NPASS Compound

Structure

NPC470731 OpenBabel07101718182D 32 38 0 0 1 0 0 0 0 0999 V2000 -0.7207 2.3389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4913 -0.1358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9576 -4.1082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3154 -0.6710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1066 -4.5996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6157 -0.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9576 -3.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2640 -1.6524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2555 -4.1082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1528 -3.0991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3019 -0.7753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7064 1.6610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5643 -1.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1066 -2.6342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8006 -2.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3884 -2.0985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2555 -3.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9250 -1.5703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5717 0.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1304 -0.1178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9022 -1.6730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5717 -0.1178 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1304 0.8649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1341 -3.0477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5253 -2.4680 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 1.3562 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 -0.6091 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 1.5602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4227 1.3562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9814 -0.6091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7575 -0.4373 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 1 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 19 29 2 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 20 30 2 0 0 0 0 21 15 1 1 0 0 0 22 11 1 1 0 0 0 22 27 1 0 0 0 0 22 31 1 0 0 0 0 23 12 1 1 0 0 0 23 26 1 0 0 0 0 23 32 1 0 0 0 0 31 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.1
Volume:	430.117
LogP:	3.463
LogD:	2.155
LogS:	-4.629
# Rotatable Bonds:	2
TPSA:	88.67
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	5.856
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.414
MDCK Permeability:	8.487645573040936e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.572
Plasma Protein Binding (PPB):	89.06568145751953%
Volume Distribution (VD):	1.103
Pgp-substrate:	4.799697399139404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.975
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.819
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.977

ADMET: Excretion

Clearance (CL):	10.262
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.518
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.571
Skin Sensitization:	0.832
Carcinogencity:	0.656
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC470731

Natural Product ID:	NPC470731
*Common Name:**	Luteoalbusin A
IUPAC Name:	n.a.
Synonyms:	Luteoalbusin A
Standard InCHIKey:	XHPIWHHLWCZQEF-PVSGBFIBSA-N
Standard InCHI:	InChI=1S/C23H20N4O3S2/c1-26-19(29)22-11-21(15-10-24-16-8-4-2-6-13(15)16)14-7-3-5-9-17(14)25-18(21)27(22)20(30)23(26,12-28)32-31-22/h2-10,18,24-25,28H,11-12H2,1H3/t18-,21+,22+,23+/m1/s1
SMILES:	CN1C(=O)C23CC4(C(N2C(=O)C1(SS3)CO)NC5=CC=CC=C54)C6=CNC7=CC=CC=C76
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2207538
PubChem CID:	71452523
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO32990	acrostalagmus luteoalbus scsio f457	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23079524]

☑ 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

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	910.0	nM	PMID[489560]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1150.0	nM	PMID[489560]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	230.0	nM	PMID[489560]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	460.0	nM	PMID[489560]

☑ 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 NPC470731 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	398
0.1-0.2	3142
0.2-0.3	22219
0.3-0.4	10773
0.4-0.5	2238
0.5-0.6	2306
0.6-0.7	1384
0.7-0.8	215
0.8-0.85	2
0.85-0.9	9
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC470732
0.9409	High Similarity	NPC477175
0.9409	High Similarity	NPC470730
0.9363	High Similarity	NPC475969
0.9363	High Similarity	NPC475859
0.9317	High Similarity	NPC165743
0.9208	High Similarity	NPC327095
0.9208	High Similarity	NPC312942
0.9163	High Similarity	NPC40455
0.9126	High Similarity	NPC477176
0.9126	High Similarity	NPC470729
0.9118	High Similarity	NPC19170
0.9082	High Similarity	NPC474877
0.9082	High Similarity	NPC477177
0.8995	High Similarity	NPC63279
0.8986	High Similarity	NPC297862
0.8976	High Similarity	NPC476817
0.8952	High Similarity	NPC297642
0.8744	High Similarity	NPC253987
0.8244	Intermediate Similarity	NPC54420
0.8241	Intermediate Similarity	NPC294693
0.8164	Intermediate Similarity	NPC162860
0.8122	Intermediate Similarity	NPC272174
0.8041	Intermediate Similarity	NPC11126
0.803	Intermediate Similarity	NPC17059
0.8	Intermediate Similarity	NPC474896
0.798	Intermediate Similarity	NPC94752
0.797	Intermediate Similarity	NPC228835
0.7963	Intermediate Similarity	NPC31097
0.7941	Intermediate Similarity	NPC171317
0.7927	Intermediate Similarity	NPC161861
0.7905	Intermediate Similarity	NPC107077
0.7905	Intermediate Similarity	NPC223791
0.7861	Intermediate Similarity	NPC128582
0.786	Intermediate Similarity	NPC477714
0.7854	Intermediate Similarity	NPC473640
0.7826	Intermediate Similarity	NPC475506
0.782	Intermediate Similarity	NPC478158
0.7814	Intermediate Similarity	NPC477715
0.7799	Intermediate Similarity	NPC473376
0.7793	Intermediate Similarity	NPC75634
0.7788	Intermediate Similarity	NPC155143
0.775	Intermediate Similarity	NPC308931
0.775	Intermediate Similarity	NPC99939
0.7733	Intermediate Similarity	NPC478028
0.7727	Intermediate Similarity	NPC16659
0.7723	Intermediate Similarity	NPC213629
0.7721	Intermediate Similarity	NPC478157
0.7711	Intermediate Similarity	NPC17273
0.7711	Intermediate Similarity	NPC141612
0.7711	Intermediate Similarity	NPC135601
0.7703	Intermediate Similarity	NPC56109
0.7703	Intermediate Similarity	NPC191382
0.7696	Intermediate Similarity	NPC281049
0.7677	Intermediate Similarity	NPC265710
0.7674	Intermediate Similarity	NPC54744
0.7667	Intermediate Similarity	NPC317701
0.7665	Intermediate Similarity	NPC478029
0.7638	Intermediate Similarity	NPC91179
0.7636	Intermediate Similarity	NPC155444
0.7628	Intermediate Similarity	NPC75726
0.7628	Intermediate Similarity	NPC31385
0.7628	Intermediate Similarity	NPC110602
0.7626	Intermediate Similarity	NPC473380
0.7626	Intermediate Similarity	NPC240088
0.7581	Intermediate Similarity	NPC320968
0.756	Intermediate Similarity	NPC100321
0.7549	Intermediate Similarity	NPC321708
0.7512	Intermediate Similarity	NPC474389
0.7511	Intermediate Similarity	NPC69843
0.7489	Intermediate Similarity	NPC14812
0.7476	Intermediate Similarity	NPC476460
0.7476	Intermediate Similarity	NPC293917
0.7444	Intermediate Similarity	NPC64216
0.7443	Intermediate Similarity	NPC471192
0.7429	Intermediate Similarity	NPC52557
0.7419	Intermediate Similarity	NPC54981
0.7418	Intermediate Similarity	NPC477179
0.7406	Intermediate Similarity	NPC300183
0.7402	Intermediate Similarity	NPC133003
0.7389	Intermediate Similarity	NPC470205
0.7385	Intermediate Similarity	NPC471193
0.7385	Intermediate Similarity	NPC6865
0.7385	Intermediate Similarity	NPC153980
0.7385	Intermediate Similarity	NPC471194
0.7383	Intermediate Similarity	NPC477178
0.7383	Intermediate Similarity	NPC477180
0.7383	Intermediate Similarity	NPC254850
0.7383	Intermediate Similarity	NPC477181
0.7379	Intermediate Similarity	NPC175474
0.7376	Intermediate Similarity	NPC475736
0.7368	Intermediate Similarity	NPC89987
0.7366	Intermediate Similarity	NPC125181
0.7366	Intermediate Similarity	NPC242872
0.7366	Intermediate Similarity	NPC263117
0.7356	Intermediate Similarity	NPC47190
0.7353	Intermediate Similarity	NPC472294
0.7349	Intermediate Similarity	NPC477174
0.7349	Intermediate Similarity	NPC470490
0.7349	Intermediate Similarity	NPC477173
0.7345	Intermediate Similarity	NPC476491
0.7339	Intermediate Similarity	NPC72956
0.7327	Intermediate Similarity	NPC248041
0.7327	Intermediate Similarity	NPC213468
0.7327	Intermediate Similarity	NPC126709
0.7321	Intermediate Similarity	NPC304203
0.7315	Intermediate Similarity	NPC470488
0.7308	Intermediate Similarity	NPC117244
0.7308	Intermediate Similarity	NPC473763
0.7304	Intermediate Similarity	NPC325976
0.7297	Intermediate Similarity	NPC473310
0.7281	Intermediate Similarity	NPC471945
0.7281	Intermediate Similarity	NPC470491
0.7281	Intermediate Similarity	NPC475259
0.7281	Intermediate Similarity	NPC71238
0.7281	Intermediate Similarity	NPC471950
0.7277	Intermediate Similarity	NPC145885
0.7277	Intermediate Similarity	NPC284775
0.7277	Intermediate Similarity	NPC470497
0.7277	Intermediate Similarity	NPC68354
0.7277	Intermediate Similarity	NPC14113
0.7277	Intermediate Similarity	NPC84827
0.7277	Intermediate Similarity	NPC252338
0.7273	Intermediate Similarity	NPC471386
0.7273	Intermediate Similarity	NPC56233
0.7268	Intermediate Similarity	NPC477003
0.7259	Intermediate Similarity	NPC21174
0.7259	Intermediate Similarity	NPC271797
0.7257	Intermediate Similarity	NPC474196
0.7248	Intermediate Similarity	NPC471946
0.7248	Intermediate Similarity	NPC471951
0.7241	Intermediate Similarity	NPC248462
0.7241	Intermediate Similarity	NPC283219
0.7238	Intermediate Similarity	NPC326422
0.7235	Intermediate Similarity	NPC323927
0.7232	Intermediate Similarity	NPC474195
0.723	Intermediate Similarity	NPC268744
0.723	Intermediate Similarity	NPC475914
0.723	Intermediate Similarity	NPC201266
0.723	Intermediate Similarity	NPC474318
0.723	Intermediate Similarity	NPC153123
0.723	Intermediate Similarity	NPC220797
0.7228	Intermediate Similarity	NPC280852
0.7228	Intermediate Similarity	NPC267885
0.7217	Intermediate Similarity	NPC227582
0.7215	Intermediate Similarity	NPC475359
0.7215	Intermediate Similarity	NPC191817
0.7209	Intermediate Similarity	NPC476874
0.7208	Intermediate Similarity	NPC194881
0.7206	Intermediate Similarity	NPC24864
0.7205	Intermediate Similarity	NPC326363
0.7196	Intermediate Similarity	NPC166209
0.7196	Intermediate Similarity	NPC195461
0.7196	Intermediate Similarity	NPC81654
0.7196	Intermediate Similarity	NPC249150
0.7196	Intermediate Similarity	NPC49196
0.7196	Intermediate Similarity	NPC313985
0.7196	Intermediate Similarity	NPC269203
0.7196	Intermediate Similarity	NPC77241
0.7196	Intermediate Similarity	NPC13456
0.7196	Intermediate Similarity	NPC79129
0.7194	Intermediate Similarity	NPC135141
0.7194	Intermediate Similarity	NPC92796
0.7193	Intermediate Similarity	NPC475258
0.7192	Intermediate Similarity	NPC64436
0.7192	Intermediate Similarity	NPC59269
0.7184	Intermediate Similarity	NPC165495
0.7183	Intermediate Similarity	NPC131887
0.7183	Intermediate Similarity	NPC50503
0.7178	Intermediate Similarity	NPC110500
0.7178	Intermediate Similarity	NPC203468
0.7178	Intermediate Similarity	NPC37423
0.7178	Intermediate Similarity	NPC275305
0.7178	Intermediate Similarity	NPC149155
0.7177	Intermediate Similarity	NPC324091
0.7175	Intermediate Similarity	NPC238945
0.7165	Intermediate Similarity	NPC200214
0.716	Intermediate Similarity	NPC321939
0.7157	Intermediate Similarity	NPC219336
0.7156	Intermediate Similarity	NPC474180
0.7156	Intermediate Similarity	NPC188821
0.715	Intermediate Similarity	NPC201700
0.715	Intermediate Similarity	NPC15102
0.7143	Intermediate Similarity	NPC216643
0.7143	Intermediate Similarity	NPC299594
0.7143	Intermediate Similarity	NPC469762
0.7136	Intermediate Similarity	NPC163055
0.7136	Intermediate Similarity	NPC102755
0.7129	Intermediate Similarity	NPC242269
0.7123	Intermediate Similarity	NPC157828
0.7123	Intermediate Similarity	NPC195239
0.712	Intermediate Similarity	NPC314372
0.712	Intermediate Similarity	NPC470440
0.7115	Intermediate Similarity	NPC62749
0.7115	Intermediate Similarity	NPC235684
0.7108	Intermediate Similarity	NPC183662
0.7108	Intermediate Similarity	NPC15573
0.7108	Intermediate Similarity	NPC217372
0.7107	Intermediate Similarity	NPC475990
0.7107	Intermediate Similarity	NPC474880

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 NPC470731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	576
0.2-0.3	1154
0.3-0.4	2173
0.4-0.5	2152
0.5-0.6	2102
0.6-0.7	725
0.7-0.8	63
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
0.8241	Intermediate Similarity	NPD7618	Phase 3
0.8241	Intermediate Similarity	NPD7619	Phase 3
0.7962	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD7970	Approved
0.7783	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7824	Approved
0.774	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7950	Approved
0.7723	Intermediate Similarity	NPD7789	Approved
0.7723	Intermediate Similarity	NPD7790	Approved
0.7723	Intermediate Similarity	NPD7791	Approved
0.7723	Intermediate Similarity	NPD7953	Approved
0.7723	Intermediate Similarity	NPD7952	Approved
0.7723	Intermediate Similarity	NPD7951	Approved
0.7703	Intermediate Similarity	NPD7780	Approved
0.7703	Intermediate Similarity	NPD7781	Approved
0.7658	Intermediate Similarity	NPD7730	Approved
0.7658	Intermediate Similarity	NPD7731	Approved
0.7647	Intermediate Similarity	NPD7271	Approved
0.7642	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6664	Approved
0.7547	Intermediate Similarity	NPD8272	Phase 2
0.7536	Intermediate Similarity	NPD6268	Phase 1
0.7536	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5199	Approved
0.75	Intermediate Similarity	NPD5198	Approved
0.75	Intermediate Similarity	NPD3961	Discontinued
0.75	Intermediate Similarity	NPD7470	Discontinued
0.7476	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2880	Discontinued
0.7422	Intermediate Similarity	NPD6165	Phase 2
0.7422	Intermediate Similarity	NPD6164	Phase 2
0.7419	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8322	Phase 2
0.7391	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5426	Phase 3
0.7376	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6595	Phase 3
0.7368	Intermediate Similarity	NPD7944	Discontinued
0.7366	Intermediate Similarity	NPD7026	Phase 2
0.7366	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2443	Approved
0.7361	Intermediate Similarity	NPD2442	Approved
0.7352	Intermediate Similarity	NPD8094	Discontinued
0.7333	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6044	Discontinued
0.7309	Intermediate Similarity	NPD5884	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD8093	Discontinued
0.7294	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD3505	Approved
0.7277	Intermediate Similarity	NPD3506	Approved
0.7268	Intermediate Similarity	NPD7564	Discontinued
0.7252	Intermediate Similarity	NPD8256	Approved
0.7252	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD8257	Approved
0.7241	Intermediate Similarity	NPD4079	Approved
0.7241	Intermediate Similarity	NPD4076	Approved
0.7233	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7603	Discontinued
0.7222	Intermediate Similarity	NPD8115	Approved
0.7222	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8114	Approved
0.7208	Intermediate Similarity	NPD6771	Discontinued
0.7202	Intermediate Similarity	NPD7666	Phase 3
0.7202	Intermediate Similarity	NPD7665	Phase 2
0.7196	Intermediate Similarity	NPD4601	Approved
0.7196	Intermediate Similarity	NPD4600	Approved
0.7192	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD482	Approved
0.7175	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2408	Discontinued
0.7163	Intermediate Similarity	NPD7394	Phase 2
0.7149	Intermediate Similarity	NPD7711	Discontinued
0.7143	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4075	Phase 2
0.7136	Intermediate Similarity	NPD2094	Phase 2
0.7136	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2095	Phase 2
0.7136	Intermediate Similarity	NPD2092	Phase 2
0.713	Intermediate Similarity	NPD7543	Phase 2
0.7124	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6217	Discontinued
0.7112	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5491	Phase 3
0.711	Intermediate Similarity	NPD5489	Phase 1
0.7109	Intermediate Similarity	NPD4615	Phase 2
0.7109	Intermediate Similarity	NPD4922	Phase 2
0.7108	Intermediate Similarity	NPD4181	Approved
0.7101	Intermediate Similarity	NPD2091	Phase 2
0.7101	Intermediate Similarity	NPD2096	Phase 2
0.7098	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD3583	Phase 2
0.7083	Intermediate Similarity	NPD5017	Discontinued
0.7083	Intermediate Similarity	NPD7817	Phase 1
0.7078	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1506	Discontinued
0.7074	Intermediate Similarity	NPD8289	Discontinued
0.7072	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6999	Discontinued
0.707	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6470	Phase 3
0.7064	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD750	Phase 2
0.704	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7001	Phase 3
0.7032	Intermediate Similarity	NPD2008	Discontinued
0.7019	Intermediate Similarity	NPD6178	Phase 3
0.7018	Intermediate Similarity	NPD8072	Approved
0.701	Intermediate Similarity	NPD5065	Approved
0.701	Intermediate Similarity	NPD4128	Approved
0.7	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD2411	Approved
0.6991	Remote Similarity	NPD2405	Phase 3
0.699	Remote Similarity	NPD2837	Discontinued
0.6987	Remote Similarity	NPD7717	Approved
0.6987	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7716	Approved
0.6986	Remote Similarity	NPD8169	Discontinued
0.6985	Remote Similarity	NPD2511	Approved
0.6981	Remote Similarity	NPD7434	Approved
0.6974	Remote Similarity	NPD2172	Phase 1
0.6972	Remote Similarity	NPD3015	Discontinued
0.6967	Remote Similarity	NPD7175	Phase 1
0.6963	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD8316	Phase 2
0.6953	Remote Similarity	NPD8317	Phase 2
0.6951	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5487	Phase 1
0.6938	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2642	Approved
0.6931	Remote Similarity	NPD2639	Approved
0.693	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6210	Phase 3
0.6927	Remote Similarity	NPD7727	Phase 2
0.6923	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3323	Discontinued
0.6909	Remote Similarity	NPD7208	Approved
0.6909	Remote Similarity	NPD7209	Approved
0.6909	Remote Similarity	NPD7207	Approved
0.6907	Remote Similarity	NPD6986	Phase 1
0.6906	Remote Similarity	NPD4051	Discontinued
0.6901	Remote Similarity	NPD8240	Discontinued
0.6898	Remote Similarity	NPD3830	Phase 1
0.6898	Remote Similarity	NPD5446	Phase 2
0.6897	Remote Similarity	NPD2640	Approved
0.6897	Remote Similarity	NPD2641	Approved
0.6897	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8073	Approved
0.6892	Remote Similarity	NPD6521	Phase 3
0.6892	Remote Similarity	NPD6520	Phase 3
0.6886	Remote Similarity	NPD5270	Discontinued
0.6884	Remote Similarity	NPD4602	Approved
0.6881	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7957	Phase 1
0.6878	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1722	Approved
0.6872	Remote Similarity	NPD5809	Phase 3
0.687	Remote Similarity	NPD8484	Phase 2
0.6863	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8250	Phase 2
0.686	Remote Similarity	NPD2144	Approved
0.6857	Remote Similarity	NPD7483	Phase 2
0.6857	Remote Similarity	NPD7482	Phase 2
0.6852	Remote Similarity	NPD7027	Phase 3
0.6847	Remote Similarity	NPD5864	Phase 2
0.684	Remote Similarity	NPD8431	Approved
0.6835	Remote Similarity	NPD6248	Phase 2
0.6835	Remote Similarity	NPD6249	Phase 2
0.6829	Remote Similarity	NPD3610	Approved
0.6829	Remote Similarity	NPD3609	Approved
0.6825	Remote Similarity	NPD5555	Phase 1
0.6822	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6459	Phase 2
0.6816	Remote Similarity	NPD2510	Approved
0.6816	Remote Similarity	NPD2509	Approved
0.6814	Remote Similarity	NPD4638	Approved
0.6814	Remote Similarity	NPD4640	Approved
0.6814	Remote Similarity	NPD4639	Approved
0.6814	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5021	Discontinued
0.6812	Remote Similarity	NPD7168	Phase 3
0.681	Remote Similarity	NPD5106	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