NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.11
Volume:	276.095
LogP:	2.884
LogD:	3.118
LogS:	-3.316
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	2.241
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.734
MDCK Permeability:	1.8635739252204075e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.738

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	99.16886901855469%
Volume Distribution (VD):	0.615
Pgp-substrate:	1.2358537912368774%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.87
CYP2C19-substrate:	0.156
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.836
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.512
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	10.817
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.942
Carcinogencity:	0.728
Eye Corrosion:	0.013
Eye Irritation:	0.939
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC60885

Natural Product ID:	NPC60885
*Common Name:**	Hydroxyobustyrene
IUPAC Name:	3-methoxy-4-[(E)-3-phenylprop-2-enyl]benzene-1,2-diol
Synonyms:	Hydroxyobustyrene
Standard InCHIKey:	WGXMQVRYJCAUFL-VMPITWQZSA-N
Standard InCHI:	InChI=1S/C16H16O3/c1-19-16-13(10-11-14(17)15(16)18)9-5-8-12-6-3-2-4-7-12/h2-8,10-11,17-18H,9H2,1H3/b8-5+
SMILES:	COc1c(C/C=C/c2ccccc2)ccc(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL243672
PubChem CID:	11777169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14114	Dalbergia parviflora	Species	Fabaceae	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
Others	16

Activity Type	# Activity
Cell Line	12
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Survival	=	60.0	%	PMID[570441]
NPT80	Cell Line	Raji	Homo sapiens	Survival	>	80.0	%	PMID[570441]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[570442]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[570442]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.1	uM	PMID[570442]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	10.2	%	PMID[570441]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	41.3	%	PMID[570441]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	71.0	%	PMID[570441]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	100.0	%	PMID[570441]

☑ 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 NPC60885 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	393
0.1-0.2	1895
0.2-0.3	6221
0.3-0.4	13163
0.4-0.5	3590
0.5-0.6	4168
0.6-0.7	7238
0.7-0.8	4542
0.8-0.85	771
0.85-0.9	475
0.9-0.95	187
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234400
0.9916	High Similarity	NPC44748
0.9916	High Similarity	NPC28730
0.9916	High Similarity	NPC78974
0.9916	High Similarity	NPC214406
0.9916	High Similarity	NPC223136
0.9916	High Similarity	NPC18924
0.9916	High Similarity	NPC103823
0.9833	High Similarity	NPC169474
0.9833	High Similarity	NPC159968
0.9833	High Similarity	NPC74817
0.9833	High Similarity	NPC124452
0.9833	High Similarity	NPC236791
0.9833	High Similarity	NPC293054
0.9833	High Similarity	NPC282000
0.9833	High Similarity	NPC82679
0.9833	High Similarity	NPC246620
0.9833	High Similarity	NPC324112
0.9832	High Similarity	NPC82483
0.9832	High Similarity	NPC265483
0.9832	High Similarity	NPC299584
0.9672	High Similarity	NPC58164
0.9672	High Similarity	NPC10225
0.9667	High Similarity	NPC221077
0.9667	High Similarity	NPC251855
0.9667	High Similarity	NPC57490
0.9667	High Similarity	NPC208950
0.9667	High Similarity	NPC233410
0.9667	High Similarity	NPC116907
0.9667	High Similarity	NPC117214
0.9667	High Similarity	NPC203133
0.9667	High Similarity	NPC193544
0.9667	High Similarity	NPC475169
0.9667	High Similarity	NPC298757
0.9667	High Similarity	NPC472093
0.9667	High Similarity	NPC105925
0.9667	High Similarity	NPC17943
0.9664	High Similarity	NPC95168
0.9593	High Similarity	NPC234488
0.9593	High Similarity	NPC299221
0.9593	High Similarity	NPC311680
0.9593	High Similarity	NPC126836
0.9593	High Similarity	NPC51840
0.959	High Similarity	NPC154866
0.959	High Similarity	NPC28765
0.958	High Similarity	NPC262253
0.958	High Similarity	NPC41562
0.958	High Similarity	NPC71579
0.958	High Similarity	NPC473411
0.9516	High Similarity	NPC474356
0.9516	High Similarity	NPC12275
0.9516	High Similarity	NPC45715
0.9512	High Similarity	NPC212015
0.9508	High Similarity	NPC252131
0.9508	High Similarity	NPC266555
0.9508	High Similarity	NPC210355
0.9508	High Similarity	NPC236760
0.9508	High Similarity	NPC127587
0.95	High Similarity	NPC282496
0.95	High Similarity	NPC197757
0.95	High Similarity	NPC136319
0.95	High Similarity	NPC121115
0.95	High Similarity	NPC228922
0.95	High Similarity	NPC233526
0.9496	High Similarity	NPC75713
0.944	High Similarity	NPC6451
0.9431	High Similarity	NPC98631
0.9431	High Similarity	NPC470213
0.9431	High Similarity	NPC206615
0.9431	High Similarity	NPC266691
0.9431	High Similarity	NPC186843
0.9426	High Similarity	NPC223953
0.9426	High Similarity	NPC76451
0.9421	High Similarity	NPC206487
0.9421	High Similarity	NPC122792
0.9421	High Similarity	NPC5796
0.9421	High Similarity	NPC228972
0.9412	High Similarity	NPC166759
0.9407	High Similarity	NPC20674
0.9365	High Similarity	NPC471391
0.9365	High Similarity	NPC475840
0.9365	High Similarity	NPC471390
0.9365	High Similarity	NPC229442
0.9365	High Similarity	NPC168059
0.9365	High Similarity	NPC32778
0.936	High Similarity	NPC232275
0.9355	High Similarity	NPC190144
0.9355	High Similarity	NPC476968
0.9355	High Similarity	NPC170844
0.9328	High Similarity	NPC474565
0.9328	High Similarity	NPC232084
0.9328	High Similarity	NPC10932
0.9328	High Similarity	NPC247364
0.9328	High Similarity	NPC61516
0.9291	High Similarity	NPC317380
0.9286	High Similarity	NPC86655
0.9286	High Similarity	NPC202762
0.9286	High Similarity	NPC127624
0.928	High Similarity	NPC91291
0.928	High Similarity	NPC192687
0.928	High Similarity	NPC214860
0.928	High Similarity	NPC224157
0.928	High Similarity	NPC472338
0.9262	High Similarity	NPC183446
0.9244	High Similarity	NPC226629
0.9237	High Similarity	NPC259638
0.9219	High Similarity	NPC108198
0.9219	High Similarity	NPC474206
0.9219	High Similarity	NPC158142
0.9219	High Similarity	NPC472337
0.9219	High Similarity	NPC94750
0.9219	High Similarity	NPC69029
0.9219	High Similarity	NPC200557
0.9219	High Similarity	NPC121812
0.9219	High Similarity	NPC313081
0.9219	High Similarity	NPC112246
0.9219	High Similarity	NPC10314
0.9219	High Similarity	NPC256262
0.9219	High Similarity	NPC294884
0.9219	High Similarity	NPC112939
0.9219	High Similarity	NPC470356
0.9213	High Similarity	NPC36661
0.9206	High Similarity	NPC472597
0.9206	High Similarity	NPC474017
0.9206	High Similarity	NPC470096
0.9206	High Similarity	NPC15543
0.9206	High Similarity	NPC470095
0.92	High Similarity	NPC469963
0.92	High Similarity	NPC469951
0.92	High Similarity	NPC45824
0.9194	High Similarity	NPC242032
0.9194	High Similarity	NPC470699
0.918	High Similarity	NPC84086
0.9174	High Similarity	NPC285289
0.9174	High Similarity	NPC49341
0.9153	High Similarity	NPC193067
0.9147	High Similarity	NPC143139
0.9147	High Similarity	NPC16435
0.9147	High Similarity	NPC248727
0.9147	High Similarity	NPC265433
0.9147	High Similarity	NPC202846
0.9147	High Similarity	NPC227503
0.9147	High Similarity	NPC230734
0.9147	High Similarity	NPC474639
0.9147	High Similarity	NPC270456
0.9147	High Similarity	NPC306441
0.9147	High Similarity	NPC472334
0.9147	High Similarity	NPC162659
0.9147	High Similarity	NPC472336
0.9141	High Similarity	NPC7515
0.9141	High Similarity	NPC289258
0.9141	High Similarity	NPC276026
0.9141	High Similarity	NPC206737
0.9141	High Similarity	NPC56764
0.9141	High Similarity	NPC209199
0.9141	High Similarity	NPC106215
0.9141	High Similarity	NPC125649
0.9141	High Similarity	NPC469659
0.9141	High Similarity	NPC555
0.9141	High Similarity	NPC188378
0.9134	High Similarity	NPC160991
0.9134	High Similarity	NPC16208
0.9134	High Similarity	NPC184447
0.9134	High Similarity	NPC7903
0.9134	High Similarity	NPC201587
0.9134	High Similarity	NPC35932
0.9134	High Similarity	NPC253105
0.9113	High Similarity	NPC181361
0.9113	High Similarity	NPC112596
0.9098	High Similarity	NPC474864
0.9098	High Similarity	NPC135414
0.9098	High Similarity	NPC246967
0.9091	High Similarity	NPC102639
0.9083	High Similarity	NPC475961
0.9083	High Similarity	NPC254625
0.9077	High Similarity	NPC6262
0.9077	High Similarity	NPC107551
0.9077	High Similarity	NPC276490
0.9077	High Similarity	NPC211549
0.9077	High Similarity	NPC474282
0.9077	High Similarity	NPC272157
0.9077	High Similarity	NPC326797
0.9077	High Similarity	NPC102904
0.9077	High Similarity	NPC90615
0.9077	High Similarity	NPC176051
0.9077	High Similarity	NPC73535
0.9077	High Similarity	NPC103976
0.9077	High Similarity	NPC56329
0.9077	High Similarity	NPC242715
0.9077	High Similarity	NPC201145
0.9077	High Similarity	NPC25111
0.9076	High Similarity	NPC33270
0.9076	High Similarity	NPC69261
0.9076	High Similarity	NPC474933
0.907	High Similarity	NPC180602
0.907	High Similarity	NPC260898
0.907	High Similarity	NPC241241
0.907	High Similarity	NPC214853
0.907	High Similarity	NPC234333
0.907	High Similarity	NPC61946

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 NPC60885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	996
0.2-0.3	1859
0.3-0.4	2731
0.4-0.5	1562
0.5-0.6	881
0.6-0.7	611
0.7-0.8	116
0.8-0.85	10
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD3027	Phase 3
0.8968	High Similarity	NPD1529	Clinical (unspecified phase)
0.8889	High Similarity	NPD1530	Clinical (unspecified phase)
0.8837	High Similarity	NPD1613	Approved
0.8837	High Similarity	NPD1612	Clinical (unspecified phase)
0.874	High Similarity	NPD3018	Phase 2
0.8729	High Similarity	NPD228	Approved
0.8571	High Similarity	NPD2982	Phase 2
0.8571	High Similarity	NPD2983	Phase 2
0.8492	Intermediate Similarity	NPD2981	Phase 2
0.8387	Intermediate Similarity	NPD1548	Phase 1
0.8281	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD5283	Phase 1
0.8268	Intermediate Similarity	NPD1610	Phase 2
0.8244	Intermediate Similarity	NPD4908	Phase 1
0.812	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2801	Approved
0.8045	Intermediate Similarity	NPD4625	Phase 3
0.8043	Intermediate Similarity	NPD3540	Phase 1
0.8014	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD4749	Approved
0.8	Intermediate Similarity	NPD1558	Phase 1
0.7973	Intermediate Similarity	NPD3882	Suspended
0.7971	Intermediate Similarity	NPD3539	Phase 1
0.7951	Intermediate Similarity	NPD3021	Approved
0.7951	Intermediate Similarity	NPD3022	Approved
0.7881	Intermediate Similarity	NPD1242	Phase 1
0.7846	Intermediate Similarity	NPD422	Phase 1
0.7838	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1511	Approved
0.782	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD940	Approved
0.7815	Intermediate Similarity	NPD846	Approved
0.7761	Intermediate Similarity	NPD2861	Phase 2
0.774	Intermediate Similarity	NPD1653	Approved
0.7737	Intermediate Similarity	NPD3620	Phase 2
0.7737	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD5536	Phase 2
0.7727	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1512	Approved
0.7721	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4357	Discontinued
0.7664	Intermediate Similarity	NPD2674	Phase 3
0.7661	Intermediate Similarity	NPD4750	Phase 3
0.7632	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1357	Approved
0.7613	Intermediate Similarity	NPD6166	Phase 2
0.7613	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4060	Phase 1
0.7609	Intermediate Similarity	NPD1240	Approved
0.7581	Intermediate Similarity	NPD2684	Approved
0.7578	Intermediate Similarity	NPD6671	Approved
0.7576	Intermediate Similarity	NPD3705	Approved
0.7569	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3060	Approved
0.755	Intermediate Similarity	NPD3817	Phase 2
0.7533	Intermediate Similarity	NPD37	Approved
0.7517	Intermediate Similarity	NPD4675	Approved
0.7517	Intermediate Similarity	NPD7124	Phase 2
0.7517	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7468	Intermediate Similarity	NPD7054	Approved
0.7464	Intermediate Similarity	NPD3144	Approved
0.7464	Intermediate Similarity	NPD3145	Approved
0.7458	Intermediate Similarity	NPD2934	Approved
0.7458	Intermediate Similarity	NPD9296	Approved
0.7458	Intermediate Similarity	NPD2933	Approved
0.7451	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4005	Discontinued
0.7448	Intermediate Similarity	NPD2219	Phase 1
0.7447	Intermediate Similarity	NPD6111	Discontinued
0.7444	Intermediate Similarity	NPD1091	Approved
0.7431	Intermediate Similarity	NPD5177	Phase 3
0.7421	Intermediate Similarity	NPD7074	Phase 3
0.7421	Intermediate Similarity	NPD7472	Approved
0.7419	Intermediate Similarity	NPD7199	Phase 2
0.7413	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD2922	Phase 1
0.7405	Intermediate Similarity	NPD3818	Discontinued
0.7395	Intermediate Similarity	NPD2859	Approved
0.7395	Intermediate Similarity	NPD2860	Approved
0.7394	Intermediate Similarity	NPD1510	Phase 2
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD9494	Approved
0.7365	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD943	Approved
0.7355	Intermediate Similarity	NPD3020	Approved
0.7347	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7843	Approved
0.7343	Intermediate Similarity	NPD6099	Approved
0.7343	Intermediate Similarity	NPD6100	Approved
0.7342	Intermediate Similarity	NPD7473	Discontinued
0.7338	Intermediate Similarity	NPD4055	Discovery
0.7325	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4236	Phase 3
0.731	Intermediate Similarity	NPD4237	Approved
0.7308	Intermediate Similarity	NPD7157	Approved
0.7305	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD6584	Phase 3
0.7297	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7447	Phase 1
0.7296	Intermediate Similarity	NPD7228	Approved
0.7293	Intermediate Similarity	NPD4626	Approved
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.728	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD6797	Phase 2
0.7255	Intermediate Similarity	NPD1465	Phase 2
0.7244	Intermediate Similarity	NPD5451	Approved
0.7241	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2238	Phase 2
0.723	Intermediate Similarity	NPD7213	Phase 3
0.723	Intermediate Similarity	NPD6799	Approved
0.723	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7222	Intermediate Similarity	NPD7251	Discontinued
0.7214	Intermediate Similarity	NPD5109	Approved
0.7214	Intermediate Similarity	NPD5718	Phase 2
0.7214	Intermediate Similarity	NPD5111	Phase 2
0.7214	Intermediate Similarity	NPD5110	Phase 2
0.7195	Intermediate Similarity	NPD8054	Approved
0.7195	Intermediate Similarity	NPD8053	Approved
0.7192	Intermediate Similarity	NPD1652	Phase 2
0.7192	Intermediate Similarity	NPD6674	Discontinued
0.7181	Intermediate Similarity	NPD1424	Approved
0.7181	Intermediate Similarity	NPD4123	Phase 3
0.7178	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7808	Phase 3
0.7176	Intermediate Similarity	NPD709	Approved
0.7172	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5846	Approved
0.7164	Intermediate Similarity	NPD6516	Phase 2
0.7161	Intermediate Similarity	NPD6788	Approved
0.7153	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2978	Approved
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD2977	Approved
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD4097	Suspended
0.7133	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2230	Approved
0.7132	Intermediate Similarity	NPD2232	Approved
0.7132	Intermediate Similarity	NPD2233	Approved
0.7124	Intermediate Similarity	NPD5090	Approved
0.7124	Intermediate Similarity	NPD5089	Approved
0.7123	Intermediate Similarity	NPD1549	Phase 2
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7107	Intermediate Similarity	NPD844	Approved
0.7105	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2796	Approved
0.7097	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2677	Approved
0.7095	Intermediate Similarity	NPD5241	Discontinued
0.7095	Intermediate Similarity	NPD6190	Approved
0.7092	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD4536	Approved
0.7083	Intermediate Similarity	NPD4538	Approved
0.7083	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6583	Phase 3
0.708	Intermediate Similarity	NPD6582	Phase 2
0.7075	Intermediate Similarity	NPD4162	Approved
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2668	Approved
0.7037	Intermediate Similarity	NPD2667	Approved
0.7037	Intermediate Similarity	NPD1778	Approved
0.7032	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6696	Suspended
0.7027	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6331	Phase 2
0.7025	Intermediate Similarity	NPD5494	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5297	Approved
0.6987	Remote Similarity	NPD2560	Approved
0.6987	Remote Similarity	NPD2563	Approved
0.6986	Remote Similarity	NPD1551	Phase 2
0.6985	Remote Similarity	NPD3496	Discontinued
0.6985	Remote Similarity	NPD3847	Discontinued
0.6978	Remote Similarity	NPD3053	Approved
0.6978	Remote Similarity	NPD2797	Approved
0.6978	Remote Similarity	NPD3055	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