NPASS Compound

Structure

NPC261597 OpenBabel07101718182D 27 31 0 0 1 0 0 0 0 0999 V2000 -0.8660 -0.5000 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 -3.5686 -0.9945 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 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 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4533 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -5.0468 -0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 3 1 0 0 0 0 2 5 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 25 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 25 1 0 0 0 0 11 18 1 0 0 0 0 11 26 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 1 0 0 0 14 12 1 6 0 0 0 14 27 1 0 0 0 0 15 21 2 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 16 27 1 0 0 0 0 17 19 1 6 0 0 0 18 20 1 6 0 0 0 19 23 1 6 0 0 0 20 17 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	360.043
LogP:	1.753
LogD:	1.181
LogS:	-4.026
# Rotatable Bonds:	1
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	5.632
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:	-5.491
MDCK Permeability:	1.030751627695281e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	83.0107192993164%
Volume Distribution (VD):	1.009
Pgp-substrate:	26.69522476196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.204
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	3.255
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.257
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.078
Carcinogencity:	0.96
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC261597

Natural Product ID:	NPC261597
*Common Name:**	RUQALRIJPOPIRU-ACJWFVACSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RUQALRIJPOPIRU-ACJWFVACSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-17-9-14(12-4-8-25-10-12)27-16(22)19(17,23)7-6-18-11-26-15(21)13(18)3-2-5-20(17,18)24/h2,4-5,8,10,13-14,23-24H,3,6-7,9,11H2,1H3/t13-,14-,17+,18-,19+,20-/m1/s1
SMILES:	C[C@]12C[C@H](c3ccoc3)OC(=O)[C@]1(CC[C@@]13COC(=O)[C@H]1CC=C[C@@]23O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431787
PubChem CID:	72705254
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33426	salvia shannoni	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24099364]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	85.8	ug.mL-1	PMID[508188]
NPT3535	Organism	Entamoeba histolytica HM-1:IMSS	Entamoeba histolytica HM-1:IMSS	IC50	=	79.7	ug.mL-1	PMID[508188]

☑ 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 NPC261597 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	345
0.1-0.2	1251
0.2-0.3	2974
0.3-0.4	4998
0.4-0.5	9619
0.5-0.6	10281
0.6-0.7	9205
0.7-0.8	3462
0.8-0.85	256
0.85-0.9	253
0.9-0.95	45
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC36655
0.9865	High Similarity	NPC214541
0.9865	High Similarity	NPC44675
0.9733	High Similarity	NPC187149
0.9669	High Similarity	NPC475967
0.9474	High Similarity	NPC299038
0.9416	High Similarity	NPC149896
0.9351	High Similarity	NPC477402
0.9338	High Similarity	NPC44577
0.9324	High Similarity	NPC346
0.9295	High Similarity	NPC470940
0.929	High Similarity	NPC82851
0.929	High Similarity	NPC18347
0.9286	High Similarity	NPC477403
0.9276	High Similarity	NPC57998
0.9262	High Similarity	NPC250228
0.9245	High Similarity	NPC160818
0.9245	High Similarity	NPC169299
0.9241	High Similarity	NPC271235
0.9231	High Similarity	NPC469338
0.9231	High Similarity	NPC292389
0.9221	High Similarity	NPC472776
0.9221	High Similarity	NPC472778
0.9221	High Similarity	NPC45101
0.9221	High Similarity	NPC249021
0.9221	High Similarity	NPC472777
0.9177	High Similarity	NPC472651
0.9177	High Similarity	NPC173516
0.9172	High Similarity	NPC469849
0.9172	High Similarity	NPC276551
0.9172	High Similarity	NPC470182
0.9172	High Similarity	NPC271657
0.9167	High Similarity	NPC5079
0.9167	High Similarity	NPC69028
0.9167	High Similarity	NPC200782
0.9167	High Similarity	NPC329938
0.9156	High Similarity	NPC469485
0.915	High Similarity	NPC282445
0.9119	High Similarity	NPC471397
0.9119	High Similarity	NPC472652
0.9114	High Similarity	NPC470875
0.9108	High Similarity	NPC234660
0.9108	High Similarity	NPC477405
0.9108	High Similarity	NPC51568
0.9108	High Similarity	NPC134254
0.9108	High Similarity	NPC39986
0.9108	High Similarity	NPC302369
0.9103	High Similarity	NPC472653
0.9103	High Similarity	NPC335761
0.9097	High Similarity	NPC173544
0.9091	High Similarity	NPC264943
0.9085	High Similarity	NPC469503
0.9085	High Similarity	NPC268905
0.9062	High Similarity	NPC82602
0.906	High Similarity	NPC137295
0.9057	High Similarity	NPC476850
0.9057	High Similarity	NPC476861
0.9057	High Similarity	NPC472775
0.9057	High Similarity	NPC472774
0.9051	High Similarity	NPC123088
0.9045	High Similarity	NPC193798
0.9032	High Similarity	NPC209364
0.9018	High Similarity	NPC478177
0.9013	High Similarity	NPC195325
0.9012	High Similarity	NPC94763
0.9012	High Similarity	NPC236004
0.9	High Similarity	NPC160651
0.8994	High Similarity	NPC472141
0.8987	High Similarity	NPC198047
0.8987	High Similarity	NPC224394
0.8987	High Similarity	NPC472773
0.8987	High Similarity	NPC663
0.8987	High Similarity	NPC472139
0.8987	High Similarity	NPC469846
0.8981	High Similarity	NPC25255
0.8974	High Similarity	NPC286722
0.8961	High Similarity	NPC476201
0.8938	High Similarity	NPC100333
0.8938	High Similarity	NPC472282
0.8933	High Similarity	NPC251865
0.8933	High Similarity	NPC476944
0.8931	High Similarity	NPC476857
0.8931	High Similarity	NPC476856
0.8931	High Similarity	NPC476858
0.8931	High Similarity	NPC476860
0.8924	High Similarity	NPC211777
0.8924	High Similarity	NPC117986
0.8924	High Similarity	NPC472771
0.8924	High Similarity	NPC263432
0.8917	High Similarity	NPC475295
0.8917	High Similarity	NPC473473
0.891	High Similarity	NPC126723
0.891	High Similarity	NPC60973
0.891	High Similarity	NPC107646
0.8903	High Similarity	NPC178932
0.8903	High Similarity	NPC30222
0.8896	High Similarity	NPC18135
0.8889	High Similarity	NPC125182
0.8889	High Similarity	NPC69647
0.8882	High Similarity	NPC255414
0.8882	High Similarity	NPC221809
0.8875	High Similarity	NPC478178
0.8875	High Similarity	NPC23387
0.8868	High Similarity	NPC88841
0.8868	High Similarity	NPC165218
0.8868	High Similarity	NPC288602
0.8867	High Similarity	NPC223415
0.8861	High Similarity	NPC305016
0.8861	High Similarity	NPC470789
0.8854	High Similarity	NPC472772
0.8854	High Similarity	NPC472283
0.8854	High Similarity	NPC470118
0.8846	High Similarity	NPC35000
0.8846	High Similarity	NPC469336
0.8846	High Similarity	NPC476262
0.8841	High Similarity	NPC262386
0.8839	High Similarity	NPC75906
0.8839	High Similarity	NPC476940
0.8839	High Similarity	NPC476939
0.8831	High Similarity	NPC476122
0.8827	High Similarity	NPC470995
0.882	High Similarity	NPC476853
0.8808	High Similarity	NPC86935
0.8805	High Similarity	NPC96443
0.8805	High Similarity	NPC470939
0.8805	High Similarity	NPC188649
0.8805	High Similarity	NPC290400
0.8805	High Similarity	NPC470792
0.8797	High Similarity	NPC475226
0.8797	High Similarity	NPC307383
0.8795	High Similarity	NPC470938
0.8792	High Similarity	NPC90296
0.879	High Similarity	NPC263265
0.8788	High Similarity	NPC472665
0.878	High Similarity	NPC469576
0.878	High Similarity	NPC471437
0.8773	High Similarity	NPC159232
0.8766	High Similarity	NPC472654
0.8765	High Similarity	NPC296558
0.8765	High Similarity	NPC327922
0.8758	High Similarity	NPC93172
0.8758	High Similarity	NPC149945
0.8758	High Similarity	NPC470941
0.8758	High Similarity	NPC97574
0.875	High Similarity	NPC419
0.875	High Similarity	NPC285567
0.875	High Similarity	NPC283209
0.8742	High Similarity	NPC243577
0.8742	High Similarity	NPC470741
0.8742	High Similarity	NPC191828
0.8742	High Similarity	NPC475381
0.8734	High Similarity	NPC167142
0.8727	High Similarity	NPC469633
0.8726	High Similarity	NPC281258
0.8726	High Similarity	NPC155939
0.8726	High Similarity	NPC141538
0.8726	High Similarity	NPC296807
0.8725	High Similarity	NPC90953
0.8718	High Similarity	NPC33938
0.8718	High Similarity	NPC147168
0.8716	High Similarity	NPC310830
0.871	High Similarity	NPC159927
0.871	High Similarity	NPC196864
0.871	High Similarity	NPC469335
0.871	High Similarity	NPC477404
0.8704	High Similarity	NPC478179
0.8701	High Similarity	NPC476942
0.8701	High Similarity	NPC476941
0.8696	High Similarity	NPC146991
0.8688	High Similarity	NPC207978
0.8688	High Similarity	NPC18986
0.8679	High Similarity	NPC472779
0.8679	High Similarity	NPC262872
0.8679	High Similarity	NPC237155
0.8675	High Similarity	NPC121158
0.8671	High Similarity	NPC104736
0.8662	High Similarity	NPC34421
0.8662	High Similarity	NPC98206
0.8662	High Similarity	NPC237259
0.865	High Similarity	NPC472765
0.865	High Similarity	NPC472766
0.8645	High Similarity	NPC211625
0.8642	High Similarity	NPC475779
0.8642	High Similarity	NPC214600
0.8642	High Similarity	NPC121995
0.8636	High Similarity	NPC476938
0.8636	High Similarity	NPC476937
0.8627	High Similarity	NPC5676
0.8625	High Similarity	NPC287559
0.8618	High Similarity	NPC476946
0.8616	High Similarity	NPC197137
0.8616	High Similarity	NPC194499
0.8616	High Similarity	NPC88007
0.8616	High Similarity	NPC304692
0.8608	High Similarity	NPC92979
0.8608	High Similarity	NPC469850
0.8599	High Similarity	NPC246164
0.8598	High Similarity	NPC472659
0.8591	High Similarity	NPC470742
0.8591	High Similarity	NPC186626

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 NPC261597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	880
0.2-0.3	2090
0.3-0.4	2616
0.4-0.5	1929
0.5-0.6	983
0.6-0.7	315
0.7-0.8	40
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD5760	Phase 2
0.8608	High Similarity	NPD5761	Phase 2
0.8471	Intermediate Similarity	NPD8434	Phase 2
0.8171	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6764	Approved
0.7861	Intermediate Similarity	NPD6765	Approved
0.7711	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6785	Approved
0.7684	Intermediate Similarity	NPD6784	Approved
0.7679	Intermediate Similarity	NPD7075	Discontinued
0.7636	Intermediate Similarity	NPD6599	Discontinued
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.744	Intermediate Similarity	NPD6801	Discontinued
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7819	Suspended
0.7389	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD3749	Approved
0.7349	Intermediate Similarity	NPD920	Approved
0.7347	Intermediate Similarity	NPD8404	Phase 2
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD2533	Approved
0.7326	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD3882	Suspended
0.731	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5844	Phase 1
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5494	Approved
0.7251	Intermediate Similarity	NPD5402	Approved
0.7251	Intermediate Similarity	NPD3817	Phase 2
0.7235	Intermediate Similarity	NPD1934	Approved
0.7229	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD7411	Suspended
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD1247	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD2800	Approved
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7119	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6166	Phase 2
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4966	Approved
0.711	Intermediate Similarity	NPD4965	Approved
0.711	Intermediate Similarity	NPD4967	Phase 2
0.7108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6232	Discontinued
0.7095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7473	Discontinued
0.7073	Intermediate Similarity	NPD1549	Phase 2
0.7073	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD3226	Approved
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7052	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5401	Approved
0.7017	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2346	Discontinued
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7012	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD8312	Approved
0.6994	Remote Similarity	NPD2801	Approved
0.6988	Remote Similarity	NPD3750	Approved
0.6982	Remote Similarity	NPD6273	Approved
0.6966	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6100	Approved
0.6951	Remote Similarity	NPD6099	Approved
0.6951	Remote Similarity	NPD2796	Approved
0.6949	Remote Similarity	NPD6959	Discontinued
0.6944	Remote Similarity	NPD7228	Approved
0.6944	Remote Similarity	NPD7799	Discontinued
0.6936	Remote Similarity	NPD37	Approved
0.6931	Remote Similarity	NPD4111	Phase 1
0.6931	Remote Similarity	NPD4665	Approved
0.6928	Remote Similarity	NPD1243	Approved
0.6927	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6797	Phase 2
0.6914	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD6355	Discontinued
0.691	Remote Similarity	NPD5711	Approved
0.691	Remote Similarity	NPD5710	Approved
0.691	Remote Similarity	NPD3787	Discontinued
0.6907	Remote Similarity	NPD7435	Discontinued
0.6905	Remote Similarity	NPD7236	Approved
0.6897	Remote Similarity	NPD1465	Phase 2
0.689	Remote Similarity	NPD7033	Discontinued
0.689	Remote Similarity	NPD2799	Discontinued
0.6885	Remote Similarity	NPD7251	Discontinued
0.6882	Remote Similarity	NPD1512	Approved
0.6872	Remote Similarity	NPD3926	Phase 2
0.6868	Remote Similarity	NPD7074	Phase 3
0.6865	Remote Similarity	NPD8407	Phase 2
0.6863	Remote Similarity	NPD7907	Approved
0.686	Remote Similarity	NPD7458	Discontinued
0.6854	Remote Similarity	NPD8127	Discontinued
0.6854	Remote Similarity	NPD7199	Phase 2
0.6848	Remote Similarity	NPD7808	Phase 3
0.6848	Remote Similarity	NPD2935	Discontinued
0.6839	Remote Similarity	NPD6778	Approved
0.6839	Remote Similarity	NPD6782	Approved
0.6839	Remote Similarity	NPD6781	Approved
0.6839	Remote Similarity	NPD6777	Approved
0.6839	Remote Similarity	NPD6780	Approved
0.6839	Remote Similarity	NPD6779	Approved
0.6839	Remote Similarity	NPD6776	Approved
0.6824	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD447	Suspended
0.6807	Remote Similarity	NPD6004	Phase 3
0.6807	Remote Similarity	NPD2344	Approved
0.6807	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6005	Phase 3
0.6807	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6002	Phase 3
0.6796	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8368	Discontinued
0.6788	Remote Similarity	NPD3748	Approved
0.6788	Remote Similarity	NPD1510	Phase 2
0.6776	Remote Similarity	NPD7472	Approved
0.6769	Remote Similarity	NPD3057	Approved
0.6765	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1511	Approved
0.6753	Remote Similarity	NPD4107	Approved
0.6746	Remote Similarity	NPD6190	Approved
0.6735	Remote Similarity	NPD7497	Discontinued
0.6728	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3764	Approved
0.6728	Remote Similarity	NPD2313	Discontinued
0.6728	Remote Similarity	NPD6798	Discontinued
0.6722	Remote Similarity	NPD7229	Phase 3
0.672	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5762	Approved
0.6707	Remote Similarity	NPD230	Phase 1
0.6707	Remote Similarity	NPD5763	Approved
0.6705	Remote Similarity	NPD7239	Suspended
0.6703	Remote Similarity	NPD7685	Pre-registration
0.6703	Remote Similarity	NPD7240	Approved
0.67	Remote Similarity	NPD7874	Approved
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6233	Phase 2
0.6687	Remote Similarity	NPD4308	Phase 3
0.6686	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7003	Approved
0.6684	Remote Similarity	NPD3533	Approved
0.6684	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD1607	Approved
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7697	Approved
0.6648	Remote Similarity	NPD2403	Approved
0.6647	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2309	Approved
0.6646	Remote Similarity	NPD1240	Approved
0.6646	Remote Similarity	NPD4060	Phase 1
0.6646	Remote Similarity	NPD9717	Approved
0.6646	Remote Similarity	NPD1608	Approved
0.6646	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4482	Phase 3
0.6632	Remote Similarity	NPD8360	Approved
0.6632	Remote Similarity	NPD8361	Approved
0.6626	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3268	Approved
0.6625	Remote Similarity	NPD2797	Approved
0.6625	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8319	Approved
0.6616	Remote Similarity	NPD8320	Phase 1
0.6616	Remote Similarity	NPD7871	Phase 2
0.6616	Remote Similarity	NPD7870	Phase 2
0.6606	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5124	Phase 1
0.6605	Remote Similarity	NPD7048	Phase 3
0.6605	Remote Similarity	NPD6832	Phase 2
0.66	Remote Similarity	NPD7701	Phase 2
0.6599	Remote Similarity	NPD2491	Approved
0.6591	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4110	Phase 3
0.6584	Remote Similarity	NPD5647	Approved
0.6584	Remote Similarity	NPD7801	Approved
0.658	Remote Similarity	NPD6535	Approved
0.658	Remote Similarity	NPD6534	Approved
0.6568	Remote Similarity	NPD2424	Discontinued
0.6566	Remote Similarity	NPD6651	Approved
0.6564	Remote Similarity	NPD5952	Clinical (unspecified phase)

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