NPASS Compound

Structure

CID241512 OpenBabel06191716042D 26 28 0 0 1 0 0 0 0 0999 V2000 3.4641 -0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -4.3301 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 2.5981 -1.5000 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 0.8660 1.5000 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 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 1 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 21 1 1 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 3 1 6 0 0 0 22 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	3.381
LogD:	2.909
LogS:	-4.626
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.357
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.783
MDCK Permeability:	2.335767749173101e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.239
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	91.02216339111328%
Volume Distribution (VD):	0.485
Pgp-substrate:	2.509171962738037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.661
CYP1A2-substrate:	0.847
CYP2C19-inhibitor:	0.45
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.633
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	1.895
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.748
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.941
Carcinogencity:	0.796
Eye Corrosion:	0.04
Eye Irritation:	0.126
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC241512

Natural Product ID:	NPC241512
*Common Name:**	5-Epiilimaquinone
IUPAC Name:	3-[[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	5-Epiilimaquinone
Standard InCHIKey:	JJWITJNSXCXULM-UPOGBMBOSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21-,22+/m0/s1
SMILES:	COC1=CC(=O)C(=C(C1=O)C[C@]1(C)[C@@H](C)CC[C@@]2([C@H]1CCCC2=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521729
PubChem CID:	21727418
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
NPO32618	Hyrtios	Genus	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785412]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978215]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542344]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21155589]
NPO40703	Verongula cf. rigida Esper	Strain	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32040314]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964793]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
LD50	1
Others	4

Activity Type	# Activity
Cell Line	3
CELL-LINE	3
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[447775]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[447775]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[447775]
NPT140	Organism	Artemia	Artemia	LD50	=	4.0	mg/L	PMID[447774]
NPT2	Others	Unspecified		Inhibition	<=	50.0	%	PMID[447775]
NPT20972	CELL-LINE	SU.86.86	Homo sapiens	Activity	>	30.0	%	PMID[447776]
NPT20972	CELL-LINE	SU.86.86	Homo sapiens	Activity	>	20.0	%	PMID[447776]

☑ 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 NPC241512 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	186
0.1-0.2	1182
0.2-0.3	4563
0.3-0.4	12280
0.4-0.5	11986
0.5-0.6	7030
0.6-0.7	4136
0.7-0.8	1223
0.8-0.85	79
0.85-0.9	19
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC6185
0.975	High Similarity	NPC8518
0.975	High Similarity	NPC263997
0.975	High Similarity	NPC132228
0.9268	High Similarity	NPC474680
0.925	High Similarity	NPC55869
0.925	High Similarity	NPC474085
0.9176	High Similarity	NPC475823
0.9176	High Similarity	NPC474209
0.9125	High Similarity	NPC108955
0.9036	High Similarity	NPC133652
0.9024	High Similarity	NPC105803
0.9012	High Similarity	NPC99308
0.8902	High Similarity	NPC103486
0.8736	High Similarity	NPC223093
0.8659	High Similarity	NPC2482
0.8642	High Similarity	NPC30321
0.8625	High Similarity	NPC92080
0.8625	High Similarity	NPC26504
0.8608	High Similarity	NPC147438
0.8571	High Similarity	NPC53733
0.8554	High Similarity	NPC225515
0.8554	High Similarity	NPC278459
0.8554	High Similarity	NPC121984
0.8539	High Similarity	NPC263780
0.8537	High Similarity	NPC192329
0.8537	High Similarity	NPC27817
0.8488	Intermediate Similarity	NPC94666
0.8471	Intermediate Similarity	NPC237712
0.8444	Intermediate Similarity	NPC23170
0.8434	Intermediate Similarity	NPC476809
0.8427	Intermediate Similarity	NPC174167
0.8427	Intermediate Similarity	NPC470036
0.8427	Intermediate Similarity	NPC26865
0.8415	Intermediate Similarity	NPC189485
0.8415	Intermediate Similarity	NPC476808
0.8395	Intermediate Similarity	NPC1254
0.8372	Intermediate Similarity	NPC469993
0.8333	Intermediate Similarity	NPC116797
0.8316	Intermediate Similarity	NPC179208
0.8313	Intermediate Similarity	NPC475681
0.8313	Intermediate Similarity	NPC476177
0.8295	Intermediate Similarity	NPC53454
0.8293	Intermediate Similarity	NPC165711
0.8293	Intermediate Similarity	NPC472300
0.8293	Intermediate Similarity	NPC476811
0.8276	Intermediate Similarity	NPC327115
0.8256	Intermediate Similarity	NPC144258
0.8214	Intermediate Similarity	NPC18955
0.8214	Intermediate Similarity	NPC472478
0.8202	Intermediate Similarity	NPC65615
0.8202	Intermediate Similarity	NPC326627
0.8202	Intermediate Similarity	NPC68148
0.8202	Intermediate Similarity	NPC477973
0.8202	Intermediate Similarity	NPC112454
0.8202	Intermediate Similarity	NPC310010
0.8193	Intermediate Similarity	NPC74410
0.8193	Intermediate Similarity	NPC23778
0.8171	Intermediate Similarity	NPC180886
0.8171	Intermediate Similarity	NPC470525
0.8171	Intermediate Similarity	NPC110725
0.8161	Intermediate Similarity	NPC469948
0.8161	Intermediate Similarity	NPC33663
0.8161	Intermediate Similarity	NPC32037
0.8161	Intermediate Similarity	NPC255174
0.8152	Intermediate Similarity	NPC777
0.8152	Intermediate Similarity	NPC147232
0.8132	Intermediate Similarity	NPC211230
0.8125	Intermediate Similarity	NPC474539
0.8118	Intermediate Similarity	NPC90055
0.8118	Intermediate Similarity	NPC472684
0.8118	Intermediate Similarity	NPC473217
0.8118	Intermediate Similarity	NPC44963
0.8118	Intermediate Similarity	NPC471898
0.8118	Intermediate Similarity	NPC475833
0.8111	Intermediate Similarity	NPC38952
0.809	Intermediate Similarity	NPC307298
0.8072	Intermediate Similarity	NPC283087
0.8068	Intermediate Similarity	NPC51014
0.8068	Intermediate Similarity	NPC203795
0.8068	Intermediate Similarity	NPC474778
0.8068	Intermediate Similarity	NPC145879
0.8068	Intermediate Similarity	NPC474733
0.8068	Intermediate Similarity	NPC20688
0.8068	Intermediate Similarity	NPC474732
0.8068	Intermediate Similarity	NPC31564
0.8049	Intermediate Similarity	NPC175079
0.8046	Intermediate Similarity	NPC329043
0.8046	Intermediate Similarity	NPC321187
0.8046	Intermediate Similarity	NPC476412
0.8046	Intermediate Similarity	NPC214043
0.8046	Intermediate Similarity	NPC85774
0.8046	Intermediate Similarity	NPC58841
0.8046	Intermediate Similarity	NPC96095
0.8046	Intermediate Similarity	NPC161423
0.8046	Intermediate Similarity	NPC227064
0.8043	Intermediate Similarity	NPC474882
0.8043	Intermediate Similarity	NPC474328
0.8043	Intermediate Similarity	NPC196485
0.8043	Intermediate Similarity	NPC245972
0.8023	Intermediate Similarity	NPC193347
0.8023	Intermediate Similarity	NPC310989
0.8023	Intermediate Similarity	NPC238991
0.8023	Intermediate Similarity	NPC302661
0.8023	Intermediate Similarity	NPC212083
0.8023	Intermediate Similarity	NPC151519
0.8023	Intermediate Similarity	NPC48362
0.8022	Intermediate Similarity	NPC168027
0.8022	Intermediate Similarity	NPC185936
0.8022	Intermediate Similarity	NPC248913
0.8022	Intermediate Similarity	NPC99380
0.8	Intermediate Similarity	NPC119416
0.8	Intermediate Similarity	NPC469637
0.8	Intermediate Similarity	NPC31985
0.8	Intermediate Similarity	NPC184663
0.8	Intermediate Similarity	NPC474245
0.8	Intermediate Similarity	NPC104545
0.8	Intermediate Similarity	NPC1015
0.7978	Intermediate Similarity	NPC230016
0.7978	Intermediate Similarity	NPC470523
0.7978	Intermediate Similarity	NPC220930
0.7978	Intermediate Similarity	NPC93778
0.7978	Intermediate Similarity	NPC475740
0.7978	Intermediate Similarity	NPC272039
0.7978	Intermediate Similarity	NPC58063
0.7976	Intermediate Similarity	NPC471409
0.7976	Intermediate Similarity	NPC321514
0.7976	Intermediate Similarity	NPC62336
0.7976	Intermediate Similarity	NPC275494
0.7957	Intermediate Similarity	NPC280725
0.7957	Intermediate Similarity	NPC295347
0.7955	Intermediate Similarity	NPC29447
0.7955	Intermediate Similarity	NPC474537
0.7955	Intermediate Similarity	NPC90287
0.7955	Intermediate Similarity	NPC476426
0.7952	Intermediate Similarity	NPC263582
0.7952	Intermediate Similarity	NPC69143
0.7938	Intermediate Similarity	NPC131366
0.7935	Intermediate Similarity	NPC233118
0.7931	Intermediate Similarity	NPC8091
0.7931	Intermediate Similarity	NPC307258
0.7931	Intermediate Similarity	NPC49019
0.7931	Intermediate Similarity	NPC102197
0.7912	Intermediate Similarity	NPC129913
0.7912	Intermediate Similarity	NPC476437
0.7912	Intermediate Similarity	NPC113393
0.7912	Intermediate Similarity	NPC476369
0.7907	Intermediate Similarity	NPC14151
0.7907	Intermediate Similarity	NPC475863
0.7907	Intermediate Similarity	NPC3915
0.7907	Intermediate Similarity	NPC149237
0.7907	Intermediate Similarity	NPC470034
0.7907	Intermediate Similarity	NPC189237
0.7889	Intermediate Similarity	NPC230387
0.7889	Intermediate Similarity	NPC48107
0.7889	Intermediate Similarity	NPC470524
0.7889	Intermediate Similarity	NPC206060
0.7882	Intermediate Similarity	NPC474113
0.7882	Intermediate Similarity	NPC199595
0.7882	Intermediate Similarity	NPC472490
0.7882	Intermediate Similarity	NPC170394
0.7875	Intermediate Similarity	NPC262673
0.7865	Intermediate Similarity	NPC472974
0.7857	Intermediate Similarity	NPC266193
0.7857	Intermediate Similarity	NPC197659
0.7857	Intermediate Similarity	NPC257666
0.7857	Intermediate Similarity	NPC40170
0.7857	Intermediate Similarity	NPC97377
0.7849	Intermediate Similarity	NPC212812
0.7848	Intermediate Similarity	NPC243272
0.7841	Intermediate Similarity	NPC53385
0.7841	Intermediate Similarity	NPC180834
0.7841	Intermediate Similarity	NPC473246
0.7841	Intermediate Similarity	NPC59453
0.7841	Intermediate Similarity	NPC472265
0.7841	Intermediate Similarity	NPC221758
0.7831	Intermediate Similarity	NPC279666
0.7831	Intermediate Similarity	NPC192540
0.7826	Intermediate Similarity	NPC230064
0.7826	Intermediate Similarity	NPC131872
0.7816	Intermediate Similarity	NPC69101
0.7816	Intermediate Similarity	NPC320514
0.7816	Intermediate Similarity	NPC251779
0.7812	Intermediate Similarity	NPC472972
0.7802	Intermediate Similarity	NPC5509
0.7802	Intermediate Similarity	NPC262043
0.7802	Intermediate Similarity	NPC36668
0.7802	Intermediate Similarity	NPC477943
0.7802	Intermediate Similarity	NPC474918
0.7802	Intermediate Similarity	NPC186688
0.7802	Intermediate Similarity	NPC26959
0.7802	Intermediate Similarity	NPC305039
0.7802	Intermediate Similarity	NPC268406
0.7802	Intermediate Similarity	NPC76879
0.7802	Intermediate Similarity	NPC474700
0.7802	Intermediate Similarity	NPC118011
0.7791	Intermediate Similarity	NPC287063
0.7791	Intermediate Similarity	NPC477057
0.7791	Intermediate Similarity	NPC37038
0.7789	Intermediate Similarity	NPC208094

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 NPC241512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1494
0.2-0.3	3780
0.3-0.4	2491
0.4-0.5	782
0.5-0.6	188
0.6-0.7	127
0.7-0.8	112
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9367	High Similarity	NPD4695	Discontinued
0.8415	Intermediate Similarity	NPD3617	Approved
0.8256	Intermediate Similarity	NPD4197	Approved
0.8202	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD4753	Phase 2
0.8161	Intermediate Similarity	NPD5329	Approved
0.809	Intermediate Similarity	NPD6672	Approved
0.809	Intermediate Similarity	NPD5737	Approved
0.8068	Intermediate Similarity	NPD5690	Phase 2
0.8046	Intermediate Similarity	NPD3133	Approved
0.8046	Intermediate Similarity	NPD3666	Approved
0.8046	Intermediate Similarity	NPD3665	Phase 1
0.8023	Intermediate Similarity	NPD4221	Approved
0.8023	Intermediate Similarity	NPD4223	Phase 3
0.8023	Intermediate Similarity	NPD3667	Approved
0.7979	Intermediate Similarity	NPD6083	Phase 2
0.7979	Intermediate Similarity	NPD6084	Phase 2
0.7957	Intermediate Similarity	NPD5695	Phase 3
0.7957	Intermediate Similarity	NPD5210	Approved
0.7957	Intermediate Similarity	NPD4629	Approved
0.7895	Intermediate Similarity	NPD5696	Approved
0.7872	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5222	Approved
0.7872	Intermediate Similarity	NPD5221	Approved
0.7865	Intermediate Similarity	NPD5280	Approved
0.7865	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD3618	Phase 1
0.7865	Intermediate Similarity	NPD5279	Phase 3
0.7865	Intermediate Similarity	NPD4694	Approved
0.7841	Intermediate Similarity	NPD4786	Approved
0.7802	Intermediate Similarity	NPD6673	Approved
0.7802	Intermediate Similarity	NPD6080	Approved
0.7802	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD5173	Approved
0.7684	Intermediate Similarity	NPD4697	Phase 3
0.7667	Intermediate Similarity	NPD5205	Approved
0.7667	Intermediate Similarity	NPD4690	Approved
0.7667	Intermediate Similarity	NPD4519	Discontinued
0.7667	Intermediate Similarity	NPD4623	Approved
0.7667	Intermediate Similarity	NPD4693	Phase 3
0.7667	Intermediate Similarity	NPD4138	Approved
0.7667	Intermediate Similarity	NPD4689	Approved
0.7667	Intermediate Similarity	NPD4688	Approved
0.766	Intermediate Similarity	NPD7748	Approved
0.764	Intermediate Similarity	NPD3668	Phase 3
0.7634	Intermediate Similarity	NPD6079	Approved
0.7634	Intermediate Similarity	NPD5693	Phase 1
0.7634	Intermediate Similarity	NPD7515	Phase 2
0.7629	Intermediate Similarity	NPD5286	Approved
0.7629	Intermediate Similarity	NPD4696	Approved
0.7629	Intermediate Similarity	NPD5285	Approved
0.7609	Intermediate Similarity	NPD5328	Approved
0.7604	Intermediate Similarity	NPD4755	Approved
0.7561	Intermediate Similarity	NPD4691	Approved
0.7553	Intermediate Similarity	NPD6399	Phase 3
0.7551	Intermediate Similarity	NPD5223	Approved
0.7527	Intermediate Similarity	NPD5692	Phase 3
0.7525	Intermediate Similarity	NPD5697	Approved
0.7475	Intermediate Similarity	NPD5226	Approved
0.7475	Intermediate Similarity	NPD5224	Approved
0.7475	Intermediate Similarity	NPD4633	Approved
0.7475	Intermediate Similarity	NPD5211	Phase 2
0.7475	Intermediate Similarity	NPD5225	Approved
0.7473	Intermediate Similarity	NPD7146	Approved
0.7473	Intermediate Similarity	NPD6098	Approved
0.7473	Intermediate Similarity	NPD7521	Approved
0.7473	Intermediate Similarity	NPD7334	Approved
0.7473	Intermediate Similarity	NPD6409	Approved
0.7473	Intermediate Similarity	NPD6684	Approved
0.7473	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD4195	Approved
0.7451	Intermediate Similarity	NPD6011	Approved
0.7451	Intermediate Similarity	NPD6899	Approved
0.7451	Intermediate Similarity	NPD6881	Approved
0.7449	Intermediate Similarity	NPD4700	Approved
0.7447	Intermediate Similarity	NPD6050	Approved
0.7447	Intermediate Similarity	NPD5694	Approved
0.7439	Intermediate Similarity	NPD4137	Phase 3
0.7426	Intermediate Similarity	NPD6675	Approved
0.7426	Intermediate Similarity	NPD6402	Approved
0.7426	Intermediate Similarity	NPD7128	Approved
0.7426	Intermediate Similarity	NPD5739	Approved
0.7423	Intermediate Similarity	NPD7902	Approved
0.74	Intermediate Similarity	NPD5175	Approved
0.74	Intermediate Similarity	NPD5174	Approved
0.7391	Intermediate Similarity	NPD3573	Approved
0.7379	Intermediate Similarity	NPD6014	Approved
0.7379	Intermediate Similarity	NPD6013	Approved
0.7379	Intermediate Similarity	NPD6012	Approved
0.7368	Intermediate Similarity	NPD4202	Approved
0.7353	Intermediate Similarity	NPD5701	Approved
0.7349	Intermediate Similarity	NPD4747	Approved
0.7342	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4788	Approved
0.7327	Intermediate Similarity	NPD5141	Approved
0.7312	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6903	Approved
0.7308	Intermediate Similarity	NPD7102	Approved
0.7308	Intermediate Similarity	NPD7290	Approved
0.7308	Intermediate Similarity	NPD6883	Approved
0.73	Intermediate Similarity	NPD5091	Approved
0.7294	Intermediate Similarity	NPD4058	Approved
0.7284	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3704	Approved
0.7282	Intermediate Similarity	NPD7320	Approved
0.7263	Intermediate Similarity	NPD5281	Approved
0.7263	Intermediate Similarity	NPD5284	Approved
0.7241	Intermediate Similarity	NPD4756	Discovery
0.7238	Intermediate Similarity	NPD6617	Approved
0.7238	Intermediate Similarity	NPD6869	Approved
0.7238	Intermediate Similarity	NPD6650	Approved
0.7238	Intermediate Similarity	NPD6847	Approved
0.7238	Intermediate Similarity	NPD6649	Approved
0.7238	Intermediate Similarity	NPD8130	Phase 1
0.7228	Intermediate Similarity	NPD4754	Approved
0.7222	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD6373	Approved
0.7188	Intermediate Similarity	NPD5133	Approved
0.717	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7614	Phase 1
0.7128	Intermediate Similarity	NPD5208	Approved
0.7115	Intermediate Similarity	NPD4729	Approved
0.7115	Intermediate Similarity	NPD4730	Approved
0.7115	Intermediate Similarity	NPD5128	Approved
0.7115	Intermediate Similarity	NPD5168	Approved
0.7113	Intermediate Similarity	NPD5282	Discontinued
0.7113	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD4768	Approved
0.7087	Intermediate Similarity	NPD4767	Approved
0.7075	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5654	Approved
0.7	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5169	Approved
0.6981	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4634	Approved
0.6981	Remote Similarity	NPD5248	Approved
0.6981	Remote Similarity	NPD5250	Approved
0.6981	Remote Similarity	NPD5247	Approved
0.6981	Remote Similarity	NPD5135	Approved
0.6981	Remote Similarity	NPD5251	Approved
0.6981	Remote Similarity	NPD5249	Phase 3
0.6979	Remote Similarity	NPD4096	Approved
0.6972	Remote Similarity	NPD6274	Approved
0.6972	Remote Similarity	NPD6868	Approved
0.697	Remote Similarity	NPD7732	Phase 3
0.6947	Remote Similarity	NPD4518	Approved
0.6944	Remote Similarity	NPD4632	Approved
0.6932	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6916	Remote Similarity	NPD5127	Approved
0.6916	Remote Similarity	NPD5215	Approved
0.6916	Remote Similarity	NPD5216	Approved
0.6916	Remote Similarity	NPD5217	Approved
0.6909	Remote Similarity	NPD6317	Approved
0.6909	Remote Similarity	NPD6009	Approved
0.6905	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5959	Approved
0.6897	Remote Similarity	NPD5733	Approved
0.6897	Remote Similarity	NPD4687	Approved
0.6867	Remote Similarity	NPD7331	Phase 2
0.686	Remote Similarity	NPD5276	Approved
0.6857	Remote Similarity	NPD6412	Phase 2
0.6857	Remote Similarity	NPD6614	Approved
0.6847	Remote Similarity	NPD6313	Approved
0.6847	Remote Similarity	NPD6314	Approved
0.6847	Remote Similarity	NPD6335	Approved
0.6818	Remote Similarity	NPD6942	Approved
0.6818	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD1696	Phase 3
0.6804	Remote Similarity	NPD5207	Approved
0.6786	Remote Similarity	NPD7100	Approved
0.6786	Remote Similarity	NPD7101	Approved
0.6768	Remote Similarity	NPD6001	Approved
0.6747	Remote Similarity	NPD7341	Phase 2
0.6735	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD5167	Approved
0.6726	Remote Similarity	NPD6054	Approved
0.6726	Remote Similarity	NPD6319	Approved
0.6705	Remote Similarity	NPD4784	Approved
0.6705	Remote Similarity	NPD4785	Approved
0.6703	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6632	Remote Similarity	NPD1694	Approved
0.6609	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD5988	Approved
0.6607	Remote Similarity	NPD7115	Discovery
0.6604	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD7640	Approved
0.6602	Remote Similarity	NPD7639	Approved
0.6579	Remote Similarity	NPD6059	Approved
0.6559	Remote Similarity	NPD8028	Phase 2

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