Structure

Physi-Chem Properties

Molecular Weight:  304.17
Volume:  324.75
LogP:  5.522
LogD:  4.041
LogS:  -3.391
# Rotatable Bonds:  8
TPSA:  70.67
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.704
Synthetic Accessibility Score:  2.363
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.862
MDCK Permeability:  2.3589685952174477e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.41
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  98.73377990722656%
Volume Distribution (VD):  1.639
Pgp-substrate:  2.063554525375366%

ADMET: Metabolism

CYP1A2-inhibitor:  0.98
CYP1A2-substrate:  0.509
CYP2C19-inhibitor:  0.943
CYP2C19-substrate:  0.085
CYP2C9-inhibitor:  0.762
CYP2C9-substrate:  0.974
CYP2D6-inhibitor:  0.856
CYP2D6-substrate:  0.824
CYP3A4-inhibitor:  0.481
CYP3A4-substrate:  0.08

ADMET: Excretion

Clearance (CL):  4.687
Half-life (T1/2):  0.631

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.064
Drug-inuced Liver Injury (DILI):  0.455
AMES Toxicity:  0.624
Rat Oral Acute Toxicity:  0.114
Maximum Recommended Daily Dose:  0.686
Skin Sensitization:  0.947
Carcinogencity:  0.092
Eye Corrosion:  0.163
Eye Irritation:  0.97
Respiratory Toxicity:  0.632

Download Data

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

  Natural Product: NPC10971

Natural Product ID:  NPC10971
Common Name*:   5,7-Dihydroxy-2-Nonylchromen-4-One
IUPAC Name:   5,7-dihydroxy-2-nonylchromen-4-one
Synonyms:  
Standard InCHIKey:  GNPQWPVJZHHCFA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H24O4/c1-2-3-4-5-6-7-8-9-14-12-16(21)18-15(20)10-13(19)11-17(18)22-14/h10-12,19-20H,2-9H2,1H3
SMILES:  CCCCCCCCCc1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2003972
PubChem CID:   5378621
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0000144] Chromones

*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
NPO1768 Sansevieria ehrenbergii Species Asparagaceae Eukaryota n.a. African n.a. PMID[15921418]
NPO8160 Diospyros montana Species Ebenaceae Eukaryota n.a. n.a. n.a. PMID[17400463]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19102656]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16062 Trichilia dregeana Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12642 Podadenia thwaitesii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1768 Sansevieria ehrenbergii Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO668 Cnidoscolus texanus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17154 Hymenaea oblongifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17009 Ptelea crenulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9374 Veronica anagallis-aquatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22851 Kryptoperidinium foliaceum Species Peridiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14332 Uvaria ferruginea Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17618 Flaveria bidentis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2535 Bunodactis xanthogrammica Species Actiniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14611 Teucrium fragile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8160 Diospyros montana Species Ebenaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[520205]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 22233.1 nM PMID[520205]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 18535.32 nM PMID[520205]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 16943.38 nM PMID[520205]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 19010.78 nM PMID[520205]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 14321.88 nM PMID[520205]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 16255.49 nM PMID[520205]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 17298.16 nM PMID[520205]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 20230.19 nM PMID[520205]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 16405.9 nM PMID[520205]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 19769.7 nM PMID[520205]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 18071.74 nM PMID[520205]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 10185.91 nM PMID[520205]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 15739.83 nM PMID[520205]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 4909.08 nM PMID[520205]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 14791.08 nM PMID[520205]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 17619.76 nM PMID[520205]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 28641.78 nM PMID[520205]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 20230.19 nM PMID[520205]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 16634.13 nM PMID[520205]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 18923.44 nM PMID[520205]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[520205]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 15170.5 nM PMID[520205]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 18793.17 nM PMID[520205]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 27925.44 nM PMID[520205]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 15100.8 nM PMID[520205]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 18113.4 nM PMID[520205]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 6668.07 nM PMID[520205]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 5861.38 nM PMID[520205]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 19998.62 nM PMID[520205]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 24322.04 nM PMID[520205]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 21777.1 nM PMID[520205]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 18923.44 nM PMID[520205]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 18450.15 nM PMID[520205]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 18071.74 nM PMID[520205]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 21086.28 nM PMID[520205]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 18836.49 nM PMID[520205]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 21677.04 nM PMID[520205]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 3819.44 nM PMID[520205]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 18663.8 nM PMID[520205]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 17988.71 nM PMID[520205]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 22233.1 nM PMID[520205]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 17060.82 nM PMID[520205]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 22646.44 nM PMID[520205]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[520205]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 18749.95 nM PMID[520205]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 16481.62 nM PMID[520205]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 18663.8 nM PMID[520205]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 16672.47 nM PMID[520205]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 21577.44 nM PMID[520205]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 19724.23 nM PMID[520205]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 24266.1 nM PMID[520205]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 17782.79 nM PMID[520205]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 19098.53 nM PMID[520205]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 19186.69 nM PMID[520205]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 27227.01 nM PMID[520205]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 15066.07 nM PMID[520205]

☑ 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 NPC10971 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
0.9841 High Similarity NPC270369
0.9841 High Similarity NPC5515
0.9764 High Similarity NPC31872
0.9764 High Similarity NPC473584
0.9764 High Similarity NPC475589
0.9692 High Similarity NPC13408
0.9692 High Similarity NPC174999
0.9688 High Similarity NPC203817
0.9688 High Similarity NPC25937
0.9612 High Similarity NPC108113
0.9612 High Similarity NPC93756
0.9612 High Similarity NPC223457
0.9545 High Similarity NPC131130
0.9545 High Similarity NPC470668
0.9545 High Similarity NPC470669
0.9542 High Similarity NPC231772
0.9542 High Similarity NPC47815
0.9542 High Similarity NPC234133
0.9542 High Similarity NPC473887
0.9542 High Similarity NPC194281
0.9542 High Similarity NPC29353
0.9542 High Similarity NPC124784
0.9542 High Similarity NPC127447
0.9538 High Similarity NPC236974
0.9538 High Similarity NPC125920
0.9538 High Similarity NPC144027
0.9528 High Similarity NPC187907
0.9474 High Similarity NPC23257
0.9474 High Similarity NPC139554
0.9474 High Similarity NPC96565
0.9474 High Similarity NPC216978
0.9474 High Similarity NPC220062
0.9474 High Similarity NPC55018
0.9474 High Similarity NPC301217
0.9474 High Similarity NPC303633
0.947 High Similarity NPC250266
0.947 High Similarity NPC266597
0.947 High Similarity NPC188879
0.9466 High Similarity NPC60667
0.9462 High Similarity NPC213216
0.9462 High Similarity NPC274121
0.9462 High Similarity NPC50898
0.9462 High Similarity NPC78540
0.9449 High Similarity NPC473907
0.9403 High Similarity NPC261227
0.9403 High Similarity NPC241100
0.9403 High Similarity NPC270883
0.9403 High Similarity NPC471587
0.9403 High Similarity NPC172986
0.9403 High Similarity NPC159275
0.9398 High Similarity NPC201395
0.9398 High Similarity NPC470672
0.9398 High Similarity NPC470671
0.9398 High Similarity NPC124269
0.9398 High Similarity NPC474504
0.9398 High Similarity NPC474487
0.9394 High Similarity NPC187826
0.9394 High Similarity NPC240147
0.9394 High Similarity NPC240593
0.9394 High Similarity NPC470397
0.9394 High Similarity NPC470398
0.9394 High Similarity NPC121243
0.9394 High Similarity NPC156910
0.9389 High Similarity NPC172262
0.9375 High Similarity NPC473894
0.937 High Similarity NPC49852
0.937 High Similarity NPC128428
0.937 High Similarity NPC475496
0.937 High Similarity NPC305518
0.9333 High Similarity NPC262094
0.9333 High Similarity NPC156590
0.9333 High Similarity NPC147688
0.9333 High Similarity NPC205006
0.9333 High Similarity NPC118840
0.9333 High Similarity NPC110969
0.9333 High Similarity NPC90582
0.9333 High Similarity NPC64908
0.9333 High Similarity NPC282300
0.9328 High Similarity NPC241838
0.9328 High Similarity NPC143799
0.9328 High Similarity NPC78913
0.9328 High Similarity NPC217186
0.9328 High Similarity NPC152042
0.9328 High Similarity NPC53181
0.9328 High Similarity NPC140890
0.9328 High Similarity NPC18260
0.9323 High Similarity NPC228661
0.9318 High Similarity NPC242712
0.9318 High Similarity NPC101752
0.9318 High Similarity NPC151113
0.9313 High Similarity NPC204960
0.9313 High Similarity NPC18877
0.9313 High Similarity NPC56031
0.9313 High Similarity NPC192304
0.9313 High Similarity NPC57601
0.9313 High Similarity NPC139813
0.9313 High Similarity NPC159623
0.9313 High Similarity NPC337373
0.9313 High Similarity NPC188646
0.9313 High Similarity NPC175098
0.9313 High Similarity NPC144051
0.9313 High Similarity NPC472365
0.9313 High Similarity NPC28753
0.9313 High Similarity NPC263670
0.9313 High Similarity NPC294593
0.9313 High Similarity NPC242294
0.9313 High Similarity NPC312318
0.9313 High Similarity NPC20560
0.9313 High Similarity NPC82225
0.9308 High Similarity NPC113006
0.9265 High Similarity NPC59739
0.9265 High Similarity NPC62840
0.9265 High Similarity NPC204469
0.9265 High Similarity NPC226636
0.9265 High Similarity NPC299080
0.9265 High Similarity NPC11561
0.9265 High Similarity NPC293852
0.9265 High Similarity NPC200694
0.9265 High Similarity NPC214236
0.9265 High Similarity NPC217083
0.9265 High Similarity NPC78803
0.9259 High Similarity NPC129853
0.9259 High Similarity NPC184536
0.9259 High Similarity NPC188243
0.9259 High Similarity NPC6407
0.9259 High Similarity NPC103342
0.9259 High Similarity NPC269652
0.9259 High Similarity NPC103904
0.9259 High Similarity NPC69769
0.9259 High Similarity NPC146679
0.9259 High Similarity NPC475680
0.9259 High Similarity NPC76445
0.9259 High Similarity NPC235239
0.9259 High Similarity NPC284550
0.9259 High Similarity NPC150522
0.9259 High Similarity NPC230285
0.9259 High Similarity NPC59951
0.9259 High Similarity NPC477272
0.9259 High Similarity NPC281207
0.9259 High Similarity NPC110228
0.9259 High Similarity NPC305355
0.9254 High Similarity NPC276905
0.9254 High Similarity NPC188947
0.9254 High Similarity NPC280284
0.9254 High Similarity NPC470399
0.9254 High Similarity NPC57380
0.9254 High Similarity NPC99333
0.9248 High Similarity NPC187432
0.9248 High Similarity NPC216361
0.9248 High Similarity NPC256042
0.9248 High Similarity NPC281917
0.9248 High Similarity NPC116775
0.9242 High Similarity NPC286336
0.9237 High Similarity NPC212631
0.9237 High Similarity NPC129132
0.9237 High Similarity NPC205468
0.9237 High Similarity NPC87231
0.9237 High Similarity NPC101294
0.9237 High Similarity NPC473655
0.9237 High Similarity NPC257756
0.9231 High Similarity NPC137264
0.9225 High Similarity NPC212379
0.9225 High Similarity NPC69235
0.9197 High Similarity NPC24821
0.9197 High Similarity NPC190637
0.9197 High Similarity NPC473812
0.9197 High Similarity NPC11700
0.9197 High Similarity NPC9117
0.9197 High Similarity NPC219915
0.9197 High Similarity NPC158874
0.9197 High Similarity NPC212932
0.9197 High Similarity NPC293053
0.9197 High Similarity NPC38219
0.9197 High Similarity NPC473813
0.9191 High Similarity NPC166689
0.9191 High Similarity NPC136840
0.9191 High Similarity NPC96408
0.9191 High Similarity NPC103362
0.9191 High Similarity NPC258630
0.9191 High Similarity NPC156190
0.9191 High Similarity NPC17170
0.9191 High Similarity NPC279650
0.9191 High Similarity NPC14871
0.9185 High Similarity NPC225153
0.9185 High Similarity NPC20709
0.9185 High Similarity NPC274784
0.9185 High Similarity NPC310135
0.9185 High Similarity NPC265871
0.9185 High Similarity NPC329203
0.9185 High Similarity NPC150648
0.9185 High Similarity NPC230902
0.9185 High Similarity NPC471697
0.9185 High Similarity NPC222342
0.9179 High Similarity NPC131782
0.9179 High Similarity NPC290291
0.9179 High Similarity NPC138047
0.9179 High Similarity NPC299379
0.9179 High Similarity NPC160972
0.9179 High Similarity NPC275055
0.9179 High Similarity NPC474624

  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 NPC10971 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
0.913 High Similarity NPD4378 Clinical (unspecified phase)
0.9037 High Similarity NPD1550 Clinical (unspecified phase)
0.9037 High Similarity NPD1552 Clinical (unspecified phase)
0.9015 High Similarity NPD1240 Approved
0.8993 High Similarity NPD7410 Clinical (unspecified phase)
0.8971 High Similarity NPD1549 Phase 2
0.8889 High Similarity NPD1510 Phase 2
0.8881 High Similarity NPD1607 Approved
0.8832 High Similarity NPD970 Clinical (unspecified phase)
0.8824 High Similarity NPD2796 Approved
0.8786 High Similarity NPD1511 Approved
0.8662 High Similarity NPD1512 Approved
0.8652 High Similarity NPD6799 Approved
0.8633 High Similarity NPD2800 Approved
0.863 High Similarity NPD2801 Approved
0.8503 High Similarity NPD2393 Clinical (unspecified phase)
0.8493 Intermediate Similarity NPD7411 Suspended
0.8467 Intermediate Similarity NPD6651 Approved
0.8446 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8444 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD3750 Approved
0.8435 Intermediate Similarity NPD1934 Approved
0.8425 Intermediate Similarity NPD4380 Phase 2
0.8389 Intermediate Similarity NPD3882 Suspended
0.8369 Intermediate Similarity NPD1243 Approved
0.8333 Intermediate Similarity NPD7075 Discontinued
0.8333 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD422 Phase 1
0.8311 Intermediate Similarity NPD6801 Discontinued
0.831 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8299 Intermediate Similarity NPD6599 Discontinued
0.8286 Intermediate Similarity NPD1551 Phase 2
0.8258 Intermediate Similarity NPD9717 Approved
0.8255 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD7819 Suspended
0.8209 Intermediate Similarity NPD1203 Approved
0.82 Intermediate Similarity NPD3817 Phase 2
0.8112 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD2654 Approved
0.8099 Intermediate Similarity NPD2344 Approved
0.8095 Intermediate Similarity NPD5403 Approved
0.8092 Intermediate Similarity NPD3749 Approved
0.8085 Intermediate Similarity NPD3748 Approved
0.8082 Intermediate Similarity NPD2532 Approved
0.8082 Intermediate Similarity NPD2533 Approved
0.8082 Intermediate Similarity NPD2534 Approved
0.8052 Intermediate Similarity NPD6959 Discontinued
0.8028 Intermediate Similarity NPD6099 Approved
0.8028 Intermediate Similarity NPD6100 Approved
0.8026 Intermediate Similarity NPD7768 Phase 2
0.8013 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6166 Phase 2
0.8013 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7054 Approved
0.7973 Intermediate Similarity NPD920 Approved
0.7959 Intermediate Similarity NPD5401 Approved
0.7958 Intermediate Similarity NPD2799 Discontinued
0.7945 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD7472 Approved
0.7914 Intermediate Similarity NPD3268 Approved
0.7911 Intermediate Similarity NPD3818 Discontinued
0.7902 Intermediate Similarity NPD2935 Discontinued
0.7899 Intermediate Similarity NPD6832 Phase 2
0.7879 Intermediate Similarity NPD1548 Phase 1
0.7877 Intermediate Similarity NPD2309 Approved
0.7875 Intermediate Similarity NPD6797 Phase 2
0.7838 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD7251 Discontinued
0.7812 Intermediate Similarity NPD7074 Phase 3
0.781 Intermediate Similarity NPD2797 Approved
0.7808 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD943 Approved
0.7792 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1296 Phase 2
0.7786 Intermediate Similarity NPD2313 Discontinued
0.7778 Intermediate Similarity NPD7808 Phase 3
0.7778 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD5953 Discontinued
0.7754 Intermediate Similarity NPD2798 Approved
0.775 Intermediate Similarity NPD7286 Phase 2
0.7744 Intermediate Similarity NPD9545 Approved
0.7737 Intermediate Similarity NPD3225 Approved
0.7727 Intermediate Similarity NPD9493 Approved
0.7727 Intermediate Similarity NPD5402 Approved
0.7708 Intermediate Similarity NPD7033 Discontinued
0.7708 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD4628 Phase 3
0.7669 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD411 Approved
0.7658 Intermediate Similarity NPD6232 Discontinued
0.7647 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD5494 Approved
0.7643 Intermediate Similarity NPD4908 Phase 1
0.7634 Intermediate Similarity NPD1241 Discontinued
0.7625 Intermediate Similarity NPD7473 Discontinued
0.7622 Intermediate Similarity NPD230 Phase 1
0.7622 Intermediate Similarity NPD447 Suspended
0.7586 Intermediate Similarity NPD4308 Phase 3
0.758 Intermediate Similarity NPD919 Approved
0.7554 Intermediate Similarity NPD3266 Approved
0.7554 Intermediate Similarity NPD3267 Approved
0.7536 Intermediate Similarity NPD4749 Approved
0.7535 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD7390 Discontinued
0.7518 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD1610 Phase 2
0.7516 Intermediate Similarity NPD3226 Approved
0.75 Intermediate Similarity NPD5124 Phase 1
0.75 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1019 Discontinued
0.75 Intermediate Similarity NPD3926 Phase 2
0.75 Intermediate Similarity NPD6559 Discontinued
0.7484 Intermediate Similarity NPD1247 Approved
0.7466 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD1608 Approved
0.7464 Intermediate Similarity NPD3972 Approved
0.7438 Intermediate Similarity NPD5710 Approved
0.7438 Intermediate Similarity NPD5711 Approved
0.7436 Intermediate Similarity NPD1465 Phase 2
0.7394 Intermediate Similarity NPD6104 Discontinued
0.7389 Intermediate Similarity NPD4288 Approved
0.7379 Intermediate Similarity NPD1933 Approved
0.7379 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD1729 Discontinued
0.7365 Intermediate Similarity NPD2346 Discontinued
0.7346 Intermediate Similarity NPD2403 Approved
0.7338 Intermediate Similarity NPD1481 Phase 2
0.7333 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD4363 Phase 3
0.7326 Intermediate Similarity NPD4360 Phase 2
0.7324 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5844 Phase 1
0.731 Intermediate Similarity NPD3142 Approved
0.731 Intermediate Similarity NPD3140 Approved
0.731 Intermediate Similarity NPD4307 Phase 2
0.7299 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD4361 Phase 2
0.7283 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2296 Approved
0.7273 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1652 Phase 2
0.7266 Intermediate Similarity NPD1535 Discovery
0.7252 Intermediate Similarity NPD9266 Approved
0.7252 Intermediate Similarity NPD74 Approved
0.7246 Intermediate Similarity NPD17 Approved
0.7241 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4625 Phase 3
0.7197 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD940 Approved
0.7188 Intermediate Similarity NPD846 Approved
0.7176 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD9267 Approved
0.7176 Intermediate Similarity NPD9263 Approved
0.7176 Intermediate Similarity NPD9264 Approved
0.7172 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6798 Discontinued
0.7172 Intermediate Similarity NPD3764 Approved
0.7171 Intermediate Similarity NPD2354 Approved
0.7143 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1201 Approved
0.7134 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1471 Phase 3
0.7122 Intermediate Similarity NPD1778 Approved
0.7101 Intermediate Similarity NPD1894 Discontinued
0.7093 Intermediate Similarity NPD4287 Approved
0.7092 Intermediate Similarity NPD9269 Phase 2
0.7083 Intermediate Similarity NPD9494 Approved
0.708 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD1613 Approved
0.7075 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1164 Approved
0.7063 Intermediate Similarity NPD1470 Approved
0.705 Intermediate Similarity NPD9268 Approved
0.7048 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6844 Discontinued
0.7032 Intermediate Similarity NPD4662 Approved
0.7032 Intermediate Similarity NPD4661 Approved
0.7027 Intermediate Similarity NPD6355 Discontinued
0.7025 Intermediate Similarity NPD6585 Discontinued
0.702 Intermediate Similarity NPD2353 Approved
0.702 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6233 Phase 2
0.7007 Intermediate Similarity NPD6671 Approved
0.6993 Remote Similarity NPD1876 Approved
0.6987 Remote Similarity NPD5049 Phase 3
0.6986 Remote Similarity NPD3027 Phase 3
0.6982 Remote Similarity NPD3658 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5890 Approved
0.6981 Remote Similarity NPD5889 Approved
0.6975 Remote Similarity NPD6971 Discontinued
0.6974 Remote Similarity NPD2424 Discontinued
0.6968 Remote Similarity NPD7212 Phase 2
0.6968 Remote Similarity NPD7213 Phase 3
0.6962 Remote Similarity NPD7458 Discontinued
0.6954 Remote Similarity NPD5405 Approved
0.6954 Remote Similarity NPD5408 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