NPASS Compound

Structure

NPC472762 OpenBabel07101719152D 33 39 0 0 1 0 0 0 0 0999 V2000 3.4238 0.0624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9112 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0356 0.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9892 0.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7344 1.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6415 1.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2479 -1.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0921 -0.5556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4406 3.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9364 1.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1754 3.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5235 -0.8568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4037 -0.5556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2848 3.3437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3867 2.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3402 2.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4037 3.3437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0921 2.3689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0921 0.4192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4037 0.4192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2479 1.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2479 3.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5235 0.7205 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8857 0.0931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9364 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2479 0.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8276 3.0158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4037 2.3689 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2479 4.8060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0317 -1.4842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0965 -0.0682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0921 3.3437 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 25 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 31 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 27 1 0 0 0 0 17 9 1 1 0 0 0 17 22 1 0 0 0 0 17 28 1 0 0 0 0 18 10 1 1 0 0 0 18 21 1 0 0 0 0 18 32 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 6 0 0 0 20 23 1 0 0 0 0 20 26 1 6 0 0 0 21 28 2 0 0 0 0 22 29 2 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 30 2 0 0 0 0 24 33 1 0 0 0 0 26 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.18
Volume:	443.21
LogP:	4.068
LogD:	3.306
LogS:	-4.183
# Rotatable Bonds:	2
TPSA:	89.98
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	5.52
Fsp3:	0.5
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:	-4.763
MDCK Permeability:	1.823273669288028e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.403

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	86.34778594970703%
Volume Distribution (VD):	2.447
Pgp-substrate:	14.000539779663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.467
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.546
CYP2D6-substrate:	0.597
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.454

ADMET: Excretion

Clearance (CL):	6.929
Half-life (T1/2):	0.031

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.268
Carcinogencity:	0.778
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC472762

Natural Product ID:	NPC472762
*Common Name:**	KJGOXXYRSAWVEF-LNXYMLJESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KJGOXXYRSAWVEF-LNXYMLJESA-N
Standard InCHI:	InChI=1S/C26H26N2O5/c1-25(2)10-18-21(26-19(25)8-7-13-12-31-23(20(13)26)33-24(26)30)28-17(22(29)32-18)9-14-11-27-16-6-4-3-5-15(14)16/h3-7,11,17-20,23,27H,8-10,12H2,1-2H3/t17-,18-,19-,20+,23?,26+/m0/s1
SMILES:	O=C1O[C@H]2CC(C)(C)[C@H]3[C@@]4(C2=N[C@H]1Cc1c[nH]c2c1cccc2)C(=O)OC1[C@H]4C(=CC3)CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582031
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0000394] Alpha amino acid esters

*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
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24262004]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25951057]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	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	6
Others	3

Activity Type	# Activity
Cell Line	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4590	Cell Line	EL4	Mus musculus	IC50	=	4000.0	nM	PMID[545096]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6700.0	nM	PMID[545096]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	13400.0	nM	PMID[545096]
NPT2788	Cell Line	3T3	Mus musculus	IC50	>	1230000	nM	PubChem BioAssay data set
NPT2788	Cell Line	3T3	Mus musculus	GI	=	32	%	PMID[19902967]
NPT27	Others	Unspecified		IC50	>	1230000.0	nM	PMID[545096]
NPT27	Others	Unspecified		GI	=	41.0	%	PMID[545096]
NPT27	Others	Unspecified		GI	=	20.0	%	PMID[545096]

☑ 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 NPC472762 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	384
0.1-0.2	1599
0.2-0.3	5620
0.3-0.4	22468
0.4-0.5	7956
0.5-0.6	2568
0.6-0.7	1814
0.7-0.8	287
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8009	Intermediate Similarity	NPC229348
0.7973	Intermediate Similarity	NPC235885
0.7892	Intermediate Similarity	NPC235684
0.789	Intermediate Similarity	NPC313640
0.7848	Intermediate Similarity	NPC475271
0.7838	Intermediate Similarity	NPC2395
0.7822	Intermediate Similarity	NPC57690
0.7793	Intermediate Similarity	NPC476874
0.7783	Intermediate Similarity	NPC214428
0.7783	Intermediate Similarity	NPC82070
0.7773	Intermediate Similarity	NPC36405
0.7768	Intermediate Similarity	NPC266192
0.7742	Intermediate Similarity	NPC478158
0.7731	Intermediate Similarity	NPC474905
0.7729	Intermediate Similarity	NPC70155
0.7727	Intermediate Similarity	NPC478157
0.7699	Intermediate Similarity	NPC267926
0.7692	Intermediate Similarity	NPC203614
0.7692	Intermediate Similarity	NPC204491
0.7685	Intermediate Similarity	NPC213468
0.7655	Intermediate Similarity	NPC141428
0.7644	Intermediate Similarity	NPC321708
0.7642	Intermediate Similarity	NPC290529
0.7635	Intermediate Similarity	NPC145885
0.7635	Intermediate Similarity	NPC84827
0.7635	Intermediate Similarity	NPC14113
0.7628	Intermediate Similarity	NPC193761
0.7623	Intermediate Similarity	NPC281049
0.7613	Intermediate Similarity	NPC476114
0.7606	Intermediate Similarity	NPC67288
0.7605	Intermediate Similarity	NPC476516
0.7604	Intermediate Similarity	NPC277350
0.7602	Intermediate Similarity	NPC234078
0.7602	Intermediate Similarity	NPC221100
0.7593	Intermediate Similarity	NPC476115
0.7589	Intermediate Similarity	NPC52254
0.7586	Intermediate Similarity	NPC267885
0.7581	Intermediate Similarity	NPC300183
0.7557	Intermediate Similarity	NPC87856
0.7557	Intermediate Similarity	NPC151976
0.7549	Intermediate Similarity	NPC151939
0.7546	Intermediate Similarity	NPC260900
0.7537	Intermediate Similarity	NPC110500
0.7537	Intermediate Similarity	NPC203468
0.7537	Intermediate Similarity	NPC149155
0.7535	Intermediate Similarity	NPC254240
0.7535	Intermediate Similarity	NPC312870
0.7535	Intermediate Similarity	NPC294909
0.7535	Intermediate Similarity	NPC128265
0.7535	Intermediate Similarity	NPC199851
0.7534	Intermediate Similarity	NPC132211
0.7534	Intermediate Similarity	NPC127677
0.7534	Intermediate Similarity	NPC258062
0.7533	Intermediate Similarity	NPC147446
0.7523	Intermediate Similarity	NPC54744
0.7523	Intermediate Similarity	NPC267965
0.7512	Intermediate Similarity	NPC126709
0.7512	Intermediate Similarity	NPC98715
0.7512	Intermediate Similarity	NPC248041
0.7512	Intermediate Similarity	NPC283219
0.7511	Intermediate Similarity	NPC475258
0.7489	Intermediate Similarity	NPC225821
0.7489	Intermediate Similarity	NPC46225
0.7489	Intermediate Similarity	NPC474412
0.7488	Intermediate Similarity	NPC74413
0.7488	Intermediate Similarity	NPC472097
0.7477	Intermediate Similarity	NPC475778
0.7467	Intermediate Similarity	NPC909
0.7467	Intermediate Similarity	NPC475424
0.7467	Intermediate Similarity	NPC475338
0.7467	Intermediate Similarity	NPC79107
0.7466	Intermediate Similarity	NPC234999
0.7453	Intermediate Similarity	NPC55493
0.7441	Intermediate Similarity	NPC314333
0.744	Intermediate Similarity	NPC71037
0.7421	Intermediate Similarity	NPC162860
0.7421	Intermediate Similarity	NPC271862
0.7421	Intermediate Similarity	NPC469743
0.7412	Intermediate Similarity	NPC155444
0.7403	Intermediate Similarity	NPC56109
0.7403	Intermediate Similarity	NPC191382
0.7399	Intermediate Similarity	NPC207020
0.7391	Intermediate Similarity	NPC300688
0.7389	Intermediate Similarity	NPC477714
0.7385	Intermediate Similarity	NPC474116
0.7383	Intermediate Similarity	NPC220151
0.7383	Intermediate Similarity	NPC19692
0.7373	Intermediate Similarity	NPC252338
0.7373	Intermediate Similarity	NPC313985
0.7373	Intermediate Similarity	NPC49196
0.7373	Intermediate Similarity	NPC195461
0.7373	Intermediate Similarity	NPC81654
0.7373	Intermediate Similarity	NPC79129
0.7373	Intermediate Similarity	NPC249150
0.7364	Intermediate Similarity	NPC18661
0.7358	Intermediate Similarity	NPC329858
0.7354	Intermediate Similarity	NPC82370
0.7349	Intermediate Similarity	NPC245916
0.7349	Intermediate Similarity	NPC11445
0.734	Intermediate Similarity	NPC78020
0.7339	Intermediate Similarity	NPC267853
0.7331	Intermediate Similarity	NPC15801
0.733	Intermediate Similarity	NPC475835
0.733	Intermediate Similarity	NPC54420
0.7321	Intermediate Similarity	NPC118940
0.7321	Intermediate Similarity	NPC75634
0.7316	Intermediate Similarity	NPC24370
0.7316	Intermediate Similarity	NPC319232
0.7315	Intermediate Similarity	NPC227582
0.7311	Intermediate Similarity	NPC46413
0.7308	Intermediate Similarity	NPC244897
0.7308	Intermediate Similarity	NPC469896
0.7306	Intermediate Similarity	NPC162730
0.7302	Intermediate Similarity	NPC195239
0.7302	Intermediate Similarity	NPC157828
0.7299	Intermediate Similarity	NPC315555
0.7292	Intermediate Similarity	NPC476517
0.7291	Intermediate Similarity	NPC474561
0.7291	Intermediate Similarity	NPC49954
0.729	Intermediate Similarity	NPC47190
0.7289	Intermediate Similarity	NPC473547
0.7289	Intermediate Similarity	NPC472291
0.7289	Intermediate Similarity	NPC475602
0.7288	Intermediate Similarity	NPC57453
0.7285	Intermediate Similarity	NPC238457
0.7284	Intermediate Similarity	NPC192712
0.7281	Intermediate Similarity	NPC50503
0.7273	Intermediate Similarity	NPC125597
0.7269	Intermediate Similarity	NPC477715
0.7265	Intermediate Similarity	NPC315062
0.7264	Intermediate Similarity	NPC17059
0.726	Intermediate Similarity	NPC6093
0.7257	Intermediate Similarity	NPC97388
0.7255	Intermediate Similarity	NPC63751
0.7253	Intermediate Similarity	NPC33949
0.7252	Intermediate Similarity	NPC323927
0.7251	Intermediate Similarity	NPC280290
0.7246	Intermediate Similarity	NPC316411
0.724	Intermediate Similarity	NPC473376
0.7237	Intermediate Similarity	NPC174788
0.7234	Intermediate Similarity	NPC89987
0.723	Intermediate Similarity	NPC111602
0.723	Intermediate Similarity	NPC102338
0.723	Intermediate Similarity	NPC63199
0.723	Intermediate Similarity	NPC196251
0.7229	Intermediate Similarity	NPC64216
0.7225	Intermediate Similarity	NPC472027
0.7217	Intermediate Similarity	NPC471506
0.7215	Intermediate Similarity	NPC315491
0.7215	Intermediate Similarity	NPC45459
0.7212	Intermediate Similarity	NPC59269
0.7204	Intermediate Similarity	NPC228835
0.7203	Intermediate Similarity	NPC323752
0.7202	Intermediate Similarity	NPC477044
0.7202	Intermediate Similarity	NPC171317
0.7202	Intermediate Similarity	NPC477041
0.7198	Intermediate Similarity	NPC21638
0.7196	Intermediate Similarity	NPC95783
0.7186	Intermediate Similarity	NPC477788
0.7177	Intermediate Similarity	NPC55772
0.7171	Intermediate Similarity	NPC201700
0.7169	Intermediate Similarity	NPC293917
0.7169	Intermediate Similarity	NPC241024
0.7169	Intermediate Similarity	NPC477045
0.7167	Intermediate Similarity	NPC37473
0.7161	Intermediate Similarity	NPC475720
0.7161	Intermediate Similarity	NPC474192
0.7156	Intermediate Similarity	NPC469358
0.7156	Intermediate Similarity	NPC123839
0.7156	Intermediate Similarity	NPC126066
0.7156	Intermediate Similarity	NPC475165
0.715	Intermediate Similarity	NPC213629
0.715	Intermediate Similarity	NPC34271
0.7149	Intermediate Similarity	NPC155143
0.7149	Intermediate Similarity	NPC137589
0.7143	Intermediate Similarity	NPC282231
0.7143	Intermediate Similarity	NPC473317
0.7143	Intermediate Similarity	NPC470280
0.7137	Intermediate Similarity	NPC476491
0.7137	Intermediate Similarity	NPC473757
0.713	Intermediate Similarity	NPC472292
0.713	Intermediate Similarity	NPC472113
0.7129	Intermediate Similarity	NPC111275
0.7124	Intermediate Similarity	NPC250129
0.7124	Intermediate Similarity	NPC476818
0.7122	Intermediate Similarity	NPC160105
0.7122	Intermediate Similarity	NPC54988
0.7118	Intermediate Similarity	NPC162812
0.7116	Intermediate Similarity	NPC472112
0.7111	Intermediate Similarity	NPC107077
0.7111	Intermediate Similarity	NPC284102
0.7111	Intermediate Similarity	NPC223791
0.7111	Intermediate Similarity	NPC477548
0.711	Intermediate Similarity	NPC472293
0.7108	Intermediate Similarity	NPC311276
0.7108	Intermediate Similarity	NPC194640
0.7105	Intermediate Similarity	NPC471284
0.7105	Intermediate Similarity	NPC264674
0.7105	Intermediate Similarity	NPC477979
0.7105	Intermediate Similarity	NPC4421

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 NPC472762 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	531
0.2-0.3	709
0.3-0.4	2150
0.4-0.5	3054
0.5-0.6	1963
0.6-0.7	482
0.7-0.8	54
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
0.7934	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD7957	Phase 1
0.7834	Intermediate Similarity	NPD7470	Discontinued
0.7745	Intermediate Similarity	NPD2092	Phase 2
0.7745	Intermediate Similarity	NPD2094	Phase 2
0.7745	Intermediate Similarity	NPD2095	Phase 2
0.7707	Intermediate Similarity	NPD2091	Phase 2
0.7707	Intermediate Similarity	NPD2096	Phase 2
0.7647	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD482	Approved
0.7535	Intermediate Similarity	NPD4500	Approved
0.7535	Intermediate Similarity	NPD4501	Approved
0.75	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2509	Approved
0.7455	Intermediate Similarity	NPD2510	Approved
0.7446	Intermediate Similarity	NPD7824	Approved
0.7441	Intermediate Similarity	NPD4499	Approved
0.7431	Intermediate Similarity	NPD8072	Approved
0.7422	Intermediate Similarity	NPD8326	Phase 3
0.7422	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD8325	Phase 3
0.7403	Intermediate Similarity	NPD7781	Approved
0.7403	Intermediate Similarity	NPD7780	Approved
0.7393	Intermediate Similarity	NPD7234	Approved
0.7393	Intermediate Similarity	NPD7233	Approved
0.7378	Intermediate Similarity	NPD3389	Approved
0.7378	Intermediate Similarity	NPD3393	Approved
0.7378	Intermediate Similarity	NPD3394	Approved
0.7373	Intermediate Similarity	NPD4600	Approved
0.7373	Intermediate Similarity	NPD4601	Approved
0.7373	Intermediate Similarity	NPD6479	Discontinued
0.7359	Intermediate Similarity	NPD7731	Approved
0.7359	Intermediate Similarity	NPD7730	Approved
0.735	Intermediate Similarity	NPD7791	Approved
0.735	Intermediate Similarity	NPD7952	Approved
0.735	Intermediate Similarity	NPD7950	Approved
0.735	Intermediate Similarity	NPD7951	Approved
0.735	Intermediate Similarity	NPD7953	Approved
0.735	Intermediate Similarity	NPD7789	Approved
0.735	Intermediate Similarity	NPD7790	Approved
0.7348	Intermediate Similarity	NPD7271	Approved
0.7318	Intermediate Similarity	NPD5901	Discontinued
0.7317	Intermediate Similarity	NPD750	Phase 2
0.7309	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD8073	Approved
0.7277	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5003	Discontinued
0.7232	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD484	Approved
0.7212	Intermediate Similarity	NPD2144	Approved
0.719	Intermediate Similarity	NPD3038	Discontinued
0.7172	Intermediate Similarity	NPD5482	Discontinued
0.7169	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5426	Phase 3
0.7156	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3006	Discontinued
0.7136	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8468	Phase 2
0.7103	Intermediate Similarity	NPD8431	Approved
0.7095	Intermediate Similarity	NPD4079	Approved
0.7095	Intermediate Similarity	NPD4076	Approved
0.7093	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6595	Phase 3
0.7048	Intermediate Similarity	NPD3505	Approved
0.7048	Intermediate Similarity	NPD3506	Approved
0.7046	Intermediate Similarity	NPD7688	Phase 1
0.7043	Intermediate Similarity	NPD5818	Discontinued
0.704	Intermediate Similarity	NPD6176	Phase 1
0.7026	Intermediate Similarity	NPD6242	Discontinued
0.7022	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4427	Phase 2
0.6983	Remote Similarity	NPD6770	Approved
0.6978	Remote Similarity	NPD7001	Phase 3
0.6978	Remote Similarity	NPD7010	Phase 3
0.697	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6529	Discontinued
0.6959	Remote Similarity	NPD2564	Approved
0.6959	Remote Similarity	NPD2565	Phase 2
0.6959	Remote Similarity	NPD6281	Approved
0.6946	Remote Similarity	NPD4885	Approved
0.6942	Remote Similarity	NPD6635	Approved
0.6941	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3947	Discontinued
0.693	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5072	Discontinued
0.6929	Remote Similarity	NPD5891	Approved
0.6927	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5913	Phase 3
0.6919	Remote Similarity	NPD4075	Phase 2
0.6914	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7944	Discontinued
0.6902	Remote Similarity	NPD5450	Discontinued
0.69	Remote Similarity	NPD5475	Discontinued
0.6887	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8363	Approved
0.6887	Remote Similarity	NPD8364	Approved
0.6885	Remote Similarity	NPD7576	Discontinued
0.6884	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7707	Approved
0.6875	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8093	Discontinued
0.6867	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3961	Discontinued
0.6858	Remote Similarity	NPD8283	Approved
0.6858	Remote Similarity	NPD56	Approved
0.6858	Remote Similarity	NPD8282	Approved
0.6853	Remote Similarity	NPD5612	Discontinued
0.6847	Remote Similarity	NPD7948	Phase 1
0.6842	Remote Similarity	NPD8423	Phase 2
0.6842	Remote Similarity	NPD8399	Phase 1
0.684	Remote Similarity	NPD8094	Discontinued
0.6835	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7619	Phase 3
0.6833	Remote Similarity	NPD7618	Phase 3
0.6828	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2920	Discontinued
0.6812	Remote Similarity	NPD4506	Discontinued
0.6811	Remote Similarity	NPD7708	Approved
0.681	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7970	Approved
0.6807	Remote Similarity	NPD7603	Discontinued
0.6793	Remote Similarity	NPD7717	Approved
0.6793	Remote Similarity	NPD7716	Approved
0.6792	Remote Similarity	NPD5065	Approved
0.679	Remote Similarity	NPD6735	Approved
0.6787	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD1038	Approved
0.6784	Remote Similarity	NPD8272	Phase 2
0.6773	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7956	Approved
0.6772	Remote Similarity	NPD7955	Approved
0.6771	Remote Similarity	NPD6664	Approved
0.6762	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD2844	Phase 3
0.6761	Remote Similarity	NPD5104	Approved
0.6756	Remote Similarity	NPD5043	Discontinued
0.6751	Remote Similarity	NPD6995	Phase 1
0.6744	Remote Similarity	NPD5899	Approved
0.6744	Remote Similarity	NPD5897	Approved
0.6744	Remote Similarity	NPD5898	Approved
0.6741	Remote Similarity	NPD7777	Approved
0.6741	Remote Similarity	NPD7778	Approved
0.6741	Remote Similarity	NPD53	Approved
0.673	Remote Similarity	NPD8465	Approved
0.673	Remote Similarity	NPD8466	Approved
0.673	Remote Similarity	NPD8429	Approved
0.673	Remote Similarity	NPD8427	Approved
0.673	Remote Similarity	NPD8428	Approved
0.673	Remote Similarity	NPD8467	Approved
0.6727	Remote Similarity	NPD8063	Discontinued
0.6726	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8374	Phase 3
0.6722	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3178	Discontinued
0.6711	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6999	Discontinued
0.6709	Remote Similarity	NPD4301	Approved
0.6705	Remote Similarity	NPD7803	Approved
0.6699	Remote Similarity	NPD3323	Discontinued
0.6697	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3794	Approved
0.6695	Remote Similarity	NPD3795	Approved
0.6682	Remote Similarity	NPD4639	Approved
0.6682	Remote Similarity	NPD4602	Approved
0.6682	Remote Similarity	NPD4638	Approved
0.6682	Remote Similarity	NPD4640	Approved
0.6681	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8358	Approved
0.6667	Remote Similarity	NPD2172	Phase 1
0.6667	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1996	Discontinued
0.6667	Remote Similarity	NPD6154	Approved
0.6667	Remote Similarity	NPD7711	Discontinued
0.6654	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5632	Approved
0.6653	Remote Similarity	NPD8412	Phase 1
0.6652	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7069	Discontinued
0.6652	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6178	Phase 3
0.664	Remote Similarity	NPD8100	Phase 3
0.6639	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8098	Approved
0.6638	Remote Similarity	NPD6987	Phase 1
0.6637	Remote Similarity	NPD6248	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