NPASS Compound

Structure

NPC130447 OpenBabel07101719512D 36 41 0 0 1 0 0 0 0 0999 V2000 -1.3930 -2.1807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5642 -0.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5527 2.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4607 -0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1409 0.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0588 -0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1928 -1.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3868 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0588 0.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3923 3.1052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3268 2.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5947 0.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0276 -1.2498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5660 -0.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 1.7039 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4607 1.5225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5947 2.0225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4607 0.5225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3268 -0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1928 1.5225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3106 0.8911 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0598 -0.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3268 0.0225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7287 1.5225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1928 0.5225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9855 2.1916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7287 0.5225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9309 0.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0588 1.0225 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4607 -1.4775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0588 2.0225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6030 0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7126 -1.6333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0866 2.6297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5335 -0.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 27 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 21 1 0 0 0 0 15 26 1 6 0 0 0 16 11 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 24 1 6 0 0 0 18 23 1 6 0 0 0 19 23 1 0 0 0 0 19 30 2 0 0 0 0 20 25 1 6 0 0 0 20 31 1 0 0 0 0 21 28 1 1 0 0 0 21 32 1 0 0 0 0 22 33 2 0 0 0 0 22 36 1 0 0 0 0 23 25 1 6 0 0 0 24 26 1 1 0 0 0 25 29 1 1 0 0 0 26 34 1 6 0 0 0 27 24 1 6 0 0 0 27 35 1 0 0 0 0 28 27 1 6 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.22
Volume:	507.702
LogP:	2.547
LogD:	1.594
LogS:	-4.382
# Rotatable Bonds:	0
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	6.389
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.436
MDCK Permeability:	1.1703776181093417e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.658

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	70.70893859863281%
Volume Distribution (VD):	0.512
Pgp-substrate:	20.849872589111328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.752
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.437

ADMET: Excretion

Clearance (CL):	5.009
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.283
Carcinogencity:	0.907
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC130447

Natural Product ID:	NPC130447
*Common Name:**	Jaborosalactone 10
IUPAC Name:	(2aR,3R,4R,5S,5aR,6aS,6bS,10aR,11R,12aS,12bS,12cS)-10a-chloro-2a,4,5a,11-tetrahydroxy-3,3',4',6b,12c-pentamethylspiro[2,3,4,6,6a,10,11,12,12a,12b-decahydro-1H-benzo[j]aceanthrylene-5,5'-furan]-2',7-dione
Synonyms:	Jaborosalactone 10
Standard InCHIKey:	PLGCEFWZUFZCIA-ZWSLVCJESA-N
Standard InCHI:	InChI=1S/C28H37ClO7/c1-13-14(2)28(36-22(13)33)21(32)15(3)26(34)10-8-17-16-11-20(31)25(29)9-6-7-19(30)23(25,4)18(16)12-27(28,35)24(17,26)5/h6-7,15-18,20-21,31-32,34-35H,8-12H2,1-5H3/t15-,16+,17+,18+,20-,21-,23+,24+,25+,26-,27-,28+/m1/s1
SMILES:	O=C1O[C@@]2(C(=C1C)C)[C@H](O)[C@@H](C)[C@]1([C@]3([C@]2(O)C[C@H]2[C@H]([C@@H]3CC1)C[C@H]([C@@]1([C@]2(C)C(=O)C=CC1)Cl)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462855
PubChem CID:	11731038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO29151	Jaborosa odonelliana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO29151	Jaborosa odonelliana	Species	Solanaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	7.32	uM	PMID[484884]
NPT2	Others	Unspecified		Ratio	>	5.2	n.a.	PMID[484884]
NPT27	Others	Unspecified		IC50	>	38000.0	nM	PMID[484884]

☑ 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 NPC130447 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	293
0.1-0.2	1650
0.2-0.3	4677
0.3-0.4	8413
0.4-0.5	13106
0.5-0.6	7266
0.6-0.7	5762
0.7-0.8	1484
0.8-0.85	35
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.937	High Similarity	NPC296617
0.9225	High Similarity	NPC245017
0.896	High Similarity	NPC473979
0.8906	High Similarity	NPC231529
0.8529	High Similarity	NPC473396
0.8519	High Similarity	NPC473233
0.8462	Intermediate Similarity	NPC156797
0.8346	Intermediate Similarity	NPC475041
0.8244	Intermediate Similarity	NPC293112
0.8231	Intermediate Similarity	NPC11895
0.8222	Intermediate Similarity	NPC198361
0.8189	Intermediate Similarity	NPC284068
0.8182	Intermediate Similarity	NPC287423
0.8182	Intermediate Similarity	NPC287903
0.8168	Intermediate Similarity	NPC172154
0.8168	Intermediate Similarity	NPC81736
0.8154	Intermediate Similarity	NPC170538
0.8154	Intermediate Similarity	NPC222688
0.8154	Intermediate Similarity	NPC269642
0.814	Intermediate Similarity	NPC474585
0.814	Intermediate Similarity	NPC79579
0.8125	Intermediate Similarity	NPC311554
0.8125	Intermediate Similarity	NPC257457
0.8125	Intermediate Similarity	NPC153440
0.811	Intermediate Similarity	NPC190286
0.811	Intermediate Similarity	NPC196931
0.8106	Intermediate Similarity	NPC473635
0.8095	Intermediate Similarity	NPC250109
0.8092	Intermediate Similarity	NPC469789
0.8077	Intermediate Similarity	NPC310511
0.8077	Intermediate Similarity	NPC46570
0.8074	Intermediate Similarity	NPC471855
0.8062	Intermediate Similarity	NPC5292
0.8045	Intermediate Similarity	NPC470882
0.803	Intermediate Similarity	NPC8369
0.803	Intermediate Similarity	NPC8374
0.8016	Intermediate Similarity	NPC207251
0.8015	Intermediate Similarity	NPC107493
0.8	Intermediate Similarity	NPC476961
0.8	Intermediate Similarity	NPC474370
0.7985	Intermediate Similarity	NPC311534
0.797	Intermediate Similarity	NPC470973
0.7969	Intermediate Similarity	NPC266728
0.7969	Intermediate Similarity	NPC49492
0.7955	Intermediate Similarity	NPC27363
0.7953	Intermediate Similarity	NPC962
0.7941	Intermediate Similarity	NPC93416
0.7939	Intermediate Similarity	NPC67569
0.7926	Intermediate Similarity	NPC471407
0.7926	Intermediate Similarity	NPC175186
0.7926	Intermediate Similarity	NPC104382
0.7923	Intermediate Similarity	NPC270850
0.7923	Intermediate Similarity	NPC230513
0.7923	Intermediate Similarity	NPC264954
0.7923	Intermediate Similarity	NPC305260
0.7923	Intermediate Similarity	NPC472667
0.7923	Intermediate Similarity	NPC61520
0.792	Intermediate Similarity	NPC284828
0.792	Intermediate Similarity	NPC173905
0.792	Intermediate Similarity	NPC472216
0.792	Intermediate Similarity	NPC5475
0.791	Intermediate Similarity	NPC471357
0.791	Intermediate Similarity	NPC473253
0.791	Intermediate Similarity	NPC117702
0.791	Intermediate Similarity	NPC473265
0.791	Intermediate Similarity	NPC179412
0.791	Intermediate Similarity	NPC146456
0.791	Intermediate Similarity	NPC471356
0.791	Intermediate Similarity	NPC469757
0.7907	Intermediate Similarity	NPC470959
0.7907	Intermediate Similarity	NPC471854
0.7907	Intermediate Similarity	NPC55296
0.7907	Intermediate Similarity	NPC476965
0.7895	Intermediate Similarity	NPC473255
0.7895	Intermediate Similarity	NPC469790
0.7891	Intermediate Similarity	NPC326542
0.7891	Intermediate Similarity	NPC67259
0.7891	Intermediate Similarity	NPC147912
0.7883	Intermediate Similarity	NPC225385
0.7883	Intermediate Similarity	NPC298783
0.7883	Intermediate Similarity	NPC157817
0.7883	Intermediate Similarity	NPC104585
0.7879	Intermediate Similarity	NPC470265
0.7879	Intermediate Similarity	NPC88326
0.7879	Intermediate Similarity	NPC153700
0.7879	Intermediate Similarity	NPC23786
0.7874	Intermediate Similarity	NPC470063
0.7868	Intermediate Similarity	NPC253456
0.7868	Intermediate Similarity	NPC16569
0.7868	Intermediate Similarity	NPC159338
0.7868	Intermediate Similarity	NPC471170
0.7863	Intermediate Similarity	NPC472004
0.7863	Intermediate Similarity	NPC143755
0.7863	Intermediate Similarity	NPC251226
0.7863	Intermediate Similarity	NPC268530
0.7863	Intermediate Similarity	NPC154491
0.7852	Intermediate Similarity	NPC473888
0.7846	Intermediate Similarity	NPC709
0.7846	Intermediate Similarity	NPC329736
0.7846	Intermediate Similarity	NPC50774
0.784	Intermediate Similarity	NPC472825
0.784	Intermediate Similarity	NPC217201
0.7836	Intermediate Similarity	NPC250556
0.7836	Intermediate Similarity	NPC469750
0.7829	Intermediate Similarity	NPC72772
0.7829	Intermediate Similarity	NPC148458
0.7829	Intermediate Similarity	NPC176840
0.7829	Intermediate Similarity	NPC469794
0.782	Intermediate Similarity	NPC120724
0.7812	Intermediate Similarity	NPC73300
0.7812	Intermediate Similarity	NPC108721
0.7812	Intermediate Similarity	NPC317210
0.781	Intermediate Similarity	NPC19124
0.781	Intermediate Similarity	NPC42670
0.7803	Intermediate Similarity	NPC4021
0.7803	Intermediate Similarity	NPC159456
0.7794	Intermediate Similarity	NPC471360
0.7794	Intermediate Similarity	NPC471359
0.7794	Intermediate Similarity	NPC197707
0.7794	Intermediate Similarity	NPC86159
0.7794	Intermediate Similarity	NPC6108
0.7794	Intermediate Similarity	NPC471352
0.7794	Intermediate Similarity	NPC70542
0.7794	Intermediate Similarity	NPC469754
0.7794	Intermediate Similarity	NPC469753
0.7794	Intermediate Similarity	NPC469751
0.7794	Intermediate Similarity	NPC9499
0.7794	Intermediate Similarity	NPC284406
0.7794	Intermediate Similarity	NPC469752
0.7794	Intermediate Similarity	NPC89514
0.7794	Intermediate Similarity	NPC471358
0.7794	Intermediate Similarity	NPC469755
0.7794	Intermediate Similarity	NPC471361
0.7794	Intermediate Similarity	NPC470880
0.7794	Intermediate Similarity	NPC180079
0.7794	Intermediate Similarity	NPC219085
0.7794	Intermediate Similarity	NPC91
0.7794	Intermediate Similarity	NPC221414
0.7794	Intermediate Similarity	NPC10823
0.7794	Intermediate Similarity	NPC251866
0.7794	Intermediate Similarity	NPC17896
0.7786	Intermediate Similarity	NPC473636
0.7786	Intermediate Similarity	NPC77689
0.7786	Intermediate Similarity	NPC42673
0.7778	Intermediate Similarity	NPC11710
0.7778	Intermediate Similarity	NPC240070
0.7778	Intermediate Similarity	NPC329784
0.7769	Intermediate Similarity	NPC239273
0.7769	Intermediate Similarity	NPC134430
0.7769	Intermediate Similarity	NPC167606
0.7769	Intermediate Similarity	NPC286528
0.7769	Intermediate Similarity	NPC470492
0.7769	Intermediate Similarity	NPC140055
0.7769	Intermediate Similarity	NPC20302
0.776	Intermediate Similarity	NPC83744
0.776	Intermediate Similarity	NPC475060
0.776	Intermediate Similarity	NPC220229
0.776	Intermediate Similarity	NPC477916
0.776	Intermediate Similarity	NPC67321
0.776	Intermediate Similarity	NPC144459
0.776	Intermediate Similarity	NPC187435
0.7754	Intermediate Similarity	NPC477709
0.7754	Intermediate Similarity	NPC142756
0.7754	Intermediate Similarity	NPC476221
0.7752	Intermediate Similarity	NPC474181
0.7752	Intermediate Similarity	NPC178289
0.7734	Intermediate Similarity	NPC236217
0.7734	Intermediate Similarity	NPC475524
0.7734	Intermediate Similarity	NPC100267
0.7734	Intermediate Similarity	NPC472002
0.773	Intermediate Similarity	NPC290746
0.773	Intermediate Similarity	NPC79250
0.7727	Intermediate Similarity	NPC4548
0.7727	Intermediate Similarity	NPC41123
0.7727	Intermediate Similarity	NPC109973
0.7727	Intermediate Similarity	NPC114939
0.7727	Intermediate Similarity	NPC145074
0.7721	Intermediate Similarity	NPC473620
0.7717	Intermediate Similarity	NPC239097
0.7717	Intermediate Similarity	NPC37116
0.7717	Intermediate Similarity	NPC5284
0.7717	Intermediate Similarity	NPC197428
0.7714	Intermediate Similarity	NPC59288
0.771	Intermediate Similarity	NPC146280
0.771	Intermediate Similarity	NPC146786
0.771	Intermediate Similarity	NPC124676
0.7704	Intermediate Similarity	NPC15095
0.7704	Intermediate Similarity	NPC159499
0.7698	Intermediate Similarity	NPC65941
0.7698	Intermediate Similarity	NPC275539
0.7698	Intermediate Similarity	NPC189075
0.7698	Intermediate Similarity	NPC476823
0.7698	Intermediate Similarity	NPC329417
0.7692	Intermediate Similarity	NPC470793
0.7692	Intermediate Similarity	NPC64318
0.7692	Intermediate Similarity	NPC270929
0.7692	Intermediate Similarity	NPC471816
0.7692	Intermediate Similarity	NPC106228
0.7692	Intermediate Similarity	NPC138372
0.7687	Intermediate Similarity	NPC204812

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 NPC130447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	1673
0.2-0.3	3855
0.3-0.4	2256
0.4-0.5	669
0.5-0.6	241
0.6-0.7	126
0.7-0.8	88
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8385	Intermediate Similarity	NPD6336	Discontinued
0.8346	Intermediate Similarity	NPD7101	Approved
0.8062	Intermediate Similarity	NPD7100	Approved
0.7937	Intermediate Similarity	NPD5216	Approved
0.7937	Intermediate Similarity	NPD5217	Approved
0.7836	Intermediate Similarity	NPD7507	Approved
0.7829	Intermediate Similarity	NPD6868	Approved
0.7812	Intermediate Similarity	NPD4632	Approved
0.7794	Intermediate Similarity	NPD7319	Approved
0.7769	Intermediate Similarity	NPD7115	Discovery
0.7669	Intermediate Similarity	NPD5983	Phase 2
0.7656	Intermediate Similarity	NPD5215	Approved
0.7652	Intermediate Similarity	NPD7516	Approved
0.7615	Intermediate Similarity	NPD5167	Approved
0.7597	Intermediate Similarity	NPD8297	Approved
0.7576	Intermediate Similarity	NPD7328	Approved
0.7576	Intermediate Similarity	NPD7327	Approved
0.7576	Intermediate Similarity	NPD6335	Approved
0.7559	Intermediate Similarity	NPD6881	Approved
0.7559	Intermediate Similarity	NPD6899	Approved
0.7519	Intermediate Similarity	NPD6649	Approved
0.7519	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD5697	Approved
0.7464	Intermediate Similarity	NPD7736	Approved
0.7463	Intermediate Similarity	NPD6319	Approved
0.7444	Intermediate Similarity	NPD6313	Approved
0.7444	Intermediate Similarity	NPD6314	Approved
0.7442	Intermediate Similarity	NPD6883	Approved
0.7442	Intermediate Similarity	NPD7290	Approved
0.7442	Intermediate Similarity	NPD7102	Approved
0.7422	Intermediate Similarity	NPD7320	Approved
0.7422	Intermediate Similarity	NPD5168	Approved
0.7402	Intermediate Similarity	NPD7128	Approved
0.7402	Intermediate Similarity	NPD5739	Approved
0.7402	Intermediate Similarity	NPD6402	Approved
0.7402	Intermediate Similarity	NPD6675	Approved
0.7385	Intermediate Similarity	NPD6847	Approved
0.7385	Intermediate Similarity	NPD6617	Approved
0.7385	Intermediate Similarity	NPD6869	Approved
0.7385	Intermediate Similarity	NPD8130	Phase 1
0.7372	Intermediate Similarity	NPD7492	Approved
0.7364	Intermediate Similarity	NPD6013	Approved
0.7364	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD6012	Approved
0.7364	Intermediate Similarity	NPD6373	Approved
0.7364	Intermediate Similarity	NPD6014	Approved
0.7364	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6054	Approved
0.7328	Intermediate Similarity	NPD6882	Approved
0.7319	Intermediate Similarity	NPD6616	Approved
0.7287	Intermediate Similarity	NPD6011	Approved
0.7279	Intermediate Similarity	NPD8335	Approved
0.7279	Intermediate Similarity	NPD8296	Approved
0.7279	Intermediate Similarity	NPD8379	Approved
0.7279	Intermediate Similarity	NPD8378	Approved
0.7279	Intermediate Similarity	NPD8033	Approved
0.7279	Intermediate Similarity	NPD8380	Approved
0.7266	Intermediate Similarity	NPD6008	Approved
0.7266	Intermediate Similarity	NPD7078	Approved
0.7226	Intermediate Similarity	NPD6370	Approved
0.7214	Intermediate Similarity	NPD6033	Approved
0.7209	Intermediate Similarity	NPD5701	Approved
0.7206	Intermediate Similarity	NPD8377	Approved
0.7206	Intermediate Similarity	NPD8294	Approved
0.72	Intermediate Similarity	NPD7638	Approved
0.7176	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5169	Approved
0.7176	Intermediate Similarity	NPD4634	Approved
0.7174	Intermediate Similarity	NPD7604	Phase 2
0.7165	Intermediate Similarity	NPD5211	Phase 2
0.7154	Intermediate Similarity	NPD5128	Approved
0.7154	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6016	Approved
0.7153	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7132	Intermediate Similarity	NPD4522	Approved
0.7121	Intermediate Similarity	NPD5127	Approved
0.7113	Intermediate Similarity	NPD5956	Approved
0.7101	Intermediate Similarity	NPD5988	Approved
0.708	Intermediate Similarity	NPD6059	Approved
0.7068	Intermediate Similarity	NPD6053	Discontinued
0.7054	Intermediate Similarity	NPD5141	Approved
0.7031	Intermediate Similarity	NPD5224	Approved
0.7031	Intermediate Similarity	NPD5226	Approved
0.7031	Intermediate Similarity	NPD4633	Approved
0.7031	Intermediate Similarity	NPD5225	Approved
0.7029	Intermediate Similarity	NPD7503	Approved
0.7021	Intermediate Similarity	NPD8293	Discontinued
0.6992	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4755	Approved
0.6977	Remote Similarity	NPD5174	Approved
0.6977	Remote Similarity	NPD5175	Approved
0.6953	Remote Similarity	NPD5223	Approved
0.6947	Remote Similarity	NPD6412	Phase 2
0.6947	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6274	Approved
0.6906	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD4700	Approved
0.6861	Remote Similarity	NPD6317	Approved
0.6855	Remote Similarity	NPD6079	Approved
0.685	Remote Similarity	NPD6083	Phase 2
0.685	Remote Similarity	NPD6084	Phase 2
0.68	Remote Similarity	NPD6399	Phase 3
0.6797	Remote Similarity	NPD4225	Approved
0.6767	Remote Similarity	NPD4729	Approved
0.6767	Remote Similarity	NPD4730	Approved
0.6719	Remote Similarity	NPD7902	Approved
0.6694	Remote Similarity	NPD5328	Approved
0.6693	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5344	Discontinued
0.669	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6642	Remote Similarity	NPD8133	Approved
0.6641	Remote Similarity	NPD5222	Approved
0.6641	Remote Similarity	NPD5221	Approved
0.6641	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7632	Discontinued
0.6617	Remote Similarity	NPD4767	Approved
0.6617	Remote Similarity	NPD4768	Approved
0.6614	Remote Similarity	NPD7748	Approved
0.6613	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4754	Approved
0.6589	Remote Similarity	NPD5173	Approved
0.6587	Remote Similarity	NPD7515	Phase 2
0.6567	Remote Similarity	NPD6614	Approved
0.6562	Remote Similarity	NPD4629	Approved
0.6562	Remote Similarity	NPD5695	Phase 3
0.6562	Remote Similarity	NPD5210	Approved
0.6561	Remote Similarity	NPD7236	Approved
0.6549	Remote Similarity	NPD6921	Approved
0.6544	Remote Similarity	NPD5135	Approved
0.6544	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4697	Phase 3
0.6486	Remote Similarity	NPD7260	Phase 2
0.6484	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6903	Approved
0.6471	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8035	Phase 2
0.6457	Remote Similarity	NPD5281	Approved
0.6457	Remote Similarity	NPD8034	Phase 2
0.6457	Remote Similarity	NPD5284	Approved
0.6457	Remote Similarity	NPD5693	Phase 1
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD7521	Approved
0.6452	Remote Similarity	NPD6684	Approved
0.6452	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD5330	Approved
0.6452	Remote Similarity	NPD7146	Approved
0.6452	Remote Similarity	NPD7334	Approved
0.6444	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8516	Approved
0.6434	Remote Similarity	NPD8517	Approved
0.6434	Remote Similarity	NPD8515	Approved
0.6434	Remote Similarity	NPD8513	Phase 3
0.6429	Remote Similarity	NPD4753	Phase 2
0.642	Remote Similarity	NPD6784	Approved
0.642	Remote Similarity	NPD6785	Approved
0.64	Remote Similarity	NPD3573	Approved
0.6391	Remote Similarity	NPD5091	Approved
0.6383	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD6648	Approved
0.6358	Remote Similarity	NPD7239	Suspended
0.6357	Remote Similarity	NPD6001	Approved
0.6345	Remote Similarity	NPD6067	Discontinued
0.634	Remote Similarity	NPD6334	Approved
0.634	Remote Similarity	NPD6333	Approved
0.6308	Remote Similarity	NPD5654	Approved
0.6308	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6673	Approved
0.6299	Remote Similarity	NPD6904	Approved
0.6299	Remote Similarity	NPD6080	Approved
0.629	Remote Similarity	NPD3133	Approved
0.629	Remote Similarity	NPD3665	Phase 1
0.629	Remote Similarity	NPD4786	Approved
0.629	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD5207	Approved
0.6243	Remote Similarity	NPD7799	Discontinued
0.624	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.624	Remote Similarity	NPD1694	Approved
0.6225	Remote Similarity	NPD6845	Suspended
0.622	Remote Similarity	NPD5737	Approved
0.622	Remote Similarity	NPD6672	Approved
0.6212	Remote Similarity	NPD5959	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