NPASS Compound

Structure

CID39819 OpenBabel06191715372D 22 24 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -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 -3.4641 2.0000 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 -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 -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 -0.8660 0.5000 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 1.7321 -1.0000 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 -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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.618
LogD:	2.263
LogS:	-3.831
# Rotatable Bonds:	3
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	2.426
Fsp3:	0.125
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:	-4.93
MDCK Permeability:	1.2375551705190446e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.234
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	86.65093231201172%
Volume Distribution (VD):	0.944
Pgp-substrate:	14.958888053894043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.811
CYP2C19-inhibitor:	0.489
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.757
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.737
CYP2D6-substrate:	0.321
CYP3A4-inhibitor:	0.499
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	2.968
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.413
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.524
Carcinogencity:	0.028
Eye Corrosion:	0.006
Eye Irritation:	0.917
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC39819

Natural Product ID:	NPC39819
*Common Name:**	Sydowinin A
IUPAC Name:	methyl 8-hydroxy-6-(hydroxymethyl)-9-oxoxanthene-1-carboxylate
Synonyms:	Sydowinin A
Standard InCHIKey:	UBYOEDLUKKPPPN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-16(20)9-3-2-4-11-13(9)15(19)14-10(18)5-8(7-17)6-12(14)22-11/h2-6,17-18H,7H2,1H3
SMILES:	COC(=O)c1cccc2c1c(=O)c1c(o2)cc(cc1O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812028
PubChem CID:	23872092
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	28.73	%	PMID[529721]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[529721]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	38.1	%	PMID[529721]

☑ 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 NPC39819 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	379
0.1-0.2	1733
0.2-0.3	3930
0.3-0.4	8998
0.4-0.5	9490
0.5-0.6	3741
0.6-0.7	5808
0.7-0.8	4941
0.8-0.85	2978
0.85-0.9	660
0.9-0.95	31
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC281272
0.9589	High Similarity	NPC70764
0.9452	High Similarity	NPC71055
0.9392	High Similarity	NPC470107
0.9262	High Similarity	NPC295036
0.9257	High Similarity	NPC228012
0.9205	High Similarity	NPC135522
0.9184	High Similarity	NPC469764
0.9133	High Similarity	NPC202595
0.9128	High Similarity	NPC2569
0.9128	High Similarity	NPC172329
0.9122	High Similarity	NPC469758
0.9041	High Similarity	NPC145673
0.902	High Similarity	NPC237560
0.9013	High Similarity	NPC154683
0.9013	High Similarity	NPC474843
0.9013	High Similarity	NPC40356
0.9013	High Similarity	NPC473967
0.9013	High Similarity	NPC273483
0.9007	High Similarity	NPC290954
0.9007	High Similarity	NPC147735
0.9007	High Similarity	NPC255641
0.9	High Similarity	NPC5537
0.8968	High Similarity	NPC186113
0.8926	High Similarity	NPC184649
0.8926	High Similarity	NPC303185
0.8919	High Similarity	NPC310340
0.8904	High Similarity	NPC18457
0.8903	High Similarity	NPC44199
0.8903	High Similarity	NPC263483
0.8889	High Similarity	NPC217447
0.8867	High Similarity	NPC267509
0.8867	High Similarity	NPC196114
0.8867	High Similarity	NPC300540
0.8867	High Similarity	NPC299011
0.8859	High Similarity	NPC113770
0.8839	High Similarity	NPC146211
0.8831	High Similarity	NPC477691
0.8824	High Similarity	NPC232645
0.8824	High Similarity	NPC470569
0.8824	High Similarity	NPC72958
0.8816	High Similarity	NPC291049
0.8816	High Similarity	NPC233267
0.8812	High Similarity	NPC234331
0.8808	High Similarity	NPC118027
0.8808	High Similarity	NPC126767
0.8808	High Similarity	NPC190648
0.8808	High Similarity	NPC56433
0.8808	High Similarity	NPC245584
0.8808	High Similarity	NPC312929
0.8808	High Similarity	NPC289042
0.8805	High Similarity	NPC178281
0.88	High Similarity	NPC311144
0.88	High Similarity	NPC32470
0.88	High Similarity	NPC131766
0.88	High Similarity	NPC134621
0.8797	High Similarity	NPC473961
0.8792	High Similarity	NPC202981
0.8792	High Similarity	NPC1534
0.8792	High Similarity	NPC73028
0.8784	High Similarity	NPC275734
0.8776	High Similarity	NPC1268
0.8776	High Similarity	NPC268691
0.8773	High Similarity	NPC68381
0.8766	High Similarity	NPC253904
0.8766	High Similarity	NPC271681
0.8766	High Similarity	NPC87708
0.8766	High Similarity	NPC321363
0.8766	High Similarity	NPC175978
0.8766	High Similarity	NPC477690
0.8758	High Similarity	NPC470568
0.8758	High Similarity	NPC227122
0.8758	High Similarity	NPC474660
0.8758	High Similarity	NPC325983
0.8758	High Similarity	NPC475717
0.8758	High Similarity	NPC294646
0.8758	High Similarity	NPC119929
0.875	High Similarity	NPC7025
0.875	High Similarity	NPC105415
0.875	High Similarity	NPC29160
0.875	High Similarity	NPC27221
0.875	High Similarity	NPC39195
0.875	High Similarity	NPC153417
0.875	High Similarity	NPC256672
0.8742	High Similarity	NPC99454
0.8742	High Similarity	NPC163846
0.8742	High Similarity	NPC237208
0.8742	High Similarity	NPC130176
0.8742	High Similarity	NPC225173
0.8742	High Similarity	NPC211565
0.8733	High Similarity	NPC19896
0.8733	High Similarity	NPC95123
0.8733	High Similarity	NPC274085
0.8733	High Similarity	NPC66404
0.8733	High Similarity	NPC89664
0.8726	High Similarity	NPC324736
0.8725	High Similarity	NPC250755
0.8725	High Similarity	NPC49108
0.8725	High Similarity	NPC105648
0.8718	High Similarity	NPC154341
0.871	High Similarity	NPC214632
0.871	High Similarity	NPC208806
0.871	High Similarity	NPC472799
0.871	High Similarity	NPC210942
0.871	High Similarity	NPC169990
0.8704	High Similarity	NPC241874
0.8701	High Similarity	NPC133856
0.8701	High Similarity	NPC70016
0.8701	High Similarity	NPC207346
0.8701	High Similarity	NPC215921
0.8701	High Similarity	NPC258249
0.8701	High Similarity	NPC474417
0.8701	High Similarity	NPC149526
0.8701	High Similarity	NPC478148
0.8701	High Similarity	NPC46564
0.8701	High Similarity	NPC115324
0.8699	High Similarity	NPC141934
0.8696	High Similarity	NPC76647
0.8693	High Similarity	NPC65589
0.8693	High Similarity	NPC100985
0.8693	High Similarity	NPC266499
0.8693	High Similarity	NPC77325
0.8693	High Similarity	NPC97029
0.8693	High Similarity	NPC10027
0.8693	High Similarity	NPC474052
0.8693	High Similarity	NPC288036
0.8693	High Similarity	NPC97028
0.8693	High Similarity	NPC65775
0.8693	High Similarity	NPC158338
0.8693	High Similarity	NPC73236
0.8693	High Similarity	NPC4423
0.8684	High Similarity	NPC22005
0.8684	High Similarity	NPC7943
0.8684	High Similarity	NPC146884
0.8684	High Similarity	NPC46941
0.8684	High Similarity	NPC472036
0.8684	High Similarity	NPC308200
0.8684	High Similarity	NPC123202
0.8684	High Similarity	NPC125801
0.8679	High Similarity	NPC278329
0.8679	High Similarity	NPC146837
0.8675	High Similarity	NPC475161
0.8675	High Similarity	NPC477860
0.8675	High Similarity	NPC29577
0.8671	High Similarity	NPC143050
0.8671	High Similarity	NPC130955
0.8667	High Similarity	NPC51106
0.8667	High Similarity	NPC469542
0.8667	High Similarity	NPC159855
0.8667	High Similarity	NPC476473
0.8667	High Similarity	NPC169479
0.8667	High Similarity	NPC472006
0.8662	High Similarity	NPC164110
0.8662	High Similarity	NPC246647
0.8662	High Similarity	NPC158542
0.8662	High Similarity	NPC201127
0.8662	High Similarity	NPC212967
0.8662	High Similarity	NPC477833
0.8662	High Similarity	NPC96342
0.8658	High Similarity	NPC124365
0.8658	High Similarity	NPC182421
0.8658	High Similarity	NPC220106
0.8654	High Similarity	NPC326910
0.8654	High Similarity	NPC255807
0.8654	High Similarity	NPC89625
0.8654	High Similarity	NPC31018
0.8654	High Similarity	NPC175192
0.8654	High Similarity	NPC67396
0.8654	High Similarity	NPC149618
0.865	High Similarity	NPC30432
0.865	High Similarity	NPC76128
0.865	High Similarity	NPC111536
0.865	High Similarity	NPC5029
0.865	High Similarity	NPC271385
0.8649	High Similarity	NPC280284
0.8649	High Similarity	NPC99333
0.8649	High Similarity	NPC188947
0.8645	High Similarity	NPC207624
0.8645	High Similarity	NPC75069
0.8642	High Similarity	NPC165979
0.8642	High Similarity	NPC99613
0.8642	High Similarity	NPC222455
0.8642	High Similarity	NPC49487
0.8642	High Similarity	NPC163130
0.8636	High Similarity	NPC60413
0.8636	High Similarity	NPC158866
0.8636	High Similarity	NPC213382
0.8636	High Similarity	NPC164527
0.8636	High Similarity	NPC150928
0.8636	High Similarity	NPC267117
0.8636	High Similarity	NPC473466
0.8634	High Similarity	NPC477835
0.8634	High Similarity	NPC125465
0.8634	High Similarity	NPC178173
0.863	High Similarity	NPC161632
0.8627	High Similarity	NPC35150
0.8627	High Similarity	NPC186397
0.8627	High Similarity	NPC471642
0.8627	High Similarity	NPC471641
0.8627	High Similarity	NPC240622

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 NPC39819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	955
0.2-0.3	1651
0.3-0.4	2537
0.4-0.5	1970
0.5-0.6	1111
0.6-0.7	341
0.7-0.8	148
0.8-0.85	51
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8836	High Similarity	NPD2346	Discontinued
0.8831	High Similarity	NPD7819	Suspended
0.8816	High Similarity	NPD3226	Approved
0.8767	High Similarity	NPD1551	Phase 2
0.8658	High Similarity	NPD3750	Approved
0.8533	High Similarity	NPD1878	Clinical (unspecified phase)
0.8523	High Similarity	NPD1549	Phase 2
0.8456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD6232	Discontinued
0.8431	Intermediate Similarity	NPD2532	Approved
0.8431	Intermediate Similarity	NPD2533	Approved
0.8431	Intermediate Similarity	NPD2534	Approved
0.8428	Intermediate Similarity	NPD3749	Approved
0.8418	Intermediate Similarity	NPD5402	Approved
0.8408	Intermediate Similarity	NPD1934	Approved
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6959	Discontinued
0.8354	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD3748	Approved
0.8322	Intermediate Similarity	NPD1510	Phase 2
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8312	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1607	Approved
0.8303	Intermediate Similarity	NPD5844	Phase 1
0.8289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8263	Intermediate Similarity	NPD6559	Discontinued
0.825	Intermediate Similarity	NPD7768	Phase 2
0.8239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD5403	Approved
0.8199	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD5401	Approved
0.8176	Intermediate Similarity	NPD1240	Approved
0.8166	Intermediate Similarity	NPD8313	Approved
0.8166	Intermediate Similarity	NPD8312	Approved
0.8165	Intermediate Similarity	NPD4380	Phase 2
0.8163	Intermediate Similarity	NPD2313	Discontinued
0.8146	Intermediate Similarity	NPD2796	Approved
0.8146	Intermediate Similarity	NPD2935	Discontinued
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6799	Approved
0.8129	Intermediate Similarity	NPD1511	Approved
0.8125	Intermediate Similarity	NPD2801	Approved
0.8121	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8069	Intermediate Similarity	NPD1203	Approved
0.8063	Intermediate Similarity	NPD6801	Discontinued
0.8046	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6100	Approved
0.8026	Intermediate Similarity	NPD6099	Approved
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8025	Intermediate Similarity	NPD1512	Approved
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2799	Discontinued
0.7961	Intermediate Similarity	NPD4308	Phase 3
0.7945	Intermediate Similarity	NPD1470	Approved
0.7935	Intermediate Similarity	NPD4628	Phase 3
0.7929	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD411	Approved
0.7905	Intermediate Similarity	NPD6832	Phase 2
0.7895	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5711	Approved
0.7892	Intermediate Similarity	NPD5710	Approved
0.7881	Intermediate Similarity	NPD447	Suspended
0.7879	Intermediate Similarity	NPD5494	Approved
0.7871	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7054	Approved
0.7862	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD9717	Approved
0.7852	Intermediate Similarity	NPD4625	Phase 3
0.7824	Intermediate Similarity	NPD7472	Approved
0.7811	Intermediate Similarity	NPD3751	Discontinued
0.78	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2800	Approved
0.7742	Intermediate Similarity	NPD2344	Approved
0.7742	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7703	Intermediate Similarity	NPD2797	Approved
0.7697	Intermediate Similarity	NPD4307	Phase 2
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7682	Intermediate Similarity	NPD3268	Approved
0.7682	Intermediate Similarity	NPD3764	Approved
0.7677	Intermediate Similarity	NPD5408	Approved
0.7677	Intermediate Similarity	NPD5406	Approved
0.7677	Intermediate Similarity	NPD5404	Approved
0.7677	Intermediate Similarity	NPD5405	Approved
0.7671	Intermediate Similarity	NPD1201	Approved
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.7651	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD1243	Approved
0.7636	Intermediate Similarity	NPD4288	Approved
0.7622	Intermediate Similarity	NPD37	Approved
0.7619	Intermediate Similarity	NPD1608	Approved
0.7614	Intermediate Similarity	NPD8150	Discontinued
0.7613	Intermediate Similarity	NPD7033	Discontinued
0.761	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7435	Discontinued
0.759	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD4967	Phase 2
0.759	Intermediate Similarity	NPD4965	Approved
0.7578	Intermediate Similarity	NPD6273	Approved
0.7568	Intermediate Similarity	NPD4749	Approved
0.7566	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.755	Intermediate Similarity	NPD4908	Phase 1
0.7547	Intermediate Similarity	NPD2309	Approved
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7533	Intermediate Similarity	NPD1019	Discontinued
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7528	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6844	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7484	Intermediate Similarity	NPD7003	Approved
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3267	Approved
0.7467	Intermediate Similarity	NPD3266	Approved
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD422	Phase 1
0.743	Intermediate Similarity	NPD4287	Approved
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7697	Approved
0.7415	Intermediate Similarity	NPD17	Approved
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7405	Intermediate Similarity	NPD1471	Phase 3
0.74	Intermediate Similarity	NPD1283	Approved
0.74	Intermediate Similarity	NPD3225	Approved
0.7399	Intermediate Similarity	NPD7228	Approved
0.7386	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7871	Phase 2
0.738	Intermediate Similarity	NPD7870	Phase 2
0.7379	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7874	Approved
0.7368	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6823	Phase 2
0.7353	Intermediate Similarity	NPD6746	Phase 2
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1247	Approved
0.7308	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1778	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2979	Phase 3
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7783	Phase 2
0.7229	Intermediate Similarity	NPD7458	Discontinued
0.7225	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8285	Discontinued
0.72	Intermediate Similarity	NPD1611	Approved
0.72	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1281	Approved
0.7196	Intermediate Similarity	NPD8320	Phase 1

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