NPASS Compound

Structure

CID3188 OpenBabel06191715322D 22 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 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 3.4641 -0.0000 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 4.3301 0.5000 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 -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 -2.5981 0.5000 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 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 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 -0.8660 1.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	2.921
LogD:	2.61
LogS:	-3.263
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	2.667
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	1.3758823115495034e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	99.75736236572266%
Volume Distribution (VD):	0.469
Pgp-substrate:	0.8247584104537964%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.722
CYP2C9-substrate:	0.646
CYP2D6-inhibitor:	0.412
CYP2D6-substrate:	0.416
CYP3A4-inhibitor:	0.541
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	13.34
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.896
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.933
Carcinogencity:	0.737
Eye Corrosion:	0.003
Eye Irritation:	0.917
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC3188

Natural Product ID:	NPC3188
*Common Name:**	(E)-5,7-Dihydroxy-3-(4'-Hydroxybenzylidene)-6-Methylchroman-4-One
IUPAC Name:	(3E)-5,7-dihydroxy-3-[(4-hydroxyphenyl)methylidene]-6-methylchromen-4-one
Synonyms:
Standard InCHIKey:	QQNUVAQAOFSXSN-IZZDOVSWSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-9-13(19)7-14-15(16(9)20)17(21)11(8-22-14)6-10-2-4-12(18)5-3-10/h2-7,18-20H,8H2,1H3/b11-6+
SMILES:	Cc1c(cc2c(c1O)C(=O)/C(=C/c1ccc(cc1)O)/CO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078177
PubChem CID:	44557156
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids

*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
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	>	100000.0	nM	PMID[571494]

☑ 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 NPC3188 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	356
0.1-0.2	1580
0.2-0.3	4097
0.3-0.4	10544
0.4-0.5	7584
0.5-0.6	3550
0.6-0.7	5653
0.7-0.8	5101
0.8-0.85	2104
0.85-0.9	1266
0.9-0.95	636
0.95-1	226

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC150408
0.9854	High Similarity	NPC310130
0.9854	High Similarity	NPC164980
0.9854	High Similarity	NPC91560
0.9854	High Similarity	NPC175504
0.9854	High Similarity	NPC75049
0.9854	High Similarity	NPC143896
0.9854	High Similarity	NPC221432
0.9854	High Similarity	NPC149026
0.9854	High Similarity	NPC68104
0.9854	High Similarity	NPC169591
0.9854	High Similarity	NPC257097
0.9854	High Similarity	NPC39329
0.9853	High Similarity	NPC213322
0.9853	High Similarity	NPC324386
0.9853	High Similarity	NPC312391
0.9853	High Similarity	NPC4743
0.9783	High Similarity	NPC209040
0.9783	High Similarity	NPC197252
0.9783	High Similarity	NPC473013
0.9783	High Similarity	NPC473015
0.9783	High Similarity	NPC236766
0.9781	High Similarity	NPC223500
0.9781	High Similarity	NPC125855
0.9781	High Similarity	NPC107572
0.9781	High Similarity	NPC265040
0.9781	High Similarity	NPC10937
0.9781	High Similarity	NPC324436
0.9781	High Similarity	NPC167624
0.9781	High Similarity	NPC40833
0.9781	High Similarity	NPC1089
0.9781	High Similarity	NPC161506
0.9781	High Similarity	NPC228504
0.9781	High Similarity	NPC78
0.9781	High Similarity	NPC66515
0.9781	High Similarity	NPC166482
0.9781	High Similarity	NPC194432
0.9781	High Similarity	NPC328164
0.9781	High Similarity	NPC32739
0.9781	High Similarity	NPC227579
0.9781	High Similarity	NPC64915
0.9781	High Similarity	NPC148757
0.9781	High Similarity	NPC324134
0.9781	High Similarity	NPC76372
0.9781	High Similarity	NPC220998
0.9781	High Similarity	NPC182852
0.9781	High Similarity	NPC296917
0.9781	High Similarity	NPC37496
0.9781	High Similarity	NPC166934
0.9781	High Similarity	NPC177354
0.9781	High Similarity	NPC306829
0.9781	High Similarity	NPC76338
0.9779	High Similarity	NPC69769
0.9778	High Similarity	NPC99333
0.9778	High Similarity	NPC280284
0.9778	High Similarity	NPC188947
0.971	High Similarity	NPC478086
0.971	High Similarity	NPC125894
0.971	High Similarity	NPC278249
0.971	High Similarity	NPC223812
0.971	High Similarity	NPC214166
0.971	High Similarity	NPC185276
0.971	High Similarity	NPC77794
0.971	High Similarity	NPC85162
0.971	High Similarity	NPC18585
0.971	High Similarity	NPC81697
0.971	High Similarity	NPC166138
0.971	High Similarity	NPC316816
0.971	High Similarity	NPC107177
0.971	High Similarity	NPC106985
0.9708	High Similarity	NPC166689
0.9708	High Similarity	NPC96408
0.9708	High Similarity	NPC279650
0.9708	High Similarity	NPC248372
0.9708	High Similarity	NPC258630
0.9708	High Similarity	NPC17170
0.9708	High Similarity	NPC156190
0.9708	High Similarity	NPC110969
0.9708	High Similarity	NPC110038
0.9706	High Similarity	NPC150648
0.9706	High Similarity	NPC222342
0.9706	High Similarity	NPC274784
0.9706	High Similarity	NPC329203
0.9706	High Similarity	NPC78913
0.9706	High Similarity	NPC18260
0.9706	High Similarity	NPC225153
0.9706	High Similarity	NPC265871
0.9706	High Similarity	NPC20709
0.9706	High Similarity	NPC261234
0.9706	High Similarity	NPC310135
0.9704	High Similarity	NPC275055
0.9704	High Similarity	NPC290291
0.9643	High Similarity	NPC110303
0.9643	High Similarity	NPC23728
0.964	High Similarity	NPC235217
0.964	High Similarity	NPC131579
0.964	High Similarity	NPC473014
0.964	High Similarity	NPC271288
0.964	High Similarity	NPC131568
0.9638	High Similarity	NPC202981
0.9638	High Similarity	NPC147145
0.9638	High Similarity	NPC226636
0.9638	High Similarity	NPC144499
0.9638	High Similarity	NPC11561
0.9635	High Similarity	NPC284550
0.9635	High Similarity	NPC76445
0.9635	High Similarity	NPC241100
0.9635	High Similarity	NPC110228
0.9635	High Similarity	NPC6407
0.9635	High Similarity	NPC188243
0.9635	High Similarity	NPC270883
0.9635	High Similarity	NPC172986
0.9635	High Similarity	NPC261227
0.9635	High Similarity	NPC159275
0.9635	High Similarity	NPC129853
0.9632	High Similarity	NPC118813
0.9632	High Similarity	NPC201395
0.9632	High Similarity	NPC124269
0.9632	High Similarity	NPC472460
0.9632	High Similarity	NPC147686
0.9632	High Similarity	NPC329225
0.9574	High Similarity	NPC39195
0.9574	High Similarity	NPC132592
0.9574	High Similarity	NPC160821
0.9571	High Similarity	NPC312973
0.9571	High Similarity	NPC267375
0.9571	High Similarity	NPC88964
0.9571	High Similarity	NPC285630
0.9571	High Similarity	NPC470132
0.9571	High Similarity	NPC301276
0.9571	High Similarity	NPC470133
0.9571	High Similarity	NPC475052
0.9571	High Similarity	NPC127059
0.9571	High Similarity	NPC470131
0.9571	High Similarity	NPC111786
0.9571	High Similarity	NPC67805
0.9571	High Similarity	NPC473078
0.9571	High Similarity	NPC470647
0.9571	High Similarity	NPC195621
0.9571	High Similarity	NPC472629
0.9571	High Similarity	NPC54577
0.9571	High Similarity	NPC477955
0.9571	High Similarity	NPC83357
0.9571	High Similarity	NPC109183
0.9571	High Similarity	NPC246948
0.9571	High Similarity	NPC142405
0.9571	High Similarity	NPC214774
0.9571	High Similarity	NPC470134
0.9571	High Similarity	NPC176229
0.9571	High Similarity	NPC20488
0.9568	High Similarity	NPC38219
0.9565	High Similarity	NPC118840
0.9565	High Similarity	NPC64908
0.9565	High Similarity	NPC282300
0.9565	High Similarity	NPC156590
0.9565	High Similarity	NPC147688
0.9565	High Similarity	NPC205006
0.9565	High Similarity	NPC103362
0.9562	High Similarity	NPC216978
0.9562	High Similarity	NPC301217
0.9562	High Similarity	NPC220062
0.9562	High Similarity	NPC303633
0.9562	High Similarity	NPC217186
0.9562	High Similarity	NPC53181
0.9562	High Similarity	NPC295384
0.9562	High Similarity	NPC96565
0.9562	High Similarity	NPC140890
0.9562	High Similarity	NPC55018
0.9559	High Similarity	NPC32441
0.9559	High Similarity	NPC287246
0.9559	High Similarity	NPC12296
0.9559	High Similarity	NPC296490
0.9559	High Similarity	NPC13768
0.9559	High Similarity	NPC250266
0.9559	High Similarity	NPC243083
0.9559	High Similarity	NPC476480
0.9559	High Similarity	NPC295261
0.9559	High Similarity	NPC266597
0.9559	High Similarity	NPC188879
0.9559	High Similarity	NPC107586
0.9559	High Similarity	NPC84585
0.9559	High Similarity	NPC79943
0.9556	High Similarity	NPC239495
0.9556	High Similarity	NPC9985
0.9504	High Similarity	NPC283234
0.9504	High Similarity	NPC296998
0.9504	High Similarity	NPC472627
0.9504	High Similarity	NPC201731
0.9504	High Similarity	NPC473077
0.9504	High Similarity	NPC24673
0.9504	High Similarity	NPC300988
0.9504	High Similarity	NPC97716
0.9504	High Similarity	NPC79469
0.9504	High Similarity	NPC10990
0.9504	High Similarity	NPC308200
0.9504	High Similarity	NPC237635
0.9504	High Similarity	NPC104406
0.95	High Similarity	NPC87486
0.95	High Similarity	NPC110776
0.95	High Similarity	NPC271590

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 NPC3188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	959
0.2-0.3	1489
0.3-0.4	2571
0.4-0.5	1918
0.5-0.6	1197
0.6-0.7	467
0.7-0.8	146
0.8-0.85	47
0.85-0.9	20
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9632	High Similarity	NPD1549	Phase 2
0.9559	High Similarity	NPD1550	Clinical (unspecified phase)
0.9559	High Similarity	NPD1552	Clinical (unspecified phase)
0.9362	High Similarity	NPD4378	Clinical (unspecified phase)
0.927	High Similarity	NPD1510	Phase 2
0.9259	High Similarity	NPD1240	Approved
0.9241	High Similarity	NPD7411	Suspended
0.9225	High Similarity	NPD7410	Clinical (unspecified phase)
0.9124	High Similarity	NPD1607	Approved
0.9116	High Similarity	NPD2393	Clinical (unspecified phase)
0.9065	High Similarity	NPD2796	Approved
0.906	High Similarity	NPD7075	Discontinued
0.9054	High Similarity	NPD8443	Clinical (unspecified phase)
0.9041	High Similarity	NPD4380	Phase 2
0.8986	High Similarity	NPD7096	Clinical (unspecified phase)
0.8986	High Similarity	NPD7819	Suspended
0.8919	High Similarity	NPD1934	Approved
0.8792	High Similarity	NPD6801	Discontinued
0.8759	High Similarity	NPD6799	Approved
0.8741	High Similarity	NPD7421	Clinical (unspecified phase)
0.871	High Similarity	NPD7852	Clinical (unspecified phase)
0.8684	High Similarity	NPD4381	Clinical (unspecified phase)
0.863	High Similarity	NPD1511	Approved
0.8618	High Similarity	NPD7768	Phase 2
0.8552	High Similarity	NPD3750	Approved
0.8533	High Similarity	NPD6599	Discontinued
0.8531	High Similarity	NPD1551	Phase 2
0.8516	High Similarity	NPD6959	Discontinued
0.8514	High Similarity	NPD1512	Approved
0.8497	Intermediate Similarity	NPD3882	Suspended
0.8487	Intermediate Similarity	NPD2801	Approved
0.8483	Intermediate Similarity	NPD2800	Approved
0.8442	Intermediate Similarity	NPD3749	Approved
0.8429	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1243	Approved
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD920	Approved
0.8322	Intermediate Similarity	NPD6651	Approved
0.8311	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD2935	Discontinued
0.8219	Intermediate Similarity	NPD2344	Approved
0.8212	Intermediate Similarity	NPD5403	Approved
0.821	Intermediate Similarity	NPD5953	Discontinued
0.8207	Intermediate Similarity	NPD3748	Approved
0.8207	Intermediate Similarity	NPD2799	Discontinued
0.8201	Intermediate Similarity	NPD1203	Approved
0.82	Intermediate Similarity	NPD5401	Approved
0.82	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7286	Phase 2
0.8194	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD2313	Discontinued
0.816	Intermediate Similarity	NPD6559	Discontinued
0.8148	Intermediate Similarity	NPD7074	Phase 3
0.8141	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7054	Approved
0.8082	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2533	Approved
0.8079	Intermediate Similarity	NPD2532	Approved
0.8043	Intermediate Similarity	NPD1610	Phase 2
0.8037	Intermediate Similarity	NPD7472	Approved
0.8028	Intermediate Similarity	NPD4908	Phase 1
0.8028	Intermediate Similarity	NPD6832	Phase 2
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD2309	Approved
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD3226	Approved
0.7986	Intermediate Similarity	NPD9717	Approved
0.7975	Intermediate Similarity	NPD5844	Phase 1
0.7973	Intermediate Similarity	NPD2346	Discontinued
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7939	Intermediate Similarity	NPD7251	Discontinued
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7931	Intermediate Similarity	NPD943	Approved
0.7925	Intermediate Similarity	NPD919	Approved
0.7905	Intermediate Similarity	NPD6100	Approved
0.7905	Intermediate Similarity	NPD6099	Approved
0.7892	Intermediate Similarity	NPD7808	Phase 3
0.7848	Intermediate Similarity	NPD5402	Approved
0.7838	Intermediate Similarity	NPD7033	Discontinued
0.7826	Intermediate Similarity	NPD1247	Approved
0.7815	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD3268	Approved
0.7786	Intermediate Similarity	NPD422	Phase 1
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2798	Approved
0.7755	Intermediate Similarity	NPD5124	Phase 1
0.7755	Intermediate Similarity	NPD1933	Approved
0.7755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD9545	Approved
0.7746	Intermediate Similarity	NPD4363	Phase 3
0.7746	Intermediate Similarity	NPD4360	Phase 2
0.7718	Intermediate Similarity	NPD4308	Phase 3
0.7711	Intermediate Similarity	NPD1729	Discontinued
0.7692	Intermediate Similarity	NPD2797	Approved
0.7673	Intermediate Similarity	NPD1465	Phase 2
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7390	Discontinued
0.7657	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1241	Discontinued
0.7635	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2654	Approved
0.7622	Intermediate Similarity	NPD3225	Approved
0.7622	Intermediate Similarity	NPD3926	Phase 2
0.7609	Intermediate Similarity	NPD9493	Approved
0.7606	Intermediate Similarity	NPD3972	Approved
0.7603	Intermediate Similarity	NPD4625	Phase 3
0.76	Intermediate Similarity	NPD4361	Phase 2
0.76	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3266	Approved
0.7569	Intermediate Similarity	NPD3267	Approved
0.7568	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1613	Approved
0.7561	Intermediate Similarity	NPD5711	Approved
0.7561	Intermediate Similarity	NPD5710	Approved
0.7547	Intermediate Similarity	NPD5889	Approved
0.7547	Intermediate Similarity	NPD5890	Approved
0.7534	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7532	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1019	Discontinued
0.7517	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4288	Approved
0.7515	Intermediate Similarity	NPD6104	Discontinued
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1608	Approved
0.7466	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4307	Phase 2
0.7448	Intermediate Similarity	NPD1164	Approved
0.7448	Intermediate Similarity	NPD1470	Approved
0.7432	Intermediate Similarity	NPD1296	Phase 2
0.7432	Intermediate Similarity	NPD3764	Approved
0.7432	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD6798	Discontinued
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4287	Approved
0.7413	Intermediate Similarity	NPD1201	Approved
0.7407	Intermediate Similarity	NPD2296	Approved
0.74	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7381	Intermediate Similarity	NPD3751	Discontinued
0.7377	Intermediate Similarity	NPD7584	Approved
0.7375	Intermediate Similarity	NPD6585	Discontinued
0.7355	Intermediate Similarity	NPD7003	Approved
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7333	Intermediate Similarity	NPD3140	Approved
0.7333	Intermediate Similarity	NPD3142	Approved
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.732	Intermediate Similarity	NPD5408	Approved
0.732	Intermediate Similarity	NPD5404	Approved
0.732	Intermediate Similarity	NPD5405	Approved
0.732	Intermediate Similarity	NPD5406	Approved
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD2354	Approved
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7284	Intermediate Similarity	NPD7577	Discontinued
0.7278	Intermediate Similarity	NPD4662	Approved
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4661	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7262	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1876	Approved
0.7255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1894	Discontinued
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7233	Intermediate Similarity	NPD5049	Phase 3
0.723	Intermediate Similarity	NPD2861	Phase 2
0.7226	Intermediate Similarity	NPD2424	Discontinued
0.7215	Intermediate Similarity	NPD7213	Phase 3
0.7215	Intermediate Similarity	NPD7212	Phase 2
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4477	Approved
0.7208	Intermediate Similarity	NPD4476	Approved
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3887	Approved
0.7186	Intermediate Similarity	NPD7199	Phase 2
0.7179	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD6279	Approved
0.7178	Intermediate Similarity	NPD6280	Approved
0.7176	Intermediate Similarity	NPD7177	Discontinued
0.7176	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1535	Discovery

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