NPASS Compound

Structure

NPC473369 OpenBabel07101718332D 21 23 0 0 1 0 0 0 0 0999 V2000 4.6557 2.5887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4844 1.0966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3650 1.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8280 3.8585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2778 1.9910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9773 0.1101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.8672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9000 1.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1393 1.8921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4621 0.2904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5548 3.0355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7615 1.2944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8672 -0.8672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1575 -0.4050 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1607 0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8672 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2946 2.8606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1066 0.4988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 1.7393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3401 -0.1570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 10 13 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 13 17 1 1 0 0 0 14 15 1 0 0 0 0 14 17 1 1 0 0 0 15 6 1 1 0 0 0 15 21 1 0 0 0 0 16 17 1 1 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	301.534
LogP:	2.891
LogD:	2.441
LogS:	-4.108
# Rotatable Bonds:	5
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	5.894
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.916
MDCK Permeability:	2.7049778509535827e-05
Pgp-inhibitor:	0.471
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.222
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	75.4808578491211%
Volume Distribution (VD):	1.406
Pgp-substrate:	25.268957138061523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.379
CYP1A2-substrate:	0.617
CYP2C19-inhibitor:	0.559
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.412
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	3.073
Half-life (T1/2):	0.654

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.693
Drug-inuced Liver Injury (DILI):	0.54
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.611
Carcinogencity:	0.396
Eye Corrosion:	0.882
Eye Irritation:	0.907
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC473369

Natural Product ID:	NPC473369
*Common Name:**	Clavigerin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BKOKHVZCDIZBDJ-ALYAQQCSSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-9(2)5-12(19)8-17-13-7-14(17)15(6-10(13)3)21-16(17)20-11(4)18/h5-6,13-16H,7-8H2,1-4H3/t13-,14+,15-,16+,17+/m1/s1
SMILES:	CC1=CC2C3CC1C3(C(O2)OC(=O)C)CC(=O)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403495
PubChem CID:	10870006
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO25378	Lepidolaena clavigera	Species	Lepidolaenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18232639]
NPO25378	Lepidolaena clavigera	Species	Lepidolaenaceae	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	9

Activity Type	# Activity
NON-MOLECULAR	3
ORGANISM	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		Activity	=	-74.0	%	PMID[480190]
NPT21294	ORGANISM	Tineola bisselliella	Tineola bisselliella	Survival	=	27.0	%	PMID[480190]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	-78.0	%	PMID[480190]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	-79.0	%	PMID[480190]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	-34.0	%	PMID[480190]
NPT2	Others	Unspecified		Survival	=	95.0	%	PMID[480190]
NPT2	Others	Unspecified		Survival	=	98.0	%	PMID[480190]
NPT27	Others	Unspecified		IZ	=	1.0	mm	PMID[480190]

☑ 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 NPC473369 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	230
0.1-0.2	1473
0.2-0.3	6011
0.3-0.4	13471
0.4-0.5	10167
0.5-0.6	7005
0.6-0.7	3865
0.7-0.8	463
0.8-0.85	8
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC471571
0.9462	High Similarity	NPC473384
0.9432	High Similarity	NPC174765
0.8804	High Similarity	NPC65513
0.8673	High Similarity	NPC471365
0.8673	High Similarity	NPC471364
0.8673	High Similarity	NPC132395
0.8632	High Similarity	NPC112654
0.8351	Intermediate Similarity	NPC204054
0.8351	Intermediate Similarity	NPC257726
0.8333	Intermediate Similarity	NPC193198
0.828	Intermediate Similarity	NPC226863
0.8261	Intermediate Similarity	NPC220478
0.8252	Intermediate Similarity	NPC112457
0.8242	Intermediate Similarity	NPC71626
0.8211	Intermediate Similarity	NPC141831
0.8152	Intermediate Similarity	NPC300985
0.8152	Intermediate Similarity	NPC189311
0.8125	Intermediate Similarity	NPC166346
0.8105	Intermediate Similarity	NPC232426
0.8105	Intermediate Similarity	NPC152467
0.8105	Intermediate Similarity	NPC469595
0.8105	Intermediate Similarity	NPC220454
0.8105	Intermediate Similarity	NPC212679
0.8105	Intermediate Similarity	NPC281942
0.8085	Intermediate Similarity	NPC477128
0.8061	Intermediate Similarity	NPC311166
0.8041	Intermediate Similarity	NPC477130
0.8041	Intermediate Similarity	NPC477129
0.8021	Intermediate Similarity	NPC179517
0.8021	Intermediate Similarity	NPC165904
0.802	Intermediate Similarity	NPC134077
0.8	Intermediate Similarity	NPC284561
0.7978	Intermediate Similarity	NPC471220
0.7961	Intermediate Similarity	NPC127790
0.7957	Intermediate Similarity	NPC110405
0.7957	Intermediate Similarity	NPC472442
0.7944	Intermediate Similarity	NPC157441
0.7938	Intermediate Similarity	NPC475657
0.7935	Intermediate Similarity	NPC22611
0.7935	Intermediate Similarity	NPC472440
0.7921	Intermediate Similarity	NPC63249
0.7921	Intermediate Similarity	NPC472643
0.7917	Intermediate Similarity	NPC469372
0.79	Intermediate Similarity	NPC176845
0.7895	Intermediate Similarity	NPC215831
0.7895	Intermediate Similarity	NPC196407
0.7857	Intermediate Similarity	NPC474554
0.7857	Intermediate Similarity	NPC88507
0.785	Intermediate Similarity	NPC194951
0.785	Intermediate Similarity	NPC12046
0.7849	Intermediate Similarity	NPC149869
0.7849	Intermediate Similarity	NPC474359
0.7835	Intermediate Similarity	NPC284185
0.7822	Intermediate Similarity	NPC472644
0.7812	Intermediate Similarity	NPC73995
0.7812	Intermediate Similarity	NPC5509
0.7812	Intermediate Similarity	NPC293044
0.7802	Intermediate Similarity	NPC195424
0.78	Intermediate Similarity	NPC69385
0.78	Intermediate Similarity	NPC474343
0.78	Intermediate Similarity	NPC84335
0.78	Intermediate Similarity	NPC476768
0.78	Intermediate Similarity	NPC38530
0.78	Intermediate Similarity	NPC76266
0.7789	Intermediate Similarity	NPC312561
0.7767	Intermediate Similarity	NPC254202
0.7766	Intermediate Similarity	NPC177932
0.7755	Intermediate Similarity	NPC476597
0.7755	Intermediate Similarity	NPC476598
0.7732	Intermediate Similarity	NPC471818
0.7732	Intermediate Similarity	NPC477782
0.7732	Intermediate Similarity	NPC253144
0.7723	Intermediate Similarity	NPC473154
0.7723	Intermediate Similarity	NPC23364
0.7723	Intermediate Similarity	NPC222011
0.7717	Intermediate Similarity	NPC475665
0.7717	Intermediate Similarity	NPC149237
0.77	Intermediate Similarity	NPC319692
0.77	Intermediate Similarity	NPC17578
0.77	Intermediate Similarity	NPC240673
0.77	Intermediate Similarity	NPC325960
0.7692	Intermediate Similarity	NPC469690
0.7692	Intermediate Similarity	NPC119493
0.7692	Intermediate Similarity	NPC469620
0.7685	Intermediate Similarity	NPC222834
0.7677	Intermediate Similarity	NPC476415
0.7677	Intermediate Similarity	NPC470697
0.7677	Intermediate Similarity	NPC148463
0.7677	Intermediate Similarity	NPC53685
0.7677	Intermediate Similarity	NPC475572
0.7677	Intermediate Similarity	NPC476596
0.7667	Intermediate Similarity	NPC187568
0.7667	Intermediate Similarity	NPC41780
0.766	Intermediate Similarity	NPC30486
0.766	Intermediate Similarity	NPC159635
0.7653	Intermediate Similarity	NPC123177
0.7653	Intermediate Similarity	NPC70595
0.7653	Intermediate Similarity	NPC477783
0.7653	Intermediate Similarity	NPC150978
0.7653	Intermediate Similarity	NPC74103
0.7647	Intermediate Similarity	NPC470761
0.7647	Intermediate Similarity	NPC473219
0.7647	Intermediate Similarity	NPC469402
0.7647	Intermediate Similarity	NPC476274
0.7642	Intermediate Similarity	NPC473288
0.7634	Intermediate Similarity	NPC178676
0.7634	Intermediate Similarity	NPC200513
0.7634	Intermediate Similarity	NPC186276
0.7629	Intermediate Similarity	NPC470734
0.7629	Intermediate Similarity	NPC251528
0.7629	Intermediate Similarity	NPC168131
0.7624	Intermediate Similarity	NPC472188
0.7624	Intermediate Similarity	NPC475709
0.7619	Intermediate Similarity	NPC469401
0.7619	Intermediate Similarity	NPC469607
0.7619	Intermediate Similarity	NPC472645
0.76	Intermediate Similarity	NPC316215
0.76	Intermediate Similarity	NPC183012
0.7596	Intermediate Similarity	NPC151516
0.7582	Intermediate Similarity	NPC128276
0.7579	Intermediate Similarity	NPC474860
0.7579	Intermediate Similarity	NPC471300
0.7579	Intermediate Similarity	NPC78089
0.7579	Intermediate Similarity	NPC161957
0.7576	Intermediate Similarity	NPC470576
0.7573	Intermediate Similarity	NPC476240
0.7573	Intermediate Similarity	NPC476223
0.7573	Intermediate Similarity	NPC224720
0.7573	Intermediate Similarity	NPC310981
0.7568	Intermediate Similarity	NPC23046
0.7553	Intermediate Similarity	NPC469
0.7551	Intermediate Similarity	NPC8062
0.7549	Intermediate Similarity	NPC476800
0.7549	Intermediate Similarity	NPC472186
0.7549	Intermediate Similarity	NPC471366
0.7549	Intermediate Similarity	NPC318917
0.7527	Intermediate Similarity	NPC281949
0.7527	Intermediate Similarity	NPC25684
0.7527	Intermediate Similarity	NPC282293
0.7527	Intermediate Similarity	NPC301477
0.7526	Intermediate Similarity	NPC472302
0.7525	Intermediate Similarity	NPC470801
0.7525	Intermediate Similarity	NPC73858
0.7524	Intermediate Similarity	NPC189616
0.7524	Intermediate Similarity	NPC476763
0.7524	Intermediate Similarity	NPC476764
0.75	Intermediate Similarity	NPC107787
0.75	Intermediate Similarity	NPC471299
0.75	Intermediate Similarity	NPC235369
0.75	Intermediate Similarity	NPC235014
0.75	Intermediate Similarity	NPC474555
0.75	Intermediate Similarity	NPC84893
0.75	Intermediate Similarity	NPC244174
0.75	Intermediate Similarity	NPC476769
0.75	Intermediate Similarity	NPC474062
0.75	Intermediate Similarity	NPC250075
0.75	Intermediate Similarity	NPC253906
0.75	Intermediate Similarity	NPC118266
0.75	Intermediate Similarity	NPC38830
0.75	Intermediate Similarity	NPC31058
0.75	Intermediate Similarity	NPC469606
0.75	Intermediate Similarity	NPC273005
0.7477	Intermediate Similarity	NPC189075
0.7477	Intermediate Similarity	NPC275539
0.7477	Intermediate Similarity	NPC469844
0.7476	Intermediate Similarity	NPC472187
0.7476	Intermediate Similarity	NPC117685
0.7476	Intermediate Similarity	NPC476933
0.7476	Intermediate Similarity	NPC473204
0.7476	Intermediate Similarity	NPC473545
0.7475	Intermediate Similarity	NPC186363
0.7475	Intermediate Similarity	NPC49420
0.7475	Intermediate Similarity	NPC219874
0.7475	Intermediate Similarity	NPC233345
0.7475	Intermediate Similarity	NPC221282
0.7475	Intermediate Similarity	NPC474631
0.7474	Intermediate Similarity	NPC100391
0.7474	Intermediate Similarity	NPC475100
0.7474	Intermediate Similarity	NPC469569
0.7473	Intermediate Similarity	NPC57744
0.7473	Intermediate Similarity	NPC316500
0.7456	Intermediate Similarity	NPC204731
0.7453	Intermediate Similarity	NPC476761
0.7453	Intermediate Similarity	NPC476762
0.7453	Intermediate Similarity	NPC252296
0.7453	Intermediate Similarity	NPC476760
0.7451	Intermediate Similarity	NPC53844
0.7451	Intermediate Similarity	NPC226986
0.7449	Intermediate Similarity	NPC288699
0.7449	Intermediate Similarity	NPC173042
0.7447	Intermediate Similarity	NPC173609
0.7434	Intermediate Similarity	NPC475834
0.7434	Intermediate Similarity	NPC474179
0.7434	Intermediate Similarity	NPC158963
0.7431	Intermediate Similarity	NPC474750
0.7429	Intermediate Similarity	NPC476770
0.7429	Intermediate Similarity	NPC475321
0.7426	Intermediate Similarity	NPC472189
0.7426	Intermediate Similarity	NPC471362

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 NPC473369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2021
0.2-0.3	3961
0.3-0.4	2046
0.4-0.5	557
0.5-0.6	256
0.6-0.7	109
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
0.7766	Intermediate Similarity	NPD1694	Approved
0.7634	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7521	Approved
0.732	Intermediate Similarity	NPD6409	Approved
0.732	Intermediate Similarity	NPD5330	Approved
0.732	Intermediate Similarity	NPD7146	Approved
0.732	Intermediate Similarity	NPD7334	Approved
0.732	Intermediate Similarity	NPD6684	Approved
0.7315	Intermediate Similarity	NPD6686	Approved
0.7255	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5737	Approved
0.7172	Intermediate Similarity	NPD6903	Approved
0.7172	Intermediate Similarity	NPD6672	Approved
0.7172	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7900	Approved
0.713	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD6399	Phase 3
0.6952	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6412	Phase 2
0.6903	Remote Similarity	NPD6882	Approved
0.69	Remote Similarity	NPD3573	Approved
0.6882	Remote Similarity	NPD8039	Approved
0.6863	Remote Similarity	NPD5207	Approved
0.6827	Remote Similarity	NPD7748	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6786	Remote Similarity	NPD6373	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6768	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6904	Approved
0.6765	Remote Similarity	NPD6673	Approved
0.6765	Remote Similarity	NPD6080	Approved
0.6762	Remote Similarity	NPD5695	Phase 3
0.6757	Remote Similarity	NPD5697	Approved
0.6757	Remote Similarity	NPD5701	Approved
0.6735	Remote Similarity	NPD5209	Approved
0.6729	Remote Similarity	NPD5696	Approved
0.6729	Remote Similarity	NPD7638	Approved
0.6729	Remote Similarity	NPD4225	Approved
0.6699	Remote Similarity	NPD5692	Phase 3
0.6699	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6637	Remote Similarity	NPD6013	Approved
0.6637	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD5694	Approved
0.6635	Remote Similarity	NPD7515	Phase 2
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD6050	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6634	Remote Similarity	NPD3618	Phase 1
0.6613	Remote Similarity	NPD7319	Approved
0.6612	Remote Similarity	NPD8328	Phase 3
0.6609	Remote Similarity	NPD6053	Discontinued
0.6607	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6051	Approved
0.6602	Remote Similarity	NPD5328	Approved
0.66	Remote Similarity	NPD3666	Approved
0.66	Remote Similarity	NPD3665	Phase 1
0.66	Remote Similarity	NPD3133	Approved
0.6585	Remote Similarity	NPD8293	Discontinued
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6542	Remote Similarity	NPD4697	Phase 3
0.6535	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7736	Approved
0.6529	Remote Similarity	NPD6370	Approved
0.6525	Remote Similarity	NPD6009	Approved
0.6525	Remote Similarity	NPD7115	Discovery
0.6522	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6847	Approved
0.6481	Remote Similarity	NPD4755	Approved
0.6476	Remote Similarity	NPD6411	Approved
0.6476	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD6098	Approved
0.6466	Remote Similarity	NPD8297	Approved
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD8513	Phase 3
0.6442	Remote Similarity	NPD1695	Approved
0.6436	Remote Similarity	NPD3668	Phase 3
0.6435	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7492	Approved
0.6415	Remote Similarity	NPD5779	Approved
0.6415	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD3667	Approved
0.6396	Remote Similarity	NPD5211	Phase 2
0.6389	Remote Similarity	NPD5222	Approved
0.6389	Remote Similarity	NPD5221	Approved
0.6389	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6698	Approved
0.6381	Remote Similarity	NPD46	Approved
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD6059	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6355	Remote Similarity	NPD5282	Discontinued
0.6348	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6052	Approved
0.633	Remote Similarity	NPD5173	Approved
0.6327	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6311	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4519	Discontinued
0.6311	Remote Similarity	NPD4623	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD5279	Phase 3
0.6311	Remote Similarity	NPD5786	Approved
0.6306	Remote Similarity	NPD5223	Approved
0.6303	Remote Similarity	NPD6274	Approved
0.6296	Remote Similarity	NPD5654	Approved
0.6293	Remote Similarity	NPD6371	Approved
0.6286	Remote Similarity	NPD4753	Phase 2
0.6286	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6101	Approved
0.6283	Remote Similarity	NPD5141	Approved
0.6275	Remote Similarity	NPD4786	Approved
0.6271	Remote Similarity	NPD4632	Approved
0.6264	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD7732	Phase 3
0.6238	Remote Similarity	NPD4223	Phase 3
0.6238	Remote Similarity	NPD4221	Approved
0.6214	Remote Similarity	NPD5363	Approved
0.6214	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6067	Discontinued
0.62	Remote Similarity	NPD5368	Approved
0.62	Remote Similarity	NPD4695	Discontinued
0.6198	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD6314	Approved
0.6198	Remote Similarity	NPD7327	Approved
0.6198	Remote Similarity	NPD6313	Approved
0.6198	Remote Similarity	NPD7328	Approved
0.6195	Remote Similarity	NPD4754	Approved
0.6195	Remote Similarity	NPD5174	Approved
0.6195	Remote Similarity	NPD5175	Approved
0.6182	Remote Similarity	NPD5959	Approved
0.6179	Remote Similarity	NPD7503	Approved
0.6174	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6914	Discontinued
0.617	Remote Similarity	NPD4137	Phase 3
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6167	Remote Similarity	NPD6868	Approved
0.6154	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7101	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD7516	Approved
0.6147	Remote Similarity	NPD4629	Approved
0.6147	Remote Similarity	NPD5210	Approved
0.6136	Remote Similarity	NPD287	Approved
0.6134	Remote Similarity	NPD8133	Approved
0.6132	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4197	Approved
0.6116	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7632	Discontinued
0.6105	Remote Similarity	NPD4747	Approved
0.6105	Remote Similarity	NPD4691	Approved
0.6102	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8294	Approved
0.6098	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD8377	Approved
0.6087	Remote Similarity	NPD4767	Approved
0.6087	Remote Similarity	NPD4768	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