NPASS Compound

Structure

CID315306 OpenBabel06191716132D 32 35 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 -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 -1.4945 -0.9706 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 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 -0.9945 -0.1045 0.0000 C 0 0 2 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 -2.4945 -0.9706 0.0000 O 0 0 0 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 25 1 0 0 0 0 3 25 1 0 0 0 0 5 31 1 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 28 2 0 0 0 0 18 22 2 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 6 0 0 0 20 32 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 30 2 0 0 0 0 24 32 1 0 0 0 0 26 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.22
Volume:	458.312
LogP:	4.406
LogD:	3.186
LogS:	-5.646
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	4.568
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.745
MDCK Permeability:	2.14E-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	94.92%
Volume Distribution (VD):	0.744
Pgp-substrate:	1.42%

ADMET: Metabolism

CYP1A2-inhibitor:	0.801
CYP1A2-substrate:	0.782
CYP2C19-inhibitor:	0.464
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.9
CYP2D6-substrate:	0.436
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	5.114
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.446
Drug-inuced Liver Injury (DILI):	0.105
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.672
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.259
Carcinogencity:	0.567
Eye Corrosion:	0.003
Eye Irritation:	0.111
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC315306

Natural Product ID:	NPC315306
*Common Name:**	Marfuraquinocin C
IUPAC Name:	(2S,3S)-3-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-4-hydroxy-2-(hydroxymethyl)-7-methoxy-3-methyl-2H-benzo[g][1]benzofuran-6,9-dione
Synonyms:
Standard InCHIKey:	FOTKGFOGIIZYTA-FVKAXFGDSA-N
Standard InCHI:	InChI=1S/C26H32O6/c1-14-7-6-9-25(2,3)16(14)8-10-26(4)20(13-27)32-24-21-15(11-18(29)22(24)26)23(30)19(31-5)12-17(21)28/h11-12,16,20,27,29H,1,6-10,13H2,2-5H3/t16?,20-,26-/m1/s1
SMILES:	OC[C@H]1Oc2c([C@]1(C)CCC1C(=C)CCCC1(C)C)c(O)cc1c2C(=O)C=C(C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092698
PubChem CID:	73603997
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
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	18900.0	nM	PMID[527901]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	17900.0	nM	PMID[527901]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	11900.0	nM	PMID[527901]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4400.0	nM	PMID[527901]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[527901]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	128.0	ug.mL-1	PMID[527901]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	128.0	ug.mL-1	PMID[527901]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	128.0	ug.mL-1	PMID[527901]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[527901]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	8.0	ug.mL-1	PMID[527901]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[527901]

☑ 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 NPC315306 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	421
0.1-0.2	1475
0.2-0.3	3149
0.3-0.4	7028
0.4-0.5	10530
0.5-0.6	5277
0.6-0.7	5246
0.7-0.8	6627
0.8-0.85	2486
0.85-0.9	446
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC313717
0.9748	High Similarity	NPC316262
0.9748	High Similarity	NPC314653
0.9497	High Similarity	NPC313368
0.9202	High Similarity	NPC100849
0.9141	High Similarity	NPC475106
0.9136	High Similarity	NPC470810
0.9064	High Similarity	NPC475148
0.9064	High Similarity	NPC475656
0.9048	High Similarity	NPC469393
0.9048	High Similarity	NPC475080
0.9	High Similarity	NPC470340
0.8988	High Similarity	NPC118128
0.8982	High Similarity	NPC286074
0.8982	High Similarity	NPC54903
0.8976	High Similarity	NPC85047
0.8976	High Similarity	NPC17274
0.8976	High Similarity	NPC120857
0.897	High Similarity	NPC476822
0.8963	High Similarity	NPC117985
0.8953	High Similarity	NPC228209
0.8935	High Similarity	NPC154986
0.8935	High Similarity	NPC98776
0.8922	High Similarity	NPC193222
0.8916	High Similarity	NPC21016
0.8916	High Similarity	NPC146584
0.8916	High Similarity	NPC472049
0.8909	High Similarity	NPC211107
0.8908	High Similarity	NPC240808
0.8882	High Similarity	NPC294149
0.8882	High Similarity	NPC154683
0.8882	High Similarity	NPC40356
0.8882	High Similarity	NPC275878
0.8876	High Similarity	NPC472620
0.8869	High Similarity	NPC213416
0.8869	High Similarity	NPC473096
0.8869	High Similarity	NPC20734
0.8869	High Similarity	NPC473095
0.8862	High Similarity	NPC469394
0.8862	High Similarity	NPC476255
0.8862	High Similarity	NPC62444
0.8862	High Similarity	NPC476056
0.8855	High Similarity	NPC18100
0.8855	High Similarity	NPC208120
0.8855	High Similarity	NPC474240
0.8855	High Similarity	NPC469395
0.8855	High Similarity	NPC173587
0.8848	High Similarity	NPC187354
0.8848	High Similarity	NPC476929
0.8844	High Similarity	NPC8927
0.8841	High Similarity	NPC477410
0.8834	High Similarity	NPC164427
0.883	High Similarity	NPC475233
0.883	High Similarity	NPC98943
0.883	High Similarity	NPC478050
0.8827	High Similarity	NPC193200
0.8827	High Similarity	NPC293286
0.8827	High Similarity	NPC155686
0.882	High Similarity	NPC46882
0.882	High Similarity	NPC470569
0.882	High Similarity	NPC132990
0.8817	High Similarity	NPC193698
0.881	High Similarity	NPC473094
0.881	High Similarity	NPC232936
0.8802	High Similarity	NPC473286
0.8802	High Similarity	NPC472277
0.8802	High Similarity	NPC475888
0.8795	High Similarity	NPC94796
0.8788	High Similarity	NPC472618
0.8786	High Similarity	NPC208069
0.878	High Similarity	NPC196448
0.878	High Similarity	NPC246466
0.878	High Similarity	NPC201127
0.8779	High Similarity	NPC77179
0.8779	High Similarity	NPC23553
0.8773	High Similarity	NPC326910
0.8773	High Similarity	NPC175192
0.8773	High Similarity	NPC471116
0.8765	High Similarity	NPC138288
0.8765	High Similarity	NPC5029
0.8765	High Similarity	NPC35567
0.8765	High Similarity	NPC216035
0.8765	High Similarity	NPC271385
0.8765	High Similarity	NPC87708
0.8765	High Similarity	NPC217149
0.8765	High Similarity	NPC113608
0.8765	High Similarity	NPC180944
0.8765	High Similarity	NPC470338
0.8765	High Similarity	NPC51824
0.8765	High Similarity	NPC76128
0.8765	High Similarity	NPC111536
0.8765	High Similarity	NPC30432
0.8765	High Similarity	NPC243171
0.8765	High Similarity	NPC171651
0.8765	High Similarity	NPC470337
0.8765	High Similarity	NPC169018
0.8765	High Similarity	NPC268992
0.8758	High Similarity	NPC470568
0.8758	High Similarity	NPC202595
0.8758	High Similarity	NPC147735
0.8757	High Similarity	NPC472619
0.875	High Similarity	NPC53640
0.875	High Similarity	NPC475109
0.875	High Similarity	NPC125465
0.8743	High Similarity	NPC473313
0.8743	High Similarity	NPC205265
0.8743	High Similarity	NPC197972
0.8743	High Similarity	NPC475055
0.8743	High Similarity	NPC329669
0.8743	High Similarity	NPC472278
0.8743	High Similarity	NPC472281
0.8736	High Similarity	NPC246153
0.8735	High Similarity	NPC30655
0.8735	High Similarity	NPC74854
0.8735	High Similarity	NPC103816
0.8735	High Similarity	NPC61382
0.8735	High Similarity	NPC269117
0.8735	High Similarity	NPC474239
0.8735	High Similarity	NPC45124
0.8728	High Similarity	NPC473607
0.8727	High Similarity	NPC470339
0.8727	High Similarity	NPC472617
0.8727	High Similarity	NPC125969
0.8727	High Similarity	NPC85121
0.8721	High Similarity	NPC46958
0.8721	High Similarity	NPC324220
0.8721	High Similarity	NPC312630
0.872	High Similarity	NPC472050
0.872	High Similarity	NPC20530
0.872	High Similarity	NPC10754
0.872	High Similarity	NPC477674
0.872	High Similarity	NPC215917
0.872	High Similarity	NPC180924
0.8713	High Similarity	NPC471969
0.8712	High Similarity	NPC60084
0.8712	High Similarity	NPC209760
0.8712	High Similarity	NPC100134
0.8704	High Similarity	NPC232645
0.8704	High Similarity	NPC72958
0.8704	High Similarity	NPC474772
0.8704	High Similarity	NPC262039
0.8704	High Similarity	NPC230848
0.8704	High Similarity	NPC472423
0.8704	High Similarity	NPC262038
0.8704	High Similarity	NPC474744
0.8704	High Similarity	NPC470675
0.8704	High Similarity	NPC473131
0.8704	High Similarity	NPC278476
0.8704	High Similarity	NPC254412
0.8704	High Similarity	NPC319910
0.8704	High Similarity	NPC478148
0.8698	High Similarity	NPC150131
0.8698	High Similarity	NPC470456
0.8698	High Similarity	NPC225419
0.8698	High Similarity	NPC476459
0.8698	High Similarity	NPC95715
0.8698	High Similarity	NPC472622
0.869	High Similarity	NPC473908
0.869	High Similarity	NPC25361
0.869	High Similarity	NPC326520
0.8683	High Similarity	NPC472402
0.8683	High Similarity	NPC473961
0.8683	High Similarity	NPC470694
0.8679	High Similarity	NPC28632
0.8675	High Similarity	NPC321399
0.8675	High Similarity	NPC472055
0.8675	High Similarity	NPC476283
0.8675	High Similarity	NPC306978
0.8675	High Similarity	NPC475107
0.8675	High Similarity	NPC43490
0.8671	High Similarity	NPC5671
0.8671	High Similarity	NPC477683
0.8671	High Similarity	NPC246877
0.8671	High Similarity	NPC221820
0.8671	High Similarity	NPC477682
0.8667	High Similarity	NPC164110
0.8667	High Similarity	NPC246647
0.8667	High Similarity	NPC281137
0.8667	High Similarity	NPC474637
0.8667	High Similarity	NPC272196
0.8667	High Similarity	NPC282390
0.8667	High Similarity	NPC212967
0.8667	High Similarity	NPC96342
0.8663	High Similarity	NPC162248
0.8663	High Similarity	NPC475398
0.8663	High Similarity	NPC68381
0.8663	High Similarity	NPC245975
0.8659	High Similarity	NPC68727
0.8659	High Similarity	NPC267242
0.8655	High Similarity	NPC477529
0.865	High Similarity	NPC253904
0.865	High Similarity	NPC476238
0.865	High Similarity	NPC210597
0.865	High Similarity	NPC285623
0.865	High Similarity	NPC477957
0.865	High Similarity	NPC327269
0.865	High Similarity	NPC31627
0.865	High Similarity	NPC470353
0.865	High Similarity	NPC321363
0.865	High Similarity	NPC473996

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 NPC315306 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	884
0.2-0.3	1830
0.3-0.4	2585
0.4-0.5	1901
0.5-0.6	998
0.6-0.7	404
0.7-0.8	159
0.8-0.85	29
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8554	High Similarity	NPD7075	Discontinued
0.8494	Intermediate Similarity	NPD3882	Suspended
0.8485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6599	Discontinued
0.8373	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8314	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8303	Intermediate Similarity	NPD4380	Phase 2
0.8294	Intermediate Similarity	NPD6959	Discontinued
0.8263	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD2800	Approved
0.8235	Intermediate Similarity	NPD5494	Approved
0.8218	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8177	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3818	Discontinued
0.8156	Intermediate Similarity	NPD8434	Phase 2
0.815	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6166	Phase 2
0.814	Intermediate Similarity	NPD6232	Discontinued
0.8107	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6799	Approved
0.8047	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7978	Intermediate Similarity	NPD7251	Discontinued
0.7963	Intermediate Similarity	NPD1549	Phase 2
0.7952	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD6100	Approved
0.795	Intermediate Similarity	NPD6099	Approved
0.7933	Intermediate Similarity	NPD7808	Phase 3
0.7921	Intermediate Similarity	NPD6797	Phase 2
0.7901	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4628	Phase 3
0.7865	Intermediate Similarity	NPD7074	Phase 3
0.7853	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3751	Discontinued
0.7849	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2796	Approved
0.7833	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1511	Approved
0.7811	Intermediate Similarity	NPD3226	Approved
0.7809	Intermediate Similarity	NPD7054	Approved
0.7798	Intermediate Similarity	NPD5403	Approved
0.779	Intermediate Similarity	NPD8313	Approved
0.779	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7771	Intermediate Similarity	NPD1247	Approved
0.7765	Intermediate Similarity	NPD7472	Approved
0.7764	Intermediate Similarity	NPD1607	Approved
0.7764	Intermediate Similarity	NPD6651	Approved
0.776	Intermediate Similarity	NPD8150	Discontinued
0.7749	Intermediate Similarity	NPD7435	Discontinued
0.7727	Intermediate Similarity	NPD5710	Approved
0.7727	Intermediate Similarity	NPD5711	Approved
0.7722	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7411	Suspended
0.7701	Intermediate Similarity	NPD3749	Approved
0.7684	Intermediate Similarity	NPD6776	Approved
0.7684	Intermediate Similarity	NPD6782	Approved
0.7684	Intermediate Similarity	NPD6779	Approved
0.7684	Intermediate Similarity	NPD6777	Approved
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.7684	Intermediate Similarity	NPD6781	Approved
0.7684	Intermediate Similarity	NPD6778	Approved
0.7684	Intermediate Similarity	NPD6780	Approved
0.7679	Intermediate Similarity	NPD5401	Approved
0.7657	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD3750	Approved
0.7644	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD1240	Approved
0.763	Intermediate Similarity	NPD5761	Phase 2
0.763	Intermediate Similarity	NPD5760	Phase 2
0.7581	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2346	Discontinued
0.7572	Intermediate Similarity	NPD37	Approved
0.7565	Intermediate Similarity	NPD7698	Approved
0.7565	Intermediate Similarity	NPD7696	Phase 3
0.7565	Intermediate Similarity	NPD7697	Approved
0.7557	Intermediate Similarity	NPD6234	Discontinued
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7542	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7528	Intermediate Similarity	NPD3787	Discontinued
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD920	Approved
0.7475	Intermediate Similarity	NPD7801	Approved
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1471	Phase 3
0.747	Intermediate Similarity	NPD2344	Approved
0.7459	Intermediate Similarity	NPD7228	Approved
0.7444	Intermediate Similarity	NPD2403	Approved
0.7436	Intermediate Similarity	NPD8319	Approved
0.7436	Intermediate Similarity	NPD8320	Phase 1
0.7435	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7229	Phase 3
0.7421	Intermediate Similarity	NPD6535	Approved
0.7421	Intermediate Similarity	NPD6534	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7399	Intermediate Similarity	NPD7458	Discontinued
0.7399	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7700	Phase 2
0.7396	Intermediate Similarity	NPD7699	Phase 2
0.7381	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1243	Approved
0.7374	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2799	Discontinued
0.7349	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3748	Approved
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7337	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6273	Approved
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8366	Approved
0.7317	Intermediate Similarity	NPD4060	Phase 1
0.7297	Intermediate Similarity	NPD6765	Approved
0.7297	Intermediate Similarity	NPD6764	Approved
0.7294	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5762	Approved
0.7262	Intermediate Similarity	NPD5763	Approved
0.7251	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7233	Intermediate Similarity	NPD7907	Approved
0.722	Intermediate Similarity	NPD4111	Phase 1
0.722	Intermediate Similarity	NPD4665	Approved
0.7214	Intermediate Similarity	NPD7783	Phase 2
0.7214	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD943	Approved
0.7195	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8127	Discontinued
0.7177	Intermediate Similarity	NPD8491	Approved
0.7174	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD230	Phase 1
0.7168	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3057	Approved
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD4360	Phase 2
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6784	Approved
0.7143	Intermediate Similarity	NPD6785	Approved
0.7135	Intermediate Similarity	NPD7003	Approved
0.7134	Intermediate Similarity	NPD4625	Phase 3
0.7122	Intermediate Similarity	NPD8404	Phase 2
0.7113	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4361	Phase 2
0.7112	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7240	Approved
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2493	Approved
0.7107	Intermediate Similarity	NPD2494	Approved
0.7099	Intermediate Similarity	NPD1470	Approved
0.7093	Intermediate Similarity	NPD6190	Approved
0.7091	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD4582	Approved
0.7085	Intermediate Similarity	NPD4583	Approved
0.7081	Intermediate Similarity	NPD4749	Approved
0.7081	Intermediate Similarity	NPD7799	Discontinued
0.7076	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2972	Approved
0.7071	Intermediate Similarity	NPD3533	Approved
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7236	Approved
0.7042	Intermediate Similarity	NPD8067	Phase 3
0.7037	Intermediate Similarity	NPD6696	Suspended
0.7035	Intermediate Similarity	NPD4004	Approved
0.7035	Intermediate Similarity	NPD4002	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