NPASS Compound

Structure

CID301163 OpenBabel06191716112D 22 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 18 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 14 2 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 13 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	303.15
Volume:	315.814
LogP:	2.243
LogD:	2.008
LogS:	-2.743
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.85
Synthetic Accessibility Score:	2.545
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.61
MDCK Permeability:	2.680801298993174e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.202

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	90.98026275634766%
Volume Distribution (VD):	0.997
Pgp-substrate:	4.879075527191162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.706
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.742
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	7.456
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.571
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.416
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.072
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.458

Download Data

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

Natural Product: NPC301163

Natural Product ID:	NPC301163
*Common Name:**	Orixalone A
IUPAC Name:	4,8-dimethoxy-1-methyl-3-(3-methyl-2-oxobutyl)quinolin-2-one
Synonyms:
Standard InCHIKey:	DIUJWBJYQHUELV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H21NO4/c1-10(2)13(19)9-12-16(22-5)11-7-6-8-14(21-4)15(11)18(3)17(12)20/h6-8,10H,9H2,1-5H3
SMILES:	CC(C)C(=O)Cc1c(c2cccc(c2n(C)c1=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522635
PubChem CID:	11278088
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568765]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
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	Inhibition	=	47.3	%	PMID[548512]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	54.8	%	PMID[548512]

☑ 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 NPC301163 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	451
0.1-0.2	2991
0.2-0.3	12622
0.3-0.4	4253
0.4-0.5	15930
0.5-0.6	4803
0.6-0.7	1371
0.7-0.8	264
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8402	Intermediate Similarity	NPC262725
0.7941	Intermediate Similarity	NPC287152
0.7866	Intermediate Similarity	NPC93653
0.7838	Intermediate Similarity	NPC250476
0.7803	Intermediate Similarity	NPC314659
0.7771	Intermediate Similarity	NPC87391
0.775	Intermediate Similarity	NPC242000
0.7746	Intermediate Similarity	NPC197335
0.7658	Intermediate Similarity	NPC308197
0.7644	Intermediate Similarity	NPC116096
0.7644	Intermediate Similarity	NPC472163
0.7632	Intermediate Similarity	NPC231382
0.7605	Intermediate Similarity	NPC257763
0.7602	Intermediate Similarity	NPC73280
0.7541	Intermediate Similarity	NPC112937
0.7443	Intermediate Similarity	NPC270301
0.7412	Intermediate Similarity	NPC299582
0.7386	Intermediate Similarity	NPC85613
0.7306	Intermediate Similarity	NPC470481
0.7306	Intermediate Similarity	NPC470482
0.7261	Intermediate Similarity	NPC266425
0.7241	Intermediate Similarity	NPC471604
0.7228	Intermediate Similarity	NPC471825
0.7191	Intermediate Similarity	NPC5167
0.7168	Intermediate Similarity	NPC127362
0.7166	Intermediate Similarity	NPC100863
0.7158	Intermediate Similarity	NPC473569
0.7102	Intermediate Similarity	NPC307640
0.7097	Intermediate Similarity	NPC198401
0.7083	Intermediate Similarity	NPC195787
0.7083	Intermediate Similarity	NPC246140
0.7081	Intermediate Similarity	NPC473004
0.7055	Intermediate Similarity	NPC476462
0.7045	Intermediate Similarity	NPC471648
0.7022	Intermediate Similarity	NPC8467
0.7	Intermediate Similarity	NPC166169
0.7	Intermediate Similarity	NPC283810
0.6984	Remote Similarity	NPC71124
0.6978	Remote Similarity	NPC302235
0.6973	Remote Similarity	NPC45389
0.697	Remote Similarity	NPC316297
0.697	Remote Similarity	NPC314817
0.697	Remote Similarity	NPC66191
0.697	Remote Similarity	NPC260601
0.6959	Remote Similarity	NPC212123
0.6957	Remote Similarity	NPC138365
0.6936	Remote Similarity	NPC320064
0.6935	Remote Similarity	NPC1820
0.6919	Remote Similarity	NPC30749
0.6894	Remote Similarity	NPC29650
0.6891	Remote Similarity	NPC207971
0.6891	Remote Similarity	NPC41216
0.6886	Remote Similarity	NPC9373
0.6875	Remote Similarity	NPC471652
0.6865	Remote Similarity	NPC21425
0.6864	Remote Similarity	NPC144691
0.6862	Remote Similarity	NPC254957
0.6862	Remote Similarity	NPC470485
0.6856	Remote Similarity	NPC268077
0.6851	Remote Similarity	NPC474815
0.6848	Remote Similarity	NPC473007
0.6845	Remote Similarity	NPC22476
0.6842	Remote Similarity	NPC161804
0.6837	Remote Similarity	NPC329567
0.6837	Remote Similarity	NPC330683
0.6836	Remote Similarity	NPC33507
0.6834	Remote Similarity	NPC268223
0.6832	Remote Similarity	NPC475609
0.6825	Remote Similarity	NPC230313
0.6825	Remote Similarity	NPC243626
0.6823	Remote Similarity	NPC138830
0.6813	Remote Similarity	NPC70092
0.6806	Remote Similarity	NPC265642
0.6806	Remote Similarity	NPC138615
0.6806	Remote Similarity	NPC132874
0.6806	Remote Similarity	NPC218733
0.68	Remote Similarity	NPC148391
0.6792	Remote Similarity	NPC283079
0.6791	Remote Similarity	NPC473008
0.6786	Remote Similarity	NPC308943
0.6784	Remote Similarity	NPC305542
0.6782	Remote Similarity	NPC57512
0.678	Remote Similarity	NPC314861
0.6772	Remote Similarity	NPC218323
0.6771	Remote Similarity	NPC5374
0.6769	Remote Similarity	NPC470484
0.6761	Remote Similarity	NPC118511
0.6757	Remote Similarity	NPC322621
0.6755	Remote Similarity	NPC470483
0.675	Remote Similarity	NPC114468
0.6749	Remote Similarity	NPC222046
0.6736	Remote Similarity	NPC127178
0.6735	Remote Similarity	NPC477161
0.6724	Remote Similarity	NPC169742
0.672	Remote Similarity	NPC116007
0.6716	Remote Similarity	NPC2905
0.6707	Remote Similarity	NPC307682
0.6706	Remote Similarity	NPC324081
0.6705	Remote Similarity	NPC476580
0.6702	Remote Similarity	NPC174629
0.6701	Remote Similarity	NPC478075
0.67	Remote Similarity	NPC134702
0.6685	Remote Similarity	NPC476569
0.6684	Remote Similarity	NPC475147
0.6684	Remote Similarity	NPC473422
0.6683	Remote Similarity	NPC474366
0.6683	Remote Similarity	NPC76478
0.6683	Remote Similarity	NPC7560
0.6667	Remote Similarity	NPC1464
0.6667	Remote Similarity	NPC471316
0.6667	Remote Similarity	NPC470707
0.6667	Remote Similarity	NPC41488
0.6667	Remote Similarity	NPC214036
0.6667	Remote Similarity	NPC113236
0.6667	Remote Similarity	NPC92803
0.6649	Remote Similarity	NPC67904
0.6649	Remote Similarity	NPC18890
0.6647	Remote Similarity	NPC119669
0.6646	Remote Similarity	NPC180647
0.6633	Remote Similarity	NPC477160
0.6632	Remote Similarity	NPC17677
0.6632	Remote Similarity	NPC193906
0.6632	Remote Similarity	NPC23080
0.6627	Remote Similarity	NPC315051
0.6627	Remote Similarity	NPC231572
0.6626	Remote Similarity	NPC132308
0.6618	Remote Similarity	NPC195120
0.6618	Remote Similarity	NPC87560
0.6617	Remote Similarity	NPC10732
0.6615	Remote Similarity	NPC470023
0.6614	Remote Similarity	NPC474059
0.661	Remote Similarity	NPC191863
0.661	Remote Similarity	NPC133470
0.661	Remote Similarity	NPC289776
0.6607	Remote Similarity	NPC168750
0.6606	Remote Similarity	NPC106606
0.6603	Remote Similarity	NPC13249
0.6603	Remote Similarity	NPC470480
0.6602	Remote Similarity	NPC118189
0.6599	Remote Similarity	NPC163829
0.6588	Remote Similarity	NPC146370
0.6585	Remote Similarity	NPC288987
0.6585	Remote Similarity	NPC173295
0.6583	Remote Similarity	NPC100573
0.6583	Remote Similarity	NPC207873
0.658	Remote Similarity	NPC470021
0.658	Remote Similarity	NPC316282
0.6576	Remote Similarity	NPC321211
0.6575	Remote Similarity	NPC112336
0.6575	Remote Similarity	NPC474814
0.6571	Remote Similarity	NPC471649
0.657	Remote Similarity	NPC148124
0.6569	Remote Similarity	NPC126556
0.6567	Remote Similarity	NPC82541
0.6566	Remote Similarity	NPC476475
0.6566	Remote Similarity	NPC158551
0.6566	Remote Similarity	NPC225745
0.6566	Remote Similarity	NPC252107
0.6555	Remote Similarity	NPC285254
0.6554	Remote Similarity	NPC231862
0.6553	Remote Similarity	NPC118154
0.6553	Remote Similarity	NPC157983
0.6552	Remote Similarity	NPC55470
0.655	Remote Similarity	NPC475133
0.6548	Remote Similarity	NPC473460
0.6546	Remote Similarity	NPC234933
0.6545	Remote Similarity	NPC73883
0.6545	Remote Similarity	NPC136330
0.6545	Remote Similarity	NPC196609
0.6545	Remote Similarity	NPC255817
0.6545	Remote Similarity	NPC230698
0.6545	Remote Similarity	NPC204970
0.6545	Remote Similarity	NPC196708
0.6545	Remote Similarity	NPC205178
0.6545	Remote Similarity	NPC277042
0.6545	Remote Similarity	NPC251454
0.6543	Remote Similarity	NPC83511
0.6541	Remote Similarity	NPC222524
0.6537	Remote Similarity	NPC182853
0.6537	Remote Similarity	NPC77777
0.6537	Remote Similarity	NPC131885
0.6536	Remote Similarity	NPC70172
0.6536	Remote Similarity	NPC153631
0.6536	Remote Similarity	NPC24954
0.6535	Remote Similarity	NPC474428
0.6533	Remote Similarity	NPC16249
0.6531	Remote Similarity	NPC469732
0.6528	Remote Similarity	NPC170333
0.6526	Remote Similarity	NPC5630
0.6522	Remote Similarity	NPC315631
0.6522	Remote Similarity	NPC99724
0.6522	Remote Similarity	NPC172403
0.652	Remote Similarity	NPC234772
0.6517	Remote Similarity	NPC230942
0.6517	Remote Similarity	NPC315498
0.6515	Remote Similarity	NPC87714
0.6515	Remote Similarity	NPC14339
0.6512	Remote Similarity	NPC314702
0.651	Remote Similarity	NPC203972
0.651	Remote Similarity	NPC78284

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 NPC301163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	671
0.2-0.3	946
0.3-0.4	1274
0.4-0.5	2996
0.5-0.6	2227
0.6-0.7	661
0.7-0.8	97
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
0.7904	Intermediate Similarity	NPD5847	Phase 1
0.7824	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4515	Suspended
0.7572	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1769	Discontinued
0.7529	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4201	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7126	Discontinued
0.7414	Intermediate Similarity	NPD6645	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3793	Phase 3
0.7353	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2681	Approved
0.7326	Intermediate Similarity	NPD2680	Approved
0.7299	Intermediate Similarity	NPD5858	Discontinued
0.7283	Intermediate Similarity	NPD5186	Approved
0.7283	Intermediate Similarity	NPD5183	Approved
0.7225	Intermediate Similarity	NPD6457	Approved
0.7176	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4205	Phase 3
0.7158	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2791	Discontinued
0.7095	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3416	Discontinued
0.7053	Intermediate Similarity	NPD6321	Discontinued
0.7031	Intermediate Similarity	NPD6644	Discontinued
0.7029	Intermediate Similarity	NPD2249	Approved
0.7029	Intermediate Similarity	NPD2247	Approved
0.7026	Intermediate Similarity	NPD5860	Discontinued
0.7021	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4082	Approved
0.6988	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5938	Phase 3
0.6943	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1012	Discontinued
0.6927	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD743	Approved
0.691	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4493	Discontinued
0.6903	Remote Similarity	NPD1421	Approved
0.6903	Remote Similarity	NPD1420	Approved
0.6895	Remote Similarity	NPD5071	Phase 2
0.6889	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5113	Approved
0.6882	Remote Similarity	NPD5114	Approved
0.6882	Remote Similarity	NPD5112	Approved
0.6879	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6238	Discontinued
0.6872	Remote Similarity	NPD7043	Discontinued
0.6872	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4596	Phase 1
0.6872	Remote Similarity	NPD7263	Phase 2
0.6856	Remote Similarity	NPD4467	Phase 2
0.6856	Remote Similarity	NPD4465	Phase 2
0.6853	Remote Similarity	NPD3893	Discontinued
0.6845	Remote Similarity	NPD5994	Discontinued
0.6837	Remote Similarity	NPD2907	Approved
0.6837	Remote Similarity	NPD4022	Approved
0.6837	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2906	Approved
0.6837	Remote Similarity	NPD3472	Approved
0.6828	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3301	Approved
0.6824	Remote Similarity	NPD1670	Discontinued
0.6823	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4430	Phase 2
0.6805	Remote Similarity	NPD2335	Discontinued
0.6804	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3437	Discontinued
0.6798	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2594	Approved
0.6797	Remote Similarity	NPD2595	Approved
0.6791	Remote Similarity	NPD4428	Discontinued
0.6788	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4492	Approved
0.6784	Remote Similarity	NPD4494	Approved
0.6774	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1880	Phase 3
0.6769	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3372	Discontinued
0.6766	Remote Similarity	NPD5481	Discontinued
0.6754	Remote Similarity	NPD5515	Phase 2
0.6753	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2821	Approved
0.6734	Remote Similarity	NPD1945	Phase 1
0.6724	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7317	Phase 3
0.6722	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3802	Phase 3
0.6703	Remote Similarity	NPD5600	Discontinued
0.6702	Remote Similarity	NPD3964	Approved
0.67	Remote Similarity	NPD3888	Discontinued
0.6699	Remote Similarity	NPD3912	Discontinued
0.6687	Remote Similarity	NPD7752	Approved
0.6687	Remote Similarity	NPD7753	Approved
0.6686	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1559	Discontinued
0.6684	Remote Similarity	NPD6874	Approved
0.6683	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7805	Phase 3
0.6667	Remote Similarity	NPD4455	Discontinued
0.6667	Remote Similarity	NPD2388	Discontinued
0.6667	Remote Similarity	NPD2899	Discontinued
0.6667	Remote Similarity	NPD850	Approved
0.6667	Remote Similarity	NPD7467	Discontinued
0.6667	Remote Similarity	NPD849	Approved
0.6667	Remote Similarity	NPD848	Approved
0.6648	Remote Similarity	NPD7318	Phase 3
0.6648	Remote Similarity	NPD6379	Discontinued
0.6647	Remote Similarity	NPD824	Approved
0.6647	Remote Similarity	NPD4598	Approved
0.6647	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4597	Approved
0.6647	Remote Similarity	NPD6357	Discontinued
0.6634	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3479	Discontinued
0.663	Remote Similarity	NPD2248	Approved
0.663	Remote Similarity	NPD2246	Approved
0.6628	Remote Similarity	NPD3639	Approved
0.6628	Remote Similarity	NPD3641	Approved
0.6628	Remote Similarity	NPD3640	Phase 3
0.6617	Remote Similarity	NPD7225	Discontinued
0.6615	Remote Similarity	NPD5582	Discontinued
0.6609	Remote Similarity	NPD3684	Discontinued
0.6609	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2670	Approved
0.6601	Remote Similarity	NPD8149	Discontinued
0.6597	Remote Similarity	NPD4539	Phase 1
0.6595	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2904	Discontinued
0.6583	Remote Similarity	NPD4859	Phase 1
0.6579	Remote Similarity	NPD7668	Phase 2
0.6579	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7479	Phase 2
0.6575	Remote Similarity	NPD5242	Approved
0.6575	Remote Similarity	NPD4083	Discontinued
0.6573	Remote Similarity	NPD1309	Phase 2
0.6573	Remote Similarity	NPD3789	Approved
0.6573	Remote Similarity	NPD1307	Phase 2
0.6571	Remote Similarity	NPD2672	Discontinued
0.657	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7272	Discontinued
0.6566	Remote Similarity	NPD822	Approved
0.6564	Remote Similarity	NPD6519	Phase 2
0.6562	Remote Similarity	NPD2987	Approved
0.6562	Remote Similarity	NPD2990	Approved
0.6561	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3983	Phase 3
0.6554	Remote Similarity	NPD5977	Approved
0.6554	Remote Similarity	NPD5978	Approved
0.6553	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4372	Phase 1
0.6545	Remote Similarity	NPD2492	Phase 1
0.6538	Remote Similarity	NPD6894	Phase 1
0.6538	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4796	Discontinued
0.6535	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7248	Discontinued
0.6534	Remote Similarity	NPD1861	Discovery
0.6533	Remote Similarity	NPD5514	Discontinued
0.6532	Remote Similarity	NPD3277	Phase 3
0.6532	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7131	Phase 3
0.6532	Remote Similarity	NPD3627	Approved
0.6529	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6032	Approved
0.6526	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3140	Approved
0.6524	Remote Similarity	NPD3142	Approved
0.6522	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2230	Approved
0.6519	Remote Similarity	NPD2232	Approved
0.6519	Remote Similarity	NPD2233	Approved
0.6517	Remote Similarity	NPD4871	Phase 2
0.6517	Remote Similarity	NPD1742	Approved
0.6517	Remote Similarity	NPD1743	Approved
0.6517	Remote Similarity	NPD19	Approved
0.6497	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6738	Phase 2
0.6497	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6737	Phase 2
0.6495	Remote Similarity	NPD7238	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