NPASS Compound

Structure

NPC61813 OpenBabel07101719402D 42 47 0 0 1 0 0 0 0 0999 V2000 8.3739 -1.6558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2219 -0.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2219 0.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3739 2.2609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3711 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8815 1.1104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2977 0.8945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5259 -0.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5259 0.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6779 -0.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6779 1.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9820 -0.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9820 1.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6272 -1.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3739 -0.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3739 1.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8300 -0.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8300 0.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -0.9792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1340 -0.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2027 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 0.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6272 0.3026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 1.4688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3919 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6960 -0.0000 0.0000 C 0 0 1 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 3.2027 1.0947 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 7 35 1 0 0 0 0 9 11 1 0 0 0 0 9 21 2 0 0 0 0 10 12 1 0 0 0 0 10 22 2 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 15 35 1 0 0 0 0 16 37 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 27 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 23 24 1 0 0 0 0 25 36 1 6 0 0 0 26 27 1 0 0 0 0 26 29 2 0 0 0 0 27 32 2 0 0 0 0 28 31 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 33 1 0 0 0 0 30 39 2 0 0 0 0 31 14 1 1 0 0 0 31 42 1 0 0 0 0 32 36 1 0 0 0 0 32 38 1 0 0 0 0 33 34 1 1 0 0 0 33 42 1 0 0 0 0 34 40 1 0 0 0 0 35 36 1 6 0 0 0 36 8 1 6 0 0 0 37 35 1 6 0 0 0 37 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	571.37
Volume:	622.235
LogP:	7.189
LogD:	4.316
LogS:	-4.63
# Rotatable Bonds:	5
TPSA:	82.55
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	5.254
Fsp3:	0.595
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	1.700975735730026e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.73
Plasma Protein Binding (PPB):	90.12154388427734%
Volume Distribution (VD):	3.108
Pgp-substrate:	8.547446250915527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.204
CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.688
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.465
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.873

ADMET: Excretion

Clearance (CL):	12.694
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.291
Human Hepatotoxicity (H-HT):	0.901
Drug-inuced Liver Injury (DILI):	0.345
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.655
Carcinogencity:	0.875
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC61813

Natural Product ID:	NPC61813
*Common Name:**	YMPSZJNRZBHLRI-OGYDQXLWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YMPSZJNRZBHLRI-OGYDQXLWSA-N
Standard InCHI:	InChI=1S/C37H49NO4/c1-21(2)9-11-23-17-26-27-19-25-13-16-37(41)28-20-30(39)33(34(5,6)40)42-31(28)14-15-35(37,7)36(25,8)32(27)38-29(26)18-24(23)12-10-22(3)4/h9-10,17-18,20,25,31,33,38,40-41H,11-16,19H2,1-8H3/t25-,31-,33-,35+,36+,37+/m0/s1
SMILES:	CC(=CCc1cc2c3C[C@@H]4CC[C@]5(C6=CC(=O)[C@@H](C(C)(C)O)O[C@H]6CC[C@]5(C)[C@@]4(C)c3[nH]c2cc1CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408944
PubChem CID:	71745339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO32542	penicillium camemberti oucmdz-1492	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23886345]

☑ 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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	73300.0	nM	PMID[485719]

☑ 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 NPC61813 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	373
0.1-0.2	1586
0.2-0.3	3862
0.3-0.4	14458
0.4-0.5	17607
0.5-0.6	3552
0.6-0.7	1102
0.7-0.8	96
0.8-0.85	30
0.85-0.9	16
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC96131
0.9541	High Similarity	NPC235900
0.9463	High Similarity	NPC282033
0.9444	High Similarity	NPC471284
0.9082	High Similarity	NPC123019
0.9065	High Similarity	NPC470843
0.9065	High Similarity	NPC94541
0.8818	High Similarity	NPC250129
0.881	High Similarity	NPC79107
0.881	High Similarity	NPC475424
0.8768	High Similarity	NPC475165
0.8689	High Similarity	NPC97388
0.8663	High Similarity	NPC187456
0.8641	High Similarity	NPC473547
0.86	High Similarity	NPC475151
0.8537	High Similarity	NPC284102
0.8512	High Similarity	NPC473806
0.8512	High Similarity	NPC471634
0.851	High Similarity	NPC160527
0.851	High Similarity	NPC473650
0.85	High Similarity	NPC473747
0.8469	Intermediate Similarity	NPC34271
0.839	Intermediate Similarity	NPC18661
0.8349	Intermediate Similarity	NPC242446
0.8349	Intermediate Similarity	NPC475476
0.8173	Intermediate Similarity	NPC165201
0.8141	Intermediate Similarity	NPC119700
0.814	Intermediate Similarity	NPC470874
0.8128	Intermediate Similarity	NPC231342
0.8071	Intermediate Similarity	NPC302191
0.806	Intermediate Similarity	NPC206967
0.802	Intermediate Similarity	NPC198339
0.7923	Intermediate Similarity	NPC32200
0.7919	Intermediate Similarity	NPC470873
0.791	Intermediate Similarity	NPC99428
0.7902	Intermediate Similarity	NPC181502
0.7902	Intermediate Similarity	NPC85066
0.7879	Intermediate Similarity	NPC6093
0.7766	Intermediate Similarity	NPC97525
0.7763	Intermediate Similarity	NPC473565
0.7758	Intermediate Similarity	NPC249342
0.7738	Intermediate Similarity	NPC469312
0.7738	Intermediate Similarity	NPC41318
0.7668	Intermediate Similarity	NPC245756
0.7608	Intermediate Similarity	NPC205403
0.7606	Intermediate Similarity	NPC477135
0.76	Intermediate Similarity	NPC57690
0.76	Intermediate Similarity	NPC183426
0.7595	Intermediate Similarity	NPC131273
0.7595	Intermediate Similarity	NPC473441
0.7589	Intermediate Similarity	NPC235885
0.7589	Intermediate Similarity	NPC141428
0.7532	Intermediate Similarity	NPC188239
0.7466	Intermediate Similarity	NPC204491
0.7466	Intermediate Similarity	NPC203614
0.7457	Intermediate Similarity	NPC278540
0.7437	Intermediate Similarity	NPC154293
0.7425	Intermediate Similarity	NPC471782
0.7425	Intermediate Similarity	NPC471583
0.7424	Intermediate Similarity	NPC290529
0.7404	Intermediate Similarity	NPC46413
0.7401	Intermediate Similarity	NPC267926
0.7385	Intermediate Similarity	NPC127677
0.7385	Intermediate Similarity	NPC258062
0.7378	Intermediate Similarity	NPC2395
0.7364	Intermediate Similarity	NPC204303
0.7353	Intermediate Similarity	NPC270009
0.7343	Intermediate Similarity	NPC476319
0.7339	Intermediate Similarity	NPC225821
0.7339	Intermediate Similarity	NPC46225
0.7313	Intermediate Similarity	NPC266192
0.7313	Intermediate Similarity	NPC147446
0.73	Intermediate Similarity	NPC311451
0.7277	Intermediate Similarity	NPC249428
0.7252	Intermediate Similarity	NPC151976
0.7252	Intermediate Similarity	NPC87856
0.7246	Intermediate Similarity	NPC472444
0.7243	Intermediate Similarity	NPC472589
0.7238	Intermediate Similarity	NPC473389
0.7232	Intermediate Similarity	NPC132211
0.7202	Intermediate Similarity	NPC98715
0.7197	Intermediate Similarity	NPC199259
0.7195	Intermediate Similarity	NPC477548
0.7182	Intermediate Similarity	NPC474905
0.716	Intermediate Similarity	NPC472588
0.7157	Intermediate Similarity	NPC34508
0.7149	Intermediate Similarity	NPC61637
0.7108	Intermediate Similarity	NPC126492
0.7101	Intermediate Similarity	NPC472443
0.71	Intermediate Similarity	NPC112547
0.71	Intermediate Similarity	NPC473320
0.7098	Intermediate Similarity	NPC475778
0.7085	Intermediate Similarity	NPC234999
0.7072	Intermediate Similarity	NPC470280
0.7067	Intermediate Similarity	NPC300688
0.7067	Intermediate Similarity	NPC267965
0.7045	Intermediate Similarity	NPC476115
0.704	Intermediate Similarity	NPC271862
0.7035	Intermediate Similarity	NPC184476
0.703	Intermediate Similarity	NPC472587
0.7014	Intermediate Similarity	NPC477043
0.7	Intermediate Similarity	NPC19679
0.6987	Remote Similarity	NPC253482
0.6983	Remote Similarity	NPC476818
0.6976	Remote Similarity	NPC280548
0.6959	Remote Similarity	NPC11445
0.6957	Remote Similarity	NPC472586
0.6955	Remote Similarity	NPC107836
0.6952	Remote Similarity	NPC192270
0.6949	Remote Similarity	NPC319880
0.6949	Remote Similarity	NPC244839
0.6949	Remote Similarity	NPC320324
0.6948	Remote Similarity	NPC89549
0.6942	Remote Similarity	NPC6982
0.6941	Remote Similarity	NPC476175
0.692	Remote Similarity	NPC70155
0.692	Remote Similarity	NPC237702
0.6916	Remote Similarity	NPC61435
0.6912	Remote Similarity	NPC195239
0.6912	Remote Similarity	NPC157828
0.6909	Remote Similarity	NPC79129
0.6909	Remote Similarity	NPC195461
0.6909	Remote Similarity	NPC249150
0.6909	Remote Similarity	NPC81654
0.6909	Remote Similarity	NPC49196
0.6909	Remote Similarity	NPC313985
0.6907	Remote Similarity	NPC473689
0.6907	Remote Similarity	NPC292416
0.6907	Remote Similarity	NPC477531
0.6904	Remote Similarity	NPC6786
0.6903	Remote Similarity	NPC9894
0.6901	Remote Similarity	NPC475648
0.69	Remote Similarity	NPC471458
0.6898	Remote Similarity	NPC67551
0.6895	Remote Similarity	NPC477041
0.6895	Remote Similarity	NPC477044
0.6894	Remote Similarity	NPC252251
0.6891	Remote Similarity	NPC35208
0.689	Remote Similarity	NPC151939
0.6884	Remote Similarity	NPC469497
0.6884	Remote Similarity	NPC106833
0.6878	Remote Similarity	NPC300183
0.6872	Remote Similarity	NPC48353
0.687	Remote Similarity	NPC82070
0.6864	Remote Similarity	NPC209174
0.6864	Remote Similarity	NPC192674
0.6862	Remote Similarity	NPC38959
0.6862	Remote Similarity	NPC327904
0.6854	Remote Similarity	NPC473189
0.6852	Remote Similarity	NPC129909
0.6851	Remote Similarity	NPC87152
0.6851	Remote Similarity	NPC475600
0.6851	Remote Similarity	NPC475631
0.6851	Remote Similarity	NPC476110
0.6837	Remote Similarity	NPC128751
0.6837	Remote Similarity	NPC246700
0.6835	Remote Similarity	NPC150698
0.6835	Remote Similarity	NPC96801
0.683	Remote Similarity	NPC476106
0.6829	Remote Similarity	NPC476516
0.6826	Remote Similarity	NPC314552
0.6822	Remote Similarity	NPC471977
0.6822	Remote Similarity	NPC470486
0.6822	Remote Similarity	NPC471190
0.6822	Remote Similarity	NPC475644
0.682	Remote Similarity	NPC475406
0.6818	Remote Similarity	NPC50503
0.6818	Remote Similarity	NPC475844
0.681	Remote Similarity	NPC293472
0.6809	Remote Similarity	NPC472762
0.68	Remote Similarity	NPC193777
0.6795	Remote Similarity	NPC475271
0.6787	Remote Similarity	NPC477045
0.6784	Remote Similarity	NPC124005
0.6784	Remote Similarity	NPC475422
0.6783	Remote Similarity	NPC476114
0.6781	Remote Similarity	NPC477532
0.6781	Remote Similarity	NPC280799
0.678	Remote Similarity	NPC146824
0.678	Remote Similarity	NPC228377
0.678	Remote Similarity	NPC477787
0.678	Remote Similarity	NPC122968
0.678	Remote Similarity	NPC328186
0.6777	Remote Similarity	NPC472207
0.6776	Remote Similarity	NPC280290
0.6773	Remote Similarity	NPC153042
0.6771	Remote Similarity	NPC162730
0.6771	Remote Similarity	NPC474116
0.6767	Remote Similarity	NPC52254
0.6765	Remote Similarity	NPC475596
0.6765	Remote Similarity	NPC475303
0.6762	Remote Similarity	NPC288785
0.6757	Remote Similarity	NPC214428
0.6753	Remote Similarity	NPC6981
0.6751	Remote Similarity	NPC475362
0.675	Remote Similarity	NPC263937
0.675	Remote Similarity	NPC94428
0.6748	Remote Similarity	NPC470508
0.6743	Remote Similarity	NPC55493
0.6743	Remote Similarity	NPC47190

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 NPC61813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	567
0.2-0.3	665
0.3-0.4	2254
0.4-0.5	3509
0.5-0.6	1618
0.6-0.7	274
0.7-0.8	3
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
0.7195	Intermediate Similarity	NPD5834	Phase 3
0.7195	Intermediate Similarity	NPD5835	Phase 3
0.7083	Intermediate Similarity	NPD5003	Discontinued
0.7018	Intermediate Similarity	NPD6248	Phase 2
0.7018	Intermediate Similarity	NPD6249	Phase 2
0.7009	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6995	Phase 1
0.6968	Remote Similarity	NPD2920	Discontinued
0.6926	Remote Similarity	NPD5507	Approved
0.6926	Remote Similarity	NPD5506	Approved
0.6909	Remote Similarity	NPD4601	Approved
0.6909	Remote Similarity	NPD4600	Approved
0.6884	Remote Similarity	NPD2564	Approved
0.6884	Remote Similarity	NPD2565	Phase 2
0.687	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5164	Discontinued
0.6816	Remote Similarity	NPD5487	Phase 1
0.6812	Remote Similarity	NPD7707	Approved
0.6773	Remote Similarity	NPD6206	Phase 1
0.6765	Remote Similarity	NPD7688	Phase 1
0.6756	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6261	Phase 3
0.6739	Remote Similarity	NPD4897	Phase 2
0.6731	Remote Similarity	NPD8465	Approved
0.6731	Remote Similarity	NPD8428	Approved
0.6731	Remote Similarity	NPD8429	Approved
0.6731	Remote Similarity	NPD8467	Approved
0.6731	Remote Similarity	NPD8466	Approved
0.6731	Remote Similarity	NPD8427	Approved
0.6697	Remote Similarity	NPD5913	Phase 3
0.6697	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7957	Phase 1
0.6681	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5444	Phase 1
0.6651	Remote Similarity	NPD1325	Approved
0.6651	Remote Similarity	NPD1326	Approved
0.664	Remote Similarity	NPD7955	Approved
0.664	Remote Similarity	NPD7956	Approved
0.6636	Remote Similarity	NPD8431	Approved
0.6629	Remote Similarity	NPD8459	Approved
0.6629	Remote Similarity	NPD8426	Approved
0.6629	Remote Similarity	NPD8460	Approved
0.6629	Remote Similarity	NPD8425	Approved
0.6615	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7708	Approved
0.6609	Remote Similarity	NPD5936	Approved
0.6609	Remote Similarity	NPD5939	Approved
0.6606	Remote Similarity	NPD4334	Discontinued
0.6592	Remote Similarity	NPD7778	Approved
0.6592	Remote Similarity	NPD53	Approved
0.6592	Remote Similarity	NPD7777	Approved
0.6583	Remote Similarity	NPD7824	Approved
0.6583	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7455	Approved
0.658	Remote Similarity	NPD7454	Approved
0.6578	Remote Similarity	NPD4511	Phase 1
0.6569	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6978	Phase 2
0.656	Remote Similarity	NPD7769	Phase 3
0.6555	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD3925	Approved
0.6553	Remote Similarity	NPD6455	Phase 3
0.6552	Remote Similarity	NPD8094	Discontinued
0.655	Remote Similarity	NPD8399	Phase 1
0.655	Remote Similarity	NPD8423	Phase 2
0.6549	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4079	Approved
0.6542	Remote Similarity	NPD4076	Approved
0.654	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4500	Approved
0.6533	Remote Similarity	NPD4501	Approved
0.6525	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5021	Discontinued
0.6522	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4315	Phase 2
0.6512	Remote Similarity	NPD5899	Approved
0.6512	Remote Similarity	NPD7803	Approved
0.6512	Remote Similarity	NPD5897	Approved
0.6512	Remote Similarity	NPD5898	Approved
0.6511	Remote Similarity	NPD7878	Phase 2
0.6509	Remote Similarity	NPD6182	Approved
0.6509	Remote Similarity	NPD43	Approved
0.6509	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8093	Discontinued
0.65	Remote Similarity	NPD8363	Approved
0.65	Remote Similarity	NPD8364	Approved
0.65	Remote Similarity	NPD7731	Approved
0.65	Remote Similarity	NPD7730	Approved
0.6496	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3505	Approved
0.6495	Remote Similarity	NPD3506	Approved
0.6494	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7271	Approved
0.6473	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7796	Approved
0.6461	Remote Similarity	NPD7797	Approved
0.6453	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6176	Phase 1
0.6447	Remote Similarity	NPD3777	Phase 3
0.6445	Remote Similarity	NPD2844	Phase 3
0.6444	Remote Similarity	NPD7717	Approved
0.6444	Remote Similarity	NPD7716	Approved
0.644	Remote Similarity	NPD8468	Phase 2
0.6435	Remote Similarity	NPD5429	Discontinued
0.6435	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7951	Approved
0.6434	Remote Similarity	NPD7952	Approved
0.6434	Remote Similarity	NPD7789	Approved
0.6434	Remote Similarity	NPD7791	Approved
0.6434	Remote Similarity	NPD7950	Approved
0.6434	Remote Similarity	NPD7790	Approved
0.6434	Remote Similarity	NPD7953	Approved
0.6426	Remote Similarity	NPD8160	Phase 2
0.6425	Remote Similarity	NPD6281	Approved
0.6422	Remote Similarity	NPD4462	Approved
0.6422	Remote Similarity	NPD4463	Approved
0.6419	Remote Similarity	NPD5901	Discontinued
0.6419	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7474	Suspended
0.641	Remote Similarity	NPD7276	Approved
0.641	Remote Similarity	NPD7277	Approved
0.6409	Remote Similarity	NPD6456	Discontinued
0.6405	Remote Similarity	NPD7780	Approved
0.6405	Remote Similarity	NPD7781	Approved
0.6402	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7921	Approved
0.64	Remote Similarity	NPD1592	Phase 3
0.6389	Remote Similarity	NPD8386	Phase 2
0.6388	Remote Similarity	NPD6479	Discontinued
0.6386	Remote Similarity	NPD7770	Phase 3
0.6379	Remote Similarity	NPD4506	Discontinued
0.6379	Remote Similarity	NPD7941	Phase 3
0.6376	Remote Similarity	NPD5596	Phase 2
0.6367	Remote Similarity	NPD7558	Phase 2
0.6367	Remote Similarity	NPD7181	Phase 3
0.6364	Remote Similarity	NPD8489	Phase 1
0.6364	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7418	Discontinued
0.6352	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4499	Approved
0.6348	Remote Similarity	NPD8282	Approved
0.6348	Remote Similarity	NPD8283	Approved
0.6348	Remote Similarity	NPD6987	Phase 1
0.6348	Remote Similarity	NPD56	Approved
0.6347	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7417	Discontinued
0.6344	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5254	Discontinued
0.6336	Remote Similarity	NPD6376	Discontinued
0.6329	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD8325	Phase 3
0.6329	Remote Similarity	NPD8326	Phase 3
0.6325	Remote Similarity	NPD7470	Discontinued
0.6325	Remote Similarity	NPD6220	Phase 3
0.632	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7010	Phase 3
0.632	Remote Similarity	NPD6245	Phase 2
0.632	Remote Similarity	NPD3003	Approved
0.6316	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5427	Suspended
0.6314	Remote Similarity	NPD5903	Approved
0.6314	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD5902	Approved
0.6313	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7234	Approved
0.6306	Remote Similarity	NPD7233	Approved
0.6305	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD8016	Phase 3
0.6303	Remote Similarity	NPD7395	Discontinued
0.6301	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7946	Pre-registration
0.6296	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6531	Approved
0.6293	Remote Similarity	NPD6530	Approved
0.6287	Remote Similarity	NPD3393	Approved
0.6287	Remote Similarity	NPD5612	Discontinued
0.6287	Remote Similarity	NPD3394	Approved
0.6287	Remote Similarity	NPD3389	Approved
0.6285	Remote Similarity	NPD8358	Approved
0.6279	Remote Similarity	NPD7772	Phase 3
0.6271	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3794	Approved
0.6271	Remote Similarity	NPD3795	Approved
0.6267	Remote Similarity	NPD2144	Approved
0.6267	Remote Similarity	NPD6642	Approved
0.6267	Remote Similarity	NPD6641	Approved
0.6266	Remote Similarity	NPD2916	Discontinued
0.6266	Remote Similarity	NPD2509	Approved
0.6266	Remote Similarity	NPD2510	Approved
0.6261	Remote Similarity	NPD7187	Phase 2

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