NPASS Compound

Structure

NPC26504 OpenBabel07101719132D 26 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6797 3.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7479 2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0656 0.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8692 0.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1280 1.5176 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4209 2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4550 1.9659 0.0000 C 0 0 2 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 1.7321 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 0.8660 1.5000 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 -5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 15 2 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 19 2 0 0 0 0 15 16 1 0 0 0 0 16 22 1 1 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 23 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	391.297
LogP:	5.538
LogD:	3.826
LogS:	-4.493
# Rotatable Bonds:	5
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	4.15
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	2.681451769603882e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.11
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.792
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	99.61321258544922%
Volume Distribution (VD):	5.439
Pgp-substrate:	3.8203108310699463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.684
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.684
CYP2C9-inhibitor:	0.411
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.766
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	8.441
Half-life (T1/2):	0.584

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.713
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.772
Skin Sensitization:	0.97
Carcinogencity:	0.329
Eye Corrosion:	0.01
Eye Irritation:	0.891
Respiratory Toxicity:	0.834

Download Data

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

Natural Product: NPC26504

Natural Product ID:	NPC26504
*Common Name:**	Metachromin C
IUPAC Name:	2-hydroxy-5-methoxy-3-[(E)-3-methyl-5-[(1R,2S)-1,2,3-trimethylcyclohex-3-en-1-yl]pent-2-enyl]cyclohexa-2,5-diene-1,4-dione
Synonyms:	Metachromin C
Standard InCHIKey:	RDBDWSGJCBFVNX-ABZGJHIISA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-14(10-12-22(4)11-6-7-15(2)16(22)3)8-9-17-20(24)18(23)13-19(26-5)21(17)25/h7-8,13,16,24H,6,9-12H2,1-5H3/b14-8+/t16-,22-/m1/s1
SMILES:	COC1=CC(=O)C(=C(C1=O)C/C=C(/CC[C@@]1(C)CCC=C([C@H]1C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484235
PubChem CID:	6440837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO33163	hippospongia metachromia	Species	Spongiidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11421749]
NPO33163	hippospongia metachromia	Species	Spongiidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[2607352]

☑ 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	8

Activity Type	# Activity
Cell Line	4
CELL-LINE	1
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.0	ug.mL-1	PMID[549632]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	0.92	ug.mL-1	PMID[549632]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[549633]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.0	ug.mL-1	PMID[549633]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	>	200.0	ug.mL-1	PMID[549633]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	>	200.0	ug.mL-1	PMID[549633]
NPT610	Others	Molecular identity unknown		IC50	=	3000.0	nM	PMID[549632]
NPT27801	CELL-LINE	HeLa/Fucci2	Homo sapiens	IC50	=	53000.0	nM	PMID[549634]

☑ 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 NPC26504 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	168
0.1-0.2	1239
0.2-0.3	6855
0.3-0.4	18085
0.4-0.5	9073
0.5-0.6	5765
0.6-0.7	1388
0.7-0.8	114
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC147438
0.8889	High Similarity	NPC474539
0.8861	High Similarity	NPC8518
0.8861	High Similarity	NPC132228
0.8861	High Similarity	NPC263997
0.8831	High Similarity	NPC99308
0.8625	High Similarity	NPC241512
0.8625	High Similarity	NPC6185
0.8354	Intermediate Similarity	NPC474085
0.8354	Intermediate Similarity	NPC55869
0.8333	Intermediate Similarity	NPC27817
0.825	Intermediate Similarity	NPC103486
0.8228	Intermediate Similarity	NPC108955
0.8182	Intermediate Similarity	NPC1254
0.8182	Intermediate Similarity	NPC110725
0.7952	Intermediate Similarity	NPC133652
0.7952	Intermediate Similarity	NPC474680
0.7949	Intermediate Similarity	NPC470525
0.7907	Intermediate Similarity	NPC474209
0.7907	Intermediate Similarity	NPC475823
0.7901	Intermediate Similarity	NPC225515
0.7901	Intermediate Similarity	NPC475833
0.7867	Intermediate Similarity	NPC474060
0.775	Intermediate Similarity	NPC189485
0.775	Intermediate Similarity	NPC74410
0.775	Intermediate Similarity	NPC30321
0.7738	Intermediate Similarity	NPC255174
0.7738	Intermediate Similarity	NPC32037
0.7722	Intermediate Similarity	NPC92080
0.7711	Intermediate Similarity	NPC105803
0.7692	Intermediate Similarity	NPC264178
0.7683	Intermediate Similarity	NPC116797
0.7674	Intermediate Similarity	NPC53454
0.7632	Intermediate Similarity	NPC262673
0.7625	Intermediate Similarity	NPC283087
0.76	Intermediate Similarity	NPC243272
0.7595	Intermediate Similarity	NPC175079
0.7561	Intermediate Similarity	NPC74086
0.7532	Intermediate Similarity	NPC291062
0.7532	Intermediate Similarity	NPC94743
0.7531	Intermediate Similarity	NPC23778
0.7531	Intermediate Similarity	NPC475994
0.7529	Intermediate Similarity	NPC90287
0.7529	Intermediate Similarity	NPC470177
0.7528	Intermediate Similarity	NPC263780
0.75	Intermediate Similarity	NPC223093
0.75	Intermediate Similarity	NPC288281
0.75	Intermediate Similarity	NPC263382
0.75	Intermediate Similarity	NPC53733
0.75	Intermediate Similarity	NPC112680
0.75	Intermediate Similarity	NPC292589
0.75	Intermediate Similarity	NPC180886
0.75	Intermediate Similarity	NPC125578
0.75	Intermediate Similarity	NPC38952
0.75	Intermediate Similarity	NPC146376
0.747	Intermediate Similarity	NPC470034
0.747	Intermediate Similarity	NPC475863
0.747	Intermediate Similarity	NPC6663
0.7444	Intermediate Similarity	NPC23170
0.7442	Intermediate Similarity	NPC203795
0.7439	Intermediate Similarity	NPC475681
0.7439	Intermediate Similarity	NPC19900
0.7436	Intermediate Similarity	NPC474884
0.7416	Intermediate Similarity	NPC174167
0.7416	Intermediate Similarity	NPC470036
0.7412	Intermediate Similarity	NPC53385
0.7403	Intermediate Similarity	NPC94488
0.7386	Intermediate Similarity	NPC210216
0.7375	Intermediate Similarity	NPC474885
0.7356	Intermediate Similarity	NPC470523
0.7349	Intermediate Similarity	NPC287063
0.7349	Intermediate Similarity	NPC2482
0.7333	Intermediate Similarity	NPC251118
0.7326	Intermediate Similarity	NPC33663
0.7326	Intermediate Similarity	NPC33881
0.7317	Intermediate Similarity	NPC62336
0.7317	Intermediate Similarity	NPC478247
0.7317	Intermediate Similarity	NPC478246
0.7308	Intermediate Similarity	NPC286154
0.7297	Intermediate Similarity	NPC288253
0.7294	Intermediate Similarity	NPC8091
0.7294	Intermediate Similarity	NPC49019
0.7294	Intermediate Similarity	NPC291999
0.7294	Intermediate Similarity	NPC309309
0.7284	Intermediate Similarity	NPC263582
0.7284	Intermediate Similarity	NPC250621
0.7273	Intermediate Similarity	NPC188292
0.7273	Intermediate Similarity	NPC307298
0.7273	Intermediate Similarity	NPC87141
0.7273	Intermediate Similarity	NPC470524
0.7273	Intermediate Similarity	NPC260474
0.7273	Intermediate Similarity	NPC155198
0.7262	Intermediate Similarity	NPC44963
0.7262	Intermediate Similarity	NPC90055
0.7262	Intermediate Similarity	NPC121984
0.7262	Intermediate Similarity	NPC189237
0.7262	Intermediate Similarity	NPC278459
0.7262	Intermediate Similarity	NPC472684
0.725	Intermediate Similarity	NPC75485
0.725	Intermediate Similarity	NPC168975
0.7241	Intermediate Similarity	NPC472974
0.7241	Intermediate Similarity	NPC94666
0.7229	Intermediate Similarity	NPC192329
0.7229	Intermediate Similarity	NPC476177
0.7229	Intermediate Similarity	NPC170394
0.7229	Intermediate Similarity	NPC472490
0.7222	Intermediate Similarity	NPC99380
0.7222	Intermediate Similarity	NPC26865
0.7209	Intermediate Similarity	NPC237712
0.7209	Intermediate Similarity	NPC472265
0.72	Intermediate Similarity	NPC34622
0.72	Intermediate Similarity	NPC474400
0.7195	Intermediate Similarity	NPC97377
0.7195	Intermediate Similarity	NPC165711
0.7195	Intermediate Similarity	NPC203403
0.7191	Intermediate Similarity	NPC112454
0.7191	Intermediate Similarity	NPC65615
0.7191	Intermediate Similarity	NPC474918
0.7191	Intermediate Similarity	NPC68148
0.7188	Intermediate Similarity	NPC179208
0.7179	Intermediate Similarity	NPC256846
0.7176	Intermediate Similarity	NPC158411
0.7176	Intermediate Similarity	NPC38796
0.7176	Intermediate Similarity	NPC92226
0.7174	Intermediate Similarity	NPC295347
0.7174	Intermediate Similarity	NPC147232
0.7174	Intermediate Similarity	NPC777
0.716	Intermediate Similarity	NPC114236
0.7159	Intermediate Similarity	NPC220930
0.7159	Intermediate Similarity	NPC272039
0.7159	Intermediate Similarity	NPC473097
0.7143	Intermediate Similarity	NPC211230
0.7143	Intermediate Similarity	NPC96962
0.7143	Intermediate Similarity	NPC317796
0.7143	Intermediate Similarity	NPC472478
0.7143	Intermediate Similarity	NPC474619
0.7143	Intermediate Similarity	NPC476809
0.7126	Intermediate Similarity	NPC469993
0.7126	Intermediate Similarity	NPC79573
0.7113	Intermediate Similarity	NPC40170
0.7111	Intermediate Similarity	NPC113393
0.7111	Intermediate Similarity	NPC129913
0.7111	Intermediate Similarity	NPC212369
0.7111	Intermediate Similarity	NPC472325
0.7108	Intermediate Similarity	NPC321514
0.7108	Intermediate Similarity	NPC478122
0.7108	Intermediate Similarity	NPC469996
0.7108	Intermediate Similarity	NPC275494
0.7108	Intermediate Similarity	NPC471409
0.7108	Intermediate Similarity	NPC476808
0.7105	Intermediate Similarity	NPC98897
0.7093	Intermediate Similarity	NPC168188
0.7093	Intermediate Similarity	NPC470015
0.7083	Intermediate Similarity	NPC224103
0.7083	Intermediate Similarity	NPC200831
0.7083	Intermediate Similarity	NPC299369
0.7079	Intermediate Similarity	NPC58271
0.7079	Intermediate Similarity	NPC475001
0.7079	Intermediate Similarity	NPC185059
0.7067	Intermediate Similarity	NPC477830
0.7067	Intermediate Similarity	NPC53109
0.7067	Intermediate Similarity	NPC57463
0.7067	Intermediate Similarity	NPC151728
0.7067	Intermediate Similarity	NPC143168
0.7065	Intermediate Similarity	NPC474882
0.7065	Intermediate Similarity	NPC474328
0.7059	Intermediate Similarity	NPC136150
0.7059	Intermediate Similarity	NPC149237
0.7051	Intermediate Similarity	NPC310992
0.7051	Intermediate Similarity	NPC117804
0.7045	Intermediate Similarity	NPC118648
0.7045	Intermediate Similarity	NPC477479
0.7045	Intermediate Similarity	NPC222613
0.7045	Intermediate Similarity	NPC477478
0.7045	Intermediate Similarity	NPC327115
0.7045	Intermediate Similarity	NPC475022
0.7037	Intermediate Similarity	NPC22134
0.7037	Intermediate Similarity	NPC215050
0.7033	Intermediate Similarity	NPC248913
0.7027	Intermediate Similarity	NPC127582
0.7024	Intermediate Similarity	NPC470429
0.7024	Intermediate Similarity	NPC308038
0.7021	Intermediate Similarity	NPC208094
0.7013	Intermediate Similarity	NPC16119
0.7011	Intermediate Similarity	NPC144258
0.7011	Intermediate Similarity	NPC469884
0.7011	Intermediate Similarity	NPC474359
0.7011	Intermediate Similarity	NPC476412
0.7011	Intermediate Similarity	NPC33913
0.7011	Intermediate Similarity	NPC473246
0.7	Intermediate Similarity	NPC118011
0.7	Intermediate Similarity	NPC474805
0.7	Intermediate Similarity	NPC23117
0.7	Intermediate Similarity	NPC95863
0.7	Intermediate Similarity	NPC5509
0.7	Intermediate Similarity	NPC326627
0.7	Intermediate Similarity	NPC310010
0.7	Intermediate Similarity	NPC123912
0.7	Intermediate Similarity	NPC280833
0.7	Intermediate Similarity	NPC36668

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 NPC26504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1844
0.2-0.3	4330
0.3-0.4	2148
0.4-0.5	354
0.5-0.6	267
0.6-0.7	46
0.7-0.8	7
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
0.8228	Intermediate Similarity	NPD4695	Discontinued
0.7561	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5690	Phase 2
0.7241	Intermediate Similarity	NPD5279	Phase 3
0.7191	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5695	Phase 3
0.7108	Intermediate Similarity	NPD3617	Approved
0.7083	Intermediate Similarity	NPD8779	Phase 3
0.7067	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4694	Approved
0.7045	Intermediate Similarity	NPD5280	Approved
0.7013	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3704	Approved
0.7011	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD4753	Phase 2
0.6988	Remote Similarity	NPD4756	Discovery
0.6932	Remote Similarity	NPD5329	Approved
0.6889	Remote Similarity	NPD6672	Approved
0.6889	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD4691	Approved
0.6842	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD6083	Phase 2
0.6824	Remote Similarity	NPD4195	Approved
0.6818	Remote Similarity	NPD3665	Phase 1
0.6818	Remote Similarity	NPD3666	Approved
0.6818	Remote Similarity	NPD3133	Approved
0.6809	Remote Similarity	NPD5210	Approved
0.6809	Remote Similarity	NPD4629	Approved
0.679	Remote Similarity	NPD5276	Approved
0.6782	Remote Similarity	NPD3667	Approved
0.6782	Remote Similarity	NPD4223	Phase 3
0.6782	Remote Similarity	NPD4221	Approved
0.6771	Remote Similarity	NPD5696	Approved
0.675	Remote Similarity	NPD4137	Phase 3
0.6742	Remote Similarity	NPD1696	Phase 3
0.6739	Remote Similarity	NPD5692	Phase 3
0.6737	Remote Similarity	NPD5222	Approved
0.6737	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5221	Approved
0.6705	Remote Similarity	NPD6110	Phase 1
0.6702	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.663	Remote Similarity	NPD6080	Approved
0.663	Remote Similarity	NPD6904	Approved
0.663	Remote Similarity	NPD6673	Approved
0.6629	Remote Similarity	NPD4786	Approved
0.6627	Remote Similarity	NPD5733	Approved
0.6627	Remote Similarity	NPD4058	Approved
0.6627	Remote Similarity	NPD4687	Approved
0.6582	Remote Similarity	NPD7331	Phase 2
0.6562	Remote Similarity	NPD4697	Phase 3
0.6548	Remote Similarity	NPD8264	Approved
0.6533	Remote Similarity	NPD287	Approved
0.6531	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD5285	Approved
0.6531	Remote Similarity	NPD5286	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6522	Remote Similarity	NPD4518	Approved
0.6495	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD5693	Phase 1
0.6489	Remote Similarity	NPD5284	Approved
0.6489	Remote Similarity	NPD7515	Phase 2
0.6489	Remote Similarity	NPD6079	Approved
0.6489	Remote Similarity	NPD5281	Approved
0.6484	Remote Similarity	NPD4689	Approved
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD4623	Approved
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD5205	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD5223	Approved
0.6452	Remote Similarity	NPD5328	Approved
0.6444	Remote Similarity	NPD3668	Phase 3
0.6421	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD5133	Approved
0.6408	Remote Similarity	NPD6881	Approved
0.6408	Remote Similarity	NPD6011	Approved
0.6408	Remote Similarity	NPD6899	Approved
0.6404	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD4633	Approved
0.6383	Remote Similarity	NPD4096	Approved
0.6373	Remote Similarity	NPD5739	Approved
0.6373	Remote Similarity	NPD6402	Approved
0.6373	Remote Similarity	NPD7128	Approved
0.6373	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6346	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD6014	Approved
0.6346	Remote Similarity	NPD6012	Approved
0.6337	Remote Similarity	NPD5175	Approved
0.6337	Remote Similarity	NPD5174	Approved
0.6327	Remote Similarity	NPD7902	Approved
0.6316	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.6304	Remote Similarity	NPD7334	Approved
0.6304	Remote Similarity	NPD7521	Approved
0.6304	Remote Similarity	NPD7146	Approved
0.6304	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD5330	Approved
0.6304	Remote Similarity	NPD6098	Approved
0.6304	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD5654	Approved
0.6286	Remote Similarity	NPD7290	Approved
0.6286	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD7102	Approved
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5141	Approved
0.6264	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.6238	Remote Similarity	NPD5091	Approved
0.6237	Remote Similarity	NPD3573	Approved
0.6226	Remote Similarity	NPD6617	Approved
0.6226	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD8130	Phase 1
0.6226	Remote Similarity	NPD6649	Approved
0.6226	Remote Similarity	NPD6869	Approved
0.6226	Remote Similarity	NPD6847	Approved
0.6224	Remote Similarity	NPD7614	Phase 1
0.622	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD6372	Approved
0.6176	Remote Similarity	NPD4754	Approved
0.617	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8297	Approved
0.6168	Remote Similarity	NPD6882	Approved
0.6163	Remote Similarity	NPD7339	Approved
0.6163	Remote Similarity	NPD6942	Approved
0.6162	Remote Similarity	NPD5959	Approved
0.6154	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4788	Approved
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6111	Remote Similarity	NPD8028	Phase 2
0.6111	Remote Similarity	NPD4692	Approved
0.6111	Remote Similarity	NPD4139	Approved
0.6105	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6101	Approved
0.6095	Remote Similarity	NPD4729	Approved
0.6095	Remote Similarity	NPD5128	Approved
0.6095	Remote Similarity	NPD5168	Approved
0.6095	Remote Similarity	NPD4730	Approved
0.6076	Remote Similarity	NPD4193	Approved
0.6076	Remote Similarity	NPD4192	Approved
0.6076	Remote Similarity	NPD4191	Approved
0.6076	Remote Similarity	NPD4194	Approved
0.6075	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7144	Approved
0.6071	Remote Similarity	NPD7143	Approved
0.6067	Remote Similarity	NPD7645	Phase 2
0.6061	Remote Similarity	NPD7732	Phase 3
0.6058	Remote Similarity	NPD4768	Approved
0.6058	Remote Similarity	NPD4767	Approved
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.6047	Remote Similarity	NPD4785	Approved
0.6047	Remote Similarity	NPD4784	Approved
0.6042	Remote Similarity	NPD5785	Approved
0.6042	Remote Similarity	NPD5207	Approved
0.602	Remote Similarity	NPD7900	Approved
0.602	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD4243	Approved
0.5981	Remote Similarity	NPD5251	Approved
0.5981	Remote Similarity	NPD5135	Approved
0.5981	Remote Similarity	NPD5247	Approved
0.5981	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4634	Approved
0.5981	Remote Similarity	NPD5169	Approved
0.5981	Remote Similarity	NPD5248	Approved
0.5981	Remote Similarity	NPD5249	Phase 3
0.5981	Remote Similarity	NPD5250	Approved
0.5979	Remote Similarity	NPD7637	Suspended
0.5963	Remote Similarity	NPD4632	Approved
0.596	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6317	Approved
0.5946	Remote Similarity	NPD6009	Approved
0.5941	Remote Similarity	NPD7638	Approved
0.5926	Remote Similarity	NPD5217	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