NPASS Compound

Structure

NPC470548 OpenBabel07101719512D 22 26 0 0 1 0 0 0 0 0999 V2000 -2.7615 1.1006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1627 0.3552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9154 1.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7177 -0.3650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4704 0.4058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8715 -0.3396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6375 0.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 N 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 -2.3479 -2.7058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3715 1.5209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.08
Volume:	287.078
LogP:	1.356
LogD:	1.366
LogS:	-4.207
# Rotatable Bonds:	0
TPSA:	60.85
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	3.443
Fsp3:	0.176
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:	-4.756
MDCK Permeability:	3.999695763923228e-05
Pgp-inhibitor:	0.829
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	58.31365203857422%
Volume Distribution (VD):	0.588
Pgp-substrate:	39.7024040222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.553
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	1.809
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.714
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.851
Carcinogencity:	0.1
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC470548

Natural Product ID:	NPC470548
*Common Name:**	DMWBWCODLSCGLM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DMWBWCODLSCGLM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12N2O3/c20-14-9-17(22)11-6-2-4-8-13(11)19-15(21)10-5-1-3-7-12(10)18(14)16(17)19/h1-8,16,22H,9H2
SMILES:	O=C1CC2(C3N1c1ccccc1C(=O)N3c1c2cccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063172
PubChem CID:	60155951
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	47.0	%	PMID[496831]

☑ 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 NPC470548 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	326
0.1-0.2	1997
0.2-0.3	9539
0.3-0.4	11408
0.4-0.5	14982
0.5-0.6	3760
0.6-0.7	628
0.7-0.8	52
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC471124
0.8642	High Similarity	NPC471122
0.8588	High Similarity	NPC470787
0.8588	High Similarity	NPC472539
0.8588	High Similarity	NPC472540
0.8539	High Similarity	NPC472542
0.8539	High Similarity	NPC472541
0.8353	Intermediate Similarity	NPC475594
0.8314	Intermediate Similarity	NPC475761
0.8304	Intermediate Similarity	NPC475607
0.8256	Intermediate Similarity	NPC474081
0.8208	Intermediate Similarity	NPC474041
0.8023	Intermediate Similarity	NPC355
0.7968	Intermediate Similarity	NPC295548
0.7889	Intermediate Similarity	NPC473815
0.7884	Intermediate Similarity	NPC225400
0.7874	Intermediate Similarity	NPC177261
0.7842	Intermediate Similarity	NPC470786
0.7842	Intermediate Similarity	NPC471155
0.7842	Intermediate Similarity	NPC472538
0.7801	Intermediate Similarity	NPC270241
0.7674	Intermediate Similarity	NPC476231
0.7526	Intermediate Similarity	NPC285192
0.7448	Intermediate Similarity	NPC471436
0.7378	Intermediate Similarity	NPC469560
0.7371	Intermediate Similarity	NPC472117
0.7371	Intermediate Similarity	NPC88970
0.7368	Intermediate Similarity	NPC471199
0.7363	Intermediate Similarity	NPC248601
0.7362	Intermediate Similarity	NPC471123
0.733	Intermediate Similarity	NPC204867
0.7313	Intermediate Similarity	NPC244425
0.7313	Intermediate Similarity	NPC15384
0.7308	Intermediate Similarity	NPC475094
0.7288	Intermediate Similarity	NPC471130
0.7263	Intermediate Similarity	NPC472118
0.7247	Intermediate Similarity	NPC182131
0.7234	Intermediate Similarity	NPC471195
0.7234	Intermediate Similarity	NPC471196
0.7229	Intermediate Similarity	NPC315051
0.7228	Intermediate Similarity	NPC471197
0.7202	Intermediate Similarity	NPC106118
0.72	Intermediate Similarity	NPC113946
0.7193	Intermediate Similarity	NPC237649
0.7193	Intermediate Similarity	NPC300596
0.7192	Intermediate Similarity	NPC471198
0.7189	Intermediate Similarity	NPC470317
0.7186	Intermediate Similarity	NPC43477
0.7175	Intermediate Similarity	NPC472120
0.7175	Intermediate Similarity	NPC472101
0.7174	Intermediate Similarity	NPC475685
0.7159	Intermediate Similarity	NPC36495
0.7151	Intermediate Similarity	NPC144691
0.7151	Intermediate Similarity	NPC279527
0.7151	Intermediate Similarity	NPC214960
0.7151	Intermediate Similarity	NPC472114
0.7151	Intermediate Similarity	NPC472115
0.7135	Intermediate Similarity	NPC189116
0.7119	Intermediate Similarity	NPC472102
0.7119	Intermediate Similarity	NPC309531
0.711	Intermediate Similarity	NPC154602
0.7104	Intermediate Similarity	NPC471743
0.7095	Intermediate Similarity	NPC472106
0.7074	Intermediate Similarity	NPC150308
0.7069	Intermediate Similarity	NPC117032
0.7039	Intermediate Similarity	NPC272174
0.7039	Intermediate Similarity	NPC313757
0.7033	Intermediate Similarity	NPC318183
0.703	Intermediate Similarity	NPC253476
0.7011	Intermediate Similarity	NPC129624
0.7011	Intermediate Similarity	NPC66936
0.7006	Intermediate Similarity	NPC122553
0.7005	Intermediate Similarity	NPC474896
0.6995	Remote Similarity	NPC251212
0.6995	Remote Similarity	NPC214626
0.6995	Remote Similarity	NPC139085
0.6982	Remote Similarity	NPC471164
0.6971	Remote Similarity	NPC31097
0.697	Remote Similarity	NPC477179
0.6963	Remote Similarity	NPC313293
0.6963	Remote Similarity	NPC105055
0.6963	Remote Similarity	NPC22689
0.6954	Remote Similarity	NPC471944
0.6954	Remote Similarity	NPC473329
0.6935	Remote Similarity	NPC477178
0.6935	Remote Similarity	NPC477181
0.6935	Remote Similarity	NPC254850
0.6935	Remote Similarity	NPC477180
0.6933	Remote Similarity	NPC209389
0.6931	Remote Similarity	NPC322621
0.6927	Remote Similarity	NPC27904
0.6923	Remote Similarity	NPC472243
0.6923	Remote Similarity	NPC33507
0.6902	Remote Similarity	NPC285622
0.6902	Remote Similarity	NPC96901
0.69	Remote Similarity	NPC470490
0.69	Remote Similarity	NPC477174
0.69	Remote Similarity	NPC477173
0.6898	Remote Similarity	NPC298320
0.6895	Remote Similarity	NPC473615
0.6882	Remote Similarity	NPC186284
0.6882	Remote Similarity	NPC470301
0.6882	Remote Similarity	NPC22082
0.6879	Remote Similarity	NPC324445
0.6878	Remote Similarity	NPC471742
0.6875	Remote Similarity	NPC285381
0.6872	Remote Similarity	NPC276085
0.6866	Remote Similarity	NPC470488
0.6859	Remote Similarity	NPC229484
0.6854	Remote Similarity	NPC29285
0.6848	Remote Similarity	NPC314098
0.6847	Remote Similarity	NPC475359
0.6847	Remote Similarity	NPC191817
0.6842	Remote Similarity	NPC259626
0.6833	Remote Similarity	NPC68650
0.6832	Remote Similarity	NPC471945
0.6832	Remote Similarity	NPC471950
0.6832	Remote Similarity	NPC470491
0.6832	Remote Similarity	NPC475259
0.6825	Remote Similarity	NPC122886
0.6824	Remote Similarity	NPC207554
0.6823	Remote Similarity	NPC18890
0.6823	Remote Similarity	NPC292675
0.6816	Remote Similarity	NPC222029
0.6816	Remote Similarity	NPC61013
0.6813	Remote Similarity	NPC257490
0.6802	Remote Similarity	NPC100863
0.6802	Remote Similarity	NPC308197
0.6798	Remote Similarity	NPC471951
0.6798	Remote Similarity	NPC471946
0.6796	Remote Similarity	NPC199737
0.6789	Remote Similarity	NPC2933
0.6788	Remote Similarity	NPC128582
0.6788	Remote Similarity	NPC45389
0.6782	Remote Similarity	NPC478075
0.6782	Remote Similarity	NPC243850
0.6778	Remote Similarity	NPC193410
0.6766	Remote Similarity	NPC329833
0.6755	Remote Similarity	NPC99043
0.6755	Remote Similarity	NPC218594
0.6753	Remote Similarity	NPC92803
0.6744	Remote Similarity	NPC472241
0.6742	Remote Similarity	NPC295021
0.674	Remote Similarity	NPC248117
0.674	Remote Similarity	NPC225319
0.6739	Remote Similarity	NPC223595
0.6739	Remote Similarity	NPC167724
0.6739	Remote Similarity	NPC224970
0.6737	Remote Similarity	NPC256288
0.6725	Remote Similarity	NPC242933
0.6723	Remote Similarity	NPC243756
0.672	Remote Similarity	NPC166169
0.6717	Remote Similarity	NPC474916
0.6705	Remote Similarity	NPC242000
0.6703	Remote Similarity	NPC469915
0.6703	Remote Similarity	NPC293458
0.6703	Remote Similarity	NPC286871
0.6702	Remote Similarity	NPC260075
0.6701	Remote Similarity	NPC473569
0.6686	Remote Similarity	NPC300299
0.6686	Remote Similarity	NPC471574
0.6667	Remote Similarity	NPC113056
0.6667	Remote Similarity	NPC268534
0.6667	Remote Similarity	NPC138293
0.6667	Remote Similarity	NPC321211
0.6667	Remote Similarity	NPC471663
0.6667	Remote Similarity	NPC292265
0.6667	Remote Similarity	NPC203628
0.665	Remote Similarity	NPC221687
0.6649	Remote Similarity	NPC477159
0.6649	Remote Similarity	NPC221873
0.6648	Remote Similarity	NPC315368
0.6648	Remote Similarity	NPC254798
0.6648	Remote Similarity	NPC474058
0.6647	Remote Similarity	NPC231382
0.6634	Remote Similarity	NPC41216
0.6633	Remote Similarity	NPC132874
0.6633	Remote Similarity	NPC138615
0.6633	Remote Similarity	NPC265642
0.6633	Remote Similarity	NPC218733
0.6632	Remote Similarity	NPC286994
0.6632	Remote Similarity	NPC135601
0.6632	Remote Similarity	NPC141612
0.6632	Remote Similarity	NPC17273
0.663	Remote Similarity	NPC123241
0.6629	Remote Similarity	NPC472242
0.6628	Remote Similarity	NPC130251
0.6627	Remote Similarity	NPC316104
0.6627	Remote Similarity	NPC162417
0.6626	Remote Similarity	NPC254698
0.6615	Remote Similarity	NPC97584
0.6615	Remote Similarity	NPC5630
0.6612	Remote Similarity	NPC176983
0.6612	Remote Similarity	NPC85651
0.6607	Remote Similarity	NPC207428
0.6601	Remote Similarity	NPC470489
0.6588	Remote Similarity	NPC173295
0.6585	Remote Similarity	NPC285394
0.6584	Remote Similarity	NPC291962
0.6584	Remote Similarity	NPC226143

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 NPC470548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	581
0.2-0.3	772
0.3-0.4	1211
0.4-0.5	3401
0.5-0.6	2567
0.6-0.7	418
0.7-0.8	9
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
0.7455	Intermediate Similarity	NPD2365	Approved
0.7425	Intermediate Similarity	NPD6017	Discontinued
0.741	Intermediate Similarity	NPD2820	Phase 3
0.741	Intermediate Similarity	NPD4430	Phase 2
0.7407	Intermediate Similarity	NPD2791	Discontinued
0.7356	Intermediate Similarity	NPD33	Approved
0.7356	Intermediate Similarity	NPD4393	Approved
0.7178	Intermediate Similarity	NPD1527	Phase 2
0.7151	Intermediate Similarity	NPD5923	Phase 1
0.7143	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2288	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5042	Phase 1
0.7101	Intermediate Similarity	NPD1625	Approved
0.7093	Intermediate Similarity	NPD4888	Discontinued
0.7069	Intermediate Similarity	NPD3248	Phase 1
0.7041	Intermediate Similarity	NPD6566	Discontinued
0.7041	Intermediate Similarity	NPD5552	Discontinued
0.7029	Intermediate Similarity	NPD2790	Discontinued
0.7011	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4942	Approved
0.6994	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5856	Discontinued
0.697	Remote Similarity	NPD7086	Phase 2
0.697	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5918	Discontinued
0.6954	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4515	Suspended
0.6941	Remote Similarity	NPD1189	Approved
0.694	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6557	Phase 2
0.6927	Remote Similarity	NPD4311	Approved
0.6927	Remote Similarity	NPD2506	Approved
0.6914	Remote Similarity	NPD3277	Phase 3
0.6902	Remote Similarity	NPD5997	Discontinued
0.6901	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3792	Approved
0.6882	Remote Similarity	NPD3625	Discontinued
0.6864	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1626	Approved
0.6859	Remote Similarity	NPD6484	Approved
0.6859	Remote Similarity	NPD6483	Approved
0.6859	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5748	Phase 2
0.6839	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3780	Phase 2
0.6816	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4330	Approved
0.6809	Remote Similarity	NPD4329	Approved
0.6794	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2427	Approved
0.6774	Remote Similarity	NPD2359	Approved
0.6772	Remote Similarity	NPD3990	Phase 3
0.6766	Remote Similarity	NPD2949	Approved
0.6766	Remote Similarity	NPD2950	Approved
0.6758	Remote Similarity	NPD3790	Phase 2
0.6753	Remote Similarity	NPD5504	Discontinued
0.6744	Remote Similarity	NPD6768	Approved
0.6742	Remote Similarity	NPD5086	Approved
0.6739	Remote Similarity	NPD2037	Approved
0.6738	Remote Similarity	NPD2361	Approved
0.6736	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5932	Phase 3
0.6724	Remote Similarity	NPD5933	Phase 3
0.6724	Remote Similarity	NPD5931	Phase 3
0.672	Remote Similarity	NPD3989	Phase 3
0.6718	Remote Similarity	NPD7569	Approved
0.6718	Remote Similarity	NPD7570	Approved
0.6714	Remote Similarity	NPD7186	Phase 3
0.6705	Remote Similarity	NPD4161	Discontinued
0.6703	Remote Similarity	NPD5183	Approved
0.6703	Remote Similarity	NPD5186	Approved
0.6702	Remote Similarity	NPD3449	Discontinued
0.6686	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2287	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1541	Approved
0.6667	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3782	Discontinued
0.6667	Remote Similarity	NPD6395	Phase 2
0.6667	Remote Similarity	NPD2431	Approved
0.6667	Remote Similarity	NPD2432	Approved
0.6667	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3227	Phase 2
0.6632	Remote Similarity	NPD6878	Phase 2
0.6632	Remote Similarity	NPD6879	Phase 2
0.663	Remote Similarity	NPD7011	Discontinued
0.663	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1230	Approved
0.6627	Remote Similarity	NPD4549	Discontinued
0.6614	Remote Similarity	NPD5600	Discontinued
0.6613	Remote Similarity	NPD7795	Phase 2
0.6607	Remote Similarity	NPD1920	Approved
0.6607	Remote Similarity	NPD1919	Approved
0.66	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6999	Discontinued
0.6598	Remote Similarity	NPD4948	Discontinued
0.6598	Remote Similarity	NPD6891	Phase 2
0.6596	Remote Similarity	NPD3422	Phase 3
0.6596	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3423	Phase 2
0.6591	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3141	Discontinued
0.6588	Remote Similarity	NPD2331	Discontinued
0.6585	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5159	Phase 2
0.6585	Remote Similarity	NPD5157	Phase 1
0.6582	Remote Similarity	NPD8240	Discontinued
0.6582	Remote Similarity	NPD6659	Phase 2
0.6578	Remote Similarity	NPD3776	Discontinued
0.6578	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD951	Approved
0.6571	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2813	Phase 3
0.6569	Remote Similarity	NPD6260	Discontinued
0.6567	Remote Similarity	NPD6805	Discontinued
0.6566	Remote Similarity	NPD4980	Approved
0.6561	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD2455	Approved
0.6559	Remote Similarity	NPD2454	Approved
0.6559	Remote Similarity	NPD2404	Discontinued
0.6556	Remote Similarity	NPD3229	Phase 2
0.6552	Remote Similarity	NPD7205	Discontinued
0.655	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5937	Approved
0.6545	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6320	Approved
0.6544	Remote Similarity	NPD6199	Discontinued
0.6543	Remote Similarity	NPD3377	Discontinued
0.6541	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5430	Discontinued
0.6526	Remote Similarity	NPD4092	Approved
0.6526	Remote Similarity	NPD5498	Phase 2
0.6524	Remote Similarity	NPD1575	Approved
0.6524	Remote Similarity	NPD2369	Discontinued
0.6524	Remote Similarity	NPD1573	Approved
0.6522	Remote Similarity	NPD5860	Discontinued
0.652	Remote Similarity	NPD4465	Phase 2
0.652	Remote Similarity	NPD4467	Phase 2
0.6519	Remote Similarity	NPD1175	Approved
0.6519	Remote Similarity	NPD7072	Phase 2
0.6517	Remote Similarity	NPD979	Approved
0.6514	Remote Similarity	NPD5024	Approved
0.6512	Remote Similarity	NPD6342	Discontinued
0.651	Remote Similarity	NPD3470	Approved
0.651	Remote Similarity	NPD3471	Approved
0.6508	Remote Similarity	NPD5466	Approved
0.6508	Remote Similarity	NPD3522	Approved
0.65	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5515	Phase 2
0.6497	Remote Similarity	NPD2336	Approved
0.6494	Remote Similarity	NPD2010	Phase 3
0.6492	Remote Similarity	NPD3997	Approved
0.6492	Remote Similarity	NPD3999	Approved
0.6492	Remote Similarity	NPD3998	Approved
0.6492	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1913	Phase 1
0.6488	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7001	Phase 3
0.6488	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1663	Discontinued
0.648	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1544	Phase 1
0.6474	Remote Similarity	NPD4091	Approved
0.6468	Remote Similarity	NPD5196	Approved
0.6468	Remote Similarity	NPD5194	Approved
0.6468	Remote Similarity	NPD5197	Approved
0.6467	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD8146	Phase 2
0.6464	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3315	Phase 3
0.6458	Remote Similarity	NPD5445	Approved
0.6453	Remote Similarity	NPD6321	Discontinued
0.6448	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1574	Approved
0.644	Remote Similarity	NPD3994	Approved
0.644	Remote Similarity	NPD3991	Approved
0.644	Remote Similarity	NPD3993	Approved
0.644	Remote Similarity	NPD3992	Approved
0.644	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.644	Remote Similarity	NPD3995	Approved
0.644	Remote Similarity	NPD3996	Approved
0.6436	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6309	Approved
0.6433	Remote Similarity	NPD6310	Approved
0.6433	Remote Similarity	NPD6311	Approved
0.6425	Remote Similarity	NPD5637	Discontinued
0.6425	Remote Similarity	NPD7666	Phase 3
0.6425	Remote Similarity	NPD7665	Phase 2
0.6422	Remote Similarity	NPD3775	Approved
0.6422	Remote Similarity	NPD3774	Approved
0.6422	Remote Similarity	NPD3773	Approved
0.6422	Remote Similarity	NPD7071	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