NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	464.24
Volume:	460.586
LogP:	2.852
LogD:	3.011
LogS:	-4.517
# Rotatable Bonds:	6
TPSA:	89.52
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	6.229
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.067
MDCK Permeability:	3.425622344366275e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.179

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	80.22821807861328%
Volume Distribution (VD):	1.745
Pgp-substrate:	4.981066703796387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.79

ADMET: Excretion

Clearance (CL):	8.428
Half-life (T1/2):	0.178

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.665
AMES Toxicity:	0.979
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.295
Carcinogencity:	0.92
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.579

Download Data

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

Natural Product: NPC476762

Natural Product ID:	NPC476762
*Common Name:**	methyl (2S,4R,9R,10S,13R,15S)-4-ethoxy-15,17-dimethoxy-9-methyl-6-oxo-5,16-dioxapentacyclo[12.3.3.01,13.02,10.04,8]icos-7-ene-14-carboxylate
IUPAC Name:	methyl (2S,4R,9R,10S,13R,15S)-4-ethoxy-15,17-dimethoxy-9-methyl-6-oxo-5,16-dioxapentacyclo[12.3.3.01,13.02,10.04,8]icos-7-ene-14-carboxylate
Synonyms:
Standard InCHIKey:	DWKJKUNLLVLOGB-HWLKAPJPSA-N
Standard InCHI:	InChI=1S/C25H36O8/c1-6-31-25-13-17-15(14(2)16(25)12-19(26)33-25)8-9-18-23(17)10-7-11-24(18,20(27)28-3)22(30-5)32-21(23)29-4/h12,14-15,17-18,21-22H,6-11,13H2,1-5H3/t14-,15+,17+,18-,21?,22+,23?,24?,25-/m1/s1
SMILES:	CCO[C@@]12C[C@H]3[C@@H](CC[C@@H]4C35CCCC4([C@H](OC5OC)OC)C(=O)OC)[C@H](C1=CC(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162818951
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	28400	nM	PMID[26398312]

☑ 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 NPC476762 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	272
0.1-0.2	1689
0.2-0.3	4884
0.3-0.4	9121
0.4-0.5	12628
0.5-0.6	7391
0.6-0.7	4633
0.7-0.8	1978
0.8-0.85	86
0.85-0.9	7
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476760
1.0	High Similarity	NPC476761
0.9897	High Similarity	NPC476763
0.9897	High Similarity	NPC476764
0.9505	High Similarity	NPC476759
0.9412	High Similarity	NPC476766
0.9216	High Similarity	NPC476765
0.8824	High Similarity	NPC476770
0.8776	High Similarity	NPC477722
0.8725	High Similarity	NPC476769
0.8716	High Similarity	NPC474483
0.8585	High Similarity	NPC112457
0.8529	High Similarity	NPC476767
0.8515	High Similarity	NPC476768
0.8505	High Similarity	NPC472666
0.8482	Intermediate Similarity	NPC476127
0.8482	Intermediate Similarity	NPC476150
0.8447	Intermediate Similarity	NPC477717
0.8411	Intermediate Similarity	NPC31522
0.8396	Intermediate Similarity	NPC475570
0.8362	Intermediate Similarity	NPC117702
0.8362	Intermediate Similarity	NPC469757
0.8362	Intermediate Similarity	NPC146456
0.8362	Intermediate Similarity	NPC471357
0.835	Intermediate Similarity	NPC477716
0.835	Intermediate Similarity	NPC477721
0.8319	Intermediate Similarity	NPC470312
0.8318	Intermediate Similarity	NPC90946
0.8318	Intermediate Similarity	NPC392
0.8318	Intermediate Similarity	NPC300614
0.8318	Intermediate Similarity	NPC177524
0.8318	Intermediate Similarity	NPC473483
0.8318	Intermediate Similarity	NPC219900
0.8273	Intermediate Similarity	NPC157441
0.8261	Intermediate Similarity	NPC27363
0.8246	Intermediate Similarity	NPC476204
0.8246	Intermediate Similarity	NPC170084
0.8235	Intermediate Similarity	NPC319692
0.8235	Intermediate Similarity	NPC325960
0.822	Intermediate Similarity	NPC471361
0.822	Intermediate Similarity	NPC251866
0.822	Intermediate Similarity	NPC197707
0.822	Intermediate Similarity	NPC89514
0.822	Intermediate Similarity	NPC17896
0.822	Intermediate Similarity	NPC284406
0.822	Intermediate Similarity	NPC70542
0.822	Intermediate Similarity	NPC86159
0.822	Intermediate Similarity	NPC9499
0.822	Intermediate Similarity	NPC471352
0.822	Intermediate Similarity	NPC219085
0.822	Intermediate Similarity	NPC471360
0.822	Intermediate Similarity	NPC469751
0.822	Intermediate Similarity	NPC471359
0.822	Intermediate Similarity	NPC469752
0.822	Intermediate Similarity	NPC471358
0.822	Intermediate Similarity	NPC6108
0.822	Intermediate Similarity	NPC469754
0.822	Intermediate Similarity	NPC469753
0.822	Intermediate Similarity	NPC469755
0.822	Intermediate Similarity	NPC10823
0.822	Intermediate Similarity	NPC180079
0.8182	Intermediate Similarity	NPC194951
0.8182	Intermediate Similarity	NPC12046
0.8158	Intermediate Similarity	NPC281840
0.8155	Intermediate Similarity	NPC477719
0.8155	Intermediate Similarity	NPC477718
0.8155	Intermediate Similarity	NPC204054
0.8155	Intermediate Similarity	NPC257726
0.8148	Intermediate Similarity	NPC325054
0.8148	Intermediate Similarity	NPC61411
0.8136	Intermediate Similarity	NPC311534
0.812	Intermediate Similarity	NPC250556
0.812	Intermediate Similarity	NPC469750
0.8119	Intermediate Similarity	NPC472303
0.8113	Intermediate Similarity	NPC254202
0.81	Intermediate Similarity	NPC8062
0.8095	Intermediate Similarity	NPC471075
0.8058	Intermediate Similarity	NPC8954
0.8058	Intermediate Similarity	NPC94905
0.8051	Intermediate Similarity	NPC329784
0.8051	Intermediate Similarity	NPC240070
0.8051	Intermediate Similarity	NPC471356
0.8051	Intermediate Similarity	NPC179412
0.8039	Intermediate Similarity	NPC84893
0.8036	Intermediate Similarity	NPC472274
0.8034	Intermediate Similarity	NPC318135
0.802	Intermediate Similarity	NPC289479
0.8017	Intermediate Similarity	NPC247190
0.8017	Intermediate Similarity	NPC469749
0.8017	Intermediate Similarity	NPC116075
0.8017	Intermediate Similarity	NPC146857
0.8017	Intermediate Similarity	NPC32793
0.8	Intermediate Similarity	NPC471413
0.8	Intermediate Similarity	NPC117685
0.7982	Intermediate Similarity	NPC239293
0.7981	Intermediate Similarity	NPC475709
0.7965	Intermediate Similarity	NPC471816
0.7951	Intermediate Similarity	NPC329636
0.7946	Intermediate Similarity	NPC264153
0.7944	Intermediate Similarity	NPC471364
0.7944	Intermediate Similarity	NPC132395
0.7944	Intermediate Similarity	NPC471365
0.7928	Intermediate Similarity	NPC270586
0.7928	Intermediate Similarity	NPC31839
0.7925	Intermediate Similarity	NPC471412
0.7917	Intermediate Similarity	NPC477196
0.7917	Intermediate Similarity	NPC276838
0.7917	Intermediate Similarity	NPC232785
0.7917	Intermediate Similarity	NPC140092
0.7917	Intermediate Similarity	NPC188234
0.7917	Intermediate Similarity	NPC329986
0.7917	Intermediate Similarity	NPC91
0.7917	Intermediate Similarity	NPC125077
0.7913	Intermediate Similarity	NPC122971
0.7905	Intermediate Similarity	NPC476800
0.7905	Intermediate Similarity	NPC471366
0.7905	Intermediate Similarity	NPC472186
0.7905	Intermediate Similarity	NPC318917
0.7899	Intermediate Similarity	NPC298841
0.7899	Intermediate Similarity	NPC470516
0.7895	Intermediate Similarity	NPC473405
0.7895	Intermediate Similarity	NPC473968
0.7886	Intermediate Similarity	NPC194716
0.7885	Intermediate Similarity	NPC194132
0.7885	Intermediate Similarity	NPC73858
0.7885	Intermediate Similarity	NPC29952
0.7876	Intermediate Similarity	NPC110861
0.787	Intermediate Similarity	NPC222161
0.7857	Intermediate Similarity	NPC222834
0.7857	Intermediate Similarity	NPC471967
0.7857	Intermediate Similarity	NPC1046
0.7857	Intermediate Similarity	NPC90952
0.7857	Intermediate Similarity	NPC48249
0.7857	Intermediate Similarity	NPC80843
0.7857	Intermediate Similarity	NPC4573
0.7857	Intermediate Similarity	NPC277769
0.7857	Intermediate Similarity	NPC71626
0.7851	Intermediate Similarity	NPC475167
0.7851	Intermediate Similarity	NPC477197
0.7851	Intermediate Similarity	NPC172374
0.7851	Intermediate Similarity	NPC159338
0.7851	Intermediate Similarity	NPC478064
0.7851	Intermediate Similarity	NPC475377
0.7851	Intermediate Similarity	NPC173435
0.7851	Intermediate Similarity	NPC300655
0.7851	Intermediate Similarity	NPC43589
0.7851	Intermediate Similarity	NPC16569
0.7851	Intermediate Similarity	NPC301639
0.7851	Intermediate Similarity	NPC478155
0.7851	Intermediate Similarity	NPC311178
0.7851	Intermediate Similarity	NPC45346
0.7851	Intermediate Similarity	NPC222951
0.7851	Intermediate Similarity	NPC264566
0.7851	Intermediate Similarity	NPC262796
0.7851	Intermediate Similarity	NPC253456
0.7851	Intermediate Similarity	NPC476074
0.7851	Intermediate Similarity	NPC329993
0.7851	Intermediate Similarity	NPC173347
0.7851	Intermediate Similarity	NPC134914
0.7851	Intermediate Similarity	NPC25998
0.7851	Intermediate Similarity	NPC478065
0.785	Intermediate Similarity	NPC134077
0.785	Intermediate Similarity	NPC162973
0.785	Intermediate Similarity	NPC121423
0.785	Intermediate Similarity	NPC165250
0.7845	Intermediate Similarity	NPC151616
0.7843	Intermediate Similarity	NPC474631
0.7838	Intermediate Similarity	NPC242611
0.7833	Intermediate Similarity	NPC477078
0.7833	Intermediate Similarity	NPC472269
0.7833	Intermediate Similarity	NPC475281
0.7833	Intermediate Similarity	NPC112492
0.7833	Intermediate Similarity	NPC472270
0.7833	Intermediate Similarity	NPC329923
0.7833	Intermediate Similarity	NPC477075
0.7833	Intermediate Similarity	NPC23020
0.7833	Intermediate Similarity	NPC477192
0.7833	Intermediate Similarity	NPC245094
0.7833	Intermediate Similarity	NPC477193
0.7833	Intermediate Similarity	NPC472268
0.7833	Intermediate Similarity	NPC477191
0.7833	Intermediate Similarity	NPC477194
0.7833	Intermediate Similarity	NPC476859
0.783	Intermediate Similarity	NPC477720
0.783	Intermediate Similarity	NPC473219
0.783	Intermediate Similarity	NPC475156
0.783	Intermediate Similarity	NPC472187
0.783	Intermediate Similarity	NPC473204
0.783	Intermediate Similarity	NPC470761
0.783	Intermediate Similarity	NPC473576
0.783	Intermediate Similarity	NPC473545
0.7826	Intermediate Similarity	NPC473828
0.7826	Intermediate Similarity	NPC473617
0.7826	Intermediate Similarity	NPC471548
0.7823	Intermediate Similarity	NPC59288
0.7823	Intermediate Similarity	NPC329675
0.7818	Intermediate Similarity	NPC189075
0.7818	Intermediate Similarity	NPC275539
0.781	Intermediate Similarity	NPC100912
0.781	Intermediate Similarity	NPC472188

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 NPC476762 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1826
0.2-0.3	3860
0.3-0.4	2104
0.4-0.5	721
0.5-0.6	256
0.6-0.7	107
0.7-0.8	28
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8318	Intermediate Similarity	NPD6686	Approved
0.822	Intermediate Similarity	NPD7319	Approved
0.812	Intermediate Similarity	NPD7507	Approved
0.7736	Intermediate Similarity	NPD7638	Approved
0.7672	Intermediate Similarity	NPD7328	Approved
0.7672	Intermediate Similarity	NPD7327	Approved
0.7664	Intermediate Similarity	NPD7639	Approved
0.7664	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8328	Phase 3
0.7607	Intermediate Similarity	NPD7516	Approved
0.7542	Intermediate Similarity	NPD8377	Approved
0.7542	Intermediate Similarity	NPD8294	Approved
0.7479	Intermediate Similarity	NPD8380	Approved
0.7479	Intermediate Similarity	NPD8296	Approved
0.7479	Intermediate Similarity	NPD8335	Approved
0.7479	Intermediate Similarity	NPD8379	Approved
0.7479	Intermediate Similarity	NPD8378	Approved
0.7479	Intermediate Similarity	NPD8033	Approved
0.7478	Intermediate Similarity	NPD8133	Approved
0.7411	Intermediate Similarity	NPD6412	Phase 2
0.7288	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7736	Approved
0.7257	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7900	Approved
0.7196	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7748	Approved
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3573	Approved
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7632	Discontinued
0.7049	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD8513	Phase 3
0.7049	Intermediate Similarity	NPD8516	Approved
0.7049	Intermediate Similarity	NPD7503	Approved
0.7049	Intermediate Similarity	NPD8517	Approved
0.7048	Intermediate Similarity	NPD6672	Approved
0.7048	Intermediate Similarity	NPD5737	Approved
0.704	Intermediate Similarity	NPD8293	Discontinued
0.7019	Intermediate Similarity	NPD7521	Approved
0.7019	Intermediate Similarity	NPD7334	Approved
0.7019	Intermediate Similarity	NPD7146	Approved
0.7019	Intermediate Similarity	NPD6684	Approved
0.7019	Intermediate Similarity	NPD5330	Approved
0.7019	Intermediate Similarity	NPD6409	Approved
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD7902	Approved
0.6992	Remote Similarity	NPD6370	Approved
0.6983	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6882	Approved
0.6937	Remote Similarity	NPD4225	Approved
0.6887	Remote Similarity	NPD6903	Approved
0.688	Remote Similarity	NPD7492	Approved
0.687	Remote Similarity	NPD6008	Approved
0.6852	Remote Similarity	NPD5693	Phase 1
0.6829	Remote Similarity	NPD6054	Approved
0.6829	Remote Similarity	NPD6059	Approved
0.6825	Remote Similarity	NPD6616	Approved
0.6772	Remote Similarity	NPD7078	Approved
0.6762	Remote Similarity	NPD1694	Approved
0.6752	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6402	Approved
0.6724	Remote Similarity	NPD7128	Approved
0.6724	Remote Similarity	NPD5739	Approved
0.6724	Remote Similarity	NPD6675	Approved
0.6697	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD6084	Phase 2
0.6696	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6372	Approved
0.6695	Remote Similarity	NPD6373	Approved
0.6694	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.664	Remote Similarity	NPD6015	Approved
0.664	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD6399	Phase 3
0.6636	Remote Similarity	NPD5778	Approved
0.6636	Remote Similarity	NPD5779	Approved
0.6615	Remote Similarity	NPD6914	Discontinued
0.661	Remote Similarity	NPD6881	Approved
0.661	Remote Similarity	NPD6899	Approved
0.661	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD6698	Approved
0.6606	Remote Similarity	NPD46	Approved
0.6587	Remote Similarity	NPD5988	Approved
0.6585	Remote Similarity	NPD6009	Approved
0.6583	Remote Similarity	NPD6649	Approved
0.6583	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD8034	Phase 2
0.6545	Remote Similarity	NPD8035	Phase 2
0.6529	Remote Similarity	NPD8297	Approved
0.6529	Remote Similarity	NPD6053	Discontinued
0.6525	Remote Similarity	NPD5697	Approved
0.6525	Remote Similarity	NPD5701	Approved
0.6518	Remote Similarity	NPD5695	Phase 3
0.6514	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6101	Approved
0.6514	Remote Similarity	NPD6051	Approved
0.6514	Remote Similarity	NPD5328	Approved
0.6509	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7290	Approved
0.65	Remote Similarity	NPD7102	Approved
0.65	Remote Similarity	NPD6883	Approved
0.6491	Remote Similarity	NPD5696	Approved
0.6462	Remote Similarity	NPD8337	Approved
0.6462	Remote Similarity	NPD8336	Approved
0.646	Remote Similarity	NPD7732	Phase 3
0.6449	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6869	Approved
0.6446	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6617	Approved
0.6446	Remote Similarity	NPD8130	Phase 1
0.6446	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD5208	Approved
0.6417	Remote Similarity	NPD6012	Approved
0.6417	Remote Similarity	NPD6014	Approved
0.6417	Remote Similarity	NPD6013	Approved
0.6406	Remote Similarity	NPD6067	Discontinued
0.6396	Remote Similarity	NPD7637	Suspended
0.6396	Remote Similarity	NPD6079	Approved
0.6396	Remote Similarity	NPD6050	Approved
0.6389	Remote Similarity	NPD6098	Approved
0.6389	Remote Similarity	NPD3618	Phase 1
0.6385	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4632	Approved
0.6336	Remote Similarity	NPD6033	Approved
0.6333	Remote Similarity	NPD6011	Approved
0.6316	Remote Similarity	NPD7839	Suspended
0.6311	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5692	Phase 3
0.6283	Remote Similarity	NPD6001	Approved
0.6275	Remote Similarity	NPD8039	Approved
0.6269	Remote Similarity	NPD8338	Approved
0.6261	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD6921	Approved
0.6239	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4634	Approved
0.623	Remote Similarity	NPD6371	Approved
0.6228	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3133	Approved
0.6204	Remote Similarity	NPD4786	Approved
0.6204	Remote Similarity	NPD3668	Phase 3
0.6204	Remote Similarity	NPD3665	Phase 1
0.6204	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD5211	Phase 2
0.6174	Remote Similarity	NPD5221	Approved
0.6174	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5222	Approved
0.6174	Remote Similarity	NPD4697	Phase 3
0.6174	Remote Similarity	NPD7614	Phase 1
0.6168	Remote Similarity	NPD5209	Approved
0.6168	Remote Similarity	NPD3667	Approved
0.6161	Remote Similarity	NPD5785	Approved
0.6161	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD4700	Approved
0.6154	Remote Similarity	NPD7830	Approved
0.6154	Remote Similarity	NPD7829	Approved
0.6154	Remote Similarity	NPD7625	Phase 1
0.6154	Remote Similarity	NPD5286	Approved
0.614	Remote Similarity	NPD5282	Discontinued
0.6124	Remote Similarity	NPD5983	Phase 2
0.6121	Remote Similarity	NPD5173	Approved
0.6111	Remote Similarity	NPD6274	Approved
0.6111	Remote Similarity	NPD6868	Approved
0.6106	Remote Similarity	NPD7983	Approved
0.6094	Remote Similarity	NPD7101	Approved
0.6094	Remote Similarity	NPD7100	Approved
0.6091	Remote Similarity	NPD4519	Discontinued
0.6091	Remote Similarity	NPD4623	Approved
0.6083	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD1780	Approved
0.6075	Remote Similarity	NPD1779	Approved
0.6074	Remote Similarity	NPD7260	Phase 2
0.6061	Remote Similarity	NPD6336	Discontinued
0.6053	Remote Similarity	NPD4202	Approved
0.605	Remote Similarity	NPD4633	Approved
0.605	Remote Similarity	NPD5224	Approved
0.605	Remote Similarity	NPD5225	Approved
0.605	Remote Similarity	NPD5226	Approved
0.6038	Remote Similarity	NPD7645	Phase 2
0.6033	Remote Similarity	NPD4768	Approved
0.6033	Remote Similarity	NPD4767	Approved
0.6019	Remote Similarity	NPD4223	Phase 3
0.6019	Remote Similarity	NPD4221	Approved
0.6017	Remote Similarity	NPD6648	Approved
0.6016	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6908	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