NPASS Compound

Structure

NPC280853 OpenBabel07101719522D 21 21 0 0 0 0 0 0 0 0999 V2000 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 1.7321 -3.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 -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 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 5 1 0 0 0 0 2 6 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 8 2 0 0 0 0 8 10 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 16 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.2
Volume:	326.723
LogP:	4.737
LogD:	3.594
LogS:	-3.901
# Rotatable Bonds:	7
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	3.278
Fsp3:	0.5
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:	-4.738
MDCK Permeability:	2.8316448151599616e-05
Pgp-inhibitor:	0.173
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	99.78217315673828%
Volume Distribution (VD):	2.216
Pgp-substrate:	0.8199860453605652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.812
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.846
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.65
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.664
CYP2D6-substrate:	0.701
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	3.655
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.551
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.402
Carcinogencity:	0.287
Eye Corrosion:	0.004
Eye Irritation:	0.119
Respiratory Toxicity:	0.386

Download Data

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

Natural Product: NPC280853

Natural Product ID:	NPC280853
*Common Name:**	Iromycin C
IUPAC Name:	4-hydroxy-3-methyl-6-[(2E,5E)-3-methylocta-2,5-dienyl]-5-propyl-1H-pyridin-2-one
Synonyms:	Iromycin C
Standard InCHIKey:	CYTLCZVDDYEJPL-IGOCJVNJSA-N
Standard InCHI:	InChI=1S/C18H27NO2/c1-5-7-8-10-13(3)11-12-16-15(9-6-2)17(20)14(4)18(21)19-16/h7-8,11H,5-6,9-10,12H2,1-4H3,(H2,19,20,21)/b8-7+,13-11+
SMILES:	CC/C=C/C/C(=C/Cc1c(CCC)c(c(C)c(n1)O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257864
PubChem CID:	54708418
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002224] Hydropyridines [CHEMONTID:0001160] Pyridinones

*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
NPO33217	streptomyces sp. dra 17	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18054490]

☑ 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
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5098	Protein Complex	Mitochondrial complex I; NADH oxidoreductase	Bos taurus	IC50	=	3520.0	nM	PMID[559500]

☑ 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 NPC280853 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	314
0.1-0.2	2992
0.2-0.3	13432
0.3-0.4	9504
0.4-0.5	11957
0.5-0.6	3689
0.6-0.7	679
0.7-0.8	115
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC285016
0.9924	High Similarity	NPC471596
0.9924	High Similarity	NPC245657
0.9704	High Similarity	NPC471598
0.9478	High Similarity	NPC471594
0.8483	Intermediate Similarity	NPC161292
0.8291	Intermediate Similarity	NPC283152
0.8255	Intermediate Similarity	NPC153769
0.8113	Intermediate Similarity	NPC288943
0.8113	Intermediate Similarity	NPC194724
0.8082	Intermediate Similarity	NPC60553
0.8065	Intermediate Similarity	NPC473057
0.8037	Intermediate Similarity	NPC320394
0.7962	Intermediate Similarity	NPC108469
0.7818	Intermediate Similarity	NPC62069
0.7806	Intermediate Similarity	NPC132680
0.7806	Intermediate Similarity	NPC269919
0.7785	Intermediate Similarity	NPC470404
0.7785	Intermediate Similarity	NPC470403
0.7785	Intermediate Similarity	NPC470394
0.7771	Intermediate Similarity	NPC315214
0.7771	Intermediate Similarity	NPC47298
0.7756	Intermediate Similarity	NPC84508
0.7722	Intermediate Similarity	NPC159319
0.7722	Intermediate Similarity	NPC32028
0.7688	Intermediate Similarity	NPC44161
0.7682	Intermediate Similarity	NPC470395
0.7679	Intermediate Similarity	NPC66083
0.7677	Intermediate Similarity	NPC63562
0.7665	Intermediate Similarity	NPC42591
0.7613	Intermediate Similarity	NPC26872
0.761	Intermediate Similarity	NPC263439
0.7602	Intermediate Similarity	NPC141915
0.7602	Intermediate Similarity	NPC280964
0.7602	Intermediate Similarity	NPC114335
0.7582	Intermediate Similarity	NPC257142
0.7562	Intermediate Similarity	NPC471178
0.7546	Intermediate Similarity	NPC259545
0.7546	Intermediate Similarity	NPC471294
0.7531	Intermediate Similarity	NPC126481
0.7484	Intermediate Similarity	NPC322976
0.7484	Intermediate Similarity	NPC324203
0.7484	Intermediate Similarity	NPC63338
0.7468	Intermediate Similarity	NPC26850
0.7438	Intermediate Similarity	NPC124542
0.7438	Intermediate Similarity	NPC177404
0.7438	Intermediate Similarity	NPC471177
0.7438	Intermediate Similarity	NPC59779
0.7436	Intermediate Similarity	NPC284348
0.7431	Intermediate Similarity	NPC278451
0.7412	Intermediate Similarity	NPC61350
0.7391	Intermediate Similarity	NPC211187
0.7365	Intermediate Similarity	NPC232340
0.7341	Intermediate Similarity	NPC469390
0.7333	Intermediate Similarity	NPC474409
0.731	Intermediate Similarity	NPC314573
0.7294	Intermediate Similarity	NPC190007
0.7278	Intermediate Similarity	NPC317572
0.7273	Intermediate Similarity	NPC476688
0.7273	Intermediate Similarity	NPC476686
0.7273	Intermediate Similarity	NPC105758
0.7262	Intermediate Similarity	NPC72980
0.7257	Intermediate Similarity	NPC279401
0.7257	Intermediate Similarity	NPC79293
0.7256	Intermediate Similarity	NPC278874
0.7251	Intermediate Similarity	NPC94943
0.725	Intermediate Similarity	NPC116573
0.7235	Intermediate Similarity	NPC133306
0.7222	Intermediate Similarity	NPC224632
0.7222	Intermediate Similarity	NPC66815
0.7219	Intermediate Similarity	NPC478032
0.7212	Intermediate Similarity	NPC256828
0.7186	Intermediate Similarity	NPC303225
0.7178	Intermediate Similarity	NPC97367
0.717	Intermediate Similarity	NPC36168
0.716	Intermediate Similarity	NPC25899
0.7143	Intermediate Similarity	NPC164374
0.7143	Intermediate Similarity	NPC137929
0.7135	Intermediate Similarity	NPC474188
0.7135	Intermediate Similarity	NPC212535
0.7135	Intermediate Similarity	NPC224928
0.7126	Intermediate Similarity	NPC183805
0.7102	Intermediate Similarity	NPC56170
0.7088	Intermediate Similarity	NPC469440
0.7076	Intermediate Similarity	NPC144114
0.7069	Intermediate Similarity	NPC206186
0.7062	Intermediate Similarity	NPC289786
0.7059	Intermediate Similarity	NPC67659
0.7059	Intermediate Similarity	NPC472168
0.7059	Intermediate Similarity	NPC88363
0.7024	Intermediate Similarity	NPC208060
0.7012	Intermediate Similarity	NPC48192
0.7012	Intermediate Similarity	NPC79911
0.7011	Intermediate Similarity	NPC194040
0.7011	Intermediate Similarity	NPC304183
0.7006	Intermediate Similarity	NPC473764
0.7006	Intermediate Similarity	NPC314940
0.6983	Remote Similarity	NPC473053
0.6982	Remote Similarity	NPC312872
0.6981	Remote Similarity	NPC288445
0.6977	Remote Similarity	NPC477891
0.6971	Remote Similarity	NPC46580
0.6966	Remote Similarity	NPC45850
0.6964	Remote Similarity	NPC252590
0.6964	Remote Similarity	NPC158129
0.6959	Remote Similarity	NPC212125
0.6951	Remote Similarity	NPC120798
0.6944	Remote Similarity	NPC243834
0.6944	Remote Similarity	NPC153042
0.6944	Remote Similarity	NPC70956
0.6939	Remote Similarity	NPC151489
0.6932	Remote Similarity	NPC246700
0.6932	Remote Similarity	NPC230805
0.6932	Remote Similarity	NPC128751
0.6923	Remote Similarity	NPC249040
0.6919	Remote Similarity	NPC52831
0.6919	Remote Similarity	NPC325705
0.6919	Remote Similarity	NPC249662
0.6919	Remote Similarity	NPC168486
0.6919	Remote Similarity	NPC222592
0.6905	Remote Similarity	NPC164664
0.6901	Remote Similarity	NPC96890
0.6893	Remote Similarity	NPC469497
0.6893	Remote Similarity	NPC3715
0.6893	Remote Similarity	NPC106833
0.6879	Remote Similarity	NPC470474
0.6867	Remote Similarity	NPC118511
0.6857	Remote Similarity	NPC314002
0.6855	Remote Similarity	NPC220523
0.6818	Remote Similarity	NPC171171
0.6818	Remote Similarity	NPC204385
0.68	Remote Similarity	NPC204717
0.6793	Remote Similarity	NPC155792
0.6783	Remote Similarity	NPC476566
0.678	Remote Similarity	NPC238242
0.6776	Remote Similarity	NPC280714
0.6768	Remote Similarity	NPC141353
0.6766	Remote Similarity	NPC476118
0.6757	Remote Similarity	NPC475112
0.6757	Remote Similarity	NPC475085
0.6757	Remote Similarity	NPC291535
0.6755	Remote Similarity	NPC470931
0.6744	Remote Similarity	NPC134586
0.6743	Remote Similarity	NPC220765
0.6742	Remote Similarity	NPC110741
0.6733	Remote Similarity	NPC471313
0.6733	Remote Similarity	NPC306397
0.6733	Remote Similarity	NPC471311
0.6733	Remote Similarity	NPC165370
0.673	Remote Similarity	NPC471323
0.6725	Remote Similarity	NPC247980
0.6722	Remote Similarity	NPC99666
0.6721	Remote Similarity	NPC306376
0.6721	Remote Similarity	NPC472284
0.672	Remote Similarity	NPC223427
0.671	Remote Similarity	NPC29702
0.6705	Remote Similarity	NPC211997
0.6705	Remote Similarity	NPC184964
0.6704	Remote Similarity	NPC144381
0.6703	Remote Similarity	NPC472193
0.6686	Remote Similarity	NPC95898
0.6685	Remote Similarity	NPC18487
0.6685	Remote Similarity	NPC36498
0.6685	Remote Similarity	NPC329541
0.6667	Remote Similarity	NPC477889
0.6667	Remote Similarity	NPC256893
0.6667	Remote Similarity	NPC241025
0.6649	Remote Similarity	NPC474145
0.6649	Remote Similarity	NPC475841
0.6649	Remote Similarity	NPC472111
0.6648	Remote Similarity	NPC32771
0.6648	Remote Similarity	NPC276517
0.6648	Remote Similarity	NPC472289
0.6646	Remote Similarity	NPC318935
0.6643	Remote Similarity	NPC9336
0.6632	Remote Similarity	NPC469589
0.6631	Remote Similarity	NPC53144
0.6631	Remote Similarity	NPC200836
0.663	Remote Similarity	NPC133140
0.663	Remote Similarity	NPC195268
0.663	Remote Similarity	NPC324149
0.6628	Remote Similarity	NPC191310
0.6621	Remote Similarity	NPC81561
0.6615	Remote Similarity	NPC202605
0.6615	Remote Similarity	NPC112206
0.6615	Remote Similarity	NPC203168
0.6615	Remote Similarity	NPC473822
0.6614	Remote Similarity	NPC53344
0.6614	Remote Similarity	NPC193777
0.6612	Remote Similarity	NPC242209
0.661	Remote Similarity	NPC84478
0.6603	Remote Similarity	NPC328029
0.6597	Remote Similarity	NPC219664
0.6596	Remote Similarity	NPC475070
0.6595	Remote Similarity	NPC476167
0.6593	Remote Similarity	NPC106937
0.6593	Remote Similarity	NPC230403
0.6591	Remote Similarity	NPC206201
0.6591	Remote Similarity	NPC314394
0.6588	Remote Similarity	NPC41717

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 NPC280853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	686
0.2-0.3	859
0.3-0.4	1347
0.4-0.5	3638
0.5-0.6	2079
0.6-0.7	292
0.7-0.8	27
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
0.7901	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD9383	Approved
0.7806	Intermediate Similarity	NPD9382	Approved
0.7771	Intermediate Similarity	NPD1684	Approved
0.7771	Intermediate Similarity	NPD1685	Approved
0.775	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3525	Discontinued
0.7622	Intermediate Similarity	NPD6159	Phase 2
0.7562	Intermediate Similarity	NPD925	Approved
0.7562	Intermediate Similarity	NPD926	Approved
0.75	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2882	Phase 1
0.7284	Intermediate Similarity	NPD862	Approved
0.7284	Intermediate Similarity	NPD861	Approved
0.7284	Intermediate Similarity	NPD863	Approved
0.7267	Intermediate Similarity	NPD2383	Phase 1
0.7215	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6158	Phase 2
0.7202	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4203	Approved
0.7176	Intermediate Similarity	NPD4204	Approved
0.7169	Intermediate Similarity	NPD2123	Phase 3
0.7152	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5256	Discontinued
0.7108	Intermediate Similarity	NPD7474	Suspended
0.7101	Intermediate Similarity	NPD6642	Approved
0.7101	Intermediate Similarity	NPD6641	Approved
0.7099	Intermediate Similarity	NPD5255	Approved
0.7093	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3920	Phase 2
0.7052	Intermediate Similarity	NPD2762	Phase 2
0.7051	Intermediate Similarity	NPD3813	Approved
0.7048	Intermediate Similarity	NPD2781	Approved
0.7039	Intermediate Similarity	NPD1229	Phase 2
0.703	Intermediate Similarity	NPD2780	Approved
0.703	Intermediate Similarity	NPD2782	Approved
0.7024	Intermediate Similarity	NPD7418	Discontinued
0.7011	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5316	Approved
0.6988	Remote Similarity	NPD424	Approved
0.6988	Remote Similarity	NPD425	Approved
0.697	Remote Similarity	NPD444	Approved
0.6961	Remote Similarity	NPD2177	Approved
0.6961	Remote Similarity	NPD2176	Approved
0.6961	Remote Similarity	NPD2175	Phase 3
0.6959	Remote Similarity	NPD9284	Approved
0.6941	Remote Similarity	NPD5100	Phase 3
0.6932	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD9510	Approved
0.6918	Remote Similarity	NPD4703	Approved
0.6918	Remote Similarity	NPD4702	Approved
0.6906	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD9470	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD9690	Approved
0.6879	Remote Similarity	NPD3717	Discontinued
0.6879	Remote Similarity	NPD3386	Phase 2
0.6862	Remote Similarity	NPD648	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1649	Discontinued
0.6839	Remote Similarity	NPD852	Discontinued
0.6835	Remote Similarity	NPD1352	Discontinued
0.6835	Remote Similarity	NPD8823	Approved
0.6831	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4375	Approved
0.6815	Remote Similarity	NPD1592	Phase 3
0.6813	Remote Similarity	NPD2727	Phase 2
0.6798	Remote Similarity	NPD1213	Phase 3
0.6786	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6492	Phase 2
0.6782	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6361	Phase 2
0.6766	Remote Similarity	NPD5138	Approved
0.6766	Remote Similarity	NPD5140	Approved
0.6747	Remote Similarity	NPD112	Approved
0.6747	Remote Similarity	NPD9705	Discontinued
0.674	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3395	Approved
0.674	Remote Similarity	NPD3396	Approved
0.6733	Remote Similarity	NPD9080	Approved
0.6727	Remote Similarity	NPD2582	Approved
0.6727	Remote Similarity	NPD2581	Approved
0.6725	Remote Similarity	NPD3224	Phase 2
0.6722	Remote Similarity	NPD6569	Phase 2
0.6722	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5020	Approved
0.6707	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD9363	Approved
0.6685	Remote Similarity	NPD9364	Phase 2
0.6667	Remote Similarity	NPD9506	Approved
0.6667	Remote Similarity	NPD2916	Discontinued
0.6667	Remote Similarity	NPD6227	Discontinued
0.6667	Remote Similarity	NPD4889	Approved
0.6649	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6590	Discontinued
0.6648	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6991	Approved
0.663	Remote Similarity	NPD3923	Approved
0.663	Remote Similarity	NPD3922	Approved
0.663	Remote Similarity	NPD3924	Approved
0.663	Remote Similarity	NPD3921	Approved
0.6624	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7222	Phase 2
0.6614	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1326	Approved
0.6608	Remote Similarity	NPD1325	Approved
0.6595	Remote Similarity	NPD3814	Phase 1
0.6595	Remote Similarity	NPD8395	Approved
0.6595	Remote Similarity	NPD8396	Approved
0.6593	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4551	Phase 2
0.6593	Remote Similarity	NPD802	Phase 2
0.6576	Remote Similarity	NPD7948	Phase 1
0.6576	Remote Similarity	NPD2952	Discontinued
0.6562	Remote Similarity	NPD5939	Approved
0.6562	Remote Similarity	NPD5936	Approved
0.6561	Remote Similarity	NPD5530	Phase 1
0.6559	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD408	Approved
0.6554	Remote Similarity	NPD5596	Phase 2
0.6552	Remote Similarity	NPD2382	Approved
0.6552	Remote Similarity	NPD2380	Approved
0.6552	Remote Similarity	NPD313	Approved
0.6552	Remote Similarity	NPD2381	Approved
0.655	Remote Similarity	NPD2844	Phase 3
0.6526	Remote Similarity	NPD6290	Phase 2
0.6522	Remote Similarity	NPD6594	Discontinued
0.6522	Remote Similarity	NPD5512	Phase 3
0.6522	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3925	Approved
0.6497	Remote Similarity	NPD9362	Approved
0.6497	Remote Similarity	NPD3037	Phase 1
0.6497	Remote Similarity	NPD7867	Phase 1
0.6494	Remote Similarity	NPD5065	Approved
0.6492	Remote Similarity	NPD7671	Approved
0.6492	Remote Similarity	NPD7672	Approved
0.6489	Remote Similarity	NPD3931	Approved
0.6489	Remote Similarity	NPD3928	Approved
0.6486	Remote Similarity	NPD1622	Discontinued
0.6477	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4502	Phase 2
0.6474	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5088	Discontinued
0.6467	Remote Similarity	NPD2469	Approved
0.6467	Remote Similarity	NPD2468	Approved
0.6464	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD4021	Phase 2
0.6452	Remote Similarity	NPD7419	Discontinued
0.645	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3315	Phase 3
0.6442	Remote Similarity	NPD7469	Discontinued
0.6441	Remote Similarity	NPD6452	Discontinued
0.644	Remote Similarity	NPD7453	Approved
0.644	Remote Similarity	NPD7452	Approved
0.6429	Remote Similarity	NPD3321	Discontinued
0.6429	Remote Similarity	NPD8063	Discontinued
0.6429	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4484	Phase 1
0.6421	Remote Similarity	NPD4039	Approved
0.6421	Remote Similarity	NPD4037	Approved
0.6421	Remote Similarity	NPD4038	Approved
0.6421	Remote Similarity	NPD4035	Approved
0.6421	Remote Similarity	NPD4036	Approved
0.6421	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4122	Approved
0.6421	Remote Similarity	NPD31	Approved
0.6421	Remote Similarity	NPD32	Approved
0.6421	Remote Similarity	NPD4034	Approved
0.6421	Remote Similarity	NPD4033	Approved
0.6417	Remote Similarity	NPD1768	Approved
0.6415	Remote Similarity	NPD2896	Discontinued
0.6413	Remote Similarity	NPD9695	Approved
0.6413	Remote Similarity	NPD1038	Approved
0.6406	Remote Similarity	NPD6376	Discontinued
0.6402	Remote Similarity	NPD6975	Discontinued
0.6398	Remote Similarity	NPD6988	Phase 1
0.6393	Remote Similarity	NPD2334	Discontinued
0.6393	Remote Similarity	NPD4699	Discontinued
0.6391	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3082	Discontinued
0.6387	Remote Similarity	NPD3003	Approved
0.6387	Remote Similarity	NPD9207	Approved
0.6387	Remote Similarity	NPD9206	Approved
0.6379	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4418	Discontinued
0.6378	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4437	Phase 3
0.6368	Remote Similarity	NPD4044	Discontinued
0.6364	Remote Similarity	NPD8109	Clinical (unspecified phase)

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