NPASS Compound

Structure

NPC219874 OpenBabel07101718322D 22 23 0 0 1 0 0 0 0 0999 V2000 -3.2597 -2.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1428 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3730 -0.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9659 -1.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1994 0.7405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4936 0.4397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6276 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -1.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9654 1.3832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8012 -2.9245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8012 1.9245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1428 -2.6321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 1.0825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 2 0 0 0 0 3 10 1 0 0 0 0 4 17 1 0 0 0 0 5 17 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 10 22 1 0 0 0 0 11 7 1 1 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 1 0 0 0 13 16 1 0 0 0 0 13 17 1 6 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	316.244
LogP:	2.323
LogD:	1.648
LogS:	-3.473
# Rotatable Bonds:	2
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	4.933
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.789
MDCK Permeability:	2.102219696098473e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.769

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	89.2570571899414%
Volume Distribution (VD):	0.346
Pgp-substrate:	16.143821716308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.423
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.551
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	3.503
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.481
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.715
Carcinogencity:	0.209
Eye Corrosion:	0.092
Eye Irritation:	0.143
Respiratory Toxicity:	0.698

Download Data

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

Natural Product: NPC219874

Natural Product ID:	NPC219874
*Common Name:**	Naematolon
IUPAC Name:	[(1S,4R,5E,8R,9R)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxo-4-bicyclo[7.2.0]undec-5-enyl] acetate
Synonyms:	Naematolon
Standard InCHIKey:	BBRNVDBLOTVLMB-WDVDPGPOSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-8-6-12(22-10(3)18)15(20)9(2)11-7-17(4,5)13(11)16(21)14(8)19/h6,11-13,16,21H,2,7H2,1,3-5H3/b8-6+/t11-,12-,13+,16-/m1/s1
SMILES:	CC(=O)O[C@@H]1/C=C(C)/C(=O)[C@@H]([C@@H]2[C@@H](C(=C)C1=O)CC2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477125
PubChem CID:	10335298
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32956	panus sp.	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]

☑ 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	1
LD50	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2.0	ug.mL-1	PMID[529628]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	225.0	mg.kg-1	PMID[529628]

☑ 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 NPC219874 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	232
0.1-0.2	1373
0.2-0.3	5394
0.3-0.4	11984
0.4-0.5	12669
0.5-0.6	6789
0.6-0.7	3766
0.7-0.8	481
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8706	High Similarity	NPC304795
0.8353	Intermediate Similarity	NPC211279
0.8333	Intermediate Similarity	NPC222011
0.8333	Intermediate Similarity	NPC261721
0.8229	Intermediate Similarity	NPC69385
0.8132	Intermediate Similarity	NPC202394
0.8125	Intermediate Similarity	NPC184065
0.8105	Intermediate Similarity	NPC469632
0.8065	Intermediate Similarity	NPC212598
0.8046	Intermediate Similarity	NPC321180
0.8041	Intermediate Similarity	NPC474343
0.8	Intermediate Similarity	NPC476049
0.8	Intermediate Similarity	NPC222358
0.8	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC52609
0.8	Intermediate Similarity	NPC474703
0.8	Intermediate Similarity	NPC1761
0.798	Intermediate Similarity	NPC472753
0.798	Intermediate Similarity	NPC472643
0.7959	Intermediate Similarity	NPC141191
0.7935	Intermediate Similarity	NPC234038
0.7917	Intermediate Similarity	NPC121825
0.7917	Intermediate Similarity	NPC148463
0.7912	Intermediate Similarity	NPC474776
0.7912	Intermediate Similarity	NPC474359
0.79	Intermediate Similarity	NPC472754
0.79	Intermediate Similarity	NPC118405
0.7895	Intermediate Similarity	NPC45579
0.7879	Intermediate Similarity	NPC472644
0.7872	Intermediate Similarity	NPC5509
0.7872	Intermediate Similarity	NPC295312
0.7857	Intermediate Similarity	NPC169205
0.7849	Intermediate Similarity	NPC471738
0.7849	Intermediate Similarity	NPC312561
0.7835	Intermediate Similarity	NPC48803
0.7835	Intermediate Similarity	NPC193645
0.7835	Intermediate Similarity	NPC90121
0.7835	Intermediate Similarity	NPC275960
0.7826	Intermediate Similarity	NPC261380
0.7822	Intermediate Similarity	NPC472747
0.7822	Intermediate Similarity	NPC472750
0.7816	Intermediate Similarity	NPC471726
0.7816	Intermediate Similarity	NPC474527
0.7812	Intermediate Similarity	NPC109414
0.7812	Intermediate Similarity	NPC475302
0.7812	Intermediate Similarity	NPC469645
0.7812	Intermediate Similarity	NPC469692
0.7802	Intermediate Similarity	NPC53867
0.78	Intermediate Similarity	NPC473384
0.78	Intermediate Similarity	NPC185141
0.78	Intermediate Similarity	NPC110443
0.78	Intermediate Similarity	NPC46998
0.78	Intermediate Similarity	NPC128733
0.78	Intermediate Similarity	NPC133907
0.7789	Intermediate Similarity	NPC281942
0.7789	Intermediate Similarity	NPC51486
0.7789	Intermediate Similarity	NPC145666
0.7789	Intermediate Similarity	NPC232426
0.7789	Intermediate Similarity	NPC471818
0.7789	Intermediate Similarity	NPC469368
0.7778	Intermediate Similarity	NPC54843
0.7778	Intermediate Similarity	NPC325031
0.7778	Intermediate Similarity	NPC112868
0.7767	Intermediate Similarity	NPC475294
0.7766	Intermediate Similarity	NPC475902
0.7766	Intermediate Similarity	NPC469631
0.7766	Intermediate Similarity	NPC469653
0.7766	Intermediate Similarity	NPC471047
0.7766	Intermediate Similarity	NPC469628
0.7766	Intermediate Similarity	NPC475906
0.7755	Intermediate Similarity	NPC185553
0.7753	Intermediate Similarity	NPC469690
0.7753	Intermediate Similarity	NPC469620
0.7745	Intermediate Similarity	NPC472748
0.7742	Intermediate Similarity	NPC475461
0.7742	Intermediate Similarity	NPC220478
0.7742	Intermediate Similarity	NPC305475
0.7742	Intermediate Similarity	NPC116575
0.7732	Intermediate Similarity	NPC53685
0.7732	Intermediate Similarity	NPC476596
0.7717	Intermediate Similarity	NPC243618
0.7717	Intermediate Similarity	NPC196487
0.7717	Intermediate Similarity	NPC9868
0.7717	Intermediate Similarity	NPC82297
0.7717	Intermediate Similarity	NPC14575
0.7717	Intermediate Similarity	NPC70424
0.7708	Intermediate Similarity	NPC111114
0.7708	Intermediate Similarity	NPC141831
0.7708	Intermediate Similarity	NPC261607
0.7708	Intermediate Similarity	NPC300312
0.7708	Intermediate Similarity	NPC221282
0.7692	Intermediate Similarity	NPC474291
0.7692	Intermediate Similarity	NPC145963
0.7684	Intermediate Similarity	NPC115179
0.7684	Intermediate Similarity	NPC106040
0.7684	Intermediate Similarity	NPC268298
0.7677	Intermediate Similarity	NPC87090
0.7677	Intermediate Similarity	NPC208094
0.767	Intermediate Similarity	NPC472749
0.767	Intermediate Similarity	NPC472751
0.766	Intermediate Similarity	NPC474765
0.7653	Intermediate Similarity	NPC472469
0.7653	Intermediate Similarity	NPC295347
0.7653	Intermediate Similarity	NPC209355
0.7653	Intermediate Similarity	NPC470974
0.7653	Intermediate Similarity	NPC470978
0.7653	Intermediate Similarity	NPC272050
0.7653	Intermediate Similarity	NPC474490
0.7647	Intermediate Similarity	NPC475945
0.7647	Intermediate Similarity	NPC475871
0.764	Intermediate Similarity	NPC93763
0.764	Intermediate Similarity	NPC128276
0.764	Intermediate Similarity	NPC108816
0.7634	Intermediate Similarity	NPC86316
0.7634	Intermediate Similarity	NPC165162
0.7634	Intermediate Similarity	NPC106416
0.7634	Intermediate Similarity	NPC255307
0.7634	Intermediate Similarity	NPC65661
0.7634	Intermediate Similarity	NPC137033
0.7634	Intermediate Similarity	NPC474547
0.7634	Intermediate Similarity	NPC96621
0.7634	Intermediate Similarity	NPC161957
0.7629	Intermediate Similarity	NPC476598
0.7629	Intermediate Similarity	NPC476597
0.7629	Intermediate Similarity	NPC139692
0.7624	Intermediate Similarity	NPC474742
0.7624	Intermediate Similarity	NPC476270
0.7624	Intermediate Similarity	NPC477356
0.7614	Intermediate Similarity	NPC61863
0.7609	Intermediate Similarity	NPC193198
0.7609	Intermediate Similarity	NPC11620
0.7604	Intermediate Similarity	NPC476004
0.7604	Intermediate Similarity	NPC474761
0.7604	Intermediate Similarity	NPC129419
0.76	Intermediate Similarity	NPC23364
0.76	Intermediate Similarity	NPC316598
0.7582	Intermediate Similarity	NPC471325
0.7579	Intermediate Similarity	NPC202672
0.7579	Intermediate Similarity	NPC153805
0.7579	Intermediate Similarity	NPC474471
0.7579	Intermediate Similarity	NPC227379
0.7576	Intermediate Similarity	NPC202833
0.7573	Intermediate Similarity	NPC472756
0.7573	Intermediate Similarity	NPC203659
0.7573	Intermediate Similarity	NPC118911
0.7558	Intermediate Similarity	NPC40327
0.7556	Intermediate Similarity	NPC469617
0.7556	Intermediate Similarity	NPC470239
0.7556	Intermediate Similarity	NPC470244
0.7556	Intermediate Similarity	NPC178277
0.7553	Intermediate Similarity	NPC164393
0.7553	Intermediate Similarity	NPC122502
0.7553	Intermediate Similarity	NPC279859
0.7553	Intermediate Similarity	NPC38576
0.7553	Intermediate Similarity	NPC150755
0.7553	Intermediate Similarity	NPC284902
0.7551	Intermediate Similarity	NPC65829
0.7551	Intermediate Similarity	NPC167219
0.7551	Intermediate Similarity	NPC476415
0.7549	Intermediate Similarity	NPC474747
0.7549	Intermediate Similarity	NPC189609
0.7549	Intermediate Similarity	NPC197835
0.7549	Intermediate Similarity	NPC140591
0.7549	Intermediate Similarity	NPC303653
0.7549	Intermediate Similarity	NPC291500
0.7528	Intermediate Similarity	NPC116177
0.7528	Intermediate Similarity	NPC7563
0.7528	Intermediate Similarity	NPC57744
0.7528	Intermediate Similarity	NPC320630
0.7527	Intermediate Similarity	NPC149869
0.7527	Intermediate Similarity	NPC141193
0.7527	Intermediate Similarity	NPC114979
0.7527	Intermediate Similarity	NPC476804
0.7527	Intermediate Similarity	NPC31086
0.7527	Intermediate Similarity	NPC96259
0.7527	Intermediate Similarity	NPC72464
0.7527	Intermediate Similarity	NPC191476
0.7526	Intermediate Similarity	NPC30515
0.7526	Intermediate Similarity	NPC74103
0.7526	Intermediate Similarity	NPC284185
0.7526	Intermediate Similarity	NPC475972
0.7526	Intermediate Similarity	NPC472814
0.7526	Intermediate Similarity	NPC150978
0.7526	Intermediate Similarity	NPC303697
0.7526	Intermediate Similarity	NPC177037
0.7526	Intermediate Similarity	NPC70595
0.7526	Intermediate Similarity	NPC20713
0.7526	Intermediate Similarity	NPC123177
0.7525	Intermediate Similarity	NPC174314
0.7525	Intermediate Similarity	NPC117685
0.7525	Intermediate Similarity	NPC472972
0.7524	Intermediate Similarity	NPC476479
0.75	Intermediate Similarity	NPC85772
0.75	Intermediate Similarity	NPC254496
0.75	Intermediate Similarity	NPC83423
0.75	Intermediate Similarity	NPC280833
0.75	Intermediate Similarity	NPC221231
0.75	Intermediate Similarity	NPC474032
0.75	Intermediate Similarity	NPC168131
0.75	Intermediate Similarity	NPC89555

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 NPC219874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	2006
0.2-0.3	3640
0.3-0.4	2198
0.4-0.5	702
0.5-0.6	255
0.6-0.7	101
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7835	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5785	Approved
0.7312	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5697	Approved
0.7083	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD1694	Approved
0.7071	Intermediate Similarity	NPD6698	Approved
0.7071	Intermediate Similarity	NPD46	Approved
0.7065	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6881	Approved
0.7037	Intermediate Similarity	NPD6011	Approved
0.7037	Intermediate Similarity	NPD6899	Approved
0.701	Intermediate Similarity	NPD5786	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.699	Remote Similarity	NPD6084	Phase 2
0.699	Remote Similarity	NPD6083	Phase 2
0.6972	Remote Similarity	NPD6014	Approved
0.6972	Remote Similarity	NPD6012	Approved
0.6972	Remote Similarity	NPD6013	Approved
0.6961	Remote Similarity	NPD5695	Phase 3
0.6957	Remote Similarity	NPD4756	Discovery
0.6947	Remote Similarity	NPD6435	Approved
0.6947	Remote Similarity	NPD5209	Approved
0.6944	Remote Similarity	NPD5701	Approved
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6915	Remote Similarity	NPD4695	Discontinued
0.6909	Remote Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD6883	Approved
0.6909	Remote Similarity	NPD7102	Approved
0.6909	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD7320	Approved
0.6875	Remote Similarity	NPD7154	Phase 3
0.6875	Remote Similarity	NPD5362	Discontinued
0.6869	Remote Similarity	NPD5737	Approved
0.6869	Remote Similarity	NPD6672	Approved
0.6847	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD6650	Approved
0.6847	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD6617	Approved
0.6847	Remote Similarity	NPD6869	Approved
0.6847	Remote Similarity	NPD8130	Phase 1
0.6832	Remote Similarity	NPD5693	Phase 1
0.6818	Remote Similarity	NPD6373	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8297	Approved
0.6786	Remote Similarity	NPD6882	Approved
0.6771	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6762	Remote Similarity	NPD7638	Approved
0.6762	Remote Similarity	NPD5696	Approved
0.6737	Remote Similarity	NPD5368	Approved
0.6733	Remote Similarity	NPD7838	Discovery
0.6731	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5221	Approved
0.6727	Remote Similarity	NPD6686	Approved
0.6699	Remote Similarity	NPD7748	Approved
0.6699	Remote Similarity	NPD5282	Discontinued
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6609	Remote Similarity	NPD6868	Approved
0.6609	Remote Similarity	NPD6274	Approved
0.6602	Remote Similarity	NPD6399	Phase 3
0.6574	Remote Similarity	NPD5211	Phase 2
0.6571	Remote Similarity	NPD4697	Phase 3
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4252	Approved
0.6559	Remote Similarity	NPD8039	Approved
0.6552	Remote Similarity	NPD6317	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD4696	Approved
0.6542	Remote Similarity	NPD5285	Approved
0.6542	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD4755	Approved
0.6509	Remote Similarity	NPD7902	Approved
0.6505	Remote Similarity	NPD6079	Approved
0.65	Remote Similarity	NPD7146	Approved
0.65	Remote Similarity	NPD7334	Approved
0.65	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD6684	Approved
0.65	Remote Similarity	NPD5330	Approved
0.6496	Remote Similarity	NPD6313	Approved
0.6496	Remote Similarity	NPD6335	Approved
0.6496	Remote Similarity	NPD6314	Approved
0.6491	Remote Similarity	NPD6053	Discontinued
0.6481	Remote Similarity	NPD5223	Approved
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6904	Approved
0.6471	Remote Similarity	NPD6080	Approved
0.6471	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5328	Approved
0.6471	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD3665	Phase 1
0.6465	Remote Similarity	NPD3666	Approved
0.6465	Remote Similarity	NPD3133	Approved
0.6465	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5141	Approved
0.6441	Remote Similarity	NPD7101	Approved
0.6441	Remote Similarity	NPD7100	Approved
0.6436	Remote Similarity	NPD3573	Approved
0.6435	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.6422	Remote Similarity	NPD5224	Approved
0.6422	Remote Similarity	NPD5226	Approved
0.6422	Remote Similarity	NPD4633	Approved
0.6422	Remote Similarity	NPD5225	Approved
0.6415	Remote Similarity	NPD7839	Suspended
0.641	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD5692	Phase 3
0.6404	Remote Similarity	NPD7331	Phase 2
0.6404	Remote Similarity	NPD3704	Approved
0.64	Remote Similarity	NPD1696	Phase 3
0.6392	Remote Similarity	NPD4822	Approved
0.6392	Remote Similarity	NPD4820	Approved
0.6392	Remote Similarity	NPD4819	Approved
0.6392	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4821	Approved
0.6389	Remote Similarity	NPD4700	Approved
0.6387	Remote Similarity	NPD6319	Approved
0.6373	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD5331	Approved
0.6364	Remote Similarity	NPD5332	Approved
0.6364	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD4268	Approved
0.6354	Remote Similarity	NPD4271	Approved
0.6346	Remote Similarity	NPD5694	Approved
0.6346	Remote Similarity	NPD6050	Approved
0.6337	Remote Similarity	NPD3618	Phase 1
0.6333	Remote Similarity	NPD5983	Phase 2
0.6327	Remote Similarity	NPD4790	Discontinued
0.6321	Remote Similarity	NPD5210	Approved
0.6321	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD1695	Approved
0.63	Remote Similarity	NPD4786	Approved
0.6296	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7341	Phase 2
0.627	Remote Similarity	NPD7260	Phase 2
0.6263	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7604	Phase 2
0.6226	Remote Similarity	NPD7900	Approved
0.6226	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4754	Approved
0.6198	Remote Similarity	NPD6909	Approved
0.6198	Remote Similarity	NPD6908	Approved
0.6198	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7637	Suspended
0.6182	Remote Similarity	NPD5344	Discontinued
0.618	Remote Similarity	NPD3197	Phase 1
0.6179	Remote Similarity	NPD7492	Approved
0.6176	Remote Similarity	NPD4249	Approved
0.6176	Remote Similarity	NPD6098	Approved
0.6176	Remote Similarity	NPD5690	Phase 2
0.6176	Remote Similarity	NPD6422	Discontinued
0.614	Remote Similarity	NPD4729	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5168	Approved
0.614	Remote Similarity	NPD5128	Approved
0.614	Remote Similarity	NPD4730	Approved
0.6139	Remote Similarity	NPD4197	Approved
0.6129	Remote Similarity	NPD6616	Approved
0.6129	Remote Similarity	NPD6336	Discontinued
0.6126	Remote Similarity	NPD7632	Discontinued
0.6121	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD4250	Approved
0.6116	Remote Similarity	NPD6054	Approved
0.6106	Remote Similarity	NPD4767	Approved
0.6106	Remote Similarity	NPD4768	Approved
0.6106	Remote Similarity	NPD6008	Approved
0.6098	Remote Similarity	NPD8328	Phase 3
0.6087	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7078	Approved
0.6078	Remote Similarity	NPD5329	Approved
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6044	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5284	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