NPASS Compound

Structure

NPC197252 OpenBabel07101719252D 34 36 0 0 1 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 4.3301 -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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 1.7321 1.0000 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 -2.5981 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -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 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 1.7321 0.0000 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 -3.4641 1.0000 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 3.4641 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 13 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 24 1 0 0 0 0 14 26 2 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 17 28 1 0 0 0 0 21 26 1 0 0 0 0 23 29 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 30 2 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 28 22 1 1 0 0 0 28 34 1 0 0 0 0 29 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.26
Volume:	510.563
LogP:	8.267
LogD:	4.71
LogS:	-3.839
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	3.698
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.746
MDCK Permeability:	1.8327027646591887e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.335
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.569

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	84.22782135009766%
Volume Distribution (VD):	4.37
Pgp-substrate:	14.879364013671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.921
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.426
CYP2D6-substrate:	0.45
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	20.691
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.898
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.486
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC197252

Natural Product ID:	NPC197252
*Common Name:**	Prostratol
IUPAC Name:	(2S)-7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:	Prostratol
Standard InCHIKey:	PEALLWJXGZSLMC-NDEPHWFRSA-N
Standard InCHI:	InChI=1S/C30H36O4/c1-18(2)7-10-21-15-22(12-14-26(21)31)28-17-27(32)25-16-23(11-8-19(3)4)29(33)24(30(25)34-28)13-9-20(5)6/h7-9,12,14-16,28,31,33H,10-11,13,17H2,1-6H3/t28-/m0/s1
SMILES:	CC(=CCc1c2O[C@@H](CC(=O)c2cc(c1O)CC=C(C)C)c1ccc(c(c1)CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561966
PubChem CID:	45268825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	980.0	nM	PMID[495477]

☑ 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 NPC197252 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	359
0.1-0.2	1421
0.2-0.3	3549
0.3-0.4	9150
0.4-0.5	9482
0.5-0.6	3562
0.6-0.7	5655
0.7-0.8	5313
0.8-0.85	2206
0.85-0.9	1226
0.9-0.95	565
0.95-1	209

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236766
0.9928	High Similarity	NPC143896
0.9928	High Similarity	NPC39329
0.9928	High Similarity	NPC221432
0.9928	High Similarity	NPC68104
0.9928	High Similarity	NPC91560
0.9928	High Similarity	NPC257097
0.9928	High Similarity	NPC310130
0.9928	High Similarity	NPC75049
0.9928	High Similarity	NPC164980
0.9928	High Similarity	NPC149026
0.9928	High Similarity	NPC150408
0.9928	High Similarity	NPC175504
0.9928	High Similarity	NPC169591
0.9928	High Similarity	NPC185276
0.9856	High Similarity	NPC235217
0.9856	High Similarity	NPC473014
0.9856	High Similarity	NPC473015
0.9856	High Similarity	NPC473013
0.9856	High Similarity	NPC209040
0.9855	High Similarity	NPC10937
0.9855	High Similarity	NPC167624
0.9855	High Similarity	NPC107572
0.9855	High Similarity	NPC194432
0.9855	High Similarity	NPC182852
0.9855	High Similarity	NPC1089
0.9855	High Similarity	NPC125855
0.9855	High Similarity	NPC227579
0.9855	High Similarity	NPC166934
0.9855	High Similarity	NPC177354
0.9855	High Similarity	NPC220998
0.9855	High Similarity	NPC76372
0.9855	High Similarity	NPC306829
0.9855	High Similarity	NPC223500
0.9855	High Similarity	NPC32739
0.9855	High Similarity	NPC161506
0.9855	High Similarity	NPC265040
0.9855	High Similarity	NPC37496
0.9855	High Similarity	NPC296917
0.9855	High Similarity	NPC328164
0.9855	High Similarity	NPC324134
0.9855	High Similarity	NPC228504
0.9855	High Similarity	NPC76338
0.9855	High Similarity	NPC78
0.9855	High Similarity	NPC166482
0.9855	High Similarity	NPC148757
0.9855	High Similarity	NPC64915
0.9855	High Similarity	NPC40833
0.9855	High Similarity	NPC324436
0.9855	High Similarity	NPC66515
0.9787	High Similarity	NPC132592
0.9787	High Similarity	NPC160821
0.9786	High Similarity	NPC127059
0.9786	High Similarity	NPC285630
0.9784	High Similarity	NPC223812
0.9784	High Similarity	NPC316816
0.9784	High Similarity	NPC278249
0.9784	High Similarity	NPC85162
0.9784	High Similarity	NPC478086
0.9784	High Similarity	NPC81697
0.9784	High Similarity	NPC214166
0.9784	High Similarity	NPC107177
0.9784	High Similarity	NPC77794
0.9784	High Similarity	NPC125894
0.9783	High Similarity	NPC96408
0.9783	High Similarity	NPC248372
0.9783	High Similarity	NPC4743
0.9783	High Similarity	NPC279650
0.9783	High Similarity	NPC312391
0.9783	High Similarity	NPC258630
0.9783	High Similarity	NPC213322
0.9783	High Similarity	NPC3188
0.9783	High Similarity	NPC110038
0.9783	High Similarity	NPC324386
0.9783	High Similarity	NPC156190
0.9783	High Similarity	NPC17170
0.9783	High Similarity	NPC166689
0.9716	High Similarity	NPC23728
0.9716	High Similarity	NPC283234
0.9716	High Similarity	NPC110303
0.9714	High Similarity	NPC131579
0.9714	High Similarity	NPC131568
0.9712	High Similarity	NPC147145
0.971	High Similarity	NPC110228
0.971	High Similarity	NPC188243
0.971	High Similarity	NPC69769
0.971	High Similarity	NPC6407
0.9645	High Similarity	NPC176229
0.9645	High Similarity	NPC475052
0.9645	High Similarity	NPC470134
0.9645	High Similarity	NPC111786
0.9645	High Similarity	NPC312973
0.9645	High Similarity	NPC470647
0.9645	High Similarity	NPC109183
0.9645	High Similarity	NPC301276
0.9645	High Similarity	NPC20488
0.9645	High Similarity	NPC246948
0.9645	High Similarity	NPC54577
0.9645	High Similarity	NPC88964
0.9645	High Similarity	NPC470131
0.9645	High Similarity	NPC142405
0.9645	High Similarity	NPC267375
0.9645	High Similarity	NPC473078
0.9645	High Similarity	NPC195621
0.9645	High Similarity	NPC472629
0.9645	High Similarity	NPC470132
0.9645	High Similarity	NPC67805
0.9645	High Similarity	NPC83357
0.9645	High Similarity	NPC470133
0.9645	High Similarity	NPC214774
0.9643	High Similarity	NPC18585
0.9643	High Similarity	NPC106985
0.9643	High Similarity	NPC166138
0.964	High Similarity	NPC110969
0.9638	High Similarity	NPC222342
0.9638	High Similarity	NPC140890
0.9638	High Similarity	NPC20709
0.9638	High Similarity	NPC225153
0.9638	High Similarity	NPC265871
0.9638	High Similarity	NPC274784
0.9638	High Similarity	NPC150648
0.9638	High Similarity	NPC310135
0.9638	High Similarity	NPC329203
0.958	High Similarity	NPC472628
0.9577	High Similarity	NPC10990
0.9577	High Similarity	NPC473077
0.9577	High Similarity	NPC300988
0.9577	High Similarity	NPC472627
0.9577	High Similarity	NPC296998
0.9574	High Similarity	NPC124780
0.9574	High Similarity	NPC87486
0.9574	High Similarity	NPC470136
0.9574	High Similarity	NPC319752
0.9574	High Similarity	NPC470135
0.9574	High Similarity	NPC470890
0.9574	High Similarity	NPC39045
0.9574	High Similarity	NPC271288
0.9571	High Similarity	NPC11561
0.9571	High Similarity	NPC144499
0.9571	High Similarity	NPC226636
0.9568	High Similarity	NPC129853
0.9568	High Similarity	NPC284550
0.9568	High Similarity	NPC172986
0.9568	High Similarity	NPC76445
0.9568	High Similarity	NPC261227
0.9568	High Similarity	NPC241100
0.9568	High Similarity	NPC270883
0.9568	High Similarity	NPC159275
0.9565	High Similarity	NPC99333
0.9565	High Similarity	NPC188947
0.9565	High Similarity	NPC329225
0.9565	High Similarity	NPC147686
0.9565	High Similarity	NPC124269
0.9565	High Similarity	NPC472460
0.9565	High Similarity	NPC280284
0.9517	High Similarity	NPC477957
0.951	High Similarity	NPC145467
0.951	High Similarity	NPC168085
0.951	High Similarity	NPC161191
0.951	High Similarity	NPC39195
0.9507	High Similarity	NPC474161
0.9507	High Similarity	NPC187282
0.9507	High Similarity	NPC228779
0.9507	High Similarity	NPC290133
0.9507	High Similarity	NPC215885
0.9507	High Similarity	NPC24136
0.9507	High Similarity	NPC476088
0.9507	High Similarity	NPC2416
0.9507	High Similarity	NPC477955
0.9507	High Similarity	NPC476153
0.9504	High Similarity	NPC471621
0.9504	High Similarity	NPC38219
0.95	High Similarity	NPC147688
0.95	High Similarity	NPC118840
0.95	High Similarity	NPC282300
0.95	High Similarity	NPC103362
0.95	High Similarity	NPC156590
0.95	High Similarity	NPC205006
0.95	High Similarity	NPC64908
0.9496	High Similarity	NPC11566
0.9496	High Similarity	NPC261234
0.9496	High Similarity	NPC220062
0.9496	High Similarity	NPC78913
0.9496	High Similarity	NPC96565
0.9496	High Similarity	NPC216978
0.9496	High Similarity	NPC301217
0.9496	High Similarity	NPC303633
0.9496	High Similarity	NPC217186
0.9496	High Similarity	NPC470211
0.9496	High Similarity	NPC55018
0.9496	High Similarity	NPC53181
0.9496	High Similarity	NPC18260
0.9493	High Similarity	NPC259685
0.9493	High Similarity	NPC84585
0.9493	High Similarity	NPC243083
0.9493	High Similarity	NPC32441
0.9493	High Similarity	NPC13768
0.9493	High Similarity	NPC12296
0.9493	High Similarity	NPC476480
0.9493	High Similarity	NPC287246

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 NPC197252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	918
0.2-0.3	1502
0.3-0.4	2502
0.4-0.5	2006
0.5-0.6	1193
0.6-0.7	478
0.7-0.8	167
0.8-0.85	39
0.85-0.9	16
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9565	High Similarity	NPD1549	Phase 2
0.9493	High Similarity	NPD1552	Clinical (unspecified phase)
0.9493	High Similarity	NPD1550	Clinical (unspecified phase)
0.9301	High Similarity	NPD4378	Clinical (unspecified phase)
0.9262	High Similarity	NPD7075	Discontinued
0.9257	High Similarity	NPD8443	Clinical (unspecified phase)
0.9189	High Similarity	NPD2393	Clinical (unspecified phase)
0.9189	High Similarity	NPD7096	Clinical (unspecified phase)
0.9184	High Similarity	NPD7411	Suspended
0.9167	High Similarity	NPD7410	Clinical (unspecified phase)
0.9143	High Similarity	NPD2796	Approved
0.9116	High Similarity	NPD4380	Phase 2
0.9071	High Similarity	NPD1510	Phase 2
0.906	High Similarity	NPD7819	Suspended
0.9058	High Similarity	NPD1240	Approved
0.8929	High Similarity	NPD1607	Approved
0.8867	High Similarity	NPD6801	Discontinued
0.8867	High Similarity	NPD1934	Approved
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.8707	High Similarity	NPD6799	Approved
0.8693	High Similarity	NPD7768	Phase 2
0.869	High Similarity	NPD7421	Clinical (unspecified phase)
0.8662	High Similarity	NPD7852	Clinical (unspecified phase)
0.8616	High Similarity	NPD7804	Clinical (unspecified phase)
0.859	High Similarity	NPD6959	Discontinued
0.8511	High Similarity	NPD6859	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8456	Intermediate Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD3882	Suspended
0.8442	Intermediate Similarity	NPD2801	Approved
0.8428	Intermediate Similarity	NPD6166	Phase 2
0.8428	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD5494	Approved
0.8403	Intermediate Similarity	NPD6651	Approved
0.8378	Intermediate Similarity	NPD3750	Approved
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8344	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8311	Intermediate Similarity	NPD2800	Approved
0.8289	Intermediate Similarity	NPD5403	Approved
0.828	Intermediate Similarity	NPD3749	Approved
0.8272	Intermediate Similarity	NPD7286	Phase 2
0.8272	Intermediate Similarity	NPD7054	Approved
0.8261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6559	Discontinued
0.8231	Intermediate Similarity	NPD2935	Discontinued
0.8221	Intermediate Similarity	NPD7472	Approved
0.8217	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD3818	Discontinued
0.8188	Intermediate Similarity	NPD1243	Approved
0.8171	Intermediate Similarity	NPD5953	Discontinued
0.817	Intermediate Similarity	NPD920	Approved
0.8163	Intermediate Similarity	NPD2799	Discontinued
0.8158	Intermediate Similarity	NPD5401	Approved
0.8153	Intermediate Similarity	NPD3817	Phase 2
0.8146	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7251	Discontinued
0.8121	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD6832	Phase 2
0.8072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7808	Phase 3
0.8061	Intermediate Similarity	NPD6797	Phase 2
0.8054	Intermediate Similarity	NPD2344	Approved
0.8049	Intermediate Similarity	NPD5844	Phase 1
0.8041	Intermediate Similarity	NPD3748	Approved
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2532	Approved
0.8037	Intermediate Similarity	NPD7473	Discontinued
0.8028	Intermediate Similarity	NPD1203	Approved
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD6100	Approved
0.7986	Intermediate Similarity	NPD4908	Phase 1
0.7963	Intermediate Similarity	NPD6232	Discontinued
0.7962	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD7033	Discontinued
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1610	Phase 2
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2309	Approved
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7838	Intermediate Similarity	NPD5124	Phase 1
0.7838	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD3226	Approved
0.7829	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD9717	Approved
0.7816	Intermediate Similarity	NPD4363	Phase 3
0.7816	Intermediate Similarity	NPD4360	Phase 2
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD919	Approved
0.777	Intermediate Similarity	NPD943	Approved
0.7755	Intermediate Similarity	NPD3268	Approved
0.7738	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2798	Approved
0.7683	Intermediate Similarity	NPD1247	Approved
0.7679	Intermediate Similarity	NPD1729	Discontinued
0.7655	Intermediate Similarity	NPD2797	Approved
0.7628	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD422	Phase 1
0.761	Intermediate Similarity	NPD7458	Discontinued
0.761	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1933	Approved
0.76	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7589	Intermediate Similarity	NPD9545	Approved
0.7588	Intermediate Similarity	NPD6104	Discontinued
0.758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4361	Phase 2
0.7571	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3972	Approved
0.7568	Intermediate Similarity	NPD4625	Phase 3
0.7566	Intermediate Similarity	NPD4308	Phase 3
0.7541	Intermediate Similarity	NPD7584	Approved
0.7533	Intermediate Similarity	NPD1613	Approved
0.7533	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD5710	Approved
0.7517	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1241	Discontinued
0.7469	Intermediate Similarity	NPD6844	Discontinued
0.7466	Intermediate Similarity	NPD3225	Approved
0.7456	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9493	Approved
0.744	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7415	Intermediate Similarity	NPD3266	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.74	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4288	Approved
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7362	Intermediate Similarity	NPD7577	Discontinued
0.7358	Intermediate Similarity	NPD4662	Approved
0.7358	Intermediate Similarity	NPD4661	Approved
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7346	Intermediate Similarity	NPD6585	Discontinued
0.7329	Intermediate Similarity	NPD1608	Approved
0.7325	Intermediate Similarity	NPD7003	Approved
0.7317	Intermediate Similarity	NPD8455	Phase 2
0.7317	Intermediate Similarity	NPD5761	Phase 2
0.7317	Intermediate Similarity	NPD5760	Phase 2
0.7315	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2861	Phase 2
0.7308	Intermediate Similarity	NPD2424	Discontinued
0.7303	Intermediate Similarity	NPD3142	Approved
0.7303	Intermediate Similarity	NPD4307	Phase 2
0.7303	Intermediate Similarity	NPD3140	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD1164	Approved
0.7296	Intermediate Similarity	NPD7213	Phase 3
0.7296	Intermediate Similarity	NPD7212	Phase 2
0.729	Intermediate Similarity	NPD5406	Approved
0.729	Intermediate Similarity	NPD5408	Approved
0.729	Intermediate Similarity	NPD5405	Approved
0.729	Intermediate Similarity	NPD5404	Approved
0.7288	Intermediate Similarity	NPD4287	Approved
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7285	Intermediate Similarity	NPD411	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7279	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD3887	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD2296	Approved
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.726	Intermediate Similarity	NPD1201	Approved
0.7255	Intermediate Similarity	NPD447	Suspended
0.725	Intermediate Similarity	NPD7447	Phase 1
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7233	Intermediate Similarity	NPD7440	Discontinued
0.7225	Intermediate Similarity	NPD3823	Discontinued
0.7219	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6780	Approved
0.7213	Intermediate Similarity	NPD6781	Approved
0.7213	Intermediate Similarity	NPD6778	Approved
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6776	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