NPASS Compound

Structure

NPC104682 OpenBabel07101719522D 27 31 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -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 -3.4641 -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 -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 -1.7321 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 1 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 26 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 6 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.11
Volume:	360.64
LogP:	3.522
LogD:	3.376
LogS:	-5.364
# Rotatable Bonds:	2
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	3.607
Fsp3:	0.286
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:	-4.843
MDCK Permeability:	3.409741839277558e-05
Pgp-inhibitor:	0.09
Pgp-substrate:	0.103
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	87.7235336303711%
Volume Distribution (VD):	0.682
Pgp-substrate:	8.267861366271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.478
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.288
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.74

ADMET: Excretion

Clearance (CL):	7.743
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.848
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.268
Carcinogencity:	0.47
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.548

Download Data

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

Natural Product: NPC104682

Natural Product ID:	NPC104682
*Common Name:**	OQUXSJDSDHAMOY-TZIWHRDSSA-N
IUPAC Name:	n.a.
Synonyms:	12-Hydroxyerosone
Standard InCHIKey:	OQUXSJDSDHAMOY-TZIWHRDSSA-N
Standard InCHI:	InChI=1S/C21H18O6/c1-24-17-8-11-3-4-19-21(23,14(11)9-18(17)25-2)20(22)13-7-12-5-6-26-15(12)10-16(13)27-19/h5-10,19,23H,3-4H2,1-2H3/t19-,21-/m1/s1
SMILES:	COc1cc2CC[C@@H]3[C@](c2cc1OC)(C(=O)c1cc2ccoc2cc1O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481057
PubChem CID:	44575274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones

*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
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[523270]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.8	ug.mL-1	PMID[523270]

☑ 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 NPC104682 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	443
0.1-0.2	1823
0.2-0.3	4057
0.3-0.4	10276
0.4-0.5	7980
0.5-0.6	3802
0.6-0.7	5306
0.7-0.8	5267
0.8-0.85	2576
0.85-0.9	1137
0.9-0.95	29
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9515	High Similarity	NPC150131
0.9176	High Similarity	NPC277510
0.9172	High Similarity	NPC131866
0.9112	High Similarity	NPC152477
0.9102	High Similarity	NPC472581
0.9064	High Similarity	NPC310794
0.9059	High Similarity	NPC279209
0.9059	High Similarity	NPC102277
0.9059	High Similarity	NPC190351
0.9053	High Similarity	NPC241820
0.9017	High Similarity	NPC246877
0.9006	High Similarity	NPC121333
0.9006	High Similarity	NPC248593
0.9006	High Similarity	NPC28589
0.9	High Similarity	NPC242395
0.8989	High Similarity	NPC60848
0.8988	High Similarity	NPC186686
0.8935	High Similarity	NPC62261
0.8935	High Similarity	NPC293319
0.8935	High Similarity	NPC38914
0.8929	High Similarity	NPC219861
0.8929	High Similarity	NPC476247
0.8922	High Similarity	NPC472624
0.8922	High Similarity	NPC36217
0.8895	High Similarity	NPC4200
0.8889	High Similarity	NPC288813
0.8889	High Similarity	NPC165456
0.8882	High Similarity	NPC53640
0.8882	High Similarity	NPC43319
0.8882	High Similarity	NPC477517
0.8882	High Similarity	NPC170245
0.8882	High Similarity	NPC277480
0.8882	High Similarity	NPC173292
0.8876	High Similarity	NPC65846
0.8876	High Similarity	NPC472625
0.8876	High Similarity	NPC474240
0.8876	High Similarity	NPC124038
0.8869	High Similarity	NPC74854
0.8869	High Similarity	NPC474239
0.8869	High Similarity	NPC45124
0.8869	High Similarity	NPC30655
0.8864	High Similarity	NPC228209
0.8862	High Similarity	NPC250076
0.8857	High Similarity	NPC476273
0.8851	High Similarity	NPC156635
0.8851	High Similarity	NPC8127
0.8851	High Similarity	NPC49667
0.8844	High Similarity	NPC65885
0.8837	High Similarity	NPC51404
0.883	High Similarity	NPC8965
0.883	High Similarity	NPC476459
0.883	High Similarity	NPC218226
0.883	High Similarity	NPC247973
0.8824	High Similarity	NPC326520
0.8824	High Similarity	NPC472277
0.8824	High Similarity	NPC475888
0.8824	High Similarity	NPC300053
0.8824	High Similarity	NPC37183
0.8824	High Similarity	NPC234052
0.8824	High Similarity	NPC108433
0.8817	High Similarity	NPC472635
0.8817	High Similarity	NPC474033
0.8817	High Similarity	NPC201800
0.8817	High Similarity	NPC472964
0.8817	High Similarity	NPC474034
0.8817	High Similarity	NPC193998
0.8817	High Similarity	NPC272722
0.8817	High Similarity	NPC211107
0.8814	High Similarity	NPC476170
0.881	High Similarity	NPC474960
0.881	High Similarity	NPC299436
0.881	High Similarity	NPC472902
0.881	High Similarity	NPC287328
0.881	High Similarity	NPC328102
0.881	High Similarity	NPC118256
0.881	High Similarity	NPC475784
0.881	High Similarity	NPC119209
0.881	High Similarity	NPC282009
0.881	High Similarity	NPC192686
0.8802	High Similarity	NPC284820
0.8802	High Similarity	NPC27337
0.8802	High Similarity	NPC291508
0.8802	High Similarity	NPC473272
0.8802	High Similarity	NPC67876
0.88	High Similarity	NPC23553
0.88	High Similarity	NPC77179
0.8793	High Similarity	NPC287243
0.8786	High Similarity	NPC174700
0.8786	High Similarity	NPC157522
0.8779	High Similarity	NPC300307
0.8772	High Similarity	NPC235610
0.8772	High Similarity	NPC471213
0.8772	High Similarity	NPC272502
0.8772	High Similarity	NPC128293
0.8772	High Similarity	NPC119589
0.8765	High Similarity	NPC205265
0.8765	High Similarity	NPC18100
0.8765	High Similarity	NPC133065
0.8765	High Similarity	NPC472582
0.8765	High Similarity	NPC472281
0.8765	High Similarity	NPC475985
0.8757	High Similarity	NPC173137
0.8757	High Similarity	NPC134783
0.8757	High Similarity	NPC474038
0.8757	High Similarity	NPC472632
0.8757	High Similarity	NPC471210
0.8757	High Similarity	NPC471499
0.8757	High Similarity	NPC142252
0.8757	High Similarity	NPC8927
0.8757	High Similarity	NPC240508
0.875	High Similarity	NPC210459
0.875	High Similarity	NPC22192
0.875	High Similarity	NPC473990
0.875	High Similarity	NPC55738
0.8743	High Similarity	NPC107244
0.8743	High Similarity	NPC291878
0.8743	High Similarity	NPC208152
0.8743	High Similarity	NPC278778
0.8743	High Similarity	NPC24640
0.8743	High Similarity	NPC35038
0.8743	High Similarity	NPC195796
0.8743	High Similarity	NPC78492
0.8736	High Similarity	NPC473834
0.8736	High Similarity	NPC216842
0.8736	High Similarity	NPC82217
0.8736	High Similarity	NPC476640
0.8735	High Similarity	NPC122365
0.8728	High Similarity	NPC74559
0.8728	High Similarity	NPC472276
0.8728	High Similarity	NPC476641
0.8722	High Similarity	NPC295436
0.8721	High Similarity	NPC474024
0.8721	High Similarity	NPC260266
0.8721	High Similarity	NPC117854
0.8721	High Similarity	NPC50394
0.8721	High Similarity	NPC6588
0.8721	High Similarity	NPC477154
0.8721	High Similarity	NPC186392
0.8721	High Similarity	NPC476306
0.8715	High Similarity	NPC240808
0.8713	High Similarity	NPC72787
0.8713	High Similarity	NPC275780
0.8713	High Similarity	NPC303174
0.8713	High Similarity	NPC239752
0.8713	High Similarity	NPC224280
0.8713	High Similarity	NPC39306
0.8713	High Similarity	NPC36320
0.8713	High Similarity	NPC472450
0.8713	High Similarity	NPC7688
0.8713	High Similarity	NPC7154
0.8713	High Similarity	NPC58223
0.8713	High Similarity	NPC36916
0.8713	High Similarity	NPC45449
0.8713	High Similarity	NPC125039
0.8713	High Similarity	NPC36
0.8706	High Similarity	NPC312056
0.8706	High Similarity	NPC474162
0.8706	High Similarity	NPC474150
0.8706	High Similarity	NPC84515
0.8706	High Similarity	NPC472402
0.8706	High Similarity	NPC229632
0.8706	High Similarity	NPC475144
0.8698	High Similarity	NPC470326
0.8698	High Similarity	NPC470183
0.8698	High Similarity	NPC470810
0.8698	High Similarity	NPC304839
0.8698	High Similarity	NPC471973
0.8698	High Similarity	NPC174953
0.8698	High Similarity	NPC321399
0.8698	High Similarity	NPC220582
0.8693	High Similarity	NPC221820
0.8693	High Similarity	NPC67302
0.8693	High Similarity	NPC469600
0.869	High Similarity	NPC471209
0.869	High Similarity	NPC472963
0.869	High Similarity	NPC52889
0.869	High Similarity	NPC65504
0.869	High Similarity	NPC474055
0.869	High Similarity	NPC471515
0.869	High Similarity	NPC472598
0.869	High Similarity	NPC136674
0.869	High Similarity	NPC471479
0.869	High Similarity	NPC268360
0.869	High Similarity	NPC52530
0.869	High Similarity	NPC78071
0.8686	High Similarity	NPC224165
0.8686	High Similarity	NPC53917
0.8686	High Similarity	NPC469601
0.8686	High Similarity	NPC227906
0.8683	High Similarity	NPC148938
0.8683	High Similarity	NPC477503
0.8683	High Similarity	NPC45849
0.8683	High Similarity	NPC200761
0.8683	High Similarity	NPC470327
0.8683	High Similarity	NPC67396
0.8683	High Similarity	NPC226025
0.8678	High Similarity	NPC118128
0.8678	High Similarity	NPC230619
0.8678	High Similarity	NPC54098
0.8675	High Similarity	NPC473996

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 NPC104682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	956
0.2-0.3	1803
0.3-0.4	2645
0.4-0.5	1833
0.5-0.6	943
0.6-0.7	403
0.7-0.8	115
0.8-0.85	27
0.85-0.9	16
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8713	High Similarity	NPD6168	Clinical (unspecified phase)
0.8713	High Similarity	NPD6166	Phase 2
0.8713	High Similarity	NPD6167	Clinical (unspecified phase)
0.8647	High Similarity	NPD1247	Approved
0.8623	High Similarity	NPD2393	Clinical (unspecified phase)
0.8588	High Similarity	NPD5494	Approved
0.8563	High Similarity	NPD5844	Phase 1
0.8563	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD919	Approved
0.8418	Intermediate Similarity	NPD6559	Discontinued
0.8353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6959	Discontinued
0.8294	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7411	Suspended
0.8276	Intermediate Similarity	NPD6232	Discontinued
0.8256	Intermediate Similarity	NPD3749	Approved
0.8256	Intermediate Similarity	NPD7075	Discontinued
0.8246	Intermediate Similarity	NPD3817	Phase 2
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8229	Intermediate Similarity	NPD3926	Phase 2
0.8225	Intermediate Similarity	NPD4380	Phase 2
0.8198	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8187	Intermediate Similarity	NPD2801	Approved
0.8144	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7074	Phase 3
0.8095	Intermediate Similarity	NPD1512	Approved
0.8079	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD7808	Phase 3
0.8056	Intermediate Similarity	NPD6797	Phase 2
0.8045	Intermediate Similarity	NPD7054	Approved
0.8036	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6801	Discontinued
0.8011	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD7472	Approved
0.7976	Intermediate Similarity	NPD1511	Approved
0.7967	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD8434	Phase 2
0.7892	Intermediate Similarity	NPD1549	Phase 2
0.7889	Intermediate Similarity	NPD3751	Discontinued
0.7874	Intermediate Similarity	NPD1465	Phase 2
0.787	Intermediate Similarity	NPD6799	Approved
0.7836	Intermediate Similarity	NPD920	Approved
0.7831	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6599	Discontinued
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7771	Intermediate Similarity	NPD2796	Approved
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5402	Approved
0.7725	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7199	Phase 2
0.7706	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3226	Approved
0.763	Intermediate Similarity	NPD5403	Approved
0.763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2534	Approved
0.7616	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD2533	Approved
0.7605	Intermediate Similarity	NPD1510	Phase 2
0.7529	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD2344	Approved
0.7514	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7486	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD4966	Approved
0.7486	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD3750	Approved
0.747	Intermediate Similarity	NPD1240	Approved
0.7457	Intermediate Similarity	NPD7390	Discontinued
0.7449	Intermediate Similarity	NPD6782	Approved
0.7449	Intermediate Similarity	NPD6778	Approved
0.7449	Intermediate Similarity	NPD6780	Approved
0.7449	Intermediate Similarity	NPD6776	Approved
0.7449	Intermediate Similarity	NPD6781	Approved
0.7449	Intermediate Similarity	NPD6777	Approved
0.7449	Intermediate Similarity	NPD6779	Approved
0.7447	Intermediate Similarity	NPD8313	Approved
0.7447	Intermediate Similarity	NPD8312	Approved
0.7443	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2800	Approved
0.7421	Intermediate Similarity	NPD8150	Discontinued
0.7414	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1471	Phase 3
0.7405	Intermediate Similarity	NPD7228	Approved
0.7381	Intermediate Similarity	NPD1607	Approved
0.7377	Intermediate Similarity	NPD7229	Phase 3
0.7374	Intermediate Similarity	NPD5761	Phase 2
0.7374	Intermediate Similarity	NPD5760	Phase 2
0.7368	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7907	Approved
0.7356	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4287	Approved
0.7343	Intermediate Similarity	NPD4665	Approved
0.7343	Intermediate Similarity	NPD4111	Phase 1
0.7341	Intermediate Similarity	NPD2309	Approved
0.7337	Intermediate Similarity	NPD7435	Discontinued
0.7327	Intermediate Similarity	NPD8151	Discontinued
0.7314	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2163	Approved
0.731	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2346	Discontinued
0.7308	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7870	Phase 2
0.73	Intermediate Similarity	NPD7871	Phase 2
0.7296	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3748	Approved
0.7294	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3057	Approved
0.7283	Intermediate Similarity	NPD4628	Phase 3
0.7262	Intermediate Similarity	NPD1613	Approved
0.7262	Intermediate Similarity	NPD943	Approved
0.7262	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD2935	Discontinued
0.7251	Intermediate Similarity	NPD1551	Phase 2
0.725	Intermediate Similarity	NPD7698	Approved
0.725	Intermediate Similarity	NPD7697	Approved
0.725	Intermediate Similarity	NPD7696	Phase 3
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD2972	Approved
0.72	Intermediate Similarity	NPD3533	Approved
0.7194	Intermediate Similarity	NPD6535	Approved
0.7194	Intermediate Similarity	NPD6534	Approved
0.7192	Intermediate Similarity	NPD7701	Phase 2
0.7189	Intermediate Similarity	NPD5710	Approved
0.7189	Intermediate Similarity	NPD5711	Approved
0.7171	Intermediate Similarity	NPD7783	Phase 2
0.7171	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7240	Approved
0.7151	Intermediate Similarity	NPD6100	Approved
0.7151	Intermediate Similarity	NPD6099	Approved
0.715	Intermediate Similarity	NPD2493	Approved
0.715	Intermediate Similarity	NPD2494	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4908	Phase 1
0.7122	Intermediate Similarity	NPD7874	Approved
0.7122	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2975	Approved
0.7121	Intermediate Similarity	NPD2973	Approved
0.7121	Intermediate Similarity	NPD2974	Approved
0.7118	Intermediate Similarity	NPD447	Suspended
0.7114	Intermediate Similarity	NPD2491	Approved
0.7112	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2799	Discontinued
0.7088	Intermediate Similarity	NPD8455	Phase 2
0.7087	Intermediate Similarity	NPD7801	Approved
0.7085	Intermediate Similarity	NPD7700	Phase 2
0.7085	Intermediate Similarity	NPD7699	Phase 2
0.7083	Intermediate Similarity	NPD4625	Phase 3
0.7083	Intermediate Similarity	NPD3027	Phase 3
0.7068	Intermediate Similarity	NPD6764	Approved
0.7068	Intermediate Similarity	NPD6765	Approved
0.7068	Intermediate Similarity	NPD7685	Pre-registration
0.7066	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3450	Approved
0.7065	Intermediate Similarity	NPD3452	Approved
0.7052	Intermediate Similarity	NPD5406	Approved
0.7052	Intermediate Similarity	NPD5404	Approved
0.7052	Intermediate Similarity	NPD5408	Approved
0.7052	Intermediate Similarity	NPD5405	Approved
0.7044	Intermediate Similarity	NPD4583	Approved
0.7044	Intermediate Similarity	NPD4582	Approved
0.7043	Intermediate Similarity	NPD8127	Discontinued
0.7041	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7177	Discontinued
0.703	Intermediate Similarity	NPD3448	Approved
0.703	Intermediate Similarity	NPD6823	Phase 2
0.702	Intermediate Similarity	NPD4360	Phase 2
0.702	Intermediate Similarity	NPD4363	Phase 3
0.7018	Intermediate Similarity	NPD1933	Approved
0.7018	Intermediate Similarity	NPD230	Phase 1
0.7016	Intermediate Similarity	NPD5953	Discontinued
0.7015	Intermediate Similarity	NPD4107	Approved
0.7015	Intermediate Similarity	NPD4580	Approved
0.7005	Intermediate Similarity	NPD6808	Phase 2
0.7005	Intermediate Similarity	NPD5676	Approved
0.7	Intermediate Similarity	NPD7286	Phase 2
0.6995	Remote Similarity	NPD4002	Approved
0.6995	Remote Similarity	NPD4004	Approved
0.6989	Remote Similarity	NPD7003	Approved
0.6989	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6273	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