NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	422.19
Volume:	408.698
LogP:	1.849
LogD:	2.513
LogS:	-4.1
# Rotatable Bonds:	3
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	6.183
Fsp3:	0.818
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:	-5.226
MDCK Permeability:	5.2370145567692816e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.78
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.365

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	66.39102935791016%
Volume Distribution (VD):	1.426
Pgp-substrate:	28.75126838684082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.397

ADMET: Excretion

Clearance (CL):	3.891
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.384
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.89
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.076
Carcinogencity:	0.917
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC476766

Natural Product ID:	NPC476766
*Common Name:**	methyl (2S,4R,9R,10S,13R)-4,15-dihydroxy-17-methoxy-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)-4,15-dihydroxy-17-methoxy-9-methyl-6-oxo-5,16-dioxapentacyclo[12.3.3.01,13.02,10.04,8]icos-7-ene-14-carboxylate
Synonyms:
Standard InCHIKey:	GZUTZXLQXVQYME-QRSASCIISA-N
Standard InCHI:	InChI=1S/C22H30O8/c1-11-12-5-6-15-20(14(12)10-22(26)13(11)9-16(23)30-22)7-4-8-21(15,17(24)27-2)18(25)29-19(20)28-3/h9,11-12,14-15,18-19,25-26H,4-8,10H2,1-3H3/t11-,12+,14+,15-,18?,19?,20?,21?,22-/m1/s1
SMILES:	C[C@@H]1[C@@H]2CC[C@@H]3C4([C@H]2C[C@@]5(C1=CC(=O)O5)O)CCCC3(C(OC4OC)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162818947
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	=	520	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 NPC476766 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	236
0.1-0.2	1469
0.2-0.3	4230
0.3-0.4	7888
0.4-0.5	13053
0.5-0.6	7794
0.6-0.7	5072
0.7-0.8	2616
0.8-0.85	304
0.85-0.9	26
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC476765
0.9706	High Similarity	NPC476759
0.9412	High Similarity	NPC476760
0.9412	High Similarity	NPC476762
0.9412	High Similarity	NPC476761
0.9314	High Similarity	NPC476764
0.9314	High Similarity	NPC476763
0.9109	High Similarity	NPC476767
0.8909	High Similarity	NPC474483
0.8835	High Similarity	NPC477717
0.8785	High Similarity	NPC31522
0.875	High Similarity	NPC476769
0.8738	High Similarity	NPC477721
0.8738	High Similarity	NPC477716
0.8704	High Similarity	NPC472666
0.8692	High Similarity	NPC300614
0.8692	High Similarity	NPC90946
0.8673	High Similarity	NPC476127
0.8673	High Similarity	NPC476150
0.8547	High Similarity	NPC469757
0.8547	High Similarity	NPC471357
0.8547	High Similarity	NPC117702
0.8547	High Similarity	NPC146456
0.8544	High Similarity	NPC477719
0.8544	High Similarity	NPC475709
0.8544	High Similarity	NPC477718
0.8519	High Similarity	NPC177524
0.8519	High Similarity	NPC392
0.8519	High Similarity	NPC219900
0.8519	High Similarity	NPC325054
0.8515	High Similarity	NPC472303
0.8509	High Similarity	NPC281840
0.8509	High Similarity	NPC470312
0.8476	Intermediate Similarity	NPC471075
0.8468	Intermediate Similarity	NPC157441
0.8448	Intermediate Similarity	NPC27363
0.8435	Intermediate Similarity	NPC170084
0.8435	Intermediate Similarity	NPC476204
0.8426	Intermediate Similarity	NPC475570
0.8416	Intermediate Similarity	NPC289479
0.8403	Intermediate Similarity	NPC469751
0.8403	Intermediate Similarity	NPC284406
0.8403	Intermediate Similarity	NPC10823
0.8403	Intermediate Similarity	NPC251866
0.8403	Intermediate Similarity	NPC471359
0.8403	Intermediate Similarity	NPC70542
0.8403	Intermediate Similarity	NPC6108
0.8403	Intermediate Similarity	NPC469754
0.8403	Intermediate Similarity	NPC471352
0.8403	Intermediate Similarity	NPC469755
0.8403	Intermediate Similarity	NPC197707
0.8403	Intermediate Similarity	NPC471361
0.8403	Intermediate Similarity	NPC469752
0.8403	Intermediate Similarity	NPC9499
0.8403	Intermediate Similarity	NPC471358
0.8403	Intermediate Similarity	NPC86159
0.8403	Intermediate Similarity	NPC180079
0.8403	Intermediate Similarity	NPC89514
0.8403	Intermediate Similarity	NPC219085
0.8403	Intermediate Similarity	NPC469753
0.8403	Intermediate Similarity	NPC471360
0.8403	Intermediate Similarity	NPC17896
0.8393	Intermediate Similarity	NPC472274
0.8381	Intermediate Similarity	NPC117685
0.8378	Intermediate Similarity	NPC194951
0.8378	Intermediate Similarity	NPC12046
0.8376	Intermediate Similarity	NPC318135
0.8349	Intermediate Similarity	NPC473483
0.8319	Intermediate Similarity	NPC311534
0.8318	Intermediate Similarity	NPC476770
0.8317	Intermediate Similarity	NPC477782
0.8305	Intermediate Similarity	NPC250556
0.8305	Intermediate Similarity	NPC469750
0.8304	Intermediate Similarity	NPC264153
0.8269	Intermediate Similarity	NPC134072
0.8269	Intermediate Similarity	NPC17578
0.8269	Intermediate Similarity	NPC240673
0.8269	Intermediate Similarity	NPC242848
0.8269	Intermediate Similarity	NPC234993
0.8261	Intermediate Similarity	NPC122971
0.8252	Intermediate Similarity	NPC477722
0.8246	Intermediate Similarity	NPC473968
0.8235	Intermediate Similarity	NPC477783
0.8235	Intermediate Similarity	NPC471356
0.8235	Intermediate Similarity	NPC240070
0.8235	Intermediate Similarity	NPC329784
0.8235	Intermediate Similarity	NPC179412
0.8224	Intermediate Similarity	NPC121423
0.8214	Intermediate Similarity	NPC90952
0.8208	Intermediate Similarity	NPC477720
0.8197	Intermediate Similarity	NPC146857
0.8197	Intermediate Similarity	NPC116075
0.8197	Intermediate Similarity	NPC247190
0.8197	Intermediate Similarity	NPC469749
0.8197	Intermediate Similarity	NPC32793
0.8174	Intermediate Similarity	NPC239293
0.8167	Intermediate Similarity	NPC476859
0.8167	Intermediate Similarity	NPC112492
0.8167	Intermediate Similarity	NPC23020
0.8167	Intermediate Similarity	NPC472268
0.8167	Intermediate Similarity	NPC472270
0.8167	Intermediate Similarity	NPC472269
0.8158	Intermediate Similarity	NPC471816
0.8148	Intermediate Similarity	NPC471208
0.8148	Intermediate Similarity	NPC95899
0.8131	Intermediate Similarity	NPC198992
0.8131	Intermediate Similarity	NPC471412
0.813	Intermediate Similarity	NPC329636
0.8125	Intermediate Similarity	NPC270586
0.8125	Intermediate Similarity	NPC31839
0.8115	Intermediate Similarity	NPC324933
0.8115	Intermediate Similarity	NPC473679
0.8115	Intermediate Similarity	NPC233223
0.8115	Intermediate Similarity	NPC319719
0.8115	Intermediate Similarity	NPC196874
0.8115	Intermediate Similarity	NPC475444
0.8115	Intermediate Similarity	NPC183816
0.8115	Intermediate Similarity	NPC475177
0.8115	Intermediate Similarity	NPC322904
0.8113	Intermediate Similarity	NPC325229
0.8113	Intermediate Similarity	NPC275086
0.8108	Intermediate Similarity	NPC112457
0.8099	Intermediate Similarity	NPC188234
0.8099	Intermediate Similarity	NPC232785
0.8099	Intermediate Similarity	NPC125077
0.8099	Intermediate Similarity	NPC476851
0.8099	Intermediate Similarity	NPC329986
0.8099	Intermediate Similarity	NPC477196
0.8099	Intermediate Similarity	NPC476854
0.8099	Intermediate Similarity	NPC276838
0.8099	Intermediate Similarity	NPC140092
0.8087	Intermediate Similarity	NPC473405
0.8083	Intermediate Similarity	NPC298841
0.8083	Intermediate Similarity	NPC470516
0.8077	Intermediate Similarity	NPC474555
0.8077	Intermediate Similarity	NPC474554
0.8073	Intermediate Similarity	NPC222161
0.8073	Intermediate Similarity	NPC471937
0.807	Intermediate Similarity	NPC110861
0.8067	Intermediate Similarity	NPC470922
0.8065	Intermediate Similarity	NPC194716
0.8058	Intermediate Similarity	NPC472814
0.8058	Intermediate Similarity	NPC177037
0.8056	Intermediate Similarity	NPC134077
0.8056	Intermediate Similarity	NPC165250
0.8053	Intermediate Similarity	NPC277769
0.8053	Intermediate Similarity	NPC4573
0.8053	Intermediate Similarity	NPC80843
0.8053	Intermediate Similarity	NPC1046
0.8053	Intermediate Similarity	NPC471967
0.8053	Intermediate Similarity	NPC48249
0.8039	Intermediate Similarity	NPC251528
0.8037	Intermediate Similarity	NPC324841
0.8037	Intermediate Similarity	NPC471413
0.8037	Intermediate Similarity	NPC476299
0.8037	Intermediate Similarity	NPC251680
0.8037	Intermediate Similarity	NPC474012
0.8036	Intermediate Similarity	NPC242611
0.8033	Intermediate Similarity	NPC173347
0.8033	Intermediate Similarity	NPC16569
0.8033	Intermediate Similarity	NPC300655
0.8033	Intermediate Similarity	NPC478155
0.8033	Intermediate Similarity	NPC173435
0.8033	Intermediate Similarity	NPC262796
0.8033	Intermediate Similarity	NPC159338
0.8033	Intermediate Similarity	NPC478064
0.8033	Intermediate Similarity	NPC476852
0.8033	Intermediate Similarity	NPC476862
0.8033	Intermediate Similarity	NPC45346
0.8033	Intermediate Similarity	NPC477197
0.8033	Intermediate Similarity	NPC478065
0.8033	Intermediate Similarity	NPC222951
0.8033	Intermediate Similarity	NPC264566
0.8033	Intermediate Similarity	NPC253456
0.8033	Intermediate Similarity	NPC172374
0.8033	Intermediate Similarity	NPC25998
0.8033	Intermediate Similarity	NPC475167
0.8033	Intermediate Similarity	NPC329993
0.8033	Intermediate Similarity	NPC476074
0.8033	Intermediate Similarity	NPC476855
0.8033	Intermediate Similarity	NPC311178
0.8033	Intermediate Similarity	NPC475377
0.8033	Intermediate Similarity	NPC43589
0.8033	Intermediate Similarity	NPC476863
0.8033	Intermediate Similarity	NPC134914
0.8033	Intermediate Similarity	NPC301639
0.8019	Intermediate Similarity	NPC51499
0.8019	Intermediate Similarity	NPC476768
0.8018	Intermediate Similarity	NPC189075
0.8018	Intermediate Similarity	NPC275539
0.8017	Intermediate Similarity	NPC245094
0.8017	Intermediate Similarity	NPC477193
0.8017	Intermediate Similarity	NPC475281
0.8017	Intermediate Similarity	NPC329923
0.8017	Intermediate Similarity	NPC477191
0.8017	Intermediate Similarity	NPC477192
0.8017	Intermediate Similarity	NPC477194
0.8017	Intermediate Similarity	NPC477075
0.8017	Intermediate Similarity	NPC473617
0.8017	Intermediate Similarity	NPC471548

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 NPC476766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1683
0.2-0.3	3707
0.3-0.4	2290
0.4-0.5	769
0.5-0.6	305
0.6-0.7	161
0.7-0.8	33
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
0.8519	High Similarity	NPD6686	Approved
0.8403	Intermediate Similarity	NPD7319	Approved
0.8305	Intermediate Similarity	NPD7507	Approved
0.8037	Intermediate Similarity	NPD7640	Approved
0.8037	Intermediate Similarity	NPD7639	Approved
0.7944	Intermediate Similarity	NPD7638	Approved
0.7863	Intermediate Similarity	NPD7327	Approved
0.7863	Intermediate Similarity	NPD7328	Approved
0.7833	Intermediate Similarity	NPD8328	Phase 3
0.7797	Intermediate Similarity	NPD7516	Approved
0.7731	Intermediate Similarity	NPD8294	Approved
0.7731	Intermediate Similarity	NPD8377	Approved
0.7672	Intermediate Similarity	NPD8133	Approved
0.7667	Intermediate Similarity	NPD8380	Approved
0.7667	Intermediate Similarity	NPD8335	Approved
0.7667	Intermediate Similarity	NPD8379	Approved
0.7667	Intermediate Similarity	NPD8378	Approved
0.7667	Intermediate Similarity	NPD8296	Approved
0.7667	Intermediate Similarity	NPD8033	Approved
0.7611	Intermediate Similarity	NPD6412	Phase 2
0.7479	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4225	Approved
0.744	Intermediate Similarity	NPD7736	Approved
0.7411	Intermediate Similarity	NPD7632	Discontinued
0.7377	Intermediate Similarity	NPD8516	Approved
0.7377	Intermediate Similarity	NPD8513	Phase 3
0.7377	Intermediate Similarity	NPD8517	Approved
0.7377	Intermediate Similarity	NPD8515	Approved
0.7353	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7115	Discovery
0.7328	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7748	Approved
0.7236	Intermediate Similarity	NPD7503	Approved
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7222	Intermediate Similarity	NPD8293	Discontinued
0.7177	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7063	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD7902	Approved
0.7016	Intermediate Similarity	NPD6319	Approved
0.7016	Intermediate Similarity	NPD6059	Approved
0.7016	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.696	Remote Similarity	NPD6015	Approved
0.696	Remote Similarity	NPD6016	Approved
0.6953	Remote Similarity	NPD7078	Approved
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6911	Remote Similarity	NPD6009	Approved
0.6909	Remote Similarity	NPD6411	Approved
0.6905	Remote Similarity	NPD5988	Approved
0.6903	Remote Similarity	NPD6083	Phase 2
0.6903	Remote Similarity	NPD6084	Phase 2
0.6891	Remote Similarity	NPD6373	Approved
0.6891	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5701	Approved
0.6864	Remote Similarity	NPD5697	Approved
0.6852	Remote Similarity	NPD3573	Approved
0.6818	Remote Similarity	NPD6698	Approved
0.6818	Remote Similarity	NPD46	Approved
0.6807	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6881	Approved
0.6807	Remote Similarity	NPD7320	Approved
0.6794	Remote Similarity	NPD6914	Discontinued
0.6789	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7900	Approved
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6650	Approved
0.6777	Remote Similarity	NPD6649	Approved
0.6759	Remote Similarity	NPD3618	Phase 1
0.6757	Remote Similarity	NPD7637	Suspended
0.675	Remote Similarity	NPD6014	Approved
0.675	Remote Similarity	NPD6013	Approved
0.675	Remote Similarity	NPD6012	Approved
0.6727	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6101	Approved
0.6727	Remote Similarity	NPD5328	Approved
0.6726	Remote Similarity	NPD5695	Phase 3
0.6721	Remote Similarity	NPD6053	Discontinued
0.6721	Remote Similarity	NPD8297	Approved
0.6696	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6008	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD6672	Approved
0.6609	Remote Similarity	NPD4755	Approved
0.6607	Remote Similarity	NPD8035	Phase 2
0.6607	Remote Similarity	NPD8034	Phase 2
0.6607	Remote Similarity	NPD5693	Phase 1
0.6607	Remote Similarity	NPD6079	Approved
0.6606	Remote Similarity	NPD7334	Approved
0.6606	Remote Similarity	NPD6684	Approved
0.6606	Remote Similarity	NPD6409	Approved
0.6606	Remote Similarity	NPD5330	Approved
0.6606	Remote Similarity	NPD7521	Approved
0.6606	Remote Similarity	NPD7146	Approved
0.6589	Remote Similarity	NPD6067	Discontinued
0.6579	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4753	Phase 2
0.6574	Remote Similarity	NPD3666	Approved
0.6574	Remote Similarity	NPD3133	Approved
0.6574	Remote Similarity	NPD3665	Phase 1
0.6557	Remote Similarity	NPD4634	Approved
0.6557	Remote Similarity	NPD6371	Approved
0.6555	Remote Similarity	NPD5141	Approved
0.6552	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3667	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD4697	Phase 3
0.6518	Remote Similarity	NPD5785	Approved
0.6515	Remote Similarity	NPD6033	Approved
0.6514	Remote Similarity	NPD1694	Approved
0.6504	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4700	Approved
0.6496	Remote Similarity	NPD4696	Approved
0.6496	Remote Similarity	NPD5285	Approved
0.6496	Remote Similarity	NPD5286	Approved
0.6486	Remote Similarity	NPD6903	Approved
0.6466	Remote Similarity	NPD5173	Approved
0.646	Remote Similarity	NPD7983	Approved
0.6455	Remote Similarity	NPD4623	Approved
0.6455	Remote Similarity	NPD4519	Discontinued
0.6455	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6921	Approved
0.6434	Remote Similarity	NPD5983	Phase 2
0.6429	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4786	Approved
0.6417	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4202	Approved
0.6387	Remote Similarity	NPD5226	Approved
0.6387	Remote Similarity	NPD4633	Approved
0.6387	Remote Similarity	NPD5225	Approved
0.6387	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6348	Remote Similarity	NPD5282	Discontinued
0.6336	Remote Similarity	NPD7604	Phase 2
0.6336	Remote Similarity	NPD7829	Approved
0.6336	Remote Similarity	NPD7830	Approved
0.6333	Remote Similarity	NPD5175	Approved
0.6333	Remote Similarity	NPD5174	Approved
0.6319	Remote Similarity	NPD7625	Phase 1
0.6311	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5344	Discontinued
0.6303	Remote Similarity	NPD5223	Approved
0.6299	Remote Similarity	NPD6868	Approved
0.6293	Remote Similarity	NPD5210	Approved
0.6293	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4629	Approved
0.6283	Remote Similarity	NPD6080	Approved
0.6283	Remote Similarity	NPD6673	Approved
0.6283	Remote Similarity	NPD6904	Approved
0.6279	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD7101	Approved
0.6262	Remote Similarity	NPD7645	Phase 2
0.626	Remote Similarity	NPD4730	Approved
0.626	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD6317	Approved
0.6241	Remote Similarity	NPD6336	Discontinued
0.6239	Remote Similarity	NPD4223	Phase 3
0.6239	Remote Similarity	NPD7614	Phase 1
0.6239	Remote Similarity	NPD4221	Approved
0.6204	Remote Similarity	NPD4695	Discontinued
0.6202	Remote Similarity	NPD6314	Approved
0.6202	Remote Similarity	NPD6313	Approved
0.6202	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD4754	Approved
0.6195	Remote Similarity	NPD5208	Approved
0.6183	Remote Similarity	NPD6908	Approved
0.6183	Remote Similarity	NPD6909	Approved
0.6176	Remote Similarity	NPD5956	Approved
0.6174	Remote Similarity	NPD5281	Approved
0.6174	Remote Similarity	NPD5284	Approved
0.6168	Remote Similarity	NPD6115	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