NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	420.21
Volume:	417.204
LogP:	2.671
LogD:	2.821
LogS:	-4.145
# Rotatable Bonds:	4
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	6.042
Fsp3:	0.826
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:	-5.296
MDCK Permeability:	2.2171334421727806e-05
Pgp-inhibitor:	0.167
Pgp-substrate:	0.663
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.266

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	81.92011260986328%
Volume Distribution (VD):	1.343
Pgp-substrate:	3.87715482711792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.578

ADMET: Excretion

Clearance (CL):	8.216
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.369
AMES Toxicity:	0.98
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.233
Carcinogencity:	0.849
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.281

Download Data

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

Natural Product: NPC476759

Natural Product ID:	NPC476759
*Common Name:**	methyl (2S,4R,9R,10S,13R,17R)-4-ethoxy-17-hydroxy-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,17R)-4-ethoxy-17-hydroxy-9-methyl-6-oxo-5,16-dioxapentacyclo[12.3.3.01,13.02,10.04,8]icos-7-ene-14-carboxylate
Synonyms:
Standard InCHIKey:	YYHHIADJWFSLJF-UAQXTFKHSA-N
Standard InCHI:	InChI=1S/C23H32O7/c1-4-29-23-11-16-14(13(2)15(23)10-18(24)30-23)6-7-17-21(19(25)27-3)8-5-9-22(16,17)20(26)28-12-21/h10,13-14,16-17,20,26H,4-9,11-12H2,1-3H3/t13-,14+,16+,17+,20-,21?,22?,23-/m1/s1
SMILES:	CCO[C@@]12C[C@H]3[C@@H](CC[C@@H]4C35CCCC4(CO[C@H]5O)C(=O)OC)[C@H](C1=CC(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162818953
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	=	7400	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 NPC476759 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	233
0.1-0.2	1466
0.2-0.3	4287
0.3-0.4	8026
0.4-0.5	13135
0.5-0.6	7487
0.6-0.7	5012
0.7-0.8	2706
0.8-0.85	308
0.85-0.9	28
0.9-0.95	1
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC476766
0.9703	High Similarity	NPC476765
0.96	High Similarity	NPC476764
0.96	High Similarity	NPC476763
0.9505	High Similarity	NPC476762
0.9505	High Similarity	NPC476761
0.9505	High Similarity	NPC476760
0.902	High Similarity	NPC476769
0.901	High Similarity	NPC476767
0.8991	High Similarity	NPC474483
0.8868	High Similarity	NPC31522
0.8824	High Similarity	NPC477721
0.8824	High Similarity	NPC477716
0.8785	High Similarity	NPC472666
0.8774	High Similarity	NPC300614
0.8774	High Similarity	NPC90946
0.875	High Similarity	NPC476150
0.875	High Similarity	NPC476127
0.8738	High Similarity	NPC477717
0.8716	High Similarity	NPC157441
0.8679	High Similarity	NPC475570
0.8627	High Similarity	NPC477719
0.8627	High Similarity	NPC477718
0.8624	High Similarity	NPC12046
0.8624	High Similarity	NPC194951
0.8621	High Similarity	NPC469757
0.8621	High Similarity	NPC117702
0.8621	High Similarity	NPC146456
0.8621	High Similarity	NPC471357
0.8598	High Similarity	NPC392
0.8598	High Similarity	NPC219900
0.8598	High Similarity	NPC177524
0.8598	High Similarity	NPC473483
0.8598	High Similarity	NPC325054
0.8584	High Similarity	NPC470312
0.8558	High Similarity	NPC471075
0.8522	High Similarity	NPC27363
0.8515	High Similarity	NPC477722
0.8509	High Similarity	NPC476204
0.8509	High Similarity	NPC170084
0.8475	Intermediate Similarity	NPC469752
0.8475	Intermediate Similarity	NPC86159
0.8475	Intermediate Similarity	NPC471359
0.8475	Intermediate Similarity	NPC9499
0.8475	Intermediate Similarity	NPC471358
0.8475	Intermediate Similarity	NPC180079
0.8475	Intermediate Similarity	NPC469754
0.8475	Intermediate Similarity	NPC89514
0.8475	Intermediate Similarity	NPC471361
0.8475	Intermediate Similarity	NPC471360
0.8475	Intermediate Similarity	NPC219085
0.8475	Intermediate Similarity	NPC10823
0.8475	Intermediate Similarity	NPC469751
0.8475	Intermediate Similarity	NPC469753
0.8475	Intermediate Similarity	NPC17896
0.8475	Intermediate Similarity	NPC471352
0.8475	Intermediate Similarity	NPC284406
0.8475	Intermediate Similarity	NPC251866
0.8475	Intermediate Similarity	NPC70542
0.8475	Intermediate Similarity	NPC6108
0.8475	Intermediate Similarity	NPC197707
0.8475	Intermediate Similarity	NPC469755
0.8462	Intermediate Similarity	NPC117685
0.8447	Intermediate Similarity	NPC475709
0.8421	Intermediate Similarity	NPC281840
0.8416	Intermediate Similarity	NPC472303
0.8396	Intermediate Similarity	NPC476770
0.8393	Intermediate Similarity	NPC471816
0.839	Intermediate Similarity	NPC311534
0.8381	Intermediate Similarity	NPC471412
0.8376	Intermediate Similarity	NPC469750
0.8376	Intermediate Similarity	NPC250556
0.8364	Intermediate Similarity	NPC270586
0.8349	Intermediate Similarity	NPC112457
0.8318	Intermediate Similarity	NPC222161
0.8317	Intermediate Similarity	NPC289479
0.8305	Intermediate Similarity	NPC179412
0.8305	Intermediate Similarity	NPC240070
0.8305	Intermediate Similarity	NPC329784
0.8305	Intermediate Similarity	NPC471356
0.8304	Intermediate Similarity	NPC472274
0.8304	Intermediate Similarity	NPC110861
0.8302	Intermediate Similarity	NPC134077
0.8302	Intermediate Similarity	NPC165250
0.8291	Intermediate Similarity	NPC318135
0.8288	Intermediate Similarity	NPC277769
0.8288	Intermediate Similarity	NPC4573
0.8288	Intermediate Similarity	NPC90952
0.8286	Intermediate Similarity	NPC477720
0.8286	Intermediate Similarity	NPC471413
0.8269	Intermediate Similarity	NPC51499
0.8269	Intermediate Similarity	NPC476768
0.8264	Intermediate Similarity	NPC247190
0.8264	Intermediate Similarity	NPC146857
0.8264	Intermediate Similarity	NPC116075
0.8264	Intermediate Similarity	NPC469749
0.8264	Intermediate Similarity	NPC32793
0.8257	Intermediate Similarity	NPC275539
0.8257	Intermediate Similarity	NPC189075
0.8246	Intermediate Similarity	NPC239293
0.823	Intermediate Similarity	NPC44170
0.823	Intermediate Similarity	NPC469794
0.823	Intermediate Similarity	NPC72772
0.823	Intermediate Similarity	NPC268954
0.8224	Intermediate Similarity	NPC471208
0.8224	Intermediate Similarity	NPC45897
0.8224	Intermediate Similarity	NPC95899
0.8218	Intermediate Similarity	NPC477782
0.8214	Intermediate Similarity	NPC264153
0.8208	Intermediate Similarity	NPC63249
0.8198	Intermediate Similarity	NPC31839
0.8197	Intermediate Similarity	NPC329636
0.819	Intermediate Similarity	NPC275086
0.819	Intermediate Similarity	NPC325229
0.8182	Intermediate Similarity	NPC471250
0.8182	Intermediate Similarity	NPC475030
0.8174	Intermediate Similarity	NPC122971
0.8173	Intermediate Similarity	NPC242848
0.8173	Intermediate Similarity	NPC17578
0.8173	Intermediate Similarity	NPC29952
0.8173	Intermediate Similarity	NPC240673
0.8173	Intermediate Similarity	NPC234993
0.8173	Intermediate Similarity	NPC134072
0.8167	Intermediate Similarity	NPC477196
0.8167	Intermediate Similarity	NPC276838
0.8167	Intermediate Similarity	NPC329986
0.8167	Intermediate Similarity	NPC140092
0.8167	Intermediate Similarity	NPC188234
0.8167	Intermediate Similarity	NPC125077
0.8167	Intermediate Similarity	NPC232785
0.8165	Intermediate Similarity	NPC110496
0.8158	Intermediate Similarity	NPC473968
0.8158	Intermediate Similarity	NPC473405
0.8151	Intermediate Similarity	NPC470516
0.8151	Intermediate Similarity	NPC298841
0.8142	Intermediate Similarity	NPC69576
0.8142	Intermediate Similarity	NPC471633
0.8142	Intermediate Similarity	NPC84949
0.8142	Intermediate Similarity	NPC31354
0.8137	Intermediate Similarity	NPC477783
0.8131	Intermediate Similarity	NPC121423
0.8131	Intermediate Similarity	NPC162973
0.8131	Intermediate Similarity	NPC476081
0.8131	Intermediate Similarity	NPC476890
0.813	Intermediate Similarity	NPC194716
0.8125	Intermediate Similarity	NPC1046
0.8125	Intermediate Similarity	NPC48249
0.8125	Intermediate Similarity	NPC80843
0.8125	Intermediate Similarity	NPC471967
0.8119	Intermediate Similarity	NPC174342
0.8113	Intermediate Similarity	NPC477968
0.8113	Intermediate Similarity	NPC324841
0.8113	Intermediate Similarity	NPC20113
0.8113	Intermediate Similarity	NPC228251
0.8113	Intermediate Similarity	NPC474012
0.8113	Intermediate Similarity	NPC476299
0.8113	Intermediate Similarity	NPC473576
0.8113	Intermediate Similarity	NPC161527
0.8113	Intermediate Similarity	NPC475156
0.8113	Intermediate Similarity	NPC477972
0.8113	Intermediate Similarity	NPC251680
0.8113	Intermediate Similarity	NPC219285
0.8113	Intermediate Similarity	NPC477971
0.8108	Intermediate Similarity	NPC242611
0.8099	Intermediate Similarity	NPC16569
0.8099	Intermediate Similarity	NPC173435
0.8099	Intermediate Similarity	NPC301639
0.8099	Intermediate Similarity	NPC45346
0.8099	Intermediate Similarity	NPC478064
0.8099	Intermediate Similarity	NPC173347
0.8099	Intermediate Similarity	NPC478155
0.8099	Intermediate Similarity	NPC300655
0.8099	Intermediate Similarity	NPC478065
0.8099	Intermediate Similarity	NPC159338
0.8099	Intermediate Similarity	NPC262796
0.8099	Intermediate Similarity	NPC477197
0.8099	Intermediate Similarity	NPC172374
0.8099	Intermediate Similarity	NPC475167
0.8099	Intermediate Similarity	NPC329993
0.8099	Intermediate Similarity	NPC222951
0.8099	Intermediate Similarity	NPC253456
0.8099	Intermediate Similarity	NPC25998
0.8099	Intermediate Similarity	NPC134914
0.8099	Intermediate Similarity	NPC311178
0.8099	Intermediate Similarity	NPC476074
0.8099	Intermediate Similarity	NPC475377
0.8099	Intermediate Similarity	NPC43589
0.8099	Intermediate Similarity	NPC264566
0.8087	Intermediate Similarity	NPC473617
0.8087	Intermediate Similarity	NPC473828
0.8087	Intermediate Similarity	NPC471548
0.8083	Intermediate Similarity	NPC472270
0.8083	Intermediate Similarity	NPC23020
0.8083	Intermediate Similarity	NPC112492
0.8083	Intermediate Similarity	NPC472268
0.8083	Intermediate Similarity	NPC477075
0.8083	Intermediate Similarity	NPC245094
0.8083	Intermediate Similarity	NPC477078
0.8083	Intermediate Similarity	NPC475281
0.8083	Intermediate Similarity	NPC472269

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 NPC476759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1660
0.2-0.3	3707
0.3-0.4	2310
0.4-0.5	789
0.5-0.6	284
0.6-0.7	169
0.7-0.8	31
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
0.8598	High Similarity	NPD6686	Approved
0.8475	Intermediate Similarity	NPD7319	Approved
0.8376	Intermediate Similarity	NPD7507	Approved
0.819	Intermediate Similarity	NPD7638	Approved
0.8113	Intermediate Similarity	NPD7640	Approved
0.8113	Intermediate Similarity	NPD7639	Approved
0.7931	Intermediate Similarity	NPD7328	Approved
0.7931	Intermediate Similarity	NPD7327	Approved
0.7899	Intermediate Similarity	NPD8328	Phase 3
0.7863	Intermediate Similarity	NPD7516	Approved
0.7838	Intermediate Similarity	NPD6412	Phase 2
0.7797	Intermediate Similarity	NPD8294	Approved
0.7797	Intermediate Similarity	NPD8377	Approved
0.7739	Intermediate Similarity	NPD8133	Approved
0.7731	Intermediate Similarity	NPD8380	Approved
0.7731	Intermediate Similarity	NPD8335	Approved
0.7731	Intermediate Similarity	NPD8378	Approved
0.7731	Intermediate Similarity	NPD8379	Approved
0.7731	Intermediate Similarity	NPD8033	Approved
0.7731	Intermediate Similarity	NPD8296	Approved
0.7642	Intermediate Similarity	NPD7736	Approved
0.7542	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7632	Discontinued
0.7477	Intermediate Similarity	NPD7748	Approved
0.7453	Intermediate Similarity	NPD7515	Phase 2
0.7426	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7395	Intermediate Similarity	NPD7115	Discovery
0.7391	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6370	Approved
0.7364	Intermediate Similarity	NPD4225	Approved
0.7295	Intermediate Similarity	NPD8516	Approved
0.7295	Intermediate Similarity	NPD8515	Approved
0.7295	Intermediate Similarity	NPD7503	Approved
0.7295	Intermediate Similarity	NPD8513	Phase 3
0.7295	Intermediate Similarity	NPD8517	Approved
0.7273	Intermediate Similarity	NPD7902	Approved
0.7258	Intermediate Similarity	NPD7492	Approved
0.7213	Intermediate Similarity	NPD6054	Approved
0.7213	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD6882	Approved
0.72	Intermediate Similarity	NPD6616	Approved
0.7179	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7078	Approved
0.713	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD7128	Approved
0.713	Intermediate Similarity	NPD6411	Approved
0.713	Intermediate Similarity	NPD6402	Approved
0.713	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6083	Phase 2
0.7117	Intermediate Similarity	NPD6084	Phase 2
0.7064	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD5778	Approved
0.7016	Intermediate Similarity	NPD6016	Approved
0.7016	Intermediate Similarity	NPD6015	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.6967	Remote Similarity	NPD6009	Approved
0.696	Remote Similarity	NPD5988	Approved
0.6952	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6373	Approved
0.6949	Remote Similarity	NPD6372	Approved
0.6944	Remote Similarity	NPD6101	Approved
0.6944	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5328	Approved
0.6935	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6917	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD3573	Approved
0.6909	Remote Similarity	NPD6399	Phase 3
0.6891	Remote Similarity	NPD6883	Approved
0.6891	Remote Similarity	NPD7102	Approved
0.6891	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6698	Approved
0.6881	Remote Similarity	NPD46	Approved
0.6852	Remote Similarity	NPD6672	Approved
0.6852	Remote Similarity	NPD5737	Approved
0.6846	Remote Similarity	NPD6914	Discontinued
0.6833	Remote Similarity	NPD6869	Approved
0.6833	Remote Similarity	NPD8130	Phase 1
0.6833	Remote Similarity	NPD6650	Approved
0.6833	Remote Similarity	NPD6649	Approved
0.6833	Remote Similarity	NPD6847	Approved
0.6833	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD7334	Approved
0.6822	Remote Similarity	NPD3618	Phase 1
0.6822	Remote Similarity	NPD6409	Approved
0.6822	Remote Similarity	NPD6684	Approved
0.6822	Remote Similarity	NPD7521	Approved
0.6822	Remote Similarity	NPD5330	Approved
0.6822	Remote Similarity	NPD7146	Approved
0.6818	Remote Similarity	NPD7637	Suspended
0.6818	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD6079	Approved
0.6818	Remote Similarity	NPD8035	Phase 2
0.6807	Remote Similarity	NPD6014	Approved
0.6807	Remote Similarity	NPD6013	Approved
0.6807	Remote Similarity	NPD6012	Approved
0.6786	Remote Similarity	NPD5695	Phase 3
0.6777	Remote Similarity	NPD8297	Approved
0.6772	Remote Similarity	NPD6067	Discontinued
0.6754	Remote Similarity	NPD5696	Approved
0.6723	Remote Similarity	NPD6011	Approved
0.6721	Remote Similarity	NPD4632	Approved
0.6697	Remote Similarity	NPD6903	Approved
0.6695	Remote Similarity	NPD6008	Approved
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4753	Phase 2
0.6636	Remote Similarity	NPD4786	Approved
0.6636	Remote Similarity	NPD3665	Phase 1
0.6636	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD3133	Approved
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8074	Phase 3
0.6612	Remote Similarity	NPD4634	Approved
0.6612	Remote Similarity	NPD6371	Approved
0.6604	Remote Similarity	NPD3667	Approved
0.6581	Remote Similarity	NPD5211	Phase 2
0.6579	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5222	Approved
0.6579	Remote Similarity	NPD7839	Suspended
0.6579	Remote Similarity	NPD4697	Phase 3
0.6579	Remote Similarity	NPD5221	Approved
0.6577	Remote Similarity	NPD5785	Approved
0.6574	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD5286	Approved
0.6552	Remote Similarity	NPD4700	Approved
0.6552	Remote Similarity	NPD4696	Approved
0.6552	Remote Similarity	NPD5285	Approved
0.6522	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7604	Phase 2
0.6491	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6904	Approved
0.6486	Remote Similarity	NPD6080	Approved
0.6486	Remote Similarity	NPD6673	Approved
0.6484	Remote Similarity	NPD6921	Approved
0.6484	Remote Similarity	NPD5983	Phase 2
0.648	Remote Similarity	NPD6868	Approved
0.648	Remote Similarity	NPD6274	Approved
0.6476	Remote Similarity	NPD7645	Phase 2
0.6471	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5141	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4202	Approved
0.6457	Remote Similarity	NPD7101	Approved
0.6457	Remote Similarity	NPD7100	Approved
0.6441	Remote Similarity	NPD5225	Approved
0.6441	Remote Similarity	NPD5224	Approved
0.6441	Remote Similarity	NPD5226	Approved
0.6441	Remote Similarity	NPD4633	Approved
0.6435	Remote Similarity	NPD7614	Phase 1
0.6412	Remote Similarity	NPD6336	Discontinued
0.6404	Remote Similarity	NPD5282	Discontinued
0.6387	Remote Similarity	NPD5174	Approved
0.6387	Remote Similarity	NPD5175	Approved
0.6385	Remote Similarity	NPD7829	Approved
0.6385	Remote Similarity	NPD7830	Approved
0.6381	Remote Similarity	NPD6115	Approved
0.6381	Remote Similarity	NPD6118	Approved
0.6381	Remote Similarity	NPD6114	Approved
0.6381	Remote Similarity	NPD6697	Approved
0.6378	Remote Similarity	NPD6335	Approved
0.6372	Remote Similarity	NPD7983	Approved
0.6364	Remote Similarity	NPD7625	Phase 1
0.6364	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD4623	Approved
0.6364	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6908	Approved
0.6357	Remote Similarity	NPD6909	Approved
0.6356	Remote Similarity	NPD5344	Discontinued
0.6356	Remote Similarity	NPD5223	Approved
0.6348	Remote Similarity	NPD4629	Approved
0.6348	Remote Similarity	NPD5210	Approved
0.6339	Remote Similarity	NPD6051	Approved
0.6299	Remote Similarity	NPD6317	Approved
0.6296	Remote Similarity	NPD4221	Approved
0.6296	Remote Similarity	NPD4223	Phase 3
0.6293	Remote Similarity	NPD7732	Phase 3
0.6281	Remote Similarity	NPD4768	Approved
0.6281	Remote Similarity	NPD4767	Approved
0.6273	Remote Similarity	NPD5329	Approved
0.6262	Remote Similarity	NPD4695	Discontinued
0.6262	Remote Similarity	NPD7525	Registered
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD6314	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