Structure

Physi-Chem Properties

Molecular Weight:  232.11
Volume:  240.856
LogP:  1.457
LogD:  1.027
LogS:  -2.718
# Rotatable Bonds:  0
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.365
Synthetic Accessibility Score:  4.316
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.554
MDCK Permeability:  2.502112511137966e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.531
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.31
Plasma Protein Binding (PPB):  87.5287094116211%
Volume Distribution (VD):  1.426
Pgp-substrate:  6.1223063468933105%

ADMET: Metabolism

CYP1A2-inhibitor:  0.059
CYP1A2-substrate:  0.12
CYP2C19-inhibitor:  0.127
CYP2C19-substrate:  0.29
CYP2C9-inhibitor:  0.178
CYP2C9-substrate:  0.707
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.591
CYP3A4-inhibitor:  0.13
CYP3A4-substrate:  0.327

ADMET: Excretion

Clearance (CL):  15.585
Half-life (T1/2):  0.4

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.115
Drug-inuced Liver Injury (DILI):  0.458
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.489
Maximum Recommended Daily Dose:  0.648
Skin Sensitization:  0.153
Carcinogencity:  0.859
Eye Corrosion:  0.008
Eye Irritation:  0.086
Respiratory Toxicity:  0.56

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  Natural Product: NPC39588

Natural Product ID:  NPC39588
Common Name*:   5-Methyl-1-Methylidene-4,5,5A,8A,9,9A-Hexahydro-3Ah-Azuleno[6,7-B]Furan-2,8-Dione
IUPAC Name:   5-methyl-1-methylidene-4,5,5a,8a,9,9a-hexahydro-3aH-azuleno[6,7-b]furan-2,8-dione
Synonyms:  
Standard InCHIKey:  GQOWVFHMXITOCQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H16O3/c1-7-5-13-10(8(2)14(16)17-13)6-11-9(7)3-4-12(11)15/h3-4,7,9-11,13H,2,5-6H2,1H3
SMILES:  CC1CC2OC(=O)C(=C)C2CC2C1C=CC2=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2000938
PubChem CID:   319598
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[11830162]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[12809361]
NPO26193 Piper methysticum Species Piperaceae Eukaryota root n.a. n.a. PMID[25597012]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5174 Helenium mexicanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5174 Helenium mexicanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5174 Helenium mexicanum Species Asteraceae 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. 2018.37 nM PMID[567452]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 2065.38 nM PMID[567452]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1832.31 nM PMID[567452]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 3076.1 nM PMID[567452]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2897.34 nM PMID[567452]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1879.32 nM PMID[567452]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 891.25 nM PMID[567452]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 5407.54 nM PMID[567452]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2079.7 nM PMID[567452]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2051.16 nM PMID[567452]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 2142.89 nM PMID[567452]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 1455.46 nM PMID[567452]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 11455.13 nM PMID[567452]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 5128.61 nM PMID[567452]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 15922.09 nM PMID[567452]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1496.24 nM PMID[567452]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 6760.83 nM PMID[567452]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2937.65 nM PMID[567452]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 3288.52 nM PMID[567452]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 3539.97 nM PMID[567452]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1887.99 nM PMID[567452]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 15417.0 nM PMID[567452]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 3162.28 nM PMID[567452]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 824.14 nM PMID[567452]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 2722.7 nM PMID[567452]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 997.7 nM PMID[567452]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 5636.38 nM PMID[567452]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 609.54 nM PMID[567452]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1621.81 nM PMID[567452]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 1625.55 nM PMID[567452]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 7277.8 nM PMID[567452]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1706.08 nM PMID[567452]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2951.21 nM PMID[567452]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 866.96 nM PMID[567452]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 2636.33 nM PMID[567452]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 2037.04 nM PMID[567452]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 3515.6 nM PMID[567452]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 7925.01 nM PMID[567452]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5508.08 nM PMID[567452]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 4731.51 nM PMID[567452]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1853.53 nM PMID[567452]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1261.83 nM PMID[567452]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 2546.83 nM PMID[567452]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 12105.98 nM PMID[567452]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2365.92 nM PMID[567452]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 1261.83 nM PMID[567452]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 2437.81 nM PMID[567452]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 16106.46 nM PMID[567452]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2344.23 nM PMID[567452]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1706.08 nM PMID[567452]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2958.01 nM PMID[567452]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2172.7 nM PMID[567452]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 3311.31 nM PMID[567452]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 14554.59 nM PMID[567452]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 3622.43 nM PMID[567452]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 3881.5 nM PMID[567452]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 1849.27 nM PMID[567452]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 3419.79 nM PMID[567452]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 2023.02 nM PMID[567452]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1761.98 nM PMID[567452]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 1655.77 nM PMID[567452]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 427.56 nM PMID[567452]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 2636.33 nM PMID[567452]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1717.91 nM PMID[567452]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 1682.67 nM PMID[567452]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1531.09 nM PMID[567452]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1520.55 nM PMID[567452]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 5767.66 nM PMID[567452]

☑ 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 NPC39588 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
0.9747 High Similarity NPC161957
0.9359 High Similarity NPC74673
0.9359 High Similarity NPC69271
0.9259 High Similarity NPC33570
0.9259 High Similarity NPC21471
0.9241 High Similarity NPC35089
0.9241 High Similarity NPC10276
0.9114 High Similarity NPC276356
0.9114 High Similarity NPC302426
0.9059 High Similarity NPC74103
0.9059 High Similarity NPC150978
0.9059 High Similarity NPC123177
0.9059 High Similarity NPC70595
0.8941 High Similarity NPC253144
0.8875 High Similarity NPC223904
0.8837 High Similarity NPC284185
0.878 High Similarity NPC215294
0.875 High Similarity NPC264227
0.875 High Similarity NPC63649
0.875 High Similarity NPC182550
0.875 High Similarity NPC472965
0.875 High Similarity NPC275960
0.875 High Similarity NPC90121
0.875 High Similarity NPC193645
0.875 High Similarity NPC48803
0.8734 High Similarity NPC15975
0.8734 High Similarity NPC195785
0.8734 High Similarity NPC208223
0.8734 High Similarity NPC65603
0.8721 High Similarity NPC62815
0.8718 High Similarity NPC193351
0.8718 High Similarity NPC226669
0.8718 High Similarity NPC138408
0.869 High Similarity NPC107787
0.8675 High Similarity NPC115786
0.8642 High Similarity NPC290508
0.8642 High Similarity NPC293418
0.8642 High Similarity NPC73052
0.8625 High Similarity NPC472960
0.8621 High Similarity NPC261607
0.8621 High Similarity NPC300312
0.8621 High Similarity NPC111114
0.8571 High Similarity NPC78089
0.8556 High Similarity NPC169205
0.8523 High Similarity NPC135776
0.85 High Similarity NPC476794
0.85 High Similarity NPC470240
0.8481 Intermediate Similarity NPC155587
0.8471 Intermediate Similarity NPC70555
0.8471 Intermediate Similarity NPC104961
0.8471 Intermediate Similarity NPC70422
0.8462 Intermediate Similarity NPC141191
0.8462 Intermediate Similarity NPC472956
0.8462 Intermediate Similarity NPC54843
0.8444 Intermediate Similarity NPC185553
0.8434 Intermediate Similarity NPC173609
0.8427 Intermediate Similarity NPC167219
0.8395 Intermediate Similarity NPC299235
0.8391 Intermediate Similarity NPC268298
0.8375 Intermediate Similarity NPC472959
0.8375 Intermediate Similarity NPC266159
0.8375 Intermediate Similarity NPC235906
0.8375 Intermediate Similarity NPC472967
0.8354 Intermediate Similarity NPC143979
0.8354 Intermediate Similarity NPC320537
0.8333 Intermediate Similarity NPC54468
0.8313 Intermediate Similarity NPC301477
0.8313 Intermediate Similarity NPC255580
0.8313 Intermediate Similarity NPC25684
0.8313 Intermediate Similarity NPC281949
0.8313 Intermediate Similarity NPC39411
0.8295 Intermediate Similarity NPC129419
0.8293 Intermediate Similarity NPC470239
0.8293 Intermediate Similarity NPC470244
0.8276 Intermediate Similarity NPC91248
0.8272 Intermediate Similarity NPC187568
0.8272 Intermediate Similarity NPC41780
0.8256 Intermediate Similarity NPC284902
0.8193 Intermediate Similarity NPC6823
0.8182 Intermediate Similarity NPC4986
0.8182 Intermediate Similarity NPC117405
0.8182 Intermediate Similarity NPC32922
0.8182 Intermediate Similarity NPC52198
0.8171 Intermediate Similarity NPC128276
0.8161 Intermediate Similarity NPC475703
0.8161 Intermediate Similarity NPC237540
0.8148 Intermediate Similarity NPC123360
0.814 Intermediate Similarity NPC110405
0.8132 Intermediate Similarity NPC304886
0.8125 Intermediate Similarity NPC469641
0.8125 Intermediate Similarity NPC476355
0.8125 Intermediate Similarity NPC469643
0.8118 Intermediate Similarity NPC272814
0.8101 Intermediate Similarity NPC163003
0.8095 Intermediate Similarity NPC42470
0.8095 Intermediate Similarity NPC471325
0.809 Intermediate Similarity NPC152467
0.8077 Intermediate Similarity NPC144511
0.8077 Intermediate Similarity NPC296522
0.8072 Intermediate Similarity NPC178277
0.8072 Intermediate Similarity NPC617
0.8072 Intermediate Similarity NPC469690
0.8068 Intermediate Similarity NPC215831
0.8049 Intermediate Similarity NPC122264
0.8049 Intermediate Similarity NPC57744
0.8046 Intermediate Similarity NPC309757
0.8046 Intermediate Similarity NPC236692
0.8046 Intermediate Similarity NPC238593
0.8046 Intermediate Similarity NPC64153
0.8023 Intermediate Similarity NPC156485
0.8023 Intermediate Similarity NPC165287
0.8022 Intermediate Similarity NPC477131
0.8021 Intermediate Similarity NPC203659
0.8 Intermediate Similarity NPC133698
0.8 Intermediate Similarity NPC58956
0.8 Intermediate Similarity NPC131209
0.8 Intermediate Similarity NPC225353
0.8 Intermediate Similarity NPC295633
0.8 Intermediate Similarity NPC269206
0.7978 Intermediate Similarity NPC295312
0.7978 Intermediate Similarity NPC73995
0.7975 Intermediate Similarity NPC472955
0.7955 Intermediate Similarity NPC118601
0.7931 Intermediate Similarity NPC235792
0.7931 Intermediate Similarity NPC165162
0.7931 Intermediate Similarity NPC177932
0.7931 Intermediate Similarity NPC215364
0.7917 Intermediate Similarity NPC110989
0.7907 Intermediate Similarity NPC318468
0.7901 Intermediate Similarity NPC140287
0.7895 Intermediate Similarity NPC474742
0.7889 Intermediate Similarity NPC71533
0.7889 Intermediate Similarity NPC312042
0.7889 Intermediate Similarity NPC106510
0.7882 Intermediate Similarity NPC47635
0.7882 Intermediate Similarity NPC141810
0.7882 Intermediate Similarity NPC325031
0.7875 Intermediate Similarity NPC129665
0.7865 Intermediate Similarity NPC178875
0.7865 Intermediate Similarity NPC469653
0.7865 Intermediate Similarity NPC469631
0.7865 Intermediate Similarity NPC471047
0.7865 Intermediate Similarity NPC469628
0.7865 Intermediate Similarity NPC475906
0.7857 Intermediate Similarity NPC469620
0.7857 Intermediate Similarity NPC270126
0.7848 Intermediate Similarity NPC5714
0.7848 Intermediate Similarity NPC199557
0.7841 Intermediate Similarity NPC67493
0.7831 Intermediate Similarity NPC103987
0.7831 Intermediate Similarity NPC53581
0.7826 Intermediate Similarity NPC289004
0.7826 Intermediate Similarity NPC198853
0.7826 Intermediate Similarity NPC470010
0.7826 Intermediate Similarity NPC470013
0.7826 Intermediate Similarity NPC262133
0.7826 Intermediate Similarity NPC323008
0.7816 Intermediate Similarity NPC472958
0.7816 Intermediate Similarity NPC472957
0.7812 Intermediate Similarity NPC474747
0.7805 Intermediate Similarity NPC244166
0.7791 Intermediate Similarity NPC89555
0.7791 Intermediate Similarity NPC178676
0.7791 Intermediate Similarity NPC246076
0.7778 Intermediate Similarity NPC166919
0.7778 Intermediate Similarity NPC12872
0.7778 Intermediate Similarity NPC168679
0.7753 Intermediate Similarity NPC160138
0.7753 Intermediate Similarity NPC270270
0.7753 Intermediate Similarity NPC231889
0.7753 Intermediate Similarity NPC72513
0.7753 Intermediate Similarity NPC190753
0.7738 Intermediate Similarity NPC108816
0.7738 Intermediate Similarity NPC93763
0.7738 Intermediate Similarity NPC267231
0.7732 Intermediate Similarity NPC475945
0.7732 Intermediate Similarity NPC475873
0.7732 Intermediate Similarity NPC475871
0.7727 Intermediate Similarity NPC50362
0.7727 Intermediate Similarity NPC319795
0.7727 Intermediate Similarity NPC38468
0.7727 Intermediate Similarity NPC474547
0.7727 Intermediate Similarity NPC125290
0.7722 Intermediate Similarity NPC470256
0.7711 Intermediate Similarity NPC473223
0.7701 Intermediate Similarity NPC193198
0.7701 Intermediate Similarity NPC250315
0.7701 Intermediate Similarity NPC475947
0.7701 Intermediate Similarity NPC53867
0.7701 Intermediate Similarity NPC245665
0.7701 Intermediate Similarity NPC22611
0.7701 Intermediate Similarity NPC474703
0.7692 Intermediate Similarity NPC251385
0.7692 Intermediate Similarity NPC329857
0.7692 Intermediate Similarity NPC301969
0.7692 Intermediate Similarity NPC49342
0.7692 Intermediate Similarity NPC37607
0.7692 Intermediate Similarity NPC469718
0.7683 Intermediate Similarity NPC259599
0.7683 Intermediate Similarity NPC117746

  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 NPC39588 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
0.875 High Similarity NPD1698 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1695 Approved
0.7931 Intermediate Similarity NPD1694 Approved
0.7727 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5209 Approved
0.7157 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD5785 Approved
0.6957 Remote Similarity NPD5363 Approved
0.6923 Remote Similarity NPD5362 Discontinued
0.6882 Remote Similarity NPD5786 Approved
0.6813 Remote Similarity NPD6435 Approved
0.6792 Remote Similarity NPD6371 Approved
0.6739 Remote Similarity NPD7154 Phase 3
0.6737 Remote Similarity NPD6903 Approved
0.6735 Remote Similarity NPD5282 Discontinued
0.6707 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6703 Remote Similarity NPD5369 Approved
0.6702 Remote Similarity NPD6684 Approved
0.6702 Remote Similarity NPD7521 Approved
0.6702 Remote Similarity NPD7334 Approved
0.6702 Remote Similarity NPD6409 Approved
0.6702 Remote Similarity NPD7146 Approved
0.6702 Remote Similarity NPD5330 Approved
0.6632 Remote Similarity NPD3573 Approved
0.663 Remote Similarity NPD4269 Approved
0.663 Remote Similarity NPD4270 Approved
0.6598 Remote Similarity NPD5207 Approved
0.6593 Remote Similarity NPD5368 Approved
0.6591 Remote Similarity NPD8039 Approved
0.6571 Remote Similarity NPD6008 Approved
0.6562 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6101 Approved
0.6471 Remote Similarity NPD4225 Approved
0.6465 Remote Similarity NPD5778 Approved
0.6465 Remote Similarity NPD5779 Approved
0.6429 Remote Similarity NPD6698 Approved
0.6429 Remote Similarity NPD46 Approved
0.6421 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6413 Remote Similarity NPD4252 Approved
0.6392 Remote Similarity NPD5737 Approved
0.6392 Remote Similarity NPD6672 Approved
0.6374 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6411 Approved
0.6364 Remote Similarity NPD6053 Discontinued
0.6364 Remote Similarity NPD5693 Phase 1
0.6337 Remote Similarity NPD6356 Clinical (unspecified phase)
0.63 Remote Similarity NPD6399 Phase 3
0.6263 Remote Similarity NPD7838 Discovery
0.6238 Remote Similarity NPD7900 Approved
0.6238 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6001 Approved
0.6237 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6235 Remote Similarity NPD7331 Phase 2
0.6211 Remote Similarity NPD5332 Approved
0.6211 Remote Similarity NPD5331 Approved
0.6204 Remote Similarity NPD5697 Approved
0.62 Remote Similarity NPD6079 Approved
0.62 Remote Similarity NPD7983 Approved
0.6186 Remote Similarity NPD4249 Approved
0.617 Remote Similarity NPD4790 Discontinued
0.6147 Remote Similarity NPD6899 Approved
0.6147 Remote Similarity NPD6011 Approved
0.6147 Remote Similarity NPD6881 Approved
0.614 Remote Similarity NPD7115 Discovery
0.6126 Remote Similarity NPD6649 Approved
0.6126 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6126 Remote Similarity NPD6650 Approved
0.6122 Remote Similarity NPD4251 Approved
0.6122 Remote Similarity NPD4250 Approved
0.6118 Remote Similarity NPD7341 Phase 2
0.6091 Remote Similarity NPD6012 Approved
0.6091 Remote Similarity NPD6013 Approved
0.6091 Remote Similarity NPD6014 Approved
0.6078 Remote Similarity NPD7748 Approved
0.6064 Remote Similarity NPD4819 Approved
0.6064 Remote Similarity NPD4821 Approved
0.6064 Remote Similarity NPD4822 Approved
0.6064 Remote Similarity NPD4820 Approved
0.6061 Remote Similarity NPD5208 Approved
0.6058 Remote Similarity NPD7902 Approved
0.6047 Remote Similarity NPD6108 Clinical (unspecified phase)
0.604 Remote Similarity NPD5694 Approved
0.6036 Remote Similarity NPD7102 Approved
0.6036 Remote Similarity NPD6883 Approved
0.6036 Remote Similarity NPD7290 Approved
0.6022 Remote Similarity NPD4268 Approved
0.6022 Remote Similarity NPD4271 Approved
0.602 Remote Similarity NPD6422 Discontinued
0.602 Remote Similarity NPD3618 Phase 1
0.6019 Remote Similarity NPD5695 Phase 3
0.6 Remote Similarity NPD6080 Approved
0.6 Remote Similarity NPD6673 Approved
0.6 Remote Similarity NPD5696 Approved
0.6 Remote Similarity NPD7638 Approved
0.6 Remote Similarity NPD6686 Approved
0.6 Remote Similarity NPD6904 Approved
0.6 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6 Remote Similarity NPD5328 Approved
0.6 Remote Similarity NPD7320 Approved
0.5982 Remote Similarity NPD8130 Phase 1
0.5982 Remote Similarity NPD6617 Approved
0.5982 Remote Similarity NPD6847 Approved
0.5982 Remote Similarity NPD6869 Approved
0.5979 Remote Similarity NPD3133 Approved
0.5979 Remote Similarity NPD3665 Phase 1
0.5979 Remote Similarity NPD3666 Approved
0.5963 Remote Similarity NPD7128 Approved
0.5963 Remote Similarity NPD6402 Approved
0.5963 Remote Similarity NPD6675 Approved
0.5963 Remote Similarity NPD5739 Approved
0.5962 Remote Similarity NPD5221 Approved
0.5962 Remote Similarity NPD7839 Suspended
0.5962 Remote Similarity NPD5222 Approved
0.5962 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5962 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5946 Remote Similarity NPD6373 Approved
0.5946 Remote Similarity NPD6372 Approved
0.5943 Remote Similarity NPD7639 Approved
0.5943 Remote Similarity NPD7640 Approved
0.5941 Remote Similarity NPD5692 Phase 3
0.5938 Remote Similarity NPD3667 Approved
0.5938 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5932 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5929 Remote Similarity NPD8297 Approved
0.5929 Remote Similarity NPD6882 Approved
0.5914 Remote Similarity NPD4756 Discovery
0.5909 Remote Similarity NPD5701 Approved
0.5905 Remote Similarity NPD5173 Approved
0.5905 Remote Similarity NPD6083 Phase 2
0.5905 Remote Similarity NPD6084 Phase 2
0.5895 Remote Similarity NPD4695 Discontinued
0.5882 Remote Similarity NPD6050 Approved
0.5882 Remote Similarity NPD5284 Approved
0.5882 Remote Similarity NPD5281 Approved
0.5882 Remote Similarity NPD7515 Phase 2
0.5859 Remote Similarity NPD5279 Phase 3
0.5859 Remote Similarity NPD6098 Approved
0.5859 Remote Similarity NPD4519 Discontinued
0.5859 Remote Similarity NPD4623 Approved
0.5842 Remote Similarity NPD5370 Suspended
0.5841 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5211 Phase 2
0.5816 Remote Similarity NPD3668 Phase 3
0.5816 Remote Similarity NPD4786 Approved
0.581 Remote Similarity NPD4697 Phase 3
0.5794 Remote Similarity NPD5286 Approved
0.5794 Remote Similarity NPD5285 Approved
0.5794 Remote Similarity NPD4696 Approved
0.5794 Remote Similarity NPD6648 Approved
0.578 Remote Similarity NPD6052 Approved
0.578 Remote Similarity NPD6647 Phase 2
0.5776 Remote Similarity NPD6868 Approved
0.576 Remote Similarity NPD7260 Phase 2
0.5758 Remote Similarity NPD1696 Phase 3
0.5752 Remote Similarity NPD2067 Discontinued
0.5741 Remote Similarity NPD5344 Discontinued
0.5741 Remote Similarity NPD5223 Approved
0.5739 Remote Similarity NPD4632 Approved
0.5728 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5727 Remote Similarity NPD5141 Approved
0.5726 Remote Similarity NPD6317 Approved
0.5714 Remote Similarity NPD4629 Approved
0.5714 Remote Similarity NPD5210 Approved
0.5702 Remote Similarity NPD6401 Clinical (unspecified phase)
0.57 Remote Similarity NPD5690 Phase 2
0.5696 Remote Similarity NPD29 Approved
0.5696 Remote Similarity NPD28 Approved
0.5688 Remote Similarity NPD5226 Approved
0.5688 Remote Similarity NPD4633 Approved
0.5688 Remote Similarity NPD5225 Approved
0.5688 Remote Similarity NPD5224 Approved
0.5686 Remote Similarity NPD6051 Approved
0.5679 Remote Similarity NPD9298 Approved
0.5678 Remote Similarity NPD6335 Approved
0.5678 Remote Similarity NPD6314 Approved
0.5678 Remote Similarity NPD6313 Approved
0.5673 Remote Similarity NPD5781 Clinical (unspecified phase)
0.567 Remote Similarity NPD857 Phase 3
0.5667 Remote Similarity NPD8517 Approved
0.5667 Remote Similarity NPD8513 Phase 3
0.5667 Remote Similarity NPD8516 Approved
0.5667 Remote Similarity NPD8515 Approved
0.566 Remote Similarity NPD7732 Phase 3
0.5657 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5656 Remote Similarity NPD7492 Approved
0.5641 Remote Similarity NPD6274 Approved
0.5636 Remote Similarity NPD5175 Approved
0.5636 Remote Similarity NPD5174 Approved
0.5632 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5632 Remote Similarity NPD3197 Phase 1
0.563 Remote Similarity NPD7101 Approved
0.563 Remote Similarity NPD7100 Approved
0.5625 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5625 Remote Similarity NPD6614 Approved
0.5612 Remote Similarity NPD4223 Phase 3
0.5612 Remote Similarity NPD4221 Approved
0.561 Remote Similarity NPD6616 Approved
0.5607 Remote Similarity NPD4755 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