NPASS Compound

Structure

NPC474540 OpenBabel07101718312D 30 32 0 0 1 0 0 0 0 0999 V2000 -3.6945 -2.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2802 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2462 0.6554 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1780 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9192 -1.7247 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 -4.4709 -0.0517 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 -2.5391 -0.0517 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9533 -1.9836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2462 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 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 1.7321 -2.0000 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 -3.5050 -0.3105 0.0000 C 0 0 1 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 -4.5000 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 1.7321 1.0000 0.0000 O 0 0 0 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 2 0 0 0 0 3 18 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 24 1 0 0 0 0 18 26 2 0 0 0 0 18 29 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.24
Volume:	443.419
LogP:	4.991
LogD:	3.874
LogS:	-6.444
# Rotatable Bonds:	7
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	4.306
Fsp3:	0.56
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:	-4.763
MDCK Permeability:	1.6956148101598956e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.092

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	97.12906646728516%
Volume Distribution (VD):	1.477
Pgp-substrate:	6.147056579589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.538
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.232
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.734
CYP2D6-inhibitor:	0.831
CYP2D6-substrate:	0.299
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.857

ADMET: Excretion

Clearance (CL):	3.1
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.179
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.826
Carcinogencity:	0.464
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC474540

Natural Product ID:	NPC474540
*Common Name:**	Metachromin B Mono Methylate
IUPAC Name:	[(2S)-2-[2-[(1R,3R)-1,3-dimethyl-2-methylidenecyclohexyl]ethyl]-6,8-dimethoxy-2-methylchromen-5-yl] acetate
Synonyms:	Metachromin B Mono Methylate
Standard InCHIKey:	KWPUCJVPYXFYJR-YSTXUQMKSA-N
Standard InCHI:	InChI=1S/C25H34O5/c1-16-9-8-11-24(4,17(16)2)13-14-25(5)12-10-19-22(29-18(3)26)20(27-6)15-21(28-7)23(19)30-25/h10,12,15-16H,2,8-9,11,13-14H2,1,3-7H3/t16-,24-,25-/m1/s1
SMILES:	CC1CCCC(C1=C)(C)CCC2(C=CC3=C(O2)C(=CC(=C3OC(=O)C)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471293
PubChem CID:	10341744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO33163	hippospongia metachromia	Species	Spongiidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11421749]
NPO33163	hippospongia metachromia	Species	Spongiidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[2607352]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	0.53	ug.mL-1	PMID[572602]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.32	ug.mL-1	PMID[572602]

☑ 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 NPC474540 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	385
0.1-0.2	1568
0.2-0.3	3865
0.3-0.4	10467
0.4-0.5	8582
0.5-0.6	4642
0.6-0.7	9597
0.7-0.8	3444
0.8-0.85	124
0.85-0.9	14
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474530
1.0	High Similarity	NPC474521
0.9313	High Similarity	NPC474617
0.9308	High Similarity	NPC474616
0.9231	High Similarity	NPC474670
0.9185	High Similarity	NPC286843
0.9179	High Similarity	NPC474600
0.916	High Similarity	NPC474636
0.9143	High Similarity	NPC475872
0.9111	High Similarity	NPC234865
0.9084	High Similarity	NPC474821
0.9051	High Similarity	NPC19869
0.9051	High Similarity	NPC270256
0.9008	High Similarity	NPC474632
0.9007	High Similarity	NPC475896
0.8978	High Similarity	NPC476171
0.8936	High Similarity	NPC292256
0.8905	High Similarity	NPC167517
0.8889	High Similarity	NPC319969
0.8832	High Similarity	NPC311430
0.8832	High Similarity	NPC327382
0.8832	High Similarity	NPC224941
0.8824	High Similarity	NPC241341
0.8824	High Similarity	NPC36437
0.8824	High Similarity	NPC233018
0.8824	High Similarity	NPC472522
0.8759	High Similarity	NPC147030
0.875	High Similarity	NPC137669
0.8741	High Similarity	NPC240722
0.8741	High Similarity	NPC476399
0.8741	High Similarity	NPC244799
0.8731	High Similarity	NPC474651
0.8731	High Similarity	NPC474623
0.8686	High Similarity	NPC474810
0.8667	High Similarity	NPC123127
0.8667	High Similarity	NPC27239
0.8662	High Similarity	NPC110067
0.8662	High Similarity	NPC91492
0.8662	High Similarity	NPC7439
0.8662	High Similarity	NPC34245
0.8662	High Similarity	NPC256555
0.8623	High Similarity	NPC309953
0.8613	High Similarity	NPC123954
0.8613	High Similarity	NPC474635
0.8603	High Similarity	NPC79184
0.8603	High Similarity	NPC19242
0.8603	High Similarity	NPC307042
0.8593	High Similarity	NPC210674
0.8561	High Similarity	NPC472521
0.8561	High Similarity	NPC252095
0.8561	High Similarity	NPC194626
0.854	High Similarity	NPC142530
0.854	High Similarity	NPC147317
0.8521	High Similarity	NPC300611
0.8511	High Similarity	NPC43500
0.8511	High Similarity	NPC164148
0.8489	Intermediate Similarity	NPC474478
0.8483	Intermediate Similarity	NPC205361
0.8462	Intermediate Similarity	NPC323126
0.8462	Intermediate Similarity	NPC474612
0.8456	Intermediate Similarity	NPC31707
0.8444	Intermediate Similarity	NPC244364
0.844	Intermediate Similarity	NPC306365
0.8429	Intermediate Similarity	NPC195022
0.8429	Intermediate Similarity	NPC281241
0.8429	Intermediate Similarity	NPC86892
0.8429	Intermediate Similarity	NPC73071
0.8429	Intermediate Similarity	NPC471625
0.8429	Intermediate Similarity	NPC472424
0.8429	Intermediate Similarity	NPC471909
0.8425	Intermediate Similarity	NPC15577
0.8417	Intermediate Similarity	NPC296624
0.8417	Intermediate Similarity	NPC207002
0.8417	Intermediate Similarity	NPC167111
0.8417	Intermediate Similarity	NPC133956
0.8417	Intermediate Similarity	NPC471910
0.8417	Intermediate Similarity	NPC318400
0.8414	Intermediate Similarity	NPC125617
0.8403	Intermediate Similarity	NPC236419
0.8403	Intermediate Similarity	NPC138212
0.8392	Intermediate Similarity	NPC279851
0.8392	Intermediate Similarity	NPC472520
0.8385	Intermediate Similarity	NPC471503
0.8385	Intermediate Similarity	NPC471498
0.8382	Intermediate Similarity	NPC202904
0.8382	Intermediate Similarity	NPC189248
0.8382	Intermediate Similarity	NPC194841
0.8369	Intermediate Similarity	NPC55615
0.8369	Intermediate Similarity	NPC283019
0.8369	Intermediate Similarity	NPC149320
0.8369	Intermediate Similarity	NPC173660
0.8369	Intermediate Similarity	NPC471630
0.8369	Intermediate Similarity	NPC177281
0.8369	Intermediate Similarity	NPC476455
0.8369	Intermediate Similarity	NPC128529
0.8369	Intermediate Similarity	NPC160727
0.8357	Intermediate Similarity	NPC260265
0.8357	Intermediate Similarity	NPC267412
0.8357	Intermediate Similarity	NPC287182
0.8357	Intermediate Similarity	NPC47163
0.8357	Intermediate Similarity	NPC74655
0.8357	Intermediate Similarity	NPC195343
0.8357	Intermediate Similarity	NPC164269
0.8357	Intermediate Similarity	NPC127888
0.8357	Intermediate Similarity	NPC166672
0.8357	Intermediate Similarity	NPC198381
0.8357	Intermediate Similarity	NPC100986
0.8357	Intermediate Similarity	NPC319859
0.8357	Intermediate Similarity	NPC84894
0.8357	Intermediate Similarity	NPC309744
0.8357	Intermediate Similarity	NPC18804
0.8333	Intermediate Similarity	NPC237169
0.8333	Intermediate Similarity	NPC220935
0.8333	Intermediate Similarity	NPC470624
0.8333	Intermediate Similarity	NPC473290
0.8333	Intermediate Similarity	NPC471504
0.8311	Intermediate Similarity	NPC176903
0.8311	Intermediate Similarity	NPC30688
0.831	Intermediate Similarity	NPC865
0.831	Intermediate Similarity	NPC20511
0.831	Intermediate Similarity	NPC38874
0.831	Intermediate Similarity	NPC52086
0.831	Intermediate Similarity	NPC105493
0.831	Intermediate Similarity	NPC76336
0.831	Intermediate Similarity	NPC95162
0.831	Intermediate Similarity	NPC139548
0.831	Intermediate Similarity	NPC148835
0.831	Intermediate Similarity	NPC474886
0.831	Intermediate Similarity	NPC276490
0.831	Intermediate Similarity	NPC20796
0.8309	Intermediate Similarity	NPC128321
0.8299	Intermediate Similarity	NPC183083
0.8299	Intermediate Similarity	NPC275125
0.8299	Intermediate Similarity	NPC137352
0.8299	Intermediate Similarity	NPC170239
0.8299	Intermediate Similarity	NPC97937
0.8298	Intermediate Similarity	NPC240915
0.8286	Intermediate Similarity	NPC269528
0.8284	Intermediate Similarity	NPC473464
0.8284	Intermediate Similarity	NPC476332
0.8273	Intermediate Similarity	NPC82503
0.8273	Intermediate Similarity	NPC474238
0.8271	Intermediate Similarity	NPC472596
0.8264	Intermediate Similarity	NPC35216
0.8261	Intermediate Similarity	NPC474227
0.8258	Intermediate Similarity	NPC308217
0.8255	Intermediate Similarity	NPC294522
0.8255	Intermediate Similarity	NPC120426
0.8255	Intermediate Similarity	NPC21184
0.8255	Intermediate Similarity	NPC205727
0.8252	Intermediate Similarity	NPC25966
0.8252	Intermediate Similarity	NPC307883
0.8252	Intermediate Similarity	NPC319647
0.8252	Intermediate Similarity	NPC127218
0.8252	Intermediate Similarity	NPC471388
0.8252	Intermediate Similarity	NPC13067
0.8252	Intermediate Similarity	NPC245207
0.8243	Intermediate Similarity	NPC139839
0.8239	Intermediate Similarity	NPC283331
0.8239	Intermediate Similarity	NPC471719
0.8239	Intermediate Similarity	NPC143895
0.8239	Intermediate Similarity	NPC126682
0.8239	Intermediate Similarity	NPC82271
0.8239	Intermediate Similarity	NPC78047
0.8235	Intermediate Similarity	NPC471827
0.8235	Intermediate Similarity	NPC471828
0.8227	Intermediate Similarity	NPC106215
0.8227	Intermediate Similarity	NPC307412
0.8227	Intermediate Similarity	NPC7163
0.8227	Intermediate Similarity	NPC55149
0.8222	Intermediate Similarity	NPC279379
0.8222	Intermediate Similarity	NPC315807
0.8219	Intermediate Similarity	NPC471763
0.8214	Intermediate Similarity	NPC14248
0.8209	Intermediate Similarity	NPC477886
0.8207	Intermediate Similarity	NPC472562
0.8207	Intermediate Similarity	NPC469564
0.8207	Intermediate Similarity	NPC59841
0.8207	Intermediate Similarity	NPC475891
0.8207	Intermediate Similarity	NPC174522
0.8207	Intermediate Similarity	NPC80326
0.8207	Intermediate Similarity	NPC2613
0.8207	Intermediate Similarity	NPC204347
0.8201	Intermediate Similarity	NPC224157
0.8201	Intermediate Similarity	NPC192687
0.8194	Intermediate Similarity	NPC27495
0.8194	Intermediate Similarity	NPC234568
0.8194	Intermediate Similarity	NPC259519
0.8188	Intermediate Similarity	NPC63179
0.8188	Intermediate Similarity	NPC266691
0.8188	Intermediate Similarity	NPC113790
0.8182	Intermediate Similarity	NPC474282
0.8182	Intermediate Similarity	NPC131198
0.8182	Intermediate Similarity	NPC326797
0.8182	Intermediate Similarity	NPC176051
0.8182	Intermediate Similarity	NPC107551
0.8182	Intermediate Similarity	NPC14697
0.8182	Intermediate Similarity	NPC102904
0.8182	Intermediate Similarity	NPC103976
0.8176	Intermediate Similarity	NPC16269

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 NPC474540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	946
0.2-0.3	1780
0.3-0.4	2840
0.4-0.5	1702
0.5-0.6	973
0.6-0.7	517
0.7-0.8	74
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7933	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1653	Approved
0.7817	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1613	Approved
0.7681	Intermediate Similarity	NPD1611	Approved
0.7655	Intermediate Similarity	NPD5124	Phase 1
0.7655	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3817	Phase 2
0.7622	Intermediate Similarity	NPD3027	Phase 3
0.7609	Intermediate Similarity	NPD3496	Discontinued
0.7606	Intermediate Similarity	NPD3018	Phase 2
0.759	Intermediate Similarity	NPD7549	Discontinued
0.758	Intermediate Similarity	NPD2801	Approved
0.7571	Intermediate Similarity	NPD4749	Approved
0.7569	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6099	Approved
0.7568	Intermediate Similarity	NPD6100	Approved
0.7562	Intermediate Similarity	NPD5494	Approved
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7554	Intermediate Similarity	NPD422	Phase 1
0.7537	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD7095	Approved
0.7468	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5585	Approved
0.7463	Intermediate Similarity	NPD5535	Approved
0.7451	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2983	Phase 2
0.7447	Intermediate Similarity	NPD2982	Phase 2
0.7445	Intermediate Similarity	NPD7644	Approved
0.7431	Intermediate Similarity	NPD4908	Phase 1
0.7426	Intermediate Similarity	NPD6671	Approved
0.7417	Intermediate Similarity	NPD1652	Phase 2
0.7413	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7199	Phase 2
0.7405	Intermediate Similarity	NPD37	Approved
0.74	Intermediate Similarity	NPD5762	Approved
0.74	Intermediate Similarity	NPD5763	Approved
0.7375	Intermediate Similarity	NPD4966	Approved
0.7375	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD4965	Approved
0.7347	Intermediate Similarity	NPD4060	Phase 1
0.7343	Intermediate Similarity	NPD2797	Approved
0.7343	Intermediate Similarity	NPD3267	Approved
0.7343	Intermediate Similarity	NPD3266	Approved
0.7317	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1610	Phase 2
0.7301	Intermediate Similarity	NPD8127	Discontinued
0.7296	Intermediate Similarity	NPD1934	Approved
0.7286	Intermediate Similarity	NPD17	Approved
0.7286	Intermediate Similarity	NPD1778	Approved
0.7284	Intermediate Similarity	NPD919	Approved
0.7284	Intermediate Similarity	NPD6234	Discontinued
0.7279	Intermediate Similarity	NPD8032	Phase 2
0.7273	Intermediate Similarity	NPD7124	Phase 2
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7273	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.7255	Intermediate Similarity	NPD4110	Phase 3
0.7255	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2237	Approved
0.7241	Intermediate Similarity	NPD2861	Phase 2
0.7239	Intermediate Similarity	NPD5677	Discontinued
0.723	Intermediate Similarity	NPD4140	Approved
0.7229	Intermediate Similarity	NPD7473	Discontinued
0.7215	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7985	Registered
0.7211	Intermediate Similarity	NPD1296	Phase 2
0.7211	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD4359	Approved
0.72	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD6111	Discontinued
0.719	Intermediate Similarity	NPD6674	Discontinued
0.7183	Intermediate Similarity	NPD3705	Approved
0.7181	Intermediate Similarity	NPD447	Suspended
0.7181	Intermediate Similarity	NPD1933	Approved
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4481	Phase 3
0.7153	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1608	Approved
0.7125	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1511	Approved
0.7114	Intermediate Similarity	NPD4307	Phase 2
0.7105	Intermediate Similarity	NPD2796	Approved
0.7105	Intermediate Similarity	NPD3539	Phase 1
0.7097	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5691	Approved
0.7091	Intermediate Similarity	NPD1247	Approved
0.7083	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD5327	Phase 3
0.7076	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6832	Phase 2
0.7071	Intermediate Similarity	NPD5536	Phase 2
0.707	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9697	Approved
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD6599	Discontinued
0.7059	Intermediate Similarity	NPD3540	Phase 1
0.705	Intermediate Similarity	NPD7157	Approved
0.7048	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7054	Approved
0.7037	Intermediate Similarity	NPD1465	Phase 2
0.7032	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD1512	Approved
0.702	Intermediate Similarity	NPD2653	Approved
0.7012	Intermediate Similarity	NPD7075	Discontinued
0.7012	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6799	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6032	Approved
0.6993	Remote Similarity	NPD2935	Discontinued
0.6982	Remote Similarity	NPD3818	Discontinued
0.6981	Remote Similarity	NPD5403	Approved
0.698	Remote Similarity	NPD6798	Discontinued
0.6975	Remote Similarity	NPD6801	Discontinued
0.6964	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6166	Phase 2
0.6964	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5401	Approved
0.6962	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3882	Suspended
0.6944	Remote Similarity	NPD1091	Approved
0.6937	Remote Similarity	NPD3686	Approved
0.6937	Remote Similarity	NPD3687	Approved
0.6933	Remote Similarity	NPD4870	Approved
0.6928	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD7466	Approved
0.6919	Remote Similarity	NPD7240	Approved
0.6918	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6653	Approved
0.6903	Remote Similarity	NPD970	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5353	Approved
0.6889	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7808	Phase 3
0.6875	Remote Similarity	NPD920	Approved
0.6871	Remote Similarity	NPD3382	Approved
0.6871	Remote Similarity	NPD3384	Approved
0.6871	Remote Similarity	NPD3383	Approved
0.6867	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1243	Approved
0.6848	Remote Similarity	NPD7768	Phase 2
0.6846	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4340	Discontinued
0.6842	Remote Similarity	NPD5735	Approved
0.6842	Remote Similarity	NPD3657	Discovery
0.6839	Remote Similarity	NPD6005	Phase 3
0.6839	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6004	Phase 3
0.6839	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1375	Discontinued
0.6839	Remote Similarity	NPD7266	Discontinued
0.6839	Remote Similarity	NPD6002	Phase 3
0.6838	Remote Similarity	NPD1358	Approved
0.6835	Remote Similarity	NPD6667	Approved
0.6835	Remote Similarity	NPD6666	Approved
0.6835	Remote Similarity	NPD7843	Approved
0.6821	Remote Similarity	NPD7251	Discontinued
0.6815	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD3892	Phase 2
0.681	Remote Similarity	NPD7411	Suspended
0.6805	Remote Similarity	NPD3926	Phase 2
0.6805	Remote Similarity	NPD5242	Approved
0.6803	Remote Similarity	NPD2922	Phase 1
0.6788	Remote Similarity	NPD2684	Approved
0.6788	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2979	Phase 3
0.6776	Remote Similarity	NPD3620	Phase 2
0.6776	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1551	Phase 2
0.6774	Remote Similarity	NPD2438	Suspended
0.677	Remote Similarity	NPD5976	Discontinued
0.6765	Remote Similarity	NPD3134	Approved
0.6763	Remote Similarity	NPD228	Approved
0.6763	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6797	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