NPASS Compound

Structure

CID236760 OpenBabel06191716032D 21 22 0 0 0 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 1.7321 -1.0000 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 1.7321 0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 11 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 13 17 2 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	304.817
LogP:	3.501
LogD:	3.6
LogS:	-3.745
# Rotatable Bonds:	5
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.243
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	2.02117080334574e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.283
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.82
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	97.80825805664062%
Volume Distribution (VD):	0.942
Pgp-substrate:	1.466844081878662%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.632
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.586

ADMET: Excretion

Clearance (CL):	12.632
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.94
Carcinogencity:	0.098
Eye Corrosion:	0.028
Eye Irritation:	0.939
Respiratory Toxicity:	0.332

Download Data

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

Natural Product: NPC236760

Natural Product ID:	NPC236760
*Common Name:**	Stilbostemin G
IUPAC Name:	5-[2-(3-hydroxy-2-methoxyphenyl)ethyl]-3-methoxy-2-methylphenol
Synonyms:	stilbostemin G
Standard InCHIKey:	DDKZTACJHBROQB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-11-15(19)9-12(10-16(11)20-2)7-8-13-5-4-6-14(18)17(13)21-3/h4-6,9-10,18-19H,7-8H2,1-3H3
SMILES:	Cc1c(cc(CCc2cccc(c2OC)O)cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481450
PubChem CID:	11254745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33266	stemona cf. pierrei gagnep.	Species	Stemonaceae	Eukaryota	n.a.	East Thailand, Sri Sa Ket Province, between Sri Sa Ket and Surin	n.a.	PMID[15679323]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	25800.0	nM	PMID[518267]

☑ 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 NPC236760 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	406
0.1-0.2	1755
0.2-0.3	5498
0.3-0.4	13509
0.4-0.5	3891
0.5-0.6	4359
0.6-0.7	7766
0.7-0.8	4210
0.8-0.85	711
0.85-0.9	381
0.9-0.95	190
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9672	High Similarity	NPC169474
0.9672	High Similarity	NPC159968
0.9672	High Similarity	NPC236791
0.9672	High Similarity	NPC246620
0.9672	High Similarity	NPC282000
0.9672	High Similarity	NPC124452
0.9672	High Similarity	NPC324112
0.9672	High Similarity	NPC293054
0.9672	High Similarity	NPC74817
0.9672	High Similarity	NPC82679
0.9667	High Similarity	NPC95168
0.9667	High Similarity	NPC121115
0.9593	High Similarity	NPC266691
0.959	High Similarity	NPC28730
0.959	High Similarity	NPC18924
0.959	High Similarity	NPC78974
0.959	High Similarity	NPC214406
0.959	High Similarity	NPC103823
0.959	High Similarity	NPC44748
0.959	High Similarity	NPC223136
0.9508	High Similarity	NPC82483
0.9508	High Similarity	NPC116907
0.9508	High Similarity	NPC472093
0.9508	High Similarity	NPC233410
0.9508	High Similarity	NPC234400
0.9508	High Similarity	NPC57490
0.9508	High Similarity	NPC298757
0.9508	High Similarity	NPC117214
0.9508	High Similarity	NPC193544
0.9508	High Similarity	NPC475169
0.9508	High Similarity	NPC265483
0.9508	High Similarity	NPC203133
0.9508	High Similarity	NPC105925
0.9508	High Similarity	NPC60885
0.9508	High Similarity	NPC299584
0.9508	High Similarity	NPC221077
0.9508	High Similarity	NPC251855
0.9508	High Similarity	NPC208950
0.9508	High Similarity	NPC17943
0.95	High Similarity	NPC75713
0.944	High Similarity	NPC126836
0.944	High Similarity	NPC299221
0.944	High Similarity	NPC234488
0.944	High Similarity	NPC311680
0.944	High Similarity	NPC51840
0.9435	High Similarity	NPC154866
0.9435	High Similarity	NPC28765
0.9375	High Similarity	NPC201357
0.9375	High Similarity	NPC255147
0.9375	High Similarity	NPC261873
0.9375	High Similarity	NPC283009
0.9375	High Similarity	NPC281521
0.936	High Similarity	NPC10225
0.936	High Similarity	NPC212015
0.936	High Similarity	NPC58164
0.9355	High Similarity	NPC127587
0.9355	High Similarity	NPC266555
0.9355	High Similarity	NPC252131
0.9344	High Similarity	NPC282496
0.9344	High Similarity	NPC197757
0.9344	High Similarity	NPC228922
0.9344	High Similarity	NPC233526
0.9344	High Similarity	NPC136319
0.9297	High Similarity	NPC103967
0.9291	High Similarity	NPC6451
0.928	High Similarity	NPC186843
0.928	High Similarity	NPC206615
0.928	High Similarity	NPC470213
0.928	High Similarity	NPC98631
0.9274	High Similarity	NPC76451
0.9274	High Similarity	NPC112596
0.9274	High Similarity	NPC223953
0.9262	High Similarity	NPC473411
0.9262	High Similarity	NPC41562
0.9262	High Similarity	NPC71579
0.9262	High Similarity	NPC262253
0.925	High Similarity	NPC184302
0.9231	High Similarity	NPC25111
0.9231	High Similarity	NPC73535
0.9231	High Similarity	NPC272157
0.9231	High Similarity	NPC56329
0.9231	High Similarity	NPC201145
0.9231	High Similarity	NPC90615
0.9231	High Similarity	NPC6262
0.9231	High Similarity	NPC242715
0.9225	High Similarity	NPC294884
0.9225	High Similarity	NPC10314
0.9225	High Similarity	NPC108198
0.9225	High Similarity	NPC69029
0.9225	High Similarity	NPC158142
0.9225	High Similarity	NPC200557
0.9225	High Similarity	NPC313081
0.9219	High Similarity	NPC94236
0.9219	High Similarity	NPC475840
0.9219	High Similarity	NPC269528
0.9219	High Similarity	NPC32778
0.9219	High Similarity	NPC37196
0.9219	High Similarity	NPC36661
0.9213	High Similarity	NPC474356
0.9213	High Similarity	NPC45715
0.9213	High Similarity	NPC232275
0.9213	High Similarity	NPC12275
0.9206	High Similarity	NPC170844
0.9206	High Similarity	NPC476968
0.92	High Similarity	NPC210355
0.9167	High Similarity	NPC190514
0.916	High Similarity	NPC220344
0.916	High Similarity	NPC243996
0.916	High Similarity	NPC132804
0.916	High Similarity	NPC275061
0.9154	High Similarity	NPC300846
0.9154	High Similarity	NPC30632
0.9154	High Similarity	NPC476639
0.9154	High Similarity	NPC114155
0.9154	High Similarity	NPC143139
0.9154	High Similarity	NPC202846
0.9147	High Similarity	NPC317380
0.9147	High Similarity	NPC125649
0.9147	High Similarity	NPC209199
0.9141	High Similarity	NPC86655
0.9141	High Similarity	NPC218884
0.9141	High Similarity	NPC161203
0.9141	High Similarity	NPC127624
0.9141	High Similarity	NPC202762
0.9134	High Similarity	NPC224157
0.9134	High Similarity	NPC192687
0.912	High Similarity	NPC245060
0.9113	High Similarity	NPC206487
0.9113	High Similarity	NPC5796
0.9106	High Similarity	NPC77789
0.9106	High Similarity	NPC18128
0.9106	High Similarity	NPC135414
0.9098	High Similarity	NPC166759
0.9091	High Similarity	NPC295719
0.9091	High Similarity	NPC12668
0.9091	High Similarity	NPC34431
0.9091	High Similarity	NPC308768
0.9091	High Similarity	NPC73505
0.9091	High Similarity	NPC165026
0.9084	High Similarity	NPC230919
0.9084	High Similarity	NPC22902
0.9084	High Similarity	NPC200935
0.9084	High Similarity	NPC266453
0.9083	High Similarity	NPC69261
0.9083	High Similarity	NPC33270
0.9077	High Similarity	NPC241241
0.9077	High Similarity	NPC111655
0.9077	High Similarity	NPC256262
0.9077	High Similarity	NPC474206
0.9077	High Similarity	NPC112939
0.9077	High Similarity	NPC470356
0.9077	High Similarity	NPC94750
0.9077	High Similarity	NPC112246
0.9077	High Similarity	NPC121812
0.9077	High Similarity	NPC134968
0.907	High Similarity	NPC471391
0.907	High Similarity	NPC471390
0.907	High Similarity	NPC229442
0.907	High Similarity	NPC168059
0.9062	High Similarity	NPC15543
0.9062	High Similarity	NPC474017
0.9055	High Similarity	NPC469951
0.9055	High Similarity	NPC190144
0.9055	High Similarity	NPC469963
0.9048	High Similarity	NPC470699
0.9048	High Similarity	NPC242032
0.9048	High Similarity	NPC216836
0.9032	High Similarity	NPC84086
0.9023	High Similarity	NPC472089
0.9016	High Similarity	NPC232084
0.9016	High Similarity	NPC247364
0.9016	High Similarity	NPC10932
0.9016	High Similarity	NPC61516
0.9016	High Similarity	NPC474565
0.9015	High Similarity	NPC105847
0.9015	High Similarity	NPC243759
0.9015	High Similarity	NPC79622
0.9015	High Similarity	NPC29868
0.9015	High Similarity	NPC218131
0.9015	High Similarity	NPC184613
0.9015	High Similarity	NPC212942
0.9008	High Similarity	NPC248727
0.9008	High Similarity	NPC472336
0.9008	High Similarity	NPC472334
0.9008	High Similarity	NPC16435
0.9008	High Similarity	NPC265433
0.9008	High Similarity	NPC306441
0.9008	High Similarity	NPC162659
0.9008	High Similarity	NPC270456
0.9008	High Similarity	NPC476698
0.9008	High Similarity	NPC227503
0.9008	High Similarity	NPC230734
0.9008	High Similarity	NPC474639
0.9	High Similarity	NPC555
0.9	High Similarity	NPC276026
0.9	High Similarity	NPC188378
0.9	High Similarity	NPC206737
0.9	High Similarity	NPC150624
0.9	High Similarity	NPC289258
0.9	High Similarity	NPC160697

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 NPC236760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	970
0.2-0.3	1757
0.3-0.4	2812
0.4-0.5	1597
0.5-0.6	954
0.6-0.7	581
0.7-0.8	107
0.8-0.85	10
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9206	High Similarity	NPD3027	Phase 3
0.8828	High Similarity	NPD1529	Clinical (unspecified phase)
0.875	High Similarity	NPD1530	Clinical (unspecified phase)
0.8702	High Similarity	NPD1613	Approved
0.8702	High Similarity	NPD1612	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3018	Phase 2
0.8333	Intermediate Similarity	NPD4625	Phase 3
0.8295	Intermediate Similarity	NPD2982	Phase 2
0.8295	Intermediate Similarity	NPD2983	Phase 2
0.8295	Intermediate Similarity	NPD4749	Approved
0.8279	Intermediate Similarity	NPD228	Approved
0.8217	Intermediate Similarity	NPD2981	Phase 2
0.8145	Intermediate Similarity	NPD5283	Phase 1
0.812	Intermediate Similarity	NPD4908	Phase 1
0.8106	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD1548	Phase 1
0.7967	Intermediate Similarity	NPD4750	Phase 3
0.7905	Intermediate Similarity	NPD1934	Approved
0.7852	Intermediate Similarity	NPD2801	Approved
0.7823	Intermediate Similarity	NPD3021	Approved
0.7823	Intermediate Similarity	NPD3022	Approved
0.7801	Intermediate Similarity	NPD3540	Phase 1
0.7748	Intermediate Similarity	NPD3882	Suspended
0.7733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3539	Phase 1
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.7626	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1558	Phase 1
0.7626	Intermediate Similarity	NPD3620	Phase 2
0.7613	Intermediate Similarity	NPD6232	Discontinued
0.7612	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6099	Approved
0.7606	Intermediate Similarity	NPD6100	Approved
0.7603	Intermediate Similarity	NPD1511	Approved
0.7597	Intermediate Similarity	NPD6671	Approved
0.755	Intermediate Similarity	NPD37	Approved
0.7541	Intermediate Similarity	NPD846	Approved
0.7541	Intermediate Similarity	NPD940	Approved
0.7518	Intermediate Similarity	NPD2861	Phase 2
0.7518	Intermediate Similarity	NPD1607	Approved
0.7517	Intermediate Similarity	NPD1653	Approved
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD4357	Discontinued
0.7482	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5536	Phase 2
0.7468	Intermediate Similarity	NPD7473	Discontinued
0.7466	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD422	Phase 1
0.7463	Intermediate Similarity	NPD1091	Approved
0.7459	Intermediate Similarity	NPD1242	Phase 1
0.7448	Intermediate Similarity	NPD5177	Phase 3
0.7448	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2922	Phase 1
0.7417	Intermediate Similarity	NPD844	Approved
0.7415	Intermediate Similarity	NPD7124	Phase 2
0.7403	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD4967	Phase 2
0.7397	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD290	Approved
0.7376	Intermediate Similarity	NPD1240	Approved
0.7355	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4005	Discontinued
0.7338	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD9296	Approved
0.7333	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD6674	Discontinued
0.7329	Intermediate Similarity	NPD3060	Approved
0.7329	Intermediate Similarity	NPD7074	Phase 3
0.7325	Intermediate Similarity	NPD7199	Phase 2
0.7323	Intermediate Similarity	NPD2684	Approved
0.7313	Intermediate Similarity	NPD4626	Approved
0.7312	Intermediate Similarity	NPD3818	Discontinued
0.7312	Intermediate Similarity	NPD7228	Approved
0.7305	Intermediate Similarity	NPD2674	Phase 3
0.7303	Intermediate Similarity	NPD4678	Approved
0.7303	Intermediate Similarity	NPD4675	Approved
0.7299	Intermediate Similarity	NPD6696	Suspended
0.7292	Intermediate Similarity	NPD1510	Phase 2
0.7279	Intermediate Similarity	NPD3892	Phase 2
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD7054	Approved
0.7254	Intermediate Similarity	NPD943	Approved
0.7248	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4055	Discovery
0.7241	Intermediate Similarity	NPD1551	Phase 2
0.7239	Intermediate Similarity	NPD1357	Approved
0.7233	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7843	Approved
0.723	Intermediate Similarity	NPD2219	Phase 1
0.7222	Intermediate Similarity	NPD6111	Discontinued
0.7222	Intermediate Similarity	NPD7472	Approved
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD288	Approved
0.72	Intermediate Similarity	NPD7447	Phase 1
0.72	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7157	Approved
0.7192	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5762	Approved
0.7192	Intermediate Similarity	NPD7266	Discontinued
0.7192	Intermediate Similarity	NPD5763	Approved
0.719	Intermediate Similarity	NPD4380	Phase 2
0.7185	Intermediate Similarity	NPD1778	Approved
0.7174	Intermediate Similarity	NPD8651	Approved
0.7165	Intermediate Similarity	NPD968	Approved
0.7161	Intermediate Similarity	NPD1465	Phase 2
0.7153	Intermediate Similarity	NPD2232	Approved
0.7153	Intermediate Similarity	NPD4097	Suspended
0.7153	Intermediate Similarity	NPD2233	Approved
0.7153	Intermediate Similarity	NPD2230	Approved
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7212	Phase 2
0.7133	Intermediate Similarity	NPD7213	Phase 3
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7131	Intermediate Similarity	NPD2860	Approved
0.7131	Intermediate Similarity	NPD2859	Approved
0.7123	Intermediate Similarity	NPD2935	Discontinued
0.7113	Intermediate Similarity	NPD5111	Phase 2
0.7113	Intermediate Similarity	NPD5109	Approved
0.7113	Intermediate Similarity	NPD3145	Approved
0.7113	Intermediate Similarity	NPD3144	Approved
0.7113	Intermediate Similarity	NPD5110	Phase 2
0.7108	Intermediate Similarity	NPD8053	Approved
0.7108	Intermediate Similarity	NPD8054	Approved
0.7099	Intermediate Similarity	NPD7635	Approved
0.7097	Intermediate Similarity	NPD3020	Approved
0.7095	Intermediate Similarity	NPD4237	Approved
0.7095	Intermediate Similarity	NPD4236	Phase 3
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD230	Phase 1
0.7078	Intermediate Similarity	NPD6599	Discontinued
0.7075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6797	Phase 2
0.7071	Intermediate Similarity	NPD6584	Phase 3
0.7068	Intermediate Similarity	NPD709	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7049	Intermediate Similarity	NPD2933	Approved
0.7047	Intermediate Similarity	NPD3750	Approved
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7042	Intermediate Similarity	NPD7095	Approved
0.7032	Intermediate Similarity	NPD5090	Approved
0.7032	Intermediate Similarity	NPD5089	Approved
0.703	Intermediate Similarity	NPD7251	Discontinued
0.7029	Intermediate Similarity	NPD1608	Approved
0.7027	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1549	Phase 2
0.7025	Intermediate Similarity	NPD7075	Discontinued
0.7021	Intermediate Similarity	NPD9494	Approved
0.702	Intermediate Similarity	NPD6799	Approved
0.7013	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3496	Discontinued
0.7006	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD2677	Approved
0.7	Intermediate Similarity	NPD5451	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6988	Remote Similarity	NPD7808	Phase 3
0.6988	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4538	Approved
0.6986	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4536	Approved
0.6985	Remote Similarity	NPD5691	Approved
0.6985	Remote Similarity	NPD1651	Approved
0.6984	Remote Similarity	NPD291	Approved
0.698	Remote Similarity	NPD1652	Phase 2
0.6977	Remote Similarity	NPD2342	Discontinued
0.6974	Remote Similarity	NPD4123	Phase 3
0.6974	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD447	Suspended
0.6966	Remote Similarity	NPD5124	Phase 1
0.6966	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6788	Approved
0.6957	Remote Similarity	NPD1611	Approved
0.6943	Remote Similarity	NPD2977	Approved
0.6943	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2978	Approved
0.6939	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7033	Discontinued
0.6939	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6746	Phase 2
0.6937	Remote Similarity	NPD5494	Approved
0.6934	Remote Similarity	NPD5846	Approved
0.6934	Remote Similarity	NPD6516	Phase 2
0.6933	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4110	Phase 3

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