NPASS Compound

Structure

CID327382 OpenBabel06191716192D 25 27 0 0 1 0 0 0 0 0999 V2000 3.0567 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4709 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 1.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 0.4914 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 5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7297 -1.5353 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 2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1780 0.1378 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 1.8320 -0.7588 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 3.7638 -1.2765 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 -0.3105 0.0000 C 0 0 3 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2121 0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 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 21 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	376.587
LogP:	5.362
LogD:	4.625
LogS:	-5.434
# Rotatable Bonds:	4
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	3.962
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	1.760990926413797e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.085
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.354
Plasma Protein Binding (PPB):	97.35607147216797%
Volume Distribution (VD):	3.353
Pgp-substrate:	0.8544062972068787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.827
CYP1A2-substrate:	0.696
CYP2C19-inhibitor:	0.662
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.531

ADMET: Excretion

Clearance (CL):	8.463
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.647
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.078
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC327382

Natural Product ID:	NPC327382
*Common Name:**	Metachromin U
IUPAC Name:	2-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromen-6-ol
Synonyms:	Metachromin U
Standard InCHIKey:	OKZZLCIFQGFNCQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-15-7-6-10-21(2,3)18(15)9-12-22(4)11-8-16-13-17(23)14-19(24-5)20(16)25-22/h8,11,13-14,18,23H,1,6-7,9-10,12H2,2-5H3
SMILES:	CC1(CCCC(=C)C1CCC2(C=CC3=C(O2)C(=CC(=C3)O)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784270
PubChem CID:	53262704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	32000.0	nM	PMID[483250]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	29000.0	nM	PMID[483250]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	37000.0	nM	PMID[483250]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	30000.0	nM	PMID[483250]
NPT913	Cell Line	CHO-K1	Cricetulus griseus	GI50	=	27000.0	nM	PMID[483250]

☑ 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 NPC327382 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	454
0.1-0.2	1617
0.2-0.3	3823
0.3-0.4	10809
0.4-0.5	8047
0.5-0.6	4231
0.6-0.7	9045
0.7-0.8	3931
0.8-0.85	603
0.85-0.9	132
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC19869
0.9265	High Similarity	NPC323126
0.9179	High Similarity	NPC173660
0.9104	High Similarity	NPC195022
0.9084	High Similarity	NPC190144
0.9044	High Similarity	NPC127218
0.9044	High Similarity	NPC245207
0.9044	High Similarity	NPC25966
0.9044	High Similarity	NPC471388
0.9044	High Similarity	NPC319647
0.903	High Similarity	NPC106215
0.9015	High Similarity	NPC224157
0.9015	High Similarity	NPC192687
0.9008	High Similarity	NPC63179
0.8978	High Similarity	NPC27495
0.8971	High Similarity	NPC276490
0.8955	High Similarity	NPC269528
0.8947	High Similarity	NPC45715
0.8947	High Similarity	NPC474356
0.8947	High Similarity	NPC82503
0.8947	High Similarity	NPC12275
0.8913	High Similarity	NPC471389
0.8913	High Similarity	NPC35216
0.8905	High Similarity	NPC292882
0.8897	High Similarity	NPC270456
0.8897	High Similarity	NPC248727
0.8897	High Similarity	NPC265433
0.8897	High Similarity	NPC162659
0.8881	High Similarity	NPC6451
0.8872	High Similarity	NPC220935
0.8865	High Similarity	NPC475896
0.8864	High Similarity	NPC266691
0.8855	High Similarity	NPC476006
0.8849	High Similarity	NPC107161
0.8849	High Similarity	NPC59841
0.8849	High Similarity	NPC204347
0.8849	High Similarity	NPC475891
0.8849	High Similarity	NPC2613
0.8841	High Similarity	NPC234568
0.8841	High Similarity	NPC160283
0.8841	High Similarity	NPC259519
0.8841	High Similarity	NPC254759
0.8832	High Similarity	NPC474530
0.8832	High Similarity	NPC326797
0.8832	High Similarity	NPC103976
0.8832	High Similarity	NPC102904
0.8832	High Similarity	NPC107551
0.8832	High Similarity	NPC176051
0.8832	High Similarity	NPC474282
0.8832	High Similarity	NPC474521
0.8832	High Similarity	NPC474540
0.8824	High Similarity	NPC201357
0.8824	High Similarity	NPC281521
0.8824	High Similarity	NPC255147
0.8824	High Similarity	NPC134968
0.8815	High Similarity	NPC229442
0.8815	High Similarity	NPC168059
0.8806	High Similarity	NPC232275
0.8803	High Similarity	NPC21776
0.8803	High Similarity	NPC16269
0.8794	High Similarity	NPC292256
0.8794	High Similarity	NPC90645
0.8794	High Similarity	NPC472457
0.8788	High Similarity	NPC216836
0.8777	High Similarity	NPC247291
0.8768	High Similarity	NPC70682
0.8768	High Similarity	NPC260741
0.8759	High Similarity	NPC476698
0.8759	High Similarity	NPC472336
0.8759	High Similarity	NPC230734
0.8759	High Similarity	NPC205442
0.8759	High Similarity	NPC472334
0.8759	High Similarity	NPC474639
0.8759	High Similarity	NPC227503
0.875	High Similarity	NPC317380
0.875	High Similarity	NPC158784
0.875	High Similarity	NPC103967
0.8741	High Similarity	NPC86655
0.8741	High Similarity	NPC127624
0.8741	High Similarity	NPC212142
0.8741	High Similarity	NPC202762
0.8731	High Similarity	NPC311680
0.8731	High Similarity	NPC214860
0.8731	High Similarity	NPC234488
0.8731	High Similarity	NPC299221
0.8731	High Similarity	NPC229231
0.8731	High Similarity	NPC51840
0.8723	High Similarity	NPC93323
0.8723	High Similarity	NPC50250
0.8723	High Similarity	NPC45257
0.8723	High Similarity	NPC12641
0.8723	High Similarity	NPC280092
0.8712	High Similarity	NPC112596
0.8712	High Similarity	NPC245060
0.8705	High Similarity	NPC198038
0.8705	High Similarity	NPC309124
0.8705	High Similarity	NPC184797
0.8696	High Similarity	NPC476171
0.8692	High Similarity	NPC135414
0.8692	High Similarity	NPC194626
0.869	High Similarity	NPC302915
0.869	High Similarity	NPC2745
0.8686	High Similarity	NPC261873
0.8686	High Similarity	NPC121812
0.8686	High Similarity	NPC111655
0.8686	High Similarity	NPC283009
0.8686	High Similarity	NPC470356
0.8686	High Similarity	NPC112939
0.8686	High Similarity	NPC151224
0.8686	High Similarity	NPC94750
0.8686	High Similarity	NPC472337
0.8686	High Similarity	NPC61946
0.8686	High Similarity	NPC112246
0.8686	High Similarity	NPC474206
0.8676	High Similarity	NPC36661
0.8676	High Similarity	NPC94236
0.8676	High Similarity	NPC37196
0.8667	High Similarity	NPC469907
0.8662	High Similarity	NPC469557
0.8657	High Similarity	NPC472797
0.8657	High Similarity	NPC58164
0.8657	High Similarity	NPC45824
0.8657	High Similarity	NPC10225
0.8652	High Similarity	NPC102044
0.8652	High Similarity	NPC85264
0.8652	High Similarity	NPC47633
0.8652	High Similarity	NPC477616
0.8647	High Similarity	NPC50368
0.8643	High Similarity	NPC311530
0.8636	High Similarity	NPC105925
0.8633	High Similarity	NPC79622
0.8633	High Similarity	NPC212942
0.8633	High Similarity	NPC232164
0.8633	High Similarity	NPC236306
0.8633	High Similarity	NPC29868
0.8633	High Similarity	NPC473739
0.863	High Similarity	NPC160196
0.863	High Similarity	NPC157783
0.863	High Similarity	NPC325860
0.8623	High Similarity	NPC234952
0.8623	High Similarity	NPC302701
0.8623	High Similarity	NPC16435
0.8623	High Similarity	NPC269091
0.8623	High Similarity	NPC306441
0.8623	High Similarity	NPC126101
0.8621	High Similarity	NPC195561
0.8615	High Similarity	NPC285289
0.8615	High Similarity	NPC75713
0.8613	High Similarity	NPC474478
0.8611	High Similarity	NPC473876
0.8603	High Similarity	NPC218884
0.8603	High Similarity	NPC161203
0.8601	High Similarity	NPC112251
0.8601	High Similarity	NPC87794
0.8601	High Similarity	NPC233980
0.8601	High Similarity	NPC211758
0.8593	High Similarity	NPC126836
0.8593	High Similarity	NPC91291
0.8592	High Similarity	NPC473108
0.8592	High Similarity	NPC63879
0.8592	High Similarity	NPC469795
0.8582	High Similarity	NPC19694
0.8571	High Similarity	NPC223953
0.8561	High Similarity	NPC73535
0.8561	High Similarity	NPC25111
0.8561	High Similarity	NPC272157
0.8561	High Similarity	NPC201145
0.8561	High Similarity	NPC90615
0.8561	High Similarity	NPC35550
0.8561	High Similarity	NPC477938
0.8561	High Similarity	NPC6262
0.8561	High Similarity	NPC211549
0.8552	High Similarity	NPC476969
0.8551	High Similarity	NPC240279
0.8551	High Similarity	NPC47398
0.8551	High Similarity	NPC234333
0.8551	High Similarity	NPC180602
0.8551	High Similarity	NPC55239
0.8551	High Similarity	NPC214853
0.8551	High Similarity	NPC313081
0.8551	High Similarity	NPC260898
0.8551	High Similarity	NPC164787
0.855	High Similarity	NPC246967
0.855	High Similarity	NPC474864
0.855	High Similarity	NPC74137
0.8542	High Similarity	NPC101376
0.854	High Similarity	NPC105554
0.854	High Similarity	NPC263064
0.854	High Similarity	NPC11060
0.854	High Similarity	NPC475840
0.8538	High Similarity	NPC218753
0.8531	High Similarity	NPC307466
0.8529	High Similarity	NPC472590
0.8521	High Similarity	NPC34245
0.8521	High Similarity	NPC91492
0.8521	High Similarity	NPC256555
0.8521	High Similarity	NPC7439
0.8521	High Similarity	NPC474104
0.8521	High Similarity	NPC110067
0.8519	High Similarity	NPC96719

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 NPC327382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	880
0.2-0.3	1777
0.3-0.4	2788
0.4-0.5	1678
0.5-0.6	970
0.6-0.7	569
0.7-0.8	81
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD4749	Approved
0.8456	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD4625	Phase 3
0.837	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD3027	Phase 3
0.8195	Intermediate Similarity	NPD1610	Phase 2
0.8175	Intermediate Similarity	NPD4908	Phase 1
0.8169	Intermediate Similarity	NPD6099	Approved
0.8169	Intermediate Similarity	NPD6100	Approved
0.8102	Intermediate Similarity	NPD2861	Phase 2
0.8077	Intermediate Similarity	NPD6671	Approved
0.8058	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD1548	Phase 1
0.8029	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD6696	Suspended
0.7908	Intermediate Similarity	NPD2801	Approved
0.7714	Intermediate Similarity	NPD3018	Phase 2
0.7703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1653	Approved
0.7652	Intermediate Similarity	NPD5283	Phase 1
0.7613	Intermediate Similarity	NPD1934	Approved
0.7569	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3620	Phase 2
0.7554	Intermediate Similarity	NPD2983	Phase 2
0.7554	Intermediate Similarity	NPD2982	Phase 2
0.7536	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD228	Approved
0.7482	Intermediate Similarity	NPD2981	Phase 2
0.7481	Intermediate Similarity	NPD4750	Phase 3
0.7481	Intermediate Similarity	NPD7340	Approved
0.747	Intermediate Similarity	NPD7549	Discontinued
0.7452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7439	Intermediate Similarity	NPD5844	Phase 1
0.7434	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD6674	Discontinued
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD37	Approved
0.7388	Intermediate Similarity	NPD1398	Phase 1
0.7385	Intermediate Similarity	NPD968	Approved
0.7376	Intermediate Similarity	NPD8651	Approved
0.7375	Intermediate Similarity	NPD6234	Discontinued
0.7358	Intermediate Similarity	NPD4965	Approved
0.7358	Intermediate Similarity	NPD4967	Phase 2
0.7358	Intermediate Similarity	NPD4966	Approved
0.7357	Intermediate Similarity	NPD2230	Approved
0.7357	Intermediate Similarity	NPD2233	Approved
0.7357	Intermediate Similarity	NPD2232	Approved
0.7351	Intermediate Similarity	NPD3892	Phase 2
0.7338	Intermediate Similarity	NPD1512	Approved
0.7338	Intermediate Similarity	NPD3496	Discontinued
0.7329	Intermediate Similarity	NPD2238	Phase 2
0.7329	Intermediate Similarity	NPD5494	Approved
0.7324	Intermediate Similarity	NPD2797	Approved
0.7305	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6111	Discontinued
0.7296	Intermediate Similarity	NPD3817	Phase 2
0.7286	Intermediate Similarity	NPD3705	Approved
0.7286	Intermediate Similarity	NPD1091	Approved
0.7285	Intermediate Similarity	NPD5177	Phase 3
0.7285	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5735	Approved
0.7279	Intermediate Similarity	NPD7157	Approved
0.7279	Intermediate Similarity	NPD5124	Phase 1
0.7279	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6166	Phase 2
0.7256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7124	Phase 2
0.725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3882	Suspended
0.7241	Intermediate Similarity	NPD7095	Approved
0.7239	Intermediate Similarity	NPD6232	Discontinued
0.7237	Intermediate Similarity	NPD3750	Approved
0.723	Intermediate Similarity	NPD4097	Suspended
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7211	Intermediate Similarity	NPD1558	Phase 1
0.7197	Intermediate Similarity	NPD290	Approved
0.7197	Intermediate Similarity	NPD4005	Discontinued
0.7192	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2560	Approved
0.7188	Intermediate Similarity	NPD2563	Approved
0.7183	Intermediate Similarity	NPD5327	Phase 3
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7447	Phase 1
0.7153	Intermediate Similarity	NPD4624	Approved
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD4678	Approved
0.7152	Intermediate Similarity	NPD3540	Phase 1
0.7152	Intermediate Similarity	NPD5763	Approved
0.7152	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD1778	Approved
0.7133	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7054	Approved
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7124	Intermediate Similarity	NPD6331	Phase 2
0.7124	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4110	Phase 3
0.7118	Intermediate Similarity	NPD4577	Approved
0.7118	Intermediate Similarity	NPD4578	Approved
0.7114	Intermediate Similarity	NPD6353	Approved
0.7113	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7212	Phase 2
0.7097	Intermediate Similarity	NPD7213	Phase 3
0.7095	Intermediate Similarity	NPD4140	Approved
0.7093	Intermediate Similarity	NPD4663	Approved
0.7091	Intermediate Similarity	NPD2969	Approved
0.7091	Intermediate Similarity	NPD2970	Approved
0.709	Intermediate Similarity	NPD3022	Approved
0.709	Intermediate Similarity	NPD3021	Approved
0.7086	Intermediate Similarity	NPD3539	Phase 1
0.7083	Intermediate Similarity	NPD7074	Phase 3
0.7083	Intermediate Similarity	NPD7472	Approved
0.7081	Intermediate Similarity	NPD5402	Approved
0.7078	Intermediate Similarity	NPD2677	Approved
0.7077	Intermediate Similarity	NPD940	Approved
0.7077	Intermediate Similarity	NPD846	Approved
0.7075	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD1357	Approved
0.7071	Intermediate Similarity	NPD5585	Approved
0.7066	Intermediate Similarity	NPD7228	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7635	Approved
0.7052	Intermediate Similarity	NPD7906	Approved
0.7051	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD27	Approved
0.7048	Intermediate Similarity	NPD2489	Approved
0.7042	Intermediate Similarity	NPD1611	Approved
0.7039	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1375	Discontinued
0.7034	Intermediate Similarity	NPD6584	Phase 3
0.703	Intermediate Similarity	NPD6071	Discontinued
0.703	Intermediate Similarity	NPD3051	Approved
0.702	Intermediate Similarity	NPD7033	Discontinued
0.7018	Intermediate Similarity	NPD7312	Approved
0.7018	Intermediate Similarity	NPD7313	Approved
0.7018	Intermediate Similarity	NPD7310	Approved
0.7018	Intermediate Similarity	NPD7311	Approved
0.7013	Intermediate Similarity	NPD7466	Approved
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2231	Phase 2
0.6993	Remote Similarity	NPD2235	Phase 2
0.6977	Remote Similarity	NPD8053	Approved
0.6977	Remote Similarity	NPD7309	Approved
0.6977	Remote Similarity	NPD8054	Approved
0.6974	Remote Similarity	NPD2796	Approved
0.697	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD7808	Phase 3
0.6957	Remote Similarity	NPD3382	Approved
0.6957	Remote Similarity	NPD3383	Approved
0.6957	Remote Similarity	NPD3384	Approved
0.6954	Remote Similarity	NPD2200	Suspended
0.6943	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6797	Phase 2
0.6937	Remote Similarity	NPD4380	Phase 2
0.6934	Remote Similarity	NPD7843	Approved
0.6933	Remote Similarity	NPD3657	Discovery
0.6933	Remote Similarity	NPD447	Suspended
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3787	Discontinued
0.6914	Remote Similarity	NPD5929	Approved
0.6914	Remote Similarity	NPD7819	Suspended
0.6908	Remote Similarity	NPD3748	Approved
0.6908	Remote Similarity	NPD1510	Phase 2
0.6901	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD4626	Approved
0.6901	Remote Similarity	NPD17	Approved
0.6897	Remote Similarity	NPD3225	Approved
0.6894	Remote Similarity	NPD6072	Discontinued
0.689	Remote Similarity	NPD7833	Phase 2
0.689	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4055	Discovery
0.689	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7831	Phase 2
0.6883	Remote Similarity	NPD1549	Phase 2
0.6879	Remote Similarity	NPD4357	Discontinued
0.6879	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7741	Discontinued
0.6879	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1712	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