NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	2.896
LogD:	3.102
LogS:	-2.912
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	4.593
Fsp3:	0.6
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:	-4.721
MDCK Permeability:	2.3896382117527537e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.393
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.346
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.375
Plasma Protein Binding (PPB):	86.97382354736328%
Volume Distribution (VD):	1.203
Pgp-substrate:	16.915700912475586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	11.83
Half-life (T1/2):	0.607

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.566
Drug-inuced Liver Injury (DILI):	0.703
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.548
Carcinogencity:	0.892
Eye Corrosion:	0.011
Eye Irritation:	0.144
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC473891

Natural Product ID:	NPC473891
*Common Name:**	9-Alphahydroxyasterolide
IUPAC Name:	(4aS,8aR,9S,9aS)-9-hydroxy-3,8a-dimethyl-5-methylidene-4a,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:	9-Alphahydroxyasterolide
Standard InCHIKey:	RVRGUBAZBPVMKB-RMRHIDDWSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-5-4-6-15(3)11(8)7-10-9(2)14(17)18-12(10)13(15)16/h11-13,16H,1,4-7H2,2-3H3/t11-,12-,13+,15+/m0/s1
SMILES:	CC1=C2CC3C(=C)CCCC3(C(C2OC1=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454453
PubChem CID:	44587885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO12695	Hedyosmum orientale	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18651771]
NPO12695	Hedyosmum orientale	Species	Chloranthaceae	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
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3100.0	nM	PMID[507602]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8800.0	nM	PMID[507602]

☑ 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 NPC473891 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	179
0.1-0.2	1156
0.2-0.3	4200
0.3-0.4	9612
0.4-0.5	13293
0.5-0.6	7208
0.6-0.7	5854
0.7-0.8	1080
0.8-0.85	90
0.85-0.9	23
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8977	High Similarity	NPC53555
0.8889	High Similarity	NPC473153
0.8765	High Similarity	NPC189206
0.875	High Similarity	NPC310479
0.875	High Similarity	NPC280149
0.875	High Similarity	NPC221111
0.8721	High Similarity	NPC131813
0.8556	High Similarity	NPC110022
0.8556	High Similarity	NPC162615
0.8556	High Similarity	NPC205034
0.8556	High Similarity	NPC152778
0.8539	High Similarity	NPC78973
0.8539	High Similarity	NPC182136
0.8511	High Similarity	NPC303559
0.8495	Intermediate Similarity	NPC159763
0.8495	Intermediate Similarity	NPC278386
0.8495	Intermediate Similarity	NPC124512
0.8488	Intermediate Similarity	NPC32223
0.8452	Intermediate Similarity	NPC10636
0.8444	Intermediate Similarity	NPC472811
0.8444	Intermediate Similarity	NPC72845
0.8434	Intermediate Similarity	NPC184737
0.8427	Intermediate Similarity	NPC82876
0.8427	Intermediate Similarity	NPC474396
0.8427	Intermediate Similarity	NPC50488
0.8404	Intermediate Similarity	NPC38855
0.8387	Intermediate Similarity	NPC73911
0.8387	Intermediate Similarity	NPC205143
0.8372	Intermediate Similarity	NPC311070
0.8352	Intermediate Similarity	NPC472812
0.8352	Intermediate Similarity	NPC139692
0.8295	Intermediate Similarity	NPC329692
0.828	Intermediate Similarity	NPC16967
0.8276	Intermediate Similarity	NPC96055
0.8261	Intermediate Similarity	NPC191521
0.8261	Intermediate Similarity	NPC57117
0.8229	Intermediate Similarity	NPC472552
0.8229	Intermediate Similarity	NPC121423
0.8202	Intermediate Similarity	NPC473097
0.8172	Intermediate Similarity	NPC276110
0.8144	Intermediate Similarity	NPC23584
0.8144	Intermediate Similarity	NPC281378
0.814	Intermediate Similarity	NPC159148
0.8132	Intermediate Similarity	NPC472642
0.8125	Intermediate Similarity	NPC472554
0.8105	Intermediate Similarity	NPC474440
0.809	Intermediate Similarity	NPC475069
0.809	Intermediate Similarity	NPC175145
0.8085	Intermediate Similarity	NPC242848
0.8085	Intermediate Similarity	NPC134072
0.8085	Intermediate Similarity	NPC165632
0.8085	Intermediate Similarity	NPC88009
0.8085	Intermediate Similarity	NPC234993
0.8081	Intermediate Similarity	NPC187435
0.8081	Intermediate Similarity	NPC67321
0.8065	Intermediate Similarity	NPC105490
0.8065	Intermediate Similarity	NPC470255
0.8043	Intermediate Similarity	NPC78594
0.8043	Intermediate Similarity	NPC329842
0.8041	Intermediate Similarity	NPC283343
0.8041	Intermediate Similarity	NPC273668
0.8041	Intermediate Similarity	NPC472815
0.8041	Intermediate Similarity	NPC11956
0.8041	Intermediate Similarity	NPC258547
0.8023	Intermediate Similarity	NPC281880
0.8023	Intermediate Similarity	NPC268827
0.8021	Intermediate Similarity	NPC473510
0.8021	Intermediate Similarity	NPC474190
0.8	Intermediate Similarity	NPC181994
0.8	Intermediate Similarity	NPC231751
0.8	Intermediate Similarity	NPC210337
0.8	Intermediate Similarity	NPC306265
0.798	Intermediate Similarity	NPC88349
0.7979	Intermediate Similarity	NPC472441
0.7979	Intermediate Similarity	NPC183012
0.7978	Intermediate Similarity	NPC106416
0.7978	Intermediate Similarity	NPC474013
0.7978	Intermediate Similarity	NPC35933
0.7978	Intermediate Similarity	NPC86316
0.7978	Intermediate Similarity	NPC471795
0.7959	Intermediate Similarity	NPC474822
0.7957	Intermediate Similarity	NPC156553
0.7957	Intermediate Similarity	NPC7349
0.7957	Intermediate Similarity	NPC472640
0.7957	Intermediate Similarity	NPC472641
0.7955	Intermediate Similarity	NPC472377
0.7955	Intermediate Similarity	NPC321385
0.7955	Intermediate Similarity	NPC42476
0.7938	Intermediate Similarity	NPC11974
0.7938	Intermediate Similarity	NPC473160
0.7938	Intermediate Similarity	NPC475617
0.7938	Intermediate Similarity	NPC198992
0.7931	Intermediate Similarity	NPC170303
0.7921	Intermediate Similarity	NPC257853
0.7917	Intermediate Similarity	NPC473154
0.7912	Intermediate Similarity	NPC472810
0.7912	Intermediate Similarity	NPC472809
0.7912	Intermediate Similarity	NPC277771
0.79	Intermediate Similarity	NPC473586
0.7895	Intermediate Similarity	NPC154526
0.7895	Intermediate Similarity	NPC472362
0.7895	Intermediate Similarity	NPC472363
0.7889	Intermediate Similarity	NPC250981
0.7889	Intermediate Similarity	NPC471219
0.7857	Intermediate Similarity	NPC476081
0.7857	Intermediate Similarity	NPC295791
0.7849	Intermediate Similarity	NPC186363
0.7849	Intermediate Similarity	NPC303697
0.7849	Intermediate Similarity	NPC233345
0.7849	Intermediate Similarity	NPC472814
0.7849	Intermediate Similarity	NPC177037
0.7843	Intermediate Similarity	NPC177047
0.7841	Intermediate Similarity	NPC471218
0.7841	Intermediate Similarity	NPC16321
0.7835	Intermediate Similarity	NPC476299
0.7835	Intermediate Similarity	NPC117685
0.7835	Intermediate Similarity	NPC474012
0.7835	Intermediate Similarity	NPC230546
0.7835	Intermediate Similarity	NPC201406
0.7826	Intermediate Similarity	NPC79027
0.7826	Intermediate Similarity	NPC20946
0.7826	Intermediate Similarity	NPC246028
0.7822	Intermediate Similarity	NPC475263
0.7822	Intermediate Similarity	NPC38948
0.7822	Intermediate Similarity	NPC88701
0.7812	Intermediate Similarity	NPC199099
0.7812	Intermediate Similarity	NPC121402
0.7812	Intermediate Similarity	NPC151681
0.7812	Intermediate Similarity	NPC175351
0.7812	Intermediate Similarity	NPC132753
0.7812	Intermediate Similarity	NPC224356
0.7812	Intermediate Similarity	NPC51499
0.7812	Intermediate Similarity	NPC474343
0.7802	Intermediate Similarity	NPC181103
0.7802	Intermediate Similarity	NPC305029
0.7802	Intermediate Similarity	NPC166857
0.7802	Intermediate Similarity	NPC476948
0.7802	Intermediate Similarity	NPC312561
0.78	Intermediate Similarity	NPC186668
0.7789	Intermediate Similarity	NPC329435
0.7789	Intermediate Similarity	NPC111273
0.7789	Intermediate Similarity	NPC471915
0.7778	Intermediate Similarity	NPC120321
0.7778	Intermediate Similarity	NPC474124
0.7778	Intermediate Similarity	NPC476602
0.7778	Intermediate Similarity	NPC253604
0.7778	Intermediate Similarity	NPC65661
0.7778	Intermediate Similarity	NPC472821
0.7778	Intermediate Similarity	NPC159533
0.7778	Intermediate Similarity	NPC30984
0.7755	Intermediate Similarity	NPC471412
0.7753	Intermediate Similarity	NPC23748
0.7753	Intermediate Similarity	NPC79945
0.7753	Intermediate Similarity	NPC476927
0.7753	Intermediate Similarity	NPC49208
0.7745	Intermediate Similarity	NPC206618
0.7745	Intermediate Similarity	NPC475065
0.7742	Intermediate Similarity	NPC51486
0.7732	Intermediate Similarity	NPC218107
0.7732	Intermediate Similarity	NPC325229
0.7732	Intermediate Similarity	NPC275086
0.7732	Intermediate Similarity	NPC278673
0.7727	Intermediate Similarity	NPC475944
0.7727	Intermediate Similarity	NPC25554
0.7727	Intermediate Similarity	NPC142163
0.7723	Intermediate Similarity	NPC329048
0.7723	Intermediate Similarity	NPC330011
0.7723	Intermediate Similarity	NPC471205
0.7717	Intermediate Similarity	NPC93411
0.7717	Intermediate Similarity	NPC242448
0.77	Intermediate Similarity	NPC161775
0.7692	Intermediate Similarity	NPC85698
0.7692	Intermediate Similarity	NPC470063
0.7684	Intermediate Similarity	NPC472360
0.7684	Intermediate Similarity	NPC472416
0.7684	Intermediate Similarity	NPC469697
0.7684	Intermediate Similarity	NPC201725
0.7677	Intermediate Similarity	NPC32577
0.7677	Intermediate Similarity	NPC471914
0.7677	Intermediate Similarity	NPC155332
0.7677	Intermediate Similarity	NPC109195
0.7677	Intermediate Similarity	NPC476471
0.7677	Intermediate Similarity	NPC475038
0.7677	Intermediate Similarity	NPC114540
0.7677	Intermediate Similarity	NPC475344
0.7674	Intermediate Similarity	NPC283619
0.7667	Intermediate Similarity	NPC306951
0.7653	Intermediate Similarity	NPC16601
0.7653	Intermediate Similarity	NPC251680
0.7653	Intermediate Similarity	NPC472826
0.7653	Intermediate Similarity	NPC472644
0.7653	Intermediate Similarity	NPC471413
0.7653	Intermediate Similarity	NPC324841
0.7647	Intermediate Similarity	NPC473482
0.7647	Intermediate Similarity	NPC475418
0.7647	Intermediate Similarity	NPC50124
0.7647	Intermediate Similarity	NPC318363
0.764	Intermediate Similarity	NPC2524
0.764	Intermediate Similarity	NPC256112
0.7634	Intermediate Similarity	NPC116620

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 NPC473891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1429
0.2-0.3	3753
0.3-0.4	2489
0.4-0.5	879
0.5-0.6	281
0.6-0.7	153
0.7-0.8	8
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
0.8495	Intermediate Similarity	NPD4225	Approved
0.7732	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5344	Discontinued
0.7308	Intermediate Similarity	NPD6686	Approved
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7204	Intermediate Similarity	NPD1694	Approved
0.717	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7632	Discontinued
0.7117	Intermediate Similarity	NPD7516	Approved
0.7097	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7327	Approved
0.7027	Intermediate Similarity	NPD7328	Approved
0.6991	Remote Similarity	NPD8033	Approved
0.697	Remote Similarity	NPD7748	Approved
0.6961	Remote Similarity	NPD6648	Approved
0.6947	Remote Similarity	NPD3618	Phase 1
0.6939	Remote Similarity	NPD7515	Phase 2
0.6903	Remote Similarity	NPD8377	Approved
0.6903	Remote Similarity	NPD8294	Approved
0.6887	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7524	Approved
0.6842	Remote Similarity	NPD8296	Approved
0.6842	Remote Similarity	NPD8380	Approved
0.6842	Remote Similarity	NPD8378	Approved
0.6842	Remote Similarity	NPD8379	Approved
0.6842	Remote Similarity	NPD8335	Approved
0.6837	Remote Similarity	NPD46	Approved
0.6837	Remote Similarity	NPD7838	Discovery
0.6837	Remote Similarity	NPD6698	Approved
0.6778	Remote Similarity	NPD6933	Approved
0.6768	Remote Similarity	NPD7637	Suspended
0.6765	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6735	Remote Similarity	NPD5328	Approved
0.6731	Remote Similarity	NPD4159	Approved
0.6702	Remote Similarity	NPD3667	Approved
0.67	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.66	Remote Similarity	NPD6079	Approved
0.6598	Remote Similarity	NPD7334	Approved
0.6598	Remote Similarity	NPD6684	Approved
0.6598	Remote Similarity	NPD6409	Approved
0.6598	Remote Similarity	NPD7146	Approved
0.6598	Remote Similarity	NPD5330	Approved
0.6598	Remote Similarity	NPD7521	Approved
0.6593	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7319	Approved
0.6577	Remote Similarity	NPD8297	Approved
0.6574	Remote Similarity	NPD5697	Approved
0.6574	Remote Similarity	NPD5701	Approved
0.6569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6051	Approved
0.6562	Remote Similarity	NPD4786	Approved
0.6562	Remote Similarity	NPD3666	Approved
0.6562	Remote Similarity	NPD3665	Phase 1
0.6562	Remote Similarity	NPD3133	Approved
0.6559	Remote Similarity	NPD7645	Phase 2
0.6556	Remote Similarity	NPD6926	Approved
0.6556	Remote Similarity	NPD6924	Approved
0.6552	Remote Similarity	NPD7503	Approved
0.6535	Remote Similarity	NPD4202	Approved
0.6518	Remote Similarity	NPD4632	Approved
0.6514	Remote Similarity	NPD7320	Approved
0.6514	Remote Similarity	NPD6881	Approved
0.6514	Remote Similarity	NPD6899	Approved
0.6514	Remote Similarity	NPD6011	Approved
0.65	Remote Similarity	NPD5785	Approved
0.6489	Remote Similarity	NPD7525	Registered
0.6484	Remote Similarity	NPD6942	Approved
0.6484	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD7900	Approved
0.6471	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6903	Approved
0.6465	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6695	Phase 3
0.6455	Remote Similarity	NPD6013	Approved
0.6455	Remote Similarity	NPD6372	Approved
0.6455	Remote Similarity	NPD6012	Approved
0.6455	Remote Similarity	NPD6014	Approved
0.6455	Remote Similarity	NPD6373	Approved
0.6442	Remote Similarity	NPD6083	Phase 2
0.6442	Remote Similarity	NPD6084	Phase 2
0.6436	Remote Similarity	NPD8035	Phase 2
0.6436	Remote Similarity	NPD6411	Approved
0.6436	Remote Similarity	NPD8034	Phase 2
0.6396	Remote Similarity	NPD6371	Approved
0.6396	Remote Similarity	NPD7102	Approved
0.6396	Remote Similarity	NPD7290	Approved
0.6396	Remote Similarity	NPD6883	Approved
0.6395	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6929	Approved
0.6381	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD3573	Approved
0.6364	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5222	Approved
0.6346	Remote Similarity	NPD5221	Approved
0.6346	Remote Similarity	NPD4697	Phase 3
0.6339	Remote Similarity	NPD8130	Phase 1
0.6339	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6617	Approved
0.6339	Remote Similarity	NPD6847	Approved
0.6339	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6649	Approved
0.6339	Remote Similarity	NPD6869	Approved
0.6333	Remote Similarity	NPD7152	Approved
0.6333	Remote Similarity	NPD7150	Approved
0.6333	Remote Similarity	NPD7151	Approved
0.6327	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD6931	Approved
0.6316	Remote Similarity	NPD6930	Phase 2
0.6316	Remote Similarity	NPD7509	Discontinued
0.6306	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8264	Approved
0.63	Remote Similarity	NPD5737	Approved
0.63	Remote Similarity	NPD6672	Approved
0.6292	Remote Similarity	NPD6922	Approved
0.6292	Remote Similarity	NPD6923	Approved
0.6286	Remote Similarity	NPD5173	Approved
0.6286	Remote Similarity	NPD4755	Approved
0.6283	Remote Similarity	NPD6882	Approved
0.6277	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5693	Phase 1
0.6273	Remote Similarity	NPD6412	Phase 2
0.6263	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD5695	Phase 3
0.6238	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6101	Approved
0.6228	Remote Similarity	NPD8133	Approved
0.6226	Remote Similarity	NPD5696	Approved
0.6222	Remote Similarity	NPD7143	Approved
0.6222	Remote Similarity	NPD7144	Approved
0.6207	Remote Similarity	NPD6009	Approved
0.6204	Remote Similarity	NPD5211	Phase 2
0.62	Remote Similarity	NPD7750	Discontinued
0.62	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5209	Approved
0.6182	Remote Similarity	NPD6008	Approved
0.617	Remote Similarity	NPD6925	Approved
0.617	Remote Similarity	NPD5776	Phase 2
0.6168	Remote Similarity	NPD5285	Approved
0.6168	Remote Similarity	NPD4696	Approved
0.6168	Remote Similarity	NPD4700	Approved
0.6168	Remote Similarity	NPD5286	Approved
0.6162	Remote Similarity	NPD1696	Phase 3
0.6146	Remote Similarity	NPD7332	Phase 2
0.6146	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4695	Discontinued
0.6146	Remote Similarity	NPD7514	Phase 3
0.6134	Remote Similarity	NPD5983	Phase 2
0.6129	Remote Similarity	NPD8039	Approved
0.6126	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5362	Discontinued
0.6122	Remote Similarity	NPD7154	Phase 3
0.6121	Remote Similarity	NPD6868	Approved
0.6121	Remote Similarity	NPD6274	Approved
0.6111	Remote Similarity	NPD5223	Approved
0.6105	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7145	Approved
0.61	Remote Similarity	NPD4519	Discontinued
0.61	Remote Similarity	NPD4623	Approved
0.6095	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5141	Approved
0.6082	Remote Similarity	NPD6902	Approved
0.6078	Remote Similarity	NPD4753	Phase 2
0.6075	Remote Similarity	NPD5290	Discontinued
0.6068	Remote Similarity	NPD6317	Approved
0.6061	Remote Similarity	NPD3668	Phase 3
0.6055	Remote Similarity	NPD5226	Approved
0.6055	Remote Similarity	NPD4633	Approved
0.6055	Remote Similarity	NPD5224	Approved
0.6055	Remote Similarity	NPD5225	Approved
0.6042	Remote Similarity	NPD4195	Approved
0.6036	Remote Similarity	NPD6640	Phase 3
0.6033	Remote Similarity	NPD7604	Phase 2
0.6033	Remote Similarity	NPD8328	Phase 3
0.602	Remote Similarity	NPD4223	Phase 3
0.602	Remote Similarity	NPD4221	Approved
0.6017	Remote Similarity	NPD6313	Approved
0.6017	Remote Similarity	NPD6335	Approved
0.6017	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD6932	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