NPASS Compound

Structure

CID183103 OpenBabel06191715562D 23 25 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -4.3301 -0.5000 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 -1.7321 3.0000 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 -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 -1.7321 1.0000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -0.0000 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 -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 0.0000 0.0000 C 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 11 1 0 0 0 0 4 12 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 17 2 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	334.086
LogP:	5.003
LogD:	3.973
LogS:	-7.08
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	2.697
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.098
MDCK Permeability:	1.749282091623172e-05
Pgp-inhibitor:	0.863
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.718
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	100.3286361694336%
Volume Distribution (VD):	0.351
Pgp-substrate:	0.8984276056289673%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.776
CYP2C19-substrate:	0.646
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.557
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	4.075
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.863
Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.823
Carcinogencity:	0.946
Eye Corrosion:	0.022
Eye Irritation:	0.984
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC183103

Natural Product ID:	NPC183103
*Common Name:**	Multiorthoquinone
IUPAC Name:	6-methoxy-7,8-dimethyl-2-propan-2-ylphenanthrene-3,4-dione
Synonyms:	Multiorthoquinone
Standard InCHIKey:	YJIHLYMLQOIPEU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-10(2)15-8-13-6-7-14-11(3)12(4)17(23-5)9-16(14)18(13)20(22)19(15)21/h6-10H,1-5H3
SMILES:	CC(C)C1=Cc2ccc3c(C)c(C)c(cc3c2C(=O)C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506757
PubChem CID:	467784
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*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
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[11325249]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21169	Salvia blepharochlaena	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
MIC	5
Others	4

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	2.0	ug.mL-1	PMID[542303]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.1	ug.mL-1	PMID[542303]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	>	7.0	mm	PMID[542303]
NPT174	Organism	Streptococcus	Streptococcus	MIC	=	0.1	ug.mL-1	PMID[542303]
NPT174	Organism	Streptococcus	Streptococcus	IZ	>	7.0	mm	PMID[542303]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	>	7.0	mm	PMID[542303]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	2.0	ug.mL-1	PMID[542303]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IZ	>	7.0	mm	PMID[542303]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	0.5	ug.mL-1	PMID[542303]

☑ 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 NPC183103 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	458
0.1-0.2	1629
0.2-0.3	3763
0.3-0.4	10658
0.4-0.5	7798
0.5-0.6	4093
0.6-0.7	8627
0.7-0.8	5302
0.8-0.85	305
0.85-0.9	49
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9606	High Similarity	NPC239134
0.952	High Similarity	NPC474737
0.9466	High Similarity	NPC186647
0.9453	High Similarity	NPC164295
0.9308	High Similarity	NPC470406
0.9242	High Similarity	NPC471670
0.9179	High Similarity	NPC470407
0.9141	High Similarity	NPC428300
0.9062	High Similarity	NPC177925
0.9055	High Similarity	NPC75432
0.903	High Similarity	NPC290601
0.9023	High Similarity	NPC22644
0.9008	High Similarity	NPC279596
0.8986	High Similarity	NPC472836
0.8923	High Similarity	NPC96024
0.8881	High Similarity	NPC89504
0.8881	High Similarity	NPC88065
0.8881	High Similarity	NPC95485
0.8855	High Similarity	NPC57552
0.8849	High Similarity	NPC308006
0.8797	High Similarity	NPC312560
0.8769	High Similarity	NPC474264
0.8732	High Similarity	NPC472841
0.872	High Similarity	NPC469954
0.8705	High Similarity	NPC201297
0.8686	High Similarity	NPC233707
0.8667	High Similarity	NPC1249
0.8667	High Similarity	NPC209858
0.8667	High Similarity	NPC324117
0.8652	High Similarity	NPC49282
0.8647	High Similarity	NPC470725
0.8647	High Similarity	NPC245395
0.8643	High Similarity	NPC53016
0.8643	High Similarity	NPC167663
0.8623	High Similarity	NPC223336
0.8615	High Similarity	NPC199273
0.8615	High Similarity	NPC56332
0.8601	High Similarity	NPC472839
0.8582	High Similarity	NPC290038
0.8582	High Similarity	NPC189650
0.8571	High Similarity	NPC276238
0.8571	High Similarity	NPC69755
0.8561	High Similarity	NPC72667
0.8552	High Similarity	NPC306011
0.8552	High Similarity	NPC474414
0.8552	High Similarity	NPC472838
0.8551	High Similarity	NPC475104
0.855	High Similarity	NPC232387
0.8542	High Similarity	NPC80370
0.8542	High Similarity	NPC329933
0.8538	High Similarity	NPC182646
0.8531	High Similarity	NPC478163
0.8531	High Similarity	NPC58373
0.8521	High Similarity	NPC478019
0.8519	High Similarity	NPC474340
0.8485	Intermediate Similarity	NPC254492
0.8478	Intermediate Similarity	NPC301341
0.8473	Intermediate Similarity	NPC111088
0.8462	Intermediate Similarity	NPC282577
0.8456	Intermediate Similarity	NPC59459
0.8451	Intermediate Similarity	NPC309169
0.8451	Intermediate Similarity	NPC196941
0.8451	Intermediate Similarity	NPC260152
0.8444	Intermediate Similarity	NPC301717
0.844	Intermediate Similarity	NPC137920
0.844	Intermediate Similarity	NPC229218
0.844	Intermediate Similarity	NPC141817
0.844	Intermediate Similarity	NPC125134
0.844	Intermediate Similarity	NPC192597
0.844	Intermediate Similarity	NPC86455
0.844	Intermediate Similarity	NPC176030
0.844	Intermediate Similarity	NPC169214
0.8433	Intermediate Similarity	NPC171460
0.8425	Intermediate Similarity	NPC144283
0.8425	Intermediate Similarity	NPC25648
0.8425	Intermediate Similarity	NPC230848
0.8421	Intermediate Similarity	NPC176130
0.8421	Intermediate Similarity	NPC78364
0.8421	Intermediate Similarity	NPC84672
0.8421	Intermediate Similarity	NPC69424
0.8409	Intermediate Similarity	NPC470858
0.8403	Intermediate Similarity	NPC478018
0.8403	Intermediate Similarity	NPC34802
0.8394	Intermediate Similarity	NPC274876
0.8394	Intermediate Similarity	NPC213122
0.838	Intermediate Similarity	NPC472840
0.838	Intermediate Similarity	NPC84266
0.8378	Intermediate Similarity	NPC478159
0.8378	Intermediate Similarity	NPC478161
0.8372	Intermediate Similarity	NPC232958
0.837	Intermediate Similarity	NPC253488
0.837	Intermediate Similarity	NPC27659
0.8369	Intermediate Similarity	NPC149780
0.8367	Intermediate Similarity	NPC27615
0.8367	Intermediate Similarity	NPC10429
0.8359	Intermediate Similarity	NPC171023
0.8358	Intermediate Similarity	NPC181675
0.8357	Intermediate Similarity	NPC1268
0.8356	Intermediate Similarity	NPC295977
0.8356	Intermediate Similarity	NPC58310
0.8346	Intermediate Similarity	NPC312105
0.8345	Intermediate Similarity	NPC284184
0.8345	Intermediate Similarity	NPC474107
0.8345	Intermediate Similarity	NPC95526
0.8345	Intermediate Similarity	NPC24394
0.8333	Intermediate Similarity	NPC473927
0.8333	Intermediate Similarity	NPC30216
0.8333	Intermediate Similarity	NPC39361
0.8322	Intermediate Similarity	NPC471451
0.8322	Intermediate Similarity	NPC471305
0.831	Intermediate Similarity	NPC94076
0.831	Intermediate Similarity	NPC182255
0.831	Intermediate Similarity	NPC40118
0.831	Intermediate Similarity	NPC126534
0.831	Intermediate Similarity	NPC232021
0.8309	Intermediate Similarity	NPC477412
0.8309	Intermediate Similarity	NPC471851
0.8308	Intermediate Similarity	NPC144547
0.8299	Intermediate Similarity	NPC189773
0.8298	Intermediate Similarity	NPC109232
0.8288	Intermediate Similarity	NPC472837
0.8288	Intermediate Similarity	NPC65589
0.8288	Intermediate Similarity	NPC300983
0.8288	Intermediate Similarity	NPC97029
0.8288	Intermediate Similarity	NPC288036
0.8288	Intermediate Similarity	NPC472298
0.8288	Intermediate Similarity	NPC97028
0.8288	Intermediate Similarity	NPC100985
0.8288	Intermediate Similarity	NPC158338
0.8284	Intermediate Similarity	NPC45537
0.8276	Intermediate Similarity	NPC52692
0.8276	Intermediate Similarity	NPC289042
0.8276	Intermediate Similarity	NPC245584
0.8276	Intermediate Similarity	NPC190648
0.8276	Intermediate Similarity	NPC56433
0.8276	Intermediate Similarity	NPC312929
0.8276	Intermediate Similarity	NPC118027
0.8276	Intermediate Similarity	NPC126767
0.8273	Intermediate Similarity	NPC475549
0.8271	Intermediate Similarity	NPC123506
0.8261	Intermediate Similarity	NPC50924
0.8258	Intermediate Similarity	NPC141252
0.8258	Intermediate Similarity	NPC11799
0.8258	Intermediate Similarity	NPC474691
0.8255	Intermediate Similarity	NPC66508
0.8255	Intermediate Similarity	NPC226656
0.8252	Intermediate Similarity	NPC117674
0.8252	Intermediate Similarity	NPC158871
0.8252	Intermediate Similarity	NPC297600
0.8252	Intermediate Similarity	NPC277369
0.8252	Intermediate Similarity	NPC215451
0.8252	Intermediate Similarity	NPC163948
0.8243	Intermediate Similarity	NPC164912
0.8243	Intermediate Similarity	NPC87708
0.824	Intermediate Similarity	NPC470723
0.824	Intermediate Similarity	NPC23332
0.8239	Intermediate Similarity	NPC265178
0.8239	Intermediate Similarity	NPC124365
0.8239	Intermediate Similarity	NPC171094
0.8235	Intermediate Similarity	NPC108129
0.8231	Intermediate Similarity	NPC289432
0.8231	Intermediate Similarity	NPC988
0.8231	Intermediate Similarity	NPC470568
0.8231	Intermediate Similarity	NPC290954
0.8231	Intermediate Similarity	NPC474660
0.8231	Intermediate Similarity	NPC255641
0.8222	Intermediate Similarity	NPC125887
0.8222	Intermediate Similarity	NPC3009
0.8219	Intermediate Similarity	NPC256672
0.8219	Intermediate Similarity	NPC27221
0.8219	Intermediate Similarity	NPC7025
0.8219	Intermediate Similarity	NPC472056
0.8214	Intermediate Similarity	NPC470721
0.8214	Intermediate Similarity	NPC156888
0.8214	Intermediate Similarity	NPC6100
0.8214	Intermediate Similarity	NPC470722
0.8207	Intermediate Similarity	NPC163846
0.8207	Intermediate Similarity	NPC225173
0.8201	Intermediate Similarity	NPC22222
0.8201	Intermediate Similarity	NPC281513
0.82	Intermediate Similarity	NPC213401
0.82	Intermediate Similarity	NPC288353
0.8195	Intermediate Similarity	NPC107846
0.8194	Intermediate Similarity	NPC91694
0.8194	Intermediate Similarity	NPC300603
0.8188	Intermediate Similarity	NPC169990
0.8188	Intermediate Similarity	NPC477139
0.8188	Intermediate Similarity	NPC329844
0.8188	Intermediate Similarity	NPC210942
0.8188	Intermediate Similarity	NPC78307
0.8182	Intermediate Similarity	NPC49108
0.8182	Intermediate Similarity	NPC11314
0.8176	Intermediate Similarity	NPC258249
0.8176	Intermediate Similarity	NPC302783
0.8176	Intermediate Similarity	NPC474417
0.8176	Intermediate Similarity	NPC72958
0.8176	Intermediate Similarity	NPC118332
0.8176	Intermediate Similarity	NPC149526
0.8176	Intermediate Similarity	NPC473201
0.8176	Intermediate Similarity	NPC470569

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 NPC183103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	984
0.2-0.3	1186
0.3-0.4	2509
0.4-0.5	2102
0.5-0.6	1226
0.6-0.7	569
0.7-0.8	151
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.888	High Similarity	NPD1651	Approved
0.875	High Similarity	NPD3972	Approved
0.8672	High Similarity	NPD1281	Approved
0.85	High Similarity	NPD7003	Approved
0.8473	Intermediate Similarity	NPD1876	Approved
0.8473	Intermediate Similarity	NPD1283	Approved
0.8248	Intermediate Similarity	NPD2979	Phase 3
0.8209	Intermediate Similarity	NPD2798	Approved
0.8156	Intermediate Similarity	NPD2346	Discontinued
0.8154	Intermediate Similarity	NPD5691	Approved
0.8092	Intermediate Similarity	NPD4626	Approved
0.8041	Intermediate Similarity	NPD7458	Discontinued
0.8014	Intermediate Similarity	NPD2799	Discontinued
0.7958	Intermediate Similarity	NPD2531	Phase 2
0.7958	Intermediate Similarity	NPD2438	Suspended
0.7958	Intermediate Similarity	NPD2935	Discontinued
0.7958	Intermediate Similarity	NPD2796	Approved
0.7955	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7819	Suspended
0.7919	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3748	Approved
0.7872	Intermediate Similarity	NPD1607	Approved
0.7838	Intermediate Similarity	NPD6273	Approved
0.7836	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1241	Discontinued
0.78	Intermediate Similarity	NPD3226	Approved
0.7786	Intermediate Similarity	NPD8032	Phase 2
0.7785	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2344	Approved
0.7778	Intermediate Similarity	NPD1471	Phase 3
0.773	Intermediate Similarity	NPD1240	Approved
0.7707	Intermediate Similarity	NPD6232	Discontinued
0.7687	Intermediate Similarity	NPD17	Approved
0.7674	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6959	Discontinued
0.7639	Intermediate Similarity	NPD1510	Phase 2
0.7639	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD3750	Approved
0.7609	Intermediate Similarity	NPD3266	Approved
0.7609	Intermediate Similarity	NPD3267	Approved
0.7606	Intermediate Similarity	NPD4307	Phase 2
0.7594	Intermediate Similarity	NPD5536	Phase 2
0.7591	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD5494	Approved
0.7578	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD1611	Approved
0.7574	Intermediate Similarity	NPD1201	Approved
0.7568	Intermediate Similarity	NPD2309	Approved
0.7556	Intermediate Similarity	NPD2932	Approved
0.7548	Intermediate Similarity	NPD5978	Approved
0.7548	Intermediate Similarity	NPD5977	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1470	Approved
0.7482	Intermediate Similarity	NPD2797	Approved
0.7481	Intermediate Similarity	NPD3025	Approved
0.7481	Intermediate Similarity	NPD3024	Approved
0.7467	Intermediate Similarity	NPD7390	Discontinued
0.7466	Intermediate Similarity	NPD5405	Approved
0.7466	Intermediate Similarity	NPD6099	Approved
0.7466	Intermediate Similarity	NPD4476	Approved
0.7466	Intermediate Similarity	NPD4477	Approved
0.7466	Intermediate Similarity	NPD6100	Approved
0.7466	Intermediate Similarity	NPD5406	Approved
0.7466	Intermediate Similarity	NPD5404	Approved
0.7466	Intermediate Similarity	NPD5408	Approved
0.7465	Intermediate Similarity	NPD3268	Approved
0.7447	Intermediate Similarity	NPD6832	Phase 2
0.7436	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1243	Approved
0.7426	Intermediate Similarity	NPD3019	Approved
0.7424	Intermediate Similarity	NPD5283	Phase 1
0.7417	Intermediate Similarity	NPD2532	Approved
0.7417	Intermediate Similarity	NPD2534	Approved
0.7417	Intermediate Similarity	NPD2533	Approved
0.7417	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7177	Discontinued
0.7403	Intermediate Similarity	NPD6599	Discontinued
0.7403	Intermediate Similarity	NPD4380	Phase 2
0.7397	Intermediate Similarity	NPD4308	Phase 3
0.7372	Intermediate Similarity	NPD3026	Approved
0.7372	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3023	Approved
0.7365	Intermediate Similarity	NPD1549	Phase 2
0.7361	Intermediate Similarity	NPD3142	Approved
0.7361	Intermediate Similarity	NPD3140	Approved
0.7361	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD7411	Suspended
0.7353	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5327	Phase 3
0.7333	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6280	Approved
0.7308	Intermediate Similarity	NPD6279	Approved
0.7303	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4097	Suspended
0.7259	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9494	Approved
0.7244	Intermediate Similarity	NPD6873	Phase 2
0.7237	Intermediate Similarity	NPD6799	Approved
0.7235	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7075	Discontinued
0.7226	Intermediate Similarity	NPD5585	Approved
0.7222	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3887	Approved
0.7214	Intermediate Similarity	NPD1669	Approved
0.7214	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD920	Approved
0.7197	Intermediate Similarity	NPD6801	Discontinued
0.7197	Intermediate Similarity	NPD1934	Approved
0.7195	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.719	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4624	Approved
0.7181	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2353	Approved
0.7179	Intermediate Similarity	NPD7028	Phase 2
0.7178	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7768	Phase 2
0.717	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3134	Approved
0.7153	Intermediate Similarity	NPD7008	Discontinued
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD2801	Approved
0.7143	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6651	Approved
0.7133	Intermediate Similarity	NPD2897	Discontinued
0.7125	Intermediate Similarity	NPD3749	Approved
0.7124	Intermediate Similarity	NPD1511	Approved
0.7124	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4140	Approved
0.7121	Intermediate Similarity	NPD5451	Approved
0.7117	Intermediate Similarity	NPD3926	Phase 2
0.7115	Intermediate Similarity	NPD2649	Approved
0.7115	Intermediate Similarity	NPD2651	Approved
0.7113	Intermediate Similarity	NPD1164	Approved
0.7111	Intermediate Similarity	NPD5951	Approved
0.7107	Intermediate Similarity	NPD3817	Phase 2
0.7103	Intermediate Similarity	NPD6798	Discontinued
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7427	Discontinued
0.709	Intermediate Similarity	NPD7635	Approved
0.709	Intermediate Similarity	NPD5535	Approved
0.7089	Intermediate Similarity	NPD7577	Discontinued
0.7081	Intermediate Similarity	NPD919	Approved
0.7075	Intermediate Similarity	NPD4622	Approved
0.7075	Intermediate Similarity	NPD4618	Approved
0.7075	Intermediate Similarity	NPD1933	Approved
0.7063	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD709	Approved
0.7055	Intermediate Similarity	NPD7229	Phase 3
0.705	Intermediate Similarity	NPD1778	Approved
0.7037	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1512	Approved
0.7032	Intermediate Similarity	NPD5049	Phase 3
0.7029	Intermediate Similarity	NPD9545	Approved
0.7024	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD2296	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6994	Remote Similarity	NPD1247	Approved
0.6993	Remote Similarity	NPD1203	Approved
0.6993	Remote Similarity	NPD2354	Approved
0.6987	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3869	Phase 3
0.6987	Remote Similarity	NPD3873	Phase 3
0.6986	Remote Similarity	NPD411	Approved
0.698	Remote Similarity	NPD5688	Approved
0.698	Remote Similarity	NPD5689	Approved
0.6974	Remote Similarity	NPD2800	Approved
0.6974	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4359	Approved
0.697	Remote Similarity	NPD2342	Discontinued
0.6957	Remote Similarity	NPD7644	Approved
0.6957	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6808	Phase 2
0.6948	Remote Similarity	NPD3300	Phase 2
0.6944	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8313	Approved
0.6941	Remote Similarity	NPD8312	Approved
0.6941	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6663	Approved
0.6937	Remote Similarity	NPD1465	Phase 2

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