NPASS Compound

Structure

NPC474476 OpenBabel07101718332D 23 24 0 0 1 0 0 0 0 0999 V2000 -5.0468 5.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 5.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7565 -2.9745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0623 -2.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2213 -1.3272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 4.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0134 -2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 3 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 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 2.3364 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 14 17 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.17
Volume:	339.409
LogP:	5.545
LogD:	4.453
LogS:	-4.296
# Rotatable Bonds:	6
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	2.754
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.707
MDCK Permeability:	1.843141762947198e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.731

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	98.4563217163086%
Volume Distribution (VD):	1.138
Pgp-substrate:	3.768953323364258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.637
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.692
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.098
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	11.746
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.854
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.309
Carcinogencity:	0.444
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.814

Download Data

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

Natural Product: NPC474476

Natural Product ID:	NPC474476
*Common Name:**	Antrocinnamomin D
IUPAC Name:	2-hydroxy-4-[4-(3-methylbut-2-enoxy)phenyl]-3-(2-methylpropyl)-2H-furan-5-one
Synonyms:	Antrocinnamomin D
Standard InCHIKey:	WALOFELUZXOXIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H24O4/c1-12(2)9-10-22-15-7-5-14(6-8-15)17-16(11-13(3)4)18(20)23-19(17)21/h5-9,13,18,20H,10-11H2,1-4H3
SMILES:	CC(=CCOc1ccc(cc1)C1=C(CC(C)C)C(OC1=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469703
PubChem CID:	24970583
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO32621	antrodia cinnamomea	Species	Fomitopsidaceae	Eukaryota	mycelia	n.a.	n.a.	PMID[18522430]
NPO32621	antrodia cinnamomea	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28898082]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	20.0	uM	PMID[523630]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	88.2	%	PMID[523630]

☑ 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 NPC474476 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	237
0.1-0.2	1166
0.2-0.3	3510
0.3-0.4	8501
0.4-0.5	10277
0.5-0.6	5009
0.6-0.7	11222
0.7-0.8	2725
0.8-0.85	46
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC293424
0.8651	High Similarity	NPC473942
0.8583	High Similarity	NPC221798
0.8583	High Similarity	NPC17693
0.8548	High Similarity	NPC264976
0.8525	High Similarity	NPC51345
0.8487	Intermediate Similarity	NPC234639
0.8455	Intermediate Similarity	NPC128249
0.845	Intermediate Similarity	NPC475236
0.8425	Intermediate Similarity	NPC291189
0.8425	Intermediate Similarity	NPC69403
0.8374	Intermediate Similarity	NPC296526
0.8361	Intermediate Similarity	NPC109241
0.8333	Intermediate Similarity	NPC474874
0.8333	Intermediate Similarity	NPC193193
0.8321	Intermediate Similarity	NPC2596
0.8295	Intermediate Similarity	NPC89630
0.8235	Intermediate Similarity	NPC1065
0.8189	Intermediate Similarity	NPC31314
0.8182	Intermediate Similarity	NPC259554
0.8175	Intermediate Similarity	NPC471033
0.8175	Intermediate Similarity	NPC311091
0.8167	Intermediate Similarity	NPC151530
0.8167	Intermediate Similarity	NPC157473
0.816	Intermediate Similarity	NPC19290
0.8151	Intermediate Similarity	NPC473855
0.8151	Intermediate Similarity	NPC470393
0.8145	Intermediate Similarity	NPC235250
0.8134	Intermediate Similarity	NPC470977
0.8134	Intermediate Similarity	NPC196979
0.8134	Intermediate Similarity	NPC470976
0.8129	Intermediate Similarity	NPC80098
0.812	Intermediate Similarity	NPC238309
0.811	Intermediate Similarity	NPC61779
0.8102	Intermediate Similarity	NPC294470
0.8099	Intermediate Similarity	NPC31274
0.8099	Intermediate Similarity	NPC291153
0.8092	Intermediate Similarity	NPC88403
0.8092	Intermediate Similarity	NPC280767
0.8088	Intermediate Similarity	NPC34456
0.8085	Intermediate Similarity	NPC471028
0.8083	Intermediate Similarity	NPC326447
0.8083	Intermediate Similarity	NPC176971
0.8074	Intermediate Similarity	NPC169766
0.8067	Intermediate Similarity	NPC38079
0.8067	Intermediate Similarity	NPC108875
0.806	Intermediate Similarity	NPC282230
0.806	Intermediate Similarity	NPC183348
0.8042	Intermediate Similarity	NPC473149
0.803	Intermediate Similarity	NPC110211
0.8016	Intermediate Similarity	NPC33717
0.8016	Intermediate Similarity	NPC470860
0.8014	Intermediate Similarity	NPC242756
0.8	Intermediate Similarity	NPC15083
0.8	Intermediate Similarity	NPC104854
0.8	Intermediate Similarity	NPC128730
0.8	Intermediate Similarity	NPC311219
0.8	Intermediate Similarity	NPC79908
0.8	Intermediate Similarity	NPC125153
0.7986	Intermediate Similarity	NPC327612
0.7986	Intermediate Similarity	NPC319870
0.7986	Intermediate Similarity	NPC73078
0.7986	Intermediate Similarity	NPC148738
0.7985	Intermediate Similarity	NPC939
0.7985	Intermediate Similarity	NPC295970
0.7985	Intermediate Similarity	NPC241354
0.7985	Intermediate Similarity	NPC66246
0.7985	Intermediate Similarity	NPC170546
0.7983	Intermediate Similarity	NPC192596
0.7971	Intermediate Similarity	NPC246177
0.7971	Intermediate Similarity	NPC90431
0.7971	Intermediate Similarity	NPC223616
0.7971	Intermediate Similarity	NPC317045
0.797	Intermediate Similarity	NPC121104
0.7956	Intermediate Similarity	NPC471029
0.7956	Intermediate Similarity	NPC196708
0.7956	Intermediate Similarity	NPC471110
0.7953	Intermediate Similarity	NPC240664
0.7943	Intermediate Similarity	NPC65833
0.7943	Intermediate Similarity	NPC31081
0.7943	Intermediate Similarity	NPC184053
0.7943	Intermediate Similarity	NPC245219
0.7941	Intermediate Similarity	NPC269421
0.7939	Intermediate Similarity	NPC14141
0.7931	Intermediate Similarity	NPC111785
0.7926	Intermediate Similarity	NPC2989
0.7926	Intermediate Similarity	NPC86774
0.7926	Intermediate Similarity	NPC327457
0.7917	Intermediate Similarity	NPC38209
0.7917	Intermediate Similarity	NPC2518
0.7917	Intermediate Similarity	NPC283546
0.7899	Intermediate Similarity	NPC51633
0.7899	Intermediate Similarity	NPC212729
0.7899	Intermediate Similarity	NPC475011
0.7895	Intermediate Similarity	NPC204579
0.7891	Intermediate Similarity	NPC21831
0.7891	Intermediate Similarity	NPC205502
0.7891	Intermediate Similarity	NPC94298
0.7891	Intermediate Similarity	NPC187547
0.7891	Intermediate Similarity	NPC27633
0.7887	Intermediate Similarity	NPC229916
0.7887	Intermediate Similarity	NPC469367
0.7887	Intermediate Similarity	NPC475213
0.7887	Intermediate Similarity	NPC152796
0.7886	Intermediate Similarity	NPC79543
0.7883	Intermediate Similarity	NPC114116
0.7883	Intermediate Similarity	NPC475468
0.7879	Intermediate Similarity	NPC288945
0.7877	Intermediate Similarity	NPC104172
0.7877	Intermediate Similarity	NPC100818
0.7877	Intermediate Similarity	NPC182350
0.7877	Intermediate Similarity	NPC88886
0.7872	Intermediate Similarity	NPC166137
0.7872	Intermediate Similarity	NPC477535
0.7872	Intermediate Similarity	NPC475044
0.7872	Intermediate Similarity	NPC282291
0.7872	Intermediate Similarity	NPC475063
0.7872	Intermediate Similarity	NPC477537
0.7868	Intermediate Similarity	NPC470392
0.7862	Intermediate Similarity	NPC66991
0.7857	Intermediate Similarity	NPC475005
0.7857	Intermediate Similarity	NPC252004
0.7857	Intermediate Similarity	NPC474943
0.7852	Intermediate Similarity	NPC194979
0.7852	Intermediate Similarity	NPC474289
0.7852	Intermediate Similarity	NPC473019
0.7847	Intermediate Similarity	NPC474044
0.7842	Intermediate Similarity	NPC64230
0.7842	Intermediate Similarity	NPC170604
0.7842	Intermediate Similarity	NPC215109
0.7842	Intermediate Similarity	NPC71638
0.7842	Intermediate Similarity	NPC471345
0.784	Intermediate Similarity	NPC199462
0.7836	Intermediate Similarity	NPC473993
0.7836	Intermediate Similarity	NPC121740
0.7836	Intermediate Similarity	NPC258567
0.7836	Intermediate Similarity	NPC224774
0.7833	Intermediate Similarity	NPC298224
0.7833	Intermediate Similarity	NPC179686
0.7832	Intermediate Similarity	NPC473090
0.7829	Intermediate Similarity	NPC37858
0.7826	Intermediate Similarity	NPC68779
0.7826	Intermediate Similarity	NPC211164
0.7826	Intermediate Similarity	NPC176814
0.7826	Intermediate Similarity	NPC5310
0.7826	Intermediate Similarity	NPC4982
0.7826	Intermediate Similarity	NPC300776
0.7823	Intermediate Similarity	NPC25067
0.7823	Intermediate Similarity	NPC183700
0.7823	Intermediate Similarity	NPC88868
0.7823	Intermediate Similarity	NPC231251
0.782	Intermediate Similarity	NPC49938
0.782	Intermediate Similarity	NPC470858
0.782	Intermediate Similarity	NPC137416
0.782	Intermediate Similarity	NPC4164
0.7817	Intermediate Similarity	NPC52664
0.7812	Intermediate Similarity	NPC183154
0.7812	Intermediate Similarity	NPC263754
0.781	Intermediate Similarity	NPC317601
0.781	Intermediate Similarity	NPC132308
0.781	Intermediate Similarity	NPC329427
0.781	Intermediate Similarity	NPC470160
0.7808	Intermediate Similarity	NPC287294
0.7805	Intermediate Similarity	NPC291837
0.7803	Intermediate Similarity	NPC477152
0.7803	Intermediate Similarity	NPC118853
0.7801	Intermediate Similarity	NPC475045
0.7801	Intermediate Similarity	NPC71903
0.7801	Intermediate Similarity	NPC475012
0.7795	Intermediate Similarity	NPC220540
0.7795	Intermediate Similarity	NPC322358
0.7794	Intermediate Similarity	NPC477694
0.7794	Intermediate Similarity	NPC109778
0.7794	Intermediate Similarity	NPC477705
0.7793	Intermediate Similarity	NPC286038
0.7786	Intermediate Similarity	NPC470397
0.7786	Intermediate Similarity	NPC471068
0.7786	Intermediate Similarity	NPC177291
0.7786	Intermediate Similarity	NPC471069
0.7786	Intermediate Similarity	NPC114845
0.7786	Intermediate Similarity	NPC194416
0.7786	Intermediate Similarity	NPC187826
0.7778	Intermediate Similarity	NPC146540
0.7778	Intermediate Similarity	NPC219923
0.7778	Intermediate Similarity	NPC10302
0.7778	Intermediate Similarity	NPC105381
0.7778	Intermediate Similarity	NPC2401
0.7778	Intermediate Similarity	NPC469453
0.777	Intermediate Similarity	NPC303217
0.777	Intermediate Similarity	NPC236974
0.777	Intermediate Similarity	NPC144027
0.777	Intermediate Similarity	NPC36130
0.777	Intermediate Similarity	NPC475029
0.777	Intermediate Similarity	NPC134905
0.777	Intermediate Similarity	NPC476018
0.7769	Intermediate Similarity	NPC109637
0.7769	Intermediate Similarity	NPC72977
0.7769	Intermediate Similarity	NPC230951
0.7769	Intermediate Similarity	NPC470092
0.776	Intermediate Similarity	NPC23332

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 NPC474476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	813
0.2-0.3	1544
0.3-0.4	2481
0.4-0.5	2041
0.5-0.6	1312
0.6-0.7	618
0.7-0.8	131
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8211	Intermediate Similarity	NPD1241	Discontinued
0.8175	Intermediate Similarity	NPD1894	Discontinued
0.8092	Intermediate Similarity	NPD2797	Approved
0.8083	Intermediate Similarity	NPD3134	Approved
0.803	Intermediate Similarity	NPD5647	Approved
0.8015	Intermediate Similarity	NPD6355	Discontinued
0.8	Intermediate Similarity	NPD9717	Approved
0.8	Intermediate Similarity	NPD1481	Phase 2
0.7943	Intermediate Similarity	NPD4628	Phase 3
0.7926	Intermediate Similarity	NPD6798	Discontinued
0.7926	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD3268	Approved
0.7923	Intermediate Similarity	NPD1535	Discovery
0.7902	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD9545	Approved
0.7872	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD1358	Approved
0.7868	Intermediate Similarity	NPD4062	Phase 3
0.7868	Intermediate Similarity	NPD6233	Phase 2
0.7846	Intermediate Similarity	NPD3496	Discontinued
0.7842	Intermediate Similarity	NPD2799	Discontinued
0.782	Intermediate Similarity	NPD6362	Approved
0.7805	Intermediate Similarity	NPD2684	Approved
0.7778	Intermediate Similarity	NPD6832	Phase 2
0.7778	Intermediate Similarity	NPD2614	Approved
0.7727	Intermediate Similarity	NPD1608	Approved
0.771	Intermediate Similarity	NPD3847	Discontinued
0.7704	Intermediate Similarity	NPD454	Approved
0.7698	Intermediate Similarity	NPD7843	Approved
0.7698	Intermediate Similarity	NPD5535	Approved
0.7698	Intermediate Similarity	NPD6653	Approved
0.7687	Intermediate Similarity	NPD1203	Approved
0.7671	Intermediate Similarity	NPD6273	Approved
0.7669	Intermediate Similarity	NPD3685	Discontinued
0.7643	Intermediate Similarity	NPD7097	Phase 1
0.7634	Intermediate Similarity	NPD1778	Approved
0.7622	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1283	Approved
0.7606	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6002	Phase 3
0.7606	Intermediate Similarity	NPD6005	Phase 3
0.7606	Intermediate Similarity	NPD6004	Phase 3
0.7589	Intermediate Similarity	NPD7033	Discontinued
0.7586	Intermediate Similarity	NPD7440	Discontinued
0.7569	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4110	Phase 3
0.7557	Intermediate Similarity	NPD5585	Approved
0.7556	Intermediate Similarity	NPD3266	Approved
0.7556	Intermediate Similarity	NPD3267	Approved
0.7535	Intermediate Similarity	NPD4477	Approved
0.7535	Intermediate Similarity	NPD2239	Approved
0.7535	Intermediate Similarity	NPD2240	Approved
0.7535	Intermediate Similarity	NPD2935	Discontinued
0.7535	Intermediate Similarity	NPD4476	Approved
0.7519	Intermediate Similarity	NPD422	Phase 1
0.7519	Intermediate Similarity	NPD7157	Approved
0.7517	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD17	Approved
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3225	Approved
0.7465	Intermediate Similarity	NPD4308	Phase 3
0.7462	Intermediate Similarity	NPD9493	Approved
0.7448	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5958	Discontinued
0.7429	Intermediate Similarity	NPD2979	Phase 3
0.7429	Intermediate Similarity	NPD4060	Phase 1
0.7429	Intermediate Similarity	NPD4140	Approved
0.7424	Intermediate Similarity	NPD5691	Approved
0.7422	Intermediate Similarity	NPD821	Approved
0.7415	Intermediate Similarity	NPD6799	Approved
0.741	Intermediate Similarity	NPD411	Approved
0.741	Intermediate Similarity	NPD2313	Discontinued
0.7388	Intermediate Similarity	NPD1281	Approved
0.7388	Intermediate Similarity	NPD1091	Approved
0.7376	Intermediate Similarity	NPD1933	Approved
0.7376	Intermediate Similarity	NPD447	Suspended
0.7376	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5124	Phase 1
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD8032	Phase 2
0.7353	Intermediate Similarity	NPD1876	Approved
0.7338	Intermediate Similarity	NPD7095	Approved
0.7338	Intermediate Similarity	NPD5163	Phase 2
0.7333	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD7003	Approved
0.7329	Intermediate Similarity	NPD3750	Approved
0.732	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD4534	Discontinued
0.731	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3142	Approved
0.7305	Intermediate Similarity	NPD3140	Approved
0.7303	Intermediate Similarity	NPD7411	Suspended
0.7302	Intermediate Similarity	NPD290	Approved
0.7293	Intermediate Similarity	NPD1357	Approved
0.7292	Intermediate Similarity	NPD1551	Phase 2
0.729	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3764	Approved
0.7285	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD9697	Approved
0.7279	Intermediate Similarity	NPD3887	Approved
0.7279	Intermediate Similarity	NPD4359	Approved
0.7279	Intermediate Similarity	NPD2354	Approved
0.7259	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4618	Approved
0.7254	Intermediate Similarity	NPD4340	Discontinued
0.7254	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4622	Approved
0.7241	Intermediate Similarity	NPD2344	Approved
0.7241	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD196	Phase 1
0.7222	Intermediate Similarity	NPD968	Approved
0.7211	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD9494	Approved
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.7192	Intermediate Similarity	NPD2424	Discontinued
0.7188	Intermediate Similarity	NPD2067	Discontinued
0.7183	Intermediate Similarity	NPD4307	Phase 2
0.7174	Intermediate Similarity	NPD987	Approved
0.7172	Intermediate Similarity	NPD2531	Phase 2
0.7172	Intermediate Similarity	NPD2438	Suspended
0.7165	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1296	Phase 2
0.7153	Intermediate Similarity	NPD5688	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5689	Approved
0.7152	Intermediate Similarity	NPD5403	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6599	Discontinued
0.7123	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2346	Discontinued
0.7123	Intermediate Similarity	NPD2353	Approved
0.712	Intermediate Similarity	NPD6647	Phase 2
0.7115	Intermediate Similarity	NPD7768	Phase 2
0.7115	Intermediate Similarity	NPD4965	Approved
0.7115	Intermediate Similarity	NPD4967	Phase 2
0.7115	Intermediate Similarity	NPD4966	Approved
0.7113	Intermediate Similarity	NPD5745	Approved
0.7109	Intermediate Similarity	NPD2182	Approved
0.7105	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3748	Approved
0.7097	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6390	Discontinued
0.7086	Intermediate Similarity	NPD5049	Phase 3
0.7078	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6677	Suspended
0.7078	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD969	Suspended
0.7073	Intermediate Similarity	NPD6559	Discontinued
0.707	Intermediate Similarity	NPD6971	Discontinued
0.707	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD1240	Approved
0.7063	Intermediate Similarity	NPD5909	Discontinued
0.7055	Intermediate Similarity	NPD1519	Approved
0.7055	Intermediate Similarity	NPD2796	Approved
0.7055	Intermediate Similarity	NPD1537	Approved
0.7055	Intermediate Similarity	NPD1538	Phase 1
0.7055	Intermediate Similarity	NPD5712	Approved
0.7047	Intermediate Similarity	NPD2309	Approved
0.7044	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7427	Discontinued
0.7037	Intermediate Similarity	NPD3818	Discontinued
0.7037	Intermediate Similarity	NPD1651	Approved
0.7034	Intermediate Similarity	NPD1536	Approved
0.7029	Intermediate Similarity	NPD6582	Phase 2
0.7029	Intermediate Similarity	NPD6583	Phase 3
0.7027	Intermediate Similarity	NPD1652	Phase 2
0.7023	Intermediate Similarity	NPD1138	Approved
0.7021	Intermediate Similarity	NPD4908	Phase 1
0.702	Intermediate Similarity	NPD2534	Approved
0.702	Intermediate Similarity	NPD5401	Approved
0.702	Intermediate Similarity	NPD2532	Approved
0.702	Intermediate Similarity	NPD2533	Approved
0.7015	Intermediate Similarity	NPD5536	Phase 2
0.7014	Intermediate Similarity	NPD230	Phase 1
0.7013	Intermediate Similarity	NPD7028	Phase 2
0.7013	Intermediate Similarity	NPD6502	Phase 2
0.7007	Intermediate Similarity	NPD3705	Approved
0.7007	Intermediate Similarity	NPD7266	Discontinued
0.7007	Intermediate Similarity	NPD5763	Approved
0.7007	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6666	Approved
0.7	Intermediate Similarity	NPD6667	Approved
0.6994	Remote Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4870	Approved
0.6993	Remote Similarity	NPD1653	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