NPASS Compound

Structure

NPC162495 OpenBabel07101718202D 44 49 0 0 1 0 0 0 0 0999 V2000 -2.9212 13.1328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3586 1.7642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2942 0.3066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6881 -0.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0262 0.7639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2295 12.1815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5598 11.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8680 10.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1983 9.7449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5066 8.7936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 8.0510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1452 7.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4755 6.3571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7837 5.4058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1140 4.6632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4223 3.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7526 2.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0609 2.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3911 1.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9280 -0.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7056 0.7380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6381 -3.6289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4056 0.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7370 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1678 0.2510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1190 -1.1002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6757 -1.2618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4280 -2.0513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5491 -0.7748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8099 -2.2527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8771 -2.8859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5641 0.2251 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1189 -2.9755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6994 0.3240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4280 -2.0513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1827 -0.7489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4508 -4.6112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0158 -2.8603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3900 -3.7443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6591 -2.6906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0904 -3.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3888 -0.0208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 -0.1577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 23 2 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 0 0 0 0 22 37 1 0 0 0 0 24 28 1 0 0 0 0 25 36 1 1 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 27 36 1 1 0 0 0 28 35 1 0 0 0 0 28 38 2 0 0 0 0 29 32 1 6 0 0 0 29 42 1 0 0 0 0 30 33 1 1 0 0 0 30 41 1 0 0 0 0 31 33 1 6 0 0 0 31 35 1 0 0 0 0 31 39 1 0 0 0 0 32 23 1 1 0 0 0 32 43 1 0 0 0 0 33 22 1 6 0 0 0 33 41 1 0 0 0 0 34 19 1 6 0 0 0 34 42 1 0 0 0 0 34 43 1 0 0 0 0 34 44 1 0 0 0 0 35 40 1 6 0 0 0 36 44 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.38
Volume:	639.649
LogP:	7.208
LogD:	4.616
LogS:	-3.989
# Rotatable Bonds:	15
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	6.531
Fsp3:	0.806
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.886
MDCK Permeability:	2.8955937523278408e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.261

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.864
Plasma Protein Binding (PPB):	99.66141510009766%
Volume Distribution (VD):	1.825
Pgp-substrate:	3.0119879245758057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.368
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.601
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	5.769
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.745
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.787
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.935
Carcinogencity:	0.571
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC162495

Natural Product ID:	NPC162495
*Common Name:**	LRWLAXJSFDAHQE-NGOYXVJFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LRWLAXJSFDAHQE-NGOYXVJFSA-N
Standard InCHI:	InChI=1S/C36H54O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-34-42-29-27-30-33(22-37,41-30)31(39)35(40)26(20-24(4)28(35)38)36(27,44-34)25(5)21-32(29,43-34)23(2)3/h18-20,25-27,29-31,37,39-40H,2,6-17,21-22H2,1,3-5H3/b19-18+/t25-,26-,27-,29-,30+,31-,32-,33+,34-,35-,36+/m1/s1
SMILES:	CCCCCCCCCCCCC/C=C/[C@@]12O[C@H]3[C@@](O1)(C[C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502338
PubChem CID:	44559844
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane 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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]

☑ 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

Activity Type	# Activity
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.02	nmol	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	50.0	/nmol	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	94.0	%	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	6.0	%	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	100.0	%	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	69.0	%	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.7	n.a.	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.13	n.a.	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	9.7	n.a.	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	2.9	n.a.	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	94.0	%	PMID[557129]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	100.0	%	PMID[557129]

☑ 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 NPC162495 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1588
0.2-0.3	4567
0.3-0.4	7485
0.4-0.5	12821
0.5-0.6	9205
0.6-0.7	5283
0.7-0.8	1341
0.8-0.85	74
0.85-0.9	12
0.9-0.95	5
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9833	High Similarity	NPC473485
0.9833	High Similarity	NPC474508
0.9833	High Similarity	NPC180902
0.9833	High Similarity	NPC475139
0.9831	High Similarity	NPC475273
0.9831	High Similarity	NPC168849
0.975	High Similarity	NPC251564
0.975	High Similarity	NPC475314
0.975	High Similarity	NPC475606
0.975	High Similarity	NPC477189
0.9746	High Similarity	NPC217901
0.9672	High Similarity	NPC471137
0.9672	High Similarity	NPC471136
0.9672	High Similarity	NPC475500
0.9672	High Similarity	NPC475154
0.9672	High Similarity	NPC100017
0.9672	High Similarity	NPC473548
0.9672	High Similarity	NPC182266
0.9672	High Similarity	NPC223356
0.9516	High Similarity	NPC68282
0.9421	High Similarity	NPC476091
0.9421	High Similarity	NPC476078
0.9268	High Similarity	NPC473838
0.9268	High Similarity	NPC475389
0.925	High Similarity	NPC473802
0.9174	High Similarity	NPC473919
0.9174	High Similarity	NPC473709
0.9098	High Similarity	NPC471939
0.9024	High Similarity	NPC471940
0.8843	High Similarity	NPC142882
0.8651	High Similarity	NPC236999
0.8651	High Similarity	NPC270109
0.8548	High Similarity	NPC257017
0.8548	High Similarity	NPC162009
0.8492	Intermediate Similarity	NPC222307
0.848	Intermediate Similarity	NPC472399
0.84	Intermediate Similarity	NPC19464
0.8387	Intermediate Similarity	NPC329008
0.8387	Intermediate Similarity	NPC317635
0.8346	Intermediate Similarity	NPC225049
0.832	Intermediate Similarity	NPC52839
0.832	Intermediate Similarity	NPC472401
0.8281	Intermediate Similarity	NPC298841
0.8268	Intermediate Similarity	NPC145238
0.824	Intermediate Similarity	NPC471128
0.824	Intermediate Similarity	NPC145182
0.824	Intermediate Similarity	NPC471126
0.824	Intermediate Similarity	NPC157252
0.8226	Intermediate Similarity	NPC146280
0.8226	Intermediate Similarity	NPC124676
0.8182	Intermediate Similarity	NPC471234
0.8175	Intermediate Similarity	NPC102822
0.8175	Intermediate Similarity	NPC477046
0.8168	Intermediate Similarity	NPC471855
0.816	Intermediate Similarity	NPC471108
0.816	Intermediate Similarity	NPC22628
0.816	Intermediate Similarity	NPC5991
0.816	Intermediate Similarity	NPC5989
0.816	Intermediate Similarity	NPC255081
0.816	Intermediate Similarity	NPC275696
0.814	Intermediate Similarity	NPC42399
0.8125	Intermediate Similarity	NPC470922
0.8095	Intermediate Similarity	NPC143755
0.8095	Intermediate Similarity	NPC472004
0.8092	Intermediate Similarity	NPC476852
0.808	Intermediate Similarity	NPC171905
0.808	Intermediate Similarity	NPC472397
0.808	Intermediate Similarity	NPC471125
0.808	Intermediate Similarity	NPC472758
0.8077	Intermediate Similarity	NPC473620
0.8062	Intermediate Similarity	NPC473635
0.8049	Intermediate Similarity	NPC477126
0.8047	Intermediate Similarity	NPC469352
0.8043	Intermediate Similarity	NPC471172
0.8027	Intermediate Similarity	NPC49297
0.8016	Intermediate Similarity	NPC470186
0.8016	Intermediate Similarity	NPC472667
0.8016	Intermediate Similarity	NPC469488
0.8016	Intermediate Similarity	NPC476529
0.8016	Intermediate Similarity	NPC475775
0.8016	Intermediate Similarity	NPC476107
0.8015	Intermediate Similarity	NPC231529
0.8015	Intermediate Similarity	NPC476851
0.8015	Intermediate Similarity	NPC471407
0.8015	Intermediate Similarity	NPC470851
0.8015	Intermediate Similarity	NPC475371
0.8	Intermediate Similarity	NPC477116
0.8	Intermediate Similarity	NPC27999
0.8	Intermediate Similarity	NPC156252
0.8	Intermediate Similarity	NPC596
0.8	Intermediate Similarity	NPC10721
0.8	Intermediate Similarity	NPC470780
0.8	Intermediate Similarity	NPC287423
0.8	Intermediate Similarity	NPC146310
0.7986	Intermediate Similarity	NPC48813
0.7986	Intermediate Similarity	NPC194854
0.7984	Intermediate Similarity	NPC24651
0.797	Intermediate Similarity	NPC168879
0.7959	Intermediate Similarity	NPC181924
0.7955	Intermediate Similarity	NPC476855
0.7955	Intermediate Similarity	NPC471170
0.7955	Intermediate Similarity	NPC476863
0.7955	Intermediate Similarity	NPC476862
0.7953	Intermediate Similarity	NPC185876
0.7953	Intermediate Similarity	NPC475885
0.7953	Intermediate Similarity	NPC107338
0.7953	Intermediate Similarity	NPC109607
0.7953	Intermediate Similarity	NPC472759
0.7953	Intermediate Similarity	NPC48692
0.7953	Intermediate Similarity	NPC329080
0.7953	Intermediate Similarity	NPC112038
0.7953	Intermediate Similarity	NPC19336
0.7939	Intermediate Similarity	NPC470850
0.7939	Intermediate Similarity	NPC476859
0.7937	Intermediate Similarity	NPC204552
0.7937	Intermediate Similarity	NPC188667
0.7934	Intermediate Similarity	NPC29827
0.7929	Intermediate Similarity	NPC16729
0.7929	Intermediate Similarity	NPC475462
0.7926	Intermediate Similarity	NPC471089
0.7926	Intermediate Similarity	NPC190065
0.7926	Intermediate Similarity	NPC141215
0.7923	Intermediate Similarity	NPC293112
0.792	Intermediate Similarity	NPC471127
0.792	Intermediate Similarity	NPC154363
0.792	Intermediate Similarity	NPC234858
0.7907	Intermediate Similarity	NPC18945
0.7907	Intermediate Similarity	NPC105926
0.7907	Intermediate Similarity	NPC67251
0.7907	Intermediate Similarity	NPC471392
0.7907	Intermediate Similarity	NPC91693
0.7907	Intermediate Similarity	NPC11895
0.7907	Intermediate Similarity	NPC265557
0.7903	Intermediate Similarity	NPC477091
0.7903	Intermediate Similarity	NPC474937
0.7899	Intermediate Similarity	NPC5153
0.7899	Intermediate Similarity	NPC48414
0.7895	Intermediate Similarity	NPC231240
0.7895	Intermediate Similarity	NPC33378
0.7895	Intermediate Similarity	NPC102316
0.7895	Intermediate Similarity	NPC6274
0.7895	Intermediate Similarity	NPC100390
0.7895	Intermediate Similarity	NPC472769
0.7895	Intermediate Similarity	NPC254614
0.7895	Intermediate Similarity	NPC254146
0.7891	Intermediate Similarity	NPC310511
0.7891	Intermediate Similarity	NPC470779
0.7891	Intermediate Similarity	NPC204731
0.7879	Intermediate Similarity	NPC476966
0.7879	Intermediate Similarity	NPC175186
0.7879	Intermediate Similarity	NPC473593
0.7879	Intermediate Similarity	NPC476854
0.7879	Intermediate Similarity	NPC104382
0.7879	Intermediate Similarity	NPC470880
0.7874	Intermediate Similarity	NPC180640
0.7874	Intermediate Similarity	NPC236918
0.7874	Intermediate Similarity	NPC9674
0.7874	Intermediate Similarity	NPC156745
0.7874	Intermediate Similarity	NPC19028
0.7868	Intermediate Similarity	NPC140045
0.7868	Intermediate Similarity	NPC295885
0.7867	Intermediate Similarity	NPC43304
0.7867	Intermediate Similarity	NPC477190
0.7867	Intermediate Similarity	NPC477188
0.7867	Intermediate Similarity	NPC275477
0.7863	Intermediate Similarity	NPC473253
0.7863	Intermediate Similarity	NPC470882
0.7863	Intermediate Similarity	NPC305496
0.7857	Intermediate Similarity	NPC122033
0.7857	Intermediate Similarity	NPC287343
0.7857	Intermediate Similarity	NPC474654
0.7857	Intermediate Similarity	NPC470854
0.7857	Intermediate Similarity	NPC469684
0.7857	Intermediate Similarity	NPC97908
0.7852	Intermediate Similarity	NPC262813
0.7851	Intermediate Similarity	NPC474716
0.7846	Intermediate Similarity	NPC86346
0.7846	Intermediate Similarity	NPC469379
0.7846	Intermediate Similarity	NPC172154
0.7846	Intermediate Similarity	NPC81736
0.7846	Intermediate Similarity	NPC8369
0.7846	Intermediate Similarity	NPC75856
0.7846	Intermediate Similarity	NPC476729
0.784	Intermediate Similarity	NPC472400
0.784	Intermediate Similarity	NPC238667
0.784	Intermediate Similarity	NPC474872
0.7836	Intermediate Similarity	NPC316915
0.7836	Intermediate Similarity	NPC478151
0.7836	Intermediate Similarity	NPC88668
0.7833	Intermediate Similarity	NPC474741
0.7829	Intermediate Similarity	NPC170538
0.7829	Intermediate Similarity	NPC312833
0.7829	Intermediate Similarity	NPC222688
0.7823	Intermediate Similarity	NPC170212
0.7823	Intermediate Similarity	NPC221511
0.7823	Intermediate Similarity	NPC89227
0.7823	Intermediate Similarity	NPC101825
0.7823	Intermediate Similarity	NPC151216
0.7823	Intermediate Similarity	NPC17138
0.7823	Intermediate Similarity	NPC215643

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 NPC162495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1797
0.2-0.3	3832
0.3-0.4	2152
0.4-0.5	669
0.5-0.6	275
0.6-0.7	157
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7812	Intermediate Similarity	NPD6054	Approved
0.7705	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6370	Approved
0.7615	Intermediate Similarity	NPD6015	Approved
0.7615	Intermediate Similarity	NPD6016	Approved
0.7612	Intermediate Similarity	NPD7319	Approved
0.7576	Intermediate Similarity	NPD7492	Approved
0.7557	Intermediate Similarity	NPD5988	Approved
0.7538	Intermediate Similarity	NPD6059	Approved
0.7537	Intermediate Similarity	NPD7736	Approved
0.7519	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7078	Approved
0.7388	Intermediate Similarity	NPD7507	Approved
0.7348	Intermediate Similarity	NPD8516	Approved
0.7348	Intermediate Similarity	NPD8517	Approved
0.7348	Intermediate Similarity	NPD8515	Approved
0.7348	Intermediate Similarity	NPD8513	Phase 3
0.7333	Intermediate Similarity	NPD8293	Discontinued
0.7308	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD6319	Approved
0.7244	Intermediate Similarity	NPD6371	Approved
0.7239	Intermediate Similarity	NPD8328	Phase 3
0.7197	Intermediate Similarity	NPD7516	Approved
0.7154	Intermediate Similarity	NPD5344	Discontinued
0.7132	Intermediate Similarity	NPD8297	Approved
0.7132	Intermediate Similarity	NPD6882	Approved
0.7121	Intermediate Similarity	NPD7328	Approved
0.7121	Intermediate Similarity	NPD7327	Approved
0.7087	Intermediate Similarity	NPD6686	Approved
0.708	Intermediate Similarity	NPD8074	Phase 3
0.7054	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6009	Approved
0.7031	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6033	Approved
0.6977	Remote Similarity	NPD4634	Approved
0.6977	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8380	Approved
0.6963	Remote Similarity	NPD8335	Approved
0.6963	Remote Similarity	NPD8033	Approved
0.6963	Remote Similarity	NPD6921	Approved
0.6963	Remote Similarity	NPD8379	Approved
0.6963	Remote Similarity	NPD8296	Approved
0.6963	Remote Similarity	NPD8378	Approved
0.6947	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6650	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8294	Approved
0.6889	Remote Similarity	NPD8377	Approved
0.6885	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4225	Approved
0.6833	Remote Similarity	NPD6698	Approved
0.6833	Remote Similarity	NPD46	Approved
0.6822	Remote Similarity	NPD6899	Approved
0.6822	Remote Similarity	NPD6881	Approved
0.6803	Remote Similarity	NPD5282	Discontinued
0.68	Remote Similarity	NPD6648	Approved
0.6797	Remote Similarity	NPD6008	Approved
0.6794	Remote Similarity	NPD8130	Phase 1
0.6769	Remote Similarity	NPD6372	Approved
0.6769	Remote Similarity	NPD6373	Approved
0.6744	Remote Similarity	NPD6412	Phase 2
0.6744	Remote Similarity	NPD5697	Approved
0.6744	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6053	Discontinued
0.6739	Remote Similarity	NPD7604	Phase 2
0.672	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6883	Approved
0.6718	Remote Similarity	NPD7102	Approved
0.6718	Remote Similarity	NPD7290	Approved
0.6715	Remote Similarity	NPD7503	Approved
0.6693	Remote Similarity	NPD5211	Phase 2
0.6692	Remote Similarity	NPD7320	Approved
0.6692	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6641	Remote Similarity	NPD6012	Approved
0.6641	Remote Similarity	NPD6013	Approved
0.6641	Remote Similarity	NPD6014	Approved
0.6641	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD7830	Approved
0.6619	Remote Similarity	NPD7642	Approved
0.6619	Remote Similarity	NPD7829	Approved
0.6612	Remote Similarity	NPD1695	Approved
0.6597	Remote Similarity	NPD8338	Approved
0.6594	Remote Similarity	NPD5983	Phase 2
0.6589	Remote Similarity	NPD5141	Approved
0.6573	Remote Similarity	NPD5956	Approved
0.6565	Remote Similarity	NPD6011	Approved
0.6562	Remote Similarity	NPD5224	Approved
0.6562	Remote Similarity	NPD4633	Approved
0.6562	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD5226	Approved
0.6557	Remote Similarity	NPD7838	Discovery
0.655	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6336	Discontinued
0.6512	Remote Similarity	NPD5174	Approved
0.6512	Remote Similarity	NPD5175	Approved
0.6508	Remote Similarity	NPD4755	Approved
0.6504	Remote Similarity	NPD7983	Approved
0.6489	Remote Similarity	NPD5701	Approved
0.6484	Remote Similarity	NPD5223	Approved
0.6457	Remote Similarity	NPD7638	Approved
0.6439	Remote Similarity	NPD4730	Approved
0.6439	Remote Similarity	NPD4729	Approved
0.6414	Remote Similarity	NPD7260	Phase 2
0.6406	Remote Similarity	NPD7640	Approved
0.6406	Remote Similarity	NPD7639	Approved
0.6406	Remote Similarity	NPD4700	Approved
0.6369	Remote Similarity	NPD7799	Discontinued
0.6357	Remote Similarity	NPD1700	Approved
0.6357	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5249	Phase 3
0.6343	Remote Similarity	NPD5248	Approved
0.6343	Remote Similarity	NPD5247	Approved
0.6343	Remote Similarity	NPD5250	Approved
0.6343	Remote Similarity	NPD5251	Approved
0.6331	Remote Similarity	NPD7101	Approved
0.6331	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD5778	Approved
0.632	Remote Similarity	NPD5779	Approved
0.6301	Remote Similarity	NPD8407	Phase 2
0.6299	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5222	Approved
0.6299	Remote Similarity	NPD5221	Approved
0.6296	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD8451	Approved
0.6288	Remote Similarity	NPD4768	Approved
0.6288	Remote Similarity	NPD4767	Approved
0.6284	Remote Similarity	NPD8415	Approved
0.6268	Remote Similarity	NPD6067	Discontinued
0.6259	Remote Similarity	NPD6845	Suspended
0.6259	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD8448	Approved
0.6242	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD8267	Approved
0.6241	Remote Similarity	NPD8266	Approved
0.6241	Remote Similarity	NPD8268	Approved
0.6241	Remote Similarity	NPD8269	Approved
0.624	Remote Similarity	NPD6079	Approved
0.6232	Remote Similarity	NPD6274	Approved
0.6221	Remote Similarity	NPD8368	Discontinued
0.6212	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8336	Approved
0.6207	Remote Similarity	NPD8337	Approved
0.6197	Remote Similarity	NPD8080	Discontinued
0.6194	Remote Similarity	NPD5128	Approved
0.6187	Remote Similarity	NPD6317	Approved
0.6176	Remote Similarity	NPD5217	Approved
0.6176	Remote Similarity	NPD5216	Approved
0.6176	Remote Similarity	NPD5215	Approved
0.6172	Remote Similarity	NPD7839	Suspended
0.6172	Remote Similarity	NPD4697	Phase 3
0.6148	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6313	Approved
0.6143	Remote Similarity	NPD6314	Approved
0.6136	Remote Similarity	NPD4754	Approved
0.6127	Remote Similarity	NPD8444	Approved
0.6124	Remote Similarity	NPD6084	Phase 2
0.6124	Remote Similarity	NPD6083	Phase 2
0.6122	Remote Similarity	NPD8390	Approved
0.6122	Remote Similarity	NPD8391	Approved
0.6122	Remote Similarity	NPD8392	Approved
0.6111	Remote Similarity	NPD8340	Approved
0.6111	Remote Similarity	NPD8299	Approved
0.6111	Remote Similarity	NPD8342	Approved
0.6111	Remote Similarity	NPD8341	Approved
0.6103	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5135	Approved
0.6103	Remote Similarity	NPD5169	Approved
0.6094	Remote Similarity	NPD5210	Approved
0.6094	Remote Similarity	NPD4629	Approved
0.608	Remote Similarity	NPD6101	Approved
0.608	Remote Similarity	NPD5328	Approved
0.608	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD8273	Phase 1
0.6058	Remote Similarity	NPD5127	Approved
0.6032	Remote Similarity	NPD5785	Approved
0.6032	Remote Similarity	NPD3168	Discontinued
0.6028	Remote Similarity	NPD7641	Discontinued
0.6016	Remote Similarity	NPD1694	Approved
0.6014	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD6909	Approved
0.6014	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6868	Approved
0.5986	Remote Similarity	NPD4522	Approved
0.5984	Remote Similarity	NPD6411	Approved
0.5969	Remote Similarity	NPD5695	Phase 3

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