NPASS Compound

Structure

CID308799 OpenBabel06191716112D 26 27 0 0 1 0 0 0 0 0999 V2000 3.5594 2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3784 4.5589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7906 5.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2083 6.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9771 3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3893 4.3498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9716 3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7961 5.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3948 4.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1930 5.0543 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 -0.0119 3.3317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 20 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	377.519
LogP:	5.312
LogD:	3.785
LogS:	-3.833
# Rotatable Bonds:	7
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	3.59
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	1.7945314539247192e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.865
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.613

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	99.37324523925781%
Volume Distribution (VD):	4.303
Pgp-substrate:	4.213260650634766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.922
CYP2D6-substrate:	0.736
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	12.557
Half-life (T1/2):	0.444

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.26
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.843
Carcinogencity:	0.11
Eye Corrosion:	0.02
Eye Irritation:	0.918
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC308799

Natural Product ID:	NPC308799
*Common Name:**	Shikonofuran E
IUPAC Name:	[1-[5-(2,5-dihydroxyphenyl)furan-3-yl]-4-methylpent-3-enyl] 3-methylbut-2-enoate
Synonyms:	Shikonofuran E
Standard InCHIKey:	MIIXCJKPPPUPOJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-13(2)5-8-19(26-21(24)9-14(3)4)15-10-20(25-12-15)17-11-16(22)6-7-18(17)23/h5-7,9-12,19,22-23H,8H2,1-4H3
SMILES:	CC(=CCC(c1cc(c2cc(ccc2O)O)oc1)OC(=O)C=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1944654
PubChem CID:	5321290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000136] Hydroquinones

*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
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s11418-007-0221-0]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17157006]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19217780]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373224]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	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	3
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2228	Individual Protein	Neuraminidase	Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1))	IC50	>	100000.0	nM	PMID[465116]
NPT2	Others	Unspecified		IC50	=	26600.0	nM	PMID[465116]
NPT2	Others	Unspecified		Ki	=	50.0	nM	PMID[465116]
NPT2	Others	Unspecified		Kic	=	0.1	uM	PMID[465116]
NPT2	Others	Unspecified		IC50	=	200.0	nM	PMID[465116]

☑ 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 NPC308799 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	301
0.1-0.2	1435
0.2-0.3	3651
0.3-0.4	8904
0.4-0.5	9855
0.5-0.6	3917
0.6-0.7	6903
0.7-0.8	7336
0.8-0.85	373
0.85-0.9	19
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC113428
0.9929	High Similarity	NPC61284
0.8873	High Similarity	NPC278832
0.8873	High Similarity	NPC64157
0.8865	High Similarity	NPC265793
0.8701	High Similarity	NPC269495
0.8681	High Similarity	NPC130976
0.8654	High Similarity	NPC24761
0.8633	High Similarity	NPC71525
0.8621	High Similarity	NPC98395
0.8591	High Similarity	NPC98926
0.8571	High Similarity	NPC474542
0.8523	High Similarity	NPC469642
0.8521	High Similarity	NPC7012
0.8506	High Similarity	NPC290927
0.8497	Intermediate Similarity	NPC170169
0.8477	Intermediate Similarity	NPC17816
0.8472	Intermediate Similarity	NPC159786
0.8471	Intermediate Similarity	NPC169
0.8471	Intermediate Similarity	NPC49009
0.8462	Intermediate Similarity	NPC270044
0.8452	Intermediate Similarity	NPC198490
0.8446	Intermediate Similarity	NPC145673
0.8442	Intermediate Similarity	NPC67654
0.8442	Intermediate Similarity	NPC207624
0.8431	Intermediate Similarity	NPC155882
0.8431	Intermediate Similarity	NPC191104
0.8431	Intermediate Similarity	NPC230713
0.8431	Intermediate Similarity	NPC78335
0.8431	Intermediate Similarity	NPC167576
0.8418	Intermediate Similarity	NPC14822
0.8417	Intermediate Similarity	NPC4012
0.8415	Intermediate Similarity	NPC107244
0.8411	Intermediate Similarity	NPC211565
0.8411	Intermediate Similarity	NPC60389
0.8408	Intermediate Similarity	NPC476349
0.8408	Intermediate Similarity	NPC476350
0.8408	Intermediate Similarity	NPC477692
0.8405	Intermediate Similarity	NPC233956
0.84	Intermediate Similarity	NPC274085
0.84	Intermediate Similarity	NPC89664
0.8397	Intermediate Similarity	NPC160015
0.8397	Intermediate Similarity	NPC247677
0.8392	Intermediate Similarity	NPC141549
0.8389	Intermediate Similarity	NPC329493
0.8387	Intermediate Similarity	NPC183874
0.8387	Intermediate Similarity	NPC158261
0.8387	Intermediate Similarity	NPC122365
0.8387	Intermediate Similarity	NPC42458
0.8378	Intermediate Similarity	NPC477537
0.8377	Intermediate Similarity	NPC58668
0.8377	Intermediate Similarity	NPC115324
0.8377	Intermediate Similarity	NPC193976
0.8377	Intermediate Similarity	NPC156244
0.8377	Intermediate Similarity	NPC106372
0.8377	Intermediate Similarity	NPC23668
0.8375	Intermediate Similarity	NPC291110
0.8366	Intermediate Similarity	NPC88445
0.8366	Intermediate Similarity	NPC37226
0.8366	Intermediate Similarity	NPC226644
0.8366	Intermediate Similarity	NPC178202
0.8354	Intermediate Similarity	NPC239270
0.8354	Intermediate Similarity	NPC303210
0.8354	Intermediate Similarity	NPC95472
0.8344	Intermediate Similarity	NPC260902
0.8344	Intermediate Similarity	NPC296957
0.8344	Intermediate Similarity	NPC155144
0.8333	Intermediate Similarity	NPC118253
0.8333	Intermediate Similarity	NPC470160
0.8333	Intermediate Similarity	NPC148938
0.8323	Intermediate Similarity	NPC34965
0.8323	Intermediate Similarity	NPC281272
0.8323	Intermediate Similarity	NPC183536
0.8323	Intermediate Similarity	NPC253872
0.8323	Intermediate Similarity	NPC263676
0.8323	Intermediate Similarity	NPC142308
0.8322	Intermediate Similarity	NPC278787
0.8322	Intermediate Similarity	NPC7569
0.8311	Intermediate Similarity	NPC18457
0.8311	Intermediate Similarity	NPC112757
0.8301	Intermediate Similarity	NPC228012
0.8291	Intermediate Similarity	NPC472877
0.8289	Intermediate Similarity	NPC469758
0.8282	Intermediate Similarity	NPC281835
0.828	Intermediate Similarity	NPC45131
0.8278	Intermediate Similarity	NPC10302
0.8278	Intermediate Similarity	NPC105381
0.8278	Intermediate Similarity	NPC302181
0.8269	Intermediate Similarity	NPC472462
0.8269	Intermediate Similarity	NPC235333
0.8269	Intermediate Similarity	NPC470331
0.8269	Intermediate Similarity	NPC1477
0.8269	Intermediate Similarity	NPC72370
0.8269	Intermediate Similarity	NPC477691
0.8269	Intermediate Similarity	NPC213608
0.8258	Intermediate Similarity	NPC39819
0.8258	Intermediate Similarity	NPC116604
0.8255	Intermediate Similarity	NPC477535
0.825	Intermediate Similarity	NPC312056
0.825	Intermediate Similarity	NPC84515
0.825	Intermediate Similarity	NPC193998
0.8247	Intermediate Similarity	NPC296030
0.8247	Intermediate Similarity	NPC39929
0.8247	Intermediate Similarity	NPC266499
0.8247	Intermediate Similarity	NPC317492
0.8242	Intermediate Similarity	NPC224165
0.8242	Intermediate Similarity	NPC53917
0.8239	Intermediate Similarity	NPC304839
0.8239	Intermediate Similarity	NPC220582
0.8239	Intermediate Similarity	NPC115432
0.8239	Intermediate Similarity	NPC260296
0.8235	Intermediate Similarity	NPC130581
0.8235	Intermediate Similarity	NPC74539
0.8235	Intermediate Similarity	NPC12148
0.8235	Intermediate Similarity	NPC304443
0.8232	Intermediate Similarity	NPC247964
0.8228	Intermediate Similarity	NPC212967
0.8228	Intermediate Similarity	NPC164110
0.8228	Intermediate Similarity	NPC96342
0.8228	Intermediate Similarity	NPC196448
0.8228	Intermediate Similarity	NPC246647
0.8227	Intermediate Similarity	NPC4164
0.8224	Intermediate Similarity	NPC469764
0.8224	Intermediate Similarity	NPC230943
0.8217	Intermediate Similarity	NPC297531
0.8217	Intermediate Similarity	NPC99199
0.8217	Intermediate Similarity	NPC213936
0.8217	Intermediate Similarity	NPC233776
0.8212	Intermediate Similarity	NPC472006
0.8212	Intermediate Similarity	NPC53192
0.8212	Intermediate Similarity	NPC476164
0.8212	Intermediate Similarity	NPC476310
0.821	Intermediate Similarity	NPC67450
0.821	Intermediate Similarity	NPC193881
0.821	Intermediate Similarity	NPC210460
0.821	Intermediate Similarity	NPC155264
0.821	Intermediate Similarity	NPC277480
0.8205	Intermediate Similarity	NPC44606
0.8205	Intermediate Similarity	NPC474843
0.8205	Intermediate Similarity	NPC5871
0.8205	Intermediate Similarity	NPC24232
0.8205	Intermediate Similarity	NPC215811
0.8205	Intermediate Similarity	NPC477690
0.8194	Intermediate Similarity	NPC136340
0.8194	Intermediate Similarity	NPC475717
0.8194	Intermediate Similarity	NPC164527
0.8194	Intermediate Similarity	NPC37348
0.8194	Intermediate Similarity	NPC213382
0.8188	Intermediate Similarity	NPC475045
0.8187	Intermediate Similarity	NPC188486
0.8187	Intermediate Similarity	NPC304387
0.8187	Intermediate Similarity	NPC45124
0.8187	Intermediate Similarity	NPC269117
0.8187	Intermediate Similarity	NPC96031
0.8187	Intermediate Similarity	NPC30655
0.8187	Intermediate Similarity	NPC74854
0.8182	Intermediate Similarity	NPC261471
0.8182	Intermediate Similarity	NPC168085
0.8182	Intermediate Similarity	NPC37135
0.8182	Intermediate Similarity	NPC135325
0.8182	Intermediate Similarity	NPC186397
0.8176	Intermediate Similarity	NPC40583
0.8176	Intermediate Similarity	NPC16935
0.8176	Intermediate Similarity	NPC477534
0.8176	Intermediate Similarity	NPC244750
0.8176	Intermediate Similarity	NPC196879
0.817	Intermediate Similarity	NPC107625
0.817	Intermediate Similarity	NPC51641
0.817	Intermediate Similarity	NPC472033
0.817	Intermediate Similarity	NPC300267
0.817	Intermediate Similarity	NPC210826
0.8165	Intermediate Similarity	NPC180924
0.8163	Intermediate Similarity	NPC281513
0.8163	Intermediate Similarity	NPC229638
0.8163	Intermediate Similarity	NPC267539
0.8163	Intermediate Similarity	NPC71108
0.8163	Intermediate Similarity	NPC204257
0.8163	Intermediate Similarity	NPC29317
0.8163	Intermediate Similarity	NPC22222
0.8163	Intermediate Similarity	NPC254832
0.8163	Intermediate Similarity	NPC176102
0.816	Intermediate Similarity	NPC247973
0.816	Intermediate Similarity	NPC86477
0.8153	Intermediate Similarity	NPC301233
0.8151	Intermediate Similarity	NPC157478
0.8151	Intermediate Similarity	NPC289572
0.8151	Intermediate Similarity	NPC106247
0.8151	Intermediate Similarity	NPC200422
0.8151	Intermediate Similarity	NPC295406
0.8151	Intermediate Similarity	NPC43627
0.8148	Intermediate Similarity	NPC29411
0.8148	Intermediate Similarity	NPC37183
0.8148	Intermediate Similarity	NPC136641
0.8148	Intermediate Similarity	NPC36320
0.8143	Intermediate Similarity	NPC311219
0.8143	Intermediate Similarity	NPC477151
0.8143	Intermediate Similarity	NPC132518
0.8141	Intermediate Similarity	NPC240768
0.8141	Intermediate Similarity	NPC200773
0.8141	Intermediate Similarity	NPC290671

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 NPC308799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	901
0.2-0.3	1606
0.3-0.4	2477
0.4-0.5	2027
0.5-0.6	1231
0.6-0.7	479
0.7-0.8	159
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8552	High Similarity	NPD2935	Discontinued
0.8367	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD920	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD1551	Phase 2
0.8151	Intermediate Similarity	NPD447	Suspended
0.8143	Intermediate Similarity	NPD9717	Approved
0.8121	Intermediate Similarity	NPD2344	Approved
0.8105	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5402	Approved
0.8099	Intermediate Similarity	NPD1203	Approved
0.8069	Intermediate Similarity	NPD2313	Discontinued
0.8056	Intermediate Similarity	NPD6832	Phase 2
0.8027	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2346	Discontinued
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7974	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD411	Approved
0.7908	Intermediate Similarity	NPD2309	Approved
0.7888	Intermediate Similarity	NPD3749	Approved
0.7871	Intermediate Similarity	NPD2533	Approved
0.7871	Intermediate Similarity	NPD2532	Approved
0.7871	Intermediate Similarity	NPD2534	Approved
0.7853	Intermediate Similarity	NPD1247	Approved
0.7843	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD1549	Phase 2
0.7826	Intermediate Similarity	NPD3882	Suspended
0.7812	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2801	Approved
0.7812	Intermediate Similarity	NPD7819	Suspended
0.7793	Intermediate Similarity	NPD1019	Discontinued
0.7778	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.777	Intermediate Similarity	NPD9493	Approved
0.7763	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1934	Approved
0.7746	Intermediate Similarity	NPD3496	Discontinued
0.7725	Intermediate Similarity	NPD3818	Discontinued
0.7716	Intermediate Similarity	NPD7768	Phase 2
0.7702	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2796	Approved
0.7692	Intermediate Similarity	NPD6799	Approved
0.7692	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7411	Suspended
0.7683	Intermediate Similarity	NPD5494	Approved
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3226	Approved
0.7658	Intermediate Similarity	NPD5403	Approved
0.764	Intermediate Similarity	NPD6844	Discontinued
0.7632	Intermediate Similarity	NPD1510	Phase 2
0.7632	Intermediate Similarity	NPD4308	Phase 3
0.7613	Intermediate Similarity	NPD3750	Approved
0.7607	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2797	Approved
0.76	Intermediate Similarity	NPD1240	Approved
0.7597	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3268	Approved
0.7561	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2798	Approved
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3817	Phase 2
0.7532	Intermediate Similarity	NPD5401	Approved
0.7531	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD6808	Phase 2
0.7471	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD1511	Approved
0.7467	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2800	Approved
0.7434	Intermediate Similarity	NPD1933	Approved
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7425	Intermediate Similarity	NPD6959	Discontinued
0.7421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7033	Discontinued
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD6232	Discontinued
0.7375	Intermediate Similarity	NPD1512	Approved
0.7368	Intermediate Similarity	NPD4307	Phase 2
0.7353	Intermediate Similarity	NPD7473	Discontinued
0.7351	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD2296	Approved
0.7326	Intermediate Similarity	NPD7074	Phase 3
0.732	Intermediate Similarity	NPD6355	Discontinued
0.7315	Intermediate Similarity	NPD5647	Approved
0.7308	Intermediate Similarity	NPD6002	Phase 3
0.7308	Intermediate Similarity	NPD6004	Phase 3
0.7308	Intermediate Similarity	NPD6005	Phase 3
0.7308	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1471	Phase 3
0.7308	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6233	Phase 2
0.729	Intermediate Similarity	NPD3748	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7279	Intermediate Similarity	NPD1481	Phase 2
0.7267	Intermediate Similarity	NPD7286	Phase 2
0.7267	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD7054	Approved
0.7257	Intermediate Similarity	NPD8312	Approved
0.7257	Intermediate Similarity	NPD8313	Approved
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD7472	Approved
0.7212	Intermediate Similarity	NPD6280	Approved
0.7212	Intermediate Similarity	NPD6279	Approved
0.7211	Intermediate Similarity	NPD1535	Discovery
0.7209	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7203	Intermediate Similarity	NPD6671	Approved
0.7194	Intermediate Similarity	NPD9266	Approved
0.7194	Intermediate Similarity	NPD74	Approved
0.7192	Intermediate Similarity	NPD1778	Approved
0.7184	Intermediate Similarity	NPD6797	Phase 2
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5711	Approved
0.7176	Intermediate Similarity	NPD5710	Approved
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.7168	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD6653	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD6032	Approved
0.7133	Intermediate Similarity	NPD1164	Approved
0.7126	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3764	Approved
0.7122	Intermediate Similarity	NPD9267	Approved
0.7122	Intermediate Similarity	NPD9263	Approved
0.7122	Intermediate Similarity	NPD9264	Approved
0.7102	Intermediate Similarity	NPD7808	Phase 3
0.7099	Intermediate Similarity	NPD4661	Approved
0.7099	Intermediate Similarity	NPD4662	Approved
0.7073	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3225	Approved
0.7066	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7063	Intermediate Similarity	NPD7003	Approved
0.7055	Intermediate Similarity	NPD9545	Approved
0.7048	Intermediate Similarity	NPD5890	Approved
0.7048	Intermediate Similarity	NPD5889	Approved
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7039	Intermediate Similarity	NPD2861	Phase 2
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD943	Approved
0.7032	Intermediate Similarity	NPD4060	Phase 1
0.7025	Intermediate Similarity	NPD5406	Approved
0.7025	Intermediate Similarity	NPD5405	Approved
0.7025	Intermediate Similarity	NPD5408	Approved
0.7025	Intermediate Similarity	NPD5404	Approved
0.702	Intermediate Similarity	NPD1470	Approved
0.7012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7007	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.698	Remote Similarity	NPD422	Phase 1
0.698	Remote Similarity	NPD1611	Approved
0.6977	Remote Similarity	NPD7229	Phase 3
0.6975	Remote Similarity	NPD7440	Discontinued
0.6972	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4287	Approved
0.6959	Remote Similarity	NPD17	Approved
0.6959	Remote Similarity	NPD4626	Approved
0.6954	Remote Similarity	NPD1283	Approved
0.6949	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1894	Discontinued
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD2979	Phase 3
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6914	Remote Similarity	NPD3887	Approved
0.691	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6362	Approved
0.6905	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD6234	Discontinued
0.6897	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9281	Approved
0.6893	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5691	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