NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	360.456
LogP:	2.339
LogD:	2.203
LogS:	-4.606
# Rotatable Bonds:	4
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	3.286
Fsp3:	0.3
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:	-5.019
MDCK Permeability:	9.444618626730517e-06
Pgp-inhibitor:	0.025
Pgp-substrate:	0.263
Human Intestinal Absorption (HIA):	0.756
20% Bioavailability (F20%):	0.311
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	91.83647918701172%
Volume Distribution (VD):	0.795
Pgp-substrate:	4.011034965515137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.806
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.35
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.619
CYP2D6-inhibitor:	0.427
CYP2D6-substrate:	0.404
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	9.545
Half-life (T1/2):	0.412

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.9
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.134
Carcinogencity:	0.862
Eye Corrosion:	0.003
Eye Irritation:	0.092
Respiratory Toxicity:	0.102

Download Data

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

Natural Product: NPC478019

Natural Product ID:	NPC478019
*Common Name:**	(3R)-3,7-dihydroxy-8-[2-(hydroxymethyl)-3-methoxybenzoyl]-3-methyl-2,4-dihydronaphthalen-1-one
IUPAC Name:	(3R)-3,7-dihydroxy-8-[2-(hydroxymethyl)-3-methoxybenzoyl]-3-methyl-2,4-dihydronaphthalen-1-one
Synonyms:
Standard InCHIKey:	LUFFCSDTJVVITF-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-20(25)8-11-6-7-14(22)18(17(11)15(23)9-20)19(24)12-4-3-5-16(26-2)13(12)10-21/h3-7,21-22,25H,8-10H2,1-2H3/t20-/m1/s1
SMILES:	C[C@]1(CC2=C(C(=O)C1)C(=C(C=C2)O)C(=O)C3=C(C(=CC=C3)OC)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122195139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO33526	Streptomyces sp. CB01913	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26335269]

☑ 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	5
MIC	3

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT399	Cell Line	SF-295	Homo sapiens	IC50	>	100000	nM	PMID[26335269]
NPT405	Cell Line	NCI-H226	Homo sapiens	IC50	>	100000	nM	PMID[26335269]
NPT374	Cell Line	SF-539	Homo sapiens	IC50	>	100000	nM	PMID[26335269]
NPT387	Cell Line	M14	Homo sapiens	IC50	>	100000	nM	PMID[26335269]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	>	100000	nM	PMID[26335269]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	PMID[26335269]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	85	ug/ml	PMID[26335269]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	93	ug/ml	PMID[26335269]

☑ 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 NPC478019 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	356
0.1-0.2	1548
0.2-0.3	3332
0.3-0.4	8782
0.4-0.5	9776
0.5-0.6	3606
0.6-0.7	6586
0.7-0.8	6471
0.8-0.85	1836
0.85-0.9	368
0.9-0.95	35
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC290954
0.9379	High Similarity	NPC255641
0.9315	High Similarity	NPC470569
0.9252	High Similarity	NPC164912
0.9247	High Similarity	NPC470568
0.9247	High Similarity	NPC147735
0.9236	High Similarity	NPC300540
0.9184	High Similarity	NPC118427
0.9172	High Similarity	NPC478018
0.9172	High Similarity	NPC190648
0.9172	High Similarity	NPC118027
0.9172	High Similarity	NPC126767
0.9172	High Similarity	NPC312929
0.9172	High Similarity	NPC245584
0.9172	High Similarity	NPC56433
0.9172	High Similarity	NPC289042
0.9161	High Similarity	NPC53016
0.9122	High Similarity	NPC40356
0.9122	High Similarity	NPC154683
0.9097	High Similarity	NPC19896
0.9097	High Similarity	NPC193703
0.9097	High Similarity	NPC21599
0.9091	High Similarity	NPC69755
0.9073	High Similarity	NPC324736
0.906	High Similarity	NPC208806
0.9048	High Similarity	NPC329933
0.9041	High Similarity	NPC34802
0.9034	High Similarity	NPC34482
0.9034	High Similarity	NPC49282
0.9028	High Similarity	NPC66593
0.9014	High Similarity	NPC1268
0.9013	High Similarity	NPC284495
0.9	High Similarity	NPC226656
0.9	High Similarity	NPC66508
0.8986	High Similarity	NPC294646
0.8973	High Similarity	NPC470570
0.8966	High Similarity	NPC48762
0.8958	High Similarity	NPC49108
0.8936	High Similarity	NPC141934
0.8926	High Similarity	NPC46882
0.8926	High Similarity	NPC149526
0.8926	High Similarity	NPC132990
0.8926	High Similarity	NPC474417
0.8926	High Similarity	NPC478148
0.8919	High Similarity	NPC10027
0.8919	High Similarity	NPC65775
0.8904	High Similarity	NPC73416
0.8904	High Similarity	NPC160777
0.8897	High Similarity	NPC167663
0.8889	High Similarity	NPC124365
0.8881	High Similarity	NPC470407
0.8867	High Similarity	NPC470340
0.8867	High Similarity	NPC470338
0.8867	High Similarity	NPC268992
0.8867	High Similarity	NPC470337
0.8867	High Similarity	NPC51824
0.8867	High Similarity	NPC113608
0.8867	High Similarity	NPC180944
0.8857	High Similarity	NPC52407
0.8849	High Similarity	NPC93015
0.8836	High Similarity	NPC475201
0.8828	High Similarity	NPC268204
0.8828	High Similarity	NPC52789
0.8828	High Similarity	NPC55832
0.8828	High Similarity	NPC26051
0.8828	High Similarity	NPC135524
0.8819	High Similarity	NPC472366
0.8816	High Similarity	NPC478223
0.8808	High Similarity	NPC329844
0.8808	High Similarity	NPC155686
0.8808	High Similarity	NPC169990
0.8808	High Similarity	NPC107109
0.8808	High Similarity	NPC210942
0.88	High Similarity	NPC302783
0.88	High Similarity	NPC144283
0.88	High Similarity	NPC473201
0.8777	High Similarity	NPC31799
0.8776	High Similarity	NPC476055
0.8767	High Similarity	NPC84266
0.8767	High Similarity	NPC163948
0.8767	High Similarity	NPC3732
0.8759	High Similarity	NPC259166
0.8759	High Similarity	NPC101366
0.8759	High Similarity	NPC204985
0.8759	High Similarity	NPC144118
0.8759	High Similarity	NPC80962
0.8759	High Similarity	NPC204045
0.8759	High Similarity	NPC326109
0.8759	High Similarity	NPC48624
0.8759	High Similarity	NPC215311
0.8759	High Similarity	NPC172250
0.8759	High Similarity	NPC305845
0.8759	High Similarity	NPC219917
0.8759	High Similarity	NPC253822
0.8759	High Similarity	NPC213659
0.8758	High Similarity	NPC37543
0.8758	High Similarity	NPC199463
0.8758	High Similarity	NPC178976
0.875	High Similarity	NPC138099
0.875	High Similarity	NPC477408
0.875	High Similarity	NPC21350
0.875	High Similarity	NPC68727
0.875	High Similarity	NPC223336
0.875	High Similarity	NPC242994
0.8742	High Similarity	NPC312338
0.8742	High Similarity	NPC149889
0.8733	High Similarity	NPC225854
0.8733	High Similarity	NPC202595
0.8733	High Similarity	NPC205766
0.8732	High Similarity	NPC22222
0.8732	High Similarity	NPC281513
0.8725	High Similarity	NPC2569
0.8725	High Similarity	NPC172329
0.8716	High Similarity	NPC163846
0.8716	High Similarity	NPC225173
0.8707	High Similarity	NPC51887
0.8707	High Similarity	NPC476178
0.8707	High Similarity	NPC117836
0.8707	High Similarity	NPC475705
0.8705	High Similarity	NPC57552
0.8699	High Similarity	NPC126534
0.8699	High Similarity	NPC470087
0.8699	High Similarity	NPC182255
0.8699	High Similarity	NPC321980
0.8699	High Similarity	NPC94076
0.8699	High Similarity	NPC469404
0.8699	High Similarity	NPC40118
0.8699	High Similarity	NPC232021
0.8693	High Similarity	NPC279605
0.8693	High Similarity	NPC5379
0.8693	High Similarity	NPC77807
0.8693	High Similarity	NPC14561
0.869	High Similarity	NPC169452
0.869	High Similarity	NPC181560
0.869	High Similarity	NPC283429
0.869	High Similarity	NPC477956
0.869	High Similarity	NPC109232
0.869	High Similarity	NPC470211
0.869	High Similarity	NPC295384
0.8684	High Similarity	NPC214632
0.8684	High Similarity	NPC474000
0.8684	High Similarity	NPC93552
0.8684	High Similarity	NPC135522
0.8684	High Similarity	NPC475770
0.8681	High Similarity	NPC4214
0.8681	High Similarity	NPC472419
0.8681	High Similarity	NPC317119
0.8675	High Similarity	NPC230848
0.8675	High Similarity	NPC72958
0.8675	High Similarity	NPC232645
0.8671	High Similarity	NPC105414
0.8671	High Similarity	NPC324522
0.8671	High Similarity	NPC131039
0.8671	High Similarity	NPC470341
0.8671	High Similarity	NPC472058
0.8671	High Similarity	NPC234497
0.8667	High Similarity	NPC80370
0.8667	High Similarity	NPC288036
0.8667	High Similarity	NPC65589
0.8667	High Similarity	NPC100985
0.8667	High Similarity	NPC97028
0.8667	High Similarity	NPC158338
0.8667	High Similarity	NPC97029
0.8662	High Similarity	NPC1249
0.8658	High Similarity	NPC222298
0.8658	High Similarity	NPC51070
0.8658	High Similarity	NPC125801
0.8654	High Similarity	NPC478229
0.8649	High Similarity	NPC311741
0.8649	High Similarity	NPC234629
0.8645	High Similarity	NPC472618
0.8645	High Similarity	NPC470810
0.8645	High Similarity	NPC470342
0.8645	High Similarity	NPC472060
0.8645	High Similarity	NPC472052
0.8643	High Similarity	NPC136588
0.8643	High Similarity	NPC199253
0.8639	High Similarity	NPC148545
0.8639	High Similarity	NPC297600
0.8636	High Similarity	NPC67197
0.8636	High Similarity	NPC263483
0.8636	High Similarity	NPC44199
0.863	High Similarity	NPC265178
0.863	High Similarity	NPC11056
0.8627	High Similarity	NPC318270
0.8623	High Similarity	NPC177925
0.8621	High Similarity	NPC190457
0.8621	High Similarity	NPC278323
0.8621	High Similarity	NPC279668
0.8621	High Similarity	NPC90665
0.8621	High Similarity	NPC251681
0.8621	High Similarity	NPC472368
0.8621	High Similarity	NPC55162
0.8621	High Similarity	NPC309154
0.8621	High Similarity	NPC12175
0.8621	High Similarity	NPC243528
0.8618	High Similarity	NPC87708
0.8618	High Similarity	NPC474843
0.8611	High Similarity	NPC472364
0.8611	High Similarity	NPC476333

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 NPC478019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	985
0.2-0.3	1367
0.3-0.4	2483
0.4-0.5	2063
0.5-0.6	1172
0.6-0.7	537
0.7-0.8	196
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8611	High Similarity	NPD2935	Discontinued
0.8542	High Similarity	NPD1509	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7819	Suspended
0.8418	Intermediate Similarity	NPD6232	Discontinued
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8375	Intermediate Similarity	NPD7473	Discontinued
0.8301	Intermediate Similarity	NPD3226	Approved
0.8299	Intermediate Similarity	NPD2346	Discontinued
0.8286	Intermediate Similarity	NPD1470	Approved
0.8278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1607	Approved
0.8264	Intermediate Similarity	NPD1240	Approved
0.8247	Intermediate Similarity	NPD4380	Phase 2
0.8239	Intermediate Similarity	NPD6959	Discontinued
0.8205	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2344	Approved
0.8163	Intermediate Similarity	NPD2799	Discontinued
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD2534	Approved
0.8153	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD7411	Suspended
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7003	Approved
0.8012	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1201	Approved
0.7987	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD5404	Approved
0.7987	Intermediate Similarity	NPD5408	Approved
0.7987	Intermediate Similarity	NPD5405	Approved
0.7987	Intermediate Similarity	NPD5406	Approved
0.7974	Intermediate Similarity	NPD7390	Discontinued
0.7972	Intermediate Similarity	NPD2798	Approved
0.7961	Intermediate Similarity	NPD2309	Approved
0.7949	Intermediate Similarity	NPD7458	Discontinued
0.7937	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD7075	Discontinued
0.7911	Intermediate Similarity	NPD1934	Approved
0.7877	Intermediate Similarity	NPD2313	Discontinued
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7875	Intermediate Similarity	NPD3882	Suspended
0.7866	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2801	Approved
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7817	Intermediate Similarity	NPD3972	Approved
0.7815	Intermediate Similarity	NPD1471	Phase 3
0.7799	Intermediate Similarity	NPD6801	Discontinued
0.7786	Intermediate Similarity	NPD1651	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6166	Phase 2
0.7758	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6273	Approved
0.7742	Intermediate Similarity	NPD1511	Approved
0.773	Intermediate Similarity	NPD5494	Approved
0.7716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1876	Approved
0.7708	Intermediate Similarity	NPD1283	Approved
0.7698	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6779	Approved
0.7697	Intermediate Similarity	NPD6778	Approved
0.7697	Intermediate Similarity	NPD6777	Approved
0.7697	Intermediate Similarity	NPD6776	Approved
0.7697	Intermediate Similarity	NPD6780	Approved
0.7697	Intermediate Similarity	NPD6782	Approved
0.7697	Intermediate Similarity	NPD6781	Approved
0.7673	Intermediate Similarity	NPD6599	Discontinued
0.7665	Intermediate Similarity	NPD3818	Discontinued
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7655	Intermediate Similarity	NPD1203	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD1512	Approved
0.7635	Intermediate Similarity	NPD3764	Approved
0.7628	Intermediate Similarity	NPD6799	Approved
0.7622	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.7606	Intermediate Similarity	NPD4626	Approved
0.7602	Intermediate Similarity	NPD8312	Approved
0.7602	Intermediate Similarity	NPD8313	Approved
0.7597	Intermediate Similarity	NPD2800	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD8150	Discontinued
0.7569	Intermediate Similarity	NPD7696	Phase 3
0.7569	Intermediate Similarity	NPD7698	Approved
0.7569	Intermediate Similarity	NPD7697	Approved
0.7569	Intermediate Similarity	NPD7435	Discontinued
0.7566	Intermediate Similarity	NPD4308	Phase 3
0.755	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1164	Approved
0.753	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD5710	Approved
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7527	Intermediate Similarity	NPD7871	Phase 2
0.7527	Intermediate Similarity	NPD7870	Phase 2
0.7517	Intermediate Similarity	NPD3268	Approved
0.7517	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1281	Approved
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3751	Discontinued
0.7451	Intermediate Similarity	NPD3748	Approved
0.7448	Intermediate Similarity	NPD9717	Approved
0.7447	Intermediate Similarity	NPD9493	Approved
0.7442	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9494	Approved
0.7423	Intermediate Similarity	NPD5760	Phase 2
0.7423	Intermediate Similarity	NPD5761	Phase 2
0.7417	Intermediate Similarity	NPD2979	Phase 3
0.7417	Intermediate Similarity	NPD4060	Phase 1
0.7416	Intermediate Similarity	NPD6534	Approved
0.7416	Intermediate Similarity	NPD6535	Approved
0.7415	Intermediate Similarity	NPD2797	Approved
0.7413	Intermediate Similarity	NPD5691	Approved
0.7412	Intermediate Similarity	NPD7054	Approved
0.7405	Intermediate Similarity	NPD7701	Phase 2
0.74	Intermediate Similarity	NPD411	Approved
0.7378	Intermediate Similarity	NPD5402	Approved
0.7378	Intermediate Similarity	NPD2296	Approved
0.7375	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD7472	Approved
0.7362	Intermediate Similarity	NPD6844	Discontinued
0.7362	Intermediate Similarity	NPD37	Approved
0.7361	Intermediate Similarity	NPD3019	Approved
0.7353	Intermediate Similarity	NPD7177	Discontinued
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7326	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6797	Phase 2
0.7326	Intermediate Similarity	NPD7874	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6823	Phase 2
0.731	Intermediate Similarity	NPD7286	Phase 2
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4307	Phase 2
0.7293	Intermediate Similarity	NPD7700	Phase 2
0.7293	Intermediate Similarity	NPD7699	Phase 2
0.7292	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4476	Approved
0.729	Intermediate Similarity	NPD4477	Approved
0.729	Intermediate Similarity	NPD2438	Suspended
0.7287	Intermediate Similarity	NPD7801	Approved
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7251	Discontinued
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6213	Phase 3
0.7263	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6212	Phase 3
0.7261	Intermediate Similarity	NPD1243	Approved
0.7256	Intermediate Similarity	NPD6279	Approved
0.7256	Intermediate Similarity	NPD6280	Approved
0.725	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2932	Approved
0.7241	Intermediate Similarity	NPD7808	Phase 3
0.7241	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3300	Phase 2
0.7233	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4965	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7216	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD8166	Discontinued
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7208	Intermediate Similarity	NPD4097	Suspended
0.7197	Intermediate Similarity	NPD2424	Discontinued
0.7188	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3266	Approved
0.7181	Intermediate Similarity	NPD3267	Approved
0.7179	Intermediate Similarity	NPD2531	Phase 2
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD1247	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