Structure

Physi-Chem Properties

Molecular Weight:  314.19
Volume:  330.155
LogP:  4.772
LogD:  4.634
LogS:  -5.128
# Rotatable Bonds:  0
TPSA:  45.9
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.748
Synthetic Accessibility Score:  5.394
Fsp3:  0.7
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:  -4.744
MDCK Permeability:  1.4409027244255412e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.067
Plasma Protein Binding (PPB):  97.5812759399414%
Volume Distribution (VD):  1.861
Pgp-substrate:  4.43187141418457%

ADMET: Metabolism

CYP1A2-inhibitor:  0.472
CYP1A2-substrate:  0.845
CYP2C19-inhibitor:  0.16
CYP2C19-substrate:  0.837
CYP2C9-inhibitor:  0.352
CYP2C9-substrate:  0.568
CYP2D6-inhibitor:  0.468
CYP2D6-substrate:  0.646
CYP3A4-inhibitor:  0.321
CYP3A4-substrate:  0.32

ADMET: Excretion

Clearance (CL):  9.968
Half-life (T1/2):  0.087

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.724
Drug-inuced Liver Injury (DILI):  0.548
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.42
Maximum Recommended Daily Dose:  0.765
Skin Sensitization:  0.425
Carcinogencity:  0.091
Eye Corrosion:  0.153
Eye Irritation:  0.279
Respiratory Toxicity:  0.97

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

  Natural Product: NPC260796

Natural Product ID:  NPC260796
Common Name*:   OYXDHOVYZKWSRM-PHJMNMFVSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  OYXDHOVYZKWSRM-PHJMNMFVSA-N
Standard InCHI:  InChI=1S/C20H26O3/c1-11-15-12(22-17(11)21)10-14-19(4)8-5-7-18(2,3)13(19)6-9-20(14)16(15)23-20/h10,13-14,16H,5-9H2,1-4H3/t13-,14+,16-,19-,20+/m1/s1
SMILES:  CC1=C2C(=C[C@H]3[C@]4(C)CCCC(C)(C)[C@H]4CC[C@]43[C@@H]2O4)OC1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1982058
PubChem CID:   161953
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[16792421]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota whole plants Panshi, Jilin Province, China 2009-JUN PMID[21534540]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21534540]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25453801]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26702644]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[28383891]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[512517]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 25000.0 nM PMID[512518]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000.0 nM PMID[512520]
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 50000.0 nM PMID[512520]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC > 400.0 ug.mL-1 PMID[512519]
NPT23295 CELL-LINE LNCaP C4-2B Homo sapiens IC50 = 10000.0 nM PMID[512520]

☑ 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 NPC260796 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
0.9175 High Similarity NPC81630
0.8587 High Similarity NPC93411
0.8416 Intermediate Similarity NPC471206
0.8404 Intermediate Similarity NPC221111
0.8404 Intermediate Similarity NPC280149
0.8367 Intermediate Similarity NPC278673
0.8351 Intermediate Similarity NPC475380
0.8351 Intermediate Similarity NPC209297
0.8351 Intermediate Similarity NPC194132
0.8333 Intermediate Similarity NPC140277
0.8265 Intermediate Similarity NPC475446
0.8265 Intermediate Similarity NPC100912
0.8265 Intermediate Similarity NPC311241
0.8252 Intermediate Similarity NPC50124
0.8182 Intermediate Similarity NPC72647
0.8182 Intermediate Similarity NPC107806
0.8163 Intermediate Similarity NPC16967
0.8144 Intermediate Similarity NPC161998
0.8144 Intermediate Similarity NPC191521
0.8144 Intermediate Similarity NPC38830
0.8125 Intermediate Similarity NPC49420
0.81 Intermediate Similarity NPC16601
0.8081 Intermediate Similarity NPC84335
0.8081 Intermediate Similarity NPC38530
0.8065 Intermediate Similarity NPC474013
0.8061 Intermediate Similarity NPC276110
0.8058 Intermediate Similarity NPC34768
0.8041 Intermediate Similarity NPC162615
0.8041 Intermediate Similarity NPC205034
0.8041 Intermediate Similarity NPC152778
0.8039 Intermediate Similarity NPC165608
0.8021 Intermediate Similarity NPC310479
0.8 Intermediate Similarity NPC472302
0.7957 Intermediate Similarity NPC96055
0.7941 Intermediate Similarity NPC475038
0.7941 Intermediate Similarity NPC109195
0.7935 Intermediate Similarity NPC471218
0.7912 Intermediate Similarity NPC268827
0.7885 Intermediate Similarity NPC477090
0.7879 Intermediate Similarity NPC476519
0.7864 Intermediate Similarity NPC45897
0.7864 Intermediate Similarity NPC23584
0.7864 Intermediate Similarity NPC474822
0.7857 Intermediate Similarity NPC7349
0.7835 Intermediate Similarity NPC182136
0.7835 Intermediate Similarity NPC78973
0.7812 Intermediate Similarity NPC106332
0.781 Intermediate Similarity NPC179380
0.781 Intermediate Similarity NPC302788
0.781 Intermediate Similarity NPC475074
0.781 Intermediate Similarity NPC180744
0.7789 Intermediate Similarity NPC131813
0.7788 Intermediate Similarity NPC165969
0.7778 Intermediate Similarity NPC54996
0.7778 Intermediate Similarity NPC189206
0.7778 Intermediate Similarity NPC477129
0.7778 Intermediate Similarity NPC477130
0.7778 Intermediate Similarity NPC105490
0.7767 Intermediate Similarity NPC476081
0.7767 Intermediate Similarity NPC11956
0.7767 Intermediate Similarity NPC472552
0.7766 Intermediate Similarity NPC306951
0.7757 Intermediate Similarity NPC253906
0.7745 Intermediate Similarity NPC38855
0.7736 Intermediate Similarity NPC181994
0.7723 Intermediate Similarity NPC110937
0.7717 Intermediate Similarity NPC269791
0.7706 Intermediate Similarity NPC171126
0.77 Intermediate Similarity NPC474909
0.77 Intermediate Similarity NPC471915
0.77 Intermediate Similarity NPC472441
0.77 Intermediate Similarity NPC111273
0.7692 Intermediate Similarity NPC184737
0.7692 Intermediate Similarity NPC471938
0.767 Intermediate Similarity NPC11974
0.767 Intermediate Similarity NPC194028
0.767 Intermediate Similarity NPC472554
0.767 Intermediate Similarity NPC168319
0.7664 Intermediate Similarity NPC299590
0.7664 Intermediate Similarity NPC469370
0.7664 Intermediate Similarity NPC75389
0.766 Intermediate Similarity NPC12283
0.766 Intermediate Similarity NPC474193
0.7653 Intermediate Similarity NPC302280
0.7653 Intermediate Similarity NPC220454
0.7653 Intermediate Similarity NPC212679
0.7653 Intermediate Similarity NPC8062
0.7653 Intermediate Similarity NPC469595
0.7647 Intermediate Similarity NPC474440
0.7642 Intermediate Similarity NPC79298
0.7642 Intermediate Similarity NPC43063
0.7629 Intermediate Similarity NPC473879
0.7624 Intermediate Similarity NPC154526
0.7624 Intermediate Similarity NPC472362
0.7624 Intermediate Similarity NPC165632
0.7624 Intermediate Similarity NPC473153
0.7624 Intermediate Similarity NPC472363
0.7619 Intermediate Similarity NPC471937
0.7615 Intermediate Similarity NPC44537
0.7604 Intermediate Similarity NPC286153
0.7604 Intermediate Similarity NPC471219
0.7596 Intermediate Similarity NPC471914
0.7593 Intermediate Similarity NPC478209
0.7593 Intermediate Similarity NPC12795
0.7593 Intermediate Similarity NPC177047
0.7579 Intermediate Similarity NPC32223
0.7576 Intermediate Similarity NPC329842
0.7576 Intermediate Similarity NPC72845
0.7573 Intermediate Similarity NPC476299
0.7573 Intermediate Similarity NPC474012
0.757 Intermediate Similarity NPC275060
0.7551 Intermediate Similarity NPC173042
0.7551 Intermediate Similarity NPC177141
0.7549 Intermediate Similarity NPC51499
0.7549 Intermediate Similarity NPC121402
0.7549 Intermediate Similarity NPC224356
0.7549 Intermediate Similarity NPC132753
0.7549 Intermediate Similarity NPC2049
0.7549 Intermediate Similarity NPC151681
0.7549 Intermediate Similarity NPC175351
0.7547 Intermediate Similarity NPC295843
0.7547 Intermediate Similarity NPC478208
0.7547 Intermediate Similarity NPC478052
0.7547 Intermediate Similarity NPC51719
0.7547 Intermediate Similarity NPC266570
0.7526 Intermediate Similarity NPC476600
0.7526 Intermediate Similarity NPC166857
0.7524 Intermediate Similarity NPC120009
0.7524 Intermediate Similarity NPC297617
0.7524 Intermediate Similarity NPC120321
0.7523 Intermediate Similarity NPC469655
0.7523 Intermediate Similarity NPC469656
0.7523 Intermediate Similarity NPC474846
0.7522 Intermediate Similarity NPC213761
0.7522 Intermediate Similarity NPC35171
0.75 Intermediate Similarity NPC110022
0.75 Intermediate Similarity NPC472954
0.75 Intermediate Similarity NPC478204
0.75 Intermediate Similarity NPC53555
0.75 Intermediate Similarity NPC185287
0.75 Intermediate Similarity NPC472812
0.75 Intermediate Similarity NPC157380
0.75 Intermediate Similarity NPC139692
0.75 Intermediate Similarity NPC228477
0.75 Intermediate Similarity NPC472640
0.75 Intermediate Similarity NPC472641
0.75 Intermediate Similarity NPC137911
0.7477 Intermediate Similarity NPC122816
0.7477 Intermediate Similarity NPC471205
0.7477 Intermediate Similarity NPC67321
0.7477 Intermediate Similarity NPC187435
0.7476 Intermediate Similarity NPC275086
0.7476 Intermediate Similarity NPC181147
0.7476 Intermediate Similarity NPC92275
0.7476 Intermediate Similarity NPC325229
0.7475 Intermediate Similarity NPC472642
0.7475 Intermediate Similarity NPC273199
0.7475 Intermediate Similarity NPC38952
0.7475 Intermediate Similarity NPC212369
0.7474 Intermediate Similarity NPC193198
0.7474 Intermediate Similarity NPC311070
0.7474 Intermediate Similarity NPC52108
0.7474 Intermediate Similarity NPC474789
0.7456 Intermediate Similarity NPC112936
0.7455 Intermediate Similarity NPC42658
0.7455 Intermediate Similarity NPC222834
0.7453 Intermediate Similarity NPC472822
0.7451 Intermediate Similarity NPC190713
0.7449 Intermediate Similarity NPC477128
0.7449 Intermediate Similarity NPC471956
0.7447 Intermediate Similarity NPC25554
0.7434 Intermediate Similarity NPC108581
0.7434 Intermediate Similarity NPC478206
0.7434 Intermediate Similarity NPC16701
0.7434 Intermediate Similarity NPC478205
0.7431 Intermediate Similarity NPC103491
0.7429 Intermediate Similarity NPC114540
0.7429 Intermediate Similarity NPC273668
0.7429 Intermediate Similarity NPC273005
0.7429 Intermediate Similarity NPC165250
0.7429 Intermediate Similarity NPC32577
0.7429 Intermediate Similarity NPC469606
0.7429 Intermediate Similarity NPC31058
0.7429 Intermediate Similarity NPC162973
0.7429 Intermediate Similarity NPC155332
0.7426 Intermediate Similarity NPC201725
0.7426 Intermediate Similarity NPC470255
0.7426 Intermediate Similarity NPC84893
0.7426 Intermediate Similarity NPC470697
0.7407 Intermediate Similarity NPC304276
0.7407 Intermediate Similarity NPC137462
0.7404 Intermediate Similarity NPC473219
0.7404 Intermediate Similarity NPC470761
0.7404 Intermediate Similarity NPC473510
0.7404 Intermediate Similarity NPC474190
0.7404 Intermediate Similarity NPC324841
0.7404 Intermediate Similarity NPC473204
0.74 Intermediate Similarity NPC472811
0.74 Intermediate Similarity NPC78594
0.74 Intermediate Similarity NPC177641

  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 NPC260796 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
0.781 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6648 Approved
0.7188 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4225 Approved
0.7143 Intermediate Similarity NPD7638 Approved
0.7143 Intermediate Similarity NPD1694 Approved
0.7075 Intermediate Similarity NPD7639 Approved
0.7075 Intermediate Similarity NPD7640 Approved
0.7064 Intermediate Similarity NPD6008 Approved
0.7043 Intermediate Similarity NPD7115 Discovery
0.703 Intermediate Similarity NPD6051 Approved
0.6923 Remote Similarity NPD7900 Approved
0.6923 Remote Similarity NPD7901 Clinical (unspecified phase)
0.69 Remote Similarity NPD7146 Approved
0.69 Remote Similarity NPD6409 Approved
0.69 Remote Similarity NPD7334 Approved
0.69 Remote Similarity NPD6684 Approved
0.69 Remote Similarity NPD7521 Approved
0.69 Remote Similarity NPD5330 Approved
0.6852 Remote Similarity NPD5344 Discontinued
0.6838 Remote Similarity NPD7327 Approved
0.6838 Remote Similarity NPD7328 Approved
0.6832 Remote Similarity NPD3573 Approved
0.6807 Remote Similarity NPD7503 Approved
0.678 Remote Similarity NPD7516 Approved
0.6765 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6903 Approved
0.6762 Remote Similarity NPD7748 Approved
0.6757 Remote Similarity NPD6675 Approved
0.6757 Remote Similarity NPD7128 Approved
0.6757 Remote Similarity NPD6402 Approved
0.6757 Remote Similarity NPD5739 Approved
0.6731 Remote Similarity NPD5693 Phase 1
0.6729 Remote Similarity NPD7902 Approved
0.6698 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6697 Remote Similarity NPD4159 Approved
0.6696 Remote Similarity NPD5697 Approved
0.6696 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD6399 Phase 3
0.6637 Remote Similarity NPD6881 Approved
0.6637 Remote Similarity NPD7320 Approved
0.6637 Remote Similarity NPD6899 Approved
0.6636 Remote Similarity NPD7632 Discontinued
0.6604 Remote Similarity NPD6001 Approved
0.6602 Remote Similarity NPD6672 Approved
0.6602 Remote Similarity NPD5737 Approved
0.6579 Remote Similarity NPD6013 Approved
0.6579 Remote Similarity NPD6372 Approved
0.6579 Remote Similarity NPD6012 Approved
0.6579 Remote Similarity NPD6014 Approved
0.6579 Remote Similarity NPD6373 Approved
0.6571 Remote Similarity NPD7515 Phase 2
0.6569 Remote Similarity NPD3618 Phase 1
0.6556 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6529 Remote Similarity NPD8379 Approved
0.6529 Remote Similarity NPD8335 Approved
0.6529 Remote Similarity NPD8378 Approved
0.6529 Remote Similarity NPD8033 Approved
0.6529 Remote Similarity NPD8380 Approved
0.6529 Remote Similarity NPD8296 Approved
0.6522 Remote Similarity NPD6883 Approved
0.6522 Remote Similarity NPD7290 Approved
0.6522 Remote Similarity NPD7102 Approved
0.6509 Remote Similarity NPD4202 Approved
0.6491 Remote Similarity NPD6011 Approved
0.6491 Remote Similarity NPD6686 Approved
0.6476 Remote Similarity NPD5692 Phase 3
0.6476 Remote Similarity NPD5207 Approved
0.6466 Remote Similarity NPD8130 Phase 1
0.6466 Remote Similarity NPD6847 Approved
0.6466 Remote Similarity NPD6649 Approved
0.6466 Remote Similarity NPD6869 Approved
0.6466 Remote Similarity NPD6617 Approved
0.6466 Remote Similarity NPD6650 Approved
0.6446 Remote Similarity NPD8377 Approved
0.6446 Remote Similarity NPD8294 Approved
0.6442 Remote Similarity NPD5208 Approved
0.6422 Remote Similarity NPD6083 Phase 2
0.6422 Remote Similarity NPD4755 Approved
0.6422 Remote Similarity NPD6084 Phase 2
0.6415 Remote Similarity NPD7637 Suspended
0.6415 Remote Similarity NPD5694 Approved
0.6415 Remote Similarity NPD6050 Approved
0.641 Remote Similarity NPD8297 Approved
0.641 Remote Similarity NPD6882 Approved
0.641 Remote Similarity NPD6053 Discontinued
0.6389 Remote Similarity NPD5695 Phase 3
0.6381 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6381 Remote Similarity NPD6904 Approved
0.6381 Remote Similarity NPD5328 Approved
0.6381 Remote Similarity NPD6673 Approved
0.6381 Remote Similarity NPD6080 Approved
0.6373 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7645 Phase 2
0.6364 Remote Similarity NPD5696 Approved
0.6339 Remote Similarity NPD5211 Phase 2
0.6337 Remote Similarity NPD3667 Approved
0.6337 Remote Similarity NPD5209 Approved
0.6325 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6321 Remote Similarity NPD7838 Discovery
0.632 Remote Similarity NPD7507 Approved
0.6311 Remote Similarity NPD1696 Phase 3
0.6306 Remote Similarity NPD5286 Approved
0.6306 Remote Similarity NPD5285 Approved
0.6306 Remote Similarity NPD4700 Approved
0.6306 Remote Similarity NPD4696 Approved
0.63 Remote Similarity NPD7525 Registered
0.6299 Remote Similarity NPD7319 Approved
0.6289 Remote Similarity NPD8039 Approved
0.6275 Remote Similarity NPD6695 Phase 3
0.6273 Remote Similarity NPD5959 Approved
0.6262 Remote Similarity NPD6411 Approved
0.6262 Remote Similarity NPD5281 Approved
0.6262 Remote Similarity NPD6079 Approved
0.6262 Remote Similarity NPD5284 Approved
0.625 Remote Similarity NPD6098 Approved
0.625 Remote Similarity NPD6274 Approved
0.6239 Remote Similarity NPD5654 Approved
0.6228 Remote Similarity NPD5141 Approved
0.6224 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6214 Remote Similarity NPD4786 Approved
0.6214 Remote Similarity NPD3666 Approved
0.6214 Remote Similarity NPD3668 Phase 3
0.6214 Remote Similarity NPD3665 Phase 1
0.6214 Remote Similarity NPD3133 Approved
0.6207 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5226 Approved
0.6195 Remote Similarity NPD5225 Approved
0.6195 Remote Similarity NPD5224 Approved
0.6195 Remote Similarity NPD4633 Approved
0.614 Remote Similarity NPD5174 Approved
0.614 Remote Similarity NPD5175 Approved
0.6139 Remote Similarity NPD6931 Approved
0.6139 Remote Similarity NPD6930 Phase 2
0.6122 Remote Similarity NPD6942 Approved
0.6122 Remote Similarity NPD7339 Approved
0.6111 Remote Similarity NPD8035 Phase 2
0.6111 Remote Similarity NPD8034 Phase 2
0.6106 Remote Similarity NPD5223 Approved
0.6098 Remote Similarity NPD7101 Approved
0.6098 Remote Similarity NPD7100 Approved
0.6095 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6095 Remote Similarity NPD5279 Phase 3
0.6095 Remote Similarity NPD4623 Approved
0.6095 Remote Similarity NPD4519 Discontinued
0.6087 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6083 Remote Similarity NPD4632 Approved
0.6075 Remote Similarity NPD4753 Phase 2
0.6075 Remote Similarity NPD6101 Approved
0.6075 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6075 Remote Similarity NPD1695 Approved
0.6066 Remote Similarity NPD6317 Approved
0.6055 Remote Similarity NPD5778 Approved
0.6055 Remote Similarity NPD5779 Approved
0.6048 Remote Similarity NPD6319 Approved
0.604 Remote Similarity NPD4195 Approved
0.604 Remote Similarity NPD6929 Approved
0.6038 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6038 Remote Similarity NPD7524 Approved
0.6038 Remote Similarity NPD7750 Discontinued
0.6036 Remote Similarity NPD5221 Approved
0.6036 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6036 Remote Similarity NPD4697 Phase 3
0.6036 Remote Similarity NPD5222 Approved
0.6034 Remote Similarity NPD4768 Approved
0.6034 Remote Similarity NPD4767 Approved
0.602 Remote Similarity NPD6926 Approved
0.602 Remote Similarity NPD6924 Approved
0.6019 Remote Similarity NPD46 Approved
0.6019 Remote Similarity NPD4221 Approved
0.6019 Remote Similarity NPD4223 Phase 3
0.6019 Remote Similarity NPD6698 Approved
0.6016 Remote Similarity NPD6313 Approved
0.6016 Remote Similarity NPD6314 Approved
0.6016 Remote Similarity NPD6335 Approved
0.6 Remote Similarity NPD6908 Approved
0.6 Remote Similarity NPD4754 Approved
0.6 Remote Similarity NPD6909 Approved
0.6 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5982 Remote Similarity NPD5173 Approved
0.598 Remote Similarity NPD7332 Phase 2
0.598 Remote Similarity NPD7509 Discontinued
0.598 Remote Similarity NPD4695 Discontinued
0.598 Remote Similarity NPD7514 Phase 3
0.596 Remote Similarity NPD8264 Approved
0.5952 Remote Similarity NPD3412 Clinical (unspecified phase)
0.5943 Remote Similarity NPD5280 Approved
0.5943 Remote Similarity NPD4694 Approved
0.5941 Remote Similarity NPD3617 Approved
0.5935 Remote Similarity NPD6009 Approved
0.5932 Remote Similarity NPD4730 Approved
0.5932 Remote Similarity NPD4729 Approved
0.5932 Remote Similarity NPD5128 Approved
0.5922 Remote Similarity NPD6902 Approved
0.5906 Remote Similarity NPD7604 Phase 2
0.5905 Remote Similarity NPD4197 Approved
0.59 Remote Similarity NPD6933 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