Structure

Physi-Chem Properties

Molecular Weight:  338.12
Volume:  337.19
LogP:  3.857
LogD:  3.823
LogS:  -3.602
# Rotatable Bonds:  0
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.769
Synthetic Accessibility Score:  4.175
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.788
MDCK Permeability:  1.8718628780334257e-05
Pgp-inhibitor:  0.165
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.154
Plasma Protein Binding (PPB):  97.76786804199219%
Volume Distribution (VD):  0.754
Pgp-substrate:  2.8680171966552734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.441
CYP1A2-substrate:  0.717
CYP2C19-inhibitor:  0.826
CYP2C19-substrate:  0.75
CYP2C9-inhibitor:  0.793
CYP2C9-substrate:  0.948
CYP2D6-inhibitor:  0.941
CYP2D6-substrate:  0.834
CYP3A4-inhibitor:  0.842
CYP3A4-substrate:  0.372

ADMET: Excretion

Clearance (CL):  7.625
Half-life (T1/2):  0.231

ADMET: Toxicity

hERG Blockers:  0.405
Human Hepatotoxicity (H-HT):  0.924
Drug-inuced Liver Injury (DILI):  0.562
AMES Toxicity:  0.825
Rat Oral Acute Toxicity:  0.857
Maximum Recommended Daily Dose:  0.835
Skin Sensitization:  0.626
Carcinogencity:  0.837
Eye Corrosion:  0.003
Eye Irritation:  0.122
Respiratory Toxicity:  0.854

Download Data

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

  Natural Product: NPC51543

Natural Product ID:  NPC51543
Common Name*:   Didesmethylrocaglamide
IUPAC Name:   (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
Synonyms:   Didesmethylrocaglamide
Standard InCHIKey:  RMNPQEWLGQURNX-PXIJUOARSA-N
Standard InCHI:  InChI=1S/C27H27NO7/c1-32-17-11-9-16(10-12-17)27-22(15-7-5-4-6-8-15)21(25(28)30)24(29)26(27,31)23-19(34-3)13-18(33-2)14-20(23)35-27/h4-14,21-22,24,29,31H,1-3H3,(H2,28,30)/t21-,22-,24-,26+,27+/m1/s1
SMILES:  COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=N)O)O)c(OC)cc(c3)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL583207
PubChem CID:   397614
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans
        • [CHEMONTID:0003109] Flavaglines

*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
NPO4720 Aglaia perviridis Species Meliaceae Eukaryota leaves, twigs, and fruits Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam 2010-Jan PMID[23301897]
NPO4720 Aglaia perviridis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[31621322]
NPO4720 Aglaia perviridis Species Meliaceae 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. 10.0 nM PMID[505624]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 16.11 nM PMID[505624]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 19.23 nM PMID[505624]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 65.61 nM PMID[505624]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 10.21 nM PMID[505624]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 10.76 nM PMID[505624]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 10.5 nM PMID[505624]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 12.59 nM PMID[505624]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 11.22 nM PMID[505624]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 10.62 nM PMID[505624]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 14.22 nM PMID[505624]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 10.64 nM PMID[505624]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 16.41 nM PMID[505624]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 16.18 nM PMID[505624]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 10.0 nM PMID[505624]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 0.021 uM PMID[505625]
NPT2 Others Unspecified IC50 = 44.0 nM PMID[505623]
NPT27 Others Unspecified ED50 > 50.0 uM PMID[505625]
NPT721 Individual Protein Nuclear factor NF-kappa-B p65 subunit Homo sapiens ED50 > 20.0 uM PMID[505625]

☑ 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 NPC51543 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
0.966 High Similarity NPC87363
0.9375 High Similarity NPC184607
0.9306 High Similarity NPC470937
0.8993 High Similarity NPC20360
0.8974 High Similarity NPC470936
0.8599 High Similarity NPC189730
0.8535 High Similarity NPC164152
0.8438 Intermediate Similarity NPC73422
0.8438 Intermediate Similarity NPC310399
0.8389 Intermediate Similarity NPC474687
0.8375 Intermediate Similarity NPC329743
0.8375 Intermediate Similarity NPC209473
0.8356 Intermediate Similarity NPC162801
0.8333 Intermediate Similarity NPC475836
0.8322 Intermediate Similarity NPC3049
0.8311 Intermediate Similarity NPC117048
0.8311 Intermediate Similarity NPC124085
0.8272 Intermediate Similarity NPC90336
0.8243 Intermediate Similarity NPC85435
0.82 Intermediate Similarity NPC262585
0.82 Intermediate Similarity NPC18189
0.82 Intermediate Similarity NPC20829
0.8194 Intermediate Similarity NPC324492
0.8194 Intermediate Similarity NPC211758
0.8194 Intermediate Similarity NPC317053
0.8194 Intermediate Similarity NPC87794
0.8182 Intermediate Similarity NPC475621
0.8176 Intermediate Similarity NPC13005
0.8151 Intermediate Similarity NPC87224
0.8151 Intermediate Similarity NPC39064
0.8151 Intermediate Similarity NPC47283
0.8151 Intermediate Similarity NPC222572
0.8141 Intermediate Similarity NPC328567
0.8141 Intermediate Similarity NPC327412
0.8141 Intermediate Similarity NPC320970
0.8141 Intermediate Similarity NPC320671
0.8129 Intermediate Similarity NPC181615
0.8118 Intermediate Similarity NPC206061
0.8117 Intermediate Similarity NPC274721
0.8117 Intermediate Similarity NPC135767
0.8117 Intermediate Similarity NPC155392
0.8108 Intermediate Similarity NPC280653
0.8108 Intermediate Similarity NPC476166
0.8108 Intermediate Similarity NPC164574
0.8108 Intermediate Similarity NPC103799
0.8108 Intermediate Similarity NPC17343
0.8108 Intermediate Similarity NPC206224
0.8108 Intermediate Similarity NPC12875
0.8108 Intermediate Similarity NPC150011
0.8108 Intermediate Similarity NPC118114
0.8108 Intermediate Similarity NPC196765
0.8108 Intermediate Similarity NPC207892
0.8108 Intermediate Similarity NPC129784
0.8108 Intermediate Similarity NPC129106
0.8108 Intermediate Similarity NPC236014
0.8108 Intermediate Similarity NPC268917
0.8108 Intermediate Similarity NPC300875
0.8108 Intermediate Similarity NPC228369
0.8105 Intermediate Similarity NPC476334
0.8077 Intermediate Similarity NPC260397
0.8067 Intermediate Similarity NPC115335
0.8067 Intermediate Similarity NPC225696
0.8067 Intermediate Similarity NPC296915
0.8067 Intermediate Similarity NPC97834
0.8067 Intermediate Similarity NPC223008
0.8067 Intermediate Similarity NPC198154
0.8065 Intermediate Similarity NPC277951
0.8065 Intermediate Similarity NPC114119
0.8065 Intermediate Similarity NPC317237
0.8065 Intermediate Similarity NPC470097
0.8065 Intermediate Similarity NPC471415
0.8065 Intermediate Similarity NPC44530
0.8041 Intermediate Similarity NPC470225
0.8041 Intermediate Similarity NPC27187
0.8039 Intermediate Similarity NPC184797
0.8039 Intermediate Similarity NPC309124
0.8026 Intermediate Similarity NPC477938
0.8014 Intermediate Similarity NPC262573
0.8014 Intermediate Similarity NPC50315
0.8014 Intermediate Similarity NPC471215
0.8014 Intermediate Similarity NPC26879
0.8014 Intermediate Similarity NPC283049
0.8014 Intermediate Similarity NPC230479
0.8 Intermediate Similarity NPC215037
0.8 Intermediate Similarity NPC294156
0.8 Intermediate Similarity NPC256015
0.8 Intermediate Similarity NPC92805
0.7988 Intermediate Similarity NPC149502
0.7988 Intermediate Similarity NPC222665
0.7988 Intermediate Similarity NPC271755
0.7988 Intermediate Similarity NPC254071
0.7987 Intermediate Similarity NPC108674
0.7987 Intermediate Similarity NPC271945
0.7987 Intermediate Similarity NPC178054
0.7987 Intermediate Similarity NPC277331
0.7987 Intermediate Similarity NPC100482
0.7987 Intermediate Similarity NPC181497
0.7987 Intermediate Similarity NPC263261
0.7987 Intermediate Similarity NPC87725
0.7974 Intermediate Similarity NPC232164
0.7974 Intermediate Similarity NPC473739
0.7974 Intermediate Similarity NPC236306
0.7961 Intermediate Similarity NPC126101
0.7961 Intermediate Similarity NPC327735
0.7961 Intermediate Similarity NPC141717
0.7949 Intermediate Similarity NPC475492
0.7945 Intermediate Similarity NPC207179
0.7945 Intermediate Similarity NPC167571
0.7945 Intermediate Similarity NPC278552
0.7937 Intermediate Similarity NPC324517
0.7937 Intermediate Similarity NPC329343
0.7937 Intermediate Similarity NPC321972
0.7935 Intermediate Similarity NPC107161
0.7935 Intermediate Similarity NPC472353
0.7931 Intermediate Similarity NPC474160
0.7922 Intermediate Similarity NPC254759
0.7922 Intermediate Similarity NPC174787
0.7922 Intermediate Similarity NPC182509
0.7922 Intermediate Similarity NPC291101
0.7922 Intermediate Similarity NPC160283
0.7922 Intermediate Similarity NPC27495
0.7922 Intermediate Similarity NPC266197
0.7922 Intermediate Similarity NPC213607
0.7905 Intermediate Similarity NPC274717
0.7905 Intermediate Similarity NPC53986
0.7905 Intermediate Similarity NPC38664
0.7895 Intermediate Similarity NPC11727
0.7895 Intermediate Similarity NPC125579
0.7895 Intermediate Similarity NPC164787
0.7895 Intermediate Similarity NPC15109
0.7895 Intermediate Similarity NPC151224
0.7895 Intermediate Similarity NPC61946
0.7885 Intermediate Similarity NPC173203
0.7885 Intermediate Similarity NPC163508
0.7885 Intermediate Similarity NPC477616
0.7881 Intermediate Similarity NPC263064
0.7871 Intermediate Similarity NPC471389
0.7871 Intermediate Similarity NPC5155
0.7871 Intermediate Similarity NPC311530
0.7871 Intermediate Similarity NPC247291
0.7867 Intermediate Similarity NPC211413
0.7867 Intermediate Similarity NPC164804
0.7867 Intermediate Similarity NPC244888
0.7867 Intermediate Similarity NPC293203
0.7867 Intermediate Similarity NPC68205
0.7867 Intermediate Similarity NPC472590
0.7867 Intermediate Similarity NPC118683
0.7862 Intermediate Similarity NPC20757
0.7862 Intermediate Similarity NPC329836
0.7862 Intermediate Similarity NPC227516
0.7857 Intermediate Similarity NPC22517
0.7857 Intermediate Similarity NPC471388
0.7857 Intermediate Similarity NPC292882
0.7852 Intermediate Similarity NPC93962
0.7849 Intermediate Similarity NPC23593
0.7843 Intermediate Similarity NPC306441
0.7843 Intermediate Similarity NPC302701
0.7843 Intermediate Similarity NPC248727
0.7843 Intermediate Similarity NPC162659
0.7843 Intermediate Similarity NPC270456
0.7843 Intermediate Similarity NPC16435
0.7843 Intermediate Similarity NPC265433
0.7843 Intermediate Similarity NPC227503
0.7843 Intermediate Similarity NPC230734
0.7843 Intermediate Similarity NPC474639
0.7843 Intermediate Similarity NPC269091
0.7834 Intermediate Similarity NPC12641
0.7834 Intermediate Similarity NPC15659
0.7834 Intermediate Similarity NPC45257
0.7834 Intermediate Similarity NPC280092
0.7834 Intermediate Similarity NPC93323
0.7834 Intermediate Similarity NPC304894
0.7829 Intermediate Similarity NPC476617
0.7829 Intermediate Similarity NPC476615
0.7829 Intermediate Similarity NPC287745
0.7829 Intermediate Similarity NPC476616
0.7823 Intermediate Similarity NPC81641
0.7812 Intermediate Similarity NPC470098
0.7812 Intermediate Similarity NPC473266
0.7812 Intermediate Similarity NPC470826
0.7808 Intermediate Similarity NPC76465
0.7808 Intermediate Similarity NPC38761
0.7806 Intermediate Similarity NPC22317
0.7799 Intermediate Similarity NPC101376
0.7799 Intermediate Similarity NPC21776
0.7799 Intermediate Similarity NPC16269
0.7792 Intermediate Similarity NPC94994
0.7791 Intermediate Similarity NPC107739
0.7785 Intermediate Similarity NPC469557
0.7778 Intermediate Similarity NPC93783
0.7778 Intermediate Similarity NPC260898
0.7778 Intermediate Similarity NPC474206
0.7778 Intermediate Similarity NPC234333
0.7778 Intermediate Similarity NPC470356
0.7778 Intermediate Similarity NPC121812
0.7778 Intermediate Similarity NPC112246
0.7778 Intermediate Similarity NPC47398
0.7778 Intermediate Similarity NPC112939
0.7778 Intermediate Similarity NPC99572
0.7778 Intermediate Similarity NPC94750

  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 NPC51543 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
0.8027 Intermediate Similarity NPD4908 Phase 1
0.7919 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD1613 Approved
0.7697 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD1610 Phase 2
0.76 Intermediate Similarity NPD2861 Phase 2
0.7582 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD5735 Approved
0.7515 Intermediate Similarity NPD7199 Phase 2
0.75 Intermediate Similarity NPD3027 Phase 3
0.7484 Intermediate Similarity NPD7466 Approved
0.7455 Intermediate Similarity NPD6072 Discontinued
0.7434 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD1548 Phase 1
0.7372 Intermediate Similarity NPD2157 Approved
0.7368 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD7213 Phase 3
0.7346 Intermediate Similarity NPD7212 Phase 2
0.7326 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD7447 Phase 1
0.7296 Intermediate Similarity NPD6002 Phase 3
0.7296 Intermediate Similarity NPD6004 Phase 3
0.7296 Intermediate Similarity NPD5762 Approved
0.7296 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6005 Phase 3
0.7296 Intermediate Similarity NPD5763 Approved
0.7296 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD4097 Suspended
0.7235 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4749 Approved
0.7195 Intermediate Similarity NPD7020 Approved
0.7195 Intermediate Similarity NPD7019 Approved
0.7161 Intermediate Similarity NPD4625 Phase 3
0.716 Intermediate Similarity NPD3892 Phase 2
0.716 Intermediate Similarity NPD6331 Phase 2
0.716 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6353 Approved
0.7143 Intermediate Similarity NPD2424 Discontinued
0.7124 Intermediate Similarity NPD3094 Phase 2
0.7117 Intermediate Similarity NPD2677 Approved
0.7099 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6355 Discontinued
0.7089 Intermediate Similarity NPD5124 Phase 1
0.7086 Intermediate Similarity NPD1091 Approved
0.7076 Intermediate Similarity NPD4967 Phase 2
0.7076 Intermediate Similarity NPD4965 Approved
0.7076 Intermediate Similarity NPD4966 Approved
0.7073 Intermediate Similarity NPD5058 Phase 3
0.707 Intermediate Similarity NPD7477 Discontinued
0.7063 Intermediate Similarity NPD5588 Approved
0.7059 Intermediate Similarity NPD8651 Approved
0.7044 Intermediate Similarity NPD6653 Approved
0.7025 Intermediate Similarity NPD2238 Phase 2
0.7025 Intermediate Similarity NPD4140 Approved
0.7025 Intermediate Similarity NPD1558 Phase 1
0.7025 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD3620 Phase 2
0.7019 Intermediate Similarity NPD2161 Phase 2
0.7006 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6798 Discontinued
0.7 Intermediate Similarity NPD37 Approved
0.7 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4536 Approved
0.7 Intermediate Similarity NPD4538 Approved
0.6994 Remote Similarity NPD1652 Phase 2
0.6994 Remote Similarity NPD6234 Discontinued
0.6993 Remote Similarity NPD6582 Phase 2
0.6993 Remote Similarity NPD5327 Phase 3
0.6993 Remote Similarity NPD6583 Phase 3
0.6988 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6988 Remote Similarity NPD3985 Discontinued
0.6986 Remote Similarity NPD821 Approved
0.6982 Remote Similarity NPD4675 Approved
0.6982 Remote Similarity NPD4678 Approved
0.697 Remote Similarity NPD3122 Phase 3
0.6968 Remote Similarity NPD6584 Phase 3
0.6962 Remote Similarity NPD3162 Approved
0.6962 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6962 Remote Similarity NPD3163 Approved
0.6959 Remote Similarity NPD5929 Approved
0.6959 Remote Similarity NPD7157 Approved
0.6957 Remote Similarity NPD7033 Discontinued
0.6954 Remote Similarity NPD6516 Phase 2
0.6954 Remote Similarity NPD5846 Approved
0.6946 Remote Similarity NPD7526 Approved
0.6946 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6946 Remote Similarity NPD52 Approved
0.6944 Remote Similarity NPD2684 Approved
0.6928 Remote Similarity NPD2231 Phase 2
0.6928 Remote Similarity NPD2235 Phase 2
0.6923 Remote Similarity NPD4005 Discontinued
0.6923 Remote Similarity NPD1712 Approved
0.6919 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4060 Phase 1
0.6918 Remote Similarity NPD3597 Clinical (unspecified phase)
0.6914 Remote Similarity NPD5712 Approved
0.6906 Remote Similarity NPD7549 Discontinued
0.6901 Remote Similarity NPD1934 Approved
0.6893 Remote Similarity NPD6166 Phase 2
0.6893 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6893 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6882 Remote Similarity NPD4380 Phase 2
0.6879 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6875 Remote Similarity NPD290 Approved
0.6871 Remote Similarity NPD7843 Approved
0.6863 Remote Similarity NPD3092 Approved
0.686 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6859 Remote Similarity NPD3690 Phase 2
0.6859 Remote Similarity NPD3691 Phase 2
0.6859 Remote Similarity NPD4624 Approved
0.6859 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6746 Phase 2
0.6855 Remote Similarity NPD1423 Approved
0.6855 Remote Similarity NPD6233 Phase 2
0.6852 Remote Similarity NPD3846 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5960 Phase 3
0.6839 Remote Similarity NPD6971 Discontinued
0.6839 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6835 Remote Similarity NPD3180 Approved
0.6835 Remote Similarity NPD3179 Approved
0.6826 Remote Similarity NPD6087 Phase 1
0.6821 Remote Similarity NPD7741 Discontinued
0.6821 Remote Similarity NPD2415 Discontinued
0.6816 Remote Similarity NPD7228 Approved
0.6796 Remote Similarity NPD7007 Discovery
0.6788 Remote Similarity NPD5062 Approved
0.6788 Remote Similarity NPD5061 Approved
0.6788 Remote Similarity NPD6674 Discontinued
0.6786 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6786 Remote Similarity NPD681 Clinical (unspecified phase)
0.678 Remote Similarity NPD7229 Phase 3
0.6778 Remote Similarity NPD5844 Phase 1
0.6774 Remote Similarity NPD3685 Discontinued
0.6768 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6768 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6667 Approved
0.6766 Remote Similarity NPD6815 Approved
0.6766 Remote Similarity NPD6666 Approved
0.6763 Remote Similarity NPD5772 Approved
0.6763 Remote Similarity NPD8455 Phase 2
0.6763 Remote Similarity NPD5773 Approved
0.6763 Remote Similarity NPD5761 Phase 2
0.6763 Remote Similarity NPD5760 Phase 2
0.6763 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6758 Remote Similarity NPD6559 Discontinued
0.6753 Remote Similarity NPD422 Phase 1
0.675 Remote Similarity NPD840 Approved
0.675 Remote Similarity NPD839 Approved
0.6748 Remote Similarity NPD2155 Approved
0.6748 Remote Similarity NPD2156 Approved
0.6748 Remote Similarity NPD2154 Approved
0.6747 Remote Similarity NPD4628 Phase 3
0.6746 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6744 Remote Similarity NPD3778 Approved
0.6743 Remote Similarity NPD7075 Discontinued
0.673 Remote Similarity NPD7095 Approved
0.673 Remote Similarity NPD6179 Discontinued
0.6728 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6728 Remote Similarity NPD3054 Approved
0.6728 Remote Similarity NPD3052 Approved
0.6727 Remote Similarity NPD1549 Phase 2
0.6727 Remote Similarity NPD7037 Approved
0.6726 Remote Similarity NPD4357 Discontinued
0.6725 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6725 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6722 Remote Similarity NPD3818 Discontinued
0.6711 Remote Similarity NPD6580 Approved
0.6711 Remote Similarity NPD6581 Approved
0.6709 Remote Similarity NPD3018 Phase 2
0.6707 Remote Similarity NPD2796 Approved
0.6707 Remote Similarity NPD6100 Approved
0.6707 Remote Similarity NPD6099 Approved
0.6707 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6801 Discontinued
0.6688 Remote Similarity NPD6362 Approved
0.6687 Remote Similarity NPD1048 Approved
0.6687 Remote Similarity NPD5177 Phase 3
0.6687 Remote Similarity NPD7097 Phase 1
0.6687 Remote Similarity NPD2200 Suspended
0.6686 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6686 Remote Similarity NPD3536 Discontinued
0.6686 Remote Similarity NPD7773 Phase 2
0.6686 Remote Similarity NPD3882 Suspended
0.6686 Remote Similarity NPD4123 Phase 3
0.6686 Remote Similarity NPD6502 Phase 2
0.6686 Remote Similarity NPD7768 Phase 2
0.6686 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6685 Remote Similarity NPD3051 Approved
0.6667 Remote Similarity NPD1375 Discontinued
0.6667 Remote Similarity NPD4666 Phase 3
0.6667 Remote Similarity NPD2801 Approved
0.6667 Remote Similarity NPD5494 Approved
0.6667 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1653 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