NPASS Compound

Structure

NPC287294 OpenBabel07101718282D 33 36 0 0 1 0 0 0 0 0999 V2000 -6.5358 0.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3548 2.1341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5303 0.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3493 2.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -4.9535 1.1160 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 -4.3776 -1.4067 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 -5.9480 1.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9371 1.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -5.0468 -0.6636 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 0.2024 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 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -8.9316 1.5341 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 -6.0413 -0.7681 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.0055 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 3 1 0 0 0 0 1 11 2 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 24 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 27 2 0 0 0 0 16 32 1 0 0 0 0 17 31 1 0 0 0 0 18 7 1 1 0 0 0 18 31 1 0 0 0 0 19 10 1 1 0 0 0 19 20 1 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 32 1 1 0 0 0 23 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.14
Volume:	438.949
LogP:	1.312
LogD:	1.149
LogS:	-2.525
# Rotatable Bonds:	6
TPSA:	173.21
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	4.034
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.136
MDCK Permeability:	6.079659669921966e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.35
Human Intestinal Absorption (HIA):	0.246
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	97.4537124633789%
Volume Distribution (VD):	0.646
Pgp-substrate:	2.0284194946289062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.286
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.272
CYP2C9-substrate:	0.754
CYP2D6-inhibitor:	0.521
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.257
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	8.194
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.175
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.143
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.462
Carcinogencity:	0.135
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC287294

Natural Product ID:	NPC287294
*Common Name:**	Spinonin
IUPAC Name:	(2R)-2-[(4-hydroxyphenyl)methyl]-5-[4-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]furan-3-one
Synonyms:	Spinonin
Standard InCHIKey:	UVBIDKJGBSKHAV-FHJOOOADSA-N
Standard InCHI:	InChI=1S/C23H24O10/c24-10-19-20(28)21(29)22(30)23(33-19)32-16-8-13(26)5-6-14(16)17-9-15(27)18(31-17)7-11-1-3-12(25)4-2-11/h1-6,8-9,18-26,28-30H,7,10H2/t18-,19-,20-,21+,22-,23-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)ccc2C2=CC(=O)[C@H](O2)Cc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465777
PubChem CID:	10813816
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:0004165] Phenolic glycosides

*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
NPO6731.1	Ononis spinosa	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9182126]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	200.0	ug.mL-1	PMID[560044]

☑ 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 NPC287294 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	362
0.1-0.2	1445
0.2-0.3	3557
0.3-0.4	9076
0.4-0.5	9720
0.5-0.6	4590
0.6-0.7	6405
0.7-0.8	6684
0.8-0.85	753
0.85-0.9	98
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC288084
0.9205	High Similarity	NPC54802
0.9205	High Similarity	NPC77672
0.9205	High Similarity	NPC133671
0.9205	High Similarity	NPC197304
0.9205	High Similarity	NPC135391
0.9205	High Similarity	NPC78263
0.9145	High Similarity	NPC111929
0.9145	High Similarity	NPC320283
0.9145	High Similarity	NPC472459
0.9145	High Similarity	NPC41121
0.9139	High Similarity	NPC203500
0.9139	High Similarity	NPC323593
0.9139	High Similarity	NPC307938
0.9122	High Similarity	NPC100818
0.9091	High Similarity	NPC150164
0.9085	High Similarity	NPC471079
0.9085	High Similarity	NPC153342
0.9085	High Similarity	NPC470405
0.9085	High Similarity	NPC304741
0.9079	High Similarity	NPC6985
0.9079	High Similarity	NPC182634
0.9079	High Similarity	NPC108831
0.9067	High Similarity	NPC259182
0.9067	High Similarity	NPC121001
0.9067	High Similarity	NPC88484
0.9067	High Similarity	NPC259767
0.9026	High Similarity	NPC163242
0.9026	High Similarity	NPC129217
0.9026	High Similarity	NPC181465
0.9026	High Similarity	NPC476215
0.9026	High Similarity	NPC159579
0.9026	High Similarity	NPC276377
0.9026	High Similarity	NPC215710
0.9026	High Similarity	NPC139320
0.9026	High Similarity	NPC265885
0.9026	High Similarity	NPC282169
0.9026	High Similarity	NPC170052
0.9026	High Similarity	NPC253788
0.9026	High Similarity	NPC224530
0.9026	High Similarity	NPC85707
0.9026	High Similarity	NPC216496
0.9026	High Similarity	NPC64305
0.9026	High Similarity	NPC297987
0.9026	High Similarity	NPC470125
0.9026	High Similarity	NPC259957
0.9026	High Similarity	NPC473438
0.9026	High Similarity	NPC246943
0.9026	High Similarity	NPC135846
0.9026	High Similarity	NPC173582
0.9026	High Similarity	NPC116458
0.9026	High Similarity	NPC48093
0.9026	High Similarity	NPC249281
0.9013	High Similarity	NPC149368
0.9013	High Similarity	NPC265480
0.9007	High Similarity	NPC39360
0.9007	High Similarity	NPC83283
0.9007	High Similarity	NPC106625
0.9007	High Similarity	NPC143851
0.9007	High Similarity	NPC29763
0.9007	High Similarity	NPC210003
0.8974	High Similarity	NPC72016
0.8968	High Similarity	NPC27942
0.8968	High Similarity	NPC240306
0.8961	High Similarity	NPC136761
0.8961	High Similarity	NPC187379
0.8954	High Similarity	NPC122809
0.8947	High Similarity	NPC39351
0.8947	High Similarity	NPC26195
0.8947	High Similarity	NPC27408
0.8947	High Similarity	NPC99233
0.8947	High Similarity	NPC95090
0.8947	High Similarity	NPC97052
0.8947	High Similarity	NPC72649
0.8947	High Similarity	NPC169248
0.891	High Similarity	NPC121703
0.891	High Similarity	NPC278419
0.891	High Similarity	NPC66087
0.891	High Similarity	NPC179198
0.8896	High Similarity	NPC104677
0.8889	High Similarity	NPC206378
0.8889	High Similarity	NPC127406
0.8889	High Similarity	NPC170475
0.8861	High Similarity	NPC48640
0.8861	High Similarity	NPC149244
0.8859	High Similarity	NPC302989
0.8854	High Similarity	NPC19240
0.8854	High Similarity	NPC205824
0.8854	High Similarity	NPC129264
0.8854	High Similarity	NPC292929
0.8854	High Similarity	NPC85751
0.8854	High Similarity	NPC76831
0.8854	High Similarity	NPC289667
0.8846	High Similarity	NPC259834
0.8846	High Similarity	NPC131745
0.8839	High Similarity	NPC200708
0.8839	High Similarity	NPC306978
0.8831	High Similarity	NPC60966
0.8831	High Similarity	NPC473512
0.8831	High Similarity	NPC258035
0.8831	High Similarity	NPC44931
0.8831	High Similarity	NPC313163
0.8831	High Similarity	NPC43638
0.8831	High Similarity	NPC65003
0.8831	High Similarity	NPC23817
0.8831	High Similarity	NPC161749
0.8831	High Similarity	NPC197896
0.8831	High Similarity	NPC129827
0.8831	High Similarity	NPC156457
0.8808	High Similarity	NPC191154
0.88	High Similarity	NPC199335
0.8797	High Similarity	NPC186816
0.8797	High Similarity	NPC276222
0.8797	High Similarity	NPC256188
0.8797	High Similarity	NPC281131
0.8797	High Similarity	NPC64425
0.8797	High Similarity	NPC32641
0.8797	High Similarity	NPC255615
0.8797	High Similarity	NPC118284
0.8797	High Similarity	NPC308404
0.8797	High Similarity	NPC189564
0.8797	High Similarity	NPC253662
0.8797	High Similarity	NPC12013
0.8797	High Similarity	NPC179950
0.8797	High Similarity	NPC145038
0.8797	High Similarity	NPC142142
0.8797	High Similarity	NPC88789
0.8797	High Similarity	NPC67037
0.8797	High Similarity	NPC221342
0.8797	High Similarity	NPC11432
0.8797	High Similarity	NPC203145
0.8797	High Similarity	NPC476470
0.8797	High Similarity	NPC477613
0.8797	High Similarity	NPC56077
0.8797	High Similarity	NPC274618
0.879	High Similarity	NPC183672
0.879	High Similarity	NPC80068
0.8784	High Similarity	NPC226722
0.8774	High Similarity	NPC308265
0.8774	High Similarity	NPC138811
0.8774	High Similarity	NPC22062
0.8774	High Similarity	NPC473634
0.8774	High Similarity	NPC73511
0.8766	High Similarity	NPC261866
0.875	High Similarity	NPC134819
0.875	High Similarity	NPC72249
0.875	High Similarity	NPC166180
0.8742	High Similarity	NPC127546
0.8742	High Similarity	NPC92565
0.8742	High Similarity	NPC160156
0.8742	High Similarity	NPC317489
0.8742	High Similarity	NPC52550
0.8742	High Similarity	NPC84362
0.8742	High Similarity	NPC223424
0.8742	High Similarity	NPC173637
0.8734	High Similarity	NPC277205
0.8734	High Similarity	NPC55786
0.8734	High Similarity	NPC34531
0.8734	High Similarity	NPC240431
0.8734	High Similarity	NPC287889
0.8734	High Similarity	NPC135358
0.8734	High Similarity	NPC139060
0.8734	High Similarity	NPC19388
0.8733	High Similarity	NPC23084
0.8718	High Similarity	NPC246469
0.8718	High Similarity	NPC142860
0.8718	High Similarity	NPC271270
0.8718	High Similarity	NPC473623
0.8718	High Similarity	NPC97285
0.8718	High Similarity	NPC271479
0.8718	High Similarity	NPC472320
0.8707	High Similarity	NPC31081
0.8707	High Similarity	NPC245219
0.8696	High Similarity	NPC245452
0.869	High Similarity	NPC87777
0.869	High Similarity	NPC262328
0.8688	High Similarity	NPC120099
0.8688	High Similarity	NPC225434
0.8688	High Similarity	NPC270578
0.8688	High Similarity	NPC5319
0.8688	High Similarity	NPC52382
0.8688	High Similarity	NPC223747
0.8688	High Similarity	NPC203050
0.8688	High Similarity	NPC219904
0.8684	High Similarity	NPC213723
0.8684	High Similarity	NPC214454
0.8684	High Similarity	NPC106025
0.8684	High Similarity	NPC477240
0.8679	High Similarity	NPC21100
0.8679	High Similarity	NPC254306
0.8679	High Similarity	NPC73855
0.8679	High Similarity	NPC328940
0.8679	High Similarity	NPC113968
0.8679	High Similarity	NPC277174
0.8679	High Similarity	NPC197285
0.8679	High Similarity	NPC135599
0.8662	High Similarity	NPC270675
0.8662	High Similarity	NPC47923
0.8662	High Similarity	NPC472994
0.8662	High Similarity	NPC477628

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 NPC287294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	821
0.2-0.3	1696
0.3-0.4	2740
0.4-0.5	1976
0.5-0.6	1075
0.6-0.7	425
0.7-0.8	105
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8831	High Similarity	NPD4381	Clinical (unspecified phase)
0.8688	High Similarity	NPD7804	Clinical (unspecified phase)
0.858	High Similarity	NPD6797	Phase 2
0.8528	High Similarity	NPD7251	Discontinued
0.8476	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7808	Phase 3
0.8395	Intermediate Similarity	NPD3818	Discontinued
0.8366	Intermediate Similarity	NPD5403	Approved
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD7054	Approved
0.8303	Intermediate Similarity	NPD6559	Discontinued
0.8293	Intermediate Similarity	NPD7472	Approved
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8235	Intermediate Similarity	NPD5401	Approved
0.8217	Intermediate Similarity	NPD6801	Discontinued
0.8205	Intermediate Similarity	NPD4380	Phase 2
0.817	Intermediate Similarity	NPD6799	Approved
0.8165	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD5402	Approved
0.8085	Intermediate Similarity	NPD1091	Approved
0.8079	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD1653	Approved
0.8049	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7987	Intermediate Similarity	NPD1934	Approved
0.7959	Intermediate Similarity	NPD6798	Discontinued
0.7959	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3751	Discontinued
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3882	Suspended
0.7937	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD8455	Phase 2
0.7927	Intermediate Similarity	NPD3787	Discontinued
0.7905	Intermediate Similarity	NPD6233	Phase 2
0.7879	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.7852	Intermediate Similarity	NPD1613	Approved
0.7852	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1512	Approved
0.7811	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6355	Discontinued
0.7764	Intermediate Similarity	NPD37	Approved
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7744	Intermediate Similarity	NPD6234	Discontinued
0.7742	Intermediate Similarity	NPD3750	Approved
0.7738	Intermediate Similarity	NPD7228	Approved
0.773	Intermediate Similarity	NPD4966	Approved
0.773	Intermediate Similarity	NPD4967	Phase 2
0.773	Intermediate Similarity	NPD4965	Approved
0.7716	Intermediate Similarity	NPD2801	Approved
0.7707	Intermediate Similarity	NPD1511	Approved
0.7702	Intermediate Similarity	NPD7411	Suspended
0.7677	Intermediate Similarity	NPD1652	Phase 2
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.7669	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1510	Phase 2
0.7597	Intermediate Similarity	NPD2796	Approved
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.7584	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4908	Phase 1
0.758	Intermediate Similarity	NPD6190	Approved
0.7571	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4062	Phase 3
0.7548	Intermediate Similarity	NPD7266	Discontinued
0.7547	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5124	Phase 1
0.7451	Intermediate Similarity	NPD4340	Discontinued
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD3748	Approved
0.7417	Intermediate Similarity	NPD3027	Phase 3
0.7403	Intermediate Similarity	NPD1607	Approved
0.7389	Intermediate Similarity	NPD2424	Discontinued
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7383	Intermediate Similarity	NPD2797	Approved
0.7368	Intermediate Similarity	NPD3268	Approved
0.7356	Intermediate Similarity	NPD7240	Approved
0.7337	Intermediate Similarity	NPD6959	Discontinued
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7768	Phase 2
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1465	Phase 2
0.7285	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7262	Intermediate Similarity	NPD3749	Approved
0.7261	Intermediate Similarity	NPD6100	Approved
0.7261	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7244	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7097	Phase 1
0.7234	Intermediate Similarity	NPD7584	Approved
0.7226	Intermediate Similarity	NPD1933	Approved
0.7213	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5058	Phase 3
0.7189	Intermediate Similarity	NPD6776	Approved
0.7189	Intermediate Similarity	NPD6781	Approved
0.7189	Intermediate Similarity	NPD6778	Approved
0.7189	Intermediate Similarity	NPD6780	Approved
0.7189	Intermediate Similarity	NPD6777	Approved
0.7189	Intermediate Similarity	NPD6779	Approved
0.7189	Intermediate Similarity	NPD6782	Approved
0.717	Intermediate Similarity	NPD5958	Discontinued
0.7166	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7124	Intermediate Similarity	NPD6832	Phase 2
0.7114	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1535	Discovery
0.711	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7585	Approved
0.7093	Intermediate Similarity	NPD6232	Discontinued
0.7078	Intermediate Similarity	NPD7095	Approved
0.7075	Intermediate Similarity	NPD1894	Discontinued
0.7069	Intermediate Similarity	NPD7473	Discontinued
0.7067	Intermediate Similarity	NPD1481	Phase 2
0.7063	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4534	Discontinued
0.7053	Intermediate Similarity	NPD7583	Approved
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD2935	Discontinued
0.7039	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD3267	Approved
0.7019	Intermediate Similarity	NPD2800	Approved
0.7019	Intermediate Similarity	NPD6674	Discontinued
0.7018	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6005	Phase 3
0.7	Intermediate Similarity	NPD5763	Approved
0.7	Intermediate Similarity	NPD6004	Phase 3
0.6993	Remote Similarity	NPD5647	Approved
0.6984	Remote Similarity	NPD7696	Phase 3
0.6984	Remote Similarity	NPD7697	Approved
0.6984	Remote Similarity	NPD7698	Approved
0.6981	Remote Similarity	NPD5588	Approved
0.697	Remote Similarity	NPD5049	Phase 3
0.6968	Remote Similarity	NPD4625	Phase 3
0.6966	Remote Similarity	NPD1241	Discontinued
0.6961	Remote Similarity	NPD8434	Phase 2
0.6959	Remote Similarity	NPD6971	Discontinued
0.6954	Remote Similarity	NPD3926	Phase 2
0.6952	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7213	Phase 3
0.6951	Remote Similarity	NPD7212	Phase 2
0.6947	Remote Similarity	NPD7870	Phase 2
0.6947	Remote Similarity	NPD7871	Phase 2
0.6946	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7874	Approved
0.6936	Remote Similarity	NPD1247	Approved
0.6933	Remote Similarity	NPD2354	Approved
0.6933	Remote Similarity	NPD3887	Approved
0.6931	Remote Similarity	NPD6823	Phase 2
0.6928	Remote Similarity	NPD920	Approved
0.6927	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7701	Phase 2
0.6923	Remote Similarity	NPD2313	Discontinued
0.6923	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD6535	Approved
0.6918	Remote Similarity	NPD4536	Approved
0.6918	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4538	Approved
0.6914	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5953	Discontinued
0.6909	Remote Similarity	NPD2532	Approved
0.6909	Remote Similarity	NPD2534	Approved
0.6909	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2533	Approved
0.6909	Remote Similarity	NPD3536	Discontinued
0.6908	Remote Similarity	NPD4749	Approved
0.6908	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD290	Approved
0.6899	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD7843	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