Structure

Physi-Chem Properties

Molecular Weight:  240.04
Volume:  239.1
LogP:  3.723
LogD:  2.818
LogS:  -5.482
# Rotatable Bonds:  0
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.629
Synthetic Accessibility Score:  2.037
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.916
MDCK Permeability:  1.4298786481958814e-05
Pgp-inhibitor:  0.069
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.098
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.225
Plasma Protein Binding (PPB):  99.36072540283203%
Volume Distribution (VD):  0.507
Pgp-substrate:  1.0770334005355835%

ADMET: Metabolism

CYP1A2-inhibitor:  0.96
CYP1A2-substrate:  0.118
CYP2C19-inhibitor:  0.247
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.632
CYP2C9-substrate:  0.587
CYP2D6-inhibitor:  0.584
CYP2D6-substrate:  0.251
CYP3A4-inhibitor:  0.666
CYP3A4-substrate:  0.138

ADMET: Excretion

Clearance (CL):  8.199
Half-life (T1/2):  0.143

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.045
Drug-inuced Liver Injury (DILI):  0.948
AMES Toxicity:  0.883
Rat Oral Acute Toxicity:  0.241
Maximum Recommended Daily Dose:  0.078
Skin Sensitization:  0.61
Carcinogencity:  0.934
Eye Corrosion:  0.008
Eye Irritation:  0.989
Respiratory Toxicity:  0.049

Download Data

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

  Natural Product: NPC375356

Natural Product ID:  NPC375356
Common Name*:   Anthrarufin
IUPAC Name:   1,5-dihydroxyanthracene-9,10-dione
Synonyms:   1,5-Dihydroxy-Anthraquinone; Anthrarufin
Standard InCHIKey:  JPICKYUTICNNNJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16H
SMILES:  c1cc2c(c(c1)O)C(=O)c1cccc(c1C2=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL55761
PubChem CID:   8328
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11076555]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[11459643]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[1517743]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8277318]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae 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
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[496518]
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[496518]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[496520]
NPT544 Protein Family Estrogen receptor Homo sapiens Control = 105.7 % PMID[496515]
NPT544 Protein Family Estrogen receptor Homo sapiens Control = 107.0 % PMID[496515]
NPT544 Protein Family Estrogen receptor Homo sapiens Control = 113.9 % PMID[496515]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 1000.0 nM PMID[496516]
NPT2 Others Unspecified Activity < 50.0 % PMID[496517]
NPT2 Others Unspecified Inhibition = 100.0 % PMID[496518]
NPT2 Others Unspecified Inhibition = 92.3 % PMID[496518]
NPT2 Others Unspecified Inhibition = 70.1 % PMID[496518]
NPT2 Others Unspecified Inhibition = 27.1 % PMID[496518]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens Activity = 0.0 pm/min/mg PMID[496519]
NPT1365 Organism Trichoplusia ni Trichoplusia ni mortality = 15.0 % PMID[496521]
NPT1365 Organism Trichoplusia ni Trichoplusia ni FDI = -58.6 % PMID[496521]

☑ 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 NPC375356 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
0.9914 High Similarity NPC300274
0.9831 High Similarity NPC103540
0.9748 High Similarity NPC96915
0.9587 High Similarity NPC282923
0.958 High Similarity NPC142956
0.9508 High Similarity NPC99731
0.9431 High Similarity NPC136588
0.9431 High Similarity NPC199253
0.9426 High Similarity NPC48248
0.9421 High Similarity NPC3224
0.9355 High Similarity NPC205992
0.935 High Similarity NPC34414
0.935 High Similarity NPC146647
0.9322 High Similarity NPC206778
0.9322 High Similarity NPC285829
0.928 High Similarity NPC70622
0.9274 High Similarity NPC31799
0.9256 High Similarity NPC173978
0.925 High Similarity NPC307174
0.925 High Similarity NPC91478
0.9206 High Similarity NPC115458
0.9206 High Similarity NPC225051
0.9206 High Similarity NPC294226
0.9206 High Similarity NPC52407
0.92 High Similarity NPC244699
0.9167 High Similarity NPC120545
0.9145 High Similarity NPC108288
0.9134 High Similarity NPC44437
0.9134 High Similarity NPC288089
0.912 High Similarity NPC55949
0.9106 High Similarity NPC306765
0.9106 High Similarity NPC231774
0.9098 High Similarity NPC310540
0.9062 High Similarity NPC80035
0.9062 High Similarity NPC283088
0.9055 High Similarity NPC53896
0.8992 High Similarity NPC155211
0.8992 High Similarity NPC141934
0.8992 High Similarity NPC193358
0.8992 High Similarity NPC272268
0.8992 High Similarity NPC474813
0.8984 High Similarity NPC50924
0.8976 High Similarity NPC58685
0.8943 High Similarity NPC74507
0.8943 High Similarity NPC234890
0.8923 High Similarity NPC245923
0.8923 High Similarity NPC53206
0.8923 High Similarity NPC53414
0.8917 High Similarity NPC232178
0.8915 High Similarity NPC258502
0.8898 High Similarity NPC93015
0.8898 High Similarity NPC161304
0.888 High Similarity NPC471530
0.8855 High Similarity NPC4214
0.8855 High Similarity NPC61398
0.8855 High Similarity NPC416
0.8855 High Similarity NPC13715
0.8846 High Similarity NPC254847
0.8843 High Similarity NPC7151
0.8843 High Similarity NPC216297
0.8843 High Similarity NPC473662
0.8824 High Similarity NPC477453
0.8819 High Similarity NPC475741
0.8819 High Similarity NPC31539
0.881 High Similarity NPC234175
0.881 High Similarity NPC237225
0.88 High Similarity NPC160499
0.879 High Similarity NPC68756
0.879 High Similarity NPC152525
0.879 High Similarity NPC236189
0.8788 High Similarity NPC138099
0.8788 High Similarity NPC1268
0.8788 High Similarity NPC242994
0.8788 High Similarity NPC26924
0.878 High Similarity NPC283514
0.8779 High Similarity NPC147418
0.8779 High Similarity NPC471905
0.8769 High Similarity NPC161632
0.876 High Similarity NPC171968
0.876 High Similarity NPC314048
0.875 High Similarity NPC474517
0.875 High Similarity NPC72669
0.8722 High Similarity NPC315578
0.8722 High Similarity NPC169452
0.8722 High Similarity NPC96421
0.8722 High Similarity NPC181560
0.8722 High Similarity NPC203063
0.8699 High Similarity NPC198336
0.8692 High Similarity NPC287604
0.8692 High Similarity NPC161964
0.8692 High Similarity NPC472262
0.8682 High Similarity NPC110609
0.8682 High Similarity NPC246693
0.8682 High Similarity NPC242358
0.8672 High Similarity NPC117609
0.8672 High Similarity NPC198305
0.8661 High Similarity NPC95537
0.8657 High Similarity NPC124365
0.8651 High Similarity NPC1991
0.8651 High Similarity NPC51037
0.8647 High Similarity NPC190457
0.8647 High Similarity NPC143438
0.8636 High Similarity NPC305060
0.8629 High Similarity NPC244351
0.8615 High Similarity NPC267205
0.8594 High Similarity NPC278928
0.8593 High Similarity NPC69755
0.8593 High Similarity NPC257644
0.8593 High Similarity NPC73061
0.8593 High Similarity NPC239136
0.8593 High Similarity NPC193555
0.8593 High Similarity NPC19631
0.8583 High Similarity NPC240163
0.8582 High Similarity NPC225243
0.856 High Similarity NPC135062
0.855 High Similarity NPC282780
0.855 High Similarity NPC166480
0.8538 High Similarity NPC309430
0.8534 High Similarity NPC141523
0.8529 High Similarity NPC471682
0.8529 High Similarity NPC66593
0.8529 High Similarity NPC238629
0.8525 High Similarity NPC41567
0.8519 High Similarity NPC305845
0.8519 High Similarity NPC290550
0.8519 High Similarity NPC204045
0.8519 High Similarity NPC246638
0.8516 High Similarity NPC165257
0.8516 High Similarity NPC96024
0.8504 High Similarity NPC8745
0.8485 Intermediate Similarity NPC22222
0.8485 Intermediate Similarity NPC281513
0.8468 Intermediate Similarity NPC472046
0.8467 Intermediate Similarity NPC193703
0.8467 Intermediate Similarity NPC79627
0.8467 Intermediate Similarity NPC21599
0.8462 Intermediate Similarity NPC85342
0.8462 Intermediate Similarity NPC224584
0.8462 Intermediate Similarity NPC17083
0.8456 Intermediate Similarity NPC474300
0.8456 Intermediate Similarity NPC135524
0.8455 Intermediate Similarity NPC184579
0.8455 Intermediate Similarity NPC233165
0.845 Intermediate Similarity NPC57552
0.845 Intermediate Similarity NPC276238
0.845 Intermediate Similarity NPC25736
0.8444 Intermediate Similarity NPC183345
0.8443 Intermediate Similarity NPC269414
0.8443 Intermediate Similarity NPC125252
0.8438 Intermediate Similarity NPC176130
0.8438 Intermediate Similarity NPC78364
0.8438 Intermediate Similarity NPC84672
0.8438 Intermediate Similarity NPC69424
0.8433 Intermediate Similarity NPC61590
0.8433 Intermediate Similarity NPC173980
0.8425 Intermediate Similarity NPC10926
0.8421 Intermediate Similarity NPC472308
0.8421 Intermediate Similarity NPC191976
0.8421 Intermediate Similarity NPC315275
0.8413 Intermediate Similarity NPC275145
0.8413 Intermediate Similarity NPC477153
0.8409 Intermediate Similarity NPC1249
0.8409 Intermediate Similarity NPC12070
0.8406 Intermediate Similarity NPC73416
0.8406 Intermediate Similarity NPC160777
0.8406 Intermediate Similarity NPC478019
0.8406 Intermediate Similarity NPC471683
0.8394 Intermediate Similarity NPC476473
0.8385 Intermediate Similarity NPC27659
0.8385 Intermediate Similarity NPC108129
0.8382 Intermediate Similarity NPC477275
0.8376 Intermediate Similarity NPC34715
0.8374 Intermediate Similarity NPC184527
0.8372 Intermediate Similarity NPC247250
0.8372 Intermediate Similarity NPC767
0.837 Intermediate Similarity NPC114620
0.837 Intermediate Similarity NPC295339
0.837 Intermediate Similarity NPC103337
0.8359 Intermediate Similarity NPC136342
0.8359 Intermediate Similarity NPC295202
0.8359 Intermediate Similarity NPC254492
0.8359 Intermediate Similarity NPC49647
0.8359 Intermediate Similarity NPC227741
0.8358 Intermediate Similarity NPC238108
0.8358 Intermediate Similarity NPC62272
0.8346 Intermediate Similarity NPC72918
0.8346 Intermediate Similarity NPC249272
0.8346 Intermediate Similarity NPC199273
0.8346 Intermediate Similarity NPC13238
0.8346 Intermediate Similarity NPC164014
0.8345 Intermediate Similarity NPC300540
0.8345 Intermediate Similarity NPC314437
0.8345 Intermediate Similarity NPC147250
0.8333 Intermediate Similarity NPC19896
0.8333 Intermediate Similarity NPC176208
0.8333 Intermediate Similarity NPC471906
0.8333 Intermediate Similarity NPC254603
0.8333 Intermediate Similarity NPC114183
0.8333 Intermediate Similarity NPC282577
0.8333 Intermediate Similarity NPC217756

  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 NPC375356 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
0.9831 High Similarity NPD1470 Approved
0.9492 High Similarity NPD1201 Approved
0.9145 High Similarity NPD405 Clinical (unspecified phase)
0.8846 High Similarity NPD1509 Clinical (unspecified phase)
0.8358 Intermediate Similarity NPD5404 Approved
0.8358 Intermediate Similarity NPD5406 Approved
0.8358 Intermediate Similarity NPD5408 Approved
0.8358 Intermediate Similarity NPD5405 Approved
0.8162 Intermediate Similarity NPD2346 Discontinued
0.814 Intermediate Similarity NPD1164 Approved
0.812 Intermediate Similarity NPD943 Approved
0.8042 Intermediate Similarity NPD3226 Approved
0.7953 Intermediate Similarity NPD3019 Approved
0.7943 Intermediate Similarity NPD7390 Discontinued
0.7872 Intermediate Similarity NPD3300 Phase 2
0.7851 Intermediate Similarity NPD9266 Approved
0.7851 Intermediate Similarity NPD74 Approved
0.7836 Intermediate Similarity NPD3764 Approved
0.7836 Intermediate Similarity NPD2313 Discontinued
0.7812 Intermediate Similarity NPD2932 Approved
0.7803 Intermediate Similarity NPD2798 Approved
0.7769 Intermediate Similarity NPD9267 Approved
0.7769 Intermediate Similarity NPD9264 Approved
0.7769 Intermediate Similarity NPD9263 Approved
0.7769 Intermediate Similarity NPD2342 Discontinued
0.7762 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD2935 Discontinued
0.7643 Intermediate Similarity NPD2344 Approved
0.7638 Intermediate Similarity NPD9493 Approved
0.7626 Intermediate Similarity NPD2799 Discontinued
0.7626 Intermediate Similarity NPD1510 Phase 2
0.7619 Intermediate Similarity NPD5951 Approved
0.7594 Intermediate Similarity NPD1203 Approved
0.7557 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD1471 Phase 3
0.7482 Intermediate Similarity NPD1607 Approved
0.7481 Intermediate Similarity NPD3026 Approved
0.7481 Intermediate Similarity NPD3023 Approved
0.748 Intermediate Similarity NPD9281 Approved
0.7464 Intermediate Similarity NPD1240 Approved
0.7462 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD3025 Approved
0.7462 Intermediate Similarity NPD3024 Approved
0.7438 Intermediate Similarity NPD9261 Approved
0.7431 Intermediate Similarity NPD2309 Approved
0.7377 Intermediate Similarity NPD1237 Approved
0.7368 Intermediate Similarity NPD4878 Approved
0.7361 Intermediate Similarity NPD7003 Approved
0.7361 Intermediate Similarity NPD3750 Approved
0.7355 Intermediate Similarity NPD6232 Discontinued
0.7343 Intermediate Similarity NPD1549 Phase 2
0.7325 Intermediate Similarity NPD7473 Discontinued
0.7323 Intermediate Similarity NPD7635 Approved
0.7315 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD288 Approved
0.7273 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD1283 Approved
0.7259 Intermediate Similarity NPD1876 Approved
0.7239 Intermediate Similarity NPD9717 Approved
0.7237 Intermediate Similarity NPD7819 Suspended
0.7227 Intermediate Similarity NPD844 Approved
0.7222 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD1932 Approved
0.7211 Intermediate Similarity NPD1511 Approved
0.7208 Intermediate Similarity NPD3749 Approved
0.7203 Intermediate Similarity NPD1551 Phase 2
0.72 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1651 Approved
0.7194 Intermediate Similarity NPD411 Approved
0.7163 Intermediate Similarity NPD447 Suspended
0.7162 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD1929 Approved
0.7154 Intermediate Similarity NPD1930 Approved
0.7154 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6663 Approved
0.7133 Intermediate Similarity NPD4308 Phase 3
0.7131 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD8166 Discontinued
0.7123 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1512 Approved
0.7109 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD5736 Approved
0.707 Intermediate Similarity NPD6959 Discontinued
0.7055 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD3020 Approved
0.7039 Intermediate Similarity NPD4380 Phase 2
0.7037 Intermediate Similarity NPD1281 Approved
0.7034 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD520 Approved
0.7015 Intermediate Similarity NPD2286 Discontinued
0.7014 Intermediate Similarity NPD3748 Approved
0.7013 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD8313 Approved
0.7012 Intermediate Similarity NPD8312 Approved
0.7008 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6273 Approved
0.7 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.6992 Remote Similarity NPD3091 Approved
0.6985 Remote Similarity NPD3972 Approved
0.6974 Remote Similarity NPD7458 Discontinued
0.6968 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6963 Remote Similarity NPD4879 Approved
0.6957 Remote Similarity NPD2797 Approved
0.6953 Remote Similarity NPD3022 Approved
0.6953 Remote Similarity NPD3021 Approved
0.695 Remote Similarity NPD3268 Approved
0.6948 Remote Similarity NPD1934 Approved
0.6947 Remote Similarity NPD497 Approved
0.6942 Remote Similarity NPD2859 Approved
0.6942 Remote Similarity NPD2860 Approved
0.6934 Remote Similarity NPD1755 Approved
0.6933 Remote Similarity NPD2532 Approved
0.6933 Remote Similarity NPD2534 Approved
0.6933 Remote Similarity NPD2533 Approved
0.6929 Remote Similarity NPD6832 Phase 2
0.6923 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7768 Phase 2
0.6917 Remote Similarity NPD845 Approved
0.6917 Remote Similarity NPD1202 Approved
0.6903 Remote Similarity NPD2801 Approved
0.6889 Remote Similarity NPD4059 Approved
0.6889 Remote Similarity NPD4626 Approved
0.6886 Remote Similarity NPD8150 Discontinued
0.6883 Remote Similarity NPD7411 Suspended
0.6879 Remote Similarity NPD7008 Discontinued
0.6875 Remote Similarity NPD2329 Discontinued
0.687 Remote Similarity NPD498 Approved
0.687 Remote Similarity NPD495 Approved
0.687 Remote Similarity NPD496 Approved
0.6866 Remote Similarity NPD9545 Approved
0.6861 Remote Similarity NPD9269 Phase 2
0.6861 Remote Similarity NPD1608 Approved
0.686 Remote Similarity NPD2933 Approved
0.686 Remote Similarity NPD688 Clinical (unspecified phase)
0.686 Remote Similarity NPD2934 Approved
0.6859 Remote Similarity NPD2296 Approved
0.6859 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6853 Remote Similarity NPD4307 Phase 2
0.6849 Remote Similarity NPD2796 Approved
0.6839 Remote Similarity NPD6844 Discontinued
0.6825 Remote Similarity NPD164 Approved
0.6824 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6822 Remote Similarity NPD4750 Phase 3
0.6815 Remote Similarity NPD4093 Discontinued
0.6815 Remote Similarity NPD3882 Suspended
0.6815 Remote Similarity NPD9268 Approved
0.6812 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6807 Remote Similarity NPD9256 Approved
0.6807 Remote Similarity NPD9258 Approved
0.6805 Remote Similarity NPD8397 Clinical (unspecified phase)
0.68 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6788 Remote Similarity NPD3092 Approved
0.6788 Remote Similarity NPD5031 Approved
0.6788 Remote Similarity NPD5029 Approved
0.6788 Remote Similarity NPD5027 Approved
0.6779 Remote Similarity NPD1196 Approved
0.6779 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6774 Remote Similarity NPD2066 Phase 3
0.6772 Remote Similarity NPD7075 Discontinued
0.6769 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3095 Discontinued
0.6755 Remote Similarity NPD1543 Discontinued
0.6752 Remote Similarity NPD5402 Approved
0.6747 Remote Similarity NPD5034 Approved
0.6747 Remote Similarity NPD5026 Approved
0.6747 Remote Similarity NPD36 Approved
0.6747 Remote Similarity NPD4955 Approved
0.6747 Remote Similarity NPD5028 Approved
0.6747 Remote Similarity NPD4954 Approved
0.6738 Remote Similarity NPD9494 Approved
0.6735 Remote Similarity NPD6099 Approved
0.6735 Remote Similarity NPD6100 Approved
0.6728 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6721 Remote Similarity NPD1432 Clinical (unspecified phase)
0.672 Remote Similarity NPD1242 Phase 1
0.6716 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6714 Remote Similarity NPD3266 Approved
0.6714 Remote Similarity NPD3094 Phase 2
0.6714 Remote Similarity NPD3267 Approved
0.6711 Remote Similarity NPD1195 Approved
0.6711 Remote Similarity NPD2800 Approved
0.6695 Remote Similarity NPD650 Approved
0.6692 Remote Similarity NPD1792 Phase 2
0.6691 Remote Similarity NPD4379 Clinical (unspecified phase)
0.669 Remote Similarity NPD1933 Approved
0.6688 Remote Similarity NPD1465 Phase 2
0.6688 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6687 Remote Similarity NPD5030 Phase 2
0.6686 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6686 Remote Similarity NPD6213 Phase 3
0.6686 Remote Similarity NPD6212 Phase 3
0.6667 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4628 Phase 3
0.6667 Remote Similarity NPD7610 Discontinued

  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