NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.949
LogD:	1.889
LogS:	-2.37
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	4.235
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:	-4.63
MDCK Permeability:	2.3905880880192854e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.497
Plasma Protein Binding (PPB):	82.52962493896484%
Volume Distribution (VD):	1.709
Pgp-substrate:	18.392009735107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.598

ADMET: Excretion

Clearance (CL):	8.896
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.507
AMES Toxicity:	0.633
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.966
Carcinogencity:	0.886
Eye Corrosion:	0.158
Eye Irritation:	0.577
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC266159

Natural Product ID:	NPC266159
*Common Name:**	11Beta-13-Dihydroxanthatin
IUPAC Name:	(3S,3aR,7S,8aS)-3,7-dimethyl-6-[(E)-3-oxobut-1-enyl]-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-2-one
Synonyms:
Standard InCHIKey:	OJOBWKNNIJPJRN-FXSQWFEKSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,11,13-14H,7-8H2,1-3H3/b5-4+/t9-,11-,13+,14-/m0/s1
SMILES:	C[C@H]1C[C@H]2[C@H](CC=C1/C=C/C(=O)C)[C@H](C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594244
PubChem CID:	11379652
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:0000502] Xanthanolides

*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
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17612	Xanthium sibiricum	Species	Asteraceae	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[494916]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	>	35000.0	nM	PMID[494916]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[494916]

☑ 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 NPC266159 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	187
0.1-0.2	1061
0.2-0.3	6433
0.3-0.4	15849
0.4-0.5	9979
0.5-0.6	6335
0.6-0.7	2460
0.7-0.8	338
0.8-0.85	37
0.85-0.9	9
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472967
0.9324	High Similarity	NPC63649
0.9324	High Similarity	NPC472965
0.9324	High Similarity	NPC264227
0.9296	High Similarity	NPC472956
0.9143	High Similarity	NPC296522
0.9143	High Similarity	NPC144511
0.8919	High Similarity	NPC472959
0.88	High Similarity	NPC15975
0.88	High Similarity	NPC195785
0.8784	High Similarity	NPC138408
0.8784	High Similarity	NPC226669
0.8784	High Similarity	NPC193351
0.875	High Similarity	NPC472955
0.8553	High Similarity	NPC65603
0.8462	Intermediate Similarity	NPC302426
0.84	Intermediate Similarity	NPC469643
0.84	Intermediate Similarity	NPC469641
0.84	Intermediate Similarity	NPC472966
0.8375	Intermediate Similarity	NPC39588
0.8356	Intermediate Similarity	NPC199557
0.8354	Intermediate Similarity	NPC39411
0.8354	Intermediate Similarity	NPC255580
0.8354	Intermediate Similarity	NPC42470
0.8333	Intermediate Similarity	NPC182550
0.8312	Intermediate Similarity	NPC476794
0.8312	Intermediate Similarity	NPC470240
0.8289	Intermediate Similarity	NPC155587
0.8228	Intermediate Similarity	NPC69271
0.8228	Intermediate Similarity	NPC74673
0.8205	Intermediate Similarity	NPC472960
0.8205	Intermediate Similarity	NPC128276
0.8171	Intermediate Similarity	NPC161957
0.8171	Intermediate Similarity	NPC33570
0.8171	Intermediate Similarity	NPC21471
0.8133	Intermediate Similarity	NPC288667
0.8125	Intermediate Similarity	NPC25684
0.8125	Intermediate Similarity	NPC35089
0.8125	Intermediate Similarity	NPC281949
0.8125	Intermediate Similarity	NPC301477
0.8125	Intermediate Similarity	NPC10276
0.8101	Intermediate Similarity	NPC470239
0.8101	Intermediate Similarity	NPC470244
0.8077	Intermediate Similarity	NPC187568
0.8077	Intermediate Similarity	NPC41780
0.8077	Intermediate Similarity	NPC57744
0.8072	Intermediate Similarity	NPC107787
0.8049	Intermediate Similarity	NPC472957
0.8049	Intermediate Similarity	NPC472958
0.8049	Intermediate Similarity	NPC115786
0.8049	Intermediate Similarity	NPC165287
0.8	Intermediate Similarity	NPC276356
0.7975	Intermediate Similarity	NPC299235
0.7952	Intermediate Similarity	NPC78089
0.7949	Intermediate Similarity	NPC235906
0.7927	Intermediate Similarity	NPC318468
0.7922	Intermediate Similarity	NPC476355
0.7901	Intermediate Similarity	NPC471325
0.7901	Intermediate Similarity	NPC470241
0.7901	Intermediate Similarity	NPC475665
0.7895	Intermediate Similarity	NPC129665
0.7895	Intermediate Similarity	NPC163003
0.7875	Intermediate Similarity	NPC178277
0.7857	Intermediate Similarity	NPC70555
0.7857	Intermediate Similarity	NPC104961
0.7857	Intermediate Similarity	NPC70422
0.7821	Intermediate Similarity	NPC324762
0.7805	Intermediate Similarity	NPC173609
0.7792	Intermediate Similarity	NPC269206
0.7792	Intermediate Similarity	NPC58956
0.7792	Intermediate Similarity	NPC295633
0.7778	Intermediate Similarity	NPC223904
0.7765	Intermediate Similarity	NPC237540
0.7763	Intermediate Similarity	NPC475310
0.7738	Intermediate Similarity	NPC165162
0.7738	Intermediate Similarity	NPC177932
0.7738	Intermediate Similarity	NPC125290
0.7733	Intermediate Similarity	NPC476614
0.7722	Intermediate Similarity	NPC123360
0.7711	Intermediate Similarity	NPC215294
0.7701	Intermediate Similarity	NPC62815
0.7701	Intermediate Similarity	NPC253144
0.7692	Intermediate Similarity	NPC294434
0.7692	Intermediate Similarity	NPC15499
0.7692	Intermediate Similarity	NPC140287
0.7692	Intermediate Similarity	NPC259599
0.7692	Intermediate Similarity	NPC117746
0.7674	Intermediate Similarity	NPC215831
0.7654	Intermediate Similarity	NPC469690
0.7654	Intermediate Similarity	NPC617
0.7654	Intermediate Similarity	NPC270126
0.7632	Intermediate Similarity	NPC477448
0.7632	Intermediate Similarity	NPC5714
0.7632	Intermediate Similarity	NPC477449
0.7625	Intermediate Similarity	NPC180290
0.7619	Intermediate Similarity	NPC139566
0.7619	Intermediate Similarity	NPC156485
0.7614	Intermediate Similarity	NPC284185
0.7614	Intermediate Similarity	NPC70595
0.7614	Intermediate Similarity	NPC150978
0.7614	Intermediate Similarity	NPC74103
0.7614	Intermediate Similarity	NPC123177
0.7595	Intermediate Similarity	NPC244166
0.759	Intermediate Similarity	NPC89555
0.7586	Intermediate Similarity	NPC52198
0.7586	Intermediate Similarity	NPC73995
0.7586	Intermediate Similarity	NPC117405
0.7586	Intermediate Similarity	NPC268298
0.7564	Intermediate Similarity	NPC470237
0.7561	Intermediate Similarity	NPC304795
0.7558	Intermediate Similarity	NPC478144
0.7531	Intermediate Similarity	NPC108816
0.7531	Intermediate Similarity	NPC267231
0.7531	Intermediate Similarity	NPC93763
0.7531	Intermediate Similarity	NPC192006
0.7531	Intermediate Similarity	NPC35574
0.7529	Intermediate Similarity	NPC235792
0.75	Intermediate Similarity	NPC218477
0.75	Intermediate Similarity	NPC129419
0.75	Intermediate Similarity	NPC474842
0.75	Intermediate Similarity	NPC229252
0.75	Intermediate Similarity	NPC475965
0.75	Intermediate Similarity	NPC469372
0.75	Intermediate Similarity	NPC470256
0.75	Intermediate Similarity	NPC143857
0.75	Intermediate Similarity	NPC473223
0.75	Intermediate Similarity	NPC266119
0.75	Intermediate Similarity	NPC471726
0.75	Intermediate Similarity	NPC474527
0.75	Intermediate Similarity	NPC475947
0.7471	Intermediate Similarity	NPC190718
0.747	Intermediate Similarity	NPC325031
0.747	Intermediate Similarity	NPC141810
0.7468	Intermediate Similarity	NPC320537
0.7468	Intermediate Similarity	NPC143979
0.7468	Intermediate Similarity	NPC167049
0.7468	Intermediate Similarity	NPC469691
0.7467	Intermediate Similarity	NPC154728
0.7467	Intermediate Similarity	NPC126899
0.7467	Intermediate Similarity	NPC304665
0.7444	Intermediate Similarity	NPC477130
0.7444	Intermediate Similarity	NPC477129
0.7444	Intermediate Similarity	NPC167219
0.7444	Intermediate Similarity	NPC56525
0.7442	Intermediate Similarity	NPC67493
0.7442	Intermediate Similarity	NPC38576
0.7442	Intermediate Similarity	NPC234038
0.7442	Intermediate Similarity	NPC279859
0.7439	Intermediate Similarity	NPC469620
0.7439	Intermediate Similarity	NPC89128
0.7436	Intermediate Similarity	NPC29328
0.7416	Intermediate Similarity	NPC300312
0.7416	Intermediate Similarity	NPC111114
0.7416	Intermediate Similarity	NPC261607
0.7412	Intermediate Similarity	NPC196487
0.7412	Intermediate Similarity	NPC30486
0.7412	Intermediate Similarity	NPC96259
0.7412	Intermediate Similarity	NPC14575
0.7412	Intermediate Similarity	NPC141193
0.7407	Intermediate Similarity	NPC141789
0.7407	Intermediate Similarity	NPC7563
0.7407	Intermediate Similarity	NPC208223
0.7407	Intermediate Similarity	NPC116177
0.7407	Intermediate Similarity	NPC97516
0.7407	Intermediate Similarity	NPC171204
0.7407	Intermediate Similarity	NPC474760
0.7407	Intermediate Similarity	NPC320630
0.7407	Intermediate Similarity	NPC476028
0.7403	Intermediate Similarity	NPC473603
0.7403	Intermediate Similarity	NPC476059
0.7381	Intermediate Similarity	NPC178676
0.7381	Intermediate Similarity	NPC471326
0.7381	Intermediate Similarity	NPC221231
0.7381	Intermediate Similarity	NPC85772
0.7375	Intermediate Similarity	NPC469678
0.7375	Intermediate Similarity	NPC469669
0.7375	Intermediate Similarity	NPC255060
0.7375	Intermediate Similarity	NPC475771
0.7363	Intermediate Similarity	NPC90121
0.7363	Intermediate Similarity	NPC193645
0.7363	Intermediate Similarity	NPC48803
0.7363	Intermediate Similarity	NPC275960
0.7361	Intermediate Similarity	NPC143834
0.7356	Intermediate Similarity	NPC478145
0.7349	Intermediate Similarity	NPC474510
0.7349	Intermediate Similarity	NPC73052
0.7349	Intermediate Similarity	NPC293418
0.7349	Intermediate Similarity	NPC290508
0.7349	Intermediate Similarity	NPC281132
0.7349	Intermediate Similarity	NPC469920
0.7349	Intermediate Similarity	NPC6823
0.7333	Intermediate Similarity	NPC474329
0.7333	Intermediate Similarity	NPC474304
0.7326	Intermediate Similarity	NPC197903
0.7326	Intermediate Similarity	NPC215364
0.7326	Intermediate Similarity	NPC110405
0.7326	Intermediate Similarity	NPC28887
0.7326	Intermediate Similarity	NPC99395
0.7326	Intermediate Similarity	NPC470177
0.7317	Intermediate Similarity	NPC11796

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 NPC266159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1568
0.2-0.3	4052
0.3-0.4	2302
0.4-0.5	648
0.5-0.6	315
0.6-0.7	81
0.7-0.8	9
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
0.7738	Intermediate Similarity	NPD1694	Approved
0.7381	Intermediate Similarity	NPD5209	Approved
0.7363	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1695	Approved
0.7126	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5363	Approved
0.7111	Intermediate Similarity	NPD5207	Approved
0.7059	Intermediate Similarity	NPD5369	Approved
0.7045	Intermediate Similarity	NPD7146	Approved
0.7045	Intermediate Similarity	NPD6684	Approved
0.7045	Intermediate Similarity	NPD7521	Approved
0.7045	Intermediate Similarity	NPD7334	Approved
0.7045	Intermediate Similarity	NPD5330	Approved
0.7045	Intermediate Similarity	NPD6409	Approved
0.6977	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6435	Approved
0.6951	Remote Similarity	NPD8039	Approved
0.6923	Remote Similarity	NPD5785	Approved
0.6889	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4269	Approved
0.6782	Remote Similarity	NPD4270	Approved
0.6744	Remote Similarity	NPD5368	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7154	Phase 3
0.6705	Remote Similarity	NPD5362	Discontinued
0.6703	Remote Similarity	NPD5737	Approved
0.6703	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.663	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6101	Approved
0.6593	Remote Similarity	NPD3573	Approved
0.6559	Remote Similarity	NPD5692	Phase 3
0.6552	Remote Similarity	NPD4252	Approved
0.6526	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5282	Discontinued
0.6526	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD5284	Approved
0.6489	Remote Similarity	NPD6050	Approved
0.6489	Remote Similarity	NPD5281	Approved
0.6489	Remote Similarity	NPD6411	Approved
0.6484	Remote Similarity	NPD5279	Phase 3
0.6458	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4058	Approved
0.6421	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD5779	Approved
0.6421	Remote Similarity	NPD5778	Approved
0.6395	Remote Similarity	NPD4756	Discovery
0.6375	Remote Similarity	NPD7331	Phase 2
0.6375	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7748	Approved
0.6354	Remote Similarity	NPD6001	Approved
0.6344	Remote Similarity	NPD5208	Approved
0.6327	Remote Similarity	NPD7902	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3618	Phase 1
0.6289	Remote Similarity	NPD5695	Phase 3
0.6286	Remote Similarity	NPD6371	Approved
0.6277	Remote Similarity	NPD6080	Approved
0.6277	Remote Similarity	NPD6904	Approved
0.6277	Remote Similarity	NPD6673	Approved
0.6264	Remote Similarity	NPD3666	Approved
0.6264	Remote Similarity	NPD3133	Approved
0.6264	Remote Similarity	NPD3665	Phase 1
0.6263	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD28	Approved
0.625	Remote Similarity	NPD29	Approved
0.6235	Remote Similarity	NPD4687	Approved
0.6226	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD6698	Approved
0.6211	Remote Similarity	NPD46	Approved
0.6211	Remote Similarity	NPD3672	Approved
0.6211	Remote Similarity	NPD7838	Discovery
0.6211	Remote Similarity	NPD3673	Approved
0.6196	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5276	Approved
0.618	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD4820	Approved
0.618	Remote Similarity	NPD4822	Approved
0.618	Remote Similarity	NPD4821	Approved
0.6176	Remote Similarity	NPD6647	Phase 2
0.6162	Remote Similarity	NPD6084	Phase 2
0.6162	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD6079	Approved
0.6146	Remote Similarity	NPD5693	Phase 1
0.6146	Remote Similarity	NPD7515	Phase 2
0.6136	Remote Similarity	NPD4271	Approved
0.6136	Remote Similarity	NPD4268	Approved
0.6129	Remote Similarity	NPD4249	Approved
0.6129	Remote Similarity	NPD6098	Approved
0.6125	Remote Similarity	NPD3197	Phase 1
0.6122	Remote Similarity	NPD5654	Approved
0.6111	Remote Similarity	NPD4790	Discontinued
0.61	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4225	Approved
0.6095	Remote Similarity	NPD6011	Approved
0.6095	Remote Similarity	NPD6899	Approved
0.6095	Remote Similarity	NPD6881	Approved
0.6081	Remote Similarity	NPD3172	Approved
0.6075	Remote Similarity	NPD6649	Approved
0.6075	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD4691	Approved
0.6064	Remote Similarity	NPD4251	Approved
0.6064	Remote Similarity	NPD4250	Approved
0.6061	Remote Similarity	NPD7839	Suspended
0.6049	Remote Similarity	NPD7341	Phase 2
0.6047	Remote Similarity	NPD5733	Approved
0.6044	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD6014	Approved
0.6038	Remote Similarity	NPD6013	Approved
0.602	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.6	Remote Similarity	NPD3194	Approved
0.6	Remote Similarity	NPD3196	Approved
0.6	Remote Similarity	NPD3195	Phase 2
0.6	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4266	Approved
0.5981	Remote Similarity	NPD7102	Approved
0.5981	Remote Similarity	NPD7290	Approved
0.5981	Remote Similarity	NPD6883	Approved
0.5979	Remote Similarity	NPD7637	Suspended
0.5963	Remote Similarity	NPD7094	Approved
0.5963	Remote Similarity	NPD6858	Approved
0.596	Remote Similarity	NPD4629	Approved
0.596	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD5690	Phase 2
0.5957	Remote Similarity	NPD6422	Discontinued
0.5957	Remote Similarity	NPD5280	Approved
0.5957	Remote Similarity	NPD4694	Approved
0.5952	Remote Similarity	NPD4137	Phase 3
0.5949	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5370	Suspended
0.5938	Remote Similarity	NPD5328	Approved
0.5926	Remote Similarity	NPD6847	Approved
0.5926	Remote Similarity	NPD6617	Approved
0.5926	Remote Similarity	NPD8130	Phase 1
0.5926	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6869	Approved
0.5914	Remote Similarity	NPD4786	Approved
0.5914	Remote Similarity	NPD3668	Phase 3
0.5905	Remote Similarity	NPD5739	Approved
0.5905	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD6675	Approved
0.5905	Remote Similarity	NPD6402	Approved
0.59	Remote Similarity	NPD5221	Approved
0.59	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5222	Approved
0.5888	Remote Similarity	NPD6373	Approved
0.5888	Remote Similarity	NPD6372	Approved
0.5882	Remote Similarity	NPD4747	Approved
0.5882	Remote Similarity	NPD2066	Phase 3
0.5872	Remote Similarity	NPD8297	Approved
0.5872	Remote Similarity	NPD6882	Approved
0.587	Remote Similarity	NPD4221	Approved
0.587	Remote Similarity	NPD4223	Phase 3
0.5865	Remote Similarity	NPD6052	Approved
0.5851	Remote Similarity	NPD1696	Phase 3
0.5849	Remote Similarity	NPD5701	Approved
0.5849	Remote Similarity	NPD6614	Approved
0.5842	Remote Similarity	NPD5173	Approved
0.5833	Remote Similarity	NPD5343	Approved
0.5833	Remote Similarity	NPD2067	Discontinued
0.5816	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7115	Discovery
0.5802	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.58	Remote Similarity	NPD1693	Approved
0.5794	Remote Similarity	NPD7320	Approved
0.5794	Remote Similarity	NPD6686	Approved
0.5789	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD9298	Approved
0.5789	Remote Similarity	NPD4623	Approved
0.5789	Remote Similarity	NPD4519	Discontinued
0.5784	Remote Similarity	NPD7638	Approved
0.5775	Remote Similarity	NPD3174	Discontinued
0.5773	Remote Similarity	NPD4753	Phase 2
0.5761	Remote Similarity	NPD857	Phase 3
0.5758	Remote Similarity	NPD4202	Approved
0.5758	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7641	Discontinued
0.5745	Remote Similarity	NPD4197	Approved
0.5743	Remote Similarity	NPD1989	Approved
0.5743	Remote Similarity	NPD4697	Phase 3
0.5743	Remote Similarity	NPD7732	Phase 3
0.5739	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD1087	Approved
0.5728	Remote Similarity	NPD7639	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