NPASS Compound

Structure

CID320154 OpenBabel06191716152D 26 29 0 0 1 0 0 0 0 0999 V2000 4.0071 -1.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7893 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1787 -0.3269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3965 -0.7785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7893 0.9311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3965 1.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8619 0.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4655 1.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8061 1.3964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1247 -0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0071 -0.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6124 0.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4655 0.1247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2249 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6124 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4186 1.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4187 -0.4654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2248 0.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3965 0.1247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8062 -0.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4185 2.2997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4187 -1.3687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8062 -1.3786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0070 1.3827 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 1 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 25 1 0 0 0 0 20 8 1 1 0 0 0 20 26 1 0 0 0 0 21 24 1 1 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.19
Volume:	370.952
LogP:	4.014
LogD:	3.319
LogS:	-4.366
# Rotatable Bonds:	1
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	5.953
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	1.602741758688353e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.101
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.777
Plasma Protein Binding (PPB):	95.10810089111328%
Volume Distribution (VD):	3.439
Pgp-substrate:	6.67018985748291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.315
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.39
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.604

ADMET: Excretion

Clearance (CL):	12.303
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.686
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.416
Carcinogencity:	0.862
Eye Corrosion:	0.004
Eye Irritation:	0.554
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC320154

Natural Product ID:	NPC320154
*Common Name:**	Komaroviquinone
IUPAC Name:	n.a.
Synonyms:	Komaroviquinone
Standard InCHIKey:	DUWHKUPNNGPNFK-ZEWGMFERSA-N
Standard InCHI:	InChI=1S/C21H28O5/c1-11(2)14-17(23)15-12(16(22)18(14)25-5)9-20-8-6-7-19(3,4)13(20)10-21(15,24)26-20/h11,13,24H,6-10H2,1-5H3/t13-,20-,21-/m0/s1
SMILES:	CC(C)C1=C(C(=O)C2=C(C1=O)C3(CC4C(CCCC4(C2)O3)(C)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463213
PubChem CID:	637171
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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
NPO26040	Dracocephalum komarovi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542361]
NPO31246	Dracocephalum komarovii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[12542361]
NPO26040	Dracocephalum komarovi	Species	Lamiaceae	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
IC50	1
LD50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2788	Cell Line	3T3	Mus musculus	LD50	=	0.091	nM	PMID[26037321]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	MLC	=	0.4	uM	PMID[542982]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	250.0	nM	PMID[542983]

☑ 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 NPC320154 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	228
0.1-0.2	1492
0.2-0.3	4561
0.3-0.4	8124
0.4-0.5	13872
0.5-0.6	8522
0.6-0.7	5202
0.7-0.8	693
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8018	Intermediate Similarity	NPC261330
0.7921	Intermediate Similarity	NPC271652
0.79	Intermediate Similarity	NPC113393
0.7895	Intermediate Similarity	NPC268958
0.789	Intermediate Similarity	NPC20192
0.789	Intermediate Similarity	NPC220705
0.7879	Intermediate Similarity	NPC307298
0.7876	Intermediate Similarity	NPC477116
0.7876	Intermediate Similarity	NPC27999
0.785	Intermediate Similarity	NPC146731
0.7818	Intermediate Similarity	NPC478209
0.7818	Intermediate Similarity	NPC235014
0.7798	Intermediate Similarity	NPC322903
0.7788	Intermediate Similarity	NPC478216
0.7778	Intermediate Similarity	NPC478208
0.7778	Intermediate Similarity	NPC472645
0.7757	Intermediate Similarity	NPC471208
0.7757	Intermediate Similarity	NPC159533
0.7757	Intermediate Similarity	NPC291154
0.7736	Intermediate Similarity	NPC207885
0.7736	Intermediate Similarity	NPC472643
0.7736	Intermediate Similarity	NPC112613
0.7727	Intermediate Similarity	NPC31522
0.7712	Intermediate Similarity	NPC470922
0.7692	Intermediate Similarity	NPC287236
0.7685	Intermediate Similarity	NPC296950
0.7679	Intermediate Similarity	NPC269530
0.7664	Intermediate Similarity	NPC273005
0.7664	Intermediate Similarity	NPC58329
0.7664	Intermediate Similarity	NPC31058
0.7664	Intermediate Similarity	NPC80781
0.7664	Intermediate Similarity	NPC469606
0.7658	Intermediate Similarity	NPC478211
0.7652	Intermediate Similarity	NPC240509
0.7647	Intermediate Similarity	NPC73457
0.7642	Intermediate Similarity	NPC54705
0.7636	Intermediate Similarity	NPC90946
0.7636	Intermediate Similarity	NPC325054
0.7636	Intermediate Similarity	NPC300614
0.7624	Intermediate Similarity	NPC474918
0.7619	Intermediate Similarity	NPC478233
0.7615	Intermediate Similarity	NPC469607
0.7611	Intermediate Similarity	NPC25909
0.7611	Intermediate Similarity	NPC478212
0.76	Intermediate Similarity	NPC272039
0.76	Intermediate Similarity	NPC220930
0.7596	Intermediate Similarity	NPC227494
0.7593	Intermediate Similarity	NPC131366
0.7589	Intermediate Similarity	NPC247031
0.7589	Intermediate Similarity	NPC317107
0.7589	Intermediate Similarity	NPC97939
0.7589	Intermediate Similarity	NPC132790
0.7589	Intermediate Similarity	NPC100329
0.7586	Intermediate Similarity	NPC476107
0.7568	Intermediate Similarity	NPC478210
0.7568	Intermediate Similarity	NPC87335
0.7568	Intermediate Similarity	NPC101018
0.7565	Intermediate Similarity	NPC469684
0.7563	Intermediate Similarity	NPC24651
0.7563	Intermediate Similarity	NPC476729
0.7547	Intermediate Similarity	NPC264378
0.7544	Intermediate Similarity	NPC247069
0.7542	Intermediate Similarity	NPC312833
0.7525	Intermediate Similarity	NPC58271
0.7525	Intermediate Similarity	NPC53454
0.7524	Intermediate Similarity	NPC94337
0.7523	Intermediate Similarity	NPC222161
0.7522	Intermediate Similarity	NPC317687
0.7521	Intermediate Similarity	NPC478051
0.75	Intermediate Similarity	NPC5103
0.75	Intermediate Similarity	NPC225049
0.75	Intermediate Similarity	NPC472666
0.75	Intermediate Similarity	NPC272898
0.75	Intermediate Similarity	NPC478206
0.75	Intermediate Similarity	NPC165250
0.75	Intermediate Similarity	NPC473036
0.75	Intermediate Similarity	NPC108581
0.75	Intermediate Similarity	NPC478205
0.7479	Intermediate Similarity	NPC91693
0.7479	Intermediate Similarity	NPC265557
0.7479	Intermediate Similarity	NPC18945
0.7479	Intermediate Similarity	NPC105926
0.7479	Intermediate Similarity	NPC67251
0.7478	Intermediate Similarity	NPC270478
0.7477	Intermediate Similarity	NPC472644
0.7477	Intermediate Similarity	NPC151393
0.7456	Intermediate Similarity	NPC159333
0.7456	Intermediate Similarity	NPC475966
0.7453	Intermediate Similarity	NPC471916
0.7451	Intermediate Similarity	NPC205548
0.7451	Intermediate Similarity	NPC280833
0.7434	Intermediate Similarity	NPC304180
0.7434	Intermediate Similarity	NPC179798
0.7431	Intermediate Similarity	NPC230918
0.7414	Intermediate Similarity	NPC243065
0.7414	Intermediate Similarity	NPC478204
0.7411	Intermediate Similarity	NPC228477
0.7411	Intermediate Similarity	NPC23497
0.7411	Intermediate Similarity	NPC77947
0.7411	Intermediate Similarity	NPC137911
0.7411	Intermediate Similarity	NPC286174
0.7407	Intermediate Similarity	NPC323441
0.7407	Intermediate Similarity	NPC470184
0.74	Intermediate Similarity	NPC253604
0.7391	Intermediate Similarity	NPC323821
0.7391	Intermediate Similarity	NPC45218
0.7391	Intermediate Similarity	NPC268238
0.7391	Intermediate Similarity	NPC143268
0.7387	Intermediate Similarity	NPC112780
0.7387	Intermediate Similarity	NPC202524
0.7383	Intermediate Similarity	NPC316598
0.7381	Intermediate Similarity	NPC251998
0.7379	Intermediate Similarity	NPC38952
0.7373	Intermediate Similarity	NPC17938
0.7373	Intermediate Similarity	NPC107338
0.7373	Intermediate Similarity	NPC112038
0.7373	Intermediate Similarity	NPC109607
0.7368	Intermediate Similarity	NPC12046
0.7368	Intermediate Similarity	NPC194951
0.7364	Intermediate Similarity	NPC294259
0.7364	Intermediate Similarity	NPC258532
0.7358	Intermediate Similarity	NPC17578
0.7358	Intermediate Similarity	NPC240673
0.7358	Intermediate Similarity	NPC272411
0.7355	Intermediate Similarity	NPC477745
0.7353	Intermediate Similarity	NPC143025
0.735	Intermediate Similarity	NPC297179
0.735	Intermediate Similarity	NPC21326
0.735	Intermediate Similarity	NPC113448
0.735	Intermediate Similarity	NPC475913
0.7345	Intermediate Similarity	NPC99760
0.7345	Intermediate Similarity	NPC129689
0.7339	Intermediate Similarity	NPC295791
0.7339	Intermediate Similarity	NPC476193
0.7339	Intermediate Similarity	NPC137430
0.7333	Intermediate Similarity	NPC212812
0.7333	Intermediate Similarity	NPC474555
0.7328	Intermediate Similarity	NPC16081
0.7328	Intermediate Similarity	NPC173686
0.7323	Intermediate Similarity	NPC596
0.7323	Intermediate Similarity	NPC295885
0.7323	Intermediate Similarity	NPC140045
0.7321	Intermediate Similarity	NPC275539
0.7321	Intermediate Similarity	NPC189075
0.7317	Intermediate Similarity	NPC476851
0.7317	Intermediate Similarity	NPC473593
0.7315	Intermediate Similarity	NPC472972
0.7315	Intermediate Similarity	NPC474012
0.7315	Intermediate Similarity	NPC470761
0.7315	Intermediate Similarity	NPC473219
0.7315	Intermediate Similarity	NPC476299
0.7315	Intermediate Similarity	NPC476767
0.7311	Intermediate Similarity	NPC129434
0.7311	Intermediate Similarity	NPC67569
0.7308	Intermediate Similarity	NPC78594
0.7308	Intermediate Similarity	NPC248913
0.7308	Intermediate Similarity	NPC324157
0.7304	Intermediate Similarity	NPC469463
0.7304	Intermediate Similarity	NPC33360
0.7304	Intermediate Similarity	NPC469496
0.7304	Intermediate Similarity	NPC157441
0.7304	Intermediate Similarity	NPC321496
0.7304	Intermediate Similarity	NPC56448
0.7304	Intermediate Similarity	NPC472926
0.7304	Intermediate Similarity	NPC469454
0.7304	Intermediate Similarity	NPC474271
0.7304	Intermediate Similarity	NPC51978
0.7302	Intermediate Similarity	NPC262813
0.7297	Intermediate Similarity	NPC1679
0.7297	Intermediate Similarity	NPC477125
0.7297	Intermediate Similarity	NPC127609
0.7297	Intermediate Similarity	NPC181357
0.7295	Intermediate Similarity	NPC476008
0.729	Intermediate Similarity	NPC132753
0.729	Intermediate Similarity	NPC121402
0.729	Intermediate Similarity	NPC151681
0.729	Intermediate Similarity	NPC91695
0.729	Intermediate Similarity	NPC208094
0.729	Intermediate Similarity	NPC224356
0.729	Intermediate Similarity	NPC175351
0.729	Intermediate Similarity	NPC70145
0.7288	Intermediate Similarity	NPC475775
0.7288	Intermediate Similarity	NPC472933
0.7288	Intermediate Similarity	NPC476529
0.7288	Intermediate Similarity	NPC158963
0.7288	Intermediate Similarity	NPC474179
0.7288	Intermediate Similarity	NPC230513
0.7288	Intermediate Similarity	NPC470777
0.7288	Intermediate Similarity	NPC475834
0.7281	Intermediate Similarity	NPC474846
0.7281	Intermediate Similarity	NPC469656
0.7281	Intermediate Similarity	NPC115303
0.7281	Intermediate Similarity	NPC469655
0.7281	Intermediate Similarity	NPC324683
0.728	Intermediate Similarity	NPC168879
0.7273	Intermediate Similarity	NPC8196
0.7273	Intermediate Similarity	NPC271059
0.7273	Intermediate Similarity	NPC99266
0.7273	Intermediate Similarity	NPC25666
0.7273	Intermediate Similarity	NPC95899

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 NPC320154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1846
0.2-0.3	3770
0.3-0.4	2221
0.4-0.5	696
0.5-0.6	233
0.6-0.7	185
0.7-0.8	2
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
0.7333	Intermediate Similarity	NPD5282	Discontinued
0.7083	Intermediate Similarity	NPD6059	Approved
0.7083	Intermediate Similarity	NPD6054	Approved
0.7043	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6015	Approved
0.7025	Intermediate Similarity	NPD6016	Approved
0.699	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7115	Discovery
0.6967	Remote Similarity	NPD5988	Approved
0.6967	Remote Similarity	NPD6370	Approved
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD4695	Discontinued
0.6869	Remote Similarity	NPD3617	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6847	Remote Similarity	NPD7640	Approved
0.6847	Remote Similarity	NPD7639	Approved
0.6822	Remote Similarity	NPD5693	Phase 1
0.68	Remote Similarity	NPD6616	Approved
0.6789	Remote Similarity	NPD5695	Phase 3
0.6783	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7638	Approved
0.6757	Remote Similarity	NPD5696	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6746	Remote Similarity	NPD7078	Approved
0.6731	Remote Similarity	NPD1694	Approved
0.6726	Remote Similarity	NPD7632	Discontinued
0.6724	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6009	Approved
0.6693	Remote Similarity	NPD6033	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.664	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD6053	Discontinued
0.6639	Remote Similarity	NPD6882	Approved
0.6638	Remote Similarity	NPD5701	Approved
0.6638	Remote Similarity	NPD5697	Approved
0.6581	Remote Similarity	NPD6011	Approved
0.6581	Remote Similarity	NPD7320	Approved
0.6581	Remote Similarity	NPD6881	Approved
0.6581	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6899	Approved
0.6579	Remote Similarity	NPD5211	Phase 2
0.6555	Remote Similarity	NPD6649	Approved
0.6555	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD5737	Approved
0.6542	Remote Similarity	NPD6672	Approved
0.6525	Remote Similarity	NPD6012	Approved
0.6525	Remote Similarity	NPD6013	Approved
0.6525	Remote Similarity	NPD6014	Approved
0.6518	Remote Similarity	NPD4755	Approved
0.6518	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD4519	Discontinued
0.6509	Remote Similarity	NPD3618	Phase 1
0.6509	Remote Similarity	NPD4623	Approved
0.6496	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6412	Phase 2
0.6486	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6904	Approved
0.6481	Remote Similarity	NPD6673	Approved
0.6481	Remote Similarity	NPD6080	Approved
0.6481	Remote Similarity	NPD4753	Phase 2
0.648	Remote Similarity	NPD8513	Phase 3
0.6476	Remote Similarity	NPD4197	Approved
0.6471	Remote Similarity	NPD6371	Approved
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD5141	Approved
0.6455	Remote Similarity	NPD6399	Phase 3
0.6446	Remote Similarity	NPD4632	Approved
0.6442	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4697	Phase 3
0.6422	Remote Similarity	NPD5692	Phase 3
0.6417	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD8130	Phase 1
0.6417	Remote Similarity	NPD6617	Approved
0.6417	Remote Similarity	NPD6847	Approved
0.6417	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5329	Approved
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD4700	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.6396	Remote Similarity	NPD7748	Approved
0.6387	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6845	Suspended
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6355	Remote Similarity	NPD5690	Phase 2
0.6355	Remote Similarity	NPD4694	Approved
0.6355	Remote Similarity	NPD5280	Approved
0.6355	Remote Similarity	NPD5279	Phase 3
0.6349	Remote Similarity	NPD7503	Approved
0.6349	Remote Similarity	NPD8515	Approved
0.6349	Remote Similarity	NPD8516	Approved
0.6349	Remote Similarity	NPD5983	Phase 2
0.6349	Remote Similarity	NPD8517	Approved
0.6348	Remote Similarity	NPD5223	Approved
0.6339	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4629	Approved
0.6339	Remote Similarity	NPD5210	Approved
0.6336	Remote Similarity	NPD5956	Approved
0.6306	Remote Similarity	NPD4202	Approved
0.6306	Remote Similarity	NPD5778	Approved
0.6306	Remote Similarity	NPD5779	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.6293	Remote Similarity	NPD5226	Approved
0.6288	Remote Similarity	NPD7260	Phase 2
0.6286	Remote Similarity	NPD4223	Phase 3
0.6286	Remote Similarity	NPD4221	Approved
0.6286	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5221	Approved
0.6283	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5222	Approved
0.6279	Remote Similarity	NPD7507	Approved
0.6273	Remote Similarity	NPD5785	Approved
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6001	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD4754	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6228	Remote Similarity	NPD5173	Approved
0.6216	Remote Similarity	NPD7515	Phase 2
0.621	Remote Similarity	NPD6274	Approved
0.6204	Remote Similarity	NPD6098	Approved
0.6195	Remote Similarity	NPD5654	Approved
0.6182	Remote Similarity	NPD5328	Approved
0.6168	Remote Similarity	NPD3665	Phase 1
0.6168	Remote Similarity	NPD3666	Approved
0.6168	Remote Similarity	NPD3133	Approved
0.616	Remote Similarity	NPD6317	Approved
0.6154	Remote Similarity	NPD6336	Discontinued
0.6147	Remote Similarity	NPD3573	Approved
0.6134	Remote Similarity	NPD4768	Approved
0.6134	Remote Similarity	NPD4767	Approved
0.6132	Remote Similarity	NPD3667	Approved
0.6126	Remote Similarity	NPD5207	Approved
0.6124	Remote Similarity	NPD6067	Discontinued
0.6117	Remote Similarity	NPD4756	Discovery
0.6111	Remote Similarity	NPD6335	Approved
0.6111	Remote Similarity	NPD6314	Approved
0.6111	Remote Similarity	NPD1696	Phase 3
0.6111	Remote Similarity	NPD6313	Approved
0.6107	Remote Similarity	NPD8074	Phase 3
0.6094	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6914	Discontinued
0.6087	Remote Similarity	NPD5959	Approved
0.6082	Remote Similarity	NPD3704	Approved
0.6075	Remote Similarity	NPD6110	Phase 1
0.6071	Remote Similarity	NPD6411	Approved
0.6071	Remote Similarity	NPD6079	Approved
0.6063	Remote Similarity	NPD7100	Approved
0.6063	Remote Similarity	NPD7101	Approved
0.6055	Remote Similarity	NPD4690	Approved
0.6055	Remote Similarity	NPD5205	Approved
0.6055	Remote Similarity	NPD7334	Approved
0.6055	Remote Similarity	NPD6409	Approved
0.6055	Remote Similarity	NPD5330	Approved
0.6055	Remote Similarity	NPD6684	Approved
0.6055	Remote Similarity	NPD4689	Approved
0.6055	Remote Similarity	NPD7146	Approved
0.6055	Remote Similarity	NPD4693	Phase 3
0.6055	Remote Similarity	NPD4138	Approved
0.6055	Remote Similarity	NPD7521	Approved
0.6055	Remote Similarity	NPD4688	Approved
0.6038	Remote Similarity	NPD4692	Approved
0.6038	Remote Similarity	NPD4139	Approved
0.6034	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5128	Approved
0.6033	Remote Similarity	NPD4729	Approved
0.6033	Remote Similarity	NPD4730	Approved
0.6019	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4786	Approved
0.6018	Remote Similarity	NPD5133	Approved
0.5984	Remote Similarity	NPD7328	Approved
0.5984	Remote Similarity	NPD7327	Approved
0.5982	Remote Similarity	NPD46	Approved
0.5982	Remote Similarity	NPD6698	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