Structure

Physi-Chem Properties

Molecular Weight:  270.05
Volume:  265.186
LogP:  3.647
LogD:  2.417
LogS:  -4.182
# Rotatable Bonds:  0
TPSA:  94.83
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.638
Synthetic Accessibility Score:  2.622
Fsp3:  0.067
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.025
MDCK Permeability:  1.2970081115781795e-05
Pgp-inhibitor:  0.113
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.082
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.009
Plasma Protein Binding (PPB):  99.69035339355469%
Volume Distribution (VD):  0.335
Pgp-substrate:  2.5158560276031494%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.206
CYP2C19-inhibitor:  0.208
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.757
CYP2C9-substrate:  0.494
CYP2D6-inhibitor:  0.602
CYP2D6-substrate:  0.178
CYP3A4-inhibitor:  0.372
CYP3A4-substrate:  0.097

ADMET: Excretion

Clearance (CL):  5.013
Half-life (T1/2):  0.599

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.284
Drug-inuced Liver Injury (DILI):  0.905
AMES Toxicity:  0.851
Rat Oral Acute Toxicity:  0.744
Maximum Recommended Daily Dose:  0.897
Skin Sensitization:  0.918
Carcinogencity:  0.776
Eye Corrosion:  0.013
Eye Irritation:  0.955
Respiratory Toxicity:  0.246

Download Data

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

  Natural Product: NPC205992

Natural Product ID:  NPC205992
Common Name*:   Islandicin
IUPAC Name:   1,4,5-trihydroxy-2-methylanthracene-9,10-dione
Synonyms:   Islandicin
Standard InCHIKey:  FHFHNVHRVKQQHN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O5/c1-6-5-9(17)11-12(13(6)18)14(19)7-3-2-4-8(16)10(7)15(11)20/h2-5,16-18H,1H3
SMILES:  Oc1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL477724
PubChem CID:   10151
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
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. PMID[11374975]
NPO12925 Streptomyces spinoverrucosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23057874]
NPO12925 Streptomyces spinoverrucosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26489038]
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23982 Ventilago leiocarpa Species Rhamnaceae 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
NPT1306 Cell Line WISH Homo sapiens IC50 > 100000.0 nM PMID[521438]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 100000.0 nM PMID[521438]
NPT80 Cell Line Raji Homo sapiens IC50 > 100000.0 nM PMID[521438]
NPT111 Cell Line K562 Homo sapiens IC50 > 100000.0 nM PMID[521438]
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000.0 nM PMID[521438]
NPT1307 Cell Line Calu-1 Homo sapiens IC50 > 100000.0 nM PMID[521438]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 60813.5 nM PMID[521439]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 47752.93 nM PMID[521439]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 43052.66 nM PMID[521439]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[521439]
NPT2311 Cell Line Calu-3 Homo sapiens IC50 > 50000.0 nM PMID[521440]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[521440]

☑ 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 NPC205992 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
0.9758 High Similarity NPC282923
0.9612 High Similarity NPC474813
0.9612 High Similarity NPC272268
0.9597 High Similarity NPC96915
0.9538 High Similarity NPC245923
0.9524 High Similarity NPC99731
0.9516 High Similarity NPC103540
0.9453 High Similarity NPC70622
0.9435 High Similarity NPC173978
0.9435 High Similarity NPC142956
0.938 High Similarity NPC115458
0.9355 High Similarity NPC375356
0.9313 High Similarity NPC155211
0.9308 High Similarity NPC288089
0.9297 High Similarity NPC136588
0.9297 High Similarity NPC199253
0.9291 High Similarity NPC48248
0.9286 High Similarity NPC3224
0.9274 High Similarity NPC300274
0.9254 High Similarity NPC124365
0.9248 High Similarity NPC143438
0.9242 High Similarity NPC305060
0.9237 High Similarity NPC283088
0.9219 High Similarity NPC278928
0.9219 High Similarity NPC146647
0.9219 High Similarity NPC34414
0.9154 High Similarity NPC58685
0.9147 High Similarity NPC55949
0.9134 High Similarity NPC306765
0.912 High Similarity NPC307174
0.9098 High Similarity NPC53414
0.9098 High Similarity NPC53206
0.9091 High Similarity NPC161632
0.9084 High Similarity NPC52407
0.9084 High Similarity NPC225051
0.9084 High Similarity NPC314048
0.903 High Similarity NPC416
0.903 High Similarity NPC13715
0.903 High Similarity NPC61398
0.9023 High Similarity NPC254847
0.9008 High Similarity NPC246693
0.9008 High Similarity NPC242358
0.9008 High Similarity NPC110609
0.9 High Similarity NPC31799
0.9 High Similarity NPC31539
0.8986 High Similarity NPC471683
0.8984 High Similarity NPC231774
0.8984 High Similarity NPC1991
0.8963 High Similarity NPC242994
0.8963 High Similarity NPC138099
0.8963 High Similarity NPC26924
0.8963 High Similarity NPC1268
0.8955 High Similarity NPC147418
0.8955 High Similarity NPC471905
0.8947 High Similarity NPC80035
0.8939 High Similarity NPC53896
0.8931 High Similarity NPC244699
0.8931 High Similarity NPC72669
0.8931 High Similarity NPC474517
0.8921 High Similarity NPC300540
0.8915 High Similarity NPC471530
0.8897 High Similarity NPC315578
0.8897 High Similarity NPC181560
0.8897 High Similarity NPC169452
0.8881 High Similarity NPC141934
0.888 High Similarity NPC285829
0.888 High Similarity NPC206778
0.8872 High Similarity NPC472262
0.8872 High Similarity NPC50924
0.8872 High Similarity NPC161964
0.8872 High Similarity NPC287604
0.8872 High Similarity NPC44437
0.8841 High Similarity NPC471682
0.8832 High Similarity NPC187843
0.8828 High Similarity NPC152525
0.8828 High Similarity NPC68756
0.8828 High Similarity NPC310540
0.8824 High Similarity NPC190457
0.881 High Similarity NPC472046
0.8806 High Similarity NPC258502
0.88 High Similarity NPC232178
0.8797 High Similarity NPC267205
0.8788 High Similarity NPC85342
0.8777 High Similarity NPC10764
0.8768 High Similarity NPC257644
0.8768 High Similarity NPC239136
0.8768 High Similarity NPC474300
0.8768 High Similarity NPC19631
0.8768 High Similarity NPC193555
0.8759 High Similarity NPC96421
0.8759 High Similarity NPC225243
0.875 High Similarity NPC4214
0.8741 High Similarity NPC472308
0.8722 High Similarity NPC309430
0.8712 High Similarity NPC475741
0.8712 High Similarity NPC198305
0.8705 High Similarity NPC476473
0.8705 High Similarity NPC238629
0.8696 High Similarity NPC290550
0.8696 High Similarity NPC204045
0.8696 High Similarity NPC305845
0.8696 High Similarity NPC246638
0.8692 High Similarity NPC227741
0.8692 High Similarity NPC295202
0.8692 High Similarity NPC49647
0.8692 High Similarity NPC160499
0.8692 High Similarity NPC136342
0.8682 High Similarity NPC234890
0.8682 High Similarity NPC74507
0.8672 High Similarity NPC91478
0.8671 High Similarity NPC315520
0.8657 High Similarity NPC294226
0.8647 High Similarity NPC17083
0.8647 High Similarity NPC93015
0.8643 High Similarity NPC193703
0.8643 High Similarity NPC21599
0.8643 High Similarity NPC244691
0.8643 High Similarity NPC471906
0.8633 High Similarity NPC73061
0.8633 High Similarity NPC135524
0.8629 High Similarity NPC161304
0.8629 High Similarity NPC240163
0.8623 High Similarity NPC183345
0.8615 High Similarity NPC131799
0.8603 High Similarity NPC191976
0.8603 High Similarity NPC315275
0.8603 High Similarity NPC193358
0.8594 High Similarity NPC120545
0.8593 High Similarity NPC1249
0.8593 High Similarity NPC12070
0.8593 High Similarity NPC282780
0.8593 High Similarity NPC166480
0.8582 High Similarity NPC88864
0.8561 High Similarity NPC237225
0.856 High Similarity NPC108288
0.8551 High Similarity NPC471602
0.8551 High Similarity NPC216312
0.8551 High Similarity NPC256463
0.8551 High Similarity NPC299405
0.8551 High Similarity NPC111422
0.8551 High Similarity NPC29771
0.8551 High Similarity NPC306835
0.8551 High Similarity NPC476477
0.8542 High Similarity NPC294646
0.8538 High Similarity NPC236189
0.8529 High Similarity NPC22222
0.8529 High Similarity NPC281513
0.8529 High Similarity NPC249272
0.8521 High Similarity NPC147250
0.8519 High Similarity NPC193169
0.8519 High Similarity NPC171968
0.8519 High Similarity NPC114183
0.8519 High Similarity NPC254603
0.8511 High Similarity NPC48762
0.85 High Similarity NPC69755
0.85 High Similarity NPC474961
0.8493 Intermediate Similarity NPC474824
0.8493 Intermediate Similarity NPC470408
0.8493 Intermediate Similarity NPC218870
0.8493 Intermediate Similarity NPC182921
0.8492 Intermediate Similarity NPC269414
0.8489 Intermediate Similarity NPC327916
0.8489 Intermediate Similarity NPC241349
0.8489 Intermediate Similarity NPC42262
0.8489 Intermediate Similarity NPC203063
0.8489 Intermediate Similarity NPC32749
0.8489 Intermediate Similarity NPC147542
0.8489 Intermediate Similarity NPC37992
0.8489 Intermediate Similarity NPC220496
0.8478 Intermediate Similarity NPC206207
0.8462 Intermediate Similarity NPC119767
0.8462 Intermediate Similarity NPC37709
0.8462 Intermediate Similarity NPC275145
0.8462 Intermediate Similarity NPC477153
0.8456 Intermediate Similarity NPC270899
0.8451 Intermediate Similarity NPC34482
0.844 Intermediate Similarity NPC66593
0.8438 Intermediate Similarity NPC7151
0.8438 Intermediate Similarity NPC216297
0.8438 Intermediate Similarity NPC473662
0.8435 Intermediate Similarity NPC66029
0.8433 Intermediate Similarity NPC108129
0.8429 Intermediate Similarity NPC471444
0.8429 Intermediate Similarity NPC477275
0.8429 Intermediate Similarity NPC257003
0.8425 Intermediate Similarity NPC41567
0.8421 Intermediate Similarity NPC96024
0.8421 Intermediate Similarity NPC165257
0.8417 Intermediate Similarity NPC103337
0.8417 Intermediate Similarity NPC114620
0.8413 Intermediate Similarity NPC477453
0.8409 Intermediate Similarity NPC51037
0.8406 Intermediate Similarity NPC53001
0.8406 Intermediate Similarity NPC62272
0.8392 Intermediate Similarity NPC470570
0.8392 Intermediate Similarity NPC285122
0.838 Intermediate Similarity NPC79627
0.8378 Intermediate Similarity NPC474861
0.837 Intermediate Similarity NPC41847
0.8369 Intermediate Similarity NPC469520

  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 NPC205992 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
0.9516 High Similarity NPD1470 Approved
0.9194 High Similarity NPD1201 Approved
0.9023 High Similarity NPD1509 Clinical (unspecified phase)
0.856 High Similarity NPD405 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD5405 Approved
0.8406 Intermediate Similarity NPD5408 Approved
0.8406 Intermediate Similarity NPD5404 Approved
0.8406 Intermediate Similarity NPD5406 Approved
0.8345 Intermediate Similarity NPD3226 Approved
0.8252 Intermediate Similarity NPD7390 Discontinued
0.8214 Intermediate Similarity NPD2346 Discontinued
0.8069 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD943 Approved
0.7887 Intermediate Similarity NPD2935 Discontinued
0.7808 Intermediate Similarity NPD3300 Phase 2
0.7794 Intermediate Similarity NPD1164 Approved
0.7692 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD7635 Approved
0.7643 Intermediate Similarity NPD3764 Approved
0.7643 Intermediate Similarity NPD6232 Discontinued
0.7643 Intermediate Similarity NPD2313 Discontinued
0.7612 Intermediate Similarity NPD3019 Approved
0.761 Intermediate Similarity NPD7473 Discontinued
0.7559 Intermediate Similarity NPD2342 Discontinued
0.7557 Intermediate Similarity NPD5951 Approved
0.7552 Intermediate Similarity NPD1607 Approved
0.7482 Intermediate Similarity NPD2798 Approved
0.7481 Intermediate Similarity NPD2932 Approved
0.7448 Intermediate Similarity NPD2799 Discontinued
0.7448 Intermediate Similarity NPD1510 Phase 2
0.7413 Intermediate Similarity NPD1240 Approved
0.7364 Intermediate Similarity NPD9266 Approved
0.7364 Intermediate Similarity NPD74 Approved
0.7358 Intermediate Similarity NPD6959 Discontinued
0.7351 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD2344 Approved
0.7329 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD7003 Approved
0.7313 Intermediate Similarity NPD9493 Approved
0.7308 Intermediate Similarity NPD7819 Suspended
0.7294 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD497 Approved
0.7287 Intermediate Similarity NPD9264 Approved
0.7287 Intermediate Similarity NPD9263 Approved
0.7287 Intermediate Similarity NPD9267 Approved
0.7279 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD8150 Discontinued
0.7237 Intermediate Similarity NPD2532 Approved
0.7237 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD2534 Approved
0.7237 Intermediate Similarity NPD2533 Approved
0.723 Intermediate Similarity NPD1471 Phase 3
0.7226 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD498 Approved
0.7218 Intermediate Similarity NPD496 Approved
0.7218 Intermediate Similarity NPD495 Approved
0.7214 Intermediate Similarity NPD1283 Approved
0.72 Intermediate Similarity NPD3750 Approved
0.7197 Intermediate Similarity NPD2801 Approved
0.7197 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD8313 Approved
0.7186 Intermediate Similarity NPD8312 Approved
0.7181 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD1549 Phase 2
0.7174 Intermediate Similarity NPD3026 Approved
0.7174 Intermediate Similarity NPD3023 Approved
0.7171 Intermediate Similarity NPD1511 Approved
0.7163 Intermediate Similarity NPD1203 Approved
0.7162 Intermediate Similarity NPD1551 Phase 2
0.7161 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD1651 Approved
0.7153 Intermediate Similarity NPD3024 Approved
0.7153 Intermediate Similarity NPD3025 Approved
0.7152 Intermediate Similarity NPD2309 Approved
0.7133 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD288 Approved
0.7115 Intermediate Similarity NPD4380 Phase 2
0.7114 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6535 Approved
0.711 Intermediate Similarity NPD6534 Approved
0.7091 Intermediate Similarity NPD5844 Phase 1
0.7086 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD1512 Approved
0.7063 Intermediate Similarity NPD3749 Approved
0.7052 Intermediate Similarity NPD6213 Phase 3
0.7052 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD6212 Phase 3
0.7044 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD844 Approved
0.7037 Intermediate Similarity NPD9281 Approved
0.7034 Intermediate Similarity NPD411 Approved
0.7025 Intermediate Similarity NPD1934 Approved
0.7023 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD447 Suspended
0.7006 Intermediate Similarity NPD6779 Approved
0.7006 Intermediate Similarity NPD6777 Approved
0.7006 Intermediate Similarity NPD6776 Approved
0.7006 Intermediate Similarity NPD6778 Approved
0.7006 Intermediate Similarity NPD6781 Approved
0.7006 Intermediate Similarity NPD6782 Approved
0.7006 Intermediate Similarity NPD6780 Approved
0.7 Intermediate Similarity NPD1611 Approved
0.7 Intermediate Similarity NPD1281 Approved
0.7 Intermediate Similarity NPD7768 Phase 2
0.7 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7699 Phase 2
0.6989 Remote Similarity NPD7700 Phase 2
0.698 Remote Similarity NPD4308 Phase 3
0.6977 Remote Similarity NPD1929 Approved
0.6977 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6977 Remote Similarity NPD1930 Approved
0.6977 Remote Similarity NPD9261 Approved
0.6975 Remote Similarity NPD5494 Approved
0.6972 Remote Similarity NPD1876 Approved
0.6966 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6964 Remote Similarity NPD5027 Approved
0.6964 Remote Similarity NPD5029 Approved
0.6964 Remote Similarity NPD5031 Approved
0.6962 Remote Similarity NPD7411 Suspended
0.695 Remote Similarity NPD4878 Approved
0.695 Remote Similarity NPD9717 Approved
0.6943 Remote Similarity NPD7458 Discontinued
0.6937 Remote Similarity NPD5402 Approved
0.6923 Remote Similarity NPD1237 Approved
0.6918 Remote Similarity NPD6844 Discontinued
0.6917 Remote Similarity NPD4750 Phase 3
0.6908 Remote Similarity NPD2800 Approved
0.6899 Remote Similarity NPD1932 Approved
0.6889 Remote Similarity NPD7435 Discontinued
0.6889 Remote Similarity NPD7698 Approved
0.6889 Remote Similarity NPD7697 Approved
0.6889 Remote Similarity NPD7696 Phase 3
0.6871 Remote Similarity NPD6663 Approved
0.6867 Remote Similarity NPD3748 Approved
0.6864 Remote Similarity NPD6559 Discontinued
0.6863 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6863 Remote Similarity NPD8166 Discontinued
0.6857 Remote Similarity NPD4626 Approved
0.6857 Remote Similarity NPD2286 Discontinued
0.6852 Remote Similarity NPD7075 Discontinued
0.6851 Remote Similarity NPD7871 Phase 2
0.6851 Remote Similarity NPD7870 Phase 2
0.6849 Remote Similarity NPD4625 Phase 3
0.6849 Remote Similarity NPD7008 Discontinued
0.6842 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6835 Remote Similarity NPD9545 Approved
0.6833 Remote Similarity NPD6823 Phase 2
0.6831 Remote Similarity NPD1608 Approved
0.6831 Remote Similarity NPD3972 Approved
0.6831 Remote Similarity NPD9269 Phase 2
0.6828 Remote Similarity NPD5736 Approved
0.6826 Remote Similarity NPD7177 Discontinued
0.6824 Remote Similarity NPD5028 Approved
0.6824 Remote Similarity NPD5026 Approved
0.6824 Remote Similarity NPD4954 Approved
0.6824 Remote Similarity NPD5034 Approved
0.6824 Remote Similarity NPD4955 Approved
0.6824 Remote Similarity NPD36 Approved
0.6821 Remote Similarity NPD6100 Approved
0.6821 Remote Similarity NPD6099 Approved
0.6821 Remote Similarity NPD2796 Approved
0.6815 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6807 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6803 Remote Similarity NPD1699 Clinical (unspecified phase)
0.679 Remote Similarity NPD3882 Suspended
0.6786 Remote Similarity NPD6020 Phase 2
0.6786 Remote Similarity NPD9268 Approved
0.6779 Remote Similarity NPD1899 Clinical (unspecified phase)
0.677 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5030 Phase 2
0.6763 Remote Similarity NPD5038 Approved
0.6763 Remote Similarity NPD5037 Approved
0.6753 Remote Similarity NPD4628 Phase 3
0.6752 Remote Similarity NPD6273 Approved
0.6746 Remote Similarity NPD845 Approved
0.6744 Remote Similarity NPD3020 Approved
0.6741 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7701 Phase 2
0.6738 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6736 Remote Similarity NPD6696 Suspended
0.6728 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6716 Remote Similarity NPD2329 Discontinued
0.6714 Remote Similarity NPD3091 Approved
0.6711 Remote Similarity NPD2979 Phase 3
0.6711 Remote Similarity NPD4307 Phase 2
0.6707 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6166 Phase 2
0.6707 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5036 Approved
0.6691 Remote Similarity NPD7325 Clinical (unspecified phase)
0.669 Remote Similarity NPD2797 Approved
0.669 Remote Similarity NPD3094 Phase 2
0.6689 Remote Similarity NPD3268 Approved
0.6687 Remote Similarity NPD5711 Approved
0.6687 Remote Similarity NPD5710 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data