NPASS Compound

Structure

CID316262 OpenBabel06191716132D 31 34 0 0 1 0 0 0 0 0999 V2000 -4.5817 2.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9454 -1.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2763 -0.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1444 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9486 0.2421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7407 1.2202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0955 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2055 -0.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7897 1.5292 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 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0465 0.8601 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2544 -0.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9400 -0.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 2.9781 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 14 2 0 0 0 0 2 15 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 17 1 0 0 0 0 15 26 1 6 0 0 0 15 31 1 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 27 2 0 0 0 0 19 22 2 0 0 0 0 19 28 1 0 0 0 0 20 23 1 0 0 0 0 20 30 1 0 0 0 0 21 24 2 0 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 29 2 0 0 0 0 24 31 1 0 0 0 0 26 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.22
Volume:	449.522
LogP:	5.374
LogD:	3.9
LogS:	-6.403
# Rotatable Bonds:	4
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	4.495
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89
MDCK Permeability:	2.003290683205705e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	97.37510681152344%
Volume Distribution (VD):	0.641
Pgp-substrate:	0.9465335011482239%

ADMET: Metabolism

CYP1A2-inhibitor:	0.74
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.463
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.83
CYP2D6-substrate:	0.684
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	3.547
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.763
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.19
Carcinogencity:	0.619
Eye Corrosion:	0.003
Eye Irritation:	0.173
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC316262

Natural Product ID:	NPC316262
*Common Name:**	Marfuraquinocin A
IUPAC Name:	(2R,3S)-3-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-4-hydroxy-7-methoxy-2,3-dimethyl-2H-benzo[g][1]benzofuran-6,9-dione
Synonyms:
Standard InCHIKey:	OOGVVQMYQYWZGB-OIVWUYHGSA-N
Standard InCHI:	InChI=1S/C26H32O5/c1-14-8-7-10-25(3,4)17(14)9-11-26(5)15(2)31-24-21-16(12-19(28)22(24)26)23(29)20(30-6)13-18(21)27/h12-13,15,17,28H,1,7-11H2,2-6H3/t15-,17?,26-/m1/s1
SMILES:	C=C1CCCC(C)(C)C1CC[C@]1(C)[C@@H](C)Oc2c3c(cc(c12)O)C(=O)C(=CC3=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092696
PubChem CID:	73603998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO6655.3	Streptomyces niveus SCSIO 3406	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24251399]

☑ 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	4
MIC	7

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	26700.0	nM	PMID[500200]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	17500.0	nM	PMID[500200]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12900.0	nM	PMID[500200]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	3700.0	nM	PMID[500200]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[500200]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	128.0	ug.mL-1	PMID[500200]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	128.0	ug.mL-1	PMID[500200]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	128.0	ug.mL-1	PMID[500200]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[500200]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	64.0	ug.mL-1	PMID[500200]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[500200]

☑ 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 NPC316262 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	418
0.1-0.2	1545
0.2-0.3	3130
0.3-0.4	7416
0.4-0.5	10602
0.5-0.6	4950
0.6-0.7	5398
0.7-0.8	6457
0.8-0.85	2382
0.85-0.9	378
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC314653
0.9748	High Similarity	NPC313717
0.9748	High Similarity	NPC315306
0.9742	High Similarity	NPC313368
0.9371	High Similarity	NPC475106
0.9313	High Similarity	NPC100849
0.9108	High Similarity	NPC40356
0.9108	High Similarity	NPC154683
0.9085	High Similarity	NPC54903
0.9085	High Similarity	NPC286074
0.908	High Similarity	NPC120857
0.908	High Similarity	NPC85047
0.908	High Similarity	NPC17274
0.9036	High Similarity	NPC475080
0.9006	High Similarity	NPC470810
0.9	High Similarity	NPC196448
0.9	High Similarity	NPC201127
0.8987	High Similarity	NPC87708
0.8981	High Similarity	NPC470568
0.8976	High Similarity	NPC118128
0.897	High Similarity	NPC20734
0.8963	High Similarity	NPC125465
0.8957	High Similarity	NPC469395
0.8951	High Similarity	NPC61382
0.8951	High Similarity	NPC103816
0.8941	High Similarity	NPC475656
0.8941	High Similarity	NPC475148
0.8938	High Similarity	NPC180924
0.8931	High Similarity	NPC193200
0.8924	High Similarity	NPC230848
0.8924	High Similarity	NPC232645
0.8924	High Similarity	NPC478148
0.8924	High Similarity	NPC470569
0.8924	High Similarity	NPC72958
0.8922	High Similarity	NPC469393
0.8916	High Similarity	NPC193698
0.8909	High Similarity	NPC193222
0.8903	High Similarity	NPC28632
0.8889	High Similarity	NPC472618
0.8882	High Similarity	NPC246647
0.8882	High Similarity	NPC164110
0.8882	High Similarity	NPC272196
0.8882	High Similarity	NPC96342
0.8882	High Similarity	NPC474637
0.8882	High Similarity	NPC212967
0.8868	High Similarity	NPC470340
0.8868	High Similarity	NPC470353
0.8861	High Similarity	NPC147735
0.8861	High Similarity	NPC202595
0.8861	High Similarity	NPC321896
0.8861	High Similarity	NPC476185
0.8848	High Similarity	NPC62444
0.8848	High Similarity	NPC476255
0.8848	High Similarity	NPC476056
0.8841	High Similarity	NPC476822
0.8834	High Similarity	NPC476929
0.8834	High Similarity	NPC187354
0.8827	High Similarity	NPC239118
0.8827	High Similarity	NPC472617
0.882	High Similarity	NPC477674
0.8812	High Similarity	NPC210942
0.8812	High Similarity	NPC169990
0.8812	High Similarity	NPC472799
0.8812	High Similarity	NPC477669
0.8805	High Similarity	NPC149526
0.8805	High Similarity	NPC473131
0.8805	High Similarity	NPC474417
0.8805	High Similarity	NPC470675
0.8797	High Similarity	NPC100985
0.8797	High Similarity	NPC80370
0.8797	High Similarity	NPC317492
0.8797	High Similarity	NPC269420
0.8797	High Similarity	NPC65589
0.8797	High Similarity	NPC471114
0.8797	High Similarity	NPC97028
0.8797	High Similarity	NPC97029
0.8797	High Similarity	NPC158338
0.8797	High Similarity	NPC288036
0.879	High Similarity	NPC289042
0.879	High Similarity	NPC118027
0.879	High Similarity	NPC56433
0.879	High Similarity	NPC245584
0.879	High Similarity	NPC259632
0.879	High Similarity	NPC312929
0.879	High Similarity	NPC190648
0.879	High Similarity	NPC126767
0.8788	High Similarity	NPC473286
0.8782	High Similarity	NPC474630
0.878	High Similarity	NPC94796
0.878	High Similarity	NPC473022
0.8765	High Similarity	NPC158542
0.8765	High Similarity	NPC281137
0.8765	High Similarity	NPC282390
0.8758	High Similarity	NPC148938
0.8758	High Similarity	NPC297531
0.8758	High Similarity	NPC213936
0.875	High Similarity	NPC169018
0.8742	High Similarity	NPC290954
0.8742	High Similarity	NPC294646
0.8742	High Similarity	NPC255641
0.8735	High Similarity	NPC475109
0.8734	High Similarity	NPC145467
0.8734	High Similarity	NPC7025
0.8734	High Similarity	NPC470460
0.8734	High Similarity	NPC39195
0.8734	High Similarity	NPC27221
0.8734	High Similarity	NPC256672
0.8734	High Similarity	NPC168085
0.8727	High Similarity	NPC208120
0.8727	High Similarity	NPC473313
0.8727	High Similarity	NPC173587
0.8727	High Similarity	NPC329669
0.8727	High Similarity	NPC472278
0.8727	High Similarity	NPC18100
0.8726	High Similarity	NPC24136
0.8726	High Similarity	NPC187282
0.8726	High Similarity	NPC470570
0.8726	High Similarity	NPC290133
0.8721	High Similarity	NPC228209
0.872	High Similarity	NPC117985
0.8718	High Similarity	NPC473812
0.8718	High Similarity	NPC473813
0.8712	High Similarity	NPC125969
0.8712	High Similarity	NPC85121
0.8712	High Similarity	NPC4950
0.8712	High Similarity	NPC186113
0.8712	High Similarity	NPC218818
0.8704	High Similarity	NPC164244
0.8704	High Similarity	NPC470352
0.8704	High Similarity	NPC470354
0.8704	High Similarity	NPC4547
0.8698	High Similarity	NPC98776
0.8698	High Similarity	NPC470333
0.8698	High Similarity	NPC154986
0.8696	High Similarity	NPC135522
0.8696	High Similarity	NPC235333
0.8696	High Similarity	NPC155686
0.8696	High Similarity	NPC214632
0.8688	High Similarity	NPC106372
0.8688	High Similarity	NPC258249
0.8688	High Similarity	NPC46882
0.8688	High Similarity	NPC477673
0.8688	High Similarity	NPC132990
0.8688	High Similarity	NPC58668
0.8688	High Similarity	NPC477672
0.8683	High Similarity	NPC232936
0.8679	High Similarity	NPC470461
0.8679	High Similarity	NPC65775
0.8679	High Similarity	NPC10027
0.8678	High Similarity	NPC240808
0.8675	High Similarity	NPC25361
0.8675	High Similarity	NPC146584
0.8675	High Similarity	NPC21016
0.8675	High Similarity	NPC472277
0.8675	High Similarity	NPC472049
0.8675	High Similarity	NPC136641
0.8671	High Similarity	NPC308200
0.8671	High Similarity	NPC7943
0.8671	High Similarity	NPC123202
0.8671	High Similarity	NPC10990
0.8671	High Similarity	NPC22005
0.8671	High Similarity	NPC300988
0.8667	High Similarity	NPC211107
0.8667	High Similarity	NPC470694
0.8662	High Similarity	NPC470673
0.8662	High Similarity	NPC34482
0.8662	High Similarity	NPC472446
0.8662	High Similarity	NPC117716
0.8662	High Similarity	NPC470674
0.8662	High Similarity	NPC472447
0.8659	High Similarity	NPC476283
0.8659	High Similarity	NPC43490
0.8659	High Similarity	NPC475107
0.8655	High Similarity	NPC23553
0.8655	High Similarity	NPC5671
0.8655	High Similarity	NPC77179
0.8655	High Similarity	NPC246877
0.8654	High Similarity	NPC277369
0.8654	High Similarity	NPC215451
0.865	High Similarity	NPC263483
0.865	High Similarity	NPC44199
0.865	High Similarity	NPC268360
0.8647	High Similarity	NPC294149
0.8647	High Similarity	NPC475398
0.8642	High Similarity	NPC471116
0.8642	High Similarity	NPC477687
0.8642	High Similarity	NPC477671
0.8639	High Similarity	NPC91650
0.8639	High Similarity	NPC477529
0.8639	High Similarity	NPC472620
0.8634	High Similarity	NPC268992
0.8634	High Similarity	NPC207624
0.8634	High Similarity	NPC180944
0.8634	High Similarity	NPC45934
0.8634	High Similarity	NPC470337
0.8634	High Similarity	NPC51824
0.8634	High Similarity	NPC113608
0.8634	High Similarity	NPC142308
0.8634	High Similarity	NPC273483
0.8634	High Similarity	NPC5871

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 NPC316262 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	937
0.2-0.3	1702
0.3-0.4	2583
0.4-0.5	1966
0.5-0.6	1011
0.6-0.7	407
0.7-0.8	157
0.8-0.85	27
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8544	High Similarity	NPD2533	Approved
0.8544	High Similarity	NPD2534	Approved
0.8544	High Similarity	NPD2532	Approved
0.8494	Intermediate Similarity	NPD6959	Discontinued
0.8466	Intermediate Similarity	NPD7819	Suspended
0.8462	Intermediate Similarity	NPD2800	Approved
0.8424	Intermediate Similarity	NPD7075	Discontinued
0.8364	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.8282	Intermediate Similarity	NPD6599	Discontinued
0.8214	Intermediate Similarity	NPD5494	Approved
0.8165	Intermediate Similarity	NPD1549	Phase 2
0.8153	Intermediate Similarity	NPD6100	Approved
0.8153	Intermediate Similarity	NPD6099	Approved
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD1934	Approved
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4380	Phase 2
0.805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD3226	Approved
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7962	Intermediate Similarity	NPD6651	Approved
0.7962	Intermediate Similarity	NPD1607	Approved
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6559	Discontinued
0.7933	Intermediate Similarity	NPD8434	Phase 2
0.7931	Intermediate Similarity	NPD3818	Discontinued
0.7927	Intermediate Similarity	NPD1512	Approved
0.7919	Intermediate Similarity	NPD6166	Phase 2
0.7919	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2801	Approved
0.7914	Intermediate Similarity	NPD6799	Approved
0.7907	Intermediate Similarity	NPD5710	Approved
0.7907	Intermediate Similarity	NPD5711	Approved
0.7904	Intermediate Similarity	NPD7411	Suspended
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD3749	Approved
0.787	Intermediate Similarity	NPD3817	Phase 2
0.784	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD1240	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7805	Intermediate Similarity	NPD1511	Approved
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5402	Approved
0.7764	Intermediate Similarity	NPD2346	Discontinued
0.7753	Intermediate Similarity	NPD7251	Discontinued
0.7746	Intermediate Similarity	NPD1247	Approved
0.7719	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7808	Phase 3
0.7706	Intermediate Similarity	NPD5760	Phase 2
0.7706	Intermediate Similarity	NPD5761	Phase 2
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD7390	Discontinued
0.7665	Intermediate Similarity	NPD920	Approved
0.7657	Intermediate Similarity	NPD3926	Phase 2
0.7654	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD1471	Phase 3
0.764	Intermediate Similarity	NPD7074	Phase 3
0.763	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD919	Approved
0.7627	Intermediate Similarity	NPD3751	Discontinued
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7611	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7229	Phase 3
0.7595	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2935	Discontinued
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.7584	Intermediate Similarity	NPD7054	Approved
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1243	Approved
0.756	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7472	Approved
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7531	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7471	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2309	Approved
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7696	Phase 3
0.7448	Intermediate Similarity	NPD7697	Approved
0.7448	Intermediate Similarity	NPD7698	Approved
0.7442	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD5401	Approved
0.7429	Intermediate Similarity	NPD6234	Discontinued
0.7425	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD2403	Approved
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4965	Approved
0.7414	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7399	Intermediate Similarity	NPD1465	Phase 2
0.7396	Intermediate Similarity	NPD6273	Approved
0.7391	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD8366	Approved
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7458	Discontinued
0.736	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7342	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4625	Phase 3
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7305	Intermediate Similarity	NPD7003	Approved
0.7303	Intermediate Similarity	NPD3787	Discontinued
0.7296	Intermediate Similarity	NPD7701	Phase 2
0.7292	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD7801	Approved
0.7268	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4749	Approved
0.7238	Intermediate Similarity	NPD7228	Approved
0.7233	Intermediate Similarity	NPD8491	Approved
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD8319	Approved
0.7229	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6696	Suspended
0.7211	Intermediate Similarity	NPD4360	Phase 2
0.7211	Intermediate Similarity	NPD4363	Phase 3
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7188	Intermediate Similarity	NPD7700	Phase 2
0.7188	Intermediate Similarity	NPD7699	Phase 2
0.7184	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4060	Phase 1
0.7178	Intermediate Similarity	NPD943	Approved
0.7174	Intermediate Similarity	NPD6765	Approved
0.7174	Intermediate Similarity	NPD6764	Approved
0.7173	Intermediate Similarity	NPD4361	Phase 2
0.7173	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD5406	Approved
0.7169	Intermediate Similarity	NPD5404	Approved
0.7169	Intermediate Similarity	NPD5408	Approved
0.7151	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7135	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD230	Phase 1
0.7122	Intermediate Similarity	NPD7907	Approved
0.7118	Intermediate Similarity	NPD7236	Approved
0.7095	Intermediate Similarity	NPD8067	Phase 3
0.7089	Intermediate Similarity	NPD3972	Approved
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD3764	Approved
0.7052	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7177	Discontinued
0.7041	Intermediate Similarity	NPD6823	Phase 2
0.7041	Intermediate Similarity	NPD2654	Approved
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7025	Intermediate Similarity	NPD1201	Approved
0.7025	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7024	Intermediate Similarity	NPD5763	Approved
0.7024	Intermediate Similarity	NPD5762	Approved
0.7024	Intermediate Similarity	NPD4111	Phase 1
0.7024	Intermediate Similarity	NPD4665	Approved
0.7021	Intermediate Similarity	NPD6784	Approved
0.7021	Intermediate Similarity	NPD6785	Approved
0.7019	Intermediate Similarity	NPD2798	Approved
0.7015	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7783	Phase 2
0.7012	Intermediate Similarity	NPD8032	Phase 2
0.7011	Intermediate Similarity	NPD7239	Suspended

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