NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	469.837
LogP:	3.989
LogD:	4.406
LogS:	-2.948
# Rotatable Bonds:	10
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	4.517
Fsp3:	0.76
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:	-4.991
MDCK Permeability:	1.1777252439060248e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	93.61480712890625%
Volume Distribution (VD):	1.715
Pgp-substrate:	2.1533570289611816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.311
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	7.821
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.374
Human Hepatotoxicity (H-HT):	0.601
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.853
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.662
Carcinogencity:	0.741
Eye Corrosion:	0.942
Eye Irritation:	0.602
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC477040

Natural Product ID:	NPC477040
*Common Name:**	[(2S)-2-[2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-5-(furan-3-yl)pentyl] hydrogen sulfate;1,1-dimethylguanidine
IUPAC Name:	[(2S)-2-[2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-5-(furan-3-yl)pentyl] hydrogen sulfate;1,1-dimethylguanidine
Synonyms:
Standard InCHIKey:	XQHUNCZWANSTLT-IEPCCHDWSA-N
Standard InCHI:	InChI=1S/C25H40O5S.C3H9N3/c1-19-7-5-10-23-24(19,3)14-11-20(2)25(23,4)15-12-21(18-30-31(26,27)28)8-6-9-22-13-16-29-17-22;1-6(2)3(4)5/h13,16-17,20-21,23H,1,5-12,14-15,18H2,2-4H3,(H,26,27,28);1-2H3,(H3,4,5)/t20-,21+,23+,24-,25+;/m1./s1
SMILES:	C[C@@H]1CC[C@]2([C@@H]([C@@]1(C)CC[C@H](CCCC3=COC=C3)COS(=O)(=O)O)CCCC2=C)C.CN(C)C(=N)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492072
PubChem CID:	49797589
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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	2
MIC	6

Activity Type	# Activity
Individual Protein	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	31300	nM	PMID[18824352]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	185500	nM	PMID[18824352]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50	ug/ml	PMID[18824352]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug/ml	PMID[18824352]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	25	ug/ml	PMID[18824352]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	25	ug/ml	PMID[18824352]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100	ug/ml	PMID[18824352]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	6.25	ug/ml	PMID[18824352]

☑ 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 NPC477040 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	205
0.1-0.2	1224
0.2-0.3	3388
0.3-0.4	10496
0.4-0.5	13721
0.5-0.6	12364
0.6-0.7	1099
0.7-0.8	183
0.8-0.85	9
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC476925
0.9835	High Similarity	NPC477123
0.9835	High Similarity	NPC477966
0.9672	High Similarity	NPC476917
0.9672	High Similarity	NPC477039
0.9672	High Similarity	NPC327527
0.9504	High Similarity	NPC477965
0.9504	High Similarity	NPC477038
0.9339	High Similarity	NPC317217
0.9113	High Similarity	NPC179354
0.9106	High Similarity	NPC16922
0.904	High Similarity	NPC23086
0.904	High Similarity	NPC46536
0.904	High Similarity	NPC138139
0.8984	High Similarity	NPC89133
0.8917	High Similarity	NPC150895
0.8898	High Similarity	NPC112706
0.8898	High Similarity	NPC207294
0.8889	High Similarity	NPC74612
0.8871	High Similarity	NPC477967
0.8819	High Similarity	NPC83178
0.877	High Similarity	NPC212918
0.872	High Similarity	NPC36255
0.8712	High Similarity	NPC476947
0.8699	High Similarity	NPC243704
0.8692	High Similarity	NPC61788
0.8661	High Similarity	NPC230979
0.8661	High Similarity	NPC303010
0.8651	High Similarity	NPC272899
0.8583	High Similarity	NPC83115
0.8583	High Similarity	NPC130275
0.8561	High Similarity	NPC218838
0.8538	High Similarity	NPC223063
0.8538	High Similarity	NPC120836
0.8529	High Similarity	NPC67003
0.8507	High Similarity	NPC46896
0.8462	Intermediate Similarity	NPC26532
0.8433	Intermediate Similarity	NPC158525
0.8421	Intermediate Similarity	NPC471006
0.8409	Intermediate Similarity	NPC298190
0.8406	Intermediate Similarity	NPC121158
0.8397	Intermediate Similarity	NPC59502
0.8397	Intermediate Similarity	NPC198904
0.8394	Intermediate Similarity	NPC56197
0.8385	Intermediate Similarity	NPC246392
0.8385	Intermediate Similarity	NPC290955
0.8382	Intermediate Similarity	NPC476943
0.837	Intermediate Similarity	NPC146872
0.8346	Intermediate Similarity	NPC471817
0.8346	Intermediate Similarity	NPC97566
0.8345	Intermediate Similarity	NPC476946
0.8333	Intermediate Similarity	NPC205765
0.8321	Intermediate Similarity	NPC90953
0.8321	Intermediate Similarity	NPC202260
0.832	Intermediate Similarity	NPC144745
0.832	Intermediate Similarity	NPC208906
0.8309	Intermediate Similarity	NPC310830
0.8309	Intermediate Similarity	NPC42400
0.8309	Intermediate Similarity	NPC307401
0.8296	Intermediate Similarity	NPC92941
0.8295	Intermediate Similarity	NPC243269
0.8284	Intermediate Similarity	NPC470740
0.8273	Intermediate Similarity	NPC52412
0.8258	Intermediate Similarity	NPC208389
0.8254	Intermediate Similarity	NPC87466
0.8231	Intermediate Similarity	NPC473885
0.8231	Intermediate Similarity	NPC471074
0.8227	Intermediate Similarity	NPC5676
0.8227	Intermediate Similarity	NPC185456
0.8214	Intermediate Similarity	NPC243577
0.8214	Intermediate Similarity	NPC267632
0.8209	Intermediate Similarity	NPC471995
0.8209	Intermediate Similarity	NPC473982
0.8182	Intermediate Similarity	NPC279877
0.8182	Intermediate Similarity	NPC329707
0.8175	Intermediate Similarity	NPC470742
0.8156	Intermediate Similarity	NPC251865
0.8156	Intermediate Similarity	NPC199044
0.8156	Intermediate Similarity	NPC142113
0.8156	Intermediate Similarity	NPC238843
0.8156	Intermediate Similarity	NPC476944
0.8154	Intermediate Similarity	NPC178382
0.8143	Intermediate Similarity	NPC263337
0.813	Intermediate Similarity	NPC277525
0.8129	Intermediate Similarity	NPC90296
0.8116	Intermediate Similarity	NPC220094
0.8116	Intermediate Similarity	NPC236532
0.8112	Intermediate Similarity	NPC216755
0.8112	Intermediate Similarity	NPC255414
0.8112	Intermediate Similarity	NPC302987
0.8112	Intermediate Similarity	NPC471174
0.8092	Intermediate Similarity	NPC300098
0.8092	Intermediate Similarity	NPC290193
0.8088	Intermediate Similarity	NPC471998
0.8056	Intermediate Similarity	NPC471007
0.8047	Intermediate Similarity	NPC473969
0.8043	Intermediate Similarity	NPC215109
0.8043	Intermediate Similarity	NPC170604
0.8042	Intermediate Similarity	NPC470999
0.8042	Intermediate Similarity	NPC471292
0.8016	Intermediate Similarity	NPC28054
0.8015	Intermediate Similarity	NPC118853
0.8014	Intermediate Similarity	NPC473152
0.8	Intermediate Similarity	NPC69647
0.8	Intermediate Similarity	NPC148374
0.8	Intermediate Similarity	NPC234494
0.8	Intermediate Similarity	NPC472654
0.8	Intermediate Similarity	NPC470998
0.8	Intermediate Similarity	NPC125182
0.7986	Intermediate Similarity	NPC71821
0.7972	Intermediate Similarity	NPC56731
0.797	Intermediate Similarity	NPC476016
0.7955	Intermediate Similarity	NPC75557
0.7955	Intermediate Similarity	NPC71274
0.7945	Intermediate Similarity	NPC212257
0.7945	Intermediate Similarity	NPC196846
0.7945	Intermediate Similarity	NPC470997
0.7943	Intermediate Similarity	NPC20500
0.7931	Intermediate Similarity	NPC93666
0.7917	Intermediate Similarity	NPC346
0.7917	Intermediate Similarity	NPC262198
0.7914	Intermediate Similarity	NPC4764
0.7914	Intermediate Similarity	NPC310043
0.791	Intermediate Similarity	NPC474438
0.791	Intermediate Similarity	NPC474279
0.7907	Intermediate Similarity	NPC137710
0.7895	Intermediate Similarity	NPC474260
0.7895	Intermediate Similarity	NPC81912
0.7895	Intermediate Similarity	NPC329694
0.7895	Intermediate Similarity	NPC329922
0.7891	Intermediate Similarity	NPC217180
0.7891	Intermediate Similarity	NPC272590
0.7891	Intermediate Similarity	NPC131801
0.7891	Intermediate Similarity	NPC312525
0.7886	Intermediate Similarity	NPC471521
0.7886	Intermediate Similarity	NPC473356
0.7883	Intermediate Similarity	NPC293253
0.7879	Intermediate Similarity	NPC188377
0.7879	Intermediate Similarity	NPC65735
0.7877	Intermediate Similarity	NPC470791
0.7877	Intermediate Similarity	NPC195325
0.7877	Intermediate Similarity	NPC470790
0.7877	Intermediate Similarity	NPC471001
0.7863	Intermediate Similarity	NPC471549
0.7863	Intermediate Similarity	NPC473379
0.7862	Intermediate Similarity	NPC470941
0.7862	Intermediate Similarity	NPC250228
0.7862	Intermediate Similarity	NPC221809
0.7857	Intermediate Similarity	NPC471996
0.7842	Intermediate Similarity	NPC214572
0.784	Intermediate Similarity	NPC105249
0.7838	Intermediate Similarity	NPC121615
0.7838	Intermediate Similarity	NPC472672
0.7838	Intermediate Similarity	NPC294511
0.7838	Intermediate Similarity	NPC33938
0.7838	Intermediate Similarity	NPC246164
0.7838	Intermediate Similarity	NPC470996
0.7838	Intermediate Similarity	NPC469503
0.7836	Intermediate Similarity	NPC95567
0.7836	Intermediate Similarity	NPC474830
0.7836	Intermediate Similarity	NPC319140
0.7832	Intermediate Similarity	NPC223415
0.7832	Intermediate Similarity	NPC470741
0.7823	Intermediate Similarity	NPC177331
0.7823	Intermediate Similarity	NPC196864
0.7823	Intermediate Similarity	NPC228842
0.7823	Intermediate Similarity	NPC46551
0.7823	Intermediate Similarity	NPC159927
0.7823	Intermediate Similarity	NPC477404
0.7823	Intermediate Similarity	NPC156189
0.7823	Intermediate Similarity	NPC469335
0.7823	Intermediate Similarity	NPC476122
0.782	Intermediate Similarity	NPC474829
0.7812	Intermediate Similarity	NPC45536
0.7808	Intermediate Similarity	NPC476942
0.7808	Intermediate Similarity	NPC476941
0.7803	Intermediate Similarity	NPC476351
0.7793	Intermediate Similarity	NPC233763
0.7785	Intermediate Similarity	NPC282445
0.7785	Intermediate Similarity	NPC30222
0.7785	Intermediate Similarity	NPC34421
0.7785	Intermediate Similarity	NPC178932
0.7785	Intermediate Similarity	NPC237259
0.7785	Intermediate Similarity	NPC302054
0.7785	Intermediate Similarity	NPC253201
0.7785	Intermediate Similarity	NPC98206
0.7778	Intermediate Similarity	NPC1811
0.7778	Intermediate Similarity	NPC26157
0.777	Intermediate Similarity	NPC18135
0.777	Intermediate Similarity	NPC471000
0.7754	Intermediate Similarity	NPC474426
0.7754	Intermediate Similarity	NPC474407
0.7754	Intermediate Similarity	NPC474425
0.7746	Intermediate Similarity	NPC201370
0.7746	Intermediate Similarity	NPC473983
0.774	Intermediate Similarity	NPC476937
0.774	Intermediate Similarity	NPC10088
0.774	Intermediate Similarity	NPC476938
0.7734	Intermediate Similarity	NPC205523
0.7733	Intermediate Similarity	NPC296807

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 NPC477040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	682
0.2-0.3	1272
0.3-0.4	2816
0.4-0.5	2905
0.5-0.6	1270
0.6-0.7	70
0.7-0.8	0
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
0.7733	Intermediate Similarity	NPD5761	Phase 2
0.7733	Intermediate Similarity	NPD5760	Phase 2
0.7552	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7192	Intermediate Similarity	NPD1471	Phase 3
0.7174	Intermediate Similarity	NPD1876	Approved
0.7162	Intermediate Similarity	NPD4628	Phase 3
0.7115	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD8032	Phase 2
0.7059	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2799	Discontinued
0.7045	Intermediate Similarity	NPD1241	Discontinued
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD7003	Approved
0.6928	Remote Similarity	NPD6765	Approved
0.6928	Remote Similarity	NPD6764	Approved
0.6884	Remote Similarity	NPD3023	Approved
0.6884	Remote Similarity	NPD3026	Approved
0.6861	Remote Similarity	NPD5585	Approved
0.6857	Remote Similarity	NPD5327	Phase 3
0.6849	Remote Similarity	NPD6355	Discontinued
0.6846	Remote Similarity	NPD2346	Discontinued
0.6824	Remote Similarity	NPD8434	Phase 2
0.6806	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7458	Discontinued
0.6795	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4307	Phase 2
0.6781	Remote Similarity	NPD2979	Phase 3
0.6779	Remote Similarity	NPD2531	Phase 2
0.6776	Remote Similarity	NPD2309	Approved
0.6761	Remote Similarity	NPD2797	Approved
0.6759	Remote Similarity	NPD2313	Discontinued
0.6755	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3025	Approved
0.6739	Remote Similarity	NPD1651	Approved
0.6739	Remote Similarity	NPD3024	Approved
0.6714	Remote Similarity	NPD1281	Approved
0.6711	Remote Similarity	NPD4308	Phase 3
0.6711	Remote Similarity	NPD4110	Phase 3
0.6711	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD17	Approved
0.6691	Remote Similarity	NPD7157	Approved
0.669	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD3869	Phase 3
0.6667	Remote Similarity	NPD1551	Phase 2
0.6646	Remote Similarity	NPD6599	Discontinued
0.6644	Remote Similarity	NPD3268	Approved
0.6643	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6625	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4359	Approved
0.66	Remote Similarity	NPD3748	Approved
0.6599	Remote Similarity	NPD4062	Phase 3
0.6585	Remote Similarity	NPD8127	Discontinued
0.6564	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6279	Approved
0.6562	Remote Similarity	NPD6280	Approved
0.6556	Remote Similarity	NPD6100	Approved
0.6556	Remote Similarity	NPD4477	Approved
0.6556	Remote Similarity	NPD4476	Approved
0.6556	Remote Similarity	NPD2438	Suspended
0.6556	Remote Similarity	NPD2935	Discontinued
0.6556	Remote Similarity	NPD6099	Approved
0.6554	Remote Similarity	NPD3142	Approved
0.6554	Remote Similarity	NPD3140	Approved
0.6549	Remote Similarity	NPD9717	Approved
0.6541	Remote Similarity	NPD2182	Approved
0.6538	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3764	Approved
0.6528	Remote Similarity	NPD1203	Approved
0.6528	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7440	Discontinued
0.6513	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5735	Approved
0.65	Remote Similarity	NPD5691	Approved
0.6494	Remote Similarity	NPD8166	Discontinued
0.6494	Remote Similarity	NPD3750	Approved
0.6488	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1019	Discontinued
0.6481	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3226	Approved
0.6467	Remote Similarity	NPD6353	Approved
0.6463	Remote Similarity	NPD7095	Approved
0.6454	Remote Similarity	NPD1778	Approved
0.6452	Remote Similarity	NPD3887	Approved
0.6442	Remote Similarity	NPD7768	Phase 2
0.6438	Remote Similarity	NPD7028	Phase 2
0.6433	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6559	Discontinued
0.6429	Remote Similarity	NPD1894	Discontinued
0.6429	Remote Similarity	NPD1243	Approved
0.6424	Remote Similarity	NPD5494	Approved
0.642	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6798	Discontinued
0.6419	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3496	Discontinued
0.6405	Remote Similarity	NPD6002	Phase 3
0.6405	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5763	Approved
0.6405	Remote Similarity	NPD6005	Phase 3
0.6405	Remote Similarity	NPD5762	Approved
0.6405	Remote Similarity	NPD6004	Phase 3
0.6405	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4618	Approved
0.64	Remote Similarity	NPD1933	Approved
0.64	Remote Similarity	NPD4622	Approved
0.6398	Remote Similarity	NPD6873	Phase 2
0.6397	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2614	Approved
0.6391	Remote Similarity	NPD3134	Approved
0.6377	Remote Similarity	NPD5951	Approved
0.6376	Remote Similarity	NPD6663	Approved
0.6376	Remote Similarity	NPD4870	Approved
0.6375	Remote Similarity	NPD2649	Approved
0.6375	Remote Similarity	NPD2651	Approved
0.6369	Remote Similarity	NPD6799	Approved
0.6364	Remote Similarity	NPD4534	Discontinued
0.6364	Remote Similarity	NPD1549	Phase 2
0.6364	Remote Similarity	NPD919	Approved
0.6364	Remote Similarity	NPD6287	Discontinued
0.6358	Remote Similarity	NPD7577	Discontinued
0.6352	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7008	Discontinued
0.635	Remote Similarity	NPD7843	Approved
0.635	Remote Similarity	NPD5535	Approved
0.6347	Remote Similarity	NPD6808	Phase 2
0.6341	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD2932	Approved
0.6338	Remote Similarity	NPD4626	Approved
0.6338	Remote Similarity	NPD3019	Approved
0.6333	Remote Similarity	NPD4060	Phase 1
0.6331	Remote Similarity	NPD6387	Discontinued
0.6329	Remote Similarity	NPD4661	Approved
0.6329	Remote Similarity	NPD4662	Approved
0.6327	Remote Similarity	NPD5736	Approved
0.6327	Remote Similarity	NPD9494	Approved
0.6323	Remote Similarity	NPD2800	Approved
0.6316	Remote Similarity	NPD5689	Approved
0.6316	Remote Similarity	NPD5688	Approved
0.6309	Remote Similarity	NPD411	Approved
0.6308	Remote Similarity	NPD1238	Approved
0.6306	Remote Similarity	NPD7236	Approved
0.6303	Remote Similarity	NPD7075	Discontinued
0.6303	Remote Similarity	NPD3749	Approved
0.6301	Remote Similarity	NPD6362	Approved
0.6299	Remote Similarity	NPD2353	Approved
0.6299	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7411	Suspended
0.6296	Remote Similarity	NPD6677	Suspended
0.6296	Remote Similarity	NPD2684	Approved
0.6291	Remote Similarity	NPD3657	Discovery
0.6289	Remote Similarity	NPD5049	Phase 3
0.6287	Remote Similarity	NPD1247	Approved
0.628	Remote Similarity	NPD2296	Approved
0.6275	Remote Similarity	NPD1510	Phase 2
0.6272	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6233	Phase 2
0.6259	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5647	Approved
0.6259	Remote Similarity	NPD4624	Approved
0.6258	Remote Similarity	NPD6844	Discontinued
0.6258	Remote Similarity	NPD2897	Discontinued
0.6258	Remote Similarity	NPD5958	Discontinued
0.625	Remote Similarity	NPD1611	Approved
0.625	Remote Similarity	NPD1607	Approved
0.625	Remote Similarity	NPD6653	Approved
0.625	Remote Similarity	NPD7229	Phase 3
0.6242	Remote Similarity	NPD3882	Suspended
0.6242	Remote Similarity	NPD2354	Approved
0.6241	Remote Similarity	NPD5536	Phase 2
0.6241	Remote Similarity	NPD164	Approved
0.6233	Remote Similarity	NPD8651	Approved
0.6233	Remote Similarity	NPD6696	Suspended
0.6226	Remote Similarity	NPD2533	Approved
0.6226	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2532	Approved
0.6226	Remote Similarity	NPD2534	Approved
0.6225	Remote Similarity	NPD1240	Approved
0.6224	Remote Similarity	NPD3095	Discontinued
0.6222	Remote Similarity	NPD1358	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