NPASS Compound

Structure

NPC132990 OpenBabel07101718322D 22 24 0 0 1 0 0 0 0 0999 V2000 2.8569 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 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 -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 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 0.8660 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 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 0 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 -1.7321 -1.0000 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 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 3.3914 0.8912 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 2 22 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 11 2 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 6 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 1 1 1 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.09
Volume:	296.545
LogP:	2.409
LogD:	1.478
LogS:	-2.613
# Rotatable Bonds:	1
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	3.59
Fsp3:	0.312
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:	-5.215
MDCK Permeability:	8.514704859408084e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	94.3172836303711%
Volume Distribution (VD):	0.75
Pgp-substrate:	9.760807037353516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.614
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.646
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.175
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	16.107
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.48
AMES Toxicity:	0.557
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.292
Skin Sensitization:	0.9
Carcinogencity:	0.035
Eye Corrosion:	0.004
Eye Irritation:	0.529
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC132990

Natural Product ID:	NPC132990
*Common Name:**	Altersolanol B
IUPAC Name:	(2R,3S)-2,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1H-anthracene-9,10-dione
Synonyms:	Altersolanol B
Standard InCHIKey:	AAHQQIFXAQHGBD-WBMJQRKESA-N
Standard InCHI:	InChI=1S/C16H16O6/c1-16(21)6-10-8(5-12(16)18)15(20)13-9(14(10)19)3-7(22-2)4-11(13)17/h3-4,12,17-18,21H,5-6H2,1-2H3/t12-,16+/m1/s1
SMILES:	COc1cc(O)c2c(c1)C(=O)C1=C(C2=O)C[C@H]([C@@](C1)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011669
PubChem CID:	161389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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]
NPO33215	Stemphylium sp. 33231	Species	Pleosporaceae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25136754]
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	7
MIC	9

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	9
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[447455]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[447455]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[447455]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[447457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[447455]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[447456]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	12.5	ug.mL-1	PMID[447456]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7800.0	nM	PMID[447457]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	7800.0	nM	PMID[447457]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	10000.0	nM	PMID[447457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[447457]
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	>	10000.0	nM	PMID[447457]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	10000.0	nM	PMID[447457]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	7800.0	nM	PMID[447457]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7800.0	nM	PMID[447457]
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 NPC132990 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	380
0.1-0.2	1456
0.2-0.3	3558
0.3-0.4	8141
0.4-0.5	10346
0.5-0.6	3722
0.6-0.7	5565
0.7-0.8	6348
0.8-0.85	2495
0.85-0.9	623
0.9-0.95	58
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46882
0.9863	High Similarity	NPC155686
0.966	High Similarity	NPC470340
0.9597	High Similarity	NPC472050
0.9396	High Similarity	NPC470338
0.9396	High Similarity	NPC268992
0.9396	High Similarity	NPC51824
0.9396	High Similarity	NPC180944
0.9396	High Similarity	NPC470337
0.9396	High Similarity	NPC113608
0.9329	High Similarity	NPC470569
0.9272	High Similarity	NPC68727
0.9262	High Similarity	NPC470568
0.9262	High Similarity	NPC225854
0.9247	High Similarity	NPC475201
0.9216	High Similarity	NPC477410
0.9178	High Similarity	NPC277369
0.9178	High Similarity	NPC215451
0.9172	High Similarity	NPC470341
0.9172	High Similarity	NPC472058
0.9172	High Similarity	NPC234497
0.9172	High Similarity	NPC324522
0.9172	High Similarity	NPC105414
0.9167	High Similarity	NPC472051
0.9167	High Similarity	NPC472057
0.9161	High Similarity	NPC472059
0.9133	High Similarity	NPC255641
0.9133	High Similarity	NPC147735
0.9133	High Similarity	NPC290954
0.9116	High Similarity	NPC19896
0.9103	High Similarity	NPC472053
0.9103	High Similarity	NPC469523
0.9091	High Similarity	NPC470339
0.9067	High Similarity	NPC270160
0.9067	High Similarity	NPC237440
0.9067	High Similarity	NPC134293
0.906	High Similarity	NPC312929
0.906	High Similarity	NPC126767
0.906	High Similarity	NPC245584
0.906	High Similarity	NPC190648
0.906	High Similarity	NPC118027
0.906	High Similarity	NPC289042
0.906	High Similarity	NPC56433
0.9048	High Similarity	NPC3732
0.9045	High Similarity	NPC472049
0.9032	High Similarity	NPC472055
0.9026	High Similarity	NPC246466
0.9013	High Similarity	NPC154683
0.9013	High Similarity	NPC40356
0.898	High Similarity	NPC49108
0.8973	High Similarity	NPC156872
0.8973	High Similarity	NPC109007
0.8961	High Similarity	NPC164427
0.8954	High Similarity	NPC93552
0.8954	High Similarity	NPC107109
0.894	High Similarity	NPC77325
0.894	High Similarity	NPC4423
0.8933	High Similarity	NPC51070
0.8933	High Similarity	NPC34802
0.8933	High Similarity	NPC222298
0.8926	High Similarity	NPC34482
0.8926	High Similarity	NPC478019
0.8926	High Similarity	NPC28632
0.8919	High Similarity	NPC472006
0.891	High Similarity	NPC161947
0.891	High Similarity	NPC155302
0.891	High Similarity	NPC470810
0.8903	High Similarity	NPC199463
0.8903	High Similarity	NPC37543
0.8896	High Similarity	NPC234485
0.8889	High Similarity	NPC477991
0.8889	High Similarity	NPC477992
0.8882	High Similarity	NPC294646
0.8882	High Similarity	NPC85131
0.8874	High Similarity	NPC172329
0.8874	High Similarity	NPC2569
0.8874	High Similarity	NPC153417
0.8874	High Similarity	NPC215711
0.8874	High Similarity	NPC73411
0.8867	High Similarity	NPC470570
0.8867	High Similarity	NPC316769
0.8859	High Similarity	NPC210425
0.8859	High Similarity	NPC86373
0.8859	High Similarity	NPC48762
0.8859	High Similarity	NPC280404
0.8859	High Similarity	NPC277426
0.8859	High Similarity	NPC95751
0.8854	High Similarity	NPC87431
0.8854	High Similarity	NPC117985
0.8851	High Similarity	NPC232021
0.8851	High Similarity	NPC40118
0.8851	High Similarity	NPC126534
0.8846	High Similarity	NPC324736
0.8839	High Similarity	NPC5379
0.8839	High Similarity	NPC14561
0.8839	High Similarity	NPC77807
0.8831	High Similarity	NPC127172
0.8831	High Similarity	NPC208806
0.8824	High Similarity	NPC478148
0.8824	High Similarity	NPC232645
0.8824	High Similarity	NPC149526
0.8824	High Similarity	NPC72958
0.8824	High Similarity	NPC215921
0.8824	High Similarity	NPC474417
0.8824	High Similarity	NPC70016
0.882	High Similarity	NPC313717
0.882	High Similarity	NPC315306
0.8816	High Similarity	NPC10027
0.8816	High Similarity	NPC65775
0.8816	High Similarity	NPC329933
0.8808	High Similarity	NPC210320
0.8808	High Similarity	NPC77598
0.88	High Similarity	NPC49282
0.8792	High Similarity	NPC469542
0.8792	High Similarity	NPC51106
0.8792	High Similarity	NPC167663
0.8792	High Similarity	NPC84266
0.879	High Similarity	NPC472618
0.879	High Similarity	NPC313368
0.8784	High Similarity	NPC1704
0.8784	High Similarity	NPC253822
0.8784	High Similarity	NPC265178
0.8784	High Similarity	NPC67650
0.8782	High Similarity	NPC178976
0.8782	High Similarity	NPC472889
0.8782	High Similarity	NPC474637
0.8774	High Similarity	NPC326910
0.8774	High Similarity	NPC99381
0.8774	High Similarity	NPC175192
0.8774	High Similarity	NPC226656
0.8774	High Similarity	NPC66508
0.8766	High Similarity	NPC474843
0.8766	High Similarity	NPC324233
0.8766	High Similarity	NPC115249
0.8766	High Similarity	NPC312338
0.8766	High Similarity	NPC87708
0.8766	High Similarity	NPC478224
0.8766	High Similarity	NPC167903
0.8766	High Similarity	NPC149889
0.8766	High Similarity	NPC323626
0.8758	High Similarity	NPC202595
0.8758	High Similarity	NPC469619
0.8758	High Similarity	NPC469670
0.8758	High Similarity	NPC179178
0.8758	High Similarity	NPC472891
0.875	High Similarity	NPC166036
0.875	High Similarity	NPC178173
0.875	High Similarity	NPC238279
0.875	High Similarity	NPC203077
0.875	High Similarity	NPC20237
0.8742	High Similarity	NPC473023
0.8742	High Similarity	NPC107625
0.8742	High Similarity	NPC100849
0.8742	High Similarity	NPC249181
0.8742	High Similarity	NPC472033
0.8742	High Similarity	NPC476822
0.8733	High Similarity	NPC475705
0.8733	High Similarity	NPC476178
0.8733	High Similarity	NPC117836
0.8733	High Similarity	NPC51887
0.8733	High Similarity	NPC193703
0.8733	High Similarity	NPC21599
0.8733	High Similarity	NPC244691
0.8726	High Similarity	NPC85121
0.8726	High Similarity	NPC329091
0.8725	High Similarity	NPC321980
0.8725	High Similarity	NPC55832
0.8725	High Similarity	NPC182255
0.8725	High Similarity	NPC26051
0.8725	High Similarity	NPC52789
0.8725	High Similarity	NPC470087
0.8725	High Similarity	NPC469579
0.8725	High Similarity	NPC94076
0.8725	High Similarity	NPC474385
0.8725	High Similarity	NPC268204
0.8725	High Similarity	NPC135524
0.8718	High Similarity	NPC478223
0.8718	High Similarity	NPC24640
0.8716	High Similarity	NPC472366
0.8716	High Similarity	NPC470211
0.8716	High Similarity	NPC201541
0.8712	High Similarity	NPC154986
0.8712	High Similarity	NPC98776
0.8712	High Similarity	NPC469393
0.871	High Similarity	NPC478231
0.871	High Similarity	NPC469405
0.871	High Similarity	NPC137301
0.871	High Similarity	NPC192189
0.871	High Similarity	NPC472799
0.871	High Similarity	NPC210942
0.871	High Similarity	NPC169990
0.8701	High Similarity	NPC471676
0.8701	High Similarity	NPC200773
0.8701	High Similarity	NPC230848
0.8701	High Similarity	NPC244577
0.8701	High Similarity	NPC240768
0.8701	High Similarity	NPC472422
0.8701	High Similarity	NPC472420
0.8701	High Similarity	NPC263384
0.8699	High Similarity	NPC84699

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 NPC132990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	943
0.2-0.3	1736
0.3-0.4	2620
0.4-0.5	1863
0.5-0.6	1045
0.6-0.7	414
0.7-0.8	156
0.8-0.85	34
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD4380	Phase 2
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1510	Phase 2
0.8431	Intermediate Similarity	NPD2532	Approved
0.8431	Intermediate Similarity	NPD2533	Approved
0.8431	Intermediate Similarity	NPD2534	Approved
0.84	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8322	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1607	Approved
0.8299	Intermediate Similarity	NPD1240	Approved
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8291	Intermediate Similarity	NPD1934	Approved
0.8278	Intermediate Similarity	NPD1549	Phase 2
0.8272	Intermediate Similarity	NPD6959	Discontinued
0.8212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7075	Discontinued
0.8194	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2796	Approved
0.8137	Intermediate Similarity	NPD3882	Suspended
0.8125	Intermediate Similarity	NPD2801	Approved
0.8125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6801	Discontinued
0.8052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.8013	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2800	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7943	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD3750	Approved
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1512	Approved
0.7898	Intermediate Similarity	NPD6799	Approved
0.7888	Intermediate Similarity	NPD7411	Suspended
0.7879	Intermediate Similarity	NPD5494	Approved
0.787	Intermediate Similarity	NPD5844	Phase 1
0.7866	Intermediate Similarity	NPD3749	Approved
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7824	Intermediate Similarity	NPD7074	Phase 3
0.7821	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD943	Approved
0.7792	Intermediate Similarity	NPD2935	Discontinued
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD5711	Approved
0.7784	Intermediate Similarity	NPD5710	Approved
0.7765	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3226	Approved
0.7744	Intermediate Similarity	NPD5402	Approved
0.7744	Intermediate Similarity	NPD3817	Phase 2
0.7727	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7472	Approved
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7703	Intermediate Similarity	NPD1470	Approved
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD5403	Approved
0.7637	Intermediate Similarity	NPD6781	Approved
0.7637	Intermediate Similarity	NPD6779	Approved
0.7637	Intermediate Similarity	NPD6782	Approved
0.7637	Intermediate Similarity	NPD6778	Approved
0.7637	Intermediate Similarity	NPD6777	Approved
0.7637	Intermediate Similarity	NPD6776	Approved
0.7637	Intermediate Similarity	NPD6780	Approved
0.763	Intermediate Similarity	NPD7251	Discontinued
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD37	Approved
0.7614	Intermediate Similarity	NPD8150	Discontinued
0.7613	Intermediate Similarity	NPD3748	Approved
0.7586	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7808	Phase 3
0.7576	Intermediate Similarity	NPD1465	Phase 2
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7514	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD5953	Discontinued
0.7451	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7432	Intermediate Similarity	NPD1201	Approved
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7423	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD1243	Approved
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD7697	Approved
0.7417	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2799	Discontinued
0.7386	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7871	Phase 2
0.738	Intermediate Similarity	NPD7870	Phase 2
0.7379	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7363	Intermediate Similarity	NPD6535	Approved
0.7363	Intermediate Similarity	NPD6534	Approved
0.7354	Intermediate Similarity	NPD7701	Phase 2
0.7342	Intermediate Similarity	NPD5404	Approved
0.7342	Intermediate Similarity	NPD5405	Approved
0.7342	Intermediate Similarity	NPD5406	Approved
0.7342	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4749	Approved
0.7329	Intermediate Similarity	NPD2309	Approved
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2654	Approved
0.731	Intermediate Similarity	NPD1247	Approved
0.7303	Intermediate Similarity	NPD2798	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7294	Intermediate Similarity	NPD919	Approved
0.7284	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3300	Phase 2
0.7277	Intermediate Similarity	NPD7874	Approved
0.7277	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5760	Phase 2
0.7262	Intermediate Similarity	NPD5761	Phase 2
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7286	Phase 2
0.7255	Intermediate Similarity	NPD9494	Approved
0.7243	Intermediate Similarity	NPD7699	Phase 2
0.7243	Intermediate Similarity	NPD7700	Phase 2
0.724	Intermediate Similarity	NPD7801	Approved
0.7229	Intermediate Similarity	NPD7458	Discontinued
0.7226	Intermediate Similarity	NPD3764	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.717	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD7003	Approved
0.7152	Intermediate Similarity	NPD3972	Approved
0.7152	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6190	Approved
0.7115	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2313	Discontinued
0.7105	Intermediate Similarity	NPD8320	Phase 1
0.7105	Intermediate Similarity	NPD8319	Approved
0.7097	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4908	Phase 1
0.7093	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD447	Suspended
0.7089	Intermediate Similarity	NPD5124	Phase 1
0.7086	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2403	Approved
0.7081	Intermediate Similarity	NPD4363	Phase 3
0.7081	Intermediate Similarity	NPD4360	Phase 2
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7067	Intermediate Similarity	NPD4626	Approved
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD1876	Approved
0.7047	Intermediate Similarity	NPD9545	Approved
0.7039	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9269	Phase 2
0.7039	Intermediate Similarity	NPD9717	Approved
0.7037	Intermediate Similarity	NPD2424	Discontinued
0.7029	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6212	Phase 3
0.7027	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6213	Phase 3
0.7027	Intermediate Similarity	NPD9493	Approved
0.7018	Intermediate Similarity	NPD4288	Approved
0.7013	Intermediate Similarity	NPD1203	Approved
0.7006	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD1651	Approved
0.6994	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6832	Phase 2
0.6974	Remote Similarity	NPD1610	Phase 2

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