NPASS Compound

Structure

NPC473619 OpenBabel07101718332D 25 26 0 0 1 0 0 0 0 0999 V2000 5.1114 -4.5901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6251 -3.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1603 -4.8991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4172 -4.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4661 -4.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2582 -5.5171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7230 -3.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 13 2 0 0 0 0 10 11 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 14 1 1 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 6 0 0 0 18 25 1 1 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	365.496
LogP:	2.399
LogD:	2.659
LogS:	-3.404
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	4.883
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.724
MDCK Permeability:	2.086209315166343e-05
Pgp-inhibitor:	0.532
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.94
20% Bioavailability (F20%):	0.78
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	93.68761444091797%
Volume Distribution (VD):	1.41
Pgp-substrate:	4.447581768035889%

ADMET: Metabolism

CYP1A2-inhibitor:	0.407
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.543
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.301
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.854
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	8.23
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.453
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.657
Carcinogencity:	0.047
Eye Corrosion:	0.318
Eye Irritation:	0.126
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC473619

Natural Product ID:	NPC473619
*Common Name:**	SLFNZRXROGKMKG-DPCOETHOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SLFNZRXROGKMKG-DPCOETHOSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-6-12(3)19(22)25-18-13(4)9-7-8-11(2)10-15-16(17(18)21)14(5)20(23)24-15/h6,9-10,15-18,21H,5,7-8H2,1-4H3/b11-10+,12-6+,13-9-/t15-,16-,17+,18+/m0/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1/C(=CCC/C(=C/[C@H]2[C@@H]([C@H]1O)C(=C)C(=O)O2)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447313
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104492]
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	100.0	uM	PMID[493224]
NPT2	Others	Unspecified		Activity	=	20.0	uM	PMID[493224]

☑ 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 NPC473619 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	200
0.1-0.2	1279
0.2-0.3	4946
0.3-0.4	9196
0.4-0.5	14514
0.5-0.6	7454
0.6-0.7	3805
0.7-0.8	945
0.8-0.85	227
0.85-0.9	111
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC473321
0.954	High Similarity	NPC288240
0.954	High Similarity	NPC273579
0.954	High Similarity	NPC295204
0.954	High Similarity	NPC162205
0.9529	High Similarity	NPC473715
0.9438	High Similarity	NPC477921
0.9326	High Similarity	NPC477922
0.9326	High Similarity	NPC471142
0.9231	High Similarity	NPC471144
0.9195	High Similarity	NPC474032
0.9176	High Similarity	NPC21469
0.9101	High Similarity	NPC475912
0.9022	High Similarity	NPC473326
0.9011	High Similarity	NPC473859
0.9	High Similarity	NPC303942
0.9	High Similarity	NPC57405
0.8989	High Similarity	NPC30515
0.8989	High Similarity	NPC184463
0.8941	High Similarity	NPC40746
0.8941	High Similarity	NPC169575
0.8925	High Similarity	NPC288876
0.8925	High Similarity	NPC475949
0.8901	High Similarity	NPC270013
0.8901	High Similarity	NPC36954
0.8901	High Similarity	NPC475659
0.8901	High Similarity	NPC14961
0.8889	High Similarity	NPC81419
0.8889	High Similarity	NPC179746
0.8889	High Similarity	NPC476300
0.8889	High Similarity	NPC212486
0.8876	High Similarity	NPC474232
0.8876	High Similarity	NPC475855
0.8876	High Similarity	NPC51004
0.8864	High Similarity	NPC202672
0.8851	High Similarity	NPC469910
0.8804	High Similarity	NPC279621
0.8804	High Similarity	NPC306041
0.8791	High Similarity	NPC81386
0.8791	High Similarity	NPC474035
0.8778	High Similarity	NPC208886
0.8778	High Similarity	NPC12172
0.8764	High Similarity	NPC307411
0.8737	High Similarity	NPC149371
0.8736	High Similarity	NPC470755
0.8721	High Similarity	NPC131669
0.8721	High Similarity	NPC59097
0.8721	High Similarity	NPC116543
0.8721	High Similarity	NPC473390
0.8706	High Similarity	NPC24417
0.8696	High Similarity	NPC471141
0.869	High Similarity	NPC98557
0.869	High Similarity	NPC167881
0.8681	High Similarity	NPC125674
0.8681	High Similarity	NPC228451
0.8681	High Similarity	NPC475838
0.8667	High Similarity	NPC144133
0.8667	High Similarity	NPC474761
0.8667	High Similarity	NPC179394
0.8667	High Similarity	NPC476004
0.8652	High Similarity	NPC475819
0.8652	High Similarity	NPC476803
0.8636	High Similarity	NPC112685
0.8636	High Similarity	NPC475461
0.8636	High Similarity	NPC305475
0.8632	High Similarity	NPC47880
0.8621	High Similarity	NPC476804
0.8621	High Similarity	NPC158756
0.8617	High Similarity	NPC474213
0.8605	High Similarity	NPC229825
0.8602	High Similarity	NPC476315
0.8587	High Similarity	NPC474247
0.8587	High Similarity	NPC473316
0.8587	High Similarity	NPC473330
0.8571	High Similarity	NPC477513
0.8556	High Similarity	NPC295312
0.8556	High Similarity	NPC151770
0.8556	High Similarity	NPC477011
0.8556	High Similarity	NPC166919
0.8523	High Similarity	NPC255307
0.8471	Intermediate Similarity	NPC270126
0.8454	Intermediate Similarity	NPC475945
0.8454	Intermediate Similarity	NPC475871
0.8452	Intermediate Similarity	NPC476028
0.8452	Intermediate Similarity	NPC171204
0.8452	Intermediate Similarity	NPC141789
0.8444	Intermediate Similarity	NPC40376
0.8444	Intermediate Similarity	NPC48338
0.8444	Intermediate Similarity	NPC20339
0.8444	Intermediate Similarity	NPC89001
0.8444	Intermediate Similarity	NPC21208
0.8444	Intermediate Similarity	NPC233551
0.8444	Intermediate Similarity	NPC280621
0.8444	Intermediate Similarity	NPC476805
0.8438	Intermediate Similarity	NPC474339
0.8438	Intermediate Similarity	NPC476270
0.8438	Intermediate Similarity	NPC164598
0.8427	Intermediate Similarity	NPC107717
0.8427	Intermediate Similarity	NPC171174
0.8427	Intermediate Similarity	NPC240695
0.8427	Intermediate Similarity	NPC62118
0.8427	Intermediate Similarity	NPC150755
0.8427	Intermediate Similarity	NPC231096
0.8427	Intermediate Similarity	NPC475581
0.8427	Intermediate Similarity	NPC114694
0.8427	Intermediate Similarity	NPC232555
0.8427	Intermediate Similarity	NPC142117
0.8421	Intermediate Similarity	NPC187268
0.8409	Intermediate Similarity	NPC114979
0.8409	Intermediate Similarity	NPC141193
0.8409	Intermediate Similarity	NPC191476
0.8409	Intermediate Similarity	NPC96259
0.8404	Intermediate Similarity	NPC230800
0.8404	Intermediate Similarity	NPC17585
0.8387	Intermediate Similarity	NPC471147
0.8372	Intermediate Similarity	NPC281132
0.8367	Intermediate Similarity	NPC203659
0.8367	Intermediate Similarity	NPC100487
0.8353	Intermediate Similarity	NPC471465
0.8353	Intermediate Similarity	NPC93763
0.8353	Intermediate Similarity	NPC108816
0.8353	Intermediate Similarity	NPC196653
0.8352	Intermediate Similarity	NPC280612
0.8352	Intermediate Similarity	NPC477017
0.8352	Intermediate Similarity	NPC477016
0.8351	Intermediate Similarity	NPC474747
0.8351	Intermediate Similarity	NPC471148
0.8351	Intermediate Similarity	NPC324017
0.8351	Intermediate Similarity	NPC320019
0.8333	Intermediate Similarity	NPC231889
0.8333	Intermediate Similarity	NPC186148
0.8333	Intermediate Similarity	NPC178215
0.8315	Intermediate Similarity	NPC107986
0.8315	Intermediate Similarity	NPC132496
0.8315	Intermediate Similarity	NPC319795
0.8315	Intermediate Similarity	NPC286338
0.8315	Intermediate Similarity	NPC103284
0.8315	Intermediate Similarity	NPC477018
0.8315	Intermediate Similarity	NPC231009
0.8315	Intermediate Similarity	NPC110710
0.8315	Intermediate Similarity	NPC473651
0.8315	Intermediate Similarity	NPC38468
0.8315	Intermediate Similarity	NPC473478
0.8315	Intermediate Similarity	NPC473669
0.8315	Intermediate Similarity	NPC100921
0.8315	Intermediate Similarity	NPC120398
0.8315	Intermediate Similarity	NPC223871
0.8315	Intermediate Similarity	NPC82795
0.8315	Intermediate Similarity	NPC471567
0.8315	Intermediate Similarity	NPC283085
0.8315	Intermediate Similarity	NPC66346
0.8315	Intermediate Similarity	NPC1083
0.8315	Intermediate Similarity	NPC50362
0.8283	Intermediate Similarity	NPC243998
0.8276	Intermediate Similarity	NPC52861
0.8265	Intermediate Similarity	NPC110989
0.8261	Intermediate Similarity	NPC80875
0.8261	Intermediate Similarity	NPC251385
0.8261	Intermediate Similarity	NPC239517
0.8261	Intermediate Similarity	NPC49342
0.8261	Intermediate Similarity	NPC475748
0.8247	Intermediate Similarity	NPC201718
0.8247	Intermediate Similarity	NPC474742
0.8247	Intermediate Similarity	NPC15993
0.8247	Intermediate Similarity	NPC473332
0.8242	Intermediate Similarity	NPC242364
0.8242	Intermediate Similarity	NPC172821
0.8242	Intermediate Similarity	NPC320569
0.8242	Intermediate Similarity	NPC100454
0.8242	Intermediate Similarity	NPC58219
0.8242	Intermediate Similarity	NPC287164
0.8242	Intermediate Similarity	NPC191929
0.8242	Intermediate Similarity	NPC274446
0.8242	Intermediate Similarity	NPC39754
0.8242	Intermediate Similarity	NPC171135
0.8242	Intermediate Similarity	NPC261952
0.8242	Intermediate Similarity	NPC151403
0.8242	Intermediate Similarity	NPC81045
0.8242	Intermediate Similarity	NPC234077
0.8242	Intermediate Similarity	NPC177629
0.8242	Intermediate Similarity	NPC153805
0.8242	Intermediate Similarity	NPC133730
0.8242	Intermediate Similarity	NPC169511
0.8242	Intermediate Similarity	NPC61257
0.8235	Intermediate Similarity	NPC320630
0.8235	Intermediate Similarity	NPC7563
0.8235	Intermediate Similarity	NPC116177
0.8222	Intermediate Similarity	NPC103523
0.8222	Intermediate Similarity	NPC279267
0.8222	Intermediate Similarity	NPC134885
0.8222	Intermediate Similarity	NPC473687
0.8222	Intermediate Similarity	NPC69082
0.8222	Intermediate Similarity	NPC50637
0.8222	Intermediate Similarity	NPC309211
0.8222	Intermediate Similarity	NPC134865
0.8222	Intermediate Similarity	NPC210218
0.8222	Intermediate Similarity	NPC204686
0.8222	Intermediate Similarity	NPC308412
0.8222	Intermediate Similarity	NPC47937
0.8222	Intermediate Similarity	NPC134807

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 NPC473619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1916
0.2-0.3	3702
0.3-0.4	2223
0.4-0.5	754
0.5-0.6	289
0.6-0.7	71
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8315	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD46	Approved
0.8261	Intermediate Similarity	NPD6698	Approved
0.7789	Intermediate Similarity	NPD7983	Approved
0.7684	Intermediate Similarity	NPD7838	Discovery
0.767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6371	Approved
0.7264	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD4225	Approved
0.7157	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4249	Approved
0.7064	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1695	Approved
0.701	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD4251	Approved
0.697	Remote Similarity	NPD5785	Approved
0.6947	Remote Similarity	NPD7154	Phase 3
0.6857	Remote Similarity	NPD5344	Discontinued
0.6847	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6435	Approved
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.681	Remote Similarity	NPD8516	Approved
0.681	Remote Similarity	NPD8515	Approved
0.681	Remote Similarity	NPD8517	Approved
0.681	Remote Similarity	NPD8513	Phase 3
0.6809	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5363	Approved
0.6771	Remote Similarity	NPD6110	Phase 1
0.6735	Remote Similarity	NPD5786	Approved
0.6635	Remote Similarity	NPD7839	Suspended
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5368	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.6598	Remote Similarity	NPD5362	Discontinued
0.6596	Remote Similarity	NPD4268	Approved
0.6596	Remote Similarity	NPD4271	Approved
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7830	Approved
0.6555	Remote Similarity	NPD7829	Approved
0.6555	Remote Similarity	NPD7642	Approved
0.6552	Remote Similarity	NPD7641	Discontinued
0.6529	Remote Similarity	NPD8074	Phase 3
0.6509	Remote Similarity	NPD7638	Approved
0.6495	Remote Similarity	NPD4270	Approved
0.6495	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4269	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.6465	Remote Similarity	NPD1694	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4252	Approved
0.6458	Remote Similarity	NPD4820	Approved
0.6449	Remote Similarity	NPD7640	Approved
0.6449	Remote Similarity	NPD6648	Approved
0.6449	Remote Similarity	NPD7639	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6404	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5369	Approved
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4632	Approved
0.6328	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5209	Approved
0.6316	Remote Similarity	NPD2204	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.629	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8444	Approved
0.6228	Remote Similarity	NPD6421	Discontinued
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7260	Phase 2
0.618	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8451	Approved
0.6161	Remote Similarity	NPD6008	Approved
0.6146	Remote Similarity	NPD4756	Discovery
0.6129	Remote Similarity	NPD8448	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD5697	Approved
0.6106	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5331	Approved
0.61	Remote Similarity	NPD5332	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6095	Remote Similarity	NPD7637	Suspended
0.6078	Remote Similarity	NPD6422	Discontinued
0.6067	Remote Similarity	NPD3197	Phase 1
0.6061	Remote Similarity	NPD4790	Discontinued
0.6058	Remote Similarity	NPD5370	Suspended
0.6053	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.605	Remote Similarity	NPD6009	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.6038	Remote Similarity	NPD6399	Phase 3
0.6034	Remote Similarity	NPD6650	Approved
0.6034	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD6054	Approved
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD6845	Suspended
0.6016	Remote Similarity	NPD8328	Phase 3
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD8390	Approved
0.5984	Remote Similarity	NPD8392	Approved
0.5984	Remote Similarity	NPD8391	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5968	Remote Similarity	NPD8342	Approved
0.5968	Remote Similarity	NPD8341	Approved
0.5968	Remote Similarity	NPD8299	Approved
0.5968	Remote Similarity	NPD8340	Approved
0.5965	Remote Similarity	NPD5701	Approved
0.5952	Remote Similarity	NPD7736	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5943	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD8039	Approved
0.5935	Remote Similarity	NPD6370	Approved
0.5935	Remote Similarity	NPD5988	Approved
0.5934	Remote Similarity	NPD7331	Phase 2
0.592	Remote Similarity	NPD8273	Phase 1
0.5917	Remote Similarity	NPD7500	Approved
0.5913	Remote Similarity	NPD7320	Approved
0.5913	Remote Similarity	NPD6011	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5897	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7632	Discontinued
0.5887	Remote Similarity	NPD7604	Phase 2
0.5873	Remote Similarity	NPD8293	Discontinued
0.5872	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7327	Approved
0.5868	Remote Similarity	NPD7328	Approved
0.5854	Remote Similarity	NPD8033	Approved
0.5854	Remote Similarity	NPD7503	Approved
0.5847	Remote Similarity	NPD6882	Approved
0.5842	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7516	Approved
0.5818	Remote Similarity	NPD6083	Phase 2
0.5818	Remote Similarity	NPD7902	Approved
0.5818	Remote Similarity	NPD6084	Phase 2
0.5812	Remote Similarity	NPD4634	Approved
0.5812	Remote Similarity	NPD2067	Discontinued
0.5806	Remote Similarity	NPD8080	Discontinued
0.5798	Remote Similarity	NPD8133	Approved
0.5794	Remote Similarity	NPD6336	Discontinued
0.5785	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5695	Phase 3
0.5772	Remote Similarity	NPD8294	Approved
0.5772	Remote Similarity	NPD8377	Approved
0.5766	Remote Similarity	NPD5696	Approved
0.5752	Remote Similarity	NPD5211	Phase 2
0.573	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8378	Approved
0.5726	Remote Similarity	NPD8379	Approved
0.5726	Remote Similarity	NPD8266	Approved
0.5726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8268	Approved
0.5726	Remote Similarity	NPD8267	Approved
0.5726	Remote Similarity	NPD8335	Approved
0.5726	Remote Similarity	NPD8269	Approved
0.5726	Remote Similarity	NPD8380	Approved
0.5726	Remote Similarity	NPD8296	Approved
0.5714	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5702	Remote Similarity	NPD6274	Approved
0.5702	Remote Similarity	NPD6647	Phase 2
0.5688	Remote Similarity	NPD7748	Approved
0.5682	Remote Similarity	NPD9119	Approved
0.5682	Remote Similarity	NPD69	Approved
0.5676	Remote Similarity	NPD4755	Approved
0.5656	Remote Similarity	NPD7505	Discontinued
0.5652	Remote Similarity	NPD7341	Phase 2
0.5652	Remote Similarity	NPD5141	Approved
0.5648	Remote Similarity	NPD6079	Approved
0.5648	Remote Similarity	NPD7515	Phase 2
0.5639	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5330	Approved
0.5619	Remote Similarity	NPD7521	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