NPASS Compound

Structure

NPC472458 OpenBabel07101718202D 39 42 0 0 1 0 0 0 0 0999 V2000 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7023 4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3641 5.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0769 4.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 4.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 5.0032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 8 34 1 0 0 0 0 9 34 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 23 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 31 1 0 0 0 0 17 27 1 0 0 0 0 17 32 1 0 0 0 0 18 30 1 0 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 19 34 1 0 0 0 0 20 35 2 0 0 0 0 20 38 1 0 0 0 0 21 36 2 0 0 0 0 21 39 1 0 0 0 0 22 11 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 1 0 0 0 26 29 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 38 1 0 0 0 0 28 29 1 0 0 0 0 28 33 1 1 0 0 0 29 39 1 1 0 0 0 30 33 2 3 0 0 0 30 37 1 0 0 0 0 31 6 1 1 0 0 0 32 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.37
Volume:	580.565
LogP:	4.246
LogD:	3.894
LogS:	-4.269
# Rotatable Bonds:	9
TPSA:	84.94
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	5.088
Fsp3:	0.781
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.961
MDCK Permeability:	1.6957748812274076e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.201

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	66.9981689453125%
Volume Distribution (VD):	1.394
Pgp-substrate:	23.01282501220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.268
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.457
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.762
CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.597

ADMET: Excretion

Clearance (CL):	4.686
Half-life (T1/2):	0.424

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.555
Drug-inuced Liver Injury (DILI):	0.534
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.089
Carcinogencity:	0.465
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC472458

Natural Product ID:	NPC472458
*Common Name:**	Acetic Acid 2-Acetoxy-17-(1-Dimethylamino-Ethyl)-10,13-Dimethyl-3-((E)-2-Methyl-But-2-Enoylamino)-2,3,4,5,6,7,8,9,10,11,12,13,14,15-Tetradecahydro-1H-Cyclopenta[A]Phenanthren-4-Yl Ester
IUPAC Name:	[(3S,4R,8R,9S,10R,13S)-4-acetyloxy-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-3-[[(E)-2-methylbut-2-enoyl]amino]-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-2-yl] acetate
Synonyms:
Standard InCHIKey:	SHJJWNZZBFZGIB-GOBYDMEKSA-N
Standard InCHI:	InChI=1S/C32H50N2O5/c1-10-18(2)30(37)33-28-27(38-20(4)35)17-32(7)25-15-16-31(6)23(19(3)34(8)9)13-14-24(31)22(25)11-12-26(32)29(28)39-21(5)36/h10,13,19,22,24-29H,11-12,14-17H2,1-9H3,(H,33,37)/b18-10+/t19-,22-,24?,25-,26?,27?,28-,29+,31+,32+/m0/s1
SMILES:	CC=C(C)C(=O)NC1C(CC2(C(C1OC(=O)C)CCC3C2CCC4(C3CC=C4C(C)N(C)C)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL342245
PubChem CID:	44358121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

*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
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	Species	Buxaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	50118.72	nM	PMID[480342]

☑ 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 NPC472458 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	105
0.1-0.2	678
0.2-0.3	3186
0.3-0.4	18883
0.4-0.5	11442
0.5-0.6	7335
0.6-0.7	1050
0.7-0.8	9
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC242692
0.9402	High Similarity	NPC237286
0.9123	High Similarity	NPC165396
0.9027	High Similarity	NPC80834
0.9027	High Similarity	NPC469968
0.885	High Similarity	NPC472359
0.8333	Intermediate Similarity	NPC36497
0.8333	Intermediate Similarity	NPC55462
0.8136	Intermediate Similarity	NPC66862
0.7913	Intermediate Similarity	NPC247060
0.7913	Intermediate Similarity	NPC471083
0.7899	Intermediate Similarity	NPC72753
0.7759	Intermediate Similarity	NPC50815
0.7692	Intermediate Similarity	NPC275839
0.7355	Intermediate Similarity	NPC25340
0.7339	Intermediate Similarity	NPC474452
0.7328	Intermediate Similarity	NPC476903
0.7317	Intermediate Similarity	NPC472313
0.7258	Intermediate Similarity	NPC474459
0.725	Intermediate Similarity	NPC474583
0.72	Intermediate Similarity	NPC56796
0.7131	Intermediate Similarity	NPC258130
0.7131	Intermediate Similarity	NPC86906
0.7119	Intermediate Similarity	NPC4834
0.7107	Intermediate Similarity	NPC90538
0.7034	Intermediate Similarity	NPC276103
0.7034	Intermediate Similarity	NPC54248
0.7009	Intermediate Similarity	NPC474922
0.7	Intermediate Similarity	NPC35037
0.6991	Remote Similarity	NPC166458
0.6975	Remote Similarity	NPC140300
0.697	Remote Similarity	NPC469943
0.6929	Remote Similarity	NPC477291
0.6917	Remote Similarity	NPC325229
0.6917	Remote Similarity	NPC102426
0.6917	Remote Similarity	NPC300179
0.6917	Remote Similarity	NPC275086
0.6917	Remote Similarity	NPC119036
0.6911	Remote Similarity	NPC119329
0.6875	Remote Similarity	NPC478137
0.6863	Remote Similarity	NPC235460
0.685	Remote Similarity	NPC79238
0.6842	Remote Similarity	NPC217801
0.6833	Remote Similarity	NPC51499
0.6829	Remote Similarity	NPC241879
0.6829	Remote Similarity	NPC97487
0.6829	Remote Similarity	NPC10232
0.6829	Remote Similarity	NPC473523
0.6829	Remote Similarity	NPC222153
0.6829	Remote Similarity	NPC187302
0.6829	Remote Similarity	NPC196471
0.6829	Remote Similarity	NPC189588
0.6825	Remote Similarity	NPC218602
0.6812	Remote Similarity	NPC90814
0.6812	Remote Similarity	NPC475472
0.6812	Remote Similarity	NPC189393
0.6803	Remote Similarity	NPC235920
0.6803	Remote Similarity	NPC289670
0.6803	Remote Similarity	NPC96784
0.6794	Remote Similarity	NPC471121
0.6794	Remote Similarity	NPC471118
0.6794	Remote Similarity	NPC9714
0.678	Remote Similarity	NPC38232
0.678	Remote Similarity	NPC93027
0.6777	Remote Similarity	NPC470067
0.6777	Remote Similarity	NPC218107
0.6777	Remote Similarity	NPC470066
0.6777	Remote Similarity	NPC470068
0.6774	Remote Similarity	NPC473543
0.6763	Remote Similarity	NPC73829
0.6763	Remote Similarity	NPC119794
0.6754	Remote Similarity	NPC152684
0.6752	Remote Similarity	NPC194485
0.6752	Remote Similarity	NPC53890
0.6752	Remote Similarity	NPC219937
0.6752	Remote Similarity	NPC123252
0.675	Remote Similarity	NPC304899
0.675	Remote Similarity	NPC253115
0.6748	Remote Similarity	NPC476471
0.6748	Remote Similarity	NPC475344
0.6748	Remote Similarity	NPC226509
0.6746	Remote Similarity	NPC472219
0.6746	Remote Similarity	NPC472217
0.6746	Remote Similarity	NPC159367
0.6746	Remote Similarity	NPC472218
0.6728	Remote Similarity	NPC203005
0.6721	Remote Similarity	NPC251680
0.6721	Remote Similarity	NPC275686
0.6721	Remote Similarity	NPC471041
0.672	Remote Similarity	NPC470055
0.672	Remote Similarity	NPC470056
0.6718	Remote Similarity	NPC471120
0.6718	Remote Similarity	NPC471117
0.6716	Remote Similarity	NPC478138
0.6714	Remote Similarity	NPC76999
0.6695	Remote Similarity	NPC234335
0.6694	Remote Similarity	NPC293299
0.6694	Remote Similarity	NPC474124
0.6694	Remote Similarity	NPC45365
0.6692	Remote Similarity	NPC470540
0.6667	Remote Similarity	NPC473922
0.6667	Remote Similarity	NPC25177
0.6667	Remote Similarity	NPC279974
0.6667	Remote Similarity	NPC470054
0.6667	Remote Similarity	NPC280941
0.6667	Remote Similarity	NPC295110
0.6667	Remote Similarity	NPC299963
0.6667	Remote Similarity	NPC102048
0.6667	Remote Similarity	NPC222875
0.6667	Remote Similarity	NPC75318
0.6667	Remote Similarity	NPC247701
0.6667	Remote Similarity	NPC475617
0.6667	Remote Similarity	NPC235772
0.6667	Remote Similarity	NPC268829
0.6667	Remote Similarity	NPC470276
0.6644	Remote Similarity	NPC36463
0.6644	Remote Similarity	NPC298005
0.6642	Remote Similarity	NPC204556
0.6642	Remote Similarity	NPC476504
0.6639	Remote Similarity	NPC26046
0.6639	Remote Similarity	NPC247233
0.662	Remote Similarity	NPC243902
0.662	Remote Similarity	NPC145899
0.6613	Remote Similarity	NPC152718
0.6613	Remote Similarity	NPC470053
0.6612	Remote Similarity	NPC471903
0.661	Remote Similarity	NPC10274
0.6609	Remote Similarity	NPC75810
0.6587	Remote Similarity	NPC119855
0.6587	Remote Similarity	NPC220217
0.6585	Remote Similarity	NPC208358
0.6581	Remote Similarity	NPC160304
0.6581	Remote Similarity	NPC34754
0.6573	Remote Similarity	NPC132847
0.6562	Remote Similarity	NPC475030
0.656	Remote Similarity	NPC45897
0.656	Remote Similarity	NPC160583
0.656	Remote Similarity	NPC85742
0.6557	Remote Similarity	NPC240650
0.6557	Remote Similarity	NPC476878
0.6557	Remote Similarity	NPC476879
0.6555	Remote Similarity	NPC41239
0.6555	Remote Similarity	NPC177641
0.6555	Remote Similarity	NPC329842
0.6555	Remote Similarity	NPC219516
0.6555	Remote Similarity	NPC130840
0.6552	Remote Similarity	NPC119633
0.6552	Remote Similarity	NPC171698
0.6552	Remote Similarity	NPC168231
0.6552	Remote Similarity	NPC172365
0.6552	Remote Similarity	NPC270957
0.6552	Remote Similarity	NPC210729
0.6552	Remote Similarity	NPC474970
0.6552	Remote Similarity	NPC321340
0.6552	Remote Similarity	NPC82931
0.6538	Remote Similarity	NPC470063
0.6535	Remote Similarity	NPC475781
0.6535	Remote Similarity	NPC471205
0.6535	Remote Similarity	NPC169375
0.6532	Remote Similarity	NPC155974
0.6529	Remote Similarity	NPC276110
0.6529	Remote Similarity	NPC241047
0.6528	Remote Similarity	NPC200788
0.6528	Remote Similarity	NPC476558
0.6528	Remote Similarity	NPC243680
0.6525	Remote Similarity	NPC16265
0.6525	Remote Similarity	NPC170633
0.6522	Remote Similarity	NPC222634
0.6512	Remote Similarity	NPC328052
0.6508	Remote Similarity	NPC470060
0.6508	Remote Similarity	NPC470061
0.6508	Remote Similarity	NPC470059
0.6508	Remote Similarity	NPC470064
0.6508	Remote Similarity	NPC470062
0.6508	Remote Similarity	NPC470058
0.6508	Remote Similarity	NPC470043
0.6508	Remote Similarity	NPC470057
0.6504	Remote Similarity	NPC477876
0.6504	Remote Similarity	NPC477875
0.65	Remote Similarity	NPC473678
0.65	Remote Similarity	NPC7349
0.65	Remote Similarity	NPC476304
0.6496	Remote Similarity	NPC476503
0.6496	Remote Similarity	NPC166857
0.6491	Remote Similarity	NPC472504
0.6486	Remote Similarity	NPC298067
0.6486	Remote Similarity	NPC214821
0.6484	Remote Similarity	NPC88701
0.6483	Remote Similarity	NPC180770
0.6479	Remote Similarity	NPC477072
0.6475	Remote Similarity	NPC292718
0.6475	Remote Similarity	NPC111834
0.6475	Remote Similarity	NPC289140
0.6475	Remote Similarity	NPC327788
0.6475	Remote Similarity	NPC476957
0.6475	Remote Similarity	NPC195366
0.6475	Remote Similarity	NPC306797
0.6475	Remote Similarity	NPC88009
0.6475	Remote Similarity	NPC114743
0.6475	Remote Similarity	NPC169270

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 NPC472458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	86
0.1-0.2	380
0.2-0.3	2352
0.3-0.4	4265
0.4-0.5	1683
0.5-0.6	351
0.6-0.7	33
0.7-0.8	0
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
0.6899	Remote Similarity	NPD7754	Approved
0.6899	Remote Similarity	NPD7755	Approved
0.6723	Remote Similarity	NPD5771	Approved
0.6721	Remote Similarity	NPD8418	Phase 2
0.6721	Remote Similarity	NPD7639	Approved
0.6721	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8078	Approved
0.6667	Remote Similarity	NPD8077	Approved
0.6639	Remote Similarity	NPD7638	Approved
0.6619	Remote Similarity	NPD6914	Discontinued
0.6615	Remote Similarity	NPD8298	Phase 2
0.6406	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6909	Approved
0.6397	Remote Similarity	NPD6908	Approved
0.6341	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5357	Phase 1
0.6328	Remote Similarity	NPD6640	Phase 3
0.6299	Remote Similarity	NPD7987	Approved
0.6299	Remote Similarity	NPD7912	Approved
0.6299	Remote Similarity	NPD7986	Approved
0.6299	Remote Similarity	NPD7911	Approved
0.626	Remote Similarity	NPD6421	Discontinued
0.6231	Remote Similarity	NPD8174	Phase 2
0.623	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7632	Discontinued
0.6202	Remote Similarity	NPD8040	Discontinued
0.6202	Remote Similarity	NPD7333	Discontinued
0.6176	Remote Similarity	NPD7328	Approved
0.6176	Remote Similarity	NPD7327	Approved
0.6159	Remote Similarity	NPD8380	Approved
0.6159	Remote Similarity	NPD8379	Approved
0.6159	Remote Similarity	NPD8335	Approved
0.6159	Remote Similarity	NPD8378	Approved
0.6159	Remote Similarity	NPD8296	Approved
0.6154	Remote Similarity	NPD7989	Approved
0.6154	Remote Similarity	NPD7990	Approved
0.6148	Remote Similarity	NPD7637	Suspended
0.6131	Remote Similarity	NPD7516	Approved
0.6087	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD8377	Approved
0.6081	Remote Similarity	NPD6333	Approved
0.6081	Remote Similarity	NPD6334	Approved
0.6078	Remote Similarity	NPD7625	Phase 1
0.6077	Remote Similarity	NPD6920	Discontinued
0.6069	Remote Similarity	NPD8338	Approved
0.6063	Remote Similarity	NPD6404	Discontinued
0.6048	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7748	Approved
0.6043	Remote Similarity	NPD8033	Approved
0.6039	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7525	Registered
0.6017	Remote Similarity	NPD6695	Phase 3
0.6016	Remote Similarity	NPD8034	Phase 2
0.6016	Remote Similarity	NPD8035	Phase 2
0.6015	Remote Similarity	NPD6420	Discontinued
0.6014	Remote Similarity	NPD8336	Approved
0.6014	Remote Similarity	NPD8337	Approved
0.5987	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6399	Phase 3
0.5966	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7122	Discontinued
0.595	Remote Similarity	NPD7750	Discontinued
0.5946	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6921	Approved
0.592	Remote Similarity	NPD5707	Approved
0.5906	Remote Similarity	NPD7902	Approved
0.5868	Remote Similarity	NPD8308	Discontinued
0.5865	Remote Similarity	NPD6415	Discontinued
0.5859	Remote Similarity	NPD4225	Approved
0.5854	Remote Similarity	NPD6051	Approved
0.585	Remote Similarity	NPD8449	Approved
0.5833	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD4211	Phase 1
0.5833	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD7128	Approved
0.5833	Remote Similarity	NPD6402	Approved
0.5821	Remote Similarity	NPD6413	Approved
0.582	Remote Similarity	NPD7524	Approved
0.5812	Remote Similarity	NPD6929	Approved
0.5812	Remote Similarity	NPD7645	Phase 2
0.5811	Remote Similarity	NPD8450	Suspended
0.5785	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD7260	Phase 2
0.5781	Remote Similarity	NPD7919	Phase 3
0.5781	Remote Similarity	NPD7920	Phase 3
0.5776	Remote Similarity	NPD8144	Approved
0.5776	Remote Similarity	NPD8143	Approved
0.5772	Remote Similarity	NPD8415	Approved
0.5764	Remote Similarity	NPD7507	Approved
0.5763	Remote Similarity	NPD6930	Phase 2
0.5763	Remote Similarity	NPD6931	Approved
0.5763	Remote Similarity	NPD7332	Phase 2
0.576	Remote Similarity	NPD7515	Phase 2
0.5755	Remote Similarity	NPD7115	Discovery
0.5753	Remote Similarity	NPD7319	Approved
0.5748	Remote Similarity	NPD7991	Discontinued
0.5746	Remote Similarity	NPD7320	Approved
0.5746	Remote Similarity	NPD6881	Approved
0.5746	Remote Similarity	NPD6899	Approved
0.5736	Remote Similarity	NPD8088	Phase 1
0.5735	Remote Similarity	NPD8130	Phase 1
0.5734	Remote Similarity	NPD7604	Phase 2
0.5704	Remote Similarity	NPD6372	Approved
0.5704	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD6373	Approved
0.5704	Remote Similarity	NPD7503	Approved
0.5694	Remote Similarity	NPD8299	Approved
0.5694	Remote Similarity	NPD8341	Approved
0.5694	Remote Similarity	NPD8340	Approved
0.5694	Remote Similarity	NPD8342	Approved
0.5693	Remote Similarity	NPD8297	Approved
0.5693	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD7336	Phase 2
0.5693	Remote Similarity	NPD7335	Phase 2
0.5691	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.568	Remote Similarity	NPD3168	Discontinued
0.5672	Remote Similarity	NPD5701	Approved
0.5672	Remote Similarity	NPD5697	Approved
0.5669	Remote Similarity	NPD7900	Approved
0.5669	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD7102	Approved
0.5662	Remote Similarity	NPD7290	Approved
0.5662	Remote Similarity	NPD6883	Approved
0.5659	Remote Similarity	NPD6083	Phase 2
0.5659	Remote Similarity	NPD6084	Phase 2
0.5655	Remote Similarity	NPD8273	Phase 1
0.5649	Remote Similarity	NPD5344	Discontinued
0.5641	Remote Similarity	NPD6925	Approved
0.5641	Remote Similarity	NPD5776	Phase 2
0.5638	Remote Similarity	NPD6845	Suspended
0.5635	Remote Similarity	NPD7087	Discontinued
0.563	Remote Similarity	NPD7514	Phase 3
0.563	Remote Similarity	NPD6686	Approved
0.562	Remote Similarity	NPD6650	Approved
0.562	Remote Similarity	NPD6869	Approved
0.562	Remote Similarity	NPD6649	Approved
0.562	Remote Similarity	NPD6617	Approved
0.562	Remote Similarity	NPD6847	Approved
0.5616	Remote Similarity	NPD8074	Phase 3
0.5608	Remote Similarity	NPD8392	Approved
0.5608	Remote Similarity	NPD8390	Approved
0.5608	Remote Similarity	NPD8391	Approved
0.5606	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD6942	Approved
0.5603	Remote Similarity	NPD7339	Approved
0.56	Remote Similarity	NPD5328	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