NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.13
Volume:	246.23
LogP:	-0.412
LogD:	-0.315
LogS:	-1.625
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	4.514
Fsp3:	0.75
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:	-5.1
MDCK Permeability:	7.765341433696449e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.402
30% Bioavailability (F30%):	0.56

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.764
Plasma Protein Binding (PPB):	24.717750549316406%
Volume Distribution (VD):	0.328
Pgp-substrate:	59.41293716430664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.696
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.594

ADMET: Excretion

Clearance (CL):	2.128
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.608
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.149
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.46
Carcinogencity:	0.898
Eye Corrosion:	0.197
Eye Irritation:	0.915
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC471987

Natural Product ID:	NPC471987
*Common Name:**	KMBKVLDJXQMMRB-JXJOLMDKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMBKVLDJXQMMRB-JXJOLMDKSA-N
Standard InCHI:	InChI=1S/C12H20O5/c1-8(13)4-5-12(17)10(2,15)6-9(14)7-11(12,3)16/h4-5,9,14-17H,6-7H2,1-3H3/b5-4+/t9-,10-,11?,12-/m1/s1
SMILES:	O[C@@H]1C[C@@](C)(O)[C@](C(C1)(C)O)(O)/C=C/C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314713
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols [CHEMONTID:0002647] Cyclohexanols

*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
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[541926]

☑ 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 NPC471987 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	175
0.1-0.2	1388
0.2-0.3	5004
0.3-0.4	8346
0.4-0.5	17164
0.5-0.6	8138
0.6-0.7	2321
0.7-0.8	152
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC471267
0.8875	High Similarity	NPC236707
0.8765	High Similarity	NPC471270
0.8642	High Similarity	NPC471266
0.8642	High Similarity	NPC95124
0.85	High Similarity	NPC149550
0.85	High Similarity	NPC85105
0.8152	Intermediate Similarity	NPC120446
0.8	Intermediate Similarity	NPC214277
0.7978	Intermediate Similarity	NPC473100
0.7907	Intermediate Similarity	NPC185605
0.7889	Intermediate Similarity	NPC473099
0.7835	Intermediate Similarity	NPC194941
0.7791	Intermediate Similarity	NPC259858
0.7701	Intermediate Similarity	NPC251475
0.7701	Intermediate Similarity	NPC169941
0.766	Intermediate Similarity	NPC472995
0.7654	Intermediate Similarity	NPC471272
0.7654	Intermediate Similarity	NPC471268
0.7654	Intermediate Similarity	NPC471271
0.7653	Intermediate Similarity	NPC473068
0.7634	Intermediate Similarity	NPC196227
0.7629	Intermediate Similarity	NPC150463
0.7609	Intermediate Similarity	NPC116726
0.7582	Intermediate Similarity	NPC314727
0.7553	Intermediate Similarity	NPC476245
0.7551	Intermediate Similarity	NPC473070
0.7526	Intermediate Similarity	NPC470184
0.7525	Intermediate Similarity	NPC163004
0.75	Intermediate Similarity	NPC191323
0.75	Intermediate Similarity	NPC79945
0.75	Intermediate Similarity	NPC19771
0.7447	Intermediate Similarity	NPC478089
0.7444	Intermediate Similarity	NPC175145
0.7444	Intermediate Similarity	NPC475069
0.7426	Intermediate Similarity	NPC473069
0.7423	Intermediate Similarity	NPC38855
0.7419	Intermediate Similarity	NPC41554
0.7419	Intermediate Similarity	NPC97404
0.7416	Intermediate Similarity	NPC302360
0.7416	Intermediate Similarity	NPC40687
0.7391	Intermediate Similarity	NPC115607
0.7349	Intermediate Similarity	NPC265485
0.7349	Intermediate Similarity	NPC220939
0.734	Intermediate Similarity	NPC110022
0.7333	Intermediate Similarity	NPC298595
0.7312	Intermediate Similarity	NPC11216
0.7312	Intermediate Similarity	NPC204188
0.7312	Intermediate Similarity	NPC291484
0.7312	Intermediate Similarity	NPC80561
0.7312	Intermediate Similarity	NPC329596
0.7312	Intermediate Similarity	NPC3345
0.7312	Intermediate Similarity	NPC134321
0.7303	Intermediate Similarity	NPC57370
0.7284	Intermediate Similarity	NPC471238
0.7283	Intermediate Similarity	NPC7280
0.7283	Intermediate Similarity	NPC229612
0.7273	Intermediate Similarity	NPC249423
0.7263	Intermediate Similarity	NPC472976
0.7263	Intermediate Similarity	NPC469491
0.7263	Intermediate Similarity	NPC103527
0.7263	Intermediate Similarity	NPC472977
0.7255	Intermediate Similarity	NPC65941
0.7255	Intermediate Similarity	NPC181994
0.7234	Intermediate Similarity	NPC473675
0.7234	Intermediate Similarity	NPC275671
0.7234	Intermediate Similarity	NPC230623
0.7234	Intermediate Similarity	NPC142838
0.7229	Intermediate Similarity	NPC23954
0.7229	Intermediate Similarity	NPC242992
0.7222	Intermediate Similarity	NPC83702
0.7216	Intermediate Similarity	NPC474785
0.7216	Intermediate Similarity	NPC474938
0.7216	Intermediate Similarity	NPC199099
0.7204	Intermediate Similarity	NPC187785
0.7204	Intermediate Similarity	NPC470361
0.7204	Intermediate Similarity	NPC82876
0.7204	Intermediate Similarity	NPC259875
0.7204	Intermediate Similarity	NPC257485
0.7204	Intermediate Similarity	NPC97103
0.72	Intermediate Similarity	NPC474822
0.7196	Intermediate Similarity	NPC27999
0.7196	Intermediate Similarity	NPC477116
0.7191	Intermediate Similarity	NPC224455
0.7191	Intermediate Similarity	NPC92226
0.7188	Intermediate Similarity	NPC469583
0.7188	Intermediate Similarity	NPC276110
0.7184	Intermediate Similarity	NPC475586
0.7174	Intermediate Similarity	NPC472324
0.7172	Intermediate Similarity	NPC472554
0.717	Intermediate Similarity	NPC472400
0.716	Intermediate Similarity	NPC476650
0.716	Intermediate Similarity	NPC82337
0.7159	Intermediate Similarity	NPC96362
0.7159	Intermediate Similarity	NPC287749
0.7158	Intermediate Similarity	NPC119379
0.7158	Intermediate Similarity	NPC310013
0.7143	Intermediate Similarity	NPC472002
0.7143	Intermediate Similarity	NPC475068
0.7128	Intermediate Similarity	NPC475751
0.7128	Intermediate Similarity	NPC128672
0.7128	Intermediate Similarity	NPC473956
0.7125	Intermediate Similarity	NPC86856
0.7113	Intermediate Similarity	NPC165632
0.7113	Intermediate Similarity	NPC288970
0.7113	Intermediate Similarity	NPC472997
0.7113	Intermediate Similarity	NPC473153
0.7113	Intermediate Similarity	NPC471903
0.7113	Intermediate Similarity	NPC210717
0.7113	Intermediate Similarity	NPC103165
0.7113	Intermediate Similarity	NPC472996
0.7111	Intermediate Similarity	NPC66764
0.7111	Intermediate Similarity	NPC110150
0.71	Intermediate Similarity	NPC11956
0.71	Intermediate Similarity	NPC472552
0.71	Intermediate Similarity	NPC470972
0.7097	Intermediate Similarity	NPC474668
0.7097	Intermediate Similarity	NPC133588
0.7093	Intermediate Similarity	NPC1973
0.7093	Intermediate Similarity	NPC167873
0.7087	Intermediate Similarity	NPC217201
0.7083	Intermediate Similarity	NPC258674
0.7083	Intermediate Similarity	NPC217624
0.7083	Intermediate Similarity	NPC119562
0.7083	Intermediate Similarity	NPC279410
0.7083	Intermediate Similarity	NPC181393
0.7079	Intermediate Similarity	NPC159148
0.7079	Intermediate Similarity	NPC476646
0.7075	Intermediate Similarity	NPC472757
0.7075	Intermediate Similarity	NPC108721
0.7075	Intermediate Similarity	NPC73300
0.7071	Intermediate Similarity	NPC475877
0.7071	Intermediate Similarity	NPC272223
0.7065	Intermediate Similarity	NPC472985
0.7065	Intermediate Similarity	NPC472974
0.7065	Intermediate Similarity	NPC299068
0.7065	Intermediate Similarity	NPC255143
0.7065	Intermediate Similarity	NPC179591
0.7065	Intermediate Similarity	NPC472986
0.7059	Intermediate Similarity	NPC22134
0.7053	Intermediate Similarity	NPC475441
0.7053	Intermediate Similarity	NPC472978
0.7053	Intermediate Similarity	NPC73457
0.7045	Intermediate Similarity	NPC470429
0.7041	Intermediate Similarity	NPC477226
0.7041	Intermediate Similarity	NPC472998
0.7041	Intermediate Similarity	NPC205143
0.7041	Intermediate Similarity	NPC99726
0.7041	Intermediate Similarity	NPC287668
0.7037	Intermediate Similarity	NPC156252
0.7037	Intermediate Similarity	NPC267027
0.703	Intermediate Similarity	NPC249187
0.703	Intermediate Similarity	NPC474575
0.703	Intermediate Similarity	NPC247957
0.703	Intermediate Similarity	NPC23584
0.7024	Intermediate Similarity	NPC477792
0.7021	Intermediate Similarity	NPC109744
0.7021	Intermediate Similarity	NPC472983
0.7021	Intermediate Similarity	NPC128066
0.7019	Intermediate Similarity	NPC20192
0.7019	Intermediate Similarity	NPC11710
0.7011	Intermediate Similarity	NPC203403
0.701	Intermediate Similarity	NPC86893
0.701	Intermediate Similarity	NPC180950
0.701	Intermediate Similarity	NPC272617
0.701	Intermediate Similarity	NPC292178
0.7	Intermediate Similarity	NPC2524
0.7	Intermediate Similarity	NPC475885
0.7	Intermediate Similarity	NPC115862
0.7	Intermediate Similarity	NPC11974
0.699	Remote Similarity	NPC475060
0.699	Remote Similarity	NPC83744
0.699	Remote Similarity	NPC187435
0.699	Remote Similarity	NPC471205
0.699	Remote Similarity	NPC477916
0.699	Remote Similarity	NPC67321
0.699	Remote Similarity	NPC220229
0.699	Remote Similarity	NPC122816
0.6989	Remote Similarity	NPC245004
0.6989	Remote Similarity	NPC473097
0.6988	Remote Similarity	NPC234511
0.6981	Remote Similarity	NPC90769
0.6979	Remote Similarity	NPC109305
0.6979	Remote Similarity	NPC53555
0.6972	Remote Similarity	NPC146280
0.6972	Remote Similarity	NPC124676
0.697	Remote Similarity	NPC312325
0.6966	Remote Similarity	NPC470946
0.6966	Remote Similarity	NPC281880
0.6966	Remote Similarity	NPC470947
0.6966	Remote Similarity	NPC470945
0.6961	Remote Similarity	NPC160843
0.6957	Remote Similarity	NPC109528
0.6957	Remote Similarity	NPC290731
0.6957	Remote Similarity	NPC470360
0.6957	Remote Similarity	NPC187529
0.6957	Remote Similarity	NPC79573
0.6951	Remote Similarity	NPC163290
0.6947	Remote Similarity	NPC472325
0.6947	Remote Similarity	NPC230332

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 NPC471987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1890
0.2-0.3	3968
0.3-0.4	2172
0.4-0.5	663
0.5-0.6	267
0.6-0.7	27
0.7-0.8	2
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
0.7895	Intermediate Similarity	NPD5344	Discontinued
0.7423	Intermediate Similarity	NPD6648	Approved
0.68	Remote Similarity	NPD4225	Approved
0.6632	Remote Similarity	NPD7524	Approved
0.6602	Remote Similarity	NPD5211	Phase 2
0.6596	Remote Similarity	NPD1696	Phase 3
0.6542	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD3168	Discontinued
0.6429	Remote Similarity	NPD7838	Discovery
0.6413	Remote Similarity	NPD7332	Phase 2
0.6413	Remote Similarity	NPD6930	Phase 2
0.6413	Remote Similarity	NPD7514	Phase 3
0.6413	Remote Similarity	NPD6931	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6408	Remote Similarity	NPD5286	Approved
0.6383	Remote Similarity	NPD6695	Phase 3
0.6341	Remote Similarity	NPD368	Approved
0.6316	Remote Similarity	NPD7516	Approved
0.6304	Remote Similarity	NPD6929	Approved
0.6296	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5225	Approved
0.6286	Remote Similarity	NPD5226	Approved
0.6286	Remote Similarity	NPD4633	Approved
0.6286	Remote Similarity	NPD5224	Approved
0.6283	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD4821	Approved
0.6237	Remote Similarity	NPD7525	Registered
0.6237	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD4822	Approved
0.6237	Remote Similarity	NPD4820	Approved
0.6228	Remote Similarity	NPD7327	Approved
0.6228	Remote Similarity	NPD7328	Approved
0.6226	Remote Similarity	NPD5174	Approved
0.6226	Remote Similarity	NPD5175	Approved
0.6222	Remote Similarity	NPD8264	Approved
0.6214	Remote Similarity	NPD4755	Approved
0.62	Remote Similarity	NPD6079	Approved
0.6196	Remote Similarity	NPD7145	Approved
0.619	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD371	Approved
0.6186	Remote Similarity	NPD3618	Phase 1
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4732	Discontinued
0.617	Remote Similarity	NPD6902	Approved
0.6161	Remote Similarity	NPD4632	Approved
0.6154	Remote Similarity	NPD7638	Approved
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6139	Remote Similarity	NPD4202	Approved
0.6122	Remote Similarity	NPD7750	Discontinued
0.6122	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5222	Approved
0.6117	Remote Similarity	NPD5221	Approved
0.61	Remote Similarity	NPD6698	Approved
0.61	Remote Similarity	NPD46	Approved
0.6095	Remote Similarity	NPD4700	Approved
0.6087	Remote Similarity	NPD6925	Approved
0.6087	Remote Similarity	NPD6932	Approved
0.6087	Remote Similarity	NPD5776	Phase 2
0.6082	Remote Similarity	NPD5363	Approved
0.6082	Remote Similarity	NPD6893	Approved
0.6058	Remote Similarity	NPD5173	Approved
0.6055	Remote Similarity	NPD5697	Approved
0.6042	Remote Similarity	NPD6110	Phase 1
0.604	Remote Similarity	NPD7637	Suspended
0.604	Remote Similarity	NPD7515	Phase 2
0.6022	Remote Similarity	NPD4268	Approved
0.6022	Remote Similarity	NPD4271	Approved
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6898	Phase 1
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6881	Approved
0.5983	Remote Similarity	NPD6319	Approved
0.5981	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6933	Approved
0.5957	Remote Similarity	NPD7645	Phase 2
0.5957	Remote Similarity	NPD4195	Approved
0.5946	Remote Similarity	NPD6012	Approved
0.5946	Remote Similarity	NPD6013	Approved
0.5946	Remote Similarity	NPD6014	Approved
0.5938	Remote Similarity	NPD3667	Approved
0.5932	Remote Similarity	NPD8296	Approved
0.5932	Remote Similarity	NPD7503	Approved
0.5932	Remote Similarity	NPD8380	Approved
0.5932	Remote Similarity	NPD8379	Approved
0.5932	Remote Similarity	NPD8378	Approved
0.5932	Remote Similarity	NPD8033	Approved
0.5932	Remote Similarity	NPD8335	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5922	Remote Similarity	NPD5282	Discontinued
0.5909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4695	Discontinued
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD5250	Approved
0.5893	Remote Similarity	NPD6371	Approved
0.5893	Remote Similarity	NPD5249	Phase 3
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD5248	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5893	Remote Similarity	NPD5251	Approved
0.5893	Remote Similarity	NPD5247	Approved
0.5882	Remote Similarity	NPD7983	Approved
0.5882	Remote Similarity	NPD7087	Discontinued
0.5865	Remote Similarity	NPD4629	Approved
0.5865	Remote Similarity	NPD5210	Approved
0.5862	Remote Similarity	NPD6009	Approved
0.5859	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4519	Discontinued
0.5859	Remote Similarity	NPD4249	Approved
0.5859	Remote Similarity	NPD4623	Approved
0.5856	Remote Similarity	NPD5128	Approved
0.5856	Remote Similarity	NPD6011	Approved
0.5851	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5290	Discontinued
0.5847	Remote Similarity	NPD8377	Approved
0.5847	Remote Similarity	NPD6054	Approved
0.5847	Remote Similarity	NPD8294	Approved
0.5842	Remote Similarity	NPD4753	Phase 2
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6649	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD5216	Approved
0.5841	Remote Similarity	NPD5217	Approved
0.5841	Remote Similarity	NPD6650	Approved
0.5841	Remote Similarity	NPD5215	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5841	Remote Similarity	NPD6617	Approved
0.5833	Remote Similarity	NPD7632	Discontinued
0.5818	Remote Similarity	NPD4768	Approved
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD4767	Approved
0.5818	Remote Similarity	NPD5357	Phase 1
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5816	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD3133	Approved
0.5816	Remote Similarity	NPD3665	Phase 1
0.5816	Remote Similarity	NPD4786	Approved
0.581	Remote Similarity	NPD4697	Phase 3
0.5806	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4251	Approved
0.58	Remote Similarity	NPD4250	Approved
0.5798	Remote Similarity	NPD6015	Approved
0.5798	Remote Similarity	NPD6016	Approved
0.5789	Remote Similarity	NPD6683	Phase 2
0.5789	Remote Similarity	NPD6882	Approved
0.5784	Remote Similarity	NPD5785	Approved
0.578	Remote Similarity	NPD4754	Approved
0.5778	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4270	Approved
0.5773	Remote Similarity	NPD4269	Approved
0.5769	Remote Similarity	NPD7748	Approved
0.5766	Remote Similarity	NPD6412	Phase 2
0.5766	Remote Similarity	NPD5701	Approved
0.5761	Remote Similarity	NPD6926	Approved
0.5761	Remote Similarity	NPD6924	Approved
0.5758	Remote Similarity	NPD1694	Approved
0.5755	Remote Similarity	NPD7902	Approved
0.5752	Remote Similarity	NPD5169	Approved
0.5752	Remote Similarity	NPD5135	Approved
0.5752	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6370	Approved
0.575	Remote Similarity	NPD5988	Approved
0.5741	Remote Similarity	NPD4159	Approved
0.5729	Remote Similarity	NPD7509	Discontinued
0.5714	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD5127	Approved
0.57	Remote Similarity	NPD5279	Phase 3
0.5699	Remote Similarity	NPD6942	Approved
0.5699	Remote Similarity	NPD7339	Approved
0.5684	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6921	Approved
0.5667	Remote Similarity	NPD5983	Phase 2
0.5664	Remote Similarity	NPD6372	Approved
0.5664	Remote Similarity	NPD6373	Approved
0.5664	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD7492	Approved
0.5631	Remote Similarity	NPD7136	Phase 2
0.563	Remote Similarity	NPD4522	Approved
0.5625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.561	Remote Similarity	NPD342	Phase 1
0.561	Remote Similarity	NPD6616	Approved
0.561	Remote Similarity	NPD7507	Approved
0.56	Remote Similarity	NPD7319	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