NPASS Compound

Structure

CID317210 OpenBabel06191716142D 34 38 0 0 1 0 0 0 0 0999 V2000 6.3061 1.6892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8431 2.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3307 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8156 -2.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7210 -0.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5353 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0011 -1.9525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6903 0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 -1.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3826 -1.9513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -2.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3307 1.6892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8431 0.8445 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8460 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8457 -0.4880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5372 -1.4639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5369 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3826 -2.9272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5372 -3.4156 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6906 -0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8677 0.8445 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0230 0.3568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6918 -1.9523 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5353 -0.4879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4130 0.0187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2590 -3.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -4.4275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3800 -0.9756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8659 0.5003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0230 1.3322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 26 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 26 1 0 0 0 0 10 28 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 30 1 6 0 0 0 21 31 1 6 0 0 0 22 26 1 6 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 27 1 6 0 0 0 24 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 6 0 0 0 27 6 1 1 0 0 0 27 32 1 0 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.31
Volume:	497.53
LogP:	2.827
LogD:	2.145
LogS:	-4.544
# Rotatable Bonds:	4
TPSA:	110.52
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	5.637
Fsp3:	0.893
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:	-4.873
MDCK Permeability:	7.62593708714121e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.21
30% Bioavailability (F30%):	0.212

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.498
Plasma Protein Binding (PPB):	75.58621215820312%
Volume Distribution (VD):	1.956
Pgp-substrate:	11.9673433303833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.443
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.505
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	5.882
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.661
Skin Sensitization:	0.198
Carcinogencity:	0.181
Eye Corrosion:	0.006
Eye Irritation:	0.021
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC317210

Natural Product ID:	NPC317210
*Common Name:**	Polyporusterone C
IUPAC Name:	(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(1R)-1-hydroxy-1-[(2R)-3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Polyporusterone C
Standard InCHIKey:	XOSHHFGXQBEREG-ZTBSBOJQSA-N
Standard InCHI:	InChI=1S/C28H44O6/c1-14(2)15(3)23-24(34-23)27(6,32)22-8-10-28(33)17-11-19(29)18-12-20(30)21(31)13-25(18,4)16(17)7-9-26(22,28)5/h11,14-16,18,20-24,30-33H,7-10,12-13H2,1-6H3/t15?,16-,18-,20+,21-,22-,23?,24+,25+,26+,27+,28+/m0/s1
SMILES:	CC(C)C(C)C1C(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL410507
PubChem CID:	44449966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

*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
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[568468]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.289	uM	PMID[568467]

☑ 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 NPC317210 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	236
0.1-0.2	1431
0.2-0.3	4413
0.3-0.4	7875
0.4-0.5	12900
0.5-0.6	6620
0.6-0.7	6096
0.7-0.8	2788
0.8-0.85	255
0.85-0.9	52
0.9-0.95	29
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC76084
0.9533	High Similarity	NPC326542
0.9528	High Similarity	NPC207251
0.9423	High Similarity	NPC83744
0.9333	High Similarity	NPC329417
0.9327	High Similarity	NPC48733
0.9327	High Similarity	NPC302607
0.9327	High Similarity	NPC202167
0.9327	High Similarity	NPC85829
0.9327	High Similarity	NPC150531
0.9327	High Similarity	NPC97202
0.9327	High Similarity	NPC476027
0.9327	High Similarity	NPC50692
0.9327	High Similarity	NPC214264
0.9327	High Similarity	NPC319077
0.9327	High Similarity	NPC49958
0.9327	High Similarity	NPC296945
0.9327	High Similarity	NPC260268
0.9327	High Similarity	NPC171137
0.9327	High Similarity	NPC152695
0.9259	High Similarity	NPC250109
0.9259	High Similarity	NPC962
0.9238	High Similarity	NPC475060
0.9238	High Similarity	NPC477916
0.9238	High Similarity	NPC220229
0.9231	High Similarity	NPC204833
0.9231	High Similarity	NPC209502
0.9151	High Similarity	NPC217201
0.9143	High Similarity	NPC149047
0.9091	High Similarity	NPC49492
0.9091	High Similarity	NPC266728
0.9065	High Similarity	NPC11710
0.9038	High Similarity	NPC477915
0.9018	High Similarity	NPC475041
0.8947	High Similarity	NPC28532
0.8909	High Similarity	NPC73300
0.8909	High Similarity	NPC108721
0.8846	High Similarity	NPC154072
0.8796	High Similarity	NPC65941
0.8783	High Similarity	NPC222688
0.8783	High Similarity	NPC269642
0.8772	High Similarity	NPC109973
0.8718	High Similarity	NPC293112
0.8716	High Similarity	NPC214644
0.8707	High Similarity	NPC469789
0.8692	High Similarity	NPC75531
0.8692	High Similarity	NPC149124
0.8684	High Similarity	NPC61520
0.8644	High Similarity	NPC473253
0.8632	High Similarity	NPC81736
0.8632	High Similarity	NPC172154
0.8598	High Similarity	NPC191892
0.8596	High Similarity	NPC329736
0.8585	High Similarity	NPC476897
0.8559	High Similarity	NPC474229
0.8547	High Similarity	NPC11895
0.8545	High Similarity	NPC87335
0.8534	High Similarity	NPC67569
0.8532	High Similarity	NPC473165
0.8532	High Similarity	NPC144459
0.8509	High Similarity	NPC218970
0.8509	High Similarity	NPC471854
0.8505	High Similarity	NPC22388
0.8505	High Similarity	NPC473424
0.85	High Similarity	NPC470880
0.8487	Intermediate Similarity	NPC470882
0.8482	Intermediate Similarity	NPC472002
0.8482	Intermediate Similarity	NPC280782
0.8475	Intermediate Similarity	NPC8374
0.8475	Intermediate Similarity	NPC8369
0.8462	Intermediate Similarity	NPC23786
0.8462	Intermediate Similarity	NPC271195
0.8462	Intermediate Similarity	NPC470265
0.8462	Intermediate Similarity	NPC170538
0.8448	Intermediate Similarity	NPC474370
0.8448	Intermediate Similarity	NPC268530
0.8448	Intermediate Similarity	NPC154491
0.844	Intermediate Similarity	NPC323834
0.844	Intermediate Similarity	NPC257353
0.8421	Intermediate Similarity	NPC298278
0.8421	Intermediate Similarity	NPC270929
0.8421	Intermediate Similarity	NPC196931
0.8417	Intermediate Similarity	NPC473888
0.8411	Intermediate Similarity	NPC471401
0.8407	Intermediate Similarity	NPC178981
0.8407	Intermediate Similarity	NPC194100
0.8403	Intermediate Similarity	NPC473635
0.839	Intermediate Similarity	NPC473979
0.8376	Intermediate Similarity	NPC46570
0.8376	Intermediate Similarity	NPC310511
0.8376	Intermediate Similarity	NPC159456
0.8376	Intermediate Similarity	NPC4021
0.8365	Intermediate Similarity	NPC111015
0.8365	Intermediate Similarity	NPC67831
0.8365	Intermediate Similarity	NPC174051
0.8364	Intermediate Similarity	NPC230541
0.8364	Intermediate Similarity	NPC165873
0.8362	Intermediate Similarity	NPC473203
0.8362	Intermediate Similarity	NPC264954
0.8349	Intermediate Similarity	NPC72255
0.8349	Intermediate Similarity	NPC471293
0.8347	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC287423
0.8333	Intermediate Similarity	NPC473265
0.8333	Intermediate Similarity	NPC238667
0.8319	Intermediate Similarity	NPC469790
0.8318	Intermediate Similarity	NPC83709
0.8318	Intermediate Similarity	NPC218383
0.8305	Intermediate Similarity	NPC88326
0.8305	Intermediate Similarity	NPC107493
0.8305	Intermediate Similarity	NPC153700
0.8302	Intermediate Similarity	NPC18509
0.8291	Intermediate Similarity	NPC79579
0.8291	Intermediate Similarity	NPC251226
0.8288	Intermediate Similarity	NPC472219
0.8288	Intermediate Similarity	NPC472218
0.8288	Intermediate Similarity	NPC472217
0.8276	Intermediate Similarity	NPC311554
0.8276	Intermediate Similarity	NPC257457
0.8276	Intermediate Similarity	NPC50774
0.8276	Intermediate Similarity	NPC153440
0.8276	Intermediate Similarity	NPC709
0.8273	Intermediate Similarity	NPC166607
0.8273	Intermediate Similarity	NPC60681
0.8273	Intermediate Similarity	NPC102352
0.8261	Intermediate Similarity	NPC190286
0.8261	Intermediate Similarity	NPC179626
0.8257	Intermediate Similarity	NPC311612
0.8257	Intermediate Similarity	NPC247957
0.8257	Intermediate Similarity	NPC117185
0.8257	Intermediate Similarity	NPC249187
0.8257	Intermediate Similarity	NPC140723
0.8257	Intermediate Similarity	NPC26478
0.8246	Intermediate Similarity	NPC471627
0.8246	Intermediate Similarity	NPC52634
0.8246	Intermediate Similarity	NPC471173
0.8246	Intermediate Similarity	NPC260665
0.823	Intermediate Similarity	NPC469655
0.823	Intermediate Similarity	NPC188738
0.823	Intermediate Similarity	NPC469656
0.823	Intermediate Similarity	NPC474846
0.823	Intermediate Similarity	NPC207689
0.823	Intermediate Similarity	NPC471243
0.822	Intermediate Similarity	NPC473256
0.822	Intermediate Similarity	NPC470878
0.8214	Intermediate Similarity	NPC475941
0.8214	Intermediate Similarity	NPC471400
0.8214	Intermediate Similarity	NPC470257
0.8214	Intermediate Similarity	NPC474901
0.8214	Intermediate Similarity	NPC141350
0.8211	Intermediate Similarity	NPC471855
0.8208	Intermediate Similarity	NPC249954
0.8208	Intermediate Similarity	NPC49371
0.8205	Intermediate Similarity	NPC5292
0.8205	Intermediate Similarity	NPC42673
0.8205	Intermediate Similarity	NPC270850
0.8205	Intermediate Similarity	NPC305260
0.8205	Intermediate Similarity	NPC472667
0.8198	Intermediate Similarity	NPC144854
0.8198	Intermediate Similarity	NPC9457
0.8198	Intermediate Similarity	NPC185
0.8198	Intermediate Similarity	NPC3316
0.8198	Intermediate Similarity	NPC59530
0.8198	Intermediate Similarity	NPC471783
0.819	Intermediate Similarity	NPC196227
0.819	Intermediate Similarity	NPC140055
0.819	Intermediate Similarity	NPC470492
0.819	Intermediate Similarity	NPC20302
0.819	Intermediate Similarity	NPC286528
0.819	Intermediate Similarity	NPC167606
0.819	Intermediate Similarity	NPC474518
0.819	Intermediate Similarity	NPC469684
0.8182	Intermediate Similarity	NPC305496
0.8182	Intermediate Similarity	NPC160843
0.8182	Intermediate Similarity	NPC28656
0.8174	Intermediate Similarity	NPC243354
0.8174	Intermediate Similarity	NPC284915
0.8174	Intermediate Similarity	NPC117712
0.8174	Intermediate Similarity	NPC178289
0.8174	Intermediate Similarity	NPC472400
0.8174	Intermediate Similarity	NPC477580
0.8173	Intermediate Similarity	NPC262870
0.8167	Intermediate Similarity	NPC473255
0.8165	Intermediate Similarity	NPC185530
0.8165	Intermediate Similarity	NPC473928
0.8165	Intermediate Similarity	NPC136289
0.8165	Intermediate Similarity	NPC87351
0.8158	Intermediate Similarity	NPC234042
0.8158	Intermediate Similarity	NPC152117
0.8158	Intermediate Similarity	NPC71348
0.8158	Intermediate Similarity	NPC269530
0.8151	Intermediate Similarity	NPC65858
0.8148	Intermediate Similarity	NPC167974
0.8148	Intermediate Similarity	NPC144956
0.8148	Intermediate Similarity	NPC476274
0.8142	Intermediate Similarity	NPC235077
0.8142	Intermediate Similarity	NPC197428
0.8142	Intermediate Similarity	NPC472214
0.8142	Intermediate Similarity	NPC253906
0.8142	Intermediate Similarity	NPC472215

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 NPC317210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1656
0.2-0.3	3933
0.3-0.4	2207
0.4-0.5	647
0.5-0.6	211
0.6-0.7	135
0.7-0.8	125
0.8-0.85	23
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD5211	Phase 2
0.8302	Intermediate Similarity	NPD4755	Approved
0.8273	Intermediate Similarity	NPD6675	Approved
0.8273	Intermediate Similarity	NPD6008	Approved
0.8273	Intermediate Similarity	NPD5739	Approved
0.8273	Intermediate Similarity	NPD6402	Approved
0.8273	Intermediate Similarity	NPD7128	Approved
0.8246	Intermediate Similarity	NPD4632	Approved
0.8214	Intermediate Similarity	NPD6372	Approved
0.8214	Intermediate Similarity	NPD6373	Approved
0.819	Intermediate Similarity	NPD7115	Discovery
0.8182	Intermediate Similarity	NPD5141	Approved
0.8158	Intermediate Similarity	NPD8297	Approved
0.8148	Intermediate Similarity	NPD5285	Approved
0.8148	Intermediate Similarity	NPD4700	Approved
0.8148	Intermediate Similarity	NPD4696	Approved
0.8148	Intermediate Similarity	NPD5286	Approved
0.8142	Intermediate Similarity	NPD4634	Approved
0.8136	Intermediate Similarity	NPD6054	Approved
0.8136	Intermediate Similarity	NPD6059	Approved
0.8136	Intermediate Similarity	NPD6319	Approved
0.8125	Intermediate Similarity	NPD6881	Approved
0.8125	Intermediate Similarity	NPD7320	Approved
0.8125	Intermediate Similarity	NPD6899	Approved
0.807	Intermediate Similarity	NPD6649	Approved
0.807	Intermediate Similarity	NPD6650	Approved
0.8036	Intermediate Similarity	NPD5701	Approved
0.8036	Intermediate Similarity	NPD5697	Approved
0.8036	Intermediate Similarity	NPD6412	Phase 2
0.8	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD5226	Approved
0.8	Intermediate Similarity	NPD5225	Approved
0.8	Intermediate Similarity	NPD4633	Approved
0.8	Intermediate Similarity	NPD5224	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.7981	Intermediate Similarity	NPD5328	Approved
0.7951	Intermediate Similarity	NPD7507	Approved
0.7934	Intermediate Similarity	NPD7604	Phase 2
0.7928	Intermediate Similarity	NPD5175	Approved
0.7928	Intermediate Similarity	NPD5174	Approved
0.7925	Intermediate Similarity	NPD4202	Approved
0.7917	Intermediate Similarity	NPD6016	Approved
0.7917	Intermediate Similarity	NPD6015	Approved
0.7913	Intermediate Similarity	NPD8130	Phase 1
0.7913	Intermediate Similarity	NPD6869	Approved
0.7913	Intermediate Similarity	NPD6847	Approved
0.7913	Intermediate Similarity	NPD6617	Approved
0.7909	Intermediate Similarity	NPD5223	Approved
0.7895	Intermediate Similarity	NPD6013	Approved
0.7895	Intermediate Similarity	NPD6012	Approved
0.7895	Intermediate Similarity	NPD6014	Approved
0.7895	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6009	Approved
0.7869	Intermediate Similarity	NPD7492	Approved
0.7851	Intermediate Similarity	NPD5988	Approved
0.7845	Intermediate Similarity	NPD6882	Approved
0.783	Intermediate Similarity	NPD6079	Approved
0.7818	Intermediate Similarity	NPD7640	Approved
0.7818	Intermediate Similarity	NPD7639	Approved
0.7807	Intermediate Similarity	NPD6011	Approved
0.7805	Intermediate Similarity	NPD6616	Approved
0.7788	Intermediate Similarity	NPD4767	Approved
0.7788	Intermediate Similarity	NPD4768	Approved
0.7769	Intermediate Similarity	NPD5983	Phase 2
0.7768	Intermediate Similarity	NPD4754	Approved
0.776	Intermediate Similarity	NPD7319	Approved
0.7759	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7078	Approved
0.7742	Intermediate Similarity	NPD8293	Discontinued
0.7727	Intermediate Similarity	NPD7638	Approved
0.7706	Intermediate Similarity	NPD4697	Phase 3
0.7692	Intermediate Similarity	NPD3618	Phase 1
0.768	Intermediate Similarity	NPD7736	Approved
0.7672	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6336	Discontinued
0.7652	Intermediate Similarity	NPD5128	Approved
0.7652	Intermediate Similarity	NPD4730	Approved
0.7652	Intermediate Similarity	NPD4729	Approved
0.7642	Intermediate Similarity	NPD4753	Phase 2
0.7636	Intermediate Similarity	NPD6083	Phase 2
0.7636	Intermediate Similarity	NPD6084	Phase 2
0.7545	Intermediate Similarity	NPD5222	Approved
0.7545	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5221	Approved
0.754	Intermediate Similarity	NPD6033	Approved
0.7521	Intermediate Similarity	NPD5247	Approved
0.7521	Intermediate Similarity	NPD5249	Phase 3
0.7521	Intermediate Similarity	NPD5251	Approved
0.7521	Intermediate Similarity	NPD5248	Approved
0.7521	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.7477	Intermediate Similarity	NPD5173	Approved
0.7459	Intermediate Similarity	NPD7101	Approved
0.7459	Intermediate Similarity	NPD7100	Approved
0.7459	Intermediate Similarity	NPD7516	Approved
0.7458	Intermediate Similarity	NPD5215	Approved
0.7458	Intermediate Similarity	NPD5217	Approved
0.7458	Intermediate Similarity	NPD5216	Approved
0.7455	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4629	Approved
0.7455	Intermediate Similarity	NPD5210	Approved
0.7431	Intermediate Similarity	NPD6399	Phase 3
0.7414	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5696	Approved
0.7395	Intermediate Similarity	NPD6053	Discontinued
0.7377	Intermediate Similarity	NPD7328	Approved
0.7377	Intermediate Similarity	NPD7327	Approved
0.7377	Intermediate Similarity	NPD6335	Approved
0.7373	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5135	Approved
0.7373	Intermediate Similarity	NPD5169	Approved
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6909	Approved
0.7339	Intermediate Similarity	NPD6908	Approved
0.7333	Intermediate Similarity	NPD4786	Approved
0.7311	Intermediate Similarity	NPD5127	Approved
0.7308	Intermediate Similarity	NPD4221	Approved
0.7308	Intermediate Similarity	NPD4223	Phase 3
0.7297	Intermediate Similarity	NPD5695	Phase 3
0.7295	Intermediate Similarity	NPD6317	Approved
0.7264	Intermediate Similarity	NPD5329	Approved
0.7258	Intermediate Similarity	NPD8294	Approved
0.7258	Intermediate Similarity	NPD8377	Approved
0.7236	Intermediate Similarity	NPD6314	Approved
0.7236	Intermediate Similarity	NPD6313	Approved
0.7227	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD8328	Phase 3
0.7222	Intermediate Similarity	NPD6067	Discontinued
0.7217	Intermediate Similarity	NPD7632	Discontinued
0.7203	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD7503	Approved
0.72	Intermediate Similarity	NPD8033	Approved
0.72	Intermediate Similarity	NPD8380	Approved
0.72	Intermediate Similarity	NPD8379	Approved
0.72	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8335	Approved
0.72	Intermediate Similarity	NPD8378	Approved
0.72	Intermediate Similarity	NPD8296	Approved
0.7196	Intermediate Similarity	NPD5330	Approved
0.7196	Intermediate Similarity	NPD6409	Approved
0.7196	Intermediate Similarity	NPD6684	Approved
0.7196	Intermediate Similarity	NPD7146	Approved
0.7196	Intermediate Similarity	NPD7521	Approved
0.7196	Intermediate Similarity	NPD7334	Approved
0.7196	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4197	Approved
0.7168	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3667	Approved
0.7131	Intermediate Similarity	NPD5167	Approved
0.713	Intermediate Similarity	NPD7524	Approved
0.7105	Intermediate Similarity	NPD4225	Approved
0.7064	Intermediate Similarity	NPD6903	Approved
0.7064	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6001	Approved
0.7054	Intermediate Similarity	NPD7748	Approved
0.7037	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD4689	Approved
0.7037	Intermediate Similarity	NPD4138	Approved
0.7037	Intermediate Similarity	NPD4690	Approved
0.7037	Intermediate Similarity	NPD4688	Approved
0.7037	Intermediate Similarity	NPD5205	Approved
0.7027	Intermediate Similarity	NPD5281	Approved
0.7027	Intermediate Similarity	NPD7515	Phase 2
0.7027	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.6983	Remote Similarity	NPD5344	Discontinued
0.6972	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7525	Registered
0.6935	Remote Similarity	NPD6868	Approved
0.6917	Remote Similarity	NPD5168	Approved
0.6916	Remote Similarity	NPD4788	Approved
0.6911	Remote Similarity	NPD8133	Approved
0.6909	Remote Similarity	NPD5737	Approved
0.6909	Remote Similarity	NPD6672	Approved
0.6905	Remote Similarity	NPD4522	Approved
0.6903	Remote Similarity	NPD7900	Approved
0.6903	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4694	Approved
0.6881	Remote Similarity	NPD5280	Approved
0.6881	Remote Similarity	NPD5690	Phase 2
0.6881	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD5693	Phase 1
0.6875	Remote Similarity	NPD8035	Phase 2
0.6875	Remote Similarity	NPD8034	Phase 2
0.6852	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4159	Approved
0.6786	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD6698	Approved
0.6767	Remote Similarity	NPD5956	Approved
0.6759	Remote Similarity	NPD6695	Phase 3
0.6757	Remote Similarity	NPD5208	Approved
0.6746	Remote Similarity	NPD8295	Clinical (unspecified phase)

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