Structure

Physi-Chem Properties

Molecular Weight:  418.24
Volume:  437.55
LogP:  4.3
LogD:  3.968
LogS:  -4.3
# Rotatable Bonds:  9
TPSA:  96.97
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  4.393
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.697
MDCK Permeability:  1.3501575267582666e-05
Pgp-inhibitor:  0.048
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.388
30% Bioavailability (F30%):  0.739

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.087
Plasma Protein Binding (PPB):  94.2379379272461%
Volume Distribution (VD):  0.622
Pgp-substrate:  2.09611439704895%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.137
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.163
CYP2C9-substrate:  0.83
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.309
CYP3A4-inhibitor:  0.358
CYP3A4-substrate:  0.11

ADMET: Excretion

Clearance (CL):  7.051
Half-life (T1/2):  0.899

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.298
Drug-inuced Liver Injury (DILI):  0.042
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.25
Maximum Recommended Daily Dose:  0.533
Skin Sensitization:  0.08
Carcinogencity:  0.374
Eye Corrosion:  0.009
Eye Irritation:  0.068
Respiratory Toxicity:  0.937

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

  Natural Product: NPC30984

Natural Product ID:  NPC30984
Common Name*:   4-[[(1R,4As,5R,8As)-1,4A-Dimethyl-6-Methylidene-5-[2-(5-Oxo-2H-Furan-3-Yl)Ethyl]-3,4,5,7,8,8A-Hexahydro-2H-Naphthalen-1-Yl]Methoxy]-4-Oxobutanoic Acid
IUPAC Name:   4-[[(1R,4aS,5R,8aS)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methoxy]-4-oxobutanoic acid
Synonyms:  
Standard InCHIKey:  POSXURGFKVMSQT-VSQYNUGQSA-N
Standard InCHI:  InChI=1S/C24H34O6/c1-16-5-8-19-23(2,15-30-21(27)10-9-20(25)26)11-4-12-24(19,3)18(16)7-6-17-13-22(28)29-14-17/h13,18-19H,1,4-12,14-15H2,2-3H3,(H,25,26)/t18-,19-,23+,24+/m1/s1
SMILES:  C=C1CC[C@@H]2[C@@](C)(CCC[C@@]2(C)[C@@H]1CCC1=CC(=O)OC1)COC(=O)CCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1966230
PubChem CID:   391020
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[18582112]
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota n.a. aerial part n.a. PMID[18582112]
NPO15946 Laurenciella marilzae Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[26967625]
NPO29069 Aplophyllum buxbaumii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29382 Bladhia japonica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6308 Protobothrops flavoviridis Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15946 Laurenciella marilzae Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25514 Oxytropis trichophysa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29228 Streptomyces sviceus Species Streptomycetaceae Bacteria 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[453861]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 5970.35 nM PMID[453861]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 42854.85 nM PMID[453861]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 10000.0 nM PMID[453861]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[453861]

☑ 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 NPC30984 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
0.9036 High Similarity NPC65661
0.8837 High Similarity NPC174342
0.881 High Similarity NPC106416
0.881 High Similarity NPC86316
0.878 High Similarity NPC14203
0.878 High Similarity NPC229584
0.878 High Similarity NPC40228
0.8675 High Similarity NPC200513
0.8652 High Similarity NPC476415
0.8571 High Similarity NPC311070
0.8523 High Similarity NPC477782
0.8523 High Similarity NPC51486
0.8488 Intermediate Similarity NPC131813
0.8427 Intermediate Similarity NPC72845
0.8427 Intermediate Similarity NPC477783
0.8409 Intermediate Similarity NPC474396
0.8409 Intermediate Similarity NPC5509
0.8409 Intermediate Similarity NPC168131
0.8409 Intermediate Similarity NPC50488
0.8353 Intermediate Similarity NPC477124
0.8333 Intermediate Similarity NPC139692
0.8333 Intermediate Similarity NPC476416
0.8333 Intermediate Similarity NPC53555
0.8333 Intermediate Similarity NPC7349
0.8315 Intermediate Similarity NPC78973
0.8313 Intermediate Similarity NPC192999
0.8313 Intermediate Similarity NPC476438
0.8295 Intermediate Similarity NPC472810
0.8295 Intermediate Similarity NPC472809
0.828 Intermediate Similarity NPC473154
0.8276 Intermediate Similarity NPC329692
0.8256 Intermediate Similarity NPC318515
0.8242 Intermediate Similarity NPC105490
0.8242 Intermediate Similarity NPC57117
0.8235 Intermediate Similarity NPC15910
0.8222 Intermediate Similarity NPC329842
0.8222 Intermediate Similarity NPC177037
0.8222 Intermediate Similarity NPC472814
0.8211 Intermediate Similarity NPC476081
0.8202 Intermediate Similarity NPC251528
0.8172 Intermediate Similarity NPC73911
0.8161 Intermediate Similarity NPC42586
0.8161 Intermediate Similarity NPC474013
0.8161 Intermediate Similarity NPC189311
0.8161 Intermediate Similarity NPC471795
0.8161 Intermediate Similarity NPC217394
0.8161 Intermediate Similarity NPC473251
0.8152 Intermediate Similarity NPC293052
0.8152 Intermediate Similarity NPC209355
0.8152 Intermediate Similarity NPC276110
0.814 Intermediate Similarity NPC42476
0.814 Intermediate Similarity NPC472440
0.814 Intermediate Similarity NPC476927
0.8132 Intermediate Similarity NPC151722
0.8132 Intermediate Similarity NPC162615
0.8132 Intermediate Similarity NPC205034
0.8132 Intermediate Similarity NPC152778
0.8132 Intermediate Similarity NPC472303
0.8118 Intermediate Similarity NPC170303
0.8111 Intermediate Similarity NPC221111
0.8111 Intermediate Similarity NPC280149
0.8111 Intermediate Similarity NPC159748
0.8111 Intermediate Similarity NPC182136
0.8111 Intermediate Similarity NPC310479
0.8111 Intermediate Similarity NPC101651
0.8105 Intermediate Similarity NPC63249
0.8105 Intermediate Similarity NPC303559
0.809 Intermediate Similarity NPC226863
0.809 Intermediate Similarity NPC93411
0.8072 Intermediate Similarity NPC61952
0.8072 Intermediate Similarity NPC189206
0.8068 Intermediate Similarity NPC471219
0.8065 Intermediate Similarity NPC234993
0.8065 Intermediate Similarity NPC16967
0.8065 Intermediate Similarity NPC29952
0.8065 Intermediate Similarity NPC242848
0.8065 Intermediate Similarity NPC134072
0.8046 Intermediate Similarity NPC96055
0.8043 Intermediate Similarity NPC324078
0.8043 Intermediate Similarity NPC469697
0.8023 Intermediate Similarity NPC471218
0.8022 Intermediate Similarity NPC289479
0.8022 Intermediate Similarity NPC472811
0.8022 Intermediate Similarity NPC477122
0.8022 Intermediate Similarity NPC476417
0.8022 Intermediate Similarity NPC470113
0.8021 Intermediate Similarity NPC134077
0.8021 Intermediate Similarity NPC162973
0.8 Intermediate Similarity NPC471654
0.8 Intermediate Similarity NPC471413
0.8 Intermediate Similarity NPC10636
0.8 Intermediate Similarity NPC477720
0.8 Intermediate Similarity NPC470734
0.7979 Intermediate Similarity NPC151681
0.7979 Intermediate Similarity NPC121402
0.7979 Intermediate Similarity NPC474343
0.7979 Intermediate Similarity NPC224356
0.7979 Intermediate Similarity NPC132753
0.7979 Intermediate Similarity NPC475709
0.7979 Intermediate Similarity NPC175351
0.7978 Intermediate Similarity NPC312561
0.7978 Intermediate Similarity NPC471796
0.7976 Intermediate Similarity NPC198240
0.7976 Intermediate Similarity NPC239098
0.7959 Intermediate Similarity NPC34768
0.7957 Intermediate Similarity NPC295347
0.7957 Intermediate Similarity NPC183012
0.7955 Intermediate Similarity NPC329738
0.7955 Intermediate Similarity NPC472442
0.7938 Intermediate Similarity NPC120321
0.7935 Intermediate Similarity NPC166346
0.7935 Intermediate Similarity NPC115021
0.7935 Intermediate Similarity NPC472871
0.7935 Intermediate Similarity NPC472812
0.7931 Intermediate Similarity NPC22611
0.7931 Intermediate Similarity NPC12283
0.7931 Intermediate Similarity NPC474193
0.7931 Intermediate Similarity NPC469
0.7917 Intermediate Similarity NPC471412
0.7912 Intermediate Similarity NPC476437
0.7912 Intermediate Similarity NPC281942
0.7912 Intermediate Similarity NPC232426
0.7912 Intermediate Similarity NPC476369
0.7895 Intermediate Similarity NPC278673
0.7895 Intermediate Similarity NPC98868
0.7895 Intermediate Similarity NPC159763
0.7895 Intermediate Similarity NPC124512
0.7895 Intermediate Similarity NPC278386
0.7889 Intermediate Similarity NPC474629
0.7889 Intermediate Similarity NPC472870
0.7889 Intermediate Similarity NPC472302
0.7882 Intermediate Similarity NPC242767
0.7882 Intermediate Similarity NPC327674
0.7879 Intermediate Similarity NPC67321
0.7879 Intermediate Similarity NPC187435
0.7872 Intermediate Similarity NPC154526
0.7872 Intermediate Similarity NPC162346
0.7872 Intermediate Similarity NPC472362
0.7872 Intermediate Similarity NPC472363
0.7872 Intermediate Similarity NPC473153
0.7857 Intermediate Similarity NPC316500
0.7849 Intermediate Similarity NPC470255
0.7849 Intermediate Similarity NPC104925
0.7849 Intermediate Similarity NPC298973
0.7849 Intermediate Similarity NPC191521
0.7841 Intermediate Similarity NPC32223
0.7841 Intermediate Similarity NPC19849
0.7841 Intermediate Similarity NPC149869
0.7841 Intermediate Similarity NPC471302
0.7841 Intermediate Similarity NPC472864
0.7841 Intermediate Similarity NPC102048
0.7835 Intermediate Similarity NPC475038
0.7835 Intermediate Similarity NPC109195
0.7835 Intermediate Similarity NPC476769
0.7826 Intermediate Similarity NPC179517
0.7826 Intermediate Similarity NPC65513
0.7826 Intermediate Similarity NPC141831
0.7826 Intermediate Similarity NPC165904
0.7816 Intermediate Similarity NPC256112
0.7816 Intermediate Similarity NPC2524
0.7816 Intermediate Similarity NPC186276
0.7812 Intermediate Similarity NPC476767
0.7812 Intermediate Similarity NPC324841
0.7812 Intermediate Similarity NPC251680
0.7812 Intermediate Similarity NPC54705
0.7812 Intermediate Similarity NPC38855
0.7812 Intermediate Similarity NPC16601
0.7812 Intermediate Similarity NPC117685
0.7812 Intermediate Similarity NPC201406
0.7802 Intermediate Similarity NPC177141
0.7802 Intermediate Similarity NPC66344
0.7802 Intermediate Similarity NPC284561
0.7791 Intermediate Similarity NPC195424
0.7791 Intermediate Similarity NPC281880
0.7791 Intermediate Similarity NPC469802
0.7789 Intermediate Similarity NPC204054
0.7789 Intermediate Similarity NPC100912
0.7789 Intermediate Similarity NPC208094
0.7789 Intermediate Similarity NPC51499
0.7789 Intermediate Similarity NPC257726
0.7789 Intermediate Similarity NPC477718
0.7789 Intermediate Similarity NPC477719
0.7789 Intermediate Similarity NPC253826
0.7778 Intermediate Similarity NPC476600
0.7778 Intermediate Similarity NPC473891
0.7778 Intermediate Similarity NPC166857
0.7766 Intermediate Similarity NPC472441
0.7765 Intermediate Similarity NPC59436
0.7765 Intermediate Similarity NPC184737
0.7755 Intermediate Similarity NPC112009
0.7755 Intermediate Similarity NPC180204
0.7753 Intermediate Similarity NPC476602
0.7742 Intermediate Similarity NPC169343
0.7742 Intermediate Similarity NPC472641
0.7742 Intermediate Similarity NPC472640
0.7742 Intermediate Similarity NPC475657
0.7742 Intermediate Similarity NPC38232
0.7738 Intermediate Similarity NPC4509
0.7738 Intermediate Similarity NPC476601
0.7732 Intermediate Similarity NPC472643

  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 NPC30984 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
0.8675 High Similarity NPD4752 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD7638 Approved
0.7895 Intermediate Similarity NPD4225 Approved
0.7812 Intermediate Similarity NPD7640 Approved
0.7812 Intermediate Similarity NPD7639 Approved
0.7742 Intermediate Similarity NPD6399 Phase 3
0.7624 Intermediate Similarity NPD6686 Approved
0.7604 Intermediate Similarity NPD7902 Approved
0.7312 Intermediate Similarity NPD6672 Approved
0.7312 Intermediate Similarity NPD5737 Approved
0.7292 Intermediate Similarity NPD7900 Approved
0.7292 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7748 Approved
0.7283 Intermediate Similarity NPD7146 Approved
0.7283 Intermediate Similarity NPD6409 Approved
0.7283 Intermediate Similarity NPD5330 Approved
0.7283 Intermediate Similarity NPD7521 Approved
0.7283 Intermediate Similarity NPD7334 Approved
0.7283 Intermediate Similarity NPD6684 Approved
0.7253 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD6084 Phase 2
0.7245 Intermediate Similarity NPD6083 Phase 2
0.7234 Intermediate Similarity NPD6051 Approved
0.7174 Intermediate Similarity NPD1694 Approved
0.7174 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5696 Approved
0.7143 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD7632 Discontinued
0.7128 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6903 Approved
0.7083 Intermediate Similarity NPD7637 Suspended
0.7083 Intermediate Similarity NPD8034 Phase 2
0.7083 Intermediate Similarity NPD5693 Phase 1
0.7083 Intermediate Similarity NPD7515 Phase 2
0.7083 Intermediate Similarity NPD8035 Phase 2
0.7048 Intermediate Similarity NPD6372 Approved
0.7048 Intermediate Similarity NPD6373 Approved
0.7041 Intermediate Similarity NPD5695 Phase 3
0.7011 Intermediate Similarity NPD8039 Approved
0.6979 Remote Similarity NPD5785 Approved
0.6923 Remote Similarity NPD6402 Approved
0.6923 Remote Similarity NPD7128 Approved
0.6923 Remote Similarity NPD5739 Approved
0.6923 Remote Similarity NPD6675 Approved
0.6916 Remote Similarity NPD6650 Approved
0.6916 Remote Similarity NPD6649 Approved
0.6915 Remote Similarity NPD3618 Phase 1
0.6909 Remote Similarity NPD7115 Discovery
0.6907 Remote Similarity NPD5284 Approved
0.6907 Remote Similarity NPD5281 Approved
0.6887 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6882 Remote Similarity NPD3665 Phase 1
0.6882 Remote Similarity NPD3666 Approved
0.6882 Remote Similarity NPD3133 Approved
0.6875 Remote Similarity NPD6904 Approved
0.6875 Remote Similarity NPD6673 Approved
0.6875 Remote Similarity NPD6080 Approved
0.6869 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6869 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6832 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4695 Discontinued
0.6804 Remote Similarity NPD46 Approved
0.6804 Remote Similarity NPD6698 Approved
0.6792 Remote Similarity NPD6881 Approved
0.6792 Remote Similarity NPD6899 Approved
0.6792 Remote Similarity NPD7320 Approved
0.6737 Remote Similarity NPD4623 Approved
0.6737 Remote Similarity NPD4519 Discontinued
0.6702 Remote Similarity NPD4786 Approved
0.6702 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6701 Remote Similarity NPD4753 Phase 2
0.6701 Remote Similarity NPD5328 Approved
0.6701 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6698 Remote Similarity NPD5701 Approved
0.6698 Remote Similarity NPD5697 Approved
0.6696 Remote Similarity NPD7327 Approved
0.6696 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6667 Remote Similarity NPD3667 Approved
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD5209 Approved
0.6667 Remote Similarity NPD4221 Approved
0.6637 Remote Similarity NPD7516 Approved
0.6636 Remote Similarity NPD6011 Approved
0.6634 Remote Similarity NPD4697 Phase 3
0.6633 Remote Similarity NPD7838 Discovery
0.6632 Remote Similarity NPD5329 Approved
0.663 Remote Similarity NPD5790 Clinical (unspecified phase)
0.663 Remote Similarity NPD7525 Registered
0.6627 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6847 Approved
0.6606 Remote Similarity NPD8130 Phase 1
0.6606 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6617 Approved
0.6606 Remote Similarity NPD6869 Approved
0.6598 Remote Similarity NPD5208 Approved
0.6596 Remote Similarity NPD6695 Phase 3
0.6593 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6581 Remote Similarity NPD7507 Approved
0.6579 Remote Similarity NPD8294 Approved
0.6579 Remote Similarity NPD8377 Approved
0.6574 Remote Similarity NPD6014 Approved
0.6574 Remote Similarity NPD6013 Approved
0.6574 Remote Similarity NPD6012 Approved
0.6566 Remote Similarity NPD6411 Approved
0.6566 Remote Similarity NPD6050 Approved
0.6566 Remote Similarity NPD6079 Approved
0.6562 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6562 Remote Similarity NPD6098 Approved
0.6562 Remote Similarity NPD5279 Phase 3
0.6548 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6882 Approved
0.6545 Remote Similarity NPD6053 Discontinued
0.6545 Remote Similarity NPD8297 Approved
0.6542 Remote Similarity NPD6412 Phase 2
0.6538 Remote Similarity NPD5344 Discontinued
0.6535 Remote Similarity NPD5210 Approved
0.6535 Remote Similarity NPD4629 Approved
0.6526 Remote Similarity NPD4197 Approved
0.6522 Remote Similarity NPD8378 Approved
0.6522 Remote Similarity NPD8380 Approved
0.6522 Remote Similarity NPD8335 Approved
0.6522 Remote Similarity NPD8296 Approved
0.6522 Remote Similarity NPD4195 Approved
0.6522 Remote Similarity NPD8379 Approved
0.6522 Remote Similarity NPD8033 Approved
0.6517 Remote Similarity NPD6926 Approved
0.6517 Remote Similarity NPD6924 Approved
0.6514 Remote Similarity NPD6371 Approved
0.65 Remote Similarity NPD5779 Approved
0.65 Remote Similarity NPD4202 Approved
0.65 Remote Similarity NPD5778 Approved
0.6495 Remote Similarity NPD3573 Approved
0.6465 Remote Similarity NPD5692 Phase 3
0.6465 Remote Similarity NPD5207 Approved
0.6458 Remote Similarity NPD5363 Approved
0.6458 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6452 Remote Similarity NPD4821 Approved
0.6452 Remote Similarity NPD4819 Approved
0.6452 Remote Similarity NPD4820 Approved
0.6452 Remote Similarity NPD4822 Approved
0.6449 Remote Similarity NPD6008 Approved
0.6444 Remote Similarity NPD7339 Approved
0.6444 Remote Similarity NPD6942 Approved
0.6442 Remote Similarity NPD6648 Approved
0.6442 Remote Similarity NPD6404 Discontinued
0.6436 Remote Similarity NPD6001 Approved
0.6421 Remote Similarity NPD5362 Discontinued
0.6421 Remote Similarity NPD7154 Phase 3
0.6417 Remote Similarity NPD7319 Approved
0.6413 Remote Similarity NPD3617 Approved
0.6413 Remote Similarity NPD4271 Approved
0.6413 Remote Similarity NPD4268 Approved
0.6408 Remote Similarity NPD4755 Approved
0.64 Remote Similarity NPD5694 Approved
0.6392 Remote Similarity NPD4690 Approved
0.6392 Remote Similarity NPD4689 Approved
0.6392 Remote Similarity NPD4138 Approved
0.6392 Remote Similarity NPD4688 Approved
0.6392 Remote Similarity NPD4693 Phase 3
0.6392 Remote Similarity NPD5205 Approved
0.6392 Remote Similarity NPD5786 Approved
0.6389 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6379 Remote Similarity NPD7503 Approved
0.6374 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6374 Remote Similarity NPD6933 Approved
0.6364 Remote Similarity NPD6101 Approved
0.6364 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6354 Remote Similarity NPD3668 Phase 3
0.6344 Remote Similarity NPD6929 Approved
0.6344 Remote Similarity NPD7645 Phase 2
0.6327 Remote Similarity NPD7524 Approved
0.6327 Remote Similarity NPD7750 Discontinued
0.6321 Remote Similarity NPD5211 Phase 2
0.6316 Remote Similarity NPD4270 Approved
0.6316 Remote Similarity NPD6435 Approved
0.6316 Remote Similarity NPD4269 Approved
0.6311 Remote Similarity NPD7614 Phase 1
0.6311 Remote Similarity NPD5221 Approved
0.6311 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5222 Approved
0.6292 Remote Similarity NPD4243 Approved
0.6286 Remote Similarity NPD4696 Approved
0.6286 Remote Similarity NPD5285 Approved
0.6286 Remote Similarity NPD5286 Approved
0.6286 Remote Similarity NPD4700 Approved
0.6277 Remote Similarity NPD7509 Discontinued
0.6277 Remote Similarity NPD6930 Phase 2
0.6277 Remote Similarity NPD6931 Approved
0.6275 Remote Similarity NPD5282 Discontinued
0.6262 Remote Similarity NPD6052 Approved
0.6261 Remote Similarity NPD6335 Approved
0.625 Remote Similarity NPD5331 Approved
0.625 Remote Similarity NPD5173 Approved
0.625 Remote Similarity NPD4788 Approved
0.625 Remote Similarity NPD6923 Approved
0.625 Remote Similarity NPD6922 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