NPASS Compound

Structure

NPC470339 OpenBabel07101718322D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 24 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 8 25 1 0 0 0 0 9 24 1 0 0 0 0 10 6 1 6 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 7 1 1 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 6 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 6 0 0 0 17 22 2 0 0 0 0 18 2 1 1 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.14
Volume:	342.564
LogP:	1.985
LogD:	1.237
LogS:	-2.107
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	4.316
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.316
MDCK Permeability:	7.535124950663885e-06
Pgp-inhibitor:	0.038
Pgp-substrate:	0.182
Human Intestinal Absorption (HIA):	0.296
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	76.49979400634766%
Volume Distribution (VD):	0.757
Pgp-substrate:	23.6806697845459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.23
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.31
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	6.816
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.554
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.404
Skin Sensitization:	0.328
Carcinogencity:	0.436
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.209

Download Data

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

Natural Product: NPC470339

Natural Product ID:	NPC470339
*Common Name:**	3-Acetyltetrahydroaltersolanol B
IUPAC Name:	[(2R,3S,4aS,9aS,10R)-3,8,10-trihydroxy-6-methoxy-3-methyl-9-oxo-1,2,4,4a,9a,10-hexahydroanthracen-2-yl] acetate
Synonyms:	3-Acetyltetrahydroaltersolanol B
Standard InCHIKey:	JRESXRRJWODGGI-IJFZLPDQSA-N
Standard InCHI:	InChI=1S/C18H22O7/c1-8(19)25-14-6-10-12(7-18(14,2)23)16(21)11-4-9(24-3)5-13(20)15(11)17(10)22/h4-5,10,12,14,16,20-21,23H,6-7H2,1-3H3/t10-,12-,14+,16-,18-/m0/s1
SMILES:	CC(=O)OC1CC2C(CC1(C)O)C(C3=C(C2=O)C(=CC(=C3)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011663
PubChem CID:	57332239
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[514980]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[514980]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[514980]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[514980]
NPT2	Others	Unspecified		IC50	>	100000	nM	PMID[22276679]

☑ 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 NPC470339 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	350
0.1-0.2	1369
0.2-0.3	3011
0.3-0.4	6205
0.4-0.5	10502
0.5-0.6	5707
0.6-0.7	4516
0.7-0.8	6962
0.8-0.85	3252
0.85-0.9	753
0.9-0.95	60
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC472055
0.9667	High Similarity	NPC113608
0.9667	High Similarity	NPC470337
0.9667	High Similarity	NPC268992
0.9667	High Similarity	NPC51824
0.9667	High Similarity	NPC470338
0.9539	High Similarity	NPC68727
0.9536	High Similarity	NPC180944
0.9408	High Similarity	NPC167903
0.9408	High Similarity	NPC470340
0.9404	High Similarity	NPC225854
0.9351	High Similarity	NPC164427
0.9351	High Similarity	NPC472050
0.9295	High Similarity	NPC155302
0.9295	High Similarity	NPC161947
0.929	High Similarity	NPC246466
0.9236	High Similarity	NPC117985
0.9236	High Similarity	NPC87431
0.9216	High Similarity	NPC215921
0.9216	High Similarity	NPC70016
0.9211	High Similarity	NPC270160
0.9211	High Similarity	NPC237440
0.9187	High Similarity	NPC472622
0.9182	High Similarity	NPC472049
0.9172	High Similarity	NPC470810
0.9161	High Similarity	NPC175192
0.9161	High Similarity	NPC16082
0.9161	High Similarity	NPC82592
0.915	High Similarity	NPC179178
0.9136	High Similarity	NPC472620
0.9125	High Similarity	NPC472621
0.9125	High Similarity	NPC20237
0.9119	High Similarity	NPC249181
0.9097	High Similarity	NPC155686
0.9097	High Similarity	NPC281477
0.9097	High Similarity	NPC478231
0.9097	High Similarity	NPC192189
0.9091	High Similarity	NPC46882
0.9091	High Similarity	NPC200773
0.9091	High Similarity	NPC132990
0.9091	High Similarity	NPC240768
0.9068	High Similarity	NPC473094
0.9068	High Similarity	NPC283041
0.9067	High Similarity	NPC472006
0.9067	High Similarity	NPC51106
0.9062	High Similarity	NPC191930
0.9057	High Similarity	NPC215612
0.9045	High Similarity	NPC190020
0.9045	High Similarity	NPC77679
0.9045	High Similarity	NPC84935
0.9038	High Similarity	NPC170189
0.9038	High Similarity	NPC208173
0.9038	High Similarity	NPC79998
0.9038	High Similarity	NPC69043
0.9038	High Similarity	NPC478230
0.9032	High Similarity	NPC115249
0.9032	High Similarity	NPC184284
0.9032	High Similarity	NPC76041
0.9026	High Similarity	NPC469619
0.9026	High Similarity	NPC469670
0.9024	High Similarity	NPC294149
0.9013	High Similarity	NPC260946
0.9013	High Similarity	NPC107625
0.9012	High Similarity	NPC473096
0.9012	High Similarity	NPC473095
0.9012	High Similarity	NPC472619
0.9007	High Similarity	NPC280404
0.9007	High Similarity	NPC277426
0.9007	High Similarity	NPC210425
0.9007	High Similarity	NPC86373
0.8981	High Similarity	NPC227062
0.8981	High Similarity	NPC150227
0.8974	High Similarity	NPC137301
0.897	High Similarity	NPC324220
0.897	High Similarity	NPC312630
0.8968	High Similarity	NPC207346
0.8968	High Similarity	NPC46564
0.8968	High Similarity	NPC470569
0.8963	High Similarity	NPC472054
0.8961	High Similarity	NPC4423
0.8961	High Similarity	NPC77325
0.8957	High Similarity	NPC298778
0.8954	High Similarity	NPC210320
0.8944	High Similarity	NPC471788
0.894	High Similarity	NPC3732
0.894	High Similarity	NPC469542
0.8938	High Similarity	NPC478229
0.8933	High Similarity	NPC67650
0.8933	High Similarity	NPC1704
0.8924	High Similarity	NPC179732
0.8924	High Similarity	NPC472889
0.8922	High Similarity	NPC208069
0.8917	High Similarity	NPC478221
0.8917	High Similarity	NPC199926
0.8917	High Similarity	NPC99381
0.8917	High Similarity	NPC472890
0.891	High Similarity	NPC273483
0.891	High Similarity	NPC478224
0.891	High Similarity	NPC256141
0.8909	High Similarity	NPC68381
0.8909	High Similarity	NPC474345
0.8903	High Similarity	NPC470568
0.8903	High Similarity	NPC472891
0.8903	High Similarity	NPC147735
0.8896	High Similarity	NPC172329
0.8896	High Similarity	NPC2569
0.8896	High Similarity	NPC215711
0.8896	High Similarity	NPC73411
0.8889	High Similarity	NPC473023
0.8889	High Similarity	NPC165460
0.8889	High Similarity	NPC13481
0.8889	High Similarity	NPC207575
0.8889	High Similarity	NPC469394
0.8875	High Similarity	NPC92589
0.8874	High Similarity	NPC469579
0.8874	High Similarity	NPC474385
0.8868	High Similarity	NPC85121
0.8868	High Similarity	NPC329091
0.8861	High Similarity	NPC146211
0.8861	High Similarity	NPC478223
0.8861	High Similarity	NPC471787
0.8861	High Similarity	NPC24640
0.8854	High Similarity	NPC472799
0.8848	High Similarity	NPC98776
0.8846	High Similarity	NPC478148
0.8846	High Similarity	NPC149526
0.8846	High Similarity	NPC474417
0.8841	High Similarity	NPC241874
0.8839	High Similarity	NPC329933
0.8834	High Similarity	NPC6588
0.8834	High Similarity	NPC477154
0.8834	High Similarity	NPC117854
0.8834	High Similarity	NPC225419
0.8834	High Similarity	NPC474024
0.8831	High Similarity	NPC81835
0.8831	High Similarity	NPC47388
0.8831	High Similarity	NPC8817
0.8831	High Similarity	NPC166583
0.8831	High Similarity	NPC470670
0.8831	High Similarity	NPC472036
0.8831	High Similarity	NPC34802
0.8831	High Similarity	NPC53362
0.8831	High Similarity	NPC473133
0.8827	High Similarity	NPC25361
0.8824	High Similarity	NPC83272
0.882	High Similarity	NPC472964
0.882	High Similarity	NPC211107
0.882	High Similarity	NPC473961
0.8812	High Similarity	NPC36217
0.8812	High Similarity	NPC24627
0.8812	High Similarity	NPC472902
0.8812	High Similarity	NPC321399
0.8805	High Similarity	NPC37543
0.8805	High Similarity	NPC302258
0.8805	High Similarity	NPC199463
0.8805	High Similarity	NPC478226
0.8805	High Similarity	NPC473395
0.8805	High Similarity	NPC263483
0.8805	High Similarity	NPC108456
0.8805	High Similarity	NPC478225
0.8797	High Similarity	NPC67396
0.8797	High Similarity	NPC317585
0.879	High Similarity	NPC175978
0.879	High Similarity	NPC295646
0.879	High Similarity	NPC40356
0.879	High Similarity	NPC217447
0.879	High Similarity	NPC474843
0.879	High Similarity	NPC321363
0.879	High Similarity	NPC253904
0.879	High Similarity	NPC154683
0.879	High Similarity	NPC87708
0.8788	High Similarity	NPC271385
0.8788	High Similarity	NPC473113
0.8788	High Similarity	NPC111536
0.8788	High Similarity	NPC5029
0.8788	High Similarity	NPC76128
0.8788	High Similarity	NPC30432
0.8788	High Similarity	NPC158226
0.8782	High Similarity	NPC180351
0.8782	High Similarity	NPC202595
0.8782	High Similarity	NPC119929
0.8782	High Similarity	NPC96501
0.8782	High Similarity	NPC150928
0.8782	High Similarity	NPC158866
0.8782	High Similarity	NPC290954
0.8782	High Similarity	NPC255641
0.8782	High Similarity	NPC475460
0.878	High Similarity	NPC99613
0.878	High Similarity	NPC165979
0.878	High Similarity	NPC222455
0.878	High Similarity	NPC49487
0.878	High Similarity	NPC163130
0.878	High Similarity	NPC188079
0.878	High Similarity	NPC102810
0.8774	High Similarity	NPC240253
0.8774	High Similarity	NPC153417
0.8774	High Similarity	NPC470359
0.8774	High Similarity	NPC240622
0.8774	High Similarity	NPC471642
0.8774	High Similarity	NPC471641

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 NPC470339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	861
0.2-0.3	1756
0.3-0.4	2520
0.4-0.5	1962
0.5-0.6	1039
0.6-0.7	479
0.7-0.8	182
0.8-0.85	33
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7473	Discontinued
0.882	High Similarity	NPD6232	Discontinued
0.8701	High Similarity	NPD2533	Approved
0.8701	High Similarity	NPD2534	Approved
0.8701	High Similarity	NPD2532	Approved
0.8675	High Similarity	NPD970	Clinical (unspecified phase)
0.8616	High Similarity	NPD2393	Clinical (unspecified phase)
0.8553	High Similarity	NPD1934	Approved
0.8544	High Similarity	NPD4380	Phase 2
0.8509	High Similarity	NPD4868	Clinical (unspecified phase)
0.85	High Similarity	NPD7819	Suspended
0.8457	Intermediate Similarity	NPD7075	Discontinued
0.8443	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD6959	Discontinued
0.8385	Intermediate Similarity	NPD2801	Approved
0.8385	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6166	Phase 2
0.8373	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD37	Approved
0.8293	Intermediate Similarity	NPD6234	Discontinued
0.8286	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD4967	Phase 2
0.8282	Intermediate Similarity	NPD4966	Approved
0.8282	Intermediate Similarity	NPD4965	Approved
0.8274	Intermediate Similarity	NPD3818	Discontinued
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6599	Discontinued
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8171	Intermediate Similarity	NPD3882	Suspended
0.8165	Intermediate Similarity	NPD6799	Approved
0.8165	Intermediate Similarity	NPD1511	Approved
0.8148	Intermediate Similarity	NPD7411	Suspended
0.814	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5494	Approved
0.8129	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3749	Approved
0.8118	Intermediate Similarity	NPD7054	Approved
0.8117	Intermediate Similarity	NPD1510	Phase 2
0.811	Intermediate Similarity	NPD5402	Approved
0.8081	Intermediate Similarity	NPD6559	Discontinued
0.8077	Intermediate Similarity	NPD1549	Phase 2
0.807	Intermediate Similarity	NPD7472	Approved
0.8063	Intermediate Similarity	NPD1512	Approved
0.8059	Intermediate Similarity	NPD7228	Approved
0.8057	Intermediate Similarity	NPD8150	Discontinued
0.8049	Intermediate Similarity	NPD1465	Phase 2
0.8036	Intermediate Similarity	NPD5710	Approved
0.8036	Intermediate Similarity	NPD5711	Approved
0.8025	Intermediate Similarity	NPD3226	Approved
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD8312	Approved
0.7987	Intermediate Similarity	NPD1607	Approved
0.7977	Intermediate Similarity	NPD7251	Discontinued
0.7975	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD4628	Phase 3
0.7974	Intermediate Similarity	NPD1240	Approved
0.7966	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7768	Phase 2
0.7949	Intermediate Similarity	NPD2796	Approved
0.7949	Intermediate Similarity	NPD2935	Discontinued
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7808	Phase 3
0.7922	Intermediate Similarity	NPD230	Phase 1
0.7914	Intermediate Similarity	NPD8151	Discontinued
0.7901	Intermediate Similarity	NPD5403	Approved
0.7898	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7199	Phase 2
0.7862	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8434	Phase 2
0.7849	Intermediate Similarity	NPD3751	Discontinued
0.7838	Intermediate Similarity	NPD7435	Discontinued
0.7834	Intermediate Similarity	NPD6099	Approved
0.7834	Intermediate Similarity	NPD6100	Approved
0.7826	Intermediate Similarity	NPD7390	Discontinued
0.7824	Intermediate Similarity	NPD3787	Discontinued
0.7799	Intermediate Similarity	NPD2800	Approved
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD5401	Approved
0.7772	Intermediate Similarity	NPD6779	Approved
0.7772	Intermediate Similarity	NPD6776	Approved
0.7772	Intermediate Similarity	NPD6778	Approved
0.7772	Intermediate Similarity	NPD6777	Approved
0.7772	Intermediate Similarity	NPD6781	Approved
0.7772	Intermediate Similarity	NPD6782	Approved
0.7772	Intermediate Similarity	NPD6780	Approved
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD6190	Approved
0.7697	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7240	Approved
0.7669	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2799	Discontinued
0.7658	Intermediate Similarity	NPD3748	Approved
0.7643	Intermediate Similarity	NPD6651	Approved
0.7628	Intermediate Similarity	NPD943	Approved
0.7616	Intermediate Similarity	NPD7229	Phase 3
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7874	Approved
0.7592	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7458	Discontinued
0.7576	Intermediate Similarity	NPD920	Approved
0.7561	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7697	Approved
0.7553	Intermediate Similarity	NPD7696	Phase 3
0.7553	Intermediate Similarity	NPD7698	Approved
0.7552	Intermediate Similarity	NPD7783	Phase 2
0.7552	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD919	Approved
0.7515	Intermediate Similarity	NPD6273	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.7513	Intermediate Similarity	NPD8320	Phase 1
0.7513	Intermediate Similarity	NPD8319	Approved
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7472	Intermediate Similarity	NPD7685	Pre-registration
0.7469	Intermediate Similarity	NPD1243	Approved
0.7468	Intermediate Similarity	NPD447	Suspended
0.7461	Intermediate Similarity	NPD7801	Approved
0.7455	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7436	Intermediate Similarity	NPD3027	Phase 3
0.743	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7003	Approved
0.7419	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5760	Phase 2
0.7412	Intermediate Similarity	NPD5761	Phase 2
0.7405	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1613	Approved
0.7405	Intermediate Similarity	NPD4060	Phase 1
0.7403	Intermediate Similarity	NPD1470	Approved
0.7389	Intermediate Similarity	NPD2313	Discontinued
0.738	Intermediate Similarity	NPD7699	Phase 2
0.738	Intermediate Similarity	NPD7700	Phase 2
0.7371	Intermediate Similarity	NPD3926	Phase 2
0.7368	Intermediate Similarity	NPD5353	Approved
0.7368	Intermediate Similarity	NPD1201	Approved
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7356	Intermediate Similarity	NPD1247	Approved
0.7356	Intermediate Similarity	NPD8127	Discontinued
0.7348	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8166	Discontinued
0.7302	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2438	Suspended
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD5242	Approved
0.7261	Intermediate Similarity	NPD4908	Phase 1
0.725	Intermediate Similarity	NPD6355	Discontinued
0.7249	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2798	Approved
0.7239	Intermediate Similarity	NPD2344	Approved
0.7239	Intermediate Similarity	NPD5763	Approved
0.7239	Intermediate Similarity	NPD5762	Approved
0.7232	Intermediate Similarity	NPD2403	Approved
0.7229	Intermediate Similarity	NPD3300	Phase 2
0.7226	Intermediate Similarity	NPD1283	Approved
0.7219	Intermediate Similarity	NPD1653	Approved
0.7219	Intermediate Similarity	NPD4360	Phase 2
0.7219	Intermediate Similarity	NPD4363	Phase 3
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7214	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8455	Phase 2
0.7208	Intermediate Similarity	NPD9269	Phase 2
0.7208	Intermediate Similarity	NPD1608	Approved
0.7197	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD1203	Approved
0.7179	Intermediate Similarity	NPD2797	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