NPASS Compound

Structure

NPC329992 OpenBabel07101719252D 41 44 0 0 1 0 0 0 0 0999 V2000 2.9676 2.7133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4485 -0.5429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2510 1.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4430 -0.4383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4986 3.7113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9053 4.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6797 1.9887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0809 3.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0591 2.5944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4163 3.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4103 3.7181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0864 2.9023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7472 2.8066 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9382 4.2079 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.9163 4.4158 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2674 1.1797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6687 2.1978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3176 5.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2620 1.2842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8336 3.2133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.7243 6.3474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8607 0.2662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6632 2.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8498 0.4752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3230 5.3293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 37 1 0 0 0 0 6 38 1 0 0 0 0 7 39 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 27 1 0 0 0 0 10 17 2 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 11 24 2 0 0 0 0 12 18 2 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 26 2 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 40 1 6 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 22 41 1 1 0 0 0 23 28 2 0 0 0 0 23 34 1 0 0 0 0 24 28 1 0 0 0 0 24 35 1 0 0 0 0 25 29 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 0 0 0 0 26 37 1 0 0 0 0 27 32 2 0 0 0 0 27 41 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 33 2 0 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	571.24
Volume:	568.381
LogP:	3.317
LogD:	3.241
LogS:	-4.507
# Rotatable Bonds:	13
TPSA:	111.22
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	4.58
Fsp3:	0.467
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.673
MDCK Permeability:	4.242973227519542e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.67
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	51.371070861816406%
Volume Distribution (VD):	0.717
Pgp-substrate:	46.83627700805664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.655
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.812
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	9.119
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.929
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.798
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.912
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC329992

Natural Product ID:	NPC329992
*Common Name:**	Pervilleine B
IUPAC Name:	[(3S,6S)-8-methyl-6-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] 3,4,5-trimethoxybenzoate
Synonyms:	Pervilleine B
Standard InCHIKey:	KKZAOZSLMGOEFU-ZAXSSQMLSA-N
Standard InCHI:	InChI=1S/C30H37NO10/c1-31-19-14-20(40-30(33)18-12-25(36-4)29(39-7)26(13-18)37-5)16-21(31)22(15-19)41-27(32)9-8-17-10-23(34-2)28(38-6)24(11-17)35-3/h8-13,19-22H,14-16H2,1-7H3/b9-8+/t19?,20-,21?,22-/m0/s1
SMILES:	COc1c(OC)cc(cc1OC)/C=C/C(=O)O[C@H]1CC2N(C1C[C@H](C2)OC(=O)c1cc(OC)c(c(c1)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486059
PubChem CID:	44576220
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives

*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
NPO33258	erythroxylum pervillei	Species	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754602]

☑ 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
ED50	8
IC50	3

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	3.1	ug ml-1	PMID[510097]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[510097]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[510097]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[510097]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	3.2	ug ml-1	PMID[510097]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	3800.0	nM	PMID[510097]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	9.4	ug ml-1	PMID[510097]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.1	ug ml-1	PMID[510097]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.8	ug ml-1	PMID[510097]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[510097]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	120.0	nM	PMID[510097]

☑ 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 NPC329992 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	274
0.1-0.2	1259
0.2-0.3	4054
0.3-0.4	10674
0.4-0.5	7453
0.5-0.6	6704
0.6-0.7	11086
0.7-0.8	1176
0.8-0.85	3
0.85-0.9	1
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9693	High Similarity	NPC473562
0.956	High Similarity	NPC474858
0.9451	High Similarity	NPC329816
0.943	High Similarity	NPC26353
0.9245	High Similarity	NPC329640
0.9112	High Similarity	NPC475566
0.8963	High Similarity	NPC329717
0.8788	High Similarity	NPC35345
0.8315	Intermediate Similarity	NPC141440
0.8297	Intermediate Similarity	NPC83019
0.8276	Intermediate Similarity	NPC35680
0.8242	Intermediate Similarity	NPC204580
0.8216	Intermediate Similarity	NPC328700
0.8216	Intermediate Similarity	NPC119818
0.8216	Intermediate Similarity	NPC2173
0.8216	Intermediate Similarity	NPC202771
0.811	Intermediate Similarity	NPC214239
0.8049	Intermediate Similarity	NPC213482
0.8	Intermediate Similarity	NPC124302
0.8	Intermediate Similarity	NPC73020
0.8	Intermediate Similarity	NPC70290
0.8	Intermediate Similarity	NPC14622
0.8	Intermediate Similarity	NPC46744
0.8	Intermediate Similarity	NPC215098
0.7978	Intermediate Similarity	NPC94499
0.7975	Intermediate Similarity	NPC288743
0.7964	Intermediate Similarity	NPC473091
0.7956	Intermediate Similarity	NPC162694
0.7941	Intermediate Similarity	NPC222185
0.7926	Intermediate Similarity	NPC286135
0.7914	Intermediate Similarity	NPC72788
0.7914	Intermediate Similarity	NPC120671
0.7914	Intermediate Similarity	NPC226652
0.7914	Intermediate Similarity	NPC314100
0.7901	Intermediate Similarity	NPC18306
0.787	Intermediate Similarity	NPC75695
0.7849	Intermediate Similarity	NPC472860
0.7836	Intermediate Similarity	NPC145425
0.7818	Intermediate Similarity	NPC469978
0.7811	Intermediate Similarity	NPC62354
0.7803	Intermediate Similarity	NPC289811
0.7803	Intermediate Similarity	NPC160780
0.7797	Intermediate Similarity	NPC227683
0.7791	Intermediate Similarity	NPC301897
0.7785	Intermediate Similarity	NPC299010
0.7759	Intermediate Similarity	NPC239966
0.7759	Intermediate Similarity	NPC53889
0.7759	Intermediate Similarity	NPC203020
0.7758	Intermediate Similarity	NPC28326
0.7751	Intermediate Similarity	NPC474648
0.7746	Intermediate Similarity	NPC158900
0.7746	Intermediate Similarity	NPC1913
0.7746	Intermediate Similarity	NPC226759
0.7733	Intermediate Similarity	NPC471746
0.7719	Intermediate Similarity	NPC475116
0.7719	Intermediate Similarity	NPC169742
0.7719	Intermediate Similarity	NPC146277
0.7719	Intermediate Similarity	NPC19380
0.7714	Intermediate Similarity	NPC472859
0.7714	Intermediate Similarity	NPC311803
0.7714	Intermediate Similarity	NPC25389
0.7711	Intermediate Similarity	NPC22176
0.7711	Intermediate Similarity	NPC121573
0.7711	Intermediate Similarity	NPC226738
0.7711	Intermediate Similarity	NPC190587
0.7708	Intermediate Similarity	NPC80472
0.7706	Intermediate Similarity	NPC243891
0.7701	Intermediate Similarity	NPC87317
0.7701	Intermediate Similarity	NPC325122
0.7701	Intermediate Similarity	NPC33256
0.7701	Intermediate Similarity	NPC470646
0.7692	Intermediate Similarity	NPC183236
0.7692	Intermediate Similarity	NPC476394
0.7692	Intermediate Similarity	NPC98809
0.7684	Intermediate Similarity	NPC477884
0.7679	Intermediate Similarity	NPC24257
0.7679	Intermediate Similarity	NPC153620
0.7674	Intermediate Similarity	NPC186507
0.767	Intermediate Similarity	NPC285108
0.767	Intermediate Similarity	NPC33298
0.7665	Intermediate Similarity	NPC293201
0.7665	Intermediate Similarity	NPC27106
0.7661	Intermediate Similarity	NPC151425
0.7661	Intermediate Similarity	NPC228662
0.7661	Intermediate Similarity	NPC93498
0.7661	Intermediate Similarity	NPC198615
0.7661	Intermediate Similarity	NPC163883
0.7661	Intermediate Similarity	NPC134905
0.7661	Intermediate Similarity	NPC473732
0.7661	Intermediate Similarity	NPC474663
0.7661	Intermediate Similarity	NPC36130
0.7661	Intermediate Similarity	NPC267091
0.7661	Intermediate Similarity	NPC476434
0.7657	Intermediate Similarity	NPC166277
0.7657	Intermediate Similarity	NPC24627
0.7657	Intermediate Similarity	NPC476373
0.7657	Intermediate Similarity	NPC477164
0.7657	Intermediate Similarity	NPC119125
0.7654	Intermediate Similarity	NPC211386
0.7654	Intermediate Similarity	NPC72796
0.7654	Intermediate Similarity	NPC44245
0.7644	Intermediate Similarity	NPC68324
0.7644	Intermediate Similarity	NPC156818
0.7644	Intermediate Similarity	NPC289322
0.7644	Intermediate Similarity	NPC114179
0.7644	Intermediate Similarity	NPC160512
0.7644	Intermediate Similarity	NPC38779
0.7633	Intermediate Similarity	NPC469539
0.7633	Intermediate Similarity	NPC470088
0.7633	Intermediate Similarity	NPC469540
0.7633	Intermediate Similarity	NPC472969
0.7633	Intermediate Similarity	NPC294972
0.7624	Intermediate Similarity	NPC309692
0.7622	Intermediate Similarity	NPC470962
0.7622	Intermediate Similarity	NPC469437
0.7619	Intermediate Similarity	NPC136278
0.7617	Intermediate Similarity	NPC476500
0.7616	Intermediate Similarity	NPC137813
0.7616	Intermediate Similarity	NPC308555
0.7614	Intermediate Similarity	NPC319749
0.7605	Intermediate Similarity	NPC473090
0.7602	Intermediate Similarity	NPC29056
0.76	Intermediate Similarity	NPC74319
0.76	Intermediate Similarity	NPC287872
0.7593	Intermediate Similarity	NPC155098
0.759	Intermediate Similarity	NPC46180
0.7588	Intermediate Similarity	NPC63256
0.7588	Intermediate Similarity	NPC476342
0.7588	Intermediate Similarity	NPC10304
0.7586	Intermediate Similarity	NPC155063
0.7586	Intermediate Similarity	NPC291948
0.7586	Intermediate Similarity	NPC300845
0.7586	Intermediate Similarity	NPC477380
0.7586	Intermediate Similarity	NPC104983
0.7586	Intermediate Similarity	NPC257277
0.7586	Intermediate Similarity	NPC88803
0.7586	Intermediate Similarity	NPC250436
0.7584	Intermediate Similarity	NPC142614
0.7584	Intermediate Similarity	NPC475738
0.7582	Intermediate Similarity	NPC84482
0.7582	Intermediate Similarity	NPC169645
0.7574	Intermediate Similarity	NPC195919
0.7574	Intermediate Similarity	NPC120924
0.7574	Intermediate Similarity	NPC216314
0.7572	Intermediate Similarity	NPC25127
0.7572	Intermediate Similarity	NPC191046
0.7572	Intermediate Similarity	NPC194095
0.7572	Intermediate Similarity	NPC478213
0.7572	Intermediate Similarity	NPC327032
0.7572	Intermediate Similarity	NPC57211
0.7572	Intermediate Similarity	NPC287504
0.7571	Intermediate Similarity	NPC476371
0.7571	Intermediate Similarity	NPC414831
0.7571	Intermediate Similarity	NPC148273
0.7571	Intermediate Similarity	NPC476372
0.756	Intermediate Similarity	NPC470932
0.756	Intermediate Similarity	NPC113089
0.756	Intermediate Similarity	NPC474158
0.7558	Intermediate Similarity	NPC104353
0.7558	Intermediate Similarity	NPC474388
0.7558	Intermediate Similarity	NPC472535
0.7558	Intermediate Similarity	NPC474170
0.7557	Intermediate Similarity	NPC298093
0.7557	Intermediate Similarity	NPC24164
0.7557	Intermediate Similarity	NPC289346
0.7556	Intermediate Similarity	NPC197708
0.7556	Intermediate Similarity	NPC658
0.7545	Intermediate Similarity	NPC185607
0.7544	Intermediate Similarity	NPC238366
0.7544	Intermediate Similarity	NPC306343
0.7543	Intermediate Similarity	NPC108456
0.7543	Intermediate Similarity	NPC258644
0.7543	Intermediate Similarity	NPC19097
0.7543	Intermediate Similarity	NPC477885
0.7532	Intermediate Similarity	NPC154275
0.7529	Intermediate Similarity	NPC248257
0.7529	Intermediate Similarity	NPC34725
0.7529	Intermediate Similarity	NPC276059
0.7529	Intermediate Similarity	NPC142528
0.7529	Intermediate Similarity	NPC10205
0.7529	Intermediate Similarity	NPC470511
0.7529	Intermediate Similarity	NPC117463
0.7529	Intermediate Similarity	NPC254163
0.7529	Intermediate Similarity	NPC122623
0.7529	Intermediate Similarity	NPC241774
0.7529	Intermediate Similarity	NPC85233
0.7529	Intermediate Similarity	NPC205522
0.7529	Intermediate Similarity	NPC203757
0.7529	Intermediate Similarity	NPC120621
0.7527	Intermediate Similarity	NPC208890
0.7515	Intermediate Similarity	NPC207516
0.7515	Intermediate Similarity	NPC296575
0.7515	Intermediate Similarity	NPC471590
0.7515	Intermediate Similarity	NPC30890
0.7515	Intermediate Similarity	NPC44573
0.7514	Intermediate Similarity	NPC209411
0.7514	Intermediate Similarity	NPC180768
0.7514	Intermediate Similarity	NPC105827
0.7514	Intermediate Similarity	NPC34376
0.7514	Intermediate Similarity	NPC239890

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 NPC329992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	585
0.2-0.3	1168
0.3-0.4	2351
0.4-0.5	2460
0.5-0.6	1572
0.6-0.7	772
0.7-0.8	68
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9182	High Similarity	NPD5353	Approved
0.8758	High Similarity	NPD6385	Approved
0.8758	High Similarity	NPD6386	Approved
0.8683	High Similarity	NPD5242	Approved
0.8216	Intermediate Similarity	NPD5006	Approved
0.8216	Intermediate Similarity	NPD5005	Approved
0.8107	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4420	Approved
0.7844	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4236	Phase 3
0.7744	Intermediate Similarity	NPD4237	Approved
0.7725	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7039	Approved
0.7722	Intermediate Similarity	NPD7038	Approved
0.763	Intermediate Similarity	NPD5977	Approved
0.763	Intermediate Similarity	NPD5978	Approved
0.7619	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3146	Approved
0.7586	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5710	Approved
0.7571	Intermediate Similarity	NPD5711	Approved
0.756	Intermediate Similarity	NPD5297	Approved
0.7558	Intermediate Similarity	NPD6873	Phase 2
0.7557	Intermediate Similarity	NPD5677	Discontinued
0.7557	Intermediate Similarity	NPD5494	Approved
0.7545	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2654	Approved
0.7529	Intermediate Similarity	NPD3817	Phase 2
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6625	Approved
0.7405	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2163	Approved
0.7399	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7565	Approved
0.7391	Intermediate Similarity	NPD7549	Discontinued
0.7389	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3140	Approved
0.7362	Intermediate Similarity	NPD3142	Approved
0.736	Intermediate Similarity	NPD7701	Phase 2
0.7356	Intermediate Similarity	NPD5890	Approved
0.7356	Intermediate Similarity	NPD5889	Approved
0.7347	Intermediate Similarity	NPD7999	Approved
0.7333	Intermediate Similarity	NPD7497	Discontinued
0.7314	Intermediate Similarity	NPD1934	Approved
0.7314	Intermediate Similarity	NPD6844	Discontinued
0.7308	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3818	Discontinued
0.7306	Intermediate Similarity	NPD8285	Discontinued
0.7306	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2975	Approved
0.7292	Intermediate Similarity	NPD2973	Approved
0.7292	Intermediate Similarity	NPD2974	Approved
0.7288	Intermediate Similarity	NPD3882	Suspended
0.7283	Intermediate Similarity	NPD4210	Discontinued
0.7268	Intermediate Similarity	NPD5844	Phase 1
0.7268	Intermediate Similarity	NPD4107	Approved
0.7267	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7110	Phase 1
0.7257	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3455	Phase 2
0.7229	Intermediate Similarity	NPD5688	Approved
0.7229	Intermediate Similarity	NPD5689	Approved
0.7212	Intermediate Similarity	NPD230	Phase 1
0.7211	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6585	Discontinued
0.7193	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6232	Discontinued
0.7182	Intermediate Similarity	NPD6808	Phase 2
0.7179	Intermediate Similarity	NPD4580	Approved
0.7176	Intermediate Similarity	NPD7466	Approved
0.7175	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2801	Approved
0.7175	Intermediate Similarity	NPD7819	Suspended
0.7175	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5772	Approved
0.7175	Intermediate Similarity	NPD5773	Approved
0.7174	Intermediate Similarity	NPD7054	Approved
0.7158	Intermediate Similarity	NPD7473	Discontinued
0.7151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD7075	Discontinued
0.715	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2493	Approved
0.7143	Intermediate Similarity	NPD7930	Approved
0.7143	Intermediate Similarity	NPD2494	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD4482	Phase 3
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7135	Intermediate Similarity	NPD7472	Approved
0.7128	Intermediate Similarity	NPD6853	Approved
0.7128	Intermediate Similarity	NPD6851	Approved
0.7127	Intermediate Similarity	NPD6107	Approved
0.7126	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.7121	Intermediate Similarity	NPD8319	Approved
0.7119	Intermediate Similarity	NPD37	Approved
0.7112	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD919	Approved
0.7108	Intermediate Similarity	NPD4618	Approved
0.7108	Intermediate Similarity	NPD4622	Approved
0.7104	Intermediate Similarity	NPD4481	Phase 3
0.7104	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6166	Phase 2
0.7102	Intermediate Similarity	NPD4678	Approved
0.7102	Intermediate Similarity	NPD4675	Approved
0.7101	Intermediate Similarity	NPD7907	Approved
0.7097	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4966	Approved
0.7095	Intermediate Similarity	NPD4965	Approved
0.7095	Intermediate Similarity	NPD4967	Phase 2
0.7093	Intermediate Similarity	NPD7124	Phase 2
0.7079	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1465	Phase 2
0.7074	Intermediate Similarity	NPD2968	Approved
0.7074	Intermediate Similarity	NPD2971	Approved
0.7068	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2492	Phase 1
0.7062	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4361	Phase 2
0.7056	Intermediate Similarity	NPD3452	Approved
0.7056	Intermediate Similarity	NPD3450	Approved
0.7056	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6799	Approved
0.7052	Intermediate Similarity	NPD4357	Discontinued
0.705	Intermediate Similarity	NPD7583	Approved
0.7049	Intermediate Similarity	NPD3926	Phase 2
0.7041	Intermediate Similarity	NPD2796	Approved
0.7035	Intermediate Similarity	NPD4582	Approved
0.7035	Intermediate Similarity	NPD6190	Approved
0.7035	Intermediate Similarity	NPD4583	Approved
0.7031	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5718	Phase 2
0.7029	Intermediate Similarity	NPD1670	Discontinued
0.7022	Intermediate Similarity	NPD7577	Discontinued
0.7021	Intermediate Similarity	NPD7808	Phase 3
0.7017	Intermediate Similarity	NPD6234	Discontinued
0.7015	Intermediate Similarity	NPD7585	Approved
0.7012	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7447	Phase 1
0.701	Intermediate Similarity	NPD4360	Phase 2
0.701	Intermediate Similarity	NPD4363	Phase 3
0.7006	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6788	Approved
0.7	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7296	Approved
0.6989	Remote Similarity	NPD5313	Approved
0.6989	Remote Similarity	NPD3687	Approved
0.6989	Remote Similarity	NPD3686	Approved
0.6989	Remote Similarity	NPD8156	Discontinued
0.6989	Remote Similarity	NPD5312	Approved
0.6988	Remote Similarity	NPD3530	Approved
0.6988	Remote Similarity	NPD3532	Approved
0.6988	Remote Similarity	NPD3531	Approved
0.6985	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4002	Approved
0.6985	Remote Similarity	NPD4004	Approved
0.698	Remote Similarity	NPD8151	Discontinued
0.6971	Remote Similarity	NPD2186	Approved
0.6968	Remote Similarity	NPD7251	Discontinued
0.6966	Remote Similarity	NPD6677	Suspended
0.6961	Remote Similarity	NPD7827	Phase 1
0.6959	Remote Similarity	NPD2897	Discontinued
0.6954	Remote Similarity	NPD7213	Phase 3
0.6954	Remote Similarity	NPD7811	Phase 3
0.6954	Remote Similarity	NPD7212	Phase 2
0.6954	Remote Similarity	NPD7810	Phase 3
0.6949	Remote Similarity	NPD2651	Approved
0.6949	Remote Similarity	NPD2649	Approved
0.6949	Remote Similarity	NPD824	Approved
0.6944	Remote Similarity	NPD5402	Approved
0.6942	Remote Similarity	NPD7047	Phase 3
0.6941	Remote Similarity	NPD2239	Approved
0.6941	Remote Similarity	NPD2240	Approved
0.694	Remote Similarity	NPD1247	Approved
0.694	Remote Similarity	NPD7199	Phase 2
0.6938	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8099	Discontinued
0.6935	Remote Similarity	NPD7177	Discontinued
0.6935	Remote Similarity	NPD8252	Approved
0.6935	Remote Similarity	NPD8251	Approved
0.6935	Remote Similarity	NPD7228	Approved
0.693	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6280	Approved
0.6927	Remote Similarity	NPD6279	Approved
0.6927	Remote Similarity	NPD6801	Discontinued
0.6927	Remote Similarity	NPD7291	Discontinued
0.6927	Remote Similarity	NPD7885	Phase 2
0.6927	Remote Similarity	NPD7886	Phase 2
0.6927	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6862	Phase 2
0.6923	Remote Similarity	NPD2899	Discontinued

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