NPASS Compound

Structure

CID225854 OpenBabel06191716022D 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 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 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 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 12 1 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 5 1 6 0 0 0 8 10 1 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 6 1 1 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 1 1 0 0 0 16 1 1 1 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.13
Volume:	301.818
LogP:	0.74
LogD:	0.224
LogS:	-2.714
# 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:	0.61
Synthetic Accessibility Score:	4.32
Fsp3:	0.562
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:	-5.333
MDCK Permeability:	7.023935268080095e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.414
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.578
Plasma Protein Binding (PPB):	75.21682739257812%
Volume Distribution (VD):	1.057
Pgp-substrate:	16.04973602294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	6.68
Half-life (T1/2):	0.41

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.189
Carcinogencity:	0.025
Eye Corrosion:	0.004
Eye Irritation:	0.109
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC225854

Natural Product ID:	NPC225854
*Common Name:**	Altersolanol J
IUPAC Name:	(2S,3R,4aS,9aS,10R)-2,3,5,10-tetrahydroxy-7-methoxy-2-methyl-1,3,4,4a,9a,10-hexahydroanthracen-9-one
Synonyms:
Standard InCHIKey:	QJPIXVDUWUJAIT-YLHGYNODSA-N
Standard InCHI:	InChI=1S/C16H20O6/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/h3-4,8,10,12,15,17-18,20-21H,5-6H2,1-2H3/t8-,10-,12+,15+,16-/m0/s1
SMILES:	COc1cc(O)c2c(c1)C(=O)[C@@H]1[C@@H]([C@H]2O)C[C@H]([C@@](C1)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449194
PubChem CID:	10913856
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
NPO40477	Cladosporium sp. NRRL 29097	Strain	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088431]
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568783]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Mentha pulegium	n.a.	n.a.	PMID[19271717]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271717]
NPO22865	Neopetrosia proxima	Species	Petrosiidae	Eukaryota	n.a.	Caribbean sea	n.a.	PMID[20727745]
NPO22865	Neopetrosia proxima	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341726]
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	reef slopes on the south side of Cocos Lagoon, Guam	n.a.	PMID[21550239]
NPO18542	Salvia sahendica	Species	Lamiaceae	Eukaryota	n.a.	collected from the plants natural habitat in Tabriz, Northwestern Iran, at an altitude of 1400 m	n.a.	PMID[21775156]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23664494]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	isolated from fresh Juncus acutus	Lake Wadi el Natrun, Egypt	2012-NOV	PMID[25010124]
NPO18279	Paraconiothyrium brasiliense	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25760674]
NPO18194	Primula modesta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18194	Primula modesta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18542	Salvia sahendica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19726	Limnatis nilotica	Species	Hirudinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18944	Vernonia filigera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19101	Deutzia gracilis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19382	Corallina elongata	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18194	Primula modesta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19321	0tholaena californica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14894	Udotea conglutinata	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22865	Neopetrosia proxima	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18279	Paraconiothyrium brasiliense	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18687	Pterocarpus gracilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18080	Peltophorum ferrugineum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13444	Centaurea ptosimopappoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15888	Streptogonopus phipsoni	n.a.	n.a.	n.a.	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
MIC	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	20.1	%	PMID[524192]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[524193]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	12.5	ug.mL-1	PMID[524193]

☑ 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 NPC225854 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	374
0.1-0.2	1344
0.2-0.3	2952
0.3-0.4	6877
0.4-0.5	10910
0.5-0.6	4597
0.6-0.7	4787
0.7-0.8	8051
0.8-0.85	2529
0.85-0.9	246
0.9-0.95	21
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC180944
0.9726	High Similarity	NPC470337
0.9726	High Similarity	NPC268992
0.9726	High Similarity	NPC51824
0.9726	High Similarity	NPC113608
0.9726	High Similarity	NPC470338
0.9595	High Similarity	NPC68727
0.9592	High Similarity	NPC470340
0.951	High Similarity	NPC3732
0.9404	High Similarity	NPC470339
0.9342	High Similarity	NPC472055
0.9267	High Similarity	NPC155686
0.9262	High Similarity	NPC132990
0.9262	High Similarity	NPC46882
0.9216	High Similarity	NPC155302
0.9216	High Similarity	NPC161947
0.9156	High Similarity	NPC87431
0.9145	High Similarity	NPC164427
0.9133	High Similarity	NPC470569
0.9103	High Similarity	NPC472049
0.9067	High Similarity	NPC147735
0.9067	High Similarity	NPC470568
0.9007	High Similarity	NPC78505
0.8968	High Similarity	NPC470810
0.8954	High Similarity	NPC175192
0.8947	High Similarity	NPC167903
0.894	High Similarity	NPC255641
0.894	High Similarity	NPC290954
0.8919	High Similarity	NPC95751
0.8919	High Similarity	NPC19896
0.8896	High Similarity	NPC472050
0.8889	High Similarity	NPC303950
0.8889	High Similarity	NPC93552
0.8889	High Similarity	NPC107109
0.8882	High Similarity	NPC272566
0.8874	High Similarity	NPC329933
0.8868	High Similarity	NPC470341
0.8868	High Similarity	NPC234497
0.8868	High Similarity	NPC472058
0.8868	High Similarity	NPC324522
0.8868	High Similarity	NPC105414
0.8867	High Similarity	NPC118027
0.8867	High Similarity	NPC222298
0.8867	High Similarity	NPC34802
0.8867	High Similarity	NPC312929
0.8867	High Similarity	NPC126767
0.8867	High Similarity	NPC245584
0.8867	High Similarity	NPC51070
0.8867	High Similarity	NPC56433
0.8867	High Similarity	NPC289042
0.8867	High Similarity	NPC190648
0.8839	High Similarity	NPC179732
0.8839	High Similarity	NPC37543
0.8839	High Similarity	NPC199463
0.8824	High Similarity	NPC324233
0.8824	High Similarity	NPC40356
0.8824	High Similarity	NPC323626
0.8824	High Similarity	NPC154683
0.8816	High Similarity	NPC85131
0.8816	High Similarity	NPC294646
0.88	High Similarity	NPC316769
0.8797	High Similarity	NPC100849
0.8792	High Similarity	NPC105213
0.879	High Similarity	NPC316457
0.8784	High Similarity	NPC49108
0.8782	High Similarity	NPC85121
0.8782	High Similarity	NPC329091
0.8782	High Similarity	NPC324736
0.8782	High Similarity	NPC477410
0.8774	High Similarity	NPC77807
0.8774	High Similarity	NPC5379
0.8774	High Similarity	NPC478223
0.8774	High Similarity	NPC24640
0.8774	High Similarity	NPC14561
0.8758	High Similarity	NPC149526
0.8758	High Similarity	NPC46564
0.8758	High Similarity	NPC207346
0.8758	High Similarity	NPC478148
0.8758	High Similarity	NPC474417
0.875	High Similarity	NPC270160
0.875	High Similarity	NPC237440
0.8742	High Similarity	NPC81835
0.8742	High Similarity	NPC77598
0.8742	High Similarity	NPC17101
0.8742	High Similarity	NPC472057
0.8742	High Similarity	NPC472051
0.8742	High Similarity	NPC77903
0.8734	High Similarity	NPC473961
0.8734	High Similarity	NPC472059
0.8734	High Similarity	NPC472964
0.8734	High Similarity	NPC215612
0.8734	High Similarity	NPC478229
0.8733	High Similarity	NPC478019
0.8733	High Similarity	NPC34482
0.8726	High Similarity	NPC84571
0.8726	High Similarity	NPC472618
0.8726	High Similarity	NPC472902
0.8726	High Similarity	NPC24627
0.8726	High Similarity	NPC321399
0.8718	High Similarity	NPC178976
0.8718	High Similarity	NPC246466
0.871	High Similarity	NPC67396
0.8704	High Similarity	NPC472620
0.8701	High Similarity	NPC474843
0.8701	High Similarity	NPC312338
0.8701	High Similarity	NPC87708
0.8701	High Similarity	NPC149889
0.8699	High Similarity	NPC24394
0.8693	High Similarity	NPC202595
0.8688	High Similarity	NPC469394
0.8684	High Similarity	NPC203077
0.8684	High Similarity	NPC238279
0.8684	High Similarity	NPC474903
0.8684	High Similarity	NPC2569
0.8684	High Similarity	NPC166036
0.8684	High Similarity	NPC172329
0.8679	High Similarity	NPC472053
0.8679	High Similarity	NPC476295
0.8675	High Similarity	NPC470570
0.8671	High Similarity	NPC311740
0.8671	High Similarity	NPC478222
0.8671	High Similarity	NPC117985
0.8667	High Similarity	NPC475201
0.8667	High Similarity	NPC476178
0.8667	High Similarity	NPC475705
0.8667	High Similarity	NPC244691
0.8667	High Similarity	NPC48762
0.8667	High Similarity	NPC51887
0.8667	High Similarity	NPC117836
0.8667	High Similarity	NPC207732
0.8662	High Similarity	NPC472617
0.8662	High Similarity	NPC4950
0.8662	High Similarity	NPC218818
0.8662	High Similarity	NPC226287
0.8662	High Similarity	NPC210459
0.8658	High Similarity	NPC126534
0.8658	High Similarity	NPC232021
0.8658	High Similarity	NPC321980
0.8658	High Similarity	NPC470087
0.8658	High Similarity	NPC40118
0.8658	High Similarity	NPC18714
0.8654	High Similarity	NPC208152
0.8654	High Similarity	NPC469474
0.8654	High Similarity	NPC78492
0.865	High Similarity	NPC469393
0.865	High Similarity	NPC98776
0.8649	High Similarity	NPC469523
0.8649	High Similarity	NPC201541
0.8645	High Similarity	NPC208806
0.8645	High Similarity	NPC62051
0.8645	High Similarity	NPC144801
0.8645	High Similarity	NPC116850
0.8645	High Similarity	NPC238672
0.8645	High Similarity	NPC469405
0.8645	High Similarity	NPC197188
0.8645	High Similarity	NPC25127
0.8645	High Similarity	NPC287504
0.8645	High Similarity	NPC43872
0.8645	High Similarity	NPC291510
0.8645	High Similarity	NPC74924
0.8642	High Similarity	NPC313717
0.8642	High Similarity	NPC315306
0.8636	High Similarity	NPC221249
0.8636	High Similarity	NPC70016
0.8636	High Similarity	NPC471676
0.8636	High Similarity	NPC472420
0.8636	High Similarity	NPC228662
0.8636	High Similarity	NPC72958
0.8636	High Similarity	NPC473131
0.8636	High Similarity	NPC151425
0.8636	High Similarity	NPC230848
0.8636	High Similarity	NPC263384
0.8636	High Similarity	NPC244577
0.8636	High Similarity	NPC215921
0.8636	High Similarity	NPC472422
0.8636	High Similarity	NPC232645
0.8636	High Similarity	NPC470675
0.8634	High Similarity	NPC225419
0.8634	High Similarity	NPC477154
0.8634	High Similarity	NPC474024
0.8634	High Similarity	NPC472622
0.8634	High Similarity	NPC6588
0.8634	High Similarity	NPC117854
0.8627	High Similarity	NPC10027
0.8627	High Similarity	NPC65775
0.8627	High Similarity	NPC89442
0.8627	High Similarity	NPC38545
0.8627	High Similarity	NPC171916
0.8627	High Similarity	NPC80370
0.8625	High Similarity	NPC25361
0.8618	High Similarity	NPC470670
0.8618	High Similarity	NPC14875
0.8618	High Similarity	NPC47388
0.8618	High Similarity	NPC473133
0.8616	High Similarity	NPC211107
0.8616	High Similarity	NPC149389
0.8609	High Similarity	NPC157133
0.8609	High Similarity	NPC49282
0.8608	High Similarity	NPC471976
0.8608	High Similarity	NPC36217

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 NPC225854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	876
0.2-0.3	1623
0.3-0.4	2575
0.4-0.5	1990
0.5-0.6	1056
0.6-0.7	515
0.7-0.8	166
0.8-0.85	24
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD2393	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6232	Discontinued
0.8354	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD1934	Approved
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8255	Intermediate Similarity	NPD1510	Phase 2
0.8247	Intermediate Similarity	NPD2532	Approved
0.8247	Intermediate Similarity	NPD2534	Approved
0.8247	Intermediate Similarity	NPD2533	Approved
0.8228	Intermediate Similarity	NPD37	Approved
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD2801	Approved
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8133	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1607	Approved
0.8108	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD1549	Phase 2
0.8086	Intermediate Similarity	NPD6234	Discontinued
0.8079	Intermediate Similarity	NPD6100	Approved
0.8079	Intermediate Similarity	NPD6099	Approved
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD4966	Approved
0.8075	Intermediate Similarity	NPD4965	Approved
0.8075	Intermediate Similarity	NPD4967	Phase 2
0.8072	Intermediate Similarity	NPD3818	Discontinued
0.8065	Intermediate Similarity	NPD1511	Approved
0.8037	Intermediate Similarity	NPD5494	Approved
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7075	Discontinued
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3750	Approved
0.7962	Intermediate Similarity	NPD1512	Approved
0.7961	Intermediate Similarity	NPD2796	Approved
0.795	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1465	Phase 2
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7888	Intermediate Similarity	NPD6801	Discontinued
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4628	Phase 3
0.787	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD7228	Approved
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7811	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3749	Approved
0.7803	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD7472	Approved
0.7764	Intermediate Similarity	NPD6599	Discontinued
0.7751	Intermediate Similarity	NPD3751	Discontinued
0.7748	Intermediate Similarity	NPD943	Approved
0.7727	Intermediate Similarity	NPD2935	Discontinued
0.7722	Intermediate Similarity	NPD6799	Approved
0.7719	Intermediate Similarity	NPD6797	Phase 2
0.7706	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD2800	Approved
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5402	Approved
0.7674	Intermediate Similarity	NPD7251	Discontinued
0.7667	Intermediate Similarity	NPD3027	Phase 3
0.7665	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD3748	Approved
0.7662	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8150	Discontinued
0.7647	Intermediate Similarity	NPD6651	Approved
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7768	Phase 2
0.7633	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7808	Phase 3
0.763	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5710	Approved
0.7619	Intermediate Similarity	NPD3787	Discontinued
0.7619	Intermediate Similarity	NPD5711	Approved
0.7595	Intermediate Similarity	NPD6190	Approved
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7586	Intermediate Similarity	NPD8312	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7582	Intermediate Similarity	NPD6778	Approved
0.7582	Intermediate Similarity	NPD6782	Approved
0.7582	Intermediate Similarity	NPD6781	Approved
0.7582	Intermediate Similarity	NPD6776	Approved
0.7582	Intermediate Similarity	NPD6780	Approved
0.7582	Intermediate Similarity	NPD6779	Approved
0.7582	Intermediate Similarity	NPD6777	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8434	Phase 2
0.754	Intermediate Similarity	NPD8151	Discontinued
0.7532	Intermediate Similarity	NPD7003	Approved
0.7517	Intermediate Similarity	NPD1470	Approved
0.7516	Intermediate Similarity	NPD6273	Approved
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5761	Phase 2
0.7515	Intermediate Similarity	NPD5760	Phase 2
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD7240	Approved
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5403	Approved
0.7467	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7435	Discontinued
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7417	Intermediate Similarity	NPD9494	Approved
0.7389	Intermediate Similarity	NPD1551	Phase 2
0.7383	Intermediate Similarity	NPD4749	Approved
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7366	Intermediate Similarity	NPD7698	Approved
0.7366	Intermediate Similarity	NPD7696	Phase 3
0.7366	Intermediate Similarity	NPD7697	Approved
0.7365	Intermediate Similarity	NPD1201	Approved
0.7346	Intermediate Similarity	NPD5401	Approved
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7870	Phase 2
0.7326	Intermediate Similarity	NPD7871	Phase 2
0.7325	Intermediate Similarity	NPD2799	Discontinued
0.7315	Intermediate Similarity	NPD3972	Approved
0.7315	Intermediate Similarity	NPD9269	Phase 2
0.7312	Intermediate Similarity	NPD6823	Phase 2
0.7312	Intermediate Similarity	NPD8166	Discontinued
0.7308	Intermediate Similarity	NPD6535	Approved
0.7308	Intermediate Similarity	NPD6534	Approved
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7701	Phase 2
0.729	Intermediate Similarity	NPD3620	Phase 2
0.729	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD5404	Approved
0.7278	Intermediate Similarity	NPD5405	Approved
0.7278	Intermediate Similarity	NPD5408	Approved
0.7277	Intermediate Similarity	NPD7801	Approved
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7262	Intermediate Similarity	NPD5353	Approved
0.7256	Intermediate Similarity	NPD920	Approved
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1247	Approved
0.7251	Intermediate Similarity	NPD8127	Discontinued
0.725	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD2798	Approved
0.7233	Intermediate Similarity	NPD2344	Approved
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.7222	Intermediate Similarity	NPD3300	Phase 2
0.7219	Intermediate Similarity	NPD1876	Approved
0.7219	Intermediate Similarity	NPD1283	Approved
0.7216	Intermediate Similarity	NPD5953	Discontinued
0.7204	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7286	Phase 2
0.7189	Intermediate Similarity	NPD7700	Phase 2
0.7189	Intermediate Similarity	NPD7699	Phase 2
0.7188	Intermediate Similarity	NPD2424	Discontinued
0.7186	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7168	Intermediate Similarity	NPD5242	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7162	Intermediate Similarity	NPD1651	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD1243	Approved
0.7135	Intermediate Similarity	NPD919	Approved
0.7134	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4360	Phase 2
0.712	Intermediate Similarity	NPD4363	Phase 3
0.7114	Intermediate Similarity	NPD3019	Approved
0.7114	Intermediate Similarity	NPD4626	Approved
0.7108	Intermediate Similarity	NPD1653	Approved
0.7107	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4308	Phase 3
0.7107	Intermediate Similarity	NPD7033	Discontinued

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