NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	586.1
Volume:	532.982
LogP:	1.43
LogD:	0.45
LogS:	-4.986
# Rotatable Bonds:	7
TPSA:	257.04
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	4.174
Fsp3:	0.185
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.349
MDCK Permeability:	9.78193202172406e-06
Pgp-inhibitor:	0.261
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.739
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	87.9762191772461%
Volume Distribution (VD):	0.663
Pgp-substrate:	16.24285316467285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.399
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	6.174
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.631
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.951
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.905
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC476773

Natural Product ID:	NPC476773
*Common Name:**	[3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxy-4-oxochromen-5-yl] 3,4,5-trihydroxybenzoate
IUPAC Name:	[3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxy-4-oxochromen-5-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	LFQZCBSAAFCIGV-GABSKDJNSA-N
Standard InCHI:	InChI=1S/C27H22O15/c28-8-18-21(35)23(37)27(41-18)42-25-22(36)19-16(39-24(25)9-1-2-12(30)13(31)3-9)6-11(29)7-17(19)40-26(38)10-4-14(32)20(34)15(33)5-10/h1-7,18,21,23,27-35,37H,8H2/t18-,21-,23+,27-/m0/s1
SMILES:	C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3OC(=O)C4=CC(=C(C(=C4)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H](O5)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11577879
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO33517	Calycolpus warszewiczianus	Species	Myrtaceae	Eukaryota	young leaves	Barro Colorado Nature Monument in Gatn Lake, Republic of Panama	2004-FEB	PMID[16724851]

☑ 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
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	86500	nM	PMID[16724851]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14500	nM	PMID[16724851]

☑ 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 NPC476773 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	438
0.1-0.2	1858
0.2-0.3	4205
0.3-0.4	9396
0.4-0.5	8871
0.5-0.6	4368
0.6-0.7	5492
0.7-0.8	5230
0.8-0.85	1746
0.85-0.9	813
0.9-0.95	271
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC296018
0.9939	High Similarity	NPC154741
0.9699	High Similarity	NPC144097
0.9699	High Similarity	NPC61904
0.9641	High Similarity	NPC35167
0.9641	High Similarity	NPC37668
0.9641	High Similarity	NPC113836
0.9641	High Similarity	NPC253521
0.9639	High Similarity	NPC214621
0.9639	High Similarity	NPC34267
0.9639	High Similarity	NPC223426
0.9639	High Similarity	NPC81042
0.9576	High Similarity	NPC20505
0.9576	High Similarity	NPC235260
0.9576	High Similarity	NPC155763
0.9524	High Similarity	NPC293626
0.9524	High Similarity	NPC258044
0.9524	High Similarity	NPC217387
0.9524	High Similarity	NPC217520
0.9524	High Similarity	NPC196127
0.9524	High Similarity	NPC267680
0.9524	High Similarity	NPC139571
0.9518	High Similarity	NPC175107
0.9518	High Similarity	NPC190003
0.9515	High Similarity	NPC138927
0.9512	High Similarity	NPC67037
0.9512	High Similarity	NPC255615
0.9471	High Similarity	NPC97119
0.9471	High Similarity	NPC135831
0.9471	High Similarity	NPC36138
0.9471	High Similarity	NPC297503
0.9461	High Similarity	NPC4390
0.9458	High Similarity	NPC244776
0.9458	High Similarity	NPC204937
0.9458	High Similarity	NPC116864
0.9458	High Similarity	NPC72249
0.9458	High Similarity	NPC149011
0.9455	High Similarity	NPC149244
0.9455	High Similarity	NPC48640
0.9451	High Similarity	NPC34531
0.9415	High Similarity	NPC470416
0.9408	High Similarity	NPC477895
0.9405	High Similarity	NPC43211
0.9405	High Similarity	NPC210094
0.9405	High Similarity	NPC115760
0.9405	High Similarity	NPC237435
0.9405	High Similarity	NPC253685
0.9405	High Similarity	NPC135277
0.9405	High Similarity	NPC49344
0.9405	High Similarity	NPC101191
0.9401	High Similarity	NPC153755
0.9401	High Similarity	NPC245452
0.9398	High Similarity	NPC476771
0.9394	High Similarity	NPC281131
0.9394	High Similarity	NPC145038
0.9394	High Similarity	NPC179950
0.9394	High Similarity	NPC253662
0.9394	High Similarity	NPC254306
0.9394	High Similarity	NPC276222
0.9394	High Similarity	NPC274618
0.9394	High Similarity	NPC118284
0.9394	High Similarity	NPC308404
0.9394	High Similarity	NPC56077
0.9394	High Similarity	NPC88789
0.9357	High Similarity	NPC156785
0.9357	High Similarity	NPC162394
0.9357	High Similarity	NPC241781
0.9357	High Similarity	NPC470718
0.9349	High Similarity	NPC472385
0.9349	High Similarity	NPC472991
0.9349	High Similarity	NPC198324
0.9349	High Similarity	NPC472992
0.9345	High Similarity	NPC472993
0.9345	High Similarity	NPC88560
0.9345	High Similarity	NPC175230
0.9345	High Similarity	NPC172033
0.9341	High Similarity	NPC206123
0.9337	High Similarity	NPC223424
0.9337	High Similarity	NPC127546
0.9337	High Similarity	NPC52550
0.9337	High Similarity	NPC317489
0.9337	High Similarity	NPC173637
0.9337	High Similarity	NPC84362
0.9333	High Similarity	NPC19388
0.9333	High Similarity	NPC55786
0.9333	High Similarity	NPC240431
0.9333	High Similarity	NPC277205
0.9302	High Similarity	NPC21359
0.9302	High Similarity	NPC25946
0.9302	High Similarity	NPC470720
0.9302	High Similarity	NPC470713
0.9302	High Similarity	NPC249560
0.9302	High Similarity	NPC460984
0.9302	High Similarity	NPC223860
0.9302	High Similarity	NPC275977
0.9302	High Similarity	NPC470717
0.929	High Similarity	NPC477848
0.929	High Similarity	NPC264735
0.9286	High Similarity	NPC47140
0.9286	High Similarity	NPC476772
0.9286	High Similarity	NPC67134
0.9281	High Similarity	NPC120099
0.9281	High Similarity	NPC225434
0.9281	High Similarity	NPC223747
0.9281	High Similarity	NPC219904
0.9281	High Similarity	NPC203050
0.9277	High Similarity	NPC197285
0.9277	High Similarity	NPC277174
0.9277	High Similarity	NPC73855
0.9277	High Similarity	NPC328940
0.9277	High Similarity	NPC135599
0.9277	High Similarity	NPC113968
0.9277	High Similarity	NPC21100
0.9273	High Similarity	NPC168822
0.9249	High Similarity	NPC470719
0.9249	High Similarity	NPC473554
0.9249	High Similarity	NPC295625
0.9249	High Similarity	NPC104910
0.9249	High Similarity	NPC474093
0.9249	High Similarity	NPC33083
0.9244	High Similarity	NPC35924
0.9244	High Similarity	NPC199172
0.9235	High Similarity	NPC233994
0.9235	High Similarity	NPC268533
0.9235	High Similarity	NPC211532
0.9235	High Similarity	NPC89127
0.9235	High Similarity	NPC471669
0.9231	High Similarity	NPC42773
0.9231	High Similarity	NPC101026
0.9231	High Similarity	NPC24043
0.9231	High Similarity	NPC45522
0.9231	High Similarity	NPC169977
0.9231	High Similarity	NPC21666
0.9226	High Similarity	NPC259896
0.9226	High Similarity	NPC255157
0.9226	High Similarity	NPC67326
0.9226	High Similarity	NPC84265
0.9226	High Similarity	NPC282987
0.9226	High Similarity	NPC254855
0.9226	High Similarity	NPC156869
0.9226	High Similarity	NPC245014
0.9226	High Similarity	NPC95866
0.9226	High Similarity	NPC29958
0.9226	High Similarity	NPC136042
0.9222	High Similarity	NPC92565
0.9222	High Similarity	NPC116745
0.9222	High Similarity	NPC226304
0.9222	High Similarity	NPC325555
0.9222	High Similarity	NPC265530
0.9222	High Similarity	NPC160156
0.9217	High Similarity	NPC85751
0.9217	High Similarity	NPC129264
0.9217	High Similarity	NPC19240
0.9217	High Similarity	NPC205824
0.9212	High Similarity	NPC77660
0.9212	High Similarity	NPC189142
0.9195	High Similarity	NPC475179
0.9195	High Similarity	NPC72554
0.9195	High Similarity	NPC97817
0.9195	High Similarity	NPC30011
0.9186	High Similarity	NPC473071
0.9186	High Similarity	NPC469371
0.9186	High Similarity	NPC222674
0.9186	High Similarity	NPC473073
0.9181	High Similarity	NPC476620
0.9181	High Similarity	NPC476623
0.9181	High Similarity	NPC476621
0.9181	High Similarity	NPC173837
0.9181	High Similarity	NPC476618
0.9181	High Similarity	NPC476619
0.9181	High Similarity	NPC476622
0.9172	High Similarity	NPC203259
0.9172	High Similarity	NPC60735
0.9172	High Similarity	NPC26230
0.9172	High Similarity	NPC134532
0.9172	High Similarity	NPC117260
0.9172	High Similarity	NPC471725
0.9172	High Similarity	NPC33054
0.9172	High Similarity	NPC471748
0.9172	High Similarity	NPC254540
0.9172	High Similarity	NPC211594
0.9172	High Similarity	NPC235575
0.9172	High Similarity	NPC172807
0.9172	High Similarity	NPC176740
0.9172	High Similarity	NPC155877
0.9172	High Similarity	NPC476405
0.9167	High Similarity	NPC280493
0.9167	High Similarity	NPC52382
0.9167	High Similarity	NPC270578
0.9157	High Similarity	NPC191306
0.9157	High Similarity	NPC19709
0.9157	High Similarity	NPC270335
0.9157	High Similarity	NPC88043
0.9157	High Similarity	NPC80068
0.9152	High Similarity	NPC282169
0.9133	High Similarity	NPC470446
0.9133	High Similarity	NPC107987
0.9133	High Similarity	NPC473072
0.9133	High Similarity	NPC470447
0.9133	High Similarity	NPC470445

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 NPC476773 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	922
0.2-0.3	2068
0.3-0.4	2684
0.4-0.5	1810
0.5-0.6	856
0.6-0.7	273
0.7-0.8	116
0.8-0.85	17
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9405	High Similarity	NPD4338	Clinical (unspecified phase)
0.9337	High Similarity	NPD3818	Discontinued
0.9172	High Similarity	NPD6797	Phase 2
0.9118	High Similarity	NPD7251	Discontinued
0.8953	High Similarity	NPD7808	Phase 3
0.8941	High Similarity	NPD7054	Approved
0.8889	High Similarity	NPD7472	Approved
0.8855	High Similarity	NPD4381	Clinical (unspecified phase)
0.8795	High Similarity	NPD4868	Clinical (unspecified phase)
0.8795	High Similarity	NPD3882	Suspended
0.8779	High Similarity	NPD7074	Phase 3
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.8735	High Similarity	NPD3817	Phase 2
0.8623	High Similarity	NPD5402	Approved
0.8621	High Similarity	NPD7993	Clinical (unspecified phase)
0.8613	High Similarity	NPD7804	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD1512	Approved
0.8466	Intermediate Similarity	NPD6559	Discontinued
0.8452	Intermediate Similarity	NPD2801	Approved
0.8424	Intermediate Similarity	NPD5403	Approved
0.8412	Intermediate Similarity	NPD7075	Discontinued
0.8393	Intermediate Similarity	NPD1934	Approved
0.8393	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD1511	Approved
0.8343	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5401	Approved
0.8274	Intermediate Similarity	NPD4380	Phase 2
0.8242	Intermediate Similarity	NPD6799	Approved
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1653	Approved
0.8152	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD5844	Phase 1
0.8057	Intermediate Similarity	NPD7199	Phase 2
0.8046	Intermediate Similarity	NPD919	Approved
0.8034	Intermediate Similarity	NPD3751	Discontinued
0.8023	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD6190	Approved
0.8011	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD5494	Approved
0.7989	Intermediate Similarity	NPD3749	Approved
0.7978	Intermediate Similarity	NPD7473	Discontinued
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8312	Approved
0.7967	Intermediate Similarity	NPD8313	Approved
0.7956	Intermediate Similarity	NPD7685	Pre-registration
0.7953	Intermediate Similarity	NPD6599	Discontinued
0.7946	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6234	Discontinued
0.7933	Intermediate Similarity	NPD7228	Approved
0.791	Intermediate Similarity	NPD3787	Discontinued
0.787	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD37	Approved
0.7831	Intermediate Similarity	NPD1549	Phase 2
0.7829	Intermediate Similarity	NPD4966	Approved
0.7829	Intermediate Similarity	NPD4967	Phase 2
0.7829	Intermediate Similarity	NPD4965	Approved
0.7816	Intermediate Similarity	NPD7819	Suspended
0.7811	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3926	Phase 2
0.7758	Intermediate Similarity	NPD1510	Phase 2
0.7753	Intermediate Similarity	NPD1247	Approved
0.7738	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7435	Discontinued
0.7722	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD2796	Approved
0.7696	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6959	Discontinued
0.7633	Intermediate Similarity	NPD3750	Approved
0.7627	Intermediate Similarity	NPD7768	Phase 2
0.7626	Intermediate Similarity	NPD8151	Discontinued
0.7577	Intermediate Similarity	NPD6778	Approved
0.7577	Intermediate Similarity	NPD6779	Approved
0.7577	Intermediate Similarity	NPD6781	Approved
0.7577	Intermediate Similarity	NPD6782	Approved
0.7577	Intermediate Similarity	NPD6777	Approved
0.7577	Intermediate Similarity	NPD6780	Approved
0.7577	Intermediate Similarity	NPD6776	Approved
0.7576	Intermediate Similarity	NPD230	Phase 1
0.7572	Intermediate Similarity	NPD920	Approved
0.756	Intermediate Similarity	NPD7266	Discontinued
0.7558	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD943	Approved
0.7514	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.7473	Intermediate Similarity	NPD7240	Approved
0.7471	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD447	Suspended
0.7463	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7783	Phase 2
0.746	Intermediate Similarity	NPD8434	Phase 2
0.7457	Intermediate Similarity	NPD2533	Approved
0.7457	Intermediate Similarity	NPD2534	Approved
0.7457	Intermediate Similarity	NPD2532	Approved
0.7442	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4628	Phase 3
0.7424	Intermediate Similarity	NPD7870	Phase 2
0.7424	Intermediate Similarity	NPD7871	Phase 2
0.741	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1613	Approved
0.7386	Intermediate Similarity	NPD3226	Approved
0.7374	Intermediate Similarity	NPD7697	Approved
0.7374	Intermediate Similarity	NPD7698	Approved
0.7374	Intermediate Similarity	NPD7696	Phase 3
0.7368	Intermediate Similarity	NPD1243	Approved
0.7365	Intermediate Similarity	NPD1933	Approved
0.7356	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7584	Approved
0.7337	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD3748	Approved
0.7337	Intermediate Similarity	NPD8319	Approved
0.7321	Intermediate Similarity	NPD1607	Approved
0.732	Intermediate Similarity	NPD6534	Approved
0.732	Intermediate Similarity	NPD6535	Approved
0.7313	Intermediate Similarity	NPD7701	Phase 2
0.7294	Intermediate Similarity	NPD2935	Discontinued
0.7289	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6798	Discontinued
0.7277	Intermediate Similarity	NPD8150	Discontinued
0.7246	Intermediate Similarity	NPD6233	Phase 2
0.7243	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5953	Discontinued
0.7228	Intermediate Similarity	NPD7585	Approved
0.7225	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7700	Phase 2
0.7206	Intermediate Similarity	NPD7801	Approved
0.72	Intermediate Similarity	NPD7680	Approved
0.7195	Intermediate Similarity	NPD1203	Approved
0.7191	Intermediate Similarity	NPD7458	Discontinued
0.7186	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD7583	Approved
0.7172	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6832	Phase 2
0.7168	Intermediate Similarity	NPD2800	Approved
0.7156	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2344	Approved
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7135	Intermediate Similarity	NPD7033	Discontinued
0.7128	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD3027	Phase 3
0.7113	Intermediate Similarity	NPD4287	Approved
0.7108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7068	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7043	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7016	Intermediate Similarity	NPD7039	Approved
0.7016	Intermediate Similarity	NPD7038	Approved
0.7012	Intermediate Similarity	NPD9269	Phase 2
0.6995	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2309	Approved
0.6982	Remote Similarity	NPD3764	Approved
0.6971	Remote Similarity	NPD1652	Phase 2
0.6965	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2346	Discontinued
0.6952	Remote Similarity	NPD5710	Approved
0.6952	Remote Similarity	NPD5711	Approved
0.6928	Remote Similarity	NPD3225	Approved
0.6927	Remote Similarity	NPD6273	Approved
0.6919	Remote Similarity	NPD6212	Phase 3
0.6919	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6213	Phase 3
0.6915	Remote Similarity	NPD5242	Approved
0.691	Remote Similarity	NPD7390	Discontinued
0.6909	Remote Similarity	NPD9717	Approved
0.6905	Remote Similarity	NPD9494	Approved
0.6902	Remote Similarity	NPD5353	Approved
0.6897	Remote Similarity	NPD5006	Approved
0.6897	Remote Similarity	NPD5005	Approved
0.6895	Remote Similarity	NPD7799	Discontinued
0.6895	Remote Similarity	NPD2163	Approved
0.6891	Remote Similarity	NPD7549	Discontinued
0.6885	Remote Similarity	NPD6844	Discontinued
0.6882	Remote Similarity	NPD3268	Approved
0.6878	Remote Similarity	NPD2403	Approved
0.6872	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4908	Phase 1
0.686	Remote Similarity	NPD5124	Phase 1
0.686	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7930	Approved
0.6848	Remote Similarity	NPD422	Phase 1
0.6848	Remote Similarity	NPD1091	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