NPASS Compound

Structure

NPC284184 OpenBabel07101718282D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 2.5981 1.5000 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 3.4641 -0.0000 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 0.8660 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 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 -0.8660 0.5000 0.0000 C 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 1.7321 3.0000 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 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 13 18 2 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.2
LogD:	2.197
LogS:	-4.892
# Rotatable Bonds:	1
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	2.678
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.529
MDCK Permeability:	2.7393187338020653e-05
Pgp-inhibitor:	0.716
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	88.88874053955078%
Volume Distribution (VD):	0.475
Pgp-substrate:	2.7593867778778076%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.193
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	7.089
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.65
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.779
Rat Oral Acute Toxicity:	0.645
Maximum Recommended Daily Dose:	0.494
Skin Sensitization:	0.104
Carcinogencity:	0.381
Eye Corrosion:	0.003
Eye Irritation:	0.229
Respiratory Toxicity:	0.296

Download Data

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

Natural Product: NPC284184

Natural Product ID:	NPC284184
*Common Name:**	9-Methoxy-4-Oxo-Alpha-Lapachone
IUPAC Name:	9-methoxy-2,2-dimethyl-3H-benzo[g]chromene-4,5,10-trione
Synonyms:
Standard InCHIKey:	IDDSRTJBQWWHPZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-16(2)7-9(17)12-13(18)8-5-4-6-10(20-3)11(8)14(19)15(12)21-16/h4-6H,7H2,1-3H3
SMILES:	COc1cccc2c1C(=O)C1=C(C2=O)C(=O)CC(O1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476293
PubChem CID:	10684597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[532603]
NPT2	Others	Unspecified		Activity	=	32.7	%	PMID[532603]
NPT2	Others	Unspecified		Activity	=	63.8	%	PMID[532603]
NPT2	Others	Unspecified		Activity	=	88.1	%	PMID[532603]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[532603]

☑ 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 NPC284184 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	435
0.1-0.2	1644
0.2-0.3	4430
0.3-0.4	10502
0.4-0.5	7846
0.5-0.6	5334
0.6-0.7	7351
0.7-0.8	5028
0.8-0.85	108
0.85-0.9	14
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC301341
0.9328	High Similarity	NPC232996
0.9098	High Similarity	NPC205360
0.8986	High Similarity	NPC477408
0.8963	High Similarity	NPC171968
0.8955	High Similarity	NPC477412
0.8939	High Similarity	NPC45537
0.8923	High Similarity	NPC182646
0.8777	High Similarity	NPC173980
0.8696	High Similarity	NPC281513
0.8696	High Similarity	NPC22222
0.8667	High Similarity	NPC57552
0.8652	High Similarity	NPC109007
0.8623	High Similarity	NPC1249
0.8601	High Similarity	NPC215451
0.8601	High Similarity	NPC277369
0.8593	High Similarity	NPC237225
0.8582	High Similarity	NPC223336
0.8561	High Similarity	NPC217914
0.8561	High Similarity	NPC22644
0.8542	High Similarity	NPC477409
0.8511	High Similarity	NPC265181
0.8493	Intermediate Similarity	NPC52106
0.8493	Intermediate Similarity	NPC252208
0.8472	Intermediate Similarity	NPC53016
0.8467	Intermediate Similarity	NPC198305
0.8451	Intermediate Similarity	NPC470407
0.8444	Intermediate Similarity	NPC51037
0.8444	Intermediate Similarity	NPC177925
0.844	Intermediate Similarity	NPC186647
0.8435	Intermediate Similarity	NPC474107
0.8433	Intermediate Similarity	NPC56332
0.8403	Intermediate Similarity	NPC69755
0.8382	Intermediate Similarity	NPC298884
0.837	Intermediate Similarity	NPC224657
0.8369	Intermediate Similarity	NPC141934
0.8356	Intermediate Similarity	NPC474630
0.8356	Intermediate Similarity	NPC478019
0.8345	Intermediate Similarity	NPC183103
0.8345	Intermediate Similarity	NPC477406
0.8345	Intermediate Similarity	NPC474340
0.8333	Intermediate Similarity	NPC124365
0.8322	Intermediate Similarity	NPC1268
0.8321	Intermediate Similarity	NPC171023
0.831	Intermediate Similarity	NPC477534
0.831	Intermediate Similarity	NPC471542
0.8309	Intermediate Similarity	NPC474264
0.8296	Intermediate Similarity	NPC310540
0.8288	Intermediate Similarity	NPC475201
0.8288	Intermediate Similarity	NPC274085
0.8288	Intermediate Similarity	NPC89664
0.8286	Intermediate Similarity	NPC470406
0.8273	Intermediate Similarity	NPC239134
0.8255	Intermediate Similarity	NPC226578
0.8252	Intermediate Similarity	NPC475104
0.8243	Intermediate Similarity	NPC478018
0.8239	Intermediate Similarity	NPC471670
0.8231	Intermediate Similarity	NPC49282
0.8231	Intermediate Similarity	NPC28632
0.8224	Intermediate Similarity	NPC3898
0.8219	Intermediate Similarity	NPC117674
0.8219	Intermediate Similarity	NPC472840
0.8219	Intermediate Similarity	NPC167663
0.8219	Intermediate Similarity	NPC316691
0.8214	Intermediate Similarity	NPC309430
0.8214	Intermediate Similarity	NPC312560
0.8207	Intermediate Similarity	NPC84273
0.8207	Intermediate Similarity	NPC283292
0.8194	Intermediate Similarity	NPC114620
0.8194	Intermediate Similarity	NPC103337
0.8188	Intermediate Similarity	NPC165257
0.8182	Intermediate Similarity	NPC290601
0.8176	Intermediate Similarity	NPC300540
0.8175	Intermediate Similarity	NPC231774
0.8175	Intermediate Similarity	NPC474737
0.8163	Intermediate Similarity	NPC472836
0.8163	Intermediate Similarity	NPC471600
0.8163	Intermediate Similarity	NPC471451
0.8156	Intermediate Similarity	NPC477536
0.8146	Intermediate Similarity	NPC230848
0.8143	Intermediate Similarity	NPC301717
0.8143	Intermediate Similarity	NPC164295
0.8143	Intermediate Similarity	NPC279596
0.8138	Intermediate Similarity	NPC477537
0.8133	Intermediate Similarity	NPC80370
0.8133	Intermediate Similarity	NPC84142
0.8125	Intermediate Similarity	NPC61590
0.812	Intermediate Similarity	NPC201284
0.8117	Intermediate Similarity	NPC294300
0.8117	Intermediate Similarity	NPC317900
0.8117	Intermediate Similarity	NPC476404
0.8117	Intermediate Similarity	NPC67197
0.8116	Intermediate Similarity	NPC470841
0.8108	Intermediate Similarity	NPC73416
0.8108	Intermediate Similarity	NPC160777
0.8108	Intermediate Similarity	NPC474261
0.8088	Intermediate Similarity	NPC135062
0.8082	Intermediate Similarity	NPC149780
0.8079	Intermediate Similarity	NPC216917
0.8079	Intermediate Similarity	NPC164762
0.8077	Intermediate Similarity	NPC478134
0.8069	Intermediate Similarity	NPC295339
0.8067	Intermediate Similarity	NPC472839
0.8067	Intermediate Similarity	NPC192069
0.8067	Intermediate Similarity	NPC280025
0.8054	Intermediate Similarity	NPC250331
0.8054	Intermediate Similarity	NPC471346
0.8043	Intermediate Similarity	NPC306765
0.8043	Intermediate Similarity	NPC237868
0.8042	Intermediate Similarity	NPC89504
0.8042	Intermediate Similarity	NPC88065
0.8042	Intermediate Similarity	NPC298900
0.8042	Intermediate Similarity	NPC95485
0.8041	Intermediate Similarity	NPC475813
0.8041	Intermediate Similarity	NPC93241
0.8041	Intermediate Similarity	NPC229787
0.8041	Intermediate Similarity	NPC184702
0.8041	Intermediate Similarity	NPC27798
0.8041	Intermediate Similarity	NPC189650
0.8041	Intermediate Similarity	NPC19896
0.8039	Intermediate Similarity	NPC155686
0.8029	Intermediate Similarity	NPC470163
0.8029	Intermediate Similarity	NPC470162
0.8028	Intermediate Similarity	NPC59459
0.8028	Intermediate Similarity	NPC254603
0.8027	Intermediate Similarity	NPC297985
0.8026	Intermediate Similarity	NPC474414
0.8026	Intermediate Similarity	NPC46882
0.8026	Intermediate Similarity	NPC144283
0.8026	Intermediate Similarity	NPC132990
0.8026	Intermediate Similarity	NPC91809
0.8014	Intermediate Similarity	NPC324488
0.8014	Intermediate Similarity	NPC477535
0.8014	Intermediate Similarity	NPC49242
0.8014	Intermediate Similarity	NPC156872
0.8013	Intermediate Similarity	NPC10027
0.8013	Intermediate Similarity	NPC65775
0.8013	Intermediate Similarity	NPC313368
0.8013	Intermediate Similarity	NPC284495
0.8	Intermediate Similarity	NPC312929
0.8	Intermediate Similarity	NPC104380
0.8	Intermediate Similarity	NPC217602
0.8	Intermediate Similarity	NPC259632
0.8	Intermediate Similarity	NPC126767
0.8	Intermediate Similarity	NPC118027
0.8	Intermediate Similarity	NPC473282
0.8	Intermediate Similarity	NPC289042
0.8	Intermediate Similarity	NPC190648
0.8	Intermediate Similarity	NPC246466
0.8	Intermediate Similarity	NPC245584
0.8	Intermediate Similarity	NPC56433
0.8	Intermediate Similarity	NPC58373
0.7987	Intermediate Similarity	NPC317585
0.7986	Intermediate Similarity	NPC475549
0.7986	Intermediate Similarity	NPC474311
0.7985	Intermediate Similarity	NPC54243
0.7974	Intermediate Similarity	NPC470340
0.7974	Intermediate Similarity	NPC470353
0.7974	Intermediate Similarity	NPC288534
0.7974	Intermediate Similarity	NPC24232
0.7973	Intermediate Similarity	NPC476473
0.7962	Intermediate Similarity	NPC316457
0.7962	Intermediate Similarity	NPC476929
0.7961	Intermediate Similarity	NPC290954
0.7961	Intermediate Similarity	NPC474660
0.7961	Intermediate Similarity	NPC255641
0.7961	Intermediate Similarity	NPC147735
0.7961	Intermediate Similarity	NPC295036
0.7961	Intermediate Similarity	NPC294646
0.7959	Intermediate Similarity	NPC171094
0.7959	Intermediate Similarity	NPC257003
0.7958	Intermediate Similarity	NPC153453
0.7958	Intermediate Similarity	NPC118253
0.7958	Intermediate Similarity	NPC472882
0.7958	Intermediate Similarity	NPC88864
0.7956	Intermediate Similarity	NPC93730
0.7947	Intermediate Similarity	NPC472056
0.7947	Intermediate Similarity	NPC219560
0.7945	Intermediate Similarity	NPC471602
0.7945	Intermediate Similarity	NPC256463
0.7945	Intermediate Similarity	NPC25427
0.7945	Intermediate Similarity	NPC111422
0.7945	Intermediate Similarity	NPC216312
0.7945	Intermediate Similarity	NPC476477
0.7945	Intermediate Similarity	NPC29771
0.7945	Intermediate Similarity	NPC299405
0.7945	Intermediate Similarity	NPC306835
0.7943	Intermediate Similarity	NPC470725
0.7943	Intermediate Similarity	NPC473271
0.7943	Intermediate Similarity	NPC253488
0.7943	Intermediate Similarity	NPC7569
0.7939	Intermediate Similarity	NPC279916
0.7935	Intermediate Similarity	NPC470352
0.7935	Intermediate Similarity	NPC276231
0.7935	Intermediate Similarity	NPC478223
0.7935	Intermediate Similarity	NPC472050
0.7935	Intermediate Similarity	NPC470354
0.7933	Intermediate Similarity	NPC136878
0.7933	Intermediate Similarity	NPC60389
0.7933	Intermediate Similarity	NPC281398

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 NPC284184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	969
0.2-0.3	1518
0.3-0.4	2630
0.4-0.5	2008
0.5-0.6	1124
0.6-0.7	412
0.7-0.8	103
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD1471	Phase 3
0.8252	Intermediate Similarity	NPD2346	Discontinued
0.8013	Intermediate Similarity	NPD3226	Approved
0.7943	Intermediate Similarity	NPD2313	Discontinued
0.7923	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2798	Approved
0.781	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1876	Approved
0.7755	Intermediate Similarity	NPD2344	Approved
0.7754	Intermediate Similarity	NPD3972	Approved
0.7748	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1470	Approved
0.7687	Intermediate Similarity	NPD2796	Approved
0.763	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7819	Suspended
0.7568	Intermediate Similarity	NPD2935	Discontinued
0.755	Intermediate Similarity	NPD2309	Approved
0.7534	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD3748	Approved
0.7466	Intermediate Similarity	NPD4307	Phase 2
0.7464	Intermediate Similarity	NPD1651	Approved
0.7431	Intermediate Similarity	NPD6832	Phase 2
0.7429	Intermediate Similarity	NPD1201	Approved
0.7421	Intermediate Similarity	NPD3817	Phase 2
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD1247	Approved
0.7403	Intermediate Similarity	NPD2533	Approved
0.7403	Intermediate Similarity	NPD2534	Approved
0.7403	Intermediate Similarity	NPD2532	Approved
0.7389	Intermediate Similarity	NPD6599	Discontinued
0.7383	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1607	Approved
0.7362	Intermediate Similarity	NPD6232	Discontinued
0.7358	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1512	Approved
0.7347	Intermediate Similarity	NPD1240	Approved
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD3267	Approved
0.7343	Intermediate Similarity	NPD3266	Approved
0.7341	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5691	Approved
0.7338	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.7317	Intermediate Similarity	NPD3926	Phase 2
0.7312	Intermediate Similarity	NPD5402	Approved
0.7308	Intermediate Similarity	NPD920	Approved
0.7305	Intermediate Similarity	NPD1281	Approved
0.7303	Intermediate Similarity	NPD2800	Approved
0.7297	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.7292	Intermediate Similarity	NPD1019	Discontinued
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD919	Approved
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD3300	Phase 2
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD3882	Suspended
0.7255	Intermediate Similarity	NPD3750	Approved
0.7255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9717	Approved
0.725	Intermediate Similarity	NPD2801	Approved
0.725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1549	Phase 2
0.723	Intermediate Similarity	NPD2979	Phase 3
0.7226	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7211	Intermediate Similarity	NPD411	Approved
0.7195	Intermediate Similarity	NPD6959	Discontinued
0.719	Intermediate Similarity	NPD1243	Approved
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6280	Approved
0.7188	Intermediate Similarity	NPD6279	Approved
0.7188	Intermediate Similarity	NPD1934	Approved
0.7188	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD1933	Approved
0.7179	Intermediate Similarity	NPD5401	Approved
0.7179	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2353	Approved
0.7163	Intermediate Similarity	NPD4626	Approved
0.7163	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7117	Intermediate Similarity	NPD3749	Approved
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1203	Approved
0.7097	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3887	Approved
0.7095	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD5403	Approved
0.7063	Intermediate Similarity	NPD1611	Approved
0.7051	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8032	Phase 2
0.7039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2182	Approved
0.7032	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6273	Approved
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7014	Intermediate Similarity	NPD1608	Approved
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2296	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6993	Remote Similarity	NPD6100	Approved
0.6992	Remote Similarity	NPD164	Approved
0.6987	Remote Similarity	NPD2354	Approved
0.6986	Remote Similarity	NPD2797	Approved
0.6982	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3764	Approved
0.6964	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6166	Phase 2
0.6964	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2403	Approved
0.6961	Remote Similarity	NPD6777	Approved
0.6961	Remote Similarity	NPD6779	Approved
0.6961	Remote Similarity	NPD6781	Approved
0.6961	Remote Similarity	NPD6778	Approved
0.6961	Remote Similarity	NPD6782	Approved
0.6961	Remote Similarity	NPD6780	Approved
0.6961	Remote Similarity	NPD6776	Approved
0.6957	Remote Similarity	NPD6585	Discontinued
0.695	Remote Similarity	NPD5536	Phase 2
0.6946	Remote Similarity	NPD6808	Phase 2
0.6943	Remote Similarity	NPD7236	Approved
0.6941	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7435	Discontinued
0.6932	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4628	Phase 3
0.6914	Remote Similarity	NPD5889	Approved
0.6914	Remote Similarity	NPD5890	Approved
0.6909	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6651	Approved
0.6903	Remote Similarity	NPD2897	Discontinued
0.6899	Remote Similarity	NPD7390	Discontinued
0.6894	Remote Similarity	NPD2651	Approved
0.6894	Remote Similarity	NPD2649	Approved
0.6892	Remote Similarity	NPD9494	Approved
0.6887	Remote Similarity	NPD4060	Phase 1
0.6887	Remote Similarity	NPD3142	Approved
0.6887	Remote Similarity	NPD3140	Approved
0.6883	Remote Similarity	NPD1551	Phase 2
0.6883	Remote Similarity	NPD2438	Suspended
0.6883	Remote Similarity	NPD2531	Phase 2
0.6882	Remote Similarity	NPD3818	Discontinued
0.6867	Remote Similarity	NPD6798	Discontinued
0.686	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD7697	Approved
0.6848	Remote Similarity	NPD7696	Phase 3
0.6848	Remote Similarity	NPD7698	Approved
0.6845	Remote Similarity	NPD5710	Approved
0.6845	Remote Similarity	NPD3787	Discontinued
0.6845	Remote Similarity	NPD5711	Approved
0.6842	Remote Similarity	NPD6355	Discontinued
0.6842	Remote Similarity	NPD5844	Phase 1
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD8312	Approved
0.6821	Remote Similarity	NPD7251	Discontinued
0.6818	Remote Similarity	NPD7033	Discontinued
0.6813	Remote Similarity	NPD5049	Phase 3
0.6813	Remote Similarity	NPD8285	Discontinued
0.6812	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7870	Phase 2
0.6811	Remote Similarity	NPD7871	Phase 2
0.68	Remote Similarity	NPD7095	Approved
0.6788	Remote Similarity	NPD5978	Approved
0.6788	Remote Similarity	NPD5977	Approved
0.6784	Remote Similarity	NPD7177	Discontinued
0.6782	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7808	Phase 3
0.6776	Remote Similarity	NPD943	Approved
0.6774	Remote Similarity	NPD5408	Approved
0.6774	Remote Similarity	NPD5406	Approved
0.6774	Remote Similarity	NPD5404	Approved
0.6774	Remote Similarity	NPD5405	Approved
0.677	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3496	Discontinued
0.6752	Remote Similarity	NPD2654	Approved
0.675	Remote Similarity	NPD4661	Approved
0.675	Remote Similarity	NPD4662	Approved
0.6747	Remote Similarity	NPD7768	Phase 2
0.6738	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5585	Approved
0.6736	Remote Similarity	NPD3025	Approved
0.6736	Remote Similarity	NPD3024	Approved
0.6732	Remote Similarity	NPD4622	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data