NPASS Compound

Structure

NPC206592 OpenBabel07101719522D 42 51 0 0 1 0 0 0 0 0999 V2000 -7.2221 0.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9128 -3.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0024 -0.3774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2615 0.6104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5975 -2.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3889 0.6496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6956 1.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 1.5588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 0.5972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9346 -0.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6032 2.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5480 1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0404 -0.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4867 1.7391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1040 -0.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6399 1.8326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6032 -0.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6979 2.8349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0797 -2.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0776 1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3377 -1.3237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8720 1.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8185 1.4639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6531 -2.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6032 0.1164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2631 2.0569 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0241 -2.9594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9377 -1.8068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7871 -0.5512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4360 1.5588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7416 2.7344 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2357 -1.8699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4360 0.5972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9157 1.0780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0173 -1.1557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1218 -1.4964 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3505 1.8559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 0.3000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5984 2.0071 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.3934 -1.1426 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 22 2 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 25 1 0 0 0 0 10 29 2 0 0 0 0 11 30 2 0 0 0 0 12 31 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 42 1 0 0 0 0 16 41 1 0 0 0 0 17 25 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 23 1 0 0 0 0 20 41 1 0 0 0 0 21 24 1 0 0 0 0 21 42 1 0 0 0 0 22 26 1 0 0 0 0 22 35 1 0 0 0 0 23 4 1 1 0 0 0 23 26 1 0 0 0 0 24 5 1 6 0 0 0 24 27 1 0 0 0 0 25 34 2 0 0 0 0 26 18 1 1 0 0 0 27 19 1 1 0 0 0 27 28 1 0 0 0 0 28 17 1 6 0 0 0 28 36 1 0 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 30 34 1 0 0 0 0 30 38 1 0 0 0 0 31 39 1 0 0 0 0 32 38 1 1 0 0 0 32 41 1 0 0 0 0 33 37 1 6 0 0 0 33 42 1 0 0 0 0 34 40 1 0 0 0 0 35 38 1 1 0 0 0 35 40 1 0 0 0 0 36 37 1 0 0 0 0 36 39 2 0 0 0 0 37 13 1 1 0 0 0 38 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.37
Volume:	603.135
LogP:	6.228
LogD:	5.148
LogS:	-5.643
# Rotatable Bonds:	4
TPSA:	30.87
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	10
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	7.256
Fsp3:	0.605
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.268
MDCK Permeability:	1.8952565369545482e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	89.36217498779297%
Volume Distribution (VD):	3.859
Pgp-substrate:	6.498498439788818%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.979
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.988
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	7.781
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.988
Human Hepatotoxicity (H-HT):	0.42
Drug-inuced Liver Injury (DILI):	0.687
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.909
Carcinogencity:	0.503
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC206592

Natural Product ID:	NPC206592
*Common Name:**	Leucoridine D
IUPAC Name:	n.a.
Synonyms:	Leucoridine D
Standard InCHIKey:	ZOKATMGICWFWCT-SYZQWITBSA-N
Standard InCHI:	InChI=1S/C38H46N4/c1-4-23-20-41-16-14-38-30-11-8-9-25(34(30)40-35(38)22(3)26(23)18-32(38)41)17-28-27-19-33-37(13-15-42(33)21-24(27)5-2)29-10-6-7-12-31(29)39-36(28)37/h6-12,23-24,26-28,32-33,35,40H,3-5,13-21H2,1-2H3/t23-,24-,26-,27+,28+,32+,33+,35+,37-,38-/m1/s1
SMILES:	CC[C@@H]1CN2CC[C@@]34c5cccc(C[C@H]6[C@H]7C[C@H]8[C@@]9(CCN8C[C@H]7CC)c7ccccc7N=C69)c5N[C@H]4C(=C)[C@H]1C[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1164917
PubChem CID:	46898053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos alkaloids

*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
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20035556]
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20515042]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	12.53	ug.mL-1	PMID[494367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13.29	ug.mL-1	PMID[494367]

☑ 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 NPC206592 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	862
0.1-0.2	4508
0.2-0.3	20867
0.3-0.4	10248
0.4-0.5	4253
0.5-0.6	1626
0.6-0.7	275
0.7-0.8	52
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9301	High Similarity	NPC469735
0.8973	High Similarity	NPC469740
0.7888	Intermediate Similarity	NPC469741
0.7831	Intermediate Similarity	NPC475097
0.7791	Intermediate Similarity	NPC475420
0.773	Intermediate Similarity	NPC264580
0.7697	Intermediate Similarity	NPC475248
0.7697	Intermediate Similarity	NPC63047
0.7569	Intermediate Similarity	NPC475915
0.756	Intermediate Similarity	NPC473880
0.756	Intermediate Similarity	NPC473743
0.75	Intermediate Similarity	NPC145754
0.7368	Intermediate Similarity	NPC320147
0.7358	Intermediate Similarity	NPC264589
0.7341	Intermediate Similarity	NPC286994
0.7333	Intermediate Similarity	NPC221786
0.7333	Intermediate Similarity	NPC474880
0.7333	Intermediate Similarity	NPC475990
0.7284	Intermediate Similarity	NPC33421
0.7267	Intermediate Similarity	NPC109787
0.7267	Intermediate Similarity	NPC478079
0.72	Intermediate Similarity	NPC252794
0.7197	Intermediate Similarity	NPC243162
0.7186	Intermediate Similarity	NPC229173
0.7175	Intermediate Similarity	NPC476095
0.7171	Intermediate Similarity	NPC9856
0.7151	Intermediate Similarity	NPC242269
0.7135	Intermediate Similarity	NPC474897
0.7095	Intermediate Similarity	NPC285841
0.7093	Intermediate Similarity	NPC201634
0.7089	Intermediate Similarity	NPC130251
0.7081	Intermediate Similarity	NPC116519
0.7066	Intermediate Similarity	NPC222029
0.7066	Intermediate Similarity	NPC167635
0.7055	Intermediate Similarity	NPC192209
0.7055	Intermediate Similarity	NPC313449
0.7055	Intermediate Similarity	NPC21605
0.7053	Intermediate Similarity	NPC87755
0.7033	Intermediate Similarity	NPC471386
0.7022	Intermediate Similarity	NPC472294
0.6979	Remote Similarity	NPC126066
0.6979	Remote Similarity	NPC475422
0.697	Remote Similarity	NPC475763
0.6964	Remote Similarity	NPC193740
0.6941	Remote Similarity	NPC99632
0.6941	Remote Similarity	NPC282339
0.6923	Remote Similarity	NPC56765
0.6923	Remote Similarity	NPC276085
0.6897	Remote Similarity	NPC187036
0.6832	Remote Similarity	NPC186284
0.6832	Remote Similarity	NPC22082
0.6832	Remote Similarity	NPC301760
0.6824	Remote Similarity	NPC41257
0.681	Remote Similarity	NPC20144
0.6791	Remote Similarity	NPC162440
0.6789	Remote Similarity	NPC52801
0.6781	Remote Similarity	NPC296163
0.6757	Remote Similarity	NPC313673
0.6748	Remote Similarity	NPC473868
0.6748	Remote Similarity	NPC469537
0.6748	Remote Similarity	NPC63157
0.6747	Remote Similarity	NPC477134
0.6728	Remote Similarity	NPC88097
0.6725	Remote Similarity	NPC206819
0.6725	Remote Similarity	NPC318065
0.6714	Remote Similarity	NPC291610
0.6706	Remote Similarity	NPC477157
0.6706	Remote Similarity	NPC477156
0.6703	Remote Similarity	NPC307396
0.6701	Remote Similarity	NPC475602
0.6687	Remote Similarity	NPC59084
0.6687	Remote Similarity	NPC2949
0.6686	Remote Similarity	NPC225319
0.6685	Remote Similarity	NPC280852
0.6667	Remote Similarity	NPC104345
0.6667	Remote Similarity	NPC286427
0.6667	Remote Similarity	NPC66936
0.6667	Remote Similarity	NPC216643
0.6667	Remote Similarity	NPC302790
0.6613	Remote Similarity	NPC276430
0.6609	Remote Similarity	NPC90723
0.6606	Remote Similarity	NPC311330
0.6588	Remote Similarity	NPC200743
0.6584	Remote Similarity	NPC471123
0.6578	Remote Similarity	NPC316359
0.6578	Remote Similarity	NPC315617
0.6577	Remote Similarity	NPC288232
0.6573	Remote Similarity	NPC474695
0.655	Remote Similarity	NPC473297
0.655	Remote Similarity	NPC476219
0.6543	Remote Similarity	NPC325252
0.6532	Remote Similarity	NPC6436
0.6497	Remote Similarity	NPC476950
0.6494	Remote Similarity	NPC215584
0.6494	Remote Similarity	NPC248117
0.6494	Remote Similarity	NPC44773
0.6489	Remote Similarity	NPC314058
0.6489	Remote Similarity	NPC316018
0.6481	Remote Similarity	NPC198988
0.648	Remote Similarity	NPC477065
0.6479	Remote Similarity	NPC239854
0.6471	Remote Similarity	NPC53947
0.6471	Remote Similarity	NPC154602
0.6471	Remote Similarity	NPC243756
0.6462	Remote Similarity	NPC329833
0.6439	Remote Similarity	NPC162748
0.6437	Remote Similarity	NPC193410
0.6437	Remote Similarity	NPC36495
0.6424	Remote Similarity	NPC104483
0.6424	Remote Similarity	NPC312092
0.642	Remote Similarity	NPC472587
0.6416	Remote Similarity	NPC51054
0.6413	Remote Similarity	NPC19679
0.6407	Remote Similarity	NPC472103
0.64	Remote Similarity	NPC477158
0.6398	Remote Similarity	NPC475450
0.6389	Remote Similarity	NPC214626
0.6389	Remote Similarity	NPC139085
0.6389	Remote Similarity	NPC251212
0.6386	Remote Similarity	NPC477155
0.6379	Remote Similarity	NPC61013
0.6374	Remote Similarity	NPC40070
0.637	Remote Similarity	NPC79618
0.6369	Remote Similarity	NPC194411
0.6358	Remote Similarity	NPC473930
0.6354	Remote Similarity	NPC232130
0.6347	Remote Similarity	NPC469766
0.6337	Remote Similarity	NPC470233
0.6335	Remote Similarity	NPC475428
0.6335	Remote Similarity	NPC53044
0.6331	Remote Similarity	NPC204141
0.6331	Remote Similarity	NPC472100
0.6328	Remote Similarity	NPC271797
0.6328	Remote Similarity	NPC21174
0.6324	Remote Similarity	NPC256288
0.6321	Remote Similarity	NPC265576
0.6321	Remote Similarity	NPC34837
0.631	Remote Similarity	NPC136002
0.6307	Remote Similarity	NPC68650
0.6307	Remote Similarity	NPC81229
0.6307	Remote Similarity	NPC255229
0.6305	Remote Similarity	NPC472027
0.6305	Remote Similarity	NPC183407
0.6303	Remote Similarity	NPC469560
0.6303	Remote Similarity	NPC251722
0.6303	Remote Similarity	NPC314102
0.6298	Remote Similarity	NPC161861
0.6296	Remote Similarity	NPC179365
0.6294	Remote Similarity	NPC474582
0.6294	Remote Similarity	NPC288838
0.629	Remote Similarity	NPC2933
0.6287	Remote Similarity	NPC469761
0.6287	Remote Similarity	NPC469779
0.6287	Remote Similarity	NPC469783
0.6287	Remote Similarity	NPC115611
0.6287	Remote Similarity	NPC469780
0.6287	Remote Similarity	NPC473757
0.6287	Remote Similarity	NPC469768
0.6287	Remote Similarity	NPC469767
0.6287	Remote Similarity	NPC469784
0.6277	Remote Similarity	NPC229484
0.6273	Remote Similarity	NPC473587
0.6271	Remote Similarity	NPC194881
0.6266	Remote Similarity	NPC122718
0.6264	Remote Similarity	NPC37423
0.6264	Remote Similarity	NPC38736
0.6264	Remote Similarity	NPC275305
0.6264	Remote Similarity	NPC476297
0.6264	Remote Similarity	NPC189812
0.6264	Remote Similarity	NPC329688
0.6259	Remote Similarity	NPC434
0.6257	Remote Similarity	NPC259626
0.625	Remote Similarity	NPC215795
0.625	Remote Similarity	NPC176199
0.6243	Remote Similarity	NPC285381
0.6243	Remote Similarity	NPC292675
0.6243	Remote Similarity	NPC126492
0.6243	Remote Similarity	NPC117032
0.6243	Remote Similarity	NPC122106
0.6242	Remote Similarity	NPC218268
0.6236	Remote Similarity	NPC317105
0.6235	Remote Similarity	NPC22079
0.6235	Remote Similarity	NPC469525
0.6231	Remote Similarity	NPC473362
0.6231	Remote Similarity	NPC166492
0.6229	Remote Similarity	NPC184476
0.6228	Remote Similarity	NPC73767
0.6228	Remote Similarity	NPC110126
0.6223	Remote Similarity	NPC473615
0.6222	Remote Similarity	NPC223595
0.6222	Remote Similarity	NPC167724
0.6222	Remote Similarity	NPC224970
0.6221	Remote Similarity	NPC318086
0.6221	Remote Similarity	NPC187951
0.6216	Remote Similarity	NPC314919
0.6216	Remote Similarity	NPC164802
0.6211	Remote Similarity	NPC128582
0.6211	Remote Similarity	NPC473762
0.6209	Remote Similarity	NPC472123
0.6201	Remote Similarity	NPC195507

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 NPC206592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	571
0.2-0.3	1300
0.3-0.4	2188
0.4-0.5	3251
0.5-0.6	1293
0.6-0.7	158
0.7-0.8	4
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
0.7785	Intermediate Similarity	NPD8401	Approved
0.7785	Intermediate Similarity	NPD8402	Approved
0.7785	Intermediate Similarity	NPD8400	Approved
0.7391	Intermediate Similarity	NPD8355	Approved
0.7391	Intermediate Similarity	NPD8353	Approved
0.7308	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD8354	Approved
0.7143	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2143	Discontinued
0.7114	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7633	Discontinued
0.7092	Intermediate Similarity	NPD4116	Approved
0.7055	Intermediate Similarity	NPD7480	Approved
0.7055	Intermediate Similarity	NPD7481	Approved
0.7	Intermediate Similarity	NPD3323	Discontinued
0.6994	Remote Similarity	NPD1683	Approved
0.6993	Remote Similarity	NPD2039	Approved
0.6993	Remote Similarity	NPD2038	Approved
0.6974	Remote Similarity	NPD6900	Discontinued
0.6959	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8630	Approved
0.6849	Remote Similarity	NPD5629	Discontinued
0.6782	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2913	Approved
0.6781	Remote Similarity	NPD2914	Approved
0.6768	Remote Similarity	NPD5254	Discontinued
0.6759	Remote Similarity	NPD3001	Approved
0.6759	Remote Similarity	NPD2999	Approved
0.6731	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3385	Approved
0.6713	Remote Similarity	NPD6299	Approved
0.6713	Remote Similarity	NPD6300	Approved
0.6689	Remote Similarity	NPD1720	Phase 2
0.6689	Remote Similarity	NPD1723	Phase 2
0.6688	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2172	Phase 1
0.6648	Remote Similarity	NPD5436	Phase 1
0.6647	Remote Similarity	NPD4547	Phase 3
0.6644	Remote Similarity	NPD2464	Approved
0.6644	Remote Similarity	NPD2463	Approved
0.6644	Remote Similarity	NPD2467	Approved
0.663	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8240	Discontinued
0.661	Remote Similarity	NPD3609	Approved
0.661	Remote Similarity	NPD3610	Approved
0.6597	Remote Similarity	NPD4114	Approved
0.6597	Remote Similarity	NPD5253	Approved
0.6597	Remote Similarity	NPD4115	Approved
0.6573	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7200	Approved
0.6558	Remote Similarity	NPD7461	Approved
0.6556	Remote Similarity	NPD4181	Approved
0.6552	Remote Similarity	NPD5315	Discontinued
0.6543	Remote Similarity	NPD4411	Phase 1
0.6543	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6358	Phase 2
0.6538	Remote Similarity	NPD1950	Approved
0.6538	Remote Similarity	NPD2840	Approved
0.6538	Remote Similarity	NPD1949	Approved
0.6528	Remote Similarity	NPD3546	Approved
0.6528	Remote Similarity	NPD3545	Approved
0.6519	Remote Similarity	NPD3424	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2940	Approved
0.6516	Remote Similarity	NPD2938	Approved
0.651	Remote Similarity	NPD5631	Phase 3
0.6506	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8125	Discontinued
0.6479	Remote Similarity	NPD4734	Approved
0.6479	Remote Similarity	NPD4735	Approved
0.6474	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD8128	Discontinued
0.6453	Remote Similarity	NPD6285	Phase 2
0.6446	Remote Similarity	NPD5526	Phase 2
0.6446	Remote Similarity	NPD6301	Phase 2
0.6446	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1953	Discontinued
0.6416	Remote Similarity	NPD7091	Discontinued
0.6416	Remote Similarity	NPD2150	Discontinued
0.6412	Remote Similarity	NPD3100	Discontinued
0.6409	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5021	Discontinued
0.6395	Remote Similarity	NPD2837	Discontinued
0.6393	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3654	Approved
0.6374	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5931	Phase 3
0.6369	Remote Similarity	NPD5933	Phase 3
0.6369	Remote Similarity	NPD5932	Phase 3
0.6358	Remote Similarity	NPD2622	Approved
0.6352	Remote Similarity	NPD7582	Discontinued
0.6347	Remote Similarity	NPD1722	Approved
0.6341	Remote Similarity	NPD1255	Approved
0.6341	Remote Similarity	NPD1256	Approved
0.6341	Remote Similarity	NPD1254	Approved
0.6341	Remote Similarity	NPD1253	Approved
0.6333	Remote Similarity	NPD5180	Approved
0.6333	Remote Similarity	NPD5181	Approved
0.6333	Remote Similarity	NPD5179	Approved
0.6322	Remote Similarity	NPD2580	Discontinued
0.6319	Remote Similarity	NPD4075	Phase 2
0.6312	Remote Similarity	NPD8263	Discontinued
0.631	Remote Similarity	NPD7099	Approved
0.6304	Remote Similarity	NPD5473	Discontinued
0.6303	Remote Similarity	NPD6554	Approved
0.6303	Remote Similarity	NPD45	Approved
0.6301	Remote Similarity	NPD990	Approved
0.6301	Remote Similarity	NPD993	Approved
0.6291	Remote Similarity	NPD1813	Discontinued
0.629	Remote Similarity	NPD7564	Discontinued
0.6286	Remote Similarity	NPD8060	Phase 1
0.6282	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4880	Discontinued
0.6279	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD5531	Discontinued
0.6277	Remote Similarity	NPD8431	Approved
0.6277	Remote Similarity	NPD7394	Phase 2
0.6273	Remote Similarity	NPD3841	Phase 3
0.6273	Remote Similarity	NPD4867	Approved
0.6273	Remote Similarity	NPD4866	Approved
0.6273	Remote Similarity	NPD5782	Phase 3
0.6273	Remote Similarity	NPD6489	Phase 3
0.6272	Remote Similarity	NPD5060	Phase 1
0.6264	Remote Similarity	NPD4128	Approved
0.6264	Remote Similarity	NPD3799	Suspended
0.6259	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2340	Discontinued
0.6258	Remote Similarity	NPD6892	Discontinued
0.6243	Remote Similarity	NPD6828	Phase 2
0.6243	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3248	Phase 1
0.6242	Remote Similarity	NPD6342	Discontinued
0.6238	Remote Similarity	NPD7454	Approved
0.6238	Remote Similarity	NPD7455	Approved
0.6237	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3475	Approved
0.6235	Remote Similarity	NPD3476	Approved
0.6235	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD6574	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD786	Approved
0.6226	Remote Similarity	NPD5838	Phase 2
0.6225	Remote Similarity	NPD3148	Approved
0.6225	Remote Similarity	NPD3150	Approved
0.6225	Remote Similarity	NPD2658	Approved
0.6225	Remote Similarity	NPD3147	Approved
0.6225	Remote Similarity	NPD3149	Approved
0.6225	Remote Similarity	NPD2659	Approved
0.6224	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD2640	Approved
0.6222	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD2641	Approved
0.6221	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3944	Approved
0.622	Remote Similarity	NPD3942	Approved
0.6216	Remote Similarity	NPD477	Phase 1
0.6216	Remote Similarity	NPD7456	Phase 2
0.6211	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD6070	Approved
0.6209	Remote Similarity	NPD6069	Approved
0.6207	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2790	Discontinued
0.6205	Remote Similarity	NPD7308	Discontinued
0.6196	Remote Similarity	NPD3506	Approved
0.6196	Remote Similarity	NPD7111	Discontinued
0.6196	Remote Similarity	NPD3505	Approved
0.6196	Remote Similarity	NPD1251	Discontinued
0.6194	Remote Similarity	NPD2210	Approved
0.6194	Remote Similarity	NPD2212	Approved
0.619	Remote Similarity	NPD3961	Discontinued
0.6186	Remote Similarity	NPD6664	Approved
0.6185	Remote Similarity	NPD4463	Approved
0.6185	Remote Similarity	NPD4462	Approved
0.618	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7824	Approved
0.6174	Remote Similarity	NPD1107	Approved
0.6174	Remote Similarity	NPD1108	Approved
0.6173	Remote Similarity	NPD947	Approved
0.6171	Remote Similarity	NPD7072	Phase 2
0.6167	Remote Similarity	NPD2639	Approved
0.6167	Remote Similarity	NPD2642	Approved
0.6166	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4079	Approved
0.6162	Remote Similarity	NPD4076	Approved
0.6159	Remote Similarity	NPD1764	Approved
0.6159	Remote Similarity	NPD1762	Approved
0.6149	Remote Similarity	NPD3011	Approved
0.6149	Remote Similarity	NPD3012	Approved
0.6149	Remote Similarity	NPD2119	Approved
0.6149	Remote Similarity	NPD3008	Approved
0.6149	Remote Similarity	NPD2118	Approved
0.6145	Remote Similarity	NPD5318	Discontinued
0.614	Remote Similarity	NPD3630	Approved
0.614	Remote Similarity	NPD3629	Approved
0.6139	Remote Similarity	NPD5787	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