NPASS Compound

Structure

NPC257353 OpenBabel07101719512D 33 36 0 0 1 0 0 0 0 0999 V2000 -2.4021 7.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0048 7.1576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 5.8276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7056 3.8607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1321 3.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4035 5.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1028 4.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0251 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 1.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0531 6.9553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7524 6.0299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7539 3.6584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4532 2.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 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 2.5279 -0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1321 0.5706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 21 1 0 0 0 0 20 29 1 6 0 0 0 21 24 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 23 30 2 0 0 0 0 24 26 1 6 0 0 0 25 27 1 1 0 0 0 26 31 1 1 0 0 0 27 32 1 1 0 0 0 28 25 1 1 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.32
Volume:	494.66
LogP:	3.831
LogD:	3.578
LogS:	-4.533
# Rotatable Bonds:	4
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	5.353
Fsp3:	0.821
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:	-4.903
MDCK Permeability:	1.7560018022777513e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.147

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	85.2895736694336%
Volume Distribution (VD):	0.944
Pgp-substrate:	2.6430177688598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.542
CYP3A4-substrate:	0.957

ADMET: Excretion

Clearance (CL):	2.153
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.488
Carcinogencity:	0.394
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC257353

Natural Product ID:	NPC257353
*Common Name:**	3Beta,5Alpha,9Alpha,14A-Tetrahydroxy-(22E,24R)-Ergosta-7,22-Dien-6-One
IUPAC Name:	(3S,5R,9S,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5,9,14-tetrahydroxy-10,13-dimethyl-2,3,4,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:
Standard InCHIKey:	RLODFSODJNFIMP-STGSRIEASA-N
Standard InCHI:	InChI=1S/C28H44O5/c1-17(2)18(3)7-8-19(4)21-10-12-26(31)22-15-23(30)28(33)16-20(29)9-11-25(28,6)27(22,32)14-13-24(21,26)5/h7-8,15,17-21,29,31-33H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,21+,24+,25+,26+,27+,28-/m0/s1
SMILES:	CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@]2(C3=CC(=O)[C@]4(C[C@H](CC[C@]4(C)[C@]3(CC[C@]12C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593352
PubChem CID:	10575956
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO33483	Diaporthe sp.	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23006147]
NPO33483	Diaporthe sp.	Species	Diaporthaceae	Eukaryota	n.a.	Mangrove-Derived Endophytic Fungus Diaporthe sp.	n.a.	PMID[23006147]
NPO33483	Diaporthe sp.	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26186257]

☑ 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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10.0	ug.mL-1	PMID[453547]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	10.0	ug.mL-1	PMID[453547]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10.0	ug.mL-1	PMID[453547]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	10.0	ug.mL-1	PMID[453547]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	10.0	ug.mL-1	PMID[453547]

☑ 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 NPC257353 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	193
0.1-0.2	1186
0.2-0.3	4177
0.3-0.4	8432
0.4-0.5	13164
0.5-0.6	6792
0.6-0.7	6048
0.7-0.8	2388
0.8-0.85	221
0.85-0.9	80
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC249187
0.9794	High Similarity	NPC247957
0.9495	High Similarity	NPC72255
0.9286	High Similarity	NPC154072
0.92	High Similarity	NPC311612
0.9143	High Similarity	NPC73300
0.9143	High Similarity	NPC108721
0.9126	High Similarity	NPC214644
0.9118	High Similarity	NPC185
0.9118	High Similarity	NPC477916
0.91	High Similarity	NPC87351
0.9072	High Similarity	NPC271195
0.902	High Similarity	NPC149047
0.8969	High Similarity	NPC245972
0.8969	High Similarity	NPC196485
0.8932	High Similarity	NPC83744
0.8932	High Similarity	NPC475060
0.8932	High Similarity	NPC220229
0.8922	High Similarity	NPC209502
0.8922	High Similarity	NPC204833
0.8846	High Similarity	NPC329417
0.8846	High Similarity	NPC65941
0.8846	High Similarity	NPC217201
0.8835	High Similarity	NPC97202
0.8835	High Similarity	NPC296945
0.8835	High Similarity	NPC476027
0.8835	High Similarity	NPC319077
0.8835	High Similarity	NPC166607
0.8835	High Similarity	NPC260268
0.8835	High Similarity	NPC48733
0.8835	High Similarity	NPC49958
0.8835	High Similarity	NPC85829
0.8835	High Similarity	NPC302607
0.8835	High Similarity	NPC214264
0.8835	High Similarity	NPC150531
0.8835	High Similarity	NPC171137
0.8835	High Similarity	NPC152695
0.8835	High Similarity	NPC50692
0.8835	High Similarity	NPC202167
0.8824	High Similarity	NPC111323
0.8824	High Similarity	NPC191892
0.88	High Similarity	NPC191565
0.88	High Similarity	NPC103051
0.8788	High Similarity	NPC49371
0.8776	High Similarity	NPC111015
0.8776	High Similarity	NPC8993
0.8763	High Similarity	NPC475806
0.8762	High Similarity	NPC11710
0.8738	High Similarity	NPC160843
0.8725	High Similarity	NPC477915
0.8713	High Similarity	NPC327431
0.8713	High Similarity	NPC144956
0.87	High Similarity	NPC18509
0.8687	High Similarity	NPC476245
0.8687	High Similarity	NPC272617
0.866	High Similarity	NPC48010
0.8624	High Similarity	NPC148458
0.86	High Similarity	NPC249954
0.8586	High Similarity	NPC474690
0.8586	High Similarity	NPC292793
0.8571	High Similarity	NPC64844
0.8571	High Similarity	NPC42847
0.8571	High Similarity	NPC473998
0.8571	High Similarity	NPC233116
0.8571	High Similarity	NPC165873
0.8557	High Similarity	NPC76879
0.8557	High Similarity	NPC474245
0.8557	High Similarity	NPC309603
0.8557	High Similarity	NPC473999
0.8557	High Similarity	NPC326627
0.8557	High Similarity	NPC1015
0.8557	High Similarity	NPC310010
0.8557	High Similarity	NPC31985
0.8557	High Similarity	NPC2983
0.8545	High Similarity	NPC471854
0.8544	High Similarity	NPC477054
0.8544	High Similarity	NPC473424
0.8529	High Similarity	NPC15390
0.8529	High Similarity	NPC474720
0.8519	High Similarity	NPC207251
0.8515	High Similarity	NPC108078
0.8515	High Similarity	NPC320306
0.8515	High Similarity	NPC474785
0.8515	High Similarity	NPC474938
0.8505	High Similarity	NPC76084
0.85	High Similarity	NPC259286
0.85	High Similarity	NPC180950
0.85	High Similarity	NPC472932
0.85	High Similarity	NPC472485
0.8496	Intermediate Similarity	NPC222688
0.8485	Intermediate Similarity	NPC233118
0.8469	Intermediate Similarity	NPC320026
0.8469	Intermediate Similarity	NPC46758
0.8468	Intermediate Similarity	NPC146786
0.8447	Intermediate Similarity	NPC477052
0.8447	Intermediate Similarity	NPC477053
0.8447	Intermediate Similarity	NPC477051
0.844	Intermediate Similarity	NPC317210
0.84	Intermediate Similarity	NPC299100
0.84	Intermediate Similarity	NPC209662
0.8396	Intermediate Similarity	NPC472925
0.8384	Intermediate Similarity	NPC131872
0.8384	Intermediate Similarity	NPC168027
0.8384	Intermediate Similarity	NPC185936
0.8381	Intermediate Similarity	NPC137657
0.8378	Intermediate Similarity	NPC239273
0.8367	Intermediate Similarity	NPC477943
0.8367	Intermediate Similarity	NPC186688
0.8365	Intermediate Similarity	NPC22388
0.8365	Intermediate Similarity	NPC234892
0.8365	Intermediate Similarity	NPC293753
0.8364	Intermediate Similarity	NPC326542
0.8351	Intermediate Similarity	NPC58063
0.8351	Intermediate Similarity	NPC475740
0.835	Intermediate Similarity	NPC83709
0.8349	Intermediate Similarity	NPC475524
0.8349	Intermediate Similarity	NPC100267
0.8349	Intermediate Similarity	NPC71348
0.8333	Intermediate Similarity	NPC126815
0.8333	Intermediate Similarity	NPC107243
0.8333	Intermediate Similarity	NPC190554
0.8333	Intermediate Similarity	NPC235077
0.8318	Intermediate Similarity	NPC472218
0.8318	Intermediate Similarity	NPC472219
0.8318	Intermediate Similarity	NPC472217
0.8317	Intermediate Similarity	NPC472824
0.8317	Intermediate Similarity	NPC297199
0.8304	Intermediate Similarity	NPC311554
0.8304	Intermediate Similarity	NPC257457
0.8302	Intermediate Similarity	NPC60681
0.83	Intermediate Similarity	NPC12722
0.83	Intermediate Similarity	NPC472930
0.83	Intermediate Similarity	NPC472942
0.83	Intermediate Similarity	NPC69454
0.83	Intermediate Similarity	NPC474736
0.8286	Intermediate Similarity	NPC251017
0.8286	Intermediate Similarity	NPC55872
0.8286	Intermediate Similarity	NPC26478
0.8286	Intermediate Similarity	NPC117185
0.8273	Intermediate Similarity	NPC250109
0.8273	Intermediate Similarity	NPC962
0.8269	Intermediate Similarity	NPC163372
0.8269	Intermediate Similarity	NPC302537
0.8265	Intermediate Similarity	NPC193360
0.8265	Intermediate Similarity	NPC471722
0.8257	Intermediate Similarity	NPC472928
0.8257	Intermediate Similarity	NPC207689
0.8252	Intermediate Similarity	NPC114274
0.8252	Intermediate Similarity	NPC477854
0.8247	Intermediate Similarity	NPC293287
0.8247	Intermediate Similarity	NPC474732
0.8247	Intermediate Similarity	NPC474778
0.8247	Intermediate Similarity	NPC94666
0.8247	Intermediate Similarity	NPC474733
0.8247	Intermediate Similarity	NPC6391
0.8247	Intermediate Similarity	NPC472985
0.8247	Intermediate Similarity	NPC469994
0.8247	Intermediate Similarity	NPC472986
0.8247	Intermediate Similarity	NPC31564
0.8247	Intermediate Similarity	NPC261266
0.8247	Intermediate Similarity	NPC145879
0.8247	Intermediate Similarity	NPC51014
0.8247	Intermediate Similarity	NPC152808
0.8241	Intermediate Similarity	NPC87335
0.8235	Intermediate Similarity	NPC192428
0.8235	Intermediate Similarity	NPC117133
0.8235	Intermediate Similarity	NPC477853
0.8224	Intermediate Similarity	NPC44063
0.8218	Intermediate Similarity	NPC279410
0.8218	Intermediate Similarity	NPC119562
0.8208	Intermediate Similarity	NPC28656
0.82	Intermediate Similarity	NPC41554
0.82	Intermediate Similarity	NPC97404
0.82	Intermediate Similarity	NPC116726
0.82	Intermediate Similarity	NPC472978
0.82	Intermediate Similarity	NPC272746
0.82	Intermediate Similarity	NPC63748
0.819	Intermediate Similarity	NPC119601
0.819	Intermediate Similarity	NPC308726
0.819	Intermediate Similarity	NPC195290
0.819	Intermediate Similarity	NPC185530
0.819	Intermediate Similarity	NPC204450
0.8182	Intermediate Similarity	NPC472971
0.8182	Intermediate Similarity	NPC119416
0.8182	Intermediate Similarity	NPC472970
0.8182	Intermediate Similarity	NPC280782
0.8182	Intermediate Similarity	NPC32830
0.8163	Intermediate Similarity	NPC317590
0.8158	Intermediate Similarity	NPC109973
0.8155	Intermediate Similarity	NPC291634
0.8155	Intermediate Similarity	NPC122294
0.8155	Intermediate Similarity	NPC57416
0.8155	Intermediate Similarity	NPC99726
0.8148	Intermediate Similarity	NPC295244
0.8148	Intermediate Similarity	NPC472825
0.8148	Intermediate Similarity	NPC177064
0.8144	Intermediate Similarity	NPC470360
0.8144	Intermediate Similarity	NPC471224
0.8144	Intermediate Similarity	NPC470574
0.8144	Intermediate Similarity	NPC474218

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 NPC257353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1437
0.2-0.3	3832
0.3-0.4	2482
0.4-0.5	738
0.5-0.6	159
0.6-0.7	146
0.7-0.8	113
0.8-0.85	59
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8911	High Similarity	NPD5211	Phase 2
0.8738	High Similarity	NPD5141	Approved
0.8713	High Similarity	NPD5286	Approved
0.8713	High Similarity	NPD5285	Approved
0.8713	High Similarity	NPD4696	Approved
0.87	High Similarity	NPD4755	Approved
0.8557	High Similarity	NPD4753	Phase 2
0.8544	High Similarity	NPD4633	Approved
0.8544	High Similarity	NPD5225	Approved
0.8544	High Similarity	NPD5226	Approved
0.8544	High Similarity	NPD5224	Approved
0.8529	High Similarity	NPD4700	Approved
0.85	High Similarity	NPD5210	Approved
0.85	High Similarity	NPD4629	Approved
0.8462	Intermediate Similarity	NPD5175	Approved
0.8462	Intermediate Similarity	NPD5174	Approved
0.8447	Intermediate Similarity	NPD5223	Approved
0.8333	Intermediate Similarity	NPD4634	Approved
0.8318	Intermediate Similarity	NPD6899	Approved
0.8318	Intermediate Similarity	NPD6881	Approved
0.8302	Intermediate Similarity	NPD6675	Approved
0.8302	Intermediate Similarity	NPD7128	Approved
0.8302	Intermediate Similarity	NPD5739	Approved
0.8302	Intermediate Similarity	NPD6402	Approved
0.83	Intermediate Similarity	NPD4202	Approved
0.8257	Intermediate Similarity	NPD6649	Approved
0.8257	Intermediate Similarity	NPD6650	Approved
0.8247	Intermediate Similarity	NPD3618	Phase 1
0.8241	Intermediate Similarity	NPD6373	Approved
0.8241	Intermediate Similarity	NPD6372	Approved
0.8235	Intermediate Similarity	NPD4697	Phase 3
0.8235	Intermediate Similarity	NPD5221	Approved
0.8235	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5222	Approved
0.8224	Intermediate Similarity	NPD5697	Approved
0.82	Intermediate Similarity	NPD6079	Approved
0.8182	Intermediate Similarity	NPD5328	Approved
0.8165	Intermediate Similarity	NPD7290	Approved
0.8165	Intermediate Similarity	NPD6883	Approved
0.8165	Intermediate Similarity	NPD7102	Approved
0.8155	Intermediate Similarity	NPD6084	Phase 2
0.8155	Intermediate Similarity	NPD6083	Phase 2
0.8155	Intermediate Similarity	NPD5173	Approved
0.8148	Intermediate Similarity	NPD7320	Approved
0.8148	Intermediate Similarity	NPD4730	Approved
0.8148	Intermediate Similarity	NPD4729	Approved
0.8144	Intermediate Similarity	NPD5329	Approved
0.8131	Intermediate Similarity	NPD4768	Approved
0.8131	Intermediate Similarity	NPD4767	Approved
0.8113	Intermediate Similarity	NPD4754	Approved
0.8091	Intermediate Similarity	NPD6617	Approved
0.8091	Intermediate Similarity	NPD8130	Phase 1
0.8091	Intermediate Similarity	NPD6847	Approved
0.8091	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD6012	Approved
0.8073	Intermediate Similarity	NPD6013	Approved
0.8073	Intermediate Similarity	NPD6014	Approved
0.8056	Intermediate Similarity	NPD5701	Approved
0.8041	Intermediate Similarity	NPD4197	Approved
0.8041	Intermediate Similarity	NPD3133	Approved
0.8041	Intermediate Similarity	NPD3666	Approved
0.8041	Intermediate Similarity	NPD4786	Approved
0.8041	Intermediate Similarity	NPD3665	Phase 1
0.8018	Intermediate Similarity	NPD8297	Approved
0.8018	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD5250	Approved
0.8	Intermediate Similarity	NPD5248	Approved
0.8	Intermediate Similarity	NPD5249	Phase 3
0.8	Intermediate Similarity	NPD5251	Approved
0.8	Intermediate Similarity	NPD5247	Approved
0.7982	Intermediate Similarity	NPD6011	Approved
0.7982	Intermediate Similarity	NPD5128	Approved
0.7946	Intermediate Similarity	NPD4632	Approved
0.7928	Intermediate Similarity	NPD5215	Approved
0.7928	Intermediate Similarity	NPD5216	Approved
0.7928	Intermediate Similarity	NPD5217	Approved
0.7905	Intermediate Similarity	NPD5696	Approved
0.7895	Intermediate Similarity	NPD7115	Discovery
0.7879	Intermediate Similarity	NPD5690	Phase 2
0.7845	Intermediate Similarity	NPD6054	Approved
0.7838	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD5135	Approved
0.7838	Intermediate Similarity	NPD5169	Approved
0.7835	Intermediate Similarity	NPD4221	Approved
0.7835	Intermediate Similarity	NPD3667	Approved
0.7835	Intermediate Similarity	NPD4223	Phase 3
0.783	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD5695	Phase 3
0.7768	Intermediate Similarity	NPD5127	Approved
0.7768	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6009	Approved
0.7736	Intermediate Similarity	NPD7638	Approved
0.7712	Intermediate Similarity	NPD6370	Approved
0.77	Intermediate Similarity	NPD5280	Approved
0.77	Intermediate Similarity	NPD4694	Approved
0.77	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5279	Phase 3
0.7692	Intermediate Similarity	NPD6059	Approved
0.7692	Intermediate Similarity	NPD6319	Approved
0.7636	Intermediate Similarity	NPD6008	Approved
0.7627	Intermediate Similarity	NPD6016	Approved
0.7627	Intermediate Similarity	NPD6015	Approved
0.7624	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7101	Approved
0.7607	Intermediate Similarity	NPD7100	Approved
0.7596	Intermediate Similarity	NPD6399	Phase 3
0.7583	Intermediate Similarity	NPD7492	Approved
0.7565	Intermediate Similarity	NPD5167	Approved
0.7563	Intermediate Similarity	NPD5988	Approved
0.7525	Intermediate Similarity	NPD5205	Approved
0.7525	Intermediate Similarity	NPD4689	Approved
0.7525	Intermediate Similarity	NPD4690	Approved
0.7525	Intermediate Similarity	NPD4688	Approved
0.7525	Intermediate Similarity	NPD4693	Phase 3
0.7525	Intermediate Similarity	NPD4138	Approved
0.7521	Intermediate Similarity	NPD6616	Approved
0.7521	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD5168	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD5284	Approved
0.7479	Intermediate Similarity	NPD5983	Phase 2
0.7476	Intermediate Similarity	NPD6080	Approved
0.7476	Intermediate Similarity	NPD6673	Approved
0.7476	Intermediate Similarity	NPD6904	Approved
0.7459	Intermediate Similarity	NPD7078	Approved
0.7453	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6317	Approved
0.7411	Intermediate Similarity	NPD6412	Phase 2
0.74	Intermediate Similarity	NPD4788	Approved
0.7398	Intermediate Similarity	NPD7736	Approved
0.7379	Intermediate Similarity	NPD5737	Approved
0.7379	Intermediate Similarity	NPD6672	Approved
0.7377	Intermediate Similarity	NPD6336	Discontinued
0.7373	Intermediate Similarity	NPD6314	Approved
0.7373	Intermediate Similarity	NPD6313	Approved
0.7364	Intermediate Similarity	NPD5091	Approved
0.7353	Intermediate Similarity	NPD6684	Approved
0.7353	Intermediate Similarity	NPD4623	Approved
0.7353	Intermediate Similarity	NPD5330	Approved
0.7353	Intermediate Similarity	NPD4519	Discontinued
0.7353	Intermediate Similarity	NPD7521	Approved
0.7353	Intermediate Similarity	NPD7334	Approved
0.7353	Intermediate Similarity	NPD6409	Approved
0.7353	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD4195	Approved
0.7333	Intermediate Similarity	NPD5693	Phase 1
0.7333	Intermediate Similarity	NPD6909	Approved
0.7333	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6908	Approved
0.7327	Intermediate Similarity	NPD3668	Phase 3
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7311	Intermediate Similarity	NPD4522	Approved
0.7273	Intermediate Similarity	NPD6931	Approved
0.7273	Intermediate Similarity	NPD4695	Discontinued
0.7273	Intermediate Similarity	NPD7525	Registered
0.7273	Intermediate Similarity	NPD6930	Phase 2
0.7273	Intermediate Similarity	NPD7514	Phase 3
0.7245	Intermediate Similarity	NPD3617	Approved
0.7228	Intermediate Similarity	NPD6695	Phase 3
0.7216	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6903	Approved
0.7212	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7632	Discontinued
0.7203	Intermediate Similarity	NPD6868	Approved
0.7196	Intermediate Similarity	NPD7748	Approved
0.7184	Intermediate Similarity	NPD6098	Approved
0.7172	Intermediate Similarity	NPD6929	Approved
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5694	Approved
0.717	Intermediate Similarity	NPD7637	Suspended
0.7157	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7902	Approved
0.712	Intermediate Similarity	NPD6033	Approved
0.7113	Intermediate Similarity	NPD7339	Approved
0.7113	Intermediate Similarity	NPD6942	Approved
0.7103	Intermediate Similarity	NPD5133	Approved
0.71	Intermediate Similarity	NPD7332	Phase 2
0.7097	Intermediate Similarity	NPD7507	Approved
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD5363	Approved
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7075	Intermediate Similarity	NPD5785	Approved
0.7071	Intermediate Similarity	NPD7145	Approved
0.7063	Intermediate Similarity	NPD7319	Approved
0.7048	Intermediate Similarity	NPD4518	Approved
0.7037	Intermediate Similarity	NPD6001	Approved
0.703	Intermediate Similarity	NPD6902	Approved
0.701	Intermediate Similarity	NPD4784	Approved
0.701	Intermediate Similarity	NPD4785	Approved
0.6983	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5776	Phase 2
0.697	Remote Similarity	NPD6932	Approved
0.697	Remote Similarity	NPD6925	Approved
0.6961	Remote Similarity	NPD4269	Approved
0.6961	Remote Similarity	NPD4270	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