NPASS Compound

Structure

NPC303727 OpenBabel07101718232D 24 25 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 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 5.1962 -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 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 5.1962 1.0000 0.0000 C 0 0 2 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 4.3301 1.5000 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 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 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 3.4641 -0.0000 0.0000 C 0 0 1 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 6 0 0 0 7 4 1 6 0 0 0 7 9 1 0 0 0 0 7 24 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 1 0 0 0 9 10 1 0 0 0 0 9 17 1 1 0 0 0 10 12 1 0 0 0 0 10 18 1 6 0 0 0 11 13 1 0 0 0 0 11 19 1 6 0 0 0 12 14 1 0 0 0 0 12 20 1 1 0 0 0 13 21 1 0 0 0 0 13 22 1 1 0 0 0 14 23 1 6 0 0 0 14 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	321.49
LogP:	-1.694
LogD:	-1.845
LogS:	-0.634
# Rotatable Bonds:	5
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.295
Synthetic Accessibility Score:	4.37
Fsp3:	1.0
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:	-5.53
MDCK Permeability:	0.00010342001041863114
Pgp-inhibitor:	0.006
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.849
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	19.924022674560547%
Volume Distribution (VD):	0.456
Pgp-substrate:	56.69779968261719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.301
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	0.971
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.516
Carcinogencity:	0.048
Eye Corrosion:	0.004
Eye Irritation:	0.293
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC303727

Natural Product ID:	NPC303727
*Common Name:**	BPIRJCXWOHGVJV-HCDYWNEASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BPIRJCXWOHGVJV-HCDYWNEASA-N
Standard InCHI:	InChI=1S/C14H26O10/c1-5(2)23-14-12(20)10(18)9(17)7(24-14)4-22-13-11(19)8(16)6(15)3-21-13/h5-20H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-,12-,13+,14-/m1/s1
SMILES:	CC(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326715
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	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	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Inhibition	=	7.49	%	PMID[521304]
NPT35	Others	n.a.		Activity	=	0.31	uM	PMID[521304]
NPT35	Others	n.a.		Activity	=	2.13	uM	PMID[521304]
NPT35	Others	n.a.		Activity	=	0.27	uM	PMID[521304]
NPT35	Others	n.a.		Activity	=	0.63	uM	PMID[521304]
NPT35	Others	n.a.		Activity	=	21.67	%	PMID[521304]

☑ 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 NPC303727 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	1002
0.1-0.2	8431
0.2-0.3	17238
0.3-0.4	10482
0.4-0.5	4274
0.5-0.6	969
0.6-0.7	182
0.7-0.8	53
0.8-0.85	30
0.85-0.9	13
0.9-0.95	11
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC157514
0.98	High Similarity	NPC89145
0.98	High Similarity	NPC242073
0.98	High Similarity	NPC58629
0.98	High Similarity	NPC145112
0.98	High Similarity	NPC246558
0.98	High Similarity	NPC269166
0.98	High Similarity	NPC165198
0.98	High Similarity	NPC107914
0.98	High Similarity	NPC67660
0.9434	High Similarity	NPC472025
0.94	High Similarity	NPC23134
0.94	High Similarity	NPC124963
0.94	High Similarity	NPC326533
0.94	High Similarity	NPC233726
0.9038	High Similarity	NPC130683
0.9038	High Similarity	NPC323361
0.9	High Similarity	NPC42503
0.9	High Similarity	NPC299781
0.9	High Similarity	NPC157193
0.9	High Similarity	NPC282143
0.8929	High Similarity	NPC477755
0.8929	High Similarity	NPC477753
0.8929	High Similarity	NPC477750
0.8929	High Similarity	NPC477757
0.8929	High Similarity	NPC477763
0.8929	High Similarity	NPC477762
0.8909	High Similarity	NPC317023
0.8909	High Similarity	NPC290179
0.8909	High Similarity	NPC34877
0.88	High Similarity	NPC14144
0.8727	High Similarity	NPC219040
0.86	High Similarity	NPC321087
0.86	High Similarity	NPC277475
0.8545	High Similarity	NPC148424
0.8462	Intermediate Similarity	NPC323574
0.84	Intermediate Similarity	NPC255377
0.84	Intermediate Similarity	NPC289758
0.84	Intermediate Similarity	NPC176017
0.84	Intermediate Similarity	NPC69445
0.84	Intermediate Similarity	NPC165846
0.84	Intermediate Similarity	NPC285364
0.84	Intermediate Similarity	NPC92246
0.84	Intermediate Similarity	NPC21209
0.84	Intermediate Similarity	NPC199857
0.84	Intermediate Similarity	NPC73906
0.8333	Intermediate Similarity	NPC190418
0.8333	Intermediate Similarity	NPC76881
0.8333	Intermediate Similarity	NPC471760
0.8333	Intermediate Similarity	NPC12040
0.8333	Intermediate Similarity	NPC147292
0.8333	Intermediate Similarity	NPC471761
0.8276	Intermediate Similarity	NPC472026
0.8269	Intermediate Similarity	NPC82512
0.8246	Intermediate Similarity	NPC320032
0.8246	Intermediate Similarity	NPC322855
0.8197	Intermediate Similarity	NPC477764
0.8197	Intermediate Similarity	NPC477752
0.8197	Intermediate Similarity	NPC477751
0.8197	Intermediate Similarity	NPC477756
0.8167	Intermediate Similarity	NPC6848
0.8103	Intermediate Similarity	NPC143326
0.8065	Intermediate Similarity	NPC477761
0.8065	Intermediate Similarity	NPC477758
0.8065	Intermediate Similarity	NPC477759
0.8065	Intermediate Similarity	NPC477754
0.8065	Intermediate Similarity	NPC477760
0.8	Intermediate Similarity	NPC320240
0.8	Intermediate Similarity	NPC70756
0.7966	Intermediate Similarity	NPC155457
0.7937	Intermediate Similarity	NPC67099
0.7937	Intermediate Similarity	NPC50228
0.7937	Intermediate Similarity	NPC97736
0.7937	Intermediate Similarity	NPC250619
0.7885	Intermediate Similarity	NPC230789
0.7885	Intermediate Similarity	NPC252918
0.7812	Intermediate Similarity	NPC211428
0.7812	Intermediate Similarity	NPC285003
0.7812	Intermediate Similarity	NPC241265
0.78	Intermediate Similarity	NPC317182
0.78	Intermediate Similarity	NPC291502
0.78	Intermediate Similarity	NPC213159
0.78	Intermediate Similarity	NPC298699
0.78	Intermediate Similarity	NPC134252
0.78	Intermediate Similarity	NPC86191
0.7705	Intermediate Similarity	NPC277570
0.7705	Intermediate Similarity	NPC268243
0.7705	Intermediate Similarity	NPC325773
0.7692	Intermediate Similarity	NPC474078
0.7692	Intermediate Similarity	NPC53760
0.7692	Intermediate Similarity	NPC52268
0.7679	Intermediate Similarity	NPC314821
0.7679	Intermediate Similarity	NPC317626
0.7679	Intermediate Similarity	NPC317501
0.7581	Intermediate Similarity	NPC13143
0.7581	Intermediate Similarity	NPC31496
0.7581	Intermediate Similarity	NPC294813
0.75	Intermediate Similarity	NPC206601
0.7463	Intermediate Similarity	NPC9763
0.7463	Intermediate Similarity	NPC163812
0.7463	Intermediate Similarity	NPC225748
0.7463	Intermediate Similarity	NPC39266
0.7463	Intermediate Similarity	NPC169085
0.7463	Intermediate Similarity	NPC206823
0.74	Intermediate Similarity	NPC266553
0.7308	Intermediate Similarity	NPC29721
0.7231	Intermediate Similarity	NPC32148
0.7206	Intermediate Similarity	NPC55652
0.7164	Intermediate Similarity	NPC471879
0.7143	Intermediate Similarity	NPC279575
0.7143	Intermediate Similarity	NPC477350
0.7115	Intermediate Similarity	NPC320189
0.7101	Intermediate Similarity	NPC166250
0.7059	Intermediate Similarity	NPC184550
0.7059	Intermediate Similarity	NPC185419
0.7042	Intermediate Similarity	NPC476781
0.7042	Intermediate Similarity	NPC216883
0.7042	Intermediate Similarity	NPC476782
0.7042	Intermediate Similarity	NPC476783
0.6957	Remote Similarity	NPC308096
0.6957	Remote Similarity	NPC470660
0.6957	Remote Similarity	NPC470659
0.6957	Remote Similarity	NPC291228
0.6957	Remote Similarity	NPC132938
0.6944	Remote Similarity	NPC146380
0.6944	Remote Similarity	NPC150557
0.6944	Remote Similarity	NPC477330
0.6944	Remote Similarity	NPC477326
0.6944	Remote Similarity	NPC113745
0.6944	Remote Similarity	NPC281563
0.6944	Remote Similarity	NPC316807
0.6944	Remote Similarity	NPC475425
0.6944	Remote Similarity	NPC477329
0.6944	Remote Similarity	NPC477328
0.6944	Remote Similarity	NPC477323
0.6944	Remote Similarity	NPC109887
0.6944	Remote Similarity	NPC477325
0.6944	Remote Similarity	NPC477320
0.6857	Remote Similarity	NPC138273
0.6857	Remote Similarity	NPC308489
0.6852	Remote Similarity	NPC207656
0.6852	Remote Similarity	NPC107091
0.6849	Remote Similarity	NPC477346
0.6849	Remote Similarity	NPC146992
0.6849	Remote Similarity	NPC85759
0.6849	Remote Similarity	NPC294748
0.6849	Remote Similarity	NPC477344
0.6849	Remote Similarity	NPC158302
0.6849	Remote Similarity	NPC170595
0.6849	Remote Similarity	NPC22742
0.6833	Remote Similarity	NPC326557
0.6757	Remote Similarity	NPC163362
0.6757	Remote Similarity	NPC471420
0.6757	Remote Similarity	NPC127295
0.6757	Remote Similarity	NPC267592
0.6724	Remote Similarity	NPC329095
0.6716	Remote Similarity	NPC179823
0.6712	Remote Similarity	NPC98750
0.6712	Remote Similarity	NPC272841
0.6667	Remote Similarity	NPC472202
0.6667	Remote Similarity	NPC475327
0.6667	Remote Similarity	NPC119583
0.6667	Remote Similarity	NPC27289
0.6667	Remote Similarity	NPC259294
0.6667	Remote Similarity	NPC184915
0.6667	Remote Similarity	NPC472203
0.6667	Remote Similarity	NPC297768
0.6667	Remote Similarity	NPC476087
0.6667	Remote Similarity	NPC477318
0.6667	Remote Similarity	NPC475667
0.6667	Remote Similarity	NPC475270
0.6667	Remote Similarity	NPC126685
0.6667	Remote Similarity	NPC477331
0.6667	Remote Similarity	NPC173328
0.6667	Remote Similarity	NPC186992
0.6667	Remote Similarity	NPC89843
0.6667	Remote Similarity	NPC477319
0.6667	Remote Similarity	NPC183888
0.6667	Remote Similarity	NPC115013
0.6667	Remote Similarity	NPC477317
0.6667	Remote Similarity	NPC123204
0.6667	Remote Similarity	NPC472200
0.6667	Remote Similarity	NPC290012
0.6667	Remote Similarity	NPC472201
0.6667	Remote Similarity	NPC472204
0.6667	Remote Similarity	NPC477347
0.6667	Remote Similarity	NPC44782
0.6667	Remote Similarity	NPC472205
0.6667	Remote Similarity	NPC143421
0.6667	Remote Similarity	NPC238056
0.6667	Remote Similarity	NPC307400
0.6667	Remote Similarity	NPC224953
0.6667	Remote Similarity	NPC169345
0.6667	Remote Similarity	NPC269318
0.6622	Remote Similarity	NPC70574
0.6622	Remote Similarity	NPC318258
0.662	Remote Similarity	NPC472174
0.662	Remote Similarity	NPC472173
0.661	Remote Similarity	NPC320043
0.661	Remote Similarity	NPC103672

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 NPC303727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1018
0.1-0.2	5337
0.2-0.3	1980
0.3-0.4	512
0.4-0.5	161
0.5-0.6	92
0.6-0.7	21
0.7-0.8	10
0.8-0.85	11
0.85-0.9	1
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.98	High Similarity	NPD890	Clinical (unspecified phase)
0.98	High Similarity	NPD892	Phase 3
0.98	High Similarity	NPD893	Approved
0.98	High Similarity	NPD888	Phase 3
0.98	High Similarity	NPD891	Phase 3
0.94	High Similarity	NPD904	Phase 3
0.94	High Similarity	NPD905	Approved
0.9038	High Similarity	NPD889	Approved
0.9038	High Similarity	NPD895	Approved
0.9038	High Similarity	NPD894	Approved
0.9038	High Similarity	NPD887	Approved
0.8846	High Similarity	NPD2269	Approved
0.8596	High Similarity	NPD6123	Approved
0.84	Intermediate Similarity	NPD8999	Phase 3
0.84	Intermediate Similarity	NPD8997	Approved
0.84	Intermediate Similarity	NPD8998	Phase 2
0.84	Intermediate Similarity	NPD8993	Phase 1
0.84	Intermediate Similarity	NPD9000	Phase 3
0.8182	Intermediate Similarity	NPD7346	Approved
0.8077	Intermediate Similarity	NPD8965	Approved
0.8077	Intermediate Similarity	NPD8966	Approved
0.807	Intermediate Similarity	NPD369	Approved
0.7895	Intermediate Similarity	NPD2267	Suspended
0.78	Intermediate Similarity	NPD8788	Approved
0.7705	Intermediate Similarity	NPD847	Phase 1
0.7679	Intermediate Similarity	NPD9035	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD9036	Phase 3
0.7308	Intermediate Similarity	NPD9006	Approved
0.7231	Intermediate Similarity	NPD898	Approved
0.7231	Intermediate Similarity	NPD897	Approved
0.7231	Intermediate Similarity	NPD896	Approved
0.7206	Intermediate Similarity	NPD3181	Approved
0.7031	Intermediate Similarity	NPD1457	Discontinued
0.6852	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9219	Approved
0.6849	Remote Similarity	NPD7329	Approved
0.6833	Remote Similarity	NPD885	Approved
0.6833	Remote Similarity	NPD884	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8994	Approved
0.661	Remote Similarity	NPD9050	Approved
0.661	Remote Similarity	NPD9049	Discontinued
0.6481	Remote Similarity	NPD8957	Approved
0.6481	Remote Similarity	NPD8958	Phase 2
0.6441	Remote Similarity	NPD1399	Approved
0.6441	Remote Similarity	NPD1400	Approved
0.6429	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.64	Remote Similarity	NPD9052	Approved
0.64	Remote Similarity	NPD9051	Approved
0.64	Remote Similarity	NPD9053	Approved
0.6389	Remote Similarity	NPD1811	Approved
0.6389	Remote Similarity	NPD1810	Approved
0.6364	Remote Similarity	NPD8961	Approved
0.6286	Remote Similarity	NPD9445	Approved
0.6111	Remote Similarity	NPD8995	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8996	Phase 3
0.6087	Remote Similarity	NPD9030	Approved
0.6087	Remote Similarity	NPD9031	Approved
0.6087	Remote Similarity	NPD9032	Approved
0.6087	Remote Similarity	NPD9033	Approved
0.6049	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD389	Phase 3
0.6	Remote Similarity	NPD8967	Approved
0.5976	Remote Similarity	NPD3207	Approved
0.5976	Remote Similarity	NPD3209	Approved
0.5976	Remote Similarity	NPD3202	Approved
0.5976	Remote Similarity	NPD3203	Approved
0.5976	Remote Similarity	NPD3201	Approved
0.5976	Remote Similarity	NPD3208	Approved
0.5932	Remote Similarity	NPD9139	Approved
0.5846	Remote Similarity	NPD8959	Approved
0.5833	Remote Similarity	NPD5795	Approved
0.5833	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5797	Approved
0.5833	Remote Similarity	NPD5794	Approved
0.5833	Remote Similarity	NPD5798	Approved
0.5818	Remote Similarity	NPD7536	Approved
0.5814	Remote Similarity	NPD1447	Phase 3
0.5814	Remote Similarity	NPD8171	Discontinued
0.5814	Remote Similarity	NPD1446	Phase 3
0.5811	Remote Similarity	NPD9034	Approved
0.5811	Remote Similarity	NPD67	Phase 2
0.5802	Remote Similarity	NPD361	Discontinued
0.58	Remote Similarity	NPD8814	Phase 3
0.5797	Remote Similarity	NPD371	Approved
0.5789	Remote Similarity	NPD372	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD2698	Approved
0.5753	Remote Similarity	NPD2686	Approved
0.5753	Remote Similarity	NPD2687	Approved
0.5753	Remote Similarity	NPD2254	Approved
0.5714	Remote Similarity	NPD9435	Approved
0.5714	Remote Similarity	NPD9434	Approved
0.5679	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3669	Approved
0.566	Remote Similarity	NPD370	Phase 3
0.5625	Remote Similarity	NPD3730	Approved
0.5625	Remote Similarity	NPD3728	Approved
0.5618	Remote Similarity	NPD6428	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