NPASS Compound

Structure

CID76084 OpenBabel06191715412D 33 37 0 0 1 0 0 0 0 0999 V2000 6.3082 1.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8447 2.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3325 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0240 -1.3325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8152 -2.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7219 -0.9941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -1.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 0.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8453 -1.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8453 1.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 -1.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6914 -2.9297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3325 1.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8447 0.8453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5361 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6912 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5376 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5375 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3828 -2.9292 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5370 -3.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8690 0.8453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0240 0.3575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6917 -1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8453 -0.4880 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 -3.4036 0.0116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2488 -3.4293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5371 -4.4175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0240 1.3331 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 6 27 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 19 2 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 15 3 1 1 0 0 0 16 4 1 1 0 0 0 16 17 1 0 0 0 0 17 27 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 29 2 0 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 31 1 6 0 0 0 24 15 1 1 0 0 0 24 25 1 0 0 0 0 24 33 1 0 0 0 0 25 16 1 6 0 0 0 25 33 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 6 0 0 0 28 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.32
Volume:	488.74
LogP:	3.963
LogD:	4.092
LogS:	-4.68
# Rotatable Bonds:	4
TPSA:	90.29
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	5.517
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:	-4.875
MDCK Permeability:	9.870301255432423e-06
Pgp-inhibitor:	0.082
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	92.16045379638672%
Volume Distribution (VD):	1.339
Pgp-substrate:	3.360690116882324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.657
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	11.377
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.367
Skin Sensitization:	0.3
Carcinogencity:	0.234
Eye Corrosion:	0.227
Eye Irritation:	0.077
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC76084

Natural Product ID:	NPC76084
*Common Name:**	Polyporusterone E
IUPAC Name:	(2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-17-[(1S)-1-[(2S,3S)-3-[(2R)-3-methylbutan-2-yl]oxiran-2-yl]ethyl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Polyporusterone E
Standard InCHIKey:	BBNQTVHCXTWVJZ-QOOAPMMESA-N
Standard InCHI:	InChI=1S/C28H44O5/c1-14(2)15(3)24-25(33-24)16(4)17-8-10-28(32)19-11-21(29)20-12-22(30)23(31)13-26(20,5)18(19)7-9-27(17,28)6/h11,14-18,20,22-25,30-32H,7-10,12-13H2,1-6H3/t15-,16+,17-,18+,20+,22-,23+,24+,25+,26-,27-,28-/m1/s1
SMILES:	C[C@@H]([C@@H]1O[C@H]1[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479334
PubChem CID:	44575602
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

Activity Type	# Activity
Cell Line	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[529441]

☑ 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 NPC76084 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	221
0.1-0.2	1411
0.2-0.3	4479
0.3-0.4	8507
0.4-0.5	12616
0.5-0.6	6593
0.6-0.7	6121
0.7-0.8	2472
0.8-0.85	216
0.85-0.9	30
0.9-0.95	29
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC317210
0.9505	High Similarity	NPC209502
0.9505	High Similarity	NPC204833
0.9412	High Similarity	NPC49958
0.9412	High Similarity	NPC152695
0.9412	High Similarity	NPC50692
0.9412	High Similarity	NPC171137
0.9412	High Similarity	NPC476027
0.9412	High Similarity	NPC85829
0.9412	High Similarity	NPC150531
0.9412	High Similarity	NPC302607
0.9412	High Similarity	NPC149047
0.9412	High Similarity	NPC202167
0.9412	High Similarity	NPC260268
0.9412	High Similarity	NPC97202
0.9412	High Similarity	NPC48733
0.9412	High Similarity	NPC296945
0.9412	High Similarity	NPC319077
0.9412	High Similarity	NPC214264
0.934	High Similarity	NPC962
0.932	High Similarity	NPC475060
0.932	High Similarity	NPC477916
0.932	High Similarity	NPC220229
0.932	High Similarity	NPC83744
0.9307	High Similarity	NPC477915
0.9252	High Similarity	NPC326542
0.9245	High Similarity	NPC207251
0.9231	High Similarity	NPC329417
0.9231	High Similarity	NPC217201
0.9167	High Similarity	NPC49492
0.9167	High Similarity	NPC266728
0.9159	High Similarity	NPC250109
0.9143	High Similarity	NPC11710
0.8922	High Similarity	NPC154072
0.8919	High Similarity	NPC475041
0.8839	High Similarity	NPC109973
0.8807	High Similarity	NPC108721
0.8807	High Similarity	NPC73300
0.8785	High Similarity	NPC214644
0.875	High Similarity	NPC473424
0.8713	High Similarity	NPC271195
0.8692	High Similarity	NPC65941
0.8684	High Similarity	NPC222688
0.8684	High Similarity	NPC28532
0.8684	High Similarity	NPC269642
0.8667	High Similarity	NPC191892
0.8649	High Similarity	NPC196931
0.8571	High Similarity	NPC471854
0.8545	High Similarity	NPC280782
0.8534	High Similarity	NPC81736
0.8534	High Similarity	NPC172154
0.8505	High Similarity	NPC323834
0.8505	High Similarity	NPC257353
0.8496	Intermediate Similarity	NPC329736
0.8476	Intermediate Similarity	NPC476897
0.8462	Intermediate Similarity	NPC293112
0.8455	Intermediate Similarity	NPC474229
0.8448	Intermediate Similarity	NPC11895
0.8448	Intermediate Similarity	NPC469789
0.8447	Intermediate Similarity	NPC249954
0.844	Intermediate Similarity	NPC475941
0.844	Intermediate Similarity	NPC474901
0.8431	Intermediate Similarity	NPC111015
0.8426	Intermediate Similarity	NPC165873
0.8421	Intermediate Similarity	NPC61520
0.8411	Intermediate Similarity	NPC149124
0.8411	Intermediate Similarity	NPC72255
0.8411	Intermediate Similarity	NPC75531
0.8396	Intermediate Similarity	NPC22388
0.839	Intermediate Similarity	NPC473253
0.8381	Intermediate Similarity	NPC218383
0.8381	Intermediate Similarity	NPC83709
0.8376	Intermediate Similarity	NPC8369
0.8362	Intermediate Similarity	NPC170538
0.835	Intermediate Similarity	NPC259286
0.835	Intermediate Similarity	NPC200702
0.8333	Intermediate Similarity	NPC166607
0.8333	Intermediate Similarity	NPC311554
0.8333	Intermediate Similarity	NPC257457
0.8333	Intermediate Similarity	NPC60681
0.8333	Intermediate Similarity	NPC69454
0.8319	Intermediate Similarity	NPC270929
0.8318	Intermediate Similarity	NPC311612
0.8318	Intermediate Similarity	NPC247957
0.8318	Intermediate Similarity	NPC249187
0.8318	Intermediate Similarity	NPC140723
0.8318	Intermediate Similarity	NPC26478
0.8302	Intermediate Similarity	NPC471401
0.8286	Intermediate Similarity	NPC103051
0.8276	Intermediate Similarity	NPC67569
0.8273	Intermediate Similarity	NPC87335
0.8269	Intermediate Similarity	NPC471463
0.8269	Intermediate Similarity	NPC49371
0.8261	Intermediate Similarity	NPC264954
0.8261	Intermediate Similarity	NPC473203
0.8257	Intermediate Similarity	NPC144459
0.8257	Intermediate Similarity	NPC230541
0.8257	Intermediate Similarity	NPC473165
0.8257	Intermediate Similarity	NPC185
0.8252	Intermediate Similarity	NPC472977
0.8252	Intermediate Similarity	NPC472976
0.8252	Intermediate Similarity	NPC196227
0.8252	Intermediate Similarity	NPC8993
0.825	Intermediate Similarity	NPC470880
0.8246	Intermediate Similarity	NPC218970
0.8241	Intermediate Similarity	NPC28656
0.8241	Intermediate Similarity	NPC471293
0.8241	Intermediate Similarity	NPC160843
0.8235	Intermediate Similarity	NPC473998
0.8235	Intermediate Similarity	NPC470882
0.8235	Intermediate Similarity	NPC233116
0.8235	Intermediate Similarity	NPC475806
0.8235	Intermediate Similarity	NPC116726
0.8235	Intermediate Similarity	NPC63748
0.823	Intermediate Similarity	NPC238667
0.8224	Intermediate Similarity	NPC136289
0.8224	Intermediate Similarity	NPC87351
0.8224	Intermediate Similarity	NPC185530
0.822	Intermediate Similarity	NPC8374
0.8218	Intermediate Similarity	NPC477943
0.8218	Intermediate Similarity	NPC309603
0.8218	Intermediate Similarity	NPC473999
0.8214	Intermediate Similarity	NPC475970
0.8214	Intermediate Similarity	NPC472002
0.8214	Intermediate Similarity	NPC71348
0.8208	Intermediate Similarity	NPC316964
0.8208	Intermediate Similarity	NPC476274
0.8208	Intermediate Similarity	NPC110149
0.8208	Intermediate Similarity	NPC112167
0.8205	Intermediate Similarity	NPC23786
0.8205	Intermediate Similarity	NPC470265
0.8198	Intermediate Similarity	NPC197428
0.819	Intermediate Similarity	NPC18509
0.819	Intermediate Similarity	NPC268530
0.819	Intermediate Similarity	NPC474370
0.819	Intermediate Similarity	NPC190554
0.819	Intermediate Similarity	NPC476961
0.819	Intermediate Similarity	NPC154491
0.8182	Intermediate Similarity	NPC472218
0.8182	Intermediate Similarity	NPC177064
0.8182	Intermediate Similarity	NPC472219
0.8182	Intermediate Similarity	NPC472825
0.8182	Intermediate Similarity	NPC472217
0.8174	Intermediate Similarity	NPC118638
0.8173	Intermediate Similarity	NPC472932
0.8173	Intermediate Similarity	NPC473170
0.8167	Intermediate Similarity	NPC473888
0.8165	Intermediate Similarity	NPC231530
0.8165	Intermediate Similarity	NPC96377
0.8165	Intermediate Similarity	NPC196528
0.8165	Intermediate Similarity	NPC278628
0.8165	Intermediate Similarity	NPC102352
0.8158	Intermediate Similarity	NPC190286
0.8158	Intermediate Similarity	NPC270958
0.8158	Intermediate Similarity	NPC148458
0.8158	Intermediate Similarity	NPC298278
0.8155	Intermediate Similarity	NPC472930
0.8155	Intermediate Similarity	NPC109305
0.8151	Intermediate Similarity	NPC473635
0.8148	Intermediate Similarity	NPC55872
0.8148	Intermediate Similarity	NPC117185
0.8148	Intermediate Similarity	NPC478057
0.8148	Intermediate Similarity	NPC236390
0.8142	Intermediate Similarity	NPC52634
0.8142	Intermediate Similarity	NPC194100
0.8142	Intermediate Similarity	NPC202889
0.8142	Intermediate Similarity	NPC178981
0.8137	Intermediate Similarity	NPC48010
0.8137	Intermediate Similarity	NPC136801
0.8136	Intermediate Similarity	NPC473979
0.8136	Intermediate Similarity	NPC204812
0.8131	Intermediate Similarity	NPC224720
0.8131	Intermediate Similarity	NPC476240
0.8131	Intermediate Similarity	NPC81530
0.8131	Intermediate Similarity	NPC476223
0.8125	Intermediate Similarity	NPC188738
0.8125	Intermediate Similarity	NPC207689
0.812	Intermediate Similarity	NPC159456
0.812	Intermediate Similarity	NPC46570
0.812	Intermediate Similarity	NPC473256
0.812	Intermediate Similarity	NPC4021
0.812	Intermediate Similarity	NPC470878
0.812	Intermediate Similarity	NPC310511
0.8119	Intermediate Similarity	NPC328539
0.8113	Intermediate Similarity	NPC477854
0.8108	Intermediate Similarity	NPC141350
0.8103	Intermediate Similarity	NPC476960
0.8103	Intermediate Similarity	NPC473270
0.8103	Intermediate Similarity	NPC42673
0.8099	Intermediate Similarity	NPC231529
0.8095	Intermediate Similarity	NPC72204
0.8095	Intermediate Similarity	NPC117133
0.8095	Intermediate Similarity	NPC7124
0.8091	Intermediate Similarity	NPC473037
0.8091	Intermediate Similarity	NPC9457
0.8091	Intermediate Similarity	NPC471783
0.8091	Intermediate Similarity	NPC3316
0.8091	Intermediate Similarity	NPC144854
0.8091	Intermediate Similarity	NPC59530
0.8087	Intermediate Similarity	NPC474518

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 NPC76084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1655
0.2-0.3	3965
0.3-0.4	2212
0.4-0.5	655
0.5-0.6	184
0.6-0.7	139
0.7-0.8	136
0.8-0.85	17
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	NPD6008	Approved
0.8224	Intermediate Similarity	NPD5211	Phase 2
0.8218	Intermediate Similarity	NPD5328	Approved
0.819	Intermediate Similarity	NPD4755	Approved
0.8165	Intermediate Similarity	NPD7128	Approved
0.8165	Intermediate Similarity	NPD6675	Approved
0.8165	Intermediate Similarity	NPD6402	Approved
0.8165	Intermediate Similarity	NPD5739	Approved
0.8142	Intermediate Similarity	NPD4632	Approved
0.8108	Intermediate Similarity	NPD6372	Approved
0.8108	Intermediate Similarity	NPD6373	Approved
0.8087	Intermediate Similarity	NPD7115	Discovery
0.8073	Intermediate Similarity	NPD5141	Approved
0.8058	Intermediate Similarity	NPD6079	Approved
0.8037	Intermediate Similarity	NPD4700	Approved
0.8037	Intermediate Similarity	NPD4696	Approved
0.8037	Intermediate Similarity	NPD7640	Approved
0.8037	Intermediate Similarity	NPD5286	Approved
0.8037	Intermediate Similarity	NPD7639	Approved
0.8037	Intermediate Similarity	NPD5285	Approved
0.8036	Intermediate Similarity	NPD4634	Approved
0.8018	Intermediate Similarity	NPD6881	Approved
0.8018	Intermediate Similarity	NPD7320	Approved
0.8018	Intermediate Similarity	NPD6899	Approved
0.7981	Intermediate Similarity	NPD4202	Approved
0.7965	Intermediate Similarity	NPD6649	Approved
0.7965	Intermediate Similarity	NPD6650	Approved
0.7963	Intermediate Similarity	NPD5223	Approved
0.7944	Intermediate Similarity	NPD7638	Approved
0.7928	Intermediate Similarity	NPD5701	Approved
0.7928	Intermediate Similarity	NPD5697	Approved
0.7925	Intermediate Similarity	NPD4697	Phase 3
0.7921	Intermediate Similarity	NPD3618	Phase 1
0.7895	Intermediate Similarity	NPD8297	Approved
0.789	Intermediate Similarity	NPD5225	Approved
0.789	Intermediate Similarity	NPD5226	Approved
0.789	Intermediate Similarity	NPD5224	Approved
0.789	Intermediate Similarity	NPD4633	Approved
0.7881	Intermediate Similarity	NPD6319	Approved
0.7881	Intermediate Similarity	NPD6054	Approved
0.7881	Intermediate Similarity	NPD6059	Approved
0.7876	Intermediate Similarity	NPD6883	Approved
0.7876	Intermediate Similarity	NPD7102	Approved
0.7876	Intermediate Similarity	NPD7290	Approved
0.7857	Intermediate Similarity	NPD6011	Approved
0.7833	Intermediate Similarity	NPD7604	Phase 2
0.7818	Intermediate Similarity	NPD5175	Approved
0.7818	Intermediate Similarity	NPD4754	Approved
0.7818	Intermediate Similarity	NPD5174	Approved
0.7807	Intermediate Similarity	NPD6847	Approved
0.7807	Intermediate Similarity	NPD8130	Phase 1
0.7807	Intermediate Similarity	NPD6869	Approved
0.7807	Intermediate Similarity	NPD6617	Approved
0.7807	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD6009	Approved
0.7768	Intermediate Similarity	NPD6412	Phase 2
0.7757	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD5221	Approved
0.7757	Intermediate Similarity	NPD5222	Approved
0.775	Intermediate Similarity	NPD6370	Approved
0.7739	Intermediate Similarity	NPD6882	Approved
0.7723	Intermediate Similarity	NPD3133	Approved
0.7723	Intermediate Similarity	NPD3666	Approved
0.7723	Intermediate Similarity	NPD3665	Phase 1
0.7705	Intermediate Similarity	NPD7507	Approved
0.7692	Intermediate Similarity	NPD4753	Phase 2
0.7685	Intermediate Similarity	NPD6084	Phase 2
0.7685	Intermediate Similarity	NPD6083	Phase 2
0.7685	Intermediate Similarity	NPD5173	Approved
0.7679	Intermediate Similarity	NPD4768	Approved
0.7679	Intermediate Similarity	NPD4767	Approved
0.7667	Intermediate Similarity	NPD6016	Approved
0.7667	Intermediate Similarity	NPD5983	Phase 2
0.7667	Intermediate Similarity	NPD6015	Approved
0.7664	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7492	Approved
0.7603	Intermediate Similarity	NPD5988	Approved
0.7561	Intermediate Similarity	NPD6336	Discontinued
0.7561	Intermediate Similarity	NPD6616	Approved
0.7549	Intermediate Similarity	NPD4786	Approved
0.7544	Intermediate Similarity	NPD4729	Approved
0.7544	Intermediate Similarity	NPD5128	Approved
0.7544	Intermediate Similarity	NPD4730	Approved
0.7525	Intermediate Similarity	NPD4223	Phase 3
0.7525	Intermediate Similarity	NPD4221	Approved
0.752	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7477	Intermediate Similarity	NPD6399	Phase 3
0.7476	Intermediate Similarity	NPD5329	Approved
0.7455	Intermediate Similarity	NPD5696	Approved
0.744	Intermediate Similarity	NPD7736	Approved
0.744	Intermediate Similarity	NPD6033	Approved
0.7417	Intermediate Similarity	NPD6335	Approved
0.7414	Intermediate Similarity	NPD5251	Approved
0.7414	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5249	Phase 3
0.7414	Intermediate Similarity	NPD5247	Approved
0.7414	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5135	Approved
0.7414	Intermediate Similarity	NPD5169	Approved
0.7414	Intermediate Similarity	NPD5248	Approved
0.7414	Intermediate Similarity	NPD5250	Approved
0.7411	Intermediate Similarity	NPD7632	Discontinued
0.7404	Intermediate Similarity	NPD7334	Approved
0.7404	Intermediate Similarity	NPD7146	Approved
0.7404	Intermediate Similarity	NPD7521	Approved
0.7404	Intermediate Similarity	NPD5330	Approved
0.7404	Intermediate Similarity	NPD6409	Approved
0.7404	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6684	Approved
0.7395	Intermediate Similarity	NPD6274	Approved
0.7379	Intermediate Similarity	NPD4197	Approved
0.7355	Intermediate Similarity	NPD7101	Approved
0.7355	Intermediate Similarity	NPD7100	Approved
0.7353	Intermediate Similarity	NPD3667	Approved
0.735	Intermediate Similarity	NPD5127	Approved
0.735	Intermediate Similarity	NPD5215	Approved
0.735	Intermediate Similarity	NPD5216	Approved
0.735	Intermediate Similarity	NPD5217	Approved
0.7339	Intermediate Similarity	NPD5695	Phase 3
0.7333	Intermediate Similarity	NPD6317	Approved
0.7288	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD6314	Approved
0.7273	Intermediate Similarity	NPD6313	Approved
0.7264	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6903	Approved
0.7248	Intermediate Similarity	NPD7748	Approved
0.7248	Intermediate Similarity	NPD6001	Approved
0.7238	Intermediate Similarity	NPD4689	Approved
0.7238	Intermediate Similarity	NPD5205	Approved
0.7238	Intermediate Similarity	NPD4693	Phase 3
0.7238	Intermediate Similarity	NPD4690	Approved
0.7238	Intermediate Similarity	NPD4688	Approved
0.7238	Intermediate Similarity	NPD4138	Approved
0.7236	Intermediate Similarity	NPD6908	Approved
0.7236	Intermediate Similarity	NPD6909	Approved
0.7236	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7213	Intermediate Similarity	NPD7516	Approved
0.7207	Intermediate Similarity	NPD7902	Approved
0.7196	Intermediate Similarity	NPD6904	Approved
0.7196	Intermediate Similarity	NPD6673	Approved
0.7196	Intermediate Similarity	NPD6080	Approved
0.717	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5167	Approved
0.7155	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7327	Approved
0.7131	Intermediate Similarity	NPD7328	Approved
0.712	Intermediate Similarity	NPD6067	Discontinued
0.7115	Intermediate Similarity	NPD4788	Approved
0.7107	Intermediate Similarity	NPD6868	Approved
0.7103	Intermediate Similarity	NPD6672	Approved
0.7103	Intermediate Similarity	NPD5737	Approved
0.7094	Intermediate Similarity	NPD5168	Approved
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5690	Phase 2
0.7075	Intermediate Similarity	NPD5280	Approved
0.7075	Intermediate Similarity	NPD5279	Phase 3
0.7075	Intermediate Similarity	NPD4694	Approved
0.7064	Intermediate Similarity	NPD5284	Approved
0.7064	Intermediate Similarity	NPD5281	Approved
0.7064	Intermediate Similarity	NPD5693	Phase 1
0.7016	Intermediate Similarity	NPD8294	Approved
0.7016	Intermediate Similarity	NPD8377	Approved
0.7009	Intermediate Similarity	NPD7524	Approved
0.6991	Remote Similarity	NPD4225	Approved
0.699	Remote Similarity	NPD7525	Registered
0.6984	Remote Similarity	NPD8328	Phase 3
0.6975	Remote Similarity	NPD6371	Approved
0.696	Remote Similarity	NPD8380	Approved
0.696	Remote Similarity	NPD8335	Approved
0.696	Remote Similarity	NPD8379	Approved
0.696	Remote Similarity	NPD8296	Approved
0.696	Remote Similarity	NPD8033	Approved
0.696	Remote Similarity	NPD8378	Approved
0.696	Remote Similarity	NPD7503	Approved
0.6949	Remote Similarity	NPD6686	Approved
0.6944	Remote Similarity	NPD5208	Approved
0.6937	Remote Similarity	NPD7900	Approved
0.6937	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4519	Discontinued
0.6916	Remote Similarity	NPD6098	Approved
0.6916	Remote Similarity	NPD4623	Approved
0.6909	Remote Similarity	NPD6050	Approved
0.6909	Remote Similarity	NPD8035	Phase 2
0.6909	Remote Similarity	NPD8034	Phase 2
0.6893	Remote Similarity	NPD4195	Approved
0.6891	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3668	Phase 3
0.6852	Remote Similarity	NPD3573	Approved
0.6822	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5207	Approved
0.6818	Remote Similarity	NPD5692	Phase 3

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