.406
30% Bioavailability (F30%):  0.704

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  94.45105743408203%
Volume Distribution (VD):  1.219
Pgp-substrate:  3.5333468914031982%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.154
CYP2C19-inhibitor:  0.012
CYP2C19-substrate:  0.224
CYP2C9-inhibitor:  0.058
CYP2C9-substrate:  0.088
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.209
CYP3A4-inhibitor:  0.075
CYP3A4-substrate:  0.094

ADMET: Excretion

Clearance (CL):  2.493
Half-life (T1/2):  0.745

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.221
Drug-inuced Liver Injury (DILI):  0.034
AMES Toxicity:  0.055
Rat Oral Acute Toxicity:  0.137
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.105
Carcinogencity:  0.062
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.938

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC392

Natural Product ID:  NPC392
Common Name*:   4-[2-[(1R,5R,8As)-5,8A-Dimethyl-2-Methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxymethyl]-3,4,4A,6,7,8-Hexahydro-1H-Naphthalen-1-Yl]Ethyl]-2H-Furan-5-One
IUPAC Name:   4-[2-[(1R,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  YGCYRQKJYWQXHG-XWISJEPMSA-N
Standard InCHI:  InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19?,20-,21+,22-,24-,25+,26+/m1/s1
SMILES:  OC[C@H]1O[C@@H](OC[C@]2(C)CCC[C@@]3(C2CCC(=C)[C@H]3CCC2=CCOC2=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1316546
PubChem CID:   24980083
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001755] Diterpene glycosides

*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
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. root n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota aerial parts purchased in Juhuacun herbal market, Kunming, Yunnan Province, China 2002-Oct PMID[16562826]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[16755060]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[17666848]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[18239311]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[18357994]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[19053511]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19785430]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19962306]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20078074]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[21598983]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[22026410]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[22372956]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota whole plants Nanning District, Guangxi Province, China 2012-Sep PMID[25647077]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota aerial parts Seoul, Korea n.a. PMID[26331882]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[27588583]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[30724564]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8377022]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21178 Chloranthus serratus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16039 Scutellaria barbata Species Lamiaceae 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
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[511814]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20596.2 nM PMID[511814]
NPT2 Others Unspecified Potency = 130.0 nM PMID[511814]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PMID[511814]

☑ 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 NPC392 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 NPC219900
1.0 High Similarity NPC177524
0.9252 High Similarity NPC474483
0.9 High Similarity NPC470312
0.9 High Similarity NPC476127
0.9 High Similarity NPC476150
0.8922 High Similarity NPC121423
0.8824 High Similarity NPC198992
0.8807 High Similarity NPC471816
0.8796 High Similarity NPC264153
0.875 High Similarity NPC170084
0.875 High Similarity NPC476204
0.8692 High Similarity NPC83005
0.8667 High Similarity NPC82251
0.8667 High Similarity NPC239961
0.8649 High Similarity NPC473828
0.8649 High Similarity NPC473617
0.8641 High Similarity NPC477717
0.8627 High Similarity NPC70733
0.8627 High Similarity NPC56071
0.8624 High Similarity NPC474410
0.8624 High Similarity NPC293658
0.8614 High Similarity NPC143446
0.8598 High Similarity NPC476759
0.8596 High Similarity NPC27363
0.8559 High Similarity NPC473968
0.8544 High Similarity NPC477721
0.8544 High Similarity NPC477716
0.8529 High Similarity NPC475709
0.8519 High Similarity NPC476766
0.8515 High Similarity NPC108141
0.8496 Intermediate Similarity NPC281840
0.8496 Intermediate Similarity NPC48692
0.8476 Intermediate Similarity NPC281378
0.8455 Intermediate Similarity NPC473159
0.8455 Intermediate Similarity NPC311592
0.8455 Intermediate Similarity NPC75167
0.8448 Intermediate Similarity NPC469750
0.8448 Intermediate Similarity NPC250556
0.8447 Intermediate Similarity NPC40182
0.8447 Intermediate Similarity NPC198422
0.8411 Intermediate Similarity NPC293512
0.8407 Intermediate Similarity NPC475775
0.8407 Intermediate Similarity NPC122971
0.8407 Intermediate Similarity NPC476529
0.84 Intermediate Similarity NPC477783
0.8393 Intermediate Similarity NPC473405
0.8381 Intermediate Similarity NPC223834
0.8381 Intermediate Similarity NPC201191
0.8378 Intermediate Similarity NPC472274
0.8378 Intermediate Similarity NPC475163
0.8378 Intermediate Similarity NPC181145
0.8376 Intermediate Similarity NPC329784
0.8376 Intermediate Similarity NPC471356
0.8376 Intermediate Similarity NPC471357
0.8376 Intermediate Similarity NPC146456
0.8376 Intermediate Similarity NPC179412
0.8376 Intermediate Similarity NPC117702
0.8376 Intermediate Similarity NPC469757
0.8376 Intermediate Similarity NPC240070
0.8364 Intermediate Similarity NPC471967
0.8362 Intermediate Similarity NPC318135
0.835 Intermediate Similarity NPC309503
0.835 Intermediate Similarity NPC239547
0.835 Intermediate Similarity NPC477719
0.835 Intermediate Similarity NPC91197
0.835 Intermediate Similarity NPC125551
0.835 Intermediate Similarity NPC477718
0.835 Intermediate Similarity NPC96597
0.835 Intermediate Similarity NPC155319
0.835 Intermediate Similarity NPC278506
0.8349 Intermediate Similarity NPC127153
0.8349 Intermediate Similarity NPC235014
0.8333 Intermediate Similarity NPC295389
0.8333 Intermediate Similarity NPC109607
0.8333 Intermediate Similarity NPC107338
0.8333 Intermediate Similarity NPC473288
0.8333 Intermediate Similarity NPC476765
0.8319 Intermediate Similarity NPC234522
0.8319 Intermediate Similarity NPC471548
0.8318 Intermediate Similarity NPC476762
0.8318 Intermediate Similarity NPC476760
0.8318 Intermediate Similarity NPC476761
0.8318 Intermediate Similarity NPC218158
0.8318 Intermediate Similarity NPC85670
0.8317 Intermediate Similarity NPC474835
0.8305 Intermediate Similarity NPC311534
0.8305 Intermediate Similarity NPC220838
0.8305 Intermediate Similarity NPC45606
0.8304 Intermediate Similarity NPC207637
0.8304 Intermediate Similarity NPC193382
0.8304 Intermediate Similarity NPC199428
0.8304 Intermediate Similarity NPC99620
0.8304 Intermediate Similarity NPC5311
0.8304 Intermediate Similarity NPC310341
0.83 Intermediate Similarity NPC477782
0.8291 Intermediate Similarity NPC297950
0.8288 Intermediate Similarity NPC157441
0.8286 Intermediate Similarity NPC280991
0.8286 Intermediate Similarity NPC11974
0.8286 Intermediate Similarity NPC154127
0.8273 Intermediate Similarity NPC263827
0.8273 Intermediate Similarity NPC250481
0.8273 Intermediate Similarity NPC285410
0.8269 Intermediate Similarity NPC472015
0.8261 Intermediate Similarity NPC202051
0.8257 Intermediate Similarity NPC246205
0.8257 Intermediate Similarity NPC137917
0.8257 Intermediate Similarity NPC237503
0.8257 Intermediate Similarity NPC306746
0.8257 Intermediate Similarity NPC204407
0.8257 Intermediate Similarity NPC206618
0.8257 Intermediate Similarity NPC167383
0.8257 Intermediate Similarity NPC57362
0.8252 Intermediate Similarity NPC54731
0.8252 Intermediate Similarity NPC234993
0.8252 Intermediate Similarity NPC134072
0.8246 Intermediate Similarity NPC477071
0.8246 Intermediate Similarity NPC470914
0.8241 Intermediate Similarity NPC187435
0.8241 Intermediate Similarity NPC67321
0.8235 Intermediate Similarity NPC469754
0.8235 Intermediate Similarity NPC469751
0.8235 Intermediate Similarity NPC10823
0.8235 Intermediate Similarity NPC284406
0.8235 Intermediate Similarity NPC471352
0.8235 Intermediate Similarity NPC469752
0.8235 Intermediate Similarity NPC2003
0.8235 Intermediate Similarity NPC89514
0.8235 Intermediate Similarity NPC471358
0.8235 Intermediate Similarity NPC6108
0.8235 Intermediate Similarity NPC125077
0.8235 Intermediate Similarity NPC471361
0.8235 Intermediate Similarity NPC471360
0.8235 Intermediate Similarity NPC251866
0.8235 Intermediate Similarity NPC70542
0.8235 Intermediate Similarity NPC471359
0.8235 Intermediate Similarity NPC477722
0.8235 Intermediate Similarity NPC140092
0.8235 Intermediate Similarity NPC471407
0.8235 Intermediate Similarity NPC219085
0.8235 Intermediate Similarity NPC9499
0.8235 Intermediate Similarity NPC86159
0.8235 Intermediate Similarity NPC188234
0.8235 Intermediate Similarity NPC476966
0.8235 Intermediate Similarity NPC17896
0.8235 Intermediate Similarity NPC232785
0.8235 Intermediate Similarity NPC197707
0.8235 Intermediate Similarity NPC469755
0.8235 Intermediate Similarity NPC25701
0.8235 Intermediate Similarity NPC180079
0.8235 Intermediate Similarity NPC469753
0.8235 Intermediate Similarity NPC276838
0.8235 Intermediate Similarity NPC329986
0.823 Intermediate Similarity NPC158344
0.823 Intermediate Similarity NPC309034
0.823 Intermediate Similarity NPC157376
0.823 Intermediate Similarity NPC50305
0.823 Intermediate Similarity NPC99728
0.823 Intermediate Similarity NPC471355
0.823 Intermediate Similarity NPC77319
0.823 Intermediate Similarity NPC152615
0.823 Intermediate Similarity NPC27507
0.823 Intermediate Similarity NPC34390
0.823 Intermediate Similarity NPC473852
0.823 Intermediate Similarity NPC84987
0.823 Intermediate Similarity NPC93883
0.823 Intermediate Similarity NPC474418
0.823 Intermediate Similarity NPC203862
0.823 Intermediate Similarity NPC87250
0.823 Intermediate Similarity NPC142066
0.823 Intermediate Similarity NPC471354
0.823 Intermediate Similarity NPC471351
0.823 Intermediate Similarity NPC243196
0.823 Intermediate Similarity NPC244402
0.823 Intermediate Similarity NPC196429
0.823 Intermediate Similarity NPC471353
0.8224 Intermediate Similarity NPC476764
0.8224 Intermediate Similarity NPC476763
0.822 Intermediate Similarity NPC470516
0.8214 Intermediate Similarity NPC84949
0.8214 Intermediate Similarity NPC31354
0.8214 Intermediate Similarity NPC165439
0.8214 Intermediate Similarity NPC74727
0.8214 Intermediate Similarity NPC69576
0.8214 Intermediate Similarity NPC471633
0.8208 Intermediate Similarity NPC94919
0.8208 Intermediate Similarity NPC134077
0.8208 Intermediate Similarity NPC476769
0.8205 Intermediate Similarity NPC469379
0.8205 Intermediate Similarity NPC86346
0.8205 Intermediate Similarity NPC75856
0.82 Intermediate Similarity NPC174342
0.82 Intermediate Similarity NPC251528
0.8198 Intermediate Similarity NPC470063
0.8198 Intermediate Similarity NPC194951
0.8198 Intermediate Similarity NPC174836
0.8198 Intermediate Similarity NPC12046
0.819 Intermediate Similarity NPC476767
0.8182 Intermediate Similarity NPC476882

  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 NPC392 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
1.0 High Similarity NPD6686 Approved
0.8448 Intermediate Similarity NPD7507 Approved
0.8411 Intermediate Similarity NPD6412 Phase 2
0.8235 Intermediate Similarity NPD7319 Approved
0.8158 Intermediate Similarity NPD7328 Approved
0.8158 Intermediate Similarity NPD7327 Approved
0.8087 Intermediate Similarity NPD7516 Approved
0.8017 Intermediate Similarity NPD8377 Approved
0.8017 Intermediate Similarity NPD8294 Approved
0.7965 Intermediate Similarity NPD8133 Approved
0.7949 Intermediate Similarity NPD8033 Approved
0.7949 Intermediate Similarity NPD8335 Approved
0.7949 Intermediate Similarity NPD8380 Approved
0.7949 Intermediate Similarity NPD7503 Approved
0.7949 Intermediate Similarity NPD8379 Approved
0.7949 Intermediate Similarity NPD8296 Approved
0.7949 Intermediate Similarity NPD8378 Approved
0.7941 Intermediate Similarity NPD6698 Approved
0.7941 Intermediate Similarity NPD46 Approved
0.7768 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7768 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7757 Intermediate Similarity NPD7638 Approved
0.7685 Intermediate Similarity NPD7640 Approved
0.7685 Intermediate Similarity NPD7639 Approved
0.7677 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD8328 Phase 3
0.7593 Intermediate Similarity NPD4225 Approved
0.7544 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7478 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD7115 Discovery
0.7311 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD6370 Approved
0.7281 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD7736 Approved
0.7265 Intermediate Similarity NPD6882 Approved
0.7264 Intermediate Similarity NPD7838 Discovery
0.7241 Intermediate Similarity NPD6371 Approved
0.7213 Intermediate Similarity NPD8517 Approved
0.7213 Intermediate Similarity NPD8516 Approved
0.7213 Intermediate Similarity NPD8513 Phase 3
0.7213 Intermediate Similarity NPD8515 Approved
0.72 Intermediate Similarity NPD8293 Discontinued
0.7184 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD7492 Approved
0.7167 Intermediate Similarity NPD6009 Approved
0.7131 Intermediate Similarity NPD6319 Approved
0.7131 Intermediate Similarity NPD6054 Approved
0.713 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD6616 Approved
0.7119 Intermediate Similarity NPD8297 Approved
0.708 Intermediate Similarity NPD7632 Discontinued
0.7069 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7078 Approved
0.7059 Intermediate Similarity NPD4632 Approved
0.7027 Intermediate Similarity NPD6083 Phase 2
0.7027 Intermediate Similarity NPD6084 Phase 2
0.6992 Remote Similarity NPD6059 Approved
0.6991 Remote Similarity NPD5344 Discontinued
0.6975 Remote Similarity NPD6053 Discontinued
0.6972 Remote Similarity NPD6399 Phase 3
0.696 Remote Similarity NPD7829 Approved
0.696 Remote Similarity NPD6067 Discontinued
0.696 Remote Similarity NPD7830 Approved
0.6935 Remote Similarity NPD6015 Approved
0.6935 Remote Similarity NPD6016 Approved
0.6923 Remote Similarity NPD6881 Approved
0.6923 Remote Similarity NPD6899 Approved
0.6909 Remote Similarity NPD7748 Approved
0.6897 Remote Similarity NPD5739 Approved
0.6897 Remote Similarity NPD7128 Approved
0.6897 Remote Similarity NPD6675 Approved
0.6897 Remote Similarity NPD6402 Approved
0.6891 Remote Similarity NPD6649 Approved
0.6891 Remote Similarity NPD6650 Approved
0.6887 Remote Similarity NPD6684 Approved
0.6887 Remote Similarity NPD7521 Approved
0.6887 Remote Similarity NPD5330 Approved
0.6887 Remote Similarity NPD7146 Approved
0.6887 Remote Similarity NPD6409 Approved
0.6887 Remote Similarity NPD7334 Approved
0.6881 Remote Similarity NPD7515 Phase 2
0.6881 Remote Similarity NPD7983 Approved
0.688 Remote Similarity NPD5988 Approved
0.6875 Remote Similarity NPD7902 Approved
0.6864 Remote Similarity NPD6373 Approved
0.6864 Remote Similarity NPD6372 Approved
0.6838 Remote Similarity NPD5697 Approved
0.6807 Remote Similarity NPD6883 Approved
0.6807 Remote Similarity NPD7102 Approved
0.6807 Remote Similarity NPD7290 Approved
0.678 Remote Similarity NPD7320 Approved
0.6759 Remote Similarity NPD6672 Approved
0.6759 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6759 Remote Similarity NPD5737 Approved
0.6759 Remote Similarity NPD6903 Approved
0.675 Remote Similarity NPD6847 Approved
0.675 Remote Similarity NPD6617 Approved
0.675 Remote Similarity NPD6869 Approved
0.675 Remote Similarity NPD8130 Phase 1
0.6727 Remote Similarity NPD6411 Approved
0.6727 Remote Similarity NPD7637 Suspended
0.6723 Remote Similarity NPD6014 Approved
0.6723 Remote Similarity NPD6013 Approved
0.6723 Remote Similarity NPD6012 Approved
0.6718 Remote Similarity NPD7260 Phase 2
0.6716 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6698 Remote Similarity NPD3665 Phase 1
0.6698 Remote Similarity NPD3133 Approved
0.6698 Remote Similarity NPD3666 Approved
0.6696 Remote Similarity NPD5695 Phase 3
0.6696 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6695 Remote Similarity NPD5701 Approved
0.6694 Remote Similarity NPD7641 Discontinued
0.6693 Remote Similarity NPD7642 Approved
0.6693 Remote Similarity NPD7604 Phase 2
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD5983 Phase 2
0.6667 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6639 Remote Similarity NPD6011 Approved
0.6636 Remote Similarity NPD5785 Approved
0.6636 Remote Similarity NPD1694 Approved
0.6609 Remote Similarity NPD6648 Approved
0.6607 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6607 Remote Similarity NPD7900 Approved
0.6589 Remote Similarity NPD6336 Discontinued
0.6589 Remote Similarity NPD8451 Approved
0.6577 Remote Similarity NPD5693 Phase 1
0.6577 Remote Similarity NPD6079 Approved
0.6574 Remote Similarity NPD3618 Phase 1
0.6545 Remote Similarity NPD6101 Approved
0.6545 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5328 Approved
0.6545 Remote Similarity NPD4753 Phase 2
0.6542 Remote Similarity NPD4786 Approved
0.6538 Remote Similarity NPD8448 Approved
0.6535 Remote Similarity NPD8444 Approved
0.6535 Remote Similarity NPD6921 Approved
0.6529 Remote Similarity NPD4634 Approved
0.6525 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6525 Remote Similarity NPD7625 Phase 1
0.6515 Remote Similarity NPD8390 Approved
0.6515 Remote Similarity NPD6914 Discontinued
0.6515 Remote Similarity NPD5956 Approved
0.6515 Remote Similarity NPD8392 Approved
0.6515 Remote Similarity NPD8391 Approved
0.6514 Remote Similarity NPD7524 Approved
0.6509 Remote Similarity NPD3667 Approved
0.6496 Remote Similarity NPD5211 Phase 2
0.6491 Remote Similarity NPD7839 Suspended
0.6489 Remote Similarity NPD8337 Approved
0.6489 Remote Similarity NPD6033 Approved
0.6489 Remote Similarity NPD8336 Approved
0.6484 Remote Similarity NPD8080 Discontinued
0.648 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4695 Discontinued
0.6475 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6008 Approved
0.6466 Remote Similarity NPD4696 Approved
0.6466 Remote Similarity NPD5285 Approved
0.6466 Remote Similarity NPD5286 Approved
0.646 Remote Similarity NPD5282 Discontinued
0.6435 Remote Similarity NPD4755 Approved
0.6429 Remote Similarity NPD8035 Phase 2
0.6429 Remote Similarity NPD8034 Phase 2
0.6422 Remote Similarity NPD5279 Phase 3
0.6418 Remote Similarity NPD6845 Suspended
0.6404 Remote Similarity NPD5210 Approved
0.6404 Remote Similarity NPD4629 Approved
0.64 Remote Similarity NPD6274 Approved
0.6396 Remote Similarity NPD6904 Approved
0.6396 Remote Similarity NPD6051 Approved
0.6396 Remote Similarity NPD6080 Approved
0.6396 Remote Similarity NPD6673 Approved
0.6389 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6387 Remote Similarity NPD5141 Approved
0.6385 Remote Similarity NPD8340 Approved
0.6385 Remote Similarity NPD8342 Approved
0.6385 Remote Similarity NPD8341 Approved
0.6385 Remote Similarity NPD8299 Approved
0.6378 Remote Similarity NPD7100 Approved
0.6378 Remote Similarity NPD7101 Approved
0.6372 Remote Similarity NPD4202 Approved
0.6364 Remote Similarity NPD3573 Approved
0.6356 Remote Similarity NPD5225 Approved
0.6356 Remote Similarity NPD5224 Approved
0.6356 Remote Similarity NPD5226 Approved
0.6356 Remote Similarity NPD4633 Approved
0.6348 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6348 Remote Similarity NPD5222 Approved
0.6348 Remote Similarity NPD5221 Approved
0.633 Remote Similarity NPD7520 Clinical (unspecified phase)
0.633 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6325 Remote Similarity NPD4700 Approved
0.6303 Remote Similarity NPD5174 Approved
0.6303 Remote Similarity NPD5175 Approved
0.6299 Remote Similarity NPD6335 Approved
0.6296 Remote Similarity NPD7154 Phase 3

  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