NPASS Compound

Structure

CID225351 OpenBabel06191716022D 21 23 0 0 0 0 0 0 0 0999 V2000 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5602 -3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -3.7872 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 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 -3.4049 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 10 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 15 2 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 16 2 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.1
Volume:	293.625
LogP:	3.252
LogD:	2.925
LogS:	-4.192
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.827
Synthetic Accessibility Score:	3.622
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.937
MDCK Permeability:	1.9478800822980702e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.216
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	95.2337875366211%
Volume Distribution (VD):	0.885
Pgp-substrate:	5.502512454986572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.327
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.561
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	0.78
Half-life (T1/2):	0.434

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.725
AMES Toxicity:	0.584
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.9
Carcinogencity:	0.704
Eye Corrosion:	0.021
Eye Irritation:	0.406
Respiratory Toxicity:	0.652

Download Data

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

Natural Product: NPC225351

Natural Product ID:	NPC225351
*Common Name:**	Trigoxyphin N
IUPAC Name:	8-hydroxy-9-methoxy-3,3,7-trimethylcyclopenta[a]naphthalene-2,5-dione
Synonyms:
Standard InCHIKey:	LFSUFCYQYMSWMN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O4/c1-8-5-10-12(18)7-11-9(6-13(19)17(11,2)3)14(10)16(21-4)15(8)20/h5-7,20H,1-4H3
SMILES:	COc1c2C3=CC(=O)C(C3=CC(=O)c2cc(c1O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2430308
PubChem CID:	72192904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO24810	Spermacoce alata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8474	Beilschmiedia tooram	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23455	Sphaeria obiones	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
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
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	5000.0	nM	PMID[546261]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4080.0	nM	PMID[546261]

☑ 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 NPC225351 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	377
0.1-0.2	1607
0.2-0.3	3601
0.3-0.4	9309
0.4-0.5	9415
0.5-0.6	3666
0.6-0.7	8795
0.7-0.8	5558
0.8-0.85	319
0.85-0.9	44
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9366	High Similarity	NPC196941
0.9366	High Similarity	NPC309169
0.9306	High Similarity	NPC52692
0.9225	High Similarity	NPC11314
0.8926	High Similarity	NPC144283
0.8889	High Similarity	NPC84273
0.8828	High Similarity	NPC169214
0.8828	High Similarity	NPC176030
0.8828	High Similarity	NPC141817
0.8828	High Similarity	NPC229218
0.8828	High Similarity	NPC192597
0.8816	High Similarity	NPC213401
0.88	High Similarity	NPC306011
0.88	High Similarity	NPC472838
0.8784	High Similarity	NPC58373
0.8767	High Similarity	NPC50954
0.8742	High Similarity	NPC164912
0.8723	High Similarity	NPC138472
0.8675	High Similarity	NPC302783
0.8675	High Similarity	NPC473201
0.8675	High Similarity	NPC118427
0.8675	High Similarity	NPC124842
0.8667	High Similarity	NPC237441
0.8649	High Similarity	NPC73416
0.8649	High Similarity	NPC160777
0.8645	High Similarity	NPC21046
0.8609	High Similarity	NPC295977
0.8609	High Similarity	NPC58310
0.8592	High Similarity	NPC111845
0.8591	High Similarity	NPC58752
0.8591	High Similarity	NPC39361
0.8562	High Similarity	NPC62051
0.8553	High Similarity	NPC75377
0.8552	High Similarity	NPC230811
0.8542	High Similarity	NPC471670
0.8533	High Similarity	NPC77598
0.8533	High Similarity	NPC470757
0.8516	High Similarity	NPC37543
0.8516	High Similarity	NPC199463
0.8491	Intermediate Similarity	NPC263212
0.8487	Intermediate Similarity	NPC31132
0.8472	Intermediate Similarity	NPC22644
0.8462	Intermediate Similarity	NPC104876
0.8462	Intermediate Similarity	NPC245891
0.8456	Intermediate Similarity	NPC275278
0.8456	Intermediate Similarity	NPC300603
0.8456	Intermediate Similarity	NPC91694
0.8452	Intermediate Similarity	NPC288353
0.8452	Intermediate Similarity	NPC14561
0.8452	Intermediate Similarity	NPC279605
0.8452	Intermediate Similarity	NPC5379
0.8452	Intermediate Similarity	NPC77807
0.8451	Intermediate Similarity	NPC239134
0.8442	Intermediate Similarity	NPC127172
0.8442	Intermediate Similarity	NPC305710
0.8435	Intermediate Similarity	NPC471853
0.8431	Intermediate Similarity	NPC78505
0.8429	Intermediate Similarity	NPC16651
0.8429	Intermediate Similarity	NPC32163
0.8421	Intermediate Similarity	NPC134293
0.8421	Intermediate Similarity	NPC472837
0.8421	Intermediate Similarity	NPC261322
0.8408	Intermediate Similarity	NPC185617
0.84	Intermediate Similarity	NPC258856
0.84	Intermediate Similarity	NPC157133
0.8397	Intermediate Similarity	NPC178976
0.8389	Intermediate Similarity	NPC46880
0.8387	Intermediate Similarity	NPC234485
0.838	Intermediate Similarity	NPC66905
0.8377	Intermediate Similarity	NPC180388
0.8365	Intermediate Similarity	NPC476822
0.8356	Intermediate Similarity	NPC119542
0.8355	Intermediate Similarity	NPC471852
0.8345	Intermediate Similarity	NPC88065
0.8345	Intermediate Similarity	NPC95485
0.8345	Intermediate Similarity	NPC89504
0.8345	Intermediate Similarity	NPC252343
0.8345	Intermediate Similarity	NPC153088
0.8344	Intermediate Similarity	NPC477410
0.8333	Intermediate Similarity	NPC327410
0.8333	Intermediate Similarity	NPC472836
0.8333	Intermediate Similarity	NPC207732
0.8333	Intermediate Similarity	NPC105213
0.8333	Intermediate Similarity	NPC276815
0.8333	Intermediate Similarity	NPC25850
0.8323	Intermediate Similarity	NPC107109
0.8323	Intermediate Similarity	NPC93552
0.8322	Intermediate Similarity	NPC164295
0.8322	Intermediate Similarity	NPC201297
0.8322	Intermediate Similarity	NPC248068
0.8313	Intermediate Similarity	NPC26386
0.8312	Intermediate Similarity	NPC272566
0.8311	Intermediate Similarity	NPC78987
0.8311	Intermediate Similarity	NPC82336
0.8301	Intermediate Similarity	NPC142654
0.8301	Intermediate Similarity	NPC303989
0.8291	Intermediate Similarity	NPC84571
0.828	Intermediate Similarity	NPC283301
0.828	Intermediate Similarity	NPC296044
0.828	Intermediate Similarity	NPC167098
0.8278	Intermediate Similarity	NPC75295
0.8267	Intermediate Similarity	NPC209085
0.8267	Intermediate Similarity	NPC46161
0.8267	Intermediate Similarity	NPC224884
0.8267	Intermediate Similarity	NPC239608
0.8264	Intermediate Similarity	NPC239302
0.8264	Intermediate Similarity	NPC312560
0.8264	Intermediate Similarity	NPC50763
0.8258	Intermediate Similarity	NPC131121
0.8258	Intermediate Similarity	NPC3744
0.8258	Intermediate Similarity	NPC149889
0.8258	Intermediate Similarity	NPC312338
0.8258	Intermediate Similarity	NPC161778
0.8258	Intermediate Similarity	NPC218628
0.8258	Intermediate Similarity	NPC137125
0.8252	Intermediate Similarity	NPC172673
0.825	Intermediate Similarity	NPC475055
0.8247	Intermediate Similarity	NPC472279
0.8247	Intermediate Similarity	NPC475718
0.8243	Intermediate Similarity	NPC223336
0.8243	Intermediate Similarity	NPC470407
0.8239	Intermediate Similarity	NPC311740
0.8239	Intermediate Similarity	NPC131905
0.8231	Intermediate Similarity	NPC277559
0.8228	Intermediate Similarity	NPC235448
0.8227	Intermediate Similarity	NPC254492
0.8227	Intermediate Similarity	NPC474737
0.8214	Intermediate Similarity	NPC30216
0.8207	Intermediate Similarity	NPC59459
0.8207	Intermediate Similarity	NPC4170
0.8207	Intermediate Similarity	NPC263817
0.8205	Intermediate Similarity	NPC477048
0.8205	Intermediate Similarity	NPC477047
0.8205	Intermediate Similarity	NPC273248
0.8205	Intermediate Similarity	NPC474000
0.82	Intermediate Similarity	NPC184935
0.82	Intermediate Similarity	NPC312256
0.8194	Intermediate Similarity	NPC70320
0.8194	Intermediate Similarity	NPC115869
0.8188	Intermediate Similarity	NPC28398
0.8187	Intermediate Similarity	NPC144843
0.8187	Intermediate Similarity	NPC470694
0.8182	Intermediate Similarity	NPC37220
0.8182	Intermediate Similarity	NPC304622
0.8169	Intermediate Similarity	NPC5018
0.8169	Intermediate Similarity	NPC72667
0.8169	Intermediate Similarity	NPC276466
0.8169	Intermediate Similarity	NPC123722
0.8169	Intermediate Similarity	NPC151167
0.8169	Intermediate Similarity	NPC123228
0.8165	Intermediate Similarity	NPC143328
0.8165	Intermediate Similarity	NPC304008
0.8165	Intermediate Similarity	NPC187745
0.8165	Intermediate Similarity	NPC219867
0.8165	Intermediate Similarity	NPC161960
0.8165	Intermediate Similarity	NPC180011
0.8153	Intermediate Similarity	NPC268008
0.8153	Intermediate Similarity	NPC180901
0.8153	Intermediate Similarity	NPC300757
0.8146	Intermediate Similarity	NPC469615
0.8143	Intermediate Similarity	NPC257976
0.8143	Intermediate Similarity	NPC242372
0.8143	Intermediate Similarity	NPC4181
0.8143	Intermediate Similarity	NPC164778
0.8141	Intermediate Similarity	NPC474993
0.8138	Intermediate Similarity	NPC183103
0.8137	Intermediate Similarity	NPC270837
0.8137	Intermediate Similarity	NPC187491
0.8137	Intermediate Similarity	NPC319200
0.8137	Intermediate Similarity	NPC220313
0.8137	Intermediate Similarity	NPC18100
0.8137	Intermediate Similarity	NPC236132
0.8133	Intermediate Similarity	NPC110419
0.8133	Intermediate Similarity	NPC475054
0.8125	Intermediate Similarity	NPC318081
0.8125	Intermediate Similarity	NPC117609
0.8117	Intermediate Similarity	NPC474556
0.8117	Intermediate Similarity	NPC55327
0.8113	Intermediate Similarity	NPC45846
0.8112	Intermediate Similarity	NPC201069
0.8108	Intermediate Similarity	NPC264022
0.8108	Intermediate Similarity	NPC49911
0.8108	Intermediate Similarity	NPC36868
0.8105	Intermediate Similarity	NPC246229
0.8105	Intermediate Similarity	NPC273798
0.8105	Intermediate Similarity	NPC165389
0.8105	Intermediate Similarity	NPC191899
0.8101	Intermediate Similarity	NPC478223
0.8101	Intermediate Similarity	NPC474167
0.8101	Intermediate Similarity	NPC109765
0.8101	Intermediate Similarity	NPC470762
0.8101	Intermediate Similarity	NPC115853
0.8099	Intermediate Similarity	NPC303680
0.8099	Intermediate Similarity	NPC179777
0.8099	Intermediate Similarity	NPC84076
0.8099	Intermediate Similarity	NPC90128
0.8095	Intermediate Similarity	NPC22222
0.8095	Intermediate Similarity	NPC139519
0.8095	Intermediate Similarity	NPC208760
0.8095	Intermediate Similarity	NPC258502

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 NPC225351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	996
0.2-0.3	1569
0.3-0.4	2670
0.4-0.5	1968
0.5-0.6	1008
0.6-0.7	505
0.7-0.8	93
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8042	Intermediate Similarity	NPD9494	Approved
0.7853	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD3882	Suspended
0.7762	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7458	Discontinued
0.7692	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD3972	Approved
0.7662	Intermediate Similarity	NPD7003	Approved
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD2801	Approved
0.764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD1934	Approved
0.7562	Intermediate Similarity	NPD7028	Phase 2
0.7548	Intermediate Similarity	NPD8166	Discontinued
0.7535	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3620	Phase 2
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2800	Approved
0.7483	Intermediate Similarity	NPD4626	Approved
0.7468	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7414	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1651	Approved
0.7355	Intermediate Similarity	NPD2344	Approved
0.7353	Intermediate Similarity	NPD3818	Discontinued
0.7347	Intermediate Similarity	NPD1876	Approved
0.7347	Intermediate Similarity	NPD1283	Approved
0.7338	Intermediate Similarity	NPD2799	Discontinued
0.7338	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1607	Approved
0.732	Intermediate Similarity	NPD6651	Approved
0.7308	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5494	Approved
0.7303	Intermediate Similarity	NPD943	Approved
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1511	Approved
0.7284	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD5536	Phase 2
0.7273	Intermediate Similarity	NPD5977	Approved
0.7273	Intermediate Similarity	NPD5978	Approved
0.7261	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD447	Suspended
0.7255	Intermediate Similarity	NPD230	Phase 1
0.7246	Intermediate Similarity	NPD6234	Discontinued
0.7241	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2932	Approved
0.7239	Intermediate Similarity	NPD4380	Phase 2
0.7239	Intermediate Similarity	NPD6599	Discontinued
0.7235	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2898	Approved
0.7235	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4110	Phase 3
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD228	Approved
0.7212	Intermediate Similarity	NPD7819	Suspended
0.7205	Intermediate Similarity	NPD1512	Approved
0.7205	Intermediate Similarity	NPD6273	Approved
0.719	Intermediate Similarity	NPD1240	Approved
0.719	Intermediate Similarity	NPD4060	Phase 1
0.7179	Intermediate Similarity	NPD6099	Approved
0.7179	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD5691	Approved
0.717	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6959	Discontinued
0.716	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1281	Approved
0.7123	Intermediate Similarity	NPD3019	Approved
0.7118	Intermediate Similarity	NPD5710	Approved
0.7118	Intermediate Similarity	NPD5711	Approved
0.7115	Intermediate Similarity	NPD1510	Phase 2
0.7107	Intermediate Similarity	NPD3750	Approved
0.7105	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6873	Phase 2
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7083	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD824	Approved
0.7069	Intermediate Similarity	NPD7074	Phase 3
0.7067	Intermediate Similarity	NPD1470	Approved
0.7066	Intermediate Similarity	NPD3817	Phase 2
0.7059	Intermediate Similarity	NPD2313	Discontinued
0.7047	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1471	Phase 3
0.7025	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4965	Approved
0.7024	Intermediate Similarity	NPD4966	Approved
0.7024	Intermediate Similarity	NPD4967	Phase 2
0.702	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD7054	Approved
0.7006	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5283	Phase 1
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6987	Remote Similarity	NPD4097	Suspended
0.6981	Remote Similarity	NPD2424	Discontinued
0.6977	Remote Similarity	NPD3926	Phase 2
0.6975	Remote Similarity	NPD7390	Discontinued
0.6971	Remote Similarity	NPD7472	Approved
0.6968	Remote Similarity	NPD2979	Phase 3
0.6962	Remote Similarity	NPD5406	Approved
0.6962	Remote Similarity	NPD5408	Approved
0.6962	Remote Similarity	NPD2438	Suspended
0.6962	Remote Similarity	NPD5404	Approved
0.6962	Remote Similarity	NPD5405	Approved
0.6959	Remote Similarity	NPD1247	Approved
0.6959	Remote Similarity	NPD7199	Phase 2
0.6954	Remote Similarity	NPD7228	Approved
0.6952	Remote Similarity	NPD2491	Approved
0.6948	Remote Similarity	NPD3764	Approved
0.6941	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1201	Approved
0.6903	Remote Similarity	NPD8032	Phase 2
0.6893	Remote Similarity	NPD6559	Discontinued
0.689	Remote Similarity	NPD5049	Phase 3
0.6889	Remote Similarity	NPD8434	Phase 2
0.6887	Remote Similarity	NPD6696	Suspended
0.6883	Remote Similarity	NPD3027	Phase 3
0.6879	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD1241	Discontinued
0.6871	Remote Similarity	NPD6799	Approved
0.6868	Remote Similarity	NPD2490	Approved
0.6868	Remote Similarity	NPD2488	Approved
0.6867	Remote Similarity	NPD9269	Phase 2
0.6867	Remote Similarity	NPD2649	Approved
0.6867	Remote Similarity	NPD2651	Approved
0.6864	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3057	Approved
0.6862	Remote Similarity	NPD3448	Approved
0.6854	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6801	Discontinued
0.6845	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6797	Phase 2
0.6832	Remote Similarity	NPD6674	Discontinued
0.6829	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8312	Approved
0.6816	Remote Similarity	NPD8313	Approved
0.6815	Remote Similarity	NPD3657	Discovery
0.6813	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3300	Phase 2
0.6798	Remote Similarity	NPD7251	Discontinued
0.6797	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4624	Approved
0.6796	Remote Similarity	NPD8150	Discontinued
0.6792	Remote Similarity	NPD3748	Approved
0.6792	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD6385	Approved
0.6786	Remote Similarity	NPD7411	Suspended
0.6786	Remote Similarity	NPD6386	Approved
0.6784	Remote Similarity	NPD3749	Approved
0.6784	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1778	Approved
0.6774	Remote Similarity	NPD7095	Approved
0.6772	Remote Similarity	NPD3533	Approved
0.6772	Remote Similarity	NPD2972	Approved
0.6766	Remote Similarity	NPD3455	Phase 2
0.6761	Remote Similarity	NPD7177	Discontinued
0.676	Remote Similarity	NPD7808	Phase 3
0.6757	Remote Similarity	NPD9545	Approved
0.675	Remote Similarity	NPD2796	Approved
0.675	Remote Similarity	NPD4477	Approved
0.675	Remote Similarity	NPD2531	Phase 2
0.675	Remote Similarity	NPD4476	Approved
0.6748	Remote Similarity	NPD2354	Approved
0.6748	Remote Similarity	NPD6190	Approved
0.6733	Remote Similarity	NPD3023	Approved
0.6733	Remote Similarity	NPD3026	Approved
0.6731	Remote Similarity	NPD411	Approved
0.6731	Remote Similarity	NPD6798	Discontinued
0.6731	Remote Similarity	NPD3268	Approved
0.6731	Remote Similarity	NPD7985	Registered
0.672	Remote Similarity	NPD2493	Approved
0.672	Remote Similarity	NPD2494	Approved
0.6713	Remote Similarity	NPD3021	Approved
0.6713	Remote Similarity	NPD3022	Approved
0.6712	Remote Similarity	NPD5951	Approved
0.6711	Remote Similarity	NPD1357	Approved
0.6711	Remote Similarity	NPD3024	Approved
0.6711	Remote Similarity	NPD3025	Approved
0.6709	Remote Similarity	NPD1933	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