NPASS Compound

Structure

NPC476202 OpenBabel07101719142D 46 52 0 0 1 0 0 0 0 0999 V2000 7.2005 -6.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4115 -3.6232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9748 -4.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4540 -6.5095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1953 -0.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0996 -0.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1682 -5.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6173 -5.0403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2910 -5.9293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2103 -5.8253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5953 -5.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0643 -4.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7867 -2.3230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0652 -5.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3026 -2.8447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3854 -5.9158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0262 -5.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9289 -4.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9176 -6.6825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1970 -2.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8198 -2.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4658 -3.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0531 -5.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5384 -6.3502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1979 -3.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8932 -6.4036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4964 -2.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3323 -4.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3320 -3.2706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3331 -5.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0251 -3.9043 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4406 -2.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1566 -6.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3306 -2.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -6.8066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4650 -2.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2983 -1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1337 -2.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1996 -5.7079 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1.4087 -3.5485 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 3.1125 -1.4859 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 3.2134 -5.8589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3297 -1.2087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2557 -0.9479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5269 -6.7105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8313 -2.4024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 39 1 0 0 0 0 2 40 1 0 0 0 0 3 40 1 0 0 0 0 4 42 1 0 0 0 0 5 43 1 0 0 0 0 6 44 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 23 1 0 0 0 0 9 26 2 0 0 0 0 10 11 2 0 0 0 0 10 24 1 0 0 0 0 11 33 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 39 1 0 0 0 0 15 40 1 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 24 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 35 1 0 0 0 0 20 25 2 0 0 0 0 20 34 1 0 0 0 0 21 29 2 0 0 0 0 21 32 1 0 0 0 0 22 28 2 0 0 0 0 22 36 1 0 0 0 0 25 28 1 0 0 0 0 26 45 1 0 0 0 0 27 29 1 0 0 0 0 27 37 2 0 0 0 0 28 30 1 0 0 0 0 29 31 1 0 0 0 0 30 39 2 0 0 0 0 31 40 1 0 0 0 0 32 38 2 0 0 0 0 32 41 1 0 0 0 0 33 35 2 0 0 0 0 33 42 1 0 0 0 0 34 36 2 0 0 0 0 34 43 1 0 0 0 0 35 45 1 0 0 0 0 36 46 1 0 0 0 0 37 38 1 0 0 0 0 37 44 1 0 0 0 0 38 46 1 0 0 0 0 M CHG 3 39 1 40 1 41 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	621.3
Volume:	647.688
LogP:	5.379
LogD:	3.382
LogS:	-5.148
# Rotatable Bonds:	3
TPSA:	72.22
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	6.524
Fsp3:	0.342
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.785
MDCK Permeability:	4.018433901364915e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.944
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	43.28519058227539%
Volume Distribution (VD):	1.039
Pgp-substrate:	32.990394592285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.39
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.35
CYP3A4-substrate:	0.937

ADMET: Excretion

Clearance (CL):	4.101
Half-life (T1/2):	0.627

ADMET: Toxicity

hERG Blockers:	0.881
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.085
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.54

Download Data

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

Natural Product: NPC476202

Natural Product ID:	NPC476202
*Common Name:**	JIOATNACEFZLHY-ATQCJDTDSA-M
IUPAC Name:	n.a.
Synonyms:	(+)-Coccuorbiculatine A
Standard InCHIKey:	JIOATNACEFZLHY-ATQCJDTDSA-M
Standard InCHI:	InChI=1S/C38H41N2O6.2ClH/c1-39-14-12-25-20-34(43-5)36-22-28(25)30(39)17-24-10-11-33(42-4)35(19-24)45-26-9-7-8-23(16-26)18-31-29-21-32(41)38(46-36)37(44-6)27(29)13-15-40(31,2)3;;/h7-11,16,19-22,31H,12-15,17-18H2,1-6H3;2*1H/q+1;;/p-1/t31-;;/m0../s1
SMILES:	C[N+]1=C2CC3=CC(=C(C=C3)OC)OC4=CC=CC(=C4)CC5C6=CC(=C(C(=C6CC[N+]5(C)C)OC)OC7=C(C=C(C2=C7)CC1)OC)O.[Cl-].[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL553447
PubChem CID:	45266407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO23690	Cocculus orbiculatus	Species	Menispermaceae	Eukaryota	n.a.	Formosan	n.a.	PMID[16038548]
NPO23690	Cocculus orbiculatus	Species	Menispermaceae	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

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[568972]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[568972]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[568972]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30.0	ug.mL-1	PMID[568972]

☑ 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 NPC476202 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	471
0.1-0.2	2185
0.2-0.3	11674
0.3-0.4	6146
0.4-0.5	7601
0.5-0.6	11231
0.6-0.7	2771
0.7-0.8	479
0.8-0.85	45
0.85-0.9	66
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC195538
0.988	High Similarity	NPC249996
0.9532	High Similarity	NPC318805
0.9532	High Similarity	NPC41122
0.9422	High Similarity	NPC85381
0.9314	High Similarity	NPC234318
0.9222	High Similarity	NPC76682
0.9222	High Similarity	NPC115284
0.9222	High Similarity	NPC276890
0.9222	High Similarity	NPC317439
0.9222	High Similarity	NPC227060
0.9222	High Similarity	NPC10908
0.9222	High Similarity	NPC63646
0.9222	High Similarity	NPC317145
0.9222	High Similarity	NPC198498
0.9167	High Similarity	NPC41376
0.9167	High Similarity	NPC251580
0.9167	High Similarity	NPC129518
0.9167	High Similarity	NPC12424
0.9059	High Similarity	NPC293093
0.8953	High Similarity	NPC475479
0.8953	High Similarity	NPC243454
0.8902	High Similarity	NPC239584
0.8902	High Similarity	NPC286119
0.8851	High Similarity	NPC49075
0.8851	High Similarity	NPC54654
0.8851	High Similarity	NPC73492
0.8851	High Similarity	NPC15414
0.8851	High Similarity	NPC181796
0.8851	High Similarity	NPC258657
0.8851	High Similarity	NPC311973
0.8851	High Similarity	NPC30779
0.8851	High Similarity	NPC185639
0.8851	High Similarity	NPC222661
0.8851	High Similarity	NPC229373
0.8851	High Similarity	NPC7715
0.8851	High Similarity	NPC42663
0.8851	High Similarity	NPC299990
0.8851	High Similarity	NPC239824
0.8851	High Similarity	NPC8836
0.8851	High Similarity	NPC328155
0.8851	High Similarity	NPC217748
0.8851	High Similarity	NPC182052
0.8851	High Similarity	NPC104196
0.8851	High Similarity	NPC279228
0.8851	High Similarity	NPC290582
0.8851	High Similarity	NPC285931
0.8851	High Similarity	NPC290005
0.8851	High Similarity	NPC90998
0.8851	High Similarity	NPC271013
0.8851	High Similarity	NPC223690
0.8851	High Similarity	NPC251735
0.88	High Similarity	NPC302275
0.88	High Similarity	NPC254441
0.88	High Similarity	NPC167116
0.88	High Similarity	NPC274716
0.875	High Similarity	NPC16357
0.875	High Similarity	NPC302245
0.875	High Similarity	NPC95426
0.8701	High Similarity	NPC139783
0.8701	High Similarity	NPC116465
0.8701	High Similarity	NPC65312
0.8701	High Similarity	NPC212237
0.8683	High Similarity	NPC216816
0.8675	High Similarity	NPC247639
0.8675	High Similarity	NPC25084
0.8667	High Similarity	NPC471113
0.8652	High Similarity	NPC22115
0.8652	High Similarity	NPC275680
0.8603	High Similarity	NPC175890
0.8603	High Similarity	NPC48490
0.8603	High Similarity	NPC82457
0.8603	High Similarity	NPC274661
0.8603	High Similarity	NPC206900
0.8603	High Similarity	NPC11296
0.8603	High Similarity	NPC281581
0.8596	High Similarity	NPC14507
0.8596	High Similarity	NPC47077
0.8556	High Similarity	NPC473716
0.8556	High Similarity	NPC475597
0.8556	High Similarity	NPC191132
0.8556	High Similarity	NPC60295
0.8508	High Similarity	NPC24260
0.8508	High Similarity	NPC478093
0.8462	Intermediate Similarity	NPC473589
0.8462	Intermediate Similarity	NPC478092
0.8462	Intermediate Similarity	NPC30182
0.8462	Intermediate Similarity	NPC256124
0.8462	Intermediate Similarity	NPC478091
0.8434	Intermediate Similarity	NPC476568
0.8421	Intermediate Similarity	NPC475393
0.8343	Intermediate Similarity	NPC10871
0.8333	Intermediate Similarity	NPC66573
0.8333	Intermediate Similarity	NPC83198
0.8333	Intermediate Similarity	NPC204908
0.8324	Intermediate Similarity	NPC240841
0.8324	Intermediate Similarity	NPC317272
0.8324	Intermediate Similarity	NPC42549
0.8324	Intermediate Similarity	NPC256012
0.8324	Intermediate Similarity	NPC250846
0.8324	Intermediate Similarity	NPC268503
0.8306	Intermediate Similarity	NPC476565
0.8251	Intermediate Similarity	NPC223236
0.8251	Intermediate Similarity	NPC259350
0.8235	Intermediate Similarity	NPC475654
0.8218	Intermediate Similarity	NPC264850
0.8218	Intermediate Similarity	NPC13916
0.8192	Intermediate Similarity	NPC232386
0.8192	Intermediate Similarity	NPC152680
0.8192	Intermediate Similarity	NPC190783
0.8176	Intermediate Similarity	NPC123323
0.8161	Intermediate Similarity	NPC24465
0.8114	Intermediate Similarity	NPC68328
0.8105	Intermediate Similarity	NPC254581
0.8084	Intermediate Similarity	NPC210437
0.8084	Intermediate Similarity	NPC106295
0.8084	Intermediate Similarity	NPC16107
0.8084	Intermediate Similarity	NPC476144
0.8084	Intermediate Similarity	NPC51957
0.8081	Intermediate Similarity	NPC476572
0.807	Intermediate Similarity	NPC325871
0.807	Intermediate Similarity	NPC99659
0.8068	Intermediate Similarity	NPC204947
0.8049	Intermediate Similarity	NPC188163
0.8049	Intermediate Similarity	NPC474915
0.8049	Intermediate Similarity	NPC213206
0.8049	Intermediate Similarity	NPC328750
0.8047	Intermediate Similarity	NPC265473
0.8047	Intermediate Similarity	NPC276665
0.8036	Intermediate Similarity	NPC7467
0.8034	Intermediate Similarity	NPC475215
0.8034	Intermediate Similarity	NPC149090
0.8034	Intermediate Similarity	NPC108434
0.8034	Intermediate Similarity	NPC239775
0.8034	Intermediate Similarity	NPC19520
0.7988	Intermediate Similarity	NPC314682
0.7978	Intermediate Similarity	NPC118274
0.7978	Intermediate Similarity	NPC168753
0.7965	Intermediate Similarity	NPC244112
0.7965	Intermediate Similarity	NPC107602
0.7952	Intermediate Similarity	NPC128019
0.7952	Intermediate Similarity	NPC476567
0.7952	Intermediate Similarity	NPC136860
0.7943	Intermediate Similarity	NPC179250
0.7943	Intermediate Similarity	NPC50380
0.7933	Intermediate Similarity	NPC231371
0.7895	Intermediate Similarity	NPC81733
0.7895	Intermediate Similarity	NPC326316
0.7886	Intermediate Similarity	NPC230956
0.7886	Intermediate Similarity	NPC205255
0.7886	Intermediate Similarity	NPC235143
0.7886	Intermediate Similarity	NPC271388
0.7886	Intermediate Similarity	NPC119649
0.7864	Intermediate Similarity	NPC201508
0.7841	Intermediate Similarity	NPC79402
0.7841	Intermediate Similarity	NPC80759
0.7829	Intermediate Similarity	NPC221864
0.7829	Intermediate Similarity	NPC7393
0.7829	Intermediate Similarity	NPC329837
0.7816	Intermediate Similarity	NPC180756
0.7816	Intermediate Similarity	NPC323443
0.7814	Intermediate Similarity	NPC474507
0.7811	Intermediate Similarity	NPC473934
0.7809	Intermediate Similarity	NPC24264
0.7809	Intermediate Similarity	NPC476432
0.7791	Intermediate Similarity	NPC127402
0.7788	Intermediate Similarity	NPC255800
0.7788	Intermediate Similarity	NPC96584
0.7778	Intermediate Similarity	NPC92541
0.7778	Intermediate Similarity	NPC75958
0.7772	Intermediate Similarity	NPC474506
0.7772	Intermediate Similarity	NPC32413
0.7771	Intermediate Similarity	NPC206736
0.7771	Intermediate Similarity	NPC195766
0.7765	Intermediate Similarity	NPC12053
0.7765	Intermediate Similarity	NPC476151
0.7765	Intermediate Similarity	NPC247389
0.7765	Intermediate Similarity	NPC117188
0.7765	Intermediate Similarity	NPC205421
0.7765	Intermediate Similarity	NPC81218
0.7765	Intermediate Similarity	NPC145832
0.7765	Intermediate Similarity	NPC158376
0.7765	Intermediate Similarity	NPC474931
0.7765	Intermediate Similarity	NPC306555
0.776	Intermediate Similarity	NPC23219
0.7759	Intermediate Similarity	NPC172765
0.7759	Intermediate Similarity	NPC80129
0.7759	Intermediate Similarity	NPC110416
0.7759	Intermediate Similarity	NPC207757
0.7759	Intermediate Similarity	NPC276588
0.7759	Intermediate Similarity	NPC54379
0.7759	Intermediate Similarity	NPC187022
0.7759	Intermediate Similarity	NPC41178
0.7759	Intermediate Similarity	NPC469817
0.7759	Intermediate Similarity	NPC2413
0.7759	Intermediate Similarity	NPC127674
0.7759	Intermediate Similarity	NPC39701
0.7759	Intermediate Similarity	NPC216459
0.7759	Intermediate Similarity	NPC189266
0.7759	Intermediate Similarity	NPC278799

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 NPC476202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	771
0.2-0.3	1071
0.3-0.4	1945
0.4-0.5	2813
0.5-0.6	1710
0.6-0.7	531
0.7-0.8	70
0.8-0.85	3
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9222	High Similarity	NPD8251	Approved
0.9222	High Similarity	NPD8099	Discontinued
0.9222	High Similarity	NPD8252	Approved
0.9167	High Similarity	NPD8156	Discontinued
0.8851	High Similarity	NPD8053	Approved
0.8851	High Similarity	NPD8054	Approved
0.828	Intermediate Similarity	NPD8095	Phase 1
0.8246	Intermediate Similarity	NPD6788	Approved
0.8084	Intermediate Similarity	NPD4584	Approved
0.8049	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4005	Discontinued
0.7952	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD7291	Discontinued
0.7784	Intermediate Similarity	NPD4055	Discovery
0.7759	Intermediate Similarity	NPD7298	Approved
0.7746	Intermediate Similarity	NPD4678	Approved
0.7746	Intermediate Similarity	NPD4675	Approved
0.7737	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6071	Discontinued
0.7588	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6030	Approved
0.7572	Intermediate Similarity	NPD6031	Approved
0.7558	Intermediate Similarity	NPD1424	Approved
0.7545	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7124	Phase 2
0.7514	Intermediate Similarity	NPD3051	Approved
0.7513	Intermediate Similarity	NPD7906	Approved
0.75	Intermediate Similarity	NPD4772	Phase 2
0.75	Intermediate Similarity	NPD4773	Phase 2
0.75	Intermediate Similarity	NPD5677	Discontinued
0.7486	Intermediate Similarity	NPD7833	Phase 2
0.7486	Intermediate Similarity	NPD7831	Phase 2
0.7486	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4017	Approved
0.7486	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7802	Discontinued
0.7457	Intermediate Similarity	NPD4123	Phase 3
0.7457	Intermediate Similarity	NPD7447	Phase 1
0.7432	Intermediate Similarity	NPD4481	Phase 3
0.7423	Intermediate Similarity	NPD7034	Discontinued
0.7377	Intermediate Similarity	NPD2970	Approved
0.7377	Intermediate Similarity	NPD2969	Approved
0.7374	Intermediate Similarity	NPD2560	Approved
0.7374	Intermediate Similarity	NPD2563	Approved
0.734	Intermediate Similarity	NPD7549	Discontinued
0.734	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5772	Approved
0.7318	Intermediate Similarity	NPD5773	Approved
0.7302	Intermediate Similarity	NPD7310	Approved
0.7302	Intermediate Similarity	NPD7312	Approved
0.7302	Intermediate Similarity	NPD7311	Approved
0.7302	Intermediate Similarity	NPD7313	Approved
0.7299	Intermediate Similarity	NPD7213	Phase 3
0.7299	Intermediate Similarity	NPD7212	Phase 2
0.7289	Intermediate Similarity	NPD5718	Phase 2
0.7288	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3692	Discontinued
0.7273	Intermediate Similarity	NPD3641	Approved
0.7273	Intermediate Similarity	NPD3639	Approved
0.7273	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2122	Discontinued
0.7273	Intermediate Similarity	NPD3640	Phase 3
0.7263	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7309	Approved
0.7246	Intermediate Similarity	NPD4474	Approved
0.7246	Intermediate Similarity	NPD4475	Approved
0.7243	Intermediate Similarity	NPD27	Approved
0.7243	Intermediate Similarity	NPD2489	Approved
0.7225	Intermediate Similarity	NPD6748	Discontinued
0.7225	Intermediate Similarity	NPD7466	Approved
0.7211	Intermediate Similarity	NPD4577	Approved
0.7211	Intermediate Similarity	NPD4578	Approved
0.7211	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5090	Approved
0.7207	Intermediate Similarity	NPD5089	Approved
0.7204	Intermediate Similarity	NPD3489	Phase 3
0.7191	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4663	Approved
0.7181	Intermediate Similarity	NPD3920	Phase 2
0.7176	Intermediate Similarity	NPD2200	Suspended
0.7174	Intermediate Similarity	NPD6107	Approved
0.7166	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5006	Approved
0.715	Intermediate Similarity	NPD5005	Approved
0.7128	Intermediate Similarity	NPD3921	Approved
0.7128	Intermediate Similarity	NPD3923	Approved
0.7128	Intermediate Similarity	NPD3924	Approved
0.7128	Intermediate Similarity	NPD3922	Approved
0.7126	Intermediate Similarity	NPD6331	Phase 2
0.712	Intermediate Similarity	NPD2971	Approved
0.712	Intermediate Similarity	NPD2968	Approved
0.7111	Intermediate Similarity	NPD6072	Discontinued
0.7086	Intermediate Similarity	NPD5241	Discontinued
0.7076	Intermediate Similarity	NPD6111	Discontinued
0.7076	Intermediate Similarity	NPD6895	Approved
0.7076	Intermediate Similarity	NPD6896	Approved
0.7071	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4010	Discontinued
0.7041	Intermediate Similarity	NPD7477	Discontinued
0.7035	Intermediate Similarity	NPD4420	Approved
0.7033	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4585	Approved
0.7024	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7153	Discontinued
0.7011	Intermediate Similarity	NPD5604	Discontinued
0.7006	Intermediate Similarity	NPD7598	Phase 2
0.7006	Intermediate Similarity	NPD3124	Discontinued
0.6989	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2975	Approved
0.6985	Remote Similarity	NPD2974	Approved
0.6985	Remote Similarity	NPD2973	Approved
0.6982	Remote Similarity	NPD5109	Approved
0.6982	Remote Similarity	NPD5110	Phase 2
0.6982	Remote Similarity	NPD5111	Phase 2
0.6978	Remote Similarity	NPD5720	Discontinued
0.6968	Remote Similarity	NPD2898	Approved
0.6947	Remote Similarity	NPD5312	Approved
0.6947	Remote Similarity	NPD5313	Approved
0.6927	Remote Similarity	NPD52	Approved
0.6927	Remote Similarity	NPD7526	Approved
0.6927	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3386	Phase 2
0.6927	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7438	Suspended
0.6919	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8070	Approved
0.6914	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2420	Approved
0.691	Remote Similarity	NPD2421	Approved
0.6907	Remote Similarity	NPD6851	Approved
0.6907	Remote Similarity	NPD6853	Approved
0.6905	Remote Similarity	NPD8149	Discontinued
0.6904	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5976	Discontinued
0.6888	Remote Similarity	NPD6841	Approved
0.6888	Remote Similarity	NPD6843	Phase 3
0.6888	Remote Similarity	NPD6842	Approved
0.6882	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4580	Approved
0.6875	Remote Similarity	NPD5177	Phase 3
0.6875	Remote Similarity	NPD6297	Approved
0.6865	Remote Similarity	NPD7773	Phase 2
0.6862	Remote Similarity	NPD4166	Phase 2
0.6857	Remote Similarity	NPD3656	Approved
0.6847	Remote Similarity	NPD3452	Approved
0.6847	Remote Similarity	NPD2494	Approved
0.6847	Remote Similarity	NPD2493	Approved
0.6847	Remote Similarity	NPD3450	Approved
0.6842	Remote Similarity	NPD7827	Phase 1
0.6842	Remote Similarity	NPD3815	Phase 1
0.6842	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2674	Phase 3
0.6842	Remote Similarity	NPD3816	Phase 1
0.6839	Remote Similarity	NPD6380	Phase 1
0.6833	Remote Similarity	NPD1349	Approved
0.6833	Remote Similarity	NPD1351	Approved
0.6833	Remote Similarity	NPD1350	Approved
0.6831	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7110	Phase 1
0.6826	Remote Similarity	NPD2922	Phase 1
0.6826	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4083	Discontinued
0.6825	Remote Similarity	NPD5242	Approved
0.6818	Remote Similarity	NPD2490	Approved
0.6818	Remote Similarity	NPD2488	Approved
0.6816	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3110	Approved
0.6802	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3109	Approved
0.68	Remote Similarity	NPD2161	Phase 2
0.6798	Remote Similarity	NPD2219	Phase 1
0.6798	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6612	Phase 2
0.6793	Remote Similarity	NPD5722	Discontinued
0.6791	Remote Similarity	NPD6997	Phase 2
0.678	Remote Similarity	NPD6364	Approved
0.678	Remote Similarity	NPD44	Approved
0.6778	Remote Similarity	NPD7019	Approved
0.6778	Remote Similarity	NPD7020	Approved
0.6772	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2843	Phase 2
0.6768	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2845	Phase 2
0.6763	Remote Similarity	NPD7263	Phase 2
0.6762	Remote Similarity	NPD7225	Discontinued
0.676	Remote Similarity	NPD3845	Phase 1
0.6758	Remote Similarity	NPD2883	Discontinued
0.6751	Remote Similarity	NPD6257	Clinical (unspecified phase)

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