Structure

Physi-Chem Properties

Molecular Weight:  349.11
Volume:  330.464
LogP:  1.525
LogD:  0.608
LogS:  -1.996
# Rotatable Bonds:  5
TPSA:  112.73
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.675
Synthetic Accessibility Score:  3.527
Fsp3:  0.438
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.063
MDCK Permeability:  0.0001572266046423465
Pgp-inhibitor:  0.0
Pgp-substrate:  0.019
Human Intestinal Absorption (HIA):  0.055
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.031
Plasma Protein Binding (PPB):  29.012496948242188%
Volume Distribution (VD):  0.245
Pgp-substrate:  73.83132934570312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.04
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.099
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.231
CYP2D6-inhibitor:  0.337
CYP2D6-substrate:  0.12
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.107

ADMET: Excretion

Clearance (CL):  2.159
Half-life (T1/2):  0.882

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.188
Drug-inuced Liver Injury (DILI):  0.801
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.088
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.21
Carcinogencity:  0.015
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.018

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

  Natural Product: NPC46896

Natural Product ID:  NPC46896
Common Name*:   (3S,4R,4As,8As)-4-[2-(Furan-3-Yl)Ethyl]-4-Hydroxy-3,4A,8,8-Tetramethyl-1,3,5,6,7,8A-Hexahydronaphthalen-2-One
IUPAC Name:   (3S,4R,4aS,8aS)-4-[2-(furan-3-yl)ethyl]-4-hydroxy-3,4a,8,8-tetramethyl-1,3,5,6,7,8a-hexahydronaphthalen-2-one
Synonyms:  
Standard InCHIKey:  UVKYPKNCQJIGKV-PEFDPPPMSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-14-16(21)12-17-18(2,3)8-5-9-19(17,4)20(14,22)10-6-15-7-11-23-13-15/h7,11,13-14,17,22H,5-6,8-10,12H2,1-4H3/t14-,17+,19+,20-/m1/s1
SMILES:  O=C1C[C@H]2C(C)(C)CCC[C@@]2([C@@]([C@@H]1C)(O)CCc1cocc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2000054
PubChem CID:   5458747
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO30707 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16724855]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[22703163]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[24328283]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[24704554]
NPO41015 Ballota hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[32818604]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[32935986]
NPO30707 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30707 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3870 Calea septuplinervia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2909 Ballota andreuzziana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1980 Senecio yegua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17 Psoroma leprolomum Species Pannariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 55080.77 nM PMID[503179]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 52966.34 nM PMID[503179]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 80352.61 nM PMID[503179]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 11534.53 nM PMID[503179]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 66374.31 nM PMID[503179]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 84333.48 nM PMID[503179]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 96382.9 nM PMID[503179]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 82035.15 nM PMID[503179]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 57411.65 nM PMID[503179]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 89536.48 nM PMID[503179]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 13427.65 nM PMID[503179]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[503179]
NPT1137 Individual Protein 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens Activity = 20.0 % PMID[503181]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = -12.83 % PMID[503180]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 1.88 % PMID[503180]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 0.26 % PMID[503180]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = -11.22 % PMID[503180]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = -8.38 % PMID[503180]
NPT20 Organism Candida albicans Candida albicans Inhibition = 5.12 % PMID[503180]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -4.02 % PMID[503180]
NPT35 Others n.a. Activity = 96.0 % PMID[503181]
NPT35 Others n.a. Activity = 97.03 % PMID[503181]
NPT35 Others n.a. Activity = 97.31 % PMID[503181]
NPT32 Organism Mus musculus Mus musculus IC50 = 1050.0 nM PMID[503181]

☑ 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 NPC46896 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
0.9767 High Similarity NPC158525
0.9265 High Similarity NPC263337
0.9259 High Similarity NPC90296
0.9259 High Similarity NPC67003
0.9197 High Similarity NPC243577
0.9124 High Similarity NPC121158
0.8993 High Similarity NPC251865
0.8929 High Similarity NPC5676
0.8889 High Similarity NPC476947
0.8889 High Similarity NPC75906
0.8872 High Similarity NPC61788
0.8849 High Similarity NPC52412
0.8811 High Similarity NPC472654
0.8811 High Similarity NPC195325
0.8803 High Similarity NPC255414
0.8803 High Similarity NPC216755
0.8803 High Similarity NPC471174
0.8779 High Similarity NPC46536
0.8779 High Similarity NPC23086
0.8779 High Similarity NPC138139
0.875 High Similarity NPC228842
0.875 High Similarity NPC212257
0.8741 High Similarity NPC218838
0.8731 High Similarity NPC89133
0.8705 High Similarity NPC148374
0.8699 High Similarity NPC30222
0.8699 High Similarity NPC178932
0.8699 High Similarity NPC282445
0.8696 High Similarity NPC471996
0.8681 High Similarity NPC69647
0.8681 High Similarity NPC211625
0.8681 High Similarity NPC125182
0.8671 High Similarity NPC221809
0.8652 High Similarity NPC476946
0.8652 High Similarity NPC103134
0.8649 High Similarity NPC472772
0.8649 High Similarity NPC249021
0.8647 High Similarity NPC112706
0.8647 High Similarity NPC207294
0.8643 High Similarity NPC205765
0.8639 High Similarity NPC35000
0.8639 High Similarity NPC469336
0.8639 High Similarity NPC264943
0.8633 High Similarity NPC202260
0.863 High Similarity NPC469503
0.8623 High Similarity NPC4764
0.8621 High Similarity NPC156189
0.8621 High Similarity NPC477404
0.8621 High Similarity NPC196864
0.8601 High Similarity NPC346
0.8592 High Similarity NPC476944
0.8582 High Similarity NPC473152
0.8582 High Similarity NPC20578
0.8582 High Similarity NPC62103
0.8571 High Similarity NPC83178
0.8571 High Similarity NPC57998
0.8561 High Similarity NPC179354
0.8561 High Similarity NPC476943
0.8552 High Similarity NPC470791
0.8552 High Similarity NPC470790
0.855 High Similarity NPC16922
0.855 High Similarity NPC272899
0.8542 High Similarity NPC470941
0.8542 High Similarity NPC250228
0.8533 High Similarity NPC25255
0.8533 High Similarity NPC287559
0.8531 High Similarity NPC185456
0.8529 High Similarity NPC471995
0.8523 High Similarity NPC299038
0.8523 High Similarity NPC81405
0.8521 High Similarity NPC267632
0.8521 High Similarity NPC64568
0.8514 High Similarity NPC44675
0.8514 High Similarity NPC214541
0.8507 High Similarity NPC477040
0.8507 High Similarity NPC279877
0.8503 High Similarity NPC268905
0.8503 High Similarity NPC121615
0.8503 High Similarity NPC246164
0.8503 High Similarity NPC294511
0.85 High Similarity NPC90953
0.8496 Intermediate Similarity NPC74612
0.8493 Intermediate Similarity NPC196846
0.8493 Intermediate Similarity NPC159927
0.8493 Intermediate Similarity NPC469335
0.8493 Intermediate Similarity NPC476122
0.8489 Intermediate Similarity NPC307401
0.8477 Intermediate Similarity NPC329938
0.8477 Intermediate Similarity NPC5079
0.8477 Intermediate Similarity NPC18986
0.8477 Intermediate Similarity NPC82851
0.8477 Intermediate Similarity NPC193798
0.8477 Intermediate Similarity NPC472771
0.8473 Intermediate Similarity NPC477967
0.8472 Intermediate Similarity NPC97904
0.8472 Intermediate Similarity NPC470999
0.8467 Intermediate Similarity NPC293253
0.8467 Intermediate Similarity NPC475967
0.8467 Intermediate Similarity NPC140952
0.8467 Intermediate Similarity NPC474611
0.8467 Intermediate Similarity NPC477403
0.8456 Intermediate Similarity NPC41880
0.8456 Intermediate Similarity NPC104736
0.845 Intermediate Similarity NPC243704
0.8446 Intermediate Similarity NPC114880
0.8444 Intermediate Similarity NPC59502
0.844 Intermediate Similarity NPC56197
0.8435 Intermediate Similarity NPC272590
0.8435 Intermediate Similarity NPC18135
0.8433 Intermediate Similarity NPC246392
0.8433 Intermediate Similarity NPC290955
0.8425 Intermediate Similarity NPC470998
0.8421 Intermediate Similarity NPC663
0.8421 Intermediate Similarity NPC477405
0.8421 Intermediate Similarity NPC292389
0.8421 Intermediate Similarity NPC234660
0.8421 Intermediate Similarity NPC419
0.8421 Intermediate Similarity NPC51568
0.8421 Intermediate Similarity NPC472773
0.8421 Intermediate Similarity NPC224394
0.8421 Intermediate Similarity NPC469338
0.8414 Intermediate Similarity NPC71821
0.8414 Intermediate Similarity NPC302987
0.8411 Intermediate Similarity NPC470789
0.8411 Intermediate Similarity NPC335761
0.8411 Intermediate Similarity NPC477402
0.8411 Intermediate Similarity NPC472653
0.8406 Intermediate Similarity NPC471998
0.8403 Intermediate Similarity NPC41182
0.84 Intermediate Similarity NPC45101
0.84 Intermediate Similarity NPC195954
0.84 Intermediate Similarity NPC88007
0.84 Intermediate Similarity NPC304692
0.84 Intermediate Similarity NPC194499
0.84 Intermediate Similarity NPC261597
0.84 Intermediate Similarity NPC7059
0.8392 Intermediate Similarity NPC470741
0.8392 Intermediate Similarity NPC223415
0.8389 Intermediate Similarity NPC155939
0.8389 Intermediate Similarity NPC469850
0.8389 Intermediate Similarity NPC141538
0.8389 Intermediate Similarity NPC92979
0.8389 Intermediate Similarity NPC296807
0.8382 Intermediate Similarity NPC476925
0.8378 Intermediate Similarity NPC476201
0.8378 Intermediate Similarity NPC470996
0.837 Intermediate Similarity NPC26532
0.837 Intermediate Similarity NPC476917
0.837 Intermediate Similarity NPC477123
0.837 Intermediate Similarity NPC327527
0.837 Intermediate Similarity NPC477966
0.8366 Intermediate Similarity NPC476856
0.8366 Intermediate Similarity NPC476858
0.8366 Intermediate Similarity NPC476860
0.8366 Intermediate Similarity NPC476857
0.8366 Intermediate Similarity NPC470940
0.8366 Intermediate Similarity NPC469849
0.8366 Intermediate Similarity NPC123088
0.8366 Intermediate Similarity NPC276551
0.8359 Intermediate Similarity NPC150895
0.8357 Intermediate Similarity NPC42400
0.8357 Intermediate Similarity NPC310830
0.8356 Intermediate Similarity NPC471007
0.8356 Intermediate Similarity NPC19747
0.8355 Intermediate Similarity NPC207978
0.8355 Intermediate Similarity NPC263432
0.8355 Intermediate Similarity NPC200782
0.8355 Intermediate Similarity NPC188649
0.8355 Intermediate Similarity NPC69028
0.8346 Intermediate Similarity NPC130275
0.8345 Intermediate Similarity NPC62799
0.8344 Intermediate Similarity NPC307383
0.8344 Intermediate Similarity NPC475226
0.8333 Intermediate Similarity NPC263265
0.8333 Intermediate Similarity NPC469485
0.8333 Intermediate Similarity NPC60973
0.8333 Intermediate Similarity NPC209364
0.8333 Intermediate Similarity NPC471006
0.8333 Intermediate Similarity NPC107646
0.8312 Intermediate Similarity NPC470875
0.8312 Intermediate Similarity NPC121995
0.8312 Intermediate Similarity NPC23387
0.8309 Intermediate Similarity NPC120836
0.8309 Intermediate Similarity NPC223063
0.8301 Intermediate Similarity NPC88841
0.8301 Intermediate Similarity NPC288602
0.8301 Intermediate Similarity NPC134254
0.8301 Intermediate Similarity NPC39986
0.8301 Intermediate Similarity NPC302369
0.8301 Intermediate Similarity NPC165218
0.8299 Intermediate Similarity NPC471001
0.8299 Intermediate Similarity NPC234494
0.8298 Intermediate Similarity NPC220094
0.8289 Intermediate Similarity NPC8389
0.8286 Intermediate Similarity NPC146872
0.8286 Intermediate Similarity NPC214572
0.8284 Intermediate Similarity NPC290193
0.8284 Intermediate Similarity NPC303010
0.8278 Intermediate Similarity NPC286722
0.8278 Intermediate Similarity NPC167142

  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 NPC46896 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
0.8639 High Similarity NPD5760 Phase 2
0.8639 High Similarity NPD5761 Phase 2
0.774 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD8434 Phase 2
0.7619 Intermediate Similarity NPD2344 Approved
0.7619 Intermediate Similarity NPD1471 Phase 3
0.7584 Intermediate Similarity NPD4628 Phase 3
0.7515 Intermediate Similarity NPD6765 Approved
0.7515 Intermediate Similarity NPD6764 Approved
0.7452 Intermediate Similarity NPD7819 Suspended
0.7432 Intermediate Similarity NPD2796 Approved
0.7432 Intermediate Similarity NPD6100 Approved
0.7432 Intermediate Similarity NPD6099 Approved
0.7417 Intermediate Similarity NPD2309 Approved
0.74 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6599 Discontinued
0.7368 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD2799 Discontinued
0.7357 Intermediate Similarity NPD3972 Approved
0.7357 Intermediate Similarity NPD1608 Approved
0.7338 Intermediate Similarity NPD6273 Approved
0.7337 Intermediate Similarity NPD6784 Approved
0.7337 Intermediate Similarity NPD6785 Approved
0.7308 Intermediate Similarity NPD3226 Approved
0.729 Intermediate Similarity NPD920 Approved
0.7273 Intermediate Similarity NPD2798 Approved
0.7273 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2346 Discontinued
0.723 Intermediate Similarity NPD1607 Approved
0.7219 Intermediate Similarity NPD1549 Phase 2
0.7211 Intermediate Similarity NPD1240 Approved
0.7205 Intermediate Similarity NPD3749 Approved
0.72 Intermediate Similarity NPD1551 Phase 2
0.7188 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD2800 Approved
0.7171 Intermediate Similarity NPD1243 Approved
0.7163 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD17 Approved
0.7143 Intermediate Similarity NPD3882 Suspended
0.7133 Intermediate Similarity NPD1510 Phase 2
0.7125 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD5494 Approved
0.7107 Intermediate Similarity NPD7411 Suspended
0.7101 Intermediate Similarity NPD6559 Discontinued
0.7097 Intermediate Similarity NPD6799 Approved
0.7075 Intermediate Similarity NPD2313 Discontinued
0.7055 Intermediate Similarity NPD919 Approved
0.7051 Intermediate Similarity NPD2532 Approved
0.7051 Intermediate Similarity NPD2534 Approved
0.7051 Intermediate Similarity NPD2533 Approved
0.7021 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD1778 Approved
0.702 Intermediate Similarity NPD7033 Discontinued
0.7014 Intermediate Similarity NPD1876 Approved
0.7013 Intermediate Similarity NPD7003 Approved
0.6994 Remote Similarity NPD7075 Discontinued
0.6993 Remote Similarity NPD970 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7458 Discontinued
0.697 Remote Similarity NPD6959 Discontinued
0.697 Remote Similarity NPD1247 Approved
0.6964 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6957 Remote Similarity NPD1934 Approved
0.6957 Remote Similarity NPD6279 Approved
0.6957 Remote Similarity NPD6280 Approved
0.6939 Remote Similarity NPD6832 Phase 2
0.6937 Remote Similarity NPD4380 Phase 2
0.6913 Remote Similarity NPD8032 Phase 2
0.6903 Remote Similarity NPD3750 Approved
0.6886 Remote Similarity NPD3926 Phase 2
0.6884 Remote Similarity NPD1241 Discontinued
0.6875 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6871 Remote Similarity NPD2296 Approved
0.6863 Remote Similarity NPD2935 Discontinued
0.6852 Remote Similarity NPD6801 Discontinued
0.6849 Remote Similarity NPD2797 Approved
0.6846 Remote Similarity NPD3268 Approved
0.6846 Remote Similarity NPD3764 Approved
0.6846 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6845 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7768 Phase 2
0.681 Remote Similarity NPD2801 Approved
0.6806 Remote Similarity NPD1201 Approved
0.6797 Remote Similarity NPD3748 Approved
0.6797 Remote Similarity NPD4308 Phase 3
0.6788 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6781 Remote Similarity NPD1283 Approved
0.6781 Remote Similarity NPD6696 Suspended
0.6776 Remote Similarity NPD6651 Approved
0.6772 Remote Similarity NPD1511 Approved
0.6768 Remote Similarity NPD3817 Phase 2
0.6766 Remote Similarity NPD8127 Discontinued
0.6765 Remote Similarity NPD7177 Discontinued
0.6765 Remote Similarity NPD3818 Discontinued
0.6763 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6761 Remote Similarity NPD9545 Approved
0.6759 Remote Similarity NPD9717 Approved
0.6755 Remote Similarity NPD4140 Approved
0.6735 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6735 Remote Similarity NPD1470 Approved
0.6735 Remote Similarity NPD1203 Approved
0.6733 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6733 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6725 Remote Similarity NPD5844 Phase 1
0.6713 Remote Similarity NPD1651 Approved
0.6713 Remote Similarity NPD5585 Approved
0.6711 Remote Similarity NPD6355 Discontinued
0.6711 Remote Similarity NPD1899 Clinical (unspecified phase)
0.671 Remote Similarity NPD6002 Phase 3
0.671 Remote Similarity NPD6003 Clinical (unspecified phase)
0.671 Remote Similarity NPD6006 Clinical (unspecified phase)
0.671 Remote Similarity NPD6005 Phase 3
0.671 Remote Similarity NPD6004 Phase 3
0.6709 Remote Similarity NPD7236 Approved
0.6706 Remote Similarity NPD7473 Discontinued
0.6688 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6688 Remote Similarity NPD4110 Phase 3
0.6688 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6687 Remote Similarity NPD1512 Approved
0.6667 Remote Similarity NPD8404 Phase 2
0.6667 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6166 Phase 2
0.6646 Remote Similarity NPD7577 Discontinued
0.6646 Remote Similarity NPD5403 Approved
0.6645 Remote Similarity NPD4307 Phase 2
0.6645 Remote Similarity NPD4476 Approved
0.6645 Remote Similarity NPD3142 Approved
0.6645 Remote Similarity NPD3140 Approved
0.6645 Remote Similarity NPD4477 Approved
0.6644 Remote Similarity NPD9494 Approved
0.6629 Remote Similarity NPD8312 Approved
0.6629 Remote Similarity NPD8313 Approved
0.6627 Remote Similarity NPD6232 Discontinued
0.6627 Remote Similarity NPD6808 Phase 2
0.6626 Remote Similarity NPD7028 Phase 2
0.6625 Remote Similarity NPD5401 Approved
0.6625 Remote Similarity NPD4662 Approved
0.6625 Remote Similarity NPD4661 Approved
0.6623 Remote Similarity NPD411 Approved
0.6622 Remote Similarity NPD3266 Approved
0.6622 Remote Similarity NPD3267 Approved
0.6619 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6603 Remote Similarity NPD5763 Approved
0.6603 Remote Similarity NPD5762 Approved
0.6601 Remote Similarity NPD5735 Approved
0.6599 Remote Similarity NPD5327 Phase 3
0.6595 Remote Similarity NPD3057 Approved
0.6577 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6575 Remote Similarity NPD1281 Approved
0.6573 Remote Similarity NPD9092 Discovery
0.6566 Remote Similarity NPD5402 Approved
0.6564 Remote Similarity NPD2649 Approved
0.6564 Remote Similarity NPD2651 Approved
0.6558 Remote Similarity NPD6353 Approved
0.6556 Remote Similarity NPD4625 Phase 3
0.6554 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5953 Discontinued
0.6552 Remote Similarity NPD3019 Approved
0.6552 Remote Similarity NPD2932 Approved
0.6545 Remote Similarity NPD6844 Discontinued
0.6543 Remote Similarity NPD3869 Phase 3
0.6543 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6543 Remote Similarity NPD3873 Phase 3
0.6541 Remote Similarity NPD2354 Approved
0.6541 Remote Similarity NPD3887 Approved
0.6536 Remote Similarity NPD2979 Phase 3
0.6533 Remote Similarity NPD2861 Phase 2
0.6532 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6529 Remote Similarity NPD5710 Approved
0.6529 Remote Similarity NPD7229 Phase 3
0.6529 Remote Similarity NPD5711 Approved
0.6527 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6514 Remote Similarity NPD3658 Clinical (unspecified phase)
0.6507 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6505 Remote Similarity NPD3533 Approved
0.6505 Remote Similarity NPD2972 Approved
0.6503 Remote Similarity NPD7239 Suspended
0.6494 Remote Similarity NPD7074 Phase 3
0.6494 Remote Similarity NPD447 Suspended
0.6486 Remote Similarity NPD4359 Approved
0.6486 Remote Similarity NPD4749 Approved
0.6483 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6483 Remote Similarity NPD5691 Approved
0.6478 Remote Similarity NPD8166 Discontinued
0.6474 Remote Similarity NPD7799 Discontinued
0.6474 Remote Similarity NPD2163 Approved
0.6474 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7199 Phase 2

  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