NPASS Compound

Structure

CID215885 OpenBabel06191716002D 23 25 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 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 3.4641 -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 3.4641 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -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 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 -0.8660 1.5000 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 -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 -1.7321 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 10 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 19 2 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 20 2 0 0 0 0 14 11 1 1 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	4.121
LogD:	2.701
LogS:	-4.07
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.881
Synthetic Accessibility Score:	3.148
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	1.5236147191899363e-05
Pgp-inhibitor:	0.326
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	97.19415283203125%
Volume Distribution (VD):	0.638
Pgp-substrate:	1.6949726343154907%

ADMET: Metabolism

CYP1A2-inhibitor:	0.365
CYP1A2-substrate:	0.673
CYP2C19-inhibitor:	0.846
CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.168
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	3.129
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.475
Skin Sensitization:	0.547
Carcinogencity:	0.85
Eye Corrosion:	0.004
Eye Irritation:	0.896
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC215885

Natural Product ID:	NPC215885
*Common Name:**	(S)-5-Hydroxy-7-Methoxy-8-Methyl-4-Oxo-2-Phenylchroman-6-Carbaldehyde
IUPAC Name:	(2S)-5-hydroxy-7-methoxy-8-methyl-4-oxo-2-phenyl-2,3-dihydrochromene-6-carbaldehyde
Synonyms:
Standard InCHIKey:	HGTSZOYDQGUVER-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-10-17(22-2)12(9-19)16(21)15-13(20)8-14(23-18(10)15)11-6-4-3-5-7-11/h3-7,9,14,21H,8H2,1-2H3/t14-/m0/s1
SMILES:	COc1c(C)c2O[C@@H](CC(=O)c2c(c1C=O)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1271363
PubChem CID:	52945746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	flower bud	n.a.	DOI[10.1021/np1002753]
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20886838]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	256250.0	nM	PMID[496507]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	268590.0	nM	PMID[496507]

☑ 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 NPC215885 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	361
0.1-0.2	1601
0.2-0.3	4143
0.3-0.4	10760
0.4-0.5	7630
0.5-0.6	3972
0.6-0.7	5919
0.7-0.8	5104
0.8-0.85	1752
0.85-0.9	1010
0.9-0.95	389
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC2416
1.0	High Similarity	NPC476153
0.9928	High Similarity	NPC271590
0.9928	High Similarity	NPC110776
0.9789	High Similarity	NPC214493
0.9714	High Similarity	NPC471621
0.9712	High Similarity	NPC110038
0.9712	High Similarity	NPC248372
0.9643	High Similarity	NPC10937
0.9643	High Similarity	NPC37496
0.9643	High Similarity	NPC324436
0.9643	High Similarity	NPC76338
0.9643	High Similarity	NPC328164
0.9643	High Similarity	NPC64915
0.9643	High Similarity	NPC227579
0.9643	High Similarity	NPC1089
0.9643	High Similarity	NPC265040
0.9643	High Similarity	NPC228504
0.9643	High Similarity	NPC223500
0.9643	High Similarity	NPC161506
0.9643	High Similarity	NPC40833
0.9643	High Similarity	NPC296917
0.9643	High Similarity	NPC32739
0.9643	High Similarity	NPC182852
0.9643	High Similarity	NPC78
0.9643	High Similarity	NPC66515
0.9643	High Similarity	NPC166482
0.9643	High Similarity	NPC148757
0.9643	High Similarity	NPC76372
0.9643	High Similarity	NPC107572
0.9643	High Similarity	NPC194432
0.9643	High Similarity	NPC324134
0.9643	High Similarity	NPC306829
0.9643	High Similarity	NPC166934
0.9643	High Similarity	NPC177354
0.9643	High Similarity	NPC220998
0.9643	High Similarity	NPC125855
0.9643	High Similarity	NPC167624
0.9574	High Similarity	NPC68104
0.9574	High Similarity	NPC310130
0.9574	High Similarity	NPC125894
0.9574	High Similarity	NPC257097
0.9574	High Similarity	NPC175504
0.9574	High Similarity	NPC85162
0.9574	High Similarity	NPC221432
0.9574	High Similarity	NPC143896
0.9574	High Similarity	NPC278249
0.9574	High Similarity	NPC91560
0.9574	High Similarity	NPC150408
0.9574	High Similarity	NPC223812
0.9574	High Similarity	NPC164980
0.9574	High Similarity	NPC478086
0.9574	High Similarity	NPC316816
0.9574	High Similarity	NPC39329
0.9574	High Similarity	NPC149026
0.9574	High Similarity	NPC185276
0.9574	High Similarity	NPC214166
0.9574	High Similarity	NPC107177
0.9574	High Similarity	NPC75049
0.9574	High Similarity	NPC81697
0.9574	High Similarity	NPC169591
0.9574	High Similarity	NPC77794
0.9571	High Similarity	NPC96408
0.9571	High Similarity	NPC22467
0.9571	High Similarity	NPC4743
0.9571	High Similarity	NPC156190
0.9571	High Similarity	NPC279650
0.9571	High Similarity	NPC324386
0.9571	High Similarity	NPC312391
0.9571	High Similarity	NPC213322
0.9571	High Similarity	NPC17170
0.9571	High Similarity	NPC166689
0.9571	High Similarity	NPC258630
0.9507	High Similarity	NPC197252
0.9507	High Similarity	NPC473015
0.9507	High Similarity	NPC131579
0.9507	High Similarity	NPC473014
0.9507	High Similarity	NPC235217
0.9507	High Similarity	NPC209040
0.9507	High Similarity	NPC236766
0.9507	High Similarity	NPC473013
0.9507	High Similarity	NPC131568
0.95	High Similarity	NPC188243
0.95	High Similarity	NPC110228
0.95	High Similarity	NPC6407
0.9441	High Similarity	NPC20488
0.9441	High Similarity	NPC111786
0.9441	High Similarity	NPC214774
0.9441	High Similarity	NPC228779
0.9441	High Similarity	NPC142405
0.9441	High Similarity	NPC470134
0.9441	High Similarity	NPC267375
0.9441	High Similarity	NPC285630
0.9441	High Similarity	NPC176229
0.9441	High Similarity	NPC470133
0.9441	High Similarity	NPC83357
0.9441	High Similarity	NPC195621
0.9441	High Similarity	NPC127059
0.9441	High Similarity	NPC470131
0.9441	High Similarity	NPC67805
0.9441	High Similarity	NPC473078
0.9441	High Similarity	NPC470647
0.9441	High Similarity	NPC88964
0.9441	High Similarity	NPC470132
0.9441	High Similarity	NPC312973
0.9441	High Similarity	NPC301276
0.9441	High Similarity	NPC54577
0.9441	High Similarity	NPC472629
0.9441	High Similarity	NPC475052
0.9441	High Similarity	NPC246948
0.9441	High Similarity	NPC109183
0.9433	High Similarity	NPC3188
0.9429	High Similarity	NPC53181
0.9429	High Similarity	NPC310135
0.9429	High Similarity	NPC225153
0.9429	High Similarity	NPC20709
0.9429	High Similarity	NPC140890
0.9429	High Similarity	NPC217186
0.9429	High Similarity	NPC222342
0.9429	High Similarity	NPC150648
0.9429	High Similarity	NPC274784
0.9429	High Similarity	NPC265871
0.9429	High Similarity	NPC329203
0.9375	High Similarity	NPC296998
0.9375	High Similarity	NPC473077
0.9375	High Similarity	NPC300988
0.9375	High Similarity	NPC23728
0.9375	High Similarity	NPC10990
0.9375	High Similarity	NPC472627
0.9375	High Similarity	NPC110303
0.9375	High Similarity	NPC283234
0.9371	High Similarity	NPC470135
0.9371	High Similarity	NPC87486
0.9371	High Similarity	NPC39045
0.9371	High Similarity	NPC470136
0.9371	High Similarity	NPC124780
0.9371	High Similarity	NPC319752
0.9371	High Similarity	NPC470890
0.9371	High Similarity	NPC271288
0.9366	High Similarity	NPC147145
0.9366	High Similarity	NPC266725
0.9362	High Similarity	NPC159275
0.9362	High Similarity	NPC69769
0.9362	High Similarity	NPC241100
0.9362	High Similarity	NPC76445
0.9362	High Similarity	NPC129853
0.9362	High Similarity	NPC284550
0.9357	High Similarity	NPC471620
0.931	High Similarity	NPC160821
0.931	High Similarity	NPC132592
0.931	High Similarity	NPC161191
0.9306	High Similarity	NPC476088
0.9306	High Similarity	NPC187282
0.9306	High Similarity	NPC82534
0.9306	High Similarity	NPC290133
0.9306	High Similarity	NPC24136
0.9306	High Similarity	NPC474161
0.9301	High Similarity	NPC18585
0.9301	High Similarity	NPC106985
0.9301	High Similarity	NPC166138
0.9296	High Similarity	NPC282300
0.9296	High Similarity	NPC110969
0.9291	High Similarity	NPC301217
0.9291	High Similarity	NPC303633
0.9291	High Similarity	NPC96565
0.9291	High Similarity	NPC216978
0.9291	High Similarity	NPC78913
0.9291	High Similarity	NPC18260
0.9291	High Similarity	NPC55018
0.9291	High Similarity	NPC220062
0.9286	High Similarity	NPC12296
0.9286	High Similarity	NPC296490
0.9286	High Similarity	NPC79943
0.9286	High Similarity	NPC295261
0.9286	High Similarity	NPC259685
0.9286	High Similarity	NPC287246
0.9286	High Similarity	NPC107586
0.9286	High Similarity	NPC243083
0.9286	High Similarity	NPC13768
0.9286	High Similarity	NPC32441
0.9257	High Similarity	NPC122365
0.9247	High Similarity	NPC19238
0.9247	High Similarity	NPC472628
0.9247	High Similarity	NPC3642
0.9247	High Similarity	NPC473016
0.9247	High Similarity	NPC164205
0.9247	High Similarity	NPC104236
0.9241	High Similarity	NPC308200
0.9236	High Similarity	NPC224714
0.9231	High Similarity	NPC144499
0.9231	High Similarity	NPC11561
0.9231	High Similarity	NPC226636
0.9225	High Similarity	NPC150522
0.9225	High Similarity	NPC261227
0.9225	High Similarity	NPC172986
0.9225	High Similarity	NPC270883
0.922	High Similarity	NPC118813
0.922	High Similarity	NPC188947
0.922	High Similarity	NPC329225
0.922	High Similarity	NPC99333

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 NPC215885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	958
0.2-0.3	1577
0.3-0.4	2672
0.4-0.5	1885
0.5-0.6	1159
0.6-0.7	397
0.7-0.8	122
0.8-0.85	30
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD1550	Clinical (unspecified phase)
0.9286	High Similarity	NPD1552	Clinical (unspecified phase)
0.922	High Similarity	NPD1549	Phase 2
0.9195	High Similarity	NPD8443	Clinical (unspecified phase)
0.9122	High Similarity	NPD7411	Suspended
0.9103	High Similarity	NPD4378	Clinical (unspecified phase)
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.8973	High Similarity	NPD7410	Clinical (unspecified phase)
0.8824	High Similarity	NPD7075	Discontinued
0.8811	High Similarity	NPD2796	Approved
0.88	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD7096	Clinical (unspecified phase)
0.8741	High Similarity	NPD1510	Phase 2
0.8723	High Similarity	NPD1240	Approved
0.8684	High Similarity	NPD1934	Approved
0.863	High Similarity	NPD7421	Clinical (unspecified phase)
0.8627	High Similarity	NPD7819	Suspended
0.8608	High Similarity	NPD7852	Clinical (unspecified phase)
0.8601	High Similarity	NPD1607	Approved
0.8562	High Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6959	Discontinued
0.84	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1551	Phase 2
0.828	Intermediate Similarity	NPD7768	Phase 2
0.8278	Intermediate Similarity	NPD1511	Approved
0.8269	Intermediate Similarity	NPD2801	Approved
0.8261	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6166	Phase 2
0.8261	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2800	Approved
0.8219	Intermediate Similarity	NPD6651	Approved
0.8194	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.817	Intermediate Similarity	NPD1512	Approved
0.8165	Intermediate Similarity	NPD3882	Suspended
0.8125	Intermediate Similarity	NPD5494	Approved
0.8117	Intermediate Similarity	NPD920	Approved
0.8092	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD3750	Approved
0.8061	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7952	Intermediate Similarity	NPD7472	Approved
0.7947	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3818	Discontinued
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7917	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6797	Phase 2
0.7904	Intermediate Similarity	NPD5953	Discontinued
0.7895	Intermediate Similarity	NPD1243	Approved
0.7892	Intermediate Similarity	NPD7286	Phase 2
0.7871	Intermediate Similarity	NPD5401	Approved
0.7867	Intermediate Similarity	NPD2799	Discontinued
0.7857	Intermediate Similarity	NPD7251	Discontinued
0.7853	Intermediate Similarity	NPD1247	Approved
0.7823	Intermediate Similarity	NPD2313	Discontinued
0.7823	Intermediate Similarity	NPD3268	Approved
0.7811	Intermediate Similarity	NPD7808	Phase 3
0.7808	Intermediate Similarity	NPD4908	Phase 1
0.7805	Intermediate Similarity	NPD6232	Discontinued
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7763	Intermediate Similarity	NPD2344	Approved
0.7748	Intermediate Similarity	NPD3748	Approved
0.7748	Intermediate Similarity	NPD7033	Discontinued
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7724	Intermediate Similarity	NPD1203	Approved
0.7706	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6099	Approved
0.7697	Intermediate Similarity	NPD6100	Approved
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7688	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6832	Phase 2
0.767	Intermediate Similarity	NPD4363	Phase 3
0.767	Intermediate Similarity	NPD4360	Phase 2
0.766	Intermediate Similarity	NPD1548	Phase 1
0.7654	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7632	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5890	Approved
0.7578	Intermediate Similarity	NPD5889	Approved
0.7564	Intermediate Similarity	NPD2309	Approved
0.7517	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD943	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7468	Intermediate Similarity	NPD7390	Discontinued
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD422	Phase 1
0.7436	Intermediate Similarity	NPD2654	Approved
0.7432	Intermediate Similarity	NPD2798	Approved
0.743	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4361	Phase 2
0.7427	Intermediate Similarity	NPD1729	Discontinued
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3225	Approved
0.7407	Intermediate Similarity	NPD6585	Discontinued
0.74	Intermediate Similarity	NPD4625	Phase 3
0.7368	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1613	Approved
0.7351	Intermediate Similarity	NPD6798	Discontinued
0.7346	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.732	Intermediate Similarity	NPD1933	Approved
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9545	Approved
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7279	Intermediate Similarity	NPD3972	Approved
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7263	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6104	Discontinued
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7584	Approved
0.7208	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.7183	Intermediate Similarity	NPD1241	Discontinued
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.7162	Intermediate Similarity	NPD1608	Approved
0.7159	Intermediate Similarity	NPD8313	Approved
0.7159	Intermediate Similarity	NPD8312	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD7213	Phase 3
0.7134	Intermediate Similarity	NPD5408	Approved
0.7134	Intermediate Similarity	NPD5406	Approved
0.7134	Intermediate Similarity	NPD5405	Approved
0.7134	Intermediate Similarity	NPD5404	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7124	Intermediate Similarity	NPD1296	Phase 2
0.7124	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4749	Approved
0.711	Intermediate Similarity	NPD3751	Discontinued
0.7108	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD1652	Phase 2
0.7099	Intermediate Similarity	NPD4662	Approved
0.7099	Intermediate Similarity	NPD4661	Approved
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD1201	Approved
0.7093	Intermediate Similarity	NPD2403	Approved
0.7093	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6002	Phase 3
0.7089	Intermediate Similarity	NPD6005	Phase 3
0.7089	Intermediate Similarity	NPD6004	Phase 3
0.7089	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1019	Discontinued
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7076	Intermediate Similarity	NPD6808	Phase 2
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7055	Intermediate Similarity	NPD5049	Phase 3
0.7055	Intermediate Similarity	NPD1894	Discontinued
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4307	Phase 2
0.7032	Intermediate Similarity	NPD3140	Approved
0.7032	Intermediate Similarity	NPD3142	Approved
0.7025	Intermediate Similarity	NPD4476	Approved
0.7025	Intermediate Similarity	NPD4477	Approved
0.7024	Intermediate Similarity	NPD2296	Approved
0.702	Intermediate Similarity	NPD1470	Approved
0.702	Intermediate Similarity	NPD1164	Approved
0.7019	Intermediate Similarity	NPD3887	Approved
0.7019	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7199	Phase 2

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