NPASS Compound

Structure

NPC147438 OpenBabel07101719512D 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 2 0 0 0 0 0 0 0 0 0 -5.4550 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 3 16 2 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 1 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 2 1 1 0 0 0 15 16 1 0 0 0 0 16 22 1 0 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:	4.87
LogD:	3.297
LogS:	-4.692
# 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:	4.149
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:	-4.956
MDCK Permeability:	2.785403557936661e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.432
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	100.48799896240234%
Volume Distribution (VD):	3.77
Pgp-substrate:	1.198731780052185%

ADMET: Metabolism

CYP1A2-inhibitor:	0.468
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.194
CYP2C19-substrate:	0.719
CYP2C9-inhibitor:	0.263
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.677
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	2.227
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.612
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.963
Carcinogencity:	0.185
Eye Corrosion:	0.004
Eye Irritation:	0.869
Respiratory Toxicity:	0.76

Download Data

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

Natural Product: NPC147438

Natural Product ID:	NPC147438
*Common Name:**	Metachromin A
IUPAC Name:	3-[(E)-5-[(1R,3R)-1,3-dimethyl-2-methylidenecyclohexyl]-3-methylpent-2-enyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	IAMSURZACLERPY-XMRYUXBUSA-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/h8,13,15,24H,3,6-7,9-12H2,1-2,4-5H3/b14-8+/t15-,22-/m1/s1
SMILES:	COC1=CC(=O)C(=C(C1=O)C/C=C(/CC[C@@]1(C)CCC[C@H](C1=C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470685
PubChem CID:	10473589
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	7

Activity Type	# Activity
Cell Line	3
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[559568]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[559570]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.4	ug.mL-1	PMID[559570]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	>	200.0	ug.mL-1	PMID[559570]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	>	200.0	ug.mL-1	PMID[559570]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.8	ug.mL-1	PMID[559568]
NPT610	Others	Molecular identity unknown		IC50	=	3000.0	nM	PMID[559569]

☑ 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 NPC147438 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	153
0.1-0.2	1131
0.2-0.3	6280
0.3-0.4	17077
0.4-0.5	9636
0.5-0.6	6263
0.6-0.7	2003
0.7-0.8	136
0.8-0.85	10
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC26504
0.942	High Similarity	NPC474539
0.8608	High Similarity	NPC263997
0.8608	High Similarity	NPC6185
0.8608	High Similarity	NPC241512
0.8608	High Similarity	NPC132228
0.8608	High Similarity	NPC8518
0.8571	High Similarity	NPC99308
0.84	Intermediate Similarity	NPC110725
0.8101	Intermediate Similarity	NPC55869
0.8101	Intermediate Similarity	NPC474085
0.8077	Intermediate Similarity	NPC27817
0.8052	Intermediate Similarity	NPC283087
0.8	Intermediate Similarity	NPC103486
0.7975	Intermediate Similarity	NPC108955
0.7927	Intermediate Similarity	NPC474680
0.7927	Intermediate Similarity	NPC32037
0.7922	Intermediate Similarity	NPC1254
0.7901	Intermediate Similarity	NPC288281
0.7882	Intermediate Similarity	NPC474209
0.7882	Intermediate Similarity	NPC475823
0.7857	Intermediate Similarity	NPC53454
0.7838	Intermediate Similarity	NPC474060
0.7838	Intermediate Similarity	NPC262673
0.7808	Intermediate Similarity	NPC243272
0.7792	Intermediate Similarity	NPC175079
0.7733	Intermediate Similarity	NPC94743
0.7733	Intermediate Similarity	NPC291062
0.7711	Intermediate Similarity	NPC255174
0.7711	Intermediate Similarity	NPC470177
0.7711	Intermediate Similarity	NPC90287
0.7711	Intermediate Similarity	NPC133652
0.7703	Intermediate Similarity	NPC125578
0.7703	Intermediate Similarity	NPC263382
0.7703	Intermediate Similarity	NPC146376
0.7683	Intermediate Similarity	NPC105803
0.7662	Intermediate Similarity	NPC264178
0.7654	Intermediate Similarity	NPC475833
0.7654	Intermediate Similarity	NPC225515
0.76	Intermediate Similarity	NPC94488
0.75	Intermediate Similarity	NPC23778
0.75	Intermediate Similarity	NPC30321
0.75	Intermediate Similarity	NPC189485
0.7471	Intermediate Similarity	NPC38952
0.7471	Intermediate Similarity	NPC223093
0.7468	Intermediate Similarity	NPC92080
0.7468	Intermediate Similarity	NPC180886
0.7468	Intermediate Similarity	NPC470525
0.7439	Intermediate Similarity	NPC116797
0.7412	Intermediate Similarity	NPC203795
0.7407	Intermediate Similarity	NPC475681
0.7403	Intermediate Similarity	NPC474884
0.7397	Intermediate Similarity	NPC34622
0.7397	Intermediate Similarity	NPC474400
0.7356	Intermediate Similarity	NPC210216
0.7353	Intermediate Similarity	NPC317796
0.7342	Intermediate Similarity	NPC474885
0.7333	Intermediate Similarity	NPC474619
0.7317	Intermediate Similarity	NPC74086
0.7317	Intermediate Similarity	NPC2482
0.7303	Intermediate Similarity	NPC263780
0.7297	Intermediate Similarity	NPC98897
0.7286	Intermediate Similarity	NPC299369
0.7286	Intermediate Similarity	NPC224103
0.7286	Intermediate Similarity	NPC200831
0.7284	Intermediate Similarity	NPC475994
0.7284	Intermediate Similarity	NPC62336
0.7284	Intermediate Similarity	NPC74410
0.7273	Intermediate Similarity	NPC286154
0.7262	Intermediate Similarity	NPC8091
0.7262	Intermediate Similarity	NPC53733
0.726	Intermediate Similarity	NPC57463
0.726	Intermediate Similarity	NPC53109
0.726	Intermediate Similarity	NPC477830
0.726	Intermediate Similarity	NPC143168
0.726	Intermediate Similarity	NPC151728
0.725	Intermediate Similarity	NPC292589
0.725	Intermediate Similarity	NPC112680
0.725	Intermediate Similarity	NPC263582
0.725	Intermediate Similarity	NPC250621
0.7237	Intermediate Similarity	NPC155198
0.7229	Intermediate Similarity	NPC472684
0.7229	Intermediate Similarity	NPC189237
0.7229	Intermediate Similarity	NPC44963
0.7229	Intermediate Similarity	NPC278459
0.7229	Intermediate Similarity	NPC121984
0.7229	Intermediate Similarity	NPC470034
0.7229	Intermediate Similarity	NPC90055
0.7229	Intermediate Similarity	NPC475863
0.7229	Intermediate Similarity	NPC6663
0.7222	Intermediate Similarity	NPC23170
0.7215	Intermediate Similarity	NPC168975
0.7215	Intermediate Similarity	NPC75485
0.7209	Intermediate Similarity	NPC94666
0.7206	Intermediate Similarity	NPC474805
0.72	Intermediate Similarity	NPC16119
0.7195	Intermediate Similarity	NPC170394
0.7195	Intermediate Similarity	NPC192329
0.7195	Intermediate Similarity	NPC476177
0.7191	Intermediate Similarity	NPC470036
0.7191	Intermediate Similarity	NPC174167
0.7191	Intermediate Similarity	NPC26865
0.7176	Intermediate Similarity	NPC472265
0.7176	Intermediate Similarity	NPC237712
0.7176	Intermediate Similarity	NPC53385
0.7162	Intermediate Similarity	NPC7029
0.716	Intermediate Similarity	NPC203403
0.716	Intermediate Similarity	NPC97377
0.716	Intermediate Similarity	NPC165711
0.7159	Intermediate Similarity	NPC280833
0.7158	Intermediate Similarity	NPC179208
0.7143	Intermediate Similarity	NPC92226
0.7143	Intermediate Similarity	NPC295347
0.7126	Intermediate Similarity	NPC473097
0.7108	Intermediate Similarity	NPC287063
0.7108	Intermediate Similarity	NPC476809
0.7108	Intermediate Similarity	NPC472478
0.7105	Intermediate Similarity	NPC96962
0.7093	Intermediate Similarity	NPC79573
0.7093	Intermediate Similarity	NPC469993
0.7093	Intermediate Similarity	NPC33663
0.7093	Intermediate Similarity	NPC33881
0.7083	Intermediate Similarity	NPC473494
0.7083	Intermediate Similarity	NPC40170
0.7079	Intermediate Similarity	NPC212369
0.7079	Intermediate Similarity	NPC472325
0.7073	Intermediate Similarity	NPC471409
0.7073	Intermediate Similarity	NPC478246
0.7073	Intermediate Similarity	NPC478122
0.7073	Intermediate Similarity	NPC476808
0.7073	Intermediate Similarity	NPC321514
0.7073	Intermediate Similarity	NPC275494
0.7073	Intermediate Similarity	NPC478247
0.7067	Intermediate Similarity	NPC251118
0.7059	Intermediate Similarity	NPC291999
0.7059	Intermediate Similarity	NPC258985
0.7059	Intermediate Similarity	NPC137396
0.7059	Intermediate Similarity	NPC309309
0.7051	Intermediate Similarity	NPC203819
0.7045	Intermediate Similarity	NPC307298
0.7045	Intermediate Similarity	NPC185059
0.7045	Intermediate Similarity	NPC475001
0.7037	Intermediate Similarity	NPC40353
0.7024	Intermediate Similarity	NPC149237
0.7013	Intermediate Similarity	NPC260474
0.7013	Intermediate Similarity	NPC188292
0.7013	Intermediate Similarity	NPC134385
0.7011	Intermediate Similarity	NPC472974
0.7011	Intermediate Similarity	NPC327115
0.7	Intermediate Similarity	NPC248913
0.7	Intermediate Similarity	NPC99380
0.7	Intermediate Similarity	NPC22134
0.7	Intermediate Similarity	NPC45579
0.7	Intermediate Similarity	NPC160540
0.6989	Remote Similarity	NPC208094
0.6988	Remote Similarity	NPC470429
0.6988	Remote Similarity	NPC19900
0.6988	Remote Similarity	NPC308038
0.6988	Remote Similarity	NPC472490
0.6986	Remote Similarity	NPC127582
0.6977	Remote Similarity	NPC33913
0.6977	Remote Similarity	NPC476412
0.6977	Remote Similarity	NPC144258
0.6974	Remote Similarity	NPC137163
0.6966	Remote Similarity	NPC36668
0.6966	Remote Similarity	NPC118011
0.6966	Remote Similarity	NPC112454
0.6966	Remote Similarity	NPC326627
0.6966	Remote Similarity	NPC65615
0.6966	Remote Similarity	NPC68148
0.6966	Remote Similarity	NPC5509
0.6966	Remote Similarity	NPC310010
0.6966	Remote Similarity	NPC474918
0.6966	Remote Similarity	NPC477973
0.6962	Remote Similarity	NPC84790
0.6957	Remote Similarity	NPC777
0.6957	Remote Similarity	NPC147232
0.6951	Remote Similarity	NPC476811
0.6951	Remote Similarity	NPC476007
0.6951	Remote Similarity	NPC470428
0.6951	Remote Similarity	NPC472300
0.6951	Remote Similarity	NPC266193
0.6951	Remote Similarity	NPC197659
0.6951	Remote Similarity	NPC473536
0.6951	Remote Similarity	NPC325946
0.6951	Remote Similarity	NPC257666
0.6951	Remote Similarity	NPC211279
0.6944	Remote Similarity	NPC139056
0.6944	Remote Similarity	NPC60772
0.6944	Remote Similarity	NPC320421
0.6941	Remote Similarity	NPC238991
0.6941	Remote Similarity	NPC212083
0.6941	Remote Similarity	NPC302661
0.6941	Remote Similarity	NPC48362
0.6933	Remote Similarity	NPC169275
0.6933	Remote Similarity	NPC52449
0.6932	Remote Similarity	NPC472324
0.6932	Remote Similarity	NPC476079
0.6932	Remote Similarity	NPC113370
0.6932	Remote Similarity	NPC230016

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 NPC147438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1484
0.2-0.3	4407
0.3-0.4	2357
0.4-0.5	434
0.5-0.6	211
0.6-0.7	114
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
0.8205	Intermediate Similarity	NPD4695	Discontinued
0.7317	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8779	Phase 3
0.726	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3704	Approved
0.72	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4756	Discovery
0.7073	Intermediate Similarity	NPD3617	Approved
0.7011	Intermediate Similarity	NPD5279	Phase 3
0.7011	Intermediate Similarity	NPD5690	Phase 2
0.6977	Remote Similarity	NPD4197	Approved
0.6966	Remote Similarity	NPD4753	Phase 2
0.6966	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD5329	Approved
0.6854	Remote Similarity	NPD6672	Approved
0.6854	Remote Similarity	NPD5737	Approved
0.6835	Remote Similarity	NPD4691	Approved
0.6818	Remote Similarity	NPD4694	Approved
0.6818	Remote Similarity	NPD5280	Approved
0.6809	Remote Similarity	NPD6083	Phase 2
0.6809	Remote Similarity	NPD6084	Phase 2
0.6786	Remote Similarity	NPD4195	Approved
0.6782	Remote Similarity	NPD3665	Phase 1
0.6782	Remote Similarity	NPD3666	Approved
0.6782	Remote Similarity	NPD3133	Approved
0.6774	Remote Similarity	NPD4629	Approved
0.6774	Remote Similarity	NPD5210	Approved
0.6753	Remote Similarity	NPD7331	Phase 2
0.6744	Remote Similarity	NPD4223	Phase 3
0.6744	Remote Similarity	NPD4221	Approved
0.6744	Remote Similarity	NPD3667	Approved
0.6737	Remote Similarity	NPD5696	Approved
0.6709	Remote Similarity	NPD4137	Phase 3
0.6702	Remote Similarity	NPD5222	Approved
0.6702	Remote Similarity	NPD5221	Approved
0.6702	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6110	Phase 1
0.6632	Remote Similarity	NPD5173	Approved
0.6629	Remote Similarity	NPD3618	Phase 1
0.6629	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4747	Approved
0.6593	Remote Similarity	NPD6673	Approved
0.6593	Remote Similarity	NPD6080	Approved
0.6593	Remote Similarity	NPD6904	Approved
0.6591	Remote Similarity	NPD4786	Approved
0.6585	Remote Similarity	NPD4058	Approved
0.6543	Remote Similarity	NPD5276	Approved
0.6526	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD5692	Phase 3
0.6517	Remote Similarity	NPD1696	Phase 3
0.6495	Remote Similarity	NPD4696	Approved
0.6495	Remote Similarity	NPD5285	Approved
0.6495	Remote Similarity	NPD5286	Approved
0.6489	Remote Similarity	NPD7748	Approved
0.6458	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD5694	Approved
0.6452	Remote Similarity	NPD7515	Phase 2
0.6452	Remote Similarity	NPD5693	Phase 1
0.6452	Remote Similarity	NPD6050	Approved
0.6452	Remote Similarity	NPD6079	Approved
0.6444	Remote Similarity	NPD4693	Phase 3
0.6444	Remote Similarity	NPD4138	Approved
0.6444	Remote Similarity	NPD4623	Approved
0.6444	Remote Similarity	NPD4688	Approved
0.6444	Remote Similarity	NPD4690	Approved
0.6444	Remote Similarity	NPD4519	Discontinued
0.6444	Remote Similarity	NPD5205	Approved
0.6444	Remote Similarity	NPD4689	Approved
0.6436	Remote Similarity	NPD5697	Approved
0.6429	Remote Similarity	NPD5223	Approved
0.6413	Remote Similarity	NPD5328	Approved
0.641	Remote Similarity	NPD7341	Phase 2
0.6404	Remote Similarity	NPD3668	Phase 3
0.6386	Remote Similarity	NPD5733	Approved
0.6386	Remote Similarity	NPD4687	Approved
0.6383	Remote Similarity	NPD6399	Phase 3
0.6373	Remote Similarity	NPD6899	Approved
0.6373	Remote Similarity	NPD6011	Approved
0.6373	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7128	Approved
0.6337	Remote Similarity	NPD5739	Approved
0.6337	Remote Similarity	NPD6675	Approved
0.6337	Remote Similarity	NPD6402	Approved
0.6327	Remote Similarity	NPD4700	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.63	Remote Similarity	NPD5174	Approved
0.63	Remote Similarity	NPD5175	Approved
0.6289	Remote Similarity	NPD7902	Approved
0.6277	Remote Similarity	NPD5281	Approved
0.6277	Remote Similarity	NPD5284	Approved
0.6275	Remote Similarity	NPD5701	Approved
0.6267	Remote Similarity	NPD287	Approved
0.6264	Remote Similarity	NPD7146	Approved
0.6264	Remote Similarity	NPD5330	Approved
0.6264	Remote Similarity	NPD6098	Approved
0.6264	Remote Similarity	NPD7521	Approved
0.6264	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD6409	Approved
0.6264	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7290	Approved
0.6238	Remote Similarity	NPD5141	Approved
0.6235	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4225	Approved
0.6222	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7320	Approved
0.6211	Remote Similarity	NPD4202	Approved
0.6211	Remote Similarity	NPD5133	Approved
0.62	Remote Similarity	NPD5091	Approved
0.6196	Remote Similarity	NPD3573	Approved
0.619	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD8130	Phase 1
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6649	Approved
0.619	Remote Similarity	NPD6617	Approved
0.6173	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4096	Approved
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6372	Approved
0.6139	Remote Similarity	NPD4754	Approved
0.6132	Remote Similarity	NPD8297	Approved
0.6132	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD6903	Approved
0.6129	Remote Similarity	NPD4518	Approved
0.6129	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD8264	Approved
0.6118	Remote Similarity	NPD6942	Approved
0.6118	Remote Similarity	NPD7339	Approved
0.6111	Remote Similarity	NPD4788	Approved
0.6098	Remote Similarity	NPD6923	Approved
0.6098	Remote Similarity	NPD6922	Approved
0.6082	Remote Similarity	NPD5654	Approved
0.6058	Remote Similarity	NPD5168	Approved
0.6058	Remote Similarity	NPD5128	Approved
0.6058	Remote Similarity	NPD4730	Approved
0.6058	Remote Similarity	NPD4729	Approved
0.6038	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4192	Approved
0.6026	Remote Similarity	NPD4191	Approved
0.6026	Remote Similarity	NPD4194	Approved
0.6026	Remote Similarity	NPD4193	Approved
0.6024	Remote Similarity	NPD7144	Approved
0.6024	Remote Similarity	NPD7143	Approved
0.6023	Remote Similarity	NPD7645	Phase 2
0.602	Remote Similarity	NPD7614	Phase 1
0.6019	Remote Similarity	NPD4767	Approved
0.6019	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD6924	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4785	Approved
0.6	Remote Similarity	NPD6926	Approved
0.6	Remote Similarity	NPD4784	Approved
0.5979	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7900	Approved
0.5978	Remote Similarity	NPD1694	Approved
0.5963	Remote Similarity	NPD6274	Approved
0.5963	Remote Similarity	NPD6868	Approved
0.596	Remote Similarity	NPD5959	Approved
0.5957	Remote Similarity	NPD5208	Approved
0.5952	Remote Similarity	NPD7150	Approved
0.5952	Remote Similarity	NPD4243	Approved
0.5952	Remote Similarity	NPD7152	Approved
0.5952	Remote Similarity	NPD7151	Approved
0.5943	Remote Similarity	NPD4634	Approved
0.5943	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5248	Approved
0.5943	Remote Similarity	NPD5250	Approved
0.5943	Remote Similarity	NPD5251	Approved
0.5943	Remote Similarity	NPD5135	Approved
0.5943	Remote Similarity	NPD5249	Phase 3
0.5943	Remote Similarity	NPD5247	Approved
0.5943	Remote Similarity	NPD5169	Approved
0.5938	Remote Similarity	NPD7637	Suspended
0.5938	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7154	Phase 3
0.5926	Remote Similarity	NPD4632	Approved
0.5918	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6009	Approved
0.5909	Remote Similarity	NPD6317	Approved
0.59	Remote Similarity	NPD7638	Approved
0.5889	Remote Similarity	NPD4692	Approved
0.5889	Remote Similarity	NPD8028	Phase 2
0.5889	Remote Similarity	NPD4139	Approved
0.5888	Remote Similarity	NPD5217	Approved
0.5888	Remote Similarity	NPD5215	Approved
0.5888	Remote Similarity	NPD5216	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