Structure

Physi-Chem Properties

Molecular Weight:  732.35
Volume:  757.261
LogP:  6.045
LogD:  4.722
LogS:  -4.909
# Rotatable Bonds:  16
TPSA:  123.53
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.117
Synthetic Accessibility Score:  4.392
Fsp3:  0.429
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
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:  -5.205
MDCK Permeability:  5.24438546563033e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.054
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  65.6393814086914%
Volume Distribution (VD):  0.429
Pgp-substrate:  16.018753051757812%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.974
CYP2C19-inhibitor:  0.221
CYP2C19-substrate:  0.93
CYP2C9-inhibitor:  0.742
CYP2C9-substrate:  0.895
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.967
CYP3A4-inhibitor:  0.896
CYP3A4-substrate:  0.948

ADMET: Excretion

Clearance (CL):  7.867
Half-life (T1/2):  0.097

ADMET: Toxicity

hERG Blockers:  0.284
Human Hepatotoxicity (H-HT):  0.059
Drug-inuced Liver Injury (DILI):  0.947
AMES Toxicity:  0.079
Rat Oral Acute Toxicity:  0.249
Maximum Recommended Daily Dose:  0.03
Skin Sensitization:  0.032
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.004

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

  Natural Product: NPC260842

Natural Product ID:  NPC260842
Common Name*:   1-(3,4-Dimethoxyphenyl)-2-[4-[(2S,3R,4R,5S)-5-[4-[1-(3,4-Dimethoxyphenyl)-1-Hydroxypropan-2-Yl]Oxy-3-Methoxyphenyl]-3,4-Dimethyloxolan-2-Yl]-2-Methoxyphenoxy]Propan-1-Ol
IUPAC Name:   1-(3,4-dimethoxyphenyl)-2-[4-[(2S,3R,4R,5S)-5-[4-[1-(3,4-dimethoxyphenyl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]propan-1-ol
Synonyms:  
Standard InCHIKey:  ZGXXNVOBEIRACL-JAWLWFRMSA-N
Standard InCHI:  InChI=1S/C42H52O11/c1-23-24(2)42(30-14-18-34(38(22-30)50-10)52-26(4)40(44)28-12-16-32(46-6)36(20-28)48-8)53-41(23)29-13-17-33(37(21-29)49-9)51-25(3)39(43)27-11-15-31(45-5)35(19-27)47-7/h11-26,39-44H,1-10H3/t23-,24-,25?,26?,39?,40?,41+,42+/m1/s1
SMILES:  COc1cc(ccc1OC(C(c1ccc(c(c1)OC)OC)O)C)[C@H]1O[C@@H]([C@@H]([C@H]1C)C)c1ccc(c(c1)OC)OC(C(c1ccc(c(c1)OC)OC)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL316331
PubChem CID:   44336126
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[10924192]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11754613]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. root n.a. PMID[14750033]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15482936]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota roots n.a. n.a. PMID[18841903]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Roots n.a. n.a. PMID[24359277]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Aerial Parts n.a. n.a. PMID[24387347]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[29099182]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[31642320]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31142 Saururus sp Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26318 Saururus sp. Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20323 Saururus chinensis Species Saururaceae 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
NPT1214 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 1 Homo sapiens IC50 = 8000.0 nM PMID[497813]
NPT2584 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 2 Homo sapiens IC50 = 39000.0 nM PMID[497813]
NPT2584 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 2 Homo sapiens IC50 = 8000.0 nM PMID[497814]
NPT1214 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 1 Homo sapiens IC50 = 39000.0 nM PMID[497814]

☑ 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 NPC260842 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
0.985 High Similarity NPC470372
0.9771 High Similarity NPC93783
0.9549 High Similarity NPC77861
0.9493 High Similarity NPC93610
0.9493 High Similarity NPC241846
0.9424 High Similarity NPC99183
0.9357 High Similarity NPC304048
0.9357 High Similarity NPC226153
0.9291 High Similarity NPC470098
0.9291 High Similarity NPC473266
0.9291 High Similarity NPC470826
0.9203 High Similarity NPC302506
0.9197 High Similarity NPC55793
0.9161 High Similarity NPC321972
0.9161 High Similarity NPC329343
0.9161 High Similarity NPC324517
0.9143 High Similarity NPC181615
0.9091 High Similarity NPC470084
0.9071 High Similarity NPC114119
0.9071 High Similarity NPC179521
0.9071 High Similarity NPC471415
0.9071 High Similarity NPC470097
0.9058 High Similarity NPC266197
0.9058 High Similarity NPC291101
0.9014 High Similarity NPC320671
0.9014 High Similarity NPC327412
0.9014 High Similarity NPC320970
0.9014 High Similarity NPC328567
0.8958 High Similarity NPC477612
0.8955 High Similarity NPC187998
0.8955 High Similarity NPC77040
0.8955 High Similarity NPC42300
0.8955 High Similarity NPC241522
0.8955 High Similarity NPC174495
0.8955 High Similarity NPC257582
0.8955 High Similarity NPC153739
0.8955 High Similarity NPC92164
0.8955 High Similarity NPC242807
0.8955 High Similarity NPC145305
0.8955 High Similarity NPC64201
0.8947 High Similarity NPC45774
0.8947 High Similarity NPC11258
0.8947 High Similarity NPC21867
0.8947 High Similarity NPC184733
0.8947 High Similarity NPC282703
0.8947 High Similarity NPC128208
0.8947 High Similarity NPC129570
0.8944 High Similarity NPC260397
0.8944 High Similarity NPC317053
0.8944 High Similarity NPC324492
0.8939 High Similarity NPC206882
0.8936 High Similarity NPC84684
0.8936 High Similarity NPC471063
0.8936 High Similarity NPC238216
0.8936 High Similarity NPC185388
0.8936 High Similarity NPC208994
0.8931 High Similarity NPC94276
0.8931 High Similarity NPC109822
0.8929 High Similarity NPC476356
0.8913 High Similarity NPC474390
0.8904 High Similarity NPC115203
0.8897 High Similarity NPC26394
0.8889 High Similarity NPC277804
0.8881 High Similarity NPC475875
0.8873 High Similarity NPC473909
0.8873 High Similarity NPC274960
0.8873 High Similarity NPC143120
0.8865 High Similarity NPC470950
0.8865 High Similarity NPC185307
0.8849 High Similarity NPC22517
0.8841 High Similarity NPC54743
0.8841 High Similarity NPC10737
0.8841 High Similarity NPC29799
0.8841 High Similarity NPC263367
0.8841 High Similarity NPC156502
0.8841 High Similarity NPC177160
0.8841 High Similarity NPC477939
0.8841 High Similarity NPC209985
0.8832 High Similarity NPC193026
0.8832 High Similarity NPC187616
0.8832 High Similarity NPC49603
0.8832 High Similarity NPC471942
0.8824 High Similarity NPC230219
0.8819 High Similarity NPC329836
0.8819 High Similarity NPC20757
0.8819 High Similarity NPC227516
0.8811 High Similarity NPC276753
0.8811 High Similarity NPC205796
0.8803 High Similarity NPC283995
0.8803 High Similarity NPC129417
0.8803 High Similarity NPC15659
0.8803 High Similarity NPC470235
0.8803 High Similarity NPC304894
0.8797 High Similarity NPC191037
0.8797 High Similarity NPC58607
0.8797 High Similarity NPC304630
0.8797 High Similarity NPC17837
0.8797 High Similarity NPC178284
0.8794 High Similarity NPC246947
0.8792 High Similarity NPC470827
0.8786 High Similarity NPC22317
0.8786 High Similarity NPC262189
0.8779 High Similarity NPC71090
0.8759 High Similarity NPC211561
0.875 High Similarity NPC228346
0.875 High Similarity NPC158079
0.875 High Similarity NPC27843
0.875 High Similarity NPC469625
0.875 High Similarity NPC115207
0.875 High Similarity NPC40432
0.875 High Similarity NPC7171
0.875 High Similarity NPC469613
0.875 High Similarity NPC30043
0.875 High Similarity NPC161557
0.8741 High Similarity NPC86030
0.8741 High Similarity NPC38041
0.8741 High Similarity NPC476301
0.8741 High Similarity NPC43508
0.8741 High Similarity NPC5851
0.8741 High Similarity NPC22150
0.8741 High Similarity NPC279298
0.8733 High Similarity NPC470828
0.8732 High Similarity NPC46092
0.8732 High Similarity NPC173203
0.8732 High Similarity NPC163508
0.8731 High Similarity NPC118787
0.8731 High Similarity NPC165045
0.8731 High Similarity NPC319625
0.8731 High Similarity NPC147821
0.8731 High Similarity NPC118533
0.8731 High Similarity NPC111247
0.8731 High Similarity NPC183181
0.8731 High Similarity NPC163332
0.8731 High Similarity NPC292056
0.8731 High Similarity NPC41706
0.8723 High Similarity NPC178054
0.8723 High Similarity NPC472711
0.8722 High Similarity NPC194519
0.8722 High Similarity NPC148627
0.8716 High Similarity NPC157333
0.8702 High Similarity NPC65933
0.8702 High Similarity NPC312713
0.8702 High Similarity NPC172676
0.8702 High Similarity NPC126935
0.8702 High Similarity NPC57268
0.8702 High Similarity NPC216929
0.8699 High Similarity NPC475224
0.8696 High Similarity NPC326095
0.8696 High Similarity NPC287745
0.8696 High Similarity NPC478085
0.8696 High Similarity NPC184269
0.8696 High Similarity NPC244983
0.869 High Similarity NPC281549
0.8686 High Similarity NPC4940
0.8686 High Similarity NPC207400
0.8686 High Similarity NPC18842
0.8686 High Similarity NPC181049
0.8681 High Similarity NPC112861
0.8676 High Similarity NPC469614
0.8676 High Similarity NPC469612
0.8671 High Similarity NPC171932
0.8671 High Similarity NPC79429
0.8671 High Similarity NPC28440
0.8671 High Similarity NPC471667
0.8671 High Similarity NPC217635
0.8667 High Similarity NPC252307
0.8667 High Similarity NPC245826
0.8667 High Similarity NPC72529
0.8667 High Similarity NPC474178
0.8667 High Similarity NPC125495
0.8662 High Similarity NPC67467
0.8652 High Similarity NPC309124
0.8652 High Similarity NPC106055
0.8652 High Similarity NPC184797
0.8652 High Similarity NPC110699
0.8647 High Similarity NPC114901
0.8647 High Similarity NPC48990
0.8647 High Similarity NPC293701
0.8643 High Similarity NPC477938
0.863 High Similarity NPC318373
0.863 High Similarity NPC475250
0.863 High Similarity NPC476969
0.863 High Similarity NPC321657
0.8623 High Similarity NPC158331
0.8621 High Similarity NPC236202
0.8621 High Similarity NPC18185
0.8621 High Similarity NPC58190
0.8621 High Similarity NPC275284
0.8621 High Similarity NPC39657
0.8621 High Similarity NPC204770
0.8621 High Similarity NPC114505
0.8621 High Similarity NPC263940
0.8621 High Similarity NPC193473
0.8621 High Similarity NPC82917
0.8621 High Similarity NPC70409
0.8621 High Similarity NPC15956
0.8621 High Similarity NPC108811
0.8621 High Similarity NPC224674
0.8621 High Similarity NPC31325
0.8621 High Similarity NPC202742

  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 NPC260842 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
0.8333 Intermediate Similarity NPD3027 Phase 3
0.8156 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8156 Intermediate Similarity NPD1613 Approved
0.8058 Intermediate Similarity NPD2861 Phase 2
0.8015 Intermediate Similarity NPD5283 Phase 1
0.8 Intermediate Similarity NPD4908 Phase 1
0.7959 Intermediate Similarity NPD6674 Discontinued
0.7939 Intermediate Similarity NPD7843 Approved
0.7902 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7902 Intermediate Similarity NPD3620 Phase 2
0.7895 Intermediate Similarity NPD7157 Approved
0.7887 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD5735 Approved
0.7801 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD8127 Discontinued
0.7754 Intermediate Similarity NPD3705 Approved
0.7714 Intermediate Similarity NPD8651 Approved
0.7692 Intermediate Similarity NPD37 Approved
0.7688 Intermediate Similarity NPD7199 Phase 2
0.7658 Intermediate Similarity NPD4965 Approved
0.7658 Intermediate Similarity NPD4967 Phase 2
0.7658 Intermediate Similarity NPD4966 Approved
0.7643 Intermediate Similarity NPD8455 Phase 2
0.7634 Intermediate Similarity NPD2684 Approved
0.7632 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD5846 Approved
0.7609 Intermediate Similarity NPD6516 Phase 2
0.76 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD228 Approved
0.7584 Intermediate Similarity NPD7266 Discontinued
0.7569 Intermediate Similarity NPD7095 Approved
0.7568 Intermediate Similarity NPD5588 Approved
0.7562 Intermediate Similarity NPD6234 Discontinued
0.7561 Intermediate Similarity NPD7228 Approved
0.755 Intermediate Similarity NPD6331 Phase 2
0.7546 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD6166 Phase 2
0.7546 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD1357 Approved
0.7534 Intermediate Similarity NPD4060 Phase 1
0.7518 Intermediate Similarity NPD5327 Phase 3
0.75 Intermediate Similarity NPD4536 Approved
0.75 Intermediate Similarity NPD4538 Approved
0.75 Intermediate Similarity NPD1610 Phase 2
0.75 Intermediate Similarity NPD7097 Phase 1
0.75 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6584 Phase 3
0.7483 Intermediate Similarity NPD6355 Discontinued
0.7483 Intermediate Similarity NPD4236 Phase 3
0.7483 Intermediate Similarity NPD4237 Approved
0.7467 Intermediate Similarity NPD5763 Approved
0.7467 Intermediate Similarity NPD5762 Approved
0.7451 Intermediate Similarity NPD5058 Phase 3
0.7444 Intermediate Similarity NPD3021 Approved
0.7444 Intermediate Similarity NPD3022 Approved
0.7438 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4110 Phase 3
0.7434 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD3051 Approved
0.7421 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD7037 Approved
0.7415 Intermediate Similarity NPD1558 Phase 1
0.7415 Intermediate Similarity NPD4140 Approved
0.7415 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6798 Discontinued
0.7394 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2982 Phase 2
0.7394 Intermediate Similarity NPD2983 Phase 2
0.7391 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7833 Phase 2
0.7391 Intermediate Similarity NPD7831 Phase 2
0.7378 Intermediate Similarity NPD2970 Approved
0.7378 Intermediate Similarity NPD2969 Approved
0.7375 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD1934 Approved
0.7355 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD1375 Discontinued
0.7347 Intermediate Similarity NPD6233 Phase 2
0.7333 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5960 Phase 3
0.7324 Intermediate Similarity NPD2981 Phase 2
0.7321 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4628 Phase 3
0.7315 Intermediate Similarity NPD6353 Approved
0.7315 Intermediate Similarity NPD6653 Approved
0.7312 Intermediate Similarity NPD5772 Approved
0.7312 Intermediate Similarity NPD5773 Approved
0.731 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD3018 Phase 2
0.7305 Intermediate Similarity NPD5844 Phase 1
0.7285 Intermediate Similarity NPD2161 Phase 2
0.7279 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7240 Approved
0.7278 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6583 Phase 3
0.7273 Intermediate Similarity NPD6582 Phase 2
0.7273 Intermediate Similarity NPD2677 Approved
0.7262 Intermediate Similarity NPD7074 Phase 3
0.726 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD3060 Approved
0.7255 Intermediate Similarity NPD4162 Approved
0.7254 Intermediate Similarity NPD1091 Approved
0.7248 Intermediate Similarity NPD3657 Discovery
0.7246 Intermediate Similarity NPD3818 Discontinued
0.7246 Intermediate Similarity NPD6671 Approved
0.7244 Intermediate Similarity NPD4123 Phase 3
0.7244 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD27 Approved
0.7229 Intermediate Similarity NPD2489 Approved
0.7225 Intermediate Similarity NPD7906 Approved
0.7215 Intermediate Similarity NPD1653 Approved
0.7214 Intermediate Similarity NPD1548 Phase 1
0.7208 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD2235 Phase 2
0.7203 Intermediate Similarity NPD2231 Phase 2
0.7202 Intermediate Similarity NPD7054 Approved
0.7197 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD52 Approved
0.7197 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7526 Approved
0.7195 Intermediate Similarity NPD5494 Approved
0.7184 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7685 Pre-registration
0.7172 Intermediate Similarity NPD3094 Phase 2
0.7164 Intermediate Similarity NPD290 Approved
0.7162 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD5241 Discontinued
0.716 Intermediate Similarity NPD7472 Approved
0.716 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2563 Approved
0.716 Intermediate Similarity NPD2560 Approved
0.7153 Intermediate Similarity NPD5535 Approved
0.7153 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD4749 Approved
0.7151 Intermediate Similarity NPD8054 Approved
0.7151 Intermediate Similarity NPD8053 Approved
0.7143 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5177 Phase 3
0.7143 Intermediate Similarity NPD5536 Phase 2
0.7135 Intermediate Similarity NPD7808 Phase 3
0.7134 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD3092 Approved
0.7124 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3882 Suspended
0.7114 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD6071 Discontinued
0.7107 Intermediate Similarity NPD3687 Approved
0.7107 Intermediate Similarity NPD3686 Approved
0.7103 Intermediate Similarity NPD6696 Suspended
0.7099 Intermediate Similarity NPD2977 Approved
0.7099 Intermediate Similarity NPD2801 Approved
0.7099 Intermediate Similarity NPD2978 Approved
0.7097 Intermediate Similarity NPD8166 Discontinued
0.7097 Intermediate Similarity NPD7466 Approved
0.7095 Intermediate Similarity NPD4625 Phase 3
0.7093 Intermediate Similarity NPD8312 Approved
0.7093 Intermediate Similarity NPD7313 Approved
0.7093 Intermediate Similarity NPD8313 Approved
0.7093 Intermediate Similarity NPD7310 Approved
0.7093 Intermediate Similarity NPD7312 Approved
0.7093 Intermediate Similarity NPD7311 Approved
0.709 Intermediate Similarity NPD968 Approved
0.7089 Intermediate Similarity NPD6273 Approved
0.7083 Intermediate Similarity NPD1608 Approved
0.7069 Intermediate Similarity NPD4663 Approved
0.7067 Intermediate Similarity NPD2238 Phase 2
0.7059 Intermediate Similarity NPD5451 Approved
0.7055 Intermediate Similarity NPD3817 Phase 2
0.7052 Intermediate Similarity NPD7309 Approved
0.7051 Intermediate Similarity NPD6190 Approved
0.7051 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD5110 Phase 2
0.7047 Intermediate Similarity NPD5109 Approved
0.7047 Intermediate Similarity NPD5111 Phase 2
0.7045 Intermediate Similarity NPD291 Approved
0.7044 Intermediate Similarity NPD2122 Discontinued
0.7044 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7549 Discontinued
0.7025 Intermediate Similarity NPD7447 Phase 1
0.702 Intermediate Similarity NPD4340 Discontinued
0.7019 Intermediate Similarity NPD4678 Approved
0.7019 Intermediate Similarity NPD4675 Approved
0.7012 Intermediate Similarity NPD7768 Phase 2
0.7007 Intermediate Similarity NPD4624 Approved
0.7007 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6815 Approved
0.7006 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7265 Discontinued
0.7 Intermediate Similarity NPD4210 Discontinued
0.7 Intermediate Similarity NPD8156 Discontinued
0.6994 Remote Similarity NPD4578 Approved
0.6994 Remote Similarity NPD4577 Approved
0.6993 Remote Similarity NPD5126 Approved
0.6993 Remote Similarity NPD5125 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