NPASS Compound

Structure

NPC161947 OpenBabel07101718232D 24 26 0 0 1 0 0 0 0 0999 V2000 2.8569 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 C 0 0 2 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 -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 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 0.0000 -0.0000 0.0000 C 0 0 2 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 -1.7321 -3.0000 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 -0.0000 -3.0000 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 3.3914 -1.1088 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 17 1 0 0 0 0 7 4 1 1 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 6 1 1 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 23 1 0 0 0 0 11 17 1 6 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 16 24 1 6 0 0 0 17 1 1 1 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.14
Volume:	327.905
LogP:	0.169
LogD:	0.051
LogS:	-1.937
# Rotatable Bonds:	2
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	4.582
Fsp3:	0.588
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:	-5.283
MDCK Permeability:	6.194993147801142e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.181
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.225

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.562
Plasma Protein Binding (PPB):	40.567039489746094%
Volume Distribution (VD):	0.897
Pgp-substrate:	33.83715057373047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.297
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	4.067
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.639
Skin Sensitization:	0.433
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC161947

Natural Product ID:	NPC161947
*Common Name:**	4A-Epi-9Alpha-Methoxydihydrodeoxybostrycin
IUPAC Name:	(2R,3S,4aS,9aR,10R)-2,3,5,8-tetrahydroxy-6,10-dimethoxy-3-methyl-1,2,4,4a,9a,10-hexahydroanthracen-9-one
Synonyms:
Standard InCHIKey:	HXASFWLBCSXPEV-HCAPWNQLSA-N
Standard InCHI:	InChI=1S/C17H22O7/c1-17(22)6-8-7(4-11(17)19)14(20)12-9(18)5-10(23-2)15(21)13(12)16(8)24-3/h5,7-8,11,16,18-19,21-22H,4,6H2,1-3H3/t7-,8+,11-,16-,17+/m1/s1
SMILES:	CO[C@@H]1[C@H]2C[C@](C)(O)[C@@H](C[C@H]2C(=O)c2c1c(O)c(cc2O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047186
PubChem CID:	59051895
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
NPO33050	nigrospora sp.	Species	Trichosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22545792]

☑ 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
MIC	9

Activity Type	# Activity
Cell Line	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[550509]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100000.0	nM	PMID[550509]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	50000.0	nM	PMID[550509]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100000.0	nM	PMID[550509]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	>	100000.0	nM	PMID[550509]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1560.0	nM	PMID[550509]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	780.0	nM	PMID[550509]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	780.0	nM	PMID[550509]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	25000.0	nM	PMID[550509]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	25000.0	nM	PMID[550509]

☑ 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 NPC161947 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	410
0.1-0.2	1609
0.2-0.3	3423
0.3-0.4	8501
0.4-0.5	9912
0.5-0.6	3953
0.6-0.7	5216
0.7-0.8	6756
0.8-0.85	2195
0.85-0.9	677
0.9-0.95	40
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC155302
0.9934	High Similarity	NPC87431
0.9608	High Similarity	NPC179732
0.9487	High Similarity	NPC215612
0.9477	High Similarity	NPC68727
0.9474	High Similarity	NPC113608
0.9474	High Similarity	NPC470338
0.9474	High Similarity	NPC51824
0.9474	High Similarity	NPC268992
0.9474	High Similarity	NPC470337
0.9351	High Similarity	NPC472048
0.9346	High Similarity	NPC180944
0.9295	High Similarity	NPC470339
0.925	High Similarity	NPC117854
0.925	High Similarity	NPC6588
0.925	High Similarity	NPC477154
0.9236	High Similarity	NPC472055
0.9236	High Similarity	NPC84571
0.9221	High Similarity	NPC470340
0.9216	High Similarity	NPC225854
0.9187	High Similarity	NPC170245
0.9182	High Similarity	NPC7483
0.9182	High Similarity	NPC475985
0.9177	High Similarity	NPC61010
0.9177	High Similarity	NPC311740
0.9172	High Similarity	NPC329091
0.9172	High Similarity	NPC476242
0.9167	High Similarity	NPC474167
0.9167	High Similarity	NPC470762
0.9167	High Similarity	NPC164427
0.9161	High Similarity	NPC273248
0.9125	High Similarity	NPC25361
0.9125	High Similarity	NPC326520
0.9114	High Similarity	NPC14353
0.9114	High Similarity	NPC228785
0.9114	High Similarity	NPC56085
0.9108	High Similarity	NPC199463
0.9108	High Similarity	NPC78103
0.9108	High Similarity	NPC241904
0.9108	High Similarity	NPC37543
0.9108	High Similarity	NPC300727
0.9108	High Similarity	NPC469584
0.9103	High Similarity	NPC134287
0.9103	High Similarity	NPC130589
0.9097	High Similarity	NPC161778
0.9085	High Similarity	NPC476058
0.9062	High Similarity	NPC236132
0.9062	High Similarity	NPC270837
0.9062	High Similarity	NPC197168
0.9062	High Similarity	NPC152659
0.9062	High Similarity	NPC236521
0.9062	High Similarity	NPC248638
0.9057	High Similarity	NPC40491
0.9057	High Similarity	NPC278052
0.9057	High Similarity	NPC474186
0.9051	High Similarity	NPC100123
0.9051	High Similarity	NPC477410
0.9045	High Similarity	NPC274730
0.9045	High Similarity	NPC5379
0.9045	High Similarity	NPC14561
0.9045	High Similarity	NPC77807
0.9038	High Similarity	NPC124714
0.9038	High Similarity	NPC250557
0.9032	High Similarity	NPC45291
0.9032	High Similarity	NPC19980
0.9012	High Similarity	NPC474024
0.9006	High Similarity	NPC275780
0.9006	High Similarity	NPC472450
0.9006	High Similarity	NPC239752
0.9006	High Similarity	NPC472049
0.9	High Similarity	NPC472964
0.9	High Similarity	NPC294965
0.9	High Similarity	NPC48860
0.9	High Similarity	NPC25152
0.8994	High Similarity	NPC320359
0.8994	High Similarity	NPC36217
0.8994	High Similarity	NPC475886
0.8994	High Similarity	NPC200746
0.8994	High Similarity	NPC474287
0.8994	High Similarity	NPC472902
0.8987	High Similarity	NPC223787
0.8987	High Similarity	NPC474208
0.8987	High Similarity	NPC472910
0.8987	High Similarity	NPC472914
0.8987	High Similarity	NPC474836
0.8987	High Similarity	NPC245758
0.8987	High Similarity	NPC222814
0.8987	High Similarity	NPC470402
0.8987	High Similarity	NPC472911
0.8987	High Similarity	NPC165977
0.8987	High Similarity	NPC96167
0.8987	High Similarity	NPC475267
0.8987	High Similarity	NPC156057
0.8987	High Similarity	NPC217677
0.8987	High Similarity	NPC162869
0.8987	High Similarity	NPC178976
0.8987	High Similarity	NPC48208
0.8987	High Similarity	NPC472913
0.8981	High Similarity	NPC16082
0.8981	High Similarity	NPC39184
0.8981	High Similarity	NPC82592
0.8981	High Similarity	NPC175192
0.8974	High Similarity	NPC131266
0.8974	High Similarity	NPC216769
0.8974	High Similarity	NPC312338
0.8974	High Similarity	NPC181209
0.8974	High Similarity	NPC100971
0.8974	High Similarity	NPC245382
0.8974	High Similarity	NPC35763
0.8974	High Similarity	NPC149889
0.8974	High Similarity	NPC121522
0.8974	High Similarity	NPC269451
0.8974	High Similarity	NPC209487
0.8974	High Similarity	NPC100263
0.8974	High Similarity	NPC291802
0.8968	High Similarity	NPC239363
0.8968	High Similarity	NPC216917
0.8957	High Similarity	NPC188079
0.8951	High Similarity	NPC39091
0.8951	High Similarity	NPC37870
0.8951	High Similarity	NPC43319
0.8951	High Similarity	NPC472452
0.8951	High Similarity	NPC20237
0.8944	High Similarity	NPC41301
0.8944	High Similarity	NPC23298
0.8944	High Similarity	NPC189473
0.8944	High Similarity	NPC186686
0.8944	High Similarity	NPC220313
0.8944	High Similarity	NPC146134
0.8944	High Similarity	NPC249181
0.8938	High Similarity	NPC266314
0.8938	High Similarity	NPC201560
0.8938	High Similarity	NPC474187
0.8938	High Similarity	NPC66288
0.8938	High Similarity	NPC475883
0.8938	High Similarity	NPC474351
0.8931	High Similarity	NPC250214
0.8931	High Similarity	NPC45846
0.8931	High Similarity	NPC95936
0.8931	High Similarity	NPC85121
0.8929	High Similarity	NPC182693
0.8924	High Similarity	NPC24640
0.8924	High Similarity	NPC255106
0.8924	High Similarity	NPC317383
0.8924	High Similarity	NPC142339
0.8924	High Similarity	NPC235165
0.8917	High Similarity	NPC155686
0.8917	High Similarity	NPC93552
0.8917	High Similarity	NPC281477
0.8917	High Similarity	NPC107109
0.8917	High Similarity	NPC89474
0.8916	High Similarity	NPC478050
0.891	High Similarity	NPC132990
0.891	High Similarity	NPC78505
0.891	High Similarity	NPC46882
0.891	High Similarity	NPC262623
0.8903	High Similarity	NPC134293
0.8903	High Similarity	NPC92722
0.8903	High Similarity	NPC102003
0.8896	High Similarity	NPC158761
0.8896	High Similarity	NPC283041
0.8896	High Similarity	NPC470456
0.8896	High Similarity	NPC126204
0.8896	High Similarity	NPC218226
0.8889	High Similarity	NPC473286
0.8889	High Similarity	NPC470457
0.8889	High Similarity	NPC102372
0.8889	High Similarity	NPC191930
0.8889	High Similarity	NPC26386
0.8889	High Similarity	NPC475888
0.8889	High Similarity	NPC50960
0.8889	High Similarity	NPC293319
0.8889	High Similarity	NPC224280
0.8882	High Similarity	NPC211107
0.8882	High Similarity	NPC81679
0.8882	High Similarity	NPC261470
0.8882	High Similarity	NPC191360
0.8882	High Similarity	NPC220912
0.8882	High Similarity	NPC201800
0.8882	High Similarity	NPC474150
0.8882	High Similarity	NPC474162
0.8882	High Similarity	NPC52204
0.8882	High Similarity	NPC229632
0.8875	High Similarity	NPC321399
0.8875	High Similarity	NPC139036
0.8875	High Similarity	NPC476980
0.8875	High Similarity	NPC470810
0.8875	High Similarity	NPC174953
0.8875	High Similarity	NPC472631
0.8875	High Similarity	NPC472630
0.8875	High Similarity	NPC263449
0.8875	High Similarity	NPC119224
0.8875	High Similarity	NPC80375
0.8868	High Similarity	NPC129684
0.8868	High Similarity	NPC474055
0.8868	High Similarity	NPC84935
0.8868	High Similarity	NPC299520
0.8868	High Similarity	NPC236796
0.8868	High Similarity	NPC262286
0.8868	High Similarity	NPC77679

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 NPC161947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	943
0.2-0.3	1901
0.3-0.4	2647
0.4-0.5	1824
0.5-0.6	909
0.6-0.7	425
0.7-0.8	126
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD2801	Approved
0.8734	High Similarity	NPD1934	Approved
0.872	High Similarity	NPD7473	Discontinued
0.8679	High Similarity	NPD2393	Clinical (unspecified phase)
0.865	High Similarity	NPD6232	Discontinued
0.8545	High Similarity	NPD6166	Phase 2
0.8545	High Similarity	NPD6167	Clinical (unspecified phase)
0.8545	High Similarity	NPD6168	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD5494	Approved
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8261	Intermediate Similarity	NPD4380	Phase 2
0.8253	Intermediate Similarity	NPD6959	Discontinued
0.8235	Intermediate Similarity	NPD7074	Phase 3
0.8232	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1511	Approved
0.8198	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7054	Approved
0.816	Intermediate Similarity	NPD37	Approved
0.8133	Intermediate Similarity	NPD6234	Discontinued
0.8129	Intermediate Similarity	NPD7472	Approved
0.8125	Intermediate Similarity	NPD1512	Approved
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD2533	Approved
0.8061	Intermediate Similarity	NPD3817	Phase 2
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4965	Approved
0.8012	Intermediate Similarity	NPD4967	Phase 2
0.8012	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7977	Intermediate Similarity	NPD6797	Phase 2
0.7952	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1510	Phase 2
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7251	Discontinued
0.7907	Intermediate Similarity	NPD7228	Approved
0.7892	Intermediate Similarity	NPD7819	Suspended
0.7886	Intermediate Similarity	NPD7808	Phase 3
0.7874	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6801	Discontinued
0.7821	Intermediate Similarity	NPD1607	Approved
0.7806	Intermediate Similarity	NPD943	Approved
0.7806	Intermediate Similarity	NPD1240	Approved
0.7799	Intermediate Similarity	NPD1549	Phase 2
0.7784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5402	Approved
0.773	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3027	Phase 3
0.7722	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2796	Approved
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.7669	Intermediate Similarity	NPD7390	Discontinued
0.7657	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD2800	Approved
0.7634	Intermediate Similarity	NPD6782	Approved
0.7634	Intermediate Similarity	NPD6778	Approved
0.7634	Intermediate Similarity	NPD6777	Approved
0.7634	Intermediate Similarity	NPD6776	Approved
0.7634	Intermediate Similarity	NPD6779	Approved
0.7634	Intermediate Similarity	NPD6780	Approved
0.7634	Intermediate Similarity	NPD6781	Approved
0.7627	Intermediate Similarity	NPD6559	Discontinued
0.7616	Intermediate Similarity	NPD1247	Approved
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.7611	Intermediate Similarity	NPD8150	Discontinued
0.7605	Intermediate Similarity	NPD6599	Discontinued
0.76	Intermediate Similarity	NPD3751	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.7572	Intermediate Similarity	NPD3787	Discontinued
0.7562	Intermediate Similarity	NPD6099	Approved
0.7562	Intermediate Similarity	NPD6100	Approved
0.7561	Intermediate Similarity	NPD6799	Approved
0.756	Intermediate Similarity	NPD7411	Suspended
0.7546	Intermediate Similarity	NPD6190	Approved
0.7544	Intermediate Similarity	NPD3749	Approved
0.753	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8313	Approved
0.7444	Intermediate Similarity	NPD8312	Approved
0.744	Intermediate Similarity	NPD3226	Approved
0.743	Intermediate Similarity	NPD7240	Approved
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7421	Intermediate Similarity	NPD7698	Approved
0.7421	Intermediate Similarity	NPD7696	Phase 3
0.7421	Intermediate Similarity	NPD7697	Approved
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7409	Intermediate Similarity	NPD8151	Discontinued
0.7386	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7768	Phase 2
0.7382	Intermediate Similarity	NPD7870	Phase 2
0.7382	Intermediate Similarity	NPD7871	Phase 2
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD3750	Approved
0.7372	Intermediate Similarity	NPD9494	Approved
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD6534	Approved
0.7366	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3620	Phase 2
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7354	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7333	Intermediate Similarity	NPD7801	Approved
0.7321	Intermediate Similarity	NPD5403	Approved
0.7299	Intermediate Similarity	NPD919	Approved
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7246	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.7244	Intermediate Similarity	NPD1470	Approved
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1201	Approved
0.7205	Intermediate Similarity	NPD447	Suspended
0.7202	Intermediate Similarity	NPD5401	Approved
0.7198	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD3300	Phase 2
0.7168	Intermediate Similarity	NPD5761	Phase 2
0.7168	Intermediate Similarity	NPD5760	Phase 2
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1551	Phase 2
0.7126	Intermediate Similarity	NPD5353	Approved
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7118	Intermediate Similarity	NPD920	Approved
0.7115	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6674	Discontinued
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2403	Approved
0.7079	Intermediate Similarity	NPD4111	Phase 1
0.7079	Intermediate Similarity	NPD4665	Approved
0.7079	Intermediate Similarity	NPD7229	Phase 3
0.7073	Intermediate Similarity	NPD3748	Approved
0.7073	Intermediate Similarity	NPD2799	Discontinued
0.7072	Intermediate Similarity	NPD7286	Phase 2
0.7066	Intermediate Similarity	NPD8166	Discontinued
0.7051	Intermediate Similarity	NPD9269	Phase 2
0.7047	Intermediate Similarity	NPD2493	Approved
0.7047	Intermediate Similarity	NPD2494	Approved
0.7039	Intermediate Similarity	NPD5242	Approved
0.7037	Intermediate Similarity	NPD6213	Phase 3
0.7037	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6212	Phase 3
0.703	Intermediate Similarity	NPD5405	Approved
0.703	Intermediate Similarity	NPD5404	Approved
0.703	Intermediate Similarity	NPD5406	Approved
0.703	Intermediate Similarity	NPD5408	Approved
0.7026	Intermediate Similarity	NPD4582	Approved
0.7026	Intermediate Similarity	NPD8319	Approved
0.7026	Intermediate Similarity	NPD4583	Approved
0.7026	Intermediate Similarity	NPD8320	Phase 1
0.7019	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD4363	Phase 3
0.7	Intermediate Similarity	NPD4360	Phase 2
0.6995	Remote Similarity	NPD5953	Discontinued
0.6988	Remote Similarity	NPD2344	Approved
0.6981	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2798	Approved
0.6974	Remote Similarity	NPD4004	Approved
0.6974	Remote Similarity	NPD4002	Approved
0.6974	Remote Similarity	NPD7680	Approved
0.6964	Remote Similarity	NPD7003	Approved
0.6959	Remote Similarity	NPD3450	Approved
0.6959	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD3452	Approved
0.6957	Remote Similarity	NPD4625	Phase 3
0.6927	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7907	Approved
0.6927	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1699	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data