Structure

Physi-Chem Properties

Molecular Weight:  504.21
Volume:  525.741
LogP:  7.483
LogD:  3.887
LogS:  -1.921
# Rotatable Bonds:  6
TPSA:  120.36
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.218
Synthetic Accessibility Score:  3.457
Fsp3:  0.3
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.867
MDCK Permeability:  1.4608980563934892e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.069
20% Bioavailability (F20%):  0.465
30% Bioavailability (F30%):  0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  96.33313751220703%
Volume Distribution (VD):  0.656
Pgp-substrate:  7.48065710067749%

ADMET: Metabolism

CYP1A2-inhibitor:  0.436
CYP1A2-substrate:  0.163
CYP2C19-inhibitor:  0.822
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.874
CYP2C9-substrate:  0.841
CYP2D6-inhibitor:  0.649
CYP2D6-substrate:  0.164
CYP3A4-inhibitor:  0.173
CYP3A4-substrate:  0.079

ADMET: Excretion

Clearance (CL):  4.421
Half-life (T1/2):  0.282

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.957
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.304
Rat Oral Acute Toxicity:  0.864
Maximum Recommended Daily Dose:  0.602
Skin Sensitization:  0.716
Carcinogencity:  0.812
Eye Corrosion:  0.003
Eye Irritation:  0.418
Respiratory Toxicity:  0.264

Download Data

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

  Natural Product: NPC237418

Natural Product ID:  NPC237418
Common Name*:   2-(3,4-Dihydroxyphenyl)-6-[(2E)-3,7-Dimethylocta-2,6-Dienyl]-3,5-Dihydroxy-8,8-Dimethylpyrano[2,3-H]Chromen-4-One
IUPAC Name:   2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-dihydroxy-8,8-dimethylpyrano[2,3-h]chromen-4-one
Synonyms:  
Standard InCHIKey:  HHAZEOQNUWGOLG-RQZCQDPDSA-N
Standard InCHI:  InChI=1S/C30H32O7/c1-16(2)7-6-8-17(3)9-11-19-24(33)23-25(34)26(35)27(18-10-12-21(31)22(32)15-18)36-29(23)20-13-14-30(4,5)37-28(19)20/h7,9-10,12-15,31-33,35H,6,8,11H2,1-5H3/b17-9+
SMILES:  CC(=CCC/C(=C/Cc1c(c2c(=O)c(c(c3ccc(c(c3)O)O)oc2c2C=CC(C)(C)Oc12)O)O)/C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1994725
PubChem CID:   5472481
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003503] 6-prenylated flavones

*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
NPO19487 Dorstenia mannii Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19487 Dorstenia mannii Species Moraceae 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. 5023.43 nM PMID[567371]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 5984.12 nM PMID[567371]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2218.2 nM PMID[567371]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 5407.54 nM PMID[567371]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 3435.58 nM PMID[567371]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1678.8 nM PMID[567371]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 2238.72 nM PMID[567371]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 1794.73 nM PMID[567371]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 2951.21 nM PMID[567371]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 665.27 nM PMID[567371]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 2443.43 nM PMID[567371]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 6324.12 nM PMID[567371]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1324.34 nM PMID[567371]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1770.11 nM PMID[567371]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 5321.08 nM PMID[567371]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 4446.31 nM PMID[567371]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 3213.66 nM PMID[567371]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2051.16 nM PMID[567371]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 7177.94 nM PMID[567371]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 5847.9 nM PMID[567371]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 5741.16 nM PMID[567371]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1836.54 nM PMID[567371]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 5236.0 nM PMID[567371]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 3451.44 nM PMID[567371]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 916.22 nM PMID[567371]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 2798.98 nM PMID[567371]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 1524.05 nM PMID[567371]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1819.7 nM PMID[567371]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2254.24 nM PMID[567371]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 7655.97 nM PMID[567371]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 6576.58 nM PMID[567371]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 3872.58 nM PMID[567371]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5223.96 nM PMID[567371]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 2570.4 nM PMID[567371]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 2098.94 nM PMID[567371]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 3556.31 nM PMID[567371]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 5164.16 nM PMID[567371]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 2786.12 nM PMID[567371]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 2570.4 nM PMID[567371]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 1648.16 nM PMID[567371]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 3372.87 nM PMID[567371]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 5308.84 nM PMID[567371]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 5333.35 nM PMID[567371]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 1778.28 nM PMID[567371]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2113.49 nM PMID[567371]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 5623.41 nM PMID[567371]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1853.53 nM PMID[567371]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 9462.37 nM PMID[567371]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 5223.96 nM PMID[567371]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 1794.73 nM PMID[567371]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 2710.19 nM PMID[567371]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 6223.0 nM PMID[567371]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 4365.16 nM PMID[567371]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 7709.03 nM PMID[567371]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1636.82 nM PMID[567371]

☑ 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 NPC237418 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
0.9799 High Similarity NPC170492
0.9735 High Similarity NPC218871
0.9735 High Similarity NPC476630
0.9732 High Similarity NPC37684
0.9732 High Similarity NPC63187
0.9732 High Similarity NPC157784
0.9669 High Similarity NPC276444
0.9669 High Similarity NPC471985
0.9664 High Similarity NPC304295
0.9664 High Similarity NPC59162
0.9664 High Similarity NPC205046
0.961 High Similarity NPC78332
0.9605 High Similarity NPC273843
0.9603 High Similarity NPC133392
0.9597 High Similarity NPC3825
0.9597 High Similarity NPC88804
0.9539 High Similarity NPC13779
0.9539 High Similarity NPC282307
0.9539 High Similarity NPC3980
0.9539 High Similarity NPC170026
0.9539 High Similarity NPC475799
0.9533 High Similarity NPC154345
0.9481 High Similarity NPC28241
0.947 High Similarity NPC249570
0.947 High Similarity NPC45934
0.9423 High Similarity NPC472625
0.9419 High Similarity NPC259456
0.9419 High Similarity NPC198829
0.9416 High Similarity NPC184755
0.9416 High Similarity NPC469658
0.9416 High Similarity NPC74178
0.9416 High Similarity NPC280680
0.9408 High Similarity NPC476631
0.94 High Similarity NPC270465
0.94 High Similarity NPC87125
0.9396 High Similarity NPC166757
0.9396 High Similarity NPC14001
0.9359 High Similarity NPC194427
0.9355 High Similarity NPC204290
0.9355 High Similarity NPC476280
0.9355 High Similarity NPC119209
0.9355 High Similarity NPC118256
0.9355 High Similarity NPC192686
0.9351 High Similarity NPC218313
0.9351 High Similarity NPC474681
0.9351 High Similarity NPC471209
0.9346 High Similarity NPC472280
0.9346 High Similarity NPC234255
0.9342 High Similarity NPC142527
0.9342 High Similarity NPC471982
0.9342 High Similarity NPC237994
0.9338 High Similarity NPC149127
0.9338 High Similarity NPC286342
0.9338 High Similarity NPC188871
0.9333 High Similarity NPC244407
0.9329 High Similarity NPC179271
0.9329 High Similarity NPC20791
0.9329 High Similarity NPC220418
0.9308 High Similarity NPC165456
0.9304 High Similarity NPC471213
0.9295 High Similarity NPC167678
0.9295 High Similarity NPC471210
0.9295 High Similarity NPC29876
0.9295 High Similarity NPC289771
0.9295 High Similarity NPC474038
0.929 High Similarity NPC22192
0.929 High Similarity NPC197856
0.929 High Similarity NPC46736
0.929 High Similarity NPC204879
0.9286 High Similarity NPC133970
0.9286 High Similarity NPC5322
0.9286 High Similarity NPC6633
0.9286 High Similarity NPC472455
0.9281 High Similarity NPC213896
0.9281 High Similarity NPC78326
0.9281 High Similarity NPC270620
0.9281 High Similarity NPC179126
0.9281 High Similarity NPC192083
0.9281 High Similarity NPC236223
0.9281 High Similarity NPC298692
0.9281 High Similarity NPC74924
0.9281 High Similarity NPC189130
0.9276 High Similarity NPC200740
0.9276 High Similarity NPC260895
0.9276 High Similarity NPC125062
0.9276 High Similarity NPC252933
0.9276 High Similarity NPC54394
0.9272 High Similarity NPC269420
0.9267 High Similarity NPC108406
0.9267 High Similarity NPC51443
0.9267 High Similarity NPC74881
0.9241 High Similarity NPC62261
0.9241 High Similarity NPC156432
0.9236 High Similarity NPC83922
0.9236 High Similarity NPC474150
0.9236 High Similarity NPC329760
0.9236 High Similarity NPC472448
0.9236 High Similarity NPC474162
0.9236 High Similarity NPC261470
0.9236 High Similarity NPC206605
0.9231 High Similarity NPC282009
0.9231 High Similarity NPC328102
0.9231 High Similarity NPC297212
0.9231 High Similarity NPC471973
0.9231 High Similarity NPC287328
0.9231 High Similarity NPC475784
0.9231 High Similarity NPC470183
0.9231 High Similarity NPC246478
0.9231 High Similarity NPC476980
0.9226 High Similarity NPC473272
0.9226 High Similarity NPC67876
0.9226 High Similarity NPC284820
0.9226 High Similarity NPC27337
0.9226 High Similarity NPC52889
0.9221 High Similarity NPC321779
0.9221 High Similarity NPC56786
0.9221 High Similarity NPC200246
0.9221 High Similarity NPC80534
0.9221 High Similarity NPC275575
0.9216 High Similarity NPC82325
0.9216 High Similarity NPC55205
0.9216 High Similarity NPC279989
0.9216 High Similarity NPC106976
0.9211 High Similarity NPC50728
0.9211 High Similarity NPC166753
0.9205 High Similarity NPC296869
0.92 High Similarity NPC124729
0.92 High Similarity NPC169749
0.9195 High Similarity NPC24821
0.9195 High Similarity NPC190637
0.9195 High Similarity NPC212932
0.9195 High Similarity NPC9117
0.9195 High Similarity NPC279121
0.9195 High Similarity NPC293053
0.9182 High Similarity NPC39091
0.9177 High Similarity NPC189473
0.9177 High Similarity NPC23298
0.9177 High Similarity NPC186686
0.9177 High Similarity NPC12461
0.9177 High Similarity NPC207690
0.9172 High Similarity NPC187354
0.9172 High Similarity NPC26326
0.9172 High Similarity NPC471211
0.9172 High Similarity NPC471499
0.9172 High Similarity NPC234644
0.9172 High Similarity NPC472632
0.9172 High Similarity NPC471212
0.9172 High Similarity NPC472634
0.9172 High Similarity NPC278427
0.9167 High Similarity NPC117418
0.9167 High Similarity NPC210459
0.9167 High Similarity NPC53545
0.9161 High Similarity NPC153512
0.9161 High Similarity NPC471500
0.9161 High Similarity NPC68093
0.9161 High Similarity NPC291878
0.9161 High Similarity NPC265511
0.9161 High Similarity NPC472626
0.9161 High Similarity NPC49824
0.9161 High Similarity NPC470328
0.9161 High Similarity NPC195796
0.9161 High Similarity NPC209614
0.9161 High Similarity NPC191146
0.9161 High Similarity NPC470600
0.9161 High Similarity NPC278778
0.9161 High Similarity NPC35038
0.9156 High Similarity NPC33051
0.9156 High Similarity NPC141212
0.9156 High Similarity NPC162351
0.9156 High Similarity NPC58382
0.9156 High Similarity NPC227337
0.9156 High Similarity NPC273462
0.9156 High Similarity NPC49402
0.9156 High Similarity NPC70433
0.915 High Similarity NPC236769
0.915 High Similarity NPC133953
0.915 High Similarity NPC50403
0.915 High Similarity NPC28274
0.9145 High Similarity NPC48479
0.9145 High Similarity NPC183950
0.9145 High Similarity NPC52005
0.9145 High Similarity NPC177298
0.9145 High Similarity NPC137062
0.9145 High Similarity NPC287101
0.9145 High Similarity NPC195351
0.9145 High Similarity NPC38545
0.9145 High Similarity NPC171916
0.9145 High Similarity NPC223579
0.9145 High Similarity NPC159103
0.9133 High Similarity NPC216538
0.9133 High Similarity NPC326500
0.9133 High Similarity NPC70136
0.9133 High Similarity NPC273538
0.9128 High Similarity NPC473042
0.9128 High Similarity NPC175013
0.9128 High Similarity NPC299080
0.9128 High Similarity NPC217083
0.9128 High Similarity NPC59739
0.9128 High Similarity NPC62840
0.9128 High Similarity NPC78803

  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 NPC237418 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
0.9329 High Similarity NPD1512 Approved
0.9281 High Similarity NPD2393 Clinical (unspecified phase)
0.9195 High Similarity NPD1511 Approved
0.9133 High Similarity NPD4378 Clinical (unspecified phase)
0.9032 High Similarity NPD2801 Approved
0.8968 High Similarity NPD1934 Approved
0.8882 High Similarity NPD6166 Phase 2
0.8882 High Similarity NPD6167 Clinical (unspecified phase)
0.8882 High Similarity NPD6168 Clinical (unspecified phase)
0.8797 High Similarity NPD3882 Suspended
0.8758 High Similarity NPD7410 Clinical (unspecified phase)
0.8734 High Similarity NPD3817 Phase 2
0.8675 High Similarity NPD7251 Discontinued
0.8625 High Similarity NPD7075 Discontinued
0.8614 High Similarity NPD6797 Phase 2
0.8606 High Similarity NPD7054 Approved
0.8599 High Similarity NPD4380 Phase 2
0.8554 High Similarity NPD7074 Phase 3
0.8554 High Similarity NPD7472 Approved
0.8553 High Similarity NPD7096 Clinical (unspecified phase)
0.8512 High Similarity NPD7808 Phase 3
0.8494 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD3818 Discontinued
0.8402 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD6801 Discontinued
0.8333 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7819 Suspended
0.8301 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD5494 Approved
0.8289 Intermediate Similarity NPD1510 Phase 2
0.8282 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7473 Discontinued
0.8247 Intermediate Similarity NPD1549 Phase 2
0.8235 Intermediate Similarity NPD2796 Approved
0.8217 Intermediate Similarity NPD6799 Approved
0.8199 Intermediate Similarity NPD7411 Suspended
0.8193 Intermediate Similarity NPD6232 Discontinued
0.816 Intermediate Similarity NPD5402 Approved
0.8146 Intermediate Similarity NPD1240 Approved
0.8146 Intermediate Similarity NPD943 Approved
0.8133 Intermediate Similarity NPD6959 Discontinued
0.807 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD5403 Approved
0.8039 Intermediate Similarity NPD1607 Approved
0.8025 Intermediate Similarity NPD6599 Discontinued
0.8025 Intermediate Similarity NPD3750 Approved
0.8024 Intermediate Similarity NPD1247 Approved
0.8012 Intermediate Similarity NPD919 Approved
0.8 Intermediate Similarity NPD7768 Phase 2
0.7988 Intermediate Similarity NPD1465 Phase 2
0.7962 Intermediate Similarity NPD2800 Approved
0.7953 Intermediate Similarity NPD5844 Phase 1
0.7937 Intermediate Similarity NPD5401 Approved
0.7898 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD2935 Discontinued
0.7882 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD3749 Approved
0.7824 Intermediate Similarity NPD3926 Phase 2
0.7821 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6559 Discontinued
0.7815 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6100 Approved
0.7771 Intermediate Similarity NPD6099 Approved
0.7736 Intermediate Similarity NPD1243 Approved
0.7736 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD2534 Approved
0.7716 Intermediate Similarity NPD2533 Approved
0.7716 Intermediate Similarity NPD2532 Approved
0.7707 Intermediate Similarity NPD3748 Approved
0.7692 Intermediate Similarity NPD6651 Approved
0.7677 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD1613 Approved
0.7662 Intermediate Similarity NPD2313 Discontinued
0.7662 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7390 Discontinued
0.7636 Intermediate Similarity NPD3226 Approved
0.7628 Intermediate Similarity NPD230 Phase 1
0.7624 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD920 Approved
0.7595 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD2799 Discontinued
0.7578 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD1551 Phase 2
0.7543 Intermediate Similarity NPD7286 Phase 2
0.7542 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD447 Suspended
0.7515 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD2346 Discontinued
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD3751 Discontinued
0.7485 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3027 Phase 3
0.7458 Intermediate Similarity NPD5953 Discontinued
0.7457 Intermediate Similarity NPD3787 Discontinued
0.7436 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD6190 Approved
0.7414 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD4625 Phase 3
0.7362 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4628 Phase 3
0.7351 Intermediate Similarity NPD4363 Phase 3
0.7351 Intermediate Similarity NPD4360 Phase 2
0.7338 Intermediate Similarity NPD1203 Approved
0.7333 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD3268 Approved
0.7317 Intermediate Similarity NPD2309 Approved
0.7308 Intermediate Similarity NPD8150 Discontinued
0.7308 Intermediate Similarity NPD4908 Phase 1
0.7308 Intermediate Similarity NPD8434 Phase 2
0.7299 Intermediate Similarity NPD7199 Phase 2
0.7296 Intermediate Similarity NPD5124 Phase 1
0.7296 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7584 Approved
0.729 Intermediate Similarity NPD2798 Approved
0.7289 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD6234 Discontinued
0.7273 Intermediate Similarity NPD3225 Approved
0.7267 Intermediate Similarity NPD4308 Phase 3
0.7267 Intermediate Similarity NPD7033 Discontinued
0.7249 Intermediate Similarity NPD6776 Approved
0.7249 Intermediate Similarity NPD6782 Approved
0.7249 Intermediate Similarity NPD6780 Approved
0.7249 Intermediate Similarity NPD6778 Approved
0.7249 Intermediate Similarity NPD6779 Approved
0.7249 Intermediate Similarity NPD6777 Approved
0.7249 Intermediate Similarity NPD6781 Approved
0.7238 Intermediate Similarity NPD8313 Approved
0.7238 Intermediate Similarity NPD8312 Approved
0.7226 Intermediate Similarity NPD2797 Approved
0.7225 Intermediate Similarity NPD7435 Discontinued
0.7222 Intermediate Similarity NPD7685 Pre-registration
0.7208 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD6832 Phase 2
0.7191 Intermediate Similarity NPD7228 Approved
0.719 Intermediate Similarity NPD422 Phase 1
0.7188 Intermediate Similarity NPD1933 Approved
0.7175 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD2403 Approved
0.7169 Intermediate Similarity NPD3300 Phase 2
0.716 Intermediate Similarity NPD1653 Approved
0.7159 Intermediate Similarity NPD7229 Phase 3
0.7159 Intermediate Similarity NPD5710 Approved
0.7159 Intermediate Similarity NPD5711 Approved
0.7152 Intermediate Similarity NPD1548 Phase 1
0.7152 Intermediate Similarity NPD7095 Approved
0.7143 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD9717 Approved
0.7143 Intermediate Similarity NPD5049 Phase 3
0.7143 Intermediate Similarity NPD9269 Phase 2
0.7135 Intermediate Similarity NPD7696 Phase 3
0.7135 Intermediate Similarity NPD7698 Approved
0.7135 Intermediate Similarity NPD7697 Approved
0.7135 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD9494 Approved
0.7128 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4361 Phase 2
0.7125 Intermediate Similarity NPD4060 Phase 1
0.7118 Intermediate Similarity NPD7458 Discontinued
0.7117 Intermediate Similarity NPD5404 Approved
0.7117 Intermediate Similarity NPD5406 Approved
0.7117 Intermediate Similarity NPD5405 Approved
0.7117 Intermediate Similarity NPD5408 Approved
0.711 Intermediate Similarity NPD4288 Approved
0.7108 Intermediate Similarity NPD2354 Approved
0.7107 Intermediate Similarity NPD6798 Discontinued
0.7098 Intermediate Similarity NPD7870 Phase 2
0.7098 Intermediate Similarity NPD7871 Phase 2
0.7097 Intermediate Similarity NPD4749 Approved
0.7093 Intermediate Similarity NPD6844 Discontinued
0.7093 Intermediate Similarity NPD37 Approved
0.7083 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6355 Discontinued
0.7081 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD1610 Phase 2
0.7078 Intermediate Similarity NPD1201 Approved
0.7077 Intermediate Similarity NPD7701 Phase 2
0.7073 Intermediate Similarity NPD1471 Phase 3
0.7069 Intermediate Similarity NPD4965 Approved
0.7069 Intermediate Similarity NPD4966 Approved
0.7069 Intermediate Similarity NPD4967 Phase 2
0.7041 Intermediate Similarity NPD8151 Discontinued
0.7019 Intermediate Similarity NPD4307 Phase 2
0.7018 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3266 Approved
0.7006 Intermediate Similarity NPD1470 Approved
0.7006 Intermediate Similarity NPD3267 Approved
0.7005 Intermediate Similarity NPD7874 Approved
0.7005 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD411 Approved
0.6988 Remote Similarity NPD2654 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