NPASS Compound

Structure

CID128429 OpenBabel06191715482D 28 29 0 0 1 0 0 0 0 0999 V2000 -0.7254 -4.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3077 -5.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7624 -1.7722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7843 -1.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0050 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -1.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7199 -4.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0933 -2.5153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9456 -1.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1266 -3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -1.3563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4023 -3.4664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2074 -0.5473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -3.3698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 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 -1.5388 -2.6654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1151 -2.3074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 11 1 0 0 0 0 4 13 2 0 0 0 0 5 14 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 10 16 1 0 0 0 0 10 21 1 0 0 0 0 11 19 1 0 0 0 0 12 3 1 6 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 14 28 1 0 0 0 0 15 9 1 1 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 1 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 13 1 6 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 6 1 6 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.18
Volume:	400.372
LogP:	2.531
LogD:	1.941
LogS:	-2.883
# Rotatable Bonds:	5
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.958
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	4.8733978474047035e-05
Pgp-inhibitor:	0.073
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.274
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.513
Plasma Protein Binding (PPB):	64.5473403930664%
Volume Distribution (VD):	0.727
Pgp-substrate:	36.46599197387695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.566
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.674
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	7.762
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.365
Skin Sensitization:	0.933
Carcinogencity:	0.473
Eye Corrosion:	0.159
Eye Irritation:	0.3
Respiratory Toxicity:	0.257

Download Data

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

Natural Product: NPC128429

Natural Product ID:	NPC128429
*Common Name:**	Lychnostatin 2
IUPAC Name:	[(3aS,4S,6R,10S,11aR)-6-acetyloxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:	Lychnostatin 2
Standard InCHIKey:	HBRKQMNFEIZZOU-AGKHZPTMSA-N
Standard InCHI:	InChI=1S/C21H28O7/c1-11(2)19(24)27-16-10-21(6,28-14(5)22)17(23)8-7-12(3)9-15-18(16)13(4)20(25)26-15/h12,15-16,18H,1,4,7-10H2,2-3,5-6H3/t12-,15+,16-,18-,21+/m0/s1
SMILES:	C[C@H]1CCC(=O)[C@](C)(OC(=O)C)C[C@@H]([C@@H]2[C@@H](C1)OC(=O)C2=C)OC(=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465064
PubChem CID:	196827
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO30091	Lychnophora antillana	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[2380713]
NPO30091	Lychnophora antillana	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[2380713]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.19	ug ml-1	PMID[545487]

☑ 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 NPC128429 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	242
0.1-0.2	2094
0.2-0.3	7053
0.3-0.4	15301
0.4-0.5	9794
0.5-0.6	6031
0.6-0.7	1665
0.7-0.8	477
0.8-0.85	27
0.85-0.9	11
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8851	High Similarity	NPC190294
0.8675	High Similarity	NPC138647
0.8675	High Similarity	NPC470238
0.8652	High Similarity	NPC31645
0.8588	High Similarity	NPC5130
0.8556	High Similarity	NPC328562
0.8556	High Similarity	NPC323421
0.8506	High Similarity	NPC329857
0.8506	High Similarity	NPC469718
0.8471	Intermediate Similarity	NPC50637
0.8444	Intermediate Similarity	NPC470883
0.8444	Intermediate Similarity	NPC76862
0.8444	Intermediate Similarity	NPC158416
0.8444	Intermediate Similarity	NPC39859
0.8409	Intermediate Similarity	NPC20713
0.8333	Intermediate Similarity	NPC273197
0.8333	Intermediate Similarity	NPC234339
0.8333	Intermediate Similarity	NPC474703
0.828	Intermediate Similarity	NPC201718
0.828	Intermediate Similarity	NPC15993
0.8256	Intermediate Similarity	NPC162071
0.8242	Intermediate Similarity	NPC301596
0.8242	Intermediate Similarity	NPC299396
0.8242	Intermediate Similarity	NPC172998
0.8214	Intermediate Similarity	NPC246076
0.8191	Intermediate Similarity	NPC324017
0.8191	Intermediate Similarity	NPC320019
0.8182	Intermediate Similarity	NPC151770
0.8182	Intermediate Similarity	NPC474951
0.8182	Intermediate Similarity	NPC166919
0.8182	Intermediate Similarity	NPC173926
0.8152	Intermediate Similarity	NPC471140
0.8132	Intermediate Similarity	NPC163228
0.8132	Intermediate Similarity	NPC475900
0.8132	Intermediate Similarity	NPC474947
0.8118	Intermediate Similarity	NPC272814
0.8095	Intermediate Similarity	NPC301477
0.8095	Intermediate Similarity	NPC25684
0.8095	Intermediate Similarity	NPC141810
0.8095	Intermediate Similarity	NPC281949
0.809	Intermediate Similarity	NPC144133
0.809	Intermediate Similarity	NPC179394
0.8085	Intermediate Similarity	NPC164598
0.8085	Intermediate Similarity	NPC474339
0.8072	Intermediate Similarity	NPC617
0.8046	Intermediate Similarity	NPC304558
0.8043	Intermediate Similarity	NPC476009
0.8043	Intermediate Similarity	NPC476275
0.8	Intermediate Similarity	NPC70251
0.8	Intermediate Similarity	NPC475881
0.7978	Intermediate Similarity	NPC472872
0.7976	Intermediate Similarity	NPC474981
0.7955	Intermediate Similarity	NPC231889
0.7955	Intermediate Similarity	NPC24728
0.7955	Intermediate Similarity	NPC186148
0.7955	Intermediate Similarity	NPC118601
0.7931	Intermediate Similarity	NPC235792
0.7912	Intermediate Similarity	NPC228451
0.7912	Intermediate Similarity	NPC125674
0.7912	Intermediate Similarity	NPC475838
0.7907	Intermediate Similarity	NPC318468
0.7907	Intermediate Similarity	NPC257358
0.7907	Intermediate Similarity	NPC474472
0.7895	Intermediate Similarity	NPC477511
0.7895	Intermediate Similarity	NPC264477
0.7895	Intermediate Similarity	NPC476270
0.7895	Intermediate Similarity	NPC47880
0.7889	Intermediate Similarity	NPC206614
0.7889	Intermediate Similarity	NPC475748
0.7889	Intermediate Similarity	NPC475855
0.7889	Intermediate Similarity	NPC474323
0.7882	Intermediate Similarity	NPC47635
0.7865	Intermediate Similarity	NPC207114
0.7865	Intermediate Similarity	NPC178875
0.7865	Intermediate Similarity	NPC58219
0.7865	Intermediate Similarity	NPC177629
0.7865	Intermediate Similarity	NPC217983
0.7865	Intermediate Similarity	NPC471149
0.7865	Intermediate Similarity	NPC202672
0.7865	Intermediate Similarity	NPC79549
0.7857	Intermediate Similarity	NPC270126
0.7857	Intermediate Similarity	NPC19841
0.7849	Intermediate Similarity	NPC17585
0.7841	Intermediate Similarity	NPC469626
0.7841	Intermediate Similarity	NPC38576
0.7841	Intermediate Similarity	NPC475491
0.7841	Intermediate Similarity	NPC64153
0.7841	Intermediate Similarity	NPC279859
0.7841	Intermediate Similarity	NPC470242
0.7831	Intermediate Similarity	NPC476028
0.7831	Intermediate Similarity	NPC476794
0.7831	Intermediate Similarity	NPC141789
0.7831	Intermediate Similarity	NPC470240
0.7831	Intermediate Similarity	NPC171204
0.7826	Intermediate Similarity	NPC474247
0.7826	Intermediate Similarity	NPC473316
0.7826	Intermediate Similarity	NPC473330
0.7826	Intermediate Similarity	NPC140543
0.7816	Intermediate Similarity	NPC115786
0.7812	Intermediate Similarity	NPC471148
0.7812	Intermediate Similarity	NPC189609
0.7812	Intermediate Similarity	NPC197835
0.7812	Intermediate Similarity	NPC140591
0.7812	Intermediate Similarity	NPC303653
0.7812	Intermediate Similarity	NPC291500
0.7812	Intermediate Similarity	NPC149371
0.7805	Intermediate Similarity	NPC155587
0.7802	Intermediate Similarity	NPC329952
0.7802	Intermediate Similarity	NPC191339
0.7802	Intermediate Similarity	NPC133698
0.7802	Intermediate Similarity	NPC286341
0.7802	Intermediate Similarity	NPC184063
0.7802	Intermediate Similarity	NPC184463
0.7778	Intermediate Similarity	NPC307411
0.7778	Intermediate Similarity	NPC475971
0.7778	Intermediate Similarity	NPC92974
0.7778	Intermediate Similarity	NPC215556
0.7778	Intermediate Similarity	NPC283409
0.7766	Intermediate Similarity	NPC474313
0.7753	Intermediate Similarity	NPC266957
0.7753	Intermediate Similarity	NPC475703
0.7727	Intermediate Similarity	NPC304509
0.7727	Intermediate Similarity	NPC149725
0.7727	Intermediate Similarity	NPC50362
0.7727	Intermediate Similarity	NPC47958
0.7727	Intermediate Similarity	NPC255307
0.7727	Intermediate Similarity	NPC319795
0.7727	Intermediate Similarity	NPC215364
0.7727	Intermediate Similarity	NPC38468
0.7717	Intermediate Similarity	NPC308656
0.7717	Intermediate Similarity	NPC473234
0.7717	Intermediate Similarity	NPC212486
0.7717	Intermediate Similarity	NPC475912
0.7717	Intermediate Similarity	NPC473273
0.7717	Intermediate Similarity	NPC476300
0.7717	Intermediate Similarity	NPC472874
0.7717	Intermediate Similarity	NPC473263
0.7717	Intermediate Similarity	NPC475302
0.7717	Intermediate Similarity	NPC60386
0.7711	Intermediate Similarity	NPC235906
0.7701	Intermediate Similarity	NPC54468
0.7701	Intermediate Similarity	NPC170286
0.7701	Intermediate Similarity	NPC250315
0.7692	Intermediate Similarity	NPC54065
0.7692	Intermediate Similarity	NPC251385
0.7692	Intermediate Similarity	NPC49342
0.7692	Intermediate Similarity	NPC51004
0.7692	Intermediate Similarity	NPC475776
0.7692	Intermediate Similarity	NPC62815
0.7692	Intermediate Similarity	NPC297474
0.7692	Intermediate Similarity	NPC312042
0.7692	Intermediate Similarity	NPC216284
0.7692	Intermediate Similarity	NPC19087
0.7684	Intermediate Similarity	NPC474213
0.7667	Intermediate Similarity	NPC475902
0.7667	Intermediate Similarity	NPC469653
0.7667	Intermediate Similarity	NPC469628
0.7667	Intermediate Similarity	NPC469631
0.7667	Intermediate Similarity	NPC471047
0.7667	Intermediate Similarity	NPC224652
0.7667	Intermediate Similarity	NPC475906
0.766	Intermediate Similarity	NPC279621
0.766	Intermediate Similarity	NPC230800
0.7653	Intermediate Similarity	NPC477510
0.7653	Intermediate Similarity	NPC471143
0.764	Intermediate Similarity	NPC187661
0.764	Intermediate Similarity	NPC475019
0.764	Intermediate Similarity	NPC107787
0.764	Intermediate Similarity	NPC475461
0.764	Intermediate Similarity	NPC238593
0.764	Intermediate Similarity	NPC474762
0.764	Intermediate Similarity	NPC305475
0.764	Intermediate Similarity	NPC284902
0.764	Intermediate Similarity	NPC150755
0.764	Intermediate Similarity	NPC474949
0.764	Intermediate Similarity	NPC476015
0.7634	Intermediate Similarity	NPC198853
0.7634	Intermediate Similarity	NPC476267
0.7634	Intermediate Similarity	NPC473331
0.7634	Intermediate Similarity	NPC474338
0.7634	Intermediate Similarity	NPC477131
0.7634	Intermediate Similarity	NPC127019
0.7634	Intermediate Similarity	NPC471147
0.7629	Intermediate Similarity	NPC474747
0.7619	Intermediate Similarity	NPC97516
0.7619	Intermediate Similarity	NPC65603
0.7614	Intermediate Similarity	NPC114979
0.7614	Intermediate Similarity	NPC96259
0.7614	Intermediate Similarity	NPC191476
0.7614	Intermediate Similarity	NPC474780
0.7614	Intermediate Similarity	NPC159635
0.7614	Intermediate Similarity	NPC141193
0.7609	Intermediate Similarity	NPC133888
0.7609	Intermediate Similarity	NPC12172
0.7609	Intermediate Similarity	NPC29821
0.7609	Intermediate Similarity	NPC30515
0.7609	Intermediate Similarity	NPC293001
0.7609	Intermediate Similarity	NPC171360
0.7609	Intermediate Similarity	NPC63193
0.7609	Intermediate Similarity	NPC35959

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 NPC128429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	2852
0.2-0.3	3774
0.3-0.4	1532
0.4-0.5	475
0.5-0.6	213
0.6-0.7	18
0.7-0.8	3
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
0.7727	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1695	Approved
0.7157	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5282	Discontinued
0.6837	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD46	Approved
0.6771	Remote Similarity	NPD6698	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6596	Remote Similarity	NPD1694	Approved
0.6574	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7838	Discovery
0.6364	Remote Similarity	NPD5693	Phase 1
0.6263	Remote Similarity	NPD5785	Approved
0.6262	Remote Similarity	NPD6008	Approved
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD7154	Phase 3
0.62	Remote Similarity	NPD7983	Approved
0.6186	Remote Similarity	NPD4249	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.617	Remote Similarity	NPD5369	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6686	Approved
0.6147	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4251	Approved
0.6122	Remote Similarity	NPD4250	Approved
0.6118	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6435	Approved
0.6105	Remote Similarity	NPD5209	Approved
0.6082	Remote Similarity	NPD5363	Approved
0.6071	Remote Similarity	NPD6053	Discontinued
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6055	Remote Similarity	NPD5697	Approved
0.6055	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.598	Remote Similarity	NPD6399	Phase 3
0.598	Remote Similarity	NPD5779	Approved
0.598	Remote Similarity	NPD5778	Approved
0.5963	Remote Similarity	NPD7128	Approved
0.5963	Remote Similarity	NPD6402	Approved
0.5963	Remote Similarity	NPD6675	Approved
0.5963	Remote Similarity	NPD5739	Approved
0.5946	Remote Similarity	NPD6012	Approved
0.5946	Remote Similarity	NPD6013	Approved
0.5946	Remote Similarity	NPD6373	Approved
0.5946	Remote Similarity	NPD6014	Approved
0.5946	Remote Similarity	NPD6372	Approved
0.5943	Remote Similarity	NPD6648	Approved
0.5941	Remote Similarity	NPD5692	Phase 3
0.5938	Remote Similarity	NPD4270	Approved
0.5938	Remote Similarity	NPD4269	Approved
0.5918	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4756	Discovery
0.5909	Remote Similarity	NPD5701	Approved
0.5895	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4822	Approved
0.5895	Remote Similarity	NPD5368	Approved
0.5895	Remote Similarity	NPD4821	Approved
0.5895	Remote Similarity	NPD4820	Approved
0.5895	Remote Similarity	NPD4819	Approved
0.5893	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5888	Remote Similarity	NPD5344	Discontinued
0.5882	Remote Similarity	NPD6050	Approved
0.5882	Remote Similarity	NPD5694	Approved
0.5876	Remote Similarity	NPD5362	Discontinued
0.587	Remote Similarity	NPD8039	Approved
0.5859	Remote Similarity	NPD5786	Approved
0.5859	Remote Similarity	NPD5330	Approved
0.5859	Remote Similarity	NPD7146	Approved
0.5859	Remote Similarity	NPD7521	Approved
0.5859	Remote Similarity	NPD6409	Approved
0.5859	Remote Similarity	NPD6684	Approved
0.5859	Remote Similarity	NPD6098	Approved
0.5859	Remote Similarity	NPD7334	Approved
0.5856	Remote Similarity	NPD7320	Approved
0.5856	Remote Similarity	NPD6011	Approved
0.5849	Remote Similarity	NPD7638	Approved
0.5847	Remote Similarity	NPD6319	Approved
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6617	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5804	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7639	Approved
0.5794	Remote Similarity	NPD7640	Approved
0.5789	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD8297	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.5769	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7900	Approved
0.5752	Remote Similarity	NPD2067	Discontinued
0.5743	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6903	Approved
0.5739	Remote Similarity	NPD4632	Approved
0.5739	Remote Similarity	NPD8133	Approved
0.5738	Remote Similarity	NPD6616	Approved
0.5729	Remote Similarity	NPD4252	Approved
0.5728	Remote Similarity	NPD8035	Phase 2
0.5728	Remote Similarity	NPD8034	Phase 2
0.5726	Remote Similarity	NPD6009	Approved
0.5726	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7078	Approved
0.5686	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6101	Approved
0.5684	Remote Similarity	NPD4268	Approved
0.5684	Remote Similarity	NPD4271	Approved
0.5684	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8517	Approved
0.5667	Remote Similarity	NPD6016	Approved
0.5667	Remote Similarity	NPD6015	Approved
0.5667	Remote Similarity	NPD8513	Phase 3
0.5667	Remote Similarity	NPD8516	Approved
0.5667	Remote Similarity	NPD8515	Approved
0.5667	Remote Similarity	NPD5983	Phase 2
0.566	Remote Similarity	NPD7839	Suspended
0.5659	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7736	Approved
0.5641	Remote Similarity	NPD6274	Approved
0.5635	Remote Similarity	NPD7260	Phase 2
0.5631	Remote Similarity	NPD5207	Approved
0.562	Remote Similarity	NPD5988	Approved
0.562	Remote Similarity	NPD6370	Approved
0.5607	Remote Similarity	NPD7902	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data